HK1194751B

HK1194751B - Silicone hydrogel contact lenses

Info

Publication number: HK1194751B
Application number: HK14108154.9A
Authority: HK
Inventors: 阿瑟．巴克; 大卫．罗伯特．默斯利; 理查德．罗杰斯; 萨拉．阿尔蒙德; 查利．陈; 刘宇文; 查尔斯．A．弗朗西斯; 洪叶
Original assignee: Coopervision International Limited
Priority date: 2011-02-28
Filing date: 2012-02-23
Publication date: 2016-06-30

Description

Silicone hydrogel contact lenses

Cross reference to related applications

This application claims the benefit of prior U.S. provisional patent application No. 61/447,161, filed 2011, 2, month 28, in accordance with 35u.s.c. § 119(e), which is incorporated herein by reference in its entirety.

Technical Field

The present invention relates to silicone hydrogel contact lenses and related compositions and methods.

Background

Commercially and clinically, silicone hydrogel contact lenses are a popular replacement for conventional hydrogel contact lenses (i.e., hydrogel contact lenses that do not contain silicone or silicone-containing components). It is believed that the presence of hydrophobic ingredients (e.g., siloxanes and other hydrophobic reactive ingredients) in silicone hydrogel contact lens formulations at least in part contributes to the frequent occurrence of clinically ophthalmically unacceptable surface wettabilities associated with the development of novel silicone hydrogel contact lenses. For example, if a macroscopically discernible (discernible under magnification) "non-wetting spot" is observed on the lens surface by an eye care practitioner using conventional techniques (e.g., slit lamp inspection), then it can be determined that the silicone hydrogel contact lens has a clinically ophthalmically unacceptable surface wettability. The non-wetting spots appear as discontinuities or breaks in the lens wearer's pre-lens tear film present on the anterior surface of the silicone hydrogel contact lens provided on the eye. Non-wetting spots differ from dry spots in that non-wetting spots are spots on the surface of the contact lens that are not covered by the tear film even after blinking of the lens wearer. In contrast, dry spots, as understood in the art, are spots on the surface of a contact lens that are covered by the pre-lens tear film after blinking, and after a period of time the pre-lens tear film breaks or breaks. It is believed that the non-wetting spots can be attributed to an increase in the amount of hydrophobic lens material (e.g., silicone) present at the location of the non-wetting spots as compared to other areas of the lens surface that can be wetted by the pre-lens tear film.

Industrial manufacture of silicone hydrogel contact lenses typically includes one or more washing steps prior to packaging that remove unreacted or partially reacted chemicals, particularly hydrophobic chemicals, from the polymeric lens body using volatile organic solvents such as alcohols. This step is commonly referred to as an extraction process to remove extractable material from the polymerized silicone hydrogel contact lens product. After extraction, the lenses are then rinsed and hydrated with an aqueous solution. The use of volatile organic solvents facilitates the removal of components of polymerized silicone hydrogel contact lenses that have lower solubility in aqueous solutions or water. However, the use of volatile organic solvents presents a safety risk at the contact lens manufacturing site and may be associated with increased cost of goods.

In addition to extraction with volatile organic solvents, a variety of other manufacturing techniques have been employed to produce silicone hydrogel contact lenses having clinically ophthalmically compatible lens surfaces. For example, some silicone hydrogel contact lenses are plasma treated to form a hydrophilic lens surface based on the chemical reactivity of the chemicals in the polymerizable lens formulation; some silicone hydrogel contact lenses are formed from polymerizable lens formulations containing a hydrophilic polymeric internal wetting agent, such as polyvinylpyrrolidone (PVP); some silicone hydrogel contact lenses are formed using polar resin contact lens molds instead of non-polar resin contact lens molds, and the lenses are free of hydrophilic polymeric internal wetting agents in the polymerizable lens formulation and are not plasma treated; and some silicone hydrogel contact lenses are formed in non-polar resin molds and provided with ophthalmically compatible lens surfaces.

More recently, silicone hydrogel contact lenses have been produced and designated as daily disposable contact lenses (e.g., 1-DAYACUVULETRUEYE (marketed in the United kingdom in 2008) and CLARITI1-DAY (marketed in the United kingdom in 11 months in 2009); both of which are obviously available in Europe). The lens material for 1-DAYACUVULETRUEYE contact lenses is Narafilcon A under the American name (USAN) and more recently Narafilcon B. The USAN of the lens material for the CLARITI1-DAY contact lenses was Filcon II 3. It is disclosed that the TRUEY (Narafilcon A) contact lens has a water content of 54%, an oxygen transmission rate of 100Dk (at-3.00D, center, no edge correction); oxygen transfer rate of 118Dk/t (10)^-9at-3.00D), a modulus of 0.66MPa, and is related to wetting agent/process. Clariti1-DAY contact lenses have been disclosed as having a water content of 56%, an oxygen transmission rate of 60Dk (at-3.00D, center, no edge correction); oxygen transfer rate of 86Dk/t (10)^-9at-3.00D), a modulus of 0.50MPa, and is related to wetting agent/process.

As understood in the industry, daily disposable contact lenses are the following contact lenses: it is removed from a sealed sterile package (original package) made by the contact lens manufacturer, placed on the person's eye, and at the end of the day, the lens that has been worn by the person is removed and discarded. Typically, a daily disposable contact lens has a lens wear duration of between 8 hours and 14 hours, and because it is sterile before opening the package, it is not cleaned or exposed to a cleaning solution before it is placed in the eye, and is then discarded. Thus, daily disposable silicone hydrogel contact lenses are disposable silicone hydrogel contact lenses that are replaced daily. In contrast, non-daily disposable contact lenses are disposable contact lenses that are replaced less frequently than daily (e.g., weekly, biweekly, or monthly). The non-daily disposable contact lenses are removed from the eye and periodically rinsed with a rinsing solution, or worn continuously without removal from the eye.

In addition to modal differences, the manufacture of daily-parabolic contact lenses may require changes in the chemistry used to prepare the lenses, changes in the manufacturing process, or both, as compared to non-daily-parabolic contact lenses, to produce industrially acceptable quantities of lenses in a cost-effective manner.

Based on the popularity of silicone hydrogel contact lenses, there remains a need in the art for novel silicone hydrogel contact lenses that are ophthalmically compatible.

Some documents describing silicone hydrogel contact lenses include: US4711943, US5712327, US5760100, US7825170, US6867245, US20060063852, US20070296914, US7572841, US20090299022, US20090234089 and US20100249356, each of which is incorporated herein by reference in its entirety.

Disclosure of Invention

It has been recognized that reducing or eliminating organic solvent-based extraction steps in the manufacture of silicone hydrogel contact lenses can provide at least one opportunity to reduce the costs associated with manufacturing daily disposable silicone hydrogel contact lenses. However, it is clearly difficult to reduce the clinical unwetted spots that appear on washed silicone hydrogel contact lenses by replacing the organic solvent-based extraction step with an aqueous washing step (e.g., extracting the silicone hydrogel contact lenses with an alcohol-based liquid, etc.). In addition, the use of an aqueous wash solution that is free of volatile organic solvents may eliminate the need for separate rinsing and hydration steps.

Novel silicone hydrogel contact lenses have been invented. The present contact lenses comprise or consist of a lens body comprising a polymeric component and a liquid component. The polymeric component comprises one or more siloxane units and one or more non-siloxane reactive ingredients. Thus, it is understood that the polymeric component is the reaction product of a polymerizable composition comprising one or more siloxanes and one or more non-siloxane reactive ingredients. The ingredients in the polymerizable composition can be monomers, macromers, prepolymers, polymers, or combinations thereof. The combination of the polymeric component and the liquid component is present as a hydrated silicone hydrogel contact lens suitable for placement on a human eye. The contact lens comprises a convex anterior surface and a concave posterior surface, and an Equilibrium Water Content (EWC) of greater than 10% (weight/weight, wt/wt). During the manufacture of silicone hydrogel contact lenses, the lens body is not extracted with a volatile organic solvent (e.g., a liquid composition comprising, consisting essentially of, or consisting of a volatile organic solvent). Examples of volatile organic solvents that are excluded from the manufacture of the present silicone hydrogel contact lenses to remove extractable components from the polymeric lens body include primary alcohols, secondary alcohols, tertiary alcohols, or any combination thereof. Unlike commercially available silicone hydrogel contact lenses, the present silicone hydrogel contact lenses are only exposed to an aqueous solution free of volatile organic solvents to remove extractable components from the polymeric lens body. The aqueous solution may contain non-volatile organic components such as surfactants, wetting agents, anti-inflammatory agents, antioxidants, stabilizers, extraction aids, and the like, as long as the aqueous solution does not contain a volatile organic solvent. Thus, the present silicone hydrogel contact lenses are understood to be aqueous extraction contact lenses. As discussed herein, aqueous extraction contact lenses are chemically and physically different and unique relative to organic solvent extraction contact lenses.

The present silicone hydrogel contact lenses comprise an aqueous extraction lens body. The aqueous extraction lens bodies each have an anterior surface and an opposite posterior surface, the posterior surface being the surface adjacent to the corneal epithelium of the eye in which the lens body is located. The incidence of non-wetting spots and the anterior surface of the lens bodies of the present invention is associated with a reduction in the incidence of non-wetting spots compared to other daily disposable silicone hydrogel contact lenses. Based on the study, other commercial daily disposable silicone hydrogel contact lenses have unwetted spots on at least 5% of the lenses when worn on the eyes of a group of contact lens wearers and observed in a conventional slit lamp examination. For some batches of commercial daily disposable silicone hydrogel contact lenses, it has been observed that the incidence of unwetted spots present on the contact lenses can exceed 20%. In contrast, the silicone hydrogel contact lenses disclosed herein have unwetted spots on less than 5% of the lenses worn on the patient's eyes using the same inspection technique.

Thus, the present inventors have invented novel silicone hydrogel contact lenses having desirable clinical surface wettability, and which do not require the use of volatile organic solvents to remove extractable materials from the lens body during its manufacture. Additionally, surface wettability has been achieved and no plasma treatment of the polymerized lens product or polymeric internal wetting agents (e.g., polyvinylpyrrolidone (PVP)) in contact lens formulations are required. It can be appreciated that the problem of producing silicone hydrogel contact lenses having clinically desirable surface wettabilities without extracting the lens body with volatile organic solvents has now been recognized and solved.

Thus, the production of silicone hydrogel contact lenses does not use volatile organic solvents to extract materials from the polymerized contact lens body, but rather is washed with an aqueous liquid. The silicone hydrogel contact lenses so produced have ophthalmically wettable lens surfaces such that less than 5% of a batch of 20 or more of the silicone hydrogel contact lenses have non-wetting spots discernible to the naked eye when the contact lenses are on an individual's eyes.

In accordance with the present disclosure, a method of manufacturing a batch of silicone hydrogel contact lenses includes providing polymerized silicone hydrogel contact lens bodies in a contact lens mold assembly. A single polymerized silicone hydrogel contact lens body is provided in a single contact lens mold assembly. Each contact lens mold assembly includes a first mold section (anterior surface mold section) having a concave optical surface for forming the anterior surface of the silicone hydrogel contact lens body and a second mold section (posterior surface mold section) having a convex optical surface for forming the posterior surface of the silicone hydrogel contact lens body. The first mold section and the second mold section are coupled together to form a contact lens mold assembly.

The method includes separating a polymerized silicone hydrogel contact lens body from a contact lens mold assembly to produce a delensed contact lens body. This can be accomplished by separating the first and second mold sections from each other such that the polymerized silicone hydrogel contact lens body remains adhered to one mold section. The polymerized silicone hydrogel contact lens body can then be mechanically separated from the mold section without the use of a liquid; or the mold section and lens can be separated from the mold section using a liquid, such as immersing the mold section and lens in a volume of liquid, or soaking the mold until the lens floats from the mold, or applying a liquid to the mold section to soak the lens body, or dissolving the mold in a liquid.

The method further comprises washing the delensed contact lens body with an aqueous liquid free of volatile organic solvents to produce a washed contact lens. These washed contact lenses can be understood as aqueous extracted contact lenses.

The washed contact lens is then sterilized in a sealed contact lens package, for example, by autoclaving the lens in a sealed package.

In one example, the silicone hydrogel contact lens is not contacted with a liquid comprising a volatile organic solvent during any step of the manufacturing process (i.e., all of the liquid of the contact lens is free of volatile organic solvent during manufacturing).

In one example, a method of manufacturing a batch of silicone hydrogel contact lenses of the invention is a method comprising: providing polymerized silicone hydrogel contact lens bodies in contact lens mold assemblies, wherein a single polymerized silicone hydrogel contact lens body is provided in a single contact lens mold assembly, and each contact lens mold assembly comprises a first mold section having a concave optical surface for forming an anterior surface of a silicone hydrogel contact lens body and a second mold section having a convex optical surface for forming a posterior surface of a silicone hydrogel contact lens body, and coupling the first mold section and the second mold section together; separating the polymerized silicone hydrogel contact lens body from the contact lens mold assembly to produce a delensed contact lens body; washing a delensed contact lens body with an aqueous liquid free of volatile organic solvents to produce a washed contact lens; and sterilizing the washed contact lens in the sealed contact lens package; wherein the batch so manufactured comprises at least 20 silicone hydrogel contact lenses and the anterior surface of the sterilized contact lenses has a clinically acceptable surface wettability such that less than 5% of the silicone hydrogel contact lenses have visually discernible non-wetting spots when positioned on the eye of an individual, and wherein the non-wetting spots are discontinuities in the pre-lens tear film of a contact lens wearer present on the anterior surface of the contact lens and are visually discernible at a total magnification of from about 6 x to about 70 x during slit lamp inspection.

The batch so produced contains at least 20 silicone hydrogel contact lenses, and the anterior surfaces of the sterilized contact lenses have a clinically acceptable surface wettability. As used herein, the clinically acceptable surface wettability is based on less than 5% of the silicone hydrogel contact lens having a non-wetting spot discernible to the naked eye when positioned on the eye of an individual or human. Unwetted spots are discontinuities in the contact lens wearer's pre-lens tear film present on the contact lens front surface and are discernible to the naked eye at a total magnification of about 6 x to about 70 x during slit lamp examination, or during use of other conventional ocular and lens examination techniques, such as those disclosed in US 47683, which provides a technique for determining the in vivo wettability of contact lenses by adding a dye (e.g., fluorescein) to the tear fluid to visualize the thin pre-lens tear film.

Another example of the invention relates to a batch of silicone hydrogel contact lenses so produced.

In one example, a batch of silicone hydrogel contact lenses of the present invention is a batch comprising: at least 20 silicone hydrogel contact lenses, each silicone hydrogel contact lens in the batch being an aqueous extracted silicone hydrogel contact lens comprising an anterior surface and an opposing posterior surface, the posterior surface sized (sized and shaped) for placement against an eye of an individual; the anterior surface of each aqueous extraction contact lens has a clinically acceptable surface wettability such that less than 5% of the silicone hydrogel contact lenses in the batch have visually discernible unwetted spots when placed on the eyes of an individual; wherein the non-wetting spots are discontinuities in the contact lens wearer's pre-lens tear film present on the front surface of the lens body and are discernible to the naked eye at a total magnification of from about 6 x to about 70 x during slit lamp inspection.

Other examples of the invention are set forth in the claims. For example, some of the present methods and silicone hydrogel contact lens batches involve the use of certain polar resins, such as polybutylene terephthalate (PBT), to form contact lens mold sections for casting silicone hydrogel contact lenses. Some of the present methods and batches of silicone hydrogel contact lenses involve a new combination of ingredients (e.g., siloxane monomers, hydrophilic monomers, hydrophobic monomers, crosslinking agents, etc.) that surprisingly provides an ophthalmically compatible or wettable lens surface even when the polymerizable composition or formulation is cast in a contact lens mold assembly prepared from a non-polar resin (e.g., polypropylene). These contact lenses having wettable surfaces are obtained without exposing or contacting the polymerized lenses with volatile organic solvents, but are washed with aqueous liquids.

Other embodiments of the polymerizable composition, the present lenses, lens products, lens batches, and methods of manufacturing contact lenses will be apparent from the following description, examples, and claims. As can be appreciated from the above and following description, each feature described herein, and each combination of two or more of such features, and each combination of one or more values defining a range, is included within the scope of the present invention provided that the features included in such combinations are not mutually inconsistent. In addition, any feature or combination of features or any value defining a range may be explicitly excluded from any embodiment of the invention.

Drawings

Detailed Description

As described herein, it has now been found that silicone hydrogel contact lenses having clinically acceptable surface wettabilities can be produced, and that polymerized silicone hydrogel contact lenses are not contacted with one or more volatile organic solvents, particularly during the processing steps between separating the lenses from the mold assembly and packaging the lenses. The clinically acceptable silicone hydrogel contact lenses can be produced without the need for surface treatment of the polymeric lens body to achieve wettability, the inclusion of a hydrophilic polymer in the formulation used to prepare the contact lens, or the use of no organic diluent in the formulation to reduce phase separation of the hydrophobic and hydrophilic components of the formulation.

In accordance with the present invention, a method of manufacturing a batch of silicone hydrogel contact lenses is provided. The method includes the step of providing a polymerized silicone hydrogel contact lens body in a contact lens mold assembly. Each contact lens mold assembly comprises a first mold section and a second mold section. The first and second mold sections are coupled together to provide a contact lens shaped cavity between the first and second mold sections. The first mold section has a concave optical surface that forms the anterior surface of the silicone hydrogel contact lens body. The first mould part may thus be understood as a front surface mould part. The second mold section has a convex optical surface that forms the posterior surface of the silicone hydrogel contact lens body. The second mould part may thus be understood as a back surface mould part.

The contact lens thus provided may be provided by: the polymerized silicone hydrogel contact lens bodies are formed in the contact lens mold assembly by polymerizing the contact lens formulation or polymerizable composition to form the silicone hydrogel contact lens bodies. The polymerization can be carried out by exposing the contact lens mold assembly to thermal radiation, ultraviolet radiation, visible light, and the like.

The providing step may also be understood as the following step: wherein the polymerized silicone hydrogel contact lens body located in the contact lens mold assembly is provided to a separation entity for further processing, such as separating the lens body from the mold assembly and washing and packaging the separated lens body. Thus, a single manufacturer may form a polymerized silicone hydrogel contact lens body and further process it to form a packaged silicone hydrogel contact lens, or a manufacturer may form a polymerized silicone hydrogel contact lens body and provide it to other companies for further processing, selling the contact lens under its own label or trademark.

In the present methods, the polymerized silicone hydrogel contact lens bodies are separated from the contact lens mold assemblies to produce delensed contact lens bodies. As discussed in more detail herein, the method can further comprise separating the first mold portion and the second mold portion such that the polymerized silicone hydrogel contact lens body remains adhered to one mold portion. The polymerized silicone hydrogel contact lens can then be mechanically separated from the mold section without the use of a liquid, or can be contacted with a liquid to release the lens body from the mold section.

The delensed contact lens body is then washed with an aqueous liquid. Washing can be effective in removing dust or debris from the lens, extracting material from the lens, hydrating the lens, or any combination thereof. The aqueous liquid is free of volatile organic solvents. The aqueous liquid may be deionized water. The aqueous liquid may be a deionized water solution comprising a salt, wherein the aqueous liquid is free of volatile organic solvents. The aqueous liquid may be a deionized water solution comprising a buffer and having a particularly desirable pH, wherein the aqueous liquid is free of volatile organic solvents. The aqueous liquid may be a deionized water solution comprising a surfactant, wherein the aqueous liquid is free of organic solvents. The aqueous liquid may be a deionized water solution containing an ophthalmically acceptable component in an amount effective to reduce lens distortion during processing, wherein the aqueous liquid is free of volatile organic solvents. The aqueous liquid may be a deionized water solution containing an ophthalmically acceptable ingredient in an amount effective to increase the amount of extractable material removed from the lens during washing, wherein the aqueous liquid is free of organic solvents. After washing, a washed contact lens is produced.

The washed contact lenses are placed in contact lens packages (e.g., blister packs or vials) prior to sealing and sterilization (e.g., autoclaving) as understood by those skilled in the art.

One example of a method of manufacturing a batch of silicone hydrogel contact lenses of the present invention is a method comprising: providing polymerized silicone hydrogel contact lens bodies in contact lens mold assemblies, wherein a single polymerized silicone hydrogel contact lens body is provided in a single contact lens mold assembly, and each contact lens mold assembly comprises a first mold section having a concave optical surface for forming an anterior surface of a silicone hydrogel contact lens body and a second mold section having a convex optical surface for forming a posterior surface of a silicone hydrogel contact lens body, and coupling the first mold section and the second mold section together; separating the polymerized silicone hydrogel contact lens body from the contact lens mold assembly to produce a delensed contact lens body; washing a delensed contact lens body with an aqueous liquid free of volatile organic solvents to produce a washed contact lens; and sterilizing the washed contact lens in the sealed contact lens package; wherein the silicone hydrogel contact lenses are not contacted with a liquid comprising a volatile organic solvent during any step of the manufacturing process, and the batch so manufactured comprises at least 20 silicone hydrogel contact lenses, and the anterior surface of the sterilized contact lenses has a clinically acceptable surface wettability, such that less than 5% of the silicone hydrogel contact lenses have macroscopically discernible non-wetted spots when positioned on the eye of an individual, and wherein the non-wetted spots are discontinuities in the pre-lens tear film of a contact lens wearer that are present on the anterior surface of the contact lens and are macroscopically discernible at a total magnification of from about 6 x to about 70 x during a slit lamp inspection.

One example of a batch of silicone hydrogel contact lenses of the present invention is a batch comprising: at least 20 silicone hydrogel contact lenses, each silicone hydrogel contact lens in the batch being an aqueous extracted silicone hydrogel contact lens that is not contacted with a liquid comprising a volatile organic solvent during any step of a manufacturing process, each contact lens comprising an anterior surface and an opposing posterior surface, the posterior surface sized (sized and shaped) for placement against an eye of a subject; the anterior surface of each aqueous extraction contact lens has a clinically acceptable surface wettability such that less than 5% of the silicone hydrogel contact lenses in the batch have visually discernible unwetted spots when placed on the eyes of an individual; wherein the non-wetting spots are discontinuities in the contact lens wearer's pre-lens tear film present on the front surface of the lens body and are discernible to the naked eye at a total magnification of from about 6 x to about 70 x during slit lamp inspection.

The batch of contact lenses so manufactured comprises at least 20 silicone hydrogel contact lenses. Typically, however, the batch will be greater than 20, and may include at least 100, at least 1000, or at least 10000 silicone hydrogel contact lenses. As disclosed herein, the anterior surface of a sterilized silicone hydrogel contact lens has a clinically acceptable surface wettability such that less than 5% of the silicone hydrogel contact lens has a non-wetted spot discernible to the naked eye when positioned on the eye of an individual or human. Unwetted spots are discontinuities in the pre-lens tear film of the contact lens wearer and are present on the anterior surface of the contact lens. The unwetted spots were visually discernible at a total magnification of about 6 x to about 70 x during a slit lamp examination by an eye care physician. Such inspection techniques to determine the presence or absence of unwetted spots are conventional techniques understood by those skilled in the art.

In some methods, at least one of the first mold portion or the second mold portion comprises a polar resin having a polarity of 1% to 7%. In some methods, both the first and second mold portions comprise the polar resin. One example of a polar resin that may be used in the process of the present invention includes a resin formed from polybutylene terephthalate (PBT). In some other examples, the polar resin (e.g., PBT) used to form the first and second mold portions has a flexural modulus of less than 3800 MPa.

One example of a method of manufacturing a batch of silicone hydrogel contact lenses of the present invention is a method comprising: providing polymerized silicone hydrogel contact lens bodies in contact lens mold assemblies, wherein a single polymerized silicone hydrogel contact lens body is provided in a single contact lens mold assembly, and each contact lens mold assembly comprises a first mold section having a concave optical surface for forming an anterior surface of a silicone hydrogel contact lens body and a second mold section having a convex optical surface for forming a posterior surface of a silicone hydrogel contact lens body, at least one of the first mold section or the second mold section comprising a polar resin having a polarity of 1% to 7%, and coupling the first mold section and the second mold section together; separating the polymerized silicone hydrogel contact lens body from the contact lens mold assembly to produce a delensed contact lens body; washing a delensed contact lens body with an aqueous liquid free of volatile organic solvents to produce a washed contact lens; and sterilizing the washed contact lens in the sealed contact lens package; wherein the batch so manufactured comprises at least 20 silicone hydrogel contact lenses and the anterior surface of the sterilized contact lenses has a clinically acceptable surface wettability such that less than 5% of the silicone hydrogel contact lenses have visually discernible non-wetting spots when positioned on the eye of an individual, and wherein the non-wetting spots are discontinuities in the pre-lens tear film of a contact lens wearer present on the anterior surface of the contact lens and are visually discernible at a total magnification of from about 6 x to about 70 x during slit lamp inspection.

One example of a batch of silicone hydrogel contact lenses of the present invention is a batch comprising: at least 20 silicone hydrogel contact lenses, each silicone hydrogel contact lens in the batch being molded in a single contact lens mold assembly, each contact lens mold assembly comprising a first mold section having a concave optical surface for forming an anterior surface of a silicone hydrogel contact lens body and a second mold section having a convex optical surface for forming a posterior surface of a silicone hydrogel contact lens body, at least one of the first mold section or the second mold section comprising a polar resin having a polarity of 1% to 7%, and each silicone hydrogel contact lens being an aqueous extracted silicone hydrogel contact lens comprising an anterior surface and an opposing posterior surface, the posterior surface being sized (sized and shaped) for placement against an eye of a subject; the anterior surface of each aqueous extraction contact lens has a clinically acceptable surface wettability such that less than 5% of the silicone hydrogel contact lenses in the batch have visually discernible unwetted spots when placed on the eyes of an individual; wherein the non-wetting spots are discontinuities in the contact lens wearer's pre-lens tear film present on the front surface of the lens body and are discernible to the naked eye at a total magnification of from about 6 x to about 70 x during slit lamp inspection.

As described herein, polymeric contact lens bodies can be obtained by polymerizing a polymerizable composition in a contact lens mold assembly using thermal radiation or ultraviolet radiation, or both. Typically, if thermal radiation is used, the polymerizable composition will include a thermal initiator. If ultraviolet radiation is used, the polymerizable composition will include an ultraviolet initiator. The curing time may vary depending on the silicone hydrogel contact lens being manufactured and is typically in the range of 20 minutes to 4 hours. In one example, the polymerizable composition can have a cure time of less than 20 minutes. In another example, the polymerizable composition can have a cure time of at least 20 minutes. In another example, the cure time may be less than 3 hours. In another example, the cure time may exceed 3 hours.

In some methods, curing may be achieved by providing the following curing conditions: wherein a certain temperature or a certain light intensity is provided and maintained for a certain length of time, after which it is changed to another temperature or intensity and maintained for another period of time.

In any of the present methods, each polymerized silicone hydrogel contact lens body is obtained by polymerizing a polymerizable composition. Generally, the polymerizable composition comprises at least one siloxane monomer, at least one hydrophilic monomer, at least one hydrophobic monomer, and at least one crosslinker. For example, the polymerizable composition can comprise a first siloxane monomer, a second siloxane monomer, one or more hydrophilic monomers, one or more hydrophobic monomers, and one or more crosslinkers. Additional details regarding the ingredients in the polymerizable composition and various examples and amounts and relationships between the ingredients are set forth herein. As an example, various polymerizable compositions of the present invention do not contain a diluent, or do not contain a hydrophilic polymer, or both.

