JP2010516873A5 - - Google Patents
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- Publication number
- JP2010516873A5 JP2010516873A5 JP2009547434A JP2009547434A JP2010516873A5 JP 2010516873 A5 JP2010516873 A5 JP 2010516873A5 JP 2009547434 A JP2009547434 A JP 2009547434A JP 2009547434 A JP2009547434 A JP 2009547434A JP 2010516873 A5 JP2010516873 A5 JP 2010516873A5
- Authority
- JP
- Japan
- Prior art keywords
- monomer
- bis
- monomer mixture
- group
- acid
- 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
Links
- 239000000178 monomer Substances 0.000 claims 21
- -1 cationic siloxane Chemical class 0.000 claims 17
- 238000000034 method Methods 0.000 claims 12
- 239000000203 mixture Substances 0.000 claims 11
- 239000003795 chemical substances by application Substances 0.000 claims 6
- 239000007795 chemical reaction product Substances 0.000 claims 4
- 239000004205 dimethyl polysiloxane Substances 0.000 claims 4
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 3
- 239000012528 membrane Substances 0.000 claims 3
- 239000002798 polar solvent Substances 0.000 claims 3
- 229920001296 polysiloxane Polymers 0.000 claims 3
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims 2
- 238000000605 extraction Methods 0.000 claims 2
- 230000002209 hydrophobic effect Effects 0.000 claims 2
- 239000007943 implant Substances 0.000 claims 2
- 238000006116 polymerization reaction Methods 0.000 claims 2
- 239000002516 radical scavenger Substances 0.000 claims 2
- SJHPCNCNNSSLPL-CSKARUKUSA-N (4e)-4-(ethoxymethylidene)-2-phenyl-1,3-oxazol-5-one Chemical compound O1C(=O)C(=C/OCC)\N=C1C1=CC=CC=C1 SJHPCNCNNSSLPL-CSKARUKUSA-N 0.000 claims 1
- VAYTZRYEBVHVLE-UHFFFAOYSA-N 1,3-dioxol-2-one Chemical compound O=C1OC=CO1 VAYTZRYEBVHVLE-UHFFFAOYSA-N 0.000 claims 1
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 claims 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 claims 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims 1
- LJDSTRZHPWMDPG-UHFFFAOYSA-N 2-(butylamino)ethanol Chemical compound CCCCNCCO LJDSTRZHPWMDPG-UHFFFAOYSA-N 0.000 claims 1
- MIJDSYMOBYNHOT-UHFFFAOYSA-N 2-(ethylamino)ethanol Chemical compound CCNCCO MIJDSYMOBYNHOT-UHFFFAOYSA-N 0.000 claims 1
- BCLSJHWBDUYDTR-UHFFFAOYSA-N 2-(propylamino)ethanol Chemical compound CCCNCCO BCLSJHWBDUYDTR-UHFFFAOYSA-N 0.000 claims 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims 1
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 claims 1
- BESKSSIEODQWBP-UHFFFAOYSA-N 3-tris(trimethylsilyloxy)silylpropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC[Si](O[Si](C)(C)C)(O[Si](C)(C)C)O[Si](C)(C)C BESKSSIEODQWBP-UHFFFAOYSA-N 0.000 claims 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical group NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical group CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims 1
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 claims 1
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 claims 1
- 150000001298 alcohols Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N alpha-methacrylic acid Natural products CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims 1
