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WO2014110693A1 - Teintures polymérisables pour lentilles de contact - Google Patents

Teintures polymérisables pour lentilles de contact Download PDF

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Publication number
WO2014110693A1
WO2014110693A1 PCT/CN2013/000053 CN2013000053W WO2014110693A1 WO 2014110693 A1 WO2014110693 A1 WO 2014110693A1 CN 2013000053 W CN2013000053 W CN 2013000053W WO 2014110693 A1 WO2014110693 A1 WO 2014110693A1
Authority
WO
WIPO (PCT)
Prior art keywords
dye
polymerizable
linking agent
monomer
reactive
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/CN2013/000053
Other languages
English (en)
Inventor
Yuan SUN
Shane Mao
Wayne Wen Lai
Xinjun Wang
Wei Guo
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
CooperVision International Holding Co LP
Original Assignee
CooperVision International Holding Co LP
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by CooperVision International Holding Co LP filed Critical CooperVision International Holding Co LP
Priority to PCT/CN2013/000053 priority Critical patent/WO2014110693A1/fr
Publication of WO2014110693A1 publication Critical patent/WO2014110693A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/16—Amino-anthraquinones
    • C09B1/20—Preparation from starting materials already containing the anthracene nucleus
    • C09B1/36—Dyes with acylated amino groups
    • C09B1/473—Dyes with acylated amino groups the acyl groups being residues of a sulfonic acid
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/16—Amino-anthraquinones
    • C09B1/20—Preparation from starting materials already containing the anthracene nucleus
    • C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
    • C09B1/32—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups
    • C09B1/34—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups sulfonated
    • C09B1/343—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups sulfonated only sulfonated in the anthracene nucleus
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/0056—Dyeing with polymeric dyes involving building the polymeric dyes on the fibres
    • D06P1/006—Dyeing with polymeric dyes involving building the polymeric dyes on the fibres by using dyes with polymerisable groups, e.g. dye ---CH=CH2
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/38—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using reactive dyes
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
    • G02B1/041—Lenses

