WO2000035982A1 - Adhesif polyester-polyurethanne et son utilisation - Google Patents
Adhesif polyester-polyurethanne et son utilisation Download PDFInfo
- Publication number
- WO2000035982A1 WO2000035982A1 PCT/EP1999/009623 EP9909623W WO0035982A1 WO 2000035982 A1 WO2000035982 A1 WO 2000035982A1 EP 9909623 W EP9909623 W EP 9909623W WO 0035982 A1 WO0035982 A1 WO 0035982A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- polyester
- polyurethane adhesive
- lactic acid
- polyester polyol
- polyols
- Prior art date
Links
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
- C08G18/42—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
- C08G18/428—Lactides
-
- 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
- C09J175/06—Polyurethanes from polyesters
Definitions
- the invention relates to a polyurethane adhesive made from polyester polyols and polyisocyanates.
- Polyurethane adhesives based on polyester polyols and polyisocyanates have been known for a long time.
- Lactic acid-based diols have also been known for at least 10 years.
- EP 0 250 994 describes their manufacture, e.g. described from ethylene glycol and lactic acid.
- the flowable to solid oligomeric esters of lactic acid or their dermatologically compatible derivatives as resorbable carriers and / or film formers for the production of a cosmetic or pharmaceutical agent for covering undamaged and / or injured areas of human or animal skin.
- Esters are mentioned as derivatives.
- polyester diols not of a petrochemical nature, but on the basis of renewable raw materials, in particular vegetable-based, for the production of polyurethane adhesives and the polyurethane adhesives produced therefrom.
- appropriate use should also be found.
- the solution of the invention can be found in the patent claims. It consists primarily of using as polyester polyol a polyester polyol based on hydroxycarboxylic acids with 2 to 5 carbon atoms, in particular based on lactic acid, for the production of the polyurethane adhesive.
- Lactic acid is technically used in extraction and fermentation processes in lactic acid fermentation, e.g. of milk and whey or of glucose and maltose made from molasses and malt on a large scale.
- the main product is corn.
- the polylactic acid (polylactide) is produced from the lactic acid or its derivatives by polymerization. This can e.g. by direct esterification with at least dihydric alcohols, by transesterification of lactic acid esters or by ring opening of lactide.
- the polylactic acid having a plurality of OH groups is preferably produced simultaneously or thereafter from the lactic acid by reaction with suitable low molecular weight polyols. Suitable low molecular weight polyols are e.g.
- Ethylene glycol propane diol-1, 2, propanediol-1, 3, butanediol-1, 3, butanediol-1, 4, butanediol-2,3, neopentyl glycol, hexanediol-1, 6, hydroquinone, resorcinol and polyhydric alcohols , especially glycerin and monoglycerides.
- low molecular weight polyalkylene diols or triols can also be used, e.g. Tripropylene glycol.
- the molecular weight of polylactic acid with several OH groups is determined by the molar ratio of lactic acid to the low molecular weight polyol.
- Polyester diols based on lactic acid are preferred, in particular oligomers based on lactic acid with two OH end groups.
- hydroxycarboxylic acids which can be used according to the invention are: glycolic acid, hydroxybutyric acid and hydroxyvaleric acid.
- the polyester polyols based on hydroxycarboxylic acids with 2 to 5 carbon atoms, in particular lactic acid with two or more OH end groups serve as the starting material for the production of polyurethanes in reaction with polyisocyanates.
- they can also be used to manufacture other synthetic resins.
- the polyurethanes can be made from one or several polyester polyols and one or more polyisocyanates are produced.
- a “polyisocyanate” is understood to mean a low molecular weight compound with two or more isocyanate groups.
- the diisocyanates are preferred. However, they can contain up to about 10% by weight of trifunctional isocyanates.
- aromatic polyisocyanates are particularly preferred TDI and MDI may be mentioned as specific examples.
- polyester polyurethanes In the case of polyester polyurethanes, a distinction can be made between whether a still reactive or a non-reactive composition is to be applied.
