RU2014152679A - Полимеры и наногелевые материалы, а также способы их получения и применения - Google Patents
Полимеры и наногелевые материалы, а также способы их получения и применения Download PDFInfo
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- RU2014152679A RU2014152679A RU2014152679A RU2014152679A RU2014152679A RU 2014152679 A RU2014152679 A RU 2014152679A RU 2014152679 A RU2014152679 A RU 2014152679A RU 2014152679 A RU2014152679 A RU 2014152679A RU 2014152679 A RU2014152679 A RU 2014152679A
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- Prior art keywords
- segment
- block copolymer
- hydrophilic
- polymerization
- group
- Prior art date
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- 229920000642 polymer Polymers 0.000 title claims abstract 29
- 239000000463 material Substances 0.000 title claims 4
- 239000000203 mixture Substances 0.000 claims abstract 48
- 229920001400 block copolymer Polymers 0.000 claims abstract 46
- 238000006116 polymerization reaction Methods 0.000 claims abstract 38
- 239000000178 monomer Substances 0.000 claims abstract 25
- 239000000758 substrate Substances 0.000 claims abstract 21
- 230000002209 hydrophobic effect Effects 0.000 claims abstract 7
- 125000005647 linker group Chemical group 0.000 claims abstract 4
- 230000000536 complexating effect Effects 0.000 claims abstract 3
- 229920001296 polysiloxane Polymers 0.000 claims 36
- 238000000034 method Methods 0.000 claims 30
- -1 polydimethylsiloxane Polymers 0.000 claims 26
- 239000003795 chemical substances by application Substances 0.000 claims 15
- 229940054534 ophthalmic solution Drugs 0.000 claims 14
- 239000002997 ophthalmic solution Substances 0.000 claims 14
- 239000003431 cross linking reagent Substances 0.000 claims 12
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 claims 10
- 239000012987 RAFT agent Substances 0.000 claims 9
- AISZNMCRXZWVAT-UHFFFAOYSA-N 2-ethylsulfanylcarbothioylsulfanyl-2-methylpropanenitrile Chemical compound CCSC(=S)SC(C)(C)C#N AISZNMCRXZWVAT-UHFFFAOYSA-N 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 125000002947 alkylene group Chemical group 0.000 claims 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 7
- 150000003254 radicals Chemical class 0.000 claims 7
- 239000011541 reaction mixture Substances 0.000 claims 7
- 238000010521 absorption reaction Methods 0.000 claims 6
- 238000004132 cross linking Methods 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 150000002632 lipids Chemical class 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 239000003999 initiator Substances 0.000 claims 5
- 229920006294 polydialkylsiloxane Polymers 0.000 claims 5
- 239000000243 solution Substances 0.000 claims 5
- 239000002904 solvent Substances 0.000 claims 5
- 230000015572 biosynthetic process Effects 0.000 claims 4
- 229920001577 copolymer Polymers 0.000 claims 4
- 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 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 230000000379 polymerizing effect Effects 0.000 claims 4
- 238000010526 radical polymerization reaction Methods 0.000 claims 4
- 125000004423 acyloxy group Chemical group 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims 3
- 238000010560 atom transfer radical polymerization reaction Methods 0.000 claims 3
- 125000000524 functional group Chemical group 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 claims 3
- 238000012705 nitroxide-mediated radical polymerization Methods 0.000 claims 3
- 239000012985 polymerization agent Substances 0.000 claims 3
- 230000001105 regulatory effect Effects 0.000 claims 3
