JP7451792B1 - シロキサンモノマー、コンタクトレンズ組成物及びコンタクトレンズ - Google Patents
シロキサンモノマー、コンタクトレンズ組成物及びコンタクトレンズ Download PDFInfo
- Publication number
- JP7451792B1 JP7451792B1 JP2023018138A JP2023018138A JP7451792B1 JP 7451792 B1 JP7451792 B1 JP 7451792B1 JP 2023018138 A JP2023018138 A JP 2023018138A JP 2023018138 A JP2023018138 A JP 2023018138A JP 7451792 B1 JP7451792 B1 JP 7451792B1
- Authority
- JP
- Japan
- Prior art keywords
- siloxane monomer
- weight
- contact lens
- parts
- less
- Prior art date
- 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.)
- Active
Links
- 239000000178 monomer Substances 0.000 title claims abstract description 122
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 title claims abstract description 102
- 239000000203 mixture Substances 0.000 title claims abstract description 52
- 238000002834 transmittance Methods 0.000 claims description 17
- 239000003999 initiator Substances 0.000 claims description 15
- 229920001223 polyethylene glycol Polymers 0.000 claims description 15
- 239000002202 Polyethylene glycol Substances 0.000 claims description 14
- YCUVUDODLRLVIC-UHFFFAOYSA-N Sudan black B Chemical compound C1=CC(=C23)NC(C)(C)NC2=CC=CC3=C1N=NC(C1=CC=CC=C11)=CC=C1N=NC1=CC=CC=C1 YCUVUDODLRLVIC-UHFFFAOYSA-N 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 239000003431 cross linking reagent Substances 0.000 claims description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- XLPJNCYCZORXHG-UHFFFAOYSA-N 1-morpholin-4-ylprop-2-en-1-one Chemical compound C=CC(=O)N1CCOCC1 XLPJNCYCZORXHG-UHFFFAOYSA-N 0.000 claims description 8
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 8
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 claims description 8
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 claims description 7
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 7
- 125000004386 diacrylate group Chemical group 0.000 claims description 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
- QRIMLDXJAPZHJE-UHFFFAOYSA-N 2,3-dihydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)CO QRIMLDXJAPZHJE-UHFFFAOYSA-N 0.000 claims description 6
- XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 claims description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 claims description 6
- -1 1,4-di(acrylamido) butene Chemical compound 0.000 claims description 5
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 claims description 5
- UUORTJUPDJJXST-UHFFFAOYSA-N n-(2-hydroxyethyl)prop-2-enamide Chemical compound OCCNC(=O)C=C UUORTJUPDJJXST-UHFFFAOYSA-N 0.000 claims description 5
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 claims description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 4
- HCLJOFJIQIJXHS-UHFFFAOYSA-N 2-[2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOCCOC(=O)C=C HCLJOFJIQIJXHS-UHFFFAOYSA-N 0.000 claims description 4
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- AYGYHGXUJBFUJU-UHFFFAOYSA-N n-[2-(prop-2-enoylamino)ethyl]prop-2-enamide Chemical compound C=CC(=O)NCCNC(=O)C=C AYGYHGXUJBFUJU-UHFFFAOYSA-N 0.000 claims description 4
- ZSZRUEAFVQITHH-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)ethyl 2-(trimethylazaniumyl)ethyl phosphate Chemical compound CC(=C)C(=O)OCCOP([O-])(=O)OCC[N+](C)(C)C ZSZRUEAFVQITHH-UHFFFAOYSA-N 0.000 claims description 3
- HWSSEYVMGDIFMH-UHFFFAOYSA-N 2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOC(=O)C(C)=C HWSSEYVMGDIFMH-UHFFFAOYSA-N 0.000 claims description 3
- LTHJXDSHSVNJKG-UHFFFAOYSA-N 2-[2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOCCOC(=O)C(C)=C LTHJXDSHSVNJKG-UHFFFAOYSA-N 0.000 claims description 3
- GJMKDUFSSQMPNG-UHFFFAOYSA-N 2-aminoacetic acid ethenyl hydrogen carbonate Chemical compound C(OC=C)(O)=O.NCC(=O)O GJMKDUFSSQMPNG-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 3
- IEVADDDOVGMCSI-UHFFFAOYSA-N 2-hydroxybutyl 2-methylprop-2-enoate Chemical compound CCC(O)COC(=O)C(C)=C IEVADDDOVGMCSI-UHFFFAOYSA-N 0.000 claims description 3
- CARNFEUGBMWTON-UHFFFAOYSA-N 3-(2-prop-2-enoxyethoxy)prop-1-ene Chemical compound C=CCOCCOCC=C CARNFEUGBMWTON-UHFFFAOYSA-N 0.000 claims description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 3
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 claims description 3
- NBOCBWJUDBATAS-UHFFFAOYSA-N [2-hydroxy-3-[3-[methyl-bis(trimethylsilyloxy)silyl]propoxy]propyl] 2-methylprop-2-enoate Chemical group CC(=C)C(=O)OCC(O)COCCC[Si](C)(O[Si](C)(C)C)O[Si](C)(C)C NBOCBWJUDBATAS-UHFFFAOYSA-N 0.000 claims description 3
- PNLUGRYDUHRLOF-UHFFFAOYSA-N n-ethenyl-n-methylacetamide Chemical compound C=CN(C)C(C)=O PNLUGRYDUHRLOF-UHFFFAOYSA-N 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 claims description 3
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 claims description 3
- 229910052719 titanium Inorganic materials 0.000 claims description 3
- 239000010936 titanium Substances 0.000 claims description 3
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 claims description 2
- ZEWNANDAGSVPKE-UHFFFAOYSA-N 3-[2-[2-(2-prop-2-enoxyethoxy)ethoxy]ethoxy]prop-1-ene Chemical compound C=CCOCCOCCOCCOCC=C ZEWNANDAGSVPKE-UHFFFAOYSA-N 0.000 claims description 2
- IFBMOBFQBJZBMV-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphanyl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C IFBMOBFQBJZBMV-UHFFFAOYSA-N 0.000 claims description 2
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims description 2
- NNNLYDWXTKOQQX-UHFFFAOYSA-N 1,1-di(prop-2-enoyloxy)propyl prop-2-enoate Chemical compound C=CC(=O)OC(CC)(OC(=O)C=C)OC(=O)C=C NNNLYDWXTKOQQX-UHFFFAOYSA-N 0.000 claims 1
- 230000005540 biological transmission Effects 0.000 claims 1
- 238000010586 diagram Methods 0.000 abstract 1
- 239000000975 dye Substances 0.000 description 21
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 17
- 150000002576 ketones Chemical class 0.000 description 13
- 239000000126 substance Substances 0.000 description 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 125000004429 atom Chemical group 0.000 description 10
- 229920001296 polysiloxane Polymers 0.000 description 10
- 125000001424 substituent group Chemical group 0.000 description 10
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 9
- 238000005259 measurement Methods 0.000 description 9
- 230000035699 permeability Effects 0.000 description 9
- 239000011248 coating agent Substances 0.000 description 8
- 238000000576 coating method Methods 0.000 description 8
- 239000000017 hydrogel Substances 0.000 description 8
- 239000006096 absorbing agent Substances 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 230000010287 polarization Effects 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 5
- 239000006184 cosolvent Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 239000007853 buffer solution Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 229920000671 polyethylene glycol diacrylate Polymers 0.000 description 4
- KUIXZSYWBHSYCN-UHFFFAOYSA-L remazol brilliant blue r Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C(N)=C2C(=O)C3=CC=CC=C3C(=O)C2=C1NC1=CC=CC(S(=O)(=O)CCOS([O-])(=O)=O)=C1 KUIXZSYWBHSYCN-UHFFFAOYSA-L 0.000 description 4
- VCYCUECVHJJFIQ-UHFFFAOYSA-N 2-[3-(benzotriazol-2-yl)-4-hydroxyphenyl]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 VCYCUECVHJJFIQ-UHFFFAOYSA-N 0.000 description 3
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 238000004043 dyeing Methods 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 230000005660 hydrophilic surface Effects 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- 235000000177 Indigofera tinctoria Nutrition 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- FHNINJWBTRXEBC-UHFFFAOYSA-N Sudan III Chemical compound OC1=CC=C2C=CC=CC2=C1N=NC(C=C1)=CC=C1N=NC1=CC=CC=C1 FHNINJWBTRXEBC-UHFFFAOYSA-N 0.000 description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 2
- 239000012964 benzotriazole Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000014509 gene expression Effects 0.000 description 2
- 125000005456 glyceride group Chemical group 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 230000036571 hydration Effects 0.000 description 2
- 238000006703 hydration reaction Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229940097275 indigo Drugs 0.000 description 2
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 229920005573 silicon-containing polymer Polymers 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000001954 sterilising effect Effects 0.000 description 2
- 238000004659 sterilization and disinfection Methods 0.000 description 2
- 229940099373 sudan iii Drugs 0.000 description 2
- LLLWMXQKXWIRDZ-UHFFFAOYSA-N 1-ethenylpyrrolidin-2-one Chemical compound C=CN1CCCC1=O.C=CN1CCCC1=O LLLWMXQKXWIRDZ-UHFFFAOYSA-N 0.000 description 1
- GTELLNMUWNJXMQ-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.CCC(CO)(CO)CO GTELLNMUWNJXMQ-UHFFFAOYSA-N 0.000 description 1
- ALRXDIKPRCRYAU-UHFFFAOYSA-N 2-methylpropan-2-ol Chemical compound CC(C)(C)O.CC(C)(C)O ALRXDIKPRCRYAU-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 206010015946 Eye irritation Diseases 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 1
- KNSXNCFKSZZHEA-UHFFFAOYSA-N [3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C KNSXNCFKSZZHEA-UHFFFAOYSA-N 0.000 description 1
- 229940117913 acrylamide Drugs 0.000 description 1
- 125000003172 aldehyde group Chemical group 0.000 description 1
- 150000001408 amides Chemical group 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 229950011260 betanaphthol Drugs 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000007975 buffered saline Substances 0.000 description 1
- MZNDIOURMFYZLE-UHFFFAOYSA-N butan-1-ol Chemical compound CCCCO.CCCCO MZNDIOURMFYZLE-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- KOMDZQSPRDYARS-UHFFFAOYSA-N cyclopenta-1,3-diene titanium Chemical compound [Ti].C1C=CC=C1.C1C=CC=C1 KOMDZQSPRDYARS-UHFFFAOYSA-N 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000009510 drug design Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical group 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 231100000013 eye irritation Toxicity 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 229950004354 phosphorylcholine Drugs 0.000 description 1
- 238000003969 polarography Methods 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 229940051201 quinoline yellow Drugs 0.000 description 1
- 235000012752 quinoline yellow Nutrition 0.000 description 1
- 239000004172 quinoline yellow Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 150000007970 thio esters Chemical group 0.000 description 1
- MWUKMLGHBBOKGG-UHFFFAOYSA-N trimethyl-[propylsilyl(trimethylsilyloxy)methoxy]silane Chemical compound CCC[SiH2]C(O[Si](C)(C)C)O[Si](C)(C)C MWUKMLGHBBOKGG-UHFFFAOYSA-N 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
- C08G77/46—Block-or graft-polymers containing polysiloxane sequences containing polyether sequences
-
- 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
- C08F226/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
- C08F226/06—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 by a heterocyclic ring containing nitrogen
- C08F226/10—N-Vinyl-pyrrolidone
-
- 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
- C08F230/00—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
- C08F230/04—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
- C08F230/08—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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/07—Aldehydes; Ketones
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/11—Esters; Ether-esters of acyclic polycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5397—Phosphine oxides
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
- G02B1/041—Lenses
- G02B1/043—Contact lenses
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Eyeglasses (AREA)
Abstract
Description
本発明の実施形態において、コンタクトレンズを製造するためのシロキサンモノマー(silicone monomer)を提供する。前記シロキサンモノマーは、下式(I)で表される構造を有する。
本発明の実施形態において、シロキサンモノマー(silicone monomer)、親水性モノマー(hydrophilic monomer)、架橋剤(crosslinking agent)、開始剤(initiator)、UV吸収剤(UV absorber)、共溶媒(co-solvent)及び染料(dye)を含む、コンタクトレンズ組成物(contact lens composition)を提供する。
以下にて、実験例S1~実験例S14に基づいて、本発明の内容を説明する。しかしながら、以下の実験例は単に、本発明を理解するためのものであって、本発明の範囲はそれらの実験例に制限されるものではない。上記の実験例において、S1~S2は比較例であり、即ち、コンタクトレンズ組成物が式(I)で表されるシロキサンモノマーを含まなかった。S3~S14は、本発明の効果を証明するための実施例であり、即ち、コンタクトレンズ組成物が式(I)で表されるシロキサンモノマーを含んだ。本実験データは、式(I)で表されるシロキサンモノマーを例として説明するが、本発明はこれに制限されるものではない。
Claims (10)
- コンタクトレンズを製造するためのシロキサンモノマーであって、前記シロキサンモノマーは、下式(I)で表される構造を有し、
R2がハロゲンで置換されていないNHR3、N(R3)2、OR3、SR3、又は
R3が
R4がH又はC1~C6アルキル基であり、
x≧0、y≧1、z≧0であることを特徴とする、シロキサンモノマー。 - 前記シロキサンモノマーの重量平均分子量又は数平均分子量は、1,000g/mol~50,000g/molである、請求項1に記載のシロキサンモノマー。
- シロキサンモノマー、親水性モノマー、架橋剤及び開始剤を含む、コンタクトレンズ組成物であって、前記シロキサンモノマーは、下式(I)で表される構造を有する第1のシロキサンモノマーを含み、
- 前記シロキサンモノマーは、第2のシロキサンモノマー、第3のシロキサンモノマー及び第4のシロキサンモノマーの中の少なくとも一つを更に含み、
前記第2のシロキサンモノマーは、下式(II)で表される構造を有し、
- 前記コンタクトレンズ組成物の総重量を100重量部として、前記第1のシロキサンモノマーの使用量が1重量部~30重量部であり、前記第2のシロキサンモノマーの使用量が40重量部以下であり、前記第3のシロキサンモノマーの使用量が40重量部以下であり、前記第4のシロキサンモノマーの使用量が30重量部以下である、請求項4に記載のコンタクトレンズ組成物。
- 前記親水性モノマーは、メタクリル酸2-ヒドロキシエチル、メタクリル酸メチル、メタクリル酸、N-ビニルピロリドン、N,N-ジメチルアクリルアミド、4-アクリロイルモルホリン、N-(2-ヒドロキシエチル)アクリルアミド(HEAA)、メタクリル酸グリシジル、モノメタクリル酸グリセロール、アクリル酸、N-ビニル-N-メチルアセトアミド、グリシンビニルカーボネート、2-メタクリロイルオキシエチルホスホリルコリン、及びメタクリル酸2-ヒドロキシブチルからなる群の少なくとも1つから選択され、
前記親水性モノマーの使用量は、30重量部~70重量部である、請求項3に記載のコンタクトレンズ組成物。 - 前記架橋剤は、ポリエチレングリコールジアクリレート、エチレングリコールジメタクリレート、ジエチレングリコールジメタクリレート、トリエチレングリコールジメタクリレート、ジメタクリル酸テトラエチレングリコール、メタクリル酸アリル、エチレングリコールジアリルエーテル、トリエチレングリコールジアリルエーテル、テトラエチレングリコールジメタクリラート、1,3,5-トリアリル-1,3,5-トリアジン-2,4,6(1H,3H,5H)-トリオン、1,1,1-トリメチロールプロパントリメタクリラート、トリメチロールプロパントリアクリラート、ペンタエリスリトールテトラアクリレート、テトラエチレングリコールジアクリレート、エチレンジアクリルアミド、及び1,4-ジ(アクリルアミド)ブテンからなる群の少なくとも1つから選択され、
前記架橋剤の使用量は、0.01重量部~5重量部である、請求項3に記載のコンタクトレンズ組成物。 - 前記開始剤は、ジ-H5-シクロペンタジエニルビス[2,6-ジフルオロ-3-(ピロール-1-イル)フェニル]チタン(4)、フェニルビス(2,4,6-トリメチルベンゾイル)ホスフィンオキシド及び2-ヒドロキシ-2-メチル-1-フェニル-1-プロパノンからなる群の少なく開始剤とも1つから選択され、
前記開始剤の使用量は、0.01重量部~2重量部である、請求項3に記載のコンタクトレンズ組成物。 - 請求項3~8のいずれか一項に記載のコンタクトレンズ組成物で製造されたコンタクトレンズであって、
前記コンタクトレンズは、レンズの表面に30°未満のヒステリシス(Hysteresis)を有し、且つレンズのスーダンブラック(Sudan black)染料で染色された後の染色透過率が70%を超えることを特徴とする、コンタクトレンズ。 - 前記コンタクトレンズは、
(i)40Barrers~150Barrersの酸素透過率、
(ii)30%~80%の平衡含水率、
(iii)0°以上30°未満の前記ヒステリシス、
(iv)70%を超え99.9%以下の前記染色透過率、
(v)0.1MPa~0.8MPaの伸長弾性率、及び
(vi)100%~500%の伸長率、を満たす、請求項9に記載のコンタクトレンズ。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
TW111137128 | 2022-09-30 | ||
TW111137128A TWI828345B (zh) | 2022-09-30 | 2022-09-30 | 矽氧烷單體、隱形眼鏡組成物及隱形眼鏡 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP7451792B1 true JP7451792B1 (ja) | 2024-03-18 |
JP2024052477A JP2024052477A (ja) | 2024-04-11 |
Family
ID=85202137
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2023018138A Active JP7451792B1 (ja) | 2022-09-30 | 2023-02-09 | シロキサンモノマー、コンタクトレンズ組成物及びコンタクトレンズ |
Country Status (4)
Country | Link |
---|---|
US (1) | US20240132670A1 (ja) |
EP (1) | EP4345122A1 (ja) |
JP (1) | JP7451792B1 (ja) |
TW (1) | TWI828345B (ja) |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2015528586A (ja) | 2012-08-28 | 2015-09-28 | クーパーヴィジョン インターナショナル ホウルディング カンパニー リミテッド パートナーシップ | Hema−相溶性ポリシロキサンマクロマー製のコンタクトレンズ |
JP2017531074A (ja) | 2014-09-26 | 2017-10-19 | ノバルティス アーゲー | 親水性置換基を有する重合性ポリシロキサン |
JP2019504140A (ja) | 2015-12-15 | 2019-02-14 | ノバルティス アーゲー | 親水化ポリジオルガノシロキサンビニル架橋剤およびその使用 |
WO2019112255A1 (ko) | 2017-12-05 | 2019-06-13 | 주식회사 인터로조 | 우수한 물성을 가지는 실리콘 하이드로겔 렌즈 |
JP2021185246A (ja) | 2016-07-06 | 2021-12-09 | ジョンソン・アンド・ジョンソン・ビジョン・ケア・インコーポレイテッドJohnson & Johnson Vision Care, Inc. | n−アルキルメタクリルアミドを含むシリコーンヒドロゲル及びそれから作製されたコンタクトレンズ |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE12156772T1 (de) * | 2011-02-28 | 2013-05-29 | Coopervision International Holding Company, Lp | Formstabile Silikonhydrogel-Kontaktlinsen |
TWI506334B (zh) * | 2011-02-28 | 2015-11-01 | Coopervision Int Holding Co Lp | 具有可接受程度之能量損失的聚矽氧水凝膠隱形眼鏡 |
KR101742352B1 (ko) * | 2011-02-28 | 2017-05-31 | 쿠퍼비젼 인터내셔날 홀딩 캄파니, 엘피 | 실리콘 히드로겔 콘택트 렌즈 |
TWI642728B (zh) * | 2016-05-12 | 2018-12-01 | 詹前慶 | 一種矽水膠組合物及其製備之鏡片 |
-
2022
- 2022-09-30 TW TW111137128A patent/TWI828345B/zh active
-
2023
- 2023-02-07 EP EP23155299.3A patent/EP4345122A1/en active Pending
- 2023-02-07 US US18/106,894 patent/US20240132670A1/en active Pending
- 2023-02-09 JP JP2023018138A patent/JP7451792B1/ja active Active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2015528586A (ja) | 2012-08-28 | 2015-09-28 | クーパーヴィジョン インターナショナル ホウルディング カンパニー リミテッド パートナーシップ | Hema−相溶性ポリシロキサンマクロマー製のコンタクトレンズ |
JP2017531074A (ja) | 2014-09-26 | 2017-10-19 | ノバルティス アーゲー | 親水性置換基を有する重合性ポリシロキサン |
JP2019504140A (ja) | 2015-12-15 | 2019-02-14 | ノバルティス アーゲー | 親水化ポリジオルガノシロキサンビニル架橋剤およびその使用 |
JP2021185246A (ja) | 2016-07-06 | 2021-12-09 | ジョンソン・アンド・ジョンソン・ビジョン・ケア・インコーポレイテッドJohnson & Johnson Vision Care, Inc. | n−アルキルメタクリルアミドを含むシリコーンヒドロゲル及びそれから作製されたコンタクトレンズ |
WO2019112255A1 (ko) | 2017-12-05 | 2019-06-13 | 주식회사 인터로조 | 우수한 물성을 가지는 실리콘 하이드로겔 렌즈 |
Also Published As
Publication number | Publication date |
---|---|
US20240132670A1 (en) | 2024-04-25 |
EP4345122A1 (en) | 2024-04-03 |
TW202415711A (zh) | 2024-04-16 |
JP2024052477A (ja) | 2024-04-11 |
TWI828345B (zh) | 2024-01-01 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
AU2017306270B2 (en) | Polymer compositions containing grafted polymeric networks and processes for their preparation and use | |
KR102117217B1 (ko) | 이온성 실리콘 하이드로겔 | |
JP6932763B2 (ja) | ポリアミドを含むシリコーンヒドロゲル | |
JP3422996B2 (ja) | 表面ぬれ性シリコーンヒドロゲル | |
TWI564313B (zh) | 包含n-乙烯基醯胺及(甲基)丙烯酸羥基烷酯或羥基烷基(甲基)丙烯醯胺之聚矽氧水凝膠 | |
KR101532394B1 (ko) | 콘택트 렌즈 | |
JP6934537B2 (ja) | シリコーンハイドロゲルコンタクトレンズ | |
AU2019213690B2 (en) | Ophthalmic devices derived from grafted polymeric networks and processes for their preparation and use | |
TWI753090B (zh) | 用於隱形眼鏡的單體組合物、用於隱形眼鏡的聚合物及其製備方法、以及隱形眼鏡及其製造方法 | |
BRPI0711964B1 (pt) | Lente de contato de silicone hidrogel extraído, produto de lente de contato de silicone hidrogel polimerizado pré-extraído, composição precursora de lente de contato de silicone hidrogel polimerizável e método para produzir uma lente de contato de silicone hidrogel | |
JP2016524178A (ja) | 一級アミン含有シリコーンヒドロゲルコンタクトレンズ並びに関連する組成物及び方法 | |
JP7358390B2 (ja) | 局所的にグラフトされたネットワークを含有する眼科用装置並びにその調製及び使用プロセス | |
KR20200013693A (ko) | 실리콘 하이드로겔 콘택트 렌즈 | |
AU2015241170B2 (en) | Silicone acrylamide copolymer | |
AU2004256111B2 (en) | Silicone hydrogels having consistent concentrations of multi-functional polysiloxanes | |
WO2023275683A1 (en) | Ophthalmic devices derived from grafted polymeric networks and processes for their preparation and use | |
JP2020084166A (ja) | シリコーンハイドロゲル組成物、シリコーンハイドロゲルレンズ、及び、シリコーンハイドロゲルレンズの製造方法 | |
TWI841916B (zh) | 隱形眼鏡材料及隱形眼鏡鏡片 | |
JP7451792B1 (ja) | シロキサンモノマー、コンタクトレンズ組成物及びコンタクトレンズ | |
WO2024065567A1 (zh) | 硅氧烷单体、隐形眼镜组成物及隐形眼镜 | |
TWI826534B (zh) | 隱形眼鏡用單體組合物及隱形眼鏡用聚合物、以及隱形眼鏡及其製造方法 | |
TW202342646A (zh) | 高透氧矽水膠組成物、使用高透氧矽水膠組成物製作的隱形眼鏡及其製作方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20230209 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20231031 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20240116 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20240220 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20240306 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 7451792 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |