JPH0999441A - Internal release agent for molding plastic lens and production of plastic lens - Google Patents

Abstract

PROBLEM TO BE SOLVED: To prevent the generation of opacity in a molding lens, to suppress coloration and to enhance release effect by using a compd. of a metal salt of phosphoric ester or a metal salt of phosphoric diester represented by formula as a molding internal release agent. SOLUTION: One or more kind of two kinds of compds. represented by formulae I, II (wherein M is K or Na, R is a 1-30C alkyl group, a 7-30C alkylphenyl group or a 7-12C phenylalkyl group. OA is alkylene carbide and n is an integer of 1-30) as an internal release agent for molding plastic. One or more kind of the internal release agent is added to the monomer mixture in the total amt. of 10-10000ppm to perform polymerization and molding.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to an internal mold release agent for molding a plastic lens and a method for producing a plastic lens using the mold release agent.

[0002]

2. Description of the Related Art Resin lenses are lighter than glass,
It is characterized by being tough, and urethane resins, thiourethane resins, epoxy resins, episulfide resins, acrylic resins, vinyl aromatic resins, allyl resins, etc. have been developed and used so far. All of these resin lenses are manufactured by cast polymerization, and a glass mold is generally widely used as a mold. Typical examples of the monomer injected into the mold are polyisocyanate compound and hydroxy group-containing compound or thiol group-containing compound in the case of urethane resin and thiourethane resin, and epoxy group or episulfide in the case of epoxy resin and episulfide resin. Group-containing compounds, acrylic resins, acrylates in the case of methacrylic resins, methacrylate compounds, styrene in the case of vinyl aromatic resins, divinylbenzene compounds, diethylene glycol diallyl carbonate in the case of allyl resins,
It is a diallyl phthalate compound, and these compounds can be mixed and used with each other to form various copolymers. All of these monomers corresponding to each resin physically or chemically adhere to the glass surface of the mold during polymerization and curing, which often makes it difficult to release the mold after polymerization.
There was a remarkable problem in the case of a monomer having a polar group such as an epoxy group, an ester group, a carbonate group, etc., and particularly a problem in the case of a monomer having an isocyanate group or an epoxy group. As a result, the yield of the lens manufacturing process becomes poor, which is an economic disadvantage. For this reason, release agents have been used to enable or facilitate release. As a releasing method using a releasing agent, an external releasing agent applied to a mold and used or an internal releasing agent added to a monomer is known. The method of applying the release agent to the mold is extremely complicated,
There are problems such as unevenness on the surface of the molded product and turbidity of the transparent molded product. Further, as the internal mold release agent, conventionally, an acidic alkyl phosphate ester (Japanese Patent Laid-Open No. 64-456)
11), acidic alkyl phosphoric acid ester salts (JP-A-6-136086), acidic ethylene oxide type alkyl phosphoric acid esters (JP-A-3-287641),
Quaternary ammonium salts, metal salts of higher fatty acids, higher fatty acid esters and the like (Japanese Patent Laid-Open No. 64-45611) have been proposed. However, unless these mold release agents are added to the mixed monomer in an amount of about 500 ppm to 10000 ppm or more, it is difficult to release the molded product from the molded product after polymerization, which inevitably affects the lens material itself. It gave a cloudiness to the lens and caused coloring. Further, as a material having a high releasing effect by adding a small amount of about 50 to 500 ppm, a fluorine-based nonionic surfactant, a silicon-based nonionic surfactant and the like can be mentioned (JP-A-64).
However, the use of these release agents has a problem in that lens turbidity occurs even when added in a small amount.

[0003]

Difficulty in mold release when manufacturing a plastic lens is improved by using an internal mold release agent. Coloring has reduced the value as an optical material and an optical product, which has been a problem. Therefore, it has been desired to develop an internal mold release agent that can solve these problems.

[0004]

An object of the present invention is to form an internal mold release for plastic lens molding, which comprises at least one kind of two kinds of compounds represented by the formulas (1) and (2). 10 to 1 of the agent in the monomer mixture
This has been solved by the method for producing a plastic lens, which is polymerized and molded by adding in the range of 10,000 ppm. That is, according to the present invention, the phosphoric acid ester metal salt-based compound represented by the general formula (1) or (2) is inert to various components such as a monomer compound and a tin-based catalyst contained in a plastic lens molding material. , Molded lenses using this do not cause cloudiness and can suppress coloration, and have a higher releasing effect than acidic phosphate esters, etc., which are conventionally known as internal releasing agents, and addition of a small amount is sufficient. It was completed after finding that it has mold release ability.

