DK2794798T3 - Hydroxy-aminopolymer og anvendelse deraf i poly-urea/polyurethan-vævsklæbemidler - Google Patents
Hydroxy-aminopolymer og anvendelse deraf i poly-urea/polyurethan-vævsklæbemidler Download PDFInfo
- Publication number
- DK2794798T3 DK2794798T3 DK12809752.4T DK12809752T DK2794798T3 DK 2794798 T3 DK2794798 T3 DK 2794798T3 DK 12809752 T DK12809752 T DK 12809752T DK 2794798 T3 DK2794798 T3 DK 2794798T3
- Authority
- DK
- Denmark
- Prior art keywords
- alkylene oxide
- component
- compound
- functional
- hydroxy
- Prior art date
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- -1 HYDROXY AMINO Chemical class 0.000 title claims description 45
- 229920000642 polymer Polymers 0.000 title claims description 40
- 239000003106 tissue adhesive Substances 0.000 title description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 title description 5
- 239000004202 carbamide Substances 0.000 title description 3
- 229940075469 tissue adhesives Drugs 0.000 title description 3
- 150000001875 compounds Chemical group 0.000 claims description 134
- 125000002947 alkylene group Chemical group 0.000 claims description 108
- 238000000034 method Methods 0.000 claims description 86
- 239000007858 starting material Substances 0.000 claims description 83
- 230000008569 process Effects 0.000 claims description 76
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 69
- 239000003054 catalyst Substances 0.000 claims description 65
- 238000006243 chemical reaction Methods 0.000 claims description 57
- 150000003077 polyols Chemical group 0.000 claims description 54
- 229920005862 polyol Polymers 0.000 claims description 53
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 49
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 41
- 229920002635 polyurethane Polymers 0.000 claims description 41
- 239000004814 polyurethane Substances 0.000 claims description 41
- 229920000570 polyether Polymers 0.000 claims description 37
- 150000001412 amines Chemical class 0.000 claims description 34
- 229910052751 metal Inorganic materials 0.000 claims description 34
- 239000002184 metal Substances 0.000 claims description 34
- 125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 claims description 33
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 32
- 125000001931 aliphatic group Chemical group 0.000 claims description 23
- 238000004519 manufacturing process Methods 0.000 claims description 22
- 125000003277 amino group Chemical group 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 16
- 239000012948 isocyanate Substances 0.000 claims description 16
- 150000002513 isocyanates Chemical class 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 229920005906 polyester polyol Polymers 0.000 claims description 10
- 239000005056 polyisocyanate Substances 0.000 claims description 10
- 229920001228 polyisocyanate Polymers 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 229910021529 ammonia Inorganic materials 0.000 claims description 8
- 239000012766 organic filler Substances 0.000 claims description 8
- 150000003512 tertiary amines Chemical class 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 229920000728 polyester Polymers 0.000 claims description 7
- 150000003254 radicals Chemical class 0.000 claims description 7
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 5
- 229920001577 copolymer Polymers 0.000 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 4
- 150000003141 primary amines Chemical class 0.000 claims description 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 3
- 125000006353 oxyethylene group Chemical group 0.000 claims description 3
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 claims description 2
- LSYBWANTZYUTGJ-UHFFFAOYSA-N 2-[2-(dimethylamino)ethyl-methylamino]ethanol Chemical compound CN(C)CCN(C)CCO LSYBWANTZYUTGJ-UHFFFAOYSA-N 0.000 claims description 2
- BYACHAOCSIPLCM-UHFFFAOYSA-N 2-[2-[bis(2-hydroxyethyl)amino]ethyl-(2-hydroxyethyl)amino]ethanol Chemical compound OCCN(CCO)CCN(CCO)CCO BYACHAOCSIPLCM-UHFFFAOYSA-N 0.000 claims description 2
- HMMBJOWWRLZEMI-UHFFFAOYSA-N 4,5,6,7-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1CCCC2=C1C(=O)OC2=O HMMBJOWWRLZEMI-UHFFFAOYSA-N 0.000 claims description 2
- CKLJMWTZIZZHCS-REOHCLBHSA-L aspartate group Chemical group N[C@@H](CC(=O)[O-])C(=O)[O-] CKLJMWTZIZZHCS-REOHCLBHSA-L 0.000 claims description 2
- XFLSMWXCZBIXLV-UHFFFAOYSA-N n,n-dimethyl-2-(4-methylpiperazin-1-yl)ethanamine Chemical compound CN(C)CCN1CCN(C)CC1 XFLSMWXCZBIXLV-UHFFFAOYSA-N 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 150000003972 cyclic carboxylic anhydrides Chemical class 0.000 claims 6
- 230000001413 cellular effect Effects 0.000 claims 2
- 239000007983 Tris buffer Substances 0.000 claims 1
- 125000004404 heteroalkyl group Chemical group 0.000 claims 1
- ZUHZZVMEUAUWHY-UHFFFAOYSA-N n,n-dimethylpropan-1-amine Chemical compound CCCN(C)C ZUHZZVMEUAUWHY-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 36
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 32
- 229920000162 poly(ureaurethane) Polymers 0.000 description 30
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical class OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 23
- 239000000047 product Substances 0.000 description 21
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical class OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 19
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 18
- 238000007792 addition Methods 0.000 description 17
- 239000000853 adhesive Substances 0.000 description 16
- 230000001070 adhesive effect Effects 0.000 description 16
- 238000002156 mixing Methods 0.000 description 15
- 150000003839 salts Chemical class 0.000 description 15
- 239000002253 acid Substances 0.000 description 14
- 239000003446 ligand Substances 0.000 description 14
- 150000002825 nitriles Chemical class 0.000 description 14
- 239000000126 substance Substances 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical class CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical class OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 11
- 239000013543 active substance Substances 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 10
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 10
- 230000009286 beneficial effect Effects 0.000 description 10
- 235000011187 glycerol Nutrition 0.000 description 10
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 10
- 239000011261 inert gas Substances 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 9
- 229910002651 NO3 Inorganic materials 0.000 description 9
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 9
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 9
- 208000027418 Wounds and injury Diseases 0.000 description 9
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical class OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 9
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 9
- 150000002540 isothiocyanates Chemical class 0.000 description 9
- 239000011701 zinc Substances 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 8
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 8
- 206010052428 Wound Diseases 0.000 description 8
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 8
- 150000001450 anions Chemical class 0.000 description 8
- 150000007942 carboxylates Chemical class 0.000 description 8
- GHLKSLMMWAKNBM-UHFFFAOYSA-N dodecane-1,12-diol Chemical class OCCCCCCCCCCCCO GHLKSLMMWAKNBM-UHFFFAOYSA-N 0.000 description 8
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- 229910052725 zinc Inorganic materials 0.000 description 8
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical class CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 7
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 7
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- 238000001816 cooling Methods 0.000 description 7
- 150000002009 diols Chemical class 0.000 description 7
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- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 7
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- 239000000725 suspension Substances 0.000 description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 6
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical class CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- 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 description 6
- SZAVHWMCBDFDCM-KTTJZPQESA-N cobalt-60(3+);hexacyanide Chemical compound [60Co+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] SZAVHWMCBDFDCM-KTTJZPQESA-N 0.000 description 6
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- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 6
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Chemical class OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 5
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical class OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 5
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 5
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- 238000013019 agitation Methods 0.000 description 5
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- 239000003102 growth factor Substances 0.000 description 5
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- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
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Classifications
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- A61L24/00—Surgical adhesives or cements; Adhesives for colostomy devices
- A61L24/04—Surgical adhesives or cements; Adhesives for colostomy devices containing macromolecular materials
- A61L24/046—Surgical adhesives or cements; Adhesives for colostomy devices containing macromolecular materials obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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- A—HUMAN NECESSITIES
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- 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
- A61L24/00—Surgical adhesives or cements; Adhesives for colostomy devices
- A61L24/001—Use of materials characterised by their function or physical properties
- A61L24/0042—Materials resorbable by the body
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- 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
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- 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
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3819—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen
- C08G18/3821—Carboxylic acids; Esters thereof with monohydroxyl compounds
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- 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
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- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4244—Polycondensates having carboxylic or carbonic ester groups in the main chain containing oxygen in the form of ether groups
- C08G18/4247—Polycondensates having carboxylic or carbonic ester groups in the main chain containing oxygen in the form of ether groups derived from polyols containing at least one ether group and polycarboxylic acids
- C08G18/4252—Polycondensates having carboxylic or carbonic ester groups in the main chain containing oxygen in the form of ether groups derived from polyols containing at least one ether group and polycarboxylic acids derived from polyols containing polyether groups and polycarboxylic acids
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- 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
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- C08G18/46—Polycondensates having carboxylic or carbonic ester groups in the main chain having heteroatoms other than oxygen
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
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- C08G18/4833—Polyethers containing oxyethylene units
- C08G18/4837—Polyethers containing oxyethylene units and other oxyalkylene units
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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Claims (15)
1. Fremgangsmåde til fremstilling af en hydroxy-aminopolymer omfattende følgende trin: a) omsætning af en H-funktionel starterforbindelse, som bærer mindst ét Zerewitinoff-aktivt H-atom, med et umættet, cyklisk carboxylsyreanhydrid og mindst én alkylenoxidforbindelse til opnåelse af en præpolymer, som bærer hydroxylgrupper, b) addition af en primær amin og/eller ammoniak til dobbeltbindingen eller dobbeltbindingerne i den ifølge trin a) opnåede præpolymer, som bærer hydroxylgrupper, til opnåelse af hydroxy-aminopolymeren, hvor forholdet mellem de adderede aminogrupper og hydroxylgrupperne i hydroxy-aminopolymeren udgør mindst 0,6.
2. Fremgangsmåde ifølge krav 1, kendetegnet ved, at - forholdet mellem de adderede aminogrupper og hydroxylgrupperne i hydroxy-aminopolymeren udgør 0,8 til 2,5, og/eller at hydroxy-aminopolymeren udviser en OH-funktionalitet på 1,5 til 6, og/eller - at den H-funktionelle starterforbindelse har 1 til 35 Zerewitinoff-aktive H-atomer.
3. Fremgangsmåde ifølge krav 1 eller 2, kendetegnet ved, at det umættede, cykliske carboxylsyreanhydrid er valgt blandt umættede, cykliske dicarboxylsyreanhydrider, såsom maleinsyreanhydrid, tetrahydrophthalsyreanhydrid, navnlig 3,4,5,6-tetrahydrophthalsyreanhydrid, samt kombinationer deraf.
4. Fremgangsmåde ifølge et af de foregående krav, kendetegnet ved, at alkylenoxidforbindelsen er valgt blandt dem med 2 til 24 carbonatomer.
5. Fremgangsmåde ifølge et af de foregående krav, kendetegnet ved, at det molære forhold mellem alkylenoxidforbindelsen og carboxylsyreanhydridet udgør mindst 1:1.
6. Fremgangsmåde ifølge et af de foregående krav, kendetegnet ved, at den H-funktionelle starterforbindelse først omsættes med en første mængde af alky-lenoxidforbindelsen og dernæst med det umættede, cykliske carboxylsyreanhydrid og en yderligere mængde af alkylenoxidforbindelsen, hvor den H-funktionelle starterforbindelse fortrinsvis har en antalsgennemsnitsmolekylvægt på 17 til 1200 g/mol.
7. Fremgangsmåde ifølge et af de foregående krav, kendetegnet ved, at omsætningen af den H-funktionelle starterforbindelse med det umættede, cykliske carboxylsyreanhydrid og/eller additionen af alkylenoxidforbindelsen gennemføres ved brug afen dobbeltmetalcyanid-katalysator (DMC-katalysator).
8. Fremgangsmåde ifølge et af kravene 1 til 5, kendetegnet ved, at den H-funktionelle starterforbindelse først omsættes med det umættede, cykliske carboxylsyreanhydrid og dernæst med alkylenoxidforbindelsen, eller at den H-funktionelle starterforbindelse omsættes samtidigt med det umættede, cykliske carboxylsyreanhydrid og alkylenoxidforbindelsen, og/eller at fremgangsmåden gennemføres under anvendelse af en aminkatalysator.
9. Hydroxy-aminopolymer, som kan opnås ved en fremgangsmåde ifølge et af kravene 1 til 8, hvor hydroxy-aminopolymeren især omfatter polyesterpolyolenheder, polyester-polyether-polyolenheder og/eller polyetherpolyolenheder, fortrinsvis polyester-polyether-polyolenheder og/eller polyetherpolyolenheder med en andel af oxyethylenenheder på 40 til 90 vægt-%, hvor hydroxy-aminopolymeren fortrinsvis har den almene formel (I)
O), hvor ’’Starter” betegner radikalet af den H-funktionelle starterforbindelse, A betegner en aspartatgruppe med følgende struktur med formlen (Ila) eller (Mb)
(Ila) (Hb), hvor R1 betegner hydrogen eller en alifatisk, cykloalifatisk eller aromatisk gruppe, som også kan indeholde heteroatomer, især nitrogenatomer eller oxygenatomer, såvel som hydroxylgrupper, R2 og R3 uafhængigt af hinanden betegner hydrogen eller en alifatisk eller aromatisk gruppe, og R2 og R3 også kan udgøre en bestanddel af et cykloalifatisk ringsystem, R4, R5, R6 og R7 uafhængigt af hinanden betegner hydrogen eller en alifatisk eller aromatisk gruppe, og R5 og R6 også kan udgøre en bestanddel af et cykloalifatisk ringsystem, I angiver antallet af Zerewitinoff-aktive hydrogenatomer i den H-funktionelle starterforbindelse, m, n og o uafhængigt af hinanden er heltal, hvor n, o=0 eller > 1, og m > 1, og forholdet o til 1 i mediet er mindst 0,6, og hvor den ækvivalente molarmasse for den i formel I viste struktur ikke overstiger værdien 18900 g/mol.
10. Polyurea-polyurethan-system, der: som komponent A) omfatter isocyanatfunktionelle præpolymerer, der kan opnås ved omsætning af alifatiske og/eller aromatiske polyisocyanater A1) med polyoler A2), som komponent B) omfatter en hydroxy-aminopolymer ifølge krav 9, eventuelt som komponent C) omfatter organiske fyldstoffer, eventuelt som komponent D) omfatter produkter af omsætning af isocyanatfunktionelle præpolymerer ifølge komponent A) med hydroxy-amino-funktionelle forbindelser ifølge komponent B) og/eller organiske fyldstoffer ifølge komponent C), og eventuelt som komponent E) omfatter vand og/eller en tertiær amin.
11. Polyurea-polyurethan-system ifølge krav 10, kendetegnet ved, at der til fremstilling af komponent A) benyttes en trifunktionel polyol.
12. Polyurea-polyurethan-system ifølge krav 10 eller 11, kendetegnet ved, at komponent E) indeholder en tertiær amin med den almene formel (IX)
(IX) hvor R8, Rg og Rio uafhængigt af hinanden kan være alkyl- eller heteroalkylgrupper med heteroatomer i alkylkæden eller ved deres ender, eller R8 og R9 sammen med det nitrogenatom, der bærer dem, kan udgøre en alifatisk, umættet eller aromatisk heterocyklus, som potentielt kan indeholde yderligere heteroatomer.
13. Polyurea-polyurethan-system ifølge et af kravene 10 til 12, kendetegnet ved, at den tertiære amin er valgt fra gruppen bestående af triethanolamin, tetrakis-(2-hydroxyethyl)ethylendiamin, N,N-dimethyl-2-(4-methylpiperazin-1-yl)ethanamin, 2-{[2-(dimethylamino)ethyl](methyl)amino}ethanol, 3,3’,3”-(1,3,5-triazinan-1,3,5-triyl)tris(N,N-dimethyl-propan-1 -amin).
14. Polyurea-polyurethan-system ifølge et af kravene 10 til 13 til lukning, forbinding, klæbning eller dækning af cellevæv eller lukning af lækager i cellevæv.
15. Doseringssystem med to kamre til et polyurea-polyurethan-system ifølge et af kravene 10 til 13, kendetegnet ved, at komponenten A) er indeholdt i det ene kammer, og at komponenten B) og eventuelt komponenterne C), D) og E) af polyurea-polyurethan-systemet er indeholdt i det andet kammer.
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| EP11194417 | 2011-12-20 | ||
| PCT/EP2012/075825 WO2013092506A1 (de) | 2011-12-20 | 2012-12-17 | Hydroxy-aminopolymer und dessen verwendung in polyharnstoffpolyurethan-gewebeklebstoffen |
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| CN104387583B (zh) * | 2014-11-04 | 2016-08-24 | 中国林业科学研究院林产化学工业研究所 | 天冬氨酸氨基树脂及其制备方法和应用 |
| AU2016277798B2 (en) | 2015-06-18 | 2020-11-26 | Tissium Sa | Sealant composition |
| US11898005B2 (en) | 2015-06-18 | 2024-02-13 | Tissium Sa | Sealant composition |
| JP6913676B2 (ja) * | 2015-06-18 | 2021-08-04 | ティシウム ソシエテ アノニム | 接着剤組成物 |
| US10590069B2 (en) | 2017-10-06 | 2020-03-17 | International Business Machines Corporation | Pinene-derived diisocyanates |
| CN109134813A (zh) * | 2018-07-20 | 2019-01-04 | 成都上泰科技有限公司 | 一种聚脲树脂合成工艺 |
| WO2020023305A1 (en) * | 2018-07-24 | 2020-01-30 | Hexion Inc. | Novel compositions and methods to produce alkoxylated triazine-arylhydroxy-aldehyde condensates |
| EP3698723A1 (de) | 2019-02-20 | 2020-08-26 | Adhesys Medical GmbH | Applikator für einen zwei-komponenten gewebekleber |
| EP3875510A1 (de) * | 2020-03-03 | 2021-09-08 | Covestro Deutschland AG | Verfahren zur herstellung eines etheresterols |
| EP3885390A1 (de) * | 2020-03-25 | 2021-09-29 | Covestro Deutschland AG | Verfahren zur herstellung eines etheresterols |
| EP4104870A1 (de) * | 2021-06-15 | 2022-12-21 | Adhesys Medical GmbH | Gewebekleber in form eines zweikomponenten-klebstoffs zur verwendung als bakterielle barriere bei der wundbehandlung, insbesondere nach chirurgischen eingriffen |
| CN113952501A (zh) * | 2021-09-22 | 2022-01-21 | 华南理工大学 | 一种用于肺部创伤修复的医用粘合剂及其使用方法 |
| CN113969096B (zh) * | 2021-11-29 | 2022-07-05 | 四川大学 | 高强室温自修复聚脲涂层材料及制备方法 |
| JP7092251B1 (ja) * | 2021-11-30 | 2022-06-28 | 東洋インキScホールディングス株式会社 | 皮膚貼付用粘着剤及び皮膚貼付用粘着テープ |
| CN119285924B (zh) * | 2024-12-11 | 2025-12-30 | 山东一诺威新材料有限公司 | 烟酸改性吡哆胺聚醚多元醇及其制备方法 |
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| EP1645581A1 (de) | 2004-10-07 | 2006-04-12 | Cytec Surface Specialties Austria GmbH | Polyurethanharze mit Säuregruppen |
| JP4928332B2 (ja) | 2007-04-12 | 2012-05-09 | トヨタホーム株式会社 | 洗面台 |
| JP5207859B2 (ja) | 2007-07-19 | 2013-06-12 | クラレノリタケデンタル株式会社 | 重合性組成物及び歯科用材料 |
| EP2083025A1 (de) * | 2008-01-24 | 2009-07-29 | Bayer MaterialScience AG | Medizinische Klebstoffe für die Chirurgie |
| EP2095832A1 (de) | 2008-02-28 | 2009-09-02 | Bayer MaterialScience AG | Polyharnstoff-Systeme und deren Anwendung als postoperative Adhäsionsbarrieren, Filme und Verbundteile. |
| JP5369461B2 (ja) | 2008-03-21 | 2013-12-18 | 東洋インキScホールディングス株式会社 | 感圧式接着剤組成物、それを用いてなる感圧式接着シート、及び積層体 |
| JP2012511597A (ja) | 2008-12-12 | 2012-05-24 | バイエル・マテリアルサイエンス・アクチェンゲゼルシャフト | 手術用医療接着剤 |
| JP5566713B2 (ja) | 2009-02-05 | 2014-08-06 | 富士フイルム株式会社 | レーザー彫刻用レリーフ印刷版原版、レリーフ印刷版及びレリーフ印刷版の製造方法 |
| JP4582268B1 (ja) | 2009-03-30 | 2010-11-17 | コニカミノルタオプト株式会社 | 固体撮像装置 |
| DE102009031584A1 (de) | 2009-07-03 | 2011-01-05 | Bayer Materialscience Ag | Verfahren zur Herstellung von Polyetherpolyolen mit primären Hydroxyl-Endgruppen |
| EP2275466A1 (de) * | 2009-07-16 | 2011-01-19 | Bayer MaterialScience AG | Polyharnstoff-basierter Gewebekleber |
| PL2571922T3 (pl) | 2010-05-18 | 2014-11-28 | Bayer Ip Gmbh | Sposób wytwarzania polioli polieterowęglanowych |
| EP2395039A1 (de) | 2010-05-21 | 2011-12-14 | Basf Se | Polymeres Flammschutzmittel |
| CA2859566A1 (en) | 2011-12-20 | 2013-06-27 | Bayer Intellectual Property Gmbh | Hydroxy-aminopolymers and method for producing same |
-
2012
- 2012-12-17 JP JP2014547899A patent/JP5873931B2/ja not_active Expired - Fee Related
- 2012-12-17 CN CN201280063350.1A patent/CN104144999B/zh not_active Expired - Fee Related
- 2012-12-17 EP EP12809752.4A patent/EP2794798B1/de not_active Not-in-force
- 2012-12-17 WO PCT/EP2012/075825 patent/WO2013092506A1/de not_active Ceased
- 2012-12-17 ES ES12809752.4T patent/ES2560031T3/es active Active
- 2012-12-17 DK DK12809752.4T patent/DK2794798T3/da active
- 2012-12-17 US US14/365,233 patent/US9580540B2/en not_active Expired - Fee Related
-
2017
- 2017-01-10 US US15/402,702 patent/US9757492B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US9757492B2 (en) | 2017-09-12 |
| US20170119921A1 (en) | 2017-05-04 |
| JP2015509117A (ja) | 2015-03-26 |
| US20140341835A1 (en) | 2014-11-20 |
| CN104144999B (zh) | 2016-08-17 |
| JP5873931B2 (ja) | 2016-03-01 |
| HK1201550A1 (zh) | 2015-09-04 |
| WO2013092506A1 (de) | 2013-06-27 |
| ES2560031T3 (es) | 2016-02-17 |
| US9580540B2 (en) | 2017-02-28 |
| CN104144999A (zh) | 2014-11-12 |
| EP2794798B1 (de) | 2015-11-25 |
| EP2794798A1 (de) | 2014-10-29 |
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