JP2012508902A5 - - Google Patents
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- Publication number
- JP2012508902A5 JP2012508902A5 JP2011536423A JP2011536423A JP2012508902A5 JP 2012508902 A5 JP2012508902 A5 JP 2012508902A5 JP 2011536423 A JP2011536423 A JP 2011536423A JP 2011536423 A JP2011536423 A JP 2011536423A JP 2012508902 A5 JP2012508902 A5 JP 2012508902A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- vinyl
- alkyl
- hydrophilic
- trimethylsiloxy
- 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.)
- Granted
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- 239000000178 monomer Substances 0.000 claims 22
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 18
- 229920002554 vinyl polymer Polymers 0.000 claims 18
- -1 siloxane units Chemical group 0.000 claims 14
- 125000000217 alkyl group Chemical group 0.000 claims 13
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims 10
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims 8
- 239000000463 material Substances 0.000 claims 8
- 229920001577 copolymer Polymers 0.000 claims 7
- 125000000524 functional group Chemical group 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 239000007983 Tris buffer Substances 0.000 claims 6
- 125000002947 alkylene group Chemical group 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 5
- 239000000017 hydrogel Substances 0.000 claims 5
- 229920001296 polysiloxane Polymers 0.000 claims 5
- 150000003254 radicals Chemical class 0.000 claims 5
- 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 4
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims 4
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 claims 4
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims 4
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims 4
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims 4
- 229920000642 polymer Polymers 0.000 claims 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims 3
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims 2
- 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 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 2
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 claims 2
- LUTFTISESXWDHG-UHFFFAOYSA-N 3-aminopropyl 2-methylprop-2-enoate;hydrochloride Chemical compound Cl.CC(=C)C(=O)OCCCN LUTFTISESXWDHG-UHFFFAOYSA-N 0.000 claims 2
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 claims 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims 2
- 239000002202 Polyethylene glycol Substances 0.000 claims 2
- 125000002843 carboxylic acid group Chemical group 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000002993 cycloalkylene group Chemical group 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 125000005647 linker group Chemical group 0.000 claims 2
- 239000011159 matrix material Substances 0.000 claims 2
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 claims 2
- DQCSJGUXTUJMAA-UHFFFAOYSA-N n,n-dimethylmethanamine;2-hydroxypropyl 2-methylprop-2-enoate;hydrochloride Chemical compound Cl.CN(C)C.CC(O)COC(=O)C(C)=C DQCSJGUXTUJMAA-UHFFFAOYSA-N 0.000 claims 2
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical group CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 claims 2
- OMNKZBIFPJNNIO-UHFFFAOYSA-N n-(2-methyl-4-oxopentan-2-yl)prop-2-enamide Chemical compound CC(=O)CC(C)(C)NC(=O)C=C OMNKZBIFPJNNIO-UHFFFAOYSA-N 0.000 claims 2
- PNLUGRYDUHRLOF-UHFFFAOYSA-N n-ethenyl-n-methylacetamide Chemical compound C=CN(C)C(C)=O PNLUGRYDUHRLOF-UHFFFAOYSA-N 0.000 claims 2
- RQAKESSLMFZVMC-UHFFFAOYSA-N n-ethenylacetamide Chemical compound CC(=O)NC=C RQAKESSLMFZVMC-UHFFFAOYSA-N 0.000 claims 2
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 claims 2
- KYKIFKUTBWKKRE-UHFFFAOYSA-N n-ethenylpropan-2-amine Chemical compound CC(C)NC=C KYKIFKUTBWKKRE-UHFFFAOYSA-N 0.000 claims 2
- 229920001223 polyethylene glycol Polymers 0.000 claims 2
- 150000003141 primary amines Chemical class 0.000 claims 2
- 230000005855 radiation Effects 0.000 claims 2
- 150000003335 secondary amines Chemical class 0.000 claims 2
- 125000005156 substituted alkylene group Chemical group 0.000 claims 2
- 150000003512 tertiary amines Chemical group 0.000 claims 2
- JWYVGKFDLWWQJX-UHFFFAOYSA-N 1-ethenylazepan-2-one Chemical group C=CN1CCCCCC1=O JWYVGKFDLWWQJX-UHFFFAOYSA-N 0.000 claims 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
- ZIFLDVXQTMSDJE-UHFFFAOYSA-N 3-[[dimethyl-[3-(2-methylprop-2-enoyloxy)propyl]silyl]oxy-dimethylsilyl]propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC[Si](C)(C)O[Si](C)(C)CCCOC(=O)C(C)=C ZIFLDVXQTMSDJE-UHFFFAOYSA-N 0.000 claims 1
- NWBTXZPDTSKZJU-UHFFFAOYSA-N 3-[dimethyl(trimethylsilyloxy)silyl]propyl 2-methylprop-2-enoate Chemical group CC(=C)C(=O)OCCC[Si](C)(C)O[Si](C)(C)C NWBTXZPDTSKZJU-UHFFFAOYSA-N 0.000 claims 1
- MXRGSJAOLKBZLU-UHFFFAOYSA-N 3-ethenylazepan-2-one Chemical compound C=CC1CCCCNC1=O MXRGSJAOLKBZLU-UHFFFAOYSA-N 0.000 claims 1
- 239000004971 Cross linker Substances 0.000 claims 1
- 239000004593 Epoxy Substances 0.000 claims 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims 1
- 235000018936 Vitellaria paradoxa Nutrition 0.000 claims 1
- PKDAKIZIHVXQTQ-UHFFFAOYSA-N [2-hydroxy-3-[3-tris(trimethylsilyloxy)silylpropoxy]propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)COCCC[Si](O[Si](C)(C)C)(O[Si](C)(C)C)O[Si](C)(C)C PKDAKIZIHVXQTQ-UHFFFAOYSA-N 0.000 claims 1
- UHPPAPGGMSFXNF-UHFFFAOYSA-N [2-hydroxy-3-[[propyl-bis(trimethylsilyloxy)silyl]methoxy]propyl] 2-methylprop-2-enoate Chemical compound CCC[Si](O[Si](C)(C)C)(O[Si](C)(C)C)COCC(O)COC(=O)C(C)=C UHPPAPGGMSFXNF-UHFFFAOYSA-N 0.000 claims 1
- 150000001412 amines Chemical group 0.000 claims 1
- 239000003242 anti bacterial agent Substances 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 239000012867 bioactive agent Substances 0.000 claims 1
- 230000000903 blocking effect Effects 0.000 claims 1
- 239000012986 chain transfer agent Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000003086 colorant Substances 0.000 claims 1
- 238000007334 copolymerization reaction Methods 0.000 claims 1
- 239000007822 coupling agent Substances 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 238000009792 diffusion process Methods 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000003700 epoxy group Chemical group 0.000 claims 1
- KZJNAICCMJTRKF-UHFFFAOYSA-N ethenyl 2-trimethylsilylethyl carbonate Chemical compound C[Si](C)(C)CCOC(=O)OC=C KZJNAICCMJTRKF-UHFFFAOYSA-N 0.000 claims 1
- BPFOYPDHLJUICH-UHFFFAOYSA-N ethenyl ethyl carbonate Chemical compound CCOC(=O)OC=C BPFOYPDHLJUICH-UHFFFAOYSA-N 0.000 claims 1
- ILHMPZFVDISGNP-UHFFFAOYSA-N ethenyl n-[3-tris(trimethylsilyloxy)silylpropyl]carbamate Chemical compound C[Si](C)(C)O[Si](O[Si](C)(C)C)(O[Si](C)(C)C)CCCNC(=O)OC=C ILHMPZFVDISGNP-UHFFFAOYSA-N 0.000 claims 1
- UJOLYBGCVQJVLI-UHFFFAOYSA-N ethenyl propyl carbonate Chemical compound CCCOC(=O)OC=C UJOLYBGCVQJVLI-UHFFFAOYSA-N 0.000 claims 1
- KRAZQXAPJAYYJI-UHFFFAOYSA-N ethenyl trimethylsilylmethyl carbonate Chemical compound C[Si](C)(C)COC(=O)OC=C KRAZQXAPJAYYJI-UHFFFAOYSA-N 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 238000007306 functionalization reaction Methods 0.000 claims 1
- 229920001477 hydrophilic polymer Polymers 0.000 claims 1
- 230000005660 hydrophilic surface Effects 0.000 claims 1
- 230000002209 hydrophobic effect Effects 0.000 claims 1
- 239000003999 initiator Substances 0.000 claims 1
- 239000012948 isocyanate Substances 0.000 claims 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims 1
- 150000002513 isocyanates Chemical class 0.000 claims 1
- 239000012633 leachable Substances 0.000 claims 1
- 239000000314 lubricant Substances 0.000 claims 1
- DCBBWYIVFRLKCD-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-2-methylprop-2-enamide Chemical compound CN(C)CCNC(=O)C(C)=C DCBBWYIVFRLKCD-UHFFFAOYSA-N 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- RSMSNGDEGGHXOY-UHFFFAOYSA-N n-ethyl-n',n',2-trimethylprop-2-enehydrazide Chemical compound CCN(N(C)C)C(=O)C(C)=C RSMSNGDEGGHXOY-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- YYEOYYNOEQBFRK-UHFFFAOYSA-N pent-1-enyl hydrogen carbonate Chemical compound CCCC=COC(O)=O YYEOYYNOEQBFRK-UHFFFAOYSA-N 0.000 claims 1
- 230000035699 permeability Effects 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 239000003504 photosensitizing agent Substances 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 claims 1
- DRNXZGJGRSUXHW-UHFFFAOYSA-N silyl carbamate Chemical compound NC(=O)O[SiH3] DRNXZGJGRSUXHW-UHFFFAOYSA-N 0.000 claims 1
- 238000004381 surface treatment Methods 0.000 claims 1
- 235000019756 total sulphur amino acid Nutrition 0.000 claims 1
- UHUUYVZLXJHWDV-UHFFFAOYSA-N trimethyl(methylsilyloxy)silane Chemical compound C[SiH2]O[Si](C)(C)C UHUUYVZLXJHWDV-UHFFFAOYSA-N 0.000 claims 1
- PGRZLADNCDNGTC-UHFFFAOYSA-N trimethyl-(methyl-propyl-trimethylsilyloxysilyl)oxysilane Chemical compound CCC[Si](C)(O[Si](C)(C)C)O[Si](C)(C)C PGRZLADNCDNGTC-UHFFFAOYSA-N 0.000 claims 1
- SVTUWEUXLNHYPF-UHFFFAOYSA-N trimethyl-[propyl-bis(trimethylsilyloxy)silyl]oxysilane Chemical compound CCC[Si](O[Si](C)(C)C)(O[Si](C)(C)C)O[Si](C)(C)C SVTUWEUXLNHYPF-UHFFFAOYSA-N 0.000 claims 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11422808P | 2008-11-13 | 2008-11-13 | |
| US61/114,228 | 2008-11-13 | ||
| PCT/US2009/063945 WO2010056687A2 (en) | 2008-11-13 | 2009-11-11 | Silicone hydrogel materials with chemically bound wetting agents |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012508902A JP2012508902A (ja) | 2012-04-12 |
| JP2012508902A5 true JP2012508902A5 (OSRAM) | 2012-12-20 |
| JP5748224B2 JP5748224B2 (ja) | 2015-07-15 |
Family
ID=41566234
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011536423A Expired - Fee Related JP5748224B2 (ja) | 2008-11-13 | 2009-11-11 | 化学結合した湿潤剤を有するシリコーンハイドロゲル材料 |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US8404759B2 (OSRAM) |
| EP (2) | EP3598181B1 (OSRAM) |
| JP (1) | JP5748224B2 (OSRAM) |
| AR (1) | AR074111A1 (OSRAM) |
| CA (1) | CA2739102C (OSRAM) |
| TW (1) | TWI465469B (OSRAM) |
| WO (1) | WO2010056687A2 (OSRAM) |
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| KR101506430B1 (ko) | 2008-12-18 | 2015-03-26 | 노파르티스 아게 | 실리콘 히드로겔 콘택트 렌즈의 제조 방법 |
| NZ621745A (en) | 2010-07-30 | 2015-01-30 | Novartis Ag | Amphiphilic polysiloxane prepolymers and uses thereof |
| KR101930686B1 (ko) * | 2010-07-30 | 2018-12-18 | 노파르티스 아게 | 가교된 친수성 코팅을 갖는 실리콘 히드로겔 렌즈 |
| 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 |
| EP2718751B1 (en) * | 2011-06-09 | 2015-07-22 | Novartis AG | Silicone hydrogel lenses with nano-textured surfaces |
| CN105518058B (zh) * | 2012-03-22 | 2019-03-26 | 莫门蒂夫性能材料股份有限公司 | 有机基-改性的有机硅聚合物和包含它的水凝胶 |
| CN104321352B (zh) | 2012-03-22 | 2017-09-26 | 莫门蒂夫性能材料股份有限公司 | 可聚合的含酰胺基的有机硅化合物、含硅聚合物以及由其制备的生物医学装置 |
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| JP5452756B1 (ja) | 2013-07-02 | 2014-03-26 | Ｈｏｙａ株式会社 | 親水性表面を有するシリコーン含有共重合体成形品を作製する方法及び親水性表面を有するシリコーンハイドロゲルコンタクトレンズ |
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2009
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- 2009-11-11 WO PCT/US2009/063945 patent/WO2010056687A2/en not_active Ceased
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- 2009-11-11 CA CA2739102A patent/CA2739102C/en active Active
- 2009-11-13 TW TW098138725A patent/TWI465469B/zh not_active IP Right Cessation
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2013
- 2013-02-26 US US13/776,787 patent/US20130172504A1/en not_active Abandoned
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