DE19958526A1 - Polyurethane adhesive useful especially for laminating applications is derived from polyisocyanate component and polyester-polyol component based on hydroxy-carboxylic acids, especially lactic acid - Google Patents
Polyurethane adhesive useful especially for laminating applications is derived from polyisocyanate component and polyester-polyol component based on hydroxy-carboxylic acids, especially lactic acidInfo
- Publication number
- DE19958526A1 DE19958526A1 DE19958526A DE19958526A DE19958526A1 DE 19958526 A1 DE19958526 A1 DE 19958526A1 DE 19958526 A DE19958526 A DE 19958526A DE 19958526 A DE19958526 A DE 19958526A DE 19958526 A1 DE19958526 A1 DE 19958526A1
- Authority
- DE
- Germany
- Prior art keywords
- polyester
- lactic acid
- polyurethane adhesive
- hydroxy
- derived
- 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.)
- Withdrawn
Links
- 239000004814 polyurethane Substances 0.000 title claims abstract description 21
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 21
- 239000000853 adhesive Substances 0.000 title claims abstract description 14
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 14
- 229920005906 polyester polyol Polymers 0.000 title claims abstract description 14
- 229920001228 polyisocyanate Polymers 0.000 title claims abstract description 12
- 239000005056 polyisocyanate Substances 0.000 title claims abstract description 12
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 title claims abstract description 7
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 title claims description 32
- 235000014655 lactic acid Nutrition 0.000 title claims description 17
- 239000004310 lactic acid Substances 0.000 title claims description 16
- 238000010030 laminating Methods 0.000 title description 3
- 150000002009 diols Chemical class 0.000 claims description 6
- 239000011347 resin Substances 0.000 claims description 4
- 229920005989 resin Polymers 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 238000003475 lamination Methods 0.000 claims description 3
- 239000004848 polyfunctional curative Substances 0.000 claims description 3
- 125000005442 diisocyanate group Chemical group 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 claims 1
- 229920000728 polyester Polymers 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 5
- 229920005862 polyol Polymers 0.000 description 5
- -1 Lactic acid polyols Chemical class 0.000 description 4
- 229920000747 poly(lactic acid) Polymers 0.000 description 4
- 150000003077 polyols Chemical class 0.000 description 4
- 239000000463 material Substances 0.000 description 3
- 239000004626 polylactic acid Substances 0.000 description 3
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- 238000000855 fermentation Methods 0.000 description 2
- 230000004151 fermentation Effects 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 1
- JRHWHSJDIILJAT-UHFFFAOYSA-N 2-hydroxypentanoic acid Chemical compound CCCC(O)C(O)=O JRHWHSJDIILJAT-UHFFFAOYSA-N 0.000 description 1
- SJZRECIVHVDYJC-UHFFFAOYSA-N 4-hydroxybutyric acid Chemical compound OCCCC(O)=O SJZRECIVHVDYJC-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 1
- GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000005862 Whey Substances 0.000 description 1
- 102000007544 Whey Proteins Human genes 0.000 description 1
- 108010046377 Whey Proteins Proteins 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 238000004026 adhesive bonding Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 150000003903 lactic acid esters Chemical class 0.000 description 1
- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 235000013379 molasses Nutrition 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 229940117969 neopentyl glycol Drugs 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-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
- C08G18/42—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
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
Description
Die Erfindung betrifft einen Polyurethan-Klebstoff aus Polyester-Polyolen und Polyisocyanaten.The invention relates to a polyurethane adhesive made of polyester and polyols 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 used for at least 10 years known. So in EP 0 250 994 their preparation, for. B. from ethylene glycol and lactic acid. It also suggests the flowable up solid oligomeric esters of lactic acid or their dermatologically compatible ones Derivatives as resorbable carriers and / or film formers for the production of a cosmetic or pharmaceutical agent for covering undamaged and / or use injured areas of human or animal skin. As Derivatives are called esters. There is no question of urethanes, nor of use of the polyester diols based on lactic acids in the adhesive Area.
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.The inventors set themselves the task, polyester diols did not petrochemical in nature, but based on renewable raw materials, especially plant-based for the production of polyurethane adhesives To make available or the polyurethane adhesives produced therefrom. In addition, appropriate use should also be found.
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 solution of the invention can be found in the patent claims. It consists of primarily in the form of a polyester polyol, a polyester polyol based on Hydroxycarboxylic acids with 2 to 5 carbon atoms, especially based on To use 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 at Lactic acid fermentation, e.g. B. from milk and whey or from glucose and maltose Molasses and malt are widely produced. The starting product is mainly corn. Lactic acid or its derivatives are converted into Polymerization produced the polylactic acid (polylactide). That can e.g. B. by direct esterification with at least dihydric alcohols, by transesterification of lactic acid esters or by ring opening of lactide. The lactic acid is preferably reacted simultaneously or thereafter with suitable low molecular weight polyols the polylactic acid with several OH Groups. Suitable low molecular weight polyols are e.g. B. ethylene Glycol, propane-diol-1,2, propanediol-1,3, butanediol-1,3, butanediol-1,4, butanediol-2,3, Neopentylglycol, 1,6-hexanediol, hydroquinone, resorcinol and polyvalent Alcohols, especially glycerin and monoglycerides. Of course you can too low molecular weight polyalkylene diols or triols are used, e.g. B. Tripropylene glycol. Due to the molar ratio of lactic acid to the low molecular weight polyol, the molecular weight of polylactic acid with determined several OH groups. Polyester-based diols are preferred of lactic acid, in particular oligomers based on lactic acid with two OH end groups. The manufacturing conditions in detail are expressly stated refer 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. The polyester polyols based on hydroxycarboxylic acids with 2 to 5 C- Serve atoms, especially lactic acid with two or more OH end groups according to the invention as a starting material for the production of polyurethanes Reaction with polyisocyanates. But you can also use it to make others Resins are used. The polyurethanes can be made from one or several polyester polyols and one or more polyisocyanates getting 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.Under a "polyisocyanate" is a low molecular weight compound with two or understood more isocyanate groups. The diisocyanates are preferred. she but can contain up to about 10 wt .-% of trifunctional isocyanates. In addition to aliphatic and cycloaliphatic polyisocyanates, above all aromatic polyisocyanates in question. In particular, as concrete examples called TDI and MDI.
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, one can differentiate between whether there is still one reactive or a non-reactive mass is to be applied. The reactive mass can in turn be differentiated between a polyester Polyurethane with still reactive NCO groups that react with water vapor (One-component system) and a system in which a polyester polyol (Resin) mixed with a polyisocyanate (hardener) immediately before application will (two-component system). The polyester according to the invention Polyurethanes made from polyester polyols based on lactic acid are suitable practically for all applications that are known for previously known polyester All types of polyurethanes are known. Express to the use for Gluing, coating and sealing (including casting compounds). The polyester polyurethanes according to the invention are particularly suitable for Glue. Here too, in principle, are all known adhesions of substrates possible. However, the use for lamination in should be emphasized Form of a two-component system.
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.Laminating becomes the binding of two or more layers of the same or understood different materials. These are papers, Textiles, plastics, metals and other materials that can be used as layers or Have foils processed. These materials are mostly in a calender in a rolling process under pressure with the polyester according to the invention Polyurethane bonded.
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. The polyester polyurethanes according to the invention based on polyester Lactic acid polyols showed surprisingly high despite the low viscosity Strength values and are therefore particularly suitable for lamination.
Sie sind umweltverträglich, und zwar nicht nur weil sie aus nachwachsenden Rohstoffen gewonnen werden, sondern auch weil sie biologisch abbaubar sind.They are environmentally friendly, and not just because they are made from renewable resources Raw materials, but also because they are biodegradable.
Die Erfindung wird nun anhand eines Beispiels im einzelnen erläutert:
Analog zum Beispiel 1c) 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).The invention will now be explained in detail using an example:
Analogously to Example 1c) of EP 0 250 994, a bifunctional oligo-lactic acid ester was produced from tripropylene glycol and ethyl lactate 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.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 Polypropylene and a 50 µm thick film made of polyethylene are used.
Der Klebstoffauftrag betrugt 3 µm.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 curing ends. The bond adhesion was then 2.4 N / 15 mm, the Polypropylene film tore. The seal seam adhesion was 38 N / 15 mm, with a Compound demolition occurred.
Claims (5)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19958526A DE19958526A1 (en) | 1998-12-17 | 1999-12-04 | Polyurethane adhesive useful especially for laminating applications is derived from polyisocyanate component and polyester-polyol component based on hydroxy-carboxylic acids, especially lactic acid |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19858240 | 1998-12-17 | ||
| DE19958526A DE19958526A1 (en) | 1998-12-17 | 1999-12-04 | Polyurethane adhesive useful especially for laminating applications is derived from polyisocyanate component and polyester-polyol component based on hydroxy-carboxylic acids, especially lactic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE19958526A1 true DE19958526A1 (en) | 2000-06-21 |
Family
ID=7891410
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19958526A Withdrawn DE19958526A1 (en) | 1998-12-17 | 1999-12-04 | Polyurethane adhesive useful especially for laminating applications is derived from polyisocyanate component and polyester-polyol component based on hydroxy-carboxylic acids, especially lactic acid |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP1153055A1 (en) |
| BR (1) | BR9916168A (en) |
| DE (1) | DE19958526A1 (en) |
| NO (1) | NO20012973L (en) |
| WO (1) | WO2000035982A1 (en) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007090373A3 (en) * | 2006-02-09 | 2008-08-07 | Univ Rostock | Novel adhesives for medical applications |
| WO2009077229A1 (en) * | 2007-12-18 | 2009-06-25 | Henkel Ag & Co. Kgaa | Bio-degradable laminating adhesive |
| US8389647B2 (en) | 2008-02-27 | 2013-03-05 | Sika Technology Ag | Laminating adhesive for demoulding at elevated temperature |
| US8496971B2 (en) | 2006-10-16 | 2013-07-30 | Universitaet Rostock | Treatment of osteoporosis |
| WO2015173298A1 (en) * | 2014-05-13 | 2015-11-19 | Henkel Ag & Co. Kgaa | Binder system with faster hardening |
| 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 |
| DE102018214839A1 (en) * | 2018-08-31 | 2020-03-05 | Kufner Holding Gmbh | Fabric with sustainable adhesive coating |
| CN115427531A (en) * | 2020-04-17 | 2022-12-02 | 东洋油墨Sc控股株式会社 | Adhesive composition and adhesive sheet |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5456431B2 (en) | 2009-10-20 | 2014-03-26 | 日東電工株式会社 | Heat release type adhesive sheet |
| CN101899139B (en) * | 2010-07-23 | 2012-02-29 | 同济大学 | A kind of preparation method of polylactic acid base high elasticity copolymer |
| 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 |
| US20170002241A1 (en) * | 2015-07-01 | 2017-01-05 | H.B. Fuller Company | Moisture curable adhesive composition based on polylactide polyols |
| WO2017003872A1 (en) * | 2015-07-01 | 2017-01-05 | H.B. Fuller Company | Adhesive composition based on polylactide polyols |
| 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 |
Family Cites Families (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 |
| JPH0794652B2 (en) * | 1989-12-12 | 1995-10-11 | 大日精化工業株式会社 | Two-component 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 |
| DE4315611A1 (en) * | 1993-05-11 | 1994-11-17 | Basf Ag | Functionalized polylactide |
-
1999
- 1999-12-04 DE DE19958526A patent/DE19958526A1/en not_active Withdrawn
- 1999-12-08 WO PCT/EP1999/009623 patent/WO2000035982A1/en not_active Ceased
- 1999-12-08 EP EP99966927A patent/EP1153055A1/en not_active Withdrawn
- 1999-12-08 BR BR9916168-0A patent/BR9916168A/en not_active Application Discontinuation
-
2001
- 2001-06-15 NO NO20012973A patent/NO20012973L/en unknown
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007090373A3 (en) * | 2006-02-09 | 2008-08-07 | Univ Rostock | Novel adhesives for medical applications |
| EP3050579A1 (en) * | 2006-02-09 | 2016-08-03 | Aesculap Ag | Novel adhesives for medical applications |
| US8496971B2 (en) | 2006-10-16 | 2013-07-30 | Universitaet Rostock | Treatment of osteoporosis |
| WO2009077229A1 (en) * | 2007-12-18 | 2009-06-25 | Henkel Ag & Co. Kgaa | Bio-degradable laminating adhesive |
| US8389647B2 (en) | 2008-02-27 | 2013-03-05 | Sika Technology Ag | Laminating adhesive for demoulding at elevated temperature |
| WO2015173298A1 (en) * | 2014-05-13 | 2015-11-19 | Henkel Ag & Co. Kgaa | Binder system with faster hardening |
| WO2016097002A1 (en) | 2014-12-17 | 2016-06-23 | Purac Biochem Bv | Substrates coated or bonded with a composition comprising a polyurethane |
| WO2016097005A1 (en) | 2014-12-17 | 2016-06-23 | Purac Biochem Bv | Substrates coated or bonded with a composition comprising a polyurethane |
| EP3034534A1 (en) | 2014-12-17 | 2016-06-22 | PURAC Biochem BV | Substrates coated or bonded with a composition comprising a polyurethane |
| DE102018214839A1 (en) * | 2018-08-31 | 2020-03-05 | Kufner Holding Gmbh | Fabric with sustainable adhesive coating |
| DE102018214839B4 (en) * | 2018-08-31 | 2021-05-12 | Kufner Holding Gmbh | Heat-sealable, textile fabric with a sustainable adhesive coating and its use |
| US12012526B2 (en) | 2018-08-31 | 2024-06-18 | Kufner Holding Gmbh | Sheet material having a sustainable adhesive coating |
| CN115427531A (en) * | 2020-04-17 | 2022-12-02 | 东洋油墨Sc控股株式会社 | Adhesive composition and adhesive sheet |
Also Published As
| Publication number | Publication date |
|---|---|
| NO20012973D0 (en) | 2001-06-15 |
| EP1153055A1 (en) | 2001-11-14 |
| WO2000035982A1 (en) | 2000-06-22 |
| NO20012973L (en) | 2001-06-15 |
| BR9916168A (en) | 2001-09-04 |
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