[0005]

BEST MODE FOR CARRYING OUT THE INVENTION The internal release agent for molding a plastic lens according to the present invention is characterized by comprising at least one kind of compounds represented by the general formulas (1) and (2).

Embedded image

Embedded image (M is one kind of metal selected from K and Na, R is an alkyl group having 1 to 30 carbon atoms, an alkylphenyl group having 7 to 30 carbon atoms, or phenylalkyl having 7 to 12 carbon atoms. And OA represents alkylene oxide,
n shows the numerical value of 1-30. )

The compound represented by the above general formula (1) is
Phosphoric acid monoester metal salt. As the monoester metal salt, specifically, n of alkylene oxide is 1 to
When 30 and R is an alkyl group having 1 to 30 carbon atoms, for example, a phosphoric acid monoester metal salt of polyoxyethylene methyl ether (wherein the carbon number is 1,
That is, R is a methyl group and OA is ethylene oxide (--CH ₂
CH ₂ O-)), polyoxyethylene ethyl ether monoester metal phosphate (in this case, having 2 carbon atoms, that is, R is an ethyl group), polyoxyethylene propyl ether phosphate monoester metal salt Polyoxyethylene butyl ether phosphate monoester metal salt, Polyoxyethylene pentyl ether phosphate monoester metal salt, Polyoxyethylene hexyl ether phosphate monoester metal salt, Polyoxyethylene heptyl ether phosphate monoester metal salt Salt, polyoxyethylene octyl ether phosphate monoester metal salt, polyoxyethylene nonyl ether phosphate monoester metal salt, polyoxyethylene decyl ether phosphate monoester metal salt, polyoxyethylene undecyl ether phosphate Monoester metal salts, phosphoric acid monoester metal salts of polyoxyethylene dodecyl ether,
Polyoxyethylene tridecyl ether phosphate monoester metal salt, polyoxyethylene tetradecyl ether phosphate monoester metal salt, polyoxyethylene pentadecyl ether phosphate monoester metal salt, polyoxyethylene hexadecyl ether phosphorus Acid monoester metal salt, polyoxyethylene heptadecyl ether phosphate monoester metal salt, polyoxyethylene stearyl ether phosphate monoester metal salt, polyoxyethylene nonadecyl ether phosphate monoester metal salt, polyoxyethylene Eicosyl ether phosphate monoester metal salt, polyoxyethylene docosyl ether phosphate monoester metal salt, polyoxyethylene tricosyl ether phosphate monoester metal salt, polyoxyethylene ether Lacosyl ether phosphate monoester metal salt, polyoxyethylene pentacosyl ether phosphate monoester metal salt, polyoxyethylene hexacosyl ether phosphate monoester metal salt, polyoxyethylene heptacosyl ether phosphate monoester Metal salts, phosphoric acid monoester metal salts of polyoxyethylene octacosyl ether, phosphoric acid monoester metal salts of polyoxyethylene nonacosyl ether, phosphoric acid monoester metal salts of polyoxyethylene tricontaether, etc. propylene methyl ether phosphoric acid monoester metal salts (in this case, R is a methyl group, OA is propylene oxide _{(-CH 2 CH (CH 3)} O
-), Phosphoric acid monoester metal salt of polyoxypropylene ethyl ether, phosphoric acid monoester metal salt of polyoxypropylene propyl ether, phosphoric acid monoester metal salt of polyoxypropylene butyl ether, phosphoric acid monoester metal salt of polyoxypropylene pentyl ether Ester metal salt, phosphoric acid monoester metal salt of polyoxypropylene hexyl ether, phosphoric acid monoester metal salt of polyoxypropylene heptyl ether, phosphoric acid monoester metal salt of polyoxypropylene octyl ether,
Polyoxypropylene nonyl ether phosphate monoester metal salt, polyoxypropylene decyl ether phosphate monoester metal salt, polyoxypropylene undecyl ether phosphate monoester metal salt, polyoxypropylene dodecyl ether phosphate monoester Metal salts, polyoxypropylene tetradecyl ether phosphate monoester metal salts, polyoxypropylene pentadecyl ether phosphate monoester metal salts, polyoxypropylene hexadecyl ether phosphate monoester metal salts, polyoxypropylene heptadecyl Phosphoric acid monoester metal salt of ether, phosphoric acid monoester metal salt of polyoxypropylene stearyl ether, phosphoric acid monoester metal salt of polyoxypropylene nonadecyl ether, polyoxy Propylene eicosyl ether phosphate monoester metal salt, polyoxypropylene docosyl ether phosphate monoester metal salt, polyoxypropylene tricosyl ether phosphate monoester metal salt, polyoxypropylene tetracosyl ether phosphate monoester Metal salts, phosphoric acid monoester metal salts of polyoxypropylene pentacosyl ether, phosphoric acid monoester metal salts of polyoxypropylene hexacosyl ether, phosphoric acid monoester metal salts of polyoxypropylene heptacosyl ether, polyoxypropylene octacocyl Metal phosphate monoester metal salts of polyether, polyoxypropylene nonacosyl ether phosphate monoester metal salts, polyoxypropylene tricontaether phosphate monoester metal salts, etc. When n of alkylene oxide is 1 to 30 and R is an alkylphenyl group having 7 to 30 carbon atoms, for example, phosphoric acid monoester metal salt of polyoxyethylene methylphenyl ether, polyoxyethylene ethyl. Phenyl ether phosphate monoester metal salt, polyoxyethylene propyl phenyl ether phosphate monoester metal salt, polyoxyethylene butyl phenyl ether phosphate monoester metal salt, polyoxyethylene pentyl phenyl ether phosphate monoester metal salt Salt, phosphoric acid monoester metal salt of polyoxyethylene hexyl phenyl ether,
