JPH11174201A - Composition for plastic lens and plastic lens - Google Patents

Abstract

PROBLEM TO BE SOLVED: To produce a plastic lens having a high refractive index with good productivity by using a compsn. prepared by compounding a specified sulfur- contg. aromatic compd. and a sulfur-contg. di(meth)acrylate compd. or the like in specified proportions. SOLUTION: This compsn. contains (A) 10 to 50 pts.wt. of a sulfur contg. aromatic compd. expressed by formula I, (B) 10 to 60 pts.wt. of a sulfur-contg. di(meth)acrylate compd. expressed by formula II, and (C) 5 to 40 pts.wt. of a (meth)acrylate compd. having at least one (meth)acryloyl group in the molecule (except components (A) and (B)) based on 100 pts.wt. in total of the components (A) to (C). In the formulae, R<1> , R<3> are each independently H or CH3 , R<2> is 2 to 6C hydrocarbon, R<4> , R<5> are each independently 1 to 4C hydrocarbon groups, X is Cl, Br or I, (m) and (n) are each independently integers of 1 to 5, and (p) is an integer of 0 to 4.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a high-refractive-index resin which is rapidly cured by irradiation with active energy rays, has good transparency, impact resistance, chemical resistance, heat resistance, etc. and has excellent surface hardness. The present invention relates to a composition for a plastic lens capable of producing a plastic lens with high productivity.

[0002]

2. Description of the Related Art Plastic lenses are lighter and harder to break than inorganic lenses, can be dyed, and are easily molded with precision. From such a point, in recent years, optical lens products such as spectacle lenses, camera lenses, Fresnel lenses, lenticular lenses, and prisms have rapidly become widespread. In particular, since heat resistance and chemical resistance are required for spectacle lenses and camera lenses, not radically polymerized thermoplastics such as methyl methacrylate or styrene are represented by radically polymerized cured products such as diethylene glycol bisallyl carbonate. Thermosetting plastics are mainly used.

[0003] Such thermosetting plastics have various characteristics such as excellent impact resistance and dyeing properties, light weight, and good workability such as machinability and abrasiveness. However, a general inorganic lens (refractive index n _D = 1.52)
In comparison with the above, the refractive index is as low as n _D = 1.50, and in order to obtain the same optical characteristics as those of an inorganic lens, it is necessary to increase the center thickness, the edge thickness, and the curvature of the lens. As a result, it was not possible to obtain a thinner and lighter lens as a whole.

Therefore, various types of resin materials for giving a high refractive index to a lens have been proposed. For example,
JP-A-57-28117 describes a resin material obtained by radical polymerization of an aromatic (meth) acrylate compound into which a bromine atom has been introduced. Further, for example, JP-A-60-217229 describes a resin material obtained by reacting a polyol compound containing a sulfur atom with a polyisocyanate compound.

[0005] However, a plastic lens obtained by using an aromatic (meth) acrylate compound into which a bromine atom is introduced as a main component has a drawback in that although the refractive index can be improved, the specific gravity becomes extremely high. Therefore, materials composed of a polyol compound containing a sulfur atom and a polyisocyanate compound have come to be used. However, as a method of molding a lens using these resin materials, a mold thermopolymerization method is generally employed, so that it takes about 20 hours to mold the lens, and there is a problem in productivity.

[0006]

SUMMARY OF THE INVENTION The present invention has been made to solve the above-mentioned problems of the prior art.
The objective is to produce a high-refractive index plastic lens that cures quickly by irradiation with active energy rays, has good transparency, impact resistance, chemical resistance, heat resistance, etc., and has excellent surface hardness. An object of the present invention is to provide a plastic lens composition that can be manufactured.

[0007]

Means for Solving the Problems The inventors of the present invention have conducted intensive studies on the materials for optical lens products in order to achieve the above-mentioned objects, and as a result, have found that specific sulfur-containing aromatic compounds and sulfur-containing di (meth) acrylates The above-mentioned object can be achieved by using a composition in which a compound or the like is blended in a specific ratio, and the composition is injected into a mold and irradiated with active energy rays to be copolymerized, whereby a plastic lens satisfying various characteristics is obtained. Was found to be able to be produced with high productivity, and the present invention was completed.

