CA2093660C - Polymeres contenant des silicones et lentilles corneennes hydrophiles permeables a l'oxygene renfermant lesdits polymeres - Google Patents

Polymeres contenant des silicones et lentilles corneennes hydrophiles permeables a l'oxygene renfermant lesdits polymeres Download PDF

Info

Publication number: CA2093660C
Authority: CA; Canada
Prior art keywords: weight; composition according; hydrophilic; block; monomers
Prior art date: 1990-10-11
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 - Lifetime

Application number

CA002093660A

Other languages

English (en)

Other versions

CA2093660A1 (fr

Inventor

Mohammed I. Ali

Waifong Anton

Henry D. Coleman

Leonard Seidner

Harry J. Spinelli

Lester Weintraub

Paul White

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Johnson and Johnson Vision Care Inc

Original Assignee

Johnson and Johnson Vision Care Inc

Priority date (The priority date 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 date listed.)

1990-10-11

Filing date

1991-10-10

Publication date

2005-06-07

1991-10-10 Application filed by Johnson and Johnson Vision Care Inc filed Critical Johnson and Johnson Vision Care Inc

1992-04-12 Publication of CA2093660A1 publication Critical patent/CA2093660A1/fr

2005-06-07 Application granted granted Critical

2005-06-07 Publication of CA2093660C publication Critical patent/CA2093660C/fr

2011-10-10 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

229920000642 polymer Polymers 0.000 title claims abstract description 243
229920001296 polysiloxane Polymers 0.000 title claims abstract description 112
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 title description 53
239000001301 oxygen Substances 0.000 title description 53
229910052760 oxygen Inorganic materials 0.000 title description 53
239000000178 monomer Substances 0.000 claims abstract description 232
239000000203 mixture Substances 0.000 claims abstract description 215
229920001577 copolymer Polymers 0.000 claims abstract description 135
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 95
239000011159 matrix material Substances 0.000 claims abstract description 73
150000002148 esters Chemical class 0.000 claims abstract description 67
229920006243 acrylic copolymer Polymers 0.000 claims abstract description 49
238000006116 polymerization reaction Methods 0.000 claims abstract description 40
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 37
238000004132 cross linking Methods 0.000 claims abstract description 16
WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 126
229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims description 120
-1 methacryloxy, acryloxy Chemical group 0.000 claims description 71
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 68
230000002209 hydrophobic effect Effects 0.000 claims description 55
NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 52
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 51
WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 21
229920001400 block copolymer Polymers 0.000 claims description 20
STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Chemical group CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 claims description 19
DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 claims description 17
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 description 13
RPHZUCPDKQHAHC-UHFFFAOYSA-N N=C=O.CC(=C)C1=CC=CC=C1 Chemical compound N=C=O.CC(=C)C1=CC=CC=C1 RPHZUCPDKQHAHC-UHFFFAOYSA-N 0.000 claims description 13
125000000962 organic group Chemical group 0.000 claims description 13
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 description 12
229920005604 random copolymer Polymers 0.000 claims description 12
230000036571 hydration Effects 0.000 claims description 11
238000006703 hydration reaction Methods 0.000 claims description 11
125000000217 alkyl group Chemical group 0.000 claims description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
