JPH0970834A - Manufacture of plastic lens - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a high quality lens product by preventing the leakage of liquid during injection, polymerization, and curing and the entrainment of external air during volume contraction by heating or heat-pressing a part on the side of a mold where pressure sensitive adhesive tapes are overlapped before the injection. SOLUTION: A pressure sensitive adhesive tape in which a polyethylene terephthalate biaxially oriented film 2 is coated with a silicone pressure sensitive adhesive 3 is fixed to two glass molds 1 which form the optical surfaces of a lens so that the space forms the shape of the lens by a jig is wound onto the side peripheral part of the circumference of the glass molds 1. For example, the tape is wound around the entire peripheral part with an overlapped part of 4-5cm to be contacted closely with the glass mold. A solder trowel heated at 60 deg.C or higher is pressed on the overlapped part and contacted with a step part several times to conduct heat press treatment. A liquid curing composition is injected into the molds 1 and heated to complete polymerization.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for manufacturing plastic lenses such as spectacles. Furthermore, the present invention relates to a method for producing a plastic lens which is excellent in the sealing property of a liquid curable compound upon cast polymerization.

[0002]

2. Description of the Related Art As a method for producing a plastic lens, a casting method in which a monomer is poured into a glass mold and hardened by heat or light, a cutting and polishing method in which a monomer is cut out from a plastic plate and polished and finished, and a thermoplastic resin is used. There are an injection molding method, a hot press method, and the like.

As a lens material, polymethylmethacrylate as a sunglasses lens, diethylene glycol bisallyl carbonate for correcting vision, a copolymer of styrene and a bromine-containing methacrylate, and an isocyanate group-containing material. A polymer of a monomer and a monomer containing a hydroxy group or a thiol group is used.

Of these methods, the cast molding method is usually used for the production of high-performance plastic lenses.

Here, the cast molding method is a method of injecting a liquid curing compound into a mold having a lens shape and curing the compound by heating or the like, and then removing the mold to obtain a lens product. Is.

[0006] In this cast molding method, it is composed of two mold glass molds processed into the curvature of the lens to be obtained, and a sealing material (so-called gasket) adhered to the peripheral side surface of the glass mold. However, since the gasket is broken at the end of the polymerization to take out the lens product inside, the service life is extremely short, and a gasket corresponding to the curvature of the mold is required, which greatly increases the manufacturing cost of the lens.

As an improved method, a method of using an adhesive tape instead of a gasket has been proposed (for example, JP-A-55-105519 and JP-A-56-135).
031, JP 57-8120, JP 61-
146511, JP-A-61-148282, JP-A-5-
255650 publication).

In these known techniques, since the adhesive layer of the tape used and the liquid monomer are in direct contact with each other, the adhesive is partially dissolved in the monomer, causing turbidity or the like in the lens and Only the description that the material of the pressure-sensitive adhesive is changed to cope with the serious defect that the product quality is significantly impaired.

However, when the adhesive tape is used for polymerization, the adhesive tapes are overlapped with each other when the tape goes around the side surface of the mold, and a gap is formed in the overlapped portion. Therefore, the liquid curable compound leaks from the overlapping portion during injection or during curing, or the liquid curable compound causes volume contraction during curing and the mold is depressurized and drawn into the air mold, causing the lens to crack. This is a major problem in terms of lens appearance.

[0010]

SUMMARY OF THE INVENTION The present invention solves the above-mentioned drawbacks of the prior art and uses heat treatment or thermocompression treatment for the overlapping portion of the adhesive tape, whereby liquid leakage and volume at the time of injection, polymerization and curing are achieved. It is an object of the present invention to provide a technique capable of obtaining a high quality lens product by eliminating the intake of external air at the time of contraction.

[0011]

In order to achieve the above object, in the method of manufacturing a plastic lens according to the first aspect of the present invention, a plastic lens is adhered around the side surfaces of two molds positioned at a predetermined interval. When a sheet-like material is brought into close contact, a liquid curable compound is injected into a mold formed by being surrounded by the two molds and an adhesive tape, and cast polymerization is carried out to produce a plastic lens. By heating or thermocompressing the part where the adhesive tape on the side of the mold overlaps before the injection, the gap between the steps of the tape overlap is eliminated, and the liquid curable compound leaks or is cured during injection or during curing. In addition, the liquid curable compound causes volume contraction, and the inside of the mold is in a depressurized state so that it is not drawn into the air mold and the defect in the lens appearance that the lens breaks is improved. That.