- the reactive mass can in turn be differentiated between a polyester polyurethane with reactive NCO groups that react with water vapor (one-component system) and a system in which a polyester polyol (resin) is used immediately before application Polyisocyanate (hardener) is mixed (two-component system).
- the polyester polyurethanes according to the invention made from the polyester polyols based on lactic acid are suitable for practically all applications which are known for all types of previously known polyester polyurethanes. We expressly refer to the use for gluing, coating and sealing (including casting compounds).
- the polyester polyurethanes according to the invention are particularly suitable for gluing. In principle, all known bonding of substrates is also possible here. However, the use for lamination in the form of a two-component system should be emphasized.
- Laminating is the binding of two or more layers of the same or different materials. These are papers, textiles, plastics, metals and other materials that can be processed as layers or foils. These materials are usually combined in a calender in a rolling process under pressure with the polyester polyurethane according to the invention. Despite the low viscosity, the polyester polyurethanes according to the invention based on polyester polyols made from lactic acid showed surprisingly high strength values and are therefore particularly suitable for laminating. They are environmentally friendly, not only because they are made from renewable raw materials, but also because they are biodegradable.
- This reaction product was used as a resin in a ratio of 1: 1, 2 with MDI as a hardener for laminating a 12 ⁇ m thick stretched film made of polypropylene and a 50 ⁇ m thick film made of polyethylene.
- the adhesive application was 3 ⁇ m.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BR9916168-0A BR9916168A (pt) | 1998-12-17 | 1999-12-08 | Adesivo de poliéster-poliuretana e seu emprego |
EP99966927A EP1153055A1 (fr) | 1998-12-17 | 1999-12-08 | Adhesif polyester-polyurethanne et son utilisation |
NO20012973A NO20012973D0 (no) | 1998-12-17 | 2001-06-15 | Polyester-polyuretanlim og anvendelsen derav |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19858240 | 1998-12-17 | ||
DE19858240.4 | 1998-12-17 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2000035982A1 true WO2000035982A1 (fr) | 2000-06-22 |
Family
ID=7891410
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1999/009623 WO2000035982A1 (fr) | 1998-12-17 | 1999-12-08 | Adhesif polyester-polyurethanne et son utilisation |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP1153055A1 (fr) |
BR (1) | BR9916168A (fr) |
DE (1) | DE19958526A1 (fr) |
NO (1) | NO20012973D0 (fr) |
WO (1) | WO2000035982A1 (fr) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101899139A (zh) * | 2010-07-23 | 2010-12-01 | 同济大学 | 一种聚乳酸基高弹性共聚物的制备方法 |
EP2781532A1 (fr) | 2013-03-22 | 2014-09-24 | Novamelt GmbH Klebstofftechnologie | Composition, procédé de fabrication et utilisation d'un adhésif à base de polylactide modifié |
US8999503B2 (en) | 2009-10-20 | 2015-04-07 | Nitto Denko Corporation | Thermally removable pressure-sensitive adhesive sheet |
WO2017003872A1 (fr) * | 2015-07-01 | 2017-01-05 | H.B. Fuller Company | Composition adhésive à base de polyols de polylactide |
WO2017003875A1 (fr) * | 2015-07-01 | 2017-01-05 | H.B. Fuller Company | Composition adhésive durcissable à l'humidité à base de polylactide polyols |
