JP3083196B2 - Sulfur-containing plastic lens and manufacturing method thereof - Google Patents

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 sulfur-containing plastic lens. More specifically, the present invention relates to a plastic lens which does not generate a peculiar smell and odor peculiar to sulfur in a cutting and polishing process of a sulfur-containing lens molded body obtained by casting polymerization, and a method for producing the same. The sulfur-containing plastic lens of the present invention is used for eyeglasses, optical materials, and the like.

[0002]

2. Description of the Related Art Plastic lenses are lighter and harder to break than inorganic lenses and can be dyed. Therefore, plastic lenses have recently been rapidly used in optical devices such as spectacle lenses and camera lenses. Currently, the most widely used resins for these purposes include those obtained by radical polymerization of diethylene glycol bis (allyl carbonate) (hereinafter referred to as DAC). This resin has various characteristics such as being excellent in impact resistance, being lightweight, being excellent in dyeing properties, being excellent in workability such as cutting property and polishing property, and the like. . However, n _D = 1 compared to the DAC lens made of a refractive index inorganic lenses (n _D = 1.52).
In order to obtain optical properties equivalent to that of a glass lens, which is as small as 50, it is necessary to increase the center thickness, edge thickness, and curvature of the lens, and it is inevitable that the lens as a whole becomes thick.
Therefore, a lens resin having a higher refractive index is desired.

Attempts have been made to introduce sulfur atoms in order to increase the refractive index of the resin. For example, a sulfur-containing urethane-based resin composed of polyisocyanate and polythiol (Japanese Patent Application Laid-Open No.
199016, JP-A-62-267316, JP-A-63-46213), polythio (meth) acrylate resin (JP-A-64-26613, JP-A-64-31759, JP-A-63-188660) or sulfur-containing poly ( (Meth) acrylate resin (JP-A-62-283109, JP-A
63-268707) has been proposed. However, since these resins contain a sulfur atom, an unusual odor and an odor peculiar to sulfur are generated at the time of cutting and polishing the lens, and the operator sometimes feels strong discomfort.

With respect to plastic lenses, a processing method for reducing or eliminating odors and odors generated during cutting and polishing has been desired and proposed. For example, in the production of a high-refractive-index plastic lens having a crosslinked structure with a refractive index of 1.50 or more, which is a radical polymerization type, by using a resin containing a fragrance imparting compound at 0.05% to 1%,
Japanese Patent Publication No. 2-56641 discloses a technique for alleviating an unpleasant odor and odor during lens cutting and polishing. However, the present inventors have studied sulfur-containing plastic lenses using the fragrance imparting compounds disclosed herein.As a result of these odor imparting compounds, sulfur-specific off-flavors,
It was found to be insufficient to reduce or deodorize odors.

[0005]

SUMMARY OF THE INVENTION It is an object of the present invention to provide a high-refractive-index sulfur-containing plastic lens which reduces or deodorizes an odor and an odor peculiar to sulfur during processing such as cutting and polishing. And a method of manufacturing the lens.

[0006]

Means for Solving the Problems The inventors of the present application have made intensive studies to solve the above-mentioned problems, and as a result, by using a certain compound, an odor peculiar to sulfur generated at the time of processing a lens, The inventors have found that the odor can be reduced or deodorized, and have completed the present invention. That is, the present invention
In a high-refractive-index sulfur-containing plastic lens having a crosslinked structure having a refractive index of 1.50 or more, β-ionone, isoamyl isovalerate, methionol, n-amyl acetate, 2-
0.005 to 0.5% by weight of at least one compound selected from phenyl-2-propanol, benzyldimethylcarbinol, isopulegol or eucalyptus oil
The present invention relates to a sulfur-containing plastic lens to be contained. Further, in the method for producing a high-refractive-index sulfur-containing plastic lens having a crosslinked structure having a refractive index of 1.50 or more, β-ionone, isoamyl isovalerate, methionol, n-amyl acetate, 2-phenyl- 2-propanol, benzyldimethylcarbinol,
0.005 to 0.5% by weight of at least one compound selected from isopulegol or eucalyptus oil;
The present invention relates to a method for producing a sulfur-containing plastic lens that undergoes heat polymerization. Furthermore, a method for producing a sulfur-containing plastic lens in which the sulfur-containing plastic lens is a sulfur-containing urethane resin and a monomer mixture in which the monomer mixture is a monomer mixture composed of a bifunctional or higher polyisocyanate compound and a bifunctional or higher polythiol compound It is about.

