KR19990022852A - 중합성 실록산 거대단량체 - Google Patents
중합성 실록산 거대단량체 Download PDFInfo
- Publication number
- KR19990022852A KR19990022852A KR1019970709321A KR19970709321A KR19990022852A KR 19990022852 A KR19990022852 A KR 19990022852A KR 1019970709321 A KR1019970709321 A KR 1019970709321A KR 19970709321 A KR19970709321 A KR 19970709321A KR 19990022852 A KR19990022852 A KR 19990022852A
- Authority
- KR
- South Korea
- Prior art keywords
- macromonomer
- formula
- group
- polymer
- diisocyanate
- 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.)
- Withdrawn
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- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 title 1
- 229920000642 polymer Polymers 0.000 claims abstract description 63
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 29
- 230000001588 bifunctional effect Effects 0.000 claims abstract description 14
- 229920001577 copolymer Polymers 0.000 claims abstract description 14
- 239000000126 substance Substances 0.000 claims abstract description 13
- 238000004519 manufacturing process Methods 0.000 claims abstract description 12
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 10
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 9
- 125000003118 aryl group Chemical group 0.000 claims abstract description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 5
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 4
- 125000000262 haloalkenyl group Chemical group 0.000 claims abstract description 4
- 125000000232 haloalkynyl group Chemical group 0.000 claims abstract description 4
- 125000003106 haloaryl group Chemical group 0.000 claims abstract description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 4
- -1 methacryloyl Chemical group 0.000 claims description 67
- 239000000203 mixture Substances 0.000 claims description 47
- 238000000034 method Methods 0.000 claims description 32
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 22
- 239000002904 solvent Substances 0.000 claims description 18
- 235000013870 dimethyl polysiloxane Nutrition 0.000 claims description 13
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical group CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 13
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims description 13
- 239000004205 dimethyl polysiloxane Substances 0.000 claims description 12
- 210000004087 cornea Anatomy 0.000 claims description 11
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 11
- 229940011051 isopropyl acetate Drugs 0.000 claims description 11
- 238000006116 polymerization reaction Methods 0.000 claims description 11
- VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical compound O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-UHFFFAOYSA-N 0.000 claims description 9
- 230000002209 hydrophobic effect Effects 0.000 claims description 9
- 239000002243 precursor Substances 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 8
- 229920001223 polyethylene glycol Polymers 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 7
- 239000002202 Polyethylene glycol Substances 0.000 claims description 6
- 125000005442 diisocyanate group Chemical group 0.000 claims description 6
- 238000009472 formulation Methods 0.000 claims description 6
- CXQXSVUQTKDNFP-UHFFFAOYSA-N octamethyltrisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C CXQXSVUQTKDNFP-UHFFFAOYSA-N 0.000 claims description 6
- 238000004987 plasma desorption mass spectroscopy Methods 0.000 claims description 6
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 claims description 5
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 5
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 4
- MHCLJIVVJQQNKQ-UHFFFAOYSA-N ethyl carbamate;2-methylprop-2-enoic acid Chemical compound CCOC(N)=O.CC(=C)C(O)=O MHCLJIVVJQQNKQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000005504 styryl group Chemical group 0.000 claims description 4
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 229920000570 polyether Polymers 0.000 claims description 3
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 claims description 3
- BOSAWIQFTJIYIS-UHFFFAOYSA-N 1,1,1-trichloro-2,2,2-trifluoroethane Chemical compound FC(F)(F)C(Cl)(Cl)Cl BOSAWIQFTJIYIS-UHFFFAOYSA-N 0.000 claims description 2
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- 230000001678 irradiating effect Effects 0.000 claims description 2
- WDQKICIMIPUDBL-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]prop-2-enamide Chemical compound CN(C)CCNC(=O)C=C WDQKICIMIPUDBL-UHFFFAOYSA-N 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- OCGWWLDZAFOHGD-UHFFFAOYSA-N 1,1,1-trifluoro-2-methylpropan-2-ol Chemical compound CC(C)(O)C(F)(F)F OCGWWLDZAFOHGD-UHFFFAOYSA-N 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 229920001281 polyalkylene Polymers 0.000 claims 1
- 230000000379 polymerizing effect Effects 0.000 claims 1
- 238000007789 sealing Methods 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 description 43
- 125000002947 alkylene group Chemical group 0.000 description 31
- 239000007943 implant Substances 0.000 description 20
- 229910052760 oxygen Inorganic materials 0.000 description 17
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 16
- 239000000463 material Substances 0.000 description 16
- 239000001301 oxygen Substances 0.000 description 16
- 210000004027 cell Anatomy 0.000 description 15
- 230000035699 permeability Effects 0.000 description 12
- 150000003254 radicals Chemical class 0.000 description 12
- 125000000732 arylene group Chemical group 0.000 description 11
- 210000001519 tissue Anatomy 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 10
- 239000012975 dibutyltin dilaurate Substances 0.000 description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
- 239000004743 Polypropylene Substances 0.000 description 8
- 230000010261 cell growth Effects 0.000 description 8
- 230000008034 disappearance Effects 0.000 description 8
- 239000012948 isocyanate Substances 0.000 description 8
- 150000002513 isocyanates Chemical class 0.000 description 8
- 229920001155 polypropylene Polymers 0.000 description 8
- 102000004169 proteins and genes Human genes 0.000 description 8
- 108090000623 proteins and genes Proteins 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
- 238000000605 extraction Methods 0.000 description 7
- 238000002329 infrared spectrum Methods 0.000 description 7
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 7
- RBQRWNWVPQDTJJ-UHFFFAOYSA-N methacryloyloxyethyl isocyanate Chemical compound CC(=C)C(=O)OCCN=C=O RBQRWNWVPQDTJJ-UHFFFAOYSA-N 0.000 description 7
- 230000003287 optical effect Effects 0.000 description 7
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 6
- 210000002919 epithelial cell Anatomy 0.000 description 6
- 230000036571 hydration Effects 0.000 description 6
- 238000006703 hydration reaction Methods 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 6
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 5
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 5
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 230000021164 cell adhesion Effects 0.000 description 5
- 238000004132 cross linking Methods 0.000 description 5
- 239000012530 fluid Substances 0.000 description 5
- 125000000524 functional group Chemical group 0.000 description 5
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 150000003926 acrylamides Chemical class 0.000 description 4
- 125000003282 alkyl amino group Chemical group 0.000 description 4
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 4
- 210000002950 fibroblast Anatomy 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 239000012528 membrane Substances 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
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- 229940088644 n,n-dimethylacrylamide Drugs 0.000 description 4
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 229910000077 silane Inorganic materials 0.000 description 4
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- VHSHLMUCYSAUQU-UHFFFAOYSA-N 2-hydroxypropyl methacrylate Chemical compound CC(O)COC(=O)C(C)=C VHSHLMUCYSAUQU-UHFFFAOYSA-N 0.000 description 3
- RIWRBSMFKVOJMN-UHFFFAOYSA-N 2-methyl-1-phenylpropan-2-ol Chemical group CC(C)(O)CC1=CC=CC=C1 RIWRBSMFKVOJMN-UHFFFAOYSA-N 0.000 description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 125000005024 alkenyl aryl group Chemical group 0.000 description 3
