CA2238227C - Crosslinked poly(amino acids) and method of preparation - Google Patents
Crosslinked poly(amino acids) and method of preparation Download PDFInfo
- Publication number
- CA2238227C CA2238227C CA002238227A CA2238227A CA2238227C CA 2238227 C CA2238227 C CA 2238227C CA 002238227 A CA002238227 A CA 002238227A CA 2238227 A CA2238227 A CA 2238227A CA 2238227 C CA2238227 C CA 2238227C
- Authority
- CA
- Canada
- Prior art keywords
- poly
- amino acid
- crosslinked poly
- ether
- weight
- 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.)
- Expired - Fee Related
Links
- -1 poly(amino acids) Polymers 0.000 title claims abstract description 80
- 229920001308 poly(aminoacid) Polymers 0.000 title claims abstract description 49
- 238000000034 method Methods 0.000 title claims abstract description 22
- 238000002360 preparation method Methods 0.000 title abstract description 6
- 239000004971 Cross linker Substances 0.000 claims abstract description 25
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- 229920000642 polymer Polymers 0.000 claims description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 14
- 239000007864 aqueous solution Substances 0.000 claims description 11
- 239000011541 reaction mixture Substances 0.000 claims description 11
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 9
- 150000007942 carboxylates Chemical group 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 7
- 239000007983 Tris buffer Substances 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- UWFRVQVNYNPBEF-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(C)C=C1C UWFRVQVNYNPBEF-UHFFFAOYSA-N 0.000 claims description 4
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 claims description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 4
- 229920000805 Polyaspartic acid Polymers 0.000 claims description 4
- 238000004132 cross linking Methods 0.000 claims description 4
- 229920002643 polyglutamic acid Polymers 0.000 claims description 4
- 150000008442 polyphenolic compounds Chemical class 0.000 claims description 4
- 235000013824 polyphenols Nutrition 0.000 claims description 4
- SEFYJVFBMNOLBK-UHFFFAOYSA-N 2-[2-[2-(oxiran-2-ylmethoxy)ethoxy]ethoxymethyl]oxirane Chemical compound C1OC1COCCOCCOCC1CO1 SEFYJVFBMNOLBK-UHFFFAOYSA-N 0.000 claims description 3
- FSYPIGPPWAJCJG-UHFFFAOYSA-N 2-[[4-(oxiran-2-ylmethoxy)phenoxy]methyl]oxirane Chemical compound C1OC1COC(C=C1)=CC=C1OCC1CO1 FSYPIGPPWAJCJG-UHFFFAOYSA-N 0.000 claims description 3
- ZFIVKAOQEXOYFY-UHFFFAOYSA-N Diepoxybutane Chemical compound C1OC1C1OC1 ZFIVKAOQEXOYFY-UHFFFAOYSA-N 0.000 claims description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 238000004108 freeze drying Methods 0.000 claims description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 229910001413 alkali metal ion Inorganic materials 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
- 238000011084 recovery Methods 0.000 claims 2
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 claims 1
- 229960004337 hydroquinone Drugs 0.000 claims 1
- 229920000247 superabsorbent polymer Polymers 0.000 abstract description 10
- 239000004583 superabsorbent polymers (SAPs) Substances 0.000 abstract description 10
- 239000000017 hydrogel Substances 0.000 abstract description 5
- 239000000463 material Substances 0.000 abstract description 4
- 229920000647 polyepoxide Polymers 0.000 abstract description 4
- 229920002873 Polyethylenimine Polymers 0.000 abstract description 3
- 239000000203 mixture Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 241001122767 Theaceae Species 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 230000007062 hydrolysis Effects 0.000 description 7
