[go: up one dir, main page]

WO2000035982A1 - Polyester-polyurethane adhesive and the use thereof - Google Patents

Polyester-polyurethane adhesive and the use thereof Download PDF

Info

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)
French (fr)
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/en
Priority to BR9916168-0A priority patent/BR9916168A/en
Publication of WO2000035982A1 publication Critical patent/WO2000035982A1/en
Priority to NO20012973A priority patent/NO20012973D0/en
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

The invention relates to a polyester-polyurethane adhesive comprised of polyester-polyols and of polyisocyanates, whereby the polyester-polyols are based on lactic acid. The inventive adhesive is preferably used for coating. The adhesive is characterized by its environmental acceptability since it is made of renewable resources and can easily biodegrade.

Description

„Polyester-Polyurethan-Klebstoff und seine Verwendung" "Polyester-polyurethane adhesive and its use"

Die Erfindung betrifft einen Polyurethan-Klebstoff aus Polyester-Polyolen und Polyisocyanaten.The invention relates to a polyurethane adhesive made from polyester polyols and polyisocyanates.

Polyurethan-Klebstoffe auf der Basis von Polyester-Polyolen und Polyisocyanaten sind seit langem bekannt.Polyurethane adhesives based on polyester polyols and polyisocyanates have been known for a long time.

Diole auf der Basis von Milchsäure sind ebenfalls seit mindestens 10 Jahren bekannt. So wird in der EP 0 250 994 deren Herstellung, z.B. aus Ethylenglykol und Milchsäure beschrieben. Dort wird auch vorgeschlagen, die fließfähigen bis festen oligomeren Ester der Milchsäure oder ihre dermatologisch verträglichen Derivate als resorbierbare Träger und/oder Filmbildner zur Herstellung eines kosmetischen oder pharmazeutischen Mittels zur Abdeckung unverletzter und/oder verletzter Bereiche menschlicher oder tierischer Haut zu verwenden. Als Derivate werden Ester genannt. Von Urethanen ist keine Rede, ebensowenig von einer Verwendung der Polyester-Diole auf Basis von Milchsäuren im Klebstoff- Bereich.Lactic acid-based diols have also been known for at least 10 years. For example, EP 0 250 994 describes their manufacture, e.g. described from ethylene glycol and lactic acid. There it is also proposed to use 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. There is no question of urethanes, nor of the use of polyester diols based on lactic acids in the adhesive sector.

Die Erfinder haben sich die Aufgabe gestellt, Polyester-Diole nicht petrochemischer Natur, sondern auf der Basis nachwachsender Rohstoffe, insbesondere pflanzlicher Basis zur Herstellung von Polyurethan-Klebstoffen zur Verfügung zu stellen bzw. die daraus hergestellten Polyurethan-Klebstoffe. Außerdem sollte auch eine zweckmäßige Verwendung gefunden werden. Die Lösung der Erfindung ist den Patentansprüchen zu entnehmen. Sie besteht in erster Linie darin, als Polyester-Polyol ein Polyester-Polyol auf der Basis von Hydroxycarbonsäuren mit 2 bis 5 C-Atomen, insbesondere auf der Basis von Milchsäure zur Herstellung des Polyurethan-Klebstoffes zu verwenden.The inventors have set themselves the task of providing 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. In addition, 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.

Die Milchsäure wird technisch in Extraktions- und Fermentationsprozessen bei der Milchsäure-Gärung, z.B. von Milch und Molke oder von Glukose und Maltose aus Melassen und Malz in breitem Umfang hergestellt. Ausgangsprodukt ist hauptsächlich Mais. Aus der Milchsäure bzw. ihren Derivaten wird durch Polymerisation die Polymilchsäure (Polylactid) hergestellt. Das kann z.B. durch direkte Veresterung mit mindestens zweiwertigen Alkoholen, durch Umesterung von Milchsäureestern oder durch Ringöffnung von Lactid geschehen. Vorzugsweise wird gleichzeitig oder danach aus der Milchsäure durch Reaktion mit geeigneten niedermolekularen Polyolen die Polymilchsäure mit mehreren OH- Gruppen hergestellt. Geeignete niedermolekulare Polyole sind z.B. Ethylen- Glykol, Propan-Diol-1 ,2, Propandiol-1 ,3, Butandiol-1 ,3, Butandiol-1 ,4, Butandiol- 2,3, Neopentylglykol, Hexandiol-1 ,6, Hydrochinon, Resorcin und mehrwertige Alkohole, insbesondere Glycerin und Monoglyceride. Natürlich können auch niedermolekulare Polyalkylendiole oder -Triole verwendet werden, z.B. Tripropylenglykol. Durch das molare Verhältnis der Milchsäure zu dem niedermolekularen Polyol wird das Molekulargewicht der Polymilchsäure mit mehreren OH-Gruppen bestimmt. Bevorzugt sind Polyester-Diole auf der Basis von Milchsäure, insbesondere Oligomere auf der Basis von Milchsäure mit zwei OH-Endgruppen. Zu den Herstellungsbedingungen im einzelnen wird ausdrücklich auf die EP 0 250 994 verwiesen.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. Of course, 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. For details of the manufacturing conditions, reference is expressly made to EP 0 250 994.

Weitere erfindungsgemäß verwendbare Hydroxycarbonsäuren sind: Glykolsäure, Hydroxybuttersäure und Hydroxyvaleriansäure.Further hydroxycarboxylic acids which can be used according to the invention are: glycolic acid, hydroxybutyric acid and hydroxyvaleric acid.

Die Polyester-Polyole auf der Basis von Hydroxycarbonsäuren mit 2 bis 5 C- Atomen, insbesondere Milchsäure mit zwei oder mehr OH-Endgruppen dienen erfindungsgemäß als Ausgangsmaterial zur Herstellung von Polyurethanen bei Reaktion mit Polyisocyanaten. Sie können aber auch zur Herstellung von anderen Kunstharzen verwendet werden. Die Polyurethane können aus einem oder mehreren Polyester-Polyolen und einem oder mehreren Polyisocyanaten hergestellt werden.According to the invention, 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. However, 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.

Unter einem „Polyisocyanat" wird eine niedermolekulare Verbindung mit zwei oder mehr Isocyanat-Gruppen verstanden. Die Diisocyanate werden bevorzugt. Sie können aber bis zu ca. 10 Gew.-% an trifunktionellen Isocyanaten enthalten. Neben aliphatischen und cycloaliphatischen Polyisocyanaten kommen vor allem aromatische Polyisocyanate in Frage. Als konkrete Beispiele seien insbesondere genannt TDI und MDI.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. In addition to aliphatic and cycloaliphatic polyisocyanates, aromatic polyisocyanates are particularly preferred TDI and MDI may be mentioned as specific examples.

Bei den Polyester-Polyurethanen kann man danach unterscheiden, ob eine noch reaktive oder eine nicht reaktive Masse appliziert werden soll. Die reaktive Masse kann ihrerseits wiederum unterschieden werden zwischen einem Polyester- Polyurethan mit noch reaktiven NCO-Gruppen, die mit Wasserdampf ausreagieren (Ein-Komponenten-System) und einem System, bei dem ein Polyester-Polyol (Harz) unmittelbar vor der Applikation mit einem Polyisocyanat (Härter) gemischt wird (Zwei-Komponenten-System). Die erfindungsgemäßen Polyester- Polyurethane aus dem Polyester-Polyolen auf der Basis von Milchsäure eignen sich praktisch für alle Anwendungen, die für bisher bekannte Polyester- Polyurethane aller Art bekannt sind. Ausdrücklich sei auf die Verwendung zum Kleben, Beschichten und Dichten (einschließlich Gießmassen) hingewiesen. Besonders geeignet sind die erfindungsgemäßen Polyester-Polyurethane zum Kleben. Auch hierbei sind im Prinzip alle bekannten Verklebungen von Substraten möglich. Hervorgehoben werden soll aber die Verwendung zum Kaschieren in Form eines Zwei-Komponenten-Systems.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.

Unter Kaschieren wird das Binden von zwei oder mehreren Lagen gleicher oder verschiedener Materialien verstanden. Dabei handelt es sich um Papiere, Textilien, Kunststoffe, Metalle und anderen Materialien, die sich als Lagen bzw. Folien verarbeiten lassen. Diese Materialien werden meistens in einem Kalander in einem Walzprozeß unter Druck mit dem erfindungsgemäßen Polyester- Polyurethan verbunden. Die erfindungsgemäßen Polyester-Polyurethane auf der Basis von Polyester- Polyolen aus Milchsäure zeigten trotz der niedrigen Viskosität überraschend hohe Festigkeitswerte und eignen sich daher insbesondere zu Kaschierungen. Sie sind umweltverträglich, und zwar nicht nur weil sie aus nachwachsenden Rohstoffen gewonnen werden, sondern auch weil sie biologisch abbaubar sind.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.

Die Erfindung wird nun anhand eines Beispiels im einzelnen erläutert: The invention will now be explained in detail using an example:

Analog zum Beispiel 1 c) der EP 0 250 994 wurde aus Tripropylenglykol und Milchsäureethylester im Molverhältnis von 1 : 8,1 ein bifunktioneller Oligo- Milchsäureester hergestellt. Die Viskosität betrug 836 mPas bei 20 °C (Haake Rotationsviskosimeter VT 500, Spindelsatz MV1).Analogously to Example 1 c) of EP 0 250 994, a bifunctional oligo-lactic acid ester was produced from tripropylene glycol and lactic acid ethyl ester in a molar ratio of 1: 8.1. The viscosity was 836 mPas at 20 ° C (Haake rotary viscometer VT 500, spindle set MV1).

Dieses Reaktionsprodukt wurde als Harz im Mengenverhältnis von 1 : 1 ,2 mit MDI als Härter zum Kaschieren einer 12 μm dicken verstreckten Folie aus Polypropylen und einer 50 μm dicken Folie aus Polyethylen verwendet. Der Klebstoffauftrag betrugt 3 μm.This reaction product was used as a resin in a ratio of 1: 1, 2 with MDI as a hardener for laminating a 12 μm thick stretched film made of polypropylene and a 50 μm thick film made of polyethylene. The adhesive application was 3 μm.

Nach einer 7tägigen Lagerung bei 20 °C und 50 % relativer Luftfeuchtigkeit war die Aushärtung beendet. Die Verbundhaftung betrug dann 2,4 N/15 mm, wobei die Polypropylen-Folie riß. Die Siegelnahthaftung betrug 38 N/15 mm, wobei ein Verbund-Abriß eintrat. After storage for 7 days at 20 ° C and 50% relative humidity, the curing was complete. The bond adhesion was then 2.4 N / 15 mm, the polypropylene film tearing. The seal seam adhesion was 38 N / 15 mm, whereby a composite tear occurred.

Claims

Patentansprüche claims 1. Polyurethan-Klebstoff aus Polyester-Polyolen und Polyisocyanaten, dadurch gekennzeichnet, daß das Polyester-Polyol auf mindestens einer Hydroxycarbonsäure mit 2 bis 5 C-Atomen basiert.1. polyurethane adhesive made of polyester polyols and polyisocyanates, characterized in that the polyester polyol is based on at least one hydroxycarboxylic acid having 2 to 5 carbon atoms. 2. Polyurethan-Klebstoff nach Anspruch 1, dadurch gekennzeichnet, daß das Polyester-Polyol ein Poly-Diol ist.2. Polyurethane adhesive according to claim 1, characterized in that the polyester polyol is a poly-diol. 3. Polyurethan-Klebstoff nach Anspruch 1, dadurch gekennzeichnet, daß das Polyester-Polyol ein Polymeres, insbesondere ein Oligomeres vorzugsweise der Milchsäure mit 2 primären und/oder sekundären OH-Endgruppen ist.3. Polyurethane adhesive according to claim 1, characterized in that the polyester polyol is a polymer, in particular an oligomer, preferably lactic acid with 2 primary and / or secondary OH end groups. 4. Polyurethan-Klebstoff nach Anspruch 1, dadurch gekennzeichnet, daß er zweikomponentig ist und die Harzkomponente aus mindestens einem Polyester-Polyol auf der Basis von Hydroxycarbonsäure mit 2 bis 5 C-Atomen und die Härter-Komponente aus einem Polyisocyanat, insbesondere einem Diisocyanat besteht.4. Polyurethane adhesive according to claim 1, characterized in that it is two-component and the resin component consists of at least one polyester polyol based on hydroxycarboxylic acid with 2 to 5 carbon atoms and the hardener component consists of a polyisocyanate, in particular a diisocyanate . 5. Verwendung des Polyurethan-Klebstoffes nach mindestens einem der Ansprüche 1 bis 4 zum Kaschieren. 5. Use of the polyurethane adhesive according to at least one of claims 1 to 4 for lamination.
PCT/EP1999/009623 1998-12-17 1999-12-08 Polyester-polyurethane adhesive and the use thereof Ceased WO2000035982A1 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP99966927A EP1153055A1 (en) 1998-12-17 1999-12-08 Polyester-polyurethane adhesive and the use thereof
BR9916168-0A BR9916168A (en) 1998-12-17 1999-12-08 Polyester-polyurethane adhesive and its use
NO20012973A NO20012973D0 (en) 1998-12-17 2001-06-15 Polyester-polyurethane glue and its use

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 (en) 2000-06-22

Family

ID=7891410

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1999/009623 Ceased WO2000035982A1 (en) 1998-12-17 1999-12-08 Polyester-polyurethane adhesive and the use thereof

Country Status (5)

Country Link
EP (1) EP1153055A1 (en)
BR (1) BR9916168A (en)
DE (1) DE19958526A1 (en)
NO (1) NO20012973D0 (en)
WO (1) WO2000035982A1 (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101899139A (en) * 2010-07-23 2010-12-01 同济大学 A kind of preparation method of polylactic acid base high elasticity copolymer
EP2781532A1 (en) 2013-03-22 2014-09-24 Novamelt GmbH Klebstofftechnologie Adhesive composition based on modified polylactide, method for its production and use of the adhesive composition
US8999503B2 (en) 2009-10-20 2015-04-07 Nitto Denko Corporation Thermally removable pressure-sensitive adhesive sheet
WO2017003872A1 (en) * 2015-07-01 2017-01-05 H.B. Fuller Company Adhesive composition based on polylactide polyols
WO2017003875A1 (en) * 2015-07-01 2017-01-05 H.B. Fuller Company Moisture curable adhesive composition based on polylactide polyols
CN114886840A (en) * 2020-07-10 2022-08-12 南京海鲸药业有限公司 Series of polymers with acid-sensitive degradation and temperature-sensitive properties and drug-loaded composition thereof

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102006006904A1 (en) * 2006-02-09 2007-08-23 Universität Rostock New haemostatic agents and adhesives for medical applications
DE102006048833A1 (en) 2006-10-16 2008-04-17 Universität Rostock Combination for preparing medicine product for treatment of osteoporosis, prophylaxis or bone fractures, or for anchorage of implants, comprises calcium-containing substance and cross linking agent
DE102007061506A1 (en) * 2007-12-18 2009-06-25 Henkel Ag & Co. Kgaa Biodegradable adhesive
ES2349900T3 (en) 2008-02-27 2011-01-12 Sika Technology Ag GLUE FOR LINING TO HIGH TEMPERATURE.
DE102014209019A1 (en) * 2014-05-13 2015-11-19 Henkel Ag & Co. Kgaa Binder system with faster curing
EP3034534A1 (en) 2014-12-17 2016-06-22 PURAC Biochem BV Substrates coated or bonded with a composition comprising a polyurethane
WO2016097002A1 (en) 2014-12-17 2016-06-23 Purac Biochem Bv Substrates coated or bonded with a composition comprising a polyurethane
DE102018214839B4 (en) * 2018-08-31 2021-05-12 Kufner Holding Gmbh Heat-sealable, textile fabric with a sustainable adhesive coating and its use
JP6881647B1 (en) * 2020-04-17 2021-06-02 東洋インキＳｃホールディングス株式会社 Adhesive composition and adhesive sheet

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 (en) * 1989-12-12 1991-08-08 Dainichiseika Color & Chem Mfg Co Ltd Two-pack curable adhesive composition
DE4225045A1 (en) * 1992-07-29 1994-02-03 Basf Ag Use of water-soluble or water-dispersible polyurethanes as auxiliaries in cosmetic and pharmaceutical preparations and polyurethanes which contain copolymerized polylactic acid polyols
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 (en) * 1989-12-12 1991-08-08 Dainichiseika Color & Chem Mfg Co Ltd Two-pack curable adhesive composition
DE4225045A1 (en) * 1992-07-29 1994-02-03 Basf Ag Use of water-soluble or water-dispersible polyurethanes as auxiliaries in cosmetic and pharmaceutical preparations and polyurethanes which contain copolymerized polylactic acid polyols
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 (en) * 2010-07-23 2010-12-01 同济大学 A kind of preparation method of polylactic acid base high elasticity copolymer
EP2781532A1 (en) 2013-03-22 2014-09-24 Novamelt GmbH Klebstofftechnologie Adhesive composition based on modified polylactide, method for its production and use of the adhesive composition
DE102013205144A1 (en) 2013-03-22 2014-09-25 Novamelt GmbH Klebstofftechnologie Adhesive composition based on optionally modified polylactide, process for their preparation and use of the adhesive composition
WO2017003872A1 (en) * 2015-07-01 2017-01-05 H.B. Fuller Company Adhesive composition based on polylactide polyols
WO2017003875A1 (en) * 2015-07-01 2017-01-05 H.B. Fuller Company Moisture curable adhesive composition based on polylactide polyols
CN114886840A (en) * 2020-07-10 2022-08-12 南京海鲸药业有限公司 Series of polymers with acid-sensitive degradation and temperature-sensitive properties and drug-loaded composition thereof
CN114886840B (en) * 2020-07-10 2023-08-25 南京海鲸药业股份有限公司 Serial polymers with acid sensitive degradation and temperature sensitive properties and medicine carrying composition thereof

Also Published As

Publication number Publication date
BR9916168A (en) 2001-09-04
EP1153055A1 (en) 2001-11-14
NO20012973L (en) 2001-06-15
DE19958526A1 (en) 2000-06-21
NO20012973D0 (en) 2001-06-15

Similar Documents

Publication Publication Date Title
EP2089450B1 (en) Polyurethane lamination adhesive
EP1153055A1 (en) Polyester-polyurethane adhesive and the use thereof
EP3265501B1 (en) Adhesives with low voc and fogging values
DE1961770A1 (en) Polyurethane adhesive
WO2018095960A1 (en) Polyester-free laminating adhesive composition
EP2011808A1 (en) Medical adhesives for surgery
EP3327056B1 (en) Low viscosity, fast curing adhesive laminate-composition
EP3265532B1 (en) Adhesives with low voc and fogging values
EP3257882A1 (en) Biodegradable adhesive compound
EP2275466A1 (en) Polyuric-based cloth adhesive
EP1030869A1 (en) Polyurethane binding agents having a low content of highly volatile monomers
EP0448825A2 (en) Melt adhesive process
DE4103347A1 (en) WAFER POLYURETHANE DISPERSIONS AND THEIR USE AS CASCASING ADHESIVES
WO2014206779A1 (en) Hydrophobic polyurethane adhesive
EP1189961B1 (en) Use of polyurethane compositions of low monomer content as pressure sensitive adhesive
EP0894122A1 (en) Compostable adhesive
WO2019043054A1 (en) REACTIVE ADHESIVES WITH LOW CONTENT ON MONOMERIC DIISOCYANATE
EP0176726B1 (en) Use of solutions of polyisocyanates and oligourethanes containing hydroxy groups as adhesives for layered-sheets products
EP3625279A1 (en) Polyurethane-based binder system
EP2781532B1 (en) Adhesive composition based on modified polylactide, method for its production and use of the adhesive composition
EP1100839A1 (en) Monomer-poor polyurethane bonding agent having an improved lubricant adhesion
EP0295422A2 (en) Polyester urethanes and their use as adhesives
DE1694079B2 (en) Process for the production of laminates
EP0894118A1 (en) Compostable waterproof coating

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