JP3260461B2 - High refractive index optical material and method for producing the same - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[Background of the Invention]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a resin for a plastic lens, and more particularly to a resin for a lens having a high refractive index and excellent impact resistance.

[0002]

2. Description of the Related Art Diethylene glycol bisaryl carbonate resins have been widely used as resins for plastic lenses. This resin has advantages such as excellent impact resistance, transparency, and good light dispersion characteristics, but has a low refractive index of 1.50, and requires a lens to obtain refraction equivalent to glass. However, there was a disadvantage that the thickness became thick.

On the other hand, it is known that various diacrylates or dimethacrylates easily undergo radical polymerization to give a lens having excellent transparency. For example, di (meth) acrylates having a bromine-containing bisphenol A skeleton (JP-A-59-184210, JP-A-59-19)
3915) and di (meth) acrylates having a sulfur-containing aromatic skeleton (JP-A-60-26010 and JP-A-62-195357) have a high refractive index. In addition, it is known to exhibit excellent optical characteristics with a high balance of a high Abebe number.

[0004] However, these compounds form a highly crosslinked structure by radical polymerization, exhibiting excellent heat resistance and polishing properties, but tend to make the cured product brittle. As a method for improving these disadvantages, a method of converting a bromine-containing bisphenol A derivative into urethane (meth) acrylate is disclosed in Japanese Patent Application Laid-Open No. 60-51706. However, since a bromine atom is contained, the specific gravity increases. Inevitably, the weather resistance deteriorates. [Summary of the Invention]

[0005]

SUMMARY OF THE INVENTION It is an object of the present invention to solve the above-mentioned problems and to provide a resin for a lens which is lightweight, has high refraction, is excellent in transparency and impact resistance. <Summary>

[0006]

According to the present invention, there is provided a high refractive index optical material comprising a composition comprising the following components A, B, and C, wherein the composition comprises heat and / or active energy rays and / or ethylenically unsaturated. It is characterized by comprising a resin which is polymerized and cured by being subjected to the action of a radical generator and / or a urethanation reaction catalyst for bonding. Component (A): a sulfur-containing (meth) acrylic monomer represented by the following formula [I] or a mixture thereof with a sulfur-containing (meth) acrylic monomer represented by the following formula [II]

[0007]

Embedded image [In each formula, R ¹ is a hydrogen atom or a methyl group,
R ² and R ³ represent a hydrocarbon group having 1 to 12 carbon atoms, X represents a halogen atom excluding fluorine, and n represents 0 or 1 to 4
Indicates an integer. A plurality of groups may be the same or different. However, the weight ratio of compound [I] / compound [II] is from 10/0 to 1/9. Component (B): a hydroxy (meth) acrylic monomer represented by the following formula [III]

[0008]

Embedded image [Wherein, R ⁵ is a hydrogen atom or a methyl group, R ⁴ is a hydrocarbon group having 2 to 20 carbon atoms which may contain ether oxygen, p
And q each represent an integer of 1 or more and p + q ≧ 3. A plurality of groups may be the same or different. However, the weight ratio of component (A) / component (B) is 9
5/5 to 50/50. Component (C): an isocyanate compound having a plurality of -NCO groups.

However, the ratio of the —NCO group of the component (C) to the total of —OH groups of the compounds of the components (A) and (B) —
NCO / -OH is 0.2-3.

[0010] The method for producing a high refractive index optical material according to the present invention comprises the steps of: preparing a composition comprising the following components (A), (B) and (C) by using a radical polymerization initiator and a urethanization reaction catalyst. The method is characterized in that radical polymerization or radical polymerization and urethanation reaction are simultaneously performed by irradiation with ultraviolet rays, and then the polymerization is completed by heating. Component (A): a sulfur-containing (meth) acrylic monomer represented by the following formula [I] or a mixture thereof with a sulfur-containing (meth) acrylic monomer represented by the following formula [II]

[0011]

Embedded image [In each formula, R ¹ is a hydrogen atom or a methyl group,
R ² and R ³ each represent a hydrocarbon group having 1 to 12 carbon atoms; X represents a halogen atom excluding fluorine;
Or an integer of 1 to 4. A plurality of groups may be the same or different. However, the weight ratio of compound [I] / compound [II] is from 10/0 to 1/9. Component (B): a hydroxy (meth) acrylic monomer represented by the following formula [III]

