GB919067A - Phosphorus containing polyurethane foams - Google Patents

Phosphorus containing polyurethane foams

Info

Publication number
GB919067A
GB919067A GB2489761A GB2489761A GB919067A GB 919067 A GB919067 A GB 919067A GB 2489761 A GB2489761 A GB 2489761A GB 2489761 A GB2489761 A GB 2489761A GB 919067 A GB919067 A GB 919067A
Authority
GB
United Kingdom
Prior art keywords
acid
acids
polyester
phosphorus
phosphorous
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
GB2489761A
Inventor
Raymond Richard Hindersinn
Michael Worsley
Blaine Orwell Schoepfle
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.)
Hooker Chemical Corp
Original Assignee
Hooker Chemical Corp
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
Application filed by Hooker Chemical Corp filed Critical Hooker Chemical Corp
Priority to GB2489761A priority Critical patent/GB919067A/en
Publication of GB919067A publication Critical patent/GB919067A/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
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30Low-molecular-weight compounds
    • C08G18/38Low-molecular-weight compounds having heteroatoms other than oxygen
    • C08G18/3878Low-molecular-weight compounds having heteroatoms other than oxygen having phosphorus

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)
  • Epoxy Resins (AREA)

Abstract

A process for the production of a fire resistant cellular reaction product comprises reacting (1) a hydroxyl-containing polymer having a hydroxyl number of between about 25 and 900, (2) an organic polyisocyanate, and (3) from 5 to 30% by weight, based on the weight of the hydroxyl-containing polymer of a phosphorus acid or a partially esterified phosphorus acid or mixtures thereof. The hydroxyl-containing polymer may be a polyester, polyether or mixtures thereof. As a modification an organic diisocyanate is first reacted with a polyester to form a prepolymer and this prepolymer is then reacted with a polyether and/or further polyester and with the phosphorus acid or partially esterified phosphorus acid. The polyesters may be prepared from malaeic, fumaric, phthalic, tetrachlorophthalic, oxalic, malonic, succinic, glutaric or adipic acids, or Diels-Alder adducts of hexahalocyclopentadiene and a polycarboxylic compound. As hydroxy compounds there may be used glycols, triols, pentaerythritol or a Diels-Alder adduct of a hexahalocyclopentadiene and a polyhydric alcohol. The polyethers are reaction products of a polyhydric alcohol or polycarboxylic acid with an epoxide such as ethylene, propylene, butylene or isobutylene oxides, 2,3-epoxyhexane, 3-ethyl-2,3-epoxyoctane, epichlorhydrin, epibromohydrin, styrene oxide, glycidyl ether, methyl glycidyl ether, phenyl glycidyl ether, butyl glycidyl sulphide, glycidylmethyl sulphone, glycidyl methacrylate or acrylate, benzoate, acetate, octanoate, or sorbate, glycidyl allyl phthalate, phenyl-(p-octadecyloxybenzoyl) ethylene oxide and compounds of the formulae <FORM:0919067/IV(a)/1> Gas is formed by reaction of the polyisocyanate with the phosphorus compound, but as an additional foaming agent there can be used fluorochlorohydrocarbons; tertiary alcohols in the presence of strong acids; secondary alcohols alone or with acids; polycarboxylic acids, or anhydrides, dimethylol ureas, polymethylol phenols, formic acid or tetrahydroxymethylphosphonium chloride. As phosphorus acids there are listed, phosphoric, phosphorous, and hypophosphorous acids and a number of phosphonic, phosphinic, and phosphonous acids, primary and secondary phosphates and phosphites, and primary phosphonates and phosphonites. Specified fillers and additives are clay, calcium sulphate, ammonium phosphate, dyes, fibrous glass, asbestos or synthetic fibres. In examples foams are prepared by reacting (1) (A) a mixture of a trimethylolpropane-propylene oxide reaction product, a polyester from trimethylolpropane and 1,4,5,6,7,7-hexachlorobicyclo-(2.2.1)-5-heptene-2,3-dicarboxylic acid and mono- and di-butyl phosphates with (B) a solution of trichlorofluoromethane and a reaction product of 1,4,5,6,7,7-hexachlorobicyclo-(2.2.1)-5-heptene-2,3-dicarboxylic acid and toluene 2.4- and 2.6-diisocyanates; (2) similar reactants but with the use of phosphorous acid in place of the butyl phosphates; (3) a mixture of a glycerine/adipic acid/1,4,5,6,7,7-hexachlorobicyclo-(2.2.1)-5-heptene-2, 3-dicarboxylic acid polyester, a trimethylolpropane/adipic acid polyester mono- and dibutyl phosphates and trichlorofluoromethane with a semi-prepolymer from a portion of the chlorine containing polyester and toluene diisocyanates; (4) an adipic acid/phthalic anhydride/trimethylolpropane polyester with other reactants and procedures as specified in Example (3). In other examples the procedure of Example (1) is followed using as the phosphorus compound (8) phosphoric acid, (9) phenylphosphonic acid, (10) dimethylphosphinic acid, (11) methylphosphonous acid, (12) phenylphosphoric acid, (13) methyl ethyl phosphoric acid, (14) butyl phosphorus acid. Specification 873,974 is referred to.ALSO:A process for the production of a fire-resistant cellular reaction product comprises reacting (1) a hydroxylcontaining polymer having a hydroxyl number of between about 25 and 900, (2) an organic polyisocyanate, and (3) from 5 to 30% by weight, based on the weight of the hydroxyl-containing polymer of a phosphorus acid or a partially esterified phosphorous acid or mixtures thereof. The hydroxyl-containing polymer may be a polyester, polyether or mixtures thereof. As a modification an organic diisocyanate is first reacted with a polyester to form a prepolymer and this is then reacted with a polyether and/or further polyester and with the phosphorous acid or partially esterified phosphorous acid. Components are listed for the preparation of the polyesters and include Diels-Alderd adducts of a bexahalocyclopentadiene with a polycarboxylic acid or with a polyhydric alcohol. Compounds list for reaction with polyalcohols or polycarboxylic acids in the preparation of polyethers include epoxides containing halogen, ether, sulphide, sulphone, ester, amino and sulphonamide groups. Gas is formed by the reaction of the polyisocyanate and the phosphorus compound, but as an additional foaming agent there can be used fluorochlorohydrocarbons; tertiary alcohols in the presence of p strong acids; secondary alcohols above or with acids; polycarboxylic acids or anhydrides, dimethylol ureas, polymethylol phenols, formic acid or tetrahydroxymethyl phosphorium chloride. As phosphorous acids these are listed phosphoric, phosphorous and hypophosphorous acids and a number of phosphonic, phosphinic and phosphonous acids primary and secondary phosphates and phosphites, and primary phosphonates and phosphonites. Specified fillers and additives are clay, calcium sulphate, ammonium phosphate, dyes, fibrous glass, asbestos or synthetic fibres. In Example (1) a foam is prepared (1) by reacting (A) a mixture of trimethylalpropane-propylene oxide reaction product, a polyester from trimethylolpropane and 1, 4, 5, 6, 7, 7-hexachlorobicyilo -(2, 2,1)-5-heptene -2, 3-decarboxylic acid and mono-and dibutyl phosphates with (B) a solution of trichlorofluoromethane and a reaction product of 1, 4, 5, 6, 7, 7- hexachlorobicyclo- (2.2.1)-5- heptene -2, 3- dicarboxylic acid and toluene -2, 4-and 2, 6- diisocyanates. In other examples the procedure of (1) is followed using as the phosphorus compound (8) phosphoric acid, (9) phenylphosphoric acid, (10) dimethylphosphinic acid, (11) methylphosphorous acid, (12) phenyl phosphoric acid, (13) methyl ethyl phosphoric acid, (14) butyl phosphorous acid. Specification 873,974 is referred to.
GB2489761A 1961-07-10 1961-07-10 Phosphorus containing polyurethane foams Expired GB919067A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB2489761A GB919067A (en) 1961-07-10 1961-07-10 Phosphorus containing polyurethane foams

