GB869988A - Catalytic process for the reaction of organic isocyanates with hydroxyl group-containing substances - Google Patents

Catalytic process for the reaction of organic isocyanates with hydroxyl group-containing substances

Info

Publication number
GB869988A
GB869988A GB1319058A GB1319058A GB869988A GB 869988 A GB869988 A GB 869988A GB 1319058 A GB1319058 A GB 1319058A GB 1319058 A GB1319058 A GB 1319058A GB 869988 A GB869988 A GB 869988A
Authority
GB
United Kingdom
Prior art keywords
pentanediono
manganese
zirconium
acetone
bis
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.)
Expired
Application number
GB1319058A
Inventor
Harry James Twitchett
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
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
Priority to BE577999D priority Critical patent/BE577999A/xx
Application filed by Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB1319058A priority patent/GB869988A/en
Priority to FR793192A priority patent/FR1225213A/en
Publication of GB869988A publication Critical patent/GB869988A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08Processes
    • C08G18/16Catalysts
    • C08G18/22Catalysts containing metal compounds
    • C08G18/222Catalysts containing metal compounds metal compounds not provided for in groups C08G18/225 - C08G18/26
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/92Ketonic chelates

Landscapes

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

Abstract

A process for the manufacture of urethane group-containing materials by reacting organic isocyanates with hydroxyl group-containing substances is characterized in that the reaction is performed in the presence of a complex of a b -diketone with manganese, thorium, titanium or zirconium. The complexes may be formed by reacting an aqueous solution of a salt of the metal, with a b -diketone, such as acetyl-acetone, benzoylacetone, dibenzoylmethane, propionyl-acetone, trifluoroacetylacetone, 3-ethylacetyl-acetone, 3-cyanoacetyl-acetone and 2-thenoyl-acetone. The catalysts may be used in admixture with p other catalysts, e.g. tertiary amines. The process is of use in the manufacture of foamed or non-foamed polyurethanes from diisocyanates (with which may be mixed triisocyanates) and polyethers, polyesters or polyesteramides. The polyesters can be prepared from succinic, adipic, glutaric, suberic, azelaic, sebacic, alkyladipic, citric, phthalic, isophthalic, terephthalic and trimesic acids, and the polybasic acids obtained by polymerization of unsaturated long-chain fatty acids. Monobasic acids and ricinoleic and dihydroxystearic acids can also be used. Glycols and higher polyalcohols for the ester preparation are listed. Ethylene diamine, hexamethylene diamine, ethanolamine, phenyldiamines and benzidine can be used in preparing the polyesteramide. The polyethers may be those prepared by the processes described in Specification 733,624 or those obtained by adding an alkylene oxide or succession of alkylene oxides with water, diols, glycerol, trimethylolpropane, triethanolamine, polyallyl alcohol, ethylene diamine, 3-hydroxymethylcyclobutane, glycidol, ricinoleic acid, dihydroxystearic acid and carbohydrates and their partially esterified or etherified derivatives. Reaction of a polyisocyanate with a hydroxyl-containing compound from a polyisocyanate and a hydroxy-compound can also be catalysed. In Examples (3) phenyl isocyanate and polypropylene glycol are reacted in the presence of bis-(2 : 4-pentanediono) manganese (II); (9) polypropylene glycol, water, and toluene-2, 4 and 2, 6-diisocyanates containing a small proportion of ethyl cellulose are reacted in the presence of tris-(2 : 4-pentanediono) manganese (III) to give a foamed product; (11) a polyester from glycerol, adipic acid and ethylene glycol, is mixed in cyclohexanone and methyl ethyl ketone with 2 : 4-tolylene diisocyanate. The gelation time of the lacquer on adding the following catalysts is given: dimethylcyclohexyl amine, bis-(2 : 4-pentanediono) manganese (II), tris-(2 : 4-pentanediono) managnese (III), bis-(1 : 3-diphenyl-1 : 3-diono) manganese(II), tetra-kis-(2 : 4-pentanediono)-zirconium (IV), tetra-kis-(3-cyano-2 : 4-pentanediono)-zirconium (IV), tetrakis-(2 : 4-pentanediono) thorium (IV), and a mixture of tetrakis-2 : 4-pentanediono) zirconium (IV) and dimethylcyclohexylamine; (12) A foam is prepared by mixing a glycerol-propylene oxide reaction product, a pyridine solution of bis-(2 : 4-pentanediono) manganese (II), an octylphenol-ethylene oxide reaction product, the sodium salt of sulphonated methyl oleate and water, and adding a diphenyl-methane diisocyanate, obtained by phosgenating an aniline/formaldehyde reaction product.ALSO:A process for the manufacture of urethane group-containing materials by reacting organic isocyanates with hydroxyl group-containing substances is