CA2811013C - Chain-extended polysiloxane crosslinkers with dangling hydrophilic polymer chains - Google Patents
Chain-extended polysiloxane crosslinkers with dangling hydrophilic polymer chains Download PDFInfo
- Publication number
- CA2811013C CA2811013C CA2811013A CA2811013A CA2811013C CA 2811013 C CA2811013 C CA 2811013C CA 2811013 A CA2811013 A CA 2811013A CA 2811013 A CA2811013 A CA 2811013A CA 2811013 C CA2811013 C CA 2811013C
- Authority
- CA
- Canada
- Prior art keywords
- group
- acrylamide
- propyl
- meth
- polysiloxane
- 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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- -1 polysiloxane Polymers 0.000 title claims abstract description 301
- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 238
- 239000004971 Cross linker Substances 0.000 title claims abstract description 112
- 229920001477 hydrophilic polymer Polymers 0.000 title claims abstract description 92
- 229920000642 polymer Polymers 0.000 claims abstract description 50
- 238000004132 cross linking Methods 0.000 claims abstract description 12
- 239000000178 monomer Substances 0.000 claims description 138
- 125000002348 vinylic group Chemical group 0.000 claims description 123
- 125000000524 functional group Chemical group 0.000 claims description 106
- 239000000203 mixture Substances 0.000 claims description 100
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 57
- 238000000034 method Methods 0.000 claims description 54
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 49
- 239000000463 material Substances 0.000 claims description 47
- 150000003254 radicals Chemical group 0.000 claims description 47
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 40
- 229910052760 oxygen Inorganic materials 0.000 claims description 40
- 239000001301 oxygen Substances 0.000 claims description 40
- 229920001577 copolymer Polymers 0.000 claims description 38
- 229920001223 polyethylene glycol Polymers 0.000 claims description 37
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 34
- 239000000017 hydrogel Substances 0.000 claims description 32
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 29
- 238000005859 coupling reaction Methods 0.000 claims description 27
- 125000005647 linker group Chemical group 0.000 claims description 27
- 230000002209 hydrophobic effect Effects 0.000 claims description 25
- 229910052757 nitrogen Inorganic materials 0.000 claims description 25
- 125000003277 amino group Chemical group 0.000 claims description 23
- 239000012986 chain transfer agent Substances 0.000 claims description 19
- 239000007822 coupling agent Substances 0.000 claims description 19
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 19
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 19
- IEJPPSMHUUQABK-UHFFFAOYSA-N 2,4-diphenyl-4h-1,3-oxazol-5-one Chemical group O=C1OC(C=2C=CC=CC=2)=NC1C1=CC=CC=C1 IEJPPSMHUUQABK-UHFFFAOYSA-N 0.000 claims description 18
- 239000006096 absorbing agent Substances 0.000 claims description 18
- 239000003999 initiator Substances 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- DQRFCVHLNUNVPL-UHFFFAOYSA-N 2h-1,3-oxazol-5-one Chemical compound O=C1OCN=C1 DQRFCVHLNUNVPL-UHFFFAOYSA-N 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 16
- 125000003700 epoxy group Chemical group 0.000 claims description 16
