JP2001300943A - Method for manufacturing plastic lens, and plastic lens - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a method for manufacturing a plastic lens having good surface accuracy, transparency and hardness and a method for using the plastic lens and a neutralization type phosphate. SOLUTION: The method for manufacturing the plastic lens comprises a first step of preparing a mixture liquid by adding the neutralization type phosphate represented by formula (I) (wherein R is a 1-12C alkylene group, R' is a 1-20C alkyl group or 7-26C alkylhydroxyphenyl group, n is an integer of 1 to 15, and m is an integer of 1 to 2) to a raw material monomer of the lens as an internal mold releasing agent, a second step of obtaining a polymer by pouring the liquid in a plastic lens mold and then polymerizing the liquid, and a third step of obtaining the lens by mold releasing the polymer from the mold. The method for using the plastic lens and the neutralization type phosphate obtained by the previous method is provided.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for producing a plastic lens, a method for using a plastic lens and a neutralized phosphate ester, and more particularly to a plastic lens having good surface precision, transparency and hardness, and a neutralizing method. The present invention relates to a method for using a type phosphate ester.

[0002]

2. Description of the Related Art In recent years, the demand for plastic lenses has been increasing because they are lighter, harder to break, and have better dyeability than glass lenses. A plastic lens is manufactured by injecting a monomer material for a plastic lens into a lens mold, polymerizing the monomer, and removing the monomer from the mold. Also, to make it easier to remove from the mold during manufacturing,
It is known to use an internal release agent such as an acid phosphate. For example, JP-A-64-45611 and JP-A-1-303302 disclose that when producing a polythiourethane lens containing a polyisocyanate compound and a polythiol compound, diisopropyl acid phosphate and dibutyl acid are used. It is disclosed to use certain internal mold release agents such as acidic phosphates such as phosphate, diethyl acid phosphate, butyl acid phosphate, and the like. However, when the internal release agents disclosed in these publications are used, a cloudy lens is easily obtained, and sufficient curing may not be obtained in some cases. In particular, when used for a lens made of a compound having an epithio group, a polyisocyanate compound, or a polythiol compound as a raw material, the lens surface is not transferred in the shape of a lens, and it is difficult to have good transparency and hardness. there were.

[0003]

SUMMARY OF THE INVENTION The present invention has been made to solve the above-mentioned problems, and a method of manufacturing a plastic lens having good surface accuracy, transparency, and hardness, a plastic lens, and a neutralized phosphorus It is to provide a method for using an acid ester.

[0004]

Means for Solving the Problems The inventors of the present invention have conducted intensive studies to develop a plastic lens having the above-mentioned preferable properties. It has been found that the purpose is achieved by using a phosphate ester, and the present invention has been completed. That is, according to the present invention, the monomer represented by the following general formula (I)

Embedded image (Wherein R is an alkylene group having 1 to 12 carbon atoms, R ′
Is an alkyl group having 1 to 20 carbon atoms or 7 to
26 alkylhydroxyphenyl groups, n is 1 to 15,
m shows 1-2. A) a step of adding a neutralized phosphate ester represented by the formula (1) as an internal mold release agent to prepare a mixture, and injecting the mixture into a plastic lens mold, followed by polymerization to obtain a polymer. And a third step of releasing the polymer from the plastic lens mold to obtain a plastic lens. Further, a plastic lens containing a polymer of a raw material monomer for a plastic lens and a neutralized phosphoric acid ester represented by the above general formula (I), and a neutralized phosphoric acid represented by the above formula (I) It also provides a method of using an ester as an internal release agent for the production of plastic lenses.

[0005]

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS The raw material monomer for a plastic lens used in the present invention is not particularly limited, and the raw material monomer for an acrylic resin lens, the monomer raw material for a lens made from diethylene glycol bisallyl carbonate, and the like. Raw material monomers for sulfur atom-containing resin lenses, raw material monomers for halogen atom-containing resin lenses, raw material monomers for polyurethane resin lenses, raw material monomers for polyurethane resin lenses, and the like. Among them, a monomer mixture of a polyisocyanate compound, which is a raw material monomer for a polyurethane lens, and an active hydrogen compound such as polythiol, polyol, or polyamine, is one of raw material monomers for a sulfur-containing resin lens. A compound having a certain epithio group, a polyisocyanate compound, and a polythio-
It is a monomer mixed with an active hydrogen compound such as toluene, polyol or polyamine. As the active hydrogen compound, a polyamine compound or a polythiol compound is preferable.