One example of a method of manufacturing a batch of silicone hydrogel contact lenses of the present invention is a method comprising: providing a polymerized silicone hydrogel contact lens body in a contact lens mold assembly, the polymerized silicone hydrogel contact lens body being a reaction product of a polymerizable composition, the polymerizable composition comprises a first siloxane monomer, a second siloxane monomer, at least one hydrophilic monomer, at least one hydrophobic monomer, and at least one crosslinker, wherein a single polymerized silicone hydrogel contact lens body is provided in a single contact lens mold assembly, and each contact lens mold assembly comprises a first mold section having a concave optical surface for forming the anterior surface of the silicone hydrogel contact lens body and a second mold section having a convex optical surface for forming the posterior surface of the silicone hydrogel contact lens body, and the first and second mold sections are coupled together; separating the polymerized silicone hydrogel contact lens body from the contact lens mold assembly to produce a delensed contact lens body; washing a delensed contact lens body with an aqueous liquid free of volatile organic solvents to produce a washed contact lens; and sterilizing the washed contact lens in the sealed contact lens package; wherein the batch so manufactured comprises at least 20 silicone hydrogel contact lenses and the anterior surface of the sterilized contact lenses has a clinically acceptable surface wettability such that less than 5% of the silicone hydrogel contact lenses have visually discernible non-wetting spots when positioned on the eye of an individual, and wherein the non-wetting spots are discontinuities in the pre-lens tear film of a contact lens wearer present on the anterior surface of the contact lens and are visually discernible at a total magnification of from about 6 x to about 70 x during slit lamp inspection.

Another example of a method of manufacturing a batch of silicone hydrogel contact lenses of the present invention is a method comprising: providing polymerized silicone hydrogel contact lens bodies in contact lens mold assemblies, the polymerized silicone hydrogel contact lens bodies being the reaction product of a polymerizable composition comprising a first siloxane monomer, a second siloxane monomer, at least one hydrophilic monomer, at least one hydrophobic monomer, and at least one crosslinking agent, wherein the polymerizable composition is free of a diluent, or free of a hydrophilic polymer, or both, and wherein single polymerized silicone hydrogel contact lens bodies are provided in a single contact lens mold assembly, and each contact lens mold assembly comprises a first mold section having a concave optical surface for forming an anterior surface of a silicone hydrogel contact lens body and a second mold section having a convex optical surface for forming a posterior surface of a silicone hydrogel contact lens body, and coupling the first mold portion and the second mold portion together; separating the polymerized silicone hydrogel contact lens body from the contact lens mold assembly to produce a delensed contact lens body; washing a delensed contact lens body with an aqueous liquid free of volatile organic solvents to produce a washed contact lens; and sterilizing the washed contact lens in the sealed contact lens package; wherein the batch so manufactured comprises at least 20 silicone hydrogel contact lenses and the anterior surface of the sterilized contact lenses has a clinically acceptable surface wettability such that less than 5% of the silicone hydrogel contact lenses have visually discernible non-wetting spots when positioned on the eye of an individual, and wherein the non-wetting spots are discontinuities in the pre-lens tear film of a contact lens wearer present on the anterior surface of the contact lens and are visually discernible at a total magnification of from about 6 x to about 70 x during slit lamp inspection.

One example of a batch of silicone hydrogel contact lenses of the present invention is a batch comprising: at least 20 polymerized silicone hydrogel contact lenses that are the reaction product of a polymerizable composition comprising a first siloxane monomer, a second siloxane monomer, at least one hydrophilic monomer, at least one hydrophobic monomer, and at least one crosslinker, each silicone hydrogel contact lens in the batch being an aqueous extracted silicone hydrogel contact lens comprising an anterior surface and an opposing posterior surface, the posterior surface sized (sized and shaped) for placement against an eye of the subject; the anterior surface of each aqueous extraction contact lens has a clinically acceptable surface wettability such that less than 5% of the silicone hydrogel contact lenses in the batch have visually discernible unwetted spots when placed on the eyes of an individual; wherein the non-wetting spots are discontinuities in the contact lens wearer's pre-lens tear film present on the front surface of the lens body and are discernible to the naked eye at a total magnification of from about 6 x to about 70 x during slit lamp inspection.

Another example of a batch of silicone hydrogel contact lenses of the present invention is a batch comprising: at least 20 polymerized silicone hydrogel contact lenses that are the reaction product of a polymerizable composition comprising a first siloxane monomer, a second siloxane monomer, at least one hydrophilic monomer, at least one hydrophobic monomer, and at least one crosslinker, wherein the polymerizable composition is free of a diluent, or free of a hydrophilic polymer, or both, and each silicone hydrogel contact lens in the batch is an aqueous extracted silicone hydrogel contact lens comprising an anterior surface and an opposing posterior surface, the posterior surface sized (sized and shaped) for placement against an eye of a subject; the anterior surface of each aqueous extraction contact lens has a clinically acceptable surface wettability such that less than 5% of the silicone hydrogel contact lenses in the batch have visually discernible unwetted spots when placed on the eyes of an individual; wherein the non-wetting spots are discontinuities in the contact lens wearer's pre-lens tear film present on the front surface of the lens body and are discernible to the naked eye at a total magnification of from about 6 x to about 70 x during slit lamp inspection.

In some detail, the siloxane monomer in the polymerizable composition of the present invention can be mono-or multifunctional, such as di-or tri-functional. The monofunctional siloxane monomer has a single polymerizable functional group such as an acrylic group, a methacrylic group, or a vinyl group. The multifunctional siloxane monomer has two or more of the polymerizable functional groups. The polymerizable functional group may be present on a side chain of the siloxane monomer, on the main chain or backbone of the siloxane monomer, or on both the side chain and the main chain (for multifunctional siloxane monomers). In some of the polymerizable compositions described herein, the first siloxane monomer is a monofunctional siloxane monomer and the second siloxane monomer is a multifunctional siloxane monomer. In other examples, the first siloxane monomer has a number average molecular weight of less than 2,000 daltons (dalton), or less than 1,000 daltons, or from 400 daltons to 700 daltons. In examples containing a second multifunctional siloxane monomer, the second siloxane monomer has a number average molecular weight greater than 3,000 daltons. Some of the second siloxane monomers have a number average molecular weight of greater than 5,000 daltons or greater than 9,000 daltons. Typically, the second multifunctional siloxane monomer has a number average molecular weight of less than 20,000 daltons. The first siloxane monomer can be present in an amount from 20 unit parts to 45 unit parts, or from 25 unit parts to 40 unit parts, or from 27 unit parts to 35 unit parts of the polymerizable composition. Additional details of siloxane monomers that can be used in any of the methods of the present invention are set forth herein.

One example of a method of manufacturing a batch of silicone hydrogel contact lenses of the present invention is a method comprising: providing polymerized silicone hydrogel contact lens bodies in contact lens mold assemblies, the polymerized silicone hydrogel contact lens bodies being the reaction product of a polymerizable composition comprising a first siloxane monomer having a number average molecular weight of 400 daltons to 700 daltons, a second siloxane monomer having a number average molecular weight of greater than 5,000 daltons, at least one hydrophilic monomer, at least one hydrophobic monomer, and at least one crosslinking agent, wherein a single polymerized silicone hydrogel contact lens body is provided in a single contact lens mold assembly, and each contact lens mold assembly comprises a first mold portion having a concave optical surface for forming the anterior surface of the silicone hydrogel contact lens body and a second mold portion having a convex optical surface for forming the posterior surface of the silicone hydrogel contact lens body, and coupling the first mold portion and the second mold portion together; separating the polymerized silicone hydrogel contact lens body from the contact lens mold assembly to produce a delensed contact lens body; washing a delensed contact lens body with an aqueous liquid free of volatile organic solvents to produce a washed contact lens; and sterilizing the washed contact lens in the sealed contact lens package; wherein the batch so manufactured comprises at least 20 silicone hydrogel contact lenses and the anterior surface of the sterilized contact lenses has a clinically acceptable surface wettability such that less than 5% of the silicone hydrogel contact lenses have visually discernible non-wetting spots when positioned on the eye of an individual, and wherein the non-wetting spots are discontinuities in the pre-lens tear film of a contact lens wearer present on the anterior surface of the contact lens and are visually discernible at a total magnification of from about 6 x to about 70 x during slit lamp inspection.

One example of a batch of silicone hydrogel contact lenses of the present invention is a batch comprising: at least 20 polymerized silicone hydrogel contact lenses that are the reaction product of a polymerizable composition comprising a first siloxane monomer having a number average molecular weight of 400 daltons to 700 daltons, a second siloxane monomer having a number average molecular weight of greater than 5,000 daltons, at least one hydrophilic monomer, at least one hydrophobic monomer, and at least one crosslinking agent, each silicone hydrogel contact lens in the batch being an aqueous extracted silicone hydrogel contact lens comprising an anterior surface and an opposing posterior surface, the posterior surface sized (sized and shaped) for placement against an eye of a subject; the anterior surface of each aqueous extraction contact lens has a clinically acceptable surface wettability such that less than 5% of the silicone hydrogel contact lenses in the batch have visually discernible unwetted spots when placed on the eyes of an individual; wherein the non-wetting spots are discontinuities in the contact lens wearer's pre-lens tear film present on the front surface of the lens body and are discernible to the naked eye at a total magnification of from about 6 x to about 70 x during slit lamp inspection.

In some of the methods of the present invention, specific combinations of ingredients are provided. For example, the present batch of silicone hydrogel contact lenses having clinically acceptable surface wettabilities can be made by including at least one hydrophilic vinyl monomer and at least one vinyl crosslinker in the polymerizable composition. The vinyl monomer and vinyl crosslinker are different from the methacrylate-type monomer and methacrylate-type crosslinker, particularly based on their different reactivity ratios.

One example of a method of manufacturing a batch of silicone hydrogel contact lenses of the present invention is a method comprising: providing a polymerized silicone hydrogel contact lens body in a contact lens mold assembly, the polymerized silicone hydrogel contact lens body being a reaction product of a polymerizable composition, the polymerizable composition comprises a first siloxane monomer, a second siloxane monomer, at least one hydrophilic vinyl-containing monomer, at least one hydrophobic monomer, and at least one crosslinker, wherein a single polymerized silicone hydrogel contact lens body is provided in a single contact lens mold assembly, and each contact lens mold assembly comprises a first mold section having a concave optical surface for forming the anterior surface of the silicone hydrogel contact lens body and a second mold section having a convex optical surface for forming the posterior surface of the silicone hydrogel contact lens body, and the first and second mold sections are coupled together; separating the polymerized silicone hydrogel contact lens body from the contact lens mold assembly to produce a delensed contact lens body; washing a delensed contact lens body with an aqueous liquid free of volatile organic solvents to produce a washed contact lens; and sterilizing the washed contact lens in the sealed contact lens package; wherein the batch so manufactured comprises at least 20 silicone hydrogel contact lenses and the anterior surface of the sterilized contact lenses has a clinically acceptable surface wettability such that less than 5% of the silicone hydrogel contact lenses have visually discernible non-wetting spots when positioned on the eye of an individual, and wherein the non-wetting spots are discontinuities in the pre-lens tear film of a contact lens wearer present on the anterior surface of the contact lens and are visually discernible at a total magnification of from about 6 x to about 70 x during slit lamp inspection.

Another example of a method of manufacturing a batch of silicone hydrogel contact lenses of the present invention is a method comprising: providing a polymerized silicone hydrogel contact lens body in a contact lens mold assembly, the polymerized silicone hydrogel contact lens body being a reaction product of a polymerizable composition, the polymerizable composition comprises a first siloxane monomer, a second siloxane monomer, at least one hydrophilic vinyl-containing monomer, at least one hydrophobic monomer, and at least one vinyl-containing crosslinking agent, wherein a single polymerized silicone hydrogel contact lens body is provided in a single contact lens mold assembly, and each contact lens mold assembly comprises a first mold section having a concave optical surface for forming the anterior surface of the silicone hydrogel contact lens body and a second mold section having a convex optical surface for forming the posterior surface of the silicone hydrogel contact lens body, and the first and second mold sections are coupled together; separating the polymerized silicone hydrogel contact lens body from the contact lens mold assembly to produce a delensed contact lens body; washing a delensed contact lens body with an aqueous liquid free of volatile organic solvents to produce a washed contact lens; and sterilizing the washed contact lens in the sealed contact lens package; wherein the batch so manufactured comprises at least 20 silicone hydrogel contact lenses and the anterior surface of the sterilized contact lenses has a clinically acceptable surface wettability such that less than 5% of the silicone hydrogel contact lenses have visually discernible non-wetting spots when positioned on the eye of an individual, and wherein the non-wetting spots are discontinuities in the pre-lens tear film of a contact lens wearer present on the anterior surface of the contact lens and are visually discernible at a total magnification of from about 6 x to about 70 x during slit lamp inspection.

Another example of a method of manufacturing a batch of silicone hydrogel contact lenses of the present invention is a method comprising: providing a polymerized silicone hydrogel contact lens body in a contact lens mold assembly, the polymerized silicone hydrogel contact lens body being a reaction product of a polymerizable composition, the polymerizable composition comprises a first siloxane monomer, a second siloxane monomer, at least one hydrophilic amide monomer having one N-vinyl group, at least one hydrophobic monomer, and at least one crosslinker, wherein a single polymerized silicone hydrogel contact lens body is provided in a single contact lens mold assembly, and each contact lens mold assembly comprises a first mold section having a concave optical surface for forming the anterior surface of the silicone hydrogel contact lens body and a second mold section having a convex optical surface for forming the posterior surface of the silicone hydrogel contact lens body, and the first and second mold sections are coupled together; separating the polymerized silicone hydrogel contact lens body from the contact lens mold assembly to produce a delensed contact lens body; washing a delensed contact lens body with an aqueous liquid free of volatile organic solvents to produce a washed contact lens; and sterilizing the washed contact lens in the sealed contact lens package; wherein the batch so manufactured comprises at least 20 silicone hydrogel contact lenses and the anterior surface of the sterilized contact lenses has a clinically acceptable surface wettability such that less than 5% of the silicone hydrogel contact lenses have visually discernible non-wetting spots when positioned on the eye of an individual, and wherein the non-wetting spots are discontinuities in the pre-lens tear film of a contact lens wearer present on the anterior surface of the contact lens and are visually discernible at a total magnification of from about 6 x to about 70 x during slit lamp inspection.

Another example of a method of manufacturing a batch of silicone hydrogel contact lenses of the present invention is a method comprising: providing a polymerized silicone hydrogel contact lens body in a contact lens mold assembly, the polymerized silicone hydrogel contact lens body being a reaction product of a polymerizable composition, the polymerizable composition comprises a first siloxane monomer, a second siloxane monomer, at least one hydrophilic amide monomer having one N-vinyl group, at least one hydrophobic monomer, and at least one vinyl-containing crosslinking agent, wherein a single polymerized silicone hydrogel contact lens body is provided in a single contact lens mold assembly, and each contact lens mold assembly comprises a first mold section having a concave optical surface for forming the anterior surface of the silicone hydrogel contact lens body and a second mold section having a convex optical surface for forming the posterior surface of the silicone hydrogel contact lens body, and the first and second mold sections are coupled together; separating the polymerized silicone hydrogel contact lens body from the contact lens mold assembly to produce a delensed contact lens body; washing a delensed contact lens body with an aqueous liquid free of volatile organic solvents to produce a washed contact lens; and sterilizing the washed contact lens in the sealed contact lens package; wherein the batch so manufactured comprises at least 20 silicone hydrogel contact lenses and the anterior surface of the sterilized contact lenses has a clinically acceptable surface wettability such that less than 5% of the silicone hydrogel contact lenses have visually discernible non-wetting spots when positioned on the eye of an individual, and wherein the non-wetting spots are discontinuities in the pre-lens tear film of a contact lens wearer present on the anterior surface of the contact lens and are visually discernible at a total magnification of from about 6 x to about 70 x during slit lamp inspection.

Another example of a method of manufacturing a batch of silicone hydrogel contact lenses of the present invention is a method comprising: providing polymerized silicone hydrogel contact lens bodies in contact lens mold assemblies, the polymerized silicone hydrogel contact lens bodies being the reaction product of a polymerizable composition comprising a first siloxane monomer, a second siloxane monomer, at least one hydrophilic vinyl-containing monomer, at least one hydrophobic monomer, and at least one crosslinker, wherein the polymerizable composition is free of diluent, or free of hydrophilic polymer, or both, and wherein single polymerized silicone hydrogel contact lens bodies are provided in a single contact lens mold assembly, and each contact lens mold assembly comprises a first mold section having a concave optical surface for forming an anterior surface of a silicone hydrogel contact lens body and a second mold section having a convex optical surface for forming a posterior surface of a silicone hydrogel contact lens body, and coupling the first mold portion and the second mold portion together; separating the polymerized silicone hydrogel contact lens body from the contact lens mold assembly to produce a delensed contact lens body; washing a delensed contact lens body with an aqueous liquid free of volatile organic solvents to produce a washed contact lens; and sterilizing the washed contact lens in the sealed contact lens package; wherein the batch so manufactured comprises at least 20 silicone hydrogel contact lenses and the anterior surface of the sterilized contact lenses has a clinically acceptable surface wettability such that less than 5% of the silicone hydrogel contact lenses have visually discernible non-wetting spots when positioned on the eye of an individual, and wherein the non-wetting spots are discontinuities in the pre-lens tear film of a contact lens wearer present on the anterior surface of the contact lens and are visually discernible at a total magnification of from about 6 x to about 70 x during slit lamp inspection.

One example of a batch of silicone hydrogel contact lenses of the present invention is a batch comprising: at least 20 polymerized silicone hydrogel contact lenses that are the reaction product of a polymerizable composition comprising a first siloxane monomer, a second siloxane monomer, at least one hydrophilic vinyl-containing monomer, at least one hydrophobic monomer, and at least one crosslinker, each silicone hydrogel contact lens in the batch being an aqueous extracted silicone hydrogel contact lens comprising an anterior surface and an opposing posterior surface, the posterior surface sized (sized and shaped) for placement against an eye of the subject; the anterior surface of each aqueous extraction contact lens has a clinically acceptable surface wettability such that less than 5% of the silicone hydrogel contact lenses in the batch have visually discernible unwetted spots when placed on the eyes of an individual; wherein the non-wetting spots are discontinuities in the contact lens wearer's pre-lens tear film present on the front surface of the lens body and are discernible to the naked eye at a total magnification of from about 6 x to about 70 x during slit lamp inspection.

Another example of a batch of silicone hydrogel contact lenses of the present invention is a batch comprising: at least 20 polymerized silicone hydrogel contact lenses that are the reaction product of a polymerizable composition comprising a first siloxane monomer, a second siloxane monomer, at least one hydrophilic vinyl-containing monomer, at least one hydrophobic monomer, and at least one vinyl-containing cross-linking agent, each silicone hydrogel contact lens in the batch being an aqueous extracted silicone hydrogel contact lens comprising an anterior surface and an opposing posterior surface, the posterior surface sized (sized and shaped) for placement against an eye of an individual; the anterior surface of each aqueous extraction contact lens has a clinically acceptable surface wettability such that less than 5% of the silicone hydrogel contact lenses in the batch have visually discernible unwetted spots when placed on the eyes of an individual; wherein the non-wetting spots are discontinuities in the contact lens wearer's pre-lens tear film present on the front surface of the lens body and are discernible to the naked eye at a total magnification of from about 6 x to about 70 x during slit lamp inspection.

Another example of a batch of silicone hydrogel contact lenses of the present invention is a batch comprising: at least 20 polymerized silicone hydrogel contact lenses that are the reaction product of a polymerizable composition comprising a first siloxane monomer, a second siloxane monomer, at least one hydrophilic amide monomer having one N-vinyl group, at least one hydrophobic monomer, and at least one crosslinking agent, each silicone hydrogel contact lens in the batch being an aqueous extracted silicone hydrogel contact lens comprising an anterior surface and an opposing posterior surface, the posterior surface sized (sized and shaped) for placement against an eye of an individual; the anterior surface of each aqueous extraction contact lens has a clinically acceptable surface wettability such that less than 5% of the silicone hydrogel contact lenses in the batch have visually discernible unwetted spots when placed on the eyes of an individual; wherein the non-wetting spots are discontinuities in the contact lens wearer's pre-lens tear film present on the front surface of the lens body and are discernible to the naked eye at a total magnification of from about 6 x to about 70 x during slit lamp inspection.

Another example of a batch of silicone hydrogel contact lenses of the present invention is a batch comprising: at least 20 polymerized silicone hydrogel contact lenses that are the reaction product of a polymerizable composition comprising a first siloxane monomer, a second siloxane monomer, at least one hydrophilic vinyl-containing monomer, at least one hydrophobic monomer, and at least one crosslinker, wherein the polymerizable composition is free of a diluent, or free of a hydrophilic polymer, or both, and each silicone hydrogel contact lens in the batch is an aqueous extracted silicone hydrogel contact lens comprising an anterior surface and an opposing posterior surface, the posterior surface sized (sized and shaped) for placement against an eye of a subject; the anterior surface of each aqueous extraction contact lens has a clinically acceptable surface wettability such that less than 5% of the silicone hydrogel contact lenses in the batch have visually discernible unwetted spots when placed on the eyes of an individual; wherein the non-wetting spots are discontinuities in the contact lens wearer's pre-lens tear film present on the front surface of the lens body and are discernible to the naked eye at a total magnification of from about 6 x to about 70 x during slit lamp inspection.

In any of the present methods, the average diameter of the batch of sterilized silicone hydrogel contact lenses (i.e., the average of each chordal diameter for each silicone hydrogel contact lens or a representative population of silicone hydrogel contact lenses) is at least 20% greater than the average diameter of the same batch of silicone hydrogel contact lens bodies prior to the washing step of the present methods. Thus, the present silicone hydrogel contact lenses are produced in a certain size in the dry state, and upon washing, the contact lenses swell to their final size that is at least 20% greater than their size in the dry state. This is in contrast to silicone hydrogel contact lenses produced using a volatile organic solvent extraction step. For example, in the silicone hydrogel contact lenses, dry lenses are produced in sizes substantially equal to their final hydrated sizes and differing by less than 20%. Thus, upon contacting the dry lenses with a volatile organic solvent (e.g., ethanol, etc.), the individual contact lenses will swell to about twice their dry size, and then produce hydrated contact lenses by removing the alcohol with an aqueous solution, which hydrated contact lenses have recovered their original size, within the specified target dimensions.

In any of the present methods, a silicone hydrogel contact lens having clinically desirable properties is produced. For example, each sterilized silicone hydrogel contact lens has an oxygen permeability of at least 55 barrers, or an equilibrium water content of about 30% wt/wt to about 70% wt/wt, or a tensile modulus of about 0.2MPa to about 0.9MPa, or any combination thereof. In some examples, each sterilized silicone hydrogel contact lens has an oxygen permeability of at least 55 barrers, or an equilibrium water content of about 30% wt/wt to about 70% wt/wt and a tensile modulus of about 0.2MPa to about 0.9 MPa.

Practicing the present method results in the manufacture of a batch of silicone hydrogel contact lenses. As described herein, the batch includes at least 20 silicone hydrogel contact lenses, although the batch may include more. Each silicone hydrogel contact lens in the batch is an aqueous extracted silicone hydrogel contact lens (e.g., it is not washed or extracted with a volatile organic solvent). Each silicone hydrogel contact lens includes an anterior surface and an opposing posterior surface. The posterior surface is sized (e.g., sized and shaped) for placement against an eye of an individual. The anterior surface of each aqueous extraction contact lens has a clinically acceptable surface wettability such that less than 5% of the silicone hydrogel contact lenses in the batch have a non-wetting spot discernible to the naked eye when positioned on the eyes of an individual. As described herein, unwetted spots are discontinuities in the contact lens wearer's pre-lens tear film that are present on the lens front surface and are discernible to the naked eye at an overall magnification of about 6 x to about 70 x during slit lamp inspection.

In some examples, the batch of silicone hydrogel contact lenses are cast-molded silicone hydrogel contact lenses that are not plasma surface treated or are free of polymeric internal wetting agents provided by including a hydrophilic polymer in a polymerizable composition used to form the silicone hydrogel contact lenses. A cast-molded contact lens is understood to be a contact lens polymerized from a polymerizable composition in a contact lens mold assembly as described herein, the mold assembly comprising a first mold section and a second mold section coupled together.

As described herein, certain examples of the present silicone hydrogel contact lens batches are cast molded between a first mold section and a second mold section formed from a polar resin having a polarity of about 1% to about 7%. In some examples, the polar resin is polybutylene terephthalate (PBT).

One example of a method of manufacturing a batch of silicone hydrogel contact lenses of the present invention is a method comprising: providing polymerized silicone hydrogel contact lens bodies in contact lens mold assemblies, wherein a single polymerized silicone hydrogel contact lens body is provided in a single contact lens mold assembly, and each contact lens mold assembly comprises a first mold section having a concave optical surface for forming an anterior surface of a silicone hydrogel contact lens body and a second mold section having a convex optical surface for forming a posterior surface of a silicone hydrogel contact lens body, at least one of the first mold section or the second mold section comprising polybutylene terephthalate (PBT), and coupling the first mold section and the second mold section together; separating the polymerized silicone hydrogel contact lens body from the contact lens mold assembly to produce a delensed contact lens body; washing a delensed contact lens body with an aqueous liquid free of volatile organic solvents to produce a washed contact lens; and sterilizing the washed contact lens in the sealed contact lens package; wherein the batch so manufactured comprises at least 20 silicone hydrogel contact lenses and the anterior surface of the sterilized contact lenses has a clinically acceptable surface wettability such that less than 5% of the silicone hydrogel contact lenses have visually discernible non-wetting spots when positioned on the eye of an individual, and wherein the non-wetting spots are discontinuities in the pre-lens tear film of a contact lens wearer present on the anterior surface of the contact lens and are visually discernible at a total magnification of from about 6 x to about 70 x during slit lamp inspection.

One example of a batch of silicone hydrogel contact lenses of the present invention is a batch comprising: at least 20 silicone hydrogel contact lenses, each silicone hydrogel contact lens in the batch being molded in a single contact lens mold assembly, each contact lens mold assembly comprising a first mold section having a concave optical surface for forming an anterior surface of a silicone hydrogel contact lens body and a second mold section having a convex optical surface for forming a posterior surface of a silicone hydrogel contact lens body, at least one of the first mold section or the second mold section comprising polybutylene terephthalate (PBT), and each silicone hydrogel contact lens being an aqueous extracted silicone hydrogel contact lens comprising an anterior surface and an opposing posterior surface, the posterior surface sized (sized and shaped) for placement against an eye of a subject; the anterior surface of each aqueous extraction contact lens has a clinically acceptable surface wettability such that less than 5% of the silicone hydrogel contact lenses in the batch have visually discernible unwetted spots when placed on the eyes of an individual; wherein the non-wetting spots are discontinuities in the contact lens wearer's pre-lens tear film present on the front surface of the lens body and are discernible to the naked eye at a total magnification of from about 6 x to about 70 x during slit lamp inspection.

Any of the present lots may comprise silicone hydrogel contact lenses, wherein each contact lens comprises a polymeric component and a liquid component. The polymeric component comprises units of at least one siloxane, units of at least one hydrophilic monomer, units of at least one hydrophobic monomer, and units of at least one crosslinker. In some examples, the polymeric component comprises units of at least one siloxane having one or more acrylic functional groups and units of one or more hydrophilic monomers having one or more non-acrylic vinyl functional groups.

Any present lot may comprise silicone hydrogel contact lenses, wherein each contact lens has an oxygen permeability of at least 55 barrers, or an equilibrium water content from about 30% wt/wt to about 70% wt/wt, or a tensile modulus from about 0.2MPa to about 0.9MPa, or any combination thereof. In some examples, each contact lens has an oxygen permeability of at least 55 barrers, or an equilibrium water content of about 30% wt/wt to about 70% wt/wt and a tensile modulus of about 0.2MPa to about 0.9 MPa.

In any of the present batches of silicone hydrogel contact lenses, each silicone hydrogel contact lens is provided in a sterile contact lens packaging solution. In certain examples, each contact lens can have a moisture extractable content of less than 10% (wt/wt), as described herein.

Additional details of the present silicone hydrogel contact lenses, silicone hydrogel contact lens batches, and methods of manufacture will now be described.

In some examples, the present silicone hydrogel contact lenses are produced from a polymerizable composition comprising a first siloxane monomer represented by formula (1) in the polymerizable composition:

wherein m in formula (1) represents an integer of 3 to 10, n in formula (1) represents an integer of 1 to 10, R in formula (1)¹Is an alkyl group having 1 to 4 carbon atoms, and each R in the formula (1)²Independently a hydrogen atom or a methyl group; and a second siloxane monomer having more than one polymerizable functional group and having a number average molecular weight of at least 3,000 daltons, such as a number average molecular weight of at least 5,000 daltons. The first siloxane monomer and the second siloxane monomer are present in an amount of at least 2: a ratio of 1 is present in the polymerizable composition.

