WO2000069932A1 - Bioadhesive polymer compositions - Google Patents
Bioadhesive polymer compositions Download PDFInfo
- Publication number
- WO2000069932A1 WO2000069932A1 PCT/US2000/011249 US0011249W WO0069932A1 WO 2000069932 A1 WO2000069932 A1 WO 2000069932A1 US 0011249 W US0011249 W US 0011249W WO 0069932 A1 WO0069932 A1 WO 0069932A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- polymer
- crosslinked
- solvent
- acids
- group
- Prior art date
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- 229920000642 polymer Polymers 0.000 title claims abstract description 136
- 239000000227 bioadhesive Substances 0.000 title claims abstract description 24
- 239000000203 mixture Substances 0.000 title claims description 34
- 238000000034 method Methods 0.000 claims abstract description 46
- 229920000831 ionic polymer Polymers 0.000 claims abstract description 39
- 150000003839 salts Chemical class 0.000 claims abstract description 24
- 239000000546 pharmaceutical excipient Substances 0.000 claims abstract description 12
- 239000003995 emulsifying agent Substances 0.000 claims abstract description 6
- 239000002562 thickening agent Substances 0.000 claims abstract description 6
- 239000000463 material Substances 0.000 claims description 62
- 239000000178 monomer Substances 0.000 claims description 52
- 239000002904 solvent Substances 0.000 claims description 52
- -1 vinylidene compound Chemical class 0.000 claims description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 33
- 239000002253 acid Substances 0.000 claims description 28
- 239000000017 hydrogel Substances 0.000 claims description 28
- 229920001577 copolymer Polymers 0.000 claims description 23
- 239000003795 chemical substances by application Substances 0.000 claims description 20
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 20
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 18
- 229920002554 vinyl polymer Polymers 0.000 claims description 18
- 150000007513 acids Chemical class 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 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 14
- 239000008177 pharmaceutical agent Substances 0.000 claims description 13
- 230000008569 process Effects 0.000 claims description 13
- 229920006037 cross link polymer Polymers 0.000 claims description 12
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 claims description 12
- 229920001519 homopolymer Polymers 0.000 claims description 12
- 239000004971 Cross linker Substances 0.000 claims description 11
- 150000001253 acrylic acids Chemical class 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 10
- 230000003472 neutralizing effect Effects 0.000 claims description 10
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 239000003381 stabilizer Substances 0.000 claims description 9
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 8
- 239000011243 crosslinked material Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000005395 methacrylic acid group Chemical class 0.000 claims description 8
- PSBDWGZCVUAZQS-UHFFFAOYSA-N (dimethylsulfonio)acetate Chemical compound C[S+](C)CC([O-])=O PSBDWGZCVUAZQS-UHFFFAOYSA-N 0.000 claims description 7
- 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 description 7
- NYUTUWAFOUJLKI-UHFFFAOYSA-N 3-prop-2-enoyloxypropane-1-sulfonic acid Chemical compound OS(=O)(=O)CCCOC(=O)C=C NYUTUWAFOUJLKI-UHFFFAOYSA-N 0.000 claims description 7
- 229960003237 betaine Drugs 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 150000002689 maleic acids Chemical class 0.000 claims description 7
- SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical group C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 claims description 7
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
- 239000011877 solvent mixture Substances 0.000 claims description 7
- 229940117986 sulfobetaine Drugs 0.000 claims description 7
- BCAIDFOKQCVACE-UHFFFAOYSA-N 3-[dimethyl-[2-(2-methylprop-2-enoyloxy)ethyl]azaniumyl]propane-1-sulfonate Chemical compound CC(=C)C(=O)OCC[N+](C)(C)CCCS([O-])(=O)=O BCAIDFOKQCVACE-UHFFFAOYSA-N 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 229920001897 terpolymer Polymers 0.000 claims description 6
- 239000008367 deionised water Substances 0.000 claims description 5
- 229910021641 deionized water Inorganic materials 0.000 claims description 5
