JPH0384031A - Polysulfide-based resin and lens consisting of the same resin - Google Patents

Abstract

PURPOSE:To obtain the title resin having high refractive index and extremely low disperse and suitable for lens by reacting bis[(mercaptoethyl) thio]mercaptopropane with a compound having plural reactive unsaturated bonds. CONSTITUTION:The objective resin obtained by reacting (A) 1,2-bis[(2- mercaptoethyl)thio]-3-mercaptopropane expressed by the formula with (B) a compound (e.g. reaction product of diaziridenepentaerythritol and ethylene glycol) having two or more reactive unsaturated bonds in one molecule.

Description

[Detailed description of the invention] [Industrial application field]

The present invention relates to a polysulfide resin having a high refractive index, extremely low dispersion, and extremely low sulfur odor during monomer handling and post-processing, and a lens made of the resin. [Prior Art] Plastic lenses are lighter, more difficult to break, and easier to dye than inorganic lenses, so they have rapidly become popular in optical elements such as eyeglass lenses and camera lenses in recent years. Resins currently widely used for these purposes include:
There are products obtained by radical polymerization of diethylene glycol bis(allyl carbonate) (hereinafter referred to as A and C). This resin has various characteristics such as excellent impact resistance, light weight, excellent dyeability, and good processability such as cutting and polishing properties. There is. However, the refractive index of an inorganic lens (no
= 1.52), which is small at no = 1.50, and in order to obtain optical properties equivalent to glass lenses, it is necessary to increase the center thickness, edge thickness, and curvature of the lens. It is inevitable that Lenses made of polyvalent allyl compounds, polyvalent acrylic compounds, and polyfunctional thiols are used as resins for lenses that provide a high refractive index (Japanese Patent Application Laid-Open Nos. 59-87213 and 59-19392).
, 63-234032) has been proposed. [Problem to be solved by the invention] The lens made of the lens resin that provides a high refractive index has the following properties:
Although the refractive index is higher than that of lenses using D, A, and C, it is still insufficient in terms of refractive index, and in order to improve the refractive index, lenses with aromatic rings such as naphthalene rings in the molecule are used. It has drawbacks such as high dispersion and poor weather resistance. Furthermore, many of the polyfunctional polythiols used in these resins have a strong sulfur odor, which causes discomfort to workers when handling the monomer or during post-processing. [Means for Solving the Problems] In view of this situation, the present inventors further investigated and found that the formula (I) H5CH2CH is a polyfunctional thiol.
2SCH2CHCH2SH(I)SC)12CH2S
A resin obtained by discovering a new mercapto compound represented by H with extremely low sulfur odor and reacting this mercapto compound with a compound having two or more reactive unsaturated bonds in one molecule, and a lens made of the resin. It was discovered that the above-mentioned problem was solved and that the material had excellent optical properties. That is, the present invention is a polysulfide resin obtained by reacting a mercapto compound represented by formula (I) with a compound having two or more reactive unsaturated bonds in one molecule, and a lens made of the resin. The compounds used in the present invention having two or more reactive unsaturated bonds in one molecule include a total of two or more reactive unsaturated bonds in one molecule.
It is a compound having more than one acryloyl group, methacryloyl group, vinyl group, allyl ether group, allyl carbonate group, allylidene group, etc. They are: ■ acetal compounds, ■ phenol and bisphenol compounds, ■ derivatives of isocyanuric acid, ■ triazine compounds,
■Other polyhydric alcohols and polyvalent thiol derivatives, ■
It is broadly classified into other compounds. These will be explained in detail below. ■Acetal compound The acetal compound used in the present invention is an unsaturated compound having at least two unsaturated cycloacecool groups in one molecule, represented by (unsaturated dioxane type) and/or (unsaturated dioxane type). It is a saturated cycloacecool compound. Examples of these 7-cetal compounds include the following compounds (i) to (2). (i) Diarylidenepentaerythritol, triarylidene sorbitol, diarylidene-2,2,6,6-
Titramethylolcyclohexanone or mixtures thereof. (ii) (a) diarylidenepentaerythritol and/or diarylidene-2,2,6,6-titramethylolcyclohexanone and (b) ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, 1. 3-butanediol, 1.6-
Hexanediol, polyethylene glycol, hydrogenated bisphenol A, bisphenol-ethylene oxide adduct, bisphenol A-propylene oxide adduct, trimethylolpropane, trimethylolethane,
Pentaerythritol, dipentaerythritol, ethylene oxide adducts of phthalic acid, isophthalic acid and terephthalic acid, polyols such as polyesters containing terminal hydroxyl groups with a molecular ff of 11,500 or less, (C) dithioglycol, dipentene dimercaptan, ethylcyclohexyl dimercaptan, 1. The total number of hydroxyl groups and/or mercapto groups per molecule, such as polythiols such as 6-hexane dimercaptan, thioglycolic acid, β-mercaptopropionic acid, or ester compounds obtained by reacting mercaptosuccinic acid with the above polyols. (d) Phenol, cresol, and phenols such as novolak, bisphenol F, and bisphenol A obtained by formalin condensation of these, (e) benzenesulfonamide, 0-toluenesulfonamide, p-toluenesulfonamide , arylsulfonamides such as chlorobenzenesulfonamide, or (f) reaction products with mixtures thereof. (iii) Monoallylidene trimethylolpropane and/or monoallylidene trimethylolethane with isocyanate compounds such as tolylene diisocyanate, polyalkylene allyl isocyanate, metaphenylene diisocyanate, xylylene diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, etc. reaction product. (iv) monoallylidene trimethylolpropane and/or monoallylidene trimethylolethane and succinic anhydride, maleic anhydride, itaconic anhydride,
Addition half-esterified product with phthalic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride. (V) Addition half-esterified product of monoallylidene trimethylolpropane and/or monoallylidene trimethyloleethane with carboxylic acid anhydride, polyglycidyl ether type epoxy compound, phthalic acid, adipic acid, dimer acid, etc. A compound obtained by reacting with an epoxy compound such as a glycidyl ester type epoxy compound. ■Phenol and bisphenol compounds The phenol and bisphenol compounds used in the present invention are:
Phenols and bisphenols having at least two acryloyl groups, methacryloyl groups, allyl ether groups, or allyl carbonate groups in one molecule, examples of which can be used in the present invention include those represented by formula (II). be done. (R++-Tr-)HRz)nz (n
), where nll nx is an integer of 1 to 4, and X is (1) to (
6) The structure represented by formula (16), R+ and Ri each independently have the structure shown by formula (16). (2) (,tl= shiH3 where (1) In the formula, Y has the structure shown in the formulas (7) to (15) etc. R4 →0- CH-CH2hiOC) T(OCl(2h C
=CH2... (16) R,0 In the formula, R,, R4 represents a hydrogen atom, a methyl group, an ethyl group, a chloromethyl group, a bromomethyl group, m is an integer of O to 5, p, q is O or l. ■ Derivatives of isocyanuric acid The isocyanuric acid derivatives used in the present invention are those having at least two acryloyl groups, methacryloyl groups, allyl ether groups, or allyl carbonate groups in one molecule, and the following are exemplified. Ru. l) Polyhydric alcohol obtained by adding alkylene oxide such as ethylene oxide or propylene oxide to isocyanuric acid. 2) Adding epichlorohydrin to isocyanuric acid,