- 238000006460 hydrolysis reaction Methods 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 150000001413 amino acids Chemical group 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 239000002250 absorbent Substances 0.000 description 3
- 235000001014 amino acid Nutrition 0.000 description 3
- 229940024606 amino acid Drugs 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 239000002504 physiological saline solution Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000004386 Erythritol Substances 0.000 description 2
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 2
- 239000004472 Lysine Substances 0.000 description 2
- 229920002197 Sodium polyaspartate Polymers 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 125000000539 amino acid group Chemical group 0.000 description 2
- 229960004424 carbon dioxide Drugs 0.000 description 2
- 235000011089 carbon dioxide Nutrition 0.000 description 2
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 2
- 229940009714 erythritol Drugs 0.000 description 2
- 235000019414 erythritol Nutrition 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 230000036571 hydration Effects 0.000 description 2
- 238000006703 hydration reaction Methods 0.000 description 2
- 125000005647 linker group Chemical group 0.000 description 2
- 230000000269 nucleophilic effect Effects 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 2
- 239000003039 volatile agent Substances 0.000 description 2
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 1
- LFKLPJRVSHJZPL-UHFFFAOYSA-N 1,2:7,8-diepoxyoctane Chemical compound C1OC1CCCCC1CO1 LFKLPJRVSHJZPL-UHFFFAOYSA-N 0.000 description 1
- PRJNEUBECVAVAG-UHFFFAOYSA-N 1,3-bis(ethenyl)benzene Chemical compound C=CC1=CC=CC(C=C)=C1 PRJNEUBECVAVAG-UHFFFAOYSA-N 0.000 description 1
- IVIDDMGBRCPGLJ-UHFFFAOYSA-N 2,3-bis(oxiran-2-ylmethoxy)propan-1-ol Chemical compound C1OC1COC(CO)COCC1CO1 IVIDDMGBRCPGLJ-UHFFFAOYSA-N 0.000 description 1
- HCPAOTGVQASBMP-UHFFFAOYSA-N 2-(oxiran-2-ylmethyl)oxirane Chemical compound C1OC1CC1CO1 HCPAOTGVQASBMP-UHFFFAOYSA-N 0.000 description 1
- HPILSDOMLLYBQF-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COC(CCC)OCC1CO1 HPILSDOMLLYBQF-UHFFFAOYSA-N 0.000 description 1
- HDPLHDGYGLENEI-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)propan-2-yloxymethyl]oxirane Chemical compound C1OC1COC(C)COCC1CO1 HDPLHDGYGLENEI-UHFFFAOYSA-N 0.000 description 1
- HTJFSXYVAKSPNF-UHFFFAOYSA-N 2-[2-(oxiran-2-yl)ethyl]oxirane Chemical compound C1OC1CCC1CO1 HTJFSXYVAKSPNF-UHFFFAOYSA-N 0.000 description 1
- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 1
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 description 1
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 description 1
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 1
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 102100036378 T-cell immunomodulatory protein Human genes 0.000 description 1
- 101710194900 T-cell immunomodulatory protein Proteins 0.000 description 1
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 description 1
- 239000004473 Threonine Substances 0.000 description 1
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 1
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000003862 amino acid derivatives Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 229960001230 asparagine Drugs 0.000 description 1
- 235000009582 asparagine Nutrition 0.000 description 1
- 229940009098 aspartate Drugs 0.000 description 1
- 239000013060 biological fluid Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 235000018417 cysteine Nutrition 0.000 description 1