SOGFHWHHBILCSX-UHFFFAOYSA-J prop-2-enoate silicon(4+) Chemical group [Si+4].[O-]C(=O)C=C.[O-]C(=O)C=C.[O-]C(=O)C=C.[O-]C(=O)C=C SOGFHWHHBILCSX-UHFFFAOYSA-J 0.000 claims description 8
239000000126 substance Substances 0.000 claims description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
125000000746 allylic group Chemical group 0.000 claims description 6
239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 6
125000005395 methacrylic acid group Chemical group 0.000 claims description 6
LTHJXDSHSVNJKG-UHFFFAOYSA-N 2-[2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOCCOC(=O)C(C)=C LTHJXDSHSVNJKG-UHFFFAOYSA-N 0.000 claims description 5
OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 claims description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 4
150000001408 amides Chemical class 0.000 claims description 4
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 3
KCTMTGOHHMRJHZ-UHFFFAOYSA-N n-(2-methylpropoxymethyl)prop-2-enamide Chemical compound CC(C)COCNC(=O)C=C KCTMTGOHHMRJHZ-UHFFFAOYSA-N 0.000 claims description 3
229910052710 silicon Inorganic materials 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
HWSSEYVMGDIFMH-UHFFFAOYSA-N 2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOC(=O)C(C)=C HWSSEYVMGDIFMH-UHFFFAOYSA-N 0.000 claims description 2
XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 2
125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 4
RQAVKYPVSDCFJQ-UHFFFAOYSA-N 2-methyl-n-(2-methylpropoxy)prop-2-enamide Chemical compound CC(C)CONC(=O)C(C)=C RQAVKYPVSDCFJQ-UHFFFAOYSA-N 0.000 claims 3
125000004846 (C1-C4) allyl group Chemical group 0.000 claims 1
150000001721 carbon Chemical group 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 claims 1
JEGUKCSWCFPDGT-UHFFFAOYSA-N h2o hydrate Chemical compound O.O JEGUKCSWCFPDGT-UHFFFAOYSA-N 0.000 claims 1
UACSZOWTRIJIFU-UHFFFAOYSA-N hydroxymethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCO UACSZOWTRIJIFU-UHFFFAOYSA-N 0.000 claims 1
229920000578 graft copolymer Polymers 0.000 abstract description 51
239000002253 acid Substances 0.000 abstract description 36
150000001252 acrylic acid derivatives Chemical class 0.000 abstract description 31
238000002360 preparation method Methods 0.000 abstract description 22
150000007513 acids Chemical class 0.000 abstract description 18
206010047571 Visual impairment Diseases 0.000 abstract description 2
238000002560 therapeutic procedure Methods 0.000 abstract description 2
208000029257 vision disease Diseases 0.000 abstract description 2
230000004393 visual impairment Effects 0.000 abstract description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 116
241000219739 Lens Species 0.000 description 93
238000006243 chemical reaction Methods 0.000 description 50
230000035699 permeability Effects 0.000 description 48
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
238000000034 method Methods 0.000 description 42
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
239000000243 solution Substances 0.000 description 39
ZSPOJBDHHFFJAP-UHFFFAOYSA-M 3-chlorobenzoate;tetrabutylazanium Chemical compound [O-]C(=O)C1=CC=CC(Cl)=C1.CCCC[N+](CCCC)(CCCC)CCCC ZSPOJBDHHFFJAP-UHFFFAOYSA-M 0.000 description 35
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 32
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 32
239000003999 initiator Substances 0.000 description 31
VBYLGQXERITIBP-UHFFFAOYSA-N n-[dimethylamino(methyl)silyl]-n-methylmethanamine Chemical compound CN(C)[SiH](C)N(C)C VBYLGQXERITIBP-UHFFFAOYSA-N 0.000 description 28
URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 26
JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 24
125000002887 hydroxy group Chemical group [H]O* 0.000 description 23
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 16
229910052757 nitrogen Inorganic materials 0.000 description 16
WUGOQZFPNUYUOO-UHFFFAOYSA-N 2-trimethylsilyloxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCO[Si](C)(C)C WUGOQZFPNUYUOO-UHFFFAOYSA-N 0.000 description 15
