WO2023068316A1 - Matériau pour lentille de contact souple ayant une fonction d'amélioration du contraste - Google Patents
Matériau pour lentille de contact souple ayant une fonction d'amélioration du contraste Download PDFInfo
- Publication number
- WO2023068316A1 WO2023068316A1 PCT/JP2022/039021 JP2022039021W WO2023068316A1 WO 2023068316 A1 WO2023068316 A1 WO 2023068316A1 JP 2022039021 W JP2022039021 W JP 2022039021W WO 2023068316 A1 WO2023068316 A1 WO 2023068316A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- meth
- group
- polymer
- acrylate
- carbon atoms
- Prior art date
Links
- 239000000463 material Substances 0.000 title abstract description 21
- 229920000642 polymer Polymers 0.000 claims abstract description 115
- 239000000178 monomer Substances 0.000 claims abstract description 97
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 22
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims abstract description 21
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 20
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 11
- 239000010703 silicon Substances 0.000 claims abstract description 11
- -1 tetraazaporphyrin compound Chemical class 0.000 claims description 84
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- 238000000862 absorption spectrum Methods 0.000 claims description 26
- 238000010521 absorption reaction Methods 0.000 claims description 16
- 125000004429 atom Chemical group 0.000 claims description 13
- 230000031700 light absorption Effects 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 239000002184 metal Substances 0.000 claims description 10
- 229910052751 metal Inorganic materials 0.000 claims description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 6
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 claims description 4
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 claims description 4
- PNLUGRYDUHRLOF-UHFFFAOYSA-N n-ethenyl-n-methylacetamide Chemical compound C=CN(C)C(C)=O PNLUGRYDUHRLOF-UHFFFAOYSA-N 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000005110 aryl thio group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 150000001721 carbon Chemical group 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 239000010949 copper Substances 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 125000005647 linker group Chemical group 0.000 claims description 3
- 150000004032 porphyrins Chemical group 0.000 claims description 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 3
- 238000000465 moulding Methods 0.000 claims description 2
- 239000003086 colorant Substances 0.000 abstract description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 92
- 239000000975 dye Substances 0.000 description 46
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 30
- 239000012965 benzophenone Substances 0.000 description 30
- 238000010828 elution Methods 0.000 description 29
- 238000012360 testing method Methods 0.000 description 24
- 239000004205 dimethyl polysiloxane Substances 0.000 description 22
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 22
- 229940076442 9,10-anthraquinone Drugs 0.000 description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 238000002835 absorbance Methods 0.000 description 17
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 230000014759 maintenance of location Effects 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 8
- 238000002834 transmittance Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000006096 absorbing agent Substances 0.000 description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
- 229910052731 fluorine Inorganic materials 0.000 description 7
- 239000011737 fluorine Substances 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 238000007334 copolymerization reaction Methods 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 230000035699 permeability Effects 0.000 description 6
- 239000003505 polymerization initiator Substances 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- 239000003085 diluting agent Substances 0.000 description 5
- 238000007922 dissolution test Methods 0.000 description 5
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 4
- 239000003431 cross linking reagent Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 230000004313 glare Effects 0.000 description 3
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 150000003440 styrenes Chemical class 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- XLPJNCYCZORXHG-UHFFFAOYSA-N 1-morpholin-4-ylprop-2-en-1-one Chemical compound C=CC(=O)N1CCOCC1 XLPJNCYCZORXHG-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
- WFRBDWRZVBPBDO-UHFFFAOYSA-N 2-methyl-2-pentanol Chemical compound CCCC(C)(C)O WFRBDWRZVBPBDO-UHFFFAOYSA-N 0.000 description 2
- KBIWOJBFYNSQKW-UHFFFAOYSA-N 3-ethenylphthalic acid Chemical compound OC(=O)C1=CC=CC(C=C)=C1C(O)=O KBIWOJBFYNSQKW-UHFFFAOYSA-N 0.000 description 2
- FRDAATYAJDYRNW-UHFFFAOYSA-N 3-methyl-3-pentanol Chemical compound CCC(C)(O)CC FRDAATYAJDYRNW-UHFFFAOYSA-N 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 150000004699 copper complex Chemical class 0.000 description 2
- 210000004087 cornea Anatomy 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- QNVRIHYSUZMSGM-UHFFFAOYSA-N hexan-2-ol Chemical compound CCCCC(C)O QNVRIHYSUZMSGM-UHFFFAOYSA-N 0.000 description 2
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 2
- SJWFXCIHNDVPSH-UHFFFAOYSA-N octan-2-ol Chemical compound CCCCCCC(C)O SJWFXCIHNDVPSH-UHFFFAOYSA-N 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 239000012860 organic pigment Substances 0.000 description 2
- JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
- MJYFYGVCLHNRKB-UHFFFAOYSA-N 1,1,2-trifluoroethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(F)(F)CF MJYFYGVCLHNRKB-UHFFFAOYSA-N 0.000 description 1
- QBEGDGXVZRFBNO-UHFFFAOYSA-N 1,1-bis[2-(2-methoxyethoxy)ethoxy]-2-methylpropane Chemical compound COCCOCCOC(C(C)C)OCCOCCOC QBEGDGXVZRFBNO-UHFFFAOYSA-N 0.000 description 1
- VNQXSTWCDUXYEZ-UHFFFAOYSA-N 1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione Chemical compound C1CC2(C)C(=O)C(=O)C1C2(C)C VNQXSTWCDUXYEZ-UHFFFAOYSA-N 0.000 description 1
- 239000005968 1-Decanol Substances 0.000 description 1
- FMSBDDXYTGRROM-UHFFFAOYSA-N 1-amino-4-(3-ethenylanilino)-9,10-dioxoanthracene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C(N)=C2C(=O)C3=CC=CC=C3C(=O)C2=C1NC1=CC=CC(C=C)=C1 FMSBDDXYTGRROM-UHFFFAOYSA-N 0.000 description 1
- NOCOYBAJWYLBMW-UHFFFAOYSA-N 1-amino-4-(4-ethenylanilino)-9,10-dioxoanthracene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C(N)=C2C(=O)C3=CC=CC=C3C(=O)C2=C1NC1=CC=C(C=C)C=C1 NOCOYBAJWYLBMW-UHFFFAOYSA-N 0.000 description 1
- NETQWKMHDYXHPQ-UHFFFAOYSA-N 1-amino-4-[(2-ethenylphenyl)methylamino]-9,10-dioxoanthracene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C(N)=C2C(=O)C3=CC=CC=C3C(=O)C2=C1NCC1=CC=CC=C1C=C NETQWKMHDYXHPQ-UHFFFAOYSA-N 0.000 description 1
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 1
- LGJCFVYMIJLQJO-UHFFFAOYSA-N 1-dodecylperoxydodecane Chemical compound CCCCCCCCCCCCOOCCCCCCCCCCCC LGJCFVYMIJLQJO-UHFFFAOYSA-N 0.000 description 1
- LVJZCPNIJXVIAT-UHFFFAOYSA-N 1-ethenyl-2,3,4,5,6-pentafluorobenzene Chemical compound FC1=C(F)C(F)=C(C=C)C(F)=C1F LVJZCPNIJXVIAT-UHFFFAOYSA-N 0.000 description 1
- JWYVGKFDLWWQJX-UHFFFAOYSA-N 1-ethenylazepan-2-one Chemical compound C=CN1CCCCCC1=O JWYVGKFDLWWQJX-UHFFFAOYSA-N 0.000 description 1
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 description 1
- PBGPBHYPCGDFEZ-UHFFFAOYSA-N 1-ethenylpiperidin-2-one Chemical compound C=CN1CCCCC1=O PBGPBHYPCGDFEZ-UHFFFAOYSA-N 0.000 description 1
- LEWNYOKWUAYXPI-UHFFFAOYSA-N 1-ethenylpiperidine Chemical compound C=CN1CCCCC1 LEWNYOKWUAYXPI-UHFFFAOYSA-N 0.000 description 1
- VOCDJQSAMZARGX-UHFFFAOYSA-N 1-ethenylpyrrolidine-2,5-dione Chemical compound C=CN1C(=O)CCC1=O VOCDJQSAMZARGX-UHFFFAOYSA-N 0.000 description 1
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 1
- JRHNUZCXXOTJCA-UHFFFAOYSA-N 1-fluoropropane Chemical compound CCCF JRHNUZCXXOTJCA-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- AFXKUUDFKHVAGI-UHFFFAOYSA-N 1-methyl-3-methylidenepyrrolidin-2-one Chemical compound CN1CCC(=C)C1=O AFXKUUDFKHVAGI-UHFFFAOYSA-N 0.000 description 1
- DGPVNNMFVYYVDF-UHFFFAOYSA-N 1-prop-2-enoylpyrrolidin-2-one Chemical compound C=CC(=O)N1CCCC1=O DGPVNNMFVYYVDF-UHFFFAOYSA-N 0.000 description 1
- GQCZPFJGIXHZMB-UHFFFAOYSA-N 1-tert-Butoxy-2-propanol Chemical compound CC(O)COC(C)(C)C GQCZPFJGIXHZMB-UHFFFAOYSA-N 0.000 description 1
- YKKXFZFBCMUAQI-UHFFFAOYSA-N 2,3,6,7-tetramethyloctane-2,3,6,7-tetrol Chemical compound CC(C)(O)C(C)(O)CCC(C)(O)C(C)(C)O YKKXFZFBCMUAQI-UHFFFAOYSA-N 0.000 description 1
- YHYCMHWTYHPIQS-UHFFFAOYSA-N 2-(2-hydroxyethoxy)-1-methoxyethanol Chemical compound COC(O)COCCO YHYCMHWTYHPIQS-UHFFFAOYSA-N 0.000 description 1
- HLIQLHSBZXDKLV-UHFFFAOYSA-N 2-(2-hydroxyethoxy)-1-phenoxyethanol Chemical compound OCCOCC(O)OC1=CC=CC=C1 HLIQLHSBZXDKLV-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical group FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- LESMLVDJJCWZAJ-UHFFFAOYSA-N 2-(diphenylphosphorylmethyl)-1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=CC(C)=C1CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 LESMLVDJJCWZAJ-UHFFFAOYSA-N 0.000 description 1
- QNVRIHYSUZMSGM-LURJTMIESA-N 2-Hexanol Natural products CCCC[C@H](C)O QNVRIHYSUZMSGM-LURJTMIESA-N 0.000 description 1
- PFHOSZAOXCYAGJ-UHFFFAOYSA-N 2-[(2-cyano-4-methoxy-4-methylpentan-2-yl)diazenyl]-4-methoxy-2,4-dimethylpentanenitrile Chemical compound COC(C)(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)(C)OC PFHOSZAOXCYAGJ-UHFFFAOYSA-N 0.000 description 1
- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 description 1
- WAEVWDZKMBQDEJ-UHFFFAOYSA-N 2-[2-(2-methoxypropoxy)propoxy]propan-1-ol Chemical compound COC(C)COC(C)COC(C)CO WAEVWDZKMBQDEJ-UHFFFAOYSA-N 0.000 description 1
- ZCSRSYOFMWMZPU-UHFFFAOYSA-N 2-[3-tert-butyl-4-hydroxy-5-(5-methylbenzotriazol-2-yl)phenoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(C)(C)C1=CC(OCCOC(=O)C(=C)C)=CC(N2N=C3C=C(C)C=CC3=N2)=C1O ZCSRSYOFMWMZPU-UHFFFAOYSA-N 0.000 description 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- TZYRSLHNPKPEFV-UHFFFAOYSA-N 2-ethyl-1-butanol Chemical compound CCC(CC)CO TZYRSLHNPKPEFV-UHFFFAOYSA-N 0.000 description 1
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 1
- FEWFXBUNENSNBQ-UHFFFAOYSA-N 2-hydroxyacrylic acid Chemical class OC(=C)C(O)=O FEWFXBUNENSNBQ-UHFFFAOYSA-N 0.000 description 1
- LTRFAFPZXDAXTK-UHFFFAOYSA-N 2-n-(4-phenyldiazenylphenyl)-6-prop-1-en-2-yl-1,3,5-triazine-2,4-diamine Chemical compound CC(=C)C1=NC(N)=NC(NC=2C=CC(=CC=2)N=NC=2C=CC=CC=2)=N1 LTRFAFPZXDAXTK-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000005351 2-phenylphenols Chemical class 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- HKADMMFLLPJEAG-UHFFFAOYSA-N 3,3,3-trifluoroprop-1-enylbenzene Chemical compound FC(F)(F)C=CC1=CC=CC=C1 HKADMMFLLPJEAG-UHFFFAOYSA-N 0.000 description 1
- NDVMXLAIXHSGNA-UHFFFAOYSA-N 3,5,7,9,11,13-hexamethoxytetradecan-1-ol Chemical compound COC(C)CC(OC)CC(OC)CC(OC)CC(OC)CC(OC)CCO NDVMXLAIXHSGNA-UHFFFAOYSA-N 0.000 description 1
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
- ZTHJQCDAHYOPIK-UHFFFAOYSA-N 3-methylbut-2-en-2-ylbenzene Chemical compound CC(C)=C(C)C1=CC=CC=C1 ZTHJQCDAHYOPIK-UHFFFAOYSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- KFDVPJUYSDEJTH-UHFFFAOYSA-N 4-ethenylpyridine Chemical compound C=CC1=CC=NC=C1 KFDVPJUYSDEJTH-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- CSWAXJNHQAKAQO-UHFFFAOYSA-N CC(C(C(C1=CC=CC=C11)=O)=C(C(NCCOC(C2=CC=C(C=C)C=C2)=O)=C2)C1=O)=C2N Chemical compound CC(C(C(C1=CC=CC=C11)=O)=C(C(NCCOC(C2=CC=C(C=C)C=C2)=O)=C2)C1=O)=C2N CSWAXJNHQAKAQO-UHFFFAOYSA-N 0.000 description 1
- OVJBJXXPTNFCLK-UHFFFAOYSA-N CN(C)C=CC1=CC=CC=C1.C=CC1=CC=CC=C1 Chemical class CN(C)C=CC1=CC=CC=C1.C=CC1=CC=CC=C1 OVJBJXXPTNFCLK-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
- 239000004641 Diallyl-phthalate Substances 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- YSVZGWAJIHWNQK-UHFFFAOYSA-N [3-(hydroxymethyl)-2-bicyclo[2.2.1]heptanyl]methanol Chemical compound C1CC2C(CO)C(CO)C1C2 YSVZGWAJIHWNQK-UHFFFAOYSA-N 0.000 description 1
- WCGSLIJTSZHWBO-UHFFFAOYSA-N [dimethyl(2-phenylethenyl)silyl] tris(trimethylsilyl) silicate Chemical compound C[Si](C)(C)O[Si](O[Si](C)(C)C)(O[Si](C)(C)C)O[Si](C)(C)C=CC1=CC=CC=C1 WCGSLIJTSZHWBO-UHFFFAOYSA-N 0.000 description 1
- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 description 1
- 239000011358 absorbing material Substances 0.000 description 1
- 150000008062 acetophenones Chemical class 0.000 description 1
- 239000002253 acid 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
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 239000001000 anthraquinone dye Substances 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 208000003464 asthenopia Diseases 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- ZPOLOEWJWXZUSP-AATRIKPKSA-N bis(prop-2-enyl) (e)-but-2-enedioate Chemical compound C=CCOC(=O)\C=C\C(=O)OCC=C ZPOLOEWJWXZUSP-AATRIKPKSA-N 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
- FPODCVUTIPDRTE-UHFFFAOYSA-N bis(prop-2-enyl) hexanedioate Chemical compound C=CCOC(=O)CCCCC(=O)OCC=C FPODCVUTIPDRTE-UHFFFAOYSA-N 0.000 description 1
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 1
- 229930006711 bornane-2,3-dione Natural products 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000003851 corona treatment Methods 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- ISAOCJYIOMOJEB-UHFFFAOYSA-N desyl alcohol Natural products C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 125000005594 diketone group Chemical group 0.000 description 1
- GYWDBBXLKZFJLS-UHFFFAOYSA-N dimethyl-[methyl-bis(trimethylsilyloxy)silyl]oxy-(2-phenylethenyl)silane Chemical compound C[Si](C)(C)O[Si](C)(O[Si](C)(C)C)O[Si](C)(C)C=CC1=CC=CC=C1 GYWDBBXLKZFJLS-UHFFFAOYSA-N 0.000 description 1
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 1
- 208000028659 discharge Diseases 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000017 hydrogel Substances 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000005641 methacryl group Chemical group 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- WFKDPJRCBCBQNT-UHFFFAOYSA-N n,2-dimethylprop-2-enamide Chemical compound CNC(=O)C(C)=C WFKDPJRCBCBQNT-UHFFFAOYSA-N 0.000 description 1
- QRWZCJXEAOZAAW-UHFFFAOYSA-N n,n,2-trimethylprop-2-enamide Chemical compound CN(C)C(=O)C(C)=C QRWZCJXEAOZAAW-UHFFFAOYSA-N 0.000 description 1
- JMCVCHBBHPFWBF-UHFFFAOYSA-N n,n-diethyl-2-methylprop-2-enamide Chemical compound CCN(CC)C(=O)C(C)=C JMCVCHBBHPFWBF-UHFFFAOYSA-N 0.000 description 1
- OVHHHVAVHBHXAK-UHFFFAOYSA-N n,n-diethylprop-2-enamide Chemical compound CCN(CC)C(=O)C=C OVHHHVAVHBHXAK-UHFFFAOYSA-N 0.000 description 1
- YKHOZZZNHLSBOA-UHFFFAOYSA-N n-(2-aminoethyl)-n-ethyl-2-methylprop-2-enamide Chemical compound NCCN(CC)C(=O)C(C)=C YKHOZZZNHLSBOA-UHFFFAOYSA-N 0.000 description 1
- BSCJIBOZTKGXQP-UHFFFAOYSA-N n-(2-hydroxyethyl)-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NCCO BSCJIBOZTKGXQP-UHFFFAOYSA-N 0.000 description 1
- UUORTJUPDJJXST-UHFFFAOYSA-N n-(2-hydroxyethyl)prop-2-enamide Chemical compound OCCNC(=O)C=C UUORTJUPDJJXST-UHFFFAOYSA-N 0.000 description 1
- QQZOPKMRPOGIEB-UHFFFAOYSA-N n-butyl methyl ketone Natural products CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
- GORGQKRVQGXVEB-UHFFFAOYSA-N n-ethenyl-n-ethylacetamide Chemical compound CCN(C=C)C(C)=O GORGQKRVQGXVEB-UHFFFAOYSA-N 0.000 description 1
- DFMIMUDDPBAKFS-UHFFFAOYSA-N n-ethenyl-n-ethylformamide Chemical compound CCN(C=C)C=O DFMIMUDDPBAKFS-UHFFFAOYSA-N 0.000 description 1
- RQAKESSLMFZVMC-UHFFFAOYSA-N n-ethenylacetamide Chemical compound CC(=O)NC=C RQAKESSLMFZVMC-UHFFFAOYSA-N 0.000 description 1
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 description 1
- KYKIFKUTBWKKRE-UHFFFAOYSA-N n-ethenylpropan-2-amine Chemical compound CC(C)NC=C KYKIFKUTBWKKRE-UHFFFAOYSA-N 0.000 description 1
- ZIWDVJPPVMGJGR-UHFFFAOYSA-N n-ethyl-2-methylprop-2-enamide Chemical compound CCNC(=O)C(C)=C ZIWDVJPPVMGJGR-UHFFFAOYSA-N 0.000 description 1
- SWPMNMYLORDLJE-UHFFFAOYSA-N n-ethylprop-2-enamide Chemical compound CCNC(=O)C=C SWPMNMYLORDLJE-UHFFFAOYSA-N 0.000 description 1
- YPHQUSNPXDGUHL-UHFFFAOYSA-N n-methylprop-2-enamide Chemical compound CNC(=O)C=C YPHQUSNPXDGUHL-UHFFFAOYSA-N 0.000 description 1
- SOEDHYUFNWMILE-UHFFFAOYSA-N naphthalen-1-yl prop-2-enoate Chemical compound C1=CC=C2C(OC(=O)C=C)=CC=CC2=C1 SOEDHYUFNWMILE-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000001005 nitro dye Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000008447 perception Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- VEVUYCJVNUZVBL-UHFFFAOYSA-N phenyl 2-hydroxy-4-(2-methylprop-2-enoyloxymethyl)benzoate Chemical compound OC1=CC(COC(=O)C(=C)C)=CC=C1C(=O)OC1=CC=CC=C1 VEVUYCJVNUZVBL-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- DFOXKPDFWGNLJU-UHFFFAOYSA-N pinacolyl alcohol Chemical compound CC(O)C(C)(C)C DFOXKPDFWGNLJU-UHFFFAOYSA-N 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- AHIHJODVQGBOND-UHFFFAOYSA-M propan-2-yl carbonate Chemical compound CC(C)OC([O-])=O AHIHJODVQGBOND-UHFFFAOYSA-M 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 210000001525 retina Anatomy 0.000 description 1
- 150000003872 salicylic acid derivatives Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YKENVNAJIQUGKU-UHFFFAOYSA-N tetraazaporphin Chemical class C=1C(C=N2)=NC2=NC(NN2)=NC2=CC(C=C2)=NC2=CC2=NC=1C=C2 YKENVNAJIQUGKU-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
Images
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
- C08F2/00—Processes of polymerisation
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
-
- 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
- C08F20/00—Homopolymers and 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
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/52—Amides or imides
- C08F20/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F20/56—Acrylamide; Methacrylamide
-
- 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
- C08F26/00—Homopolymers and 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 single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
-
- 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
- C08F30/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F30/04—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
- C08F30/08—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon
-
- 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
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
-
- G—PHYSICS
- G02—OPTICS
- G02C—SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
- G02C7/00—Optical parts
- G02C7/02—Lenses; Lens systems ; Methods of designing lenses
- G02C7/04—Contact lenses for the eyes
-
- G—PHYSICS
- G02—OPTICS
- G02C—SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
- G02C7/00—Optical parts
- G02C7/10—Filters, e.g. for facilitating adaptation of the eyes to the dark; Sunglasses
Definitions
- the present invention relates to polymers suitable for soft contact lenses and capable of improving the contrast of visually recognized objects.
- Patent No. 5778109 Japanese Patent Application Laid-Open No. 2019-66501
- Soft contact lenses are also required to have improved antiglare properties and contrast properties.
- soft contact lens materials are required to have softness suitable for wearing and water retention necessary for placing the lens directly on the cornea.
- an object of the present invention is to provide a polymer suitable for a soft contact lens material that can improve antiglare properties and contrast properties.
- the present invention is as follows.
- a polymer obtained by copolymerizing an organic dye having a yellow region light absorption ability and one or more polymerizable monomers A polymer, wherein the polymerizable monomer contains one or more selected from acrylamide-based monomers and vinyl-based monomers.
- a 1 to A 8 are each independently a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydroxy group, an amino group, a carboxyl group, a sulfonic acid group, a linear chain, branched or cyclic alkyl group, alkoxy group having 1 to 20 carbon atoms, aryloxy group having 6 to 20 carbon atoms, monoalkylamino group having 1 to 20 carbon atoms, dialkylamino group having 2 to 20 carbon atoms, carbon a dialkylamino group having 7 to 20 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, a heteroaryl group, an alkylthio group having 6 to 20 carbon atoms, and an arylthio group having 6 to 20 carbon atoms; , may form a ring other than an aromatic ring via a linking group, M is two
- Cu represents a divalent copper atom
- tBu represents a tertiary butyl group
- the four tertiary butyl groups represent four pyrrole rings present in the porphyrin skeleton in formula (2). It means that each one is bound to one carbon atom of .
- the total amount of one or more selected from acrylamide-based monomers and vinyl-based monomers is 30 parts by weight or more when the total amount of polymerizable monomers is 100 parts by weight, [1] to [6] ]
- the present invention it is possible to obtain a polymer suitable for soft contact lens materials that can improve antiglare properties and contrast properties. Since dyes are less likely to elute from such polymers, antiglare properties and contrast properties are maintained, and safety is excellent even when worn repeatedly on a daily basis.
- 1 is a graph showing UV-visible absorption spectra of the polymer of Example 1 before and after an elution test.
- 2 is a graph showing UV-visible absorption spectra of the polymer of Example 2 before and after the elution test.
- 4 is a graph showing UV-visible absorption spectra of the polymer of Example 3 before and after the elution test.
- 4 is a graph showing UV-visible absorption spectra for each polymer of Examples 1-3 after repeating the dissolution test four times.
- 4 is a graph showing UV-visible absorption spectra of the polymer of Example 4 before and after the elution test.
- 10 is a graph showing UV-visible absorption spectra of the polymer of Example 5 before and after the elution test.
- 10 is a graph showing UV-visible absorption spectra of the polymer of Example 6 before and after the elution test.
- 4 is a graph showing the UV-visible absorption spectra for each polymer of Examples 4-6 after repeating the dissolution test four times.
- 4 is a graph showing UV-visible absorption spectra of the polymer of Comparative Example 1 before and after the elution test.
- 4 is a graph showing UV-visible absorption spectra of the polymer of Comparative Example 3 before and after the elution test.
- 4 is a graph showing ultraviolet-visible absorption spectra of the polymers of Comparative Examples 1 and 3 after repeating the dissolution test four times.
- FIG. 10 is a graph showing UV-visible absorption spectra of the polymer of Example 7 before and after the elution test.
- 10 is a graph showing UV-visible absorption spectra of the polymer of Example 8 before and after the elution test.
- 10 is a graph showing the UV-visible absorption spectra of the polymer of Example 9 before and after the elution test.
- 10 is a graph showing the UV-visible absorption spectra of the polymer of Example 10 before and after the elution test.
- 11 is a graph showing UV-visible absorption spectra of the polymer of Example 11 before and after the elution test.
- FIG. 10 is a graph showing UV-visible absorption spectra of the polymer of Example 12 before and after the elution test; FIG.
- FIG. 4 is a graph showing UV-visible absorption spectra for each polymer of Examples 7-12 after repeating the dissolution test four times.
- FIG. 10 is a graph showing the relationship between the amount of dye added and the amount remaining after dissolution treatment in Test Example 3.
- FIG. 4 is a graph showing UV-visible absorption spectra for each polymer of Examples 7-12 after repeating the dissolution test four times.
- FIG. 10 is a graph showing the relationship between the amount of dye added and the amount remaining after dissolution treatment in Test Example 3.
- FIG. 10 is a graph showing the relationship between the amount of dye added and the amount remaining after dissolution treatment in Test Example 3.
- the polymer of the present invention is a polymer obtained by copolymerizing an organic dye having a light absorption ability in the yellow region and one or more polymerizable monomers.
- the polymerizable monomer is characterized by containing one or more selected from acrylamide-based monomers and vinyl-based monomers.
- acrylamide-based monomer refers to an amide compound having an acryloyl group as a polymerizable group
- vinyl-based monomer refers to a compound having a vinyl group as a polymerizable group.
- the total content of one or more selected from acrylamide-based monomers and vinyl-based monomers is preferably 30 parts by weight or more, more preferably 40 parts by weight or more when the total polymerizable monomer is 100 parts by weight. More preferably, 50 parts by weight or more is acrylamide-based monomer and/or vinyl-based monomer.
- the upper limit of the content of the acrylamide-based monomer and/or the vinyl-based monomer is not particularly limited. contains 35 parts by weight or less of acrylamide-based monomers and/or vinyl-based monomers.
- the polymer tends to have the softness (Young's modulus) and water retention (moisture content) suitable for soft contact lenses, and the polymer tends to retain the organic pigment having the ability to absorb light in the yellow region.
- the acrylamide-based monomer is not particularly limited, but acrylamide, N-methylacrylamide, N-ethylacrylamide, N-hydroxyethylacrylamide, N,N-dimethylacrylamide, N,N-diethylacrylamide, N-ethyl-N-amino Ethylacrylamide and the like can be mentioned, and among these, N,N-dimethylacrylamide is particularly preferred.
- vinyl-based monomers include, but are not limited to, N-vinyl-2-pyrrolidone, ⁇ -methylene-N-methylpyrrolidone, N-acryloylpyrrolidone, N-vinylpiperidone, N-vinylcaprolactam, N-methyl-N-vinylacetamide.
- Polymerizable monomers in the present invention may include monomers other than acrylamide-based monomers and vinyl-based monomers.
- Other polymerizable monomers are not particularly limited as long as they are commonly used, and examples thereof include the following.
- (meth)acryl is a term including "methacryl” and "acryl”.
- methacrylamide N-methylmethacrylamide, N-ethylmethacrylamide, N-hydroxyethylmethacrylamide, N,N-dimethylmethacrylamide, N,N-diethylmethacrylamide, N-ethyl-N-aminoethylmethacrylamide, etc. methacrylamides;
- Styrene pentafluorostyrene, methylstyrene, trimethylstyrene, trifluoromethylstyrene, (pentamethyl-3,3-bis(trimethylsiloxy)trisiloxanyl)styrene, (hexamethyl-3-trimethylsiloxytrisiloxanyl)styrene, dimethylaminostyrene styrene derivatives such as;
- aminoalkyl (meth)acrylates such as aminoethyl (meth)acrylate, N-methylaminoethyl (meth)acrylate, N,N-dimethylaminoethyl (meth)acrylate;
- Alkoxy group-containing (meth)acrylates such as methoxyethyl (meth)acrylate, ethoxyethyl (meth)acrylate, methoxydiethylene glycol (meth)acrylate;
- Benzyl (meth)acrylate, 2-phenoxyethyl (meth)acrylate, 2-phenylethyl (meth)acrylate, 2-hydroxy-3-phenoxypropyl (meth)acrylate, phenoxydiethylene glycol (meth)acrylate, tribromophenyl (meth)acrylate Acrylates, 2-(meth)acryloyloxyethyl-phthalic acid, 2-(meth)acryloyloxypropyl phthalic acid, 2-(meth)acryloyloxyethyl-2-hydroxyethyl-phthalic acid, neopentyl glycol-( Meth)acrylic acid-benzoate, EO-modified phenol (meth)acrylate, EO-modified nonylphenol (meth)acrylate, EO-modified orthophenylphenol (meth)acrylate, EO-modified tribromophenyl (meth)acrylate, EO-modified bisphenol A di (meth)acrylates,
- glycidyl (meth)acrylate Tetrahydrofurfuryl (meth)acrylate; N-(meth)acryloylpiperidine; N-(meth)acryloylmorpholine.
- Alkyl esters optionally substituted with alkyl groups such as itaconic acid, crotonic acid, maleic acid, fumaric acid, fluorine-containing alkyl groups, or siloxanylalkyl groups; glycidyl (meth)acrylate; Tetrahydrofurfuryl (meth)acrylate; N-(meth)acryloylpiperidine; N-(meth)acryloylmorpholine.
- one or more of the above polymerizable monomers may be selected and polymerized to form a macromonomer, which may be used as one of the polymerizable monomers for polymer production.
- polymerizable ultraviolet absorbers mainly those that absorb ultraviolet rays
- polymerizable dyes things that do not absorb ultraviolet rays and absorb mainly blue light
- polymerizable ultraviolet rays Absorbing dyes can also be used.
- the polymer of the present invention is used as a soft contact lens material as described later, it is useful because it can adjust the color tone of the soft contact lens, and can impart ultraviolet absorption ability and blue region light absorption ability.
- polymerizable UV absorber for example, a benzophenone-based polymerizable UV absorber disclosed in JP-A-2003-253248 or a benzotriazole-based polymerizable UV absorber disclosed in Japanese Patent No. 2685980 can be used.
- UV absorbers such as benzophenone; 2-(2'-hydroxy -5′-(meth)acryloyloxyethylphenyl)-2H-benzotriazole, 2-(2′-hydroxy-5′-(meth)acryloyloxyethylphenyl)-5-chloro-2H-benzotriazole, 2-( 2′-Hydroxy-5′-(meth)acryloyloxypropylphenyl)-2H-benzotriazole, 2-(2′-hydroxy-5′-(meth)acryloyloxypropyl-3
- Salicylic acid derivative-based polymerizable UV absorber such as phenyl 2-hydroxy-4-methacryloyloxymethylbenzoate; 2-cyano-3-phenyl-3-(3′-(meth)acryloyloxyphenyl) propenyl acid methyl ester, etc. These can be used alone or in combination of two or more.
- polymerizable dye for example, azo-based, anthraquinone-based, nitro-based, and phthalocyanine-based polymerizable dyes disclosed in JP-A-10-148797 can be used. These can be used alone or in combination of two or more.
- polymerizable azo dyes examples include 1-phenylazo-4-(meth)acryloyloxynaphthalene, 1-phenylazo-2-hydroxy-3-(meth)acryloyloxynaphthalene, 1-naphthylazo-2-hydroxy-3- (Meth)acryloyloxynaphthalene, 1-( ⁇ -anthriazo)-2-hydroxy-3-(meth)acryloyloxynaphthalene, 1-((4'-(phenylazo)-phenyl)azo)-2-hydroxy-3- (Meth) acryloyloxynaphthalene, 1-(2′,4′-xylylazo)-2-(meth)acryloyloxynaphthalene, 1-(o-tolylazo)-2-(meth)acryloyloxynaphthalene, 2-(m- (meth)acryloylamido-anilino)-4,6-bis(1′-(o-tolylazo)-2′-n
- polymerizable anthraquinone dyes include 1,5-bis((meth)acryloylamino)-9,10-anthraquinone, 1-(4'-vinylbenzoylamido)-9,10-anthraquinone, 4 -amino-1-(4'-vinylbenzoylamido)-9,10-anthraquinone, 5-amino-1-(4'-vinylbenzoylamido)-9,10-anthraquinone, 8-amino-1-(4' -vinylbenzoylamido)-9,10-anthraquinone, 4-nitro-1-(4'-vinylbenzoylamido)-9,10-anthraquinone, 4-hydroxy-1-(4'-vinylbenzoylamido)-9, 10-anthraquinone, 1-(3′-vinylbenzoylamide)-9,10-anthraquinone, 1-
- polymerizable nitro dyes include o-nitroanilinomethyl (meth)acrylate and the like.
- polymerizable phthalocyanine dyes include (meth)acryloylated tetraaminocopper phthalocyanine and (meth)acryloylated (dodecanoylated tetraaminocopper phthalocyanine).
- polymerizable UV-absorbing dyes include 2,4-dihydroxy-3(p-stylenoazo)benzophenone, 2,4-dihydroxy-5-(p-stylenoazo)benzophenone, 2,4-dihydroxy-3 -(p-(meth)acryloyloxymethylphenylazo)benzophenone, 2,4-dihydroxy-5-(p-(meth)acryloyloxymethylphenylazo)benzophenone, 2,4-dihydroxy-3-(p-(meth) ) acryloyloxyethylphenylazo)benzophenone, 2,4-dihydroxy-5-(p-(meth)acryloyloxyethylphenylazo)benzophenone, 2,4-dihydroxy-3-(p-(meth)acryloyloxypropylphenylazo) ) benzophenone, 2,4-dihydroxy-5-(p-(meth)acryloyloxypropylphenylazo)benzophenone, 2,
- the organic dye having the ability to absorb light in the yellow region in the present invention exhibits a specific absorption behavior.
- the organic dye has a main absorption peak (P) between 565 nm and 605 nm in a visible light absorption spectrum measured with a chloroform or toluene solution.
- the organic dye has an absorption coefficient (ml/g ⁇ cm) of 0.5 ⁇ 10 5 or more at the apex of the main absorption peak (P) (Pmax: the point showing the maximum absorption coefficient in the peak).
- the peak width at the absorbance of 1/4 of the absorbance of (Pmax) of the peak (P) is 50 nm or less, and the peak width at the absorbance of 1/2 of the absorbance of (Pmax) of the peak (P) is 30 nm or less, and the peak width at the absorbance of 2/3 of the absorbance of (Pmax) of the peak (P) is in the range of 20 nm or less.
- the organic dye has a peak apex (Pmax) of the main absorption peak (P) between 580 nm and 590 nm.
- the peak width at the absorbance of 1/4 of the absorbance of the peak apex (Pmax) of the main absorption peak (P) is 40 nm or less, and 1 of the absorbance of the peak apex (Pmax) of the main absorption peak (P)
- the peak width at the absorbance of /2 may be 25 nm or less, and the peak width at the absorbance of 2/3 of the absorbance of the peak peak (Pmax) of the main absorption peak (P) may be 20 nm or less.
- organic dyes exhibiting such absorption behavior include tetraazaporphyrin compounds represented by the following general formula (1).
- a 1 to A 8 each independently represent a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydroxy group, an amino group, a carboxyl group, a sulfonic acid group, or a linear chain having 1 to 20 carbon atoms.
- a branched or cyclic alkyl group an alkoxy group having 1 to 20 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, a monoalkylamino group having 1 to 20 carbon atoms, a dialkylamino group having 2 to 20 carbon atoms, a carbon number a dialkylamino group having 7 to 20 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, a heteroaryl group, an alkylthio group having 6 to 20 carbon atoms, an arylthio group having 6 to 20 carbon atoms, A ring other than an aromatic ring may be formed via a linking group.
- M represents two hydrogen atoms, a divalent metal atom, a divalent monosubstituted metal atom, a tetravalent disubstituted metal atom, or an oxymetal atom, preferably a divalent metal Atom, more preferably a divalent copper atom.
- M is a divalent copper atom, and one of A 1 and A 2 , A 3 and A 4 , A 5 and A 6 , and A 7 and A 8 is tertiary butyl is a group and the other is a hydrogen atom.
- a tetra-t-butyl-tetraazaporphyrin/copper complex represented by the following chemical formula (2) is particularly preferable.
- Cu represents a divalent copper atom.
- tBu represents a tertiary butyl group, and the four tertiary butyl groups are each one for one carbon atom of four pyrrole rings present in the porphyrin skeleton in formula (2). It means that they are connected one by one.
- the tetra-t-butyl-tetraazaporphyrin/copper complex represented by the chemical formula (2) is available from Mitsui Chemicals, Inc. under the product number “PD-311S”.
- the polymer of the present invention is obtained by blending an organic dye and a polymerizable monomer having an ability to absorb light in the yellow region in arbitrary amounts, mixing them uniformly, and then copolymerizing the polymerizable monomer mixture. can be done.
- the amount of the organic dye having the ability to absorb light in the yellow region is preferably 0.00001 to 0.02 parts by weight, preferably 0.0001 to 0.02 parts by weight, when the total amount of all polymerizable monomers is 100 parts by weight. 0.01 parts by weight is more preferred, and 0.001 to 0.005 parts by weight is even more preferred. If the amount is less than 0.00001 parts by weight, sufficient antiglare properties and contrast properties may not be obtained.
- the amount of components other than the polymerizable monomer used for copolymerization that is, the organic dye, the polymerization initiator described later, the cross-linking agent, the diluent, etc., when the mixture is included in the polymerizable monomer mixture is , is the amount when the entire polymerizable monomer is 100 parts by weight. Therefore, the total compounding amount of the entire polymerizable monomer mixture is expressed as exceeding 100 parts by weight.
- the polymer of the present invention can be synthesized by a method commonly practiced in the technical field. For example, an organic dye having a yellow region light absorption ability and a polymerizable monomer are uniformly mixed, and if necessary, a polymerization initiator is added and gradually heated in a temperature range of room temperature to about 130 ° C.
- the polymer can be polymerized by irradiation with electromagnetic waves such as microwaves, ultraviolet rays, and radiation (gamma rays).
- electromagnetic waves such as microwaves, ultraviolet rays, and radiation (gamma rays).
- various methods widely and commonly used by those skilled in the art such as radical polymerization, bulk polymerization or solvent polymerization can be employed. You may let
- the polymerizable monomer mixture may contain a polymerization initiator.
- polymerization initiators include lauryl peroxide, benzoyl peroxide, isopropyl carbonate, azobisisobutyronitrile, azobisdimethylvaleronitrile, 2,2′-azobis(2 ,4-dimethylvaleronitrile), 2,2′-azobis(4-methoxy-2,4-dimethylvaleronitrile), benzoyl peroxide, tert-butyl hydroperoxide, cumene hydroperoxide, and other compounds. .
- Photoinitiators such as aromatic ⁇ -hydroxyketones, alkoxyoxybenzoins, acetophenones, acylphosphine oxides, bisacylphosphine oxides and tertiary amines plus diketones can also be used.
- photoinitiators include 1-hydroxycyclohexylphenyl ketone, 2-hydroxy-2-methyl-1-phenyl-propan-1-one, bis(2,6-dimethoxybenzoyl)-2,4- 4-trimethylpentylphosphine oxide, bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide, 2,4,6-trimethylbenzyldiphenylphosphine oxide and 2,4,6-trimethylbenzoyl-diphenylphosphine oxide, benzoin methyl Examples include esters, camphoquinone and ethyl 4-(N,N-dimethylamino)benzoate. One or more of these polymerization initiators can be used.
- the amount of the polymerization initiator used is preferably 0.01 to 5.0 parts by weight, more preferably 0.05 to 2.5 parts by weight, more preferably 0.1 to 1 part by weight, when the total polymerizable monomer is 100 parts by weight. Parts by weight are more preferred.
- the polymerizable monomer mixture may contain a diluent.
- the diluent has the role of increasing the reaction rate of copolymerization and also increasing the releasability of the copolymer.
- the diluent is preferably water-soluble, such as 1-decanol, 1-octanol, 1-pentanol, 1-hexanol, 2-hexanol, 2-octanol, 3-methyl-3-pentanol, 2-pentanol.
- tertiary amyl alcohol tertiary butyl alcohol, 2-butanol, 1-butanol, 2-methyl-2-pentanol, 2-ethyl-1-butanol, 1-propanol, 2-propanol, ethanol, methanol , 3,3-dimethyl-2-butanol, decanoic acid, octanoic acid, dodecanoic acid, 1-ethoxy-2-propanol, 1-tert-butoxy-2-propanol, EH-5, 2,3,6,7- Tetrahydroxy-2,3,6,7-tetramethyloctane, 9-(1-methylethyl)-2,5,8,10,13,16-hexaoxaheptadecane, 3,5,7,9,11 , 13-hexamethoxy-1-tetradecanol, tripropylene glycol methyl ether, water and the like are preferable, and these may be used singly or in combination
- the amount of the diluent used is preferably 0 to 75 parts by weight, more preferably 10 to 70 parts by weight, and even more preferably 30 to 65 parts by weight, when the total polymerizable monomer is 100 parts by weight.
- the polymer of the present invention when the polymer of the present invention is produced by copolymerization, a three-dimensional crosslinked structure can be formed in the resulting polymer by adding a cross-linking agent to the polymerizable monomer mixture. As a result, the mechanical strength and hardness of the polymer can be improved, and the elution of monomers and dyes (including organic dyes having yellow region light absorption ability) from the polymer can be suppressed.
- the polymer of the present invention when the polymer of the present invention is used as a soft contact lens material as described later, it is possible to obtain a uniform, transparent, distortion-free soft contact lens with excellent optical properties, and the soft contact lens has durability ( Chemical resistance, heat resistance, solvent resistance) can also be imparted.
- the blending ratio is preferably in the range of 0.01 to 10 parts by weight based on 100 parts by weight of all the polymerizable monomers. If it is less than 0.01 part by weight, it is difficult to obtain the effect, and if it exceeds 10 parts by weight, the resulting polymer tends to be brittle.
- cross-linking agents examples include butanediol di(meth)acrylate, ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, ) acrylate, dipropylene glycol di(meth)acrylate, diallyl fumarate, allyl (meth)acrylate, vinyl (meth)acrylate, trimethylolpropane tri(meth)acrylate, methacryloyloxyethyl (meth)acrylate, divinylbenzene, diallyl phthalate , diallyl adipate, triallyl diisocyanate, ⁇ -methylene-N-vinylpyrrolidone, 4-vinylbenzyl (meth)acrylate, 3-vinylbenzyl (meth)acrylate, 2,2-bis((meth)acryloyloxyphenyl)hexa Fluoride, ethylene glycol
- a suitable polymerizable monomer can be selected to impart various functionalities to the polymer of the present invention.
- the polymer of the present invention is preferably applied as a soft contact lens material, it is required to have a certain level of oxygen permeability.
- silicon-containing monomers such as the above-mentioned silicon-containing (meth)acrylates and silicon-containing styrene derivatives, fluorine-containing alkyl (meth)acrylates, and the like are used as polymerizable monomers. should be selected.
- silicones having a polymerizable group may be used as polymerizable monomers. These include mono-(meth)acryloyl-terminated polysiloxanes, monoalkyl-terminated polysiloxanes, and more specifically ⁇ -(meth)acryloxypropyl terminated ⁇ -butyl (or ⁇ -methyl) Terminated polydimethylsiloxane, ⁇ -(meth)acryloxy-2-hydroxypropyloxypropyl terminated ⁇ -butyl (or ⁇ -methyl) terminated polydimethylsiloxane, ⁇ -(2-hydroxyl-methacryloxypropyloxypropyl)- ⁇ - Butyl-decamethylpentasiloxane, ⁇ -[3-(meth)acryloxyethoxy-2-hydroxypropyloxypropyl]-terminated ⁇ -butyl (or ⁇ -methyl) terminated polydi
- alkyl (meth)acrylates, styrene derivatives including styrene, or (meth)acrylic acid may be selected as polymerizable monomers.
- the polymer of the present invention can be used as a material for soft contact lenses as described later.
- a contamination function may be added.
- the polymer of the present invention contains structural units of acrylamide-based monomers and/or vinyl-based monomers, it is highly hydrophilic and can be used as a soft, water-absorbing material for soft contact lenses.
- a monomer having a hydrophilic group such as hydroxyacrylates, aminoalkyl acrylates, and acrylates may be selected.
- the polymer of the present invention can be used as a lens material with a high refractive index. .
- polymerizable monomers for imparting various functionalities to the polymer of the present invention it is preferably 0.01 weight part when the total of all polymerizable monomers is 100 parts by weight. parts or more, more preferably 0.05 parts by weight or more, and preferably 5 parts by weight or less, more preferably 3 parts by weight or less when all the polymerizable monomers are 100 parts by weight. .
- the polymer of the present invention retains an organic dye capable of absorbing light in the yellow region inside the polymer. As a result, the contrast becomes clear when viewed when applied to a soft contact lens material. In addition, the anti-glare property is also excellent due to the organic dye having the ability to absorb light in the yellow region. Specifically, the polymer of the present invention has excellent absorption of light in the yellow region, and specifically, the light transmittance at 590 nm is preferably 90% or less, more preferably 80% or less, and still more preferably 70% or less. .
- the polymer of the present invention is also excellent in retention of the organic dye that is retained inside and has the ability to absorb light in the yellow region. Since the dye hardly elutes from such a polymer, the antiglare property and contrast property are maintained, and the soft contact lens is excellent in safety even when worn repeatedly on a daily basis.
- the polymer of the present invention is a hydrogel containing structural units of hydrophilic monomers such as acrylamide-based monomers and/or vinyl-based monomers, it has high water retention.
- the water content ratio of water contained in the polymer to the weight of the polymer
- the oxygen permeability tends to be high, the eyes are less likely to dry out, and it is useful in that it provides an excellent feel when worn.
- the polymer of the present invention has excellent softness.
- the Young's modulus at 25° C. is preferably 0.9 MPa or less, and usually 0.2 MPa or more. Due to such softness, when used as a soft contact lens material, it is useful because it can be worn smoothly and has an excellent feel during wearing.
- the polymer of the present invention has excellent oxygen permeability.
- the oxygen permeability coefficient is preferably 9 to 34 ⁇ 10 ⁇ 11 (cm 2 /sec) ⁇ (mLO 2 /(mL ⁇ mmHg)) when silicon is included in the polymer structure (Si system), and does not contain silicon.
- the case (non-Si system) is preferably 80 to 140 ⁇ 10 ⁇ 11 (cm 2 /sec) ⁇ (mLO 2 /(mL ⁇ mmHg)). Owing to such oxygen permeability, when used as a material for a soft contact lens, the supply of oxygen to the cornea during wearing is less likely to be hindered, which is useful.
- the polymer of the present invention is suitable for application when it is used as a soft contact lens material because it has transparency without becoming cloudy.
- the transparency means that the transmittance of visible light (average transmittance of 400 to 700 nm) is preferably 60% or more, more preferably 70% or more.
- the polymer of the present invention is suitable as a soft contact lens material.
- a soft contact lens material When used as a soft contact lens material, it can be molded by a known method. For example, after a polymerization reaction is carried out in an appropriate mold or container to obtain a rod-shaped, block-shaped, or plate-shaped polymer, it is processed into a desired shape by mechanical processing such as cutting, polishing, or the like. After the polymerization reaction is carried out in a mold corresponding to the above to obtain a polymer molded article, mechanical finish processing is performed as necessary.
- the surface of the lens may be subjected, if necessary, to a surface modification treatment in order to make the surface hydrophilic.
- a surface modification treatment in order to make the surface hydrophilic.
- Plasma treatment or ultraviolet treatment is preferred, and corona Discharge treatment, glow discharge treatment or ultraviolet/ozone treatment is more preferable.
- a processing device and a processing method in that case conventionally known normal devices and methods can be used.
- Example 1 The components shown in Table 1 are uniformly mixed, placed in a polymerization mold (length 30 mm, width 30 mm, thickness 1 mm), polymerized at 65 ° C. for 60 minutes to prepare a polymer sheet with a thickness of 1 mm, and the polymer sheet is released from the mold. bottom.
- the obtained polymer sheet was cut into a size of 10 mm ⁇ 10 mm ⁇ 1 mm, and after being immersed in water at 23° C. for 24 hours, the light transmittance was measured (before the elution test; 0th time). After that, the polymer sheet was immersed in 10 mL of ethanol at 50° C. for 16 hours, and the light transmittance of the eluate was measured. After wiping off ethanol adhering to the surface of the polymer sheet taken out from the eluate, it was subjected to the next ethanol immersion. Elution was carried out four times per polymer sheet, and the light transmittance of the eluate was measured each time. The polymer sheet taken out after the fourth elution was dried at 50° C.
- the light transmittance of the hydrated polymer sheet was measured (after the elution test; 4th time).
- the light transmittance of the polymer sheet was measured using an integrating sphere ultraviolet-visible absorption spectrophotometer (U-4100, Hitachi High-Tech Science), and the eluate was measured using an ultraviolet-visible absorption altimeter (UV-2700, Shimadzu Corporation) in the range of 250 to 800 nm. bottom.
- the dye retention rate of the polymer sheet was calculated by the following formula from the measured absorbance at the maximum absorption wavelength near 590 nm of the polymer sheet after the 0th and 4th elutions.
- Dye retention rate (%) ⁇ 1-(4th absorbance) ⁇ (0th absorbance) ⁇ ⁇ 100
- Example 2 The components shown in Table 2 are uniformly mixed, placed in a polymerization mold (length 30 mm, width 30 mm, thickness 1 mm), polymerized at 65 ° C. for 60 minutes to prepare a polymer sheet with a thickness of 1 mm, and the polymer sheet is released from the mold. bottom. Each polymer sheet thus obtained was subjected to the following tests for evaluation. (1) Dissolution test It was carried out in the same manner as in Test Example 1.
- Moisture content (Weight of hydrated polymer sheet/Weight of dried polymer sheet - 1) x 100
- ⁇ Test Example 3> A polymer was prepared in the same manner as in Test Example 1 using the components and formulations shown in Table 4, and an elution test was performed to evaluate the dye retention rate.
Landscapes
- Health & Medical Sciences (AREA)
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Ophthalmology & Optometry (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
La présente invention a pour objet un polymère qui est approprié pour être utilisé en tant que matériau pour une lentille de contact souple qui permet d'améliorer les propriétés antireflet et le contraste. Le polymère selon l'invention est obtenu par copolymérisation d'un colorant organique ayant le pouvoir d'absorber la lumière dans la région du jaune et d'un ou plusieurs monomères polymérisables. Les monomères polymérisables comprennent un ou plusieurs types choisis parmi les monomères à base d'acrylamide et les monomères à base de vinyle. Les monomères polymérisables comprennent également un monomère contenant du silicium.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2023554733A JPWO2023068316A1 (fr) | 2021-10-20 | 2022-10-20 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2021171290 | 2021-10-20 | ||
JP2021-171290 | 2021-10-20 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2023068316A1 true WO2023068316A1 (fr) | 2023-04-27 |
Family
ID=86058299
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2022/039021 WO2023068316A1 (fr) | 2021-10-20 | 2022-10-20 | Matériau pour lentille de contact souple ayant une fonction d'amélioration du contraste |
Country Status (2)
Country | Link |
---|---|
JP (1) | JPWO2023068316A1 (fr) |
WO (1) | WO2023068316A1 (fr) |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH095682A (ja) * | 1995-02-07 | 1997-01-10 | Seiko Epson Corp | 着色コンタクトレンズおよびその製造法 |
JP2013533518A (ja) * | 2010-07-30 | 2013-08-22 | ノバルティス アーゲー | 架橋親水性コーティングを備えるシリコーンヒドロゲルレンズ |
JP2014523542A (ja) * | 2011-06-09 | 2014-09-11 | ノバルティス アーゲー | ナノテクスチャー表面を持つシリコーンヒドロゲルレンズ |
JP2017165941A (ja) * | 2015-12-25 | 2017-09-21 | 日東電工株式会社 | 有機el表示装置用粘着剤組成物、有機el表示装置用粘着剤層、有機el表示装置用粘着剤層付き偏光フィルム、及び有機el表示装置 |
JP6290170B2 (ja) * | 2013-02-28 | 2018-03-07 | 山本化成株式会社 | 自動車用合わせガラス |
JP6307209B1 (ja) * | 2016-09-30 | 2018-04-04 | 三井化学株式会社 | フォトクロミックレンズおよび重合性組成物 |
WO2019111969A1 (fr) * | 2017-12-06 | 2019-06-13 | 三井化学株式会社 | Composition polymérisable pour matériau optique et article moulé |
JP2022071514A (ja) * | 2020-10-28 | 2022-05-16 | 興和株式会社 | コントラスト改善機能を有する眼科用材料 |
-
2022
- 2022-10-20 WO PCT/JP2022/039021 patent/WO2023068316A1/fr active Application Filing
- 2022-10-20 JP JP2023554733A patent/JPWO2023068316A1/ja active Pending
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH095682A (ja) * | 1995-02-07 | 1997-01-10 | Seiko Epson Corp | 着色コンタクトレンズおよびその製造法 |
JP2013533518A (ja) * | 2010-07-30 | 2013-08-22 | ノバルティス アーゲー | 架橋親水性コーティングを備えるシリコーンヒドロゲルレンズ |
JP2014523542A (ja) * | 2011-06-09 | 2014-09-11 | ノバルティス アーゲー | ナノテクスチャー表面を持つシリコーンヒドロゲルレンズ |
JP6290170B2 (ja) * | 2013-02-28 | 2018-03-07 | 山本化成株式会社 | 自動車用合わせガラス |
JP2017165941A (ja) * | 2015-12-25 | 2017-09-21 | 日東電工株式会社 | 有機el表示装置用粘着剤組成物、有機el表示装置用粘着剤層、有機el表示装置用粘着剤層付き偏光フィルム、及び有機el表示装置 |
JP6307209B1 (ja) * | 2016-09-30 | 2018-04-04 | 三井化学株式会社 | フォトクロミックレンズおよび重合性組成物 |
WO2019111969A1 (fr) * | 2017-12-06 | 2019-06-13 | 三井化学株式会社 | Composition polymérisable pour matériau optique et article moulé |
JP2022071514A (ja) * | 2020-10-28 | 2022-05-16 | 興和株式会社 | コントラスト改善機能を有する眼科用材料 |
Also Published As
Publication number | Publication date |
---|---|
JPWO2023068316A1 (fr) | 2023-04-27 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP3195662B2 (ja) | 眼用レンズ材料 | |
JP2774233B2 (ja) | 眼用レンズ材料 | |
EP1750157B1 (fr) | Lentille de contact | |
JP4149068B2 (ja) | 眼用レンズ材料 | |
EP2657304B1 (fr) | Colorant azoïque, matériau de lentilles oculaires, procédé de production de matériau de lentilles oculaires et lentilles oculaires | |
JPH0790030A (ja) | 眼用レンズ材料 | |
JP3108550B2 (ja) | 軟質眼用レンズ材料 | |
JP3335216B2 (ja) | 眼用レンズ材料 | |
JP2515010B2 (ja) | 眼用レンズ材料 | |
JPH11286521A (ja) | 眼用レンズ材料 | |
JP2022071514A (ja) | コントラスト改善機能を有する眼科用材料 | |
WO2023068316A1 (fr) | Matériau pour lentille de contact souple ayant une fonction d'amélioration du contraste | |
JP3569373B2 (ja) | 含水性ソフトコンタクトレンズ | |
JP2716181B2 (ja) | 軟質眼用レンズ材料 | |
JPH11133201A (ja) | 光学材料 | |
JPH03228014A (ja) | 軟質眼用レンズ | |
JP3530287B2 (ja) | 低含水性眼用レンズ用材料、それからなる低含水性眼用レンズ用成形体、ならびにそれからなる低含水性眼用レンズおよびその製法 | |
EP0843184B1 (fr) | Matériau pour lentille oculaire | |
JP3084180B2 (ja) | コンタクトレンズ | |
WO2020174570A1 (fr) | Matériau polymère | |
JP3150771B2 (ja) | 眼用レンズ材料 | |
JP2804279B2 (ja) | 眼用レンズ材料 | |
JPH07196745A (ja) | 眼用レンズ材料 | |
JPH0713109A (ja) | 含水性ソフトコンタクトレンズ | |
JP2716187B2 (ja) | 軟質眼用レンズ材料 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 22883620 Country of ref document: EP Kind code of ref document: A1 |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2023554733 Country of ref document: JP |
|
NENP | Non-entry into the national phase |
Ref country code: DE |