- 239000002202 Polyethylene glycol Substances 0.000 claims description 15
- 239000007983 Tris buffer Substances 0.000 claims description 15
- 150000004820 halides Chemical class 0.000 claims description 14
- 230000008569 process Effects 0.000 claims description 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 13
- 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 description 12
- 230000000379 polymerizing effect Effects 0.000 claims description 12
- 229920002554 vinyl polymer Polymers 0.000 claims description 11
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000002947 alkylene group Chemical group 0.000 claims description 10
- 125000004069 aziridinyl group Chemical group 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000012633 leachable Substances 0.000 claims description 10
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 9
- 238000006116 polymerization reaction Methods 0.000 claims description 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 7
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical group C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 7
- 238000010560 atom transfer radical polymerization reaction Methods 0.000 claims description 7
- 239000003431 cross linking reagent Substances 0.000 claims description 7
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 6
- OXBLVCZKDOZZOJ-UHFFFAOYSA-N 2,3-Dihydrothiophene Chemical compound C1CC=CS1 OXBLVCZKDOZZOJ-UHFFFAOYSA-N 0.000 claims description 6
- 238000006596 Alder-ene reaction Methods 0.000 claims description 6
- 101710141544 Allatotropin-related peptide Proteins 0.000 claims description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 6
- 238000006845 Michael addition reaction Methods 0.000 claims description 6
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims description 6
- 239000012867 bioactive agent Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 6
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 5
- IAXXETNIOYFMLW-COPLHBTASA-N [(1s,3s,4s)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate Chemical compound C1C[C@]2(C)[C@@H](OC(=O)C(=C)C)C[C@H]1C2(C)C IAXXETNIOYFMLW-COPLHBTASA-N 0.000 claims description 5
- 239000004599 antimicrobial Substances 0.000 claims description 5
- KBLWLMPSVYBVDK-UHFFFAOYSA-N cyclohexyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC1 KBLWLMPSVYBVDK-UHFFFAOYSA-N 0.000 claims description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
- 229940119545 isobornyl methacrylate Drugs 0.000 claims description 5
- 239000000314 lubricant Substances 0.000 claims description 5
- 239000003381 stabilizer Substances 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- NWBTXZPDTSKZJU-UHFFFAOYSA-N 3-[dimethyl(trimethylsilyloxy)silyl]propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC[Si](C)(C)O[Si](C)(C)C NWBTXZPDTSKZJU-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 claims description 4
- COKCUFWYUWBZRR-UHFFFAOYSA-N C[Si](CCCC=COC(O)=O)(C)C Chemical compound C[Si](CCCC=COC(O)=O)(C)C COKCUFWYUWBZRR-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 4
- MEEXKBYFINUCHB-UHFFFAOYSA-N N-[3-[3-[bis(trimethylsilyloxy)methylsilyl]propoxy]-2-hydroxypropyl]prop-2-enamide Chemical compound C[Si](C)(C)OC(O[Si](C)(C)C)[SiH2]CCCOCC(O)CNC(=O)C=C MEEXKBYFINUCHB-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 4
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 4
- 125000005529 alkyleneoxy group Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- RQOUVVOOPXZSQH-UHFFFAOYSA-N ethenyl (2,2,4-trimethyl-4-silyloxypentan-3-yl) carbonate Chemical compound [SiH3]OC(C)(C)C(C(C)(C)C)OC(=O)OC=C RQOUVVOOPXZSQH-UHFFFAOYSA-N 0.000 claims description 4
- KZJNAICCMJTRKF-UHFFFAOYSA-N ethenyl 2-trimethylsilylethyl carbonate Chemical compound C[Si](C)(C)CCOC(=O)OC=C KZJNAICCMJTRKF-UHFFFAOYSA-N 0.000 claims description 4
- NDXTZJDCEOXFOP-UHFFFAOYSA-N ethenyl 3-tris(trimethylsilyloxy)silylpropyl carbonate Chemical compound C[Si](C)(C)O[Si](O[Si](C)(C)C)(O[Si](C)(C)C)CCCOC(=O)OC=C NDXTZJDCEOXFOP-UHFFFAOYSA-N 0.000 claims description 4
- BHBDVHVTNOYHLK-UHFFFAOYSA-N ethenyl 3-tris(trimethylsilyloxy)silylpropylsulfanylformate Chemical compound C[Si](C)(C)O[Si](O[Si](C)(C)C)(O[Si](C)(C)C)CCCSC(=O)OC=C BHBDVHVTNOYHLK-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 4
- KRAZQXAPJAYYJI-UHFFFAOYSA-N ethenyl trimethylsilylmethyl carbonate Chemical compound C[Si](C)(C)COC(=O)OC=C KRAZQXAPJAYYJI-UHFFFAOYSA-N 0.000 claims description 4
- CZYCGAZGQQOBPI-UHFFFAOYSA-N n,n-bis[2-hydroxy-3-[3-tris(trimethylsilyloxy)silylpropoxy]propyl]prop-2-enamide Chemical compound C[Si](C)(C)O[Si](O[Si](C)(C)C)(O[Si](C)(C)C)CCCOCC(O)CN(C(=O)C=C)CC(O)COCCC[Si](O[Si](C)(C)C)(O[Si](C)(C)C)O[Si](C)(C)C CZYCGAZGQQOBPI-UHFFFAOYSA-N 0.000 claims description 4
- WQDYCVSCYQRCNL-UHFFFAOYSA-N n,n-bis[3-[3-[tert-butyl(dimethyl)silyl]propoxy]-2-hydroxypropyl]prop-2-enamide Chemical compound CC(C)(C)[Si](C)(C)CCCOCC(O)CN(C(=O)C=C)CC(O)COCCC[Si](C)(C)C(C)(C)C WQDYCVSCYQRCNL-UHFFFAOYSA-N 0.000 claims description 4
- MVBJSQCJPSRKSW-UHFFFAOYSA-N n-[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]prop-2-enamide Chemical compound OCC(CO)(CO)NC(=O)C=C MVBJSQCJPSRKSW-UHFFFAOYSA-N 0.000 claims description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
- XVOUMQNXTGKGMA-OWOJBTEDSA-N (E)-glutaconic acid Chemical compound OC(=O)C\C=C\C(O)=O XVOUMQNXTGKGMA-OWOJBTEDSA-N 0.000 claims description 3
- CTXUTPWZJZHRJC-UHFFFAOYSA-N 1-ethenylpyrrole Chemical group C=CN1C=CC=C1 CTXUTPWZJZHRJC-UHFFFAOYSA-N 0.000 claims description 3
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 claims description 3
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 3
- JJRUAPNVLBABCN-UHFFFAOYSA-N 2-(ethenoxymethyl)oxirane Chemical compound C=COCC1CO1 JJRUAPNVLBABCN-UHFFFAOYSA-N 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 3
- BQBSIHIZDSHADD-UHFFFAOYSA-N 2-ethenyl-4,5-dihydro-1,3-oxazole Chemical group C=CC1=NCCO1 BQBSIHIZDSHADD-UHFFFAOYSA-N 0.000 claims description 3
- NEYTXADIGVEHQD-UHFFFAOYSA-N 2-hydroxy-2-(prop-2-enoylamino)acetic acid Chemical compound OC(=O)C(O)NC(=O)C=C NEYTXADIGVEHQD-UHFFFAOYSA-N 0.000 claims description 3
- KFDVPJUYSDEJTH-UHFFFAOYSA-N 4-ethenylpyridine Chemical group C=CC1=CC=NC=C1 KFDVPJUYSDEJTH-UHFFFAOYSA-N 0.000 claims description 3
- QMGSWHWVTKQYNL-UHFFFAOYSA-N N,N-bis[3-[3-[bis(trimethylsilyloxy)methylsilyl]propoxy]-2-hydroxypropyl]prop-2-enamide Chemical compound C[Si](C)(C)OC(O[Si](C)(C)C)[SiH2]CCCOCC(O)CN(C(=O)C=C)CC(O)COCCC[SiH2]C(O[Si](C)(C)C)O[Si](C)(C)C QMGSWHWVTKQYNL-UHFFFAOYSA-N 0.000 claims description 3
- NBOCBWJUDBATAS-UHFFFAOYSA-N [2-hydroxy-3-[3-[methyl-bis(trimethylsilyloxy)silyl]propoxy]propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)COCCC[Si](C)(O[Si](C)(C)C)O[Si](C)(C)C NBOCBWJUDBATAS-UHFFFAOYSA-N 0.000 claims description 3
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 claims description 3
- 229940018557 citraconic acid Drugs 0.000 claims description 3
- 125000001153 fluoro group Chemical class F* 0.000 claims description 3
- 239000001530 fumaric acid Substances 0.000 claims description 3
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 3
- 239000011976 maleic acid Substances 0.000 claims description 3
- HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 claims description 3
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 3
- HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 claims description 3
- UIUXUFNYAYAMOE-UHFFFAOYSA-N methylsilane Chemical compound [SiH3]C UIUXUFNYAYAMOE-UHFFFAOYSA-N 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 2
- VWNAITWBRLKIIS-UHFFFAOYSA-N 1-sulfanylpropane-1,1-diol Chemical compound CCC(O)(O)S VWNAITWBRLKIIS-UHFFFAOYSA-N 0.000 claims description 2
- PBFKVYVGYHNCGT-UHFFFAOYSA-N 1-sulfanylpropane-1,2,3-triol Chemical compound OCC(O)C(O)S PBFKVYVGYHNCGT-UHFFFAOYSA-N 0.000 claims description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 2
- DVOOXRTYGGLORL-UHFFFAOYSA-N 2-(methylazaniumyl)-3-sulfanylpropanoate Chemical compound CNC(CS)C(O)=O DVOOXRTYGGLORL-UHFFFAOYSA-N 0.000 claims description 2
- LDFDXRPEWZHIML-UHFFFAOYSA-N 2-(sulfanylmethyl)pentanedioic acid Chemical compound OC(=O)CCC(CS)C(O)=O LDFDXRPEWZHIML-UHFFFAOYSA-N 0.000 claims description 2
- CZDHUFYOXKHLME-UHFFFAOYSA-N 2-amino-3-methyl-3-sulfanylbutanoic acid;hydron;chloride Chemical compound Cl.CC(C)(S)C(N)C(O)=O CZDHUFYOXKHLME-UHFFFAOYSA-N 0.000 claims description 2
- FPPNONHSLAHRLW-UHFFFAOYSA-N 2-ethenyl-4,4-diethyl-1,3-oxazol-5-one Chemical compound CCC1(CC)N=C(C=C)OC1=O FPPNONHSLAHRLW-UHFFFAOYSA-N 0.000 claims description 2
- DMDNNZDDQOLFPX-UHFFFAOYSA-N 2-ethenyl-4-ethyl-4-methyl-1,3-oxazol-5-one Chemical compound CCC1(C)N=C(C=C)OC1=O DMDNNZDDQOLFPX-UHFFFAOYSA-N 0.000 claims description 2
- HVXHULQXOUOVJM-UHFFFAOYSA-N 4,5-dihydroxyimidazolidine-2-thione Chemical compound OC1NC(=S)NC1O HVXHULQXOUOVJM-UHFFFAOYSA-N 0.000 claims description 2
- JADFAMLCKYPIHC-UHFFFAOYSA-N 4-(2-aminoethyl)-2-sulfanylphenol Chemical compound NCCC1=CC=C(O)C(S)=C1 JADFAMLCKYPIHC-UHFFFAOYSA-N 0.000 claims description 2
- AOIHJKREJFPKDL-UHFFFAOYSA-N 4-amino-5-sulfanylpentanoic acid Chemical compound SCC(N)CCC(O)=O AOIHJKREJFPKDL-UHFFFAOYSA-N 0.000 claims description 2
- YFYYRKDBDBILSD-UHFFFAOYSA-N 6-amino-2-sulfanylidene-1h-pyrimidin-4-one Chemical compound NC1=CC(=O)NC(=S)N1 YFYYRKDBDBILSD-UHFFFAOYSA-N 0.000 claims description 2
- STUQITWXBMZUGY-UHFFFAOYSA-N 6-hydroxy-2-sulfanylidene-1h-pyrimidin-4-one Chemical compound OC1=CC(O)=NC(S)=N1 STUQITWXBMZUGY-UHFFFAOYSA-N 0.000 claims description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 2
- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical compound NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 claims description 2
- NJRXVEJTAYWCQJ-UHFFFAOYSA-N thiomalic acid Chemical compound OC(=O)CC(S)C(O)=O NJRXVEJTAYWCQJ-UHFFFAOYSA-N 0.000 claims description 2
- MRDPSMYETIZHSQ-UHFFFAOYSA-N n-[2-hydroxy-3-[3-tris(trimethylsilyloxy)silylpropoxy]propyl]-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NCC(O)COCCC[Si](O[Si](C)(C)C)(O[Si](C)(C)C)O[Si](C)(C)C MRDPSMYETIZHSQ-UHFFFAOYSA-N 0.000 claims 3
- WQALPRYWFMIFAG-UHFFFAOYSA-N n-[3-[3-[tert-butyl(dimethyl)silyl]propoxy]-2-hydroxypropyl]-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NCC(O)COCCC[Si](C)(C)C(C)(C)C WQALPRYWFMIFAG-UHFFFAOYSA-N 0.000 claims 3
- OXDDOSYQTPXHEJ-UHFFFAOYSA-N n-[3-[3-[tert-butyl(dimethyl)silyl]propoxy]-2-hydroxypropyl]prop-2-enamide Chemical compound CC(C)(C)[Si](C)(C)CCCOCC(O)CNC(=O)C=C OXDDOSYQTPXHEJ-UHFFFAOYSA-N 0.000 claims 3
- DRNXZGJGRSUXHW-UHFFFAOYSA-N silyl carbamate Chemical compound NC(=O)O[SiH3] DRNXZGJGRSUXHW-UHFFFAOYSA-N 0.000 claims 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 2
- 235000019256 formaldehyde Nutrition 0.000 claims 2
- HOICNMFDTPVMIW-UHFFFAOYSA-N n-[2-hydroxy-3-[3-tris(trimethylsilyloxy)silylpropoxy]propyl]prop-2-enamide Chemical compound C[Si](C)(C)O[Si](O[Si](C)(C)C)(O[Si](C)(C)C)CCCOCC(O)CNC(=O)C=C HOICNMFDTPVMIW-UHFFFAOYSA-N 0.000 claims 2
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 claims 1
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims 1
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
- QKPKBBFSFQAMIY-UHFFFAOYSA-N 2-ethenyl-4,4-dimethyl-1,3-oxazol-5-one Chemical compound CC1(C)N=C(C=C)OC1=O QKPKBBFSFQAMIY-UHFFFAOYSA-N 0.000 claims 1
- SQZSACNFCGPRRH-UHFFFAOYSA-N 2-ethenyl-4-methyl-4-nonyl-1,3-oxazol-5-one Chemical compound CCCCCCCCCC1(C)N=C(C=C)OC1=O SQZSACNFCGPRRH-UHFFFAOYSA-N 0.000 claims 1
- HQGFOVSJARUBLL-UHFFFAOYSA-N 4,4-dibutyl-2-ethenyl-1,3-oxazol-5-one Chemical compound CCCCC1(CCCC)N=C(C=C)OC1=O HQGFOVSJARUBLL-UHFFFAOYSA-N 0.000 claims 1
- MUWZQYSJSCDUDT-UHFFFAOYSA-N 4,4-dimethyl-2-prop-1-en-2-yl-1,3-oxazol-5-one Chemical compound CC(=C)C1=NC(C)(C)C(=O)O1 MUWZQYSJSCDUDT-UHFFFAOYSA-N 0.000 claims 1
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- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
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- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
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- 238000012719 thermal polymerization Methods 0.000 description 1
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Classifications
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- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/34—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
- C08G77/442—Block-or graft-polymers containing polysiloxane sequences containing vinyl polymer sequences
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
- C08G77/46—Block-or graft-polymers containing polysiloxane sequences containing polyether sequences
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions 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; Compositions of derivatives of such polymers
- C08L83/10—Block- or graft-copolymers containing polysiloxane sequences
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B2207/00—Coding scheme for general features or characteristics of optical elements and systems of subclass G02B, but not including elements and systems which would be classified in G02B6/00 and subgroups
- G02B2207/109—Sols, gels, sol-gel materials
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Physics & Mathematics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Optics & Photonics (AREA)