238000001035 drying Methods 0.000 description 14
239000000463 material Substances 0.000 description 14
239000002904 solvent Substances 0.000 description 14
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 13
229940063557 methacrylate Drugs 0.000 description 13
UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 12
239000012975 dibutyltin dilaurate Substances 0.000 description 12
229960005215 dichloroacetic acid Drugs 0.000 description 12
125000000524 functional group Chemical group 0.000 description 12
XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 10
150000001875 compounds Chemical class 0.000 description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
238000003756 stirring Methods 0.000 description 10
238000007334 copolymerization reaction Methods 0.000 description 9
239000007789 gas Substances 0.000 description 9
238000002156 mixing Methods 0.000 description 9
239000000017 hydrogel Substances 0.000 description 8
229920003229 poly(methyl methacrylate) Polymers 0.000 description 8
239000004926 polymethyl methacrylate Substances 0.000 description 8
230000008569 process Effects 0.000 description 8
239000004743 Polypropylene Substances 0.000 description 7
229920001155 polypropylene Polymers 0.000 description 7
230000002194 synthesizing effect Effects 0.000 description 7
238000012546 transfer Methods 0.000 description 7
238000009736 wetting Methods 0.000 description 7
SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 6
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
229920001519 homopolymer Polymers 0.000 description 6
238000004519 manufacturing process Methods 0.000 description 6
QYPPRTNMGCREIM-UHFFFAOYSA-N methylarsonic acid Chemical compound C[As](O)(O)=O QYPPRTNMGCREIM-UHFFFAOYSA-N 0.000 description 6
239000008363 phosphate buffer Substances 0.000 description 6
238000010526 radical polymerization reaction Methods 0.000 description 6
JNOGVQJEBGEKMG-UHFFFAOYSA-N (1-methoxy-2-methylprop-1-enoxy)-trimethylsilane Chemical compound COC(=C(C)C)O[Si](C)(C)C JNOGVQJEBGEKMG-UHFFFAOYSA-N 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 5
239000012948 isocyanate Substances 0.000 description 5
150000002513 isocyanates Chemical class 0.000 description 5
239000012299 nitrogen atmosphere Substances 0.000 description 5
XSCRXCDDATUDLB-UHFFFAOYSA-N 2-(2-methylpropoxymethyl)prop-2-enamide Chemical compound CC(C)COCC(=C)C(N)=O XSCRXCDDATUDLB-UHFFFAOYSA-N 0.000 description 4
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
238000012662 bulk polymerization Methods 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
239000003431 cross linking reagent Substances 0.000 description 4
SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 4
239000011737 fluorine Substances 0.000 description 4
229910052731 fluorine Inorganic materials 0.000 description 4
238000009472 formulation Methods 0.000 description 4
238000010348 incorporation Methods 0.000 description 4
239000007788 liquid Substances 0.000 description 4
229920000058 polyacrylate Polymers 0.000 description 4
230000000379 polymerizing effect Effects 0.000 description 4
150000003254 radicals Chemical class 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
125000002348 vinylic group Chemical group 0.000 description 4
230000000007 visual effect Effects 0.000 description 4
JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
241000894006 Bacteria Species 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
150000008360 acrylonitriles Chemical class 0.000 description 3
150000008064 anhydrides Chemical class 0.000 description 3
238000013459 approach Methods 0.000 description 3
230000000903 blocking effect Effects 0.000 description 3
230000007423 decrease Effects 0.000 description 3
230000007812 deficiency Effects 0.000 description 3
230000002349 favourable effect Effects 0.000 description 3
ZYMKZMDQUPCXRP-UHFFFAOYSA-N fluoro prop-2-enoate Chemical compound FOC(=O)C=C ZYMKZMDQUPCXRP-UHFFFAOYSA-N 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