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2489761A GB919067A (en) 1961-07-10 1961-07-10 Phosphorus containing polyurethane foams

Publications (1)

Publication Number Publication Date
GB919067A true GB919067A (en) 1963-02-20

Family

ID=10218992

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2489761A Expired GB919067A (en) 1961-07-10 1961-07-10 Phosphorus containing polyurethane foams

Country Status (1)

Country Link
GB (1) GB919067A (en)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3385801A (en) * 1964-05-05 1968-05-28 Monsanto Co Flame-resistant polyurethanes
US3424701A (en) * 1967-08-29 1969-01-28 Hooker Chemical Corp Polyurethane compositions
DE1301119B (en) * 1964-08-06 1969-08-14 Albright & Wilson Mfg Ltd Process for the production of polyurethanes
US3498936A (en) * 1964-05-27 1970-03-03 Hooker Chemical Corp Hydroxyalkylated phenol-sulfur halide resins and polyurethanes containing same
US3791914A (en) * 1972-01-26 1974-02-12 Ppg Industries Inc Laminated glass articles
US4666967A (en) * 1985-01-23 1987-05-19 Ciba-Geigy Corporation Flame retardants for polyurethanes
EP0853073A1 (en) * 1995-09-27 1998-07-15 Sanyo Chemical Industries Ltd. Inorganic-organic composite foam and process for the production thereof
US6610756B1 (en) 1997-07-08 2003-08-26 Sanyo Checmical Industries, Ltd. Inorganic/organic composite foam and process for producing the same
CN113698568A (en) * 2021-07-20 2021-11-26 佳化化学科技发展(上海)有限公司 Combined polyether, polyisocyanurate foam, preparation method and application thereof

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3385801A (en) * 1964-05-05 1968-05-28 Monsanto Co Flame-resistant polyurethanes
US3498936A (en) * 1964-05-27 1970-03-03 Hooker Chemical Corp Hydroxyalkylated phenol-sulfur halide resins and polyurethanes containing same
DE1301119B (en) * 1964-08-06 1969-08-14 Albright & Wilson Mfg Ltd Process for the production of polyurethanes
US3424701A (en) * 1967-08-29 1969-01-28 Hooker Chemical Corp Polyurethane compositions
US3791914A (en) * 1972-01-26 1974-02-12 Ppg Industries Inc Laminated glass articles
US4666967A (en) * 1985-01-23 1987-05-19 Ciba-Geigy Corporation Flame retardants for polyurethanes
EP0853073A1 (en) * 1995-09-27 1998-07-15 Sanyo Chemical Industries Ltd. Inorganic-organic composite foam and process for the production thereof
EP0853073A4 (en) * 1995-09-27 1998-11-25 Sanyo Chemical Ind Ltd Inorganic-organic composite foam and process for the production thereof
US6313186B1 (en) 1995-09-27 2001-11-06 Sanyo Chemical Industries, Ltd. Inorganic-organic composite foam and process for the production thereof
US6610756B1 (en) 1997-07-08 2003-08-26 Sanyo Checmical Industries, Ltd. Inorganic/organic composite foam and process for producing the same
CN113698568A (en) * 2021-07-20 2021-11-26 佳化化学科技发展(上海)有限公司 Combined polyether, polyisocyanurate foam, preparation method and application thereof

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