- 125000005250 alkyl acrylate group Chemical group 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
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- 229920006037 cross link polymer Polymers 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
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- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
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- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-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
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- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 2
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- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical class OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
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- 239000012983 Dulbecco’s minimal essential medium Substances 0.000 description 2
- 101800003838 Epidermal growth factor Proteins 0.000 description 2
- 102400001368 Epidermal growth factor Human genes 0.000 description 2
- 108010067306 Fibronectins Proteins 0.000 description 2
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- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 206010021143 Hypoxia Diseases 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
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- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 2
- 229930182555 Penicillin Natural products 0.000 description 2
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 2
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 125000004956 cyclohexylene group Chemical group 0.000 description 2
- 229940116977 epidermal growth factor Drugs 0.000 description 2
- 210000000981 epithelium Anatomy 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
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- 239000007789 gas Substances 0.000 description 2
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- LYBIZMNPXTXVMV-UHFFFAOYSA-N propan-2-yl prop-2-enoate Chemical compound CC(C)OC(=O)C=C LYBIZMNPXTXVMV-UHFFFAOYSA-N 0.000 description 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229920013730 reactive polymer Polymers 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 230000003248 secreting effect Effects 0.000 description 1
- QYHFIVBSNOWOCQ-UHFFFAOYSA-N selenic acid Chemical compound O[Se](O)(=O)=O QYHFIVBSNOWOCQ-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000002210 silicon-based material Substances 0.000 description 1
- MNCGMVDMOKPCSQ-UHFFFAOYSA-M sodium;2-phenylethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=CC1=CC=CC=C1 MNCGMVDMOKPCSQ-UHFFFAOYSA-M 0.000 description 1
- BWYYYTVSBPRQCN-UHFFFAOYSA-M sodium;ethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=C BWYYYTVSBPRQCN-UHFFFAOYSA-M 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000008467 tissue growth Effects 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000012581 transferrin Substances 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000005065 undecenyl group Chemical class C(=CCCCCCCCCC)* 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 229960000834 vinyl ether Drugs 0.000 description 1
- 125000002348 vinylic group Chemical group 0.000 description 1
- 230000004304 visual acuity Effects 0.000 description 1
- 239000011800 void material Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/81—Unsaturated isocyanates or isothiocyanates
- C08G18/8108—Unsaturated isocyanates or isothiocyanates having only one isocyanate or isothiocyanate group
- C08G18/8116—Unsaturated isocyanates or isothiocyanates having only one isocyanate or isothiocyanate group esters of acrylic or alkylacrylic acid having only one isocyanate or isothiocyanate group
-
- 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
- C08F290/02—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 end groups
- C08F290/06—Polymers provided for in subclass C08G
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/61—Polysiloxanes
-
- 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)