The heat treatment or thermocompression bonding treatment means that a rigid body such as a heated soldering iron is pressed around the overlapping portion of the tape, or an elastic body such as rubber is heated to center the overlapping portion of the tape. The gap between the steps can be eliminated by pressing it. Further, the method for manufacturing a plastic lens according to claim 2 of the invention related to the present application,
The total thickness of the adhesive and the primer of the adhesive tape is 5 to 1
When the thickness of the base material is 00 micrometers and the thickness of the base material is 25 to 100 micrometers, it is possible to suppress the step in the overlapping portion of the tape and to maintain a sufficient adhesive force. If the total thickness of the pressure-sensitive adhesive and the undercoating agent is less than 5 micrometers, the gap between the steps due to the thickness of the base material cannot be sufficiently filled, and the adhesive strength is also insufficient. When it exceeds 100 micrometers, the glass mold is liable to be misaligned and a prism is formed on the lens, which is a quality problem. When the thickness of the base material is less than 25 micrometers, the rigidity of the tape is lost and the glass mold cannot be held in a predetermined shape. If the thickness exceeds 100 micrometers, the gap between the steps of the overlapping portion due to the thickness of the base material cannot be sufficiently filled, resulting in chipping.
Preferably the total thickness of the adhesive and the primer is 10 to
50 micrometers, and the thickness of the substrate is preferably 25 to 75 micrometers. The present invention is characterized in that a plastic lens of good quality is obtained by limiting the thickness of the adhesive, the undercoating agent and the substrate of the adhesive tape.

Further, according to the third aspect of the invention of the present application, the heat treatment temperature is set to 60 ° C. or higher so that the gap between the steps of the overlapping portion can be surely eliminated. If the temperature is lower than 60 ° C., the tape base material cannot be sufficiently deformed, depending on the material of the tape, but the gap cannot be completely eliminated, resulting in chipping.

According to claim 4 of the present invention, the adhesive strength of the 180 ° stainless steel of the adhesive sheet is 100 g / 25.
It is characterized by being mm or more. If the adhesion is low,
Even if the overlapping portion is heat-treated, a gap is generated during the polymerization, which causes leakage or chipping.

The tape adhesive constituting the present invention may be selected from acrylic resin type, silicone type, natural rubber type and the like in accordance with the characteristics of the liquid curable compound for plastic lenses.

The sheet as the base material of the tape may be appropriately selected from plastic film, metal foil, paper, cloth and the like, but from the viewpoint of chemical resistance, heat resistance, strength, cost, etc., the polyimide film. , Polyethylene terephthalate film,
A polypropylene film is preferable, and a polyethylene terephthalate film is particularly preferable.

Further, the base film may be subjected to a corona discharge treatment or an undercoating treatment to improve the adhesiveness with the adhesive. In addition, a modifier such as a heat resistance improver or a modifier for improving adhesion may be appropriately added to the pressure-sensitive adhesive as long as it does not cause turbidity by being eluted in the lens monomer or hindering polymerization or curing reaction. Good.

As a method for producing an adhesive sheet, for example, when a film is used as a substrate, a catalyst is added to an adhesive solution in which the adhesive is dissolved in an organic solvent such as toluene or xylene, and this is used as a film. It can be obtained by applying it to and then reacting it at a predetermined temperature. Alternatively, an adhesive may be applied to the edge of the glass mold to bring the film into close contact.

The liquid curable compound used in the present invention is not particularly limited, but it is useful for the reaction (polyaddition, addition polymerization) of an isocyanate compound with a hydroxy compound or an isocyanate compound with a thiol compound. . This is because polyaddition with respect to radical polymerization and addition polymerization require time until the gelation state, the volume shrinkage ratio before gelation is large and a large load is applied to the tape, and a gap is formed in the overlapping portion of the tape. This is because it tends to occur, causing chipping and leakage.