- General Physics & Mathematics (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Inorganic Chemistry (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Ophthalmology & Optometry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Eyeglasses (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US39046410P | 2010-10-06 | 2010-10-06 | |
| US61/390,464 | 2010-10-06 | ||
| US42267210P | 2010-12-14 | 2010-12-14 | |
| US61/422,672 | 2010-12-14 | ||
| PCT/US2011/054870 WO2012047964A1 (en) | 2010-10-06 | 2011-10-05 | Chain-extended polysiloxane crosslinkers with dangling hydrophilic polymer chains |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2811013A1 CA2811013A1 (en) | 2012-04-12 |
| CA2811013C true CA2811013C (en) | 2016-01-19 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2811013A Active CA2811013C (en) | 2010-10-06 | 2011-10-05 | Chain-extended polysiloxane crosslinkers with dangling hydrophilic polymer chains |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US8835525B2 (enExample) |
| EP (1) | EP2625217B1 (enExample) |
| JP (1) | JP5640153B2 (enExample) |
| BR (1) | BR112013008221B1 (enExample) |
| CA (1) | CA2811013C (enExample) |
| WO (1) | WO2012047964A1 (enExample) |
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| SG188507A1 (en) * | 2010-10-06 | 2013-04-30 | Novartis Ag | Water-processable silicone-containing prepolymers and uses thereof |
| AU2013220367B2 (en) * | 2012-02-15 | 2016-06-09 | Dsm Ip Assets B.V. | Polysiloxane based block copolymers |
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| JP6154022B2 (ja) | 2012-12-14 | 2017-06-28 | ノバルティス アーゲー | 両親媒性シロキサン含有(メタ)アクリルアミド及びこれらの使用 |
| WO2014093756A1 (en) | 2012-12-14 | 2014-06-19 | Novartis Ag | Actinically-crosslinkable amphiphilic prepolymers |
| EP2931732B1 (en) | 2012-12-14 | 2020-11-25 | Alcon Inc. | Amphiphilic siloxane-containing vinylic monomers and uses thereof |
| US9486311B2 (en) | 2013-02-14 | 2016-11-08 | Shifamed Holdings, Llc | Hydrophilic AIOL with bonding |
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| SG2013035662A (en) * | 2013-05-08 | 2014-12-30 | Menicon Singapore Pte Ltd | Systems and methods for printing on a contact lens |
| EP2808707A1 (en) | 2013-05-31 | 2014-12-03 | DSM IP Assets B.V. | Macromers comprising pendant polyoxazoline groups |
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2011
- 2011-10-05 BR BR112013008221-6A patent/BR112013008221B1/pt active IP Right Grant
- 2011-10-05 EP EP11770628.3A patent/EP2625217B1/en active Active
- 2011-10-05 CA CA2811013A patent/CA2811013C/en active Active
- 2011-10-05 JP JP2013532902A patent/JP5640153B2/ja active Active
- 2011-10-05 US US13/253,177 patent/US8835525B2/en active Active
- 2011-10-05 WO PCT/US2011/054870 patent/WO2012047964A1/en not_active Ceased
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Also Published As
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|---|---|
| US20140350124A1 (en) | 2014-11-27 |
| US8835525B2 (en) | 2014-09-16 |
| US9052440B2 (en) | 2015-06-09 |
| JP2013540188A (ja) | 2013-10-31 |
| EP2625217A1 (en) | 2013-08-14 |
| EP2625217B1 (en) | 2018-07-04 |
| JP5640153B2 (ja) | 2014-12-10 |
| US20120088844A1 (en) | 2012-04-12 |
| CA2811013A1 (en) | 2012-04-12 |
| BR112013008221A2 (pt) | 2016-06-21 |
| BR112013008221B1 (pt) | 2020-02-11 |
| WO2012047964A1 (en) | 2012-04-12 |
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