CA1207939A - Resine pour verres optiques, et verres faits de ladite resine - Google Patents

Resine pour verres optiques, et verres faits de ladite resine

Info

Publication number: CA1207939A
Authority: CA; Canada
Prior art keywords: aromatic ring; acrylic; monomer; plastic lens; resin material
Prior art date: 1983-09-20
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA000437130A

Other languages

English (en)

Inventor

Tadanori Fukuda

Sadayuki Sakamoto

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Toray Industries Inc

Original Assignee

Toray Industries Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1983-09-20

Filing date

1983-09-20

Publication date

1986-07-15

1983-09-20 Application filed by Toray Industries Inc filed Critical Toray Industries Inc

1983-09-20 Priority to CA000437130A priority Critical patent/CA1207939A/fr

1986-07-15 Application granted granted Critical

1986-07-15 Publication of CA1207939A publication Critical patent/CA1207939A/fr

Status Expired legal-status Critical Current

Links

229920005989 resin Polymers 0.000 title claims abstract description 42
239000011347 resin Substances 0.000 title claims abstract description 42
229920003023 plastic Polymers 0.000 title claims abstract description 28
239000004033 plastic Substances 0.000 title claims abstract description 28
239000000463 material Substances 0.000 title claims abstract description 16
239000000178 monomer Substances 0.000 claims abstract description 52
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 24
125000005395 methacrylic acid group Chemical group 0.000 claims abstract description 23
125000003118 aryl group Chemical class 0.000 claims abstract description 22
239000012948 isocyanate Substances 0.000 claims abstract description 13
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 11
150000002513 isocyanates Chemical class 0.000 claims abstract description 11
229920000642 polymer Polymers 0.000 claims abstract description 11
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 4
230000000379 polymerizing effect Effects 0.000 claims abstract description 4
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 15
229920002554 vinyl polymer Polymers 0.000 claims description 15
150000001875 compounds Chemical class 0.000 claims description 10
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
229910052794 bromium Inorganic materials 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 4
229920001577 copolymer Polymers 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
229920001519 homopolymer Polymers 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
125000005442 diisocyanate group Chemical group 0.000 claims description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
229910052736 halogen Inorganic materials 0.000 claims 1
150000002367 halogens Chemical class 0.000 claims 1
229910052740 iodine Inorganic materials 0.000 claims 1
239000011630 iodine Substances 0.000 claims 1
239000000203 mixture Substances 0.000 description 27
238000006116 polymerization reaction Methods 0.000 description 21
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 16
MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 13
238000006243 chemical reaction Methods 0.000 description 12
230000000694 effects Effects 0.000 description 10
238000000034 method Methods 0.000 description 10
-1 ethoxy-3,5-dibromophenyl Chemical group 0.000 description 9
FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 8
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
239000007788 liquid Substances 0.000 description 8
239000003505 polymerization initiator Substances 0.000 description 8
239000001294 propane Substances 0.000 description 8
235000013849 propane Nutrition 0.000 description 8
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 description 6
230000000052 comparative effect Effects 0.000 description 6
LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 6
229940116441 divinylbenzene Drugs 0.000 description 6
RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 6
SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical compound ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 description 5
239000005057 Hexamethylene diisocyanate Substances 0.000 description 5
VZDQBADMMJDJES-UHFFFAOYSA-N [3-(2,4-dibromophenoxy)-2-hydroxypropyl] prop-2-enoate Chemical compound C=CC(=O)OCC(O)COC1=CC=C(Br)C=C1Br VZDQBADMMJDJES-UHFFFAOYSA-N 0.000 description 5
UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 5
239000012975 dibutyltin dilaurate Substances 0.000 description 5
QXRRAZIZHCWBQY-UHFFFAOYSA-N 1,1-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1(CN=C=O)CCCCC1 QXRRAZIZHCWBQY-UHFFFAOYSA-N 0.000 description 4
239000004641 Diallyl-phthalate Substances 0.000 description 4
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
CMHRNMTXLVQKCZ-UHFFFAOYSA-N [3-(2,4-dibromo-3-methylphenoxy)-2-hydroxypropyl] prop-2-enoate Chemical compound CC1=C(Br)C=CC(OCC(O)COC(=O)C=C)=C1Br CMHRNMTXLVQKCZ-UHFFFAOYSA-N 0.000 description 4
238000000576 coating method Methods 0.000 description 4
239000011521 glass Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
ZSVFYHKZQNDJEV-UHFFFAOYSA-N (2,3,4-tribromophenyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=C(Br)C(Br)=C1Br ZSVFYHKZQNDJEV-UHFFFAOYSA-N 0.000 description 3
239000005058 Isophorone diisocyanate Substances 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
YMOONIIMQBGTDU-VOTSOKGWSA-N [(e)-2-bromoethenyl]benzene Chemical compound Br\C=C\C1=CC=CC=C1 YMOONIIMQBGTDU-VOTSOKGWSA-N 0.000 description 3
MEOPNJWOBMFTLM-UHFFFAOYSA-N [2-hydroxy-3-(2,4,6-tribromo-3-methylphenoxy)propyl] prop-2-enoate Chemical compound CC1=C(Br)C=C(Br)C(OCC(O)COC(=O)C=C)=C1Br MEOPNJWOBMFTLM-UHFFFAOYSA-N 0.000 description 3
QZNRJRYGKMFKFC-UHFFFAOYSA-N [2-hydroxy-3-(2,4,6-tribromophenoxy)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(O)COC1=C(Br)C=C(Br)C=C1Br QZNRJRYGKMFKFC-UHFFFAOYSA-N 0.000 description 3
NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
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 3
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 3
239000007809 chemical reaction catalyst Substances 0.000 description 3
239000011248 coating agent Substances 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
238000000227 grinding Methods 0.000 description 3
NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 3
230000003287 optical effect Effects 0.000 description 3
230000000704 physical effect Effects 0.000 description 3
CLIGMUNFUITOMS-UHFFFAOYSA-N (1,2,2-tribromo-2-phenoxyethyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(Br)C(Br)(Br)OC1=CC=CC=C1 CLIGMUNFUITOMS-UHFFFAOYSA-N 0.000 description 2
CYLVUSZHVURAOY-UHFFFAOYSA-N 2,2-dibromoethenylbenzene Chemical compound BrC(Br)=CC1=CC=CC=C1 CYLVUSZHVURAOY-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
OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 2
GNDOBZLRZOCGAS-UHFFFAOYSA-N 2-isocyanatoethyl 2,6-diisocyanatohexanoate Chemical compound O=C=NCCCCC(N=C=O)C(=O)OCCN=C=O GNDOBZLRZOCGAS-UHFFFAOYSA-N 0.000 description 2
239000004698 Polyethylene Substances 0.000 description 2
238000012644 addition polymerization Methods 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
238000007334 copolymerization reaction Methods 0.000 description 2
230000007547 defect Effects 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
238000005259 measurement Methods 0.000 description 2
229940063557 methacrylate Drugs 0.000 description 2
238000000465 moulding Methods 0.000 description 2
229920000573 polyethylene Polymers 0.000 description 2
239000004814 polyurethane Substances 0.000 description 2
229920002635 polyurethane Polymers 0.000 description 2
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 2