According to the present invention, it becomes possible to reduce or eliminate the odor and odor peculiar to sulfur generated during cutting and polishing of a lens and to process a sulfur-containing lens without feeling uncomfortable for an operator. . The compound used in the present invention is β
-At least one compound selected from the group consisting of ionone, isoamyl isovalerate, methionol, n-amyl acetate, 2-phenyl-2-propanol, benzyldimethylcarbinol, isopulegol or eucalyptus oil; Although it depends on the sulfur-containing lens used, it is usually 0.005 to 0.5% by weight. These compounds are commercially available and readily available.

The sulfur-containing lens used in the present invention is made of a sulfur-containing urethane resin, a sulfur-containing epoxy resin, a polythio (meth) acrylate resin, or a sulfur-containing poly (meth) acrylate resin. For example, the sulfur-containing urethane-based resin is a resin obtained by reacting a polyisocyanate with a polyol having a sulfur atom, a polythiol, a mercapto compound having a hydroxy group, or the like. Specifically, as the polyisocyanate, for example, ethylene diisocyanate, trimethylene diisocyanate,
Tetramethylene diisocyanate, hexamethylene diisocyanate, octamethylene diisocyanate, nonamethylene diisocyanate, 2,2'-dimethylpentane diisocyanate, 2,2,4-trimethylhexane diisocyanate, decamethylene diisocyanate Isocyanate, butene diisocyanate, 1,3-butadiene-1,4-diisocyanate, 2,4,4-trimethylhexamethylene diisocyanate, 1,6,11-undecatriisocyanate, 1,3, 6 −
Hexamethylene triisocyanate, 1,8-diisocyanato-4-isocyanatomethyloctane, 2,5,7-
Trimethyl-1,8-diisocyanato-5-isocyanatomethyloctane, bis (isocyanatoethyl) carbonate, bis (isocyanatoethyl) ether,
1,4-butylene glycol dipropyl ether-W, W'-
Diisocyanate, lysine diisocyanate methyl ester, lysine triisocyanate, 2-isocyanatoethyl-2,6-diisocyanate hexanoate, 2-
Isocyanatopropyl-2,6-diisocyanatohexanoate, xylylenediisocyanate, bis (isocyanatoethyl) benzene, bis (isocyanatopropyl) benzene, α, α, α ′, α′-tetramethylxylylenediene Isocyanate, bis (isocyanatobutyl) benzene, bis (isocyanatomethyl) naphthalene, bis (isocyanatomethyl) diphenyl ether, bis (isocyanatoethyl) phthalate, mesitylylene triisocyanate, 2,6-di (isocyanate Aliphatic polyisocyanates such as methyl) furan,

Isophorone diisocyanate, bis (isocyanatomethyl) cyclohexane, dicyclohexylmethanediisocyanate, cyclohexanediisocyanate, methylcyclohexanediisocyanate, dicyclohexyldimethylmethanediisocyanate, 2,2′-dimethyldicyclohexylmethanediisocyanate Notate, bis (4-isocyanato-n-butylidene) pentaerythritol, diisocyanate dimerate, 2-isocyanatomethyl-3- (3-isocyanatopropyl) -5
-Isocyanatomethyl-bicyclo- [2,2,1] -heptane, 2-isocyanatomethyl-3- (3-isocyanatopropyl) -6-isocyanatomethyl-bicyclo- [2,2,1] -heptane 2-isocyanatomethyl-2- (3-isocyanatopropyl) -5-isocyanatomethyl-bicyclo- [2,2,1] -heptane, 2-
Isocyanatomethyl-2- (3-isocyanatopropyl) -6-isocyanatomethyl-bicyclo- [2,
2,1] -heptane, 2-isocyanatomethyl-3-
(3-isocyanatopropyl) -5- (2-isocyanatoethyl) -bicyclo- [2,2,1] -heptane, 2
-Isocyanatomethyl-3- (3-isocyanatopropyl) -6- (2-isocyanatoethyl) -bicyclo- [2,2,1] -heptane, 2-isocyanatomethyl-2- (3-isocyanato Propyl) -5- (2-
Isocyanatoethyl) -bicyclo- [2,2,1] -heptane, 2-isocyanatomethyl-2- (3-isocyanatopropyl) -6- (2-isocyanatoethyl)
Alicyclic polyisocyanate such as -bicyclo- [2,2,1] -heptane,