Monomers which are particularly useful in the present invention will be described below. The isocyanate compound is selected from the group consisting of polyisocyanate compounds and isocyanate compounds having an isothiocyanate group. Polyisocyanate
Examples of the compound include ethylene diisocyanate,
Trimethylene diisocyanate, tetramethylene diisocyanate, hexamethylene diisocyanate, octamethylene diisocyanate, nonamethylene diisocyanate, 2,2'-dimethylpentane diisocyanate -G
2,2,4-trimethylhexane diisocyanate, decamethylene diisocyanate, butene diisocyanate
1,3-butadiene-1,4-diisocyanate,
2,4,4-trimethylhexamethylene diisocyanate
1,6,11-undecane triisocyanate,
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-α, α'-diisocyanate, lysine diisocyanate methyl ester, lysine triisocyanate, 2
-Isocyanatoethyl-2,6-diisocyanatohexanoate, 2-isocyanatopropyl-2,6-diisocyanatohexanoate, xylylene diisocyanate-
, Bis (isocyanatoethyl) benzene, bis (isocyanatopropyl) benzene, α, α, α ', α'-tetramethylxylylene diisocyanate, bis (isocyanatobutyl) benzene, bis (isocyanatomethyl) )
Naphthalene, bis (isocyanatomethyl) diphenyl ether, bis (isocyanatoethyl) phthalate, mesitylylene triisocyanate, 2,6-di (isocyanatomethyl) furan, isophorone diisocyanate, bis (isocyanato) Methyl) cyclohexane, dicyclohexylmethane diisocyanate, cyclohexane diisocyanate, methylcyclohexane diisocyanate, dicyclohexyldimethylmethane diisocyanate, 2,
2'-Dimethyldicyclohexylmethane diisocyanate
, Bis (4-isocyanato-n-butylidene) pentaerythritol, diisocyanate dimer, 2-isocyanatomethyl-3- (3-isocyanatopropyl)-
5-isocyanatomethyl-dicyclo [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- [2,2,2 1] -heptane, 2-isocyanatomethyl-3- (3-isocyanatopropyl) -6- (2
-Isocyanatoethyl) -bicyclo- [2,2,1]-
Heptane, 2-isocyanatomethyl-2- (3-isocyanatopropyl) -5- (2-isocyanatoethyl)-
Bicyclo- [2,2,1] -heptane, 2-isocyanatomethyl-2- (3-isocyanatopropyl) -6-
(2-Isocyanatoethyl) -bicyclo- [2,2,
1] -heptane, 2,5 (or 6) -bis (isocyanatomethyl) -bicyclo [2,2,1] -heptane, and other aliphatic polyisocyanates, 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, tolidine 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 M
DI (diphenylmethane diisocyanate), naphthalene triisocyanate, diphenylmethane 2,4,4 '
-Triisocyanate, 3-methyldiphenylmethane-
4,6,4'-triisocyanate, 4-methyl-diphenylmethane-3,5,2 ', 4', 6'-pentaisocyanate, phenylisocyanatomethylisocyanate
, Phenylisocyanatoethylisocyanate, tetrahydronaphthalene 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, dibenzofurandiocyanate, carbazole diisocyanate, ethyl Examples thereof include aromatic polyisocyanates such as carbazole diisocyanate and diclocarbazole diisocyanate.

Examples of the polyisocyanate compound containing a sulfur atom include thiodiethylene diisocyanate, thiodipropyl diisocyanate, thiodihexyl diisocyanate, and dimethyl sulfone diisocyanate. , Dithiodimethyl diisocyanate, dithiodiethyl diisocyanate, dithiodipropyl diisocyanate, and other sulfur-containing aliphatic isocyanates, diphenyl sulfide-2,4'-diisocyanate, diphenyl sulfide- 4,4'-diisocyanate, 3,3'-dimethoxy-4,4'-diisocyanatodibenzylthioether, bis (4-isocyanatomethylphenyl) sulfide, 4,4'-methoxyphenylthioethylene glycol-3 Aromatic Isocyanates Having Sulfide Bonds such as 3'-diisocyanate -, diphenyl disulfide-4,4' Jiisoshiana - DOO, 2,2'-dimethyl diphenyl disulfide-5,5'-Jiisoshiana -
G, 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 Aromatic diisocyanate having disulfide bond, 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'-diisocyanatobenzylsulfone,
4,4'-Dimethyldiphenylsulfone-3,3'-diisocyanate, 4,4'-di-tert-butyldiphenylsulfone-3,3'-diisocyanate, 4,
4'-methoxyphenylethylene sulfone-3,3'-
Aromatic isocyanate having sulfone bond such as diisocyanate and 4,4'-dicyclodiphenylsulfone-3,3'-diisocyanate, 4-methyl-3-isocyanatophenylsulfonyl-4'-isocyanate Aromatic isocyanate having sulfonic acid ester bond such as phenol ester, 4-methoxy-3-isocyanatophenylsulfonyl-4'-isocyanatophenol ester, 4-methyl-3-isocyanatophenylsulfonylanilide-3'- Methyl-4'-isocyanate
Diphenylsulfonyl-ethylenediamine-4,
4'-diisocyanate, 4,4'-methoxyphenylsulfonyl-ethylenediamine-3,3'-diisocyanate, 4-methyl-3-isocyanatophenylsulfonylanilide-4-methyl-3'-isocyanate, etc. Aromatic isocyanate having sulfonic acid amide bond
And sulfur-containing heterocyclic compounds such as thiophene-2,5-diisocyanate and 1,4-diamine-2,5-diisocyanate.