One example of a method of manufacturing a batch of silicone hydrogel contact lenses of the present invention is a method comprising: providing a polymerized silicone hydrogel contact lens body in a contact lens mold assembly, the polymerized silicone hydrogel contact lens body being a reaction product of a polymerizable composition comprising a first siloxane monomer represented by formula (1):

Wherein m in formula (1) represents an integer of 3 to 10, n in formula (1) represents an integer of 1 to 10, R in formula (1)¹Is an alkyl group having 1 to 4 carbon atoms, and each R in the formula (1)²Independently a hydrogen atom or a methyl group; at least one hydrophilic vinyl-containing monomer; a second siloxane monomer having more than one polymerizable functional group and having a number average molecular weight of at least 5,000 daltons; at least one hydrophobic vinyl-containing monomer; and at least one crosslinking agent, wherein the single polymerized silicone hydrogel contact lens body is provided in a single contact lens mold assembly, and each contact lens mold assembly comprises a mold having a cavity for forming a silicone hydrogel contact lensA first mold section having a concave optical surface of the anterior surface of the lens body and a second mold section having a convex optical surface for forming the posterior surface of the silicone hydrogel contact lens body, and coupling the first mold section and the second mold section together; separating the polymerized silicone hydrogel contact lens body from the contact lens mold assembly to produce a delensed contact lens body; washing a delensed contact lens body with an aqueous liquid free of volatile organic solvents to produce a washed contact lens; and sterilizing the washed contact lens in the sealed contact lens package; wherein the batch so manufactured comprises at least 20 silicone hydrogel contact lenses and the anterior surface of the sterilized contact lenses has a clinically acceptable surface wettability such that less than 5% of the silicone hydrogel contact lenses have visually discernible non-wetting spots when positioned on the eye of an individual, and wherein the non-wetting spots are discontinuities in the pre-lens tear film of a contact lens wearer present on the anterior surface of the contact lens and are visually discernible at a total magnification of from about 6 x to about 70 x during slit lamp inspection. In one example, the at least one hydrophilic vinyl-containing monomer can comprise a hydrophilic amide monomer having one N-vinyl group, or the at least one crosslinker can comprise a vinyl-containing crosslinker, or both. In another example, the polymerizable composition can be free of diluent, or free of hydrophilic polymer, or free of N, N-Dimethylacrylamide (DMA), or any combination thereof. In another example, the silicone hydrogel contact lens may be free of a plasma surface treatment or free of a polymeric internal wetting agent provided by the inclusion of a hydrophilic polymer in the polymerizable composition used to form the silicone hydrogel contact lens, or both.

One example of a batch of silicone hydrogel contact lenses of the present invention is a batch comprising: at least 20 polymerized silicone hydrogel contact lenses that are the reaction product of a polymerizable composition comprising a first siloxane monomer represented by formula (1):

wherein m in formula (1) represents an integer of 3 to 10, n in formula (1) represents an integer of 1 to 10, R in formula (1)¹Is an alkyl group having 1 to 4 carbon atoms, and each R in the formula (1)²Independently a hydrogen atom or a methyl group; at least one hydrophilic vinyl-containing monomer; a second siloxane monomer having more than one polymerizable functional group and having a number average molecular weight of at least 5,000 daltons; at least one hydrophobic vinyl-containing monomer; and at least one cross-linking agent, each silicone hydrogel contact lens in the batch being an aqueous extracted silicone hydrogel contact lens comprising an anterior surface and an opposing posterior surface, the posterior surface sized (sized and shaped) for placement against an eye of an individual; the anterior surface of each aqueous extraction contact lens has a clinically acceptable surface wettability such that less than 5% of the silicone hydrogel contact lenses in the batch have visually discernible unwetted spots when placed on the eyes of an individual; wherein the non-wetting spots are discontinuities in the contact lens wearer's pre-lens tear film present on the front surface of the lens body and are discernible to the naked eye at a total magnification of from about 6 x to about 70 x during slit lamp inspection. In one example, the at least one hydrophilic vinyl-containing monomer can comprise a hydrophilic amide monomer having one N-vinyl group, or the at least one crosslinker can comprise a vinyl-containing crosslinker, or both. In another example, the polymerizable composition can be free of diluent, or free of hydrophilic polymer, or free of N, N-Dimethylacrylamide (DMA), or any combination thereof. In another example, the silicone hydrogel contact lens may be free of a plasma surface treatment or free of a polymeric internal wetting agent provided by the inclusion of a hydrophilic polymer in the polymerizable composition used to form the silicone hydrogel contact lens, or both.

The first siloxane monomer and the second siloxane monomer can be present in an amount of at least 2: a ratio of 1 is present in the polymerizable composition. In other words, for each weight unit part of the second siloxane monomer present in the polymerizable composition, 2 unit parts or more of the first siloxane monomer are also present in the polymerizable composition. According to the present invention, the first siloxane monomer and the second siloxane monomer may be present in an amount of about 2: 1 to about 10: a ratio of 1 is present in the polymerizable composition. In another example, the first siloxane monomer and the second siloxane monomer can be present in an amount of about 3: 1 to about 6: a ratio of 1 is present in the polymerizable composition. In another example, the first siloxane monomer and the second siloxane monomer can be present in an amount of about 4: a ratio of 1 is present in the polymerizable composition.

As used herein, "unit parts" is understood to mean unit parts by weight. For example, to prepare a formulation set forth as comprising x unit parts of a first siloxane monomer and y unit parts of a second siloxane monomer, a composition can be prepared by: combining x grams of the first silicone with y grams of the second silicone to obtain a total of x + y grams of the polymerizable composition, or combining x ounces of the first silicone with y ounces of the second silicone to obtain a total of x + y ounces of the polymerizable composition, and so forth. Where the composition further comprises other optional ingredients (e.g., z unit parts of a crosslinker), z grams of the crosslinker are combined with x grams of the first siloxane monomer and y grams of the second siloxane to obtain a total of x + y + z grams of the polymerizable composition, and so on. Typically, the polymerizable composition will be formulated from ingredients in amounts totaling from about 90 to about 110 parts by weight. When the amounts of the components in the polymerizable composition are recited herein in unit parts, it is understood that the unit parts of these components are based on a formulation that provides a total weight of the composition in a range of from about 90 unit parts to 110 unit parts. In one example, the unit parts by weight can be based on a formulation that provides a total weight of the composition ranging from about 95 unit parts by weight to 105 unit parts by weight, or about 98 unit parts by weight to 102 unit parts by weight.

As discussed herein, the present contact lenses comprise or consist of a hydrated lens body comprising a polymeric component and a liquid component. The polymeric component may comprise units of two or more siloxanes and one or more non-silicon reactive ingredients. It can thus be appreciated that the polymeric component can be the reaction product of a polymerizable composition comprising two or more siloxanes (the siloxane monomer component of the composition) and one or more silicon-free reactive ingredients. As used herein, a silicon-free reactive component is understood to be a component that has a polymerizable double bond as part of its molecular structure, but does not contain a silicon atom in its molecular structure. The ingredients in the polymerizable composition can be monomers, macromers, prepolymers, polymers, or any combination thereof. Optionally, the ingredients in the polymerizable composition can further comprise at least one hydrophilic monomer, or at least one hydrophobic monomer, or at least one crosslinker. At least one hydrophilic monomer, at least one hydrophobic monomer and at least one crosslinking agent are understood to be silicon-free reactive components. As used herein, at least one hydrophilic monomer is understood to comprise a single hydrophilic monomer, or to comprise a hydrophilic monomer component consisting of two or more hydrophilic monomers. Similarly, at least one hydrophobic monomer is understood to comprise a single hydrophobic monomer, or to comprise a hydrophobic monomer component consisting of two or more hydrophobic monomers. The at least one crosslinking agent is understood to comprise a single crosslinking agent or to comprise a crosslinking agent component consisting of two or more crosslinking agents. Additionally, the polymerizable composition may optionally include at least one initiator, or at least one organic diluent, or at least one surfactant, or at least one oxygen scavenger, or at least one colorant, or at least one UV absorber, or at least one chain transfer agent, or any combination thereof. The optional at least one initiator, at least one organic diluent, at least one surfactant, at least one oxygen scavenger, at least one colorant, at least one UV absorber, or at least one chain transfer agent is understood to be a silicon-free component and may be a non-polymerizable component or a polymerizable component (i.e., a component having a polymerizable functional group as part of its molecular structure).

The combination of the polymeric component and the liquid component is present as a hydrated lens body suitable for placement on a human eye. The hydrated lens body has an overall convex anterior surface and an overall concave posterior surface, and an Equilibrium Water Content (EWC) of greater than 10% (weight/weight, wt/wt). Thus, the present contact lenses can be understood as soft contact lenses, which as used herein refers to contact lenses that can fold upon themselves without breaking when fully hydrated.

The present contact lenses can be daily-cast contact lenses or non-daily-cast contact lenses.

In one example, the polymerizable composition of the present invention comprises a first siloxane monomer represented by formula (1):

wherein m in formula (1) represents an integer of 3 to 10, n in formula (1) represents an integer of 1 to 10, R in formula (1)¹Is an alkyl group having 1 to 4 carbon atoms, and each R in the formula (1)²Independently a hydrogen atom or a methyl group. In other words, the first R in formula (1) is on a single molecule of the siloxane monomer represented by formula 1²(said R is²R nearest to the left side of the molecule¹Terminal group) may be a hydrogen atom or a methyl group, and is not limited to the first R in the formula (1)²Is a hydrogen atom or a methyl group, a second R in the formula (1)²(said R is²Part of the methacrylate end groups to the right of the molecule) may also be hydrogen atoms or methyl groups. The polymerizable composition further comprises a second siloxane monomer. The first siloxane monomer and the second siloxane monomer are present in an amount of at least 2: a ratio of 1 is present in the polymerizable composition. The second siloxane monomer has more than one polymerizable functional group (i.e., is a multifunctional siloxane monomer) and has a number average molecular weight of at least 3,000 daltons. If the second siloxane monomer has two polymerizable functional groups (e.g., two methacrylate groups), it is difunctional A monomer. If the second siloxane monomer has three polymerizable functional groups, it is a trifunctional monomer. The polymerizable composition further comprises at least one hydrophilic monomer, or at least one hydrophobic monomer, or at least one crosslinking agent, or any combination thereof.

The present invention also relates to one or more novel silicone hydrogel contact lenses. The silicone hydrogel contact lenses of the invention comprise a polymeric lens body. The polymeric lens body is the reaction product of a polymerizable composition or a contact lens formulation. The polymerizable composition used to produce the silicone hydrogel contact lenses of the invention comprises a first siloxane monomer represented by formula (1):

wherein m in formula (1) represents an integer of 3 to 10, n in formula (1) represents an integer of 1 to 10, R in formula (1)¹Is an alkyl group having 1 to 4 carbon atoms, and each R in the formula (1)²Independently a hydrogen atom or a methyl group. The polymerizable composition also includes a second siloxane monomer having more than one polymerizable functional group and having a number average molecular weight of at least 3,000 daltons. The first siloxane monomer and the second siloxane monomer are present in an amount of at least 2: a ratio of 1 is present in the polymerizable composition. The polymerizable composition further comprises at least one hydrophilic monomer, or at least one hydrophobic monomer, or at least one crosslinking agent, or any combination thereof.

Molecular weight as used herein is understood to mean number average molecular weight. The number average molecular weight is the ordinary arithmetic mean or average of the molecular weights of the individual molecules present in the monomer sample. Since the molar masses of the individual molecules in a monomer sample may differ slightly from one another, there may be a certain level of polydispersity in the sample. As used herein, the term "molecular weight" refers to the number average molecular weight of the monomer or ingredient, when the second siloxane monomer or any other monomer, macromer, prepolymer, or polymer in the polymerizable composition has polydispersity. As one example, a sample of the second siloxane monomer can have a number average molecular weight of about 15,000 daltons, but if the sample has polydispersity, the actual molecular weight of the individual monomers present in the sample can range from 12,000 daltons to 18,000 daltons.

The number average molecular weight can be an absolute number average molecular weight as determined by proton Nuclear Magnetic Resonance (NMR) end group analysis, as understood by one of skill in the art. Molecular weight may also be determined using gel permeation chromatography, as understood by one of skill in the art, or may be provided by the supplier of the chemical.

The first siloxane monomer has a molecular weight of less than 2,000 daltons. In one example, the molecular weight of the first siloxane monomer can be less than 1,000 daltons. In another example, the first siloxane monomer can have a molecular weight of less than 400 daltons to 700 daltons. Further details regarding the first siloxane monomer can be found in US20090299022, which is incorporated herein by reference in its entirety. As can be appreciated from formula (1), the first siloxane monomer has a single methacrylic polymerizable end group.

In one example of the present contact lenses, the second siloxane monomer can have a number average molecular weight of at least 4,000 daltons, or at least 7,000 daltons, or at least 9,000 daltons, or at least 11,000 daltons. The number average molecular weight of the second siloxane monomer can be less than 20,000 daltons. Thus, in some instances, the second siloxane monomer can be considered a macromer, but can be referred to herein as a monomer since it forms 1 unit part of a polymer with other reactive components in the polymerizable composition.

The polymerizable composition further comprises at least one hydrophilic monomer, or at least one hydrophobic monomer, or at least one crosslinking agent, or any combination thereof. The foregoing three types of chemistries, as used herein, are silicon-free chemistries (i.e., the molecular structure of the chemistry does not include silicon atoms) and thus are different from the siloxane monomers present in the polymerizable composition. The polymerizable composition can be understood to comprise at least two siloxane monomers and other silicon-free hydrophilic monomers, or silicon-free hydrophobic monomers, or silicon-free crosslinkers, or any combination thereof, although the polymerizable composition can optionally further comprise at least one third siloxane monomer.

The first siloxane monomer, the second siloxane monomer, and optionally at least one third siloxane monomer comprise the siloxane monomer component of the polymerizable composition. Each of the first siloxane monomer, or the second siloxane monomer, or optionally the third siloxane monomer, or any combination thereof, can be a hydrophilic siloxane monomer, or a hydrophobic siloxane monomer, or can have both hydrophilic and hydrophobic regions, depending on the number and location of any hydrophilic component (e.g., units of ethylene glycol, polyethylene glycol, etc.) present in the molecular structure of the siloxane monomer. For example, the second siloxane monomer, or optionally at least one third siloxane monomer, or any combination thereof, can contain a hydrophilic component within the siloxane molecule backbone, can contain a hydrophilic component within one or more side chains of the siloxane molecule, or any combination thereof. For example, the siloxane monomer can have at least one ethylene glycol unit adjacent to a polymerizable functional group in the backbone of the siloxane molecule. The at least one ethylene glycol unit adjacent to the polymerizable functional group in the backbone of the siloxane molecule can be separated from the polymerizable functional group by a carbon chain of 1 to 10 units in length (i.e., where the ethylene glycol unit is bonded to the first carbon of the chain and the polymerizable functional group is bonded to the last carbon of the chain). The siloxane monomer may have at least one ethylene glycol unit adjacent to the polymerizable functional groups present on both ends of the siloxane molecular backbone. The siloxane monomer can have at least one ethylene glycol unit present in at least one side chain of the siloxane molecule. The at least one ethylene glycol unit present in the at least one side chain of the siloxane molecule can be part of a side chain bonded to a silicon atom in the backbone of the siloxane molecule. The siloxane molecules can have both at least one ethylene glycol unit adjacent to the polymerizable functional groups present on both ends of the siloxane molecule backbone, and at least one ethylene glycol unit present in at least one side chain of the siloxane molecule.

The hydrophilicity or hydrophobicity of the monomer can be determined using conventional techniques (e.g., based on the water solubility of the monomer). For the purposes of the present invention, hydrophilic monomers are monomers which are significantly soluble in aqueous solutions at room temperature (e.g., about 20-25 ℃). For example, a hydrophilic monomer is understood to be any monomer that is significantly completely soluble in 1 liter of water (i.e., > 5% soluble in water) at 20 ℃ for 50 grams of monomer as determined using standard shake flask procedures known to those skilled in the art. Hydrophobic monomers as used herein are the following monomers: which is significantly insoluble in aqueous solutions at room temperature, such that there are multiple separate visually discernible phases in the aqueous solution, or such that the aqueous solution appears cloudy and separates into two distinct phases over time upon standing at room temperature. Hydrophobic monomers are understood to be, for example, any monomers for which 50 g of the monomers are clearly not completely soluble in 1 water at 20 ℃.

In one example of a contact lens of the invention, the first siloxane monomer can be represented by formula (1), wherein m in formula (1) is 4, n in formula (1) is 1, and R in formula (1)¹Is butyl, and each R in formula (1)²Independently a hydrogen atom or a methyl group. One example of the first siloxane monomer is identified in the examples herein as Si 1.

In another example of a contact lens of the invention, the second siloxane monomer can be a double-terminal methacrylate-terminated polydimethylsiloxane having a number average molecular weight of at least 4,000 daltons. It will be understood that the siloxane monomer is a difunctional monomer.

As one example of a difunctional siloxane monomer that may be used in the silicone hydrogel contact lenses of the present invention, the second siloxane monomer may be represented by formula (2):

wherein R in formula (2)₁Selected from a hydrogen atom or a methyl group; r in the formula (2)₂Selected from hydrogen atomsOr a hydrocarbon group having 1 to 4 carbon atoms; m in formula (2) represents an integer of 0 to 10; n in formula (2) represents an integer of 4 to 100; a and b represent an integer of 1 or more; a + b equals 20 to 500; b/(a + b) equals 0.01 to 0.22; and the configuration of the siloxane units includes a random configuration. In one example where the second siloxane monomer is a monomer represented by formula (2), m in formula (2) is 0, n in formula (2) is an integer of 5 to 15, a is an integer of 65 to 90, b is an integer of 1 to 10, R in formula (2)₁Is methyl, and R in formula (2)₂Is a hydrogen atom or a hydrocarbon group having 1 to 4 carbon atoms. One example of the second siloxane monomer represented by formula (2) is abbreviated as Si2 in the examples. Such second siloxane monomer represented by formula (2) can have a number average molecular weight of from about 9,000 daltons to about 10,000 daltons. In another example, the second siloxane monomer represented by formula (2) can have a molecular weight of about 5,000 daltons to about 10,000 daltons. It can be understood that the second siloxane represented by formula (2) is a bifunctional siloxane having two terminal methacrylic groups. Further details regarding such second siloxane monomers can be found in US20090234089, which is incorporated herein by reference in its entirety.

One example of a method of manufacturing a batch of silicone hydrogel contact lenses of the present invention is a method comprising: providing a polymerized silicone hydrogel contact lens body in a contact lens mold assembly, the polymerized silicone hydrogel contact lens body being a reaction product of a polymerizable composition comprising a first siloxane monomer; a second siloxane monomer represented by formula (2):

wherein R in formula (2)₁Selected from a hydrogen atom or a methyl group; r in the formula (2)₂Selected from a hydrogen atom or a hydrocarbon group having 1 to 4 carbon atoms; m in formula (2) represents an integer of 0 to 10; n in formula (2) represents an integer of 4 to 100; a and b represent an integer of 1 or more; a is+ b is equal to 20-500; b/(a + b) is equal to 0.01-0.22; and the configuration of the siloxane units includes a random configuration; at least one hydrophobic vinyl-containing monomer; and at least one crosslinking agent, wherein a single polymerized silicone hydrogel contact lens body is provided in a single contact lens mold assembly, and each contact lens mold assembly comprises a first mold section having a concave optical surface for forming the anterior surface of the silicone hydrogel contact lens body and a second mold section having a convex optical surface for forming the posterior surface of the silicone hydrogel contact lens body, and the first and second mold sections are coupled together; separating the polymerized silicone hydrogel contact lens body from the contact lens mold assembly to produce a delensed contact lens body; washing a delensed contact lens body with an aqueous liquid free of volatile organic solvents to produce a washed contact lens; and sterilizing the washed contact lens in the sealed contact lens package; wherein the batch so manufactured comprises at least 20 silicone hydrogel contact lenses and the anterior surface of the sterilized contact lenses has a clinically acceptable surface wettability such that less than 5% of the silicone hydrogel contact lenses have visually discernible non-wetting spots when positioned on the eye of an individual, and wherein the non-wetting spots are discontinuities in the pre-lens tear film of a contact lens wearer present on the anterior surface of the contact lens and are visually discernible at a total magnification of from about 6 x to about 70 x during slit lamp inspection. In one example, the at least one hydrophilic vinyl-containing monomer can comprise a hydrophilic amide monomer having one N-vinyl group, or the at least one crosslinker can comprise a vinyl-containing crosslinker, or both. In another example, the polymerizable composition can be free of diluent, or free of hydrophilic polymer, or free of N, N-Dimethylacrylamide (DMA), or any combination thereof. In another example, the silicone hydrogel contact lens may be free of a plasma surface treatment or free of a polymeric internal wetting agent provided by the inclusion of a hydrophilic polymer in the polymerizable composition used to form the silicone hydrogel contact lens, or both.

Another example of a method of manufacturing a batch of silicone hydrogel contact lenses of the present invention is a method comprising: providing a polymerized silicone hydrogel contact lens body in a contact lens mold assembly, the polymerized silicone hydrogel contact lens body being a reaction product of a polymerizable composition comprising a first siloxane monomer having a number average molecular weight of 400 to 700 daltons; a second siloxane monomer represented by formula (2):

wherein R in formula (2)₁Selected from a hydrogen atom or a methyl group; r in the formula (2)₂Selected from a hydrogen atom or a hydrocarbon group having 1 to 4 carbon atoms; m in formula (2) represents an integer of 0 to 10; n in formula (2) represents an integer of 4 to 100; a and b represent an integer of 1 or more; a + b is equal to 20-500; b/(a + b) is equal to 0.01-0.22; and the configuration of the siloxane units includes a random configuration; at least one hydrophobic vinyl-containing monomer; and at least one crosslinking agent, wherein a single polymerized silicone hydrogel contact lens body is provided in a single contact lens mold assembly, and each contact lens mold assembly comprises a first mold section having a concave optical surface for forming the anterior surface of the silicone hydrogel contact lens body and a second mold section having a convex optical surface for forming the posterior surface of the silicone hydrogel contact lens body, and the first and second mold sections are coupled together; separating the polymerized silicone hydrogel contact lens body from the contact lens mold assembly to produce a delensed contact lens body; washing a delensed contact lens body with an aqueous liquid free of volatile organic solvents to produce a washed contact lens; and sterilizing the washed contact lens in the sealed contact lens package; wherein the batch so produced comprises at least 20 silicone hydrogel contact lenses and the anterior surface of the sterilized contact lenses has a clinically acceptable surface wettability Such that less than 5% of the silicone hydrogel contact lenses have visually discernable non-wetting spots when positioned on the eyes of an individual, and wherein the non-wetting spots are discontinuities in the pre-lens tear film of a contact lens wearer that are present on the front surface of the contact lens and are visually discernable at a total magnification of from about 6 x to about 70 x during slit lamp examination. In one example, the at least one hydrophilic vinyl-containing monomer can comprise a hydrophilic amide monomer having one N-vinyl group, or the at least one crosslinker can comprise a vinyl-containing crosslinker, or both. In another example, the polymerizable composition can be free of diluent, or free of hydrophilic polymer, or free of N, N-Dimethylacrylamide (DMA), or any combination thereof. In another example, the silicone hydrogel contact lens may be free of a plasma surface treatment or free of a polymeric internal wetting agent provided by the inclusion of a hydrophilic polymer in the polymerizable composition used to form the silicone hydrogel contact lens, or both.

Another example of a method of manufacturing a batch of silicone hydrogel contact lenses of the present invention is a method comprising: providing a polymerized silicone hydrogel contact lens body in a contact lens mold assembly, the polymerized silicone hydrogel contact lens body being a reaction product of a polymerizable composition comprising a first siloxane monomer represented by formula (1):

Wherein m in formula (1) represents an integer of 3 to 10, n in formula (1) represents an integer of 1 to 10, R in formula (1)¹Is an alkyl group having 1 to 4 carbon atoms, and each R in the formula (1)²Independently a hydrogen atom or a methyl group; a second siloxane monomer represented by formula (2):

wherein R in formula (2)₁Selected from a hydrogen atom or a methyl group; r in the formula (2)₂Selected from a hydrogen atom or a hydrocarbon group having 1 to 4 carbon atoms; m in formula (2) represents an integer of 0 to 10; n in formula (2) represents an integer of 4 to 100; a and b represent an integer of 1 or more; a + b is equal to 20-500; b/(a + b) is equal to 0.01-0.22; and the configuration of the siloxane units includes a random configuration; at least one hydrophobic vinyl-containing monomer; and at least one crosslinking agent, wherein a single polymerized silicone hydrogel contact lens body is provided in a single contact lens mold assembly, and each contact lens mold assembly comprises a first mold section having a concave optical surface for forming the anterior surface of the silicone hydrogel contact lens body and a second mold section having a convex optical surface for forming the posterior surface of the silicone hydrogel contact lens body, and the first and second mold sections are coupled together; separating the polymerized silicone hydrogel contact lens body from the contact lens mold assembly to produce a delensed contact lens body; washing a delensed contact lens body with an aqueous liquid free of volatile organic solvents to produce a washed contact lens; and sterilizing the washed contact lens in the sealed contact lens package; wherein the batch so manufactured comprises at least 20 silicone hydrogel contact lenses and the anterior surface of the sterilized contact lenses has a clinically acceptable surface wettability such that less than 5% of the silicone hydrogel contact lenses have visually discernible non-wetting spots when positioned on the eye of an individual, and wherein the non-wetting spots are discontinuities in the pre-lens tear film of a contact lens wearer present on the anterior surface of the contact lens and are visually discernible at a total magnification of from about 6 x to about 70 x during slit lamp inspection. In one example, the at least one hydrophilic vinyl-containing monomer can comprise a hydrophilic amide monomer having one N-vinyl group, or the at least one crosslinker can comprise a vinyl-containing crosslinker, or both. In another example, the polymerizable composition may be free of diluent, or Free of hydrophilic polymers, or free of N, N-Dimethylacrylamide (DMA), or any combination thereof. In another example, the silicone hydrogel contact lens may be free of a plasma surface treatment or free of a polymeric internal wetting agent provided by the inclusion of a hydrophilic polymer in the polymerizable composition used to form the silicone hydrogel contact lens, or both.

One example of a batch of silicone hydrogel contact lenses of the present invention is a batch comprising: at least 20 polymerized silicone hydrogel contact lenses that are the reaction product of a polymerizable composition comprising a first siloxane monomer; a second siloxane monomer represented by formula (2):

wherein R in formula (2)₁Selected from a hydrogen atom or a methyl group; r in the formula (2)₂Selected from a hydrogen atom or a hydrocarbon group having 1 to 4 carbon atoms; m in formula (2) represents an integer of 0 to 10; n in formula (2) represents an integer of 4 to 100; a and b represent an integer of 1 or more; a + b is equal to 20-500; b/(a + b) is equal to 0.01-0.22; and the configuration of the siloxane units includes a random configuration; at least one hydrophobic vinyl-containing monomer; and at least one cross-linking agent, each silicone hydrogel contact lens in the batch being an aqueous extracted silicone hydrogel contact lens comprising an anterior surface and an opposing posterior surface, the posterior surface sized (sized and shaped) for placement against an eye of an individual; the anterior surface of each aqueous extraction contact lens has a clinically acceptable surface wettability such that less than 5% of the silicone hydrogel contact lenses in the batch have visually discernible unwetted spots when placed on the eyes of an individual; wherein the non-wetting spots are discontinuities in the contact lens wearer's pre-lens tear film present on the front surface of the lens body and are discernible to the naked eye at a total magnification of from about 6 x to about 70 x during slit lamp inspection. At one is In examples, the at least one hydrophilic vinyl-containing monomer may comprise a hydrophilic amide monomer having one N-vinyl group, or the at least one crosslinking agent may comprise a vinyl-containing crosslinking agent, or both. In another example, the polymerizable composition can be free of diluent, or free of hydrophilic polymer, or free of N, N-Dimethylacrylamide (DMA), or any combination thereof. In another example, the silicone hydrogel contact lens may be free of a plasma surface treatment or free of a polymeric internal wetting agent provided by the inclusion of a hydrophilic polymer in the polymerizable composition used to form the silicone hydrogel contact lens, or both.

Another example of a batch of silicone hydrogel contact lenses of the present invention is a batch comprising: at least 20 polymerized silicone hydrogel contact lenses that are the reaction product of a polymerizable composition comprising a first siloxane monomer having a number average molecular weight of 400 to 700 daltons; a second siloxane monomer represented by formula (2):

wherein R in formula (2)₁Selected from a hydrogen atom or a methyl group; r in the formula (2) ₂Selected from a hydrogen atom or a hydrocarbon group having 1 to 4 carbon atoms; m in formula (2) represents an integer of 0 to 10; n in formula (2) represents an integer of 4 to 100; a and b represent an integer of 1 or more; a + b is equal to 20-500; b/(a + b) is equal to 0.01-0.22; and the configuration of the siloxane units includes a random configuration; at least one hydrophobic vinyl-containing monomer; and at least one cross-linking agent, each silicone hydrogel contact lens in the batch being an aqueous extracted silicone hydrogel contact lens comprising an anterior surface and an opposing posterior surface, the posterior surface sized (sized and shaped) for placement against an eye of an individual; the anterior surface of each aqueous extraction contact lens has a clinically acceptable surface wettability such that less than all of the batch5% of silicone hydrogel contact lenses had a non-wetting spot discernible to the naked eye when placed on an individual's eye; wherein the non-wetting spots are discontinuities in the contact lens wearer's pre-lens tear film present on the front surface of the lens body and are discernible to the naked eye at a total magnification of from about 6 x to about 70 x during slit lamp inspection. In one example, the at least one hydrophilic vinyl-containing monomer can comprise a hydrophilic amide monomer having one N-vinyl group, or the at least one crosslinker can comprise a vinyl-containing crosslinker, or both. In another example, the polymerizable composition can be free of diluent, or free of hydrophilic polymer, or free of N, N-Dimethylacrylamide (DMA), or any combination thereof. In another example, the silicone hydrogel contact lens may be free of a plasma surface treatment or free of a polymeric internal wetting agent provided by the inclusion of a hydrophilic polymer in the polymerizable composition used to form the silicone hydrogel contact lens, or both.

Another example of a batch of silicone hydrogel contact lenses of the present invention is a batch comprising: at least 20 polymerized silicone hydrogel contact lenses that are the reaction product of a polymerizable composition comprising a first siloxane monomer represented by formula (1):

wherein R in formula (2)₁Selected from a hydrogen atom or a methyl group; r in the formula (2)₂Selected from a hydrogen atom or a hydrocarbon group having 1 to 4 carbon atoms; m in formula (2) represents an integer of 0 to 10; n in formula (2) represents an integer of 4 to 100; a and b represent an integer of 1 or more; a + b is equal to 20-500; b/(a + b) is equal to 0.01-0.22; and the configuration of the siloxane units includes a random configuration; at least one hydrophobic vinyl-containing monomer; and at least one cross-linking agent, each silicone hydrogel contact lens in the batch being an aqueous extracted silicone hydrogel contact lens comprising an anterior surface and an opposing posterior surface, the posterior surface sized (sized and shaped) for placement against an eye of an individual; the anterior surface of each aqueous extraction contact lens has a clinically acceptable surface wettability such that less than 5% of the silicone hydrogel contact lenses in the batch have visually discernible unwetted spots when placed on the eyes of an individual; wherein the non-wetting spots are discontinuities in the contact lens wearer's pre-lens tear film present on the front surface of the lens body and are discernible to the naked eye at a total magnification of from about 6 x to about 70 x during slit lamp inspection. In one example, the at least one hydrophilic vinyl-containing monomer can comprise a hydrophilic amide monomer having one N-vinyl group, or the at least one crosslinker can comprise a vinyl-containing crosslinker, or both. In another example, the polymerizable composition can be free of diluent, or free of hydrophilic polymer, or free of N, N-Dimethylacrylamide (DMA), or any combination thereof. In another example, the silicone hydrogel contact lens may be free of a plasma surface treatment or free of a polymeric internal wetting agent provided by the inclusion of a hydrophilic polymer in the polymerizable composition used to form the silicone hydrogel contact lens, or both.

As another example of a difunctional siloxane monomer that may be used in the silicone hydrogel contact lenses of the present invention, the second siloxane monomer may be represented by formula (3):

wherein R is³Selected from a hydrogen atom or a methyl group, m in formula (3) represents an integer of 0 to 10, and n in formula (3) represents an integer of 1 to 500. In one example, the second siloxane monomer is represented by formula 3, and R³Is methyl, m in formula (3) is 0, and n in formula (3) is an integer of 40 to 60. The second siloxane monomer of this example is represented by formula (4), and is abbreviated in the examples as Si3 (available from courster (Gelest) corporation, morrisville, pa, usa under the product code DMS-R18):

the siloxane of formula (4) can have a number average molecular weight of about 4,000 daltons to about 4,500 daltons.

Another example of the second siloxane monomer that can be included in the polymerizable composition of the present invention is represented by the following formula (5):

wherein n is an integer from 100 to 140, m and p are both integers from 6-9, h is an integer from 3-6, and Mn =12,800, and Mw =16,200. The chemical name of the siloxane monomer of formula (5) is α - ω -bis (methacryloyloxyethyl iminocarboxy ethyloxypropyl) -poly (dimethylsiloxane) -poly (trifluoropropylmethylsiloxane) -poly (ω -methoxy-poly (ethyleneglycol) propylmethylsiloxane).

In some polymerizable compositions that include a siloxane monomer of formula (5), a monofunctional siloxane monomer represented by formula (6) can be provided in the composition:

wherein n is an integer from 13 to 16 and has a molecular weight of about 1500 daltons. The monofunctional siloxane monomer of formula (6) has the chemical name α -methacryloyloxyethyl iminocarboxy ethyloxypropyl-poly (dimethylsiloxy) -butyldimethylsilane. As described herein, silicone hydrogel contact lenses comprising siloxane monomer units of formula (5) and formula (6) can be cast molded in PBT contact lens mold assemblies and washed without the use of volatile organic solvents and with clinically acceptable surface wettability.

One example of a method of manufacturing a batch of silicone hydrogel contact lenses of the present invention is a method comprising: providing a polymerized silicone hydrogel contact lens body in a contact lens mold assembly, the polymerized silicone hydrogel contact lens body being a reaction product of a polymerizable composition comprising a siloxane monomer represented by formula (6):

wherein n is an integer from 13 to 16 and has a molecular weight of about 1500 daltons; at least one hydrophobic vinyl-containing monomer; and at least one crosslinking agent, wherein a single polymerized silicone hydrogel contact lens body is provided in a single contact lens mold assembly, and each contact lens mold assembly comprises a first mold section having a concave optical surface for forming the anterior surface of the silicone hydrogel contact lens body and a second mold section having a convex optical surface for forming the posterior surface of the silicone hydrogel contact lens body, and the first and second mold sections are coupled together; separating the polymerized silicone hydrogel contact lens body from the contact lens mold assembly to produce a delensed contact lens body; washing a delensed contact lens body with an aqueous liquid free of volatile organic solvents to produce a washed contact lens; and sterilizing the washed contact lens in the sealed contact lens package; wherein the batch so manufactured comprises at least 20 silicone hydrogel contact lenses and the anterior surface of the sterilized contact lenses has a clinically acceptable surface wettability such that less than 5% of the silicone hydrogel contact lenses have visually discernible non-wetting spots when positioned on the eye of an individual, and wherein the non-wetting spots are discontinuities in the pre-lens tear film of a contact lens wearer present on the anterior surface of the contact lens and are visually discernible at a total magnification of from about 6 x to about 70 x during slit lamp inspection. In one example, the at least one hydrophilic vinyl-containing monomer can comprise a hydrophilic amide monomer having one N-vinyl group, or the at least one crosslinker can comprise a vinyl-containing crosslinker, or both. In another example, the polymerizable composition can be free of diluent, or free of hydrophilic polymer, or free of N, N-Dimethylacrylamide (DMA), or any combination thereof. In another example, the silicone hydrogel contact lens may be free of a plasma surface treatment or free of a polymeric internal wetting agent provided by the inclusion of a hydrophilic polymer in the polymerizable composition used to form the silicone hydrogel contact lens, or both.

Another example of a method of manufacturing a batch of silicone hydrogel contact lenses of the present invention is a method comprising: providing a polymerized silicone hydrogel contact lens body in a contact lens mold assembly, the polymerized silicone hydrogel contact lens body being a reaction product of a polymerizable composition comprising a siloxane monomer represented by formula (6):

wherein n is an integer from 13 to 16 and has a molecular weight of about 1500 daltons; at least one hydrophobic vinyl-containing monomer; and at least one crosslinking agent, wherein a single polymerized silicone hydrogel contact lens body is provided in a single contact lens mold assembly, and each contact lens mold assembly comprises a first mold section having a concave optical surface for forming an anterior surface of the silicone hydrogel contact lens body and a second mold section having a convex optical surface for forming a posterior surface of the silicone hydrogel contact lens body, at least one of the first mold section and the second mold section comprising a polar material resin, and the first mold section and the second mold section are coupled together; separating the polymerized silicone hydrogel contact lens body from the contact lens mold assembly to produce a delensed contact lens body; washing a delensed contact lens body with an aqueous liquid free of volatile organic solvents to produce a washed contact lens; and sterilizing the washed contact lens in the sealed contact lens package; wherein the batch so manufactured comprises at least 20 silicone hydrogel contact lenses and the anterior surface of the sterilized contact lenses has a clinically acceptable surface wettability such that less than 5% of the silicone hydrogel contact lenses have visually discernible non-wetting spots when positioned on the eye of an individual, and wherein the non-wetting spots are discontinuities in the pre-lens tear film of a contact lens wearer present on the anterior surface of the contact lens and are visually discernible at a total magnification of from about 6 x to about 70 x during slit lamp inspection. In one example, the at least one hydrophilic vinyl-containing monomer can comprise a hydrophilic amide monomer having one N-vinyl group, or the at least one crosslinker can comprise a vinyl-containing crosslinker, or both. In another example, the polymerizable composition can be free of diluent, or free of hydrophilic polymer, or free of N, N-Dimethylacrylamide (DMA), or any combination thereof. In another example, the silicone hydrogel contact lens may be free of a plasma surface treatment or free of a polymeric internal wetting agent provided by the inclusion of a hydrophilic polymer in the polymerizable composition used to form the silicone hydrogel contact lens, or both.

One example of a batch of silicone hydrogel contact lenses of the present invention is a batch comprising: at least 20 polymerized silicone hydrogel contact lenses that are the reaction product of a polymerizable composition comprising a siloxane monomer represented by formula (6):

wherein n is an integer from 13 to 16 and has a molecular weight of about 1500 daltons; at least one hydrophobic vinyl-containing monomer; and at least one cross-linking agent, each silicone hydrogel contact lens in the batch being an aqueous extracted silicone hydrogel contact lens comprising an anterior surface and an opposing posterior surface, the posterior surface sized (sized and shaped) for placement against an eye of an individual; the anterior surface of each aqueous extraction contact lens has a clinically acceptable surface wettability such that less than 5% of the silicone hydrogel contact lenses in the batch have visually discernible unwetted spots when placed on the eyes of an individual; wherein the non-wetting spots are discontinuities in the contact lens wearer's pre-lens tear film present on the front surface of the lens body and are discernible to the naked eye at a total magnification of from about 6 x to about 70 x during slit lamp inspection. In one example, the at least one hydrophilic vinyl-containing monomer can comprise a hydrophilic amide monomer having one N-vinyl group, or the at least one crosslinker can comprise a vinyl-containing crosslinker, or both. In another example, the polymerizable composition can be free of diluent, or free of hydrophilic polymer, or free of N, N-Dimethylacrylamide (DMA), or any combination thereof. In another example, the silicone hydrogel contact lens may be free of a plasma surface treatment or free of a polymeric internal wetting agent provided by the inclusion of a hydrophilic polymer in the polymerizable composition used to form the silicone hydrogel contact lens, or both.

Another example of a batch of silicone hydrogel contact lenses of the present invention is a batch comprising: at least 20 polymerized silicone hydrogel contact lenses that are the reaction product of a polymerizable composition cured in a contact lens mold assembly, each contact lens mold assembly comprising a first mold section having a concave optical surface for forming an anterior surface of a silicone hydrogel contact lens body and a second mold section having a convex optical surface for forming a posterior surface of a silicone hydrogel contact lens body, at least one of the first mold section or the second mold section comprising a polar resin, the polymerizable composition comprising a siloxane monomer represented by formula (6):

The polymerizable compositions used to prepare the silicone hydrogel contact lenses of the invention may also include other ingredients in addition to those described above. For example, some polymerizable compositions can include at least one third siloxane monomer. The polymerizable composition can comprise one third siloxane monomer, or can comprise a third siloxane monomer component, wherein the third siloxane monomer component comprises two or more siloxane monomers, each of which is different from the first siloxane monomer and the second siloxane monomer of the polymerizable composition. Examples of the third siloxane monomer or third siloxane monomer component may include poly (organosiloxane) monomers or macromonomers or prepolymers, for example, 3- [ TRIS (trimethylsiloxy) silyl ] propylallyl carbamate, or 3- [ TRIS (trimethylsiloxy) silyl ] propyl vinyl carbamate, or trimethylsilylethyl carbonate vinyl ester, or trimethylsilylmethyl carbonate vinyl ester, or 3- [ TRIS (trimethylsiloxy) silyl ] propyl methacrylate (TRIS), or 3- (methacryloyloxy-2-hydroxypropoxy) propyl bis (trimethylsiloxy) methylsilane (SiGMA), or methyl bis (trimethylsiloxy) silylpropylglyceryl ethyl methacrylate (SiGEMA), or monomethacryloxypropyl terminated polydimethylsiloxane (MCS-M11), MCR-M07, or monomethacryloxypropyl terminated mono-n-butyl terminated polydimethylsiloxane (mPDMS), or any combination thereof. In one example of the polymerizable composition of the present disclosure, the at least one third siloxane can comprise one or more of the first siloxane described herein or the second siloxane described herein, wherein the at least one third siloxane differs from the first siloxane and the second siloxane present in the polymerizable composition based on molecular weight, molecular formula, or both molecular weight and molecular formula. For example, the third siloxane monomer can be a siloxane monomer of formula (1) having a different molecular weight than the first siloxane monomer of the polymerizable composition. In another example, the at least one third siloxane can comprise at least one siloxane disclosed in the following patents: US2007/0066706, US2008/0048350, US3808178, US4120570, US4136250, US4153641, US470533, US5070215, US5998498, US5760100, US6367929 and EP080539, the entire contents of which are incorporated herein by reference.

As previously mentioned, the polymerizable compositions of the present invention may optionally comprise at least one hydrophilic monomer. The polymerizable composition may comprise a single hydrophilic monomer, or may comprise two or more hydrophilic monomers present as the hydrophilic monomer component. Silicon-free hydrophilic monomers that can be used as hydrophilic monomers or hydrophilic monomer components in the polymerizable compositions disclosed herein include, for example, acrylamide-containing monomers, or acrylate-containing monomers, or acrylic-containing monomers, or methacrylate-containing monomers, or methacrylic-containing monomers, or any combination thereof. In one example, the hydrophilic monomer or monomer component can comprise or consist of a methacrylate-containing hydrophilic monomer. It is understood that the hydrophilic monomer or hydrophilic monomer component is a silicon-free monomer. Examples of hydrophilic monomers that may be included in the polymerizable compositions of the present disclosure may include, for example, N-Dimethylacrylamide (DMA), or 2-hydroxyethyl acrylate, or 2-hydroxyethyl methacrylate (HEMA), or 2-hydroxypropyl methacrylate, or 2-hydroxybutyl methacrylate (HOB), or 2-hydroxybutyl acrylate, or 4-hydroxybutyl acrylate, or glycerol methacrylate, or 2-hydroxyethyl methacrylamide, or polyethylene glycol monomethacrylate, or methacrylic acid, or acrylic acid, or any combination thereof.

In one example, the hydrophilic monomer or hydrophilic monomer component can comprise or consist of a vinyl-containing monomer. Examples of hydrophilic vinyl-containing monomers that can be provided in the polymerizable composition include, but are not limited to, N-vinyl formamide, or N-vinyl acetamide, or N-vinyl-N-ethyl acetamide, or N-vinyl isopropylamide, or N-vinyl-N-methyl acetamide (VMA), or N-vinyl pyrrolidone (NVP), or N-vinyl caprolactam, or N-vinyl-N-ethylformamide, or N-vinylformamide, or N-2-hydroxyethyl vinyl carbamate, or N-carboxy- β -alanine N-vinyl ester, 1, 4-Butanediol Vinyl Ether (BVE), or Ethylene Glycol Vinyl Ether (EGVE), or diethylene glycol vinyl ether (DEGVE), or any combination thereof.

In another example, the hydrophilic monomer or hydrophilic monomer component of the polymerizable composition can comprise or consist of a hydrophilic amide monomer. The hydrophilic amide monomer may be a hydrophilic amide monomer having one N-vinyl group, such as N-vinyl formamide, or N-vinyl acetamide, or N-vinyl-N-ethyl acetamide, or N-vinyl isopropylamide, or N-vinyl-N-methyl acetamide (VMA), or N-vinyl pyrrolidone (NVP), or N-vinyl caprolactam, or any combination thereof. In one example, the hydrophilic monomer or hydrophilic monomer component comprises N-vinyl-N-methylacetamide (VMA). For example, the hydrophilic monomer or monomer component can comprise or consist of VMA. In one embodiment, the hydrophilic monomer can be VMA.

In another example, the hydrophilic vinyl-containing monomer or monomer component can comprise or consist of a vinyl ether-containing monomer. Examples of vinyl ether-containing monomers include, but are not limited to, 1, 4-Butanediol Vinyl Ether (BVE), or Ethylene Glycol Vinyl Ether (EGVE), or diethylene glycol vinyl ether (DEGVE), or any combination thereof. In one example, the hydrophilic monomer component comprises or consists of BVE. In another example, the hydrophilic monomer component comprises or consists of EGVE. In another example, the hydrophilic vinyl component comprises or consists of DEGVE. In one embodiment, the vinyl ether-containing monomer can be a vinyl ether-containing monomer that is more hydrophilic than BVE, e.g., DEGVE. In another example, the hydrophilic monomer in the polymerizable composition can be a mixture of a first hydrophilic monomer (which is a vinyl-containing monomer but not a vinyl ether-containing monomer) and a second hydrophilic monomer (which is a vinyl ether-containing monomer). The mixture includes, for example, a mixture of VMA and one or more vinyl ethers (e.g., BVE, or DEGVE, or EGVE, or any combination thereof).

When present, the hydrophilic vinyl ether-containing monomer can be present in the polymerizable composition in an amount of from about 1 unit part to about 15 unit parts, or from about 3 unit parts to about 10 unit parts. When present in admixture with a hydrophilic vinyl-containing monomer that is not a vinyl ether, the hydrophilic vinyl-containing monomer that is not a vinyl ether and the hydrophilic vinyl ether-containing monomer can be present in the polymerizable composition in a ratio of at least 3: 1, or from about 3: 1 to about 15: 1, or about 4: 1, based on the ratio of the unit parts of the hydrophilic vinyl-containing monomer that is not a vinyl ether to the unit parts of the hydrophilic vinyl ether-containing monomer.

In another example, the hydrophilic vinyl-containing monomer component can comprise or consist of a combination of a first hydrophilic monomer or monomer component and a second hydrophilic monomer or hydrophilic monomer component. In one example, the first hydrophilic monomer has a different polymerizable functional group than the second hydrophilic monomer. In another example, each monomer of the first hydrophilic monomer component has a polymerizable functional group that is different from the second hydrophilic monomer. In another example, the first hydrophilic monomer has a polymerizable functional group different from each monomer of the second hydrophilic monomer component. In another example, each monomer of the first hydrophilic monomer component has a different polymerizable functional group than each monomer of the second hydrophilic monomer component.

For example, where the first hydrophilic monomer or monomer component comprises or consists of one or more amide-containing monomers, the second hydrophilic monomer or monomer component can comprise or consist of one or more amide-free monomers (i.e., one or more monomers that each do not have an amide functional group as part of their molecular structure). As another example, where the first hydrophilic monomer or monomer component comprises or consists of one or more vinyl-containing monomers, the second hydrophilic monomer or monomer component can comprise one or more non-vinyl monomers (i.e., one or more monomers each of which does not have a vinyl polymerizable functional group as part of its molecular structure). In another example, where the first hydrophilic monomer or monomer component comprises or consists of one or more amide monomers each having an N-vinyl group, the second hydrophilic monomer or monomer component can comprise or consist of one or more amide-free monomers. Where the first hydrophilic monomer or monomer component comprises or consists of one or more acrylate-free monomers (i.e., one or more monomers each having no acrylate or methacrylate polymerizable functional groups as part of its molecular structure), the second hydrophilic monomer or monomer component may comprise or consist of one or more acrylate-containing monomers or one or more methacrylate-containing monomers or any combination thereof. Where the first hydrophilic monomer or monomer component comprises or consists of one or more vinyl ether-free monomers (i.e., one or more monomers each having no vinyl ether polymerizable functional group as part of its molecular structure), the second hydrophilic monomer or monomer component can comprise or consist of one or more vinyl ether-containing monomers. In particular examples, the first hydrophilic monomer or monomer component can comprise or consist of one or more amide-containing monomers each having an N-vinyl group, and the second hydrophilic monomer or monomer component can comprise or consist of one or more vinyl ether-containing monomers.

In one example, where the first hydrophilic monomer or monomer component comprises or consists of a hydrophilic amide-containing monomer having one N-vinyl group, the second hydrophilic monomer or monomer component can comprise or consist of a vinyl ether-containing monomer. In a specific example, the first hydrophilic monomer can comprise VMA, and the second hydrophilic monomer or monomer component can comprise BVE or EGVE or DEGVE, or any combination thereof. The first hydrophilic monomer may comprise VMA and the second hydrophilic monomer may comprise BVE. The first hydrophilic monomer may comprise VMA and the second hydrophilic monomer may comprise EGVE. The first hydrophilic monomer may comprise VMA and the second hydrophilic monomer may comprise DEGVE. The first hydrophilic monomer may comprise VMA, and the second hydrophilic monomer component may comprise EGVE and DEGVE.

Similarly, the first hydrophilic monomer may be VMA, and the second hydrophilic monomer or monomer component may comprise BVE or EGVE or DEGVE, or any combination thereof. The first hydrophilic monomer can be VMA and the second hydrophilic monomer can be BVE. The first hydrophilic monomer may be VMA and the second hydrophilic monomer may be EGVE. The first hydrophilic monomer may comprise VMA and the second hydrophilic monomer may be DEGVE. The first hydrophilic monomer can be VMA and the second hydrophilic monomer component can be a combination of EGVE and DEGVE.

In another example, the silicon-free hydrophilic vinyl-containing monomer can have any molecular weight, such as a molecular weight of less than 400 daltons, or less than 300 daltons, or less than 250 daltons, or less than 200 daltons, or less than 150 daltons, or from about 75 daltons to about 200 daltons.

Where the hydrophilic monomer or hydrophilic monomer component is present in the polymerizable composition, the hydrophilic monomer or monomer component can be present in the polymerizable composition in an amount of from 30 unit parts to 60 unit parts of the polymerizable composition. The hydrophilic monomer or monomer component can be present in the polymerizable composition in a range of from 40 weight unit parts to 55 weight unit parts, or in a range of from 45 weight unit parts to 50 weight unit parts. Where the hydrophilic monomer component of the polymerizable composition comprises a first hydrophilic monomer or monomer component and a second hydrophilic monomer or monomer component, the second hydrophilic monomer or monomer component can be present in the polymerizable composition in an amount from 0.1 unit parts to 20 unit parts of the polymerizable composition. For example, the first hydrophilic monomer or monomer component can comprise from 29.9 unit parts to 40 unit parts and the second hydrophilic monomer or monomer component can comprise from 0.1 unit parts to 20 unit parts, in a total amount of from 30 unit parts to 60 unit parts of the hydrophilic monomer or monomer component present in the polymerizable composition. In another example, the second hydrophilic monomer or monomer component can be present in the polymerizable composition from 1 unit part to 15 unit parts, or from 2 unit parts to 10 unit parts, or from 3 unit parts to 7 unit parts.

As used herein, a vinyl-containing monomer is a monomer having a single polymerizable carbon-carbon double bond (i.e., a vinyl polymerizable functional group) present in its molecular structure, wherein the carbon-carbon double bond in the vinyl polymerizable functional group is less reactive than the carbon-carbon double bond present in the acrylate or methacrylate polymerizable functional group under free radical polymerization. In other words, monomers comprising a single acrylate or methacrylate polymerizable group are not considered to be vinyl-containing monomers, although as understood herein, carbon-carbon double bonds are present in acrylate and methacrylate groups. Examples of the polymerizable group having a carbon-carbon double bond (which is less reactive than the carbon-carbon double bond in the acrylate or methacrylate polymerizable group) include vinyl amide, vinyl ether, vinyl ester, and allyl ester polymerizable groups. Thus, examples of vinyl-containing monomers useful herein include monomers having a single vinyl amide, a single vinyl ether, a single vinyl ester, or a single allyl ester polymerizable group.

In addition, the polymerizable compositions of the present invention may optionally comprise at least one silicon-free hydrophobic monomer. The at least one hydrophobic monomer of the polymerizable composition can be one hydrophobic monomer, or can comprise a hydrophobic monomer component consisting of at least two hydrophobic monomers. Examples of hydrophobic monomers that can be used in the polymerizable compositions disclosed herein include, but are not limited to, acrylate-containing hydrophobic monomers or methacrylate-containing hydrophobic monomers, or any combination thereof. Examples of hydrophobic monomers include, but are not limited to, methyl acrylate, or ethyl acrylate, or propyl acrylate, or isopropyl acrylate, or cyclohexyl acrylate, or 2-ethylhexyl acrylate, or Methyl Methacrylate (MMA), or ethyl methacrylate, or propyl methacrylate, or butyl acrylate, or vinyl acetate, or vinyl propionate, or vinyl butyrate, or vinyl valerate, or styrene, or chloroprene, or vinyl chloride, or vinylidene chloride, or acrylonitrile, or 1-butene, or butadiene, or methacrylonitrile, or vinyl toluene, or vinyl ethyl ether, or perfluorohexylethylthiocarbonylaminoethyl methacrylate, or isobornyl methacrylate, or trifluoroethyl methacrylate, or hexafluoroisopropyl methacrylate, or hexafluorobutyl methacrylate, Or ethylene glycol methyl ether methacrylate (EGMA) or any combination thereof. In one embodiment, the hydrophobic monomer or monomer component may comprise or consist of methyl methacrylate or ethylene glycol methyl ether methacrylate or both.

When present in the polymerizable composition, the hydrophobic monomer or monomer component can be present in an amount of from about 5 unit parts to about 25 unit parts, or from about 10 unit parts to about 20 unit parts.

In one example, the hydrophobic monomer component can comprise at least two hydrophobic monomers each having a different polymerizable functional group. In another example, the hydrophobic monomer component can comprise at least two hydrophobic monomers each having the same polymerizable functional group. The hydrophobic monomer component may comprise or consist of two hydrophobic monomers both having the same polymerizable functional group. In one example, the hydrophobic monomer component can comprise or consist of two hydrophobic methacrylate-containing monomers. The hydrophobic monomer component may comprise or consist of MMA and EGMA. In one example, the at least two hydrophobic monomers of the hydrophobic monomer component can comprise or consist of MMA and EGMA, and the amount of MMA to EGMA present in the polymerizable composition can be in a ratio of about 6: 1 to about 1: 1 (based on unit parts of MMA to unit parts EGMA). The ratio of unit parts of MMA to EGMA present in the polymerizable composition may be about 2: 1 (based on unit parts of MMA to unit parts of EGMA).

The polymerizable composition may optionally further comprise at least one crosslinking agent. The polymerizable composition may comprise one crosslinker, or may comprise a crosslinker component comprising at least two crosslinkers. The crosslinking agent used herein is a silicon-free crosslinking agent and is therefore different from the multifunctional siloxane monomer that may be present in the polymerizable composition.

