JPH0480213A - Composition for plastic lens - Google Patents

Abstract

PURPOSE:To prepare the title compsn. giving a lens excellent in heat resistance, transparency, surface hardness, and chemical resistance by compounding, as the main components, a compd. obtd. by the reaction of a specific compd. with a compd. having an SH group and a radical polymerizable monomer or oligomer, each in a specified amt. CONSTITUTION:10-90pts.wt. compd. obtd. by the reaction of a compd. of the formula (wherein R is H or CH3) with a compd. having an SH group [e.g. 1,3-bis(mercaptomethylene)benzene] and 90-10pts.wt. radical polymerizable monomer or oligomer [e.g. 2,2-bis(3,5-dibromo-4-methacryloxyethoxyphenyl)propane] are compounded as the main components.

Description

[Detailed Description of the Invention] [Field of Industrial Application] The present invention provides a plastic that has a high refractive index, excellent heat resistance, surface hardness, chemical resistance, and transparency, and has low distortion and can be manufactured industrially. The present invention relates to a composition for lenses.

[Conventional technology]

Materials conventionally used for optical purposes include polymethyl methacrylate, polycarbonate, and polystyrene resin. However, these resins are
(thermoplastic), so none of them had satisfactory heat resistance, surface hardness, or chemical resistance. Polydiethylene glycol bisallyl carbonate, which is widely used for eyeglass lenses, is a reticular polymer (thermosetting plastic) and has improved heat resistance and chemical resistance, but is still insufficient. In order to solve these problems, in JP-A No. 57-1366 (12), the reaction between an inocyanate compound and an unsaturated compound containing a hydroquine group'
A plastic lens using a urethane resin which is produced by I-1 polymerization of a tonic acid has been disclosed. Also,
In order to obtain a high refractive index plastic lens,
-199016, JP-A-60-217229, JP-A-6
3-46213, JP-A-63-130614, JP-A-6
No. 313C1615, JP-A-63-265922, and JP-A-64-54021 disclose plastic lenses using a thiourethane resin which is polymerized with an isocyanate compound and a chemical compound containing a thiol group.

[Problem to be solved by the invention]

However, in the urethane resin obtained by addition polymerizing the reaction product of an isocyanate compound and an unsaturated compound containing a hydroxyl group, the monoisocyanate compounds include methyl isocyanate, ethyl isocyanate, butyl isocyanate, and probilisone. Ane-1., octadenylisonanate, phenylisonanate, methachlorophenylisonanate, diisocyanate compounds include hexamethylene diisocyanate, octamethylene diisocyanate-1., nonamethylene diisocyanate, isophorone diisocyanate, 2,2.4-Trimethylhexamethylene diisocyanate, n/chlorohequinylmethane neusonanate, lysine thiisonanate methyl ester, tetramethylene diisocyanate, quinrylene diisocyanate, bis(isocyanatemethyl)cyclohexane, trilene isocyanate, 44
'-diphenylmethane diisocyanate, l-lysine diisocyanate, naphthalene cysonanate, 33
There are a number of isocyanate compounds, such as '-dimethyl-4,4'-bisphenylene diisocyanate. However, there are only a few isocyanate compounds that are non-yellow type and are commercially produced. Examples of hydroquine-containing unsaturated compounds include 2-hydroquinethyl acrylate, 2-hydroquinepropyl acrylate, 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl methacrylate, There are 2-hydroxypropyl methacrylate, allyl alcohol, methallyl alcohol, etc.Although there are differences in polymerization rate and physical properties due to differences in reactive groups, the degree of influence on physical properties depends on the structure of the compound. big.

In other words, the dependence on the isocyanate compound is large, which causes the problems mentioned above.

Furthermore, since the reaction between an isocyanate compound and a thiol group-containing compound involves an addition reaction in a template, it is difficult to completely react the isocyanate groups, making it impossible to obtain desired physical properties. Furthermore, it is difficult to control the reaction and distortion is likely to occur. The present invention was made to solve the above-mentioned problems, and has a high refractive index, excellent heat resistance, surface hardness, chemical resistance, and transparency, and also has low distortion and can be manufactured industrially. Regarding plastic lenses.