Phenylene diisocyanate, tolylene diisocyanate, ethyl phenylene diisocyanate,
Isopropyl phenylene diisocyanate, dimethyl phenylene diisocyanate, diethyl phenylene diisocyanate, diisopropyl phenylene diisocyanate, trimethylbenzene triisocyanate, benzene triisocyanate, naphthalene diisocyanate, methyl naphthalene diisocyanate, biphenyl diisocyanate , Toluidine diisocyanate, 4,4'-diphenylmethane diisocyanate, 3,3'-dimethyldiphenylmethane-4,4'-diisocyanate, bibenzyl-4,4 '
-Diisocyanate, bis (isocyanatophenyl)
Ethylene, 3,3′-dimethoxybiphenyl-4,4′-diisocyanate, triphenylmethane triisocyanate,
Polymeric MDI, naphthalene triisocyanate,
Diphenylmethane-2,4,4'-triisocyanate, 3-
Methyldiphenylmethane-4,6,4'-triisocyanate, 4-methyl-diphenylmethane-3,5,2 ', 4', 6'-pentaisocyanate, phenylisocyanatomethylisocyanate, phenylisocyanatoethylisocyanate , Tetrahydronaphthylene diisocyanate, hexahydrobenzene diisocyanate, hexahydrodiphenylmethane-4,4'-diisocyanate, diphenyl ether diisocyanate, ethylene glycol diphenyl ether diisocyanate, 1,3-propylene glycol diphenyl ether diisocyanate, Benzophenone diisocyanate, diethylene glycol diphenyl ether diisocyanate, dibenzofurandi isocyanate, carbazole diisocyanate, ethyl carbazole diisocyanate Aromatic polyisocyanates such as dichloro carbazole diisocyanate,

Sulfur-containing compounds such as thiodiethyl diisocyanate, thiodipropyl diisocyanate, thiodihexyl diisocyanate, dimethyl sulfone diisocyanate, dithiodimethyl diisocyanate, dithiodiethyl diisocyanate, and dithiodipropyl diisocyanate. Aliphatic isocyanate, diphenylsulfide-2,4'-diisocyanate, diphenylsulfide-4,4'-diisocyanate, 3,3'-dimethoxy-4,4'-diisocyanatodibenzylthioether, bis ( 4-isocyanatomethylbenzene) sulfide, aromatic sulfide isocyanate such as 4,4'-methoxybenzenethioethylene glycol-3,3'-diisocyanate, diphenyldisulfide-4,4'-diisocyanate, 2 , 2'-Dimethyldiphenyl disulfide-5,5'-di Soshianato, 3,3'
Dimethyl diphenyl disulfide-5,5'-diisocyanate, 3,3'-dimethyl diphenyl disulfide-6,6'-
Diisocyanate, 4,4'-dimethyldiphenyldisulfide-5,5'-diisocyanate, 3,3'-dimethoxydiphenyldisulfide-4,4'-diisocyanate, 4,4'-
Aromatic disulfide isocyanates such as dimethoxydiphenyl disulfide-3,3′-diisocyanate;

Diphenylsulfone-4,4'-diisocyanate, diphenylsulfone-3,3'-diisocyanate,
Benzidine sulfone-4,4'-diisocyanate, diphenylmethanesulfone-4,4'-diisocyanate, 4-
Methyldiphenylsulfone-2,4'-diisocyanate,
4,4'-dimethoxydiphenylsulfone-3,3'-diisocyanate, 3,3'-dimethoxy-4,4'-diisocyanatodibenzylsulfone, 4,4'-dimethyldiphenylsulfone-3,3 ' Diisocyanate, 4,4′-di (tert-butyl) diphenylsulfone-3,3′-diisocyanate, 4,
4'-methoxybenzeneethylenedisulfone-3,3'-diisocyanate, 4,4'-dichlorodiphenylsulfone-3,
Aromatic sulfone isocyanates such as 3'-diisocyanate, 4-methyl-3-isocyanatobenzenesulfonyl-4'-isocyanatophenol ester,
Methoxy-3-isocyanatobenzenesulfonyl-4 '
Sulfonic acid ester isocyanate such as isocyanate phenol ester, 4-methyl-3-isocyanatobenzenesulfonylanilide-3′-methyl-4′-
Isocyanate, dibenzenesulfonyl-ethylenediamine-4,4'-diisocyanate, 4,4'-methoxybenzenesulfonyl-ethylenediamine-3,3'-diisocyanate, 4-methyl-3-isocyanatobenzenesulfonylanilide- Aromatic sulfonic acid amides such as 4-methyl-3'-isocyanate; sulfur-containing heterocyclic compounds such as thiophene-2,5-diisocyanate; and others; 1,4-dithiane-2,5-diisocyanate Is mentioned. Also,
These chlorine-substituted products, halogen-substituted products such as bromine-substituted products,
Alkyl-substituted, alkoxy-substituted, nitro-substituted or prepolymer-modified products with polyhydric alcohols, carbodiimide-modified products, urea-modified products, buret-modified products, dimerized or trimerized reaction products, and the like can also be used.