CN114886840A (zh) * | 2020-07-10 | 2022-08-12 | 南京海鲸药业有限公司 | 一种具有酸敏感降解、温敏性质的系列聚合物及其载药组合物 |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102006006904A1 (de) * | 2006-02-09 | 2007-08-23 | Universität Rostock | Neue Mittel zur Blutstillung und Klebstoffe für medizinische Anwendungen |
DE102006048833A1 (de) | 2006-10-16 | 2008-04-17 | Universität Rostock | Behandlung von Osteoporose |
DE102007061506A1 (de) * | 2007-12-18 | 2009-06-25 | Henkel Ag & Co. Kgaa | Biologisch abbaubarer Klebstoff |
EP2098579B1 (fr) | 2008-02-27 | 2010-07-28 | Sika Technology AG | Colle de revêtement destinée au déformage à haute température |
DE102014209019A1 (de) * | 2014-05-13 | 2015-11-19 | Henkel Ag & Co. Kgaa | Bindemittel-System mit schnellerer Aushärtung |
WO2016097002A1 (fr) | 2014-12-17 | 2016-06-23 | Purac Biochem Bv | Substrats revêtus ou liés au moyen d'une composition comprenant un polyuréthanne |
EP3034534A1 (fr) | 2014-12-17 | 2016-06-22 | PURAC Biochem BV | Substrats revêtus ou liés avec une composition comprenant un polyuréthane |
DE102018214839B4 (de) | 2018-08-31 | 2021-05-12 | Kufner Holding Gmbh | Heißsiegelbares, textiles Flächengebilde mit nachhaltiger Klebstoffbeschichtung und seine Verwendung |
JP6881647B1 (ja) * | 2020-04-17 | 2021-06-02 | 東洋インキScホールディングス株式会社 | 粘着剤組成物および粘着シート |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4804691A (en) * | 1987-08-28 | 1989-02-14 | Richards Medical Company | Method for making a biodegradable adhesive for soft living tissue |
JPH03182584A (ja) * | 1989-12-12 | 1991-08-08 | Dainichiseika Color & Chem Mfg Co Ltd | 2液硬化型接着剤組成物 |
DE4225045A1 (de) * | 1992-07-29 | 1994-02-03 | Basf Ag | Verwendung von wasserlöslichen oder in Wasser dispergierbaren Polyurethanen als Hilfsmittel in kosmetischen und pharmazeutischen Zubereitungen und Polyurethane, die Polymilchsäurepolyole einpolymerisiert enthalten |
US5574130A (en) * | 1993-05-11 | 1996-11-12 | Basf Aktiengesellschaft | Functionalized polylactide |
-
1999
- 1999-12-04 DE DE19958526A patent/DE19958526A1/de not_active Withdrawn
- 1999-12-08 WO PCT/EP1999/009623 patent/WO2000035982A1/fr not_active Application Discontinuation
- 1999-12-08 EP EP99966927A patent/EP1153055A1/fr not_active Withdrawn
- 1999-12-08 BR BR9916168-0A patent/BR9916168A/pt not_active Application Discontinuation
-
2001
- 2001-06-15 NO NO20012973A patent/NO20012973D0/no unknown
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4804691A (en) * | 1987-08-28 | 1989-02-14 | Richards Medical Company | Method for making a biodegradable adhesive for soft living tissue |
JPH03182584A (ja) * | 1989-12-12 | 1991-08-08 | Dainichiseika Color & Chem Mfg Co Ltd | 2液硬化型接着剤組成物 |
DE4225045A1 (de) * | 1992-07-29 | 1994-02-03 | Basf Ag | Verwendung von wasserlöslichen oder in Wasser dispergierbaren Polyurethanen als Hilfsmittel in kosmetischen und pharmazeutischen Zubereitungen und Polyurethane, die Polymilchsäurepolyole einpolymerisiert enthalten |
US5574130A (en) * | 1993-05-11 | 1996-11-12 | Basf Aktiengesellschaft | Functionalized polylactide |
Non-Patent Citations (1)
Title |
---|
CHEMICAL ABSTRACTS, vol. 116, no. 4, 27 January 1992, Columbus, Ohio, US; abstract no. 22574f, XP000282433 * |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8999503B2 (en) | 2009-10-20 | 2015-04-07 | Nitto Denko Corporation | Thermally removable pressure-sensitive adhesive sheet |
CN101899139A (zh) * | 2010-07-23 | 2010-12-01 | 同济大学 | 一种聚乳酸基高弹性共聚物的制备方法 |
EP2781532A1 (fr) | 2013-03-22 | 2014-09-24 | Novamelt GmbH Klebstofftechnologie | Composition, procédé de fabrication et utilisation d'un adhésif à base de polylactide modifié |