- 239000000560 biocompatible material Substances 0.000 claims 1
- 210000004204 blood vessel Anatomy 0.000 claims 1
- 210000000481 breast Anatomy 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims 1
- 230000002612 cardiopulmonary effect Effects 0.000 claims 1
- 229920005556 chlorobutyl Polymers 0.000 claims 1
- 238000000502 dialysis Methods 0.000 claims 1
- 239000003063 flame retardant Substances 0.000 claims 1
- 210000003709 heart valve Anatomy 0.000 claims 1
- 239000000017 hydrogel Substances 0.000 claims 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 claims 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims 1
- 210000003734 kidney Anatomy 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims 1
- 125000005395 methacrylic acid group Chemical group 0.000 claims 1
- DCUFMVPCXCSVNP-UHFFFAOYSA-N methacrylic anhydride Chemical compound CC(=C)C(=O)OC(=O)C(C)=C DCUFMVPCXCSVNP-UHFFFAOYSA-N 0.000 claims 1
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 claims 1
- 229940050176 methyl chloride Drugs 0.000 claims 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims 1
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 claims 1
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 claims 1
- 238000004806 packaging method and process Methods 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 230000001954 sterilising effect Effects 0.000 claims 1
- 210000000626 ureter Anatomy 0.000 claims 1
- LVLANIHJQRZTPY-UHFFFAOYSA-N vinyl carbamate Chemical compound NC(=O)OC=C LVLANIHJQRZTPY-UHFFFAOYSA-N 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US88667507P | 2007-01-26 | 2007-01-26 | |
| US60/886,675 | 2007-01-26 | ||
| US12/018,910 | 2008-01-24 | ||
| US12/018,910 US7951897B2 (en) | 2007-01-26 | 2008-01-24 | Synthesis of cationic siloxane prepolymers |
| PCT/US2008/051984 WO2008092048A1 (en) | 2007-01-26 | 2008-01-25 | Improved synthesis of cationic siloxane prepolymers |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010516873A JP2010516873A (ja) | 2010-05-20 |
| JP2010516873A5 true JP2010516873A5 (enExample) | 2011-10-27 |
| JP5307731B2 JP5307731B2 (ja) | 2013-10-02 |
Family
ID=39512817
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009547434A Expired - Fee Related JP5307731B2 (ja) | 2007-01-26 | 2008-01-25 | カチオン性シロキサンプレポリマーの改良合成法 |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US7951897B2 (enExample) |
| EP (1) | EP2125935B1 (enExample) |
| JP (1) | JP5307731B2 (enExample) |
| CN (1) | CN101589091B (enExample) |
| AT (1) | ATE499404T1 (enExample) |
| DE (1) | DE602008005118D1 (enExample) |
| WO (1) | WO2008092048A1 (enExample) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9181401B2 (en) | 2009-06-15 | 2015-11-10 | Dsm Ip Assets B.V. | Phosphorylcholine-based amphiphilic silicones for medical applications |
| US8043369B2 (en) * | 2009-06-16 | 2011-10-25 | Bausch & Lomb Incorporated | Biomedical devices |
| US9039174B2 (en) | 2009-07-09 | 2015-05-26 | Bausch & Lomb Incorporated | Ethylenically unsaturated polymerizable groups comprising polycarbosiloxane monomers |
| US8827447B2 (en) | 2009-07-09 | 2014-09-09 | Bausch & Lomb Incorporated | Mono ethylenically unsaturated polymerizable group containing polycarbosiloxane monomers |
