GB843841A - Polyurethane foams - Google Patents
Polyurethane foamsInfo
- Publication number
- GB843841A GB843841A GB2925057A GB2925057A GB843841A GB 843841 A GB843841 A GB 843841A GB 2925057 A GB2925057 A GB 2925057A GB 2925057 A GB2925057 A GB 2925057A GB 843841 A GB843841 A GB 843841A
- Authority
- GB
- United Kingdom
- Prior art keywords
- polyisocyanate
- diisocyanate
- monomeric
- xylylene
- polymer
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
- C08G59/4014—Nitrogen containing compounds
- C08G59/4028—Isocyanates; Thioisocyanates
-
- 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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
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
The invention comprises solutions in organic monomeric polyisocyanates of organic polymeric polyisocyanates which have at least one isocyanuric acid ring. It also comprises a process for the production of a polyurethane plastic by reacting an organic compound having at least two hydrogen atoms capable of reacting with a polyisocyanate with a solution in a monomeric organic polyisocyanate of an organic polymeric polyisocyanate which has at least one isocyanuric acid ring. The polyisocyanate polymer can be prepared by heating a monomeric organic polyisocyanate in the presence of a catalyst containing a tertiary amine and a carbamic acid ester mono-substituted on the nitrogen atom. The carbamic acid ester may be added as such or may be formed by adding to the reaction mixture for instance methanol, ethanol, butanol or benzyl alcohol. A mono-isocyanate may be included with the polyisocyanate in the polymerization mixture. provided the product has more than one NCO group per molecule. Before the polymerization the monomeric polyisocyanate may be reacted with compounds such as alcohols (saturated or unsaturated), phenols, glycols, polyfunctional alcohols, primary or secondary mono- or polyfunctional amines, amino-alcohols or aminophenols, provided that at least 25% unreacted-NCO groups are left. Polymerization can also be effected by the process of German Specification 951,168 or at elevated temperatures by the action of such compounds as tin tetrachloride, iron chloride and the copper or zinc complex of the Schiff's bases from stearylamine and salicyl aldehyde. Phenyl, tolyl, p-nitrophenyl, p-chlorophenyl, a -naphthyl, and benzyl isocyanates, tetra, hexa and decamethylene, m- and p-xylylene, 1- tertiary butyl -3, 5-xylylene, 4, 6-dimethyl -1, 3-xylylene, cyclohexyl-1, 4, dicyclohexyl methane- 4, 41, m- or p-phenylene, toluene, 2, 6- diethylbenzene-1, 4 diphenylmethane, diphenyldimethylmethane-4, 41, 3, 31-dimethoxydiphenylmethane and naphthalene -1, 5- diisocyanates, and 1- methyl benzene -2, 4, 6-, and triphenylmethane triisocyanates are suitable for polymerization. The polymer can be dissolved in 1-methyl -phenyl 2, 4-, 2, 6- or 3, 5- diisocyanate, tetra hexa or decamethylene diisocyanate, m- or p-xylylenediisocyanate or 2, 4, 41-diphenylether triisocyanate. In the preparation of polyurethanes the polyisocyanate solution can be reacted with polyesters polyamides, polyalkylene ether or thioether glycols, ethers from polyols and styrene oxide, epoxy resins, hydrogenation products of olefincarbon monoxide copolymers and phenolformaldehyde resins reacted with alkylene oxides. The polyesters may contain heterocyclic rings and double or triple bonds. In preparing foams a one or two stage process can be used. Fire proofing agents and plasticizers such as trichloralkyl phosphate, chlorinated paraffins and esters can be added. In an example (1) a mixture of an adipic acid/phthalic anhydride/hexanetriol polyester and an adipic acid/hexantriol/1, 3-butylene glycol polyester is