ES2346812T3 - Copolimeros actinicamente entrelazables para la fabricacion de lentes de contacto. - Google Patents
Copolimeros actinicamente entrelazables para la fabricacion de lentes de contacto. Download PDFInfo
- Publication number
- ES2346812T3 ES2346812T3 ES07812745T ES07812745T ES2346812T3 ES 2346812 T3 ES2346812 T3 ES 2346812T3 ES 07812745 T ES07812745 T ES 07812745T ES 07812745 T ES07812745 T ES 07812745T ES 2346812 T3 ES2346812 T3 ES 2346812T3
- Authority
- ES
- Spain
- Prior art keywords
- prepolymer
- reaction
- group
- hydrophilic monomer
- alkyl
- 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.)
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- 229920001577 copolymer Polymers 0.000 title claims abstract description 40
- 238000004519 manufacturing process Methods 0.000 title claims description 11
- 239000000178 monomer Substances 0.000 claims abstract description 82
- 239000000203 mixture Substances 0.000 claims abstract description 65
- -1 polysiloxane Polymers 0.000 claims abstract description 62
- 238000006243 chemical reaction Methods 0.000 claims abstract description 49
- 239000000463 material Substances 0.000 claims abstract description 49
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 48
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 29
- 125000000524 functional group Chemical group 0.000 claims abstract description 28
- 239000000017 hydrogel Substances 0.000 claims abstract description 28
- 238000012546 transfer Methods 0.000 claims abstract description 25
- 238000007334 copolymerization reaction Methods 0.000 claims abstract description 23
- 150000001875 compounds Chemical class 0.000 claims abstract description 22
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 17
- 238000000746 purification Methods 0.000 claims abstract description 10
- 239000012632 extractable Substances 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims description 69
- 229910052757 nitrogen Inorganic materials 0.000 claims description 35
- 229920000642 polymer Polymers 0.000 claims description 34
- 239000004971 Cross linker Substances 0.000 claims description 31
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 230000008569 process Effects 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 239000012986 chain transfer agent Substances 0.000 claims description 22
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 21
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 21
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 18
- 238000004132 cross linking Methods 0.000 claims description 18
- 239000011541 reaction mixture Substances 0.000 claims description 18
- 239000002202 Polyethylene glycol Substances 0.000 claims description 17
- 229920001223 polyethylene glycol Polymers 0.000 claims description 17
- 125000002947 alkylene group Chemical group 0.000 claims description 16
- 238000006116 polymerization reaction Methods 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 11
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- 150000003573 thiols Chemical class 0.000 claims description 3
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 131
- 239000000243 solution Substances 0.000 description 101
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 62
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 55
- 229920002554 vinyl polymer Polymers 0.000 description 33
- 150000003254 radicals Chemical class 0.000 description 32
- 239000000839 emulsion Substances 0.000 description 31
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 31
- 239000002904 solvent Substances 0.000 description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 22
- 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 20
- 238000007872 degassing Methods 0.000 description 20
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 18
- 229910052760 oxygen Inorganic materials 0.000 description 18
- 239000001301 oxygen Substances 0.000 description 18
- 230000035699 permeability Effects 0.000 description 18
- 238000002360 preparation method Methods 0.000 description 17
- 238000003756 stirring Methods 0.000 description 17
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 16
- OGMADIBCHLQMIP-UHFFFAOYSA-N 2-aminoethanethiol;hydron;chloride Chemical compound Cl.NCCS OGMADIBCHLQMIP-UHFFFAOYSA-N 0.000 description 15
- 229940097265 cysteamine hydrochloride Drugs 0.000 description 15
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 description 14
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 description 14
- 239000004205 dimethyl polysiloxane Substances 0.000 description 13
- 238000010438 heat treatment Methods 0.000 description 13
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- 230000005855 radiation Effects 0.000 description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- 238000003760 magnetic stirring Methods 0.000 description 12
- 238000000465 moulding Methods 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 11
- 238000000605 extraction Methods 0.000 description 11
- 239000012530 fluid Substances 0.000 description 11
- CXQXSVUQTKDNFP-UHFFFAOYSA-N octamethyltrisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C CXQXSVUQTKDNFP-UHFFFAOYSA-N 0.000 description 11
- 238000004987 plasma desorption mass spectroscopy Methods 0.000 description 11
- 238000000108 ultra-filtration Methods 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 230000007717 exclusion Effects 0.000 description 10
- 230000002209 hydrophobic effect Effects 0.000 description 10
- 239000003999 initiator Substances 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 9
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 9
- 230000000845 anti-microbial effect Effects 0.000 description 9
- 239000011248 coating agent Substances 0.000 description 9
- 238000000576 coating method Methods 0.000 description 9
- 238000009472 formulation Methods 0.000 description 9
- 238000004128 high performance liquid chromatography Methods 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 238000001816 cooling Methods 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 230000036571 hydration Effects 0.000 description 8
- 238000006703 hydration reaction Methods 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 239000011780 sodium chloride Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
- 238000013019 agitation Methods 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
- 239000008367 deionised water Substances 0.000 description 6
- 229910021641 deionized water Inorganic materials 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 238000004108 freeze drying Methods 0.000 description 6
- 150000002431 hydrogen Chemical class 0.000 description 6
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 238000005520 cutting process Methods 0.000 description 5
- 238000009792 diffusion process Methods 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 238000010348 incorporation Methods 0.000 description 5
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- 239000012299 nitrogen atmosphere Substances 0.000 description 5
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- 229920001155 polypropylene Polymers 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- IEJPPSMHUUQABK-UHFFFAOYSA-N 2,4-diphenyl-4h-1,3-oxazol-5-one Chemical compound O=C1OC(C=2C=CC=CC=2)=NC1C1=CC=CC=C1 IEJPPSMHUUQABK-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 239000000470 constituent Substances 0.000 description 4
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 description 4
- 238000011026 diafiltration Methods 0.000 description 4
- 229920001519 homopolymer Polymers 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- 150000002513 isocyanates Chemical class 0.000 description 4
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
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- 125000003277 amino group Chemical group 0.000 description 3
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- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 2
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- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2483/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen, or carbon only; Derivatives of such polymers
- C08J2483/04—Polysiloxanes
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- 2007-07-10 AT AT07812745T patent/ATE470681T1/de active
- 2007-07-10 BR BRPI0714430-0A patent/BRPI0714430A2/pt not_active IP Right Cessation
- 2007-07-10 PL PL07812745T patent/PL2038310T3/pl unknown
- 2007-07-10 MX MX2009000316A patent/MX2009000316A/es active IP Right Grant
- 2007-07-10 DK DK07812745.3T patent/DK2038310T3/da active
- 2007-07-10 CN CN2007800259565A patent/CN101490099B/zh not_active Expired - Fee Related
- 2007-07-10 PT PT07812745T patent/PT2038310E/pt unknown
- 2007-07-10 WO PCT/US2007/073119 patent/WO2008008752A2/en not_active Ceased
- 2007-07-10 CA CA2655360A patent/CA2655360C/en not_active Expired - Fee Related
- 2007-07-10 EP EP07812745A patent/EP2038310B1/en not_active Not-in-force
- 2007-07-10 AU AU2007272558A patent/AU2007272558B2/en not_active Ceased
- 2007-07-10 ES ES07812745T patent/ES2346812T3/es active Active
- 2007-07-10 US US11/825,961 patent/US8404783B2/en active Active
- 2007-07-10 TW TW096124986A patent/TWI441835B/zh not_active IP Right Cessation
- 2007-07-10 DE DE602007007082T patent/DE602007007082D1/de active Active
- 2007-07-12 AR ARP070103102A patent/AR061978A1/es not_active Application Discontinuation
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- 2013-02-27 US US13/778,882 patent/US8703875B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CN101490099B (zh) | 2013-03-27 |
| WO2008008752A3 (en) | 2008-02-28 |
| AU2007272558A1 (en) | 2008-01-17 |
| CA2655360C (en) | 2014-09-16 |
| US20080015315A1 (en) | 2008-01-17 |
| AU2007272558B2 (en) | 2010-12-09 |
| CN101490099A (zh) | 2009-07-22 |
| PL2038310T3 (pl) | 2010-11-30 |
| DE602007007082D1 (de) | 2010-07-22 |
| NO20090637L (no) | 2009-03-31 |
| PT2038310E (pt) | 2010-08-25 |
| ZA200810050B (en) | 2009-12-30 |
| CA2655360A1 (en) | 2008-01-17 |
| DK2038310T3 (da) | 2010-09-27 |
| JP2009543901A (ja) | 2009-12-10 |
| US20130172600A1 (en) | 2013-07-04 |
| AR061978A1 (es) | 2008-08-10 |
| US8404783B2 (en) | 2013-03-26 |
| JP5271902B2 (ja) | 2013-08-21 |
| TW200821332A (en) | 2008-05-16 |
| BRPI0714430A2 (pt) | 2013-03-12 |
| ATE470681T1 (de) | 2010-06-15 |
| TWI441835B (zh) | 2014-06-21 |
| EP2038310A2 (en) | 2009-03-25 |
| WO2008008752A2 (en) | 2008-01-17 |
| MX2009000316A (es) | 2009-01-26 |
| EP2038310B1 (en) | 2010-06-09 |
| NO340147B1 (no) | 2017-03-13 |
| US8703875B2 (en) | 2014-04-22 |
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