229920005684 linear copolymer Polymers 0.000 description 3
150000002632 lipids Chemical class 0.000 description 3
LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 3
NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 3
102000004169 proteins and genes Human genes 0.000 description 3
108090000623 proteins and genes Proteins 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
238000010561 standard procedure Methods 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
229920002554 vinyl polymer Polymers 0.000 description 3
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
SJIXRGNQPBQWMK-UHFFFAOYSA-N 2-(diethylamino)ethyl 2-methylprop-2-enoate Chemical compound CCN(CC)CCOC(=O)C(C)=C SJIXRGNQPBQWMK-UHFFFAOYSA-N 0.000 description 2
JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 2
INQDDHNZXOAFFD-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOC(=O)C=C INQDDHNZXOAFFD-UHFFFAOYSA-N 0.000 description 2
HCLJOFJIQIJXHS-UHFFFAOYSA-N 2-[2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOCCOC(=O)C=C HCLJOFJIQIJXHS-UHFFFAOYSA-N 0.000 description 2
ZTJNPDLOIVDEEL-UHFFFAOYSA-N 2-acetyloxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOC(C)=O ZTJNPDLOIVDEEL-UHFFFAOYSA-N 0.000 description 2
OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 2
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 2
IGAWKPMXUGZZIH-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOC(=O)C=C IGAWKPMXUGZZIH-UHFFFAOYSA-N 0.000 description 2
QQGMMQNLCCSWQL-UHFFFAOYSA-N 2-trimethylsilyloxypropyl 2-methylprop-2-enoate Chemical compound C[Si](C)(C)OC(C)COC(=O)C(C)=C QQGMMQNLCCSWQL-UHFFFAOYSA-N 0.000 description 2
NGSFHVAMOMGZFQ-UHFFFAOYSA-N 3,3-dimethoxypropyl prop-2-enoate Chemical compound COC(OC)CCOC(=O)C=C NGSFHVAMOMGZFQ-UHFFFAOYSA-N 0.000 description 2
WIYVVIUBKNTNKG-UHFFFAOYSA-N 6,7-dimethoxy-3,4-dihydronaphthalene-2-carboxylic acid Chemical compound C1CC(C(O)=O)=CC2=C1C=C(OC)C(OC)=C2 WIYVVIUBKNTNKG-UHFFFAOYSA-N 0.000 description 2
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239000004593 Epoxy Substances 0.000 description 2
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
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208000027418 Wounds and injury Diseases 0.000 description 2
QWYSJTTWCUXHQO-UHFFFAOYSA-N [F].OC(=O)C=C Chemical compound [F].OC(=O)C=C QWYSJTTWCUXHQO-UHFFFAOYSA-N 0.000 description 2
125000005370 alkoxysilyl group Chemical group 0.000 description 2
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238000010539 anionic addition polymerization reaction Methods 0.000 description 2
NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 2
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229920001971 elastomer Polymers 0.000 description 2
239000000806 elastomer Substances 0.000 description 2
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125000001153 fluoro group Chemical group F* 0.000 description 2
239000001530 fumaric acid Substances 0.000 description 2
229920001002 functional polymer Polymers 0.000 description 2
239000012528 membrane Substances 0.000 description 2
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238000012986 modification Methods 0.000 description 2
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238000000465 moulding Methods 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 2
238000006068 polycondensation reaction Methods 0.000 description 2
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239000000047 product Substances 0.000 description 2
230000005855 radiation Effects 0.000 description 2
238000000926 separation method Methods 0.000 description 2
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
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RFPCAOZQZVOGEB-UHFFFAOYSA-N trimethyl-(2-methyl-1-trimethylsilyloxyprop-1-enoxy)silane Chemical compound C[Si](C)(C)OC(=C(C)C)O[Si](C)(C)C RFPCAOZQZVOGEB-UHFFFAOYSA-N 0.000 description 1
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Classifications

- 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
- 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
- C08F287/00—Macromolecular compounds obtained by polymerising monomers on to block polymers
- 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
- C08F293/00—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule

Landscapes

Chemical & Material Sciences (AREA)
Physics & Mathematics (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Physics & Mathematics (AREA)
Optics & Photonics (AREA)
Macromonomer-Based Addition Polymer (AREA)
Eyeglasses (AREA)
Graft Or Block Polymers (AREA)
Lens Barrels (AREA)
Compositions Of Macromolecular Compounds (AREA)
Silicon Polymers (AREA)

CA002093660A 1990-10-11 1991-10-10 Polymeres contenant des silicones et lentilles corneennes hydrophiles permeables a l'oxygene renfermant lesdits polymeres Expired - Lifetime CA2093660C (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US59551290A	1990-10-11	1990-10-11
US595,512		1990-10-11
PCT/US1991/007244 WO1992007013A1 (fr)	1990-10-11	1991-10-10	Nouveaux polymeres contenant du silicone et lentilles de contact hydrophiles permeables a l'oxygene fabriquees a partir de ces polymeres

Publications (2)

Publication Number	Publication Date
CA2093660A1 CA2093660A1 (fr)	1992-04-12
CA2093660C true CA2093660C (fr)	2005-06-07

Family

ID=24383526

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002093660A Expired - Lifetime CA2093660C (fr)	1990-10-11	1991-10-10	Polymeres contenant des silicones et lentilles corneennes hydrophiles permeables a l'oxygene renfermant lesdits polymeres

Country Status (5)

Country	Link
EP (1)	EP0552306A1 (fr)
JP (1)	JP3753328B2 (fr)
AU (1)	AU8955091A (fr)
CA (1)	CA2093660C (fr)
WO (1)	WO1992007013A1 (fr)

Families Citing this family (22)

* Cited by examiner, † Cited by third party
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US5760100B1 (en) *	1994-09-06	2000-11-14	Ciba Vision Corp	Extended wear ophthalmic lens
US7468398B2 (en)	1994-09-06	2008-12-23	Ciba Vision Corporation	Extended wear ophthalmic lens
TW585882B (en) *	1995-04-04	2004-05-01	Novartis Ag	A method of using a contact lens as an extended wear lens and a method of screening an ophthalmic lens for utility as an extended-wear lens
US6943203B2 (en)	1998-03-02	2005-09-13	Johnson & Johnson Vision Care, Inc.	Soft contact lenses
US7461937B2 (en)	2001-09-10	2008-12-09	Johnson & Johnson Vision Care, Inc.	Soft contact lenses displaying superior on-eye comfort
US6367929B1 (en)	1998-03-02	2002-04-09	Johnson & Johnson Vision Care, Inc.	Hydrogel with internal wetting agent
US6849671B2 (en)	1998-03-02	2005-02-01	Johnson & Johnson Vision Care, Inc.	Contact lenses
US5981675A (en) *	1998-12-07	1999-11-09	Bausch & Lomb Incorporated	Silicone-containing macromonomers and low water materials
EP1235866B1 (fr) *	1999-10-07	2006-08-09	Johnson & Johnson Vision Care, Inc.	Lentilles de contact souples
US6488375B2 (en)	1999-10-28	2002-12-03	Ocular Sciences, Inc.	Tinted contact lens and method for making same
US7267846B2 (en)	1999-11-01	2007-09-11	Praful Doshi	Tinted lenses and methods of manufacture
US6880932B2 (en)	1999-11-01	2005-04-19	Praful Doshi	Tinted lenses and methods of manufacture
WO2003021337A1 (fr) *	2000-03-03	2003-03-13	Johnson & Johnson Vision Care, Inc.	Lentille oculaire
JP4273612B2 (ja) *	2000-03-03	2009-06-03	東レ株式会社	眼用レンズ
US6815074B2 (en)	2001-05-30	2004-11-09	Novartis Ag	Polymeric materials for making contact lenses
CN1319638C (zh)	2001-06-13	2007-06-06	能源及环境国际有限公司	本体聚合反应器和聚合方法
US6730767B2 (en)	2001-11-02	2004-05-04	Bausch & Lomb Incorporated	High refractive index aromatic-based siloxane monofunctional macromonomers
WO2003042265A1 (fr) *	2001-11-13	2003-05-22	Toray Industries, Inc.	Polymere et lentilles ophthalmologiques realisees a l'aide de ce polymere
CN101035823B (zh) *	2004-10-08	2012-07-04	弗门尼舍有限公司	两亲星型嵌段共聚物
JP4810099B2 (ja) *	2005-01-20	2011-11-09	株式会社メニコン	透明ゲルおよびそれからなるコンタクトレンズ
DE102005009066A1 (de) *	2005-02-28	2006-09-07	Osram Opto Semiconductors Gmbh	Verfahren zur Herstellung eines optischen und eines strahlungsemittierenden Bauelementes und optisches sowie strahlungsemittierendes Bauelement
WO2011108435A1 (fr) *	2010-03-02	2011-09-09	大日精化工業株式会社	Copolymère bloc contenant un groupe alkoxysilyle, son procédé de production, pigment traité avec de la résine, et dispersion de pigment

