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WO2000023491A1 - Method for producing polyurethane - Google Patents

Method for producing polyurethane Download PDF

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Publication number
WO2000023491A1
WO2000023491A1 PCT/EP1999/003959 EP9903959W WO0023491A1 WO 2000023491 A1 WO2000023491 A1 WO 2000023491A1 EP 9903959 W EP9903959 W EP 9903959W WO 0023491 A1 WO0023491 A1 WO 0023491A1
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WO
WIPO (PCT)
Prior art keywords
polyol
polyisocyanate
groups
soybean oil
polyurethane
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/EP1999/003959
Other languages
German (de)
French (fr)
Inventor
Martin Stielau
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Individual
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Individual
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Filing date
Publication date
Application filed by Individual filed Critical Individual
Priority to AU46067/99A priority Critical patent/AU4606799A/en
Priority to EP99929155A priority patent/EP1137686A1/en
Publication of WO2000023491A1 publication Critical patent/WO2000023491A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/36—Hydroxylated esters of higher fatty acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2110/00—Foam properties
    • C08G2110/0025—Foam properties rigid

Definitions

  • the invention relates to a process for the production of polyurethane, including polyurethane prepolymers. It also relates to the use of the polyurethane or prepolymer produced according to the invention.
  • Castor oil that is a natural raw material, with polyisocyanate to give polyurethane.
  • Castor oil consists of 80-85% by weight of ricinoleic acid glyceride, i.e. a triol with about 5.2% reactive OH groups. Due to the high OH value, the conversion of castor oil requires a large amount of polyisocyanate, which leads to high production costs.
  • the object of the invention is to reduce the polyurethane production costs.
  • natural soybean oil converts to a polyol during the production of polyurethane prepolymers and foams. That is, in the prepolymerization process in the presence of a polyol, natural soybean oil forms OH groups which react with the NCO groups of the polyisocyanate.
  • Diisocyanates are preferably used as the polyisocyanate, for example 4,4′-methylene di (phenyl isocyanate).
  • triols preferably castor oil, are used in particular as polyols.
  • the soybean oil is preferably used in a weight ratio of 0.2 to 5, in particular 0.5 to 2 parts and particularly preferably about one part per part by weight of castor oil.
  • the soybean oil is preferably used in an amount of 10 g to 300 g, in particular 70 g to 200 g, per OH mol equivalent of the polyol.
  • An OH mol equivalent means the molecular weight of the polyol divided by its (reactive) OH groups.
  • the molar ratio of the NCO groups of the polyisocyanate to the OH groups of the polyol is preferably 1 to 4: 1, in particular 2 to 3: 1.
  • the reaction of the polyisocyanate with the polyol and the soybean oil is preferably first carried out to form a prepolymer with free isocyanate groups.
  • the polyisocyanate is used in the reaction with the polyol and the soybean oil in a stoichiometric excess, for example such that 3% to 30%, in particular about 10%, of the NCO groups are not reacted.
  • the prepolymer obtained in this way can be cured by adding compounds with acidic OH groups, in particular water, by reacting the excess free isocyanate groups.
  • Known catalysts for polyurethane production e.g. Dibutyltin dilaurate (DBTL) can be used.
  • 100 g castor oil are mixed with 100 g soybean oil.
  • the mixture is heated to about 150 ° C. with stirring and held at this temperature for about 30 minutes.
  • about 200 g of MDI (“44V20” from Bayer) are added with stirring in the absence of moisture and the whole is kept at 90 ° C. for about 1 hour.
  • the prepolymer obtained in this way cures with atmospheric moisture to form an extremely resistant film.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

A method for producing polyurethane pre-polymers and foamed plastics, using natural soya oil. Soya oil forms OH groups in the presence of a polyol in a pre-polymerization process. Said OH groups react with NCO groups of an isocyanate.

Description

Verfahren zur Herstellung von Polyurethan Process for the production of polyurethane

Die Erfindung bezieht sich auf ein Verfahren zur Herstellung von Polyurethan, einschließlich Polyurethanpräpolymeren. Sie hat auch die Verwendung des erfindungsgemäß hergestellten Polyurethans bzw. Präpolymers zum Gegenstand.The invention relates to a process for the production of polyurethane, including polyurethane prepolymers. It also relates to the use of the polyurethane or prepolymer produced according to the invention.

