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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- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
- 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
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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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- 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
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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
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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
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Landscapes
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- Condensed Matter Physics & Semiconductors (AREA)
- Graft Or Block Polymers (AREA)
- Eyeglasses (AREA)
- Dispersion Chemistry (AREA)
- Materials For Medical Uses (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
- Silicon Polymers (AREA)
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| 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 |
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| 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 |
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- 2013-05-08 EP EP13723378.9A patent/EP2855544B1/en not_active Not-in-force
- 2013-05-08 BR BR112014029203A patent/BR112014029203A2/pt not_active Application Discontinuation
- 2013-05-08 RU RU2014152679A patent/RU2014152679A/ru unknown
- 2013-05-08 HK HK15109271.4A patent/HK1208690A1/xx unknown
- 2013-05-08 AU AU2013266802A patent/AU2013266802A1/en not_active Abandoned
- 2013-05-08 JP JP2015514043A patent/JP6250647B2/ja not_active Expired - Fee Related
- 2013-05-08 HK HK15105264.1A patent/HK1204637A1/xx unknown
- 2013-05-08 CA CA2874607A patent/CA2874607A1/en not_active Abandoned
- 2013-05-08 WO PCT/US2013/040066 patent/WO2013176886A2/en not_active Ceased
- 2013-05-08 CN CN201380027478.7A patent/CN104334596B/zh not_active Expired - Fee Related
- 2013-05-08 KR KR20147036328A patent/KR20150023484A/ko not_active Withdrawn
- 2013-05-08 SG SG11201407587RA patent/SG11201407587RA/en unknown
- 2013-05-24 TW TW102118351A patent/TWI677510B/zh not_active IP Right Cessation
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2018
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2019
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| AU2013266802A1 (en) | 2014-11-27 |
| CN104334596A (zh) | 2015-02-04 |
| HK1204637A1 (en) | 2015-11-27 |
| CN107936204A (zh) | 2018-04-20 |
| EP2855544B1 (en) | 2018-06-20 |
| JP6250647B2 (ja) | 2017-12-20 |
| TWI677510B (zh) | 2019-11-21 |
| WO2013176886A2 (en) | 2013-11-28 |
| KR20150023484A (ko) | 2015-03-05 |
| RU2014152679A (ru) | 2016-07-20 |
| SG11201407587RA (en) | 2014-12-30 |
| US20200049858A1 (en) | 2020-02-13 |
| EP2855544A2 (en) | 2015-04-08 |
| HK1208690A1 (en) | 2016-03-11 |
| JP2015525254A (ja) | 2015-09-03 |
| US10502867B2 (en) | 2019-12-10 |
| US20180341044A1 (en) | 2018-11-29 |
| WO2013176886A3 (en) | 2014-04-17 |
| JP2018040010A (ja) | 2018-03-15 |
| US10073192B2 (en) | 2018-09-11 |
| CN104334596B (zh) | 2017-12-05 |
| US10871595B2 (en) | 2020-12-22 |
| US20130317131A1 (en) | 2013-11-28 |
| BR112014029203A2 (pt) | 2017-06-27 |
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Legal Events
| Date | Code | Title | Description |
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| FZDE | Discontinued |
Effective date: 20180510 |