Further, as the isocyanate compound having an isothiocyanato group, for example, 1-isocyanato-
3-isothiocyanatopropane, 1-isocyanato-
5-isothiocyanatopentane, 1-isocyanato-6
Aliphatic compounds such as isothiocyanatohexane, isothiocyanatocarbonyl isocyanate, 1-isocyanato-4-isothiocyanatocyclohexane, 1-isocyanato-4-isothiocyanatobenzene, 4-methyl-
Aromatic compounds such as 3-isocyanato-1-isothiocyanatobenzene, heterocyclic compounds such as 2-isocyanato-4,6-diisothiocyanato-1,3,5-triazine, and further 4-isocyanato-4 '-Isothiocyanato diphenyl sulfide, 2-isocyanato-2'-
In addition to isothiocyanato groups such as isothiocyanatodiethyldisulfide, compounds containing a sulfur atom and the like can be mentioned.

Also, halogen-substituted compounds such as chlorine-substituted compounds and bromine-substituted compounds of these isocyanate compounds, and further, their burette reaction products, adduct reaction products with trimethylolpropane, dimerization or trimerization reactions. Products and the like can also be used. These may be used alone or in combination of two or more.

The active hydrogen compound used in the present invention is selected from polyol compounds, polythiol compounds and hydroxythiol compounds. Examples of the polyol compound include ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol,
Butylene glycol, neopentyl glycol, glycerin, trimethylolethane, trimethylolpropane, butanetriol, 1,2-methylglucoside,
Pentaerythritol, dipentaerythritol, tripentaerythritol, sorbitol, erythritol, threitol, ribitol, arabinitol, xylitol, allitol, mannitol, dorsitol, iditol, glycol, inositol, hexanetriol, triglycellulose, diglycerol, triethylene glycol, polyethylene glycol, Tris (2-hydroxyethyl) isocyanurate, cyclobutanediol, cyclopentanediol, cyclohexanediol, cycloheptanediol, cyclooctanediol, cyclohexanedimethanol, hydroxypropylcyclohexanol, tricyclo [5,2,1,1]
0 ^2.6 ] decane-dimethanol, bicyclo [4,3,
0] -nonanediol, dicyclohexanediol, tricyclo [5,3,1,1] dodecanediol, bicyclo [4,3,0] nonanedimethanol, tricyclo [5,3,1,1] dodecane-diethanol-, Aliphatic compounds such as hydroxypropyltricyclo [5,3,1,1] dodecanol, spiro [3,4] octanediol, butylcyclohexanediol, 1,1'-bicyclohexylidenediol, cyclohexanetriol, maltitol, lactose Polyol, dihydroxynaphthalene, trihydroxynaphthalene, tetrahydroxynaphthalene, dihydroxybenzene, benzenetriol,
Biphenyltetraol, pyrogallol, (hydroxynaphthyl) pyrogallol, trihydroxyphenanthrene, bisphenol F, xylylene glycol, di (2
-Hydroxyethoxy) benzene, bisphenol A-
Bis- (2-hydroxyethyl ether), tetrabromobisphenol A, tetrabromobisphenol A-
In addition to aromatic polyols such as bis- (2-hydroxyethyl ether), halogenated polyols such as dibromoneopentyl glycol, polymer polyols such as epoxy resins, oxalic acid, glutamic acid, adibic acid, acetic acid, propionic acid, cyclohexanecarboxylic acid. Acid, β-oxocyclohexanepropionic acid, dimer acid, phthalic acid, isophthalic acid, salicylic acid, 3-bromopropionic acid, 2-
Condensation reaction product of an organic acid such as bromoglycol, dicarboxycyclohexane, pyromellitic acid, butanetetracarboxylic acid, bromophthalic acid and the above polyol, addition reaction product of the above polyol and an alkylene oxide such as ethylene oxide or propylene oxide Products, addition reaction products of alkylene polyamines with ethylene oxide and alkylene oxides such as propylene oxide, and further bis- [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] 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-te
Examples thereof include polyols containing a sulfur atom such as rt-butyl-3-methylphenol) and 1,3-bis (2-hydroxyethylthioethyl) -cyclohexane.