Es ist bekannt, Rizinusöl, also einen Naturrohstoff, mit Polyisocyanat zu Polyurethan umzusetzen. Rizinusöl besteht zu 80-85 Gew.-% aus Rizinolsäureglycerid, also einem Triol mit etwa 5,2% reaktiven OH-Gruppen. Aufgrund des hohen OH-Wertes bedarf die Umsetzung von Rizinusöl jedoch einer großen Menge Polyisocyanat, was zu hohen Herstellungskosten führt .It is known to convert castor oil, that is a natural raw material, with polyisocyanate to give polyurethane. Castor oil consists of 80-85% by weight of ricinoleic acid glyceride, i.e. a triol with about 5.2% reactive OH groups. Due to the high OH value, the conversion of castor oil requires a large amount of polyisocyanate, which leads to high production costs.

Der Erfinder hat in dem portugisischen Patent 86.688 bereits Pflanzenöle ohne OH-Gruppen als besonders geeignete Weichmacher in Präpolymeren vorgeschlagen. Im Hinblick auf Sojaölepoxid gehört die Gewinnung von Polyolen durch partielle Öffnung des Oxiranringes mit Alkohol zum Stand der Technik.In Portuguese patent 86,688, the inventor has already proposed vegetable oils without OH groups as particularly suitable plasticizers in prepolymers. With regard to soybean oil epoxide, the production of polyols by partially opening the oxirane ring with alcohol is state of the art.

Aufgabe der Erfindung ist es, die Polyurethanherstellungskosten herabzusetzen.The object of the invention is to reduce the polyurethane production costs.

Es wird erfindungsgemäß dadurch erreicht, dass die Umsetzung des Polyisocyanats mit einem Polyol, wie Rizinusöl, in Gegenwart von Sojaöl durchgeführt wird.It is achieved according to the invention in that the reaction of the polyisocyanate with a polyol, such as castor oil, is carried out in the presence of soybean oil.

Gemische von Polyolen, insbesondere Rizinusöl mit Sojaöl sind kostengünstig und im Gemisch mit Polyisocyanaten weniger viskos. Das Sojaöl erscheint auf den ersten Blick als Weichmacher zu funktionieren, es tritt jedoch nach der Reaktion des überschüssigen Polyisocyanat mit anderen OH-Gruppen eine feste Bindung des Sojaöls auf.Mixtures of polyols, especially castor oil with soybean oil, are inexpensive and less viscous when mixed with polyisocyanates. At first glance, the soybean oil appears to function as a plasticizer, but after the excess polyisocyanate has reacted with other OH groups, the soybean oil becomes firmly bound.

Erfindungsgemäß wurde festgestellt, dass sich natürliches Sojaöl in ein Polyol während der Herstellung von Polyurethan-Präpolymeren und -Schaumstoffen umwandelt. Das heißt, in dem Präpolymerisationsverfahren in Gegenwart eines Po- lyols bildet natürliches Sojaöl OH-Gruppen, die mit den NCO-Gruppen des Polyisocyanats reagieren.According to the invention, it was found that natural soybean oil converts to a polyol during the production of polyurethane prepolymers and foams. That is, in the prepolymerization process in the presence of a polyol, natural soybean oil forms OH groups which react with the NCO groups of the polyisocyanate.

So wurde festgestellt, dass ein Gemisch von Rizinusöl und Sojaöl mit einer entsprechenden Menge von Polyisocyanat nach Präpolymerisation im Kontakt mit Luftfeuchtigkeit voll aushärtet, was bedeutet, dass das Sojaöl, das ursprünglich nicht mit Isocyanaten reagiert, während der Reaktion des überschüssigen Isocyanats in ein Polyol umgewandelt worden ist .It was found that a mixture of castor oil and soybean oil with a corresponding amount of polyisocyanate fully cured after prepolymerization in contact with atmospheric moisture, which means that the soybean oil, which originally did not react with isocyanates, was converted into a polyol during the reaction of the excess isocyanate has been .

Als Polyisocyanat werden vorzugsweise Diisocyanate eingesetzt, beispielsweise 4, 4 ' -Methylendi- (phenylisocyanat) . Als Polyole werden erfindungsgemäß insbesondere Triole verwendet, vorzugsweise Rizinusöl.Diisocyanates are preferably used as the polyisocyanate, for example 4,4′-methylene di (phenyl isocyanate). According to the invention, triols, preferably castor oil, are used in particular as polyols.