[Means to solve the problem]

The present invention uses a compound 1 obtained by reacting a compound of general formula (1)% formula (1) with a thiol group-containing compound as a main component and a radically polymerizable monomer or oligomer (1 to 90 parts by weight). -90 to 1θ parts by weight.

The present invention will be explained in detail below.

A monomer having a functional group and a thiourethane group can be obtained by reacting the isocyanate compound represented by the general formula (1) with a thiol group-containing compound. The isocyanate compounds used here are 2-isocyanate ethyl methacrylate and 2-isocyanate ethyl acrylate, and the characteristics of each monomer are that they appear as colorless and transparent liquids, have a high conversion rate, and are highly pure with no by-products. It is. Furthermore, the reaction with thiol groups is simple and fast, occurs at low temperatures, and is inexpensive. Any compound having 1 to 6 1,000-ol groups can be used as the compound to be reacted with the hexamer. The above thiol group-containing compound has a methacrylic group, an acrylic group,
It may have a functional group such as an allyl group, a methallyl group, or a vinyl group.

Further, when the compound is used as a composition for high refractive index, it is desirable that the compound has an aromatic system or a halogen atom in its structure. Next, compounds containing a thiol group will be shown, but the present invention is not limited thereto.

Monothiol group-containing compounds methanethiol, ethanethiol, propanethiol,
Aliphatic thiols such as butanethiol, pentanethiol, hexanethiol, cyclopentanethiol, cyclohexanethiol, methylcyclohexanethiol,
Alicyclic acyloalcohols such as trimethylcyclohexanethiol, norbornylthiol, adamantylthiol, dicyclopentenylthiol, tricyclodecanylthiol, tetrahydroxythiophenethiol, thiophenol, pencylthioalcohol, phenylethanethiol, phenylpro Banthiol, phenoxyethanethiol, phenoxyethoxyethanethiol, monochlorobenzenethiol, trichlorohenzenethiol, pentachlorobenzenethiol, monobromobenzenethiol, tribromobenzenethiol, pentabromobenzenethiol, monoiothohenzenethiol, triiod Benzentiol, bentaiodobenzenethiol, monobromobenzylthiol, trichlorobenzylthiol, pentachlorobenzylthiol, monobromobenzylthiol, dibromobenzylthiol, tribromobenzylthiol, pentabromobenzylthiol,
Monoiodobenzylthiol, diodobenzylthiol, triiodobenzylthiol, bentaiodobenzylthiol, thiocresol, dimethylthiophenol, trimethylthiophenol, 1-thionaphthol, 2
-thionaphthol, 1-naphthyloxyethanethiol, 2-naphthyloxyethanethiol, 1-chloro-2
-thionaphthol, 4-chloro-2-thionaphthol,
6-chloro-2-thionaphthol, 4-chloro-1-thionaphthol, ]-]bromo-2-thionaphthol 6-bromo-2-thionaphthol, 4-bromo-1-thionaphthol
4-bromo-2-thionaphthol, 1,6-dichloro-2-thionaphthol, 2゜4-dichloro-2-thionaphthol, 1,6-dibromo-2-thionaphthol, 2
, 4-dibromo 2-thionaphthol, 2-phenylthiophenol, 4-phenylthiophenol, 4-phenylphenoxyethanethiol, 2-phenylphenyl-
There are 2-methyloxyethanethiol, 2-phenylphenyl-2-hydroxyprobanthiol, 4-phenylphenyl-2-hydroxylobanethiol, etc., and these compounds and the compound of general formula (1) are basically is a compound obtained by equimolar reaction.

Dithiol group-containing compounds 1. Aliphatic dithiols such as 2-ethanedithiol, 1,4-butanedithiol, 1,6-hexanedithiol, ethylene glycoldithiocricolate, hexanedithiol, norbornyldithiol, isobornyldithiol, Adamantyldithiol, dicyclopentenyldithiol, 1-lycyclopentenyldithiol, 2,5-
Cycloaliphatic dithiols such as dimercapto-1,4-dithiane, dimercapto-hensen, bis(mercaptomethylene)
Benzene, bis(mercaptoethylene)benzene, bis(mercaptoethyleneoxy)benzene, bis(mercaptoethyleneoxy)benzene, bis(mercaptomethylenethio)benzene, bis(mercaptoethylenethio)
Benzene, 22bis(4-mercaptoethoxyphenyl)-propane, bis(4-mercaptoethoxyphenyl)ethane, bis(4-mercaptoethoxyphenyl)sulfide, bis(4-mercaptoethoxyphenyl)sulfone, bis(4-mercapto) ethquinphenyl) sulfone, 2,2-bis(3゜5-dimethyl-4-mercaptoethyl)-propane, 2,2-bis(3,5-dibromo-4-mercaptoethylphenyl)-propane,
2.2-bis(3,5-dibromo-4-mercaptoethoxyphenyl)-propane, 2,2-bis(3,5-dibromo-4-mercaptoethylenethiophenyl)propane, 2.4-dimercaptonaphthalene, 2,7-dimercaptonaphthalene, 4,4'-dimercaptobiphenyl, etc., and the general formula (1
) is basically reacted with twice the mole amount.

Compounds containing trithiol groups trimercaptoglycerin, trimercaptobenzene,
Tris(mercaptomethylene)benzene, tris(mercaptoethylene)benzene, tris(mercaptomethyleneoxy)benzene, tris(mercaptoethyleneoxy)benzene, tris(mercaptoethylenethio)benzene, tris(mercaptomethylenethio)benzene, trithiomethylolpropane etc., and these compounds 1
A compound obtained by reacting the compound of general formula (1) with basically 3 times the mole.

There are compounds containing four or more thiol groups, such as tetramercaptobenzene, pentamercaptobenzene, pentathioerythritol, dipentathioerythritol, etc., and for each thiol (mercapto) group of these compounds, a compound of general formula (1) is used. is obtained by reacting with one isocyanate group.

Thiol (mercapto) group-containing compounds other than those shown above can be synthesized from hydroxy group-containing compounds by Newman reaction.

The addition reaction between the isocyanate compound of general formula (1) and the thiol group-containing compound can be carried out using a known method, for example, using a thiol group-containing compound and a catalyst in the presence of an isocyanate compound.
For example, a mixture of di-n-butyltin n-laurate and
It can be produced by dropping and reacting under conditions of 0 to 90°C.

The radically polymerizable monomer or oligomer of the present invention is a compound having at least one polymerizable double bond in the molecule, and is used to supplement heat resistance, dyeability, impact resistance, surface hardness, etc. Furthermore, it is also a component that makes it possible to lower the viscosity of the composition. In particular, in the present invention, the general formula (
I) Many of the thiourethane (meth)acrylates obtained by reacting with thiol group-containing compounds have high viscosity, so in order to improve casting workability, it is desirable that the viscosity of the resin composition be as low as possible. .

Specific examples of radically polymerizable monomers or oligomers include methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, and (meth)acrylate.
n-butyl acrylate, butyl (meth)acrylate, t-butyl (meth)acrylate, pentyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, (
n-hexyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, butoxyethyl (meth)acrylate, allyl (meth)acrylate, (
Methallyl acrylate, glycidyl (meth)acrylate, N (meth)acrylate.

N-dimethylaminoethyl, (meth)acrylic acid N,N
-diethylaminoethyl, 2-cyanoethyl (meth)acrylate, dibromopropyl (meth)acrylate, vinyl 2-pyrrolidone (meth)acrylate, polyethylene glycol monoalkyl ether (meth)acrylate, polypropylene glycol mono(meth)acrylate Alkyl ether, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, (
2-hydroxybutyl meth)acrylate, tetrahydrofurfuryl (meth)acrylate, phosphonityl (meth)acrylate, phenyl (meth)acrylate, benzyl (meth)acrylate, phenoxyethyl (meth)
Acrylate, phenoxy-2-methylethyl (meth)
Acrylate, 3-phenoxy-2-hydroxyerlopyl (meth)acrylate, Phenyludi(oxyethyl)-(methane acrylate, Phenyl-tri(oxyethyl)-(meth)acrylate, Phenyludi(2-
Methyloxyethyl)-(meth)acrylate, Phenyl-tri(2-methyloxyethyl)-(meth)acrylate, Phenoxybutyl(meth)acrylate, Phenyludi(oxybutyl)-(meth)acrylate, Phenyl-tri(oxybutyl)- (meth)acrylate, 2-phenylphenyl (meth)acrylate, 4 phenyl phenyl (meth) acrylate, 4 phenyl phenoxyethyl (meth) acrylate, 2-phenylphenyl-2-methyloxyethyl (meth) acrylate, 4
-phenylphenyl 2-methyloxypropyl (meth)
Acrylate, 4-phenylphenyl-2-hydroxyoxypropyl (meth)acrylate, 2-naphthyl (
meth)acrylate, 1-naphthyl(meth)acrylate, 1-naphthyloxyethyl(meth)acrylate,
2-naphthyloxyethyl (meth)acrylate, 1-
naphthyroudi(oxyethyl)(meth)acrylate,
2-naphthyl-di(oxyethyl)-(meth)acrylate, 1-naphthyl-2-methyloxyethyl-(meth)acrylate, 2-naphthyl-2-methyloxyethyl (meth)acrylate, 1-naphthyl-2-hydroxypropyl (meth)acrylate, 2-naphthyl-2
-Hydroxyoxypropyl (meth)acrylate, 2
-Bromophenyl (meth)acrylate, 4-bromophenyl (meth)acrylate, 2,4-dibromophenyl (meth)acrylate, 2,4.6-tribromophenyl (meth)acrylate, 2,3.4,5. 6-pentabromophenyl (meth)acrylate, 2,4-dibromophenoxyethyl (meth)acrylate, 2°4.
6-)-ribromophenyl di(oxyethyl)-(meth)acrylate, 2,4,6-dribromophenyl-2-methyloxyethyl (meth)acrylate, 2-bromobenzyl (meth)acrylate, 4-bromohensyl ( (meth)acrylate)-12,4-dibromobenzyl (meth)acrylate, 2.4.6-)dibromobenzyl (meth)acrylate, 2,3,4,5.6-pentabromobenzyl (meth)acrylate, 2 -chlorophenyl (meth)acrylate, 2,4-dichlorophenyl (meth)acrylate, 2,4.64 dichlorophenyl (meth)acrylate, 2. 3゜4.5.6-pentachlorophenyl (meth)acrylate, 2.4-dichlorophenyloxyethyl (meth)acrylate, 2,4
．． 6-) Lichlorophenyl quinethyl (meth)acrylate, 2.4.6-) Lichlorophenyl-oxyethyl-(meth)acrylate, 2,4.6-tricrylorophenoxy 2-methyloxyethyl (meth)acrylate, 2,4.64ribromophenyl-2-hydroxyoxypropyl (meth)acrylate, 2,3,
4,5.6-bentapromophenyl-2-hydroxyoxypropyl (meth)acrylate, 2-phenyl-4
-bromophenyl (meth)acrylate, 2-(4-bromophenyl)-4,6-dibromophenyl (meth)acrylate, 2-(4-chlorophenyl)4゜6-dichlorophenyl (meth)acrylate, 2-phenyl-4
-bromophenyloxyethyl (meth)acrylate,
2-(4-bromophenyl)-4,6-dibromophenyloxyethyl (meth)acrylate, 2-(2,4
,64ribromophenyl)-4,6-dibromophenyl (meth)acrylate, 2-(2,4-dibromophenyl)-4,6-dibromophenyloxyethyl (meth)acrylate, 1-(4-chloronaphthyl)-oxyethyl -(meth)acrylate, 2-(4-chloronaphthyl)-oxyethyl(meth)acrylate, 1-(4
-bromonaphthyl)-oxyethyl (meth)acrylate, 2(4-bromonaphthyl)-oxyethyl-(meth)acrylate, 1-[3-(2-bromonaphthyl)
Co-2-hydroxypropyl (meth)acrylate, 2
- Mono (meth) such as [3-(2-bromonaphthyl)cono-hydroxyoxypropyl (meth)acrylate
Acrylate compounds; ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate,
Polyethylene glycol di(meth)acrylate compounds such as bentaethylene glycol di(meth)acrylate and nonaethylene glycol di(meth)acrylate;
Polypropylene glycols such as propylene glycol di(meth)acrylate, dibropylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, tetrabropylene glycol di(meth)acrylate, nonapropylene glycol di(meth)acrylate, etc. di(meth)acrylate compounds; butylene glycol di(meth)acrylate, dibutylene glycol di(meth)acrylate, tributylene glycol di(meth)acrylate, tetrabutylene glycol di(meth)acrylate, nonabutylene glycol di(meth)acrylate, ) Di(meth)acrylate compounds of polybutylene glycol such as acrylate; 1,3-butylene glycol di(meth)acrylate, ], 6-hexamethylene di(
(meth)acrylate), 1.14-tetradecamethylene di(meth)acrylate, neopentyl glycol di(meth)acrylate, di(meth)acrylate compound of caprolactone adduct of neopentyl glycol hydroxypivalate, neopentyl glycol adipate Ji(
meth)acrylate, dicyclopentenyl di(meth)acrylate, synchlobentanyl di(meth)acrylate, 2-(2-hydroxy-1,1-dimethyl)-5-
Hydroxy (meth)acrylate, trimethylolpropene tri(meth)acrylate, ditrimethylolpropane tetra(meth)acrylate, pentaerythritol tri(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, Di(meth)acryloyloxyethyl isocyanurate, tris(meth)acryloyloxyethyl isocyanurate, 2,2-bis(4-
(meth)acrylooxyphenyl)-propane, 2.
2-bis(4(meth)acryloyloxyjetoxyphenyl)propane, 22-bis(4-(meth)acryloyloxypentaethoxyphenyl)-propane, 2,
2-bis(4-(meth)acryloyloxyethoxy-
35-dibromophenyl)-propane, 2,2-bis(
4-(meth)acryloyloxyjethoxy-3,5-
dibromophenyl)propane, 2,2-his(4-(meth)acryloylpentaethoxyphenyl-3,5-dibromophenyl)propane, 2,2-bis(4-(meth)acryloyloxyethoxy-3-phenylphenyl) -Propane, bis(4-(meth)acryloyloxyethoxyphenyl)-sulfone, bis(4-(meth)
acryloyloxyjetoxyphenyl)-sulfone, bis(4-(meth)acryloylleoquinpentaethoxyphenyl)-sulfone, bis(4-(meth)acryloyloxyethoxy-3-phenylphenyl)-sulfone, bis(4-(meth)acryloylleoquinpentaethoxyphenyl)-sulfone, 2) Acryloyloxyethoxy-3,5-dimethylphenyl)-sulfone, bis(4-(meth)acryloyloxyphenyl)sulfide, bis(4-(meth)acryloyloxyjethoxyphenyl)-sulfide, bis(4- (meth)acryloylpentaethoxyphenyl)-sulfide, di((meth)acryloyloxyethoxy)phosphate-1.
Tri((meth)acryloyloxyethoxy)phosphate, 2.4-di(meth)acryloxynaphthalene, 2.6-di(meth)acryloxynaphthalene, 1.
Polyfunctional compounds such as 7-di(meth)acryloxynaphthalene (
Meth) acrylate compounds: styrene, chlorstyrene, bromostyrene, dibylhensen, 1-vinylhensen, 1-vinylnaphthalene, 2-vinylnaphthalene, N
- Vinyl compounds such as vinylpyrrolidone; allyl compounds such as ethylene glycol bisallyl carbonate, trimethylolpropane diallyl, dimethallyl phthalate, diallyl phthalate, (meth)acrylic acid and barium,
Examples include metal salts of lead, antimony, titanium, tin, and zinc. These may be used alone or in combination of two or more.

In the composition for plastic lenses of the present invention, if a large amount of the compound obtained by reacting the general formula (1) with a thiol group-containing compound is used, the viscosity will be high, and the cured product will be brittle and have reduced rain impact resistance. There are many things to do. When the amount is low, heat resistance and surface hardness decrease. In the present invention, since there are many compounds obtained by reacting the general formula (1) with a thiol group-containing compound, it is difficult to limit the composition ratio, or for the above-mentioned reasons, 10 to 90% by weight of the composition. parts, preferably 30 to 70 parts by weight.

The composition for plastic lenses of the present invention may contain various additives such as an antioxidant 11-agent, an anti-yellowing agent, an ultraviolet absorber, a blue ink agent, and a pigment, which may impair the effects of the present invention. It may be blended within a certain range.

Examples of the polymerization initiator used in curing the composition for plastic lenses of the present invention include organic compounds such as benzoyl peroxide, t-butylperoxyisobutyrate, and t-butylperoxy-2-ethylhexanoate. peroxide, 22'-azobisisobutyronitrile, 2,2'-
Azo compounds such as azobis(2,4-dimethylvaleronitrile), 2-hydroquine-2-methyl-1-phenylpropan-1-one, methylphenylglyoxylate,
Examples include photopolymerization initiators such as 2,4,6-trimethylhenzoylsipheniphosphine oxide. These are 1
It is used either as a species or as a mixture of two or more species. The blending ratio of the polymerization initiator is approximately 0.005 to 5 parts by weight based on the total weight of the resin components.

In the polymerization curing method, for example, the composition of the present invention containing a polymerization initiator is injected into a mold made of two mirror-polished glass plates through a cassette made of ethylene-vinyl acetate copolymer, and one side of the mold is injected. Alternatively, it is carried out by irradiating active energy rays from both sides or by heat treatment.

Moreover, irradiation and heating may be combined. Here, the molds include glass and glass, glass and plastic plates,
There are molds made of glass, metal plates, or a combination of these. (2) As a single mold, in addition to thermoplastic resin such as the one described above, two molds may be fixed with a polyester adhesive tape or the like.

〔Example〕

Hereinafter, the present invention will be explained in more detail with reference to Examples and Comparative Examples, but the present invention is not limited thereto. The abbreviations for the 711-mer are as follows.

Ml 1-Isocyanate ethyl methacrylate = 1-isocyanate ethyl acrylate: Thiourethane methacrylate obtained by reacting equimolar amounts of M1 and tricyclo(5,2,102L')decane-8-thiol UM2: Ml and 1.3 - Thiourethane acrylate made by reacting equimolar amounts of bis(mercaptomethylene)benzene (Ml4): Thiourethane methacrylate Ml and 2-mercaptonaphthalene made by reacting equimolar amounts of M1 and 2.4.6-tribromobenzylthiol Thiourethane methacrylate UM5: Ml and 1.6-hexanedithiol were reacted in equimolar amounts with 2:1
Thiourethane dimethacrylate UM6 reacted with Ml and 2,2-bis(35-mercaptophenyl)-propane in a ratio of 2=1 mole Thiourethane dimethacrylate UM7: Thiourethane dimethacrylate UAI made by reacting 2-hydroxypropyl methacrylate and xylylene diisocyanate in 2.1 moles: Thiourethane acrylate UA2 made by reacting equimolar amounts of Al and hensylthiol: A2 and 2.2-bis( Thiourethane cyacrylate-1 M2, which was reacted with 4-mercaptoethoxyphenyl (4-mercaptoethoxyphenyl)-propane in a ratio of 1=2 moles, methyl methacrylate M3 Nidrinchloro(5,2,1,026)decane-8
-yl methacrylate M4: 2.2-bis(3,5-dibromo-4 methacrylic acid quinphenyl) Propane M5: 2-methacrylooxynaphthalene Ml: Styrene M8: 2-hydroxyethyl methacrylate M9:
1-methacrylooxymethylene-2゜4.6-)ribromobenzene Mlo: hexanediol dimethacrylate Mll: 2
, 2-bis(4-acryloyloxyphenyl)-propane M12 diethylene glycol bisallyl carbonate M13: hexamethylene diisocyanate M14:1,
Example of synthesis of 3-bis(mercaptomethylene)benzene (synthesis of thiourethane(meth)acrylate) 1-Isocyanate ethyl methacrylate (synthesis of thiourethane(meth)acrylate)
Ml) 155 parts, hydroquinone monomethyl ether 0
．． Add 2 parts of tricyclo (5 parts) and stir at 60℃.
, 2,1,026) A mixture of 148 parts of decane-8-thiol and 0.2 parts of di-n-butyltin laurate was added dropwise over 3 hours. After the dropwise addition, the reaction was further continued at 70°C for 8 hours, and thiourethane methacrylate (UMI)
1″4t.

