DK2794798T3 - Hydroxy-aminopolymer og anvendelse deraf i poly-urea/polyurethan-vævsklæbemidler - Google Patents

Hydroxy-aminopolymer og anvendelse deraf i poly-urea/polyurethan-vævsklæbemidler Download PDF

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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
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alkylene oxide
component
compound
functional
hydroxy
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Heike Heckroth
Christoph Eggert
Jörg Hofmann
Klaus Lorenz
Edward Browne
Hartmut Nefzger
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Medical Adhesive Revolution Gmbh
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61LMETHODS 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
    • A61L24/00Surgical adhesives or cements; Adhesives for colostomy devices
    • A61L24/04Surgical adhesives or cements; Adhesives for colostomy devices containing macromolecular materials
    • A61L24/046Surgical adhesives or cements; Adhesives for colostomy devices containing macromolecular materials obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61LMETHODS 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
    • A61L24/00Surgical adhesives or cements; Adhesives for colostomy devices
    • A61L24/001Use of materials characterised by their function or physical properties
    • A61L24/0042Materials resorbable by the body
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    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08Processes
    • C08G18/10Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
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    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30Low-molecular-weight compounds
    • C08G18/38Low-molecular-weight compounds having heteroatoms other than oxygen
    • C08G18/3819Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen
    • C08G18/3821Carboxylic acids; Esters thereof with monohydroxyl compounds
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    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40High-molecular-weight compounds
    • C08G18/42Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C08G18/4244Polycondensates having carboxylic or carbonic ester groups in the main chain containing oxygen in the form of ether groups
    • C08G18/4247Polycondensates 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
    • C08G18/4252Polycondensates 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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    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40High-molecular-weight compounds
    • C08G18/42Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C08G18/46Polycondensates having carboxylic or carbonic ester groups in the main chain having heteroatoms other than oxygen
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    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40High-molecular-weight compounds
    • C08G18/48Polyethers
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    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40High-molecular-weight compounds
    • C08G18/48Polyethers
    • C08G18/4833Polyethers containing oxyethylene units
    • C08G18/4837Polyethers containing oxyethylene units and other oxyalkylene units
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    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40High-molecular-weight compounds
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    • C08G18/4866Polyethers having a low unsaturation value
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    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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    • C08G18/40High-molecular-weight compounds
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    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72Polyisocyanates or polyisothiocyanates
    • C08G18/73Polyisocyanates or polyisothiocyanates acyclic
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    • C08G63/91Polymers modified by chemical after-treatment
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    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J175/00Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04Polyurethanes
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    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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  • Polymers & Plastics (AREA)
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  • General Chemical & Material Sciences (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Polyethers (AREA)
  • Materials For Medical Uses (AREA)
  • Polyesters Or Polycarbonates (AREA)
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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.
DK12809752.4T 2011-12-20 2012-12-17 Hydroxy-aminopolymer og anvendelse deraf i poly-urea/polyurethan-vævsklæbemidler DK2794798T3 (da)

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PCT/EP2012/075825 WO2013092506A1 (de) 2011-12-20 2012-12-17 Hydroxy-aminopolymer und dessen verwendung in polyharnstoffpolyurethan-gewebeklebstoffen

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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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