Das Sojaöl wird dabei vorzugsweise in einem Gewichtsverhältnis von 0,2 bis 5, insbesondere 0,5 bis 2 Teilen und besonders bevorzugt etwa einem Teil je Gewichtsteil Rizinusöl verwendet.The soybean oil is preferably used in a weight ratio of 0.2 to 5, in particular 0.5 to 2 parts and particularly preferably about one part per part by weight of castor oil.

Bezogen auf das Polyol wird das Sojaöl vorzugsweise in einer Menge von 10 g bis 300 g, insbesondere 70 g bis 200 g, je OH-Mol-Equivalent des Polyols eingesetzt. Ein OH-Mol-Equivalent bedeutet dabei, das Molekulargewicht des Polyols, dividiert durch seine (reaktiven) OH-Gruppen. Das Mol-Verhältnis der NCO-Gruppen des Polyisocyanats zu den OH-Gruppen des Polyols beträgt vorzugsweise 1 bis 4 : 1, insbesondere 2 bis 3 : 1.Based on the polyol, the soybean oil is preferably used in an amount of 10 g to 300 g, in particular 70 g to 200 g, per OH mol equivalent of the polyol. An OH mol equivalent means the molecular weight of the polyol divided by its (reactive) OH groups. The molar ratio of the NCO groups of the polyisocyanate to the OH groups of the polyol is preferably 1 to 4: 1, in particular 2 to 3: 1.

Die Umsetzung des Polyisocyanats mit dem Polyol und dem Sojaöl erfolgt vorzugsweise zunächst zu einem Präpolymeren mit freien Isocyanat-Gruppen. Dazu wird das Polyisocyanat bei der Reaktion mit dem Polyol und dem Sojaöl in einem stöchiometrischen Überschuss eingesetzt, der beispielsweise so bemessen ist, dass 3% bis 30%, insbesondere etwa 10% der NCO-Gruppen nicht umgesetzt werden.The reaction of the polyisocyanate with the polyol and the soybean oil is preferably first carried out to form a prepolymer with free isocyanate groups. For this purpose, the polyisocyanate is used in the reaction with the polyol and the soybean oil in a stoichiometric excess, for example such that 3% to 30%, in particular about 10%, of the NCO groups are not reacted.

Das so erhaltene Präpolymer kann durch Hinzufügen von Verbindungen mit aciden OH-Gruppen, insbesondere Wasser, durch Umsetzung der überschüssigen, freien Isocyanatgruppen ausgehärtet werden. Auch können dazu bekannte Katalysatoren zur Polyurethan-Herstellung, z.B. Dibutylzinndilaurat (DBTL) , verwendet werden.The prepolymer obtained in this way can be cured by adding compounds with acidic OH groups, in particular water, by reacting the excess free isocyanate groups. Known catalysts for polyurethane production, e.g. Dibutyltin dilaurate (DBTL) can be used.

Beispiel 1example 1

100 g Rizinusöl werden mit 100 g Sojaöl vermischt. Das Gemisch wird unter Rühren auf etwa 150°C erwärmt und bei dieser Temperatur etwa 30 min gehalten. Nach Abkühlung auf etwa 70°C werden etwa 200 g MDI ("44V20" der Firma Bayer) unter Rühren unter Ausschluss von Feuchtigkeit hinzugefügt und das Ganze etwa 1 Std. bei 90 °C gehalten. Das so erhaltene Präpolymer härtet mit Luftfeuchtigkeit zu einem äußerst resistentem Film aus.100 g castor oil are mixed with 100 g soybean oil. The mixture is heated to about 150 ° C. with stirring and held at this temperature for about 30 minutes. After cooling to about 70 ° C., about 200 g of MDI (“44V20” from Bayer) are added with stirring in the absence of moisture and the whole is kept at 90 ° C. for about 1 hour. The prepolymer obtained in this way cures with atmospheric moisture to form an extremely resistant film.

Beispiel 2Example 2

100 g des nach dem Beispiel 1 hergestellten Präpolymers werden mit 5 g Wasser und 0,3 g DBTL vermischt. Nach exo- thermer Reaktion erhält man einen Hartschaum mit guten Fe- stigkeits- und chemischen Eigenschaften. 100 g of the prepolymer prepared according to Example 1 are mixed with 5 g of water and 0.3 g of DBTL. After exo- Thermer reaction gives a rigid foam with good strength and chemical properties.