239000002904 solvent Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
BQQKFHBEWPZGAY-UHFFFAOYSA-N (1,2,2-trichloro-2-phenoxyethyl) prop-2-enoate Chemical compound C=CC(=O)OC(Cl)C(Cl)(Cl)OC1=CC=CC=C1 BQQKFHBEWPZGAY-UHFFFAOYSA-N 0.000 description 1
OOVJBKXBWBSFQC-UHFFFAOYSA-N (2,2-dibromo-2-phenoxyethyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(Br)(Br)OC1=CC=CC=C1 OOVJBKXBWBSFQC-UHFFFAOYSA-N 0.000 description 1
CBFNQNRGWOQHJB-UHFFFAOYSA-N (2,2-dibromo-2-phenoxyethyl) prop-2-enoate Chemical compound C=CC(=O)OCC(Br)(Br)OC1=CC=CC=C1 CBFNQNRGWOQHJB-UHFFFAOYSA-N 0.000 description 1
JAOQXTFLESFCEU-UHFFFAOYSA-N (2,2-dichloro-2-phenoxyethyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(Cl)(Cl)OC1=CC=CC=C1 JAOQXTFLESFCEU-UHFFFAOYSA-N 0.000 description 1
ZJBDZAONRFEKSJ-UHFFFAOYSA-N (2,2-dichloro-2-phenoxyethyl) prop-2-enoate Chemical compound C=CC(=O)OCC(Cl)(Cl)OC1=CC=CC=C1 ZJBDZAONRFEKSJ-UHFFFAOYSA-N 0.000 description 1
OFZRSOGEOFHZKS-UHFFFAOYSA-N (2,3,4,5,6-pentabromophenyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=C(Br)C(Br)=C(Br)C(Br)=C1Br OFZRSOGEOFHZKS-UHFFFAOYSA-N 0.000 description 1
BKKVYNMMVYEBGR-UHFFFAOYSA-N (2,3,4,5,6-pentabromophenyl) prop-2-enoate Chemical compound BrC1=C(Br)C(Br)=C(OC(=O)C=C)C(Br)=C1Br BKKVYNMMVYEBGR-UHFFFAOYSA-N 0.000 description 1
BUPRYTFTHBNSBD-UHFFFAOYSA-N (2,3,4-tribromophenyl) prop-2-enoate Chemical compound BrC1=CC=C(OC(=O)C=C)C(Br)=C1Br BUPRYTFTHBNSBD-UHFFFAOYSA-N 0.000 description 1
IGWMFERXHIUPRD-UHFFFAOYSA-N (2,3,4-trichlorophenyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=C(Cl)C(Cl)=C1Cl IGWMFERXHIUPRD-UHFFFAOYSA-N 0.000 description 1
JLOIRPJHPDQHHN-UHFFFAOYSA-N (2,3,4-trichlorophenyl) prop-2-enoate Chemical compound ClC1=CC=C(OC(=O)C=C)C(Cl)=C1Cl JLOIRPJHPDQHHN-UHFFFAOYSA-N 0.000 description 1
QBRUEJWTPFYVRF-UHFFFAOYSA-N (2,3-dibromophenyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC(Br)=C1Br QBRUEJWTPFYVRF-UHFFFAOYSA-N 0.000 description 1
HYQXPEYCYNAMNO-UHFFFAOYSA-N (2,3-dibromophenyl) prop-2-enoate Chemical compound BrC1=CC=CC(OC(=O)C=C)=C1Br HYQXPEYCYNAMNO-UHFFFAOYSA-N 0.000 description 1
HEFNMVUNWYUUGC-UHFFFAOYSA-N (2,3-dichlorophenyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC(Cl)=C1Cl HEFNMVUNWYUUGC-UHFFFAOYSA-N 0.000 description 1
SGYGZPFOHVSLKX-UHFFFAOYSA-N (2,3-dichlorophenyl) prop-2-enoate Chemical compound ClC1=CC=CC(OC(=O)C=C)=C1Cl SGYGZPFOHVSLKX-UHFFFAOYSA-N 0.000 description 1
DSTSFPQVJKRKMB-UHFFFAOYSA-N (2-bromo-2-phenoxyethyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(Br)OC1=CC=CC=C1 DSTSFPQVJKRKMB-UHFFFAOYSA-N 0.000 description 1
FOBYPGIKPJMTQD-UHFFFAOYSA-N (2-bromo-2-phenoxyethyl) prop-2-enoate Chemical compound C=CC(=O)OCC(Br)OC1=CC=CC=C1 FOBYPGIKPJMTQD-UHFFFAOYSA-N 0.000 description 1
VWTOJOYJECIYNH-UHFFFAOYSA-N (2-chloro-2-phenoxyethyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(Cl)OC1=CC=CC=C1 VWTOJOYJECIYNH-UHFFFAOYSA-N 0.000 description 1
FBRABRGSIGJCTD-UHFFFAOYSA-N (2-chloro-2-phenoxyethyl) prop-2-enoate Chemical compound C=CC(=O)OCC(Cl)OC1=CC=CC=C1 FBRABRGSIGJCTD-UHFFFAOYSA-N 0.000 description 1
VMLATLXXUPZKMJ-UHFFFAOYSA-N (4-bromophenyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=C(Br)C=C1 VMLATLXXUPZKMJ-UHFFFAOYSA-N 0.000 description 1
HWWIOYDCNOHHMH-UHFFFAOYSA-N (4-bromophenyl) prop-2-enoate Chemical compound BrC1=CC=C(OC(=O)C=C)C=C1 HWWIOYDCNOHHMH-UHFFFAOYSA-N 0.000 description 1
SIADNYSYTSORRE-UHFFFAOYSA-N (4-chlorophenyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=C(Cl)C=C1 SIADNYSYTSORRE-UHFFFAOYSA-N 0.000 description 1
IGHDIBHFCIOXGK-UHFFFAOYSA-N (4-chlorophenyl) prop-2-enoate Chemical compound ClC1=CC=C(OC(=O)C=C)C=C1 IGHDIBHFCIOXGK-UHFFFAOYSA-N 0.000 description 1
ROLAGNYPWIVYTG-UHFFFAOYSA-N 1,2-bis(4-methoxyphenyl)ethanamine;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1CC(N)C1=CC=C(OC)C=C1 ROLAGNYPWIVYTG-UHFFFAOYSA-N 0.000 description 1
ATOUXIOKEJWULN-UHFFFAOYSA-N 1,6-diisocyanato-2,2,4-trimethylhexane Chemical compound O=C=NCCC(C)CC(C)(C)CN=C=O ATOUXIOKEJWULN-UHFFFAOYSA-N 0.000 description 1
CISIJYCKDJSTMX-UHFFFAOYSA-N 2,2-dichloroethenylbenzene Chemical compound ClC(Cl)=CC1=CC=CC=C1 CISIJYCKDJSTMX-UHFFFAOYSA-N 0.000 description 1
CMQUQOHNANGDOR-UHFFFAOYSA-N 2,3-dibromo-4-(2,4-dibromo-5-hydroxyphenyl)phenol Chemical group BrC1=C(Br)C(O)=CC=C1C1=CC(O)=C(Br)C=C1Br CMQUQOHNANGDOR-UHFFFAOYSA-N 0.000 description 1
ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
BNJMVIYUUNVKHZ-UHFFFAOYSA-N 2-(2,3,4,5,6-pentabromophenoxy)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOC1=C(Br)C(Br)=C(Br)C(Br)=C1Br BNJMVIYUUNVKHZ-UHFFFAOYSA-N 0.000 description 1
WPKYHACUJAHAQD-UHFFFAOYSA-N 2-(2,3,4,5,6-pentabromophenoxy)ethyl prop-2-enoate Chemical compound BrC1=C(Br)C(Br)=C(OCCOC(=O)C=C)C(Br)=C1Br WPKYHACUJAHAQD-UHFFFAOYSA-N 0.000 description 1
AMBJXYFIMKHOQE-UHFFFAOYSA-N 2-(2,4,6-tribromophenoxy)ethyl prop-2-enoate Chemical compound BrC1=CC(Br)=C(OCCOC(=O)C=C)C(Br)=C1 AMBJXYFIMKHOQE-UHFFFAOYSA-N 0.000 description 1
GMWRLARXAFKXJD-UHFFFAOYSA-N 2-[2,6-dibromo-4-[2-(3,5-dibromo-4-hydroxyphenyl)propan-2-yl]phenoxy]ethyl prop-2-enoate Chemical compound C=1C(Br)=C(OCCOC(=O)C=C)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 GMWRLARXAFKXJD-UHFFFAOYSA-N 0.000 description 1
BGVZQPHUMBWGNF-UHFFFAOYSA-N 2-[2,6-dibromo-4-[2-[3,5-dibromo-4-(2-hydroxyethoxy)phenyl]propan-2-yl]phenoxy]ethyl prop-2-enoate Chemical compound C=1C(Br)=C(OCCOC(=O)C=C)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(OCCO)C(Br)=C1 BGVZQPHUMBWGNF-UHFFFAOYSA-N 0.000 description 1
OOGPFCFGQOSOOZ-UHFFFAOYSA-N 2-[2,6-dibromo-4-[2-[3,5-dibromo-4-(2-prop-2-enoyloxyethoxy)phenyl]propan-2-yl]phenoxy]ethyl prop-2-enoate Chemical compound C=1C(Br)=C(OCCOC(=O)C=C)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(OCCOC(=O)C=C)C(Br)=C1 OOGPFCFGQOSOOZ-UHFFFAOYSA-N 0.000 description 1
JZOBIVDRMAPQDS-UHFFFAOYSA-N 2-[2,6-dibromo-4-[2-[3,5-dibromo-4-[2-(2-methylprop-2-enoyloxy)ethoxy]phenyl]propan-2-yl]phenoxy]ethyl 2-methylprop-2-enoate Chemical compound C1=C(Br)C(OCCOC(=O)C(=C)C)=C(Br)C=C1C(C)(C)C1=CC(Br)=C(OCCOC(=O)C(C)=C)C(Br)=C1 JZOBIVDRMAPQDS-UHFFFAOYSA-N 0.000 description 1
OZPOYKXYJOHGCW-UHFFFAOYSA-N 2-iodoethenylbenzene Chemical compound IC=CC1=CC=CC=C1 OZPOYKXYJOHGCW-UHFFFAOYSA-N 0.000 description 1
OELQSSWXRGADDE-UHFFFAOYSA-N 2-methylprop-2-eneperoxoic acid Chemical compound CC(=C)C(=O)OO OELQSSWXRGADDE-UHFFFAOYSA-N 0.000 description 1
UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
NNWNNQTUZYVQRK-UHFFFAOYSA-N 5-bromo-1h-pyrrolo[2,3-c]pyridine-2-carboxylic acid Chemical compound BrC1=NC=C2NC(C(=O)O)=CC2=C1 NNWNNQTUZYVQRK-UHFFFAOYSA-N 0.000 description 1
239000004925 Acrylic resin Substances 0.000 description 1
229920000178 Acrylic resin Polymers 0.000 description 1
229920002574 CR-39 Polymers 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
102100026735 Coagulation factor VIII Human genes 0.000 description 1
101000911390 Homo sapiens Coagulation factor VIII Proteins 0.000 description 1
WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
240000001987 Pyrus communis Species 0.000 description 1
OQMAFZZZMAWNQE-UHFFFAOYSA-N [2,6-dibromo-4-[2-(3,5-dibromo-2,6-diethoxy-4-hydroxyphenyl)propan-2-yl]-3,5-diethoxyphenyl] 2-methylprop-2-enoate Chemical compound CCOC1=C(Br)C(O)=C(Br)C(OCC)=C1C(C)(C)C1=C(OCC)C(Br)=C(OC(=O)C(C)=C)C(Br)=C1OCC OQMAFZZZMAWNQE-UHFFFAOYSA-N 0.000 description 1
HUOSJNPPWBJFGS-UHFFFAOYSA-N [2,6-dibromo-4-[2-[3,5-dibromo-4-(2-hydroxyethoxy)phenyl]propan-2-yl]-3-ethoxyphenyl] prop-2-enoate Chemical compound CCOC1=C(Br)C(OC(=O)C=C)=C(Br)C=C1C(C)(C)C1=CC(Br)=C(OCCO)C(Br)=C1 HUOSJNPPWBJFGS-UHFFFAOYSA-N 0.000 description 1
SBSWYHHJLIRRGE-UHFFFAOYSA-N [2,6-dibromo-4-[2-[3,5-dibromo-4-(2-hydroxyethoxy)phenyl]propan-2-yl]phenyl] prop-2-enoate Chemical compound C=1C(Br)=C(OC(=O)C=C)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(OCCO)C(Br)=C1 SBSWYHHJLIRRGE-UHFFFAOYSA-N 0.000 description 1
VIFJGPJLCPFZIO-UHFFFAOYSA-N [2-hydroxy-3-(2,4,6-tribromo-3-methylphenoxy)propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)COC1=C(Br)C=C(Br)C(C)=C1Br VIFJGPJLCPFZIO-UHFFFAOYSA-N 0.000 description 1
JGDGEEDJKIDDRC-UHFFFAOYSA-N [2-hydroxy-3-(2,4,6-triiodophenoxy)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(O)COC1=C(I)C=C(I)C=C1I JGDGEEDJKIDDRC-UHFFFAOYSA-N 0.000 description 1
TUSNCCXAJVGRLL-UHFFFAOYSA-N [2-hydroxy-3-(3-iodo-5-methylphenoxy)propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)COC1=CC(C)=CC(I)=C1 TUSNCCXAJVGRLL-UHFFFAOYSA-N 0.000 description 1
VEVOYUSBVPGLMK-UHFFFAOYSA-N [3-(2,4-dibromophenoxy)-2-hydroxypropyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)COC1=CC=C(Br)C=C1Br VEVOYUSBVPGLMK-UHFFFAOYSA-N 0.000 description 1
FSOASCCXBQCXLI-UHFFFAOYSA-N [3-(2,4-dibromophenoxy)-3-hydroxypropyl] prop-2-enoate Chemical compound C=CC(=O)OCCC(O)OC1=CC=C(Br)C=C1Br FSOASCCXBQCXLI-UHFFFAOYSA-N 0.000 description 1
GIIRJYMUMBQWMO-UHFFFAOYSA-N [3-(3-bromo-5-methylphenoxy)-2-hydroxypropyl] prop-2-enoate Chemical compound CC1=CC(Br)=CC(OCC(O)COC(=O)C=C)=C1 GIIRJYMUMBQWMO-UHFFFAOYSA-N 0.000 description 1
VCCQNTSZQMPBRW-UHFFFAOYSA-N [3-hydroxy-3-(2,4,6-tribromo-3-methylphenoxy)propyl] prop-2-enoate Chemical compound CC1=C(Br)C=C(Br)C(OC(O)CCOC(=O)C=C)=C1Br VCCQNTSZQMPBRW-UHFFFAOYSA-N 0.000 description 1
KXBFLNPZHXDQLV-UHFFFAOYSA-N [cyclohexyl(diisocyanato)methyl]cyclohexane Chemical compound C1CCCCC1C(N=C=O)(N=C=O)C1CCCCC1 KXBFLNPZHXDQLV-UHFFFAOYSA-N 0.000 description 1
238000005299 abrasion Methods 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
230000003078 antioxidant effect Effects 0.000 description 1
239000002216 antistatic agent Substances 0.000 description 1
GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 description 1
JKJWYKGYGWOAHT-UHFFFAOYSA-N bis(prop-2-enyl) carbonate Chemical compound C=CCOC(=O)OCC=C JKJWYKGYGWOAHT-UHFFFAOYSA-N 0.000 description 1
OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000011247 coating layer Substances 0.000 description 1
AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 1
238000002845 discoloration Methods 0.000 description 1
239000007850 fluorescent dye Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000008240 homogeneous mixture Substances 0.000 description 1
239000012456 homogeneous solution Substances 0.000 description 1
239000002184 metal Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
QIWKUEJZZCOPFV-UHFFFAOYSA-N phenyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC=C1 QIWKUEJZZCOPFV-UHFFFAOYSA-N 0.000 description 1
WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 description 1
229920005668 polycarbonate resin Polymers 0.000 description 1
239000004431 polycarbonate resin Substances 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
150000003077 polyols Chemical class 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
229920005990 polystyrene resin Polymers 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000000047 product Substances 0.000 description 1
RGBXDEHYFWDBKD-UHFFFAOYSA-N propan-2-yl propan-2-yloxy carbonate Chemical compound CC(C)OOC(=O)OC(C)C RGBXDEHYFWDBKD-UHFFFAOYSA-N 0.000 description 1
239000007870 radical polymerization initiator Substances 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000004381 surface treatment Methods 0.000 description 1
238000010998 test method Methods 0.000 description 1
229920001187 thermosetting polymer Polymers 0.000 description 1
DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
239000006097 ultraviolet radiation absorber Substances 0.000 description 1
238000001771 vacuum deposition Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Landscapes

Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

CA000437130A 1983-09-20 1983-09-20 Resine pour verres optiques, et verres faits de ladite resine Expired CA1207939A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000437130A CA1207939A (fr)	1983-09-20	1983-09-20	Resine pour verres optiques, et verres faits de ladite resine

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000437130A CA1207939A (fr)	1983-09-20	1983-09-20	Resine pour verres optiques, et verres faits de ladite resine

Publications (1)

Publication Number	Publication Date
CA1207939A true CA1207939A (fr)	1986-07-15

Family

ID=4126123

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000437130A Expired CA1207939A (fr)	1983-09-20	1983-09-20	Resine pour verres optiques, et verres faits de ladite resine

Country Status (1)

Country	Link
CA (1)	CA1207939A (fr)

1983
- 1983-09-20 CA CA000437130A patent/CA1207939A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2003-09-20	MKEX	Expiry
2023-05-26	MKEX	Expiry	Effective date: 20030920

Publication	Publication Date	Title
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GB2176794A (en)	1987-01-07	Copolymer having high refractive index
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US5288844A (en)	1994-02-22	High-refractive index plastic optical material
JPH07206974A (ja)	1995-08-08	重合性組成物およびそれより得られる高屈折率プラスチックレンズ
CA1207939A (fr)	1986-07-15	Resine pour verres optiques, et verres faits de ladite resine
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JPH06294901A (ja)	1994-10-21	プラスチックレンズ材料
JPH01242612A (ja)	1989-09-27	プラスチックレンズ
JPH01182314A (ja)	1989-07-20	高アッベ数レンズ用組成物
JPS6051706A (ja)	1985-03-23	高屈折率プラスチツクレンズ用樹脂
JP2961158B2 (ja)	1999-10-12	光学用樹脂成形体
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JPH0435722B2 (fr)	1992-06-12
JP2800265B2 (ja)	1998-09-21	高屈折率プラスチックレンズ用組成物