The polyol having a sulfur atom includes, for example, bis- [4- (hydroxyethoxy) phenyl]
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, and compounds obtained by adding an average of 3 molecules or less of ethylene oxide and / or propylene oxide per hydroxyl group to these compounds, di- (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) −
Thiabutyl) methane, bis (4-hydroxyphenyl)
Sulfone (trade name, bisphenol S), tetrabromobisphenol S, tetramethylbisphenol S, 4,
4'-thiobis (6-tert-butyl-3-methylphenol), 1,3-bis (2-hydroxyethylthioethyl)
Polyols containing sulfur atoms, such as cyclohexane, can also be used. These polyols may use halogen-substituted products such as chlorine-substituted products and bromine-substituted products. These may be used alone or in combination of two or more.

Examples of the polythiol include methanedithiol, 1,2-ethanedithiol, 1,1-propanedithiol, 1,2-propanedithiol, 1,3-propanedithiol, 2,2-propanedithiol, , 6−
Hexanedithiol, 1,2,3-propanetrithiol,
1,1-cyclohexanedithiol, 1,2-cyclohexanedithiol, 2,2-dimethylpropane-1,3-dithiol, 3,4-dimethoxybutane-1,2-dithiol,
-Methylcyclohexane-2,3-dithiol, bicyclo [2,2,1] peptide-exo-cis-2,3-dithiol,
1,1-bis (mercaptomethyl) cyclohexane, thiomalic acid bis (2-mercaptoethyl ester), 2,3
-Dimercaptosuccinic acid (2-mercaptoethyl ester), 2,3-dimercapto-1-propanol (2-mercaptoacetate), 2,3-dimercapto-1-propanol (3-mercaptopropionate), diethylene glycol bis ( 2-mercaptoacetate), diethylene glycol bis (3-mercaptopropionate), 1,2-dimercaptopropyl methyl ether,
2,3-dimercaptopropyl methyl ether, 2,2-bis (mercaptomethyl) -1,3-propanedithiol,
Bis (2-mercaptoethyl) ether, ethylene glycol bis (2-mercaptoacetate), ethylene glycol bis (3-mercaptopropionate), trimethylolpropanebis (2-mercaptoacetate), trimethylolpropanebis (3-mercapto Propionate), pentaerythritol tetrakis (2
-Mercaptoacetate), aliphatic polythiols such as pentaerythritol tetrakis (3-mercaptopropionate)

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 (mercaptoethyloxy) 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, 1,2,3-tris (mercaptomethyleneoxy) benzene, 1,2,4-tris (mercaptomethyleneoxy) benzene, 1,3,5-
Tris (mercaptomethyleneoxy) benzene, 1,2,3
-Tris (mercaptoethyleneoxy) 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

1,2,4,5-tetrakis (mercaptomethyl) benzene, 1,2,3,4-tetrakis (mercaptoethyl) benzene, 1,2,3,5-tetrakis (mercaptoethyl) benzene, 2,4,5-tetrakis (mercaptomethyleneoxy) benzene, 1,2,3,4-tetrakis (mercaptomethyleneoxy) benzene, 1,2,3,5-tetrakis (mercaptomethyleneoxy) benzene, 1,2,4 1,5-tetrakis (mercaptomethyleneoxy) benzene, 1,2,3,4-tetrakis (mercaptoethyleneoxy) benzene, 1,2,
3,5-tetrakis (mercaptoethyleneoxy) benzene, 1,2,4,5-tetrakis (mercaptoethyleneoxy) benzene, 2,2′-dimercaptobiphenyl, 4,4′-
Dimercaptobiphenyl, 4,4'-dimercaptobibenzyl, 2,5-toluenedithiol, 3,4-toluenedithiol, 1,4-naphthalenedithiol, 1,5-naphthalenedithiol, 2,6-naphthalenedithiol, 2 , 7-Naphthalenedithiol, 2,4-dimethylbenzene-1,3-dithiol, 4,5-dimethylbenzene-1,3-dithiol, 9,10-anthracenedimethanethiol, 1,3-di (p-methoxy Aromatic polythiols such as phenyl) propane-2,2-dithiol, 1,3-diphenylpropane-2,2-dithiol, phenylmethane-1,1-dithiol, and 2,4-di (p-mercaptophenyl) pentane; 2
-Methylamino-4,6-dithiol-sym-triazine, 2-ethylamino-4,6-dithiol-sym-triazine, 2-amino-4,6-dithiol-sym-triazine, 2-morpholino-4,6 -Dithiol-sym-triazine, 2-cyclohexylamino-4,6-dithiol-sym-triazine, 2-methoxy-4,6-dithiol-sym-triazine, 2-phenoxy-4,6-dithiol-sym-triazine, 2-thiobenzeneoxy-4,6
Polythiol containing a heterocyclic ring such as -dithiol-sym-triazine, 2-thiobutyloxy-4,6-dithiol-sym-triazine,