In the case of a thiol group-containing compound or solid, it may be dissolved in a radically polymerizable monomer or oligomer and added dropwise, or it may be mixed with an isocyanate and reacted.

Polymerization Example 1 (Example 1) 60 parts of UMI, 240 parts of M, 2.4. 6 trimethyl benzoyl phosphin oxide 0°03 parts, t-
Butyl peroquine isobutyrate 01 part, tridecyl phosphate 0.2 part, 2-hydroxybenzophenone 0
．． After mixing 2 parts and stirring well at room temperature, 50mmH
The pressure was reduced to H and degassed for 10 minutes.

This composition was injected into a mold in which two mirror-finished glasses with a diameter of 70 mm were combined to have a thickness of 4 mm and surrounded by a polyvinyl chloride gasket.

Next, 2 parts w of high-pressure mercury lamps were used on both sides of the mold.
After irradiating with ultraviolet light of 000 m j / cm 2 , it was heated at 130° C. for 2 hours. Thereafter, the lens was removed from the mold and annealed by heating at 100° C. for 1 hour. The lenses manufactured in this manner were evaluated using the following evaluation method, and the results are shown in Table 1.

Visible light transmittance (96): ASTM D-10036
Measured according to 1.

Yellowness: Measured according to the transmission measurement method of JIS K7130, and the Y and I values are shown.

Refractive index: Measured at 589.3 nm OD line using Atsube refraction g1.

Rockwell hardness: Measured according to JIS K7202.

Heat resistance: Tg at a load of 10 g was shown by TMA measurement.

Polymerization strain: Strain was observed using a ballarimeter. No O9 distortion at all △: Slight distortion ×: Much distortion Polymerization Example 2 (Example 2) UM2 5 (1 part, M450 parts, 2 parts of cyisopropyl peroxycarbonate, 2 (2 '-Hydroxy-5'
-Methylphenyl)benzotriazole (0.1 part) was mixed, and the mixture was thoroughly stirred at room temperature, and then the pressure was reduced to 50 mmHg and degassed for 10 minutes.

It was poured into a mold in the same manner as in Polymerization Example 1, and heated at 35°C for 6 hours at 50°C.
The molding was performed by storing at 4 hours at 70°C, 5 hours at 85°C. The lens was removed from the mold and annealed by heating at 100° C. for 1 hour. The lens thus produced was evaluated in the same manner as in Polymerization Example 1 (Example 1), and the results are shown in Table 1.

Polymerization Example 3 (Comparative Example 6) 49.7 parts of Ml3, 0.3 parts of M14, di-n-butyltin laurate (1,2 parts, and 2 parts of 2-hydroxyhensiphenone) were mixed and stirred at room temperature. After stirring, 5
The pressure was reduced to 0 mm Hg and degassed for 10 minutes.

The mold was poured into the same mold as in Example 1 except that a glass mold treated with a silicone-based baking f=j type mold release agent was used, and the mixture was heated at 40°C for 3 hours, at 60°C for 2 hours, and at 80°C for 2 hours. , and heated at 100°C for 2 hours.

The lens was removed from the mold and annealed by heating at 100° C. for 1 hour. The lens thus produced was evaluated in the same manner as in Polymerization Example 1 (Example 1), and the results were evaluated in the first
Shown in the table.

Examples 3 to 8 Comparative Examples 1 to 5 Monomers were used in the proportions shown in Table 1, and the polymerization was conducted as in Polymerization Example 1.
．． A lens was manufactured and evaluated in the same manner as in Example 1.2, except that either one of Example 2 was used. The results are also shown in Table 1.

〔Effect of the invention〕

The composition for plastic lenses of the present invention has excellent heat resistance, surface hardness, chemical resistance, and transparency, and has little distortion.
It can be manufactured industrially. These characteristics make it useful as an optical material for eyeglass lenses, camera lenses, optical discs, etc.

that's all Applicant: Seiko Epson Corporation

Claims (1)

[Claims] (1) Compound 10 obtained by reacting a compound of the general formula (I) ▲mathematical formula, chemical formula, table, etc.▼(I) (R is H or CH_3) with a thiol group-containing compound as the main component A composition for a plastic lens, comprising ~90 parts by weight and 90 to 10 parts by weight of a radically polymerizable monomer or oligomer.