TW200948839A - Adhesive systems containing polyisocyanate prepolymers and aspartate-ester curing agents, processes for preparing the same, medical uses therefor and dispensing systems for the same - Google Patents
Adhesive systems containing polyisocyanate prepolymers and aspartate-ester curing agents, processes for preparing the same, medical uses therefor and dispensing systems for the same Download PDFInfo
- Publication number
- TW200948839A TW200948839A TW098102729A TW98102729A TW200948839A TW 200948839 A TW200948839 A TW 200948839A TW 098102729 A TW098102729 A TW 098102729A TW 98102729 A TW98102729 A TW 98102729A TW 200948839 A TW200948839 A TW 200948839A
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- Taiwan
- Prior art keywords
- group
- isocyanate
- adhesive
- tissue
- prepolymer
- Prior art date
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- 230000001070 adhesive effect Effects 0.000 title claims abstract description 32
- 238000000034 method Methods 0.000 title claims description 14
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- 239000000227 bioadhesive Substances 0.000 description 1
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- 210000000988 bone and bone Anatomy 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- BNMJSBUIDQYHIN-UHFFFAOYSA-N butyl dihydrogen phosphate Chemical compound CCCCOP(O)(O)=O BNMJSBUIDQYHIN-UHFFFAOYSA-N 0.000 description 1
- CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 description 1
- 229960005286 carbaryl Drugs 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
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- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical compound OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 description 1
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 1
- 231100000433 cytotoxic Toxicity 0.000 description 1
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- 150000001983 dialkylethers Chemical class 0.000 description 1
- JBSLOWBPDRZSMB-FPLPWBNLSA-N dibutyl (z)-but-2-enedioate Chemical compound CCCCOC(=O)\C=C/C(=O)OCCCC JBSLOWBPDRZSMB-FPLPWBNLSA-N 0.000 description 1
- 229940028820 didecyl ether Drugs 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- JJJFUHOGVZWXNQ-UHFFFAOYSA-N enbucrilate Chemical compound CCCCOC(=O)C(=C)C#N JJJFUHOGVZWXNQ-UHFFFAOYSA-N 0.000 description 1
- 229950010048 enbucrilate Drugs 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 210000000981 epithelium Anatomy 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 1
- 235000019414 erythritol Nutrition 0.000 description 1
- 229940009714 erythritol Drugs 0.000 description 1
- DKQVJMREABFYNT-UHFFFAOYSA-N ethene Chemical group C=C.C=C DKQVJMREABFYNT-UHFFFAOYSA-N 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 239000001087 glyceryl triacetate Substances 0.000 description 1
- 235000013773 glyceryl triacetate Nutrition 0.000 description 1
- XEOCKQIQXJNTER-UHFFFAOYSA-N gold palladium platinum Chemical class [Pd].[Pd].[Pd].[Pd].[Pd].[Pt].[Pt].[Pt].[Pt].[Pt].[Pt].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au].[Au] XEOCKQIQXJNTER-UHFFFAOYSA-N 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 210000005260 human cell Anatomy 0.000 description 1
- VBUWEHVLAKVFHY-UHFFFAOYSA-N hydrazine [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound NN.C(O)C1(CCCCC1)CO VBUWEHVLAKVFHY-UHFFFAOYSA-N 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- OAOABCKPVCUNKO-UHFFFAOYSA-N isodecanoic acid Natural products CC(C)CCCCCCC(O)=O OAOABCKPVCUNKO-UHFFFAOYSA-N 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical compound COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000002107 myocardial effect Effects 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000000399 orthopedic effect Effects 0.000 description 1
- HXSACZWWBYWLIS-UHFFFAOYSA-N oxadiazine-4,5,6-trione Chemical class O=C1ON=NC(=O)C1=O HXSACZWWBYWLIS-UHFFFAOYSA-N 0.000 description 1
- 125000003544 oxime group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- WTSXICLFTPPDTL-UHFFFAOYSA-N pentane-1,3-diamine Chemical compound CCC(N)CCN WTSXICLFTPPDTL-UHFFFAOYSA-N 0.000 description 1
- GPCKFIWBUTWTDH-UHFFFAOYSA-N pentane-3,3-diamine Chemical compound CCC(N)(N)CC GPCKFIWBUTWTDH-UHFFFAOYSA-N 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 108010064470 polyaspartate Proteins 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 235000015277 pork Nutrition 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- ZUFQCVZBBNZMKD-UHFFFAOYSA-M potassium 2-ethylhexanoate Chemical compound [K+].CCCCC(CC)C([O-])=O ZUFQCVZBBNZMKD-UHFFFAOYSA-M 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- ZNZJJSYHZBXQSM-UHFFFAOYSA-N propane-2,2-diamine Chemical compound CC(C)(N)N ZNZJJSYHZBXQSM-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 231100000241 scar Toxicity 0.000 description 1
- 230000037387 scars Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 201000010153 skin papilloma Diseases 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000003894 surgical glue Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- FINHMKGKINIASC-UHFFFAOYSA-N tetramethyl-pyrazine Natural products CC1=NC(C)=C(C)N=C1C FINHMKGKINIASC-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- 150000003628 tricarboxylic acids Chemical class 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
- 235000013618 yogurt Nutrition 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-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
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4833—Polyethers containing oxyethylene units
- C08G18/4837—Polyethers containing oxyethylene units and other oxyalkylene units
-
- 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
- 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
-
- 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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/73—Polyisocyanates or polyisothiocyanates acyclic
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Surgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Materials For Medical Uses (AREA)
- Polyurethanes Or Polyureas (AREA)
- Adhesives Or Adhesive Processes (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08001290A EP2083025A1 (de) | 2008-01-24 | 2008-01-24 | Medizinische Klebstoffe für die Chirurgie |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW200948839A true TW200948839A (en) | 2009-12-01 |
Family
ID=39577927
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW098102729A TW200948839A (en) | 2008-01-24 | 2009-01-23 | Adhesive systems containing polyisocyanate prepolymers and aspartate-ester curing agents, processes for preparing the same, medical uses therefor and dispensing systems for the same |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US20090191145A1 (https=) |
| EP (2) | EP2083025A1 (https=) |
| JP (1) | JP2011511857A (https=) |
| KR (1) | KR20100117573A (https=) |
| CN (1) | CN101925625B (https=) |
| AU (1) | AU2009207883A1 (https=) |
| BR (1) | BRPI0906578A2 (https=) |
| CA (1) | CA2712648A1 (https=) |
| ES (1) | ES2396020T3 (https=) |
| TW (1) | TW200948839A (https=) |
| WO (1) | WO2009092524A1 (https=) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2011808A1 (de) * | 2007-07-03 | 2009-01-07 | 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. |
| WO2010030544A1 (en) * | 2008-09-12 | 2010-03-18 | Dow Global Technologies Inc. | Coating formulations and compositions based on polyamines, polyols and polyisocyanates, and processes of preparing and of using the same |
| EP2336212B1 (de) * | 2009-12-12 | 2012-03-07 | Bayer MaterialScience AG | Klebstoffverbundsystem zum Abdecken, Verschliessen oder Verkleben von Zellgewebe |
| DE102010019504A1 (de) * | 2010-05-06 | 2011-11-10 | Bayer Materialscience Ag | Polyisocyanatprepolymere und deren Verwendung |
| PL2673311T3 (pl) * | 2011-02-09 | 2015-02-27 | Bayer Materialscience Ag | Kleje tkankowe na bazie trójfunkcjonalnych asparginianów |
| WO2012107375A1 (de) * | 2011-02-09 | 2012-08-16 | Bayer Materialscience Ag | Gewebekleber auf basis stickstoffmodifizierter aspartate |
| EP2543395A1 (de) * | 2011-07-04 | 2013-01-09 | Bayer MaterialScience AG | Schichtaufbau zum Verschließen von Gewebeleckagen |
| JP5873931B2 (ja) * | 2011-12-20 | 2016-03-01 | メディカル・アドヒーシブ・レボリューション・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＭｅｄｉｃａｌ Ａｄｈｅｓｉｖｅ Ｒｅｖｏｌｕｔｉｏｎ ＧｍｂＨ | ヒドロキシアミノポリマーおよびポリ尿素／ポリウレタン組織接着剤におけるその使用 |
| ES2694826T3 (es) * | 2011-12-20 | 2018-12-27 | Adhesys Medical Gmbh | Prepolímero con funcionalidad isocianato para un adhesivo de tejidos biodegradable |
| ES2576702T3 (es) * | 2012-01-09 | 2016-07-08 | Adhesys Medical Gmbh | Agentes de curado (a base de aspartato) modificados por ésteres de beta-aminoácido y su uso en adhesivos de tejido de poliurea |
| EP2695900B1 (en) * | 2012-08-06 | 2019-03-20 | Novachem Industriale S.r.l. | Process for preparing a two-component polyurethane adhesive system |
| EP3456706A1 (de) | 2017-09-19 | 2019-03-20 | Covestro Deutschland AG | Polyasparaginsäureester-zusammensetzungen und verfahren zur reinigung |
| EP4410322A1 (en) * | 2023-02-02 | 2024-08-07 | Covestro Deutschland AG | Method of manufacturing a hydrogel useful for preventing post-surgical adhesions |
| EP4637853A1 (en) * | 2022-12-20 | 2025-10-29 | Covestro Deutschland AG | Method of manufacturing a hydrogel useful for preventing post-surgical adhesions |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4477604A (en) * | 1982-09-20 | 1984-10-16 | Oechsle Iii Sixtus J | Polyurethane compositions and their use as luting agents |
| US4804614A (en) * | 1984-10-01 | 1989-02-14 | The Aerospace Corporation | Photoresist process of fabricating microelectronic circuits using water processable diazonium compound containing contrast enhancement layer |
| US4740534A (en) | 1985-08-30 | 1988-04-26 | Sanyo Chemical Industries, Ltd. | Surgical adhesive |
| JPH04150866A (ja) | 1990-10-15 | 1992-05-25 | Nisshinbo Ind Inc | 外科用接着剤 |
| JP2928892B2 (ja) | 1990-11-27 | 1999-08-03 | 三洋化成工業株式会社 | 外科用接着剤 |
| US5156613A (en) | 1991-02-13 | 1992-10-20 | Interface Biomedical Laboratories Corp. | Collagen welding rod material for use in tissue welding |
| US5243012A (en) | 1992-06-10 | 1993-09-07 | Miles Inc. | Polyurea coating compositions having improved pot lives |
| US6017577A (en) | 1995-02-01 | 2000-01-25 | Schneider (Usa) Inc. | Slippery, tenaciously adhering hydrophilic polyurethane hydrogel coatings, coated polymer substrate materials, and coated medical devices |
| US6123667A (en) | 1997-03-20 | 2000-09-26 | Focal, Inc. | Retracting tissue using photoadhering adhesive |
| US6355829B2 (en) | 1999-09-02 | 2002-03-12 | Bayer Corporation | Aspartate-terminated urea/urethane prepolymers and their use in coating compositions |
| US6296607B1 (en) * | 2000-10-20 | 2001-10-02 | Praxis, Llc. | In situ bulking device |
| JP4383859B2 (ja) * | 2001-07-18 | 2009-12-16 | エヌイーシー ショット コンポーネンツ株式会社 | 温度ヒューズ |
| US8501165B2 (en) | 2001-12-12 | 2013-08-06 | Promethean Surgical Devices Llc | In situ bonds |
| US6747117B2 (en) * | 2002-06-14 | 2004-06-08 | Crompton Corporation | Polyurethane/urea composition for coating cylindrical parts |
| DE10246708A1 (de) * | 2002-10-07 | 2004-04-15 | Bayer Ag | Zweikomponenten-Systeme für die Herstellung elastischer Beschichtungen |
| US20050129733A1 (en) | 2003-12-09 | 2005-06-16 | Milbocker Michael T. | Surgical adhesive and uses therefore |
| GB2415645A (en) * | 2004-06-28 | 2006-01-04 | L & I Maritime Ltd | Cargo tank coating |
| US8044234B2 (en) * | 2005-05-05 | 2011-10-25 | Tyco Healthcare Group Lp | Bioabsorbable surgical composition |
| WO2007067761A2 (en) * | 2005-12-08 | 2007-06-14 | Tyco Healthcare Group Lp | Viscosity-reduced sprayable compositions |
| EP2011808A1 (de) * | 2007-07-03 | 2009-01-07 | Bayer MaterialScience AG | Medizinische Klebstoffe für die Chirurgie |
-
2008
- 2008-01-24 EP EP08001290A patent/EP2083025A1/de not_active Withdrawn
-
2009
- 2009-01-13 KR KR1020107016540A patent/KR20100117573A/ko not_active Withdrawn
- 2009-01-13 CN CN2009801028285A patent/CN101925625B/zh not_active Expired - Fee Related
- 2009-01-13 ES ES09703443T patent/ES2396020T3/es active Active
- 2009-01-13 CA CA2712648A patent/CA2712648A1/en not_active Abandoned
- 2009-01-13 EP EP09703443A patent/EP2245078B1/de not_active Not-in-force
- 2009-01-13 BR BRPI0906578-4A patent/BRPI0906578A2/pt not_active IP Right Cessation
- 2009-01-13 WO PCT/EP2009/000129 patent/WO2009092524A1/de not_active Ceased
- 2009-01-13 JP JP2010543413A patent/JP2011511857A/ja not_active Withdrawn
- 2009-01-13 AU AU2009207883A patent/AU2009207883A1/en not_active Abandoned
- 2009-01-23 US US12/358,346 patent/US20090191145A1/en not_active Abandoned
- 2009-01-23 TW TW098102729A patent/TW200948839A/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP2245078B1 (de) | 2012-10-24 |
| US20090191145A1 (en) | 2009-07-30 |
| EP2245078A1 (de) | 2010-11-03 |
| CN101925625B (zh) | 2012-12-05 |
| ES2396020T3 (es) | 2013-02-18 |
| WO2009092524A1 (de) | 2009-07-30 |
| AU2009207883A1 (en) | 2009-07-30 |
| CN101925625A (zh) | 2010-12-22 |
| KR20100117573A (ko) | 2010-11-03 |
| CA2712648A1 (en) | 2009-07-30 |
| JP2011511857A (ja) | 2011-04-14 |
| EP2083025A1 (de) | 2009-07-29 |
| BRPI0906578A2 (pt) | 2015-07-07 |
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