According to the invention, a crosslinker is understood to be a monomer having more than one polymerizable functional group (e.g. two or three or four polymerizable functional groups) as part of its molecular structure, i.e. a multifunctional monomer, such as a difunctional or trifunctional or tetrafunctional monomer. Silicon-free crosslinkers that may be used in the polymerizable compositions disclosed herein include, for example, but are not limited to, allyl (meth) acrylate, or lower alkylene glycol di (meth) acrylate, or poly (lower alkylene) glycol di (meth) acrylate, or lower alkylene di (meth) acrylate, or divinyl ether, or divinyl sulfone, or divinylbenzene and trivinylbenzene, or trimethylolpropane tri (meth) acrylate, or pentaerythritol tetra (meth) acrylate, or bisphenol a di (meth) acrylate, or methylenebis (meth) acrylamide, or triallyl phthalate and diallyl phthalate, or any combination thereof. Crosslinkers as disclosed in the examples include, for example, Ethylene Glycol Dimethacrylate (EGDMA), or triethylene glycol dimethacrylate (TEGDMA), or triethylene glycol divinyl ether (TEGDVE), or any combination thereof. In one example, the crosslinking agent can have a molecular weight of less than 1500 daltons, or less than 1000 daltons, or less than 500 daltons, or less than 200 daltons.

In one example, the crosslinking agent can be a vinyl-containing crosslinking agent. As used herein, a vinyl-containing crosslinking agent is a monomer having at least two polymerizable carbon-carbon double bonds (i.e., at least two vinyl polymerizable functional groups) present in its molecular structure, wherein each of the at least two polymerizable carbon-carbon double bonds present in the vinyl polymerizable functional groups of the vinyl-containing crosslinking agent is less reactive than the carbon-carbon double bonds present in the acrylate or methacrylate polymerizable functional groups. Although carbon-carbon double bonds are present in the acrylate and methacrylate polymerizable functional groups as understood herein, crosslinkers comprising one or more acrylate or methacrylate polymerizable groups (e.g., acrylate-containing crosslinkers or methacrylate-containing crosslinkers) are not considered vinyl-containing crosslinkers. Polymerizable functional groups having a carbon-carbon double bond less reactive than the carbon-carbon double bond of the acrylate or methacrylate polymerizable group include, for example, vinyl amide, vinyl ester, vinyl ether, and allyl ester polymerizable functional groups. Thus, vinyl-containing crosslinkers as used herein include, for example, crosslinkers having at least two polymerizable functional groups selected from: vinyl amides, vinyl ethers, vinyl esters, allyl esters, and any combination thereof. The mixed vinyl-containing crosslinking agent used herein is the following crosslinking agent: having at least one polymerizable carbon-carbon double bond present in its structure and less reactive than the carbon-carbon double bond present in the acrylate or methacrylate polymerizable functional group (i.e., at least one vinyl polymerizable functional group), and at least one polymerizable functional group present in its structure and having a carbon-carbon double bond at least equivalent in reactivity to the carbon-carbon double bond in the acrylate or methacrylate polymerizable functional group.

In one example, the crosslinker or crosslinker component can comprise a vinyl-containing crosslinker. For example, the vinyl-containing crosslinker or crosslinker component can comprise or consist of a vinyl ether-containing crosslinker. In another example, the crosslinker or crosslinker component can comprise or consist of an acrylate-containing crosslinker (i.e., a crosslinker having at least two acrylate polymerizable functional groups), or a methacrylate-containing crosslinker (i.e., at least two methacrylate polymerizable functional groups), or at least one acrylate-containing crosslinker and at least one methacrylate-containing crosslinker.

The crosslinker component may comprise or consist of a combination of two or more crosslinkers each having different polymerizable functional groups. For example, the crosslinker component may comprise a vinyl-containing crosslinker and an acrylate-containing crosslinker. The crosslinker component may comprise a vinyl-containing crosslinker and a methacrylate-containing crosslinking group. The crosslinker component may comprise or consist of a vinyl ether-containing crosslinker and a methacrylate-containing crosslinker.

Optionally, the polymerizable composition of the present invention may comprise or consist of at least one vinyl-containing crosslinker or crosslinker component, and may be free of silicon-free and vinyl-free crosslinkers. In other words, in this example, the polymerizable composition comprises a first siloxane monomer, a second siloxane monomer, and at least one crosslinker, wherein the at least one crosslinker is comprised of at least one vinyl-containing crosslinker (i.e., a single vinyl-containing crosslinker or a vinyl-containing crosslinker component comprising two or more vinyl-containing crosslinkers), because no non-silicone crosslinker other than the vinyl-containing crosslinker is present in the polymerizable composition. In other words, in this example, no vinyl crosslinking agent is present in the polymerizable composition.

The optional crosslinker or crosslinker component may be present in the polymerizable composition in an amount of from 0.01 unit parts to 10.0 unit parts (e.g., from 0.05 unit parts to 5.0 unit parts, or from 0.1 unit parts to 2.0 unit parts, or from 0.2 unit parts to 1.0 unit parts, or from 0.3 unit parts to 0.8 unit parts). In one example, where the crosslinker or crosslinker component comprises a vinyl-containing crosslinker, the vinyl-containing crosslinker or crosslinker component can be present in the polymerizable composition in an amount of 0.01 unit parts to 0.80 unit parts (e.g., 0.05 unit parts to 0.30 unit parts or 0.1 unit parts to 0.2 unit parts). Where the at least one crosslinker is an acrylate-or methacrylate-containing crosslinker or crosslinker component, the acrylate-or methacrylate-containing crosslinker or crosslinker component may be present in the polymerizable composition in an amount of from 0.1 unit parts to 2.0 unit parts (e.g., from 0.3 unit parts to 1.2 unit parts or from 0.5 unit parts to 0.8 unit parts). When a combination of a vinyl-containing crosslinker or crosslinker component and an acrylate-containing or methacrylate-containing crosslinker or crosslinker component is used, the vinyl-containing crosslinker or crosslinker component and the acrylate-containing or methacrylate-containing crosslinker or crosslinker component can be present in the polymerizable composition in a weight ratio of 1: 2 to 1: 20, or 1: 3 to 1: 12, or 1: 4 to 1: 7, based on the weight of the unit parts of the vinyl-containing crosslinker or crosslinker component to the unit parts of the acrylate-containing or methacrylate-containing crosslinker or crosslinker component.

While limiting the amount of vinyl-containing crosslinking agent in some polymerizable compositions can improve wettability, in many cases, the inclusion of a vinyl-containing crosslinking agent in a polymerizable composition can also improve the dimensional stability of the resulting contact lens formed from the polymerizable composition. Thus, in some polymerizable compositions, the vinyl-containing crosslinking agent can be present in the polymerizable composition in an amount effective to produce a contact lens having improved dimensional stability as compared to a contact lens produced from the same polymerizable composition but without the vinyl-containing crosslinking agent.

Another method of producing contact lenses having ophthalmically acceptably wettable surfaces of the present invention can be to include an amount of vinyl-containing crosslinking agent in the polymerizable composition based on the ratio of unit parts of hydrophilic vinyl-containing monomer present in the composition to unit parts of vinyl-containing crosslinking agent present in the composition. For example, the unit parts of the hydrophilic vinyl-containing monomer and the unit parts of the vinyl-containing crosslinking agent can be present in the polymerizable composition in a ratio of greater than about 125: 1, or from about 150: 1 to about 625: 1, or from about 200: 1 to about 600: 1, or from about 250: 1 to about 500: 1, or from about 450: 1 to about 500: 1, based on the ratio of the unit parts of the hydrophilic vinyl-containing monomer to the unit parts of the vinyl-containing crosslinking agent.

The polymerizable composition may optionally include one or more organic diluents, one or more polymerization initiators (i.e., Ultraviolet (UV) initiators or thermal initiators or both), or one or more UV absorbers, or one or more colorants, or one or more oxygen scavengers, or one or more chain transfer agents, or any combination thereof. These optional ingredients may be reactive or non-reactive ingredients. In at least one example, the polymerizable composition can be free of diluents, wherein it is free of any organic diluents that can achieve miscibility between the silicone and other lens forming ingredients (e.g., optional hydrophilic monomers, hydrophobic monomers, and crosslinking agents). Additionally, many of the polymerizable compositions of the present invention are substantially free of water (e.g., contain no more than 3.0% or 2.0% by weight water).

The polymerizable compositions disclosed herein can optionally comprise one or more organic diluents, i.e., the polymerizable compositions can comprise an organic diluent, or can comprise an organic diluent component having two or more organic diluents. Organic diluents that may optionally be included in the polymerizable compositions of the present invention include alcohols, including lower alcohols, such as, but not limited to, pentanol, or hexanol, or octanol, or decanol, or any combination thereof. When included, the organic diluent or organic diluent component can be provided in the polymerizable composition in an amount of from about 1 unit part to about 70 unit parts, or from about 2 unit parts to about 50 unit parts, or from about 5 unit parts to about 30 unit parts.

Methods commonly used to increase the miscibility of the silicone monomer and the hydrophilic monomer include adding an organic diluent to the polymerizable composition to act as a compatibilizer between the hydrophilic monomer and the generally more hydrophobic silicone monomer, or using only silicone monomers having low molecular weights (e.g., molecular weights below 2500 daltons). The use of a first siloxane as described above allows for the inclusion of both a high molecular weight second siloxane and a significant amount of one or more hydrophilic monomers in the polymerizable composition of the present invention. And while one or more organic diluents may be included in the polymerizable compositions of the present invention disclosed herein, it may not be necessary to do so in order to obtain a miscible polymerizable composition of the present invention. In other words, in at least one example, the silicone hydrogel contact lenses of the present invention are formed from a polymerizable composition that does not contain an organic diluent.

Examples of the disclosed polymerizable compositions can be miscible at the time of initial preparation, and can remain miscible during a period of time sufficient for industrial manufacture of contact lenses (e.g., 2 weeks, or 1 week, or 5 days). Typically, upon polymerization and processing into contact lenses, the miscible polymerizable composition produces contact lenses having ophthalmically acceptable clarity.

The polymerizable composition of the present invention may optionally comprise one or more polymerization initiators, i.e., the polymerizable composition may comprise an initiator, or may comprise an initiator component having two or more polymerization initiators. Polymerization initiators that may be included in the polymerizable compositions of the present invention include, for example, azo compounds or organic peroxides or both. Initiators that may be present in the polymerizable composition include, for example, but are not limited to, benzoin ethyl ether, or benzyl dimethyl ketal, or α, α -diethoxyacetophenone, or 2, 4, 6-trimethylbenzoyldiphenylphosphine oxide, or benzoin peroxide, or t-butyl peroxide, or azobisisobutyronitrile, or azobisdimethylvaleronitrile, or any combination thereof. The UV photoinitiator may include, for example, a phosphine oxide such as diphenyl (2, 4, 6-trimethylbenzoyl) phosphine oxide, or benzoin methyl ether, or 1-hydroxycyclohexyl phenyl ketone, or Darocur (available from BASF, florhn park, ny, usa), or Irgacur (also available from BASF), or any combination thereof. In the examples disclosed herein, the polymerization initiator is the thermal initiator 2, 2' -azobis-2-methylpropanenitrile (VAZO-64 from dupont nemours & Co.), wilmington, talawa, usa). Other common thermal initiators may include 2, 2 '-azobis (2, 4-dimethylvaleronitrile) (VAZO-52) and 1, 1' -azobis (cyanocyclohexane) (VAZO-88). The polymerization initiator or initiator component may be present in the polymerizable composition in an amount of from about 0.01 to about 2.0 unit parts by weight, or from about 0.1 to about 1.0 unit parts by weight, or from about 0.2 to about 0.6 unit parts by weight.

Optionally, the polymerizable compositions of the present disclosure may comprise one or more UV absorbers, i.e., the polymerizable compositions may comprise a UV absorber, or may comprise a UV absorber component having two or more UV absorbers. UV absorbers that may be included in the polymerizable compositions of the present invention include, for example, benzophenone, or benzotriazole, or any combination thereof. In the examples disclosed herein, the UV absorber is 2- (4-benzoyl-3-hydroxyphenoxy) ethyl acrylate (UV-416) or 2- (3- (2H-benzotriazol-2-yl) -4-hydroxy-phenyl) ethyl methacrylate (UV-A-S-B-E)7966 from norrek (Noramco), yadend, georgia, usa). The UV absorber or UV absorber component can be present in the polymerizable composition in an amount of from about 0.01 to about 5.0 parts by weight, or from about 0.1 to about 3.0 parts by weight, or from about 0.2 to about 2.0 parts by weight.

The polymerizable compositions of the present invention can also optionally include at least one colorant (i.e., one colorant or a colorant component comprising two or more colorants), but encompass both tinted lens products and clear lens products. In one example, the colorant can be a reactive dye or pigment effective to provide color to the resulting lens product. The colorant or colorant component in the polymerizable composition can comprise a polymerizable colorant, or can comprise a non-polymerizable colorant, or any combination thereof. The polymerizable colorant can be a colorant whose molecular structure comprises a polymerizable functional group, or can be a colorant whose molecular structure includes both a monomeric moiety and a dye moiety, i.e., the colorant can be a monomer-dye complex. Colorants can include, for example, VAT blue 6(7, 16-dichloro-6, 15-dihydroanthracene azine-5, 9, 14, 18-tetrone), or 1-amino-4- [3- (. beta. -sulfatoethylsulfonyl) anilino ] -2-anthraquinone sulfonic acid (c.i. reactive blue 19, RB-19), or a monomer-dye complex of reactive blue 19 and hydroxyethyl methacrylate (RB-19HEMA), or 1, 4-bis [4- [ (2-methacryloyl-oxyethyl) phenylamino ] anthraquinone (reactive blue 246, RB-246, available from yalan chemical company, alslon, irish), or 1, 4-bis [ (2-hydroxyethyl) amino ] -9, 10-anthracenedione bis (2-acrylate) ester (RB-247), Or reactive blue 4(RB-4), or a monomer-dye complex of reactive blue 4 and hydroxyethyl methacrylate (RB-4HEMA or "blue HEMA"), or any combination thereof. In one example, the colorant or colorant component can comprise a polymerizable colorant. The polymerizable colorant component can comprise, for example, RB-246, or RB-274, or RB-4HEMA, or RB-19HEMA, or any combination thereof. Examples of monomer-dye complexes include RB-4HEMA and RB-19 HEMA. Further examples of monomer-dye complexes are described in US5944853 and US 72169975, both of which are incorporated herein by reference in their entirety. Other exemplary colorants are disclosed, for example, in U.S. patent application publication No. 2008/0048350, the disclosure of which is incorporated herein by reference in its entirety. In the examples disclosed herein, the colorant is a reactive blue dye, such as those described in US4997897, the disclosure of which is incorporated herein by reference in its entirety. Other suitable colorants for use according to the present invention are phthalocyanine pigments (e.g. phthalocyanine blue or phthalocyanine green), or chromium-aluminum-cobalt oxide, or chromium oxide and various red, yellow, brown and black iron oxides, or any combination thereof. Opacifiers such as titanium dioxide may also be included. For some applications, combinations of colorants having different colors may be employed as the colorant component. If a colorant or colorant component is employed, it may be present in the polymerizable composition in an amount ranging from about 0.001 unit parts to about 15.0 unit parts, or from about 0.005 unit parts to about 10.0 unit parts, or from about 0.01 unit parts to about 8.0 unit parts.

The polymerizable composition of the present invention may optionally comprise at least one oxygen scavenger, i.e., one oxygen scavenger or an oxygen scavenger component comprising two or more oxygen scavengers. Examples of oxygen scavengers that may be included as an oxygen scavenger or oxygen scavenger component of the polymerizable composition of the present invention include, for example, vitamin E, or a phenolic compound, or a phosphite compound, or a phosphine compound, or an amine oxide compound, or any combination thereof. For example, the oxygen scavenger or oxygen scavenger component may consist of or comprise a phosphine-containing compound. In the examples disclosed herein, the oxygen scavenger or oxygen scavenger component is a phosphine-containing compound, such as triphenylphosphine, or a polymerizable form of triphenylphosphine, such as diphenyl (p-vinylphenyl) phosphine.

Chain transfer is a polymerization reaction that transfers the activity of a growing polymer chain to another molecule, thereby reducing the average molecular weight of the final polymer. The polymerizable composition of the present invention may optionally comprise at least one chain transfer agent, i.e., may comprise one chain transfer agent or may comprise a chain transfer agent component having at least two chain transfer agents. Examples of chain transfer agents that may be included as a chain transfer agent or chain transfer component of the polymerizable composition of the present invention include, for example, thiol compounds, or halocarbon compounds, or C3-C5 hydrocarbons, or any combination thereof. In the examples disclosed herein, the chain transfer agent is allyloxyethanol. When present in the polymerizable composition, the chain transfer agent or chain transfer agent component may be present in an amount of from about 0.01 unit parts to about 1.5 unit parts, for example from about 0.1 unit parts to about 0.5 unit parts.

In one example, the silicone hydrogel contact lenses of the present invention can have a relatively high Equilibrium Water Content (EWC). Methods of determining EWC are known to those skilled in the art and can be based on the weight loss of the lens during the drying process. For example, a silicone hydrogel contact lens, when fully hydrated, can have an equilibrium water content of 20 wt% to 75 wt%. The present contact lenses can have an EWC of about 30 wt% to about 70 wt%, or about 45 wt% to about 65 wt%, or about 50 wt% to about 63 wt%, or about 50 wt% to about 67 wt%, or about 55 wt% to about 65 wt%.

The contact lenses of the invention may have an oxygen permeability of at least 55 barrers (or Dk, Dk ≧ 55 barrers) or at least 60 barrers (Dk ≧ 60 barrers), or at least 65 barrers (Dk ≧ 65 barrers). The lens may have an oxygen permeability of about 55 to about 135, or about 60 to about 120, or about 65 to about 90, or about 50 to about 75 bara. Various methods of measuring oxygen permeability are known to those skilled in the art.

The silicone hydrogel contact lenses of the invention have an average tensile modulus of about 0.20MPa to about 0.90MPa when fully hydrated. For example, the average modulus can be from about 0.30MPa to about 0.80MPa, or from about 0.40MPa to about 0.75MPa, or from about 0.50MPa to about 0.70 MPa.

The modulus of a contact lens or lens body as used herein is understood to mean the tensile modulus, also known as Young's modulus. Which is a measure of the stiffness of an elastic material. Tensile modulus can be measured using a method that meets ANSIZ80.20 standards. In one example, the tensile modulus can be measured using an instron 3342 or 3343 mechanical testing system.

The contact lenses of the invention may have an oxygen permeability of at least 55 barrers (Dk ≧ 55 barrers), or an EWC of from about 30% to about 70%, or a tensile modulus of from about 0.2MPa to about 0.9MPa, or any combination thereof. In one example, the contact lens may have an oxygen permeability of at least 60 barrers (Dk ≧ 60 barrers), or an EWC of about 35% to about 65%, or a tensile modulus of about 0.3MPa to about 0.8MPa, or any combination thereof. In another example, the present contact lenses may have an oxygen permeability of at least 60 barrers, or an EWC of about 45% to about 65%, or a tensile modulus of about 0.40MPa to about 0.75MPa, or any combination thereof.

In one example, the present contact lenses have an oxygen permeability of at least 55 barrers, an EWC of from about 30% to about 70%, and a tensile modulus of from about 0.2MPa to about 0.9 MPa.

The silicone hydrogel contact lenses of the invention can have an average percent energy loss of about 25% to about 40% when fully hydrated. For example, the average percent energy loss may be from about 27% to about 40%, or may be from about 30% to about 37%.

Percent energy loss, as used herein, is a measure of the energy lost as heat when a cycle of energy loading and energy release is applied to a viscoelastic material. The percent energy loss can be determined using a variety of methods known to those skilled in the art. For example, the force involved in stretching a sample to 100% strain at a constant rate and then returning it to 0% can be determined and used to calculate the percent energy loss of the material.

The present contact lenses can have a thickness of less than about 8.0 x 10^-3mm²A/min, or less than about 7.0X 10^-3mm²A/min, or less than about 5.0X 10^-3mm²Ion flow/min. Various methods of determining ion current are conventional and known to those skilled in the art.

The present silicone hydrogel contact lenses can have a captive bubble dynamic advancing contact angle of less than 120 degrees, for example, less than 90 degrees when fully hydrated, less than 80 degrees when fully hydrated, less than 70 degrees when fully hydrated, or less than 65 degrees when fully hydrated, or less than 60 degrees when fully hydrated, or less than 50 degrees when fully hydrated.

The present silicone hydrogel contact lenses can have a captive bubble static contact angle of less than 70 degrees when fully hydrated, or less than 60 degrees when fully hydrated, or less than 55 degrees when fully hydrated, or less than 50 degrees when fully hydrated, or less than 45 degrees when fully hydrated.

In one example, the present contact lenses can have a wet extractable component. The wet extractable component is determined based on weight loss during methanol extraction of contact lenses that have been fully hydrated and sterilized prior to drying and extraction testing. The wet extractable component can comprise unreacted or partially reacted polymerizable ingredients of the polymerizable composition. Since the wet extractable component is comprised of extractable material that remains in the lens body after the lens body has been sufficiently processed to form a sterile contact lens, for lenses formed from polymerizable compositions that include non-reactive ingredients, it can be assumed that substantially all of the non-reactive ingredients have been removed from the lens body during processing of the lens body, and thus the wet extractable component is essentially comprised of extractable components formed from reactive ingredients in the polymerizable composition (i.e., unreacted polymerizable components and partially reacted polymerizable ingredients). In lenses prepared from polymerizable compositions that do not contain diluents, the wet extractable component can be present in the contact lens in an amount of from about 1% wt/wt to about 15% wt/wt, or from about 2% wt/wt to about 10% wt/wt, or from about 3% wt/wt to about 8% wt/wt, based on the dry weight of the lens body prior to extraction testing. In lenses prepared from polymerizable compositions comprising diluents, the wet extractable component can consist of a portion of the diluent and unreacted and partially reacted polymerizable ingredients, and can be present in the contact lens in an amount of from about 1% wt/wt to about 20% wt/wt, or from about 2% wt/wt to about 15% wt/wt, or from about 3% wt/wt to about 10% wt/wt of the lens, based on the dry weight of the lens body prior to extraction testing.

In one example, the present contact lenses have a dry extractable component. The dry extractable component is determined based on weight loss during methanol extraction of polymeric lens bodies that have not been washed, extracted (as part of the manufacturing process), hydrated, or sterilized prior to drying and extraction testing. The dry extractable component can comprise unreacted or partially reacted polymerizable ingredients of the polymerizable composition. Where optional non-reactive ingredients such as diluents are present in the polymerizable composition, the dry extractable component may further comprise non-reactive ingredients.

In lenses prepared from polymerizable compositions that do not contain diluents, the dry extractable component of the lens consists essentially of the dry extractable component contributed by the polymerizable ingredients in the polymerizable composition (i.e., unreacted or partially reacted polymerizable ingredients), and may also include minor amounts (e.g., less than 3% wt/wt) of dry extractable material (e.g., initiators, colorants, oxygen scavengers, etc.) contributed by optional non-polymerizable components present in the polymerizable composition. In lenses prepared from polymerizable compositions that do not contain diluents, the dry extractable component can be present in the polymerized lens body in an amount from about 1% wt/wt to about 30% wt/wt, or from about 2% wt/wt to about 25% wt/wt, or from about 3% wt/wt to about 20% wt/wt, or from about 4% wt/wt to about 15% wt/wt, or from 2% wt/wt to less than 10% wt/wt, based on the dry weight of the lens body prior to extraction testing.

In lenses prepared from polymerizable compositions containing significant amounts (e.g., greater than 3% wt/wt) of optional non-reactive ingredients such as diluents, the dry extractable component is made up of extractable material contributed by the reactive ingredients as well as extractable components contributed by non-polymerizable ingredients in the polymerizable composition. The total amount of reactive and non-polymerizable components present in the contact lens contributing dry extractable components can consist of from about 1% wt/wt to about 75% wt/wt, or from about 2% wt/wt to about 50% wt/wt, or from about 3% wt/wt to about 40% wt/wt, or from about 4% wt/wt to about 20% wt/wt, or from about 5% to about 10% of the lens based on the dry weight of the polymeric lens body prior to the extraction test. The total amount of dry extractable components (i.e., unreacted or partially reacted polymerizable ingredients) contributed by the polymerizable ingredients can be in an amount of about 1% wt/wt to about 30% wt/wt, or about 2% wt/wt to about 25% wt/wt, or about 3% wt/wt to about 20% wt/wt, or about 4% wt/wt to about 15% wt/wt, or 2% wt/wt to less than 10% wt/wt of the lens body based on the dry weight of the lens body prior to extraction testing.

The contact lenses of the present invention are ophthalmically acceptable contact lenses in that they are configured to be placed or disposed on the cornea of an animal or human eye. An ophthalmically acceptable contact lens as used herein is understood to be a contact lens having at least one of a plurality of different properties as described below. An ophthalmically acceptable contact lens can be formed from and packaged in ophthalmically acceptable ingredients such that the lens is non-cytotoxic and does not release irritating and/or toxic ingredients during wear. An ophthalmically acceptable contact lens can have a clarity in the optic zone of the lens (i.e., the portion of the lens that provides vision correction) sufficient for its intended use in contact with the cornea of the eye, e.g., a visible light transmittance of at least 80%, or at least 90%, or at least 95%. Ophthalmically acceptable contact lenses can have sufficient mechanical properties to facilitate lens handling and care over a duration based on their expected lifetime. For example, its modulus, tensile strength, and elongation may be sufficient to withstand insertion, wearing, removal, and optionally cleaning during the lens' expected lifetime. The level of these suitable properties will vary depending on the intended life and use of the lens (e.g., disposable, multiple use per month, etc.). An ophthalmically acceptable contact lens can have an effective or suitable ion current to substantially inhibit or substantially prevent corneal staining, e.g., corneal staining that is more severe than superficial or moderate corneal staining after 8 or more consecutive lens wear on the cornea. Ophthalmically acceptable contact lenses can have sufficient oxygen permeability levels to allow oxygen to reach the cornea of the eye wearing the lens in an amount sufficient to maintain long-term corneal health. An ophthalmically acceptable contact lens can be one that does not cause significant or excessive corneal edema of the eye on which the lens is worn, e.g., no more than about 5% or 10% corneal edema after being worn on the cornea of the eye during overnight sleep. An ophthalmically acceptable contact lens can be a lens that allows movement of the lens on the cornea of an eye wearing the lens sufficient to facilitate tear flow between the lens and the eye, in other words, without adhering the lens to the eye with sufficient force to impede normal lens movement, and with a sufficiently low level of movement on the eye to allow vision correction. An ophthalmically acceptable contact lens can be a lens that permits the lens to be worn on-eye without excess or significant discomfort and/or irritation and/or pain. An ophthalmically acceptable contact lens can be a lens that inhibits or substantially prevents the deposition of lipids and/or proteins sufficiently to allow the lens wearer to remove the lens due to the deposition. At least one of the water content, or surface wettability, or modulus or design, or any combination thereof, of the ophthalmically acceptable contact lenses is effective to promote ophthalmically compatible wearing of the contact lenses by a contact lens wearer, at least during a day. Ophthalmically compatible wear is understood to mean that the lens wearer produces little or no discomfort when wearing the lens and little or no corneal staining occurs. Conventional clinical methods can be used to determine whether a contact lens is ophthalmically acceptable, such as those performed by an eye care practitioner and as will be appreciated by those skilled in the art.

The contact lenses of the invention have ophthalmically acceptably wettable lens surfaces. For example, the contact lens can have an ophthalmically acceptably wettable lens surface when the polymerizable composition used to form the polymeric lens body does not contain an internal wetting agent, or when the polymerizable composition used to form the polymeric lens body does not contain an organic diluent, or when the polymeric lens body is extracted in water or an aqueous solution that does not contain a volatile organic solvent, or when the polymeric lens body is not subjected to a surface plasma treatment, or any combination thereof.

One method commonly used in the art to increase the wettability of contact lens surfaces is to treat or modify the lens surface. According to the present invention, silicone hydrogel contact lenses can have ophthalmically acceptably wettable lens surfaces without surface treatment or surface modification. Surface treatments include, for example, plasma and corona treatments that increase the hydrophilicity of the lens surface. While it is possible to apply one or more surface plasmonic treatments to the present lens bodies, this is not required in order to obtain silicone hydrogel contact lenses having an ophthalmically acceptably wettable lens surface when fully hydrated. In other words, in one example, the present silicone hydrogel contact lenses may not be surface plasma or corona treated.

Surface modification includes binding a wetting agent to a lens surface, for example, binding a wetting agent such as a hydrophilic polymer to at least one lens surface by chemical bonding or another form of chemical interaction. In some cases, the wetting agent can be bound to the lens surface and at least a portion of the polymeric matrix of the lens (i.e., at least a portion of the lens body) by chemical bonding or another form of chemical interaction. An ophthalmically acceptably wettable lens surface of the present invention can have ophthalmically acceptable wettability in the absence of a wetting agent (e.g., a polymeric or non-polymeric material) that is at least bound to the lens surface. While it is possible to incorporate one or more wetting agents into the lenses of the invention, this need not be done in order to obtain silicone hydrogel contact lenses having ophthalmically acceptably wettable lens surfaces when fully hydrated. Thus, in one example, the lenses of the invention can comprise a wetting agent, e.g., a hydrophilic polymer and including polyvinylpyrrolidone, bound to the lens surface. Alternatively, in another example, the silicone hydrogel contact lenses of the invention may be free of wetting agents bound to the lens surface.

Another approach to improving lens wettability is to physically entrap wetting agents within the lens body or contact lens, for example, by: the wetting agent is introduced into the lens body as the lens body expands and the lens body is then returned to a less expanded state, thereby trapping a portion of the wetting agent within the lens body. The wetting agent may be permanently trapped within the lens body, or may be released from the lens over time (e.g., during wear). An ophthalmically acceptably wettable lens surface of the present invention can have ophthalmically acceptable wettability in the absence of a wetting agent (e.g., a polymeric material or a non-polymeric material) physically entrapped in the lens body after formation of the polymeric lens body. Although it is possible to physically entrap one or more wetting agents in the lenses of the invention, this need not be done in order to obtain silicone hydrogel contact lenses having ophthalmically acceptably wettable lens surfaces when fully hydrated. Thus, in one example, the lenses of the invention can comprise a wetting agent entrapped within the lens, for example, a hydrophilic polymer and including polyvinylpyrrolidone. Alternatively, the silicone hydrogel contact lenses of the invention may be free of wetting agents physically trapped within the lens. As used herein, physically entrapped means that the wetting agent or other ingredient is immobilized in the polymeric matrix of the lens with little or no chemical bonding or interaction between the wetting agent and or other ingredient and the polymeric matrix. This is in contrast to components that are chemically bonded to the polymeric matrix, for example, by ionic bonding, covalent bonding, van der waals forces, and the like.

Another method commonly used in the art to increase the wettability of silicone hydrogel contact lenses includes adding one or more wetting agents to the polymerizable composition. In one example, the wetting agent can be a polymeric wetting agent. However, when the polymerizable composition used to form the polymeric lens body is free of wetting agents, the contact lenses of the invention can have an ophthalmically acceptably wettable lens surface. Although one or more wetting agents may be included in the polymerizable compositions of the present invention to increase the wettability of the silicone hydrogel contact lenses of the present invention, it is not necessary to do so in order to obtain silicone hydrogel contact lenses having ophthalmically acceptably wettable lens surfaces. In other words, in one example, the silicone hydrogel contact lenses of the present invention can be formed from a polymerizable composition that does not contain a wetting agent. Alternatively, in another example, the polymerizable composition of the present invention can further comprise a wetting agent.

In one example, the wetting agent can be an internal wetting agent. The internal wetting agent can be incorporated within at least a portion of the lens polymeric matrix. For example, the internal wetting agent can be incorporated within at least a portion of the lens polymeric matrix by chemical bonding or another form of chemical interaction. In some cases, wetting agents can also bind to the lens surface. The internal wetting agent may comprise a polymeric material or a non-polymeric material. While it is possible that one or more internal wetting agents may be incorporated within the polymeric matrix of the lenses of the invention, this need not be done in order to obtain silicone hydrogel contact lenses having ophthalmically acceptably wettable lens surfaces when fully hydrated. Thus, in one example, the lenses of the invention can comprise an internal wetting agent bound to at least a portion of the lens polymeric matrix. Alternatively, in another example, the silicone hydrogel contact lenses of the invention can be free of an internal wetting agent bound to at least a portion of the lens polymeric matrix.

In another example, the wetting agent can be an internal polymeric wetting agent. The internal polymeric wetting agent can be present in the polymeric lens body as part of an Interpenetrating Polymer Network (IPN) or a semi-IPN. Interpenetrating polymer networks are formed from at least two polymers, each crosslinked to itself, but not to each other. Similarly, a semi-IPN is formed from at least two polymers, at least one of which is crosslinked to itself but not to the other, and the other is neither crosslinked to itself nor to the other. In one example of the invention, a contact lens can have an ophthalmically acceptably wettable lens surface when the polymeric lens body is free of an internal polymeric wetting agent in the form of an IPN or semi-IPN in the lens body. Alternatively, the contact lens can comprise an internal polymeric wetting agent in the form of an IPN or semi-IPN in the lens body.

In another example, the wetting agent can be a linking compound present in the polymerizable composition used to form the lens body, or a linking agent that is physically entrapped within the polymerized lens body after the lens body has been formed. Where the wetting agent is a linking compound, after polymerizing the lens body or entrapping the linking agent in the polymerized lens body, the linking compound can then link the wetting agent to the lens body upon contact of the lens body with a second wetting agent. The linking can be performed as part of the manufacturing process (e.g., as a washing process), or can be performed while the lens body is in contact with the packaging solution. The linkage may be in the form of an ionic or covalent bond, or in the form of van der waals attraction. The linking agent can comprise organoboronic acid(s) moieties or groups, such that the polymeric organoboronic acid moieties or groups are present in the polymeric lens body, or such that the organoboronic acid moieties or groups are physically entrapped in the polymeric lens body. For example, where the chain-linking agent comprises an organic boronic acid form, the second wetting agent may comprise a poly (vinyl alcohol) form bound to the organic boronic acid form. Optionally, the silicone hydrogel contact lenses of the present invention can be understood to be free of a linking agent. In one example, the silicone hydrogel contact lens can be free of organoboronic acid moieties or groups (including polymerized organoboronic acid moieties or groups), that is, in particular, the silicone hydrogel contact lens can be formed from polymerizable compositions that do not contain organoboronic acid forms (e.g., polymerizable forms of organoboronic acids, including vinylphenyl organoboronic acids (VPBs)), can be formed from polymers that are free of units derived from polymerizable forms of organoboronic acids (e.g., vinylphenyl organoboronic acids (VPBs)), and the polymerized lens body and the silicone hydrogel contact lens can be free of organoboronic acid forms (including polymerized or non-polymerized forms of organoboronic acids) physically entrapped therein. Alternatively, the polymerizable composition, or the polymeric lens body, or the silicone hydrogel contact lens, or any combination thereof, can comprise at least one linking agent.

The silicone hydrogel contact lenses of the invention are not exposed to a volatile organic solvent or a solution of a volatile organic solvent (as part of the manufacturing process). In one example, the silicone hydrogel contact lenses of the present invention can be formed from polymerizable compositions that do not contain a wetting agent, or the polymerized lens body and/or hydrated contact lens can be free of a wetting agent, or not surface treated, or not surface modified, or not exposed to a volatile organic solvent or a solution of a volatile organic solvent during the manufacturing process, or any combination thereof. In contrast, for example, silicone hydrogel contact lenses can be extracted in water or an aqueous solution that is free of volatile organic solvents (e.g., free of volatile lower alcohols).

The use of volatile organic solvents to extract the lens body significantly increases production costs due to factors such as: the cost of organic solvents, the cost of disposing of solvents, the need to employ explosion-proof production equipment, the need to remove solvents from the lens prior to packaging, and the like. However, it can be challenging to develop polymerizable compositions that consistently produce contact lenses having ophthalmically acceptably wettable lens surfaces when extracted in an aqueous liquid that is free of volatile organic solvents. For example, as discussed herein, the presence of non-wetting areas is often found on the lens surface of contact lenses that have been extracted in an aqueous liquid that is free of volatile organic solvents.

As previously discussed, the contact lenses disclosed herein are contact lenses that are not exposed to volatile organic solvents (e.g., lower alcohols) during manufacture. In other words, the extraction liquid used for the lens and all liquids used in wet demolding, or wet delensing, or washing, or any other manufacturing step are free of volatile organic solvents. In one example, the polymerizable compositions used to form these fully aqueous liquid extracted lenses can comprise hydrophilic vinyl-containing monomers or monomer components, for example, hydrophilic vinyl ether-containing monomers. The vinyl-containing hydrophilic monomer or monomer component can include, for example, VMA. The vinyl ether containing monomer may include, for example, BVE, or EGVE, or DEGVE, or any combination thereof. In one embodiment, the vinyl ether-containing monomer can be a vinyl ether-containing monomer that is more hydrophilic than BVE, e.g., DEGVE. In another example, the hydrophilic monomer component of the polymerizable composition can be a mixture of a first hydrophilic monomer (which is a vinyl-containing monomer but not a vinyl ether-containing monomer) and a second hydrophilic monomer (which is a vinyl ether-containing monomer). The mixture includes, for example, a mixture of VMA and one or more vinyl ethers (e.g., BVE, or DEGVE, or EGVE, or any combination thereof).

When present, the hydrophilic vinyl ether-containing monomer or monomer component can be present in the polymerizable composition in an amount of from about 1 unit part to about 15 unit parts, or from about 3 unit parts to about 10 unit parts. When present in admixture with a hydrophilic vinyl-containing monomer other than a vinyl ether, the moieties of the hydrophilic vinyl-containing monomer or monomer component other than a vinyl ether and the hydrophilic vinyl ether-containing monomer or monomer component can be present in the polymerizable composition in a ratio of at least 3: 1, or from about 3: 1 to about 15: 1, or about 4: 1, based on the weight unit parts of the hydrophilic vinyl-containing monomer or monomer component other than a vinyl ether to the weight unit parts of the hydrophilic vinyl ether-containing monomer or monomer component.

Another method of producing the present contact lenses having ophthalmically acceptably wettable lens surfaces, particularly lenses extracted in liquids free of volatile organic solvents, can be to limit the amount of vinyl-containing crosslinking agent or crosslinker component included in the polymerizable composition. For example, the vinyl-containing crosslinking agent or crosslinker component may be present in the polymerizable composition in an amount of from about 0.01 unit parts to about 0.80 unit parts, or from 0.05 unit parts to about 0.30 unit parts, or from about 0.05 unit parts to about 0.20 unit parts, or in an amount of about 0.1 unit parts. In one example, the vinyl-containing crosslinking agent or crosslinker component can be present in the polymerizable composition in an amount effective to produce a contact lens having improved wettability as compared to a contact lens produced from the same polymerizable composition but having an amount of vinyl-containing crosslinking agent or crosslinker component greater than about 2.0 unit parts, or greater than 1.0 unit parts, or greater than about 0.8 unit parts, or greater than about 0.5 unit parts, or greater than about 0.3 unit parts.

Certain specific examples of silicone hydrogel contact lenses will now be described in accordance with the teachings of the present invention.

As one example (example a), a silicone hydrogel contact lens comprises a polymerized lens body that is the reaction product of a polymerizable composition comprising a first monofunctional siloxane monomer, e.g., a siloxane monomer represented by formula (1), wherein m in formula (1) represents one integer from 3 to 10, n in formula (1) represents one integer from 1 to 10, R in formula (1)¹Is an alkyl group having 1 to 4 carbon atoms, and each R in the formula (1)²Independently a hydrogen atom or a methyl group; a second siloxane monomer having more than one polymerizable functional group and having a number average molecular weight of at least 3,000 daltons; and a hydrophilic amide monomer or monomer component having an N-vinyl group, specifically, the hydrophilic monomer comprises or consists of N-vinyl-N-methylacetamide (VMA), wherein the first siloxane monomer and the second siloxane monomer are present in the composition in a ratio of 2: 1 based on parts by weight unit.

One example of a method of manufacturing a batch of silicone hydrogel contact lenses of the present invention is a method comprising: providing a polymerized silicone hydrogel contact lens body in a contact lens mold assembly, the polymerized silicone hydrogel contact lens body being the reaction product of a polymerizable composition comprising a first monofunctional siloxane monomer, a second siloxane monomer having one or more polymerizable functional groups and having a number average molecular weight of at least 3,000 daltons, and a hydrophilic amide monomer or monomer component having an N-vinyl group, the first siloxane monomer and the second siloxane monomer being present in the composition in a ratio of 2: 1 on a weight unit parts basis, wherein the single polymerized silicone hydrogel contact lens body is provided in a single contact lens mold assembly, and each contact lens mold assembly comprises a first hydrogel mold section having a concave optical surface for forming the anterior surface of the silicone hydrogel contact lens body and a second hydrogel contact lens section having a concave optical surface for forming the posterior surface of the silicone hydrogel contact lens body A second mold portion of the convex optical surface of the surface and coupling the first mold portion and the second mold portion together; separating the polymerized silicone hydrogel contact lens body from the contact lens mold assembly to produce a delensed contact lens body; washing a delensed contact lens body with an aqueous liquid free of volatile organic solvents to produce a washed contact lens; and sterilizing the washed contact lens in the sealed contact lens package; wherein the batch so manufactured comprises at least 20 silicone hydrogel contact lenses and the anterior surface of the sterilized contact lenses has a clinically acceptable surface wettability such that less than 5% of the silicone hydrogel contact lenses have visually discernible non-wetting spots when positioned on the eye of an individual, and wherein the non-wetting spots are discontinuities in the pre-lens tear film of a contact lens wearer present on the anterior surface of the contact lens and are visually discernible at a total magnification of from about 6 x to about 70 x during slit lamp inspection. In one example, the at least one hydrophilic vinyl-containing monomer or monomer component can comprise a hydrophilic amide monomer having one N-vinyl group (can comprise N-vinyl-N-methylacetamide (VMA)), or the first siloxane monomer can comprise a siloxane monomer represented by formula (1) as discussed above, or both. In another example, the polymerizable composition can be free of diluent, or free of hydrophilic polymer, or free of N, N-Dimethylacrylamide (DMA), or any combination thereof. In another example, the silicone hydrogel contact lens may be free of a plasma surface treatment or free of a polymeric internal wetting agent provided by the inclusion of a hydrophilic polymer in the polymerizable composition used to form the silicone hydrogel contact lens, or both.

One example of a batch of silicone hydrogel contact lenses of the present invention is a batch comprising: at least 20 polymerized silicone hydrogel contact lenses, the polymerized silicone hydrogel contact lenses being the reaction product of a polymerizable composition comprising a first monofunctional siloxane monomer, a second siloxane monomer having one or more polymerizable functional groups and having a number average molecular weight of at least 3,000 daltons, and a hydrophilic amide monomer or monomer component having one N-vinyl group, the first siloxane monomer and the second siloxane monomer being present in the composition in a ratio of 2: 1 based on weight unit parts, each silicone hydrogel contact lens in the batch being an aqueous extracted silicone hydrogel contact lens comprising an anterior surface and an opposing posterior surface, the posterior surface sized (sized and shaped) for placement against an eye of a subject; the anterior surface of each aqueous extraction contact lens has a clinically acceptable surface wettability such that less than 5% of the silicone hydrogel contact lenses in the batch have visually discernible unwetted spots when placed on the eyes of an individual; wherein the non-wetting spots are discontinuities in the contact lens wearer's pre-lens tear film present on the front surface of the lens body and are discernible to the naked eye at a total magnification of from about 6 x to about 70 x during slit lamp inspection. In one example, the at least one hydrophilic vinyl-containing monomer or monomer component can comprise a hydrophilic amide monomer having one N-vinyl group (can comprise N-vinyl-N-methylacetamide (VMA)), or the first siloxane monomer can comprise a siloxane monomer represented by formula (1) as discussed above, or both. In another example, the polymerizable composition can be free of diluent, or free of hydrophilic polymer, or free of N, N-Dimethylacrylamide (DMA), or any combination thereof. In another example, the silicone hydrogel contact lens may be free of a plasma surface treatment or free of a polymeric internal wetting agent provided by the inclusion of a hydrophilic polymer in the polymerizable composition used to form the silicone hydrogel contact lens, or both.

As a second example (example B), a silicone hydrogel contact lens comprises a polymerized lens body that is the reaction product of a polymerizable composition as described in example a, and wherein the polymerizable composition further comprises a hydrophobic monomer or monomer component, in particular, the hydrophilic monomer comprises or consists of Methyl Methacrylate (MMA).

As a third example (example C), a silicone hydrogel contact lens comprises a polymeric lens body that is the reaction product of a polymerizable composition as described in examples a or B, and wherein the polymerizable composition further comprises a vinyl ether-containing crosslinker or crosslinker component, specifically, the crosslinker or crosslinker component comprises triethylene glycol divinyl ether (TEGVE).

As a fourth example (example D), a silicone hydrogel contact lens comprises a polymerized lens body that is the reaction product of a polymerizable composition as described in examples a or B or C, and wherein the polymerizable composition further comprises a thermal initiator or thermal initiator component.

As a fifth example (example E), a silicone hydrogel contact lens comprises a polymerized lens body that is the reaction product of a polymerizable composition as described in examples a or B or C or D, and wherein the polymerizable composition further comprises an oxygen scavenger or an oxygen scavenger component.

As a sixth example (example F), a silicone hydrogel contact lens comprises a polymerized lens body that is the reaction product of a polymerizable composition as described in examples a or B or C or D or E, and wherein the polymerizable composition further comprises a UV blocker or UV blocker component.

As a seventh example (example G), a silicone hydrogel contact lens comprises a polymerized lens body that is the reaction product of a polymerizable composition as described in examples a or B or C or D or E or F, and wherein the polymerizable composition further comprises a colorant or a colorant component.

As an eighth example (example H), the silicone hydrogel contact lens comprises a polymerized lens body that is the reaction product of the polymerizable composition as described in examples a or B or C or D or E or F or G, and wherein the second siloxane monomer is represented by formula (2), wherein R in formula (2)₁Selected from a hydrogen atom or a methyl group; r in the formula (2)₂Selected from hydrogen or a hydrocarbon group having 1 to 4 carbon atoms; m in formula (2) represents an integer of 0 to 10; n in formula (2) represents an integer of 4 to 100; a and b represent an integer of 1 or more; a + b is equal to 20-500; b/(a + b) is equal to 0.01-0.22; and the configuration of the siloxane units includes a random configuration. As an example, the second siloxane monomer can be represented by formula (2), wherein m in formula (2) is 0, n in formula (2) is an integer from 5 to 10, a is an integer from 65 to 90, b is an integer from 1 to 10, R in formula (2) ₁Is methyl, and R in formula (2)₂Is a hydrogen atom or a hydrocarbon group having 1 to 4 carbon atoms.

As a ninth example (example I), a silicone hydrogel contact lens comprises a polymeric lens body that is the reaction product of the polymerizable composition as described in examples a or B or C or D or E or F or G or H, and wherein the polymerizable composition further comprises a methacrylate-containing crosslinker or crosslinker component, particularly the crosslinker or crosslinker component comprises or consists of Ethylene Glycol Dimethacrylate (EGDMA). In this example, where the polymerizable composition further comprises a vinyl ether-containing crosslinker as part of the crosslinker component, specifically, the crosslinker component can comprise or consist of a combination of triethylene glycol divinyl ether (TGDVE) and a methacrylate-containing crosslinker, which can specifically comprise or consist of Ethylene Glycol Dimethacrylate (EGDMA). In this example, it can be appreciated that the polymerizable composition comprises two crosslinkers, each having a different reactivity ratio, i.e., the polymerizable composition comprises a crosslinker component comprising or consisting of a vinyl-containing crosslinker and a methacrylate-containing crosslinker having polymerizable functional groups that are more reactive and therefore react at a faster rate than the vinyl-containing polymerizable functional groups present in the vinyl-containing crosslinker.

As a tenth example (example J), a silicone hydrogel contact lens comprises a polymerized lens body that is the reaction product of a polymerizable composition as described in examples a or B or C or D or E or F or G or H or I, and wherein the polymerizable composition further comprises a chain transfer agent or chain transfer agent component that may specifically comprise or consist of Allyloxyethanol (AE).

As an eleventh example (example K), a silicone hydrogel contact lens comprises a polymerized lens body that is the reaction product of the polymerizable composition as described in examples a or B or C or D or E or F or G or H or I or J, and wherein the polymerizable composition further comprises a hydrophobic monomer or hydrophobic monomer component that can specifically comprise or consist of ethylene glycol methyl ether methacrylate (EGMA).

As a twelfth example (example L), a silicone hydrogel contact lens comprises a polymerized lens body that is the reaction product of a polymerizable composition as described in examples a or B or C or D or E or F or G or H or I or J or K, and wherein the polymerizable composition further comprises a hydrophilic vinyl ether-containing monomer or monomer component, e.g., the hydrophilic vinyl ether-containing monomer or monomer component can comprise or consist of 1, 4-Butanediol Vinyl Ether (BVE), or Ethylene Glycol Vinyl Ether (EGVE), or diethylene glycol vinyl ether (DEGVE), or any combination thereof.

In any or each of the above examples a-L, as well as any or all of the other examples disclosed herein, the amount of the first siloxane monomer can comprise from 20 unit parts to 45 unit parts of the polymerizable composition. The amount of the first siloxane monomer can be from 25 unit parts to 40 unit parts of the polymerizable composition. The amount of the first siloxane monomer can range from 27 unit parts to 35 unit parts of the polymerizable composition.

In any or each of the above examples a-L, as well as any or all of the other examples disclosed herein, the amount of the second siloxane monomer can comprise from 1 unit part to 20 unit parts of the polymerizable composition, so long as a 2: 1 ratio is maintained based on the weight unit parts of the first siloxane to the second siloxane. The amount of the second siloxane monomer can range from 2 unit parts to 15 unit parts of the polymerizable composition. The amount of the second siloxane monomer can range from 5 unit parts to 13 unit parts of the polymerizable composition.

In any or each of the above examples a-L, as well as any or all of the other examples disclosed herein, the amount of hydrophilic monomer or monomer component present in the polymerizable composition can be from 1 unit part to 60 unit parts of the polymerizable composition. The hydrophilic monomer component can comprise from 4 unit parts to 60 unit parts of the polymerizable composition. Where the hydrophilic monomer comprises or consists of VMA, it can be present in an amount of 30 unit parts to 60 unit parts. The VMA can be present in the polymerizable composition in an amount of about 40 unit parts to about 50 unit parts. Where hydrophilic monomers (i.e., N-Dimethylacrylamide (DMA), 2-hydroxyethyl methacrylate (HEMA), or 2-hydroxybutyl methacrylate (HOB), or any combination thereof) are present in the polymerizable composition as the hydrophilic monomers in the hydrophilic monomer component, each monomer or all of the monomers may be present in an amount from about 3 unit parts to about 10 unit parts.

In any or each of the above examples a-L, as well as any or all other examples disclosed herein, the hydrophobic monomer or monomer component can be present in the polymerizable composition in an amount from 1 unit part to 30 unit parts of the polymerizable composition. For example, the total amount of hydrophobic monomer or monomer component can be from about 5 unit parts to about 20 unit parts of the polymerizable composition. In polymerizable compositions where the hydrophobic monomer MMA is present as a hydrophobic monomer or as part of a hydrophobic monomer component, MMA may be present in amounts from about 5 unit parts to about 20 unit parts, or from about 8 unit parts to about 15 unit parts.

In any or each of the above examples a-L, as well as any or all of the other examples disclosed herein, the amount of crosslinker or crosslinker component present in the polymerizable composition can range from 0.01 unit parts to 4 unit parts of the polymerizable composition. TEGDVE may be present in an amount of from 0.01 unit parts to 1.0 unit parts. EGDMA may be present in an amount of 0.01 unit parts to 1.0 unit parts. TEGDMA may be present in an amount of from 0.1 unit parts to 2.0 unit parts. Each of these silicon-free crosslinkers can be present in the polymerizable composition alone or in any combination.

In any or each of the above examples a-L, and any or all other examples disclosed herein, when the polymerizable composition contains EGMA, BVE, DEGVE, EGVE, or any combination thereof, each is present in an amount of 1 unit part to 20 unit parts of the polymerizable composition. EGMA may be present in an amount of about 2 unit parts to about 15 unit parts. BVE can be present in an amount of from 1 unit part to about 15 unit parts. BVE can be present in an amount of about 3 unit parts to about 7 unit parts. DEGVE may be present in an amount of 1 unit part to about 15 unit parts. DEGVE may be present in an amount of about 7 unit parts to about 10 unit parts. EGVE may be present in an amount of from 1 unit part to about 15 unit parts, or in an amount of from about 3 unit parts to about 7 unit parts.

In any or each of the above examples a-L, as well as any or all of the other examples disclosed herein, other optional components (e.g., an initiator or initiator component, a colorant or colorant component, a UV absorber or UV absorber component, an oxygen scavenger or oxygen scavenger component, or a chain transfer agent or chain transfer agent component) can each be present in an amount of from about 0.01 unit parts to about 3 unit parts. The initiator or initiator component may be present in the polymerizable composition in an amount of from 0.1 unit parts to 1.0 unit parts. In the presence of a thermal initiator or thermal initiator component (e.g., Vazo-64), it may be present in an amount of from about 0.3 unit parts to about 0.5 unit parts. The colorant or colorant component may be present in an amount of from 0.01 unit parts to 1 unit part. When a reactive dye (e.g., reactive blue 246 or reactive blue 247) is used as a colorant or as part of a colorant component, it can each be present in an amount of about 0.01 unit parts. The UV absorber or UV absorber component can be present in an amount of 0.1 unit parts to 2.0 unit parts. For example, the UV absorber UV1 described in the examples below may be present in an amount from about 0.8 unit parts to about 1.0 unit parts (e.g., 0.9 unit parts); or the UV absorber UV2 described in the examples below may be present in an amount of 0.5 unit parts to 2.5 unit parts (e.g., about 0.9 unit parts to about 2.1 unit parts). The oxygen scavenger or oxygen scavenger component may be present in an amount of from 0.1 unit parts to 1.0 unit parts. As an example, when Triphenylphosphine (TPP) or diphenyl (p-vinylphenyl) phosphine (pTPP), or any combination thereof, is used as the oxygen scavenger or oxygen scavenger component in the polymerizable composition, each or the combination may be present in an amount of 0.3 unit parts to 0.7 unit parts (e.g., about 0.5 unit parts). The chain transfer agent or chain transfer agent component may be present in the polymerizable composition in an amount of from 0.1 unit parts to 2.0 unit parts, and in the examples below in an amount of from 0.2 unit parts to 1.6 unit parts. For example, the chain transfer agent Allyloxyethanol (AE) may be present in an amount of about 0.3 unit parts to about 1.4 unit parts.

In any or each of the above examples a-L, as well as any or all other examples disclosed herein, the silicone hydrogel contact lens can be free of a wetting agent present in the polymerizable composition, or in the polymerized lens body, or in the silicone hydrogel contact lens. Similarly, silicone hydrogel contact lenses can have lens surfaces that are not surface treated or surface modified. However, in another example, the silicone hydrogel contact lens can include at least one wetting agent (i.e., a single wetting agent or two or more wetting agents present as wetting agent components) in the polymerizable composition, in the polymerized lens body, or in the silicone hydrogel contact lens. Silicone hydrogel contact lenses may have treated or modified lens surfaces. Additionally or alternatively, in any or each of the foregoing examples a-L, as well as any or all other examples of silicone hydrogel contact lenses disclosed herein, the contact lenses can be understood to be free of a linking agent (e.g., an organoboronic acid form).

In another example, new polymerizable compositions are provided, including each of the polymerizable compositions described herein with reference to the silicone hydrogel contact lenses and methods. The polymerizable composition can be free of diluents, wherein it is free of organic solvents, such as alcohols and the like, that can help reduce phase separation of the polymerizable composition. However, the diluent-free polymerizable composition may still contain one or more chain transfer agents, such as allyloxyethanol. However, if desired, the polymerizable composition can include a diluent or diluent component, which can be present in an amount of from 1 unit part to 20 unit parts.

As described herein, the present silicone hydrogel contact lenses are dimensionally stable comprising a polymeric lens body comprising units derived from: a first siloxane monomer represented by formula (1) and a second siloxane monomer having one or more polymerizable functional groups and having a number average molecular weight of at least 3,000 daltons (such as those represented by formula (2), (3), or (4)). The present invention also relates to a batch of silicone hydrogel contact lenses.

As used herein, a batch of silicone hydrogel contact lenses refers to a set of 20 or more than 20 silicone hydrogel contact lenses, and typically, a batch refers to at least 20, or at least 100, or at least 1,000 silicone hydrogel contact lenses. According to the present invention, a batch of silicone hydrogel contact lenses comprises at least 20 of any of the silicone hydrogel contact lenses described herein.

Lenses of a batch may exhibit a change in average physical dimension when tested first shortly after manufacture and then tested again at a subsequent point in time. Since the lenses of the invention are dimensionally stable, they can exhibit acceptable levels of variation in average physical dimensions. Dimensional stability difference as used herein is understood to mean the difference in physical dimension value between the physical dimension value determined for the batch of lenses when first tested shortly after their manufacture and the physical dimension value determined for the batch of lenses when tested again at a subsequent point in time. The subsequent time point can be, for example, at least 2 weeks after the initial time point to at most 7 years after the initial time point. The batches of silicone hydrogel contact lenses have a mean dimensional stability difference of less than +/-3% (± 3%) based on averaging lens diameter measurements for a representative number of lenses in the batch (e.g., 20 lenses in the batch). For a batch of lenses, a mean dimensional stability difference of less than +/-3% (± 3.0%) is considered a dimensionally stable batch, wherein the mean dimensional stability difference is the difference in the physical dimensional values measured at an initial time point within one day of the date of manufacture of the batch of lenses and at a second time point, wherein the second time point is two weeks to seven years after the initial time point, when the batch is stored at room temperature or when the batch is stored at a higher temperature (i.e., under accelerated shelf life test conditions), the second time point being a time point representing the batch is stored at room temperature for two weeks to seven years. In one example, an accelerated shelf life test condition that is particularly useful for determining the difference in average dimensional stability is 4 weeks at 70 ℃, although other time periods and other temperatures may be used. The mean dimensional stability difference is determined by using the actual diameter (diameter) of the first measured representative lens _Initial) And the actual diameter (diameter) of a representative lens measured at room temperature or after storage under accelerated shelf life conditions_{Finally, the product is processed}) The individual dimensional stability differences for each representative lens were determined by averaging. The first measured representative lens and the representative lens measured after storage may be the same lens or may beDifferent lenses. The average dimensional stability difference as used herein is expressed in percent (%). The individual dimensional stability differences were determined using the following equation (a):

((diameter)_{Finally, the product is processed}Diameter of_Initial) Diameter_Initial)×100(A)。

On average, the batch of silicone hydrogel contact lenses varied in diameter by less than 3% (± 3.0%) in either direction of the target value. As one example, if the contact lens has a target diameter (chord diameter) of 14.20mm, the present batch of silicone hydrogel contact lenses will have an average diameter (average of the population in the batch) of 13.77mm to 14.63 mm. In one example, the dimensional stability difference is less than +/-2% (+ -2.0%). As one example, if the contact lens has a target diameter (chord diameter) of 14.20mm, the present batch of silicone hydrogel contact lenses will have an average diameter (average of the population in the batch) of 13.92mm to 14.48 mm. Preferably, the mean diameter of the batch of silicone hydrogel contact lenses varies by no more than +/-0.20mm, typically 13.00mm to 15.00mm, from the target diameter.

In accelerated shelf life studies, the difference in average dimensional stability of contact lenses that have been stored at elevated temperatures (e.g., above 40 ℃, including, for example, 50 ℃, or 55 ℃, or 65 ℃, or 70 ℃, or 80 ℃, or 95 ℃, etc.) for a period of time can be determined. Alternatively, the average dimensional stability of a contact lens that has been stored at room temperature (e.g., about 20-25℃.) for a period of time can be determined.

For accelerated shelf life studies, the number of months to store at a particular temperature for the length of time required to store at room temperature can be determined using the following equation:

required shelf life = [ Nx 2 =^y]+n(B)

Wherein

N = number of months stored under accelerated conditions

2^y= acceleration factor

y = (test temperature-25 ℃)/10 ℃

n = lens age (in months) at the beginning of the study.

Based on this equation, the following storage times have been calculated: storage at 35 ℃ for 6 months corresponds to aging at 25 ℃ for 1 year, storage at 45 ℃ for 3 months corresponds to aging at 25 ℃ for 1 year, storage at 55 ℃ for 3 months corresponds to aging at 25 ℃ for 2 years, and storage at 65 ℃ for 3 months corresponds to aging at 25 ℃ for 4 years.

The present invention also provides methods of manufacturing silicone hydrogel contact lenses, as discussed herein. According to the teachings of the present invention, some of the present methods comprise providing a polymerizable composition. In some examples of the present methods, the polymerizable composition or contact lens formulation comprises a first siloxane monomer represented by formula (1):

The method can also include the step of polymerizing the polymerizable composition to form a polymerized contact lens body. The step of polymerizing the polymerizable composition can be carried out in a contact lens mold assembly. The polymerizable composition can be cast molded between molds formed from thermoplastic polymers. The thermoplastic polymer used to form the molding surface of the mold may comprise a polar polymer, or may comprise a non-polar polymer. Alternatively, the polymerizable composition can be formed into a lens via various methods known to those skilled in the art, such as spin casting, injection molding, forming a polymeric rod, and then lathing to form a lens body, and the like.

The method also includes contacting the polymeric lens body with an aqueous wash solution to remove extractable materials, such as unreacted monomers, uncrosslinked materials that were not physically immobilized in the polymeric contact lens body, diluents, and the like.

According to the present invention, a polymeric contact lens body can be packaged with a contact lens packaging solution in a contact lens package (e.g., a blister pack or glass vial). After packaging, the package can be sealed and the polymeric contact lens body and contact lens packaging solution sterilized, for example, by autoclaving the sealed package to produce a silicone hydrogel contact lens product.

In the present methods, the step of contacting the polymeric contact lens body with a washing liquid can be understood to be an extraction step, as extractable material can be removed from the polymeric contact lens body during the process. In the present methods, the contacting step comprises contacting the polymerized contact lens body with an aqueous wash solution that is free of volatile organic solvents. Since no volatile organic solvent is included in the washing liquid, the process can be understood as a completely aqueous washing step. Water-based wash liquids that may be used in the method include water (e.g., deionized water), saline solutions, buffer solutions, or aqueous solutions containing surfactants or other non-volatile ingredients that can facilitate removal of hydrophobic components from or reduce deformation of the polymeric contact lens body as compared to using deionized water alone.

After washing, the contact lens can be placed in a package (e.g., a plastic blister pack) containing a packaging solution (e.g., a buffered saline solution) that may or may not contain surfactants, anti-inflammatory agents, antimicrobial agents, contact lens wetting agents, and the like; and may be sealed and sterilized.

Examples of the invention

The following examples illustrate certain aspects and advantages of the present invention, which should not be construed as limiting thereof.

As can be readily determined upon review of the following examples, none of the example formulations contained an organic diluent. Likewise, all example formulations contained no N, N-Dimethylacrylamide (DMA). Additionally, all of the following example formulations did not contain polymeric wetting agents. Furthermore, all example formulations include at least one hydrophilic amide monomer having one N-vinyl group. Most example formulations include a second siloxane that is a double-terminal methacrylate-terminated polydimethylsiloxane and has a number average molecular weight of at least 5,000 daltons.

The following chemicals are mentioned in examples C1 and 1 to 25, and may be mentioned by their abbreviations.

Si 1: 2-methyl-2-propenoic acid 2- [3- (9-butyl-1, 1, 3, 3, 5, 5, 7, 7, 9, 9-decamethylpentasiloxane-1-yl) propoxy ] ethyl ester (CAS number 1052075-57-6). (Si1 was obtained from Shin-Etsu chemical Co., Ltd., Tokyo, Japan) as product number X-22-1622.

Si 2: α, ω -bis (methacryloxypropyl) -poly (dimethylsiloxane) -poly (ω -methoxy-poly (ethyleneglycol) propylmethylsiloxane) (the synthesis of this compound can be performed as described in US20090234089, which is incorporated herein by reference)

Si 3: methacryloxypropyl terminated poly (dimethylsiloxane) (CAS No. 58130-03-3; DMS-R18 available from Gerster)

VMA: N-vinyl-N-methylacetamide (CAS number 003195786)

DMA: n, N-dimethylacrylamide (CAS number 2680-03-7)

HEMA: 2-hydroxyethyl methacrylate (CAS number 868-77-9)

HOB: 2-hydroxybutyl methacrylate (CAS number 29008-35-3)

EGMA: ethylene glycol methyl ether methacrylate (CAS number 6976-93-8)

MMA: methyl methacrylate (CAS number 80-62-6)

EGDMA: ethylene glycol dimethacrylate (CAS number 97-90-5)

TEGDMA: triethylene glycol dimethacrylate (CAS number 109-16-0)

BVE: 1, 4-butanediol vinyl Ether (CAS number 17832-28-9)

DeGVE: diethylene glycol vinyl ether (CAS number 929-37-3)

EGVE: ethylene glycol vinyl ether (CAS number 764-48-7)

TEGDVE: triethylene glycol divinyl ether (CAS number 765-12-8)

AE: 2-allyloxyethanol (CAS number 111-45-5)

V-64: 2, 2' -azobis-2-methylpropanenitrile (CAS number 78-67-1)

UV 1: acrylic acid 2- (4-benzoyl-3-hydroxyphenoxy) ethyl ester (CAS number 16432-81-8)

UV 2: 2- (3- (2H-benzotriazol-2-yl) -4-hydroxy-phenyl) ethyl methacrylate (CAS number 96478-09-0)

RBT 1: 1, 4-bis [4- (2-methacryloyloxyethyl) phenylamino ] anthraquinone (CAS No. 121888-69-5)

RBT 2: 1, 4-bis [ (2-hydroxyethyl) amino ] -9, 10-anthracenedione bis (2-propenoic acid) ester (CAS registry number 109561071)

TPP: triphenylphosphine (CAS number 603-35-0)

pTPP: polymerizable TPP: diphenyl (p-vinylphenyl) phosphine (CAS number 40538-11-2)

Silicone hydrogel contact lens manufacturing and testing procedures

For each example, the compounds described in the examples were weighed out in amounts corresponding to the unit parts and combined to form a mixture. The mixture was filtered into a vial via a 0.2 micron to 5.0 micron syringe filter. The mixture was stored for up to about 2 weeks. The mixture is understood to be a polymerizable silicone hydrogel contact lens precursor composition, or a polymerizable composition as used herein. In the examples, the amounts of ingredients listed are given in parts by weight of the polymerizable composition.

A volume of polymerizable composition is cast molded by placing the composition in contact with the lens defining surface of the female mold member. In all the following examples, the molding surface of the female mold member is formed of a nonpolar resin, particularly polypropylene, but a polar resin such as PBT may also be used. The male mold member is placed in contact with the female mold member to form a contact lens mold assembly comprising a contact lens-forming cavity containing a polymerizable composition. In the following examples, the molding surface of the male mold member is formed of a nonpolar resin, in particular, polypropylene.

The contact lens mold assembly is placed in a nitrogen-flushed oven to render the precursor composition thermally curable. For all examples, the contact lens mold assembly is exposed to a temperature of at least about 55 ℃ for about 2 hours. Examples of curing conditions that can be used to cure the silicone hydrogel contact lenses described herein include exposing the contact lens mold assembly to a temperature of 55 ℃ for 40 minutes, to 80 ℃ for 40 minutes, and to 100 ℃ for 40 minutes. Other contact lenses may be manufactured with the same curing conditions, but the first temperature may be 65 ℃ instead of 55 ℃.

After polymerizing the polymerizable composition, the contact lens mold assembly is demolded to separate the male and female mold members. The polymerized contact lens body remains attached to the male or female mold. A dry demolding process may be used in which the mold assembly is not in contact with a liquid medium, or a wet demolding process may be used in which the mold assembly is in contact with a liquid medium (e.g., water or an aqueous solution). A mechanical dry demolding process may involve applying a mechanical force to a portion of one or both mold members to separate the mold members. In all of the following examples, a dry demolding process was used.

The polymerized contact lens body is then delensed from the male or female mold to produce a delensed polymerized contact lens body. In one example of a delensing process, a polymeric contact lens body can be delensed from a male mold member using a dry delensing process by, for example: manually stripping the lens from the male mold member; or compressing the male mold member and directing gas to the male mold member and the polymerized contact lens body, and lifting the dried polymerized contact lens body from the male mold member with a vacuum device and discarding the male mold member. In other methods, the polymeric contact lens bodies can be delensed using a wet delensing process by contacting the dry polymeric contact lens bodies with a liquid release medium (e.g., water or an aqueous solution). For example, the male mold member with the polymeric contact lens body attached thereto can be dipped into a container containing a liquid until the polymeric contact lens body is separated from the male mold member. Alternatively, a volume of liquid release medium may be added to the female mold to soak the polymeric contact lens body in the liquid and separate the lens body from the female mold member. In the following examples, a dry delensing process was used. After separation, the lens body can be manually lifted from the mold member using tweezers or using a vacuum device and placed in a tray.

The delensed lens product is then washed to remove extractable material from the polymerized contact lens body and hydrated. The extractable material includes polymerizable components (e.g., monomers, or crosslinkers, or any optional polymerizable ingredients (e.g., colorants or UV blockers), or combinations thereof) present in the polymerizable composition that remain present in the polymerized lens body in unreacted form, in partially reacted form, or in uncrosslinked form, or any combination thereof, after polymerization of the lens body and prior to extraction of the lens body. The extractable material can also include any non-polymerizable ingredients present in the polymerizable composition, such as any optional non-polymerizable colorant, or UV blocker, or diluent, or chain transfer agent, or any combination thereof, that remains present in the polymerized lens body after polymerization of the polymerized lens body and prior to extraction of the polymerized lens body.

In another method (e.g., a method involving delensing by compressing a male mold member and directing a gas stream toward the male mold member), a delensing polymeric contact lens body can be placed in a cavity of a lens carrier or tray, wherein the delensing polymeric lens body can then be contacted with one or more volumes of an extraction fluid (e.g., an aqueous extraction fluid free of volatile organic solvents, such as deionized water or an aqueous solution of a surfactant such as Tween (Tween) 80).

In other methods, such as those involving wet delensing by contacting the mold and lens with a liquid release medium, the delensing polymeric contact lens body can be washed with a wash solution free of volatile organic solvents, such as lower alcohols, e.g., methanol, ethanol, or any combination thereof, to remove extractable components from the lens body. For example, the lens body can be washed by contacting the delensing polymeric contact lens body with an aqueous wash solution free of volatile organic solvents (e.g., deionized water, or a surfactant solution, or a saline solution, or a buffer solution, or any combination thereof) to remove extractable components from the lens body. The washing may be performed in the final contact lens package, or may be performed in a wash tray or wash tank.

In the following examples, after the dry demolding and dry delensing steps, the dry delensing lens body is placed in the cavity of a tray, and the delensing polymeric lens body is extracted and hydrated by contacting the polymeric lens body with one or more volumes of an extraction solution. The extraction and hydration liquid used in the extraction and hydration process is comprised of an extraction and hydration liquid that is free of volatile organic solvents (i.e., a fully aqueous extraction and hydration liquid). Specifically, in the examples below, the extraction and hydration process used comprised at least three extraction and hydration steps performed in separate portions of a deionized water solution of tween 80, wherein the temperature of the tween 80 solution portions ranged from room temperature to about 90 ℃, and wherein each extraction and hydration step lasted from about 15 minutes to about 3 hours.

The washed, extracted and hydrated lenses are then individually placed in contact lens blister packages containing a phosphate buffered saline packaging solution. The blister pack is sealed and sterilized by autoclaving.

After sterilization, lens properties such as contact angle (including dynamic and static contact angles), oxygen permeability, ion flux, modulus, elongation, tensile strength, water content, and the like are determined as described herein.

For the present contact lenses, contact angles, including dynamic and static contact angles, can be determined using conventional methods known to those skilled in the art. For example, the advancing and receding contact angles of the contact lenses provided herein can be measured using conventional droplet shape methods (e.g., the sitting drop method or the captive bubble method).

In the following examples, the advancing and receding contact angles of silicone hydrogel contact lenses were determined using a kruss dsa100 instrument (kruss gmbh, hamburger) and as described in the following references: d.a. brandreth (d.a. brandreth): "dynamic contact angle and contact angle hysteresis (dynamic contact angle and contact angle hysteresis)", journal of colloid and interface science (journal of colloid and interface science), Vol.62, 1977, pp.205-212; and r. naproski (r.knapikowski), m. kudre (m.kudra): "evaluation of the error of contact angle measurement according to Williams principle statistical method (Kontaktwilklem-PrinmungnachdemWilhelmy-Prinzip-Einstastatischer Ansatzzur Feiherbeurung)", chemical technique (chem. Technik), Vol.45, 1993, p.179-185; and U.S. patent No. 6,436,481, which are incorporated herein by reference.

As an example, advancing and receding contact angles are determined using a bubble trap method with phosphate buffered saline (PBS; pH = 7.2). The lenses were laid flat on a quartz surface and rehydrated with PBS for at least 10 minutes prior to testing. An automatic injection system is used to place air bubbles on the lens surface. The size of the air bubble is increased and decreased to obtain a receding angle (plateau obtained when the bubble size is increased) and an advancing angle (plateau obtained when the bubble size is decreased).

The modulus, elongation and tensile strength values of the lenses of the invention can be determined using conventional methods known to those skilled in the art (e.g., testing methods according to ANSIZ 80.20). The modulus, elongation and tensile strength values reported herein were determined using an Instron model 3342 or 3343 mechanical testing system (Instron corporation, norwood, massachusetts, usa) and blue hill materials (BluehillMaterials) testing software, where a custom rectangular contact lens cut mold was used to prepare a rectangular sample strip. Modulus, elongation and tensile strength were measured in a room with a minimum of 70% relative humidity. Lenses intended for testing were soaked in Phosphate Buffered Saline (PBS) for at least 10 minutes prior to testing. The central strip of the lens is cut using a cutting die while the lens is held concave side up. The thickness of the strip was measured using a calibrated gauge (reed electronic thickness gauge, RehderDevelopment, inc., casterol valley, ca, usa). The strips were loaded into the grips of a calibrated instron apparatus using tweezers and the strips were fitted on at least 75% of the grip surface of each grip. Test methods designed to determine the mean and standard deviation of the maximum load (N), tensile strength (MPa), strain at maximum load (% elongation), and tensile modulus (MPa) were run and the results recorded.

The percent energy loss of the present silicone hydrogel contact lenses can be determined using conventional methods known to those skilled in the art. For the following example, the percentage energy loss was determined using an instron model 3343 (instron corporation, norwood, ma, usa) mechanical test system with a 10N force converter (instron model 2519-. The energy loss is measured in a room with a minimum relative humidity of 70%. Prior to testing, each lens was soaked in Phosphate Buffered Saline (PBS) for at least 10 minutes. The lenses are loaded into the jaws of a calibrated instron apparatus using tweezers, and the lenses are loaded vertically between the jaws as symmetrically as possible so that the lenses fit on at least 75% of the jaw surface of each jaw. A test designed to determine the energy required to stretch the lens to 100% strain at a rate of 50 mm/min and then recover it to 0% strain was then run on the lens. The test is performed only once on a single lens. The energy loss was calculated immediately after the test was completed using the following equation: energy lost (%) = (energy to 100% strain-energy to recover 0% strain)/energy to 100% strain x 100%.

The ion current of the lenses of the invention can be determined using conventional methods known to those skilled in the art. For the lenses in the examples below, ion current was measured using a technique substantially similar to the "ion current technique" described in U.S. Pat. No. 5,849,811, which is incorporated herein by reference. The hydrated lens was allowed to equilibrate in deionized water for at least 10 minutes prior to measurement. The lens to be measured is placed in the lens holding device between the convex and concave portions. The male and female portions include a flexible sealing ring between the lens and the respective male or female portion. After placing the lens in the lens holder, the lens holder is then placed in the threaded cap. The cap is screwed onto the glass tube to define the supply chamber. The supply chamber was filled with 16m10.1m nacl solution. The receiving chamber was filled with 80ml of deionized water. The leads of the conductivity meter were immersed in deionized water in the receiving chamber and a stir bar was added to the receiving chamber. The receiving chamber was placed in a water bath and the temperature was maintained at about 35 ℃. Finally, the supply chamber is immersed in the receiving chamber so that the NaCl solution in the supply chamber is level with the level in the receiving chamber. Once the temperature in the receiving chamber had equilibrated to 35 ℃, the conductivity was measured every 2 minutes for at least 10 minutes. The conductivity versus time data is substantially linear and is used to calculate the ion flow value of the lens under test.

The oxygen transmission rate (Dk) of the lenses of the invention may be determined using conventional methods known to those skilled in the art. For example, Dk values may be determined using the membrane health method, as described in U.S. patent No. 5,817,924, which is incorporated herein by reference. The Dk values for the lenses in the following examples are marked as Funkang using the model numberCommercially available instruments for the Ox-Tran system (Mocon corporation, Minneapolis, Minn., USA).

The Equilibrium Water Content (EWC) of the lenses of the invention can be determined using conventional methods known to those skilled in the art. For the lenses in the examples below, the hydrated silicone hydrogel contact lenses were removed from the aqueous liquid, wiped to remove excess surface water, and weighed. The weighed lenses can then be placed in an oven at 80 deg.f. C and drying under vacuum, and then weighing the dried lenses. The weight difference was determined by subtracting the weight of the dry lens from the weight of the hydrated lens. The water content (%) was (weight difference/hydrated weight) × 100.

The percentage of wet extractable or dry extractable components in the lens can be determined by extracting the lens in an organic solvent that does not dissolve the polymeric lens body according to methods known to those skilled in the art. For the lenses in the examples below, the extraction was performed in methanol using the soxhlet extraction process. For the determination of wet extractable components, samples of fully hydrated and sterilized contact lenses (e.g., at least 5 lenses per batch) were prepared by removing excess packaging solution from each lens and drying it overnight in a vacuum oven at 80 ℃. For determination of dry extractable components, samples of polymeric lens bodies that have not been washed, extracted, hydrated, or sterilized were prepared by drying the lens bodies overnight in a vacuum oven at 80 ℃. Upon drying and cooling, each lens was weighed to determine its initial dry weight (W1). Each lens was then placed in a porous stackable Teflon (Teflon) sleeve and the sleeves were stacked to form an extraction column with an empty sleeve placed at the top of the column. The extraction column was placed in a small soxhlet extractor attached to a condenser and a round bottom flask containing 70m1 to 80m1 methanol. Water was circulated through the condenser and methanol was heated until it boiled gently. The lenses were extracted for at least 4 hours from the time of first appearance of condensed methanol. The extracted lenses were dried again overnight in a vacuum oven at 80 ℃. Upon drying and cooling, each lens was weighed to obtain the dry weight of the extracted lens (W2), and the following calculation was performed for each lens to determine the percentage of wet extractables: [ (W1-W2)/W1] x 100.

Example 1

The polymerizable compositions were obtained by mixing and filtering the following compounds in the amounts specified using the procedures described in the silicone hydrogel contact lens manufacturing and testing procedures given above.

Compound (abbreviation)	Unit parts
		Si1	32
Si3	4
		VMA	40
EGMA	5
		MMA	12
TEGDMA	1.0
		TEGDVE	0.3
BVE	7
		V-64	0.5
UV2	0.9
		RBT2	0.01
pTPP	0.5

Batches of silicone hydrogel contact lenses were prepared and tested using this formulation according to the manufacturing procedures and testing methods described in the silicone hydrogel contact lens manufacturing and testing procedures using a dry demolding process, a dry delensing process, and a washing process using an extraction and hydration solution consisting of an extraction solution free of volatile organic solvents. This batch of lenses was not exposed to volatile organic solvents during their manufacture. These contact lenses contain units derived from two siloxane monomers, Si1 and Si 3. This batch of contact lenses had an acceptable average dimensional stability difference.

In addition, the silicone hydrogel contact lenses, when tested at the beginning of the shelf life study, had an EWC of about 55% wt/wt, about 3.1(× 10) when fully hydrated^-3mm²Min), a Dk of about 72 barrers, a modulus of about 0.70MPa, an elongation of about 345%, a tensile strength of about 2.4MPa, a water break time of greater than 20 seconds, a wet extractable component of about 3.9% wt/wt, and an energy loss of about 40%, and has an average dimensional stability difference of less than +/-3.0% after storage for more than 2 weeks at 80 ℃. The polymeric lens body has about 11% wt/wt of dry extractable components when tested prior to extraction and hydration.

Example 2

Compound (abbreviation)	Unit parts
		Si1	32
Si3	4
		VMA	50
MMA	14
		TEGDMA	0.8
TEGDVE	0.2
		V-64	0.5
UV2	0.9
		RBT2	0.01
pTPP	0.5

In addition, the silicone hydrogel contact lenses, when tested at the beginning of the shelf life study, had an EWC of about 58% wt/wt, about 4.14(× 10) when fully hydrated^-2mm²Min), a modulus of about 0.77MPa, an elongation of about 349%, a tensile strength of about 1.75MPa, a water burst time of greater than 20 seconds, a moisture extractable content of about 4.42% wt/wt, and an energy loss of about 41%, and has an average dimensional stability difference of less than +/-3.0% after storage at 80 ℃ for at least 2 weeks.

Example 3

Compound (abbreviation)	Unit parts
		Si1	23
Si2	15
		VMA	40
MMA	10
		EGMA	5
BVE	7

TEGDMA	1.0
		TEGDVE	0.1
V-64	0.5
		UV2	0.9
RBT2	0.01
		pTPP	0.5

Batches of silicone hydrogel contact lenses were prepared and tested using this formulation according to the manufacturing procedures and testing methods described in the silicone hydrogel contact lens manufacturing and testing procedures using a dry demolding process, a dry delensing process, and a washing process using an extraction and hydration solution consisting of an extraction solution free of volatile organic solvents. This batch of lenses was not exposed to volatile organic solvents during their manufacture. These contact lenses contain units derived from two siloxane monomers, Si1 and Si 2. This batch of contact lenses had an acceptable average dimensional stability difference.

In addition, the silicone hydrogel contact lenses, when tested at the beginning of the shelf life study, had an EWC of about 55% wt/wt, about 4.19(× 10) when fully hydrated^-3mm²Min), a modulus of about 0.61MPa, an elongation of about 275%, a tensile strength of about 1.51MPa, a water burst time of greater than 20 seconds, and a wet extractable component of about 4.10% wt/wt, and has an average dimensional stability difference of less than +/-3.0% after storage for more than 2 weeks at 80 ℃.

Example 4

Compound (abbreviation)	Unit parts
		Si1	23
Si2	15
		VMA	45
MMA	10
		BVE	7
TEGDMA	1.0
		TEGDVE	0.1
V-64	0.5
		UV2	0.9
RBT2	0.01
		pTPP	0.5

In addition, the silicone hydrogel contact lenses, when tested at the beginning of the shelf life study, had an EWC of about 58% wt/wt, about 2.75(× 10) when fully hydrated^-3mm²Min), a modulus of about 0.66MPa, an elongation of about 216%, a tensile strength of about 0.87MPa, a water burst time of greater than 20 seconds, and a wet extractable component of about 4.56% wt/wt, and has an average dimensional stability difference of less than +/-3.0% after 6 days of storage at 95 ℃.

Example 5

Compound (abbreviation)	Unit parts
		Si1	26
Si2	10
		VMA	40
MMA	12
		EGMA	5
BVE	7
		TEGDMA	1.2
TEGDVE	0.1
		V-64	0.5
UV2	0.9
		RBT2	0.01
pTPP	0.5

In addition, the silicone hydrogel contact lenses, when tested at the beginning of the shelf life study, had an EWC of about 56% wt/wt, about 3.54(× 10) when fully hydrated^-3mm²Min), a modulus of about 0.57MPa, an elongation of about 310%, a tensile strength of about 1.90MPa, a water burst time of greater than 20 seconds, a wet extractable component of about 4.74% wt/wt, and an energy loss of about 34% to 36%, and has an average dimensional stability difference of less than +/-3.0% after 7 days of storage at 80 ℃. The polymeric lens body has a dry extractable component of about 14.39% wt/wt when tested prior to extraction and hydration.

Example 6

Compound (abbreviation)	Unit parts
		Si1	26
Si2	10
		VMA	45
MMA	12
		EGMA	2
BVE	5
		TEGDMA	1.2
TEGDVE	0.2
		V-64	0.5
UV2	0.9
		RBT2	0.01
pTPP	0.5

In addition, the silicone hydrogel contact lenses, when tested at the beginning of the shelf life study, had an EWC of about 57% wt/wt, about 3.68(× 10) when fully hydrated^-3mm²Min), a modulus of about 0.69MPa, an elongation of about 314%, a tensile strength of about 1.30MPa, a water burst time of greater than 20 seconds, a wet extractable component of about 1.81% wt/wt, and an energy loss of about 34%, and has an average dimensional stability difference of less than +/-3.0% after 14 days of storage at 80 ℃.

Example 7

Compound (abbreviation)	Unit parts
		Si1	26
Si3	2
		Si2	10
VMA	45
		MMA	12
BVE	5
		TEGDMA	1.2
TEGDVE	0.2
		V-64	0.5
UV2	0.9
		RBT2	0.01
pTPP	0.5

Batches of silicone hydrogel contact lenses were prepared and tested using this formulation according to the manufacturing procedures and testing methods described in the silicone hydrogel contact lens manufacturing and testing procedures using a dry demolding process, a dry delensing process, and a washing process using an extraction and hydration solution consisting of an extraction solution free of volatile organic solvents. This batch of lenses was not exposed to volatile organic solvents during their manufacture. These contact lenses contain units derived from three siloxane monomers, Si1, Si2, and Si 3. This batch of contact lenses had an acceptable average dimensional stability difference.

In addition, the silicone hydrogel contact lenses, when tested at the beginning of the shelf life study, had an EWC of about 55% wt/wt, about 3.06(× 10) when fully hydrated^-3mm²Min), a modulus of about 0.85MPa, an elongation of about 284%, a tensile strength of about 1.88MPa, a water burst time of greater than 20 seconds, a wet extractable component of about 2.38% wt/wt, and an energy loss of about 36%, and has an average dimensional stability difference of less than +/-3.0% after 14 days of storage at 80 ℃.

Example 8

Compound (abbreviation)	Unit parts
		Si1	26
Si2	10
		VMA	40
MMA	12
		EGMA	5

BVE	7
		TEGDMA	1.3
TEGDVE	0.2
		V-64	0.5
UV2	0.9
		RBT2	0.01
pTPP	0.5

In addition, the silicone hydrogel contact lenses, when tested at the beginning of the shelf life study, had an EWC of about 54% wt/wt, about 3.57(× 10) when fully hydrated^-3mm²Min), a modulus of about 0.66MPa, an elongation of about 274%, a tensile strength of about 1.40MPa, and a moisture extractable content of about 3.8% wt/wt, and has an average dimensional stability difference of less than +/-3.0% after 7 days of storage at 80 ℃.

Example 9

Compound (abbreviation)	Unit parts
		Si1	26
Si3	2
		Si2	10
VMA	45
		MMA	12
BVE	5
		TEGDMA	1.1
TEGDVE	0.2
		V-64	0.5
UV2	0.9
		RBT2	0.01
pTPP	0.5

Additionally, the silicone hydrogel contact lenses, when tested at the beginning of the shelf life study, have a modulus of about 0.81MPa, an elongation of about 351%, a tensile strength of about 1.61MPa, and an EWC of 30% wt/wt to 70% wt/wt when fully hydrated, and have a mean dimensional stability difference of less than +/-3.0% after 14 days of storage at 80 ℃.

Example 10

Compound (abbreviation)	Unit parts
		Si1	26
Si3	2
		Si2	10
VMA	40
		EGMA	15
BVE	7
		TEGDMA	1.6
TEGDVE	0.2
		V-64	0.5
UV2	0.9
		RBT2	0.01
pTPP	0.5

In addition, the silicone hydrogel contact lenses have a value of about 3.33(× 10) when fully hydrated when tested at the start of the shelf life study^-3mm²Min), a modulus of about 0.74MPa, and an elongation of about 222%, and has a mean dimensional stability difference of less than +/-3.0% after 14 days of storage at 80 ℃.

Example 11

Compound (abbreviation)	Unit parts
		Si1	32
Si3	4
		VMA	45
MMA	13
		EGMA	3
BVE	3
		TEGDMA	1.0
TEGDVE	0.2
		V-64	0.5
UV2	1.3
		RBT2	0.01
pTPP	0.5

Additionally, the silicone hydrogel contact lenses, when tested at the beginning of the shelf life study, have an EWC of about 57% wt/wt, a modulus of about 0.70MPa, an energy loss of about 40%, and a captive bubble dynamic advancing contact angle of about 50 degrees to about 60 degrees when fully hydrated, and have an average dimensional stability difference of less than +/-3.0% after 14 days of storage at 80 ℃.

Example 12

Compound (abbreviation)	Unit parts
		Si1	26
Si2	10
		VMA	40

MMA	12
		EGMA	5
BVE	7
		TEGDMA	1.2
TEGDVE	0.2
		V-64	0.5
UV2	1.3
		RBT2	0.01
pTPP	0.5

Additionally, the silicone hydrogel contact lenses, when tested at the beginning of the shelf life study, have an EWC of about 56% wt/wt, a modulus of about 0.50MPa, and a captive bubble dynamic advancing contact angle of about 47 degrees to about 51 degrees when fully hydrated, and have an average dimensional stability difference of less than +/-3.0% after 4.4 weeks of storage at 80 ℃.

Example 13

Compound (abbreviation)	Unit parts
		Si1	26
Si2	10
		VMA	40
MMA	12
		EGMA	5
BVE	3
		EGDMA	0.5
TEGDVE	0.1
		V-64	0.5
UV2	1.3
		RBT2	0.01

pTPP

0.5

Additionally, the silicone hydrogel contact lenses, when tested at the beginning of the shelf life study, have an EWC of about 55% wt/wt, a modulus of about 0.60MPa, and a captive bubble dynamic advancing contact angle of about 47 degrees to about 55 degrees when fully hydrated, and have an average dimensional stability difference of less than +/-3.0% after 2 weeks of storage at 80 ℃.

Example 14

Compound (abbreviation)	Unit parts
		Si1	29
Si2	8
		VMA	42
MMA	14
		DEGVE	7
EGDMA	0.6
		TEGDVE	0.08
V-64	0.5
		UV2	1.3
RBT2	0.01
		pTPP	0.5

Additionally, the silicone hydrogel contact lenses, when tested at the beginning of the shelf life study, have an EWC of about 55% wt/wt to about 56% wt/wt, a modulus of about 0.71MPa, and a captive bubble dynamic advancing contact angle of about 45 degrees to about 47 degrees when fully hydrated, and have an average dimensional stability difference of less than +/-3.0% after storage for at least 2 weeks at 80 ℃.

Example 15

Compound (abbreviation)	Unit parts
		Si1	29
Si2	8
		VMA	44
MMA	14
		EGVE	5
EGDMA	0.6
		TEGDVE	0.15
V-64	0.5
		UV2	1.3
RBT2	0.01

Additionally, the silicone hydrogel contact lenses, when tested at the beginning of the shelf life study, have an EWC of about 56% wt/wt and a modulus of about 0.65MPa when fully hydrated, and have a mean dimensional stability difference of less than +/-3.0% after 2 weeks of storage at 80 ℃.

Example 16

Compound (abbreviation)	Unit parts
		Si1	29
Si2	8
		VMA	45
MMA	13
		HEMA	4

EGDMA	0.5
		TEGDVE	0.1
V-64	0.5
		UV2	1.7
RBT2	0.01
		pTPP	0.5
AE	0.3

Batches of silicone hydrogel contact lenses were prepared and tested using this formulation according to the manufacturing procedures and testing methods described in the silicone hydrogel contact lens manufacturing and testing procedures using a dry demolding process, a dry delensing process, and a washing process using an extraction and hydration solution consisting of an extraction solution free of volatile organic solvents. This batch of lenses was not exposed to volatile organic solvents during their manufacture. These contact lenses contain units derived from two siloxane monomers, Sil and Si 2. This batch of contact lenses had an acceptable average dimensional stability difference.

Additionally, the silicone hydrogel contact lenses, when tested at the beginning of the shelf life study, have an EWC of about 55% wt/wt to about 56% wt/wt when fully hydrated, a modulus of about 0.53MPa, a captive bubble dynamic advancing contact angle of about 5l degrees to about 53 degrees, and an energy loss of about 34%, and have a difference in average dimensional stability of less than +/-3.0% after 4.4 weeks of storage at 80 ℃.

Example 17

The polymerizable silicone composition was obtained by mixing and filtering the following compounds in the amounts specified using the procedures described in the silicone hydrogel contact lens manufacturing and testing procedures given above.

Compound (abbreviation)	Unit parts
		Si1	29
Si2	8
		VMA	42
MMA	8
		EGMA	6
DEGVE	7
		EGDMA	0.6
TEGDVE	0.1
		V-64	0.5
UV2	1.7
		RBT2	0.01
pTPP	0.5

AE

0.4

In addition, the silicone hydrogel contact lenses, when tested at the beginning of the shelf life study, had an EWC of 57% wt/wt to 58% wt/wt, about 2.9(× 10) when fully hydrated^-3mm²Min), a modulus of about 0.7MPa, an elongation of about 300%, a tensile strength of about 1.5MPa, a captive bubble dynamic advancing contact angle of about 44 degrees to about 48 degrees, a wet extractable component of about 5.10% wt/wt, and an energy loss of about 32% to about 33%, and has an average dimensional stability difference of less than +/-3.0% after 4.4 weeks of storage at 80 ℃. The polymeric lens body has about 12.2% wt/wt of dry extractable components when tested prior to extraction and hydration.

Example 18

Compound (abbreviation)	Unit parts
		Si1	29
Si2	8
		VMA	45
HOB	7
		EGMA	10
EGDMA	0.5
		TEGDVE	0.1
V-64	0.5
		UV2	1.7
RBT2	0.01
		pTPP	0.5
AE	0.3

In addition, the silicone hydrogel contact lenses, when fully hydrated, have an EWC of about 55% wt/wt to about 56% wt/wt, about 4.1(× 10) when tested at the start of the shelf life study^-3mm²Min), a modulus of about 0.6MPa, an elongation of about 275%, a tensile strength of about 1.2MPa, a captive bubble dynamic advancing contact angle of about 55 degrees to about 58 degrees, a wet extractable component of about 4.6% wt/wt, an energy loss of about 31% to about 32%, and a swelling factor of about 27%, and has an average dimensional stability difference of less than +/-3.0% after storage for 4.4 weeks at 80 ℃. The polymeric lens body has about 10.6% wt/wt of dry extractable components when tested prior to extraction and hydration.

Example 19

Compound (abbreviation)	Unit parts
		Si1	30
Si2	7
		VMA	44
MMA	8
		EGMA	6
BVE	4
		DEGVE	10
EGDMA	0.6
		TEGDVE	0.1
V-64	0.5
		UV2	1.8
RBT2	0.01
		pTPP	0.5

In addition, the silicone hydrogel contact lenses, when tested at the beginning of the shelf life study, had an EWC of about 61% wt/wt, about 3.8(× 10) when fully hydrated^-3mm²Min), a modulus of about 0.5MPa, an elongation of about 279%, a tensile strength of about 1.2MPa, a captive bubble dynamic advancing contact angle of about 45 degrees to about 47 degrees, a wet extractable component of about 4.55% wt/wt, and an energy loss of about 30% to about 33%, and has an average dimensional stability difference of less than +/-3.0% after 14 days of storage at 80 ℃. The polymeric lens body has about 13.65% wt/wt of dry extractable components when tested prior to extraction and hydration.

Example 20

Compound (abbreviation)	Unit parts
		Si1	30
Si2	7
		VMA	45
MMA	12
		EGMA	5
BVE	5
		TEGDMA	1.4
TEGDVE	0.2
		V-64	0.5
UV2	1.8
		RBT2	0.01
pTPP	0.5

In addition, the silicone hydrogel contact lenses, when fully hydrated, have an EWC of about 55% wt/wt to about 57% wt/wt, about 3.6(× 10) when tested at the start of the shelf life study^-3mm²Min), a modulus of about 0.7MPa, an elongation of about 285%, a tensile strength of about 1.3MPa, a captive bubble dynamic advancing contact angle of about 47 degrees to about 53 degrees, a wet extractable component of about 4.10% wt/wt, and an energy loss of about 34% to about 35%, and has an average dimensional stability difference of less than +/-3.0% after 14 days of storage at 80 ℃. When tested prior to extraction and hydration, the polymeric lens body was found to have about 9.80% wt/wt of dry extractable components.

While the disclosure herein refers to certain illustrated embodiments, it is to be understood that these embodiments are presented by way of example and not limitation. While exemplary embodiments are discussed, the intent of the foregoing detailed description should be construed to cover all modifications, alternatives, and equivalents of the embodiments, which may be within the spirit and scope of the invention as defined by the other disclosure.

A number of publications and patents are cited above. Each of the publications and patents cited herein is incorporated by reference in its entirety.

Claims

1. A method of manufacturing a batch of silicone hydrogel contact lenses, comprising:

providing polymerized silicone hydrogel contact lens bodies in contact lens mold assemblies, wherein a single polymerized silicone hydrogel contact lens body is provided in a single contact lens mold assembly, and each contact lens mold assembly comprises a first mold section having a concave optical surface for forming an anterior surface of the silicone hydrogel contact lens body and a second mold section having a convex optical surface for forming a posterior surface of the silicone hydrogel contact lens body, and coupling the first mold section and the second mold section together;

separating the polymerized silicone hydrogel contact lens body from the contact lens mold assembly to produce a delensed contact lens body;

washing the delensed contact lens body with an aqueous liquid free of volatile organic solvents to produce a washed contact lens; and

sterilizing the washed contact lens in a sealed contact lens package;

wherein the batch so manufactured comprises at least 20 silicone hydrogel contact lenses and the anterior surface of the sterilized contact lenses has a clinically acceptable surface wettability such that less than 5% of the silicone hydrogel contact lenses have a visually discernible non-wetting spot when positioned on an eye of an individual, and wherein the non-wetting spot is a discontinuity in the pre-lens tear film of a contact lens wearer present on the anterior surface of the contact lens and is visually discernible at a total magnification of 6 x to 70 x during slit lamp inspection;

Wherein the polymerizable composition used to form the polymerized silicone hydrogel contact lens body comprises a siloxane monomer represented by formula (1):

wherein m in formula (1) represents an integer of 3 to 10, n in formula (1) represents an integer of 1 to 10, R in formula (1)¹Is an alkyl group having 1 to 4 carbon atoms, and each R in the formula (1)²Independently a hydrogen atom or a methyl group; and wherein the polymerized silicone hydrogel contact lens body comprises a copolymer comprising polymerized units of the siloxane monomer represented by formula (1).

2. The method of claim 1, wherein at least one of the first mold portion or the second mold portion comprises a polar resin having a polarity of 1% to 7%.

3. The method of claim 1, wherein at least one of the first mold portion or the second mold portion comprises polybutylene terephthalate (PBT) resin.

4. The method of claim 1, wherein each polymerized contact lens body is obtained by polymerizing a polymerizable composition in a contact lens mold assembly using thermal radiation or ultraviolet radiation, or both.

5. The method of claim 1, wherein each polymerized silicone hydrogel contact lens body is obtained by polymerizing a polymerizable composition comprising a first siloxane monomer, a second siloxane monomer, at least one hydrophilic monomer, at least one hydrophobic monomer, and at least one crosslinker, and the polymerizable composition is free of a diluent, or free of a hydrophilic polymer, or both.

6. The method of claim 5, wherein the polymerizable composition comprises at least one hydrophilic vinyl monomer and at least one vinyl crosslinker.

7. The method of claim 1, wherein the average diameter of the batch of sterilized silicone hydrogel contact lenses is at least 20% greater than the average diameter of the same batch of silicone hydrogel contact lens bodies prior to the washing step.

8. The method of claim 1, wherein each of the sterilized silicone hydrogel contact lenses has an oxygen permeability of at least 55 barrers, or an equilibrium water content of 30% wt/wt to 70% wt/wt, or a tensile modulus of 0.2MPa to 0.9MPa, or any combination thereof.

9. The method of claim 1, wherein a polymerizable composition used to form the polymerized silicone hydrogel contact lens body comprises a hydrophilic amide monomer having one N-vinyl group, and the polymerized silicone hydrogel contact lens body comprises a copolymer comprising polymerized units of the hydrophilic amide monomer having one N-vinyl group.

10. The method of claim 1, wherein the polymerizable composition used to form the polymerized silicone hydrogel contact lens body comprises a vinyl-containing cross-linking agent, and the polymerized silicone hydrogel contact lens body comprises a copolymer comprising polymerized units of the vinyl-containing cross-linking agent.

11. A method of manufacturing a batch of silicone hydrogel contact lenses, comprising:

sterilizing the washed contact lens in a sealed contact lens package;

wherein the batch so manufactured comprises at least 20 silicone hydrogel contact lenses, and the anterior surface of the sterilized contact lenses has a clinically acceptable surface wettability such that less than 5% of the silicone hydrogel contact lenses have a visually discernible non-wetting spot when positioned on an eye of an individual, and wherein the non-wetting spot is a discontinuity in the pre-lens tear film of a contact lens wearer present on the anterior surface of the contact lens and is visually discernible at a total magnification of 6 x to 70 x during slit lamp inspection,

Wherein the polymerizable composition used to form the polymerized silicone hydrogel contact lens body comprises a siloxane monomer represented by formula (2):

wherein R in formula (2)₁Selected from a hydrogen atom or a methyl group; r in the formula (2)₂Selected from a hydrogen atom or a hydrocarbon group having 1 to 4 carbon atoms; m in formula (2) represents an integer of 0 to 10; n in formula (2) represents an integer of 4 to 100; a and b represent an integer of 1 or more; a + b equals 20 to 500; b/(a + b) equals 0.01 to 0.22; and the configuration of the siloxane units includes a random configuration; and wherein the polymerized silicone hydrogel contact lens body comprises a copolymer comprising polymerized units of the siloxane monomer represented by formula (2).

12. The method of claim 11, wherein at least one of the first mold portion or the second mold portion comprises a polar resin having a polarity of 1% to 7%.

13. The method of claim 11, wherein at least one of the first mold portion or the second mold portion comprises polybutylene terephthalate (PBT) resin.

14. The method of claim 11, wherein each polymerized contact lens body is obtained by polymerizing a polymerizable composition in a contact lens mold assembly using thermal radiation or ultraviolet radiation, or both.

15. The method of claim 11, wherein each polymerized silicone hydrogel contact lens body is obtained by polymerizing a polymerizable composition comprising a first siloxane monomer, a second siloxane monomer, at least one hydrophilic monomer, at least one hydrophobic monomer, and at least one crosslinker, and the polymerizable composition is free of a diluent, or free of a hydrophilic polymer, or both.

16. The method of claim 15, wherein the polymerizable composition comprises at least one hydrophilic vinyl monomer and at least one vinyl crosslinker.

17. The method of claim 11, wherein the average diameter of the batch of sterilized silicone hydrogel contact lenses is at least 20% greater than the average diameter of the same batch of silicone hydrogel contact lens bodies prior to the washing step.

18. The method of claim 11, wherein each of the sterilized silicone hydrogel contact lenses has an oxygen permeability of at least 55 barrers, or an equilibrium water content of 30% wt/wt to 70% wt/wt, or a tensile modulus of 0.2MPa to 0.9MPa, or any combination thereof.

19. The method of claim 11, wherein a polymerizable composition used to form the polymerized silicone hydrogel contact lens body comprises a hydrophilic amide monomer having one N-vinyl group, and the polymerized silicone hydrogel contact lens body comprises a copolymer comprising polymerized units of the hydrophilic amide monomer having one N-vinyl group.

20. The method of claim 11, wherein the polymerizable composition used to form the polymerized silicone hydrogel contact lens body comprises a vinyl-containing cross-linking agent, and the polymerized silicone hydrogel contact lens body comprises a copolymer comprising polymerized units of the vinyl-containing cross-linking agent.

21. A method of manufacturing a batch of silicone hydrogel contact lenses, comprising:

sterilizing the washed contact lens in a sealed contact lens package;

wherein the polymerizable composition used to form the polymerized silicone hydrogel contact lens body comprises a siloxane monomer represented by formula (6):

wherein n is an integer from 13 to 16 and has a molecular weight of 1500 daltons; and wherein the polymerized silicone hydrogel contact lens body comprises a copolymer comprising polymerized units of the siloxane monomer represented by formula (6).

22. The method of claim 21, wherein at least one of the first mold portion or the second mold portion comprises a polar resin having a polarity of 1% to 7%.

23. The method of claim 21, wherein at least one of the first mold portion or the second mold portion comprises polybutylene terephthalate (PBT) resin.

24. The method of claim 21, wherein each polymerized contact lens body is obtained by polymerizing a polymerizable composition in a contact lens mold assembly using thermal radiation or ultraviolet radiation, or both.

25. The method of claim 21, wherein each polymerized silicone hydrogel contact lens body is obtained by polymerizing a polymerizable composition comprising a first siloxane monomer, a second siloxane monomer, at least one hydrophilic monomer, at least one hydrophobic monomer, and at least one crosslinker, and the polymerizable composition is free of a diluent, or free of a hydrophilic polymer, or both.

26. The method of claim 25, wherein the polymerizable composition comprises at least one hydrophilic vinyl monomer and at least one vinyl crosslinker.

27. The method of claim 21, wherein the average diameter of the batch of sterilized silicone hydrogel contact lenses is at least 20% greater than the average diameter of the same batch of silicone hydrogel contact lens bodies prior to the washing step.

28. The method of claim 21, wherein each of the sterilized silicone hydrogel contact lenses has an oxygen permeability of at least 55 barrers, or an equilibrium water content of 30% wt/wt to 70% wt/wt, or a tensile modulus of 0.2MPa to 0.9MPa, or any combination thereof.

29. The method of claim 21, wherein a polymerizable composition used to form the polymerized silicone hydrogel contact lens body comprises a hydrophilic amide monomer having one N-vinyl group, and the polymerized silicone hydrogel contact lens body comprises a copolymer comprising polymerized units of the hydrophilic amide monomer having one N-vinyl group.

30. The method of claim 21, wherein the polymerizable composition used to form the polymerized silicone hydrogel contact lens body comprises a vinyl-containing cross-linking agent, and the polymerized silicone hydrogel contact lens body comprises a copolymer comprising polymerized units of the vinyl-containing cross-linking agent.

31. A batch of silicone hydrogel contact lenses, the batch comprising:

at least 20 silicone hydrogel contact lenses, each silicone hydrogel contact lens in the batch being an aqueous extracted silicone hydrogel contact lens comprising an anterior surface and an opposing posterior surface, the posterior surface sized by size and shape for placement against an eye of an individual;

the anterior surface of each of the aqueous extraction contact lenses has a clinically acceptable surface wettability such that less than 5% of the silicone hydrogel contact lenses in the batch have a non-wetted spot discernible to the naked eye when positioned on an eye of an individual;

wherein the non-wetting spots are discontinuities in the pre-lens tear film of a contact lens wearer present on the anterior surface of the contact lens and are discernible to the naked eye at a total magnification of 6 x to 70 x during slit lamp inspection, and

wherein a) a polymerizable composition used to form the silicone hydrogel contact lens comprises a siloxane monomer represented by formula (1):

wherein m in formula (1) represents an integer of 3 to 10, n in formula (1) represents an integer of 1 to 10, R in formula (1)¹Is an alkyl group having 1 to 4 carbon atoms, and each R in the formula (1) ²Independently a hydrogen atom or a methyl group; and wherein the silicone hydrogel contact lens comprises a copolymer comprising polymerized units of the siloxane monomer represented by formula (1), or

b) The polymerizable composition for forming the silicone hydrogel contact lens comprises a siloxane monomer represented by formula (2):

wherein R in formula (2)₁Selected from a hydrogen atom or a methyl group; r in the formula (2)₂Selected from a hydrogen atom or a hydrocarbon group having 1 to 4 carbon atoms; m in formula (2) represents an integer of 0 to 10; n in formula (2) represents an integer of 4 to 100; a and b represent an integer of 1 or more; a + b equals 20 to 500; b/(a + b) equals 0.01 to 0.22; and the configuration of the siloxane units includes a random configuration; and wherein the silicone hydrogel contact lens comprisesA copolymer comprising polymerized units of the siloxane monomer represented by formula (2), or

c) The polymerizable composition for forming the silicone hydrogel contact lens comprises a siloxane monomer represented by formula (6):

wherein n is an integer from 13 to 16 and has a molecular weight of 1500 daltons; and wherein the silicone hydrogel contact lens comprises a copolymer comprising polymerized units of the siloxane monomer represented by formula (6).

32. The batch of silicone hydrogel contact lenses of claim 31, wherein each silicone hydrogel contact lens is a cast-molded silicone hydrogel contact lens that is not plasma surface treated or is free of a polymeric internal wetting agent provided by including a hydrophilic polymer in the polymerizable composition used to form the silicone hydrogel contact lens.

33. The batch of silicone hydrogel contact lenses of claim 31, wherein each silicone hydrogel contact lens is a cast-molded silicone hydrogel contact lens obtained from a contact lens mold assembly comprising an anterior mold member and a posterior mold member, each mold member formed from a polar resin having a polarity of 1% to 7%.

34. The batch of silicone hydrogel contact lenses of claim 33, wherein the polar resin is polybutylene terephthalate (PBT).

35. The batch of silicone hydrogel contact lenses of claim 31, wherein each contact lens comprises a polymeric component and a liquid component, the polymeric component comprising units of at least one siloxane having one or more acrylic functional groups, and units of one or more hydrophilic monomers having one or more non-acrylic vinyl functional groups.

36. The batch of silicone hydrogel contact lenses of claim 31, wherein each contact lens has an oxygen permeability of at least 55 barrers, or an equilibrium water content of 30% wt/wt to 70% wt/wt, or a tensile modulus of 0.2MPa to 0.9MPa, or any combination thereof.

37. The batch of silicone hydrogel contact lenses of claim 31, wherein each silicone hydrogel is provided in a sterile contact lens packaging solution, and each lens body has a moisture extractable content of less than 10% (wt/wt).

38. The batch of silicone hydrogel contact lenses of claim 31, wherein the polymerizable composition used to form the silicone hydrogel contact lenses comprises a siloxane monomer represented by formula (1):

wherein m in formula (1) represents an integer of 3 to 10, n in formula (1) represents an integer of 1 to 10, R in formula (1)¹Is an alkyl group having 1 to 4 carbon atoms, and each R in the formula (1)²Independently a hydrogen atom or a methyl group; and wherein the silicone hydrogel contact lens comprises a copolymer comprising polymerized units of the siloxane monomer represented by formula (1).

39. The batch of silicone hydrogel contact lenses of claim 31, wherein the polymerizable composition used to form the silicone hydrogel contact lenses comprises a siloxane monomer represented by formula (2):

wherein R in formula (2)₁Selected from a hydrogen atom or a methyl group; r in the formula (2)₂Selected from a hydrogen atom or a hydrocarbon group having 1 to 4 carbon atoms; m in formula (2) represents an integer of 0 to 10; n in formula (2) represents an integer of 4 to 100; a and b represent an integer of 1 or more; a + b equals 20 to 500; b/(a + b) equals 0.01 to 0.22; and the configuration of the siloxane units includes a random configuration; and wherein the silicone hydrogel contact lens comprises a copolymer comprising polymerized units of the siloxane monomer represented by formula (2).

40. The batch of silicone hydrogel contact lenses of claim 31, wherein the polymerizable composition used to form the silicone hydrogel contact lenses comprises a siloxane monomer represented by formula (6):