1,2-bis (mercaptomethylthio) benzene, 1,3-bis (mercaptomethylthio) benzene,
1,4-bis (mercaptomethylthio) benzene, 1,2-
Bis (mercaptoethylthio) benzene, 1,3-bis (mercaptoethylthio) benzene, 1,4-bis (mercaptoethylthio) benzene, 1,2,3-tris (mercaptomethylthio) benzene, 1,2,4 -Tris (mercaptomethylthio) benzene, 1,3,5-tris (mercaptomethylthio) benzene, 1,2,3-tris (mercaptoethylthio) benzene, 1,2,4-tris (mercaptoethylthio) benzene, 1 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-tetra Aromatic polythiols containing a sulfur atom in addition to a mercapto group such as kiss (mercaptoethylthio) benzene and 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-mercaptopropyl) ethane, 1,3-
Bis (mercaptomethylthio) propane, 1,3-bis (2-mercaptoethylthio) propane, 1,3-bis (3-mercaptopropylthio) propane, 1,2,3-tris (mercaptomethylthio) propane, 2,3-tris (2-mercaptoethylthio) propane, 1,2,3-tris (3-mercaptopropylthio) propane, tetrakis (mercaptomethylthiomethyl) methane, tetrakis (2-mercaptoethylthiomethyl) methane, tetrakis (3-mercaptopropylthiomethyl) methane, bis (2,3-dimercaptopropyl) sulfide, 2,5-
Dimercapto-1,4-dithiane, bis (mercaptomethyl) disulfide, bis (mercaptoethyl) disulfide, bis (mercaptopropyl) disulfide, and the like, and esters of thioglycolic acid and mercaptopropionic acid;

Hydroxymethyl sulfide bis (2-mercaptoacetate), hydroxymethyl sulfide bis (3-mercaptopropionate), hydroxyethyl sulfidebis (2-mercaptoacetate), hydroxyethyl sulfidebis (3-mercaptopropionate) , Hydroxypropyl sulfide bis (2-mercaptoacetate), hydroxypropyl sulfide bis (3-mercaptopropionate), hydroxymethyl disulfidebis (2-mercaptoacetate),
Hydroxymethyldisulfidebis (3-mercaptopropionate), hydroxyethyldisulfidebis (2-mercaptoacetate), hydroxyethyldisulfidebis (3-mercaptopropionate), hydroxypropyldisulfidebis (2-mercaptoacetate), hydroxypropyl Disulfide bis (3-
Mercaptopropionate), 2-mercaptoethylether bis (2-mercaptoacetate), 2-mercaptoethyletherbis (3-mercaptopropionate), 1,4-dithiane-2,5-diolbis (2-mercaptoacetate) ), 1,4-dithiane-2,5-diolbis (3-mercaptopropionate), thiodiglycolic acid bis (2-mercaptoethyl ester), thiodipropionic acid bis (2-mercaptoethyl ester),
Bis (2-mercaptoethyl ester) 4,4-thiodibutyrate, Bis (2-mercaptoethyl ester) dithiodiglycolate, Bis (2-mercaptoethyl ester) dithiodipropionate, Bis (4,4-dithiodibutylate) 2-mercaptoethyl ester), bis (2,3-dimercaptopropyl ester) thiodiglycolate, bis (2,3-dimercaptopropyl ester) thiodipropionate, bis (2,3-dimercaptodithioglycolate) Propyl ester), dithiodipropionate bis (2,3-
It contains a sulfur atom in addition to a mercapto group such as aliphatic polythiol, 3,4-thiophenedithiol, and 2,5-dimercapto-1,3,4-thiadiazole other than a mercapto group such as dimercaptopropyl ester) And the like. Further, halogen-substituted products such as chlorine-substituted and bromine-substituted polythiols may be used. These may be used alone or in combination of two or more.