Definitions

  • the field of the invention is polymerizable dyes for contact lenses.
  • Dyes used to tint soft contact lenses can often leach during the manufacturing process when the lenses are subjected to hydration, extraction, and sterilization conditions, or they may leach during prolonged storage.
  • polymerizable groups can be covalently attached to a dye so that the dye becomes an integral part of the polymeric matrix of the contact lens.
  • Reactive Blue 19 RB 19
  • HEMA hydroxyethyl methacrylate
  • a method for making a polymerizable dye suitable for use in contact lens formulations comprises combining a reactive dye comprising a
  • the linking agent having at least a first and a second functional group, and a base under conditions in which the first functional group of the linking agent covalently attaches to the reactive dye to form an intermediate dye comprising the second functional group.
  • the first and second functional groups are independently selected from -OH, -SH, -NH 2 , and -SiH 3 .
  • the intermediate dye is then covalently attached to a monomer to form the polymerizable dye.
  • the reactive dye is RB I 9
  • the linking agent is ethylene glycol
  • the monomer is methacrylic anhydride or methacryloyl chloride.
  • the polymerizable dye prepared using the methods described herein can be used to manufacture a contact lens in a method comprising polymerizing a formulation comprising the polymerizable dye and at least one additional polymerizable monomer to form a contact lens.
  • the polymerizable dye is RB 19-HEMA and is used as a tinting agent in a silicone hydrogel contact lens.
  • FIG. 1 depicts a reaction scheme for making RB 19-HEMA in accordance with the present disclosure.
  • Described herein is an improved method for making a polymerizable dye for use in contact lens formulations.
  • the method comprises combining a reactive dye comprising a sulfonatooxyethylsulfonyl group with a linking agent having at least two functional groups to form an intermediate dye comprising at least one pendant functional group.
  • a polymerizable group is then attached to the pendant functional group of the intermediate dye to provide a polymerizable dye.
  • the method is scalable and can be used to produce a polymerizable dye suitable for use as a tinting in the manufacture of contact lenses, thus providing a significant improvement over prior methods.
  • Exemplary reactive dyes that comprise a sulfonatooxyethylsulfonyl group include Reactive Black B, Reactive Orange 16, Reactive Yellow 14, Remazol red B, and Reactive Blue 19 (RB I 9).
  • the reactive dye is RB I 9.
  • commercially available reactive dyes are less than 90% by weight (i.e. 90 wt.%) pure or even less than 80 wt.% pure and contain significant amount of inorganic salts.
  • the reactive dye may be used as- is, or may be purified before use in the method to a purity of at least 90 wt.%.
  • the reactive dye is purified using a methanol wash in which the dye is mixed with methanol at a weight ratio of about 1 :5 up to about 1 :50, respectively, for at least 1 hour, filtered and dried.
  • the methanol wash time can be increased and/or the wash repeated to increase the dye purity level.
  • the reactive dye may be purified to achieve a purity of at least 85 wt.%, 90 wt.%, or 95 wt.%, as determined by peak area of an HPLC read-out.
  • the reactive dye is RB 19 having a purity of at least 85 wt.%, 90 wt.%, or 95 wt.%.
  • the qualifier when a series of values is presented with a qualifier preceding the first value, the qualifier is intended to implicitly precede each value in the series unless context indicates otherwise. For example, in the above-mentioned purity levels it is intended that the qualifier "at least" implicitly precedes the values of 90 wt.% and 95 wt.%. Further, throughout this disclosure a reference to “examples”, “an example” or “a specific example” or similar phrase, is intended to introduce a feature or features of the method of making the polymerizable dye, or the polymerizable dye itself (depending on context) that can be combined with any combination of previously-described or subsequently-described examples (i.e. features), unless a particular combination of features is mutually exclusive, or if context indicates otherwise.
  • the reactive dye is combined with a linking agent comprising at least two functional groups and a base.
  • a linking agent comprising at least two functional groups and a base.
  • the sulfonatooxyethylsulfonyl group is converted into a vinyl sulfone group which then reacts with a first functional group of the linking agent to form an intermediate dye comprising a second functional group.
  • the first and second functional groups are independently selected from -OH, -SH, -NH 2 , and - SiH 3 .
  • the linking agent is a straight-chain or branched alkyl or alkoxy comprising two or more pendant functional groups independently selected from -OH, -SH, - NH 2 , and -S1H3.