That is, the composition for a plastic lens of the present invention comprises (A) a compound represented by the general formula (I):

[0009]

Embedded image (Wherein each R ¹ independently represents H or CH ₃ ;
² represents a hydrocarbon having 2 to 6 carbon atoms. 10 to 50 parts by weight of a sulfur-containing aromatic compound represented by the formula (I):
I)

[0010]

Embedded image (Wherein each R ³ independently represents H or CH ₃ ;
⁴ and R ⁵ each independently represent a hydrocarbon group having 1 to 4 carbon atoms, X represents Cl, Br or I, m and n
Each independently represents an integer of 1 to 5, and p represents an integer of 0 to 4. And 10 to 60 parts by weight of a sulfur-containing di (meth) acrylate compound represented by the formula (C) and (C) a (meth) acrylate compound having at least one (meth) acryloyl group in a molecule (the component (A) and ( B)
5 to 40 parts by weight (excluding components) [However, the total of the components (A) to (C) is 100 parts by weight. ] The composition for a plastic lens characterized by comprising:

The plastic lens of the present invention is a plastic lens obtained by polymerizing and curing the composition of the present invention.

In the present specification, "(meth) acrylate" means "methacrylate and / or acrylate", and "(meth) acryloyl" means "methacryloyl and / or acryloyl".

[0013]

DESCRIPTION OF THE PREFERRED EMBODIMENTS Preferred embodiments of the present invention will be described below.

<Component (A)> The component (A) used in the present invention is a sulfur-containing aromatic compound having a divalent sulfur atom and an aromatic ring in the molecule as represented by the above-mentioned general formula (I). It is a compound that gives a plastic lens high refractive index, heat resistance, transparency, surface hardness, chemical resistance, and the like.

R ² in the general formula (I) may be any group as long as it is a hydrocarbon having 2 to 6 carbon atoms.

[0016]

Embedded image -C ₂ H ₄ -, or, -C ₄ H ₈ - is preferably.

Specific examples of the component (A) include o-bis (4-vinylbenzylthioethyl) phthalate, o-bis (3-vinylbenzylthioethyl) phthalate, m-
Bis (4-vinylbenzylthioethyl) phthalate, m
-Bis (3-vinylbenzylthioethyl) phthalate,
p-bis (4-vinylbenzylthioethyl) phthalate, p-bis (3-vinylbenzylthioethyl) phthalate, bis (4-vinylbenzylthioethyl) succinate, bis (3-vinylbenzylthioethyl) succinate, bis ( 4-vinylbenzylthioethyl) adipate, bis (3-vinylbenzylthioethyl) adipate and the like.

The content of the component (A) in the composition of the present invention is in the range of 10 to 50 parts by weight, when the total amount of the components (A) to (C) is 100 parts by weight. By setting the content of the component (A) to 10 parts by weight or more, a high refractive index, heat resistance, transparency, surface hardness, chemical resistance, and the like can be imparted to the plastic lens. When the content is 50 parts by weight or less, the curability of the composition of the present invention by active energy rays is improved.

<Regarding the component (B)> The component (B) used in the present invention is a sulfur-containing di (meth) acrylate compound represented by the above general formula (II). , A component that imparts surface hardness, chemical resistance, and the like, as well as a component that reduces the viscosity of the composition of the present invention and improves the injection workability and the like.

Further, the present invention particularly relates to (A)
If the component and the component (B) are used in combination, transparency,
It is based on the knowledge that a high refractive index plastic lens having excellent heat resistance, chemical resistance, surface hardness and the like can be manufactured with high productivity.

Specific examples of the component (B) include p-bis (β- (meth) acryloyloxyethylthio) xylylene, m-bis (β- (meth) acryloyloxyethylthio) xylylene, p-bis (β -(Meth) acryloyloxyisopropylthio) xylylene, m-bis (β- (meth) acryloyloxyisopropylthio)
Xylylene, p-bis (β- (meth) acryloyloxybutylthio) xylylene, m-bis (β- (meth) acryloyloxybutylthio) xylylene, α, α′-bis (β- (meth) acryloyloxyethylthio) )-
2,3,5,6-tetrachloro-p-xylylene and the like. These can be used alone or in combination of two or more.

Of these, a particularly low-viscosity composition is obtained,
From the viewpoint that a plastic lens having a higher refractive index can be obtained, p-bis (β- (meth) acryloyloxyethylthio) xylylene and m-bis (β- (meth) acryloyloxyethylthio) xylylene are more preferable.