Polyoxyethylene heptyl phenyl ether phosphate monoester metal salt, polyoxyethylene octyl phenyl ether phosphate monoester metal salt, polyoxyethylene nonyl phenyl ether phosphate monoester metal salt, polyoxyethylene decyl phenyl ether phosphorus Acid monoester metal salt, polyoxyethylene undecyl phenyl ether phosphoric acid monoester metal salt, polyoxyethylene dodecyl phenyl ether phosphoric acid monoester metal salt, polyoxyethylene tridecyl phenyl ether phosphoric acid monoester metal salt, Polyoxyethylene tetradecyl phenyl ether phosphoric acid monoester metal salt, polyoxyethylene pentadecyl phenyl ether phosphoric acid monoester metal salt, polyoxyethylene hexadecyl Phenyl ether phosphate monoester metal salt, polyoxyethylene heptadecyl phenyl ether phosphate monoester metal salt, polyoxyethylene stearyl phenyl ether phosphate monoester metal salt, polyoxyethylene nonadecyl phenyl ether phosphate monoester Ester metal salt, phosphoric acid monoester metal salt of polyoxyethylene eicosyl phenyl ether, phosphoric acid monoester metal salt of polyoxyethylene docosyl phenyl ether, phosphoric acid monoester metal salt of polyoxyethylene tricosyl phenyl ether, poly Phosphoric acid monoester metal salt of oxyethylene tetracosyl phenyl ether, etc. Also, phosphoric acid monoester metal salt of polyoxypropylene methyl phenyl ether,
Polyoxypropylene ethyl phenyl ether phosphoric acid monoester metal salt, polyoxypropylene propyl phenyl ether phosphoric acid monoester metal salt, polyoxypropylene butyl phenyl ether phosphoric acid monoester metal salt, polyoxypropylene pentyl phenyl ether phosphorus Acid monoester metal salt, polyoxypropylene hexyl phenyl ether phosphoric acid monoester metal salt, polyoxypropylene heptyl phenyl ether phosphoric acid monoester metal salt, polyoxypropylene octyl phenyl ether phosphoric acid monoester metal salt,
Polyoxypropylene nonyl phenyl ether phosphate monoester metal salt, polyoxypropylene decyl phenyl ether phosphate monoester metal salt, polyoxypropylene undecyl phenyl ether phosphate monoester metal salt, polyoxypropylene dodecyl phenyl ether Phosphoric acid monoester metal salt, polyoxypropylene tridecyl phenyl ether phosphoric acid monoester metal salt, polyoxypropylene tetradecyl phenyl ether phosphoric acid monoester metal salt, polyoxypropylene pentadecyl phenyl ether phosphoric acid monoester metal salt Salt, phosphoric acid monoester metal salt of polyoxypropylene hexadecyl phenyl ether, phosphoric acid monoester metal salt of polyoxypropylene heptadecyl phenyl ether, Oxypropylene stearyl phenyl ether phosphate monoester metal salt, polyoxypropylene nonadecyl phenyl ether phosphate monoester metal salt, polyoxypropylene eicosyl phenyl ether phosphate monoester metal salt, polyoxypropylene docosyl phenyl ether Monophosphoric acid monoester metal salt of polyoxypropylene tricosyl phenyl ether, polyoxypropylene tetracosyl phenyl ether phosphoric acid monoester metal salt, etc., and n of alkylene oxide is from 1 to 30. And when R is a phenylalkyl group having 7 to 12 carbon atoms, for example, a phosphoric acid monoester metal salt of polyoxyethylene phenyl methoxy ether or polyoxyethylene phenyl ethoxy ether Phosphate monoester metal salts, phosphoric acid monoester metal salts of polyoxyethylene phenylpropoxy ether, phosphoric acid monoester metal salts of polyoxyethylene phenyl-butoxy ether,
Phosphoric acid monoester metal salt of polyoxyethylene phenyl pentoxy ether, phosphoric acid monoester metal salt of polyoxyethylene phenylhexoxy ether, etc., and phosphoric acid monoester metal salt of polyoxypropylene phenyl methoxy ether, polyoxypropylene Phenyl ethoxy ether phosphate monoester metal salt, polyoxypropylene phenyl propoxy ether phosphate mono ester metal salt, polyoxypropylene phenyl butoxy ether phosphate mono ester metal salt, polyoxypropylene phenyl pentoxy ether phosphate mono ester Examples thereof include ester metal salts and phosphoric acid monoester metal salts of polyoxypropylene phenylhexoxy ether. Examples of the phosphoric acid diester metal salt represented by the general formula (2) include diesters corresponding to the above monoesters. Further, in the above specific examples of the sodium salt and potassium salt of the diester, R may be the same or different from each other.