A polyhydric alcohol obtained by reacting a polyhydric alcohol with an epoxy compound obtained by dehydrochlorination. 3) A polyhydric alcohol obtained by methylolizing the reaction product of isocyanuric acid and acrylamide. In addition to the above polyhydric alcohols and isocyanuric acids, acrylic acid, methacrylic acid, allyl chloroformate, allyl alcohol, allyl halides, glycidyl acrylate,
Isocyanuric acid derivative reacted with glycidyl methacrylate. Typical examples include tris(2-acryloylxyethyl)isocyanurate, tris(2-methacryloylxyethyl)isocyanurate, bis(2-acryloylxyethyl)-2-hydroxyethylisocyanurate, bis(2-methacryloylxyethyl) )-2-hydroxyethyl isocyanurate, bis(2-acryloylxyethyl)-2-acetoxyethyl isocyanurate, bis(2-methacryloylxyethyl)acetoxyethyl isocyanurate, bis(2-acryloylxyethyl)allyl isocyanurate, Examples include bis(2-methacryloylxyethyl)allylisocyanurate and triallylisocyanurate. ■Triazine compound The triazine compound used in the present invention has at least two acryloyl groups, methacryloyl groups,
It is a triazine compound having an allyl ether group or an allyl carbonate group, such as a compound represented by formula (1'II) or a compound obtained by oligomerizing these via formalin, polyhydric alcohol, ethylene oxide, etc. (m) In the formula, x', y', z, (meth)acrylic modified hydrogen, alkyl group, alkoxyl group, provided that R1, R2 are hydrogen, aliphatic groups such as methyl group, ethyl group, propyl group an alkyl group, an aromatic alkyl group such as a benzyl group, or in the formula, R3 and R4 represent a hydrogen atom, a methyl group, an ethyl group, a chloromethyl group, or a bromomethyl group, m is an integer of O to 5, n, p, q is O or 1
It is. Representative triazine compounds include (1) N,N'-bis(meth)acryloylmethyl-N;N',N'', N-tetrakismethoxymethylmelamine,
N, N, N", N"-tetrakis(meth)acryloylmethyl-N", N"-bisethoxymethylmelamine, (2) N, N, N', N', N", N"-hexakis ( 2-(meth)acryloylethoxymethyl)melamine, (3) 2.4-bis[N,N-bis[(2-
(meth)acryloylethoxy)ethoxymethyl】〕〕
Amino-6-nitoxy 1.3.5 Triazine, (4) 2.4-bis(p-(2-(meth)acryloylethoxy)phenyloxy] -6-[[N,N-bis

[(2-(meth)acryloylethoxy)ethoxymethyl]Jamino]-1,3,5-triazine, (5)
2.2-bis[4-[[N, N', N''-trismethoxymethyl-N', N''-(2-(meth)acryloyl ethoxy)methyl] melaminyloxy J phenyl J propane, etc. . In addition, as polyhydric alcohols used for oligomerization,
Examples include ethylene glycol, diethylene glycol, propylene glycol, 1,3-butanediol, 1,6-hexanediol, hydrogenated bisphenol A, trimethylolpropane, pentaerythritol, ethylene oxide adducts of phthalic acid, isophthalic acid, and terephthalic acid. It will be done. ■Other polyhydric alcohols and polyvalent thiol derivatives The polyhydric alcohol derivatives other than those mentioned above that can be used in the present invention are: l) Ethylene glycol, trimethylolpropane,
Aliphatic polyhydric alcohols such as pentaerythritol, propylene glycol, glycerin, sorbitol, neopentyl glycol, dichloroneopentyl glycol, dibromoneopentyl glycol, dipentaerythritol. 2) [4-(hydroxyethoxy)phenyl J sulfide, bis(4-(2-hydroxypropoxy)phenyl] sulfide, bis(4-(2,3-dihydroxypropoxy)phenyl) sulfide, bis[4-(4-
hydroxycyclohexyloxy) sulfide, bis[2
-Methyl-4-(hydroxyethoxy)-6-butylphenyl] sulfide, bis(2-hydroxyethyl) sulfide, 1.2-bis(2-hydroxyethylmercapto)ethane, bis(2-hydroxyethyl) disulfide, 1. 4-dithiane-2,5-diol, bis(2
, 3-dihydroxypropyl) sulfide, tetrakis(4-hydroxy-2-thiobutyl)methane, 4,4°
- Polyhydric alcohols such as thiobis(6-tert-butyl-3-methylphenol), 1,3-bis(2-hydroxyethylthioethyl)cyclohexane, and alkylene oxides such as ethylene oxide and propylene oxide are added to them. Polyhydric alcohol and acrylic acid, methacrylic acid, allyl chloroformate,
It is a reaction product of allyl alcohol, allyl halide, glycidyl acrylate, and glycidyl methacrylate. The polyvalent thiol derivatives used in the present invention include polythiols, polythiols having at least one sulfur atom in addition to a mercapto group, compounds having a hydroxyl group and a mercapto group, and compounds having a hydroxyl group and at least one sulfur atom in addition to a mercapto group. For example, methanedithiol, 1.2-ethanedithiol, 1.1-propanedithiol, 1.2-propanedithiol, 1.3-propanedithiol, 2.2-propanedithiol, 1 .6-hexanedithiol, 1.
2.3-propane trithiol, 1.1-cyclohexanedithiol, 1.2-cyclohexanedithiol, 2
．． 2-dimethylpropane-1,3-dithiol, 3.4
-dimethoxybutane-1,2-dithiol, 2-methylcyclohexane-2,3-dithiol, 1,1-bis(
Mercaptomethyl) cyclohexane, 2.3-dimercaptosuccinic acid (2-mercaptoethyl ester), 2.
3-dimercapto-1-propatur (2-mercaptoacetate), 2.3-dimercapto-1-propatur (3-mercaptopropionate), diethylene glycol bis(2-mercaptoacetate), diethylene glycol bis(3-mercaptopropionate) pionate), 1
．． 2-dimercaptopropyl methyl ether, 2.3-
Dimercaptopropyl methyl ether, bis(2-mercaptoethyl) ether, ethylene glycol bis(2
- mercaptoacetate), ethylene glycol bis(
3-mercaptopropionate), trimethylolpropane bis(2-mercaptoacetate), trimethylolpropane bis(3-mercaptopropionate), pentaerythritol tetrakis (2-mercaptoacetate), pentaerythritol tetrakis (3-mercaptopropionate) aliphatic polythiols such as pionate), and halogen-substituted compounds such as chlorine-substituted products and bromine-substituted products thereof,
1.2-dimercaptobenzene, 1.3-dimercaptobenzene, 1.4-dimercaptobenzene, 1.2-bis(mercaptomethyl)benzene, 1.3-bis(mercaptomethyl)benzene, 1.4- Bis(mercaptomethyl)benzene, 1.2-bis(mercaptoethyl)benzene, 1.3-bis(mercaptoethyl)benzene,
1.4-bis(mercaptoethyl)benzene, 1.2-
Bis(mercaptomethyleneoxy)benzene, 1.3-
Bis(mercaptomethyleneoxy)benzene, 1.4-
Bis(mercaptomethyleneoxy)benzene, 1.2-
Bis(mercaptoethyleneoxy)benzene, 1.3-
Bis(mercaptoethyleneoxy)benzene, 1.4-
Bis(mercaptoethyleneoxy)benzene, 1.2.
3-trimercaptobenzene, 1.2.4-trimercaptobenzene, 1.3.5-trimercaptobenzene, 1.2.3-tris(mercaptomethyl)benzene, 1.2.4-tris(mercaptomethyl) Benzene, 1.3.5-tris(mercaptomethyl)benzene,
1.2.3- Tris(mercaptoethyl)benzene,
1.2.4-tris(mercaptoethyl)benzene, 1
．． 3.5-tris(mercaptoethyl)benzene, l,
2.3-tris(mercaptomethyleneoxy)benzene, 1.2.4-)lis(mercaptomethyleneoxy)benzene, 1.3.5-tris(mercaptomethyleneoxy)benzene, l, 2.3-tris(mercaptomethyleneoxy)benzene ethyleneoxy)benzene, 1.2.4-tris(mercaptoethyleneoxy)benzene, 1,3.5-tris(mercaptoethyleneoxy)benzene, 1.2.
3.4-tetramercaptobenzene, 1,2°・3.5
-tetramercaptobenzene, 1.2.4.5-tetramercaptobenzene, 1.2.3.4-tetrakis(mercaptomethyl)benzene, I, 2.3.5-tetrakis(mercaptomethyl)benzene, 1.2 .4.5-
Tetrakis(mercaptomethyl)benzene, l, 2.
3.4-tetrakis(mercaptoethyl)benzene, l
, 2.3゜5-tetrakis(mercaptoethyl)benzene, 1.2,4.5-tetrakis(mercaptoethyl)benzene, 1,2,3.4-tetrakis(mercaptomethyleneoxy)benzene, 1.2.3 .5-tetrakis(mercaptomethyleneoxy)benzene, l, 2.
4.5-tetrakis(mercaptomethyleneoxy)benzene, 1.2゜3.4-tetrakis(mercaptoethyleneoxy)benzene, 1.2.3.5-tetrakis(mercaptoethyleneoxy)benzene, 1.2.4. 5-
Tetrakis(mercaptoethyleneoxy)benzene, 2
．． 5-1-toluenedithiol, 3.4-toluenedithiol, 2.4-dimethylbenzene-1,3-dithiol, 4.5-dimethylbenzene-13-dithiol,
9.10-anthracene dimethanethiol, 1.3-di(p-methoxyphenyl)propane-2,2-dithiol, 1.3-diphenylpropane-2,2-dithiol, phenylmethane-1,1-dithiol, 2.4-di(
Aromatic polythiols such as p-mercaptophenyl)pentane, 2,5-dichlorobenzene-1,3-dithiol, 1,3-di(p-chlorophenyl)propane-2
, 2-dithiol, 3.4.5-tribromo-1,2-
Halogen-substituted aromatic polythiols such as chlorine-substituted and bromine-substituted products such as dimercaptobenzene, 2.3.4.6-tetrachloro-1,5-bis(mercaptomethyl)benzene, and 2-methylamino-4,6 -Sithiorusy
m-triazine, 2-ethylamino-46-sithio-sym-triazine, 2-amino-4,6-sithio-sym-triazine, 2-morpholino-4,6-sithio-sym-triazine, 2-cyclohexylamino-4, 6-sithio-sym-triazine, 2-
methoxy-4,6-sithio-sym-triazine,
2-phenoxy-4,6-sithio-sym-triazine, 2-thiobenzeneoxy-4,6-sithio-sym-triazine, 2-thiobutyloxy-4,6-
Polythiols containing heterocycles such as dithiol-8ym-triazine, halogen-substituted compounds thereof such as chlorine-substituted products and bromine-substituted products, and difunctional or higher-functional polythiols containing at least one sulfur atom in addition to the mercapto group: For example 1.2
-Bis(mercaptomethylthio)benzene, 1.3-bis(mercaptomethylthio)benzene, l, 2.3-
Tris(mercaptomethylthio)benzene, 1.2.4
-tris(mercaptomethylthio)benzene, 1,3.
5-t-lis(mercaptomethylthio)benzene, 1,
2.3-tris(mercaptoethylthio)benzene, 1
．． 2.4-tris(mercaptoethylthio)benzene, 1.3.5-tris(mercaptoethylthio)benzene, 1.2.3.4-tetrakis(mercaptomethylthio)benzene, 1,2.3.5-tetrakis (Mercaptomethylthio)benzene, 1, 2.4.5-Tetrakis(mercaptomethylthio)benzene, 1, 2.3.4
-tetrakis(mercaptoethylthio)benzene, 1.
2.3.5-tetrakis(mercaptoethylthio)benzene, 1.2.4.5-tetrakis(mercaptoethylthio)benzene, etc., and aromatic polythiols such as nuclear alkylated products thereof, bis(mercaptomethyl)sulfide, Bis(mercaptoethyl) sulfide, bis(mercaptopropyl) sulfide, bis(mercaptomethylthio)methane, bis(2-mercaptoethylthio)methane, bis(3-mercaptopropylthio)methane, 1.
2-bis(mercaptomethylthio)ethane, 1.2-bis(2-mercaptoethylthio)ethane, 1.2-bis(3-mercaptopropylthio)ethane,! , 3-bis(mercaptomethylthio)propane, 1.3-bis(2
-Mercaptoethylthio)propane, 1,3-bis(3
-Mercaptopropylthio>propane, 1.2.3-tris(mercaptomethylthio)propane, 1.2゜3-
Tris(2-mercaptoethylthio)propane, 1.2
．． 3-tris(3-mercaptopropylthio)propane, tetrakis(mercaptomethylthiomethyl)methane,
Tetrakis(3-mercaptopropylthiomethyl)methane, bis(mercaptomethyl) disulfide, bis(mercaptoethyl) disulfide, bis(mercaptopropyl) disulfide, etc., and esters of these thioglycolic acids and mercaptopropionic acids, hydroxymethyl sulfide bis (2-mercaptoacetate), hydroxymethylsulfide bis(3-mercaptopropionate), hydroxyethylsulfide bis(2-mercaptoacetate), hydroxyethylsulfide bis(3-mercaptopropionate), hydroxypropylsulfide bis(2-mercaptopropionate), -mercaptoacetate), hydroxypropylsulfide bis(3-mercaptopropionate), hydroxymethyl disulfide bis(2-mercaptopropionate),
-Mercaptoacetate), Hydroxymethyl disulfide bis(3-mercaptopropionate), Hydroxyethyl disulfide bis(2-mercaptoacetate), Hydroxyethyl disulfide bis(3-mercaptopropionate), Hydroxypropyl disulfide bis(2-mercaptopropionate) acetate), hydroxypropyl disulfide bis(3-mercaptopropionate)
, 2-mercaptoethyl ether bis(2-mercaptoacetate), 2-mercaptoethyl ether bis(3
-Mercaptopropione-)), 1,4-dithiane-2
, 5-diolbis(2-mercaptoacetate), 1
．． 4-dithiane-2,5-diol bis(3-mercaptopropionate), thiodiglycolic acid bis(2-mercapto earth ester), thiodipropionate bis(3-mercaptopropionate)
2-mercaptoethyl ester), 4.4-thiodibutyric acid bis(2-mercaptoethyl ester), dithioglycolic acid bis(2-mercaptoethyl ester), dithiodipropionate bis(2-mercaptoethyl ester), 4.4 - dithiodibutyric acid bis(2-mercaptoethyl ester), thiodiglycolic acid bis(2,3-
dimercaptopropyl ester), thiodipropionate bis(2,3-dimercaptopropyl ester), dithioglycolic acid bis(2,3-dimercaptopropyl ester), dithiodipropionate bis(2,3-dimercaptopropyl ester) aliphatic polythiols such as esters),
3.4-thiophenedithiol, bismuthiol, 2.
Heterocyclic compounds such as 5-dimercapto-1,3,4-thiadiazole, etc. Furthermore, halogen-substituted products such as chlorine-substituted products and bromine-substituted products. In addition, examples of mercapto compounds having a hydroxy group include 2-mercaptoethanol, 3-mercapto-
1,2-propanediol, glycerin di(mercaptoacetate), l-hydroxy-4-mercaptocyclohexane, 2,4-dimercaptophenol, 2-mercaptohydroquinone, 4-mercaptophenol, 3
, 4-dimercapto-2-propatur, 1.3-dimercapto-2-propatur, 2.3-dimercapto-
1-propatol, 1,2-dimercapto-1,3-butanediol, pentaerythritol tris(3-mercaptopropionate), pentaerythritol mono(
Examples include pentaerythritol bis(3-mercaptopropionate), pentaerythritol tris(thioglycolate), dipentaerythritol pentakis(3-mercaptopropionate), and the like. Furthermore, halogen-substituted products such as chlorine-substituted products and bromine-substituted products. Further, as a mercapto compound having a hydroxy group and containing at least one sulfur atom in addition to the mercapto group,
For example, hydroxymethyl-tris(mercaptoethylthiomethyl)methane, l-hydroxyethylthio-3-
Mercaptoethylthiobenzene, 4-hydroxy-4°
-Mercaptodiphenylsulfone, 2-(2-mercaptoethylthio)ethanol, dihydroxyethylsulfide mono(3-mercaptopropionate), dimercaptoethane mono(salcylate), hydroxyethylthiomethyl-tris(mercaptoethylthiomethyl)methane etc., as well as halogen-substituted products such as chlorine-substituted products and bromine-substituted products. polyvalent thiols such as ethylene oxide,
It is produced by reacting a polyhydric alcohol to which alkylene oxide such as propylene oxide is added with acrylic acid, methacrylic acid, allyl chloroformate, allyl alcohol, allyl halide, glycidyl acrylate, and glycidyl methacrylate. ■Other compounds Other compounds include l) Allyl esters and methallyl esters of polycarboxylic acids such as diallyl phthalate, diallyl succinate, thiodiacetic acid, dithiodiacetic acid, thiodipropionic acid, dithiodipropionic acid, and malic acid; 2) Vinyl compounds such as divinylbenzene and divinyl adipate; 3) Reaction products of polyvalent isocyanates and allyl alcohol such as isophorone diisocyanate, xylylene diisocyanate, tolylene diisocyanate and MDI; 4) polyolefin compounds such as dicyclopentadiene and dibutene. Examples include. The above compounds having two or more reactive unsaturated bonds in one molecule may be used alone or in combination of two or more. Mercapto compound represented by formula (I) and 2 in one molecule
The proportion of compounds having more than 100 reactive unsaturated bonds is usually such that the unsaturated bond/SH (functional group) molar ratio is 0.5 to 3.
．． It is within the range of 0, preferably within the range of 0.5 to 1.5. The resin of the present invention can be obtained by heating a monomer mixture or by irradiating it with ultraviolet rays. At that time, a thermal polymerization initiator or a photopolymerization initiator may be used. When carrying out thermal polymerization, benzoyl peroxide, diisopropyl peroxydicarbonate, azobisisobutyronitrile, azodicyclohexanecarbonitrile, tertiary-butylperoxy-2-ethylhexanoate,
Common radical polymerization initiators such as azobismethylvaleronitrile or mixtures thereof can be used. In the case of ultraviolet curing, the photosensitizer of commonly known benzoyl, benzoin methyl ether, benzoin ethyl ether, benzoin propyl ether, benzoin isobutyl ether, 2-hydroxy-2-benzoyl-propane, benzyl, thioxanthone, diphenyl disulfide, etc. Sensitizers can be used. These polymerization initiators generally have an I
The upper limit is about 0% by weight. The polysulfide resin of the present invention is usually obtained by a cast polymerization method. Specifically, a compound having two or more reactive unsaturated bonds in one molecule and a mercapto compound represented by formula (I) are mixed. At that time, if necessary, use the above-mentioned polymerization initiator, ultraviolet absorber, antioxidant, oil-soluble dye,
Fillers and other substances are added and injected into the mold to polymerize. The polysulfide resin of the present invention obtained in this manner does not cause discomfort due to sulfur odor when handling the monomer or discomfort due to sulfur odor during post-processing, and has a high refractive index as well as an extremely high physical property. It has low dispersion, low moisture absorption, and is transparent, lightweight, and has excellent weather resistance and impact resistance, making it suitable for optical element materials such as eyeglass lenses and camera lenses, and glazing materials. In addition, the lens of the present invention can be manufactured by a cast polymerization method using the polysulfide resin of the present invention as a material, but it can also be provided with anti-reflection, high hardness, improved abrasion resistance, improved chemical resistance, and anti-fogging properties as required. Alternatively, physical and chemical treatments such as surface polishing, antistatic treatment, hard coating treatment, anti-reflection coating treatment, dyeing treatment, and light control treatment can be performed in order to improve fashionability and the like.

[Examples and comparative examples]

Hereinafter, the present invention will be specifically explained with reference to Examples and Comparative Examples. The performance of the obtained lens was evaluated by the following test method. Refractive index, Atsbe number: 20℃ using Brufrich refractometer
It was measured with Weather resistance: The lens resin was set in a weather meter equipped with a sunshine carbon arc lamp, and after 20 hours, the lens was taken out and compared with the hue of the lens resin before the test. The evaluation criteria were: no change (○), slight yellowing (△), and yellowing (×). The appearance was observed with a second glance. Odor: When mixing monomers, those with a strong sulfur odor (×),
Items with very few items were marked as (○), and items with a small amount of items were marked as (△). Example-l 25 g of triallyl isocyanurate and 1,2-bis[(
2-mercaptoethyl)thio]-3-mercaptopropane (26 g) was mixed with 0.5 g of azobisisobutyronitrile.
g was added, poured into a mold made of a glass mold and a gasket, and then heated and cured. The resin thus obtained is colorless and transparent, has excellent impact resistance, and has a refractive index no =
1.63, Atsbe number ν. =40. Furthermore, there was no sulfur odor during monomer handling or post-processing. Examples-2 to 8. Comparative Examples 1 to 3 Resin formation was carried out using the compositions shown in Table 1 in the same manner as in Example 1, and the results are shown in Table 1.

Claims (1)

[Claims] 1) 1,2-bis[(2-mercaptoethyl) represented by formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I)
A polysulfide resin obtained by reacting thio]-3-mercaptopropane with a compound having two or more reactive unsaturated bonds in one molecule. 2) Formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼1,2-bis[(2-mercaptoethyl) represented by (I)
A lens made of a polysulfide resin obtained by reacting [thio]-3-mercaptopropane with a compound having two or more reactive unsaturated bonds in one molecule.