The content of the component (B) in the composition of the present invention is in the range of 10 to 60 parts by weight, when the total amount of the components (A) to (C) is 100 parts by weight. By adjusting the content of the component (B) to 10 parts by weight or more, the viscosity of the composition of the present invention can be reduced, the injection workability is improved, and the refractive index, surface hardness, heat resistance, and transparency are sufficiently high. A plastic lens having properties, chemical resistance and the like can be obtained. However,
Since the component (B) itself is a material having poor impact resistance, the content of the component (B) needs to be 60 parts by weight or less, and if it is used more, a plastic lens having sufficient impact resistance can be obtained. Can not be. <About the component (C)> The component (C) used in the present invention includes:
A (meth) acrylate compound having at least one (meth) acryloyl group in the molecule [excluding the component (A) and the component (B)], which improves the physical properties such as impact resistance of a plastic lens, or It is a component that imparts curability by injection of active energy rays, injection workability, and the like to the composition of the present invention. In particular, if the low-viscosity component (C) is appropriately used, the viscosity of the composition of the present invention can be reduced, and the injection workability can be further improved.

As a specific example of the component (C), bis (4-
(Meth) acryloyloxydiethoxyphenyl) methane, 2,2-bis (4- (meth) acryloyloxyethoxyphenyl) propane, 2,2-bis (4- (meth) acryloyloxydiethoxyphenyl) propane, 2-bis (4- (meth) acryloyloxypentaethoxyphenyl) propane, 2,2-bis (4-
(Meth) acryloyloxypropoxyphenyl) propane, 2,2-bis (4- (meth) acryloyloxydipropoxyphenyl) propane, 2,2-bis (4-
(Meth) acryloyloxypentapropoxyphenyl) propane, 2,2-bis (4- (meth) acryloyloxyethoxy-3,5-dibromophenyl) propane, 2,2-bis (4- (meth) acryloyloxydiethoxy) -3,5-dibromophenyl) propane, 2,2
-Bis (4- (meth) acryloyloxypentaethoxy-3,5-dibromophenyl) propane, bis (4-
(Meth) acryloyloxyethoxyphenyl) sulfone, bis (4- (meth) acryloyloxydiethoxyphenyl) sulfone, bis (4- (meth) acryloyloxythiophenyl) sulfide, bis (4- (meth) acryloyloxyethylthio) Phenyl) sulfide, bis (4- (meth) acryloyloxycyclohexyl) methane, bis (4- (meth) acryloyloxyethoxycyclohexyl) methane, bis (4- (meth)
Acryloyloxycyclohexyl) propane, bis (4- (meth) acryloyloxyethoxycyclohexyl) propane, bis (4- (meth) acryloyloxydiethoxycyclohexyl) propane, dicyclopentanedi (meth) acrylate, ethylene glycol di (meth) Acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth)
Acrylate, polyethylene glycol (n = 4-1)
5) di (meth) acrylate, propylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, polypropylene glycol (n
= 4 to 15) di (meth) acrylate, 1,4-butanediol di (meth) acrylate, polybutylene glycol (n = 2 to 15) di (meth) acrylate, neopentyl glycol di (meth) acrylate, hydroxypivalin Di (meth) acrylate of neopentyl glycol acid ester, 1,6-hexanediol di (meth) acrylate, 1,9-nonanediol di (meth)
Acrylate, methyl (meth) acrylate, butyl (meth) acrylate, hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate,
Cyclohexyl (meth) acrylate, dicyclopentanyl (meth) acrylate, dicyclopentenyl (meth) acrylate, isobornyl (meth) acrylate, bornyl (meth) acrylate, phenyl (meth)
Acrylate, benzyl (meth) acrylate, phenoxyethyl (meth) acrylate, phenoxy-2-methylethyl (meth) acrylate, 3-phenoxy-2
-Hydroxypropyl (meth) acrylate, phenyl-di (oxyethyl)-(meth) acrylate, phenyl-di (2-methyloxyethyl)-(meth) acrylate, phenyltri (2-methyloxyethyl)-(meth) acrylate Phenoxybutyl (meth) acrylate, phenyl-di (oxybutyl)-(meth) acrylate, phenyl-tri (oxybutyl)-(meth) acrylate, 2-phenylphenyl (meth) acrylate, 2-phenylphenoxyethyl (meth) acrylate 4-phenylphenoxyethyl (meth) acrylate, 2-phenylphenyl-2-methyloxyethyl (meth) acrylate, 4-phenylphenyl-2-methyloxyethyl (meth) acrylate, 3- (2-phenylphenyl)- -Hydroxypropyl (meth) acrylate, 3- (4-phenylphenyl) -2-hydroxypropyl (meth) acrylate, 1-naphthyl (meth) acrylate, 2-naphthyl (meth) acrylate, 1-naphthyloxyethyl (meth) Acrylate, 2-naphthyloxyethyl (meth) acrylate,
1-naphthyl-di (oxyethyl)-(meth) acrylate, 2-phenyl-2- (4- (meth) acryloyloxyethoxyphenyl) propane, 2-bromophenyl (meth) acrylate, 4-bromophenyl (meth)
Acrylate, 2,4-dibromophenoxyethyl (meth) acrylate, 2,4,6-tribromophenoxyethyl (meth) acrylate, phenylthioethyl (meth) acrylate, phenylthioethoxyethyl (meth) acrylate, benzylthioethyl ( (Meth) acrylate, 4-chlorobenzylthioethyl (meth) acrylate, 2-chlorobenzylthioethyl (meth) acrylate, p- (β- (meth) acryloyloxyethylthio)-(β-hydroxyethylthio) -xylylene ,
m- (β- (meth) acryloyloxyethylthio)-
Various (meth) acrylates such as (β-hydroxyethylthio) -xylylene and paracumylphenol ethylene oxide-modified (meth) acrylate are exemplified.

