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 substancesInfo
- 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
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
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/22—Catalysts containing metal compounds
- C08G18/222—Catalysts containing metal compounds metal compounds not provided for in groups C08G18/225 - C08G18/26
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/92—Ketonic 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.
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)
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 |
-
0
- BE BE577999D patent/BE577999A/xx unknown
-
1958
- 1958-04-25 GB GB1319058A patent/GB869988A/en not_active Expired
-
1959
- 1959-04-25 FR FR793192A patent/FR1225213A/en not_active Expired
Cited By (25)
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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