KR100477182B1 - Resin compositions, and optical lens prepared by them - Google Patents
Resin compositions, and optical lens prepared by them Download PDFInfo
- Publication number
- KR100477182B1 KR100477182B1 KR10-2002-0029174A KR20020029174A KR100477182B1 KR 100477182 B1 KR100477182 B1 KR 100477182B1 KR 20020029174 A KR20020029174 A KR 20020029174A KR 100477182 B1 KR100477182 B1 KR 100477182B1
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- South Korea
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- formula
- meth
- acrylate
- weight
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- 230000003287 optical effect Effects 0.000 title claims abstract description 27
- 239000011342 resin composition Substances 0.000 title claims abstract description 23
- -1 acrylate compound Chemical class 0.000 claims abstract description 32
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical group C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims abstract description 11
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 6
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 4
- 150000001334 alicyclic compounds Chemical class 0.000 claims abstract description 4
- 150000007824 aliphatic compounds Chemical class 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 4
- 229920006295 polythiol Polymers 0.000 claims abstract description 4
- 239000011593 sulfur Substances 0.000 claims abstract description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 16
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 14
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 12
- 125000004386 diacrylate group Chemical group 0.000 claims description 12
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 claims description 9
- 229940117927 ethylene oxide Drugs 0.000 claims description 9
- CNDCQWGRLNGNNO-UHFFFAOYSA-N 2-(2-sulfanylethoxy)ethanethiol Chemical compound SCCOCCS CNDCQWGRLNGNNO-UHFFFAOYSA-N 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- RHOOUTWPJJQGSK-UHFFFAOYSA-N 2-phenylsulfanylethyl prop-2-enoate Chemical compound C=CC(=O)OCCSC1=CC=CC=C1 RHOOUTWPJJQGSK-UHFFFAOYSA-N 0.000 claims description 7
- WYNSMHOXQPGMDT-UHFFFAOYSA-N 2-hexylsulfanylethyl 2-methylprop-2-enoate Chemical compound CCCCCCSCCOC(=O)C(C)=C WYNSMHOXQPGMDT-UHFFFAOYSA-N 0.000 claims description 4
- 125000002723 alicyclic group Chemical group 0.000 claims description 4
- JHWGFJBTMHEZME-UHFFFAOYSA-N 4-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OCCCCOC(=O)C=C JHWGFJBTMHEZME-UHFFFAOYSA-N 0.000 claims description 3
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 claims description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- VBJHDYCFGAXWDN-UHFFFAOYSA-N decane prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.CCCCCCCCCC VBJHDYCFGAXWDN-UHFFFAOYSA-N 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 claims description 3
- PRJNEUBECVAVAG-UHFFFAOYSA-N 1,3-bis(ethenyl)benzene Chemical compound C=CC1=CC=CC(C=C)=C1 PRJNEUBECVAVAG-UHFFFAOYSA-N 0.000 claims description 2
- IBVPVTPPYGGAEL-UHFFFAOYSA-N 1,3-bis(prop-1-en-2-yl)benzene Chemical compound CC(=C)C1=CC=CC(C(C)=C)=C1 IBVPVTPPYGGAEL-UHFFFAOYSA-N 0.000 claims description 2
- WEERVPDNCOGWJF-UHFFFAOYSA-N 1,4-bis(ethenyl)benzene Chemical compound C=CC1=CC=C(C=C)C=C1 WEERVPDNCOGWJF-UHFFFAOYSA-N 0.000 claims description 2
- ZENYUPUKNXGVDY-UHFFFAOYSA-N 1,4-bis(prop-1-en-2-yl)benzene Chemical compound CC(=C)C1=CC=C(C(C)=C)C=C1 ZENYUPUKNXGVDY-UHFFFAOYSA-N 0.000 claims description 2
- CYLVUSZHVURAOY-UHFFFAOYSA-N 2,2-dibromoethenylbenzene Chemical compound BrC(Br)=CC1=CC=CC=C1 CYLVUSZHVURAOY-UHFFFAOYSA-N 0.000 claims description 2
- CISIJYCKDJSTMX-UHFFFAOYSA-N 2,2-dichloroethenylbenzene Chemical compound ClC(Cl)=CC1=CC=CC=C1 CISIJYCKDJSTMX-UHFFFAOYSA-N 0.000 claims description 2
- LSWYGACWGAICNM-UHFFFAOYSA-N 2-(prop-2-enoxymethyl)oxirane Chemical compound C=CCOCC1CO1 LSWYGACWGAICNM-UHFFFAOYSA-N 0.000 claims description 2
- SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical compound ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 claims description 2
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 claims description 2
- YMOONIIMQBGTDU-VOTSOKGWSA-N [(e)-2-bromoethenyl]benzene Chemical compound Br\C=C\C1=CC=CC=C1 YMOONIIMQBGTDU-VOTSOKGWSA-N 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000011521 glass Substances 0.000 description 9
- 239000004033 plastic Substances 0.000 description 9
- 229920003023 plastic Polymers 0.000 description 9
- 239000011347 resin Substances 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 7
- 238000011282 treatment Methods 0.000 description 6