Examples of the mercapto compound having a hydroxy group include 2-mercaptoethanol and
3-mercapto-1,2-propanediol, glycerin di (mercaptoacetate), 1-hydroxy-4-mercaptocyclohexane, 2,4-dimercaptophenol, 2-mercaptohydroquinone, 4-mercaptophenol, 3,4-dimercapto -2-propanol,
1,3-dimercapto-2-propanol, 2,3-dimercapto-1-propanol, 1,2-dimercapto-1,3
-Butanediol, pentaerythritol tris (3-
Mercaptopropionate), pentaerythritol mono (3-mercaptopropionate), pentaerythritolbis (3-mercaptopropionate), pentaerythritol tris (thioglycolate), dipentaerythritol pentakis (3-mercaptopropionate) ), Hydroxymethyl-tris (mercaptoethylthiomethyl) methane, 1-hydroxyethylthio-3-
Mercaptoethylthiobenzene, 4-hydroxy-4'-
Mercaptodiphenyl sulfone, 2- (2-mercaptoethylthio) ethanol, dihydroxyethylsulfide mono (3-mercaptopropionate), dimercaptoethane mono (salicylate), hydroxyethylthiomethyltris (mercaptoethylthiomethyl) methane, etc. Is mentioned. Further, a halogen-substituted product of these chlorine-substituted product or bromine-substituted product may be used. They are,
Each of them may be used alone, or two or more of them may be used in combination.

[0020] Among the sulfur-containing lens materials used in the present invention, the sulfur-containing epoxy resin comprises an active hydrogen compound and an epoxy resin having two or more epoxy groups in one molecule. Examples of the active hydrogen compound include polythiols, mercapto compounds having a hydroxy group, sulfur-containing polyols, thiosalicylic acid, thioglycolic acid, 3,3-dithioisobutyric acid, and thiol. Mercaptocarboxylic acids such as lactic acid and thiomalic acid; hydroxycarboxylic acids containing a sulfur atom such as 3- (hydroxysulfoxy) propionic acid; m-benzenedisulphonic acid, o-benzenedisulfinic acid, 4-aminobenzenesulfonic acid; Sulfonic and sulfinic acid compounds such as 2-aminoethylsulfonic acid, 1,4-disulfophenol, 4-sulfobenzoic acid, 4-mercaptobenzenesulfonic acid, and bis (4-sulfobenzene) disulfide; bis (2-amino Ethyl) disulfide, bis (3-
Aminopropyl) sulfide, 4-aminobenzenethiophenol, 3,5-dihydroxybenzenesulfonamide, cystathionine, cystine, lanthionine, methionine, 2-sulfonylamidothiazole-5-benzoic acid, 3- (hydroxysulfonyloxy) propionic acid, Amines and amides having a sulfur atom such as N-ethyl-N'-methylsulfonamide;

Examples of the epoxy resin having two or more epoxy groups in one molecule include (1) diaminodiphenylmethane, metaxylylenediamine, paraxylylenediamine, metaaminobenzylamine, and paraaminobenzyl. Amine, 1,3-bisaminomethylcyclohexane, 1,4-bisaminomethylcyclohexane,
1,3-diaminocyclohexane, 1,4-diaminocyclohexane, metaphenylenediamine, paraphenylenediamine, benzylamine, diaminodiphenylsulfone, diaminodiphenylether, diaminodiphenylsulfide, diaminodiphenylketone, naphthalenediamine, aniline, toluidine, metaaminophenol , Paraaminophenol, aminonaphthol, phthalamide, isophthalamide, terephthalamide, benzamide, toluamide, parahydroxybenzamide,
Epoxy resin produced by a known production method from compounds having an amino group or an amide group such as metahydroxybenzamide,

