CA2874607A1 - Polymers and nanogel materials and methods for making and using the same - Google Patents
Polymers and nanogel materials and methods for making and using the same Download PDFInfo
- Publication number
- CA2874607A1 CA2874607A1 CA2874607A CA2874607A CA2874607A1 CA 2874607 A1 CA2874607 A1 CA 2874607A1 CA 2874607 A CA2874607 A CA 2874607A CA 2874607 A CA2874607 A CA 2874607A CA 2874607 A1 CA2874607 A1 CA 2874607A1
- Authority
- CA
- Canada
- Prior art keywords
- segment
- hydrophilic
- polymerization
- block copolymer
- vinyl
- 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.)
- Abandoned
Links
- 229920000642 polymer Polymers 0.000 title claims abstract description 128
- 238000000034 method Methods 0.000 title claims description 66
- 239000000463 material Substances 0.000 title claims description 27
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 184
- 229920001400 block copolymer Polymers 0.000 claims abstract description 153
- 239000000178 monomer Substances 0.000 claims abstract description 124
- 239000000203 mixture Substances 0.000 claims abstract description 96
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 89
- 239000000758 substrate Substances 0.000 claims abstract description 80
- 239000000017 hydrogel Substances 0.000 claims abstract description 44
- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 27
- 125000005647 linker group Chemical group 0.000 claims abstract description 14
- 238000007334 copolymerization reaction Methods 0.000 claims abstract description 8
- -1 poly(N-isopropylacrylamide) Polymers 0.000 claims description 198
- 239000000243 solution Substances 0.000 claims description 106
- 239000003795 chemical substances by application Substances 0.000 claims description 54
- 239000011541 reaction mixture Substances 0.000 claims description 50
- 239000012987 RAFT agent Substances 0.000 claims description 45
- 125000000217 alkyl group Chemical group 0.000 claims description 43
- 150000002632 lipids Chemical class 0.000 claims description 43
- 150000003254 radicals Chemical class 0.000 claims description 39
- AISZNMCRXZWVAT-UHFFFAOYSA-N 2-ethylsulfanylcarbothioylsulfanyl-2-methylpropanenitrile Chemical compound CCSC(=S)SC(C)(C)C#N AISZNMCRXZWVAT-UHFFFAOYSA-N 0.000 claims description 38
- 239000004971 Cross linker Substances 0.000 claims description 36
- 239000003999 initiator Substances 0.000 claims description 34
- 239000003431 cross linking reagent Substances 0.000 claims description 32
- 125000000524 functional group Chemical group 0.000 claims description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 30
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 28
- 238000004132 cross linking Methods 0.000 claims description 28
- 230000008569 process Effects 0.000 claims description 27
- 229920001577 copolymer Polymers 0.000 claims description 25
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims description 22
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
- 239000002997 ophthalmic solution Substances 0.000 claims description 19
- 239000002904 solvent Substances 0.000 claims description 18
- 239000004205 dimethyl polysiloxane Substances 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 229940054534 ophthalmic solution Drugs 0.000 claims description 16
- 229920002554 vinyl polymer Polymers 0.000 claims description 16
- 125000002947 alkylene group Chemical group 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 238000010526 radical polymerization reaction Methods 0.000 claims description 14
- 229920000191 poly(N-vinyl pyrrolidone) Polymers 0.000 claims description 13
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 12
- 239000002202 Polyethylene glycol Substances 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 229920001223 polyethylene glycol Polymers 0.000 claims description 11
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 claims description 11
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 10
- 229920006294 polydialkylsiloxane Polymers 0.000 claims description 10
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
- 150000003926 acrylamides Chemical class 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 238000012546 transfer Methods 0.000 claims description 9
- 238000010560 atom transfer radical polymerization reaction Methods 0.000 claims description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
- 230000000977 initiatory effect Effects 0.000 claims description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- PNLUGRYDUHRLOF-UHFFFAOYSA-N n-ethenyl-n-methylacetamide Chemical compound C=CN(C)C(C)=O PNLUGRYDUHRLOF-UHFFFAOYSA-N 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- ZSZRUEAFVQITHH-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)ethyl 2-(trimethylazaniumyl)ethyl phosphate Chemical compound CC(=C)C(=O)OCCOP([O-])(=O)OCC[N+](C)(C)C ZSZRUEAFVQITHH-UHFFFAOYSA-N 0.000 claims description 6
- NYEZZYQZRQDLEH-UHFFFAOYSA-N 2-ethyl-4,5-dihydro-1,3-oxazole Chemical compound CCC1=NCCO1 NYEZZYQZRQDLEH-UHFFFAOYSA-N 0.000 claims description 6
- GAVHQOUUSHBDAA-UHFFFAOYSA-N 3-butyl-1-ethenylaziridin-2-one Chemical compound CCCCC1N(C=C)C1=O GAVHQOUUSHBDAA-UHFFFAOYSA-N 0.000 claims description 6
- XOQMWEWYWXJOAN-UHFFFAOYSA-N 3-methyl-3-(prop-2-enoylamino)butanoic acid Chemical compound OC(=O)CC(C)(C)NC(=O)C=C XOQMWEWYWXJOAN-UHFFFAOYSA-N 0.000 claims description 6
- YRXLABUVDQYDHV-UHFFFAOYSA-N 4-(prop-2-enoylamino)butanoic acid Chemical compound OC(=O)CCCNC(=O)C=C YRXLABUVDQYDHV-UHFFFAOYSA-N 0.000 claims description 6
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 6
- 125000004423 acyloxy group Chemical group 0.000 claims description 6
- 150000001298 alcohols Chemical class 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 6
- 229920001282 polysaccharide Polymers 0.000 claims description 6
- 239000005017 polysaccharide Substances 0.000 claims description 6
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 6
- 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 5
- 150000001408 amides Chemical class 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 150000007942 carboxylates Chemical class 0.000 claims description 5
- 230000000536 complexating effect Effects 0.000 claims description 5
- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical class NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 claims description 5
- RQAKESSLMFZVMC-UHFFFAOYSA-N n-ethenylacetamide Chemical compound CC(=O)NC=C RQAKESSLMFZVMC-UHFFFAOYSA-N 0.000 claims description 5
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 claims description 5
- 230000000269 nucleophilic effect Effects 0.000 claims description 5
- 229920003213 poly(N-isopropyl acrylamide) Polymers 0.000 claims description 5
- 230000009467 reduction Effects 0.000 claims description 5
- PBGPBHYPCGDFEZ-UHFFFAOYSA-N 1-ethenylpiperidin-2-one Chemical compound C=CN1CCCCC1=O PBGPBHYPCGDFEZ-UHFFFAOYSA-N 0.000 claims description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 4
- YVAQHFNMILVVNE-UHFFFAOYSA-N 3-(prop-2-enoylamino)propanoic acid Chemical compound OC(=O)CCNC(=O)C=C YVAQHFNMILVVNE-UHFFFAOYSA-N 0.000 claims description 4
- VUYGJYAPDGKPBF-UHFFFAOYSA-N 4-(bromomethyl)benzoyl bromide Chemical compound BrCC1=CC=C(C(Br)=O)C=C1 VUYGJYAPDGKPBF-UHFFFAOYSA-N 0.000 claims description 4
- KJJYUNTVGZAHHJ-UHFFFAOYSA-N 5-(prop-2-enoylamino)pentanoic acid Chemical compound OC(=O)CCCCNC(=O)C=C KJJYUNTVGZAHHJ-UHFFFAOYSA-N 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 125000005620 boronic acid group Chemical group 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
- 150000004676 glycans Chemical class 0.000 claims description 4
- 230000007246 mechanism Effects 0.000 claims description 4
- 230000001404 mediated effect Effects 0.000 claims description 4
- QNILTEGFHQSKFF-UHFFFAOYSA-N n-propan-2-ylprop-2-enamide Chemical compound CC(C)NC(=O)C=C QNILTEGFHQSKFF-UHFFFAOYSA-N 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- HGMWQAGLTXDVEW-UHFFFAOYSA-N 1-ethenyl-3-(2-methylbutyl)aziridin-2-one Chemical compound CCC(C)CC1N(C=C)C1=O HGMWQAGLTXDVEW-UHFFFAOYSA-N 0.000 claims description 3
- JBKFPCSZNWLZAS-UHFFFAOYSA-N 1-ethenyl-4-methylpiperidin-2-one Chemical compound CC1CCN(C=C)C(=O)C1 JBKFPCSZNWLZAS-UHFFFAOYSA-N 0.000 claims description 3
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 claims description 3
- PRAMZQXXPOLCIY-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)ethanesulfonic acid Chemical compound CC(=C)C(=O)OCCS(O)(=O)=O PRAMZQXXPOLCIY-UHFFFAOYSA-N 0.000 claims description 3
- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 claims description 3
- KWTGXHDPIPNNHP-UHFFFAOYSA-N 3-[(4-ethenylphenyl)methyl-dimethylazaniumyl]propane-1-sulfonate Chemical compound [O-]S(=O)(=O)CCC[N+](C)(C)CC1=CC=C(C=C)C=C1 KWTGXHDPIPNNHP-UHFFFAOYSA-N 0.000 claims description 3
- FJINYUZGQSMNAS-UHFFFAOYSA-N 3-[dimethyl(3-prop-2-enoyloxypropyl)azaniumyl]propane-1-sulfonate Chemical compound [O-]S(=O)(=O)CCC[N+](C)(C)CCCOC(=O)C=C FJINYUZGQSMNAS-UHFFFAOYSA-N 0.000 claims description 3
- OIETYYKGJGVJFT-UHFFFAOYSA-N 3-[dimethyl-[3-(2-methylprop-2-enoylamino)propyl]azaniumyl]propane-1-sulfonate Chemical compound CC(=C)C(=O)NCCC[N+](C)(C)CCCS([O-])(=O)=O OIETYYKGJGVJFT-UHFFFAOYSA-N 0.000 claims description 3
- KVKJQOXYGGPBIW-UHFFFAOYSA-N 3-[dimethyl-[3-(prop-2-enoylamino)propyl]azaniumyl]propane-1-sulfonate Chemical compound [O-]S(=O)(=O)CCC[N+](C)(C)CCCNC(=O)C=C KVKJQOXYGGPBIW-UHFFFAOYSA-N 0.000 claims description 3
- IRLPACMLTUPBCL-KQYNXXCUSA-N 5'-adenylyl sulfate Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OS(O)(=O)=O)[C@@H](O)[C@H]1O IRLPACMLTUPBCL-KQYNXXCUSA-N 0.000 claims description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 3
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 3
- YUSAHQJQYNVBSP-UHFFFAOYSA-L [K+].[K+].C(C(=C)CC(=O)[O-])(=O)OCCCS(=O)(=O)O.S(=O)(=O)(O)CCCOC(C(=C)CC(=O)[O-])=O Chemical compound [K+].[K+].C(C(=C)CC(=O)[O-])(=O)OCCCS(=O)(=O)O.S(=O)(=O)(O)CCCOC(C(=C)CC(=O)[O-])=O YUSAHQJQYNVBSP-UHFFFAOYSA-L 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- BEJONMZMMIRQRR-UHFFFAOYSA-L disodium 3-(3-sulfopropoxycarbonyl)but-3-enoate Chemical compound [Na+].[Na+].C(C(=C)CC(=O)[O-])(=O)OCCCS(=O)(=O)O.S(=O)(=O)(O)CCCOC(C(=C)CC(=O)[O-])=O BEJONMZMMIRQRR-UHFFFAOYSA-L 0.000 claims description 3
- 229920000669 heparin Polymers 0.000 claims description 3
- 229960002897 heparin Drugs 0.000 claims description 3
- UUORTJUPDJJXST-UHFFFAOYSA-N n-(2-hydroxyethyl)prop-2-enamide Chemical compound OCCNC(=O)C=C UUORTJUPDJJXST-UHFFFAOYSA-N 0.000 claims description 3
- ZTUGCJNAJJDKDC-UHFFFAOYSA-N n-(3-hydroxypropyl)-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NCCCO ZTUGCJNAJJDKDC-UHFFFAOYSA-N 0.000 claims description 3
- DSENQNLOVPYEKP-UHFFFAOYSA-N n-ethenyl-n-methylpropanamide Chemical compound CCC(=O)N(C)C=C DSENQNLOVPYEKP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- 229920002006 poly(N-vinylimidazole) polymer Polymers 0.000 claims description 3
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 3
- ZUBIJGNKOJGGCI-UHFFFAOYSA-M potassium;prop-2-enoate Chemical class [K+].[O-]C(=O)C=C ZUBIJGNKOJGGCI-UHFFFAOYSA-M 0.000 claims description 3
- FWFUWXVFYKCSQA-UHFFFAOYSA-M sodium;2-methyl-2-(prop-2-enoylamino)propane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(C)(C)NC(=O)C=C FWFUWXVFYKCSQA-UHFFFAOYSA-M 0.000 claims description 3
- BWYYYTVSBPRQCN-UHFFFAOYSA-M sodium;ethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=C BWYYYTVSBPRQCN-UHFFFAOYSA-M 0.000 claims description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- 150000008054 sulfonate salts Chemical class 0.000 claims description 3
- 150000003871 sulfonates Chemical class 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 229920000208 temperature-responsive polymer Polymers 0.000 claims description 3
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical class OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- ZRZHXNCATOYMJH-UHFFFAOYSA-N 1-(chloromethyl)-4-ethenylbenzene Chemical compound ClCC1=CC=C(C=C)C=C1 ZRZHXNCATOYMJH-UHFFFAOYSA-N 0.000 claims description 2
- HKOOECSKKYAKJJ-UHFFFAOYSA-N 1-ethenyl-3-pentan-2-ylaziridin-2-one Chemical compound CCCC(C)C1N(C=C)C1=O HKOOECSKKYAKJJ-UHFFFAOYSA-N 0.000 claims description 2
- XRUKRHLZDVJJSX-UHFFFAOYSA-N 4-cyanopentanoic acid Chemical class N#CC(C)CCC(O)=O XRUKRHLZDVJJSX-UHFFFAOYSA-N 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 2
- 239000004593 Epoxy Substances 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical group ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical class CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 150000003863 ammonium salts Chemical class 0.000 claims description 2
- 125000005333 aroyloxy group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 229920006037 cross link polymer Polymers 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 239000012634 fragment Substances 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical class CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 claims description 2
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 claims description 2
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 claims description 2
- ZJDNTSGQAOAXNR-UHFFFAOYSA-N n-ethenyl-2-methylpropanamide Chemical compound CC(C)C(=O)NC=C ZJDNTSGQAOAXNR-UHFFFAOYSA-N 0.000 claims description 2
- MWAITTXTRUIKOM-UHFFFAOYSA-N n-ethenyl-n,2-dimethylpropanamide Chemical compound CC(C)C(=O)N(C)C=C MWAITTXTRUIKOM-UHFFFAOYSA-N 0.000 claims description 2
- 150000004714 phosphonium salts Chemical class 0.000 claims description 2
- 125000004929 pyrrolidonyl group Chemical group N1(C(CCC1)=O)* 0.000 claims description 2
- 230000002441 reversible effect Effects 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims 1
- LJKRXFYAKVYSDK-UHFFFAOYSA-N 1-ethenyl-1,3-dimethylurea Chemical compound CNC(=O)N(C)C=C LJKRXFYAKVYSDK-UHFFFAOYSA-N 0.000 claims 1
- JFUWJIKJUNAHEN-UHFFFAOYSA-N 1-ethenyl-3-ethylpyrrolidin-2-one Chemical compound CCC1CCN(C=C)C1=O JFUWJIKJUNAHEN-UHFFFAOYSA-N 0.000 claims 1
- SBEBZMZHYUEOPQ-UHFFFAOYSA-N 1-ethenyl-3-methylpiperidin-2-one Chemical compound CC1CCCN(C=C)C1=O SBEBZMZHYUEOPQ-UHFFFAOYSA-N 0.000 claims 1
- CRJHKHYPIUPQSX-UHFFFAOYSA-N 1-ethenyl-4,5-dimethylpyrrolidin-2-one Chemical compound CC1CC(=O)N(C=C)C1C CRJHKHYPIUPQSX-UHFFFAOYSA-N 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
- 229910006069 SO3H Inorganic materials 0.000 claims 1
- 239000003792 electrolyte Substances 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- XUQIDBSIIKXTTI-UHFFFAOYSA-N n,n-bis(2-hydroxyethyl)prop-2-enamide Chemical compound OCCN(CCO)C(=O)C=C XUQIDBSIIKXTTI-UHFFFAOYSA-N 0.000 claims 1
- 229910052697 platinum Inorganic materials 0.000 claims 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 1
- 150000004772 tellurides Chemical group 0.000 claims 1
- 238000009472 formulation Methods 0.000 abstract description 5
- 238000006243 chemical reaction Methods 0.000 description 42
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 36
- 239000002953 phosphate buffered saline Substances 0.000 description 36
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- 230000015572 biosynthetic process Effects 0.000 description 22
- 238000002360 preparation method Methods 0.000 description 22
- 239000000080 wetting agent Substances 0.000 description 22
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 21
- 239000003085 diluting agent Substances 0.000 description 20
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- 239000002352 surface water Substances 0.000 description 1
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- NMOALOSNPWTWRH-UHFFFAOYSA-N tert-butyl 7,7-dimethyloctaneperoxoate Chemical compound CC(C)(C)CCCCCC(=O)OOC(C)(C)C NMOALOSNPWTWRH-UHFFFAOYSA-N 0.000 description 1
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
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- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
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- 238000001149 thermolysis Methods 0.000 description 1
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- CMWCOKOTCLFJOP-UHFFFAOYSA-N titanium(3+) Chemical compound [Ti+3] CMWCOKOTCLFJOP-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- HIZCIEIDIFGZSS-UHFFFAOYSA-L trithiocarbonate Chemical compound [S-]C([S-])=S HIZCIEIDIFGZSS-UHFFFAOYSA-L 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
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Classifications
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- 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
- C08F293/005—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 using free radical "living" or "controlled" polymerisation, e.g. using a complexing agent
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L53/00—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L53/00—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
- C08L53/005—Modified block copolymers
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- 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
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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
-
- 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
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2203/00—Applications
- C08L2203/02—Applications for biomedical use
Landscapes
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- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Nanotechnology (AREA)
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- Materials Engineering (AREA)
- Crystallography & Structural Chemistry (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Graft Or Block Polymers (AREA)
- Eyeglasses (AREA)
- Dispersion Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Materials For Medical Uses (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
- Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
- Silicon Polymers (AREA)
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| PCT/US2013/040066 WO2013176886A2 (en) | 2012-05-25 | 2013-05-08 | Polymers and nanogel materials and methods for making and using the same |
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Families Citing this family (59)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9475709B2 (en) | 2010-08-25 | 2016-10-25 | Lockheed Martin Corporation | Perforated graphene deionization or desalination |
| US9170349B2 (en) | 2011-05-04 | 2015-10-27 | Johnson & Johnson Vision Care, Inc. | Medical devices having homogeneous charge density and methods for making same |
| US9744617B2 (en) | 2014-01-31 | 2017-08-29 | Lockheed Martin Corporation | Methods for perforating multi-layer graphene through ion bombardment |