mixed with adipic acid diethyl aminoethyl ester and aqueous sodium salt of castor oil sulphate and converted to a foam by adding polymerized toluylene -2, 4-diisocyanate dissolved in monomeric toluylene diisocyanate. The polymer is obtained by heating toluylene -2, 4- diisocyanate in the presence of ethanol and a reaction product of phenyl isocyanate and methyl diethanolamine. In other examples there are used polyesters prepared from reactants selected additionally from glycerine, diethylene glycol and oleic acid; a hydrogenated ethylenepropylenecarbon monooxide polymer; or a polypropylene ether glycol. Other polyisocyanates illustrated are obtained by heating in the presence of tertiary amine from methyl diethanolamine and phenyl isocyanate a reaction product still containing NCO groups of toluylene diisocyanate with (6) 2, 2, 4- trimethylpentenrediol (8) 4, 41-dihydroxy-diphenylmethane (9) 2, 2-diemethyl propanediol 1-, 3; (10) oleyl alcohol; (11) hydrogenated 4, 41- dioxydiphenyl dimethylmethane.ALSO:The invention comprises solutions in organic monomeric polyisocyanates of organic polymeric polyisocyanates which contain at least one isocyanueric acid ring. Such solutions are useful in the preparation of polyurethane plastics, particularly foamed products (see Groups IV(a) and V). The polyisocyanate polymer can be prepared by heating a monomeric polyisocyanate in the presence of a catalyst containing a tertiary amine and a carbamic acid ester mono - substituted on the nitrogen atom. The carbamic acid ester may be added as such or may be formed by adding to the reaction mixture for instance methanol, ethanol, butanol or benzyl alcohol. A monoisocyanate may be included with the polyisocyanate in the polymerisation mixture, provided that the product has more than one NCO group per molecule. Before the polymerisation the monomeric polyisocyanate may be reacted with compounds such as alcohols (saturated or unsaturated), phenols, glycols, polyfunctional alcohols, primary or secondary mono- or polyfunctional amines, aminoalcohols or aminophenols, provided that at least 25% free NCO groups are left. Polymerisation can also be effected by the process of German Specification 951,168 or by the action at elevated temperatures of such compounds as tin tetrachloride, iron chloride and the copper or zinc complex of the Schiff's base from stearylamine and salicylaldehyde. Phenyl, tolyl, p-nitrophenyl, p-chlorophenyl, a -naphthyl and benzyl isocyanates, tetra, hexa and decamethylene, m and p-xylylene, 1-tertiary butyl-3, 5-xylylene, 4,6-dimethyl- 1,3-xylylene, cyclohexyl-1,4, dicyclohexylmethane -4,41, m or p-phenylene, tolylene, 2.6-diethylbenzene - 1,4-, diphenylmethane, or diphenyldimethylmethane -4,41, 3,31-dimethoxydiphenylmethane and naphthalene-1,5-diisocyanates and 1-methylbenzene-2,4,6 and triphenylmethane triisocyanate are suitable for polymerizations. The polymer can be dissolved in 1-methyl-phenyl-2,4, 2,6 or 3,5-diisocyanate tetra, hexa or decamethylene diisocyanate, m- or p-xylylene diisocyanate or 2,3,41 - diphenylether triisocyanate. In example (1) polyisocyanates are prepared by heating tolylene-2,4-diisocyanate in the presence of ethanol and a reaction product of phenyl isocyanate and methyl diethanolamine. Other polymeric polyisocyanates are prepared by heating in the presence of a tertiary amine from methyl diethanolamine a phenyl isocyanate a reaction product still containing NCO groups of toylene diisocyanate with (6) 2,2,4-trimethylpentenediol; (8) 4,41-dihydroxydiphenylmethane; (9) 2,2-dimethylpropanediol-1,3; (10) oleyl alcohol; (11) hydrogenated 4,41-dioxydiphenyl dimethylmethane.ALSO:A process for the production of a polyurethane plastic comprises reacting