[0012]

Embedded image [Wherein, R ⁵ is a hydrogen atom or a methyl group, R ⁴ is a hydrocarbon group having 2 to 20 carbon atoms which may contain ether oxygen, p
And q each represent an integer of 1 or more and p + q ≧ 3. A plurality of groups may be the same or different. However, the weight ratio of component (A) / component (B) is 9
5/5 to 50/50. Component (C): an isocyanate compound having a plurality of -NCO groups.

However, the ratio of the —NCO group of the component (C) to the total of —OH groups of the compounds of the components (A) and (B) —
NCO / -OH is 0.2-3. <Effects> According to the present invention, lightweight, high refractive index and transparency,
A lens resin having excellent impact resistance can be obtained. [Specific description of the invention] The high refractive index optical material according to the present invention is obtained by polymerizing and curing a composition comprising the components (A), (B) and (C).

Here, "comprising" means, in addition to the listed components, that is, components (A) to (C), a small amount of auxiliary components (details described below) unless the gist of the present invention is impaired. ) May be included. <Component (A): Sulfur-Containing (Meth) acrylic Monomer> Component (A) is a sulfur-containing bis (meth) acrylate represented by the formula [I] or a sulfur-containing sulfur-containing (meth) acrylate represented by the formula [II]. A) mixtures with acrylates.

[0015]

Embedded image [In each formula, R ¹ is a hydrogen atom or a methyl group,
R ² and R ³ each represent a hydrocarbon group having 1 to 12 carbon atoms; X represents a halogen atom excluding fluorine;
Or an integer of 1 to 4. A plurality of groups may be the same or different. However, the weight ratio of compound [I] / compound [II] is from 10/0 to 1/9.

The terms "(meth) acryl" and "(meth) acrylate" are generic terms for acryl or methacryl and acrylate or methacrylate.

The compounds of the formulas (I) and (II) are bis (hydroxyalkylthioalkyl) benzene di (meth) acrylates (I) and mono (meth) acrylates (II). When both compounds are used in combination, R ¹ , R ² , R ³ , X, and n of each compound may not be the same between both compounds, but depending on how these compounds are synthesized, these groups may be substituted with both compounds. It is rather common that they are the same, and it is preferable from the viewpoint of polymerizability.

From the viewpoint of the method of synthesizing these compounds, the bis (hydroxyalkyl (R ² ) thioalkyl (R ³ )) benzene has a structure in which R ² has ² carbon atoms and R ³ has 1 carbon atom. Can be said to be one typical example.

Sulfur-containing (meta) represented by the formula (I)
Specific examples of the acrylate compound include, for example, p-
Bis (β-methacryloyloxyethylthio) xylylene (R ¹ : methyl, R ² : ethylene, R ³ : methylene,
n = 0), p-bis (β-acryloyloxyethylthio) xylylene, m-bis (β-methacryloyloxyethylthio) xylylene, m-bis (β-acryloyloxyethylthio) xylylene, p-bis (β- (Methacryloyloxyethylthio) tetrabromoxylylene and the like.

These compounds are disclosed in, for example,
195357 can be synthesized.

Specific examples of the terminal hydroxy-containing sulfur (meth) acrylate compound represented by the formula [II] include mono (meth) acrylates corresponding to the above bis (meth) acrylate, for example, p- (β-methacryloyloxyethyl). Thio)-(β-hydroxyethylthio) -xylylene (R ¹ : methyl, R ² : ethylene, R ³ : methylene, n = 0) and p- (β-acryloyloxyethylthio)-(β-hydroxyethylthio ) -Xylylene and their ortho and meta isomers. In addition, these compounds can of course be regarded as (meth) acrylate compounds, not as xylylene compounds, and they are 2- [p- (2-hydroxy (ethylthiomethyl) phenylmethylthio] ethyl =
Needless to say, it can be expressed as (meth) acrylate. <Compound (B)> The compound (B) is a terminal hydroxy (meth) acrylate represented by the following formula [III].

