CN104024300A - Polymerizable composition for optical material containing thioepoxy compound, and preparation method of optical material - Google Patents

Polymerizable composition for optical material containing thioepoxy compound, and preparation method of optical material Download PDF

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CN104024300A
CN104024300A CN201280063547.5A CN201280063547A CN104024300A CN 104024300 A CN104024300 A CN 104024300A CN 201280063547 A CN201280063547 A CN 201280063547A CN 104024300 A CN104024300 A CN 104024300A
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optical material
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CN104024300B (en
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张东奎
卢守均
金钟孝
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KOC Solution Co Ltd
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KOC Solution Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
    • C08G18/3855—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur
    • C08G18/3874—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur containing heterocyclic rings having at least one sulfur atom in the ring
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
    • G02B1/041—Lenses
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
    • C08G18/3855—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
    • C08G18/3855—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur
    • C08G18/3876—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur containing mercapto groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/04—Polyurethanes
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B3/00—Simple or compound lenses
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/50—Physical properties
    • C08G2261/57—Physical properties photorefractive, e.g. change of refractive index

Abstract

The present invention relates to a polymerizable composition for an optical material, and a preparation method of an optical material for obtaining a high quality thioepoxy-based optical material without uncuring or polymer imbalance. The present invention provides a preparation method of a thioepoxy-based optical material comprising the steps of: preparing a polymerizable composition containing a thioepoxy compound with a pH of 4-8; and template polymerizing the polymerizable composition. The thioepoxy-based optical material prepared according to the present invention can be widely used in various fields by replacing conventional optical materials.

Description

Containing optical material polymer composition and the optical material manufacture method of sulfo-epoxy group(ing) (thioepoxy) compound
Technical field
The present invention relates to the optical material manufacture method of polymerised sulphur for epoxy compounds, relate in particular to one and can avoid unhardened or polymerization non-uniform phenomenon, obtain the optical material polymer composition of high-quality sulfo-epoxy base system optical material and the manufacture method of optical material.
Background technology
Korean registered patent discloses a kind of sulfo-epoxy base system glass lens for No. 10-0681218.Sulfo-epoxy base system eyeglass refractive index is high, and has high Abbe number, and performance is outstanding, but problem is easily fragmentation of eyeglass, not easy dyeing.In order to address this problem, No. 10-0417985, Korean registered patent, the flat 11-352302 of Japanese Laid-Open Patent etc. discloses the method for two kinds of resins of different nature of polymerization, and polymerised sulphur is for the method for epoxy compounds and poly-thiol compound and polyisocyanate compounds.
Sulfo-epoxy base system eyeglass or copolymerization sulfo-epoxy group(ing) and sulphur urethane and come sulfo-epoxy base system eyeglass, when the polymerization of polymerizability synthetics injection molding, be all difficult to sclerosis, cause polymerization problem of non-uniform, cause arteries and veins reason or gonorrhoea, bubble etc., often occur the problem that eyeglass quality is low.This inhomogeneous meeting of polymerization unhardened and that cause thus causes the yield of eyeglass to reduce, and becomes the essential factor that increases production cost.At present, one of the point of contact, main pass in eyeglass field is to reduce production costs, and the unhardened and polymerization problem of non-uniform existing containing the optical material of sulfo-epoxy compounds is badly in need of improving.
Summary of the invention
The problem of invention
Each contriver of the present invention forms in the process of eyeglass in the polymerizability synthetics polymerization by comprising sulfo-epoxy compounds, and while chancing on the pH difference of sulfo-epoxy compounds, hardenability has very big difference.The pH of sulfo-epoxy compounds is than under the low or high state of the proper range of the present inventor's confirmation, and the sclerosis of synthetics is not smooth, is difficult to the normal eyeglass that obtains; even if or harden, also inhomogeneous because of polymerization, cause Quality Down; be difficult to use eyeglass, or yield declines to a great extent.But in the proper range that the pH of sulfo-epoxy compounds confirms in the present invention time, because the sclerosis of synthetics is very good, can avoid polymerization inhomogeneous, can easily manufacture high quality optical eyeglass.
The present invention is the invention completing after checking this point, its object is to provide a kind of utilization to comprise the optical material polymerizability synthetics containing more than one compound of sulfo-epoxy group(ing), avoid unhardened or polymerization is inhomogeneous, manufacture the manufacture method of high-quality sulfo-epoxy base system optical material and the sulfo-epoxy base system optical material polymerizability synthetics for this with high yield.
Embodiment
In the present invention, " sulfo-epoxy compounds " is defined as the compound with more than 1 sulfo-epoxy group(ing).
In the present invention " sulfo-epoxy base system optical material " as being not particularly limited, comprise polymerised sulphur for epoxy compounds optical material and copolymerization sulfo-epoxy group(ing) and sulphur urethane and optical material.
The invention provides a kind of sulfo-epoxy base system optical material manufacture method, comprise the polymerizability synthetics manufacturing stage containing the sulfo-epoxy compounds of pH4～8,
In the stage of described polymerizability synthetics injection molding polymerization.
The invention provides one
Contain the optical material polymerizability synthetics of the sulfo-epoxy compounds of pH4～8.
In addition, the invention provides a kind of optical material that hardens described polymerizability synthetics and obtain and the optical mirror slip being formed by this optical material.Described optical mirror slip especially comprises glasses lens or polarized lenses.
Invention effect
The present invention is controlled at the pH value of sulfo-epoxy compounds in specified range, can prevent arteries and veins reason, albefaction, bubble by unhardened or the inhomogeneous initiation of polymerization, the high-quality eyeglass that can manufacture water white transparency, nothing distortion, can improve yield, reduce production costs.
Embodiment
The invention provides a kind of sulfo-epoxy base system optical material manufacture method, comprise the polymerizability synthetics manufacturing stage containing the sulfo-epoxy compounds of pH4～8, in the stage of this polymerizability synthetics injection molding polymerization.
If the pH of sulfo-epoxy compounds is lower than 4 or higher than 8, have some setbacks when polymerization, be difficult to the normal eyeglass that obtains, even if a part is hardened, also because polymerization is inhomogeneous, causes quality and decline, be difficult to use gained eyeglass.The problem of the inhomogeneous initiation of polymerization has arteries and veins reason, albefaction, edge bubbling etc. conventionally, if exceed described scope, even if produce sclerosis to a certain degree, also can be because of the generation of arteries and veins reason, albefaction or bubble, cause the quality of eyeglass to decline, reduce yield, increase production and rise this.On the contrary, manufacture polymerizability synthetics taking the pH of sulfo-epoxy compounds as 4～8 condition, while carrying out polyreaction, even if do not change other conditions, also the sclerosis difficult problem occurring in the manufacturing processed of sulfo-epoxy base system optical material can be overcome, optical material can be easily manufactured.
Described sulfo-epoxy compounds is selected from 1 above such as being a kind, 3-and 1, 4-bis-(β-epithio is for propyl dithiocarbamate) hexanaphthene) (bis (β-epithiopropylthio) cyclo hexane), 1, 3-and 1, 4-bis-(β-epithio is for propyl dithiocarbamate methyl) hexanaphthene) (bis (β-epithiopropylthiomethyl) cyclo hexane), two [4-(β-epithio is for propyl dithiocarbamate) cyclohexyl] methane (bis[4-(β-epithiopropylthio) cyclo hexyl] methane), 2, 2-bis-[4-(β-epithio is for propyl dithiocarbamate) cyclohexyl] propane (2, 2-bis[4-(β-epithiopropylthio) cyclo hexyl] propane), two [4-(β-epithio is for propyl dithiocarbamate) cyclohexyl] sulfide (bis[4-(β-epithiopropylthio) cyclo hexyl] sulfide) etc. has the episulfide compound of alicyclic bone, 1, 3-and 1, 4-bis-(β-epithio is for propyl dithiocarbamate methyl) benzene bis (β-epithiopropylthiomethyl) benzene), two [4-(β-epithio is for propyl dithiocarbamate) phenyl] methane (bis[4-(β-epithiopropylthio) phenyl] methane), 2, 2-bis-[4-(β-epithio is for propyl dithiocarbamate) phenyl] propane (2, 2-bis[4-(β-epithiopropylthio) phenyl] propane), two [4-(β-epithio is for propyl dithiocarbamate) phenyl] sulfide (bis[4-(β-epithiopropylthio) phenyl] sulfide), two [4-(β-epithio is for propyl dithiocarbamate) phenyl] disulphide (bis[4-(β-epithiopropylthio) phenyl] disulfide), two [4-(β-epithio is for propyl dithiocarbamate) phenyl] sulphur (bis[4-(β-epithiopropylthio) phenyl] sulfin), 4, 4-bis-(β-epithio is for propyl dithiocarbamate) phenylbenzene (4, 4-bis (β-epithiopropylthio) biphenyl) etc. there is the episulfide compound of aromatic series bone, 2, 5-bis-(β-epithio is for propyl dithiocarbamate methyl)-1, 4-dithiane (2, 5-bis (β-epithiopropylthiomethyl)-1, 4-dithiane), 2, 5-bis-(β-epithio is for propyl dithiocarbamate ethylenebis dithiocarbamate methyl)-1, 4-dithiane (2, 5-bis (β-epithiopropylthioethylthiomethyl)-1, 4-dithiane), 2, 5-bis-(β-epithio is for propyl dithiocarbamate ethyl group)-1, 4-dithiane (2, 5-bis (β-epithiopropylthioethyl)-1, 4-dithiane), 2, 3, 5-tri-(β-epithio is for propyl dithiocarbamate ethyl group)-1, 4-dithiane (2, 3, 5-tri (β-epithiopropylthioethyl)-1, 4-dithiane) etc. there is the episulfide compound of dithiane (dithiane) chain bone, 2-(2-β-epithio is for propyl dithiocarbamate ethylenebis dithiocarbamate)-1, 3-bis-(β-epithio is for propyl dithiocarbamate) propane (2-(2-β-epithiopropylthioethylthio)-1, 3-bis (β-epithiopropylthio) propane), 1, 2-bis-[(2-β-epithio is for propyl dithiocarbamate ethyl group) sulfo-]-3-(β-epithio is for propyl dithiocarbamate) propane (1, 2-bis[(2-β-epithiopropylthioethyl) thio]-3-(β-epithiopropylthio) propane), four (β-epithio is for propyl dithiocarbamate methyl) methane) (Tetrakis (β-epithiopropylthiomethyl) methane), 1, 1, 1-tri-(β-epithio is for propyl dithiocarbamate methyl) propane (1, 1, 1-tris (β-epithiopropylthiomethyl) propane), two-(β-epithio is for propyl group) sulfide (bis-(β-epithiopropyl) sulfide), two-(β-epithio is for propyl group) disulphide (bis-(β-epithiopropyl) disulfide) etc. have episulfide (episulfide) compound of aliphatics bone.In addition, can also use the halogen family substitution product such as chlorine substitution product (substitution product), bromine substitution product, alkyl substitution product (alkyl substitution product), alkoxyl group substitution product (alkoxy substitution product), nitro substitution product (nitro substitution product) of the compound of band sulfuration (episulfide) base or prepolymer (prepolymer) the type denatured products (denaturant) with polythiol.Preferably use two-(2 as sulfo-epoxy compounds, 3-epithio is for propyl group) sulfide (bis-(2, 3-epithiopropyl) sulfide), two-(2, 3-epithio is for propyl group) disulphide (bis-(2, 3-epithiopropyl) disulfide), 1, 3-and 1, 4-bis-(β-epithio is for propyl dithiocarbamate) hexanaphthene), 1, 3-and 1, 4-bis-(β-epithio is for propyl dithiocarbamate methyl) hexanaphthene), 2, 5-bis-(β-epithio is for propyl dithiocarbamate methyl)-1, 4-dithiane, 2, 5-bis-(β-epithio is for propyl dithiocarbamate ethylenebis dithiocarbamate methyl)-1, 4-dithiane, 2-(2-β-epithio is for propyl dithiocarbamate ethylenebis dithiocarbamate)-1, in 3-bis-(β-epithio is for propyl dithiocarbamate) propane more than a kind.
Described polymerizability synthetics can also comprise poly-thiol compound.Described poly-thiol compound is not particularly limited, and as long as having the compound of more than 1 thiol group, can be used alone or mixes two or more use.Such as, can use two (2-mercaptoethyl) sulfide (bis (2-mercapto ethyl) sulfide), 4-mercapto methyl-1, 8-dimercapto-3, 6-dithio octane (4-mercapto methyl-1, 8-dimercapto-3, 6-dithia octane), 2, 3-bis-(2-mercaptoethyl sulfo-) propane-1-mercaptan (2, 3-bis (2-mercapto ethyl thio) propane-1-thiol), 1, 3-and 1, 4-xylyl alcohol mercaptan (benzene di methanol thiol) (1, 3-and 1, 4-xylylene two mercaptan (xylylene dithiol)), 2, 2-bis-(mercapto methyl)-1, 3-propane two mercaptan (2, 2-bis (mercapto methyl)-1, 3-propane dithiol), four (mercapto methyl) methane (Tetrakis (mercapto methyl) methane), 2-(2-mercaptoethyl sulfo-) propane-1, 3-bis-mercaptan (2-(2-mercapto ethyl thio) propane-1, 3-dithiol), 2-(2, 3-bis-(2-mercaptoethyl sulfo-) propyl dithiocarbamate) ethane mercaptan (2-(2, 3-bis (2-mercapto ethyl thio) propyl thio) ethane thiol), two (2, 3-dimercaprol dimercaptopropanol) sulfide (bis (2, 3-dimercapto propanol) sulfide), two (2, 3-dimercaprol dimercaptopropanol) disulphide (bis (2, 3-dimercapto propanol) disulfide), 1, 2-bis-(2-mercaptoethyl sulfo-)-3-sulfydryl propane (1, 2-bis (2-mercapto ethyl thio)-3-mercapto propane), 1, 2-bis-(2-(2-mercaptoethyl sulfo-)-3-sulfydryl propyl dithiocarbamate) ethane (1, 2-bis (2-(2-mercapto ethyl thio)-3-mercapto propyl thio) ethane), two (2-(2-mercaptoethyl sulfo-)-3-sulfydryl propyl group) sulfide (bis (2-(2-mercapto ethyl thio)-3-mercapto propyl) sulfide), 2-(2-mercaptoethyl sulfo-)-3-2-sulfydryl-3-[3-sulfydryl-2-(2-mercaptoethyl sulfo-)-propyl dithiocarbamate] propyl dithiocarbamate-propane-1-mercaptan (2-(2-mercapto ethyl thio)-3-2-mercapto-3-[3-mercapto-2-(2-mercapto ethyl thio)-propyl thio] propyl thio-propane-1-thiol), 2, 2-bis--(3-sulfydryl-propionyl oxygen methyl)-butyl ester (2, 2-bis-(3-mercapto-propionyl oxymethyl)-butyl ester), 2-(2-mercaptoethyl sulfo-)-3-(2-(2-[3-sulfydryl-2-(2-mercaptoethyl sulfo-)-propyl dithiocarbamate] ethylenebis dithiocarbamate) ethylenebis dithiocarbamate) propane-1-mercaptan (2-(2-mercapto ethyl thio)-3-(2-(2-[3-mercapto-2-(2-mercapto ethyl thio)-propyl thio] ethyl thio) ethyl thio) propane-1-thiol), (4R, 11S)-4, 11-bis-(mercapto methyl)-3, 6, 9, 12-tetrathio four decane-1, 14-bis-mercaptan ((4R, 11S)-4, 11-bis (mercapto methyl)-3, 6, 9, 12-Tetra thia Tetra decane-1, 14-dithiol), (S)-3-((R-2, 3-dimercapto propyl group) sulfo-) propane-1, 2-bis-mercaptan ((S)-3-((R-2, 3-dimercapto propyl) thio) propane-1, 2-dithiol), (4R, 14R)-4, 14-bis-(mercapto methyl)-3, 6, 9, 12, 15-five sulfo-heptane-1, 17-bis-mercaptan ((4R, 14R)-4, 14-bis (mercapto methyl)-3, 6, 9, 12, 15-Penta thia heptane-1, 17-dithiol), (S)-3-((R-3-sulfydryl-2-((2-mercaptoethyl) sulfo-) propyl group) sulfo-) propyl group) sulfo-)-2-((2-mercaptoethyl) sulfo-) propane-1-mercaptan ((S)-3-((R-3-mercapto-2-((2-mercapto ethyl) thio) propyl) thio) propyl) thio)-2-((2-mercapto ethyl) thio) propane-1-thiol) (annotation of translation: bracket sic herein, lower same ), 3, 3'-dithio two (propane-1, 2-bis-mercaptan) (3, 3'-dithio bis (propane-1, 2-dithiol)), (7R, 11S)-7, 11-bis-(mercapto methyl)-3, 6, 9, 12, 15-five sulfo-heptadecane 100 alkane-1, 17-bis-mercaptan ((7R, 11S)-7, 11-bis (mercapto methyl)-3, 6, 9, 12, 15-Penta thia heptadecane-1, 17-dithiol), (7R, 12S)-7, 12-bis-(mercapto methyl)-3, 6, 9, 10, 13, 16-six sulfo-octadecane-1, 18-bis-mercaptan ((7R, 12S)-7, 12-bis (mercapto methyl)-3, 6, 9, 10, 13, 16-hexa thia octadecane-1, 18-dithiol), 5, 7-dimercapto methyl-1, 11-dimercapto-3, 6, 9-trithio undecane (5, 7-dimercapto methyl-1, 11-dimercapto-3, 6, 9-trithia undecane), 4, 7-dimercapto methyl-1, 11-dimercapto-3, 6, 9-trithio undecane (4, 7-dimercapto methyl-1, 11-dimercapto-3, 6, 9-trithia undecane), 4, 8-dimercapto methyl-1, 11-dimercapto-3, 6, 9-trithio undecane (4, 8-dimercapto methyl-1, 11-dimercapto-3, 6, 9-trithia undecane), tetramethylolmethane four (3-mercaptopropionic acid ester) (Penta erythritol Tetrakis (3-mercapto propionate)), three methylol propane three (3-mercaptopropionic acid ester) (trimethylol propane tris (3-mercapto propionate)), tetramethylolmethane four (2-thioglycolate) (Pentaerythritol Tetrakis (2-mercapto acetate)), Dipentaerythritol-ether-phenylpropyl alcohol tin (3-mercaptopropionic acid ester) (bispenta erythritol-ether-hexakis (3-mercapto propionate)), 1, 1, 3, 3-tetra-(mercapto methyl sulfo-) propane (1, 1, 3, 3-Tetrakis (mercapto methyl thio) propane), 1, 1, 2, 2-tetra-(mercapto methyl sulfo-) ethane (1, 1, 2, 2-Tetrakis (mercapto methyl thio) ethane), 4, 6-bis-(mercapto methyl sulfo-)-1, 3-dithiane (4, 6-bis (mercapto methyl thio)-1, 3-dithiane) and 2-(2, 2-bis-(sulfydryl dimethyl sulphide generation) ethyl)-1, 3-dithiane (2-(2, 2-bis (mercapto dimethyl thio) ethyl)-1, 3-dithiane) etc.Outside, as long as thering is the compound of more than 1 thiol group, can use one or be mixed with two or more.In addition, also can use to poly-thiol compound and add isocyanic ester or sulfo-epoxy compounds, sulfuration cyclopropane (Thietane) or the compound with unsaturated combination with modifier use, the polymerization denatured products obtaining by prepolymerization.Preferably mixing more than a kind other poly-thiol compounds to two (2-mercaptoethyl) sulfide or two (2-mercaptoethyl) sulfide as poly-thiol compound uses.
