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WO2000035982A1 - Adhesif polyester-polyurethanne et son utilisation - Google Patents

Adhesif polyester-polyurethanne et son utilisation Download PDF

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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
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/EP1999/009623
Other languages
German (de)
English (en)
Inventor
Christian Priebe
Markus Krüdenscheidt
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Priority to EP99966927A priority Critical patent/EP1153055A1/fr
Priority to BR9916168-0A priority patent/BR9916168A/pt
Publication of WO2000035982A1 publication Critical patent/WO2000035982A1/fr
Priority to NO20012973A priority patent/NO20012973D0/no
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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

Adhésif polyester-polyuréthanne constitué de polyester-polyols et de polyisocyanates, les polyester-polyols étant à base d'acide lactique. L'adhésif selon la présente invention est utilisé de préférence pour le contrecollage. Il se caractérise par le fait qu'il est sans danger pour l'environnement étant donné qu'il est à base de matières premières renouvelables et qu'il est facilement dégradable.
PCT/EP1999/009623 1998-12-17 1999-12-08 Adhesif polyester-polyurethanne et son utilisation Ceased WO2000035982A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP99966927A EP1153055A1 (fr) 1998-12-17 1999-12-08 Adhesif polyester-polyurethanne et son utilisation
BR9916168-0A BR9916168A (pt) 1998-12-17 1999-12-08 Adesivo de poliéster-poliuretana e seu emprego
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
DE19858240.4 1998-12-17
DE19858240 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 Ceased 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)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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
ES2349900T3 (es) 2008-02-27 2011-01-12 Sika Technology Ag Pegamento para forrar a temperatura elevada.
DE102014209019A1 (de) * 2014-05-13 2015-11-19 Henkel Ag & Co. Kgaa Bindemittel-System mit schnellerer Aushärtung
EP3034534A1 (fr) 2014-12-17 2016-06-22 PURAC Biochem BV Substrats revêtus ou liés avec une composition comprenant un polyuréthane
WO2016097002A1 (fr) 2014-12-17 2016-06-23 Purac Biochem Bv Substrats revêtus ou liés au moyen d'une composition comprenant un polyuréthanne
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)

* Cited by examiner, † Cited by third party
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

Patent Citations (4)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 116, no. 4, 27 January 1992, Columbus, Ohio, US; abstract no. 22574f, XP000282433 *

Cited By (8)

* Cited by examiner, † Cited by third party
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
EP1153055A1 (fr) 2001-11-14
NO20012973L (no) 2001-06-15
DE19958526A1 (de) 2000-06-21
NO20012973D0 (no) 2001-06-15

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