[0022]

Embedded image [Wherein, R ⁵ is a hydrogen atom or a methyl group, R ⁴ is a hydrocarbon group having 2 to 20 carbon atoms which may contain ether oxygen, p
And q are each 1 or more, and p + q ≧ 3, preferably p
+ Q = 3 to 6. A plurality of groups may be the same or different. ] Terminal hydroxy (meth) acrylate compound represented by the formula [III], the polyhydroxy compounds ^- is (R 4 (OH) p + q) of the portion (meth) acrylate. When p is 2 or more, the (meth) acryloyl moieties may be the same or different, but are usually the same depending on the synthesis method of compound [III], and are also preferable from the viewpoint of polymerizability. .

R ⁴ is C ₂ which may contain ether oxygen
~C ₂₀ hydrocarbon group.

Therefore, this hydroxy compound (R ^4-
Specific examples of (OH) _{p + q} ) include (a) a polyhydroxy compound containing no ether oxygen, such as glycerol, pentaerythritol and sorbitol, and (b) a polyhydroxy compound containing ether oxygen, such as diglycerol; There are 1,2-bis (1,2-dihydroxypropyloxyethylene and dipentaerythritol.

Hydroxy (meth) represented by the formula [III]
The following are specific examples of the acrylate compound.

(I) ether oxygen-free derivatives such as 2,3-dihydroxypropyl methacrylate,
3-dihydroxypropyl acrylate, 1,3-dimethacryloyloxy-2-hydroxypropane, 1,3
-Diacloyloxy-2-hydroxypropane, 1-
Acroyloxy-3-methacryloyloxy-2-hydroxypropane, and derivatives of pentaerythritol, such as pentaerythritol trimethacrylate and pentaerythritol triacrylate, (ii)
Derivatives of polyglycerols, such as diglycerol dimethacrylate, diglycerol diacrylate, triglycerol dimethacrylate, triglycerol diacrylate, (iii) for example 4,7-dioxo-2,9
-Epoxy acrylate derivatives derived from diglycidylated products of ethylene glycol, butylene glycol or propylene glycol typified by -dihydroxy-1,10-dimetha (acyl) yloxydecane, particularly preferred among the above are 2,3- Glycerol derivatives such as dihydroxypropyl methacrylate and 2,3-dihydroxypropyl acrylate. <Component (C)> Component (C) is a polyfunctional isocyanate,
That is, an isocyanate having a plurality of, preferably two, -NCO groups. Component (C) is the component (A)
It is considered that these compounds react with the hydroxyl group of (B) to urethanize these compounds, and the component (C) contains a plurality of -N
Since it has a CO group, the urethane product also has a crosslinked structure by this reaction.

The group to which the -NCO group is bonded may be aromatic or aliphatic (including alicyclic). As the former, an unsubstituted or substituted (substituent is a lower alkyl group, a halogen group, or the like) benzene group and naphthalene group are typical, and the latter has 5 carbon atoms.
Typical are up to about 15 alkane, alkene, cycloalkane and cycloalkene groups (e.g. isophorone).

Specific examples of the polyfunctional isocyanate suitable as the component (C) in the present invention include o-xylylene diisocyanate, m-xylylene diisocyanate, p-xylylene diisocyanate, tolylene diisocyanate, naphthylene diisocyanate, and isophorone diisocyanate. , Triisocyanurates, and their hydrogenated nuclei, hexamethylene diisocyanate, and the like.

Particularly preferred among these isocyanate compounds are m-xylylene diisocyanate and the like. <Composition> The ratio of the component (A) to the component (B) is as follows.

A / B = 95 parts by weight / 5 parts by weight to 50 parts by weight / 50 parts by weight, preferably 90 parts by weight / 10 parts by weight to 70 parts by weight / 30
When the weight ratio of the component (A) to the component (B) exceeds 95/5, there is almost no effect of improving the physical properties such as the impact resistance of the cured product, and conversely, if the weight ratio is less than 50/50. The refractive index of the cured product is lowered, and the meaning as a material for a high refractive index lens is lost.