  • the linking agent is a C2-C 12 alkyl or alkoxy. In a further example, the linking agent comprises two to four functional groups. In specific examples, the linking agent comprises at least one hydroxyl (i.e. -OH) group. In further examples, the linking agent is a diol or a triol. Exemplary diols include glycols such as ethylene glycol, diethylene glycol, 1 ,3 propylene glycol and 1 ,2 propylene glycol. Exemplary triols include glycerol and 1 ,3,5 pentanetriol. Other exemplary linking agents include 2-mercaptoethanol, 1 ,2 ethanedithiol, ethanolamine, ethylenediamine, and 2-silylethylsilane.
  • the reactive dye and the linking group are typically combined in amounts to provide a number ratio of sulfonatooxyethylsulfonyl groups to molecule of linking agent of about 2: 1 to about 5: 1 , respectively.
  • the reactive dye is dissolved in an anhydrous solvent, such as dimethylformamide (DMF), at a ratio of about one liter of solvent for every 100 to 200 g of reactive dye.
  • DMF dimethylformamide
  • the linking agent is then added to the reactive dye. In one example, the entire amounts of the reactive dye and the linking agent are combined to form a mixture of the reactive dye and the linking agent prior to addition of the base.
  • sulfonatooxyethylsulfonyl group into a vinyl sulfone group which reacts with the linking agent to formation the intermediate dye such as an alkali metal containing base or alkali metal salt.
  • suitable bases include NaH, NaNH 2 , NaOH, and K2CO3.
  • the base is a sodium salt (e.g. NaH, NaNH 2 , NaOH, etc.).
  • a base is used that results in formation of an intermediate dye that is essentially free of in szYw-formed water. Examples of such bases include NaH and NaNH 2 .
  • a reaction product that is essentially free of in s tw-formed water comprises less than 0.5 wt.% in situ formed water.
  • a drying agent such as anhydrous Na 2 S0 4
  • substantially anhydrous reaction condition it is meant that the reaction mixture comprises less than 2 wt.% water, or less than 1 wt.%, or 0.5 wt.% water.
  • the base is added incrementally over a period of time, for example in roughly equal increments about every 2 to 10 minutes over a period of about 30 to 90 minutes.
  • the reaction may be carried out at a reduced temperature, for example less than about 10° C typically about 0° C.
  • the reaction may be monitored by chromatography. Additional base can be added in increments until the reaction is complete. Further, increasing the reaction temperature towards the end of the reaction to room temperature or above can facilitate complete conversion of the reactive dye.
  • the intermediate dye is typically collected by filtration, washed in an organic solvent, and then filtered and dried.
  • the intermediate dye is purified to at least 95 wt.% prior to reaction with a monomer to form the polymerizable dye.
  • the yield of intermediate dye relative to the amount of reactive dye is at least 50%. For example, if 500g of reactive dye is used in the reaction, the yield of intermediate dye is at least 250g. In various examples, the yield of intermediate dye is at least 55 wt.%, 60 wt.% or 65 wt.%.
  • the reactive dye is RB I 9
  • the linking agent is ethylene glycol
  • the base is NaH.
  • the intermediate dye is dissolved in a suitable solvent prior to reaction with the monomer, typically at a ratio of about one liter of solvent for every 100 to 200 g of reactive dye.
  • suitable solvents are dimethylformamide (DMF)
  • the term monomer means any compound that can covalently attach to the functional group of the intermediate dye to provide a polymerizable moiety.
  • the polymerizable moieties of components of contact lens formulations are independently selected from an acrylate group (i.e. CH 2 CHC(0)0-), a methacrylate group (i.e. CH 2 C(CH 3 )C(0)0-), or a vinyl group (i.e.
  • the reactive dye has a single sulfonatooxyethylsulfonyl group, such as RB I 9
  • the linking agent has two functional groups, such as ethylene glycol
  • the resulting intermediate dye will have a single pendant functional group.
  • the intermediate dye can then be reacted with a monomer that results in a polymerizable dye having a single polymerizable moiety.
  • a polymerizable dye comprising two or more polymerizable moieties can be made using the methods described herein, and thus act as a cross-linking agent in a polymerizable formulation.
  • a reactive dye such as Reactive Black 5 which comprises two sulfonatooxyethylsulfonyl groups
  • a linking agent such as ethylene glycol which has two functional groups
  • Another way to prepare a cross-linkable dye is to select a linking agent having three or more functional groups. After being attached to a sulfonatooxyethylsulfonyl group of the reactive dye, two (or more) pendant functional groups will be remain available for linking to the monomer providing the polymerizable group.
  • the linking agent 1 , 3, 5 pentanetriol comprises three functional groups and thus can be used to prepare a cross-linkable dye in accordance with the methods described herein.
  • the monomer is an acrylating agent selected from methacrylic anhydride, methacryloyl chloride, acrylic anhydride, methacrylic anhydride, 2-isocyanatoethyl methacrylate, itaconic acid, or itaconic anhydride.
  • an "acrylating agent” is a compound that can react with the intermediate dye to attach one or more methacrylate or acrylate groups.