- Macromonomer-Based Addition Polymer (AREA)
- Eyeglasses (AREA)
- Silicon Polymers (AREA)
- Materials For Medical Uses (AREA)
- Polyurethanes Or Polyureas (AREA)
- Silicates, Zeolites, And Molecular Sieves (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AUPN3545A AUPN354595A0 (en) | 1995-06-14 | 1995-06-14 | Novel materials |
| AUPN3545 | 1995-06-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR19990022852A true KR19990022852A (ko) | 1999-03-25 |
Family
ID=3787886
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019970709321A Withdrawn KR19990022852A (ko) | 1995-06-14 | 1996-06-04 | 중합성 실록산 거대단량체 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US5981615A (enExample) |
| EP (1) | EP0832142B1 (enExample) |
| JP (1) | JP3892903B2 (enExample) |
| KR (1) | KR19990022852A (enExample) |
| AT (1) | ATE203031T1 (enExample) |
| AU (1) | AUPN354595A0 (enExample) |
| BR (1) | BR9608911A (enExample) |
| CA (1) | CA2222608A1 (enExample) |
| DE (1) | DE69613841T2 (enExample) |
| IL (1) | IL122279A0 (enExample) |
| NO (1) | NO975839L (enExample) |
| WO (1) | WO1997000274A1 (enExample) |
| ZA (1) | ZA965016B (enExample) |
Families Citing this family (69)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU7533696A (en) * | 1996-12-13 | 1998-06-18 | Ciba-Geigy Ag | New materials |
| US6943203B2 (en) | 1998-03-02 | 2005-09-13 | Johnson & Johnson Vision Care, Inc. | Soft contact lenses |
| US6849671B2 (en) * | 1998-03-02 | 2005-02-01 | Johnson & Johnson Vision Care, Inc. | Contact lenses |
| US5959117A (en) * | 1998-08-10 | 1999-09-28 | Bausch & Lomb | Monomers useful for contact lens materials |
| TWI230712B (en) | 1998-09-15 | 2005-04-11 | Novartis Ag | Polymers |
| AR024237A1 (es) * | 1998-12-21 | 2002-09-25 | Novartis Ag | Copolimeros en bloque anfifilicos, procedimiento y precursores para su preparacion, y articulo moldeado obtenible a partir de los mismos |
| US6310169B1 (en) * | 1999-03-08 | 2001-10-30 | Chisso Corporation | Polymerizable terminal group-containing polyorganosiloxane and production process for the same |
| JP4489975B2 (ja) * | 1999-03-30 | 2010-06-23 | ノバルティス アーゲー | 有機化合物 |
| AUPQ197899A0 (en) * | 1999-08-02 | 1999-08-26 | Commonwealth Scientific And Industrial Research Organisation | Biomedical compositions |
| US7521519B1 (en) | 2000-03-14 | 2009-04-21 | Novartis Ag | Organic compounds |
| EP1157981B1 (en) * | 2000-05-25 | 2009-09-09 | Mitsubishi Gas Chemical Company, Inc. | Process for producing a high purity aromatic polycarboxylic acid |
| US6861123B2 (en) | 2000-12-01 | 2005-03-01 | Johnson & Johnson Vision Care, Inc. | Silicone hydrogel contact lens |
| DE10059822A1 (de) * | 2000-12-01 | 2002-06-13 | Clariant Gmbh | Saure kosmetische, pharmazeutische und dermatologische Mittel |
| US20040151755A1 (en) * | 2000-12-21 | 2004-08-05 | Osman Rathore | Antimicrobial lenses displaying extended efficacy, processes to prepare them and methods of their use |
| US20020133889A1 (en) * | 2001-02-23 | 2002-09-26 | Molock Frank F. | Colorants for use in tinted contact lenses and methods for their production |
| JP4854130B2 (ja) * | 2001-05-01 | 2012-01-18 | 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 | 親水性ポリシロキサンモノマーおよびその共重合体からなるコンタクトレンズ材料、およびコンタクトレンズ |
| US7008570B2 (en) | 2001-08-09 | 2006-03-07 | Stephen Pegram | Method and apparatus for contact lens mold assembly |
| US7169874B2 (en) * | 2001-11-02 | 2007-01-30 | Bausch & Lomb Incorporated | High refractive index polymeric siloxysilane compositions |
| AU2002950469A0 (en) * | 2002-07-30 | 2002-09-12 | Commonwealth Scientific And Industrial Research Organisation | Improved biomedical compositions |
| US20040150788A1 (en) | 2002-11-22 | 2004-08-05 | Ann-Margret Andersson | Antimicrobial lenses, processes to prepare them and methods of their use |
| US7216975B2 (en) * | 2003-07-15 | 2007-05-15 | Shinn-Gwo Hong | Method for preparing the reactive tinting compound and the tinted contact lens |
| US20050070661A1 (en) * | 2003-09-30 | 2005-03-31 | Frank Molock | Methods of preparing ophthalmic devices |
| US7416737B2 (en) * | 2003-11-18 | 2008-08-26 | Johnson & Johnson Vision Care, Inc. | Antimicrobial lenses, processes to prepare them and methods of their use |
