SE505703C2 - Linjär blockpolymer innefattande urea- och uretangrupper, förfarande för framställning av linjära blockpolymerer samt användning av blockpolymererna som implantat - Google Patents
Linjär blockpolymer innefattande urea- och uretangrupper, förfarande för framställning av linjära blockpolymerer samt användning av blockpolymererna som implantatInfo
- Publication number
- SE505703C2 SE505703C2 SE9504495A SE9504495A SE505703C2 SE 505703 C2 SE505703 C2 SE 505703C2 SE 9504495 A SE9504495 A SE 9504495A SE 9504495 A SE9504495 A SE 9504495A SE 505703 C2 SE505703 C2 SE 505703C2
- Authority
- SE
- Sweden
- Prior art keywords
- groups
- block polymer
- linear block
- diisocyanate
- diol
- Prior art date
Links
- 229920000642 polymer Polymers 0.000 title claims abstract description 45
- 239000007943 implant Substances 0.000 title claims abstract description 17
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 title claims abstract description 12
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 title claims abstract description 8
- 239000004202 carbamide Substances 0.000 title claims abstract description 7
- 238000000034 method Methods 0.000 title claims description 14
- 230000008569 process Effects 0.000 title claims description 9
- 125000004185 ester group Chemical group 0.000 claims abstract description 4
- 239000012634 fragment Substances 0.000 claims abstract description 4
- 230000007062 hydrolysis Effects 0.000 claims abstract description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 150000002009 diols Chemical class 0.000 claims description 18
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 14
- -1 polytetramethylene Polymers 0.000 claims description 13
- 239000000835 fiber Substances 0.000 claims description 11
- 235000011187 glycerol Nutrition 0.000 claims description 11
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 9
- 150000004985 diamines Chemical class 0.000 claims description 9
- 229920001610 polycaprolactone Polymers 0.000 claims description 9
- 239000004632 polycaprolactone Substances 0.000 claims description 9
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims description 8
- 150000002170 ethers Chemical class 0.000 claims description 7
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 7
- 210000003041 ligament Anatomy 0.000 claims description 7
- 239000000463 material Substances 0.000 claims description 7
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 6
- QEVGZEDELICMKH-UHFFFAOYSA-N Diglycolic acid Chemical class OC(=O)COCC(O)=O QEVGZEDELICMKH-UHFFFAOYSA-N 0.000 claims description 5
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- OZCLOSUMCCOKAB-UHFFFAOYSA-N 4-bromobutyl 3-hydroxy-2-(hydroxymethyl)-2-methylpropanoate Chemical compound OCC(C)(CO)C(=O)OCCCCBr OZCLOSUMCCOKAB-UHFFFAOYSA-N 0.000 claims description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- JXCHMDATRWUOAP-UHFFFAOYSA-N diisocyanatomethylbenzene Chemical compound O=C=NC(N=C=O)C1=CC=CC=C1 JXCHMDATRWUOAP-UHFFFAOYSA-N 0.000 claims description 4
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 4
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 claims description 3
- RCXHRHWRRACBTK-UHFFFAOYSA-N 3-(oxiran-2-ylmethoxy)propane-1,2-diol Chemical compound OCC(O)COCC1CO1 RCXHRHWRRACBTK-UHFFFAOYSA-N 0.000 claims description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 3
- 239000002202 Polyethylene glycol Substances 0.000 claims description 3
- 239000013543 active substance Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- RQEPEDPOJQCJJT-UHFFFAOYSA-N methyl 3-hydroxy-2-(hydroxymethyl)-2-methylpropanoate Chemical compound COC(=O)C(C)(CO)CO RQEPEDPOJQCJJT-UHFFFAOYSA-N 0.000 claims description 3
- 229920000728 polyester Polymers 0.000 claims description 3
- 229920001223 polyethylene glycol Polymers 0.000 claims description 3
- 241001465754 Metazoa Species 0.000 claims description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 claims description 2
- 150000004984 aromatic diamines Chemical class 0.000 claims description 2
- 210000000845 cartilage Anatomy 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 2
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 claims description 2
- 238000009826 distribution Methods 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 2
- 230000001105 regulatory effect Effects 0.000 claims description 2
- 210000003491 skin Anatomy 0.000 claims description 2
- 210000002435 tendon Anatomy 0.000 claims description 2
- PJANXHGTPQOBST-VAWYXSNFSA-N trans-stilbene Chemical group C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 claims description 2
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 claims 2
- LZDXRPVSAKWYDH-UHFFFAOYSA-N 2-ethyl-2-(prop-2-enoxymethyl)propane-1,3-diol Chemical compound CCC(CO)(CO)COCC=C LZDXRPVSAKWYDH-UHFFFAOYSA-N 0.000 claims 1
- 125000004957 naphthylene group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 20
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 239000012948 isocyanate Substances 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- 150000002513 isocyanates Chemical class 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 125000005442 diisocyanate group Chemical group 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000009987 spinning Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- 229920002396 Polyurea Polymers 0.000 description 2
- 230000001588 bifunctional effect Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000005345 coagulation Methods 0.000 description 2
- 230000015271 coagulation Effects 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 230000035876 healing Effects 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- PMDHMYFSRFZGIO-UHFFFAOYSA-N 1,4,7-trioxacyclotridecane-8,13-dione Chemical compound O=C1CCCCC(=O)OCCOCCO1 PMDHMYFSRFZGIO-UHFFFAOYSA-N 0.000 description 1
- YLFRNCMVVBJXQW-UHFFFAOYSA-N 2-(2,2-diaminoacetyl)oxyethyl 2,2-diaminoacetate Chemical compound NC(N)C(=O)OCCOC(=O)C(N)N YLFRNCMVVBJXQW-UHFFFAOYSA-N 0.000 description 1
- IGDCJKDZZUALAO-UHFFFAOYSA-N 2-prop-2-enoxypropane-1,3-diol Chemical compound OCC(CO)OCC=C IGDCJKDZZUALAO-UHFFFAOYSA-N 0.000 description 1
- PAKCOSURAUIXFG-UHFFFAOYSA-N 3-prop-2-enoxypropane-1,2-diol Chemical compound OCC(O)COCC=C PAKCOSURAUIXFG-UHFFFAOYSA-N 0.000 description 1
- 239000004970 Chain extender Substances 0.000 description 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- MVORZMQFXBLMHM-QWRGUYRKSA-N Gly-His-Lys Chemical compound NCCCC[C@@H](C(O)=O)NC(=O)[C@@H](NC(=O)CN)CC1=CN=CN1 MVORZMQFXBLMHM-QWRGUYRKSA-N 0.000 description 1
- 240000004752 Laburnum anagyroides Species 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- WMAPZFAWKYUPFD-UHFFFAOYSA-N N=C=O.N=C=O.CCOC(N)=O Chemical compound N=C=O.N=C=O.CCOC(N)=O WMAPZFAWKYUPFD-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- KXBFLNPZHXDQLV-UHFFFAOYSA-N [cyclohexyl(diisocyanato)methyl]cyclohexane Chemical compound C1CCCCC1C(N=C=O)(N=C=O)C1CCCCC1 KXBFLNPZHXDQLV-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000002730 additional effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 210000001124 body fluid Anatomy 0.000 description 1
- 239000010839 body fluid Substances 0.000 description 1
- PTIXVVCRANICNC-UHFFFAOYSA-N butane-1,1-diol;hexanedioic acid Chemical compound CCCC(O)O.OC(=O)CCCCC(O)=O PTIXVVCRANICNC-UHFFFAOYSA-N 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 210000001612 chondrocyte Anatomy 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910001431 copper ion Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 229940106012 diethylene glycol adipate Drugs 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000000578 dry spinning Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethyl mercaptane Natural products CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 108010038983 glycyl-histidyl-lysine Proteins 0.000 description 1
- 239000003102 growth factor Substances 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 210000003127 knee Anatomy 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920003226 polyurethane urea Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000005829 trimerization reaction Methods 0.000 description 1
- 238000002166 wet spinning Methods 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/675—Low-molecular-weight compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
- A61L27/14—Macromolecular materials
- A61L27/18—Macromolecular materials obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4236—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups
- C08G18/4238—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups derived from dicarboxylic acids and dialcohols
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4266—Polycondensates having carboxylic or carbonic ester groups in the main chain prepared from hydroxycarboxylic acids and/or lactones
- C08G18/4269—Lactones
- C08G18/4277—Caprolactone and/or substituted caprolactone
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Transplantation (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Dermatology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Polyurethanes Or Polyureas (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
- Materials For Medical Uses (AREA)
- Biological Depolymerization Polymers (AREA)
Priority Applications (26)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9504495A SE505703C2 (sv) | 1995-12-15 | 1995-12-15 | Linjär blockpolymer innefattande urea- och uretangrupper, förfarande för framställning av linjära blockpolymerer samt användning av blockpolymererna som implantat |
| PCT/SE1996/001530 WO1997022643A1 (en) | 1995-12-15 | 1996-11-25 | Linear block polymer comprising urea and urethane groups, method for the production of linear block polymers and use of the block polymers as implants |
| CNB961999462A CN1152899C (zh) | 1995-12-15 | 1996-11-25 | 线型嵌段聚合物和它的生产方法及其用途 |
| DE69613144T DE69613144T2 (de) | 1995-12-15 | 1996-11-25 | Harnstoff- und urethangruppen enthaltendes lineares blockpolymer, verfahren zur herstellung von linearen blockpolymeren sowie verwendung der blockpolymeren als implantate |
| RU98113712/04A RU2189993C2 (ru) | 1995-12-15 | 1996-11-25 | Линейный блок-полимер, содержащий группу мочевины и уретановую группу, способ получения линейных блок-полимеров и использование блок-полимеров в качестве имплантатов |
| HU9901201A HUP9901201A3 (en) | 1995-12-15 | 1996-11-25 | Linear block polymer comprising urea and urethane groups, method for the production of linear block polymers and use of the block polymers as implants |
| DK96942698T DK0866816T3 (da) | 1995-12-15 | 1996-11-25 | Lineær blokpolymer indeholdende urea- og urethangrupper, fremgangsmåde til fremstilling af lineære blokpolymerer samt anvendelse af blokpolymererne som implantater |
| CZ981793A CZ179398A3 (cs) | 1995-12-15 | 1996-11-25 | Lineární blokový polymer, způsob jeho výroby a použití |
| PL96327246A PL327246A1 (en) | 1995-12-15 | 1996-11-25 | Linear block polymer containing urea and urethane groups, method of obtaining them and their appliocation as an implantable material |
| AU11547/97A AU709440B2 (en) | 1995-12-15 | 1996-11-25 | Linear block polymer comprising urea and urethane groups, method for the production of linear block polymers and use of the block polymers as implants |
| EP96942698A EP0866816B1 (de) | 1995-12-15 | 1996-11-25 | Harnstoff- und urethangruppen enthaltendes lineares blockpolymer, verfahren zur herstellung von linearen blockpolymeren sowie verwendung der blockpolymeren als implantate |
| CA002240061A CA2240061A1 (en) | 1995-12-15 | 1996-11-25 | Linear block polymer comprising urea and urethane groups, method for the production of linear block polymers and use of the block polymers as implants |
| US09/091,073 US6210441B1 (en) | 1995-12-15 | 1996-11-25 | Linear block polymer comprising urea and urethane groups, method for the production of linear block polymers and use of the block polymers as implants |
| PT96942698T PT866816E (pt) | 1995-12-15 | 1996-11-25 | Polimeros lineares em blocos que compreendem grupos ureia e uretano, processo para a producao de polimeros leneares em blocos e utilizacao dos polimeros em blocos como implantes |
| NZ324479A NZ324479A (en) | 1995-12-15 | 1996-11-25 | Linear block polymer comprising urea and urethane groups, method for the production of linear block polymers and use of the block polymers as implants |
| AT96942698T ATE201704T1 (de) | 1995-12-15 | 1996-11-25 | Harnstoff- und urethangruppen enthaltendes lineares blockpolymer, verfahren zur herstellung von linearen blockpolymeren sowie verwendung der blockpolymeren als implantate |
| KR1019980704410A KR20000064383A (ko) | 1955-12-15 | 1996-11-25 | 우레아및우레탄기를포함하는선형블록공중합체,선형블록공중합체의제조방법,및삽입물로서블록공중합체의사용방법 |
| JP52269397A JP4059524B2 (ja) | 1995-12-15 | 1996-11-25 | 尿素基およびウレタン基を含む線状ブロック重合体、線状ブロック重合体の製造方法およびインプラントとしてのブロック重合体の用途 |
| TR1998/01091T TR199801091T2 (xx) | 1995-12-15 | 1996-11-25 | �re ve �retan gruplar� ihtiva eden lineer blok polimer lineer blok polimerlerin �retilmesine y�nelik metod ve blok polimerlerin implant olarak kullan�lmas�. |
| SK797-98A SK79798A3 (en) | 1995-12-15 | 1996-11-25 | Linear block polymer comprising urea and urethane groups, method for the production of linear block polymers and use of the block polymers as implants |
| ES96942698T ES2159769T3 (es) | 1995-12-15 | 1996-11-25 | Polimero en bloque lineal que comprende grupos urea y uretano, procedimiento para producirlo y su utilizacion en forma de implantes. |
| IL12488496A IL124884A (en) | 1995-12-15 | 1996-11-25 | Linear polymer blocks containing urea and urethane groups, methods for their preparation and use |
| SI9630322T SI0866816T1 (de) | 1995-12-15 | 1996-11-25 | |
| BR9612032-0A BR9612032A (pt) | 1995-12-15 | 1996-11-25 | Polìmero em blocos linear compreendendo grupos uréia e uretano, método para a produção de polìmeros em blocos lineares e uso dos polìmeros em blocos como implantes. |
| NO982703A NO982703L (no) | 1995-12-15 | 1998-06-11 | Lineµre blokkpolymerer som omfatter urea- og uretangrupper, fremgangsmÕte til fremstilling av lineµre blokkpolymerer og anvendelse av blokkpolymerene som implantater |
| GR20010401328T GR3036469T3 (en) | 1995-12-15 | 2001-08-30 | Linear block polymer comprising urea and urethane groups, method for the production of linear block polymers and use of the block polymers as implants |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9504495A SE505703C2 (sv) | 1995-12-15 | 1995-12-15 | Linjär blockpolymer innefattande urea- och uretangrupper, förfarande för framställning av linjära blockpolymerer samt användning av blockpolymererna som implantat |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| SE9504495D0 SE9504495D0 (sv) | 1995-12-15 |
| SE9504495L SE9504495L (sv) | 1997-06-16 |
| SE505703C2 true SE505703C2 (sv) | 1997-09-29 |
Family
ID=20400606
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE9504495A SE505703C2 (sv) | 1955-12-15 | 1995-12-15 | Linjär blockpolymer innefattande urea- och uretangrupper, förfarande för framställning av linjära blockpolymerer samt användning av blockpolymererna som implantat |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US6210441B1 (de) |
| EP (1) | EP0866816B1 (de) |
| JP (1) | JP4059524B2 (de) |
| KR (1) | KR20000064383A (de) |
| CN (1) | CN1152899C (de) |
| AT (1) | ATE201704T1 (de) |
| AU (1) | AU709440B2 (de) |
| BR (1) | BR9612032A (de) |
| CA (1) | CA2240061A1 (de) |
| CZ (1) | CZ179398A3 (de) |
| DE (1) | DE69613144T2 (de) |
| DK (1) | DK0866816T3 (de) |
| ES (1) | ES2159769T3 (de) |
| GR (1) | GR3036469T3 (de) |
| HU (1) | HUP9901201A3 (de) |
| IL (1) | IL124884A (de) |
| NO (1) | NO982703L (de) |
| NZ (1) | NZ324479A (de) |
| PL (1) | PL327246A1 (de) |
| PT (1) | PT866816E (de) |
| RU (1) | RU2189993C2 (de) |
| SE (1) | SE505703C2 (de) |
| SI (1) | SI0866816T1 (de) |
| SK (1) | SK79798A3 (de) |
| TR (1) | TR199801091T2 (de) |
| WO (1) | WO1997022643A1 (de) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000045869A1 (en) * | 1999-02-02 | 2000-08-10 | Artimplant Ab | A film for medical use, consisting of linear block polymers of polyurethane and a method for the production of such a film |
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|---|---|---|---|---|
| SE510868C2 (sv) | 1997-11-03 | 1999-07-05 | Artimplant Dev Artdev Ab | Formkroppar för användning som implantat i humanmedicin samt förfarande för framställning av sådana formkroppar |
| SE513491C2 (sv) | 1998-12-15 | 2000-09-18 | Artimplant Dev Artdev Ab | Implantat för insättning i människor eller djur innefattande böjliga trådformiga element |
| US20060177416A1 (en) | 2003-10-14 | 2006-08-10 | Medivas, Llc | Polymer particle delivery compositions and methods of use |
| SE0101523L (sv) * | 2000-12-29 | 2002-06-30 | Artimplant Ab | Linjär polymer |
| AR032052A1 (es) * | 2000-12-29 | 2003-10-22 | Artimplant Ab | Polimero lineal de bloques, procedimiento para su preparacion, su uso, implantes, material para relleno, composiciones farmaceuticas y material polimerico poroso que comprenden dicho polimero lineal de bloques |
| SE526106C2 (sv) * | 2002-06-20 | 2005-07-05 | Artimplant Ab | Linjär blockpolymer samt fiber, film, poröst material och implantat innefattande polymeren |
| GB0222522D0 (en) | 2002-09-27 | 2002-11-06 | Controlled Therapeutics Sct | Water-swellable polymers |
| US20050013793A1 (en) * | 2003-01-16 | 2005-01-20 | Beckman Eric J. | Biodegradable polyurethanes and use thereof |
| US20070160622A1 (en) * | 2005-12-07 | 2007-07-12 | Medivas, Llc | Method for assembling a polymer-biologic delivery composition |
| US8791073B2 (en) * | 2004-05-14 | 2014-07-29 | William Marsh Rice University | Peptide-modified polyurethane compositions and associated methods |
| GB0417401D0 (en) | 2004-08-05 | 2004-09-08 | Controlled Therapeutics Sct | Stabilised prostaglandin composition |
| US20060153796A1 (en) * | 2005-01-10 | 2006-07-13 | Fitz Benjamin D | Diisocyanate terminated macromer and formulation thereof for use as an internal adhesive or sealant |
| US7968668B2 (en) | 2005-01-10 | 2011-06-28 | Ethicon Inc. | Diisocyanate terminated macromer and formulation thereof for use as an internal adhesive or sealant |
| US7728097B2 (en) * | 2005-01-10 | 2010-06-01 | Ethicon, Inc. | Method of making a diisocyanate terminated macromer |
| US8470954B2 (en) | 2005-01-10 | 2013-06-25 | Ethicon, Inc. | Diisocyanate terminated macromer and formulation thereof for use as an internal adhesive or sealant |
| US20070167617A1 (en) * | 2006-01-17 | 2007-07-19 | Fitz Benjamin D | Method of making a diisocyanate terminated macromer |
| EP1700872A3 (de) * | 2005-03-10 | 2008-07-23 | Radi Medical Systems Ab | Polyharnstoffurethanmaterialien und Verfahren zur Herstellung |
| CA2623198C (en) | 2005-09-22 | 2014-08-05 | Medivas, Llc | Bis-(a-amino)-diol-diester-containing poly(ester amide) and poly(ester urethane) compositions and methods of use |
| EP1933881B1 (de) * | 2005-09-22 | 2019-03-13 | Medivas, LLC | Feste polymer-abgabezusammensetzungen und anwendungsverfahren dafür |
| US20070106214A1 (en) * | 2005-10-17 | 2007-05-10 | Coaptus Medical Corporation | Systems and methods for securing cardiovascular tissue, including via asymmetric inflatable members |
| US8765164B2 (en) * | 2005-10-21 | 2014-07-01 | Kenneth W. Carpenter | Poly(ester urea) polymers and methods of use |
| EP2019645A4 (de) * | 2006-05-02 | 2013-03-06 | Medivas Llc | Freisetzung ophthalmologischer wirkstoffe ausserhalb oder innerhalb des auges |
| WO2007133616A2 (en) * | 2006-05-09 | 2007-11-22 | Medivas, Llc | Biodegradable water soluble polymers |
| GB0613333D0 (en) | 2006-07-05 | 2006-08-16 | Controlled Therapeutics Sct | Hydrophilic polyurethane compositions |
| GB0613638D0 (en) | 2006-07-08 | 2006-08-16 | Controlled Therapeutics Sct | Polyurethane elastomers |
| GB0620685D0 (en) | 2006-10-18 | 2006-11-29 | Controlled Therapeutics Sct | Bioresorbable polymers |
| EP1985319B1 (de) * | 2007-04-23 | 2012-06-13 | Jointsphere B.V. | Vorrichtung zur Knorpelreparatur |
| US20090029937A1 (en) * | 2007-07-24 | 2009-01-29 | Cornell University | Biodegradable cationic polymer gene transfer compositions and methods of use |
| US8324292B2 (en) * | 2008-02-29 | 2012-12-04 | Ethicon, Inc. | Medically acceptable formulation of a diisocyanate terminated macromer for use as an internal adhesive or sealant |
| US8071663B2 (en) * | 2008-02-29 | 2011-12-06 | Ethicon, Inc. | Medically acceptable formulation of a diisocyanate terminated macromer for use as an internal adhesive or sealant |
| EP2323671A4 (de) * | 2008-08-13 | 2012-09-26 | Medivas Llc | Biologisch abbaubare aabb-poly(depsipeptid-)polymere sowie verfahren zu ihrer verwendung |
| US8962784B2 (en) * | 2008-12-19 | 2015-02-24 | Ethicon, Inc. | Isocyanate terminated macromer and formulation thereof for use as an internal adhesive or sealant |
| EP2413838A4 (de) * | 2009-04-03 | 2012-09-19 | Biomerix Corp | Zumindest teilweise resorbierbare retikulierte elastomermatrixpartikel und herstellungsverfahren |
| WO2012097381A1 (en) | 2011-01-14 | 2012-07-19 | Biomerix Corporation | At least partially resorbable reticulated elastomeric matrix elements and methods of making same |
| US9873765B2 (en) | 2011-06-23 | 2018-01-23 | Dsm Ip Assets, B.V. | Biodegradable polyesteramide copolymers for drug delivery |
| EP2723800B1 (de) | 2011-06-23 | 2015-10-07 | DSM IP Assets B.V. | Mikro- oder nanopartikel mit einem biologisch abbaubaren polyesteramid-copolymer zur verwendung bei der verabreichung von bioaktiven substanzen |
| TWI641396B (zh) * | 2011-09-23 | 2018-11-21 | Bvw控股公司 | 醫療共聚物 |
| US10434071B2 (en) | 2014-12-18 | 2019-10-08 | Dsm Ip Assets, B.V. | Drug delivery system for delivery of acid sensitivity drugs |
| CN112011049A (zh) * | 2019-05-30 | 2020-12-01 | 中国科学院化学研究所 | 一种热塑性聚脲弹性体及其制备方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE790976A (fr) * | 1971-11-06 | 1973-05-07 | Bayer Ag | Derives silyles de l'uree et leur preparation |
| US4549010A (en) * | 1984-06-27 | 1985-10-22 | Merck & Co., Inc. | Bioerodible poly(ortho ester) thermoplastic elastomer from diketene diacetal |
| CA1338678C (en) * | 1987-12-02 | 1996-10-22 | Tyndale Plains-Hunter Ltd. | Hydrophilic polyurethanes of improved strength |
| CA2038605C (en) * | 1990-06-15 | 2000-06-27 | Leonard Pinchuk | Crack-resistant polycarbonate urethane polymer prostheses and the like |
| EP0536223B1 (de) * | 1990-06-26 | 2004-09-15 | AorTech Biomaterials Pty Ltd | Elastomere polyurethan- oder polyurethan-harnstoff-zusammensetzungen |
| AU664158B2 (en) * | 1990-09-12 | 1995-11-09 | Polymedica Industries, Inc | Biostable polyurethane products |
-
1995
- 1995-12-15 SE SE9504495A patent/SE505703C2/sv not_active IP Right Cessation
-
1996
- 1996-11-25 AU AU11547/97A patent/AU709440B2/en not_active Expired
- 1996-11-25 ES ES96942698T patent/ES2159769T3/es not_active Expired - Lifetime
- 1996-11-25 TR TR1998/01091T patent/TR199801091T2/xx unknown
- 1996-11-25 PT PT96942698T patent/PT866816E/pt unknown
- 1996-11-25 SI SI9630322T patent/SI0866816T1/xx unknown
- 1996-11-25 CA CA002240061A patent/CA2240061A1/en not_active Abandoned
- 1996-11-25 US US09/091,073 patent/US6210441B1/en not_active Expired - Lifetime
- 1996-11-25 RU RU98113712/04A patent/RU2189993C2/ru not_active IP Right Cessation
- 1996-11-25 HU HU9901201A patent/HUP9901201A3/hu unknown
- 1996-11-25 DE DE69613144T patent/DE69613144T2/de not_active Expired - Lifetime
- 1996-11-25 AT AT96942698T patent/ATE201704T1/de not_active IP Right Cessation
- 1996-11-25 CN CNB961999462A patent/CN1152899C/zh not_active Expired - Lifetime
- 1996-11-25 BR BR9612032-0A patent/BR9612032A/pt not_active Application Discontinuation
- 1996-11-25 CZ CZ981793A patent/CZ179398A3/cs unknown
- 1996-11-25 NZ NZ324479A patent/NZ324479A/xx unknown
- 1996-11-25 KR KR1019980704410A patent/KR20000064383A/ko not_active Application Discontinuation
- 1996-11-25 PL PL96327246A patent/PL327246A1/xx unknown
- 1996-11-25 EP EP96942698A patent/EP0866816B1/de not_active Expired - Lifetime
- 1996-11-25 DK DK96942698T patent/DK0866816T3/da active
- 1996-11-25 JP JP52269397A patent/JP4059524B2/ja not_active Expired - Fee Related
- 1996-11-25 WO PCT/SE1996/001530 patent/WO1997022643A1/en not_active Application Discontinuation
- 1996-11-25 IL IL12488496A patent/IL124884A/en not_active IP Right Cessation
- 1996-11-25 SK SK797-98A patent/SK79798A3/sk unknown
-
1998
- 1998-06-11 NO NO982703A patent/NO982703L/no unknown
-
2001
- 2001-08-30 GR GR20010401328T patent/GR3036469T3/el not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000045869A1 (en) * | 1999-02-02 | 2000-08-10 | Artimplant Ab | A film for medical use, consisting of linear block polymers of polyurethane and a method for the production of such a film |
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| NUG | Patent has lapsed |