  • the reactive dye is RB I 9
  • the linking agent is ethylene glycol
  • the monomer is methacrylic anhydride or methacryloyl chloride, which forms RB 19-HEMA, as depicted in Figure 1.
  • RB 19-HEMA With previous methods of forming RB 19-HEMA, in which RB I 9 and HEMA are combined in the presence of a base, an undesirable side reaction in which vinyl sulfone is hydroxylated rather than methacrylated. In some prior methods, as much as 50% or more of the final product is hydroxylated, and column purification is needed to separate the hydroxylated product, remaining RB I 9-vinylsulfone intermediate, and other impurities from the RB 19-HEMA, which is not practical on a commercial scale. In one example using the methods described herein, a hydroxylated intermediate, e.g. RB 19-OH, is purposefully formed as an intermediate compound, not as an undesirable side reaction.
  • a hydroxylated intermediate e.g. RB 19-OH
  • the RB 19-OH is then reacted with the monomer to form the polymerizable dye.
  • Conventional reaction conditions can be used to link the monomer to the intermediate dye.
  • the intermediate dye with a pendant hydroxyl group e.g. RB 19-OH
  • methacrylic anhydride in the presence of an esterification catalyst (e.g. 4-dimethylaminopyridine) and triethylamine.
  • the monomer comprises one or more vinyl groups, such as ally ether or ethylene glycol divinyl ether, which is reacted with the intermediate dye using conventional methods to result in a polymerizable dye comprising a vinyl group.
  • the intermediate dye and the monomer are combined under substantially anhydrous reaction conditions.
  • an advantage of the methods disclosed herein is that they can be used to produce large batches of polymerizable dyes in high purity compared to previous methods.
  • the purity of the polymerizable dye produced by the method disclosed herein is at least 90 wt.%, 92 wt.%, or 95 wt.%.
  • the yield of polymerizable dye obtained in a single batch relative to the amount of intermediate dye is preferably at least 10%.
  • the amount of polymerizable dye obtained is at least 50g.
  • the polymerizable dye is RB 19-HEMA having a purity of at least 95% and in an amount of at least 50 g produced from single batch.
  • the method forms RB 19-HEMA at a purity of at least 90% or 95% without column purification.
  • the polymerizable dye is suitable for use as a colorant of polymerized medical devices, including ophthalmic devices such as silicone hydrogel contact lenses or traditional HEMA- based hydrogel contact lenses.
  • the polymerizable dye can be directly added to a polymerizable composition comprising at least one additional polymerizable monomer, which is then polymerized so that the polymerizable dye becomes an integral part of the resulting polymer, imparting color to it.
  • the polymerizable dye is typically added to a polymerizable formulation in an amount of about 0.001 wt.%. to about 0.5 wt.%, relative to the weight of all
  • the polymerizable dye may be added to the formulation in an amount of about 0.005 wt.% to about 0.05 wt. %.
  • Examples of polymerizable formulations for silicone hydrogel contact lenses are described in US Pat. No. 7,750,079, US Pat No. 7,572,841 , and US Publ. No.
  • a method of manufacturing a contact lens comprising: (i) making a polymerizable formulation comprising a polymerizable dye prepared as described herein and at least one additional polymerizable monomer; and (ii) polymerizing the polymerizable formulation to form a contact lens.
  • the polymerizable dye is RB 19-HEMA
  • the at least one additional polymerizable monomer is a Si-0 containing monomer.
  • the solid was collected by filtration (LC-MS purity >93%).
  • the solid was collected by filtration and dried in a vacuum drying oven (50°C, about 0.08 MPa, 24 hours). The yield was 400 g of RB 19-OH (purity >95%).
  • DMAP dimethylaminopyridine
  • the solid was then washed with 500 mL of DI water for 2 hours, filtered, and dried in vacuum oven (50°C, about 0.08 MPa, 3 days). The yield was 55 g of RB 19-HEMA (purity >95%).
  • a method for making a polymerizable dye comprising: combining a reactive dye comprising a sulfonatooxyethylsulfonyl group, a linking agent having at least a first and a second functional group, and a base under conditions in which the first functional group of the linking agent covalently attaches to the reactive dye to form an intermediate dye comprising the second functional group, wherein the first and second functional groups are independently selected from -OH, -SH, -NH 2 , and -SiH 3 ; and combining the intermediate dye with a monomer under conditions in which the second functional group of the intermediate dye covalently attaches to the monomer to form the polymerizable dye.
  • linking agent is selected from ethylene glycol, 1 ,3 propylene glycol, 1 ,2 propylene glycol, glycerol, or 1 ,3,5 pentanetriol.
  • a polymerizable dye prepared by the method of any one of 1 to 15.
  • a method of manufacturing a contact lens comprising polymerizing a polymerizable formulation comprising the polymerizable dye of 16 and at least one additional polymerizable monomer to form a contact lens.