| US7214809B2 (en) | 2004-02-11 | 2007-05-08 | Johnson & Johnson Vision Care, Inc. | (Meth)acrylamide monomers containing hydroxy and silicone functionalities |
| US7632904B2 (en) * | 2005-06-15 | 2009-12-15 | Bausch & Lomb Incorporated | High refractive-index, hydrophilic, arylsiloxy-containing monomers and polymers, and ophthalmic devices comprising such polymers |
| 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 |
| US20070218104A1 (en) * | 2006-03-15 | 2007-09-20 | Bausch & Lomb Incorporation | Rate controlled release of a pharmaceutical agent in a biodegradable device |
| US20070218103A1 (en) * | 2006-03-15 | 2007-09-20 | Bausch & Lomb Incorporated | Rate controlled release of a pharmaceutical agent in a biodegradable device |
| EP2020970A4 (en) | 2006-05-03 | 2013-11-13 | Vision Crc Ltd | EYE TREATMENT |
| WO2007128051A1 (en) * | 2006-05-03 | 2007-11-15 | Vision Crc Limited | Biological polysiloxanes |
| JP2008031307A (ja) * | 2006-07-28 | 2008-02-14 | Three Bond Co Ltd | 光硬化性オルガノポリシロキサン組成物 |
| CN101578116A (zh) * | 2006-10-31 | 2009-11-11 | 庄臣及庄臣视力保护公司 | 制备抗微生物接触透镜的方法 |
| US20080100797A1 (en) * | 2006-10-31 | 2008-05-01 | Nayiby Alvarez-Carrigan | Antimicrobial contact lenses with reduced haze and preparation thereof |
| US20080102095A1 (en) * | 2006-10-31 | 2008-05-01 | Kent Young | Acidic processes to prepare antimicrobial contact lenses |
| AT504860B1 (de) * | 2007-02-06 | 2012-02-15 | Mondi Release Liner Austria Gmbh | (meth)acrylamid-derivate von polysiloxanen |
| US8214746B2 (en) * | 2007-03-15 | 2012-07-03 | Accenture Global Services Limited | Establishment of message context in a collaboration system |
| EP2142219A2 (en) * | 2007-03-30 | 2010-01-13 | Johnson & Johnson Vision Care, Inc. | Preparation of antimicrobial contact lenses with reduced haze using swelling agents |
| US20080241225A1 (en) * | 2007-03-31 | 2008-10-02 | Hill Gregory A | Basic processes to prepare antimicrobial contact lenses |
| US20100310622A1 (en) * | 2007-12-17 | 2010-12-09 | University Of Florida Research Foundation, Inc. | Dry eye treatment by puncta plugs |
| US7802883B2 (en) | 2007-12-20 | 2010-09-28 | Johnson & Johnson Vision Care, Inc. | Cosmetic contact lenses having a sparkle effect |
| US7939579B1 (en) * | 2008-07-09 | 2011-05-10 | Contamac Limited | Hydrogels and methods of manufacture |
| US8440738B2 (en) * | 2008-07-09 | 2013-05-14 | Timothy Higgs | Silicone hydrogels and methods of manufacture |
| CA2739102C (en) * | 2008-11-13 | 2016-06-21 | Novartis Ag | Silicone hydrogel materials with chemically bound wetting agents |
| JP5460728B2 (ja) * | 2008-11-13 | 2014-04-02 | ノバルティス アーゲー | 末端親水性ポリマー鎖を有するポリシロキサン共重合体 |
| CA2760747C (en) * | 2009-05-22 | 2016-12-13 | Novartis Ag | Actinically-crosslinkable siloxane-containing copolymers |
| JP5684798B2 (ja) * | 2009-05-22 | 2015-03-18 | ノバルティス アーゲー | 化学線架橋性シロキサン含有コポリマー |
| JP5544017B2 (ja) * | 2009-09-15 | 2014-07-09 | ノバルティス アーゲー | 紫外線吸収性コンタクトレンズの製造に適したプレポリマー |
| US8697770B2 (en) | 2010-04-13 | 2014-04-15 | Johnson & Johnson Vision Care, Inc. | Pupil-only photochromic contact lenses displaying desirable optics and comfort |
| US8877103B2 (en) | 2010-04-13 | 2014-11-04 | Johnson & Johnson Vision Care, Inc. | Process for manufacture of a thermochromic contact lens material |
| US9690115B2 (en) | 2010-04-13 | 2017-06-27 | Johnson & Johnson Vision Care, Inc. | Contact lenses displaying reduced indoor glare |
| PL2598937T3 (pl) | 2010-07-30 | 2017-01-31 | Novartis Ag | Amfifilowe prepolimery polisiloksanowe i ich zastosowania |
| EP4657144A2 (en) | 2010-07-30 | 2025-12-03 | Alcon Inc. | Silicone hydrogel lenses with water-rich surfaces |
| CN103168067B (zh) | 2010-10-06 | 2015-08-05 | 诺华股份有限公司 | 可水处理的含硅氧烷预聚物及其用途 |
| US8835525B2 (en) | 2010-10-06 | 2014-09-16 | Novartis Ag | Chain-extended polysiloxane crosslinkers with dangling hydrophilic polymer chains |
| JP5784131B2 (ja) | 2010-10-06 | 2015-09-24 | ノバルティス アーゲー | ペンダント親水性基を持つ重合しうる鎖延長ポリシロキサン |
| US9005700B2 (en) | 2011-10-12 | 2015-04-14 | Novartis Ag | Method for making UV-absorbing ophthalmic lenses |