Described polymerizability synthetics can also comprise polyisocyanate compounds.Described polyisocyanate compounds is not particularly limited, can use at least with more than 1 isocyanic acid and/. or the compound of different thiocyanato.Such as, can mix and use one kind or two or more 2, 2-dimethylpentane vulcabond (2, 2-dimethyl pentane diisocyanate), 2, 2, 4-trimethyl cyclohexane vulcabond (2, 2, 4-trimethyl hexane diisocyanate), hexamethylene diisocyanate (hexa methylene diisocyanate), pentamethylene diisocyanate (Penta methylene diisocyanate), butene diisocyanate (butene diisocyanate), 1, 3-divinyl-1, 4-vulcabond (1, 3-butadiene-1, 4-diisocyanate), 2, 4, 4-trimethyl hexamethylene diisocyanate (2, 4, 4-trimethyl hexa methylene diisocyanate), 1, 6, 11-undecane triisocyanate (1, 6, 11-undecane triisocyanate), 1, 3, 6-hexa-methylene triisocyanate (1, 3, 6-hexa methylene triisocyanate), 1, 8-vulcabond-4-isocyanato methyloctane (1, 8-diisocyanate-4-isocyanato methyl octane), two (isocyanato ethyl) carbonic ether (bis (isocyanato ethyl) carbonate), the aliphatic isocyanates compounds (aliphatic isocyanate compounds) such as two (isocyanato ethyl) ether (bis (isocyanato ethyl) ether), isophorone diisocyanate (isophorone diisocyanate), 1, 2-bis-(isocyanato methyl) hexanaphthene (1, 2-bis (isocyanato methyl) cyclo hexane), 1, 3-bis-(isocyanato methyl) hexanaphthene (1, 3-bis (isocyanato methyl) cyclo hexane), 1, 4-bis-(isocyanato methyl) hexanaphthene (1, 4-bis (isocyanato methyl) cyclo hexane), dicyclohexyl methane diisocyanate (dicyclo hexyl methane diisocyanate), cyclohexyl diisocyanate (cyclo hexane diisocyanate), methylcyclohexane diisocyanate (methyl cyclo hexane diisocyanate), dicyclohexyl dimethylmethane isocyanic ester (dicyclo hexyl dimethyl methane isocyanate), 2, 2-dimethyl dicyclohexyl methyl hydride isocyanic ester (2, 2-dimethyl dicyclo hexyl methane isocyanate) etc. alicyclic isocyanate compound (Cycloaliphatic isocyanate compounds), eylylene diisocyanate (xylylene diisocyanate (XDI)), two (isocyanato ethyl) benzene (bis (isocyanatoethyl) benzene), two (isocyanato propyl group) benzene (bis (isocyanato propyl) benzene), two (isocyanato butyl) benzene (bis (isocyanato butyl) benzene), two (isocyanato methyl) naphthalene (bis (isocyanato methyl) naphthalene), two (isocyanato methyl) phenylbenzene ether (bis (isocyanato methyl) diphenyl ether), phenylene vulcabond (phenylene diisocyanate), ethyl phenylene vulcabond (ethyl phenylene diisocyanate), sec.-propyl phenylene vulcabond (isopropyl phenylene diisocyanate), dimethyl phenylene vulcabond (dimethyl phenylene diisocyanate), diethyl phenylene vulcabond (diethyl phenylene diisocyanate), di-isopropyl phenylene vulcabond (diisopropyl phenylene diisocyanate), Three methyl Benzene triisocyanate (trimethyl benzene triisocyanate), benzene triisocyanate (benzene triisocyanate), biphenyl diisocyanate (biphenyl diisocyanate), Tolylamine vulcabond (toluidine diisocyanate), 4, 4-diphenylmethanediisocyanate (4, 4-diphenyl methane diisocyanate), 3, 3-dimethyl diphenylmethane-4, 4-vulcabond (3, 3-dimethyl diphenyl methane-4, 4-diisocyanate), bibenzyl-4, 4-vulcabond (bibenzyl-4, 4-diisocyanate), two (isocyanato phenyl) ethene (bis (isocyanato phenyl) ethylene), 3, 3-dimethoxy-biphenyl-4, 4-vulcabond (3, 3-dimethoxy biphenyl-4, 4-diisocyanate), hexahydrobenzene vulcabond (hexa hydrobenzene diisocyanate), six diphenyl hydrogen methylmethane-4, 4-vulcabond (hexa hydro diphenyl methane-4, the aromatic isocyanate compound (aromatic isocyanate compounds) such as 4-diisocyanate), two (isocyanato ethyl) sulfide (bis (isocyanato ethyl) sulphide), two (isocyanato propyl group) sulfide (bis (isocyanato propyl) sulphide), two (isocyanato hexyl) sulfide (bis (isocyanato hexyl) sulphide), two (isocyanato methyl) sulfide (bis (isocyanato methyl) sulfide), two (isocyanato methyl) disulphide (bis (isocyanato methyl) disulphide), two (isocyanato propyl group) disulphide (bis (isocyanato propyl) disulphide), two (isocyanato methyl sulfo-) methane (bis (isocyanato methyl thio) methane), two (isocyanato ethylenebis dithiocarbamate) methane (bis (isocyanato ethyl thio) methane), two (isocyanato ethylenebis dithiocarbamate) ethane (bis (isocyanato ethyl thio) ethane), two (isocyanato methyl sulfo-) ethane (bis (isocyanato methyl thio) ethane), 1,5-bis-isocyanatos-2-isocyanato methyl-3-sulfo-pentane (1,5-diisocyanato-2-isocyanato methyl-3-thia pentane) etc. sulfur-bearing aliphatic isocyanates compound (sulfur aliphatic isocyanate compounds), diphenyl sulfide-2, 4-vulcabond (diphenyl sulphide-2, 4-diisocyanate), diphenyl sulfide-4, 4-vulcabond (diphenyl sulphide-4, 4-diisocyanate), 3, 3-dimethoxy-4 ', 4-bis-isocyanato diphenyl-methyl thio-ethers (3, 3-dimethoxy-4, 4-diisocyanato dibenzyl thio ether), two (4-isocyanato methylbenzene) sulfide (bis (4-isocyanato methyl benzene) sulphide), 4, 4-anisole sulfo-ethylene glycol-3, 3-vulcabond (4, 4-methoxy benzene thio ethylene glycol-3, 3-diisocyanate), Diphenyl disulfide compound-4, 4-vulcabond (diphenyl disulphide-4, 4-diisocyanate), 2, 2-dimethyl diphenyl disulphide-5, 5-vulcabond (2, 2-dimethyl diphenyl disulphide-5, 5-diisocyanate), 3, 3-dimethyl diphenyl disulphide-5, 5-vulcabond (3, 3-dimethyl diphenyl disulphide-5, 5-diisocyanate), 3, 3-dimethyl diphenyl disulphide-6, 6-vulcabond (3, 3-dimethyl diphenyl disulphide-6, 6-diisocyanate), 4, 4-dimethyl diphenyl disulphide-5, 5-vulcabond (4, 4-dimethyl diphenyl disulphide-5, 5-diisocyanate), 3, 3-dimethoxy Diphenyl disulfide compound-4, 4-vulcabond (3, 3-dimethoxy diphenyl disulphide-4, 4-diisocyanate), 4, 4-dimethoxy Diphenyl disulfide compound-3, 3-vulcabond (4, 4-dimethoxy diphenyl disulphide-3, the sulfur-containing aromatic isocyanate compound (sulfur aromatic isocyanate compounds) such as 3-diisocyanate), 2, 5-bis-isocyanato thiophene (2, 5-diisocyanato thiophene), 2, 5-bis-(isocyanato methyl) thiophene (2, 5-bis (isocyanato methyl) thiophene), 2, 5-bis-isocyanato tetramethylene sulfides (2, 5-diisocyanato Tetra hydrothiophene), 2, 5-bis-(isocyanato methyl) tetramethylene sulfide (2, 5-bis (isocyanato methyl) Tetra hydrothiophene), 3, 4-bis-(isocyanato methyl) tetramethylene sulfide (3, 4-bis (isocyanato methyl) Tetra hydrothiophene), 2, 5-bis-isocyanato-1, 4-dithiane (2, 5-diisocyanato-1, 4-dithiane), 2, 5-bis-(isocyanato methyl)-1, 4-dithiane (2, 5-bis (isocyanato methyl)-1, 4-dithiane), 4, 5-bis-isocyanato-1, 3-dithiolane (4, 5-diisocyanato-1, 3-dithiolane), 4, 5-bis-(isocyanato methyl)-1, 3-dithiolane (4, 5-bis (isocyanato methyl)-1, 3-dithiolane), 4, 5-bis-(isocyanato methyl)-2-methyl isophthalic acid, 3-dithiolane (4, 5-bis (isocyanato methyl)-2-methyl-1, the sulfur heterocyclic ring isocyanate compound (sulfur heterocyclic isocyanate compounds) such as 3-dithiolane).Can also use the chlorine substitution product (substitution product) of these compounds, the halogen family substitution products such as bromine substitution product, alkyl substitution product (alkyl substitution product), alkoxyl group substitution product (alkoxy substitution product), nitro substitution product (nitro substitution product) or with prepolymer (prepolymer) the type denatured products (denaturant) of multivalence alcohol or mercaptan, carbodiimide (carbodiimide) denatured products, urea (urea) denatured products, biuret (biuret) denatured products or dipolymer (dimer) are changed or trimer (trimer) is changed resultant of reaction etc.Preferably use and be selected from isophorone diisocyanate, hexamethylene diisocyanate, the more than a kind of cyclohexyl diisocyanate as polyisocyanate compounds.
Described polymer composition, in order to improve the optics physical property of optical material, to regulate impact resistance, proportion and monomer (monomer) viscosity etc. as object, can additionally add olefin(e) compound as modifier.Can be used as alkene (olefin) compound that reaction resin properties-correcting agent adds, such as there being vinylformic acid benzyl ester (benzylacrylate), benzyl methacrylate (benzylmethacrylate), butoxy ethyl group CALCIUM ACRYLATE (butoxy ethylacrylate), butoxymethyl methacrylate (butoxy methyl methacrylate), cyclohexyl CALCIUM ACRYLATE (cyclo hexyl acrylate), cyclohexyl methyl CALCIUM ACRYLATE (cyclo hexyl methacrylate), 2-hydroxyl ethane base CALCIUM ACRYLATE (2-hydroxyl ethylacrylate), 2-methylol methacrylate (2-hydroxyl methyl methacrylate), epoxypropyl CALCIUM ACRYLATE (glycidyl acrylate), epoxypropyl methacrylate (glycidyl methacrylate), phenoxy group ethyl group CALCIUM ACRYLATE (phenoxy ethylacrylate), phenoxy group ethyl group methacrylate (phenoxy ethylmethacrylate), phenyl methyl CALCIUM ACRYLATE (phenylmethacrylate), ethylene glycol diacrylate fat (ethylene glycol diacrylate), ethylene glycol dimethacrylate fat (ethylene glycol dimethacrylate), divinyl ethylene glycol bisthioglycolate CALCIUM ACRYLATE (diethylene glycol diacrylate), divinyl ethyleneglycol dimethacrylate fat (diethylene glycol dimethacrylate), tri-ethylene glycol diacrylate fat (triethylene glycol diacrylate), tri-ethylene glycol dimethacrylate fat (triethylene glycol dimethacrylate), tetrem allyl diglycol diacrylate fat (tetra ethylene glycol diacrylate), tetrem allyl diglycol dimethacrylate fat (tetra ethylene glycol dimethacrylate), polyethylene glycol diacrylate fat (polyethylene glycol diacrylate), polyethylene glycol dimethacrylate fat (polyethylene glycol dimethacrylate), neo-pentyl ethylene glycol bisthioglycolate CALCIUM ACRYLATE (neopentyl glycol diacrylate), neo-pentyl ethyleneglycol dimethacrylate fat (neopentyl glycol dimethacrylate), ethylene glycol diepoxy propyl group CALCIUM ACRYLATE (ethylene glycol bisglycidyl acrylate), ethylene glycol diepoxy propyl methyl acid fat (ethylene glycol bisglycidyl methacrylate), biphenol A diacrylate fat (bisphenol A diacrylate), biphenol A dimethacrylate fat (bisphenol A dimethacrylate), 2, 2-bis-(4-allyl oxygen ethoxyl phenenyl) propane (2, 2-bis (4-acryloxy ethoxy phenyl) propane), 2, 2-bis-(4-methyl allyl oxygen ethoxyl phenenyl) propane (2, 2-bis (4-methacryloxy ethoxy phenyl) propane), 2, 2-bis-(4-allyl oxygen diethoxy phenyl) propane (2, 2-bis (4-acryloxy diethoxy phenyl) propane), 2, 2-bis-(4-methyl ethoxy diethoxy phenyl) propane (2, 2-bis (4-methacryloxydiethoxy phenyl) propane), biphenol F diacrylate fat (bisphenol F diacrylate), biphenol F dimethacrylate fat (bisphenol F dimethacrylate), 1, 1-bis-(4-allyl oxygen ethoxyl phenenyl) methane (1, 1-bis (4-acryloxy ethoxy phenyl) methane), 1, 1-bis-(4-methyl allyl oxygen ethoxyl phenenyl) methane (1, 1-bis (4-methacryloxy ethoxy phenyl) methane), 1, 1-bis-(4-allyl oxygen diethoxy phenyl) methane (1, 1-bis (4-acryloxy diethoxy phenyl) methane), 1, 1-bis-(4-methyl ethoxy diethoxy phenyl) methane (1, 1-bis (4-methacryloxydiethoxy phenyl) methane), dihydroxymethyl three tristane diacrylate fat (dimethylol tricyclo decane diacrylate), trimethylolpropane triacrylate (trimethylol propane triacrylate), trimethylol propane trimethyl CALCIUM ACRYLATE (trimethylol propane trimethacrylate), glycerol diacrylate fat (glycerol diacrylate), glycerol dimethacrylate fat (glycerol dimethacrylate), five erythritol three CALCIUM ACRYLATE (Penta erythritol triacrylate), five erythritol tetrapropylene acid fat (Penta erythritol tetra acrylate), five erythritol tetramethyl-CALCIUM ACRYLATE (Penta erythritol tetra methacrylate), methyl sulfo-CALCIUM ACRYLATE (methyl thio acrylate), methylthiomethyl CALCIUM ACRYLATE (methyl thio methacrylate), phenyl sulfo-CALCIUM ACRYLATE (phenylthio acrylate), dibenzylsulfide is for methacrylate (benzylthio methacrylate), xylylene two mercaptan diacrylate fat (xylylene dithiol diacrylate), xylylene two mercaptan dimethacrylate fat (xylylene dithiol dimethacrylate), ethane thiol base sulfide diacrylate fat (mercapto ethylsulfide diacrylate), (methyl) CALCIUM ACRYLATE ((meth) acrylate) compounds such as ethane thiol base sulfide dimethacrylate fat (mercapto ethylsulfide dimethacrylate) and, allyl group glycidyl ethers (allyl glycidyl ether), diallyl phthalate (diallyl phthalate), diallyl terephthalic acid's ester (diallyl terephthalate), diallyl isophthalic ester (diallyl isophthalate), diallyl carbonic ether (diallyl carbonate), allyl group (allyl) compounds such as divinyl ethylene glycol bisthioglycolate allyl carbonate (diethylene glycol bisallyl carbonate), vinylbenzene (styrene), chloro-styrene (chlorostyrene), vinyl toluene (methyl styrene), bromostyrene (bromostyrene), dibromo-benzene ethene (dibromostyrene), Vinylstyrene (divinyl benzene), 3, 9-divinyl spiral shell two (methyl-diepoxide for example) (3, 9-divinyl Spiro bi (meth-dioxane)) etc. vinyl (vinyl) compound, but spendable compound is not limited to the compound of example above.These alkene (olefin) compound can separately or mix two or more use.
In addition, polymer composition of the present invention is by known forming method, can comprise various additives, such as various additives such as chainextender (chain extender), linking agent (cross linking agent), polymerization starter (polymerization initiator), internal mold release, photostabilizer, thermo-stabilizer, oxidation inhibitor, UV light absorber, painted preventing agent, pigment dyestuff, mineral dye, weighting agent, binding property tougheners.