The monomer of the polyisocyanate compound is not particularly restricted but includes, for example, hydrogenated 2,6-tolylene diisocyanate, hydrogenated meta and paraphenylenediisocyanate, hydrogenated 2,4-tolylene diisocyanate Alicyclic isocyanate compounds such as nate, hydrogenated diphenylmethane diisocyanate, hydrogenated meta-xylylene diisocyanate, hydrogenated para-xylylene diisocyanate, isophorone diisocyanate, meta- and para-phenylene diisocyanate, 2,6- Tolylene diisocyanate,
2,4-tolylene diisocyanate, 4,4'-diphenylmethane diisocyanate, meta and paraxylylene diisocyanate, meta and paratetramethylxylylene diisocyanate, 2,6-naphthalene diisocyanate, 1,5- Examples include naphthalene diisocyanate, and preferred are 2,4- and 2,6-tolylene diisocyanate, 4,4'-diphenylmethane diisocyanate, meta-xylylene diisocyanate, and meta-tetramethyl xylylene diisocyanate. And isocyanate compounds having an aromatic ring such as 2,6-naphthalene diisocyanate. Further, hexamethylene diisocyanate, octamethylene diisocyanate, 2,2,4
-Trimethylhexamethylene diisocyanate, tetramethylene diisocyanate, buret reaction product of hexamethylene diisocyanate, trimer of hexamethylene diisocyanate, 1,3- (diisocyanatomethyl) cyclohexane, lysine diisocyanate , Lysine triisocyanate, 1,6,11-undecane triisocyanate, isocyanate compounds having no alicyclic or aromatic ring, such as triphenylmethane triisocyanate, diphenyl disulfide-4,4'-diisocyanate Nate, 2,2'-dimethyldiphenyldisulfide-
5,5′-diisocyanate, 3,3′-dimethyldiphenyldisulfide-5,5′-diisocyanate,
3,3′-dimethyldiphenyldisulfide-6,6 ′
-Diisocyanate, 4,4'-dimethyldiphenyldisulfide-5,5'-diisocyanate, 3,3'-
Dimethoxydiphenyldisulfide-4,4'-diisocyanate, 4,4'-dimethoxydiphenyldisulfide-3,3'-diisocyanate, diphenylsulfone-4,4'-diisocyanate, diphenylsulfone-3,3 ' -Diisocyanate, benzylidene sulfone-4,4'-diisocyanate, diphenylmethanesulfone-4,4'-diisocyanate, 4-methyldiphenylmethanesulfone-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-butyldiphenylsulfone-
3,3'-diisocyanate, 4,4'-dimethoxybenzeneethylenedisulfone-3,3'-diisocyanate, 4,4'-dichlorodiphenylsulfone-3,3 '
-Diisocyanate, 4-methyl-3-isocyanatobenzenesulfonyl-4'-isocyanatophenol ester, 4-methoxy-3-isocyanatobenzenesulfonyl-4'-isocyanatophenol ester, 4-methyl-3-isocyanate Natobenzenesulfonylanilide-
3'-methyl-4'-isocyanate, dibenzenesulfonyl-ethylenediamine-4,4'-diisocyanate, 4,4'-dimethoxybenzenesulfonyl-ethylenediamine-3,3'-diisocyanate, 4-methyl- 3-isocyanatobenzenesulfonylanilide-4-
Methyl-3'-isocyanate, thiophene-2,5-
Diisocyanate, thiophene-2,5-diisocyanatomethyl, 1,4-dithiane-2,5-diisocyanate, 1,4-dithiane-2,5-diisocyanatomethyl, 1,4-dithiane- 2,3-diisocyanatomethyl, 1,4-dithiane-2-isocyanatomethyl-5
Isocyanatopropyl, 1,3-dithiolane-4,5-
Diisocyanate, 1,3-dithiolane-4,5-diisocyanatomethyl, 1,3-dithiolane-2-methyl-
4,5-diisocyanatomethyl, 1,3-dithiolane-
2,2-diisocyanatoethyl, tetrahydrothiophen-2,5-diisocyanate, tetrahydrothiophen-2,5-diisocyanatomethyl, tetrahydrothiophen-2,5-diisocyanatoethyl, tetrahydrothiophen-3,4 -A sulfur-containing isocyanate compound such as diisocyanatomethyl. These compounds may be used alone or in combination of two or more.