Among the phosphoric acid monoester and diester metal salts of the present invention, the releasability at the time of releasing the polymerization-cured resin lens added to the monomer mixed solution from the mold and the appearance of the obtained lens, If you consider the balance of physical properties,
As a preferred specific example, R in the general formulas (1) and (2) is
It is either an alkyl group, an alkylphenyl group, or a phenylalkyl group, and the alkyl group and the alkylphenyl group in the alkylphenyl group have 8 to 18 carbon atoms, and ethylene oxide is preferable, and has a structure of n = 2 to 10 Examples thereof include potassium monoester salt, potassium diester salt, sodium monoester salt, and sodium diester salt. As specific examples of the preferred phosphoric acid monoester and diester metal salts as described above, those having an ethylene oxide structure of n = 2 include those of phosphoric acid monoesters and diesters of polyoxyethylene octyl ether when R is an alkyl group. Sodium salt, sodium salt of phosphoric acid monoester and diester of polyoxyethylene nonyl ether, sodium salt of phosphoric acid monoester and diester of polyoxyethylene decyl ether, sodium salt of phosphoric acid monoester and diester of polyoxyethylene undecyl ether Salts, sodium salts of phosphoric acid monoesters and diesters of polyoxyethylene dodecyl ether, sodium salts of phosphoric acid monoesters and diesters of polyoxyethylene tridecyl ether, polyoxyethylene tetradecyl ether Sodium salt of phosphoric acid monoester and diester of ether, sodium salt of phosphoric acid monoester and diester of polyoxyethylene pentadecyl ether, sodium salt of phosphoric acid monoester and diester of polyoxyethylene hexadecyl ether, polyoxyethylene hepta Examples thereof include sodium salts of decyl ether phosphoric acid monoesters and diesters, sodium salts of phosphoric acid monoesters of polyoxyethylene stearyl ethers and diesters, and when R is an alkylphenyl group, phosphoric acid monoesters of polyoxyethylene octylphenyl ether. Ester and diester sodium salts, polyoxyethylene nonylphenyl ether phosphate monoesters and diester sodium salts, polyoxyethylene decylphenyl ether Telluric acid monoester and diester sodium salt, polyoxyethylene undecylphenyl ether phosphoric acid monoester and diester sodium salt, polyoxyethylene dodecylphenyl ether phosphoric acid monoester and diester sodium salt, polyoxyethylene Sodium salt of phosphoric acid monoester and diester of tridecyl phenyl ether, sodium salt of phosphoric acid monoester and diester of polyoxyethylene tetradecyl phenyl ether, sodium salt of phosphoric acid monoester and diester of polyoxyethylene pentadecyl phenyl ether , Polyoxyethylene hexadecyl phenyl ether phosphate monoester and diester sodium salt, polyoxyethylene heptadecyl phenyl ether And sodium salts of phosphoric acid monoesters and diesters of polyoxyethylene stearyl phenyl ether. Further, ethylene oxide is n = 3 to
In the case of 10 as well, R can be sodium salts of phosphoric acid monoesters and diesters having the same substituents as described above. In the above specific examples of the preferred sodium salt of phosphodiester, R may be the same or different from each other. These compounds are stable compounds, are inert to the monomers and catalysts contained in the plastic lens molding material, do not cause cloudiness in the lens, suppress coloring, and are capable of producing transparent lenses. .