Can separately or mix two or more as internal mold release and use phosphate compound, silica gel series interfacial agent, fluorine series interfacial agent, internal mold release preferably, with respect to the weight of polymer composition, contains 0.001～10 % by weight.Preferably use phosphate compound as internal mold release.Phosphate compound passes through to Vanadium Pentoxide in FLAKES (P 2o 5) add the alkylol cpd manufacture of 2～3 moles.Here by the alcohol kind using, can obtain various ways phosphate compound.Representational oriented fatty alcohol adds oxyethane or propylene oxide, or adds the kind of oxyethane or propylene oxide to nonylphenol (nonylphenol) base etc.When polymerizability synthetics of the present invention uses as internal mold release the phosphate compound that adds oxyethane or propylene oxide, can obtain the optical material that release property is good, of fine qualities.The phosphate compound using as internal mold release preferably (adds 5 % by weight of 5 moles, oxyethane from polyoxyethylene nonylphenol ether phosphate (poly oxy ethylene nonyl phenol ether phosphate), add 80 % by weight of 4 moles, add 10 % by weight of 3 moles, add 5 % by weight of 1 mole), polyoxyethylene nonylphenol ether phosphate (adds 3 % by weight of 9 moles, oxyethane, add 80 % by weight of 8 moles, add 5 % by weight of 9 moles, add 6 % by weight of 7 moles, add 6 % by weight of 6 moles), polyoxyethylene nonylphenol ether phosphate (adds 3 % by weight of 13 moles, oxyethane, add 80 % by weight of 12 moles, add 8 % by weight of 11 moles, add 3 % by weight of 9 moles, add 6 % by weight of 4 moles), polyoxyethylene nonylphenol ether phosphate (adds 3 % by weight of 17 moles, oxyethane, add 79 % by weight of 16 moles, add 10 % by weight of 15 moles, add 4 % by weight of 14 moles, add 4 % by weight of 13 moles), polyoxyethylene nonylphenol ether phosphate (adds 5 % by weight of 21 moles, oxyethane, add 76 % by weight of 20 moles, add 7 % by weight of 19 moles, add 6 % by weight of 18 moles, add 4 % by weight of 17 moles) etc. be added with in the phosphate compound of oxyethane or propylene oxide and select one kind or two or more use.
UV light absorber, with respect to whole monomer weight, is added 0.005～6 % by weight (50～60,000ppm), preferably adds 0.01～3 % by weight (100～30,000ppm).When addition less than 0.005 % by weight of UV light absorber, be difficult to obtain effective UV absorbing properties, when eyeglass exposes ultraviolet ray, flavescence problem is very serious.In addition, content is 6 % by weight when above, be difficult to be dissolved in synthetics, and it is bad in process of setting, can to cause a lot of polymerizations.As UV light absorber, can unrestrictedly use the known UV light absorber that can use at glasses lens.Such as, can separately or mix two or more and use 2-(2'-hydroxy-5-methyl base phenyl)-2H-benzotriazole (2-(2'-hydroxyl-5-methyl phenyl)-2H-Benzotriazol); 2-(2'-hydroxyl-3', 5'-bis--t-butyl phenyl) the chloro-2H-benzotriazole of-5-(2-(2'-hydroxyl-3', 5'-di-t-butyl phenyl)-5-chloro-2H-Benzotriazol); 2-(2'-hydroxyl-3'-t-butyl-5'-aminomethyl phenyl) the chloro-2H-benzotriazole of-5-(2-(2'-hydroxyl-3'-t-butyl-5'-methyl phenyl)-5-chloro-2H-Benzotriazol); 2-(2'-hydroxyl-3', 5'-bis--t-amyl group phenyl)-2H-benzotriazole (2-(2'-hydroxyl-3', 5'-di-t-amyl phenyl)-2H-Benzotriazol); 2-(2'-hydroxyl-3', 5'-bis--t-butyl phenyl)-2H-benzotriazole (2-(2'-hydroxyl-3', 5'-di-t-butyl phenyl)-2H-Benzotriazol); 2-(2'-hydroxyl-5'-t-butyl phenyl)-2H-benzotriazole (2-(2'-hydroxyl-5'-t-butyl phenyl)-2H-Benzotriazol); 2-(2'-hydroxyl-5'-t-octyl phenyl)-2H-benzotriazole (2-(2'-hydroxyl-5'-t-octyl phenyl)-2H-Benzotriazol); 2,4-dihydroxy-benzene ketone (2,4-dihydroxyl benzophenone); 2-hydroxyl-4-methoxy benzophenone (2-hydroxyl-4-methoxy benzophenone); The pungent oxygen benzophenone of 2-hydroxyl-4-(2-hydroxyl-4-octyl oxybenzophenone); 4-ten dioxies-2-Viosorb 110 (4-dodecyl oxy-2-hydroxyl benzophenone); 4-benzo oxygen-2-Viosorb 110 (4-benzo oxy-2-hydroxyl benzophenone); 2,2', 4,4'-tetrahydroxy phenol ketone (2,2', 4,4'-tetra hydroxyl benzophenone); 2,2'-dihydroxyl-4,4'-dimethoxy-benzene ketone (2,2'-dihydroxyl-4,4'-dimethoxy benzophenone).Preferably use wavelength field below 400nm to there is good ultraviolet line absorption ability, present 2-(2'-hydroxyl-5'-t-octyl phenyl)-2H-benzotriazole or 2 of excellent dissolution performance with synthetics of the present invention, 2'-dihydroxyl-4,4'-dimethoxy-benzene ketone etc.
Can use known pigment dyestuff as pigment dyestuff.One embodiment of the invention have been used 1-hydroxyl-4-(p-Tolylamine) anthraquinone [1-hydroxy-4-(p-toludine) anthraquinone] of company of Kyung In Synthetic Corp.'s (strain), pyrene ketone dyes (perinone dye) etc.This pigment dyestuff adds 0.5～10,000ppm by every 1kg monomer, and preferably 5～1000ppm, can prevent optical mirror slip flavescence by UV light absorber.
Polymerization starter (catalyzer) plays an important role to sclerosis.The kind of catalyzer is used epoxy curing agent conventionally, but strong amine can allow isocyanic ester vigorous reaction, should add to note when use.The present invention mainly uses Barbiturates, phosphonium salt (phosphonium salt) class, phosphuret-(t)ed hydrogen (phosphine) class of amine and is with the tertiary amine class of electron withdrawing group (electron withdrawing group), Lewis acid (Lewis acid) class, radical initiator (radical initiators) etc., the kind of catalyzer and usage quantity, can suitably be selected by those skilled in the art.Usage quantity, preferably with respect to whole monomer weight, is used 0.001～5 % by weight.
Be to have triethyl-amine (triethylamine) as amine (amine), tripropylamine (tripropyl amine), dipropyl ethyl group amine (dipropyl ethylamine), tributylamine (tributyl amine), three hexyl amines (trihexyl amine), dimethylcyclohexylam,ne (dimethyl cyclo hexyl amine), dicyclohexyl ethyl group amine (dicyclo hexyl ethylamine), thricyclohexyl amine (tricyclo hexyl amine), diethyl alkyl-cyclohexyl amine (diethylcyclo hexyl amine), dicyclohexyl ethyl group amine (dicyclo hexyl ethylamine), dipropyl cyclo-hexylamine (dipropyl cyclo hexyl amine), dicyclohexyl propyl group amine (dicyclo hexyl propyl amine), dibutyl cyclo-hexylamine (dibutyl cyclo hexyl amine), dicyclohexyl butine amine (dicyclo hexyl butyne amine), N, N-dimethyl benzyl amine (N, N-dimethyl benzylamine), N, N-diethyl alkyl benzyl amine (N, N-diethylbenzylamine), N, N-dipropyl benzyl amine (N, N-dipropyl benzylamine), N, N-dibutyl benzyl amine (N, N-dibutyl benzylamine), N-methyl-benzyl amine (N-methyl benzylamine), 2-dimethylaminomethyl phenol (2-dimethyl amino methyl phenol), 2,4,6-tri-(N, N-dimethylaminomethyl) phenol (2,4,6-tris (N, N-dimethyl amino methyl phenol), triethylene diamine (triethylene diamine), TEMED (tetra methyl ethylene diamine), tetrem alkyl ethylene diamine (tetra ethylethylene diamine), N, N-dimethylcyclohexylam,ne (N, N-dimethyl cyclo hexyl amine), N, N-dicyclohexyl methylamine (N, N-dicyclo hexyl methyl amine), tetrapropyl ethylene diamine (tetra propyl ethylene diamine), tetrabutyl ethylene diamine (tetra butyl ethylene diamine), pentamethyl-diethylenetriamine (Penta methyl diethylene triamine), five ethyl group diethylenetriamines (Penta ethyldiethylene triamine), pentapropyl diethylenetriamine (Penta propyl diethylene triamine), five butyl diethylenetriamines (Penta butyl diethylene triamine), N-methyl piperidine (N-methyl piperidine), N-ethyl group piperidines (N-ethylpiperidine), N-propyl group piperidines (N-propyl piperidine), N-butyl piperidine (N-butyl piperidine), N, N-lupetazin (N, N-dimethyl piperazine), N, N-diethyl alkylpiperazine (N, N-diethylpiperazine), N, N-dipropyl piperazine (N, N-dipropyll piperazine), N, N-dibutyl piperazine (N, N-dibutyl piperazine), vulkacit H (hexa methylene tetramine), dimethylamino ethyl group acetic ester (dimethyl amino ethylacetate), diethyl alkylamino ethyl group acetic ester (diethylamino ethylacetate), dimethylaminopropionitrile (dimethyl amino propionitrile), diethyl alkylamino propionitrile (diethylamino propionitrile), N-methyl beautiful jade (N-methyl morpholine), N-ethyl group beautiful jade (N-ethylmorpholine), N-propyl group beautiful jade (N-propyl morpholine), N-butyl beautiful jade (N-butyl morpholine), N-cyclohexyl beautiful jade (N-cyclo hexyl morpholine), N-methylpiperidone (N-methyl piperidone), N-ethyl group piperidone (N-ethylpiperidone), N-propyl group piperidone (N-propyl piperidone), N-butyl piperidine ketone (N-butyl piperidone), N-crassitude (N-methyl pyrrolidine), N-ethyl group tetramethyleneimine (N-ethylpyrrolidine), N-propyl pyrrole alkane (N-propyl pyrrolidine), N-butyl pyrrolidine (N-butyl p yrrolidine), N-Methyl pyrrolidone (N-methyl pyrrolidone), N-ethyl group pyrrolidone (N-ethylpyrrolidone), N-propyl pyrrole alkane ketone (N-propyl pyrrolidone) and N-butyl pyrrolidine ketone (N-butyl pyrrolidone) etc.As aromatic series tertiary amine (tertiary amine), there is DMA (N, N-dimethyl aniline), N, N-diethyl alkyl benzene amine (N, N-diethylaniline), N, N-dipropyl aniline (N, N-dipropyl aniline), N, N-dibutyl aniline (N, N-dibutyl aniline), N, N-cyclohexyl methyl aniline (N, N-cyclo hexyl methyl aniline), N, N-dicyclohexyl aniline (N, N-dicyclo hexyl aniline), diphenyl methyl amine (diphenylmethyl amine), diphenylethane base amine (diphenylethylamine), triphenylamine (triphenylamine), N, N-dimethyl methyl aniline (N, N-dimethyl toluidine), N, N-diethyl alkyl toluene amine (N, N-diethyltoluidine), N-cyclohexyl-N-methyl Tolylamine (N-cyclo hexyl-N-methyl toluidine), N, N-dicyclohexyl Tolylamine (N, N-dicyclo hexyl toluidine), N, N-dimethyl naphthyl amine (N, N-dimethyl naphthyl amine), N, N-diethyl alkyl ALPHA-NAPHTHYL AMINE (N, N-diethyl naphthyl amine), N, N-dimethyl methyl oxyaniline (N, N-dimethyl anisidine), N, N-bis-ethyl group methyl oxyaniline (N, N-diethylanisidine) and N, N, N`, N`-tetramethyl-phenylenediamine (N, N, N`, N`-tetra methyl phenylenediamine) etc.Can use pyridine (pyridine), picoline (picoline), lutidine (dimethyl pyridine), 2,2'-, bis-pyridines (2,2'-bipyridine), 4,4'-, bis-pyridines (4,4'-bipyridine), pyridine (pyrazole), N-methylpyrazole (N-methyl pyrazole), N-ethyl group pyrazoles (N-ethyl pyrazole), N-propyl group pyrazoles (N-propyl pyrazole), N-butyl pyrazoles (N-butyl pyrazole), N-cyclohexyl pyrazoles (N-cyclohexyl pyrazole), pyridazine (pyridazine), pyrimidine (pyrimidine), pyrroline (pyrroline), oxazole (oxazole), thiazole (thiazole), 1-Methylimidazole (1-methyl imidazole), 1-benzyl imidazole (1-benzylimidazole), 1-methyl-glyoxal ethyline (1-methyl-2-methyl imidazole), 1 benzyl 2 methyl imidazole (1-benzyl-2-methyl imidazole), 1-ethyl group-4-methylimidazole (1-ethyl-4-methyl imidazole), 1-ethyl group-2-ethyl group-4-methylol (1-ethyl-2-ethyl-4-methylol), N-methylpyrrole (N-methyl pyrrol), N-ethyl group pyrroles (N-ethylpyrrol), N-butyl pyrroles (N-butyl pyrrol), N-methylpyrroline (N-methyl pyrroline), N-ethyl group pyrroline (N-ethylpyrroline), N-butyl pyrroline (N-butyl pyrroline), pyrimidine (pyrimidine), purine (purine), quinoline (quinoline), isoquinoline 99.9 (isoquinoline), N-methyl carbazole (N-methyl carbazole), N-ethyl group carbazole (N-ethylcarbazole) and N-butyl carbazole (N-butyl carbazole) etc.In addition, as tin based compound, use or use simultaneously separately two or more butyl tin behenic acid ester (butyltin dilaurate); Dibutyl tin dichloride (dibutyltin dichloride); Dibutyl tin diacetate (dibutyltin diacetate); Octyl group acid (octylacid) the 1st tin (tin); Docosoic acid dibutyl tin (dilauric acid dibutyltin); Tetrafluoro is for tin (tetra fluoro tin); Tetrachloro tin (tetra chlorotin); Tetrabromo is for tin (tetra bromotin); The tetraiodo is for tin (tetra iodide tin); Methyl tin trichloride (methyl tin trichloride); Butyl tin trichloride (butyl tin trichloride); Tin methide dichloride (dimethyl tin dichloride); Dibutyl tin dichloride (dibutyl tin dichloride); Tin trimethyl muriate (trimethyl tin chloride); Tributyltin chloride (tributyl tin chloride); Triphenyltin muriate (triphenyltin chloride); Dibutyl tin sulfide (dibutyl tin sulfide); Two (2-ethyl group hexyl) tin-oxide (di (2-ethylhexyltin oxide).
Lewis acid is such as there being the zinc series compounds such as zinc chloride (zinc chloride), zinc acetylacetonate (zinc acetylacetone) and dibutylamino zinc formate (zinc dibuty dicarbamic); The iron such as iron(ic) chloride and ferric acetyl acetonade series compound; The aluminium series compounds such as aluminium, aluminum fluoride, aluminum chloride and triphenyl (triphenyl) aluminium.
Manufacture after polymerizability synthetics with aforesaid method, obtain optical material by injection molding polymerization.Polymer composition is injected between the mould of being sealed by sealing member or adhesive tape, carry out polyreaction.Polymerizing condition is pressed kind and the consumption of polymerizability synthetics, catalyzer, and the shape of mould presents very big difference, does not therefore limit, but at approximately-50～150 DEG C of temperature, carries out through 1～50 hour.Sometimes according to circumstances, under 10～150 DEG C of temperature ranges, maintain or heat up gradually, being hardened to suitable through 1～48 hour.The optical material obtaining by sclerosis, the processing such as can anneal as required.Treatment temp is generally 50～150 DEG C, preferably 90～140 DEG C.
Optical material of the present invention, the mould when changing injection molding polymerization, can obtain the formed body of various shape, can be used as the various optical materials such as glasses lens, camera eyeglass, photodiode (LED) and uses.Especially the optical material, the optical element that are suitable as glasses lens, camera eyeglass, photodiode etc. use.
The optical mirror slip obtaining by the present invention, can form coating as required on two sides.There are priming paint (primer) layer, [Dan, anti-reflection layer, anti-fog layer, anti-contamination layer, waterproof layer as coating.These coatings can be distinguished formation separately, or multilayer forms multiple coatings.While implementing coating on two sides, two sides forms respectively different coatings or identical coating.Optical mirror slip of the present invention can utilize dispersed color or optically variable pigments to carry out using after painted processing.
[embodiment]
For making object, technical scheme and the advantage of the embodiment of the present invention clearer, below in conjunction with the accompanying drawing in the embodiment of the present invention, technical scheme in the embodiment of the present invention is carried out to clear, complete description, obviously, described embodiment is the present invention's part embodiment, instead of whole embodiment.Based on the embodiment in the present invention, those of ordinary skill in the art, not making the every other embodiment obtaining under creative work prerequisite, belong to the scope of protection of the invention.
Physical property experiment method
The optical mirror slip of embodiment being manufactured with following experimental technique detects physical property, and result is as shown in table 1 below.
1) refractive index and Abbe number: used Atago Co., the DR-M4 model Abbe dioptrometer of company.
2) polymerization is inhomogeneous: 100, the eyeglass that obtains by operation of detecting by an unaided eye, as there is more than 3 arteries and veins reason, albefaction, edge bubble,, as do not there is record " 0 " in record " X ".
3) hardening state: do not harden or there is intense reaction, the undesired time record " X " that causes hardening, as harden good, generate colourless solid resin, record " 0 ".
4) glass transition temperature (Tg:glass transition temperature): with the through transmission technique (0.8N heavy burden, needle point 0.5mm Φ, 5 DEG C/min of intensification temperature) of TMAQ400 (TA Instruments), detected TMA in high-purity nitrogen.
1: two (the chloro-2-hydroxypropyl of 3-) sulfide (bis (3-chloro-2-hydroxylpropyl) sulfide) of synthesis example synthetic
Add Epicholorohydrin (epichlorohydrin) (5563g to 10 liters of reactors, 60.12mol) and after methyl alcohol (2500g), temperature of reaction is adjusted to 6 DEG C, in the time that arriving 6 DEG C, temperature of reaction adds caustic soda (caustic soda) (50%aq, 5g).In another 10 liters of reactors, add NaSH.xH 2o (70%NaSH, 3660g, 45.75mol), methyl alcohol (1000g) and water (500g), by stirring after thawing completely, slowly drip hydrochloric acid, the hydrogen sulfide generating is added to Epicholorohydrin solution, obtained two (the chloro-2-hydroxypropyl of 3-) sulfide.The end point of reaction is to confirm end product by GC, Epicholorohydrin and the completely dissolve of 3-chlorine-2-hydroxyl-propyl-1-mercaptan compound, the time point that two (the chloro-2-hydroxypropyl of 3-) sulfide generates.As there is 3-chlorine-2-hydroxyl-propyl-1-mercaptan, and calculate relative content by GC, by adding Epicholorohydrin, react, obtain two (the chloro-2-hydroxypropyl of 3-) sulfide.Resultant has almost obtained 99% above yield, and purity is 95%.
synthetic (pH2.5) of 2: two-(2,3-epithio is for propyl group) sulfide of synthesis example
Add two (the chloro-2-hydroxypropyl of 3-) sulfide (1072.48g, 4.89mol), toluene (toluene) 1300g, methyl alcohol 800g to 10 liters of reaction vessels, stir, temperature of reaction is transferred to 30 DEG C.While arriving 25 DEG C, drip NaOH (50%aq., 783.08g, 9.78mol), temperature of reaction when dropping is carried out at 35～37 DEG C, holding temperature, reacts.Dropping was carried out in 1 hour, under 37 DEG C of conditions, place afterwards fermentation in approximately 30 minutes, after fermentation ends, add toluene 2000g, approximately stir 10 minutes, carry out layering, with water, supernatant liquor organism being carried out to 2 times cleans, remove to greatest extent moisture, to there being which floor organic solution again to add methyl alcohol 400g, stir, at 8 DEG C of temperature of reaction, add thiourea (thiourea) (1117.65g, 14.30mol) and Glacial acetic acid (70g), temperature of reaction is heightened to 18 DEG C, react 18 hours.Reaction end point is confirmed by HPLC, the material hour that sets out, and resultant does not further change and is as the criterion.After reaction finishes, stop stirring, with water clean 3 times by layer separates obtain which floor has, to which floor obtained added 10% sulfuric acid, remove organic solvent, two-(2,3-epithio is for the propyl group) sulfide that acquisition pH is 2.5.Recording refractive index (nD, 20 DEG C) is 1.614.
synthetic (pH3.5) of 3: two-(2,3-epithio is for propyl group) sulfide of synthesis example
Add two (the chloro-2-hydroxypropyl of 3-) sulfide (1072.48g, 4.89mol), toluene (toluene) 1300g, methyl alcohol 800g to 10 liters of reaction vessels, stir, temperature of reaction is transferred to 25 DEG C.While arriving 25 DEG C, drip NaOH (50%aq., 783.08g, 9.78mol), temperature of reaction when dropping is carried out at 35～37 DEG C, holding temperature, reacts.Dropping was carried out in 1 hour, under 37 DEG C of conditions, place afterwards fermentation in approximately 30 minutes, after fermentation ends, add toluene 2000g, approximately stir 10 minutes, carry out layering, with water, supernatant liquor organism being carried out to 2 times cleans, remove to greatest extent moisture, to there being which floor organic solution again to add methyl alcohol 400g, stir, at 8 DEG C of temperature of reaction, add thiourea (thiourea) (1117.65g, 14.30mol) and Glacial acetic acid (70g), temperature of reaction is heightened to 18 DEG C, react 18 hours.Reaction end point is confirmed by HPLC, the material hour that sets out, and resultant does not further change and is as the criterion.After reaction finishes, stop stirring, with water clean 3 times by layer separates obtain which floor has, to which floor obtained added 5% sulfuric acid, remove organic solvent, two-(2,3-epithio is for the propyl group) sulfide that acquisition pH is 3.5.Recording refractive index (nD, 20 DEG C) is 1.614.
synthetic (pH5.0) of 4: two-(2,3-epithio is for propyl group) sulfide of synthesis example
Add two (the chloro-2-hydroxypropyl of 3-) sulfide (1072.48g), toluene (toluene) 1300g, methyl alcohol 800g to 10 liters of reaction vessels, stir, temperature of reaction is transferred to 25 DEG C.While arriving 25 DEG C, drip NaOH (50%aq., 783.08g), temperature of reaction when dropping maintains 37 DEG C, reacts.Dropping was carried out in 1 hour, under 37 DEG C of conditions, place afterwards fermentation in approximately 30 minutes, after fermentation ends, add toluene 2000g, approximately stir 30 minutes, carry out layering, with in 1g hydrochloric acid soln and supernatant liquor organic solution, remove to greatest extent moisture, again add methyl alcohol 400g, stir to there being which floor organic solution, at 8 DEG C of temperature of reaction, add thiourea (thiourea) (1117.65g) and Glacial acetic acid (70g), temperature of reaction is heightened to 16.5 DEG C, react 24 hours.Reaction end point is confirmed by HPLC, the material hour that sets out, and resultant does not further change and is as the criterion.After reaction finishes, stop stirring, with water clean 3 times by layer separates obtain which floor has, to which floor obtained added 0.1% sulfuric acid, clean, remove organic solvent, two-(2,3-epithio is for the propyl group) sulfide that acquisition pH is 5.0.Recording refractive index (nD, 20 DEG C) is 1.614.
synthetic (pH7.0) of 5: two-(2,3-epithio is for propyl group) sulfide of synthesis example
Add two (the chloro-2-hydroxypropyl of 3-) sulfide (1072.48g), toluene (toluene) 1300g, methyl alcohol 800g to 10 liters of reaction vessels, stir, temperature of reaction is transferred to 25 DEG C.While arriving 25 DEG C, drip NaOH (50%aq., 783.08g), temperature of reaction when dropping maintains 37 DEG C, reacts.Dropping was carried out in 1 hour, under 37 DEG C of conditions, place afterwards fermentation in approximately 30 minutes, after fermentation ends, add toluene 2000g, approximately stir 30 minutes, carry out layering, with in 1g hydrochloric acid soln and supernatant liquor organic solution, remove to greatest extent moisture, again add methyl alcohol 400g, stir to there being which floor organic solution, at 8 DEG C of temperature of reaction, add thiourea (thiourea) (1117.65g) and Glacial acetic acid (70g), temperature of reaction is heightened to 16.5 DEG C, react 24 hours.Reaction end point is confirmed by HPLC, the material hour that sets out, and resultant does not further change and is as the criterion.After reaction finishes, stop stirring, what obtain with the separation of water cleaning Multiple through then out layer has which floor, removes organic solvent, two-(2,3-epithio is for the propyl group) sulfide that acquisition pH is 7.0.Recording refractive index (nD, 20 DEG C) is 1.614.
synthetic (pH8.0) of 6: two-(2,3-epithio is for propyl group) sulfide of synthesis example
Add two (the chloro-2-hydroxypropyl of 3-) sulfide (1072.48g), toluene (toluene) 1300g, methyl alcohol 800g to 10 liters of reaction vessels, stir, temperature of reaction is transferred to 25 DEG C.While arriving 25 DEG C, drip NaOH (50%aq., 783.08g), temperature of reaction when dropping maintains 37 DEG C, reacts.Dropping was carried out in 1 hour, under 37 DEG C of conditions, place afterwards fermentation in approximately 30 minutes, after fermentation ends, add toluene 2000g, approximately stir 30 minutes, carry out layering, with in 1g hydrochloric acid soln and supernatant liquor organic solution, remove to greatest extent moisture, again add methyl alcohol 400g, stir to there being which floor organic solution, at 8 DEG C of temperature of reaction, add thiourea (thiourea) (1117.65g) and Glacial acetic acid (70g), temperature of reaction is heightened to 16.5 DEG C, react 24 hours.Reaction end point is confirmed by HPLC, the material hour that sets out, and resultant does not further change and is as the criterion.After reaction finishes, stop stirring, with water clean 3 times by layer separates obtain which floor has, which floor has add 0.1% ammoniacal liquor to what obtain, clean, remove organic solvent, acquisition pH two-(2,3-epithio is for the propyl group) sulfide that are 8.0.Recording refractive index (nD, 20 DEG C) is 1.614.