The polythiol compound includes, for example, methanedithiol, 1,2-ethanedithiol,
1,1-propanedithiol, 1,2-propanedithiol, 1,3-propanedithiol, 2,2-propanedithiol, 1,6-hexanedithiol, 1,2,3
-Propanetrithiol, tetrakis (mercaptomethyl) methane, 1,1-cyclohexanedithiol,
2-cyclohexanedithiol, 2,2-dimethylpropane-1,3-dithiol, 3,4-dimethoxybutane-1,2-dithiol, 2-methylcyclohexane-
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-
Mercaptoacetate), 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), trimethylolpropane tris (2-mercapto Acetate), trimethylolpropane tris (3-mercaptopropionate), pentaerythritol tetrakis (2-mercaptoacetate), pentaerythritol tetrakis (3
-Mercaptopropionate), aliphatic thiols such as 1,2-bis (2-mercaptoethylthio) -3-mercaptopropane, 1,2-dimercaptobenzene, 1,3
-Dimercaptobenzene, 1,4-dimercaptobenzene, 1,2-bis (mercaptomethyl) benzene, 1,
3-bis (mercaptomethyl) benzene, 1,4-bis (mercaptomethyl) benzene, 1,3-bis (mercaptoethyl) benzene, 1,4-bis (mercaptoethyl) benzene, 1,2-bis (mercaptomethoxy) ) Benzene, 1,3-bis (mercaptomethoxy) benzene, 1,4-bis (mercaptomethoxy) benzene,
1,2-bis (mercaptoethoxy) benzene, 1,3
-Bis (mercaptoethoxy) benzene, 1,4-bis (mercaptoethoxy) 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, 1,3,3 5-tris (mercaptoethyl) benzene, 1,2,3-tris (mercaptomethoxy) benzene, 1,2,4-tris (mercaptomethoxy) benzene, 1,3,5-tris (mercaptomethoxy) benzene, 1, 2,3-tris (mercaptoethoxy) benzene, 1,2,4-tris (mercaptoethoxy) benzene, 1,3,5-tris (mercaptoethoxy) benzene, 1,2,3,4-tetramercaptobenzene, 1 , 2,3,5-tetramercaptobenzene, 1,2,4,5-tetramercaptobenzene, 1,2,3 -Tetrakis (mercaptomethyl) benzene, 1,2,3,5-tetrakis (mercaptomethyl) benzene, 1,2,4,5-tetrakis (mercaptomethyl) benzene, 1,2,3,4-tetrakis (mercaptoethyl) ) Benzene, 1,2,3,5-tetrakis (mercaptoethyl) benzene, 1,2,4
5-tetrakis (mercaptoethyl) benzene, 1,
2,3,4-tetrakis (mercaptoethyl) benzene, 1,2,3,5-tetrakis (mercaptomethoxy) benzene, 1,2,4,5-tetrakis (mercaptomethoxy) benzene, 1,2,3,4 -Tetrakis (mercaptoethoxy) benzene, 1,2,3,5-tetrakis (mercaptoethoxy) benzene, 1,2,2
4,5-tetrakis (mercaptoethoxy) benzene,
2,2′-dimercaptobiphenyl, 4,4′-dimercaptobiphenyl, 4,4′-dimercaptobibenzyl, 2,5-toluenedithiol, 3,4-toluenedithiol, 1,4-naphthalenedithiol, , 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- Aromatic thiols such as methoxyphenyl) propane-2,2-dithiol, 1,3-diphenylpropane-2,2-dithiol, phenylmethane-1,1-dithiol, and 2,4-di (p-mercaptophenyl) pentane , 2,5-dichlorobenzene-
1,3-dithiol, 1,3-di (p-chlorophenyl) propane-2,2-dithiol, 3,4,5-tribromo-1,2-dimercaptobenzene, 2,3,4
6-tetrachloro-1,5-bis (mercaptomethyl)
Halogen-substituted aromatic thiols such as chlorine-substituted products such as benzene and bromine-substituted products, 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 (mercaptoethyl) Thio)
Benzene, 1,3,5-tris (mercaptoethylthio) benzene, 1,2,3,4-tetrakis (mercaptomethylthio) benzene, 1,2,3,5-tetrakis (mercaptomethylthio) benzene, 1,2,2 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 and the like, and the like Aromatic thiols containing a sulfur atom in addition to a mercapto group, such as a nucleated alkylated product, 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- (2-mercaptoethylthio) ethane, 1,2- ( 3-mercaptopropyl) ethane, 1,3-bis (mercaptomethylthio) propane, 1,3-bis (2-mercaptoethylthio) propane, 1,3-bis (3-mercaptopropylthio) propane, 1,2- Bis (2-mercaptoethylthio) -3-mercaptopropane, 2-mercaptoethylthio-1,3-propanedithiol, 1,2,3-tris (mercaptomethylthio) propane, 1,2,3-
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, hydroxymethylsulfide bis (2-mercaptoacetate), hydroxy Methyl sulfide bis (3-mercaptopropionate), hydroxyethyl sulfide bis (2-mercaptoacetate), hydroxyethyl sulfide bis (3-mercaptopropionate), hydroxypropyl sulfide bis (2-mercaptoacetate), hydroxypropyl sulfide Bis (3-mercaptopropionate), hydroxymethyldisulfidebis (2-mercaptoacetate), hydroxymethyldisulfidebis (3- Mercaptoethyloleates propionate),
Hydroxyethyl disulfide bis (2-mercaptoacetate), hydroxyethyl disulfide bis (3-
Mercaptopropionate), hydroxypropyldisulfidebis (2-mercaptoacetate), hydroxypropyldisulfidebis (3-mercaptopropionate), 2-mercaptoethyletherbis (2-mercaptoacetate), 2-mercaptoethyletherbis ( 3-mercaptopropionate), 1,4-dithiane-2,5-diolbis (2-mercaptoacetate), 1,4-dithiane-2,5-diolbis (3-
Mercaptopropionate), bis (2-mercaptoethyl ester) thioglycolate, bis (2-mercaptoethyl ester) thiodipropionate, 4,4′-
Bis (2-mercaptoethyl ester) thiodibutyrate, bis (2-mercaptoethyl ester) dithiodiglycolate, bis (2-mercaptoethyl ester) dithiodipropionate, bis (2-mercaptoethyl 4,4′-dithiodibutyrate) Ethyl ester), thiodiglycolic acid bis (2,3-dimercaptopropyl ester),
Bis (2,3-dimercaptopropyl ester) thiodipropionate, bis (2,3-dimercaptopropyl ester) dithiodiglycolate, 2,3-dimercaptopropyl ester dithiodipropionate, 4-mercapto Methyl-3,6-dithiaoctane-1,8-dithiol, bis (mercaptomethyl) -3,6,9-trithia-1,11-undecanedithiol, bis (1,3
Aliphatic thiols containing a sulfur atom in addition to a mercapto group such as -dimercapto-2-propyl) sulfide;
4-thiophenedithiol, tetrahydrothiophene-
2,5-dimercaptomethyl, 2,5-dimercapto-
1,3,4-thiadiazole, 2,5-dimercapto-
1,4-dithiane, 2,5-dimercaptomethyl-1,
Examples thereof include a heterocyclic compound containing a sulfur atom in addition to a mercapto group such as 4-dithiane. These compounds may be used alone or in combination of two or more.