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
- 125000005462 imide group Chemical group 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 229960000310 isoleucine Drugs 0.000 description 1
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 238000000643 oven drying Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 108010064470 polyaspartate Proteins 0.000 description 1
- 229920000867 polyelectrolyte Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000007420 reactivation Effects 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 238000009489 vacuum treatment Methods 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 229920003176 water-insoluble polymer Polymers 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
-
- 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
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
-
- 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
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/04—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polycarbonamides, polyesteramides or polyimides
-
- 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
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
- C08G59/5046—Amines heterocyclic
- C08G59/5053—Amines heterocyclic containing only nitrogen as a heteroatom
- C08G59/506—Amines heterocyclic containing only nitrogen as a heteroatom having one nitrogen atom in the ring
- C08G59/5066—Aziridines or their derivatives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
- C08G59/52—Amino carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/04—Preparatory processes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/028—Polyamidoamines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyamides (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Biological Depolymerization Polymers (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US4791697P | 1997-05-29 | 1997-05-29 | |
| US60/047,916 | 1997-05-29 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2238227A1 CA2238227A1 (en) | 1998-11-29 |
| CA2238227C true CA2238227C (en) | 2001-10-30 |
Family
ID=21951739
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002238227A Expired - Fee Related CA2238227C (en) | 1997-05-29 | 1998-05-21 | Crosslinked poly(amino acids) and method of preparation |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US5955549A (https=) |
| EP (1) | EP0881247B1 (https=) |
| JP (1) | JPH10330478A (https=) |
| KR (1) | KR19980087399A (https=) |
| AR (1) | AR015831A1 (https=) |
| BR (1) | BR9801700A (https=) |
| CA (1) | CA2238227C (https=) |
| DE (1) | DE69821548T2 (https=) |
| PL (1) | PL326540A1 (https=) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6106555A (en) * | 1998-12-15 | 2000-08-22 | Av Healing Llc | Method for tissue fixation |
| WO2001048056A1 (fr) * | 1999-12-28 | 2001-07-05 | Mitsui Chemicals, Incorporated | Procede de production d'acide (sel) polyaspartique reticule |
| US6365706B1 (en) | 2000-06-21 | 2002-04-02 | Mississippi Chemical Corporation | Process for production of polyasparagine and the high nitrogen content polymer formed thereby |
| JP4669121B2 (ja) * | 2000-11-14 | 2011-04-13 | 三井化学株式会社 | 架橋重合体及びその製造方法 |
| JP4669123B2 (ja) * | 2000-12-07 | 2011-04-13 | 三井化学株式会社 | 架橋ポリアスパラギン酸(塩)から得られる多孔質粒子及びその製造方法 |
| US6495658B2 (en) | 2001-02-06 | 2002-12-17 | Folia, Inc. | Comonomer compositions for production of imide-containing polyamino acids |
| JP4074905B2 (ja) * | 2001-02-28 | 2008-04-16 | 大日本インキ化学工業株式会社 | 吸水性材料、その製造方法および吸水性物品 |
| US7001988B2 (en) * | 2001-09-25 | 2006-02-21 | Keraplast Technologies, Ltd. | Methods for controlling peptide solubility, chemically modified peptides, and stable solvent systems for producing same |
| US6914126B2 (en) * | 2002-04-10 | 2005-07-05 | Keraplast Technologies, Ltd. | Methods for producing, films comprising, and methods for using heterogenous crosslinked protein networks |
| US7001987B2 (en) * | 2002-04-22 | 2006-02-21 | Keraplast Technologies, Ltd. | Hydrogel with controllable mechanical, chemical, and biological properties and method for making same |
| EP1495048B1 (en) * | 2002-04-10 | 2014-03-05 | Keraplast Technologies Ltd. | Heterogenenous protein networks crosslinked with silicone-containing links,and methos for producing them |
| US6989437B2 (en) | 2002-04-10 | 2006-01-24 | Keraplast Technologies, Ltd. | Methods for producing, films comprising, and methods for using heterogeneous crosslinked protein networks |
| US20040120910A1 (en) * | 2002-04-10 | 2004-06-24 | Dyke Mark Van | Methods for producing, films comprising, and methods for using heterogeneous crosslinked protein networks |
| US20040062793A1 (en) * | 2002-07-05 | 2004-04-01 | Dyke Mark Van | Tissue defect dressings comprising proteinaceous networks |
| US7163321B2 (en) * | 2002-07-25 | 2007-01-16 | Steven Contarino | Emergency vehicle grille |
| US20040019172A1 (en) * | 2002-07-26 | 2004-01-29 | Tou-Hsiung Yang | Biodegradable, water absorbable resin and its preparation method |
| US7294672B2 (en) * | 2003-03-31 | 2007-11-13 | Polymer Chemistry Innovations, Inc. | Method to form polymeric materials by reverse suspension/emulsion polymerization and compositions formed using that method |
| US20040206694A1 (en) * | 2003-04-16 | 2004-10-21 | John Charkoudian | Epoxide-crosslinked, charged cellulosic membrane |
| US7364879B2 (en) * | 2003-12-19 | 2008-04-29 | Tung Hai Biotechnology Corporation | Stable biodegradable, high water absorbable polyglutamic acid hydrogel by 3-dimensional cross-linking and its preparation method |
| US8795709B2 (en) | 2006-03-29 | 2014-08-05 | Incept Llc | Superabsorbent, freeze dried hydrogels for medical applications |
| EP2041214A4 (en) * | 2006-07-10 | 2009-07-08 | Medipacs Inc | SUPERELASTIC EPOXY HYDROGEL |
| EP2227635A2 (en) | 2007-12-03 | 2010-09-15 | Medipacs, Inc. | Fluid metering device |
| TWI353397B (en) * | 2009-04-07 | 2011-12-01 | Far Eastern New Century Corp | Water-insoluble polyglutamic acid fiber and produc |
| CA2977830C (en) | 2009-05-04 | 2019-09-17 | Incept, Llc | Biomaterials for track and puncture closure |
| TWI448485B (zh) * | 2010-08-03 | 2014-08-11 | Univ Nat Taiwan Normal | 半互穿網絡型水膠聚合物、其製造方法及包含其之水泥組成物 |
| WO2012092542A2 (en) * | 2010-12-30 | 2012-07-05 | University Of Massachusetts Lowell | Responsive cell culture hydrogel |
| EP2847249A4 (en) | 2012-03-14 | 2016-12-28 | Medipacs Inc | Smart polymer materials with excess reactive molecules |
| WO2018222545A1 (en) | 2017-05-27 | 2018-12-06 | Ecovia Renewables Inc. | Poly(amino acid) rheology modifier compositions and methods of use |
| US20220347655A1 (en) * | 2019-10-04 | 2022-11-03 | Ecovia Renewables Inc. | Water-absorbent cross-linked polymeric polycarboxylic acid and methods of making |
| US12239746B2 (en) | 2019-10-23 | 2025-03-04 | Kimberly-Clark Worldwide, Inc. | Superabsorbent material absorbent capacity increase with use of multifunctional chemical agents |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6018690B2 (ja) * | 1981-12-30 | 1985-05-11 | 住友精化株式会社 | 吸水性樹脂の吸水性改良方法 |
| US4654789A (en) * | 1984-04-04 | 1987-03-31 | Honeywell Information Systems Inc. | LSI microprocessor chip with backward pin compatibility |
| US5284936A (en) * | 1991-03-29 | 1994-02-08 | University Of South Alabama | Polyamino acid superabsorbents |
| US5466760A (en) * | 1992-08-07 | 1995-11-14 | Srchem, Inc. | Copolymers of polyaspartic acid |
| DE4244194A1 (de) * | 1992-12-24 | 1994-06-30 | Basf Ag | Wasserlösliche Kondensationsprodukte aus Aminogruppen enthaltenden Verbindungen und Vernetzern, Verfahren zu ihrer Herstellung und ihre Verwendung |
| US5461085A (en) * | 1993-12-17 | 1995-10-24 | Mitsui Toatsu Chemicals, Incorporated | Superabsorbent polymer and process for producing same |
| JPH07309943A (ja) * | 1994-05-16 | 1995-11-28 | Mitsubishi Chem Corp | 酸性アミノ酸系樹脂 |
| US5552516A (en) * | 1994-06-22 | 1996-09-03 | Donlar Corporation | Soluble, crosslinked polyaspartates |
| US5786429A (en) * | 1996-04-18 | 1998-07-28 | Hercules Incorporated | Highly branched polyamidoamines and their preparation |
-
1998
- 1998-05-14 EP EP98303787A patent/EP0881247B1/en not_active Expired - Lifetime
- 1998-05-14 US US09/078,743 patent/US5955549A/en not_active Expired - Fee Related
- 1998-05-14 DE DE69821548T patent/DE69821548T2/de not_active Expired - Fee Related
- 1998-05-21 CA CA002238227A patent/CA2238227C/en not_active Expired - Fee Related
- 1998-05-26 BR BR9801700-4A patent/BR9801700A/pt not_active IP Right Cessation
- 1998-05-27 KR KR1019980019175A patent/KR19980087399A/ko not_active Ceased
- 1998-05-27 AR ARP980102465A patent/AR015831A1/es unknown
- 1998-05-28 PL PL98326540A patent/PL326540A1/xx unknown
- 1998-05-29 JP JP10149461A patent/JPH10330478A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP0881247A1 (en) | 1998-12-02 |
| BR9801700A (pt) | 1999-12-14 |
| CA2238227A1 (en) | 1998-11-29 |
| EP0881247B1 (en) | 2004-02-11 |
| AR015831A1 (es) | 2001-05-30 |
| DE69821548T2 (de) | 2004-12-30 |
| DE69821548D1 (de) | 2004-03-18 |
| KR19980087399A (ko) | 1998-12-05 |
| PL326540A1 (en) | 1998-12-07 |
| US5955549A (en) | 1999-09-21 |
| JPH10330478A (ja) | 1998-12-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2238227C (en) | Crosslinked poly(amino acids) and method of preparation | |
| JP5232141B2 (ja) | マルチアームポリ(エチレングリコール)アミンを調製する方法 | |
| KR100512483B1 (ko) | 신규한 폴리에틸렌글리콜-말레이미드 유도체의 합성방법 | |
| ES2321800T3 (es) | Procedimiento de preparacion de esteres de 1-benzotriazolil carbonato de polimeros solubles en agua. | |
| US8454946B2 (en) | N-maleimidyl polymer derivatives | |
| JP2003518526A (ja) | ポリ(エチレングリコール)の加水分解的に分解可能なカルバメート誘導体 | |
| CA2628579C (en) | Carbodiimide crosslinking of functionalized polethylene glycols | |
| US5229466A (en) | Powdery absorbing material for aqueous liquids based on water-swellable carboxylate polymers | |
| CN105482040A (zh) | 一种水溶性可降解交联剂、利用该交联剂制备γ-聚谷氨酸吸水材料的方法 | |
| JP5150297B2 (ja) | ヘテロ二官能性ポリエチレングリコール誘導体およびその調製方法 | |
| CN102206409B (zh) | 一种温和条件下快速形成共价交联的水凝胶及其制备方法 | |
| CN112263706B (zh) | 一种可生物降解的生物粘合剂及其制备方法 | |
| MXPA98003857A (en) | Entrelazados poly (aminoacidos) and supreparac method | |
| CN114835892A (zh) | 一种阳离子型共聚氨基酸及其制备方法 | |
| Garner et al. | Types and Chemistry of Synthetic Hydrogels | |
| CN102827367A (zh) | 一种脂肪族聚酯-聚氨基酸嵌段共聚物及其制备方法以及一种水凝胶及其制备方法 | |
| BAT ÖZMATARA et al. | Synthesis of isocyanate containing cryogels for fast (bio) molecular immobilization | |
| Rabiee et al. | Photocurable antibacterial bioadhesives derived from itaconated polyhydroxyurethane prepolymer and partially methacrylated tannic acid | |
| JP2000290502A (ja) | 吸水性材料 | |
| CN119119710A (zh) | 一种三组分双反应的水凝胶材料、其制备方法及应用 | |
| JP2000212372A (ja) | 吸水性樹脂 | |
| JPS63199205A (ja) | 高吸水性ポリマ−の製造方法 | |
| JPH1160728A (ja) | ポリ酸性アミノ酸系吸水性架橋体およびその製造方法 | |
| CN120585728A (zh) | 一种光响应的药物凝胶载体及其制备方法 | |
| WO2023183954A1 (en) | An aqueous antimicrobial polymer dispersion |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |