CA1257040A - Oxygen permeable soft contact lens material - Google Patents
Oxygen permeable soft contact lens materialInfo
- Publication number
- CA1257040A CA1257040A CA000496961A CA496961A CA1257040A CA 1257040 A CA1257040 A CA 1257040A CA 000496961 A CA000496961 A CA 000496961A CA 496961 A CA496961 A CA 496961A CA 1257040 A CA1257040 A CA 1257040A
- Authority
- CA
- Canada
- Prior art keywords
- contact lens
- group
- polyorganosiloxane
- monomer
- hydrophilic
- 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.)
- Expired
Links
- 239000000463 material Substances 0.000 title claims abstract description 47
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 title claims abstract description 28
- 239000001301 oxygen Substances 0.000 title claims abstract description 28
- 229910052760 oxygen Inorganic materials 0.000 title claims abstract description 28
- 239000000178 monomer Substances 0.000 claims abstract description 61
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 37
- 229920001577 copolymer Polymers 0.000 claims abstract description 25
- 238000005828 desilylation reaction Methods 0.000 claims abstract description 10
- 239000000203 mixture Substances 0.000 claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims description 14
- 125000003700 epoxy group Chemical group 0.000 claims description 10
- 230000002209 hydrophobic effect Effects 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 20
- 230000035699 permeability Effects 0.000 description 20
- 238000006116 polymerization reaction Methods 0.000 description 14
- 238000000034 method Methods 0.000 description 13
- -1 thio-urethane Chemical compound 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 238000009736 wetting Methods 0.000 description 9
- 230000035515 penetration Effects 0.000 description 7
- 125000005375 organosiloxane group Chemical group 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 5
- 210000004087 cornea Anatomy 0.000 description 5
- 239000003505 polymerization initiator Substances 0.000 description 5
- 229920002379 silicone rubber Polymers 0.000 description 5
- 239000004945 silicone rubber Substances 0.000 description 5
- 239000004593 Epoxy Substances 0.000 description 4
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- JWTGRKUQJXIWCV-UHFFFAOYSA-N 1,2,3-trihydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(O)C(O)CO JWTGRKUQJXIWCV-UHFFFAOYSA-N 0.000 description 2
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-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
- JESXATFQYMPTNL-UHFFFAOYSA-N 2-ethenylphenol Chemical compound OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 238000005520 cutting process Methods 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
- 239000002504 physiological saline solution Substances 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 238000007142 ring opening reaction Methods 0.000 description 2
- 238000004381 surface treatment Methods 0.000 description 2
- HFQYAVPDOBKWAX-UHFFFAOYSA-N (2-hydroxynaphthalen-1-yl) 2-methylprop-2-enoate Chemical compound C1=CC=C2C(OC(=O)C(=C)C)=C(O)C=CC2=C1 HFQYAVPDOBKWAX-UHFFFAOYSA-N 0.000 description 1
- HZBSQYSUONRRMW-UHFFFAOYSA-N (2-hydroxyphenyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC=C1O HZBSQYSUONRRMW-UHFFFAOYSA-N 0.000 description 1
- IUSXXDHQFMPZQX-UHFFFAOYSA-N (2-hydroxyphenyl) prop-2-enoate Chemical compound OC1=CC=CC=C1OC(=O)C=C IUSXXDHQFMPZQX-UHFFFAOYSA-N 0.000 description 1
- OBKYRXNHGYFYAK-UHFFFAOYSA-N (2-hydroxyphenyl)methyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1O OBKYRXNHGYFYAK-UHFFFAOYSA-N 0.000 description 1
- 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
- XJYSCKKDXUWWRZ-UHFFFAOYSA-N 1-(2-ethylhexoxy)propane-1,2,3-triol Chemical compound CCCCC(CC)COC(O)C(O)CO XJYSCKKDXUWWRZ-UHFFFAOYSA-N 0.000 description 1
- KFWFMRKYAUHUOC-UHFFFAOYSA-N 1-ethoxy-3-[1-(1-hydroxypropan-2-yloxy)propan-2-yloxy]propan-2-ol Chemical compound CCOCC(O)COC(C)COC(C)CO KFWFMRKYAUHUOC-UHFFFAOYSA-N 0.000 description 1
- VVAZMETTYLVIJR-UHFFFAOYSA-N 1-phenoxypropane-1,2,3-triol Chemical compound OCC(O)C(O)OC1=CC=CC=C1 VVAZMETTYLVIJR-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
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- QFPKSTNFHFEHJL-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)benzoic acid Chemical compound CC(=C)C(=O)OC1=CC=CC=C1C(O)=O QFPKSTNFHFEHJL-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- MUUOUUYKIVSIAR-UHFFFAOYSA-N 2-but-3-enyloxirane Chemical compound C=CCCC1CO1 MUUOUUYKIVSIAR-UHFFFAOYSA-N 0.000 description 1
- XUDBVJCTLZTSDC-UHFFFAOYSA-N 2-ethenylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C=C XUDBVJCTLZTSDC-UHFFFAOYSA-N 0.000 description 1
- IUGFLBOXRUKMEN-UHFFFAOYSA-N 2-hept-6-enyloxirane Chemical compound C=CCCCCCC1CO1 IUGFLBOXRUKMEN-UHFFFAOYSA-N 0.000 description 1
- UKTHULMXFLCNAV-UHFFFAOYSA-N 2-hex-5-enyloxirane Chemical compound C=CCCCCC1CO1 UKTHULMXFLCNAV-UHFFFAOYSA-N 0.000 description 1
- FCZHJHKCOZGQJZ-UHFFFAOYSA-N 2-oct-7-enyloxirane Chemical compound C=CCCCCCCC1CO1 FCZHJHKCOZGQJZ-UHFFFAOYSA-N 0.000 description 1
- KCCIMXJIZJBZPX-UHFFFAOYSA-N 2-pent-4-enyloxirane Chemical compound C=CCCCC1CO1 KCCIMXJIZJBZPX-UHFFFAOYSA-N 0.000 description 1
- ZSQWQTABLXAFEZ-UHFFFAOYSA-N 2-phenylbut-3-enoic acid Chemical compound OC(=O)C(C=C)C1=CC=CC=C1 ZSQWQTABLXAFEZ-UHFFFAOYSA-N 0.000 description 1
- SPXXVGQMQJYJJO-UHFFFAOYSA-N 2-prop-2-enyloxirane Chemical compound C=CCC1CO1 SPXXVGQMQJYJJO-UHFFFAOYSA-N 0.000 description 1
- DXIJHCSGLOHNES-UHFFFAOYSA-N 3,3-dimethylbut-1-enylbenzene Chemical compound CC(C)(C)C=CC1=CC=CC=C1 DXIJHCSGLOHNES-UHFFFAOYSA-N 0.000 description 1
- CEBRPXLXYCFYGU-UHFFFAOYSA-N 3-methylbut-1-enylbenzene Chemical compound CC(C)C=CC1=CC=CC=C1 CEBRPXLXYCFYGU-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- 229910001369 Brass Inorganic materials 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
- 238000006136 alcoholysis reaction Methods 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 229960003328 benzoyl peroxide Drugs 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000010951 brass Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004202 carbamide Substances 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
- 238000005266 casting Methods 0.000 description 1
- ANTSCNMPPGJYLG-UHFFFAOYSA-N chlordiazepoxide Chemical compound O=N=1CC(NC)=NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 ANTSCNMPPGJYLG-UHFFFAOYSA-N 0.000 description 1
- YGZSVWMBUCGDCV-UHFFFAOYSA-N chloro(methyl)silane Chemical compound C[SiH2]Cl YGZSVWMBUCGDCV-UHFFFAOYSA-N 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000003851 corona treatment Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- ZEFVHSWKYCYFFL-UHFFFAOYSA-N diethyl 2-methylidenebutanedioate Chemical compound CCOC(=O)CC(=C)C(=O)OCC ZEFVHSWKYCYFFL-UHFFFAOYSA-N 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- ZWWQRMFIZFPUAA-UHFFFAOYSA-N dimethyl 2-methylidenebutanedioate Chemical compound COC(=O)CC(=C)C(=O)OC ZWWQRMFIZFPUAA-UHFFFAOYSA-N 0.000 description 1
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 208000028659 discharge Diseases 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 210000003128 head Anatomy 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
- 229920001519 homopolymer Polymers 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 125000005027 hydroxyaryl group Chemical group 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000010297 mechanical methods and process Methods 0.000 description 1
- 230000005226 mechanical processes and functions Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-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
- 230000000704 physical effect Effects 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
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- ZHDCHCTZRODSEN-HWKANZROSA-N propyl (e)-but-2-enoate Chemical compound CCCOC(=O)\C=C\C ZHDCHCTZRODSEN-HWKANZROSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035807 sensation Effects 0.000 description 1
- 125000005401 siloxanyl group Chemical group 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 238000006884 silylation reaction Methods 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/08—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated side groups
- C08F290/14—Polymers provided for in subclass C08G
- C08F290/148—Polysiloxanes
-
- 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
- C08F8/00—Chemical modification by after-treatment
-
- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/42—Introducing metal atoms or metal-containing groups
-
- 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)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- General Physics & Mathematics (AREA)
- Eyeglasses (AREA)
- Graft Or Block Polymers (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP261040/1984 | 1984-12-10 | ||
| JP59261040A JPS61138613A (ja) | 1984-12-10 | 1984-12-10 | 酸素透過性軟質コンタクトレンズ用材料 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1257040A true CA1257040A (en) | 1989-07-04 |
Family
ID=17356215
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000496961A Expired CA1257040A (en) | 1984-12-10 | 1985-12-05 | Oxygen permeable soft contact lens material |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4649184A (enExample) |
| EP (1) | EP0184800B1 (enExample) |
| JP (1) | JPS61138613A (enExample) |
| AU (1) | AU576135B2 (enExample) |
| CA (1) | CA1257040A (enExample) |
| DE (1) | DE3585947D1 (enExample) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4734475A (en) * | 1986-12-15 | 1988-03-29 | Ciba-Geigy Corporation | Wettable surface modified contact lens fabricated from an oxirane containing hydrophobic polymer |
| DE69014611T2 (de) * | 1989-12-29 | 1995-05-04 | Hoya Corp | Kontaktlinsenmaterial und kontaktlinse. |
| US5314960A (en) * | 1990-04-10 | 1994-05-24 | Permeable Technologies, Inc. | Silicone-containing polymers, oxygen permeable hydrophilic contact lenses and methods for making these lenses and treating patients with visual impairment |
| US5244981A (en) * | 1990-04-10 | 1993-09-14 | Permeable Technologies, Inc. | Silicone-containing contact lens polymers, oxygen permeable contact lenses and methods for making these lenses and treating patients with visual impairment |
| JP2690609B2 (ja) * | 1990-08-14 | 1997-12-10 | 旭化成工業株式会社 | コンタクトレンズ |
| US5371147A (en) * | 1990-10-11 | 1994-12-06 | Permeable Technologies, Inc. | Silicone-containing acrylic star polymers, block copolymers and macromonomers |
| US5274008A (en) * | 1990-11-27 | 1993-12-28 | Bausch & Lomb Incorporated | Mold materials for silicone containing lens materials |
| US5387329A (en) * | 1993-04-09 | 1995-02-07 | Ciba Corning Diagnostics Corp. | Extended use planar sensors |
| US7468398B2 (en) | 1994-09-06 | 2008-12-23 | Ciba Vision Corporation | Extended wear ophthalmic lens |
| US5760100B1 (en) | 1994-09-06 | 2000-11-14 | Ciba Vision Corp | Extended wear ophthalmic lens |
| US6822016B2 (en) | 2001-09-10 | 2004-11-23 | Johnson & Johnson Vision Care, Inc. | Biomedical devices containing internal wetting agents |
| US7461937B2 (en) * | 2001-09-10 | 2008-12-09 | Johnson & Johnson Vision Care, Inc. | Soft contact lenses displaying superior on-eye comfort |
| US20070043140A1 (en) * | 1998-03-02 | 2007-02-22 | Lorenz Kathrine O | Method for the mitigation of symptoms of contact lens related dry eye |
| US7052131B2 (en) * | 2001-09-10 | 2006-05-30 | J&J Vision Care, Inc. | Biomedical devices containing internal wetting agents |
| US6031059A (en) * | 1998-09-30 | 2000-02-29 | Johnson & Johnson Vision Products, Inc. | Optically transparent hydrogels and processes for their production |
| US20030151825A1 (en) * | 2001-12-28 | 2003-08-14 | California Institute Of Technology | Polyacrylate-based light adjustable optical element |
| JP3829933B2 (ja) * | 2002-05-16 | 2006-10-04 | 信越化学工業株式会社 | 難燃性シリコーン組成物 |
| US20070138692A1 (en) * | 2002-09-06 | 2007-06-21 | Ford James D | Process for forming clear, wettable silicone hydrogel articles |
| US20040119174A1 (en) * | 2002-12-19 | 2004-06-24 | Hofmann Gregory J. | Method for forming ophthalmic lenses using reusable molds |
| US8097565B2 (en) * | 2003-06-30 | 2012-01-17 | Johnson & Johnson Vision Care, Inc. | Silicone hydrogels having consistent concentrations of multi-functional polysiloxanes |
| US9322958B2 (en) | 2004-08-27 | 2016-04-26 | Coopervision International Holding Company, Lp | Silicone hydrogel contact lenses |
| US20060063852A1 (en) | 2004-08-27 | 2006-03-23 | Asahikasei Aime Co. Ltd. | Silicone hydrogel contact lens |
| US7297160B2 (en) * | 2005-06-15 | 2007-11-20 | Bausch & Lomb Incorporated | High refractive-index, hydrophilic, arylsiloxy-containing macromonomers and polymers, and ophthalmic devices comprising such polymers |
| US20090295004A1 (en) * | 2008-06-02 | 2009-12-03 | Pinsly Jeremy B | Silicone hydrogel contact lenses displaying reduced protein uptake |
| MY159465A (en) * | 2009-10-01 | 2017-01-13 | Coopervision Int Holding Co Lp | Silicone hydrogel contact lenses and methods of making silicone hydrogel contact lenses |
| JP5879963B2 (ja) * | 2010-11-25 | 2016-03-08 | 三菱レイヨン株式会社 | 熱硬化性樹脂組成物、その硬化物からなる光学部材 |
| TWI512048B (zh) | 2011-02-28 | 2015-12-11 | Coopervision Int Holding Co Lp | 聚矽氧水凝膠隱形眼鏡 |
| CN104011110B (zh) | 2011-02-28 | 2016-05-04 | 库柏维景国际控股公司 | 尺寸稳定的硅酮水凝胶隐形眼镜 |
| SG192187A1 (en) | 2011-02-28 | 2013-08-30 | Coopervision Int Holding Co Lp | Phosphine-containing hydrogel contact lenses |
| SG192236A1 (en) | 2011-02-28 | 2013-09-30 | Coopervision Int Holding Co Lp | Wettable silicone hydrogel contact lenses |
| EP2681616B1 (en) | 2011-02-28 | 2019-01-23 | CooperVision International Holding Company, LP | Silicone hydrogel contact lenses having acceptable levels of energy loss |
| ES2693275T3 (es) | 2011-02-28 | 2018-12-10 | Coopervision International Holding Company, Lp | Lentes de contacto de hidrogel de silicona |
| HUE042074T2 (hu) | 2011-02-28 | 2019-06-28 | Coopervision Int Holding Co Lp | Szilikon hidrogél kontaktlencsék valamint ezekkel kapcsolatos kompozíciók és eljárások |
| WO2025153483A1 (en) | 2024-01-18 | 2025-07-24 | Bausch + Lomb Ireland Limited | Silicone biomedical device with polymerizable glycosaminoglycans |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL124649C (enExample) * | 1964-10-13 | 1900-01-01 | ||
| US4261875A (en) * | 1979-01-31 | 1981-04-14 | American Optical Corporation | Contact lenses containing hydrophilic silicone polymers |
| US4260725A (en) * | 1979-12-10 | 1981-04-07 | Bausch & Lomb Incorporated | Hydrophilic contact lens made from polysiloxanes which are thermally bonded to polymerizable groups and which contain hydrophilic sidechains |
| US4463149A (en) * | 1982-03-29 | 1984-07-31 | Polymer Technology Corporation | Silicone-containing contact lens material and contact lenses made thereof |
| EP0094153A2 (en) * | 1982-05-10 | 1983-11-16 | Dow Corning Corporation | Inherently wettable silicone resin optical devices |
| US4419505A (en) * | 1982-07-14 | 1983-12-06 | Paragon Optical, Inc. | Contact lens composition, article and method of manufacture |
| US4486577A (en) * | 1982-10-12 | 1984-12-04 | Ciba-Geigy Corporation | Strong, silicone containing polymers with high oxygen permeability |
| JPS5978236A (ja) * | 1982-10-28 | 1984-05-07 | Toagosei Chem Ind Co Ltd | ビニル重合反応性直鎖シリコ−ン高分子量モノマ−の製造法 |
| US4481322A (en) * | 1983-03-30 | 1984-11-06 | Union Carbide Corporation | Novel reinforcing additive and method of reinforcing thermoplastic polymer therewith |
| US4575546A (en) * | 1984-06-22 | 1986-03-11 | Loctite Corporation | Terminal cluster vinyl silicones and acrylate cluster silicones therefrom |
-
1984
- 1984-12-10 JP JP59261040A patent/JPS61138613A/ja active Granted
-
1985
- 1985-12-05 CA CA000496961A patent/CA1257040A/en not_active Expired
- 1985-12-07 DE DE8585115604T patent/DE3585947D1/de not_active Expired - Lifetime
- 1985-12-07 EP EP85115604A patent/EP0184800B1/en not_active Expired
- 1985-12-09 AU AU50895/85A patent/AU576135B2/en not_active Ceased
- 1985-12-09 US US06/806,864 patent/US4649184A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US4649184A (en) | 1987-03-10 |
| EP0184800A2 (en) | 1986-06-18 |
| EP0184800B1 (en) | 1992-04-29 |
| AU576135B2 (en) | 1988-08-11 |
| AU5089585A (en) | 1986-06-19 |
| JPS61138613A (ja) | 1986-06-26 |
| JPH0155653B2 (enExample) | 1989-11-27 |
| EP0184800A3 (en) | 1989-02-22 |
| DE3585947D1 (de) | 1992-06-04 |
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| Date | Code | Title | Description |
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| MKEX | Expiry | ||
| MKEX | Expiry |
Effective date: 20060704 |