As the polyol compound, for example,
Ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, butylene glycol, neopentyl glycol, glycerin, trimethylolethane, trimethylolpropane, butanetriol, 1,2-methylglucoside, pentaerythritol, dipentaerythritol, tripentaerythritol , Triethylene glycol, polyethylene glycol, tris (2-hydroxyethyl) isocyanurate, cyclobutanediol, cyclopentanediol,
Cyclohexanediol, cycloheptanediol, cyclooctanediol, bicyclo [4,3,0] -nonanediol, dicyclohexanediol, tricyclo [5,3,1,1] dodecanediol, spiro [3
4] octanediol, aliphatic polyols such as butylcyclohexanediol, dihydroxynaphthalene, trihydroxynaphthalene, tetrahydroxynaphthalene,
Aromatic polyols such as dihydroxybenzene, benzenetriol, trihydroxyphenanthrene, bisphenol A, bisphenol F, xylylene glycol, and tetrabromobisphenol A, and addition reaction products thereof with alkylene oxides such as ethylene oxide and propylene oxide; [4- (hydroxyethoxy) phenyl] sulfide, bis- [4- (2-
Hydroxypropoxy) phenyl] sulfide, bis-
[4- (2,3-dihydroxypropoxy) phenyl]
Sulfide, bis- [4- (4-hydroxycyclohexyloxy) phenyl] sulfide, bis- [2-methyl-4- (hydroxyethoxy) -6-butylphenyl]
Sulfides, compounds obtained by adding ethylene oxide and / or propylene oxide in an average of not more than 3 molecules 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-
Examples of the polyol include a sulfur atom-containing polyol such as bis (2-hydroxyethylthioethyl) -cyclohexane. These compounds may be used alone or in combination of two or more.

As the polyamine compound, for example,
Ethylenediamine, diaminopropane, diaminobutane, diaminopentane, bisaminocyclohexane, bisaminomethylcyclohexane, 4,4′-diamino-
3,3′-dimethyldicyclohexylmethane, 4,4 ′
-Diamino-3,3'-dimethyldicyclohexyl,
4,4'-diamino-3,3'-dimethyldicyclohexyl sulfide, 4,4'-diamino-3,3 ', 5
5'-tetramethyldicyclohexylmethane, 4,4 '
-Diamino-3,3 ', 5,5'-tetramethyldicyclohexyl and the like. These compounds may be used alone or in combination of two or more.

The compounds having an epithio group include:
Any known one may be used.
No. 80, JP-A-09-110797, JP-A-09-255581, JP-A-03-08320
JP, JP-A-11-140070, JP-A-11-11070
-183702, JP-A-11-189592, JP-A-11-180977, JP-A-01-8
No. 10,575, and the like. In particular,
1,3 and 1,4-bis (β-epithiopropylthio)
Cyclohexane, 1,3 and 1,4-bis (β-epithiopropylthiomethyl) cyclohexane, bis [4-
(Β-epithiopropylthio) cyclohexyl] methane, 2,2 bis [4- (β-epithiopropylthio)
Episulfide compounds having an alicyclic skeleton, such as cyclohexyl] propane, bis (β-epithiopropyl) sulfide, bis [4- (β-epithiopropylthio) cyclohexyl] sulfide, 1,3 and 1,4-bis ( β
-Epithiopropylthio) benzene, 1,3 and 1,4
-Bis (β-epithiopropylthiomethyl) benzene,
Bis [4- (β-epithiopropylthio) phenyl] methane, 2,2-bis [4- (β-epithiopropylthio) phenyl] propane, bis [4- (β-epithiopropylthio) phenyl] Sulfide, bis [4- (β-
Epithiopropylthio) phenyl] sulfine, 4,4
Episulfide compounds having an aromatic skeleton such as -bis (β-epithiopropylthio) biphenyl, 2,5-bis (β-epithiopropylthiomethyl) -1,4-dithiane, 2,5-bis (β- Epithiopropylthioethylthiomethyl) -1,4-dithiane, 2,5-bis (β-epithiopropylthioethyl) -1,4-dithiane,
3,5-tri (β-epithiopropylthioethyl)-
Episulfide compounds having a dithiane ring skeleton such as 1,4-dithiane, 2- (2-β-epithiopropylthioethylthio) -1,3-bis (β-epithiopropylthio) propane, 1,2-bis [(2-β-epithiopropylthioethyl) thio] -3- (β-epithiopropylthio) propane, tetrakis (β-epithiopropylthiomethyl) methane, 1,1,1-tris (β-epithio Episulfide compounds having an aliphatic skeleton such as thiopropylthiomethyl) propane and bis- (β-epithiopropyl) sulfide. Particularly, bis (β-epithiopropyl) sulfide is preferable. These compounds may be used alone or in combination of two or more.

The internal release agent used in the present invention has the following general formula (I):

Embedded image (Wherein R is an alkylene group having 1 to 12 carbon atoms, R ′
Is an alkyl group having 1 to 20 carbon atoms or 7 to
26 alkylhydroxyphenyl groups, n is 1 to 15,
m shows 1-2. It is important that it is a neutralized phosphate ester represented by the formula (1). R in the above general formula (I)
Examples thereof include an alkylene group such as a methylene group, an ethylene group, a propylene group, a butylene group, a pentylene group, a hexylene group, a heptylene group, and an octylene group. R ′ represents a methyl group, an ethyl group, a propyl group,
An alkyl group such as a butyl group, a pentyl group, a hexyl group, a heptyl group, and an octyl group; and a phenol group having a hydroxyl group at the 2-, 3- or 4-position.
-, 3- or 4-position methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl,
Examples thereof include an alkylhydroxyphenyl group having an alkyl group such as an octyl group. These compounds may be used alone or in combination of two or more. The above general formula (I)
Examples of the neutralized phosphate ester represented by
Is an alkylene group having 2 carbon atoms, and R ′ is 6 to
And a neutralized phosphoric acid ester having 15 alkyl groups and 6 to 10 ethylene oxides. By using the neutralized phosphate represented by the above general formula (I) as an internal release agent, it is possible to obtain a lens having not only excellent release properties but also excellent surface accuracy, transparency and hardness. Can be.

The amount of the internal release agent comprising the neutralized phosphate ester is not particularly limited, but it is preferable to add 10 to 10,000 ppm to the raw material monomer of the plastic lens.

When a plastic lens is produced by the method of the present invention, an auxiliary agent such as an ultraviolet absorber, an antioxidant, a colorant, and a catalyst can be added as long as the effect is not impaired. As a catalyst, in the case of a lens obtained by polymerizing a polyisocyanate compound, a polythiol compound, or a compound having an epithio group, tetra-methyl-diacetoxy-distannoxane, tetra-ethyl-diacetoxy-distannoxane, tetra-propyl-diacetoxy -Distannoxane or tetra-butyl-diacetoxy-distannoxane is preferably used, and in the case of a polyurethane or polythiourethane lens, an organic tin compound such as dibutyltin dichloride or a known amine compound is preferably used, and in the case of an acrylic lens, An azo catalyst is preferably used. Further, on the released plastic lens, for improving abrasion resistance, an organic silicon compound or an acrylic compound containing fine particulate inorganic matter such as tin oxide, silicon oxide, zirconium oxide or titanium oxide.
A cured film may be formed by using a priming liquid, and a primer layer containing polyurethane as a main component may be formed on a plastic lens to improve impact resistance. Furthermore, in order to impart antireflection performance, an antireflection film made of an inorganic substance such as silicon oxide, titanium dioxide, zirconium oxide, or tantalum oxide may be formed on the cured film to improve water repellency. Alternatively, a water-repellent film made of an organosilicon compound containing a fluorine atom may be formed on the antireflection film.

[0014]

EXAMPLES The present invention will be described in more detail with reference to the following examples, but the present invention is not limited to these examples. The evaluation of the physical properties of the plastic lenses obtained in Examples and Comparative Examples was performed as follows. (1) Releasability Evaluated according to the following evaluation criteria. ：: When the plastic lens is peeled from the glass mold, the lens and the mold can be released without damage. ×: The mold cannot be released at all, or the lens and the glass mold break. A part of a plastic mold adheres, a part of a plastic lens adheres to a glass mold, or a plastic lens is cracked. (2) Appearance After releasing the plastic lens from the mold, the lens was visually observed. (3) Refractive index and Abbe number 2
It was measured at 0 ° C.

Example 1 43.50 parts by weight of m-xylylene diisocyanate as a polyisocyanate compound, 0.05 parts by weight of dibutyltin dilaurate as a catalyst, and the following general formula (I) as an internal mold release agent

Embedded image In the formula, n = 10, m = 2, and R ′ has 12 to 12 carbon atoms.
Monoalkylamine salt of ether phosphate ester having 15 alkyl groups and R is an ethylene group (phosphanol RS-7108M: Toho Chemical Industry Co., Ltd.) 0.30 part by weight, 2- (2'- Hydroxy-4-
Octyloxyphenyl) benzotriazole 0.05
After stirring and dissolving by weight, 56.50 parts by weight of pentaerythritol tetrakismercaptopropionate as a polythiol compound was added, and about 1333 Pa
The mixture was stirred and mixed under reduced pressure for 30 minutes to prepare a monomer composition for lenses. This monomer composition for a lens is poured into a lens mold (0.00D, lens diameter 80 mm, wall thickness 1.6 mm) composed of a glass mold and a resin gasket prepared in advance, and the mixture is placed in an electric furnace. ℃ to 12
Gradually raise the temperature to 0 ° C over 22 hours,
The polymerization was carried out while keeping the temperature for an hour. After the polymerization was completed, the resin gasket was removed, and then released from the glass mold to obtain a plastic lens. The mold was easily released without breakage of both the mold and the lens at the time of release.
The lens surface was transcribed according to the lens pattern. The above lenses (1) to (3) were evaluated for the obtained lens. Table 1 shows the results.

EXAMPLE 2 47,538 parts by weight of 1,3- (diisocyanatomethyl) cyclohexane as a polyisocyanate compound, 0.45 part by weight of dimethyltin dichloride as a catalyst, and the above general formula as an internal mold release agent In (I), n
= 4, m = 2, R ′ is an alkyl group having 10 to 14 carbon atoms, and R is an ethylene group, a monoethanolamine salt of an ether phosphate (phosphanol RA-6008).
M: 0.20 parts by weight of Toho Chemical Industry Co., Ltd., and 0.05 parts by weight of 2- (2′-hydroxy-4-octyloxyphenyl) benzotriazole as an ultraviolet absorber were added, followed by stirring and dissolving. 2,5 as polythiol compounds
-Dimercaptomethyl-1,4-dithiane 26.467
Parts by weight and 25.995 parts by weight of pentaerythritol tetrakismercaptoacetate,
The mixture was stirred and mixed under reduced pressure for 30 minutes to prepare a monomer composition for lenses. This monomer composition for a lens is poured into a lens mold (0.00D, lens diameter 80 mm, wall thickness 1.6 mm) composed of a glass mold and a resin gasket prepared in advance, and the mixture is placed in an electric furnace. ℃ to 12
Gradually raise the temperature to 0 ° C over 22 hours,
The polymerization was carried out while keeping the temperature for an hour. After the polymerization was completed, the resin gasket was removed, and then released from the glass mold to obtain a plastic lens. The mold was easily released without breakage of both the mold and the lens at the time of release.
The lens surface was transcribed according to the lens pattern. The above lenses (1) to (3) were evaluated for the obtained lens. Table 1 shows the results.

Example 3 80.0 parts by weight of bis (β-epithiopropyl) sulfide as a compound having an epithio group, 15.65 parts by weight of bis (mercaptomethyl) -1,4-dithiane as a polythiol compound, 3. Bis (diisocyanatomethyl) bicycloheptane which is a polyisocyanate compound
35 parts by weight were stirred and mixed, and in the above general formula (I), n = 3, m = 2, and R ′ had 1 carbon atom as an internal release agent.
Monoethanolamine salt of an ether phosphate having 2 to 15 alkyl groups and R is an ethylene group (Phosphanol RS-4108M: Toho Chemical Industry Co., Ltd.) 0.10
Parts by weight, 2- (2′-hydroxy-
4-octyloxyphenyl) benzotriazole
05 parts by weight, 0.05 parts by weight of tetrabutylphosphonium bromide as a catalyst and tetra-n-butyl-1,3
After adding 0.005 parts by weight of diacetoxy-distannoxane, stirring and dissolving, 1 part under reduced pressure of about 1333 Pa.
The mixture was stirred and mixed for 0 minute to prepare a monomer composition for a lens. A lens molding die (0.00D, lens diameter 80 mm, wall thickness 1.6 mm) composed of a glass mold and a resin gasket prepared in advance with the lens monomer composition.
In an electric furnace from 20 ° C to 120 ° C.
The temperature was gradually raised over time, and the temperature was kept at 100 ° C. for 1 hour to carry out polymerization. After the polymerization was completed, the resin gasket was removed, and then released from the glass mold to obtain a plastic lens. The mold was easily released without breakage of both the mold and the lens at the time of release. The lens surface was transcribed according to the lens pattern. The above lenses (1) to (3) were evaluated for the obtained lens. Table 1 shows the results.

Example 4 52.02 parts by weight of m-xylylene diisocyanate as a polyisocyanate compound, 0.01 part by weight of dimethyltin dichloride as a catalyst, and n in the above general formula (I) as an internal release agent 4, m = 2, R 'is an alkyl group having 10 to 14 carbon atoms, and R is an ethylene group. Monoethanolamine salt of ether phosphate (phosphanol RA-6008M: Toho Chemical Industry Co., Ltd.)
0.20 parts by weight, and 0.05 parts by weight of 2- (2'-hydroxy-4-octyloxyphenyl) benzotriazole as an ultraviolet absorber were added thereto, followed by stirring and dissolving. 47.98 parts by weight of bis [(2-mercaptoethyl) thio] -3-mercaptopropane was added, and the mixture was stirred and mixed under a reduced pressure of about 1333 Pa for 30 minutes to prepare a monomer composition for lenses. This lens monomer composition was prepared in advance using a glass mold and a resin gasket.
D, lens diameter 80 mm, wall thickness 1.6 mm), gradually heated from 20 ° C. to 120 ° C. over 22 hours in an electric furnace, and kept at 120 ° C. for 3 hours to perform polymerization. . After the polymerization is completed, after removing the resin gasket,
A plastic lens was obtained by releasing from the glass mold. The mold was easily released without breakage of both the mold and the lens at the time of release. The lens surface was transcribed according to the lens pattern. The above lenses (1) to (3) were evaluated for the obtained lens. Table 1 shows the results.

EXAMPLE 5 26.79 parts by weight of 1,3,5- (triisocyanatomethyl) cyclohexane as a polyisocyanate compound, 0.10 part by weight of dimethyltin dichloride as a catalyst, and the above as an internal mold release agent In the general formula (I),
n = 4, m = 2, R ′ is an alkyl group having 10 to 14 carbon atoms, and R is an ethylene group, a monoethanolamine salt of ether phosphate (Phosphanol RA-600
8M: 0.20 parts by weight of Toho Chemical Industry Co., Ltd., and 0.05 parts by weight of 2- (2'-hydroxy-4-octyloxyphenyl) benzotriazole as an ultraviolet absorber were added, followed by stirring and dissolving. 2, as polythiol compounds
5-bismercaptoethyl-1,4-dithiane 43.3
5 parts by weight and 29.86 parts by weight of 2,5-bisthiobutenyl-1,4-dithiane were added, and the mixture was stirred and mixed under a reduced pressure of about 1333 Pa for 30 minutes to prepare a monomer composition for lenses. A lens molding die (0.00D, lens diameter 80 mm, wall thickness 1.6 m) composed of a glass mold and a resin gasket prepared in advance from the lens monomer composition.
m), the temperature was gradually increased from 20 ° C. to 120 ° C. in an electric furnace over 22 hours, and the temperature was kept at 120 ° C. for 3 hours to carry out polymerization. After the polymerization was completed, the resin gasket was removed, and then released from the glass mold to obtain a plastic lens. The mold was easily released without breakage of both the mold and the lens at the time of release. The lens surface was transcribed according to the lens pattern. The above lenses (1) to (3) were evaluated for the obtained lens. Table 1 shows the results.

Example 6 51.16 parts by weight of m-xylylene diisocyanate as a polyisocyanate compound, 0.05 part by weight of dibutyltin dilaurate as a catalyst, and n as an internal mold release agent in the above general formula (I) = 10, m = 2, R ′ is an alkyl group having 12 to 15 carbon atoms, and R is an ethylene group. Monoethanolamine salt of ether phosphate (phosphanol RS-7108M: Toho Chemical Industry Co., Ltd.) 0 40 parts by weight, 2-
After adding and stirring and dissolving 0.05 part by weight of (2'-hydroxy-4-octyloxyphenyl) benzotriazole, 39.84 parts by weight of pentaerythritol tetrakismercaptopropionate and 2,3 as a polythiol compound were added. -Dimercapto-1-propanol 9.0
0 parts by weight were added, and the mixture was stirred and mixed under a reduced pressure of about 1333 Pa for 30 minutes to prepare a monomer composition for lenses. A lens mold (0.0%) comprising a glass mold and a resin gasket prepared in advance with the lens monomer composition.
(0D, lens diameter 80 mm, wall thickness 1.6 mm), the temperature was gradually raised from 20 ° C. to 120 ° C. over 22 hours in an electric furnace, and the temperature was kept at 120 ° C. for 3 hours to perform polymerization. . After the polymerization is completed, after removing the resin gasket,
A plastic lens was obtained by releasing from the glass mold. The mold was easily released without breakage of both the mold and the lens at the time of release. The lens surface was transcribed according to the lens pattern. The above lenses (1) to (3) were evaluated for the obtained lens. Table 1 shows the results.

Comparative Example 1 Polymerization was carried out in the same manner as in Example 1 except that the internal release agent was not used. After the polymerization was completed, the resin gasket was removed, and then the mold was released from the glass mold. Molding was performed but could not be released. Comparative Example 2 Polymerization was performed in the same manner as in Example 2 except that the internal release agent was not used, and after the polymerization was completed, the resin gasket was removed, and then the mold release from the glass mold was performed. However, it could not be released.

Comparative Example 3 In Example 2, instead of 0.20 parts by weight of phosphanol RA-6008M as an internal release agent, the following general formula (II) was used.

Embedded image In the same manner as above, except that 0.10 parts by weight of a sodium salt of an ether phosphate in which n = 4, m = 2, and R ′ is an alkyl group having 12 carbon atoms was used, polymerization was carried out, and polymerization was completed. Thereafter, after removing the resin gasket, the mold was released from the glass mold. However, although the mold was released, the lens was white. The above lenses (1) to (3) were evaluated for the obtained lens. Table 2 shows the results.

Comparative Example 4 Polymerization was carried out in the same manner as in Example 3 except that the internal release agent was not used. After the polymerization was completed, the resin gasket was removed, and the resin was released from the glass mold. When the mold was released, the lens was cracked at the time of release, and adhered substances remained on a part of the mold, so that sufficient release could not be performed. The above lenses (1) to (3) were evaluated for the obtained lens. Table 2 shows the results.

Comparative Example 5 In Example 3, the following general formula (III) was used in place of phosphanol RS-4108M as an internal release agent.

Embedded image The same applies except that n = 1, m = 2 and 1 (the ratio of m = 2: m = 1 is about 4: 6), and ether phosphates in which R ′ is an alkyl group having 4 carbon atoms are used. The composition was not cured sufficiently and was in the form of a soft jelly. About the obtained lens, said (1)-
(3) was evaluated. Table 1 shows the results.

Comparative Example 6 Polymerization was carried out in the same manner as in Example 4 except that the internal mold release agent was not used. After the polymerization was completed, the resin gasket was removed, and then the mold was released from the glass mold. Molding was performed but could not be released. Comparative Example 7 Polymerization was carried out in the same manner as in Example 5 except that the internal release agent was not used. After the polymerization was completed, the resin gasket was removed, and then the mold was released from the glass mold. However, it could not be released. Comparative Example 8 Polymerization was performed in the same manner as in Example 6 except that the internal release agent was not used. After the polymerization was completed, the resin gasket was removed, and then the mold release from the glass mold was performed. However, it could not be released.

[0026]

[Table 1]

* M-XDI: meta-xylylene diisocyanate PETMP: pentaerythritol tetrakismercaptopropionate PETMA: pentaerythritol tetrakismercaptoacetate HXDI: 1,3- (diisocyanatomethyl) cyclohexane DMMD: 2,5-dimercapto Methyl-1,4-dithiane BEPS: bis (β-epithiopropyl) sulfide NBDI: bis (isocyanatemethyl) bicycloheptane BETMP: 1,2-bis [(2-mercaptoethyl)
Thio] -3-mercaptopropane HMTI: 1,3,5- (triisocyanatomethyl)
Cyclohexane TBD: 2,5-bisthiobutenyl-1,4-dithiane DMP: 2,3-dimercapto-1-propanol

[0028]

[Table 2]

[0029]

As described in detail above, the plastic lens obtained by the manufacturing method of the present invention has a lens surface transferred to a lens shape, has sufficient hardness, and can be easily peeled. It is colorless and transparent and has high transparency. Further, the plastic lens of the present invention has a high refractive index and a high Abbe number.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification code FI Theme coat ゛ (Reference) G02B 1/04 G02B 1/04 // B29K 75:00 B29K 75:00 B29L 11:00 B29L 11: 00F Terms (reference) 4F071 AA53 AC15 AE22 AF25 AF30 AF58 BA02 BB12 BC07 4F204 AH74 EA03 EB01 EF27 EK25 4J002 CK021 EW046 FD166 GP01 4J034 CA14 CA15 CA16 CA32 HA06 HA07 HC11 HC12 HC17 HC22 HC46 HC52 HC61 HC71 MA16

Claims (9)

[Claims] 1. A raw material monomer for a plastic lens,
The following general formula (I): (Wherein R is an alkylene group having 1 to 12 carbon atoms, R ′
Is an alkyl group having 1 to 20 carbon atoms or 7 to
26 alkylhydroxyphenyl groups, n is 1 to 15,
m shows 1-2. A) a step of adding a neutralized phosphate ester represented by the formula (1) as an internal mold release agent to prepare a mixture, and injecting the mixture into a plastic lens mold, followed by polymerization to obtain a polymer. And a third step of releasing the polymer from the plastic lens mold to obtain a plastic lens. 2. A raw material monomer for the plastic lens.
Is a mixed monomer containing a polyisocyanate compound and an active hydrogen compound.
A method for producing the plastic lens described in the above. 3. A raw material monomer for the plastic lens.
2. The method for producing a plastic lens according to claim 1, wherein is a mixed monomer containing a compound having an epithio group, a polyisocyanate compound, and an active hydrogen compound. 4. The method according to claim 3, wherein the compound having an epithio group is bis (β-epithiopropyl) sulfide. 5. The method according to claim 2, wherein the active hydrogen compound is a polyamine compound. 6. The method according to claim 2, wherein the active hydrogen compound is a polythiol compound. 7. The method for producing a plastic lens according to claim 1, wherein the neutralized phosphate ester is added to the raw material monomer of the plastic lens in an amount of 10 to 10000 ppm. 8. A polymer of a raw material monomer for a plastic lens, and a compound represented by the following general formula (I): (Wherein R is an alkylene group having 1 to 12 carbon atoms, R ′
Is an alkyl group having 1 to 20 carbon atoms or 7 to
26 alkylhydroxyphenyl groups, n is 1 to 15,
m shows 1-2. A plastic lens comprising a neutralized phosphate represented by the formula (1): 9. The following general formula (I): (Wherein R is an alkylene group having 1 to 12 carbon atoms, R ′
Represents an alkyl group or an alkylhydroxyphenyl group having 1 to 20 carbon atoms, n represents 1 to 15, and m represents 1 to 2. )
A method for using a neutralized phosphate ester comprising using the neutralized phosphate ester represented by the formula (1) as an internal mold release agent for producing a plastic lens.