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  • Engineering & Computer Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Textile Engineering (AREA)
  • Structural Engineering (AREA)
  • Eyeglasses (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

L'invention concerne une teinture polymérisable destinée à être utilisée dans des formulations de lentille de contact ; celle-ci est préparée en combinant une teinture réactive comprenant un groupe sulfonato-oxyéthylsulfonyle avec un agent de liaison possédant au moins deux groupes fonctionnels pour former une teinture intermédiaire comprenant au moins un groupe fonctionnel greffé auquel est fixé un groupe polymérisable.
PCT/CN2013/000053 2013-01-18 2013-01-18 Teintures polymérisables pour lentilles de contact Ceased WO2014110693A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PCT/CN2013/000053 WO2014110693A1 (fr) 2013-01-18 2013-01-18 Teintures polymérisables pour lentilles de contact

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Application Number Priority Date Filing Date Title
PCT/CN2013/000053 WO2014110693A1 (fr) 2013-01-18 2013-01-18 Teintures polymérisables pour lentilles de contact

Publications (1)

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WO2014110693A1 true WO2014110693A1 (fr) 2014-07-24

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023030717A1 (fr) * 2021-08-31 2023-03-09 Bausch + Lomb Ireland Limited Dispositifs ophtalmiques et procédé de fabrication
CN117946535A (zh) * 2022-10-28 2024-04-30 视阳光学股份有限公司 反应性染料、其制造方法、及隐形眼镜

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4468229A (en) * 1981-08-12 1984-08-28 Ciba-Geigy Corporation Tinted contact lenses and a method for their preparation with reactive dyes
CN1090930A (zh) * 1992-10-26 1994-08-17 庄臣及庄臣视力产品有限公司 制造经著色隐形眼镜镜片之方法
US20050049425A1 (en) * 2003-08-25 2005-03-03 Pearson Jason Clay Ethylenically-unsaturated red anthraquinone dyes
US20050251929A1 (en) * 2003-07-15 2005-11-17 Shinn-Gwo Hong Method for preparing the reactive tinting compound and the tinted contact lens
US20060252844A1 (en) * 2005-05-05 2006-11-09 Key Medical Technologies, Inc. Ultra violet, violet, and blue light filtering polymers for ophthalmic applications
US20070100018A1 (en) * 2005-11-03 2007-05-03 Hagting Joke G Functionalized dyes and use thereof in ophthalmic lens material

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4468229A (en) * 1981-08-12 1984-08-28 Ciba-Geigy Corporation Tinted contact lenses and a method for their preparation with reactive dyes
CN1090930A (zh) * 1992-10-26 1994-08-17 庄臣及庄臣视力产品有限公司 制造经著色隐形眼镜镜片之方法
US20050251929A1 (en) * 2003-07-15 2005-11-17 Shinn-Gwo Hong Method for preparing the reactive tinting compound and the tinted contact lens
US20050049425A1 (en) * 2003-08-25 2005-03-03 Pearson Jason Clay Ethylenically-unsaturated red anthraquinone dyes
US20060252844A1 (en) * 2005-05-05 2006-11-09 Key Medical Technologies, Inc. Ultra violet, violet, and blue light filtering polymers for ophthalmic applications
US20070100018A1 (en) * 2005-11-03 2007-05-03 Hagting Joke G Functionalized dyes and use thereof in ophthalmic lens material

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023030717A1 (fr) * 2021-08-31 2023-03-09 Bausch + Lomb Ireland Limited Dispositifs ophtalmiques et procédé de fabrication
CN117946535A (zh) * 2022-10-28 2024-04-30 视阳光学股份有限公司 反应性染料、其制造方法、及隐形眼镜

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