The internal release agent of the present invention is at least one of the compounds represented by the above general formulas (1) and (2).
10 to 10,000p in molding material
Add in the range of pm. If it is less than 10 ppm, it is difficult to release the mold, and if it exceeds 10,000 ppm, the lens may be clouded, striae or colored. It is preferably 10 to 5000 ppm, more preferably 10 to 1000 in total in the combined system of the general formulas (1) and (2).
Addition within the range of ppm improves the lens appearance and lens physical properties.

The present invention further relates to a method of manufacturing a plastic lens using the above internal release agent. In the present invention, the lens material is used as urethane resin, thiourethane resin, epoxy resin, episulfide resin, acrylic resin, vinyl aromatic resin, allyl resin, and copolymer resins thereof.

Urethane resin and thiourethane resin are
It is produced by casting polymerization of a bifunctional or higher polyisocyanate compound and a hydroxy compound or a thiol compound. The internal release agent of the present invention may be added to any of a polyisocyanate compound, a hydroxy compound or a thiol compound, and may be added after mixing these, and further, as will be described later, various auxiliary materials, additives, It may be added together with the catalyst by any addition method. Specific examples of the polyisocyanate compound include hydrogenated 2,6-tolylene diisocyanate, hydrogenated meta and paraphenylene diisocyanate, hydrogenated 2,4-tolylene diisocyanate, hydrogenated diphenylmethane diisocyanate, hydrogenated metaxylylene diisocyanate, Alicyclic diisocyanate compounds such as hydrogenated paraxylylene diisocyanate, isophorone diisocyanate, bicycloheptane diisocyanates having a structure in which two isocyanate groups are bonded directly to a bicycloheptane ring via a methylene group; meta and paraphenylene diisocyanates, 2 , 6-tolylene diisocyanate, 2,4-tolylene diisocyanate, 4,4'-diphenylmethane diisocyanate, meta and para-xylylene diisocyanate, meta and Para-tetramethylxylylene diisocyanate, 2,6-naphthalene diisocyanate,
Aromatic diisocyanate compounds such as 1,5-naphthalene diisocyanate; hexamethylene diisocyanate,
Octamethylene diisocyanate, 2,2,4-trimethylhexamethylene diisocyanate, tetramethylene diisocyanate, burette reaction product of hexamethylene diisocyanate, hexamethylene diisocyanate trimer, lysine diisocyanate, lysine triisocyanate, 1, 6, Other polyisocyanates such as 11-undecane triisocyanate and triphenylmethane triisocyanate can be used. Preferred polyisocyanate compounds are hexamethylene diisosonate, hydrogenated 4,4′-diphenylmethane diisocyanate, hydrogenated metaxylylene diisocyanate, isophorone diisocyanate and metaxylylene diisocyanate.

Specific examples of the hydroxy compound include ethylene glycol, diethylene glycol, propylene glycol, 1,4-butanediol, β, β.
′ -Dihydroxydiethyl ether, dipropylene glycol, 1,3-butylene glycol, 1,4-butylene glycol, neopentyl glycol, polyethylene glycol, polypropylene glycol, 1,12 dodecanediol, 2-hydroxy-1,3-di Methacryloxypropane, 1,4-cyclohexanedimethanol, glycerin, trimethylolethane, trimethylolpropane, butanetriol, 1,2-methaneglucoside, 1,2,6-hexanetriol, pentaerythritol, dipentaerythritol, Aliphatic or alicyclic alcohol compounds such as tripentaerythritol, sorbitol, cyclohexanediol, cyclohexanetriol; 2-hydroxyethyl acrylate, acrylic acid-2- Droxypropyl, 2-hydroxybutyl acrylate, 2-hydroxy-3-chloropropyl acrylate, 2-hydroxyethyl methacrylate, 3-hydroxypropyl methacrylate, 4-hydroxybutyl methacrylate, methacrylic acid -2-
Acrylic acid or methacrylic acid ester having hydroxy group such as hydroxy-3-chloropropyl; 2-
(Vinylbenzylthio) ethanol, bis (vinylbenzylthio) propanol, 2- (bis (vinylbenzylthio) propylthio) 2-ethanol and the like sulfur-containing aromatic hydroxy compounds containing unsaturated bonds, these hydroxy compounds alone, Alternatively, two or more kinds can be mixed and used, and preferable hydroxy compounds include 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, and 2- (vinylbenzylthio) ethanol.

Specific examples of thiol compounds include:
Di (2-mercaptoethyl) ether, 2-mercaptoethanol, 1,3-propanedithiol, 1,5-dimercapto-3-thiapentane, 1,2-ethanedithiol, 1,4-butanedithiol, 2,3-di Mercaptopropanol, 1,2-dihydroxy-3-mercaptopropane, di (2-mercaptoethyl) sulfide,
1,2-bis-2-mercaptoethylthioethane, 1,1,
3-bis-2-mercaptoethylthiopropane, 1,4
-Bis-2-mercaptoethylthiobutane, 1,6-bis-2-mercaptoethylthiohexane, bis-2-
(2-mercaptoethylthio) ethyl sulfide, bis-2-mercaptoethoxymethane, 1,2-bis-2-
Mercaptoethoxyethane, bis-2- (2-mercaptoethoxy) ethyl ether, ethylene glycol dithioglycolate, trimethylolpropane tris (thioglycolate), pentaerythritoliol, pentaerythritol tetrakis (thioglycolate) benzenedithiol, tetrakis (Mercaptomethyl) methane,
1,1,1-tris (mercaptomethyl) ethane, 2-
Ethyl-2- (mercaptomethyl) propane, 1,2-
Bis [(2-mercaptoethyl) thio] -3-mercaptopropane, pentaerythritol tetrakismercaptopropionate, pentaerythritol tetrakismercaptoacetate, 2,5-bis (mercaptomethyl) -2,5-dimethyl-1,4- Dithian, 2,5-
Dimercaptomethyl-1,4-dithiane, 2,5-bis (2-mercaptoethylthiomethyl) -1,4-dithiane, 2,5-bis (2-mercaptopropyl) -1,4
-Dithiane, 4-mercaptophenol, 1,2-benzenedithiol, 1,3-benzenedithiol, 1,4
-Benzenedithiol, 1,3,5-benzenetrithiol, bis (mercaptomethylene) benzene, bis (mercaptoethylene) benzene, bis (2-mercaptoethylenethio) benzene, bis (2-mercaptoethylenethiomethylene) benzene, methacryl Examples thereof include acid-2-mercaptoethylthioester and 2- (vinylbenzylthio) ethanethiol. These thiol compounds may be used alone or in combination of two or more,
Preferred are methacrylic acid-2-mercaptoethyl thioester and 2- (vinylbenzylthio) ethanethiol.

The resin having a urethane or thiourethane structure can be produced by addition-polymerizing a polyisocyanate compound and a hydroxy compound or a thiol compound in various combinations according to the purpose. For example, a resin obtained from hexamethylene diisosonate, hydrogenated metaxylylene diisocyanate, isophorone diisocyanate, metaxylylene diisocyanate and 2- (vinylbenzylthio) ethanol is a resin molded by a urethane reaction and a radical polymerization reaction. It is a lens material excellent in physical properties such as high refractive index, transparency, heat resistance, light weight, impact resistance, and workability. The polyisocyanate compound and the hydroxy compound or the thiol compound are the sum of -NCO group / -OH group and -SH group = 0.5 to
Mix to a ratio of 2.0, preferably 0.75 to 1.5. Outside this range, desirable physical properties of the lens, such as the refractive index and workability, deteriorate.

In the method for producing a urethane or thiourethane resin lens of the present invention, the monomer mixture and the internal mold release agent of the present invention are used as essential components, and the reaction of the hydroxy compound and the thiol compound with the polyisocyanate in the monomer mixture. In order to proceed sufficiently, a known catalyst such as a tin catalyst can be added in a trace amount. Specific examples of the tin catalyst include dibutyltin dilaurate, dibutyltin di-2-ethylhexoate, dibutyltin dimaleate,
Examples thereof include tin-based catalysts such as dibutyltin dichloride, tetrachlorotin, dibutyltin sulfide, dibutyltin diacetate, tin tartrate, and di (2-ethylhexyl) tin oxide. Among them, dibutyltin dilaurate is preferable.