On the other hand, the amount of the polyfunctional isocyanate (component (C)) added when the mixture of the above components (A) and (B) is urethanized depends on the number of —OH groups in the mixture and the amount of the polyfunctional isocyanate. The ratio of the number of —NCO groups is as follows.

-NCO / -OH = 0.2-3, preferably 0.5-1.5 If the number of -NCO groups is more than 3 by weight to -OH, heat resistance is lowered, and If it is less than the above, the bending characteristics are deteriorated. If the heat resistance decreases, cracks tend to occur in the coating film applied to the lens, and if the bending characteristics deteriorate, the center thickness of the lens cannot be reduced, which is not preferable. <Auxiliary component> The high refractive index optical material according to the present invention is obtained by polymerizing and curing a composition containing components (A) to (C), and this composition may contain a small amount of an auxiliary component. Is as described above. Accordingly, the resin for a lens of the present invention can be produced by mixing a relatively small amount of another monomer capable of radical polymerization into the composition before curing and copolymerizing the mixture. Other monomers used in this case include, for example, nuclei such as styrene, chlorostyrene, dichlorostyrene, bromostyrene, dibromostyrene, divinylbenzene, α-methylstyrene and / or
Side chain substituted and unsubstituted styrene, phenyl (meth) acrylate, phenoxyethyl (meth) acrylate, and halogen-substituted halogens other than fluorine,
Trimethylolpropane tri (meth) acrylate,
2,2-bis [4 (β-methacryloyloxyethoxy)
(Phenyl) propane, 2,2-bis [4 (β-acryloyloxyethoxy) phenyl] propane, and (meth) acrylate compounds such as triethylene glycol di (meth) acrylate. Of these other monomers, styrene, chlorostyrene, dibromostyrene, divinylbenzene, 4,4'-bis (methacryloyloxyethoxy) diphenylpropane, and mixtures thereof are particularly preferred.

As the auxiliary component, there can be further included an antioxidant, an ultraviolet absorber, a dye / pigment, a filler, and the like. <Polymerization Curing> The high refractive index optical material according to the present invention is characterized in that a composition comprising components A, B, and C is used as a radical generator for heat and / or active energy rays and / or ethylenically unsaturated bonds (specifically, Specifically, it is made of a resin which is polymerized and cured by being subjected to the action of a radical polymerization initiator) and / or a urethanization reaction catalyst.

The type and strength of these excitation means to be applied are arbitrary as long as a predetermined polymerized cured product can be obtained. However, from the viewpoint of improving operability and productivity of the resulting cured product, the components (A) to The composition containing (C) is irradiated with ultraviolet rays in the presence of a radical polymerization initiator and a urethanization reaction catalyst to perform radical polymerization or urethanation reaction with the radical polymerization, and then heat to complete the polymerization. Is preferred.

The amount of ultraviolet light to be irradiated is arbitrary as long as the photopolymerization initiator generates radicals. If the amount is extremely small, the effect of photopolymerization cannot be obtained. Cause degradation of the polymer by light,
Total energy of ultraviolet light of 0.01 nm to 390 nm is 0.01
It is preferable to appropriately select an ultraviolet ray in the range of J to 300 J in accordance with the composition of the monomer and the type of additive such as the type of photopolymerization initiator. Specific examples of the lamp to be used include a metal halide lamp and a high-pressure mercury lamp.

The temperature and time of the heat polymerization after the irradiation of the ultraviolet rays vary depending on the type or amount of the thermal polymerization initiator and the urethanization reaction catalyst to be added, and are selected according to the physical properties of the objective lens. In general, excessive heating usually results in a yellowing of the resulting lens, and the use of a catalyst that is too active at low temperatures makes the composition unstable during handling.
Polymerization is carried out at a temperature of 0 ° C. for 0.05 to 10 hours.

The term “thermal polymerization” as used herein includes post-treatment steps of a lens molded product, for example, polymerization by heat during coating.

By using this method, the polymerization time can be significantly reduced as compared with the case of heating polymerization alone, and
The problem of thickening or separation in some cases when a compound which has been urethanized beforehand is mixed with the compound of the formula [I] is solved, and productivity and operability are improved. In general, when urethane acrylate is copolymerized to improve physical properties, it is inevitable that the viscosity increases during mixing, especially when a liquid is injected like a lens.
It is desirable to use the above method.

The photopolymerization initiator used here is 2,2.
6-dimethylbenzoyldiphenylphosphine oxide, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, 2,4,6-trimethylbenzoylphenylphosphinic acid methyl ester, 2,6-dichlorobenzoyldiphenylphosphine oxide, ,
Acylphosphine oxides and acylphosphinic esters such as 6-dimethoxybenzoyldiphenylphosphine oxide, 1-phenyl-2-hydroxy-2-methylpropan-1-one, 1-hydroxycyclohexylphenyl ketone, 4-diphenoxy Dichloroacetophenone, diethoxyacetophenone, 1- (4
Acetophenone compounds such as -isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, benzophenone, methyl benzoylbenzoate,
Phenylbenzophenone, hydroxybenzophenone,
Benzophenone compounds such as 3,3'-dimethyl-4-methoxybenzophenone and diphenoxybenzophenone.

Preferred photopolymerization initiators are 2,4,6-trimethylbenzoyldiphenylphosphine oxide,
Trimethylbenzoylphenylphosphinic acid methyl ester, 1-hydroxycyclohexylphenylketone, benzophenone and diphenoxybenzophenone.

The ratio of these photopolymerization initiators is from 0.01 to 0.1 based on 100 parts by weight of the diethylenically unsaturated monomer.
It is about 3 parts by weight, preferably about 0.02 to 0.2 parts by weight. If the mixing ratio of the photopolymerization initiator is too large, not only is the internal homogeneity of the cured resin inferior, but also the hue is deteriorated.If the photopolymerization initiator is too small, the composition can be sufficiently cured. Disappears.

Although the thermal polymerization initiator is not always essential, it is desirable to add it in order to complete the polymerization better. The amount used is preferably 5 parts by weight or less based on 100 parts by weight of the composition. Excessive use is not preferred because it has adverse effects such as deterioration of the hue of the cured product. Specific examples of the thermal polymerization initiator include benzoyl peroxide, diisopropyl peroxycarbonate, ralloyl peroxide, t-butylperoxy (2-ethylhexanoate), azobisisobutyronitrile, and the like.
In general, any of those used for thermal polymerization of (meth) acrylates can be used. These generally belong to the category of radical generators for ethylenically unsaturated bonds.

On the other hand, as the catalyst for the urethanization reaction, a known catalyst can be used. Specific examples include metal compounds such as dibutyltin dilaurate and aluminum triisopropoxide, and Lewis bases such as tertiary amines and tertiary phosphines.

The amount used is about 10 to 10000 ppm, preferably 1 to 1 ppm, based on the composition comprising the components (A) to (C).
It is about 00 to 1000 ppm. When the amount of the urethanization reaction catalyst exceeds 10,000 ppm, components (A) to
Injection becomes difficult because the composition of (C) thickens due to the urethane-forming reaction. Conversely, if it is less than 10 ppm, the polymerization will not be completed, and various physical properties will be reduced.

In the present invention, as described above, the composition before curing can be cured by adding an antioxidant, an ultraviolet absorber, a coloring agent, and the like as auxiliary components. The cured resin molded into a shape can be subjected to a surface treatment such as a hard coat and an anti-reflection coat.

[0046]

The following examples serve to explain the present invention more specifically. In addition, the part in an example shows a weight part. Various properties of the cured product described in the examples were measured by the following test methods. (1) Appearance Visual observation (2) Refractive index Measured at 25 ° C. using an Abbe refractometer (manufactured by Atago). (3) Optical distortion The cured product obtained using the lens mold was inspected with a distortion inspection machine (manufactured by Toshiba Glass Co., Ltd.). (4) Impact resistance A rigid ball (weight 16.3 g, diameter 15.9 mm) was dropped from a height of 127 cm on a flat plate with a thickness of 2 mm according to the FDA standard. Is indicated by x. Measurement temperature: 25 ° C. (5) Flexural modulus A plate having a width of 1 cm and a thickness of 2 mm was measured by an autograph at a distance between supporting points of 3 cm. Measurement temperature 2
5 ° C. (6) Heat resistance In the Vicat softening test, those in which the indenter penetrated 0.2 mm or more at 80 ° C. or less were evaluated as ×, and those which did not enter were evaluated as ○. Indenter cross-sectional area 1.0 mm ² , load 5 kg, heating rate 50 ° C / Hr

Example 1 34.7 parts of p-bis (β-methacryloyloxyethylthio) xylylene, 34.7 parts of 2- [p- (2-hydroxyethylthiomethyl) phenylmethylthio] ethyl methacrylate, 34.7 parts of glycerol methacrylate ( 9.2 parts of Nippon Yushi Co., Ltd. "Blemmer GLM"), 21.4 parts of m-xylylene diisocyanate, and 2,4,6-trimethylbenzoyldiphenylphosphine oxide (manufactured by BASF) as a polymerization initiator and a polymerization catalyst. Lucilin TPO ”), 0.05 part, t-butyl peroxy-2-ethylhexanoate (“ Perbutyl O ”manufactured by NOF Corporation) 0.3 part and dibutyltin dilaurate 0.001 part. Then, the mixture was defoamed to obtain a composition.

This composition was poured into a 2 mm deep mold composed of a mirror-finished glass plate and a gasket made of an ethylene-vinyl acetate copolymer, and a distance of 40 mm from the glass surface.
Ultraviolet rays were irradiated for 10 minutes while being passed on a conveyor between metal halide lamps having an output of 80 W / cm, which were placed above and below each cm. Further, after that, the resultant was heated and polymerized in an oven at 80 ° C. for 2 hours and at 100 ° C. for 2 hours, and then demolded to obtain a colorless and transparent cured product. Table 1 shows the measurement results of the physical properties of the cured product.
Was as shown in FIG. In addition, the defoamed composition was similarly poured into a lens mold for a minus lens having a diameter of 80 mm and a center thickness of 1.3 mm composed of a glass mold and a gasket made of an ethylene-vinyl acetate copolymer. Similarly, after irradiation with ultraviolet rays, the mixture was polymerized by heating and demolded to obtain a colorless and transparent lens. The optical distortion of this lens was as shown in Table 1.

Example 2 34.7 parts of p-bis (β-methacryloyloxyethylthio) xylylene, 34.7 parts of 2- [p- (2-hydroxyethylthiomethyl) phenylmethylthio] ethyl methacrylate, glycerol dimethacrylate ("Blemmer GMR" manufactured by NOF Corporation) 14.2 parts and m-
A cured product was obtained in exactly the same manner as in Example 1 except that 16.4 parts of xylylene diisocyanate was used. The measurement results of physical properties and the optical distortion of the lens were as shown in Table 1.

Example 3 80.0 parts of p-bis (β-methacryloyloxyethylthio) xylylene, 9.2 parts of glycerol methacrylate (“Blenmer GLM” manufactured by NOF Corporation) and 10.8 parts of m-xylylene diisocyanate were used. Except for using, a cured product was obtained in the same manner as in Example 1. The measurement results of physical properties and the optical distortion of the lens were as shown in Table 1.

Example 4 31.3 parts of p-bis (β-methacryloyloxyethylthio) xylylene, 31.3 parts of 2- [p- (2-hydroxyethylthiomethyl) phenylmethylthio] ethyl methacrylate, 31.3 parts of glycerol methacrylate ( A cured product was obtained in the same manner as in Example 1 except that 8.3 parts of “Blenmer GLM” manufactured by NOF Corporation and 29.1 parts of m-xylylene diisocyanate were used. The measurement results of physical properties and the optical distortion of the lens were as shown in Table 1.

Comparative Example 1 100 parts of p-bis (β-methacryloyloxyethylthioxyrylene) and “Lucirin T.
P. A cured product was obtained in the same manner as in Example 1 using 0.05 parts of “O” and 0.3 parts of “perbutyl O”. The measurement results of physical properties and the optical distortion of the lens were as shown in Table 1.

Comparative Example 2 20.4 parts of p-bis (β-methacryloyloxyethylthio) xylylene, 61.1 parts of 2- [p- (2-hydroxyethylthiomethyl) phenylmethylthio] ethyl methacrylate, and m- In the same manner as in Example 1 except that 18.5 parts of xylylene diisocyanate was used,
A cured product was obtained. Physical property measurement result and optical distortion of lens
As shown in Table 1.

Comparative Example 3 p-bis (β-methacryloyloxyethylthio) xylylene 44.1 parts 2- [p- (2-hydroxyethylthiomethyl) phenylmethylthio] ethyl methacrylate 44.7 parts glycerol methacrylate (Nippon Oil & Fats) 11.8 parts Cured product was obtained in the same manner as in Example 1 using 0.05 parts of "Lucillin TPO" and 0.3 parts of "Perbutyl O" as a polymerization initiator. Was. Physical property measurement results and lens optical distortion were as shown in Table 1.

[0055]

[Table 1]

[0056]

According to the present invention, it is possible to obtain a resin for a lens which is improved in light weight, high refractive index, transparency and impact resistance according to the present invention. .

──────────────────────────────────────────────────続 き Continued on the front page (58) Field surveyed (Int.Cl. ⁷ , DB name) C08G 18/00-18/87 G02B 1/04 G02C 7/02

Claims (2)

(57) [Claims] 1. A composition comprising the following components A, B and C: a radical generator and / or a urethanization reaction catalyst for heat and / or active energy rays and / or ethylenically unsaturated bonds. A high-refractive-index optical material comprising a resin that is polymerized and cured by being subjected to an action. Component (A): a sulfur-containing (meth) acrylic monomer represented by the following formula [I] or a mixture thereof with a sulfur-containing (meth) acrylic monomer represented by the following formula [II] [In each formula, R ¹ is a hydrogen atom or a methyl group,
R ² and R ³ each represent a hydrocarbon group having 1 to 12 carbon atoms; X represents a halogen atom excluding fluorine;
Or an integer of 1 to 4. A plurality of groups may be the same or different. However, the weight ratio of compound [I] / compound [II] is from 10/0 to 1/9. Component (B): a hydroxy (meth) acrylic monomer represented by the following formula [III]: [Wherein, R ⁵ is a hydrogen atom or a methyl group, R ⁴ is a hydrocarbon group having 2 to 20 carbon atoms which may contain ether oxygen, p
And q each represent an integer of 1 or more and p + q ≧ 3. A plurality of groups may be the same or different. However, the weight ratio of component (A) / component (B) is 9
5/5 to 50/50. Component (C): an isocyanate compound having a plurality of -NCO groups. However, the ratio of the -NCO group of the component (C) to the total of the -OH groups of the compounds of the components (A) and (B) is -NCO / -O
H is 0.2-3. 2. A composition comprising the following components (A), (B) and (C), which is subjected to ultraviolet irradiation in the presence of a radical polymerization initiator and a urethanation reaction catalyst to perform radical polymerization or A method for producing a high-refractive-index optical material, wherein a radical polymerization and a urethanization reaction are simultaneously performed, followed by heating to complete the polymerization. Component (A): a sulfur-containing (meth) acrylic monomer represented by the following formula [I] or a mixture thereof with a sulfur-containing (meth) acrylic monomer represented by the following formula [II] [In each formula, R ¹ is a hydrogen atom or a methyl group,
R ² and R ³ each represent a hydrocarbon group having 1 to 12 carbon atoms; X represents a halogen atom excluding fluorine;
Or an integer of 1 to 4. A plurality of groups may be the same or different. However, the weight ratio of compound [I] / compound [II] is from 10/0 to 1/9. Component (B): a hydroxy (meth) acrylic monomer represented by the following formula [III]: [Wherein, R ⁵ is a hydrogen atom or a methyl group, R ⁴ is a hydrocarbon group having 2 to 20 carbon atoms which may contain ether oxygen, p
And q each represent an integer of 1 or more and p + q ≧ 3. A plurality of groups may be the same or different. However, the weight ratio of component (A) / component (B) is 9
5/5 to 50/50. Component (C): an isocyanate compound having a plurality of -NCO groups. However, the ratio of the -NCO group of the component (C) to the sum of the -OH groups of the compounds of the components (A) and (B) is -NCO / -O
H is 0.2-3.