an organic compound having at least two hydrogen atoms capable of reacting with a polyisocyanate with a solution in a monomeric organic polyisocyanate of an organic polymeric polyisocyanate which has at least one isocyanuric acid ring. The process is of advantage in the production of foamed products. The polyisocyanate polymer can be prepared by heating a monomeric organic polyisocyanate in the presence of a catalyst containing a tertiary amine and a carbamic acid ester mono-substituted on the nitrogen atom (see Group IV(b)). A monoisocyanate may be included with the polyisocyanate in the polymerisation mixture. Before the polymerisation the monomeric polyisocyanate may be reacted with compounds such as alcohols, primary or secondary amines, amino-alcohols, or amino-phenols provided that at least 25% unreacted NCO groups are left. Phenyl, tolyl, p-nitrophenyl, p-chlorophenyl, a -naphthyl, and benzyl isocyanates, tetra, hexa, and decamethylene, m- and p-xylylene, 1-tertiary butyl-3, 5-xylylene, 4,6-dimethyl-1, 3-xylylene, cyclohexyl-1,4, dicyclohexylmethane-4, 41, m- or p-phenylene, tolylene, 2, 6-diethylenbenzene1, 4-, diphenylmethane, diphenyldmethylmethane-4, 41, 3, 31-dimethoxydiphenylmethane and naphthalene-1, 5- diisocyanates and 1-methylbenzene-2, 4, 6,- and triphenylmethane triisocyanate are suitable for polymerisation. The polymer can be dissolved in 1-methylphenyl- 2, 4, 2, 6-, or 3, 5- diisocyanate, tetra orhexa ordecamethylene diisocyanate, m- or p-xylylenediisocyanate or 2, 4, 41-diphenyl-ether triisocyanate. In the preparation of polyurethanes the polyisocyanate solution can be reacted with ethers from polyols and styrene oxide, polyesters, polyamides, polyalkylene ether or thioether glycols, epoxy resins, hydrogenated products of olefin-carbon monoxide copolymers and phenolformaldehyde resins reacted with alkylene oxides. The polyesters may contain heterocyclic rings or double or triple bonds. In preparing foams a one or two stage process can be used. Fire-proofing agents and plasticisers such as trichloroalkyl phosphate, chlorinated paraffins and esters can be added. In an example (1) a mixture of an adipic acid/phthalic anhydride/hexanetriol/polyester and an adipic acid/hexanetriol/1, 3-butylene glycol polyester is mixed with adipic acid diethylaminoethyl ester and aqueous sodium salt of castor sulphate and converted to a foam by adding polymerised toluylene -2, 4-diisocyanate dissolved in monomeric toluylene diisocyanate. The polymer is obtained by heating toluylene-2, 4-diisocyanate in the presence of ethanol and a reaction product of phenyl isocyanate and methyl diethanolamine. In other examples there are used polyesters prepared from reactants selected additionally from glycerine diethylene glycol andolein acid; a hydrogenated ethylene-propylene-carbon monoxide polymer; or a polypropylene ether glycol. Other polyisocyanates are obtained by heating in the presence of a tertiary amine from methyl diethanolamine and phenyl isocyanate a reaction product still containing NCO groups of toluylene diisocyanate with (6) 2, 2, 4-trimethylpentenediol; (8) 4, 41-
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEF21339A DE1022789B (en) | 1956-09-29 | 1956-09-29 | Process for the production of foams from polyoxy and / or polycarboxyl compounds and polyisocyanates |
Publications (1)
Publication Number | Publication Date |
---|---|
GB843841A true GB843841A (en) | 1960-08-10 |
Family
ID=7090034
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2925057A Expired GB843841A (en) | 1956-09-29 | 1957-09-17 | Polyurethane foams |
Country Status (3)
Country | Link |
---|---|
DE (1) | DE1022789B (en) |
FR (1) | FR1183538A (en) |
GB (1) | GB843841A (en) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3516950A (en) * | 1965-04-29 | 1970-06-23 | Ici Ltd | Foamed polymers |
US3993608A (en) * | 1974-06-27 | 1976-11-23 | Minnesota Mining And Manufacturing Company | Poly(urethane-isocyanurate) foams containing hollow glass spheres |
US8042864B2 (en) | 2007-09-26 | 2011-10-25 | Bayer Materialscience Ag | Roof module for a motor vehicle |
CN109836551A (en) * | 2019-01-28 | 2019-06-04 | 上海鸿得聚氨酯有限公司 | A kind of polyurethane sport protection foam spacer composition and preparation method thereof |
US10699828B2 (en) | 2012-06-06 | 2020-06-30 | !Obac Limited | Magnetic floor surface |
CN114163609A (en) * | 2021-11-29 | 2022-03-11 | 万华化学(宁波)有限公司 | Polyisocyanate composition, preparation method thereof and coating composition |
US12091543B2 (en) | 2019-05-24 | 2024-09-17 | Covestro Intellectual Property Gmbh & Co. Kg | Process for producing polyoxyalkylene-polyol mixtures |
Families Citing this family (37)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE596036A (en) * | 1959-10-15 | |||
DE2637170A1 (en) * | 1976-08-18 | 1978-02-23 | Bayer Ag | PROCESS FOR THE PRODUCTION OF ISOCYANURATE GROUPS AND PLASTICS CONTAINING URETHANE GROUPS |
DE3244407A1 (en) * | 1982-12-01 | 1984-06-07 | Bayer Ag, 5090 Leverkusen | NEW POLYISOCYANATE MIXTURES, A METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS A BUILD-UP COMPONENT IN THE PRODUCTION OF POLYURETHANE PLASTICS |
US6005062A (en) | 1998-07-02 | 1999-12-21 | 3M Innovative Properties Company | Secondary aspartic acid amide esters |
ES2860724T3 (en) | 2004-05-24 | 2021-10-05 | Hontek Corp | Abrasion resistant coatings |
EP2502679B1 (en) | 2005-12-14 | 2017-11-22 | Hontek Corporation | Method for protecting and repairing an airfoil Surface |
US20080159870A1 (en) | 2006-12-14 | 2008-07-03 | Hontek Corporation | Method and coating for protecting and repairing an airfoil surface using molded boots, sheet or tape |
US8399595B2 (en) | 2007-07-23 | 2013-03-19 | Dow Global Technologies Llc | Two part polyurethane curable composition having substantially consistent G-modulus across the range of use temperatures |
DE102008051882A1 (en) | 2008-10-16 | 2010-04-29 | Bayer Materialscience Ag | Process for the preparation of polyetherester polyols |
US10239985B2 (en) | 2008-12-23 | 2019-03-26 | Covestro Llc | Polymer polyols comprising a natural oil base polyol, polyurethane foams comprising these polymer polyols and processes for their preparation |
US20110135832A1 (en) | 2009-12-04 | 2011-06-09 | Basf Coatings Ag | Method and composition for refinish coatings |
EP2630177B1 (en) | 2010-10-20 | 2015-08-12 | BASF Coatings GmbH | Scratch-resistant refinish clearcoat |
WO2012084760A1 (en) | 2010-12-20 | 2012-06-28 | Bayer Materialscience Ag | Method for producing polyether ester polyols |
US20120163981A1 (en) | 2010-12-22 | 2012-06-28 | Hong Shek C | Method and coating for protecting and repairing an airfoil surface |
WO2013127850A1 (en) | 2012-02-29 | 2013-09-06 | Bayer Intellectual Property Gmbh | 2-k pultrusion formulation and process |
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US20160312091A1 (en) | 2013-12-23 | 2016-10-27 | Dow Global Technologies Llc | Adhesive Containing High Solid Copolymer Polyol Polyurethane Prepolymer |
EP2894180A1 (en) | 2014-01-08 | 2015-07-15 | Bayer MaterialScience AG | Polymer Polyols comprising a Polyether Carbonate Polyol as the Base Polyol |
DE202014101620U1 (en) | 2014-04-07 | 2014-04-29 | Franken Systems Gmbh | Container with 2-component polyurea synthetic resins |
DE102015108232A1 (en) | 2015-05-26 | 2016-12-01 | Franken Systems Gmbh | Process for the moisture-resistant primer of mineral substrates |
DE102015110841A1 (en) | 2015-07-06 | 2017-01-12 | Franken Systems Gmbh | Use of a reactive system for building waterproofing and structural waterproofing |
WO2017112012A2 (en) | 2015-09-17 | 2017-06-29 | Jerez Roberto Velozzi | Load-bearing composite panels, materials, products, and processes to make and use same |
WO2018046335A1 (en) | 2016-09-08 | 2018-03-15 | Basf Coatings Gmbh | Radiation-curable hyperbranched polymers with dicarboxylic acid cores |
WO2018046334A1 (en) | 2016-09-08 | 2018-03-15 | Basf Coatings Gmbh | Coatings with radiation-curable hyperbranched polymers |
US10689541B2 (en) | 2016-09-15 | 2020-06-23 | Basf Coatings Gmbh | Coatings with wax-modified hyperbranched and flexible hyperbranched polyols |
US20190106592A1 (en) | 2017-10-11 | 2019-04-11 | Basf Coatings Gmbh | Hyperbranched polymers for organic pigment dispersions and water-sensitive pigments |
CN111670112B (en) | 2018-02-02 | 2022-12-20 | 巴斯夫欧洲公司 | Simultaneous optimization of fiber sizing in-line with pultrusion process |
WO2019211127A1 (en) | 2018-04-30 | 2019-11-07 | Evonik Degussa Gmbh | Polyurea compositions from polyaspartic esters and secondary heterocyclic amines derived aspartic esters |
EP3838963A1 (en) | 2019-12-17 | 2021-06-23 | Covestro Deutschland AG | Method for producing polyoxyalkylene polyesterpolyols |
CA3162657A1 (en) | 2019-12-30 | 2021-07-08 | Basf Coatings Gmbh | Coatings containing branched polyester polyols as plasticizers |
JP2023539342A (en) | 2020-08-28 | 2023-09-13 | ビーエーエスエフ コーティングス ゲゼルシャフト ミット ベシュレンクテル ハフツング | Solvent-based two-component anticorrosive coating composition |
WO2022060685A1 (en) | 2020-09-15 | 2022-03-24 | Dow Global Technologies Llc | Low odor polyurethane adhesives |
WO2022090358A1 (en) | 2020-10-28 | 2022-05-05 | Basf Se | Production of a polyester polyol with low voc emission |
WO2022096390A1 (en) | 2020-11-06 | 2022-05-12 | Covestro Deutschland Ag | Method for producing a polyol mixture |
EP4388053A1 (en) | 2021-08-17 | 2024-06-26 | Evonik Operations GmbH | Polyurea compositions from polyaspartic esters and 2-substituted butanedioic acid esters |
WO2023057328A1 (en) | 2021-10-07 | 2023-04-13 | Covestro Deutschland Ag | Process for preparing polyoxyalkylene polyester polyols |
-
1956
- 1956-09-29 DE DEF21339A patent/DE1022789B/en active Pending
-
1957
- 1957-09-17 GB GB2925057A patent/GB843841A/en not_active Expired
- 1957-09-28 FR FR1183538D patent/FR1183538A/en not_active Expired
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3516950A (en) * | 1965-04-29 | 1970-06-23 | Ici Ltd | Foamed polymers |
US3993608A (en) * | 1974-06-27 | 1976-11-23 | Minnesota Mining And Manufacturing Company | Poly(urethane-isocyanurate) foams containing hollow glass spheres |
US8042864B2 (en) | 2007-09-26 | 2011-10-25 | Bayer Materialscience Ag | Roof module for a motor vehicle |
US10699828B2 (en) | 2012-06-06 | 2020-06-30 | !Obac Limited | Magnetic floor surface |
US10720270B2 (en) | 2012-06-06 | 2020-07-21 | !Obac Limited | Magnetic floor surface |
CN109836551A (en) * | 2019-01-28 | 2019-06-04 | 上海鸿得聚氨酯有限公司 | A kind of polyurethane sport protection foam spacer composition and preparation method thereof |
US12091543B2 (en) | 2019-05-24 | 2024-09-17 | Covestro Intellectual Property Gmbh & Co. Kg | Process for producing polyoxyalkylene-polyol mixtures |
CN114163609A (en) * | 2021-11-29 | 2022-03-11 | 万华化学(宁波)有限公司 | Polyisocyanate composition, preparation method thereof and coating composition |
CN114163609B (en) * | 2021-11-29 | 2024-05-03 | 万华化学(宁波)有限公司 | Polyisocyanate composition, preparation method thereof and coating composition |
Also Published As
Publication number | Publication date |
---|---|
FR1183538A (en) | 1959-07-08 |
DE1022789B (en) | 1958-01-16 |
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