- 238000004043 dyeing Methods 0.000 description 5
- 230000005484 gravity Effects 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 238000007342 radical addition reaction Methods 0.000 description 3
- KDGNCLDCOVTOCS-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy propan-2-yl carbonate Chemical compound CC(C)OC(=O)OOC(C)(C)C KDGNCLDCOVTOCS-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- 238000007259 addition reaction Methods 0.000 description 2
- 238000000137 annealing Methods 0.000 description 2
- SYFOAKAXGNMQAX-UHFFFAOYSA-N bis(prop-2-enyl) carbonate;2-(2-hydroxyethoxy)ethanol Chemical compound OCCOCCO.C=CCOC(=O)OCC=C SYFOAKAXGNMQAX-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 238000005498 polishing Methods 0.000 description 2
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 2
- 239000007870 radical polymerization initiator Substances 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- 150000003440 styrenes Chemical class 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- ZODNDDPVCIAZIQ-UHFFFAOYSA-N (2-hydroxy-3-prop-2-enoyloxypropyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)COC(=O)C=C ZODNDDPVCIAZIQ-UHFFFAOYSA-N 0.000 description 1
- OXYKVVLTXXXVRT-UHFFFAOYSA-N (4-chlorobenzoyl) 4-chlorobenzenecarboperoxoate Chemical compound C1=CC(Cl)=CC=C1C(=O)OOC(=O)C1=CC=C(Cl)C=C1 OXYKVVLTXXXVRT-UHFFFAOYSA-N 0.000 description 1
- NOBYOEQUFMGXBP-UHFFFAOYSA-N (4-tert-butylcyclohexyl) (4-tert-butylcyclohexyl)oxycarbonyloxy carbonate Chemical compound C1CC(C(C)(C)C)CCC1OC(=O)OOC(=O)OC1CCC(C(C)(C)C)CC1 NOBYOEQUFMGXBP-UHFFFAOYSA-N 0.000 description 1
- HIACAHMKXQESOV-UHFFFAOYSA-N 1,2-bis(prop-1-en-2-yl)benzene Chemical compound CC(=C)C1=CC=CC=C1C(C)=C HIACAHMKXQESOV-UHFFFAOYSA-N 0.000 description 1
- AHWAAQOJHMFNIV-UHFFFAOYSA-N 2-tert-butylperoxy-2-ethylhexanoic acid Chemical compound CCCCC(CC)(C(O)=O)OOC(C)(C)C AHWAAQOJHMFNIV-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- KRIUARSVMCZLRE-UHFFFAOYSA-N C(C=C)(=O)O.C1(=CC=CC=C1)SCCCC Chemical compound C(C=C)(=O)O.C1(=CC=CC=C1)SCCCC KRIUARSVMCZLRE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004641 Diallyl-phthalate Substances 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- FHLPGTXWCFQMIU-UHFFFAOYSA-N [4-[2-(4-prop-2-enoyloxyphenyl)propan-2-yl]phenyl] prop-2-enoate Chemical compound C=1C=C(OC(=O)C=C)C=CC=1C(C)(C)C1=CC=C(OC(=O)C=C)C=C1 FHLPGTXWCFQMIU-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000002390 adhesive tape Substances 0.000 description 1
- 239000006117 anti-reflective coating Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 230000009545 invasion Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 230000003863 physical function Effects 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- BWJUFXUULUEGMA-UHFFFAOYSA-N propan-2-yl propan-2-yloxycarbonyloxy carbonate Chemical compound CC(C)OC(=O)OOC(=O)OC(C)C BWJUFXUULUEGMA-UHFFFAOYSA-N 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/38—Esters containing sulfur
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/37—Thiols
- C08K5/372—Sulfides, e.g. R-(S)x-R'
-
- 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
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B7/00—Mountings, adjusting means, or light-tight connections, for optical elements
- G02B7/02—Mountings, adjusting means, or light-tight connections, for optical elements for lenses
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
본 발명은 광학용 수지 조성물에 관한 것으로, (A) 화학식 1로 표시되는 비스페놀 A 골격을 갖는 (메타)아크릴레이트 화합물 10~75 중량부, (B) 화학식 2로 표시되는 지방족 폴리티올 화합물 1~70 중량부, (C) 화학식 3으로 표시되는 황을 함유하는 (메타)아크릴레이트 화합물 1~40 중량부, 및 (D) 화학식 4로 표시되는 지방족 또는 지환족을 가지는 (메타)아크릴레이트 화합물 1~45 중량부를 포함한다.The present invention relates to an optical resin composition, wherein (A) 10 to 75 parts by weight of a (meth) acrylate compound having a bisphenol A skeleton represented by the formula (1), and (B) an aliphatic polythiol compound represented by the formula (2) 1 to 40 parts by weight of a (meth) acrylate compound containing 70 parts by weight, (C) sulfur represented by the formula (3), and (D) an (meth) acrylate compound having an aliphatic or alicyclic compound represented by the formula (4) And ˜45 parts by weight.
또한 본 발명은 수지 조성물을 중합 및 경화시켜 고굴절률, 고아베수, 투명성, 광학적 균일성 및 경량성이 우수한 광학 렌즈를 제공한다.The present invention also polymerizes and hardens the resin composition to provide an optical lens having excellent high refractive index, high Abbe number, transparency, optical uniformity and light weight.
Description
본 발명은 수지 조성물 및 그 조성물을 중합 및 경화시켜 제조된 광학 렌즈에 관한 것이다.The present invention relates to a resin composition and an optical lens produced by polymerizing and curing the composition.