DE102013205144A1 (de) | 2013-03-22 | 2014-09-25 | Novamelt GmbH Klebstofftechnologie | Klebstoffzusammensetzung auf Basis von gegebenenfalls modifiziertem Polylactid, Verfahren zu deren Herstellung sowie Verwendung der Klebstoffzusammensetzung |
WO2017003872A1 (fr) * | 2015-07-01 | 2017-01-05 | H.B. Fuller Company | Composition adhésive à base de polyols de polylactide |
WO2017003875A1 (fr) * | 2015-07-01 | 2017-01-05 | H.B. Fuller Company | Composition adhésive durcissable à l'humidité à base de polylactide polyols |
CN114886840A (zh) * | 2020-07-10 | 2022-08-12 | 南京海鲸药业有限公司 | 一种具有酸敏感降解、温敏性质的系列聚合物及其载药组合物 |
CN114886840B (zh) * | 2020-07-10 | 2023-08-25 | 南京海鲸药业股份有限公司 | 一种具有酸敏感降解、温敏性质的系列聚合物及其载药组合物 |
Also Published As
Publication number | Publication date |
---|---|
BR9916168A (pt) | 2001-09-04 |
DE19958526A1 (de) | 2000-06-21 |
NO20012973L (no) | 2001-06-15 |
EP1153055A1 (fr) | 2001-11-14 |
NO20012973D0 (no) | 2001-06-15 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP2089450B1 (fr) | Adhésif en polyuréthanne pour stratification | |
WO2000035982A1 (fr) | Adhesif polyester-polyurethanne et son utilisation | |
WO2018095962A1 (fr) | Composition d'adhésif de contrecollage à faible viscosité et durcissement rapide | |
EP3265501B1 (fr) | Colles pauvres en voc et ayant des valeurs d'embuage réduites | |
EP3327056B1 (fr) | Composition de colle de contrecollage peu visqueuse, durcissant rapidement | |
DE1961770A1 (de) | Polyurethan-Klebstoff | |
EP0777695A1 (fr) | Compositions de polyurethanne a faible teneur en diisocyanates monomeres | |
EP3257882A1 (fr) | Substance adhésive biodégradable | |
EP3265532A1 (fr) | Adhésifs à faibles valeurs de cov et de condensation | |
WO2010066525A1 (fr) | Adhésifs pu pour films composites stérilisables | |
DE4103347A1 (de) | Waessrige polyurethan-dispersionen und ihre verwendung als kaschierklebstoffe | |
EP2877507A1 (fr) | Formulations d'adhésif | |
EP0448825A2 (fr) | Procédé pour un adhésif de fusion | |
WO2014206779A1 (fr) | Adhésif polyuréthane hydrophobe | |
EP1189961B1 (fr) | Utilisation de une composition de polyurethane a faible teneur en momomere comme auto-adhesive | |
WO2019043054A1 (fr) | Adhésif réactif pourvu ayant une faible teneur en diisocyanate monomère | |
WO2018210568A1 (fr) | Système de liant à base de polyuréthane | |
EP0894122A1 (fr) | Adhesif compostable | |
EP0176726B1 (fr) | Utilisation de solutions de polyisocyanates et d'oligouréthanes contenant des groupes hydroxyliques comme matières adhésives pour produits stratifiés à base de feuilles | |
EP2781532B1 (fr) | Composition, procédé de fabrication et utilisation d'un adhésif à base de polylactide modifié | |
WO2000005290A1 (fr) | Liant polyurethane presentant une meilleure adherence de lubrifiant | |
DE1694079B2 (de) | Verfahren zur Herstellung von Schichtstoffen | |
WO1997040111A1 (fr) | Revetement hydrofuge compostable |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AK | Designated states |
Kind code of ref document: A1 Designated state(s): BR HU NO PL US |
|
AL | Designated countries for regional patents |
Kind code of ref document: A1 Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE |
|
DFPE | Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101) | ||
121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
WWE | Wipo information: entry into national phase |
Ref document number: 1999966927 Country of ref document: EP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 09868392 Country of ref document: US |
|
WWP | Wipo information: published in national office |
Ref document number: 1999966927 Country of ref document: EP |
|
WWW | Wipo information: withdrawn in national office |
Ref document number: 1999966927 Country of ref document: EP |