- 229920002554 vinyl polymer Polymers 0.000 claims 3
- PBGPBHYPCGDFEZ-UHFFFAOYSA-N 1-ethenylpiperidin-2-one Chemical compound C=CN1CCCCC1=O PBGPBHYPCGDFEZ-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- KFNGWPXYNSJXOP-UHFFFAOYSA-N 3-(2-methylprop-2-enoyloxy)propane-1-sulfonic acid Chemical compound CC(=C)C(=O)OCCCS(O)(=O)=O KFNGWPXYNSJXOP-UHFFFAOYSA-N 0.000 claims 2
- GAVHQOUUSHBDAA-UHFFFAOYSA-N 3-butyl-1-ethenylaziridin-2-one Chemical compound CCCCC1N(C=C)C1=O GAVHQOUUSHBDAA-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- 125000004104 aryloxy group Chemical group 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 150000007942 carboxylates Chemical class 0.000 claims 2
- 238000004891 communication Methods 0.000 claims 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims 2
- 239000012634 fragment Substances 0.000 claims 2
- 239000000017 hydrogel Substances 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 claims 2
- PNLUGRYDUHRLOF-UHFFFAOYSA-N n-ethenyl-n-methylacetamide Chemical compound C=CN(C)C(C)=O PNLUGRYDUHRLOF-UHFFFAOYSA-N 0.000 claims 2
- RQAKESSLMFZVMC-UHFFFAOYSA-N n-ethenylacetamide Chemical compound CC(=O)NC=C RQAKESSLMFZVMC-UHFFFAOYSA-N 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 229910052698 phosphorus Inorganic materials 0.000 claims 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 2
- 229920003213 poly(N-isopropyl acrylamide) Polymers 0.000 claims 2
- 229920001515 polyalkylene glycol Polymers 0.000 claims 2
- 239000005017 polysaccharide Substances 0.000 claims 2
- 229920001282 polysaccharide Polymers 0.000 claims 2
- 159000000000 sodium salts Chemical class 0.000 claims 2
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- ZRZHXNCATOYMJH-UHFFFAOYSA-N 1-(chloromethyl)-4-ethenylbenzene Chemical compound ClCC1=CC=C(C=C)C=C1 ZRZHXNCATOYMJH-UHFFFAOYSA-N 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
- 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 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
- 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 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
- JBKFPCSZNWLZAS-UHFFFAOYSA-N 1-ethenyl-4-methylpiperidin-2-one Chemical compound CC1CCN(C=C)C(=O)C1 JBKFPCSZNWLZAS-UHFFFAOYSA-N 0.000 claims 1
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-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
- NYEZZYQZRQDLEH-UHFFFAOYSA-N 2-ethyl-4,5-dihydro-1,3-oxazole Chemical compound CCC1=NCCO1 NYEZZYQZRQDLEH-UHFFFAOYSA-N 0.000 claims 1
- JNDVNJWCRZQGFQ-UHFFFAOYSA-N 2-methyl-N,N-bis(methylamino)hex-2-enamide Chemical compound CCCC=C(C)C(=O)N(NC)NC JNDVNJWCRZQGFQ-UHFFFAOYSA-N 0.000 claims 1
- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 claims 1
- YVAQHFNMILVVNE-UHFFFAOYSA-N 3-(prop-2-enoylamino)propanoic acid Chemical compound OC(=O)CCNC(=O)C=C YVAQHFNMILVVNE-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- VUYGJYAPDGKPBF-UHFFFAOYSA-N 4-(bromomethyl)benzoyl bromide Chemical compound BrCC1=CC=C(C(Br)=O)C=C1 VUYGJYAPDGKPBF-UHFFFAOYSA-N 0.000 claims 1
- YRXLABUVDQYDHV-UHFFFAOYSA-N 4-(prop-2-enoylamino)butanoic acid Chemical compound OC(=O)CCCNC(=O)C=C YRXLABUVDQYDHV-UHFFFAOYSA-N 0.000 claims 1
- XRUKRHLZDVJJSX-UHFFFAOYSA-N 4-cyanopentanoic acid Chemical class N#CC(C)CCC(O)=O XRUKRHLZDVJJSX-UHFFFAOYSA-N 0.000 claims 1
- MMPFUGWXFWSETK-UHFFFAOYSA-N 5,6-dihydroxy-2-methylhex-2-enamide Chemical compound OC(CC=C(C(=O)N)C)CO MMPFUGWXFWSETK-UHFFFAOYSA-N 0.000 claims 1
- KJJYUNTVGZAHHJ-UHFFFAOYSA-N 5-(prop-2-enoylamino)pentanoic acid Chemical compound OC(=O)CCCCNC(=O)C=C KJJYUNTVGZAHHJ-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims 1
- 239000004593 Epoxy Substances 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims 1
- 239000004698 Polyethylene Substances 0.000 claims 1
- 239000004372 Polyvinyl alcohol Substances 0.000 claims 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical class CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 150000003863 ammonium salts Chemical class 0.000 claims 1
- 229920006187 aquazol Polymers 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 229920006037 cross link polymer Polymers 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 239000004205 dimethyl polysiloxane Substances 0.000 claims 1
- GHDKCGUBCYSUPJ-UHFFFAOYSA-N dimethyl-(3-prop-2-enoyloxypropyl)-propylazanium Chemical compound CCC[N+](C)(C)CCCOC(=O)C=C GHDKCGUBCYSUPJ-UHFFFAOYSA-N 0.000 claims 1
- KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical compound [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 claims 1
- 239000003792 electrolyte Substances 0.000 claims 1
- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical class NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 claims 1
- RZBXSLICNMYVAJ-UHFFFAOYSA-N ethenyl acetate;2-methylprop-2-enoic acid Chemical compound CC(=O)OC=C.CC(=C)C(O)=O RZBXSLICNMYVAJ-UHFFFAOYSA-N 0.000 claims 1
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Chemical compound CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000000499 gel Substances 0.000 claims 1
- 150000004676 glycans Chemical class 0.000 claims 1
- 229920000669 heparin Polymers 0.000 claims 1
- 229960002897 heparin Drugs 0.000 claims 1
- 229920001477 hydrophilic polymer Polymers 0.000 claims 1
- 230000000977 initiatory effect Effects 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- 150000002500 ions Chemical class 0.000 claims 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical class CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 claims 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical class CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 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
- BSCJIBOZTKGXQP-UHFFFAOYSA-N n-(2-hydroxyethyl)-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NCCO BSCJIBOZTKGXQP-UHFFFAOYSA-N 0.000 claims 1
- UUORTJUPDJJXST-UHFFFAOYSA-N n-(2-hydroxyethyl)prop-2-enamide Chemical compound OCCNC(=O)C=C UUORTJUPDJJXST-UHFFFAOYSA-N 0.000 claims 1
- OKPYIWASQZGASP-UHFFFAOYSA-N n-(2-hydroxypropyl)-2-methylprop-2-enamide Chemical compound CC(O)CNC(=O)C(C)=C OKPYIWASQZGASP-UHFFFAOYSA-N 0.000 claims 1
- ZTUGCJNAJJDKDC-UHFFFAOYSA-N n-(3-hydroxypropyl)-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NCCCO ZTUGCJNAJJDKDC-UHFFFAOYSA-N 0.000 claims 1
- ZJDNTSGQAOAXNR-UHFFFAOYSA-N n-ethenyl-2-methylpropanamide Chemical compound CC(C)C(=O)NC=C ZJDNTSGQAOAXNR-UHFFFAOYSA-N 0.000 claims 1
- MWAITTXTRUIKOM-UHFFFAOYSA-N n-ethenyl-n,2-dimethylpropanamide Chemical compound CC(C)C(=O)N(C)C=C MWAITTXTRUIKOM-UHFFFAOYSA-N 0.000 claims 1
- DSENQNLOVPYEKP-UHFFFAOYSA-N n-ethenyl-n-methylpropanamide Chemical compound CCC(=O)N(C)C=C DSENQNLOVPYEKP-UHFFFAOYSA-N 0.000 claims 1
- QNILTEGFHQSKFF-UHFFFAOYSA-N n-propan-2-ylprop-2-enamide Chemical compound CC(C)NC(=O)C=C QNILTEGFHQSKFF-UHFFFAOYSA-N 0.000 claims 1
- 230000000269 nucleophilic effect Effects 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 150000004714 phosphonium salts Chemical class 0.000 claims 1
- 229910052697 platinum Inorganic materials 0.000 claims 1
- 229920002006 poly(N-vinylimidazole) polymer Polymers 0.000 claims 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims 1
- 229920000573 polyethylene Polymers 0.000 claims 1
- 229920002451 polyvinyl alcohol Polymers 0.000 claims 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims 1
- KCXFHTAICRTXLI-UHFFFAOYSA-M propane-1-sulfonate Chemical compound CCCS([O-])(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-M 0.000 claims 1
- 125000004929 pyrrolidonyl group Chemical group N1(C(CCC1)=O)* 0.000 claims 1
- 230000002441 reversible effect Effects 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 229910000077 silane Inorganic materials 0.000 claims 1
- 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 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 1
- 150000003871 sulfonates Chemical class 0.000 claims 1
- 150000003460 sulfonic acids Chemical class 0.000 claims 1
- 150000004772 tellurides Chemical group 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F293/00—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule
- 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
-
- 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
-
- 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
-
- 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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-
2013
- 2013-03-15 US US13/840,919 patent/US10073192B2/en active Active
- 2013-05-08 SG SG11201407587RA patent/SG11201407587RA/en unknown
- 2013-05-08 WO PCT/US2013/040066 patent/WO2013176886A2/en not_active Ceased
- 2013-05-08 AU AU2013266802A patent/AU2013266802A1/en not_active Abandoned
- 2013-05-08 CA CA2874607A patent/CA2874607A1/en not_active Abandoned
- 2013-05-08 HK HK15105264.1A patent/HK1204637A1/xx unknown
- 2013-05-08 CN CN201380027478.7A patent/CN104334596B/zh not_active Expired - Fee Related
- 2013-05-08 HK HK15109271.4A patent/HK1208690A1/xx unknown
- 2013-05-08 JP JP2015514043A patent/JP6250647B2/ja not_active Expired - Fee Related
- 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 KR KR20147036328A patent/KR20150023484A/ko not_active Withdrawn
- 2013-05-08 CN CN201711237139.8A patent/CN107936204A/zh active Pending
- 2013-05-08 RU RU2014152679A patent/RU2014152679A/ru unknown
- 2013-05-24 TW TW102118351A patent/TWI677510B/zh not_active IP Right Cessation
-
2017
- 2017-11-17 JP JP2017221671A patent/JP2018040010A/ja not_active Ceased
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2018
- 2018-08-03 US US16/053,865 patent/US10502867B2/en not_active Expired - Fee Related
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2019
- 2019-10-22 US US16/659,633 patent/US10871595B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP2018040010A (ja) | 2018-03-15 |
| CA2874607A1 (en) | 2013-11-28 |
| KR20150023484A (ko) | 2015-03-05 |
| SG11201407587RA (en) | 2014-12-30 |
| EP2855544A2 (en) | 2015-04-08 |
| HK1204637A1 (en) | 2015-11-27 |
| CN104334596B (zh) | 2017-12-05 |
| TW201410719A (zh) | 2014-03-16 |
| TWI677510B (zh) | 2019-11-21 |
| US20200049858A1 (en) | 2020-02-13 |
| WO2013176886A2 (en) | 2013-11-28 |
| CN104334596A (zh) | 2015-02-04 |
| JP6250647B2 (ja) | 2017-12-20 |
| AU2013266802A1 (en) | 2014-11-27 |
| US10871595B2 (en) | 2020-12-22 |
| HK1208690A1 (en) | 2016-03-11 |
| EP2855544B1 (en) | 2018-06-20 |
| US20130317131A1 (en) | 2013-11-28 |
| US20180341044A1 (en) | 2018-11-29 |
| CN107936204A (zh) | 2018-04-20 |
| BR112014029203A2 (pt) | 2017-06-27 |
| WO2013176886A3 (en) | 2014-04-17 |
| US10073192B2 (en) | 2018-09-11 |
| US10502867B2 (en) | 2019-12-10 |
| JP2015525254A (ja) | 2015-09-03 |
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