- 230000001804 emulsifying effect Effects 0.000 claims description 5
- 230000001376 precipitating effect Effects 0.000 claims description 5
- RFIMISVNSAUMBU-UHFFFAOYSA-N 2-(hydroxymethyl)-2-(prop-2-enoxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC=C RFIMISVNSAUMBU-UHFFFAOYSA-N 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 238000000518 rheometry Methods 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 4
- 239000004711 α-olefin Substances 0.000 claims description 4
- 229940086737 allyl sucrose Drugs 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- JQRRFDWXQOQICD-UHFFFAOYSA-N biphenylen-1-ylboronic acid Chemical compound C12=CC=CC=C2C2=C1C=CC=C2B(O)O JQRRFDWXQOQICD-UHFFFAOYSA-N 0.000 claims description 2
- 238000012674 dispersion polymerization Methods 0.000 claims description 2
- 238000007720 emulsion polymerization reaction Methods 0.000 claims description 2
- 239000002198 insoluble material Substances 0.000 claims description 2
- 229920002959 polymer blend Polymers 0.000 claims description 2
- 238000012673 precipitation polymerization Methods 0.000 claims description 2
- 230000002441 reversible effect Effects 0.000 claims description 2
- 230000003381 solubilizing effect Effects 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 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 5
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 claims 5
- 238000013270 controlled release Methods 0.000 abstract description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
- 238000006116 polymerization reaction Methods 0.000 description 23
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 17
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- 229920005989 resin Polymers 0.000 description 14
- 239000011347 resin Substances 0.000 description 14
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical class COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- 229920002125 Sokalan® Polymers 0.000 description 12
- 230000035587 bioadhesion Effects 0.000 description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 12
- 239000000499 gel Substances 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
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- 230000008719 thickening Effects 0.000 description 8
- 150000001735 carboxylic acids Chemical class 0.000 description 7
- 239000000839 emulsion Substances 0.000 description 7
- 229940093499 ethyl acetate Drugs 0.000 description 7
- 235000019439 ethyl acetate Nutrition 0.000 description 7
- 239000002245 particle Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 239000012530 fluid Substances 0.000 description 6
- 125000005647 linker group Chemical group 0.000 description 6
- 125000006239 protecting group Chemical group 0.000 description 6
- 229920000536 2-Acrylamido-2-methylpropane sulfonic acid Polymers 0.000 description 5
- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 description 5
- 150000008064 anhydrides Chemical class 0.000 description 5
- 239000003242 anti bacterial agent Substances 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
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- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 5
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- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 4
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 4
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- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
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- 150000003857 carboxamides Chemical class 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical class O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 4
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- 239000013557 residual solvent Substances 0.000 description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 4
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- 229960001567 sodium stibogluconate Drugs 0.000 description 1
- JJICLMJFIKGAAU-UHFFFAOYSA-M sodium;2-amino-9-(1,3-dihydroxypropan-2-yloxymethyl)purin-6-olate Chemical compound [Na+].NC1=NC([O-])=C2N=CN(COC(CO)CO)C2=N1 JJICLMJFIKGAAU-UHFFFAOYSA-M 0.000 description 1
- RMLUKZWYIKEASN-UHFFFAOYSA-M sodium;2-amino-9-(2-hydroxyethoxymethyl)purin-6-olate Chemical compound [Na+].O=C1[N-]C(N)=NC2=C1N=CN2COCCO RMLUKZWYIKEASN-UHFFFAOYSA-M 0.000 description 1
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- 238000003860 storage Methods 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229960002673 sulfacetamide Drugs 0.000 description 1
- SKIVFJLNDNKQPD-UHFFFAOYSA-N sulfacetamide Chemical compound CC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 SKIVFJLNDNKQPD-UHFFFAOYSA-N 0.000 description 1
- 229960004306 sulfadiazine Drugs 0.000 description 1
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 1
- 229960000654 sulfafurazole Drugs 0.000 description 1
- 229960005404 sulfamethoxazole Drugs 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- JLKIGFTWXXRPMT-UHFFFAOYSA-N sulphamethoxazole Chemical compound O1C(C)=CC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 JLKIGFTWXXRPMT-UHFFFAOYSA-N 0.000 description 1
- 229920000247 superabsorbent polymer Polymers 0.000 description 1
- 239000004583 superabsorbent polymers (SAPs) Substances 0.000 description 1
- 229960005314 suramin Drugs 0.000 description 1
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- 229940037128 systemic glucocorticoids Drugs 0.000 description 1
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- IWVCMVBTMGNXQD-UHFFFAOYSA-N terramycin dehydrate Natural products C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-UHFFFAOYSA-N 0.000 description 1
- 235000019364 tetracycline Nutrition 0.000 description 1
- 229940072172 tetracycline antibiotic Drugs 0.000 description 1
- 150000003522 tetracyclines Chemical class 0.000 description 1
- 229940040944 tetracyclines Drugs 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 229940041007 third-generation cephalosporins Drugs 0.000 description 1
- 230000009974 thixotropic effect Effects 0.000 description 1
- 229940036555 thyroid hormone Drugs 0.000 description 1
- 239000005495 thyroid hormone Substances 0.000 description 1
- 229960004659 ticarcillin Drugs 0.000 description 1
- OHKOGUYZJXTSFX-KZFFXBSXSA-N ticarcillin Chemical compound C=1([C@@H](C(O)=O)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)C=CSC=1 OHKOGUYZJXTSFX-KZFFXBSXSA-N 0.000 description 1
- 229960000707 tobramycin Drugs 0.000 description 1
- NLVFBUXFDBBNBW-PBSUHMDJSA-N tobramycin Chemical compound N[C@@H]1C[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N NLVFBUXFDBBNBW-PBSUHMDJSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 238000013271 transdermal drug delivery Methods 0.000 description 1
- JVYCFGPPVMLAAL-UHFFFAOYSA-N triacontyl prop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCOC(=O)C=C JVYCFGPPVMLAAL-UHFFFAOYSA-N 0.000 description 1
- 229960003962 trifluridine Drugs 0.000 description 1
- VSQQQLOSPVPRAZ-RRKCRQDMSA-N trifluridine Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(C(F)(F)F)=C1 VSQQQLOSPVPRAZ-RRKCRQDMSA-N 0.000 description 1
- 229940096522 trimethylolpropane triacrylate Drugs 0.000 description 1
- 102000003390 tumor necrosis factor Human genes 0.000 description 1
- 229960002703 undecylenic acid Drugs 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
- 229960003165 vancomycin Drugs 0.000 description 1
- MYPYJXKWCTUITO-LYRMYLQWSA-N vancomycin Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-N 0.000 description 1
- MYPYJXKWCTUITO-UHFFFAOYSA-N vancomycin Natural products O1C(C(=C2)Cl)=CC=C2C(O)C(C(NC(C2=CC(O)=CC(O)=C2C=2C(O)=CC=C3C=2)C(O)=O)=O)NC(=O)C3NC(=O)C2NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(CC(C)C)NC)C(O)C(C=C3Cl)=CC=C3OC3=CC2=CC1=C3OC1OC(CO)C(O)C(O)C1OC1CC(C)(N)C(O)C(C)O1 MYPYJXKWCTUITO-UHFFFAOYSA-N 0.000 description 1
- 229960003636 vidarabine Drugs 0.000 description 1
- 229960003048 vinblastine Drugs 0.000 description 1
- JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 description 1
- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 1
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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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/04—Acids; Metal salts or ammonium salts thereof
- C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
-
- 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
- C08F6/00—Post-polymerisation treatments
- C08F6/06—Treatment of polymer solutions
- C08F6/12—Separation of polymers from solutions
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S526/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S526/923—Ethylenic monomers containing at least one salt group
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S526/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S526/93—Water swellable or hydrophilic
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S526/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S526/932—Thickener or dispersant for aqueous system
Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
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EP00926403A EP1185565B1 (en) | 1999-05-19 | 2000-04-27 | Bioadhesive polymer compositions |
AU44934/00A AU4493400A (en) | 1999-05-19 | 2000-04-27 | Bioadhesive polymer compositions |
DE60009900T DE60009900T2 (en) | 1999-05-19 | 2000-04-27 | BIOADHESIVE POLYMERIC COMPOSITIONS |
AT00926403T ATE264348T1 (en) | 1999-05-19 | 2000-04-27 | BIOADHESIVE COMPOSITIONS MADE OF POLYMERS |
Applications Claiming Priority (2)
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US09/314,842 | 1999-05-19 | ||
US09/314,842 US6297337B1 (en) | 1999-05-19 | 1999-05-19 | Bioadhesive polymer compositions |
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WO2000069932A1 true WO2000069932A1 (en) | 2000-11-23 |
Family
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PCT/US2000/011249 WO2000069932A1 (en) | 1999-05-19 | 2000-04-27 | Bioadhesive polymer compositions |
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US (1) | US6297337B1 (en) |
EP (1) | EP1185565B1 (en) |
AT (1) | ATE264348T1 (en) |
AU (1) | AU4493400A (en) |
DE (1) | DE60009900T2 (en) |
WO (1) | WO2000069932A1 (en) |
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US8048086B2 (en) | 2004-02-25 | 2011-11-01 | Femasys Inc. | Methods and devices for conduit occlusion |
US20060024246A1 (en) * | 2004-07-29 | 2006-02-02 | Prithwiraj Maitra | Oral care compositions with film forming polymers |
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US20060258788A1 (en) * | 2005-05-13 | 2006-11-16 | Scott Coggins | Polymeric hydrogel compositions |
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US20100004124A1 (en) * | 2006-12-05 | 2010-01-07 | David Taft | Systems and methods for delivery of materials for agriculture and aquaculture |
US8399007B2 (en) * | 2006-12-05 | 2013-03-19 | Landec Corporation | Method for formulating a controlled-release pharmaceutical formulation |
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ATE543507T1 (en) * | 2007-11-07 | 2012-02-15 | Ono Pharmaceutical Co | SUSTAINED RELEASE COMPOSITION CONTAINING SDF-1 |
US8114883B2 (en) * | 2007-12-04 | 2012-02-14 | Landec Corporation | Polymer formulations for delivery of bioactive materials |
US9554826B2 (en) | 2008-10-03 | 2017-01-31 | Femasys, Inc. | Contrast agent injection system for sonographic imaging |
US10070888B2 (en) | 2008-10-03 | 2018-09-11 | Femasys, Inc. | Methods and devices for sonographic imaging |
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WO2016011729A1 (en) * | 2014-07-24 | 2016-01-28 | 深圳大学 | Betaine-based shape memory polymer and preparation method therefor |
WO2016202582A1 (en) | 2015-06-17 | 2016-12-22 | Clariant International Ltd | Water-soluble or water-swellable polymers as water-loss reducers in cement slurries |
AU2016353345B2 (en) | 2015-11-12 | 2021-12-23 | University Of Virginia Patent Foundation | Compositions and methods for vas-occlusive contraception and reversal thereof |
JP7089487B2 (en) | 2016-06-20 | 2022-06-22 | クラリアント・インターナシヨナル・リミテツド | Compounds containing certain levels of biobase carbon |
US20180028715A1 (en) | 2016-07-27 | 2018-02-01 | Contraline, Inc. | Carbon-based compositions useful for occlusive medical devices and methods of making and using them |
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- 2000-04-27 WO PCT/US2000/011249 patent/WO2000069932A1/en active Search and Examination
- 2000-04-27 AT AT00926403T patent/ATE264348T1/en not_active IP Right Cessation
- 2000-04-27 AU AU44934/00A patent/AU4493400A/en not_active Abandoned
- 2000-04-27 DE DE60009900T patent/DE60009900T2/en not_active Expired - Fee Related
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Also Published As
Publication number | Publication date |
---|---|
EP1185565B1 (en) | 2004-04-14 |
AU4493400A (en) | 2000-12-05 |
ATE264348T1 (en) | 2004-04-15 |
DE60009900T2 (en) | 2005-03-17 |
DE60009900D1 (en) | 2004-05-19 |
US6297337B1 (en) | 2001-10-02 |
EP1185565A1 (en) | 2002-03-13 |
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