As the polythiol, 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, 1,1-cyclohexanedithiol, 1,2-cyclohexanedithiol, 2,2-dimethyl Propane-1,3-dithiol, 3,4-dimethoxybutane-1,2-dithiol, 2-methylcyclohexane-2,3-dithiol, bicyclo [2,2,1] pepta-exo-cis-2,3- Dithiol, 1,1-
Bis (mercaptomethyl) cyclohexane, bis (2-mercaptoethyl ester) thiomalate, 2,3-dimercaptosuccinic acid (2-mercaptoethyl ester), 2,3-dimercapto-1-propanol (2-
Mercapto acetate), 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-mercaptoacetate), trimethylolpropane tris (3-mercaptopropionate) pentaerythritol tetrakis (2-mercaptoacetate) pentaerythritol tetrakis (3-mercaptopropionate), 1,
Aliphatic polythiols such as 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,
1,2-bis (mercaptoethyl) benzene, 1,3-
Bis (mercaptoethyl) benzene, 1,4-bis (mercaptoethyl) benzene, 1,2-bis (mercaptomethyleneoxy) benzene, 1,3-bis (mercaptomethyleneoxy) benzene, 1,4-bis (mercaptomethylene) (Oxy) 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 (mercaptomethyl) 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, 1,2,3,5-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 (mercaptomethyleneoxy)
Benzene, 1,2,4,5-tetrakis (mercaptomethyleneoxy) benzene, 1,2,3,4-tetrakis (mercaptoethyleneoxy) benzene, 1,2,
3,5-tetrakis (mercaptoethyleneoxy) benzene, 1,2,4,5, -tetrakis (mercaptoethyleneoxy) benzene, 2,2′-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-anthracene dimethanethiol, 1,3-di (p
-Methoxyphenyl) propane-2,2-dithiol,
1,3-diphenylpropane-2,2-dithiol, phenylmethane-1,1-dithiol, 2,4-di (p-
Aromatic polythiols such as mercaptophenyl) pentane, 2,5-dichlorobenzene-1,3-dithiol, 1,3-di (p-chlorophenyl) propane-
2,2-dithiol, 3,5,4-tribromo-1,2
-Chlorine-substituted aromatic polythiols such as dimercaptobenzene and 2,3,4,6-tetrachloro-1,5-bis (mercaptomethyl) benzene, and bromine-substituted aromatic polythiols, and 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-dithiol-sym-triazine, 2-thiobutyloxy-
Polythiols containing heterocycles such as 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, 1,3,5-tris (Mercaptoethylthio) benzene, 1,2,3,4-tetrakis (mercaptomethylthio) benzene, 1,2,3,5-tetrakis (mercaptomethylthio) benzene, 1,2,
4,5-Tetrakis (mercaptomethylthio) benzene, 1,2,3,4-tetrakis (mercaptoethylthio) benzene, 1,2,3,5-tetrakis (mercaptoethylthio) benzene, 1,2,4,5 -Tetrakis (mercaptoethylthio) benzene, etc., and aromatic polythiols containing a sulfur atom in addition to the mercapto group such as the alkylated products thereof, bis (mercaptomethyl) sulfide, bis (mercaptoethyl) sulfide, bis (mercaptopropyl) Sulfide, bis (mercaptomethylthio) methane, bis (2-mercaptoethylthio) methane, bis (3-mercaptopropyl) 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, 1,2,3 -Tris (mercaptomethylthio) propane, 1,2,3-tris (2-mercaptoethylthio) propane, 1,2,3-
Tris (3-tris (3-mercaptopropylthio) propane, tetrakis (mercaptomethylthiomethyl) methane, tetrakis (2-mercaptoethylthioethyl)
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, etc., and their thioglycolic acid and mercaptopropionic acid esters, hydroxymethylsulfide bis (2-mercaptoacetate), hydroxymethylsulfide bis (3-mercaptopropionate), hydroxyethyl sulfide bis (2-mercaptoacetate), hydroxyethyl sulfide bis (3-mercaptopropionate), hydroxypropyl sulfide bis (2-mercaptoacetate), hydroxypropyl sulfide bis (3 -Mercaptopropionate), hydroxymethyl disulfide bis (2-
Mercaptoacetate), hydroxymethyldisulfidebis (3-mercaptopropionate), hydroxyethyldisulfidebis (2-mercaptoacetate), hydroxyethyldisulfidebis (3-mercaptopropionate), hydroxypropyldisulfidebis (2-mercaptoacetate) ), Hydroxypropyl disulfide bis (3-mercaptopropionate), 2-mercaptoethyl ether bis (2-mercaptoacetate), 2-mercaptoethyl ether bis (3-mercaptopropionate), 1,4-dithiane-2. , 5-diolbis (2-mercaptoacetate), 1,4-dithiane-2,5-diolbis (3-
Mercaptopropionate), thioglycolic acid bis (2-mercaptoethyl ester), thiodipropionic acid bis (2-mercaptoethyl ester), 4,4-thiodibutyric acid bis (2-mercaptoethyl ester),
Bis (2-mercaptoethyl ester) dithiodiglycolic acid, bis (2-mercaptoethyl ester) dithiodipropionate, bis (2-mercaptoethyl ester) 4,4-dithiodibutylate
Mercaptoethyl ester), thiodiglycolic acid bis (2,3-dimercaptopropyl ester), thiodipropionic acid bis (2,3-dimercaptopropyl ester), thiodipropionic acid bis (2,3-dimercaptopropyl) Ester), bis (2,3) dithioglycolate
-Dimercaptopropyl ester), dithiodipropionic acid (2,3-dimercaptopropyl ester), and the like, an aliphatic polythiol containing a sulfur atom in addition to the mercapto group, 3,4-thiophenedithiol, 2,5-dimercapto-1 And a heterocyclic compound containing a sulfur atom in addition to a mercapto group such as 3,4-thiadiazole.