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA1281449C (fr) *	1986-08-29	1991-03-12	Clyde S. Hutchins	Polymeres acryliques hybrides en etoile et leur preparation
US5106930A (en) *	1988-09-28	1992-04-21	Ioptex Research Inc.	Contact lenses
US5032647A (en) *	1989-09-29	1991-07-16	E. I. Du Pont De Nemours And Company	Process for making hybrid acrylic star polymers with polysiloxane cores
US5036139A (en) *	1989-09-29	1991-07-30	E. I. Du Pont De Nemours And Company	Hybrid acrylic star polymers with polysiloxane cores
US5057578A (en) *	1990-04-10	1991-10-15	E. I. Du Pont De Nemours And Company	Silicone-containing block copolymers and macromonomers
US5019628A (en) *	1990-04-10	1991-05-28	E. I. Du Pont De Nemours And Company	Silicone containing acrylic star polymers

1991
- 1991-10-10 CA CA002093660A patent/CA2093660C/fr not_active Expired - Lifetime
- 1991-10-10 JP JP51854091A patent/JP3753328B2/ja not_active Expired - Lifetime
- 1991-10-10 WO PCT/US1991/007244 patent/WO1992007013A1/fr not_active Ceased
- 1991-10-10 EP EP19910920611 patent/EP0552306A1/fr not_active Ceased
- 1991-10-10 AU AU89550/91A patent/AU8955091A/en not_active Abandoned

Also Published As

Publication number	Publication date
AU8955091A (en)	1992-05-20
JP3753328B2 (ja)	2006-03-08
CA2093660A1 (fr)	1992-04-12
JPH06503103A (ja)	1994-04-07
EP0552306A1 (fr)	1993-07-28
WO1992007013A1 (fr)	1992-04-30

Legal Events

Date	Code	Title	Description
1998-09-17	EEER	Examination request
2011-10-10	MKEX	Expiry

Publication	Publication Date	Title
US5371147A (en)	1994-12-06	Silicone-containing acrylic star polymers, block copolymers and macromonomers
US5314960A (en)	1994-05-24	Silicone-containing polymers, oxygen permeable hydrophilic contact lenses and methods for making these lenses and treating patients with visual impairment
CA2093660C (fr)	2005-06-07	Polymeres contenant des silicones et lentilles corneennes hydrophiles permeables a l'oxygene renfermant lesdits polymeres
US5314961A (en)	1994-05-24	Silicone-containing polymers, compositions and improved oxygen permeable hydrophilic contact lenses
US5244981A (en)	1993-09-14	Silicone-containing contact lens polymers, oxygen permeable contact lenses and methods for making these lenses and treating patients with visual impairment
US5057578A (en)	1991-10-15	Silicone-containing block copolymers and macromonomers
US5563184A (en)	1996-10-08	Macromonomers
US4625007A (en)	1986-11-25	Silicone-containing contact lens material and contact lenses made thereof
JP2003526707A (ja)	2003-09-09	ソフト・コンタクト・レンズ
HK1001590B (en)	1998-06-26	Novel macromonomers
WO2002050144A2 (fr)	2002-06-27	Biomateriaux polymeriques contenant des monomeres de silsesquioxane
JP3441024B2 (ja)	2003-08-25	親水性含フッ素シロキサンモノマー及びその樹脂からなる眼科用レンズ材料
US7084188B2 (en)	2006-08-01	Surface modification of contact lenses
EP1706438A1 (fr)	2006-10-04	Nouveaux prepolymeres pour la modification de surface amelioree de lentilles de contact
US5019628A (en)	1991-05-28	Silicone containing acrylic star polymers
WO1992007014A1 (fr)	1992-04-30	Nouveaux polymeres acryliques etoiles, copolymeres sequences et macromonomeres contenant du silicone
US20020075448A1 (en)	2002-06-20	Poly(2-oxazoline) biomedical devices
JP2876013B2 (ja)	1999-03-31	酸素透過性成形物
WO2023209855A1 (fr)	2023-11-02	Polymère d'addition et matériau de lentille en silicone hydrogel
MXPA06006230A (en)	2006-10-17	Novel prepolymers for improved surface modification of contact lenses