characterised in that the reaction is performed in the presence of a complex of a beta-diketone with manganese, thorium, titanium or zirconium. Examples of b -diketones are acetylacetone, benzoylacetone, dibenzoylmethane, propionylacetone, trifluoroacetylacetone, 3-ethylacetylacetone, 3-cyanoacetyl acetone and 2-thenylacetone. In Example (1) an aqueous ammoniacal solution of acetylacetone is reacted in a nitrogen atmosphere with manganese acetate to give bis-(2:4-pentanediono) manganese (II). In further examples there are reacted (4) aqueous manganese acetate and ethanolic dibenzoylmethane; (5) acetylacetone and thorium nitrate; (6) zirconyl chloride (ZrOCl2) and acetyl-acetone ;(7) titanic chloride and acetylacetone; (8) acetylacetone and tetra-isopropyl orthotitanate (to give a product diisopropoxy-bis-(2:4-pentanediono) titanium (IV). The products are used in preparing polyurethanes (see Group IV(a) and also in accelerating the reaction between phenyl isocyanate and (1) glycol, (2) n-butanol (3) polypropylene glycol. Specification 733,624 is referred to.ALSO:A process for the manufacture of urethane group-containing materials such as polyurethane foams by reacting organic isocyanates with hydroxyl group-containing substances is characterised in that the reaction is performed in the presence of a complex of a b -diketone with manganese, thorium, titanium or zirconium. The complexes may be formed by reacting on aqueous solution of a salt of the metal, with a b -diketone, such as acetyl-acetone, benzoylacetone, dibenzoylmethane, propionylacetone, triflouroacetylacetone, 3-ethylacetylacetone, 3-cyanoacetylacetone and 2-thenoylacetone. The catalysts may be used in admixture with other catalysts e.g. tertiary amines. The polyurethanes are prepared from diisocyanates (with which may be mixed triisocyanates) and polyethers, polyesters or polyesteramides. The polyesters can be prepared from succinic, adipic, glutaric, suberic, azelaic, sebacic, alkyladipic, citric, phthalic, isophthalic, terephthalic and trimesic acids, and the polybasic acids obtained by polymerisation of unsaturated long-chain fatty acids. Monobasic acids and ricinoleic and dihydroxystearic acids can also be used. Glycols and higher polyalcohols for the ester preparation are listed. Ethylene diamine, hexamethylene diamine, ethanolamine, phenyldiamines and benzidine can be used in preparing the polyesteramide. The polyethers may be those prepared by the processes described in Specification 733,624 or those obtained by adding an alkylene oxide or succession of alkylene oxides with water, diols, glycerol, trimethylpropane, triethanolamine, polyallyl alcohol, ethylene diamine, 3-hydroxymethylcyclobutane, glycidol, ricinoleic acid, dihydroxystearic acid and carbohydrates and their partially esterified or etherified derivatives. In Examples (9) polyproylene glycol, water, and toluene -2,4 and 2,6 diisocyanates containing a small proportion of ethyl cellulose are reacted in the presence of tris-(2: 4- pentanediono) manganese (III) to give a foamed product; (12) A foam is prepared by mixing a glycerol-propylene oxide reaction product, a pyridine solution of bis-(2: 4-pentanediono) manganese (II), an octylphenolethylene oxide reaction product, the sodium salt of sulphonated methyl oleate and water, and adding a diphenylmethane diisocyanate, obtained by phosgenating an amiline/formaldehyde reaction product. Other catalysts mentioned are tetrakis-(2: 4-pentanediono)zirconium (IV), bis-1 : 3-diphenyl-1 : 3-diono) manganese (II), tetrakis-(3-cyano-2: 4-pentanediono) zirconium (IV), tetrakis-(2: 4-pentanediono) Thorium (IV), and a mixture of tetrakis-(2: 4-pentanediono) zirconium (IV) and dimethylcyclohexylamine.
GB1319058A 1958-04-25 1958-04-25 Catalytic process for the reaction of organic isocyanates with hydroxyl group-containing substances Expired GB869988A (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
BE577999D BE577999A (en) 1958-04-25
GB1319058A GB869988A (en) 1958-04-25 1958-04-25 Catalytic process for the reaction of organic isocyanates with hydroxyl group-containing substances
FR793192A FR1225213A (en) 1958-04-25 1959-04-25 Catalytic process of reactions between organic isocyanates and polyesters, polyesteramides

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1319058A GB869988A (en) 1958-04-25 1958-04-25 Catalytic process for the reaction of organic isocyanates with hydroxyl group-containing substances

Publications (1)

Publication Number Publication Date
GB869988A true GB869988A (en) 1961-06-07

Family

ID=10018493

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1319058A Expired GB869988A (en) 1958-04-25 1958-04-25 Catalytic process for the reaction of organic isocyanates with hydroxyl group-containing substances

Country Status (3)

Country Link
BE (1) BE577999A (en)
FR (1) FR1225213A (en)
GB (1) GB869988A (en)