Examples of hydroxy thiol compounds include 2-mercaptoethanol, 3-mercapto-1,2-propanediol, glycerin di (mercaptoacetate), 1-hydroxy-4-mercaptocyclohexane and 2,4-dimercapto. Phenol, 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), pentaerythritol bis (3-mercaptopropionate), pentaerythritol tris (thioglycolate), pentaerythritol pentakis (3-mercaptopropionate) ), Hydroxymethyl-tris (mercaptoethylthioethyl) methane, 1-hydroxyethylthio-3-
Mercaptoethylthiobenzene, 4-hydroxy-4 '
-Mercaptodiphenyl sulfone, 2- (2-mercaptoethylthio) ethanol, dihydroxyethyl sulfide mono (3-mercaptopropionate), dimercaptoethane mono (sulfylate), hydroxyethylthiomethyl-tris (mercaptoethylthio) methane, etc. Is mentioned.

Further, a chlorine-substituted product or a bromine-substituted product of these active hydrogen compounds may be used.
These may be used alone or in combination of two or more. The ratio of these isocyanate compounds and active hydrogen compounds used is (NCO + NCS)
/ (OH + SH) functional group molar ratio is usually 0.5 to 3.
It is in the range of 0, preferably in the range of 0.5 to 1.5.

Known chain extenders, crosslinking agents, light stabilizers, ultraviolet absorbers, antioxidants, oil-soluble dyes,
You may add various substances, such as a filler and an internal mold release agent.
In order to control the reaction rate, a known reaction catalyst used in the production of polyurethane can be appropriately added.

[0029]

BEST MODE FOR CARRYING OUT THE INVENTION The present invention will be described in detail, but the present invention is not limited to these examples.

Example 1 An adhesive tape (180 ° stainless steel adhesive force 700 g / 25 mm) obtained by coating a polyethylene terephthalate biaxially stretched film having a width of 25 mm and a thickness of 50 μm with a silicone adhesive of 25 μm was used as an optical surface of a lens. The two glass molds forming the glass mold were fixed with a jig so that the distance between them formed a lens shape, and the glass molds were wound around the side surface of the outer periphery of the glass mold. It was wound around once with an overlapped portion of about 4 to 5 cm, and brought into close contact with the glass mold.

Thereafter, a soldering iron at 200 ° C. was pressed against the tape overlapping portion, and the step portion was traced several times. The states before and after the heat treatment are shown in FIG.

1,2-Bis [(2-mercaptoethyl) thio] -3-in the mold thus assembled
87 g of mercaptopropane, 94 g of m-xylylene diisocyanate, internal release agent (manufactured by Daikin Industries, Ltd.
Brand name "DS-401") 0.1 g, di-n-butyltin dichloride 0.002 g, 2- (2-hydroxy-5)
A liquid curable composition consisting of 0.2 g of -ethyl) benzotriazole was injected, the temperature was raised from 30 ° C to 120 ° C over 12 hours, and the temperature was kept constant at 120 ° C for 2 hours to complete the polymerization. After slowly cooling to room temperature, remove it from the polymerization tank and
Removed. Leakage during injection, leakage during polymerization and chipping were evaluated and are shown in Table 1.

(Comparative Example 1) The same procedure as in Example 1 was performed except that the heat treatment with the soldering iron was not performed in Example 1. The results were evaluated in the same manner as in Example 1,
The results are shown in Table 1.

(Comparative Example 2) The same procedure as in Example 1 was carried out except that the pressure-sensitive adhesive used in Example 1 had a thickness of 2 μm. The results were evaluated in the same manner as in Example 1 and shown in Table 1.

Comparative Example 3 The procedure of Example 1 was repeated except that the thickness of the base material of the adhesive tape used in Example 1 was changed to 250 μm. See Example 1 for results.
Table 1 shows the evaluation results.

(Comparative Example 4) The same procedure as in Example 1 was carried out except that the thickness of the base material of the adhesive tape used in Example 1 was changed to 250 μm and the heat treatment by the soldering iron was not performed. The results were evaluated in the same manner as in Example 1 and shown in Table 1.

Comparative Example 5 The same procedure as in Example 1 was carried out except that the temperature of the soldering iron was changed to 50 ° C. in Example 1. The results were evaluated in the same manner as in Example 1,
The results are shown in Table 1.

(Comparative Example 6) The adhesive strength of the adhesive tape in Example 1 was changed to 180 ° stainless steel adhesive strength 60 g / 25 mm.
The same procedure as in Example 1 was carried out except that the above procedure was changed.
The results were evaluated in the same manner as in Example 1 and shown in Table 1.

(Example 2) The same procedure as in Example 1 was carried out except that the heating with the soldering iron was stopped in Example 1 and the silicon rubber heated to 180 ° C was pressed against the tape overlapping portion for 30 seconds. The results were evaluated in the same manner as in Example 1 and shown in Table 1.

[0040]

[Table 1]

[0041]

EFFECTS OF THE INVENTION According to the present invention, (1) since there is no leakage at the time of injecting the raw material into the glass mold and at the time of polymerization, contamination by the raw material can be prevented, the lens appearance does not have a problem, and a high yield can be secured.

(2) Since no chipping due to drawing of outside air occurs during polymerization, there is no problem in the lens appearance and a high yield can be secured.

[Brief description of drawings]

FIG. 1 shows a state of adhesion of an adhesive tape to a glass mold before and after heat treatment of the present invention.

[Explanation of symbols]

 A: State before heat treatment B: State after heat treatment 1: Glass mold 2: Tape base material 3: Adhesive 4: Gap

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁶ Identification code Office reference number FI technical display location B29L 11:00

Claims (4)

[Claims] 1. An adhesive sheet is adhered to the periphery of the side surfaces of two molds positioned at a predetermined interval, and is formed by being surrounded by the two molds and the adhesive tape. When manufacturing a plastic lens by injecting a liquid curable compound into a mold and casting polymerization, a plastic lens characterized by heat-treating or thermocompression-bonding the part of the side of the mold where the adhesive tape overlaps before injection. Manufacturing method. 2. The total thickness of the pressure-sensitive adhesive and the primer of the pressure-sensitive adhesive tape is 5 to 100 micrometers, and the thickness of the substrate is 25.
To 100 micrometers, The manufacturing method of the plastic lens of Claim 1 characterized by the above-mentioned. 3. The method for producing a plastic lens according to claim 1, wherein the heat treatment temperature is 60 ° C. or higher. 4. The method for producing a plastic lens according to claim 1, wherein the adhesive strength of the 180 ° stainless steel of the adhesive sheet is 100 g / 25 mm or more.