synthetic (pH10.0) of 7: two-(2,3-epithio is for propyl group) sulfide of synthesis example
Add two (the chloro-2-hydroxypropyl of 3-) sulfide (1072.48g), toluene (toluene) 1300g, methyl alcohol 800g to 10 liters of reaction vessels, stir, temperature of reaction is transferred to 25 DEG C.While arriving 25 DEG C, drip NaOH (50%aq., 783.08g), temperature of reaction when dropping maintains 37 DEG C, reacts.Dropping was carried out in 1 hour, under 37 DEG C of conditions, place afterwards fermentation in approximately 30 minutes, after fermentation ends, add toluene 2000g, approximately stir 30 minutes, carry out layering, with in 1g hydrochloric acid soln and supernatant liquor organic solution, remove to greatest extent moisture, again add methyl alcohol 400g, stir to there being which floor organic solution, at 8 DEG C of temperature of reaction, add thiourea (thiourea) (1117.65g) and Glacial acetic acid (70g), temperature of reaction is heightened to 16.5 DEG C, react 24 hours.Reaction end point is confirmed by HPLC, the material hour that sets out, and resultant does not further change and is as the criterion.After reaction finishes, stop stirring, with water clean 3 times by layer separates obtain which floor has, which floor has add 0.1% ammoniacal liquor to what obtain, remove organic solvent, acquisition pH two-(2,3-epithio is for the propyl group) sulfide that are 10.0.Recording refractive index (nD, 20 DEG C) is 1.614.
embodiment 1
The pH obtaining to synthesis example 5 be 7.0 two-(2,3-epithio is for propyl group) sulfide 100g, add internal mold release 8-PENPP0.01g, UV light absorber HOPBT1.0g, polymerization starter TBPB0.4g, pigment dyestuff HTAQ (20ppm) and PRD (10ppm), be uniformly mixed at 20 DEG C, obtained homogeneous solution.To this mixing solutions, with 400Pa condition, carry out deaeration in 1 hour.Afterwards, filter by 1 μ m PTFE strainer processed, be injected in the mould being formed by glass template and adhesive tape.This mould is put into polymerization baking box, under 30 DEG C of conditions 8 hours, with 30～100 DEG C of temperature, slowly heated up through 15 hours, carry out polymerization.After polymerization finishes, take out mould from baking box.The release property of mould presents well.The resin obtaining is carried out to 2 hours anneal at 110 DEG C.The physical property obtaining is refractive index (nE) 1.702, Abbe number 34.5,95 DEG C of thermotolerances (Tg).The solution state that injects mould is observed by naked eyes, after the demoulding, confirmed foreign matter, no abnormal, do not occur albefaction and arteries and veins reason.
embodiment 2～3
With the method identical with embodiment 1, the various proportionings of recording by table 1 are manufactured respectively after each synthetics and wafer, and its evaluation result is recorded in to table 1.
comparative example 1
The pH obtaining to synthesis example 2 be 2.5 two-(2,3-epithio is for propyl group) sulfide 100g, add internal mold release 8-PENPP0.01g, UV light absorber HOPBT1.0g, polymerization starter TBPB0.4g, pigment dyestuff HTAQ (20ppm) and PRD (10ppm), be uniformly mixed at 20 DEG C, obtained homogeneous solution.To this mixing solutions, with 400Pa condition, carry out deaeration in 1 hour.Afterwards, filter by 1 μ m PTFE strainer processed, be injected in the mould being formed by glass template and adhesive tape.This mould is put into polymerization baking box, under 30 DEG C of conditions 8 hours, with 30～100 DEG C of temperature, slowly heated up through 15 hours, carry out polymerization.But resin composition hardens, but its colour changed into yellow.
comparative example 2～3
With the method identical with comparative example 1, hardening resin synthetics, obtain data logging at table 1.
[abbreviation]
EPS: two (2,3-epithio is for propyl group) sulfide (bis (2,3-epithiopropyl) sulfide)
8-PENPP: polyoxyethylene nonylphenol ether phosphate (polyoxyethylenenonylphenoletherphosphate)
HOPBT:2-(2'-hydroxyl-5'-t-octyl phenyl)-2H-benzotriazole (2-(2'-hydroxy-5'-t-octylphenyl)-2H-benzotriazole)
TBPB: tetrabutyl phosphonium bromide phosphorus (tetrabutylphosphonium bromide)
HTQA:1-hydroxyl-4-(p-Tolylamine)-anthraquinone (1-hydroxy-4-(p-toluidine) anthraquinone
PRD: pyrene ketone dyes (perinone dye)
Industry is utilized feasibility
The present invention can avoid unhardened and polymerization is inhomogeneous, easily the good sulfo-epoxy base system optical material of quality bills of materials.The sulfo-epoxy base system optical material of manufacture of the present invention can replace existing optical material, is widely used in various fields.Particularly, can be used for plastic eyeglass lens, the 3D polarized lenses that light polarizing film is manufactured is installed on glasses lens, and camera eyeglass etc., in addition can also be used in the multiple optical articles such as recording medium substrate or painted strainer and ultraviolet radiation absorption strainer such as bevelled mirror, fiber optics, CD.

Claims (14)

1. a sulfo-epoxy base system optical material manufacture method, is characterized in that: comprise
Contain the polymerizability synthetics manufacturing stage of the sulfo-epoxy compounds of pH4～8,
In the stage of described polymerizability synthetics injection molding polymerization.
2. sulfo-epoxy base system optical material manufacture method according to claim 1, is characterized in that:
Described sulfo-epoxy compounds is to be selected from two-(2, 3-epithio is for propyl group) sulfide (bis-(2, 3-epithiopropyl) sulfide), two-(2, 3-epithio is for propyl group) disulphide (bis-(2, 3-epithiopropyl) disulfide), 1, 3-and 1, 4-bis-(β-epithio is for propyl dithiocarbamate) hexanaphthene), 1, 3-and 1, 4-bis-(β-epithio is for propyl dithiocarbamate methyl) hexanaphthene), 2, 5-bis-(β-epithio is for propyl dithiocarbamate methyl)-1, 4-dithiane, 2, 5-bis-(β-epithio is for propyl dithiocarbamate ethylenebis dithiocarbamate methyl)-1, 4-dithiane, 2-(2-β-epithio is for propyl dithiocarbamate ethylenebis dithiocarbamate)-1, the one kind or two or more compound of 3-bis-(β-epithio is for propyl dithiocarbamate) propane.
3. sulfo-epoxy base system optical material manufacture method according to claim 1, is characterized in that:
Described polymerizability synthetics also comprises poly-thiol compound.
4. sulfo-epoxy base system optical material manufacture method according to claim 3, is characterized in that:
Described polymerizability synthetics also comprises polyisocyanate compounds.
5. according to a certain described sulfo-epoxy base system optical material manufacture method in claim 1 to 4, it is characterized in that:
Described polymerizability synthetics also comprises olefin(e) compound as reaction resin properties-correcting agent.
6. according to a certain described sulfo-epoxy base system optical material manufacture method in claim 1 to 4, it is characterized in that:
Described polymerizability synthetics also comprises phosphate compound as internal mold release.
7. sulfo-epoxy base system optical material manufacture method according to claim 6, is characterized in that:
Described phosphate compound is to be selected from polyoxyethylene nonylphenol ether phosphate (poly oxy ethylene nonyl phenol ether phosphate) (to add 5 % by weight of 5 moles, oxyethane, add 80 % by weight of 4 moles, add 10 % by weight of 3 moles, add 5 % by weight of 1 mole), polyoxyethylene nonylphenol ether phosphate (adds 3 % by weight of 9 moles, oxyethane, add 80 % by weight of 8 moles, add 5 % by weight of 9 moles, add 6 % by weight of 7 moles, add 6 % by weight of 6 moles), polyoxyethylene nonylphenol ether phosphate (adds 3 % by weight of 13 moles, oxyethane, add 80 % by weight of 12 moles, add 8 % by weight of 11 moles, add 3 % by weight of 9 moles, add 6 % by weight of 4 moles), polyoxyethylene nonylphenol ether phosphate (adds 3 % by weight of 17 moles, oxyethane, add 79 % by weight of 16 moles, add 10 % by weight of 15 moles, add 4 % by weight of 14 moles, add 4 % by weight of 13 moles), polyoxyethylene nonylphenol ether phosphate (adds 5 % by weight of 21 moles, oxyethane, add 76 % by weight of 20 moles, add 7 % by weight of 19 moles, add 6 % by weight of 18 moles, add 4 % by weight of 17 moles), and Zelec UN tMone kind or two or more compound.
8. an optical material polymerizability synthetics, is characterized in that:
Comprise the sulfo-epoxy compounds of pH4～8.
9. optical material according to claim 8 polymerizability synthetics, is characterized in that:
Also comprise poly-thiol compound.
10. optical material according to claim 9 polymerizability synthetics, is characterized in that:
Also comprise polyisocyanate compounds.
A certain described optical material polymerizability synthetics in 11. according to Claim 8 to 10, is characterized in that:
Comprise phosphate compound as internal mold release.
12. 1 kinds of optical materials, is characterized in that:
Obtain with polymerizability synthetics by a certain optical material in heat embrittlement claim 8 to 10.
13. 1 kinds of optical mirror slips, is characterized in that:
Formed by optical material described in claim 12.
14. optical mirror slips according to claim 13, is characterized in that:
Described optical mirror slip is glasses lens or polarized lenses.
CN201280063547.5A 2011-12-21 2012-12-20 Sulfur-bearing is for optical material polymer composition and the optical material manufacture method of epoxy radicals (thioepoxy) compound Expired - Fee Related CN104024300B (en)

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