Further, a urethane di (meth) acrylate compound obtained by reacting xylylene diisocyanate with hydroxypropyl (meth) acrylate, a urethane di (meth) acrylate compound obtained by reacting isophorone diisocyanate with hydroxypropyl (meth) acrylate, bisphenol A Diglycidyl ether and (meth)
An epoxy di (meth) acrylate compound obtained by reacting acrylic acid, an epoxy di (meth) acrylate compound obtained by reacting tetrabromobisphenol A diglycidyl ether with (meth) acrylic acid, and the like can be given.

These various monomers may be used alone or in a combination of two or more.

The content of the component (C) in the composition of the present invention is in the range of 5 to 40 parts by weight, when the total amount of the components (A) to (C) is 100 parts by weight. When the content of the component (C) is 5 parts by weight or more, any one or more of impact resistance, curability upon irradiation with active energy rays, injection workability, and the like can be improved. Further, by setting the content to 40 parts by weight or less, it is possible to prevent a decrease in the refractive index, heat resistance, and the like of the lens.

The composition of the present invention comprises the components (A) to
It contains the component (C) as a main component, but may further contain, if necessary, a vinyl compound (D) copolymerizable with the components (A) to (C). It is also preferable to mix and use a radical polymerization initiator in order to impart curability. Examples of the radical polymerization initiator include an active energy ray-sensitive radical polymerization initiator (E) and a heat-sensitive radical polymerization initiator (F), and these can be used alone or in combination. In particular, it is preferable to use the active energy ray-sensitive radical polymerization initiator (E) and the heat-sensitive radical polymerization initiator (F) in combination from the viewpoint of productivity of the plastic lens.

<Component (D)> Specific examples of the vinyl compound (D) copolymerizable with the components (A) to (C) include styrene, chlorostyrene, bromostyrene, dibromostyrene, divinylbenzene, and cyclohexane. Vinyl compounds such as dimethanol divinyl ether; allyl compounds such as diethylene glycol bisallyl carbonate, diallyl phthalate and diallyl biphenylate;

In the present invention, the content of the component (D) is preferably 10 parts by weight or less based on 100 parts by weight of the total of the components (A) to (C). By setting the content of the component (D) to 10 parts by weight or less, a plastic lens having more sufficient heat resistance and surface hardness can be obtained without lowering impact resistance.

<Regarding the component (E)> As the active energy ray-sensitive radical polymerization initiator (E), those capable of generating a radical source mainly in response to ultraviolet rays having a wavelength of 200 to 400 nm are preferable. Specific examples of the component (E) include benzoin, benzoin monomethyl ether, benzoin isopropyl ether, benzyl, benzophenone, p-methoxybenzophenone, benzyldimethyl ketal, 2,2-diethoxyacetophenone,
Carbonyl compounds such as 1-hydroxycyclohexylphenyl ketone, methylphenylglyoxylate, ethylphenylglyoxylate, 2-hydroxy-2-methyl-1-phenylpropan-1-one; tetramethylthiuram monosulfide, tetramethylthiuramdi Sulfur compounds such as sulfide; 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bis (2,6
-Dimethoxybenzoyl) -2,4,4-trimethylpentylphosphine oxide and other acylphosphine oxides; These can be used alone or in a mixture of two or more.