| US9834809B2 (en) | 2014-02-28 | 2017-12-05 | Lockheed Martin Corporation | Syringe for obtaining nano-sized materials for selective assays and related methods of use |
| US10653824B2 (en) | 2012-05-25 | 2020-05-19 | Lockheed Martin Corporation | Two-dimensional materials and uses thereof |
| US10073192B2 (en) * | 2012-05-25 | 2018-09-11 | Johnson & Johnson Vision Care, Inc. | Polymers and nanogel materials and methods for making and using the same |
| US9244196B2 (en) * | 2012-05-25 | 2016-01-26 | Johnson & Johnson Vision Care, Inc. | Polymers and nanogel materials and methods for making and using the same |
| US10376845B2 (en) | 2016-04-14 | 2019-08-13 | Lockheed Martin Corporation | Membranes with tunable selectivity |
| US9610546B2 (en) | 2014-03-12 | 2017-04-04 | Lockheed Martin Corporation | Separation membranes formed from perforated graphene and methods for use thereof |
| US10213746B2 (en) | 2016-04-14 | 2019-02-26 | Lockheed Martin Corporation | Selective interfacial mitigation of graphene defects |
| WO2014164621A1 (en) | 2013-03-12 | 2014-10-09 | Lockheed Martin Corporation | Method for forming filter with uniform aperture size |
| US9572918B2 (en) | 2013-06-21 | 2017-02-21 | Lockheed Martin Corporation | Graphene-based filter for isolating a substance from blood |
| SG11201606287VA (en) | 2014-01-31 | 2016-08-30 | Lockheed Corp | Processes for forming composite structures with a two-dimensional material using a porous, non-sacrificial supporting layer |
| WO2015116946A1 (en) | 2014-01-31 | 2015-08-06 | Lockheed Martin Corporation | Perforating two-dimensional materials using broad ion field |
| CN106232205A (zh) | 2014-03-12 | 2016-12-14 | 洛克希德马丁公司 | 由有孔石墨烯形成的分离膜 |
| MX2017002738A (es) | 2014-09-02 | 2017-08-02 | Lockheed Corp | Membranas de hemodialisis y hemofiltracion basadas en un material de membrana bidimensional y metodos que emplean las mismas. |
| US11192292B2 (en) | 2014-12-05 | 2021-12-07 | University Of Florida Research Foundation, Inc. | 3D printing using phase changing matertials as support |
| CN104530311B (zh) * | 2014-12-17 | 2016-05-11 | 长春工业大学 | 一种缺口不敏感性强韧水凝胶及其制备方法 |
| WO2016130953A1 (en) | 2015-02-13 | 2016-08-18 | University Of Florida Research Foundation, Inc. | High speed 3d printing system for wound and tissue replacement |
| WO2016161144A1 (en) * | 2015-04-01 | 2016-10-06 | The Regents Of The University Of Colorado, A Body Corporate | Nanogels for ophthalmic applications |
| JP6998215B2 (ja) | 2015-05-08 | 2022-02-10 | ユニバーシティ オブ フロリダ リサーチ ファンデーション インコーポレーティッド | ３次元細胞培養のための成長培地 |
| WO2017023376A1 (en) | 2015-08-05 | 2017-02-09 | Lockheed Martin Corporation | Perforatable sheets of graphene-based material |
| JP2018530499A (ja) | 2015-08-06 | 2018-10-18 | ロッキード・マーチン・コーポレーション | グラフェンのナノ粒子変性及び穿孔 |
| US11027483B2 (en) | 2015-09-03 | 2021-06-08 | University Of Florida Research Foundation, Inc. | Valve incorporating temporary phase change material |
| KR101964276B1 (ko) | 2015-10-21 | 2019-04-01 | 주식회사 엘지화학 | 딥 성형용 라텍스 조성물 및 이로부터 제조된 성형품 |
| WO2017096263A1 (en) * | 2015-12-04 | 2017-06-08 | University Of Florida Research Foundation, Incorporated | Crosslinkable or functionalizable polymers for 3d printing of soft materials |
| US10259971B2 (en) * | 2015-12-18 | 2019-04-16 | Hrl Laboratories, Llc | Anti-fouling coatings fabricated from polymers containing ionic species |
| CN105670013B (zh) * | 2016-01-05 | 2018-08-07 | 宁夏医科大学 | 六重环境敏感型半互穿网络水凝胶薄膜及其制备方法和应用 |
| US10122054B2 (en) * | 2016-03-17 | 2018-11-06 | GM Global Technology Operations LLC | Battery pack systems that include polymers |
| KR20180133430A (ko) | 2016-04-14 | 2018-12-14 | 록히드 마틴 코포레이션 | 결함 형성 또는 힐링의 인 시츄 모니터링 및 제어를 위한 방법 |
| KR20190018410A (ko) | 2016-04-14 | 2019-02-22 | 록히드 마틴 코포레이션 | 흐름 통로들을 갖는 2차원 막 구조들 |
| EP3442739A4 (en) | 2016-04-14 | 2020-03-04 | Lockheed Martin Corporation | PROCESS FOR PROCESSING GRAPHENE SHEETS FOR LARGE SCALE TRANSFER USING A FREE FLOATING PROCESS |
| WO2017180134A1 (en) | 2016-04-14 | 2017-10-19 | Lockheed Martin Corporation | Methods for in vivo and in vitro use of graphene and other two-dimensional materials |
| CN107556433B (zh) * | 2016-06-30 | 2020-07-31 | 翁秋梅 | 一种具有杂化交联网络的动态聚合物弹性体及其应用 |
| US11021558B2 (en) | 2016-08-05 | 2021-06-01 | Johnson & Johnson Vision Care, Inc. | Polymer compositions containing grafted polymeric networks and processes for their preparation and use |
| US11124644B2 (en) | 2016-09-01 | 2021-09-21 | University Of Florida Research Foundation, Inc. | Organic microgel system for 3D printing of silicone structures |
| US10676575B2 (en) * | 2016-10-06 | 2020-06-09 | Johnson & Johnson Vision Care, Inc. | Tri-block prepolymers and their use in silicone hydrogels |
| ES2678773B1 (es) * | 2017-01-16 | 2019-06-12 | Consejo Superior Investigacion | Recubrimientos tipo hidrogel en base vinil-lactamas |
| CN108047402B (zh) * | 2017-12-18 | 2020-12-18 | 华东理工大学 | 一种基于atrp机理的三嵌段共聚物及制备方法 |
| US11034789B2 (en) | 2018-01-30 | 2021-06-15 | Johnson & Johnson Vision Care, Inc. | Ophthalmic devices containing localized grafted networks and processes for their preparation and use |
| JP7128632B2 (ja) * | 2018-02-26 | 2022-08-31 | 株式会社日本触媒 | 医療用具用コーティング剤、医療用具用硬化性コーティング剤、医療用具用重合体、コーティング方法、医療用具及びその製造方法 |
| CN108546308B (zh) * | 2018-04-17 | 2020-02-18 | 华南理工大学 | 基于超两亲分子的多重响应性离子凝胶及其制备方法 |
| CN113613998B (zh) * | 2019-01-29 | 2023-04-11 | 鲍希与洛姆伯股份有限公司 | 用于隐形眼镜的包装溶液 |
| US12209154B2 (en) * | 2019-02-26 | 2025-01-28 | Menicon Co., Ltd. | Polymer material |
| WO2020232111A1 (en) * | 2019-05-15 | 2020-11-19 | President And Fellows Of Harvard College | Instant and tough adhesion |
| EP3738988B1 (en) * | 2019-05-16 | 2022-07-13 | 3M Innovative Properties Company | Amphiphilic triblock copolymer |
| CN114269811B (zh) * | 2019-08-28 | 2023-08-08 | 波士顿科学国际有限公司 | 包含自由基可聚合单体的多臂聚合物 |
| US11891526B2 (en) | 2019-09-12 | 2024-02-06 | Johnson & Johnson Vision Care, Inc. | Ink composition for cosmetic contact lenses |
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| EP4209345A4 (en) * | 2020-09-03 | 2024-10-23 | Daikin Industries, Ltd. | HARDENABLE COMPOSITION |
| WO2022054851A1 (ja) * | 2020-09-09 | 2022-03-17 | 日本ペイント・オートモーティブコーティングス株式会社 | 塗料用組成物 |
| CN112625599B (zh) * | 2020-12-11 | 2022-03-04 | 中国科学院海洋研究所 | 一种快速自修复超韧有机硅改性聚脲硫脲防污涂层及其制备方法 |