When the hydroxy compound and the thiol compound contain a vinyl group, an acrylate, a methacrylate, an allyl group, etc., a radical polymerization initiator can be used as a polymerization accelerator. Specific examples include cumylperoxy. Neodecanoate, diisopropyl peroxydicarbonate, diallyl peroxydicarbonate,
Di-n-propyl peroxy dicarbonate, dimyristyl peroxy dicarbonate, cumyl peroxy neohexanoate, tert-hexyl peroxy neodecanoate, tert-butyl peroxy neodecanoate, tert-hexyl peroxy Neohexanoate, tert-butylperoxy neohexanoate,
2,4-dichlorobenzoyl peroxide, benzoyl peroxide, dicumyl peroxide, di-te
Peroxides such as rt-butyl peroxide; Hydroperoxides such as cumene hydroperoxide and tert-butyl hydroperoxide; 2,2′-
Azobis (4-methoxy-2,4-dimethylvaleronitrile), 2,2'-azobis (2-cyclopropylpropionitrile), 2,2'-azobis (2,4-dimethylvaleronitrile), 2,2 '-Azobisisobutyronitrile, 2,2'-azobis (2-methylbutyronitrile), 1,1'-azobis (cyclohexane-1-carbonitrile), 1-[(1-cyano-1-methyl Known thermal polymerization agents such as azo compounds such as ethyl) azo] formamide and 2-phenylazo-4-methoxy-2,4-dimethyl-valeronitrile, and known photopolymerization agents such as benzophenone and benzoin benzoin methyl ether. Among these, 2,2′-azobis (4
-Methoxy-2,4-dimethylvaleronitrile), 2,
2′-azobis (2-cyclopropylpropionitrile), 2,2′-azobis (2,4-dimethylvaleronitrile), 2,2′-azobisisobutyronitrile,
2,2′-azobis (2-methylbutyronitrile),
1,1'-azobis (cyclohexane-1-carbonitrile) can be mentioned.

In addition to the above-mentioned components, styrene, α-methylstyrene, divinylbenzene, diallyl phthalate, diethylene glycol bisallyl carbonate, methyl methacrylate, allyl may be used in the production of the urethane or thiourethane resin lens of the present invention. Methacrylate, 2-ethylhexyl methacrylate, n-
In addition to chain extenders such as butyl acrylate, diethylene glycol dimethacrylate, and phenyl methacrylate, crosslinking agents, light stabilizers, ultraviolet absorbers, antioxidants, oil-soluble dyes, fillers and the like can be added. In the production method of the present invention, the polymerization and curing are carried out by mixing or dissolving the above-mentioned various monomers with a catalyst, a polymerization initiator and various additives, and then injecting the raw material into a glass or metal mold, and heating and / or Alternatively, it is manufactured by removing it from the mold after proceeding the polymerization and curing reaction by irradiation with ultraviolet rays or electron beams. Curing time is 0.1-1
00 hours, usually 6 to 48 hours, and the curing temperature is -10.
˜160 ° C., usually −10 to 140 ° C. Further, surface treatment such as hard coating, antireflection and antifogging property can be carried out if necessary.

The method for producing the plastic lens of the present invention has been described above for the urethane and thiourethane resins.
Epoxy resins, episulfide resins, acrylic resins, vinyl aromatic resins, allyl resins, etc. are also produced by using known monomers and under various known conditions, using various auxiliary materials and additives in combination. At this time, the internal release agent of the present invention is used, but the addition method and the like are similar to those of urethane and thiourethane resins.

[0018]

INDUSTRIAL APPLICABILITY The internal release agent of the present invention is inert to various components such as various monomer compounds and catalysts contained in the plastic lens molding material, does not cause cloudiness in the lens, and suppresses coloring. In addition, it has a higher releasing effect than conventional internal releasing agents such as acidic phosphoric acid esters.
Therefore, by using the internal mold release agent of the present invention, a colorless and transparent plastic lens can be easily manufactured, and mold release can be easily carried out.

The present invention will be described in more detail based on the following examples, but the invention is not intended to be limited thereto.

【Example】

Example 2- (Vinylbenzylthio) ethanol (57.6 parts by weight), isophorone diisocyanate (32.4 parts by weight), and styrene (10 parts by weight) were mixed and homogenized, and then n = 4 as an internal release agent was oxidized in this liquid. Separately added 0.0001 parts by weight to 0.5 parts by weight of mixed sodium salt of phosphoric acid monoester and diester of polyoxyethylene dodecyl ether having an ethylene structure (in order, 1 ppm, 10 ppm,
50ppm, 100ppm, 500ppm, 1000p
pm, 5000 ppm of 7 kinds), and 0.003 parts by weight of dibutyltin dilaurate as a catalyst were added to each of the above 7 kinds of liquids, and 2,2'-azobis (2,4-dimethylvalero) was used as a radical polymerization initiator. 0.2 parts by weight of nitrile) and 0.2 parts by weight of 1,1′-azobis (cyclohexane-1-carbonitrile) were similarly added to each and dissolved, and a degassing operation was performed as necessary. The above monomer mixture is poured into a mold made of two spherical glasses and a gasket made of a soft thermoplastic resin, and a mold made of two flat glasses and a gasket made of the same material, and the temperature is 10 ° C to 120 ° C. The temperature was gradually raised to 24 ° C. over 24 hours, and then maintained at 120 ° C. for 1 hour to polymerize and cure. The amount of the internal release agent added to the resin lens after the polymerization is 0.000
1 part by weight (1 ppm), 0.001 part by weight (10 pp
m) Other than the addition and molding, the lens was easily released from the mold, and the obtained lens was colorless and transparent and had good surface accuracy. Using the lens and the lens flat plate obtained as described above, color evaluation and cloudiness evaluation were performed. The results are shown in Table 1. Also, the mold release evaluation is shown. The evaluation method is as follows.

The mold release evaluation was performed in the following four stages. ◎: Very good (Releasable very easily) ○: Good (Releasable by simple demolding operation) △: Slightly bad (Releasing but resistance or
Mold peeling to the lens side) ×: Poor (all mold peeling to the lens side,
The lens flat plate (diameter 50 mm, thickness 4 mm) is evaluated for coloring.
Valuable material, JUKI spectrocolorimeter (JP7100
It was measured in F). The color of the lens is L^*a^*b ^*Da
Eargram b^*Indicated by value (automatically displayed by the device), b
^*The coloring degree of the lens is evaluated according to the range of values as follows.
Was. 0.50 ≧ b^* : Good 0.65 ≧ b^* > 0.50: Slightly good 0.75 ≧ b^* > 0.65: Somewhat bad b^* > 0.75: Poor cloudiness was evaluated by illuminating the lens with fluorescent light in a dark room.
Observe the transparency visually and check the whiteness of the lens in the following three steps.
evaluated. ◯: Good Δ: Slightly bad ×: Bad

Comparative Example Without adding the above-mentioned mixed sodium salt of phosphoric acid monoester and diester of polyoxyethylene dodecyl ether having an ethylene oxide structure of n = 4 as an internal release agent,
Di-n-butyl acid phosphate, isodecyl acid phosphate, sodium salt of octyl acid phosphate, polyoxyethylene dodecyl ether acid phosphate, zinc stearate, trimethyloctyl ammonium chloride, stearyl glyceryl ether, Unidyne DS-401 ( Fluorine-based, Daikin Industries, DK-8X (silicon-based, Dow Corning) were added in the same manner as in Example 1 (1 ppm, 10 p
pm, 50ppm, 100ppm, 500ppm, 10
00 ppm, 5000 ppm), and lens molding was performed. The mold release evaluation, the color evaluation, and the white turbidity evaluation were performed in the same manner. The results are shown in Tables 1 and 2.

[0022]

[Table 1]

[0023]

[Table 2]

 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Minoru Ohashi 6-1 1-1 Shinjuku, Katsushika-ku, Tokyo Mitsubishi Gas Chemical Co., Ltd. Tokyo Research Laboratory

Claims (5)

[Claims] 1. An internal mold release agent for molding a plastic lens, which comprises at least one kind of two kinds of compounds represented by the general formulas (1) and (2). Embedded image Embedded image (M is one kind of metal selected from K and Na, R is an alkyl group having 1 to 30 carbon atoms, an alkylphenyl group having 7 to 30 carbon atoms, or phenylalkyl having 7 to 12 carbon atoms. And OA represents alkylene oxide,
n shows the numerical value of 1-30. ) 2. A total of 10 to 10 of at least one kind of the internal release agent according to claim 1 in the monomer mixture.
A method for producing a plastic lens in which 000 ppm is added for polymerization and molding. 3. Two kinds of internal mold release agents represented by the general formulas (1) and (2) according to claim 1 are added together in the monomer mixture, and polymerization and molding are carried out at a total of 10 to 10,000 ppm. A method of manufacturing a plastic lens, comprising: 4. The method for producing a plastic lens according to claim 2, wherein the material of the plastic lens is a urethane resin, a thiourethane resin, an epoxy resin, an episulfide resin, an acrylic resin, a vinyl aromatic resin or an allyl resin. 5. A monomer mixture containing a polyisocyanate compound having two or more functional groups and a hydroxy group-containing compound or a thiol group-containing compound, and a product obtained by polymerizing and curing this monomer mixture has at least a urethane or thiourethane structure. The method of manufacturing a plastic lens according to claim 2 or 3, which is a resin lens included as a part.