Of these, considering compatibility with the composition of the present invention, benzophenone, benzoin isopropyl ether, methylphenylglyoxylate, 1-
Hydroxycyclohexylphenyl ketone, benzyldimethyl ketal, 2,4,6-trimethylbenzoyldiphenylphosphine oxide are more preferred.

In the present invention, the content of the component (E) is preferably in the range of 0.005 to 5 parts by weight, more preferably 0. 5 parts by weight, based on 100 parts by weight of the total of the components (A) to (C). A range of .02 to 2 parts by weight is preferred. When the content of the component (E) is 0.005 parts by weight or more (particularly preferably 0.02 parts by weight or more), the composition of the present invention can sufficiently impart curability. Further, when the amount is 5 parts by weight or less (particularly preferably 2 parts by weight or less), the composition of the present invention can have more excellent deep curability and can prevent coloring of the plastic lens.

<Regarding the component (F)> As the heat-sensitive radical polymerization initiator (F), organic peroxides, azo compounds and the like are preferable. Specific examples of the component (F) include benzoyl peroxide, octanoyl peroxide, diisopropyl peroxydicarbonate, bis (4-t-butylcyclohexyl) peroxydicarbonate, t-butylperoxyisobutyrate, and t-butylperoxyisobutyrate. Butyl peroxy-
Organic peroxides such as 2-ethylhexanoate; 2,2′-
Azobis (2,4-dimethylvaleronitrile), 2,2 '
-Azobisisobutyronitrile, 2,2'-azobis (4
-Methoxy-2,4-dimethylvaleronitrile), 2,
Azo compounds such as 2′-azobis (2-methylbutyronitrile); and the like.

In the present invention, when the component (F) is used, the content is preferably 5 parts by weight or less, more preferably 0.02 to 2 parts by weight, based on 100 parts by weight of the total of the components (A) to (C). Is preferable. By setting the content of the component (F) to 0.02 parts by weight or more, the curability of the composition of the present invention can be improved and sufficient heat resistance can be imparted. When the amount is 5 parts by weight or less (particularly preferably 2 parts by weight or less), it is possible to obtain a plastic lens which is hardly colored, has good transparency and the like, does not cause cracks, and has excellent lens moldability. .

When the component (E) and the component (F) are used in combination in the composition of the present invention, the total amount of both components is based on 100 parts by weight of the total of the components (A) to (C). And 0.
The range is preferably from 005 to 5 parts by weight, particularly from 0.02 to 2 parts by weight.
A range of parts by weight is preferred.

The composition of the present invention may contain an antioxidant, an anti-yellowing agent, an ultraviolet absorber, a bluing agent, a pigment, an anti-settling agent, an antifoaming agent, an antistatic agent, Various additives such as a clouding agent may be added.

The composition of the present invention described above is very useful for production of plastic lenses. That is,
The plastic lens of the present invention is a plastic lens obtained by polymerizing and curing the composition of the present invention.

As a method for producing a plastic lens by curing and molding by using the composition of the present invention with active energy rays or heat or a combination of active energy rays and heat, for example, first, the composition of the present invention is used. The glass, plastic, or two metal molds whose inner surfaces are mirror-polished are poured into a matrix formed by fixing a gasket made of an ethylene-vinyl acetate copolymer or the like, and then heated and heated. And / or a method of curing by irradiation with an active energy ray so as to form a crosslinked polymer having a three-dimensional structure. The curing method, curing time, and the like at this time may be appropriately selected according to the selected resin composition and the like.

When a curing method using an active energy ray is employed as a method for curing the composition of the present invention, it is efficient in terms of labor saving and productivity. For example, the composition of the present invention is injected into the mold, and an active energy ray having a wavelength of 100 to 600 nm of 1 to 100 J / cm ² is applied from one or both sides thereof using a high-pressure mercury lamp, a metal halide lamp, or a halogen lamp. A method of polymerizing and curing by irradiation within the range is preferable. The atmosphere for irradiating the active energy ray may be air or an inert gas such as nitrogen or argon.

The irradiation amount of the active energy ray is set at 0.5.
After gelling and immobilizing the injected composition of the present invention at ７7 J / cm ² , it was left in a hot air oven at 70 to 150 ° C. or in hot water at 70 to 100 ° C. for 1 to 5 hours. Alternatively, a two-step curing method using an active energy ray and heat to complete the polymerization may be employed.