플라스틱 렌즈는 무기 유리렌즈에 비하여 가볍고, 잘 부서지지 않으며 쉽게 착색되므로 광학 기구에서 광범위하게 사용되고 있다.Plastic lenses are widely used in optical instruments because they are lighter, less brittle, and easier to color than inorganic glass lenses.
플라스틱 렌즈의 원료로 사용되는 수지 가운데 디에틸렌글리콜비스알릴카르보네이트는 비중(1.32)이 무기 유리렌즈의 비중(2.54)보다 작으므로, 렌즈의 무게를 크게 감소시킬 수 있는 장점이 있다. 그러나, 이러한 수지에 의해 만들어진 렌즈는 무기 유리렌즈의 굴절률(n D 20=1.52)보다 굴절률(n D 20=1.50)이 작으므로, 무기 유리렌즈와 비교하여 중앙두께, 주변두께가 지나치게 두껍게 되는 단점이 있다.Among the resins used as raw materials for the plastic lens, diethylene glycol bisallylcarbonate has a specific gravity (1.32) smaller than the specific gravity (2.54) of the inorganic glass lens, so that the weight of the lens can be greatly reduced. However, the lens made by such a resin has a smaller refractive index ( n D 20 = 1.50) than the refractive index of the inorganic glass lens ( n D 20 = 1.52), so that the center thickness and the peripheral thickness become too thick as compared with the inorganic glass lens. There is this.
고굴절율을 갖는 플라스틱 렌즈의 원료로 사용되는 수지 가운데 폴리카르보네이트(n 20 D=1.58) 및 폴리스티렌(n D 20=1.60)은 불충분한 연마 가공성, 불충분한 표면 경도에 기인하는 저내소성(抵耐搔性, low scratch resistance) 및 유기용매에 대한 낮은 내성 때문에, 광학분야에서 그 용도가 비교적 좁은 분야에 한정된다.Among the resins used as raw materials for high refractive index plastic lenses, polycarbonate ( n 20 D = 1.58) and polystyrene ( n D 20 = 1.60) have low plasticity due to insufficient polishing processability and insufficient surface hardness. Because of its low scratch resistance and low resistance to organic solvents, its use in the optical field is limited to a relatively narrow field.
고굴절률을 갖는 플라스틱 렌즈의 원료로 사용되는 또다른 물질들로 (1) 비스페놀 A에서 유도된 디아크릴레이트 또는 디메타크릴레이트[일본 특허공개공보 제 116,301/83호], (2) 할로겐화 비스페놀 A에서 유도된 디아크릴레이트 또는 디메타크릴레이트[일본 특허공개공보 제 10,491/82호], (3) 할로겐화 스티렌 단량체 및 다 작용성 메타크릴레이트의 결합물[일본 특허공개공보 제 104,101/82호, 제 28,118/82호 및 제 28,116/82호], 및 (4) 디알릴프탈레이트 단량체[일본 특허공개공보 제 212,401/82호 및 15,513/83호] 등이 제안되었다. 그러나 (1)의 물질은 1.60 이상의 굴절률을 갖는 입체가교결합 플라스틱을 제공하기 어렵고, (2),(3) 및 (4)의 물질은 유입(cast) 중합 중 변색되는 경향이 있으며, 내후성 및 가시광선 투과율에서도 만족스럽지 못하다.Other materials used as raw materials for high refractive index plastic lenses include (1) diacrylates or dimethacrylates derived from bisphenol A [Japanese Patent Laid-Open No. 116,301 / 83], (2) halogenated bisphenol A Diacrylates or dimethacrylates derived from Japanese Patent Application Laid-Open No. 10,491 / 82, (3) combinations of halogenated styrene monomers and polyfunctional methacrylates [Japanese Patent Laid-Open No. 104,101 / 82, 28,118 / 82 and 28,116 / 82, and (4) diallyl phthalate monomers (Japanese Patent Laid-Open Nos. 212,401 / 82 and 15,513 / 83) and the like have been proposed. However, the material of (1) is difficult to provide a stereocrosslinked plastic having a refractive index of 1.60 or more, and the materials of (2), (3) and (4) tend to discolor during cast polymerization, weather resistance and visibility Even the light transmittance is not satisfactory.
따라서, 상기 기재한 문제점을 모두 극복하고 고굴절율 및 고아베수를 갖는 렌즈를 제조할 수 있는 새로운 광학용 수지의 개발이 필요하다.Therefore, there is a need for the development of a new optical resin that can overcome all the problems described above and produce a lens having a high refractive index and a high Abbe's number.
본 발명은 상기 문제점을 해결하고, 고굴절률, 고아베수, 투명성, 광학적 균일성 및 경량성이 우수한 광학 렌즈를 제조할 수 있는 수지 조성물과 그에 의해 제조된 광학 렌즈를 제공하는데 목적이 있다.SUMMARY OF THE INVENTION An object of the present invention is to solve the above problems and to provide a resin composition capable of producing an optical lens excellent in high refractive index, high Abbe number, transparency, optical uniformity and light weight, and an optical lens produced thereby.
본 발명은, (A) 화학식 1로 표시되는 비스페놀 A 골격을 갖는 (메타)아크릴레이트 화합물 10~75 중량부, (B) 화학식 2로 표시되는 지방족 폴리티올 화합물 1~70 중량부, (C) 화학식 3으로 표시되는 황을 함유하는 (메타)아크릴레이트 화합물 1~40 중량부, 및 (D) 화학식 4로 표시되는 지방족 또는 지환족을 가지는 (메타)아크릴레이트 화합물 1~45 중량부를 포함하는 광학용 수지 조성물을 제공한다.The present invention provides (A) 10 to 75 parts by weight of a (meth) acrylate compound having a bisphenol A skeleton represented by the formula (1), (B) 1 to 70 parts by weight of an aliphatic polythiol compound represented by the formula (2), (C) 1 to 40 parts by weight of the (meth) acrylate compound containing sulfur represented by the formula (3), and (D) an optical including 1 to 45 parts by weight of the (meth) acrylate compound having an aliphatic or alicyclic compound represented by the formula (4) The resin composition for this is provided.
상기 화학식 1에서 R1, R2는 H 또는 CH3를 나타내고, m, n은 각각 정수 0~4, m+n은 0~8, Y는 H, OH를 나타낸다.In Formula 1, R 1 and R 2 represent H or CH 3 , m and n each represent an integer of 0 to 4, m + n represents 0 to 8, and Y represents H and OH.
상기 화학식 2에서 R은 S 또는 C 이고, R3, R4는 CH2SH, CH2CH 2SH, COOCH2SH, COOCH2CH2SH 중에서 선택된 하나이며, R5, R6는 R이 C이면 CH 2SH 이고, R이 S이면 존재하지 않는다.In Formula 2, R is S or C, R 3 , R 4 is one selected from CH 2 SH, CH 2 CH 2 SH, COOCH 2 SH, COOCH 2 CH 2 SH, R 5 , R 6 is R is C If CH 2 SH, and if R is S it is absent.
상기 화학식 3에서 X는 지환족, 방향족을 나타내며, Y는 H, CH3 이다.In Formula 3, X represents alicyclic and aromatic, and Y is H, CH 3 .
상기 화학식 4에서 X는 지방족 또는 지환족을 나타내며, Y는 H, CH3 이다.In Formula 4, X represents aliphatic or alicyclic, and Y is H, CH 3 .
본 발명의 조성물은 성분 (A) 20~70 중량부, 성분 (B) 1~20 중량부, 성분 (C) 1~20 중량부, 및 성분 (D) 1~15 중량부를 포함하는 것이 바람직하다.It is preferable that the composition of this invention contains 20-70 weight part of components (A), 1-20 weight part of components (B), 1-20 weight part of components (C), and 1-15 weight part of components (D). .
또한 본 발명은, 상기 조성물을 중합 및 경화시켜 고굴절률, 고아베수, 투명성, 광학적 균일성 및 경량성이 우수한 광학 렌즈를 제공한다.The present invention also polymerizes and hardens the composition to provide an optical lens excellent in high refractive index, high Abbe number, transparency, optical uniformity and lightness.
본 발명의 광학용 수지 조성물을 구성하는 각각의 성분을 상세히 설명하면 다음과 같다.When explaining each component which comprises the optical resin composition of this invention in detail, it is as follows.
(A) 화학식 1로 표시되는 비스페놀 A 골격을 갖는 (메타)아크릴레이트 화합물(A) (meth) acrylate compound which has bisphenol A frame | skeleton represented by General formula (1)
성분 (A)는 고굴절률, 저점도이며, 2 이상의 작용기를 갖는 것을 특징으로 한다. 성분 (A)는 2 이상의 작용기를 가지므로 라디칼 부가가 가능하다.Component (A) is high refractive index, low viscosity, and is characterized by having two or more functional groups. Component (A) has two or more functional groups so radical addition is possible.
라디칼 부가란 폴리엔 화합물이나 (메타)아크릴 화합물의 불포화 결합에 대한 티올의 부가반응, 또는 불포화 결합끼리의 부가반응을 의미한다.The radical addition means the addition reaction of thiol to the unsaturated bond of a polyene compound or a (meth) acryl compound, or the addition reaction of unsaturated bonds.
성분 (A)로 바람직한 것은 BPA-2A(Ethyleneoxide(2mol) added Diacrylate of Bisphenol A Diglycidyl ether), BPA-4EA(Diacrylate of ethyleneoxide modified bisphenol A), BPA-4PA(Diacrylate of propyleneoxide modified bisphenol A), BPA-2EM(Dimethacrylate of ethyleneoxide modified bisphenol A) 등이다.Preferred as component (A) are ethylene oxide (2 mol) added Diacrylate of Bisphenol A Diglycidyl ether (BPA-2A), diacrylate of ethyleneoxide modified bisphenol A (BPA-4EA), diacrylate of propyleneoxide modified bisphenol A (BPA-4PA), and BPA- 2EM (Dimethacrylate of ethyleneoxide modified bisphenol A).
성분 (A)는 전체 수지 조성물 중에서 10~75 중량부 범위로 사용하며, 20~70 중량부가 바람직하다.Component (A) is used in the range of 10-75 weight part in all the resin composition, and 20-70 weight part is preferable.
(B) 화학식 2로 표시되는 지방족 폴리티올 화합물(B) aliphatic polythiol compound represented by formula (2)
성분 (B)는 2 작용기 이상의 티올 화합물이 바람직하고, 상기 성분 (A)와 라디칼 부가가 가능하다.Component (B) is preferably a thiol compound having two or more functional groups, and the component (A) and radical addition are possible.
성분 (B)로 바람직한 것은 DMDS(Dimercapto Dimethylsulfide), BMEE(Bis(2-mercaptoethyl)ether) 등이다.Preferred as component (B) are Dimercapto Dimethylsulfide (DMDS), Bis (2-mercaptoethyl) ether (BMEE) and the like.
성분 (B)는 전체 수지 조성물 중에서 1~70 중량부 범위로 사용하며, 1~20 중량부가 바람직하다.Component (B) is used in the range of 1-70 weight part in all the resin compositions, and 1-20 weight part is preferable.
(C) 화학식 3으로 표시되는 황을 함유하는 (메타)아크릴레이트 화합물(C) (meth) acrylate compound containing sulfur represented by General formula (3)
성분 (C)는 성분 (A)와 라디칼 공중합이 가능하고, PTEA(Phenylthioethyl acrylate), HTEMA(Hexylthioethyl methacrylate), PTEEA(Phenylthioethyl ethacrylate) 등이 바람직하다.Component (C) is capable of radical copolymerization with component (A), and preferred are phenylthioethyl acrylate (PTEA), hexylthioethyl methacrylate (HTEMA), phenylthioethyl ethacrylate (PTEEA), and the like.
성분 (C)는 전체 수지 조성물 중에서 1~40 중량부 범위로 사용하며, 1~20 중량부가 바람직하다.Component (C) is used in 1-40 weight part of the whole resin composition, and 1-20 weight part is preferable.
(D) 화학식 4로 표시되는 지방족 또는 지환족을 가지는 (메타)아크릴레이트 화합물(D) an (meth) acrylate compound having an aliphatic or alicyclic compound represented by the formula (4)
성분 (D)는 성분 (A), (B), (C)와 라디칼 공중합이 가능하며, DTDDA(Dimethylol tricyclo decane diacrylate), HAPMA(2-Hydroxy-3-acryloyloxy propylmethacrylate), TMGDA(poly tetramethylene glycol diacrylate) 등이 바람직하다.Component (D) is capable of radical copolymerization with components (A), (B), and (C), dimethylol tricyclo decane diacrylate (DTDDA), 2-Hydroxy-3-acryloyloxy propylmethacrylate (HAPMA), and poly tetramethylene glycol diacrylate ) Is preferred.
성분 (D)는 전체 수지 조성물 중에서 1~45 중량부 범위로 사용하며, 1~15 중량부가 바람직하다.Component (D) is used in the range of 1 to 45 parts by weight in the total resin composition, and 1 to 15 parts by weight is preferable.
본 발명의 수지 조성물은 희석제로 디비닐벤젠, 디이소프로페닐벤젠, 스티렌, 핵치환 스티렌, 단 작용성 (메타)아크릴레이트 등을 사용하여 수지의 점도와 굴절율을 조절할 수 있다. 구체적으로는, o-디비닐벤젠, m-디비닐벤젠, p-디비닐벤젠, m-디이소프로페닐벤젠, p-디이소프로페닐벤젠, 스티렌, 메틸스티렌, 클로로스티렌, 디클로로스티렌, 브로모스티렌, 디브로모스티렌, 메틸(메타)아크릴레이트, 에틸(메타)아크릴레이트, 프로필(메타)아크릴레이트, 이소프로필(메타)아크릴레이트, 시클로헥실(메타)아크릴레이트, 벤질(메타)아크릴레이트, 페녹시에틸(메타)아크릴레이트, 글리시딜(메타)아크릴레이트, 글리시딜알릴에테르 등을 사용할 수 있으며, 그 중에서도 디비닐벤젠과 스티렌이 보다 바람직하다.The resin composition of the present invention can adjust the viscosity and refractive index of the resin using divinylbenzene, diisopropenylbenzene, styrene, nuclear substituted styrene, monofunctional (meth) acrylate and the like as a diluent. Specifically, o-divinylbenzene, m-divinylbenzene, p-divinylbenzene, m-diisopropenylbenzene, p-diisopropenylbenzene, styrene, methyl styrene, chloro styrene, dichloro styrene, bro Mostyrene, dibromostyrene, methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, isopropyl (meth) acrylate, cyclohexyl (meth) acrylate, benzyl (meth) acrylic The rate, phenoxyethyl (meth) acrylate, glycidyl (meth) acrylate, glycidyl allyl ether, etc. can be used, Especially, divinylbenzene and styrene are more preferable.
본 발명의 수지 조성물은 본 발명의 효과를 손상하지 않는 범위에서, 필요에 따라 자외선흡수제, 산화방지제, 황변 방지제, 염료, 향료, 중합조절제 및 이형제 등의 각종 첨가제를 배합해서 바람직한 물성이나 기능을 발현시킬 수 있다.The resin composition of the present invention may be blended with various additives such as ultraviolet absorbers, antioxidants, anti-yellowing agents, dyes, flavoring agents, polymerization regulators and mold release agents to express desirable physical properties and functions, if necessary, within a range that does not impair the effects of the present invention. You can.
본 발명의 수지 조성물을 중합 및 경화해서 굴절률(n D 20) 1.59 이상의 고굴절률 및 고아베수를 가진 광학 렌즈를 얻는다. 필요에 따라 경화 후 어닐링 처리를 할 수도 있다. 또한 반사방지, 고경도 부여 혹은 패션성 부여 등의 개량을 행하기 위해 표면연마, 대전방지 처리, 하드코팅 처리, 무반사 코팅 처리 및 염색처리 등의 물리적 혹은 화학적 처리를 실시할 수 있다.The resin composition of the present invention is polymerized and cured to obtain an optical lens having a high refractive index and a high Abbe's number of refractive index ( n D 20 ) of 1.59 or more. If necessary, annealing treatment may be performed after curing. In addition, physical or chemical treatments such as surface polishing, antistatic treatment, hard coating treatment, anti-reflective coating treatment, and dyeing treatment may be performed to improve reflection prevention, hardening, or fashion.
본 발명의 광학 렌즈는 공지의 라디칼 중합을 사용한 주형중합 방법으로 제조한다. 구체적으로는, 본 발명의 수지 조성물에 라디칼 중합 개시제 및 광중합 개시제 등의 촉매를 첨가하여, 잘 혼합한 후, 여과하고, 감압하에서 충분히 탈포한 후, 몰드속에 주입해서 라디칼 중합을 행한다.The optical lens of this invention is manufactured by the casting-polymerization method using well-known radical polymerization. Specifically, catalysts such as a radical polymerization initiator and a photopolymerization initiator are added to the resin composition of the present invention, mixed well, filtered, degassed sufficiently under reduced pressure, and then injected into a mold to perform radical polymerization.
몰드는 폴리에스테르 점착 테이프 또는 가스켓을 사용하여 2매의 주형(鑄型)에 의해 구성된다. 주형으로는 유리와 유리, 유리와 플라스틱판, 유리와 금속판 등의 조합 주형을 사용할 수 있다.The mold is constituted by two molds using a polyester adhesive tape or a gasket. As the mold, combination molds such as glass and glass, glass and plastic plates, and glass and metal plates can be used.
본 발명의 렌즈를 제조하기 위한 중합반응에서는, 촉매, 즉, 라디칼 중합 개시제로서, 공지의 과산화벤조일, p-클로로벤조일퍼옥사이드, 라우로일퍼옥사이드, 아세틸퍼옥사이드, 디-t-부틸퍼옥사이드, 1,1-디-t-부틸퍼옥시-3,3,5-트리메틸시클로헥산, t-부틸퍼옥시피발레이트, t-부틸퍼옥시-2-에틸헥산오에이트, t-부틸퍼옥시벤조에이트, 비스(4-t-부틸시클로헥실)퍼옥시디카보네이트, 디이소프로필퍼옥시디카보네이트, t-부틸퍼옥시이소프로필카보네이트 등의 과산화물 및 아조비스이소부티로 니트릴 등의 아조화합물 또는 2종 이상의 혼합물을 0.001~5 중량부, 바람직하게는 0.01~3 중량부의 비율로 사용할 수 있다.In the polymerization reaction for producing the lens of the present invention, as a catalyst, that is, a radical polymerization initiator, known benzoyl peroxide, p-chlorobenzoyl peroxide, lauroyl peroxide, acetyl peroxide, di-t-butyl peroxide, 1,1-di-t-butylperoxy-3,3,5-trimethylcyclohexane, t-butylperoxy pivalate, t-butylperoxy-2-ethylhexaneoate, t-butylperoxybenzoate Azo compounds such as peroxides such as bis (4-t-butylcyclohexyl) peroxydicarbonate, diisopropylperoxydicarbonate, t-butylperoxyisopropylcarbonate and azobisisobutyronitrile or mixtures of two or more thereof 0.001-5 weight part, Preferably it can be used in the ratio of 0.01-3 weight part.
상기 성분비는 중합온도, 중합시간, 사용하는 라디칼 및 경화물의 크기 등에 따라 결정된다.The component ratio is determined according to the polymerization temperature, the polymerization time, the radical used and the size of the cured product.
본 발명의 렌즈는 본 발명의 수지 조성물을 혼합하여 몰드에 주입한 후, 25~110℃ 까지 15~30간 동안 가열하여 중합 및 경화시켜 제조한다.The lens of the present invention is prepared by mixing the resin composition of the present invention and injecting it into a mold, followed by heating to 25 to 110 ° C. for 15 to 30 minutes to polymerize and cure.
이하 본 발명의 대표적인 실시예를 구체적으로 설명하지만, 본 발명이 이에 국한되는 것은 아니다.Hereinafter, exemplary embodiments of the present invention will be described in detail, but the present invention is not limited thereto.
실시예 1Example 1
실온에서 비스페놀 A계 디아크릴레이트 47g, 헥실티오에틸메타타크릴레이트 15g, 2-히드록시-3-아크릴로일옥시프로필메타크릴레이트 5g, 비스(2-메르캅토에틸)에테르 12g, 스티렌 5g, 디비닐벤젠 16g을 균일하게 교반한 뒤 t-부틸퍼옥시이소프로필카보네이트 0.3g을 넣고 다시 교반하여 혼합하였다. 이 혼합물을 2매의 유리 몰드에 주입하여 35~110℃ 까지 19시간 동안 가열 경화하고, 경화가 끝나면 40℃ 까지 냉각하여 주형에서 경화 성형물을 꺼내고, 90~110℃에서 1~2시간 어닐링하여 잔류응력을 제거한 뒤 플라스틱 렌즈를 제조하였다.47 g of bisphenol A-based diacrylate, 15 g of hexylthioethyl methacrylate, 5 g of 2-hydroxy-3-acryloyloxypropyl methacrylate, 12 g of bis (2-mercaptoethyl) ether, 5 g of styrene, After 16 g of divinylbenzene was uniformly stirred, 0.3 g of t-butylperoxyisopropyl carbonate was added thereto, and the mixture was stirred and mixed again. The mixture was poured into two glass molds and cured by heating to 35 to 110 ° C. for 19 hours, and after curing, the mixture was cooled to 40 ° C. to remove the cured molding from the mold, followed by annealing at 90 to 110 ° C. for 1 to 2 hours. The plastic lens was manufactured after the stress was removed.
실시예 2~5Examples 2-5
실시예 1과 같은 방법으로 표 1에 나타낸 배합비에 맞춰 플라스틱 렌즈를 제조하였다.A plastic lens was manufactured according to the blending ratios shown in Table 1 in the same manner as in Example 1.
비교예Comparative example
비스페놀 A계 디아크릴레이트 40g, 에틸렌옥사이드 부가된 비스페놀 A계 메타크릴레이트 21g, 페닐티오에틸에타크릴레이트 8g, 디메티롤트리시클로데칸 디아크릴레이트 3g, 스티렌 10g, 비닐톨루엔 18g을 균일하게 혼합하여 상기 실시예 1과 같은 방법으로 주형 중합하여 플라스틱 렌즈를 제조하였다.40 g of bisphenol A diacrylate, 21 g of ethylene oxide-added bisphenol A methacrylate, 8 g of phenylthioethyl ethane acrylate, 3 g of dimethyrol tricyclodecane diacrylate, 10 g of styrene, and 18 g of vinyltoluene were mixed uniformly. A plastic lens was prepared by casting polymerization in the same manner as in Example 1.
실험예Experimental Example : 물성 측정 Property measurement
실시예 1~5 및 비교예에서 제조한 렌즈의 물성평가는 다음 시험방법에 따라 측정하였다.Evaluation of physical properties of the lenses prepared in Examples 1 to 5 and Comparative Examples was measured according to the following test method.
(1) 투명성 : 육안으로 관찰하여 색, 탁함 및 변형이 없는 것을 양호한 것으로 하였다.(1) Transparency: Observation was made with the naked eye, and the thing without color, haze, and deformation was made favorable.
(2) 굴절률 및 아베수 : 플프리히 굴절계를 이용하여 측정하였다. 단, 프리폴리머의 굴절률은 아베 굴절계를 이용하여 측정하였다.(2) Refractive index and Abbe's number: It measured using the Fleich refractometer. However, the refractive index of the prepolymer was measured using an Abbe refractometer.
(3) 내충격성 : 중심두께 1.5~1.6㎜인 렌즈를 150㎝ 높이에서 28.5g의 강철구를 사용한 낙구 시험을 행하여, 합격된 것을 O, 합격되지 않은 것을 X 로 하였다.(3) Impact resistance: A dropping test using a 28.5 g steel ball was carried out at 150 cm in height for a lens having a center thickness of 1.5 to 1.6 mm, and the pass was O and the pass was X.
(4) 내열성 : 침입법에 의한 TMA를 측정하여, 80℃ 이하에 변형점이 있는 것을 X, 80℃ 이상인 것을 O로 하였다.(4) Heat resistance: TMA by the invasion method was measured, and the thing which has a strain point at 80 degrees C or less was made into X and 80 degreeC or more.
(5) 염색성 : 염색욕 속에서, 디에틸렌글리콜 비스알릴카보네이트 수지와 동시에 염색을 행하여, 육안관찰에 의해 동등 혹은 그 이상으로 염색되어 있는 것을 O, 떨어지는 것을 X로 하였다.(5) Dyeing property: Dyeing was performed simultaneously with diethylene glycol bisallylcarbonate resin in a dyeing bath, and the dyeing of the same or more dyes by visual observation was O and the falling one was X.
(6) 내후성 : 선샤인 카아본 방전 램프를 장비한 내후성 시험기에 렌즈용 수지를 세트하고, 200시간 경과한 시점에서 렌즈를 꺼내어 시험전의 렌즈용 수지와 색상을 비교하였다. 평가기준은 변화 없음(O), 황색으로 변함(X)으로 하였다.(6) Weather resistance: Lens resin was set in the weather resistance tester equipped with the sunshine carbon discharge lamp, the lens was taken out after 200 hours, and the color of the lens resin before a test was compared. Evaluation criteria were made into no change (O) and turned yellow (X).
본 발명의 렌즈의 물성 측정 결과는 표 1에 나타내었다.The measurement results of the physical properties of the lens of the present invention are shown in Table 1.
* BPA-2A : Ethyleneoxide(2mol) added Diacrylate of Bisphenol A Diglycidyl ether* BPA-2A: Ethyleneoxide (2mol) added Diacrylate of Bisphenol A Diglycidyl ether
* BPA-4EA : Diacrylate of ethyleneoxide modified bisphenol A* BPA-4EA: Diacrylate of ethyleneoxide modified bisphenol A
* BPA-4PA : Diacrylate of propyleneoxide modified bisphenol A* BPA-4PA: Diacrylate of propyleneoxide modified bisphenol A
* BPA-2EM : Dimethacrylate of ethyleneoxide modified bisphenol A* BPA-2EM: Dimethacrylate of ethyleneoxide modified bisphenol A
* DMDS : Dimercapto DimethylsulfideDMDS: Dimercapto Dimethylsulfide
* BMEE : Bis(2-mercaptoethyl)ether* BMEE: Bis (2-mercaptoethyl) ether
* PTEA : Phenylthioethyl acrylate* PTEA: Phenylthioethyl acrylate
* HTEMA : Hexylthioethyl methacrylate* HTEMA: Hexylthioethyl methacrylate
* PTEEA : Phenylthioethyl ethacrylate* PTEEA: Phenylthioethyl ethacrylate
* DTDDA : Dimethylol tricyclo decane diacrylate* DTDDA: Dimethylol tricyclo decane diacrylate
* HAPMA : 2-Hydroxy-3-acryloyloxy propylmethacrylate* HAPMA: 2-Hydroxy-3-acryloyloxy propylmethacrylate
* TMGDA : poly tetramethylene glycol diacrylate* TMGDA: poly tetramethylene glycol diacrylate
* SM : Styrene Monomer* SM: Styrene Monomer
* DVB : Divinyl BenzeneDVB: Divinyl Benzene
* VT : Vinyl Toluene* VT: Vinyl Toluene
표 1에 나타난 바와 같이, 실시예 1~5에 의해 제조된 본 발명의 렌즈는 고굴절률, 고아베수를 확인할 수 있고, 또한 내충격성, 내후성, 염색성 및 내열성이 우수함을 확인할 수 있다.As shown in Table 1, the lens of the present invention prepared by Examples 1 to 5 can confirm the high refractive index, the high Abbe number, and also it can be confirmed that the impact resistance, weather resistance, staining and heat resistance is excellent.
본 발명의 경화된 물질의 비중은 1.14~1.16로 CR-39(1.32) 및 디메탈릴프탈레이트(1.22)와 비교해 볼때 작으므로, 광학 렌즈를 제조하는데 알맞으며, 기존에 제조된 제품보다 무게가 훨씬 가벼운 제품을 생산할 수 있다.The specific gravity of the cured material of the present invention is 1.14 to 1.16, which is small compared to CR-39 (1.32) and dimetall phthalate (1.22), which is suitable for manufacturing optical lenses, and is much heavier than conventionally manufactured products. Can produce light products.
본 발명은 수지 조성물을 중합 및 경화시켜 고굴절률, 고아베수, 투명성, 광학적 균일성 및 경량성이 우수한 광학 렌즈를 얻을 수 있다.The present invention can polymerize and cure the resin composition to obtain an optical lens excellent in high refractive index, high Abbe number, transparency, optical uniformity and light weight.
Claims (8)
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| PCT/KR2002/001034 WO2002100911A1 (en) | 2001-05-31 | 2002-05-31 | Resin compositions, and optical lens prepared thereby |
| CNA028110765A CN1513006A (en) | 2001-05-31 | 2002-05-31 | Resin compositions, and optical lens prepared thereby |
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| KR100474586B1 (en) * | 2002-06-12 | 2005-03-08 | 주식회사 두산 | Resin compositions, and optical lens prepared by them |
| KR100523077B1 (en) * | 2003-01-14 | 2005-10-20 | 주식회사 니드필 | Resin composition for producing optical lens having high refraction index, and optical lens produced with the same |
| KR100819998B1 (en) * | 2007-04-27 | 2008-04-08 | 주식회사 두산 | Photochromic resin, preparation method thereof and optical product |
| KR100838529B1 (en) * | 2007-07-03 | 2008-06-17 | 김기현 | Photochromic composition and high refractive index optical lens, optical product manufactured using the same |
| KR101452440B1 (en) * | 2012-12-03 | 2014-10-24 | 주식회사 제일화성 | Resin composition for optical lens |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR900700562A (en) * | 1987-12-28 | 1990-08-16 | 에이. 더블유. 카람벨라스 | Liquid Crystal Droplet Dispersion in Photopolymerized Matrix and Apparatus Made therefrom |
| US5916987A (en) * | 1996-05-29 | 1999-06-29 | Mitsui Chemicals, Inc. | Thiol and Sulfur-containing O-(meth) acrylate compounds and use thereof |
| US6022497A (en) * | 1998-07-10 | 2000-02-08 | Ppg Industries Ohio, Inc. | Photochromic six-membered heterocyclic-fused naphthopyrans |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR900700562A (en) * | 1987-12-28 | 1990-08-16 | 에이. 더블유. 카람벨라스 | Liquid Crystal Droplet Dispersion in Photopolymerized Matrix and Apparatus Made therefrom |
| US5916987A (en) * | 1996-05-29 | 1999-06-29 | Mitsui Chemicals, Inc. | Thiol and Sulfur-containing O-(meth) acrylate compounds and use thereof |
| US6114485A (en) * | 1996-05-29 | 2000-09-05 | Mitsui Chemicals, Inc. | Thiol and sulfur-containing O-(meth)acrylate compounds and use thereof |
| US6022497A (en) * | 1998-07-10 | 2000-02-08 | Ppg Industries Ohio, Inc. | Photochromic six-membered heterocyclic-fused naphthopyrans |
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