| CN112724325B (zh) * | 2020-12-30 | 2022-08-09 | 合肥工业大学 | 纳米硅交联剂和快速响应水凝胶的制备方法及应用 |
| CN113350047B (zh) * | 2021-06-03 | 2022-09-09 | 嫒赟（上海）生物科技股份有限公司 | 一种负离子卫生巾 |
| KR102553747B1 (ko) * | 2021-10-28 | 2023-07-11 | 한국화학연구원 | 광경화성 해체형 점착제 조성물 및 이의 제조방법 |
| CN114369206B (zh) * | 2021-11-29 | 2025-07-15 | 南京林业大学 | 一种有机硅基raft试剂制备丙烯酸酯防涂鸦乳液及其制备方法 |
| US12510690B2 (en) * | 2022-02-24 | 2025-12-30 | Bausch + Lomb Ireland Limited | Ophthalmic devices |
| WO2024081452A1 (en) * | 2022-10-11 | 2024-04-18 | The Trustees Of Indiana University | Xeno-free peha polymers for 3d printing and methods of making and using the same |
| WO2025064359A1 (en) * | 2023-09-20 | 2025-03-27 | Isp Investments Llc | Block copolymers with polyether moieties and applications thereof |
Family Cites Families (178)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL285986A (https=) | 1961-12-27 | |||
| NL128305C (https=) | 1963-09-11 | |||
| US3808178A (en) | 1972-06-16 | 1974-04-30 | Polycon Laboratories | Oxygen-permeable contact lens composition,methods and article of manufacture |
| US4197266A (en) | 1974-05-06 | 1980-04-08 | Bausch & Lomb Incorporated | Method for forming optical lenses |
| US4113224A (en) | 1975-04-08 | 1978-09-12 | Bausch & Lomb Incorporated | Apparatus for forming optical lenses |
| US3929741A (en) | 1974-07-16 | 1975-12-30 | Datascope Corp | Hydrophilic acrylamido polymers |
| US4018853A (en) | 1974-11-21 | 1977-04-19 | Warner-Lambert Company | Crosslinked, hydrophilic rods of pyrrolidone-methacrylate graft copolymers |
| US4120570A (en) | 1976-06-22 | 1978-10-17 | Syntex (U.S.A.) Inc. | Method for correcting visual defects, compositions and articles of manufacture useful therein |
| US4136250A (en) | 1977-07-20 | 1979-01-23 | Ciba-Geigy Corporation | Polysiloxane hydrogels |
| US4153641A (en) | 1977-07-25 | 1979-05-08 | Bausch & Lomb Incorporated | Polysiloxane composition and contact lens |
| JPS5466853A (en) | 1977-11-08 | 1979-05-29 | Toyo Contact Lens Co Ltd | Soft contact lens |
| US4168112A (en) | 1978-01-05 | 1979-09-18 | Polymer Technology Corporation | Contact lens with a hydrophilic, polyelectrolyte complex coating and method for forming same |
| US4287175A (en) | 1978-06-22 | 1981-09-01 | Merck & Co., Inc. | Contact lens wetting agents |
| US4190277A (en) | 1978-08-30 | 1980-02-26 | England Robert C | Device for insertion, manipulation and removal of soft contact lenses |
| US4436730A (en) | 1979-06-25 | 1984-03-13 | Polymer Technology Corporation | Ionic opthalmic cellulose polymer solutions |
| US4495313A (en) | 1981-04-30 | 1985-01-22 | Mia Lens Production A/S | Preparation of hydrogel for soft contact lens with water displaceable boric acid ester |
| DE3174584D1 (en) | 1981-11-27 | 1986-06-12 | Tsuetaki George F | Polymers primarily for contact lenses, and contact lenses made from them |
| US4557264A (en) | 1984-04-09 | 1985-12-10 | Ethicon Inc. | Surgical filament from polypropylene blended with polyethylene |
| US4680336A (en) | 1984-11-21 | 1987-07-14 | Vistakon, Inc. | Method of forming shaped hydrogel articles |
| US4663409A (en) | 1984-12-24 | 1987-05-05 | Bausch & Lomb Incorporated | Alpha, beta-unsaturated carbonyl modified amino acid monomer and polymers for biomedical uses |
| US4740533A (en) | 1987-07-28 | 1988-04-26 | Ciba-Geigy Corporation | Wettable, flexible, oxygen permeable, substantially non-swellable contact lens containing block copolymer polysiloxane-polyoxyalkylene backbone units, and use thereof |
| US5385996A (en) | 1986-12-05 | 1995-01-31 | Commonwealth Scientific And Industrial Research Organisation | Control of molecular weight and end-group functionality of polymers |
| US5006622A (en) | 1987-04-02 | 1991-04-09 | Bausch & Lomb Incorporated | Polymer compositions for contact lenses |
| US4910277A (en) | 1988-02-09 | 1990-03-20 | Bambury Ronald E | Hydrophilic oxygen permeable polymers |
| US4889664A (en) | 1988-11-25 | 1989-12-26 | Vistakon, Inc. | Method of forming shaped hydrogel articles including contact lenses |
| US5039459A (en) | 1988-11-25 | 1991-08-13 | Johnson & Johnson Vision Products, Inc. | Method of forming shaped hydrogel articles including contact lenses |
| US5070215A (en) | 1989-05-02 | 1991-12-03 | Bausch & Lomb Incorporated | Novel vinyl carbonate and vinyl carbamate contact lens material monomers |
| US5034461A (en) | 1989-06-07 | 1991-07-23 | Bausch & Lomb Incorporated | Novel prepolymers useful in biomedical devices |
| US5319569A (en) | 1989-09-19 | 1994-06-07 | Hewlett-Packard Company | Block averaging of time varying signal attribute measurements |
| US5314960A (en) | 1990-04-10 | 1994-05-24 | Permeable Technologies, Inc. | Silicone-containing polymers, oxygen permeable hydrophilic contact lenses and methods for making these lenses and treating patients with visual impairment |
| US5244981A (en) | 1990-04-10 | 1993-09-14 | Permeable Technologies, Inc. | Silicone-containing contact lens polymers, oxygen permeable contact lenses and methods for making these lenses and treating patients with visual impairment |
| US5371147A (en) | 1990-10-11 | 1994-12-06 | Permeable Technologies, Inc. | Silicone-containing acrylic star polymers, block copolymers and macromonomers |
| US5219965A (en) | 1990-11-27 | 1993-06-15 | Bausch & Lomb Incorporated | Surface modification of polymer objects |
| US5177165A (en) | 1990-11-27 | 1993-01-05 | Bausch & Lomb Incorporated | Surface-active macromonomers |
| EP0493320B1 (en) | 1990-12-20 | 1996-07-31 | Ciba-Geigy Ag | Fluorine and/or Silicone containing poly(alkylene-oxide)-block copolymer hydrogels and contact lenses thereof |
| WO1993005085A1 (en) | 1991-09-12 | 1993-03-18 | Bausch & Lomb Incorporated | Wettable silicone hydrogel compositions and methods |
| US5352714A (en) | 1991-11-05 | 1994-10-04 | Bausch & Lomb Incorporated | Wettable silicone hydrogel compositions and methods for their manufacture |
| DE4143239A1 (de) | 1991-12-31 | 1993-07-01 | Joerg Dipl Chem Schierholz | Pharmazeutische wirkstoffe enthaltende implantierbare vorrichtung aus einem polymeren material sowie verfahren zu deren herstellung |
| JP2966638B2 (ja) | 1992-04-17 | 1999-10-25 | 三菱電機株式会社 | ダイナミック型連想メモリ装置 |
| US5805264A (en) | 1992-06-09 | 1998-09-08 | Ciba Vision Corporation | Process for graft polymerization on surfaces of preformed substates to modify surface properties |
| US5260000A (en) | 1992-08-03 | 1993-11-09 | Bausch & Lomb Incorporated | Process for making silicone containing hydrogel lenses |
| US5944853A (en) | 1992-10-26 | 1999-08-31 | Johnson & Johnson Vision Products, Inc. | Method for preparing halotriazine dye- and vinyl sulfone dye-monomer compounds |
| US5256751A (en) | 1993-02-08 | 1993-10-26 | Vistakon, Inc. | Ophthalmic lens polymer incorporating acyclic monomer |
| US5321108A (en) | 1993-02-12 | 1994-06-14 | Bausch & Lomb Incorporated | Fluorosilicone hydrogels |
| DE4337492C2 (de) | 1993-11-03 | 1999-06-02 | Joerg Michael Dr Re Schierholz | Verfahren zur Inkorporierung lipophiler pharmazeutisch wirksamer Substanzen in weiche Kontaktlinsen zur Erstellung ophthalmologischer kontrollierter Freisetzungssysteme mittels diffusionskontrollierter Sorption |
| US7468398B2 (en) | 1994-09-06 | 2008-12-23 | Ciba Vision Corporation | Extended wear ophthalmic lens |
| US5760100B1 (en) | 1994-09-06 | 2000-11-14 | Ciba Vision Corp | Extended wear ophthalmic lens |
| US5700559A (en) | 1994-12-16 | 1997-12-23 | Advanced Surface Technology | Durable hydrophilic surface coatings |
| FI972737A7 (fi) | 1994-12-30 | 1997-08-27 | Novartis Ag | Möhkälepolymeereihin perustavat polymeerit |
| DE69629230D1 (de) | 1995-03-24 | 2003-09-04 | Ocular Res Of Bonton Inc | Hydrogellinse mit Lipid-Vorbeschichtigung |
| US5723255A (en) | 1995-06-07 | 1998-03-03 | Eastman Kodak Company | Nanoparticulate thermal solvents |
| AU1849297A (en) | 1996-02-14 | 1997-09-02 | Vision Pharmaceuticals L.P. | Compositions and methods for enzyme deactivation |
| US6277365B1 (en) | 1997-09-18 | 2001-08-21 | Bausch & Lomb Incorporated | Ophthalmic composition including a cationic glycoside and an anionic therapeutic agent |
| US6020445A (en) | 1997-10-09 | 2000-02-01 | Johnson & Johnson Vision Products, Inc. | Silicone hydrogel polymers |
| US6451871B1 (en) | 1998-11-25 | 2002-09-17 | Novartis Ag | Methods of modifying surface characteristics |
| US5998498A (en) | 1998-03-02 | 1999-12-07 | Johnson & Johnson Vision Products, Inc. | Soft contact lenses |
| US5962548A (en) | 1998-03-02 | 1999-10-05 | Johnson & Johnson Vision Products, Inc. | Silicone hydrogel polymers |
| US6822016B2 (en) | 2001-09-10 | 2004-11-23 | Johnson & Johnson Vision Care, Inc. | Biomedical devices containing internal wetting agents |
| US7052131B2 (en) | 2001-09-10 | 2006-05-30 | J&J Vision Care, Inc. | Biomedical devices containing internal wetting agents |
| US6367929B1 (en) | 1998-03-02 | 2002-04-09 | Johnson & Johnson Vision Care, Inc. | Hydrogel with internal wetting agent |
| JPH11305172A (ja) | 1998-04-16 | 1999-11-05 | Seiko Epson Corp | 含水性ソフトコンタクトレンズ |
| US6087415A (en) | 1998-06-11 | 2000-07-11 | Johnson & Johnson Vision Care, Inc. | Biomedical devices with hydrophilic coatings |
| US6099852A (en) | 1998-09-23 | 2000-08-08 | Johnson & Johnson Vision Products, Inc. | Wettable silicone-based lenses |
| US6440571B1 (en) | 1999-05-20 | 2002-08-27 | Bausch & Lomb Incorporated | Surface treatment of silicone medical devices with reactive hydrophilic polymers |
| AU769468B2 (en) | 1999-05-25 | 2004-01-29 | Samsung Electronics Co., Ltd. | GPS receiver with emergency communication channel |
| US6458142B1 (en) | 1999-10-05 | 2002-10-01 | Ethicon Endo-Surgery, Inc. | Force limiting mechanism for an ultrasonic surgical instrument |
| ATE441132T1 (de) | 1999-12-16 | 2009-09-15 | Asahikasei Aime Co Ltd | Zum tragen über lange zeiträume geeignete weiche kontaktlinsen |
| AR027348A1 (es) | 2000-02-04 | 2003-03-26 | Novartis Ag | Proceso para recubrir una superficie |
| US6533415B2 (en) | 2000-03-21 | 2003-03-18 | Menicon Co., Ltd. | Ocular lens material having hydrophilic surface and process for preparing the same |
| JP5242876B2 (ja) | 2000-03-24 | 2013-07-24 | ノバルティス アーゲー | 架橋結合性または重合性プレポリマー |
| US6599559B1 (en) | 2000-04-03 | 2003-07-29 | Bausch & Lomb Incorporated | Renewable surface treatment of silicone medical devices with reactive hydrophilic polymers |
| US6689480B2 (en) | 2000-05-10 | 2004-02-10 | Toray Industries, Inc. | Surface-treated plastic article and method of surface treatment |
| US6589665B2 (en) | 2000-05-30 | 2003-07-08 | Novartis Ag | Coated articles |
| US6428839B1 (en) | 2000-06-02 | 2002-08-06 | Bausch & Lomb Incorporated | Surface treatment of medical device |
| FR2813815B1 (fr) | 2000-09-14 | 2003-02-21 | Christian Salesse | Dispositif d'equilibrage d'une force, a hautes performances |
| US6433061B1 (en) | 2000-10-24 | 2002-08-13 | Noveon Ip Holdings Corp. | Rheology modifying copolymer composition |
| US7109276B2 (en) | 2001-05-04 | 2006-09-19 | Rhodia Chimie | Method for free radical reduction of dithiocarbonylated or dithiophosphorylated functions borne by a polymer |
| US6634783B2 (en) | 2001-08-09 | 2003-10-21 | Vitality Beverages, Inc. | Apparatus for agitating a fluid suspension |
| EP1469893A1 (de) | 2002-02-01 | 2004-10-27 | Sustech GmbH & Co. KG | Sternformige prapolymere fur die herstellung ultradunner hydrogel-bildender beschichtungen |
| US6794486B2 (en) | 2002-02-19 | 2004-09-21 | Rhodia Chimie | Process for removing a dithiocarbonyl group at the end of a polymer chain |
| US8273366B2 (en) | 2002-06-05 | 2012-09-25 | University Of Florida Research Foundation, Incorporated | Ophthalmic drug delivery system |
| US8158695B2 (en) | 2002-09-06 | 2012-04-17 | Johnson & Johnson Vision Care, Inc. | Forming clear, wettable silicone hydrogel articles without surface treatments |
| US6896926B2 (en) | 2002-09-11 | 2005-05-24 | Novartis Ag | Method for applying an LbL coating onto a medical device |
| US7049351B2 (en) | 2002-11-01 | 2006-05-23 | Novartis Ag | Moldings and preparation and uses thereof |
| US6958169B2 (en) | 2002-12-17 | 2005-10-25 | Bausch & Lomb Incorporated | Surface treatment of medical device |
| US8728508B2 (en) | 2002-12-20 | 2014-05-20 | Coloplast A/S | Hydrophilic coating and a method for the preparation thereof |
| ATE432484T1 (de) | 2003-04-03 | 2009-06-15 | Seed Co Ltd | Kontaktlinsen mit der fähigkeit einer andauernden medikamentenfreigabe und schutzlösungen dafür |
| US20050208102A1 (en) | 2003-04-09 | 2005-09-22 | Schultz Clyde L | Hydrogels used to deliver medicaments to the eye for the treatment of posterior segment diseases |
| US20040208983A1 (en) | 2003-04-16 | 2004-10-21 | Hill Gregory A. | Antimicrobial coatings for ophthalmic devices |
| GB0322640D0 (en) | 2003-09-26 | 2003-10-29 | 1800 Contacts | Process |
| US7214809B2 (en) | 2004-02-11 | 2007-05-08 | Johnson & Johnson Vision Care, Inc. | (Meth)acrylamide monomers containing hydroxy and silicone functionalities |
| US20050192610A1 (en) | 2004-02-27 | 2005-09-01 | Houser Kevin L. | Ultrasonic surgical shears and tissue pad for same |
| US7786185B2 (en) | 2004-03-05 | 2010-08-31 | Johnson & Johnson Vision Care, Inc. | Wettable hydrogels comprising acyclic polyamides |
| US7807755B2 (en) | 2004-05-12 | 2010-10-05 | Commonwealth Scientific And Industrial Research Organisation | Method for removing sulfur-containing end groups |
| CN101163991A (zh) | 2004-08-27 | 2008-04-16 | 旭化成爱目股份有限公司 | 硅水凝胶隐形眼镜 |
| ES2732439T3 (es) | 2004-08-27 | 2019-11-22 | Coopervision Int Holding Co Lp | Lentes de contacto de hidrogel de silicona |
| US7249848B2 (en) | 2004-09-30 | 2007-07-31 | Johnson & Johnson Vision Care, Inc. | Wettable hydrogels comprising reactive, hydrophilic, polymeric internal wetting agents |
| US7247692B2 (en) | 2004-09-30 | 2007-07-24 | Johnson & Johnson Vision Care, Inc. | Biomedical devices containing amphiphilic block copolymers |
| ATE452659T1 (de) | 2004-10-01 | 2010-01-15 | Menicon Co Ltd | Verfahren zur sterilisation verpackter kontaktlinsen mit verpackungslösung |
| US9297928B2 (en) | 2004-11-22 | 2016-03-29 | Johnson & Johnson Vision Care, Inc. | Ophthalmic compositions comprising polyether substituted polymers |
| US20060127345A1 (en) | 2004-12-10 | 2006-06-15 | Hilvert Jennifer E | Conditioning shampoo containing stabilized silicone particles |
| US7592341B2 (en) | 2004-12-15 | 2009-09-22 | Kansas State University Research Foundation | Peptide-enhanced corneal drug delivery |
| US7468153B2 (en) * | 2004-12-30 | 2008-12-23 | The Goodyear Tire & Rubber Co. | Degradable blading for tire curing molds |
| KR101484499B1 (ko) | 2005-02-14 | 2015-01-20 | 존슨 앤드 존슨 비젼 케어, 인코포레이티드 | 안과용 렌즈의 제조방법, 안과용 장치 및 콘택트 렌즈 |
| US7585922B2 (en) | 2005-02-15 | 2009-09-08 | L'oreal, S.A. | Polymer particle dispersion, cosmetic compositions comprising it and cosmetic process using it |
| PT1864181T (pt) | 2005-03-01 | 2016-10-06 | Carl Zeiss Vision Australia Holdings Ltd | Revestimentos para elementos de lentes oftálmicas |
| JP4412226B2 (ja) | 2005-05-11 | 2010-02-10 | Ｎｏｋ株式会社 | ポリオール架橋可能なフッ素ゴム組成物 |
| US7988988B2 (en) | 2005-11-21 | 2011-08-02 | Bausch & Lomb Incorporated | Contact lenses with mucin affinity |
| WO2007064594A2 (en) | 2005-11-29 | 2007-06-07 | Bausch & Lomb Incorporated | New coatings on ophthalmic lenses |
| US20070149428A1 (en) | 2005-12-14 | 2007-06-28 | Bausch & Lomb Incorporated | Method of Packaging a Lens |
| US20070155851A1 (en) | 2005-12-30 | 2007-07-05 | Azaam Alli | Silicone containing polymers formed from non-reactive silicone containing prepolymers |
| US20070155907A1 (en) | 2005-12-30 | 2007-07-05 | Zhao Jonathon Z | Biologically active block copolymers |
| EP1989237A1 (en) | 2006-02-23 | 2008-11-12 | Commonwealth Scientific and Industrial Research Organisation | Process for synthesizing thiol terminated polymers |
| DE102006009004A1 (de) | 2006-02-23 | 2007-09-06 | Sustech Gmbh & Co. Kg | Multifunktionelle sternförmige Präpolymere, deren Herstellung und Verwendung |
| US8044112B2 (en) | 2006-03-30 | 2011-10-25 | Novartis Ag | Method for applying a coating onto a silicone hydrogel lens |
| US7858000B2 (en) | 2006-06-08 | 2010-12-28 | Novartis Ag | Method of making silicone hydrogel contact lenses |
| US7960465B2 (en) | 2006-06-30 | 2011-06-14 | Johnson & Johnson Vision Care, Inc. | Antimicrobial lenses, processes to prepare them and methods of their use |
| CN101166334B (zh) | 2006-10-18 | 2010-06-09 | 中兴通讯股份有限公司 | 无线通信系统远端射频单元的信息记录的实现方法 |
| US7968650B2 (en) | 2006-10-31 | 2011-06-28 | Johnson & Johnson Vision Care, Inc. | Polymeric compositions comprising at least one volume excluding polymer |
| KR101454041B1 (ko) | 2006-11-06 | 2014-10-27 | 노파르티스 아게 | 안구 장치 및 그의 제조 및 사용 방법 |
| GB0623299D0 (en) | 2006-11-22 | 2007-01-03 | Sauflon Cl Ltd | Contact lens |
| WO2008076528A1 (en) | 2006-12-15 | 2008-06-26 | Bausch & Lomb Incorporated | Surface treatment of biomedical devices |
| EP2097712B1 (en) | 2006-12-21 | 2014-10-15 | Johnson and Johnson Vision Care, Inc. | Interferometry testing of lenses, and systems and devices for same |
| AU2007347458B2 (en) | 2007-02-23 | 2013-11-14 | Commonwealth Scientific And Industrial Research Organisation | Process for transforming the end groups of polymers |
| AU2008224989B2 (en) | 2007-03-15 | 2011-11-24 | Dsm Ip Assets B.V. | Novel PDMS-PVP block copolymers |
| WO2008124093A1 (en) | 2007-04-04 | 2008-10-16 | The University Of Akron | Amphiphilic networks, process for producing same, and products made therefrom |
| HUE029331T2 (en) | 2007-04-12 | 2017-02-28 | Nihon Nohyaku Co Ltd | Worm-control agent for use in the preparation and method |
| RU2334770C1 (ru) | 2007-04-13 | 2008-09-27 | Институт Катализа Имени Г.К. Борескова Сибирского Отделения Российской Академии Наук | Полимерная композиция для мягких контактных линз продленного ношения и способ ее получения |
| US20080314767A1 (en) | 2007-06-22 | 2008-12-25 | Bausch & Lomb Incorporated | Ophthalmic Solutions |
| US8080622B2 (en) | 2007-06-29 | 2011-12-20 | Johnson & Johnson Vision Care, Inc. | Soluble silicone prepolymers |
| US20090108479A1 (en) | 2007-10-26 | 2009-04-30 | Bausch & Lomb Incorporated | Method for Making Biomedical Devices |
| US20090142292A1 (en) | 2007-12-03 | 2009-06-04 | Blackwell Richard I | Method For The Mitigation of Symptoms of Dry Eye |
| BRPI0821408A2 (pt) | 2007-12-19 | 2015-06-16 | Janssen Pharmaceutica Nv | Regime de dosagem associado a ésteres de paliperidona injetáveis de longa ação |
| WO2009085754A1 (en) | 2007-12-27 | 2009-07-09 | Bausch & Lomb Incorporated | Segmented interactive block copolymers |
| WO2009085759A1 (en) | 2007-12-27 | 2009-07-09 | Bausch & Lomb Incorporated | Segmented reactive block copolymers |
| JP2011508059A (ja) | 2007-12-27 | 2011-03-10 | ボーシュ アンド ローム インコーポレイティド | セグメント化反応性ブロックコポリマーを含むコーティング溶液 |
| WO2009085756A1 (en) | 2007-12-27 | 2009-07-09 | Bausch & Lomb Incorporated | Coating solutions comprising segmented interactive block copolymers |
| US20090171049A1 (en) | 2007-12-27 | 2009-07-02 | Linhardt Jeffrey G | Segmented reactive block copolymers |
| US7837934B2 (en) | 2008-01-09 | 2010-11-23 | Bausch & Lomb Incorporated | Packaging solutions |
| ATE551177T1 (de) | 2008-01-23 | 2012-04-15 | Novartis Ag | Verfahren zur beschichtung von silikon-hydrogelen |
| JP5033657B2 (ja) | 2008-01-25 | 2012-09-26 | 株式会社メニコン | コンタクトレンズ用液剤及びコンタクトレンズ並びにコンタクトレンズに対する殺菌剤の付着防止方法 |
| US20100069522A1 (en) | 2008-03-17 | 2010-03-18 | Linhardt Jeffrey G | Lenses comprising amphiphilic multiblock copolymers |
| US8460743B2 (en) | 2008-03-18 | 2013-06-11 | Novartis Ag | Coating process for ophthalmic lenses |
| US8470906B2 (en) | 2008-09-30 | 2013-06-25 | Johnson & Johnson Vision Care, Inc. | Ionic silicone hydrogels having improved hydrolytic stability |
| US20130203812A1 (en) | 2008-09-30 | 2013-08-08 | Johnson & Johnson Vision Care, Inc. | Ionic silicone hydrogels comprising pharmaceutical and/or nutriceutical components and having improved hydrolytic stability |
| US8788212B2 (en) | 2008-10-31 | 2014-07-22 | The Invention Science Fund I, Llc | Compositions and methods for biological remodeling with frozen particle compositions |
| BRPI0921894A2 (pt) | 2008-11-13 | 2015-12-29 | Novartis Ag | copolímeros de polissiloxano com cadeias de polímero hidrofílicas terminais |
| EP2358795A1 (en) | 2008-11-17 | 2011-08-24 | DSM IP Assets B.V. | Surface modification of polymers via surface active and reactive end groups |
| TWI506333B (zh) | 2008-12-05 | 2015-11-01 | Novartis Ag | 用以傳遞疏水性舒適劑之眼用裝置及其製造方法 |
| NZ592674A (en) | 2008-12-18 | 2012-08-31 | Novartis Ag | Method for making silicone hydrogel contact lenses |
| WO2010077708A1 (en) * | 2008-12-30 | 2010-07-08 | Bausch & Lomb Incorporated | Packaging solutions |
| US8454689B2 (en) * | 2008-12-30 | 2013-06-04 | Bausch & Lomb Incorporated | Brush copolymers |
| WO2010077646A2 (en) | 2008-12-30 | 2010-07-08 | Bausch & Lomb Incorporated | Method of applying renewable polymeric lens coating |
| US20100249273A1 (en) | 2009-03-31 | 2010-09-30 | Scales Charles W | Polymeric articles comprising oxygen permeability enhancing particles |
| US8173750B2 (en) | 2009-04-23 | 2012-05-08 | ATRP Solutions, Inc. | Star macromolecules for personal and home care |
| CA2761218C (en) | 2009-05-22 | 2016-06-28 | Novartis Ag | Actinically-crosslinkable siloxane-containing copolymers |
| CA2760747C (en) * | 2009-05-22 | 2016-12-13 | Novartis Ag | Actinically-crosslinkable siloxane-containing copolymers |
| US8043369B2 (en) | 2009-06-16 | 2011-10-25 | Bausch & Lomb Incorporated | Biomedical devices |
| US8133960B2 (en) | 2009-06-16 | 2012-03-13 | Bausch & Lomb Incorporated | Biomedical devices |
| US9285508B2 (en) | 2009-06-16 | 2016-03-15 | Bausch & Lomb Incorporated | Biomedical devices |
| US8083348B2 (en) | 2009-06-16 | 2011-12-27 | Bausch & Lomb Incorporated | Biomedical devices |
| US20100315588A1 (en) | 2009-06-16 | 2010-12-16 | Bausch & Lomb Incorporated | Biomedical devices |
| US20110189291A1 (en) | 2009-08-04 | 2011-08-04 | Hu Yang | Dendrimer hydrogels |
| MY156206A (en) | 2009-11-04 | 2016-01-29 | Novartis Ag | A silicone hydrogel lens with a grafted hydrophilic coating |
| TWI483996B (zh) | 2009-12-08 | 2015-05-11 | Novartis Ag | 具有共價貼合塗層之聚矽氧水凝膠鏡片 |
| TWI401263B (zh) | 2009-12-31 | 2013-07-11 | Far Eastern New Century Corp | 增進聚矽氧水膠潤濕性之共聚物、包含其之聚矽氧水膠組成物及由此製得之眼用物件 |
| JP5720103B2 (ja) | 2010-03-18 | 2015-05-20 | 東レ株式会社 | シリコーンハイドロゲル、眼用レンズおよびコンタクトレンズ |
| US9522980B2 (en) | 2010-05-06 | 2016-12-20 | Johnson & Johnson Vision Care, Inc. | Non-reactive, hydrophilic polymers having terminal siloxanes and methods for making and using the same |
| ES2423914T3 (es) | 2010-07-30 | 2013-09-25 | Novartis Ag | Lentes de hidrogel de silicona con superficies ricas en agua |
| US20130203813A1 (en) | 2011-05-04 | 2013-08-08 | Johnson & Johnson Vision Care, Inc. | Medical devices having homogeneous charge density and methods for making same |
| US9170349B2 (en) | 2011-05-04 | 2015-10-27 | Johnson & Johnson Vision Care, Inc. | Medical devices having homogeneous charge density and methods for making same |
| JP5990579B2 (ja) | 2011-06-09 | 2016-09-14 | ノバルティス アーゲー | ナノテクスチャー表面を持つシリコーンヒドロゲルレンズ |
| HUE027313T2 (en) | 2011-11-15 | 2016-10-28 | Novartis Ag | Silicone hydrogel lens with cross-linked hydrophilic coating |
| US9125808B2 (en) | 2011-12-23 | 2015-09-08 | Johnson & Johnson Vision Care, Inc. | Ionic silicone hydrogels |
| US8993705B2 (en) * | 2012-03-26 | 2015-03-31 | John R. Dorgan | Polylactide-graft-lignin blends and copolymers |
| US9244196B2 (en) | 2012-05-25 | 2016-01-26 | Johnson & Johnson Vision Care, Inc. | Polymers and nanogel materials and methods for making and using the same |
| US10073192B2 (en) * | 2012-05-25 | 2018-09-11 | Johnson & Johnson Vision Care, Inc. | Polymers and nanogel materials and methods for making and using the same |
| CN104837612B (zh) | 2012-12-11 | 2017-08-25 | 诺华股份有限公司 | 将涂层施加于硅酮水凝胶透镜上的方法 |
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| EP2855544B1 (en) | 2018-06-20 |
| EP2855544A2 (en) | 2015-04-08 |
| SG11201407587RA (en) | 2014-12-30 |
| WO2013176886A3 (en) | 2014-04-17 |
| HK1208690A1 (en) | 2016-03-11 |
| CN104334596A (zh) | 2015-02-04 |
| KR20150023484A (ko) | 2015-03-05 |
| BR112014029203A2 (pt) | 2017-06-27 |
| US20130317131A1 (en) | 2013-11-28 |
| CN107936204A (zh) | 2018-04-20 |
| US20180341044A1 (en) | 2018-11-29 |
| JP2018040010A (ja) | 2018-03-15 |
| JP2015525254A (ja) | 2015-09-03 |
| TW201410719A (zh) | 2014-03-16 |
| HK1204637A1 (en) | 2015-11-27 |
| CN104334596B (zh) | 2017-12-05 |
| WO2013176886A2 (en) | 2013-11-28 |
| US10502867B2 (en) | 2019-12-10 |
| TWI677510B (zh) | 2019-11-21 |
| RU2014152679A (ru) | 2016-07-20 |
| JP6250647B2 (ja) | 2017-12-20 |
| AU2013266802A1 (en) | 2014-11-27 |
| US10871595B2 (en) | 2020-12-22 |
| US20200049858A1 (en) | 2020-02-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20180510 |