When a plastic lens is molded using the composition of the present invention, as the above-mentioned mold, for example, molds of the same material such as glass and glass can be used. Alternatively, a mold in which different materials selected from metal and the like are combined can be used. In addition, as the gasket, in addition to the thermoplastic resin such as the above-described ethylene-vinyl acetate copolymer, a polyester adhesive tape or the like can be used.

The plastic lens of the present invention may be provided with antireflection, high hardness, abrasion resistance, chemical resistance, antifogging property, surface polishing property, antistatic property, etc., on one or both sides, if necessary. , Or a chemical treatment such as a hard coat treatment, a non-reflection coat treatment, a dyeing treatment, a light control treatment, or a physical treatment.

[0044]

The present invention will be described below in more detail with reference to Examples and Comparative Examples.

<Example 1> As the component (A), o-bis (4-vinylbenzylthioethyl) phthalate (ODP) was used.
SB) as the component (B) and p-bis (β-methacryloyloxyethylthio) xylylene (BMCX) as the component (B).
35 g, benzyl methacrylate (BZM) 5 g as component (C) and 2,2-bis (4-methacryloyloxydiethoxyphenyl) propane (BP2MA)
10 g, 0.05 g of 2,4,6-trimethylbenzoyldiphenylphosphine oxide (TPO) as the component (E) and 0.1 g of t-butyl peroxyoxybutyrate (TBB) as the component (F) are added and mixed. After sufficiently stirring at room temperature, the pressure was reduced to 50 mmHg, and the mixture was degassed for 10 minutes.

This composition was divided into three types of molds, that is, two flat glass plates having a diameter of 70 mm, the inner surfaces of which were mirror-finished in advance, and an inner thickness of 2 mm surrounded by a polyester tape.
And two types of plastic plate molds of 5 mm in size and
A combination of a diameter of 70 mm, a center thickness of 1.5 mm, and a power of minus 6.0 degrees was injected into a plastic lens molding matrix surrounded by a polyester tape.

Next, 3 kW from both sides of each molding master
The composition was irradiated with ultraviolet rays of 50 J / cm ² for about 6 minutes using a high pressure mercury lamp of No. 1 to complete the curing of the composition. Thereafter, the cured product was released from the mold and heated at 130 ° C. for 1 hour to carry out an annealing treatment to obtain a plastic lens and a plastic flat plate for an evaluation test.

<Examples 2 to 5> A composition of the present invention was prepared in the same manner as in Example 1 except that the components shown in Table 1 were used, and a plastic lens and a plastic plate for evaluation test were prepared. I got

Example 6 The first step (irradiation energy is shown in Table 1) of irradiating ultraviolet rays for about 1 minute using each component in the ratio shown in Table 1 was followed by a heat treatment using a hot air dryer. A composition of the present invention was prepared in the same manner as in Example 1 except that two steps (heating temperature and heating time are shown in Table 1) were performed, and a plastic lens and a plastic flat plate for an evaluation test were obtained.

Comparative Example 1 100 g of diethylene glycol bisallyl carbonate (trade name: CR-39, manufactured by PPG) and 3 g of diisopropyl peroxydicarbonate (trade name: Parloyl IPP, manufactured by NOF Corporation) were mixed and mixed well. After stirring, the mixture was poured into each of the same molds as used in Example 1, and the mixture was poured at 45 ° C for 10 hours, at 60 ° C for 3 hours,
After holding at 80 ° C. for 3 hours and at 90 ° C. for 6 hours, removing the cured product from the matrix, annealing was performed by heating at 120 ° C. for 1 hour to obtain a plastic lens and a plastic flat plate for an evaluation test. .

<Comparative Examples 2 to 7> Compositions were prepared in the same manner as in Example 1 except that the respective components were used in the proportions shown in Table 2, and plastic lenses and plastic flat plates for evaluation tests were obtained. . In Comparative Example 6, the photocurability was extremely poor, and no cured product was obtained. In Comparative Example 7,
The curability of the composition was poor, and a cured product in which uncured portions remained was obtained.

<Evaluation> The following evaluations were made on the plastic lenses and flat plates obtained in each of the examples and comparative examples. Table 3 shows the evaluation results.

Visible light transmittance (%): Measured according to ASTM D-1003 using a flat plate having a thickness of 2 mm.

Refractive index: using a flat plate having a thickness of 2 mm, width 10
mm, length 20mm, and Abbe refractometer,
The refractive index of the 589.3 nm D line was measured at 20 ° C.

Surface hardness: Using a flat plate having a thickness of 5 mm, Rockwell hardness (L scale) was measured according to JIS K7202.

Heat resistance (Tg, ° C): Tg (° C) under a load of 10 g was measured by TMA measurement using a flat plate having a thickness of 2 mm.

Impact resistance: A minus lens having a center thickness of 1.5 mm was used, and a height of 127 cm was applied to the center of the lens.
A 6.3 g steel ball was dropped, and the collision portion of the lens was observed. If there was no crack, chip, or break, it was good (○). If there was any crack, chip, or break, it was bad (×). And

Chemical resistance: Using a minus lens having a center thickness of 1.5 mm, wiping the surface of the lens with gauze containing acetone and toluene, examining the change, and checking the change without change as good (〇), whitening the surface The result was evaluated as bad (x).

Injection workability: The degree of difficulty in injecting the composition into the matrix was judged. A sample having an appropriate viscosity and easy to inject was evaluated as good (良), and a sample having a high viscosity and difficult to inject and causing injection distortion. Was evaluated as poor (x).

Productivity: Expressed by the time required for curing.

[0061]

[Table 1]

[0062]

[Table 2] The abbreviations in Tables 1 and 2 indicate the following compounds.

ODPSB: o-bis (4-vinylbenzylthioethyl) phthalate KBSB: bis (4-vinylbenzylthioethyl) succinate MDPSB: m-bis (4-vinylbenzylthioethyl) phthalate BMCX: p-bis (β -Methacryloyloxyethylthio) xylylene BZM: benzyl methacrylate NEGMA: nonaethylene glycol dimethacrylate BPMA: 2,2-bis (4-methacryloyloxyethoxyphenyl) propane BP2MA: 2,2-bis (4-methacryloyloxydiethoxyphenyl) Propane PCPHA: 2-phenyl-2- (4-acryloyloxyethoxyphenyl) propane POA: Phenoxyethyl acrylate DVB: Divinylbenzene TPO: 2,4,6-trime Tylbenzoyldiphenylphosphine oxide TBB: t-butyl peroxyoxybutyrate IPP: diisopropyl peroxydicarbonate CR39: diethylene glycol bisallyl carbonate

[0064]

[Table 3]

[0065]

As described above, the composition of the present invention is rapidly cured by irradiation with active energy rays,
By using this composition, a plastic lens having an extremely high refractive index, excellent transparency, impact resistance, chemical resistance, heat resistance and the like and excellent surface hardness can be produced with high productivity.

The present invention relates to a spectacle lens, a Fresnel lens,
It is also suitable for various optical lens products such as rod lenses, lenticular lenses and fθ lenses, and optical products such as prisms such as triangular prisms and triangular prism sheets.

 ──────────────────────────────────────────────────続 き Continuing on the front page (72) Inventor Tetsuya Ikemoto 20-1 Miyukicho, Otake City, Hiroshima Prefecture Inside Mitsubishi Rayon Co., Ltd. Central Research Laboratory

Claims (3)

[Claims] (A) General formula (I) (Wherein each R ¹ independently represents H or CH ₃ ;
² represents a hydrocarbon having 2 to 6 carbon atoms. 10 to 50 parts by weight of a sulfur-containing aromatic compound represented by the formula (I):
I) (Wherein each R ³ independently represents H or CH ₃ ;
⁴ and R ⁵ each independently represent a hydrocarbon group having 1 to 4 carbon atoms, X represents Cl, Br or I, m and n
Each independently represents an integer of 1 to 5, and p represents an integer of 0 to 4. And 10 to 60 parts by weight of a sulfur-containing di (meth) acrylate compound represented by the formula (C) and (C) a (meth) acrylate compound having at least one (meth) acryloyl group in a molecule (the component (A) and ( B)
5 to 40 parts by weight (excluding components) [However, the total of the components (A) to (C) is 100 parts by weight. ] A composition for a plastic lens, comprising: (2) R ² in the general formula (I) is -C ₂ H ₄ -, or, -C ₄ H ₈ - plastic lens composition of claim 1 wherein representing the. 3. A plastic lens obtained by polymerizing and curing the composition according to claim 1.