(2) Hydroquinone, catechol, resorcin, bisphenol A, bisphenol F, bisphenol sulfone, brominated bisphenol A, novolak resin, cresol novolak resin, phenols such as tetraphenylethane and triphenylethane by a known production method. Manufactured epoxy resin, (3) ethylene glycol, diethylene glycol, triethylene glycol, polyethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, 1,4-butanediol, 1,6-hexanediol, neopentyl glycol, dibromo Neopentyl glycol, trimethylolpropane, glycerin, pentaerythritol, polycaprolactone, polytetramethylene ether glyco , Polybutadiene glycol, hydrogenated bisphenol A, cyclohexanedimethanol, polyhydric alcohols such as bisphenol A / ethylene oxide adducts, bisphenol A / propylene oxide adducts, and polyester polyols made from these polyhydric alcohols and polycarboxylic acids (4) Cyclopentadiene epoxide, epoxidized soybean oil epoxidized polybutadiene, vinylcyclohexene epoxide, trade name ERL-4 of Union Carbide Co.
221, epoxides of unsaturated compounds known as ERL-4234, ERL-4299, etc., (5) adipic acid,
Sebacic acid, dodecanedicarboxylic acid, dimer acid, phthalic acid, isophthalic acid, terephthalic acid, tetrahydrophthalic acid, methyltetrahydrophthalic acid, hexahydrophthalic acid, hetonic acid, nadic acid, maleic acid, fumaric acid, trimellitic acid, benzene Tetracarboxylic acid, butanetetracarboxylic acid, benzophenonetetracarboxylic acid, 5- (2,5-dioxotetrahydrofuryl) -3
Epoxy resin produced by known production methods from polycarboxylic acids such as -methyl-cyclohexene-1,2-dicarboxylic acid,

(6) A compound having an active hydrogen group such as a hydroxy group, an amino group or an amide group and a polyisocyanate having two or more functional groups (for example, tolylene diisocyanate, diphenylmethane-4,4'-diisocyanate, hexa Methylene diisocyanate, isophorone diisocyanate,
Urethane epoxy resin produced from xylylene diisocyanate, naphthalene diisocyanate, etc.) and glycidol or 3-hydroxypropylene sulfide;
(7) 3,4-epoxycyclohexyl-3,4-epoxycyclohexanecarboxylate, vinylcyclohexene dioxide, 2- (3,4-epoxycyclohexyl-5,5-spiro-3,4-epoxy) dichlorohexane-meta Alicyclic epoxy resins such as dioxane and bis (3,4-epoxycyclohexyl) adipate;
((8) Other epoxy resins include tris epoxy isocyanurate, glycidyl (meth) acrylate copolymer, 1,2-propylene sulfide (meth) acrylate copolymer, and the above-mentioned epoxy polyisocyanate, dicarboxylic acid, A modified resin with a polyhydric phenol or the like can be used.

Among the materials for the sulfur-containing lens used in the present invention, the raw material monomers for the polythio (meth) acrylate resin include polythiols and hydroxy groups among the compounds mentioned above as the raw materials for the sulfur-containing urethane resin. And acrylic esters or methacrylic esters of mercapto compounds having the formula: Furthermore, among the materials for the sulfur-containing lens used in the present invention, as the raw material monomer for the sulfur-containing poly (meth) acrylate resin, the polythiol having a sulfur atom among the compounds mentioned above as the raw material for the sulfur-containing urethane-based resin Acrylic ester or methacrylic ester. Each plastic lens made of these resins is a high refractive index plastic lens having a refractive index of 1.50 or more.

The sulfur-containing plastic lens of the present invention comprises:
Usually, it is obtained by cast polymerization. Specifically, the monomer mixture and the above-mentioned compound used in the present invention are mixed well, and if necessary, the mixed solution is defoamed by an appropriate method, then poured into a mold, and heated. Polymerize. At this time, a known release treatment may be applied to the mold in order to facilitate release after polymerization. Further, in order to adjust the reaction rate to a desired one, a known catalyst may be appropriately added. The polymerization temperature and the polymerization time are appropriately determined depending on the combination of the monomers to be used, the type of the compound to be added, and the like. For example, the polymerization can be performed at 20 to 200 ° C. for 0.5 to 100 hours.

When the sulfur-containing plastic lens of the present invention is a plastic lens made of, for example, a sulfur-containing urethane resin, when the compound used in the present invention is a compound having active hydrogen, it is preliminarily reacted with an isocyanate compound. You can put it. Also, if necessary, as in the known molding method, an internal release agent, a chain extender, a crosslinking agent, a light stabilizer, an ultraviolet absorber, an antioxidant, an oil-soluble dye,
Various substances such as fillers may be added. In addition, the sulfur-containing plastic lens of the present invention may have a surface polished surface for improving anti-reflection, imparting high hardness, improving abrasion resistance, improving chemical resistance, imparting anti-fogging property or imparting fashionability, if necessary. And physical or chemical treatments such as antistatic treatment, hard coat treatment, anti-reflection coat treatment, dyeing treatment, and light control treatment.