Claims

Patentansprüche claims 1. Verfahren zur Herstellung von Polyurethan, bei dem ein Polyisocyanat mit einem Polyol umgesetzt wird, dadurch gekennzeichnet, dass die Umsetzung des Polyisocyanats mit dem Polyol in Gegenwart von Sojaöl durchgeführt wird.1. A process for the production of polyurethane, in which a polyisocyanate is reacted with a polyol, characterized in that the reaction of the polyisocyanate with the polyol is carried out in the presence of soybean oil. 2. Verfahren nach Anspruch 1, dadurch gekennzeichnet, dass das Sojaöl in einer Menge von 10 g bis 300 g, bezogen auf ein OH-Mol-Equivalent des Polyols, eingesetzt wird.2. The method according to claim 1, characterized in that the soybean oil is used in an amount of 10 g to 300 g, based on an OH mol equivalent of the polyol. 3. Verfahren nach Anspruch 1 oder 2, dadurch gekennzeichnet, dass das Mol-Verhältnis der NCO-Gruppen des Polyisocyanats zu den OH-Gruppen des Polyols 1 bis 4 : 1 beträgt .3. The method according to claim 1 or 2, characterized in that the molar ratio of the NCO groups of the polyisocyanate to the OH groups of the polyol is 1 to 4: 1. 4. Verfahren nach einem der vorstehenden Ansprüche, dadurch gekennzeichnet, dass als Polyol Rizinusöl verwendet wird.4. The method according to any one of the preceding claims, characterized in that castor oil is used as the polyol. 5. Verfahren nach Anspruch 1, dadurch gekennzeichnet, dass zur Bildung eines Präpolymeren mit freien Isocyanat- Gruppen das Polyisocyanat bei der Umsetzung mit dem Polyol und dem Sojaöl im Überschuss eingesetzt wird.5. The method according to claim 1, characterized in that the polyisocyanate is used in the reaction with the polyol and the soybean oil in excess to form a prepolymer with free isocyanate groups. 6. Verfahren nach Anspruch 5, dadurch gekennzeichnet, dass das Präpolymere mit einer Verbindung, die aciden Wasserstoff enthält, umgesetzt wird. 6. The method according to claim 5, characterized in that the prepolymer is reacted with a compound containing acidic hydrogen. 7. Verwendung des nach einem der vorstehenden Ansprüchen hergestellten Polyurethans zur Herstellung von Polyurethan-Schaumstoff.7. Use of the polyurethane produced according to one of the preceding claims for the production of polyurethane foam. 8. Verwendung nach Anspruch 7, dadurch gekennzeichnet, dass das Präpolymere nach Anspruch 6 zur Herstellung des Polyurethan-Schaumstoffs eingesetzt wird. 8. Use according to claim 7, characterized in that the prepolymer according to claim 6 is used for the production of the polyurethane foam.
PCT/EP1999/003959 1998-10-15 1999-06-08 Method for producing polyurethane Ceased WO2000023491A1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
AU46067/99A AU4606799A (en) 1998-10-15 1999-06-08 Method for producing polyurethane
EP99929155A EP1137686A1 (en) 1998-10-15 1999-06-08 Method for producing polyurethane

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
PT102214A PT102214B (en) 1998-10-15 1998-10-15 THE NATURAL SOYBEAN OIL IN POLYURETHANE MANUFACTURING
PT102214 1998-10-15

Publications (1)

Publication Number Publication Date
WO2000023491A1 true WO2000023491A1 (en) 2000-04-27

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EP (1) EP1137686A1 (en)
AU (1) AU4606799A (en)
PT (1) PT102214B (en)
WO (1) WO2000023491A1 (en)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1264850A1 (en) * 2001-06-07 2002-12-11 Bayer Corporation Polyurethane foams having improved heat sag and a process for their production
US6864296B2 (en) 1998-09-17 2005-03-08 Urethane Soy Systems Company Plastic material
US6962636B2 (en) 1998-09-17 2005-11-08 Urethane Soy Systems Company, Inc. Method of producing a bio-based carpet material
US6979477B2 (en) 2000-09-06 2005-12-27 Urethane Soy Systems Company Vegetable oil-based coating and method for application
US7063877B2 (en) 1998-09-17 2006-06-20 Urethane Soy Systems Company, Inc. Bio-based carpet material
US7084230B2 (en) 1998-09-17 2006-08-01 Urethane Soy Systems Company, Inc. Oxylated vegetable-based polyol having increased functionality and urethane materials formed using the polyol
WO2006108833A1 (en) * 2005-04-14 2006-10-19 Basf Aktiengesellschaft Method for producing polyurethane and polyisocyanurate rigid foam
WO2009026426A1 (en) * 2007-08-21 2009-02-26 Renosol Systems, Llc Isocyanato terminated precursor and method of making the same
US7595094B2 (en) 1998-09-17 2009-09-29 Urethane Soy Systems, Co. Vegetable oil-based coating and method for application
US9045581B2 (en) 2005-03-03 2015-06-02 Rhino Linings Corporation Polyols derived from a vegetable oil using an oxidation process
WO2025117005A1 (en) 2023-12-01 2025-06-05 Basf Se Bio-containing polyisocyanate prepolymers for increasing overall bio-content in polyurethane products

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB947973A (en) * 1961-03-28 1964-01-29 Beck & Company G M B H Dr Improvements in or relating to polyurethane lacquers
EP0256355A2 (en) * 1986-08-02 1988-02-24 Henkel Kommanditgesellschaft auf Aktien Polyurethane prepolymers from oleochemic polyols, their preparation and use

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB947973A (en) * 1961-03-28 1964-01-29 Beck & Company G M B H Dr Improvements in or relating to polyurethane lacquers
EP0256355A2 (en) * 1986-08-02 1988-02-24 Henkel Kommanditgesellschaft auf Aktien Polyurethane prepolymers from oleochemic polyols, their preparation and use

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7084230B2 (en) 1998-09-17 2006-08-01 Urethane Soy Systems Company, Inc. Oxylated vegetable-based polyol having increased functionality and urethane materials formed using the polyol
US7595094B2 (en) 1998-09-17 2009-09-29 Urethane Soy Systems, Co. Vegetable oil-based coating and method for application
US6864296B2 (en) 1998-09-17 2005-03-08 Urethane Soy Systems Company Plastic material
US6867239B2 (en) 1998-09-17 2005-03-15 Urethane Soy Systems Company Plastic material
US6881763B2 (en) 1998-09-17 2005-04-19 Urethane Soy Systems Company Plastic material
US6962636B2 (en) 1998-09-17 2005-11-08 Urethane Soy Systems Company, Inc. Method of producing a bio-based carpet material
US7063877B2 (en) 1998-09-17 2006-06-20 Urethane Soy Systems Company, Inc. Bio-based carpet material
US7537665B2 (en) 1998-09-17 2009-05-26 Urethane Soy Systems Company, Inc. Method for producing a bio-based carpet material
US6979477B2 (en) 2000-09-06 2005-12-27 Urethane Soy Systems Company Vegetable oil-based coating and method for application
US6649667B2 (en) 2001-06-07 2003-11-18 Bayer Polymers Llc Polyurethane foams having improved heat sag and a process for their production
EP1264850A1 (en) * 2001-06-07 2002-12-11 Bayer Corporation Polyurethane foams having improved heat sag and a process for their production
US9045581B2 (en) 2005-03-03 2015-06-02 Rhino Linings Corporation Polyols derived from a vegetable oil using an oxidation process
WO2006108833A1 (en) * 2005-04-14 2006-10-19 Basf Aktiengesellschaft Method for producing polyurethane and polyisocyanurate rigid foam
US7678936B2 (en) 2007-08-21 2010-03-16 Lear Corporation Isocyanato terminated precursor and method of making the same
WO2009026426A1 (en) * 2007-08-21 2009-02-26 Renosol Systems, Llc Isocyanato terminated precursor and method of making the same
WO2025117005A1 (en) 2023-12-01 2025-06-05 Basf Se Bio-containing polyisocyanate prepolymers for increasing overall bio-content in polyurethane products

Also Published As

Publication number Publication date
AU4606799A (en) 2000-05-08
PT102214A (en) 2000-04-28
EP1137686A1 (en) 2001-10-04
PT102214B (en) 2002-09-30

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