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0109014A1 (en) * 1982-11-05 1984-05-23 E.I. Du Pont De Nemours And Company Titanium ester compositions having depressed freezing points
WO1998015585A1 (en) * 1996-10-05 1998-04-16 Tioxide Specialties Limited Catalysts
WO1998041322A1 (en) * 1997-03-19 1998-09-24 King Industries, Inc. Novel zirconium urethane catalysts
US6288200B1 (en) 1995-11-06 2001-09-11 Imperial Chemical Industries Plc Polyisocyanate composition
WO2002062738A1 (en) * 2001-02-02 2002-08-15 Roche Vitamins Ag Process for the purification of 1,3-diketones
AU751731B2 (en) * 1995-11-06 2002-08-29 Huntsman International Llc Polyisocyanate composition
US7485729B2 (en) 2004-08-12 2009-02-03 King Industries, Inc. Organometallic compositions and coating compositions
WO2009063245A2 (en) * 2007-11-16 2009-05-22 Johnson Matthey Plc Method and catalyst for the manufacture of a polyurethane
WO2010057824A1 (en) * 2008-11-21 2010-05-27 Basf Se Metal oxo complex as catalyst for polyurethane curing
US8912113B2 (en) 2011-03-06 2014-12-16 King Industries, Inc. Compositions of a metal amidine complex and second compound, coating compositions comprising same
CN109897161A (en) * 2019-03-04 2019-06-18 武汉科技大学 Polyurethane elastomer and preparation method thereof is answered in a kind of hot repair containing ketal structure
CN110283063A (en) * 2019-06-11 2019-09-27 中山华明泰科技股份有限公司 A kind of preparation method and application of Acetylacetone lanthanum
CN114671749A (en) * 2022-04-01 2022-06-28 国科广化韶关新材料研究院 Preparation method and application of zirconium-containing environment-friendly polyurethane catalyst
CN117720956A (en) * 2023-12-12 2024-03-19 东莞市唯纳孚润滑科技有限公司 Low-noise lubricating grease with good shearing resistance and preparation method thereof

Cited By (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0109014A1 (en) * 1982-11-05 1984-05-23 E.I. Du Pont De Nemours And Company Titanium ester compositions having depressed freezing points
US6288200B1 (en) 1995-11-06 2001-09-11 Imperial Chemical Industries Plc Polyisocyanate composition
AU751731B2 (en) * 1995-11-06 2002-08-29 Huntsman International Llc Polyisocyanate composition
EP0859805B1 (en) * 1995-11-06 2003-04-02 Huntsman International Llc Polyisocyanate composition for binding lignocellulosic material
CN1109700C (en) * 1995-11-06 2003-05-28 亨茨曼Ici化学品有限公司 Polyisocyantates composition
WO1998015585A1 (en) * 1996-10-05 1998-04-16 Tioxide Specialties Limited Catalysts
WO1998041322A1 (en) * 1997-03-19 1998-09-24 King Industries, Inc. Novel zirconium urethane catalysts
US5846897A (en) * 1997-03-19 1998-12-08 King Industries, Inc. Zirconium urethane catalysts
US5965686A (en) * 1997-03-19 1999-10-12 King Industries, Inc. Zirconium urethane catalysts
EP1163956A1 (en) * 1997-03-19 2001-12-19 King Industries, Inc. Urethane catalyst based on zirconium acetylacetonate
WO2002062738A1 (en) * 2001-02-02 2002-08-15 Roche Vitamins Ag Process for the purification of 1,3-diketones
US6844470B2 (en) 2001-02-02 2005-01-18 Roche Vitamins Inc. Process for the purification of 1,3-diketones
US7485729B2 (en) 2004-08-12 2009-02-03 King Industries, Inc. Organometallic compositions and coating compositions
US8088846B2 (en) 2004-08-12 2012-01-03 King Industries, Inc. Organometallic compositions and coating compositions
US9006316B2 (en) 2004-08-12 2015-04-14 King Industries, Inc. Organometallic compositions and coating compositions
WO2009063245A2 (en) * 2007-11-16 2009-05-22 Johnson Matthey Plc Method and catalyst for the manufacture of a polyurethane
WO2009063245A3 (en) * 2007-11-16 2009-07-16 Johnson Matthey Plc Method and catalyst for the manufacture of a polyurethane
WO2010057824A1 (en) * 2008-11-21 2010-05-27 Basf Se Metal oxo complex as catalyst for polyurethane curing
US8912113B2 (en) 2011-03-06 2014-12-16 King Industries, Inc. Compositions of a metal amidine complex and second compound, coating compositions comprising same
CN109897161A (en) * 2019-03-04 2019-06-18 武汉科技大学 Polyurethane elastomer and preparation method thereof is answered in a kind of hot repair containing ketal structure
CN109897161B (en) * 2019-03-04 2021-03-02 武汉科技大学 Heat-repairing polyurethane elastomer containing ketal structure and preparation method thereof
CN110283063A (en) * 2019-06-11 2019-09-27 中山华明泰科技股份有限公司 A kind of preparation method and application of Acetylacetone lanthanum
CN110283063B (en) * 2019-06-11 2020-06-16 中山华明泰科技股份有限公司 Preparation method and application of lanthanum acetylacetonate
CN114671749A (en) * 2022-04-01 2022-06-28 国科广化韶关新材料研究院 Preparation method and application of zirconium-containing environment-friendly polyurethane catalyst
CN117720956A (en) * 2023-12-12 2024-03-19 东莞市唯纳孚润滑科技有限公司 Low-noise lubricating grease with good shearing resistance and preparation method thereof

Also Published As

Publication number Publication date
BE577999A (en)
FR1225213A (en) 1960-06-29

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