[0027]

EXAMPLES The present invention will be described in more detail with reference to the following Examples, but it should not be construed that the present invention is limited thereto. Example 1 After 46.5 parts by weight of m-xylylene diisocyanate, 53.5 parts by weight of pentaerythritol tetrakis (thioglycolate), 0.1% by weight of dibutyltin dilaurate and 0.1% by weight of benzyldimethylcarbinol were thoroughly mixed and sufficiently defoamed. This mixture was poured into a mold subjected to a release treatment. Initially, heat at 50 ° C for 5 hours,
The polymerization was carried out by heating at 90 ° C for 5 hours, at 100 ° C for 5 hours, and at 120 ° C for 5 hours. After the completion of the polymerization, the mixture was gradually cooled, and the polymer was taken out of the mold. The obtained lens was colorless and transparent, and no odor was felt even when approached to the nose. When this was cut and polished with an edger for processing eyeglass lenses, the inherent smell inherent to sulfur almost disappeared,
The worker did not feel any discomfort.

Example 2 A lens was obtained in the same manner as in Example 1, except that 0.1% by weight of methionol was used instead of benzyldimethylcarbinol. The obtained lens was used in Example 1.
As a result of cutting and polishing in the same manner as described above, the inherent odor peculiar to sulfur almost disappeared, and the operator did not feel discomfort.

Example 3 The procedure of Example 1 was repeated, except that 0.01% by weight of isoamyl isovalerate was used instead of benzyldimethylcarbinol.
A lens was obtained in the same manner as in Example 1. When the obtained lens was cut and polished in the same manner as in Example 1, the inherent odor peculiar to sulfur almost disappeared, and the operator did not feel discomfort.

Comparative Example 1 The procedure of Example 1 was repeated, except that benzyldimethylcarbinol used in Example 1 was replaced by l-bornyl acetate, a fragrance imparting compound disclosed in Japanese Patent Publication No. 2-56641. A lens was obtained in the same manner as described above. When the obtained lens was cut and polished in the same manner as in Example 1, an odor peculiar to sulfur was strongly generated, and the operator felt strong discomfort.

Comparative Example 2 A lens was obtained in the same manner as in Example 1 except that benzyldimethylcarbinol was not used.
When the obtained lens was cut and polished in the same manner as in Example 1, an odor peculiar to sulfur was strongly generated, and the operator felt strong discomfort.

[0032]

The sulfur-containing plastic lens of the present invention
During processing such as cutting and polishing of the sulfur-containing lens, almost no odor or odor peculiar to sulfur is generated. Therefore, it is possible for the worker to process the sulfur-containing lens without feeling uncomfortable, and when the spectacle lens or the like is normally mounted, there is no odor at all, so that it can be handled in exactly the same manner as the conventional product. .

──────────────────────────────────────────────────続 き Continued on the front page (58) Field surveyed (Int. Cl. ⁷ , DB name) G02B 1/04 C08G 18/00-18/87 C08G 71/00-71/04

Claims (4)

(57) [Claims] 1. A high-refractive-index sulfur-containing plastic lens having a crosslinked structure having a refractive index of 1.50 or more, comprising β-ionone, isoamyl isovalerate, methionol, and n-acetic acid.
-At least one compound selected from amyl, 2-phenyl-2-propanol, benzyldimethylcarbinol, isopulegol or eucalyptus oil in an amount of 0.005
A sulfur-containing plastic lens, characterized by containing 0.5 to 0.5% by weight. 2. In the production of a high refractive index sulfur-containing plastic lens having a crosslinked structure having a refractive index of 1.50 or more,
Β-ionone, isoamyl isovalerate, methionol, n-amyl acetate, 2-phenyl-2
-A method for producing a sulfur-containing plastic lens, comprising adding 0.005 to 0.5% by weight of at least one compound selected from propanol, benzyldimethylcarbinol, isopulegol or eucalyptus oil and heating and polymerizing the compound. 3. The sulfur-containing plastic lens according to claim 1, wherein the sulfur-containing plastic lens is a plastic lens made of a sulfur-containing urethane resin. 4. The method for producing a sulfur-containing plastic lens according to claim 2, wherein the monomer mixture is a monomer mixture comprising a bifunctional or higher functional polyisocyanate compound and a bifunctional or higher functional polythiol compound.