| US7994356B2 (en) | 2009-07-09 | 2011-08-09 | Bausch & Lomb Incorporated | Mono ethylenically unsaturated polycarbosiloxane monomers |
| SG176987A1 (en) * | 2009-07-09 | 2012-01-30 | Bausch & Lomb | Mono ethylenically unsaturated polymerizable group containing polycarbosiloxane monomers |
| US8492569B2 (en) * | 2009-12-18 | 2013-07-23 | Cheil Industries, Inc. | Anthraquinone dye-containing material, composition including the same, camera including the same, and associated methods |
| US20130319958A1 (en) * | 2010-11-30 | 2013-12-05 | Chemrus Inc. | Multi-functional disposable separatory funnels |
| CN103827175B (zh) * | 2011-02-28 | 2016-08-10 | 库柏维景国际控股公司 | 硅酮水凝胶隐形眼镜 |
| US20120283381A1 (en) * | 2011-05-04 | 2012-11-08 | Ryuta Tamiya | Macroinitiator containing hydrophobic segment |
| US8937110B2 (en) | 2011-12-23 | 2015-01-20 | Johnson & Johnson Vision Care, Inc. | Silicone hydrogels having a structure formed via controlled reaction kinetics |
| US9399011B2 (en) * | 2012-03-29 | 2016-07-26 | Momentive Performance Materials Gmbh | Low viscosity polyorganosiloxanes comprising quaternary ammonium groups, methods for the production and the use thereof |
| WO2015001584A1 (ja) * | 2013-07-02 | 2015-01-08 | 株式会社メニコン | コンタクトレンズおよびコンタクトレンズの製造方法 |
| US9668916B2 (en) | 2013-11-04 | 2017-06-06 | Vance M. Thompson | Conjunctival cover and methods therefor |
| EP2873673B1 (en) * | 2013-11-14 | 2017-06-28 | Shin-Etsu Chemical Co., Ltd. | Silicone compound and a use thereof |
| US9869883B2 (en) | 2015-03-11 | 2018-01-16 | Vance M. Thompson | Tear shaping for refractive correction |
| CN105622944B (zh) * | 2016-03-30 | 2018-08-07 | 科凯精细化工（上海）有限公司 | 一种季铵化有机硅油及其制备方法 |
| US10353220B2 (en) | 2016-10-17 | 2019-07-16 | Vance M. Thompson | Tear shaping for refractive correction |
| US10678067B2 (en) | 2018-04-06 | 2020-06-09 | Vance M. Thompson | Tear shaping for refractive correction |
| CN109021184B (zh) * | 2018-07-18 | 2021-03-02 | 常州大学 | 改性聚硅氧烷/聚甲基丙烯酸甲酯复合材料的制备方法 |
| JP6958511B2 (ja) * | 2018-08-17 | 2021-11-02 | 信越化学工業株式会社 | オルガノポリシロキサン化合物およびその製造方法並びにそれを含有する帯電防止剤および硬化性組成物 |
| US20200085564A1 (en) | 2018-09-18 | 2020-03-19 | Vance M. Thompson | Structures and methods for tear shaping for refractive correction |
| JP2025009288A (ja) * | 2023-07-07 | 2025-01-20 | 信越化学工業株式会社 | 分子鎖中に第３級アミノ基または第４級アンモニウムカチオン部位を有する両末端（メタ）アクリル変性シリコーンマクロマーおよびその製造方法 |
| CN116854915A (zh) * | 2023-09-05 | 2023-10-10 | 广东粤港澳大湾区黄埔材料研究院 | 一种有机硅季铵盐抗菌剂和抗菌母粒及其制备方法 |
| CN119752133B (zh) * | 2025-03-10 | 2025-08-15 | 科伦塑业集团股份有限公司 | 一种高透光农用棚膜及其制备方法 |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3808179A (en) * | 1972-06-16 | 1974-04-30 | Polycon Laboratories | Oxygen-permeable contact lens composition,methods and article of manufacture |
| US4153641A (en) * | 1977-07-25 | 1979-05-08 | Bausch & Lomb Incorporated | Polysiloxane composition and contact lens |
| 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 |
| US4910277A (en) * | 1988-02-09 | 1990-03-20 | Bambury Ronald E | Hydrophilic oxygen permeable polymers |
| US5070215A (en) * | 1989-05-02 | 1991-12-03 | Bausch & Lomb Incorporated | Novel vinyl carbonate and vinyl carbamate contact lens material monomers |
| US5152984A (en) * | 1990-11-20 | 1992-10-06 | Dow Corning Corporation | Hair fixatives |
| JPH05164995A (ja) * | 1991-12-17 | 1993-06-29 | Asahi Chem Ind Co Ltd | 耐汚れ付着性ソフトコンタクトレンズ材料 |
| US5358995A (en) * | 1992-05-15 | 1994-10-25 | Bausch & Lomb Incorporated | Surface wettable silicone hydrogels |
| JP3254018B2 (ja) * | 1992-10-20 | 2002-02-04 | 昭和電工株式会社 | ポリオルガノシルセスキオキサン及びその製造方法 |
| US5321108A (en) * | 1993-02-12 | 1994-06-14 | Bausch & Lomb Incorporated | Fluorosilicone hydrogels |
| US5374662A (en) * | 1993-03-15 | 1994-12-20 | Bausch & Lomb Incorporated | Fumarate and fumaramide siloxane hydrogel compositions |
| US5451651A (en) * | 1993-12-17 | 1995-09-19 | Bausch & Lomb Incorporated | Urea and urethane monomers for contact lens materials |
| US5962548A (en) * | 1998-03-02 | 1999-10-05 | Johnson & Johnson Vision Products, Inc. | Silicone hydrogel polymers |
| JP2001098188A (ja) * | 1999-09-29 | 2001-04-10 | Mitsubishi Chemicals Corp | 活性エネルギー線硬化性被覆組成物 |
| KR100332466B1 (ko) * | 2000-05-17 | 2002-04-13 | 박찬구 | 할로겐으로 치환된 다가 반응성 폴리실록산 화합물 및 그제조방법 |
| DE10141356A1 (de) * | 2001-08-23 | 2003-03-06 | Goldschmidt Ag Th | UV-Licht absorbierende quartäre Polysiloxane |
| US6777522B2 (en) * | 2001-11-02 | 2004-08-17 | Bausch & Lomb Incorporated | High refractive index aromatic-based prepolymers |
| JP4656854B2 (ja) * | 2004-04-06 | 2011-03-23 | 富士通セミコンダクター株式会社 | 半導体装置の製造方法 |
| US20060004165A1 (en) * | 2004-06-30 | 2006-01-05 | Phelan John C | Silicone hydrogels with lathability at room temperature |
| US7759408B2 (en) * | 2005-12-21 | 2010-07-20 | Bausch & Lomb Incorporated | Silicon-containing monomers end-capped with polymerizable cationic hydrophilic groups |
| US7622512B2 (en) * | 2005-12-21 | 2009-11-24 | Bausch & Lomb Incorporated | Cationic hydrophilic siloxanyl monomers |
| US7528208B2 (en) * | 2006-01-06 | 2009-05-05 | Bausch & Lomb Incorporated | Siloxane prepolymer containing pendant and end-capping cationic and polymerizable groups |
| US7601766B2 (en) * | 2006-06-30 | 2009-10-13 | Bausch & Lomb Incorporated | Carboxylic siloxanyl monomers with pendant polymerizable groups |
| US7557231B2 (en) * | 2006-06-30 | 2009-07-07 | Bausch & Lomb Incorporated | Carboxylic tris-like siloxanyl monomers |
| US7468397B2 (en) | 2006-06-30 | 2008-12-23 | Bausch & Lomb Incorporated | Polymerizable siloxane-quaternary amine copolymers |
-
2008
- 2008-01-24 US US12/018,910 patent/US7951897B2/en not_active Expired - Fee Related
- 2008-01-25 EP EP08728246A patent/EP2125935B1/en not_active Not-in-force
- 2008-01-25 DE DE602008005118T patent/DE602008005118D1/de active Active
- 2008-01-25 WO PCT/US2008/051984 patent/WO2008092048A1/en not_active Ceased
- 2008-01-25 CN CN2008800028989A patent/CN101589091B/zh not_active Expired - Fee Related
- 2008-01-25 AT AT08728246T patent/ATE499404T1/de not_active IP Right Cessation
- 2008-01-25 JP JP2009547434A patent/JP5307731B2/ja not_active Expired - Fee Related
-
2011
- 2011-03-03 US US13/039,912 patent/US8138288B2/en not_active Expired - Fee Related
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