| US9594188B2 (en) | 2011-12-06 | 2017-03-14 | University Of Florida Research Foundation, Inc. | UV blocker loaded contact lenses |
| TWI496838B (zh) * | 2012-11-30 | 2015-08-21 | Pegavision Corp | 矽水膠組成物及以該組成物製備之矽水膠鏡片 |
| EP2931767B1 (en) | 2012-12-14 | 2017-11-08 | Novartis AG | Amphiphilic siloxane-containing (meth)acrylamides and uses thereof |
| CA3030638C (en) | 2012-12-14 | 2020-09-15 | Novartis Ag | Amphiphilic siloxane-containing vinylic monomers and uses thereof |
| US10338408B2 (en) | 2012-12-17 | 2019-07-02 | Novartis Ag | Method for making improved UV-absorbing ophthalmic lenses |
| US9708087B2 (en) | 2013-12-17 | 2017-07-18 | Novartis Ag | Silicone hydrogel lens with a crosslinked hydrophilic coating |
| WO2016032926A1 (en) | 2014-08-26 | 2016-03-03 | Novartis Ag | Method for applying stable coating on silicone hydrogel contact lenses |
| MY184638A (en) | 2015-12-15 | 2021-04-13 | Alcon Inc | Method for applying stable coating on silicone hydrogel contact lenses |
| US10307369B2 (en) * | 2016-09-08 | 2019-06-04 | Yichieh Shiuey | Antimicrobial polymer for use in ophthalmic implants |
| EP3724698B1 (en) | 2017-12-13 | 2021-12-15 | Alcon Inc. | Method for producing mps-compatible water gradient contact lenses |
| US20210077249A1 (en) * | 2018-01-31 | 2021-03-18 | KeraMed, Inc. | Antimicrobial Polymer for Use in Ophthalmic implants |
| US11724471B2 (en) | 2019-03-28 | 2023-08-15 | Johnson & Johnson Vision Care, Inc. | Methods for the manufacture of photoabsorbing contact lenses and photoabsorbing contact lenses produced thereby |
| CN114051497B (zh) | 2019-06-27 | 2024-06-28 | 株式会社德山 | 色烯化合物和光致变色光学物品 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2064480T3 (es) * | 1988-02-26 | 1995-02-01 | Ciba Geigy Ag | Una lente de contacto humectable, rigida, permeable a los gases y practicamente no hinchable. |
| ATE64999T1 (de) * | 1988-02-26 | 1991-07-15 | Ciba Geigy Ag | Benetzbare, flexible, sauerstoffdurchlaessge kontaktlinse, bestehend aus blockcopolymeren mit polysiloxan-polyoxyalkylen gliedern in der hauptkette. |
| JP3195662B2 (ja) * | 1992-08-24 | 2001-08-06 | 株式会社メニコン | 眼用レンズ材料 |
| JP2774233B2 (ja) * | 1992-08-26 | 1998-07-09 | 株式会社メニコン | 眼用レンズ材料 |
| US5336797A (en) * | 1992-12-30 | 1994-08-09 | Bausch & Lomb Incorporated | Siloxane macromonomers |
-
1995
- 1995-06-14 AU AUPN3545A patent/AUPN354595A0/en not_active Abandoned
-
1996
- 1996-06-04 KR KR1019970709321A patent/KR19990022852A/ko not_active Withdrawn
- 1996-06-04 JP JP50258197A patent/JP3892903B2/ja not_active Expired - Lifetime
- 1996-06-04 US US08/981,077 patent/US5981615A/en not_active Expired - Lifetime
- 1996-06-04 EP EP96921926A patent/EP0832142B1/en not_active Expired - Lifetime
- 1996-06-04 WO PCT/EP1996/002421 patent/WO1997000274A1/en not_active Ceased
- 1996-06-04 CA CA002222608A patent/CA2222608A1/en not_active Abandoned
- 1996-06-04 BR BR9608911A patent/BR9608911A/pt not_active Application Discontinuation
- 1996-06-04 IL IL12227996A patent/IL122279A0/xx unknown
- 1996-06-04 DE DE69613841T patent/DE69613841T2/de not_active Expired - Lifetime
- 1996-06-04 AT AT96921926T patent/ATE203031T1/de not_active IP Right Cessation
- 1996-06-13 ZA ZA965016A patent/ZA965016B/xx unknown
-
1997
- 1997-12-11 NO NO975839A patent/NO975839L/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE69613841D1 (de) | 2001-08-16 |
| EP0832142A1 (en) | 1998-04-01 |
| JP3892903B2 (ja) | 2007-03-14 |
| AUPN354595A0 (en) | 1995-07-06 |
| CA2222608A1 (en) | 1997-01-03 |
| ATE203031T1 (de) | 2001-07-15 |
| ZA965016B (en) | 1996-12-17 |
| DE69613841T2 (de) | 2002-04-04 |
| NO975839D0 (no) | 1997-12-11 |
| IL122279A0 (en) | 1998-04-05 |
| NO975839L (no) | 1998-02-12 |
| WO1997000274A1 (en) | 1997-01-03 |
| MX9710041A (es) | 1998-03-29 |
| US5981615A (en) | 1999-11-09 |
| BR9608911A (pt) | 1999-03-02 |
| EP0832142B1 (en) | 2001-07-11 |
| JPH11507682A (ja) | 1999-07-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 19971212 Patent event code: PA01051R01D Comment text: International Patent Application |
|
| PG1501 | Laying open of application | ||
| PC1203 | Withdrawal of no request for examination | ||
| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |