GB904700A - Halogen-containing polyurethane foams and method of preparation - Google Patents

Halogen-containing polyurethane foams and method of preparation

Info

Publication number
GB904700A
GB904700A GB2086060A GB2086060A GB904700A GB 904700 A GB904700 A GB 904700A GB 2086060 A GB2086060 A GB 2086060A GB 2086060 A GB2086060 A GB 2086060A GB 904700 A GB904700 A GB 904700A
Authority
GB
United Kingdom
Prior art keywords
reaction product
polyhydric alcohol
hexahalocyclopentadiene
epoxide
polycarboxylic
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
GB2086060A
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
Priority claimed from US821722A external-priority patent/US3036999A/en
Priority claimed from US853689A external-priority patent/US3055850A/en
Priority claimed from US853688A external-priority patent/US3055849A/en
Priority claimed from US853687A external-priority patent/US3146220A/en
Application filed by Hooker Chemical Corp filed Critical Hooker Chemical Corp
Publication of GB904700A publication Critical patent/GB904700A/en
Expired legal-status Critical Current

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
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/81—Unsaturated isocyanates or isothiocyanates
    • C08G18/8141—Unsaturated isocyanates or isothiocyanates masked
    • C08G18/815—Polyisocyanates or polyisothiocyanates masked with unsaturated compounds having active hydrogen
    • 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
    • C08G18/40—High-molecular-weight compounds
    • C08G18/56—Polyacetals
    • 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
    • C08G18/67—Unsaturated compounds having active hydrogen
    • C08G18/675—Low-molecular-weight compounds
    • C08G18/677—Low-molecular-weight compounds containing heteroatoms other than oxygen and the nitrogen of primary or secondary amino groups
    • C08G18/6775—Low-molecular-weight compounds containing heteroatoms other than oxygen and the nitrogen of primary or secondary amino groups containing halogen
    • G—PHYSICS
    • G06—COMPUTING; CALCULATING OR COUNTING
    • G06K—GRAPHICAL DATA READING; PRESENTATION OF DATA; RECORD CARRIERS; HANDLING RECORD CARRIERS
    • G06K7/00—Methods or arrangements for sensing record carriers, e.g. for reading patterns
    • G06K7/10—Methods or arrangements for sensing record carriers, e.g. for reading patterns by electromagnetic radiation, e.g. optical sensing; by corpuscular radiation
    • G06K7/10544—Methods or arrangements for sensing record carriers, e.g. for reading patterns by electromagnetic radiation, e.g. optical sensing; by corpuscular radiation by scanning of the records by radiation in the optical part of the electromagnetic spectrum
    • G06K7/10821—Methods or arrangements for sensing record carriers, e.g. for reading patterns by electromagnetic radiation, e.g. optical sensing; by corpuscular radiation by scanning of the records by radiation in the optical part of the electromagnetic spectrum further details of bar or optical code scanning devices
    • G06K7/10881—Methods or arrangements for sensing record carriers, e.g. for reading patterns by electromagnetic radiation, e.g. optical sensing; by corpuscular radiation by scanning of the records by radiation in the optical part of the electromagnetic spectrum further details of bar or optical code scanning devices constructional details of hand-held scanners

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Electromagnetism (AREA)
  • Engineering & Computer Science (AREA)
  • Toxicology (AREA)
  • Theoretical Computer Science (AREA)
  • General Physics & Mathematics (AREA)
  • Computer Vision & Pattern Recognition (AREA)
  • Artificial Intelligence (AREA)
  • General Health & Medical Sciences (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Polyesters Or Polycarbonates (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

A process for preparing a liquid resinous reaction product comprises reacting (1) one mole. of a halogen containing polyhydric alcohol which is the reaction product of (A) a hexahalocyclopentadiene and a dihydric alcohol containing aliphatic carbon to carbon unsaturation, wherein the halogen is chlorine, bromine or fluorine or a mixture thereof, or (B) decachlorotetrahydro-4,7-methanoindenone and a polyhydric alcohol containing at least three hydroxyl groups, and (2) at least four moles. of an organic polyisocyanate. To prepare a foam the liquid resinous reaction product is reacted, together with a foaming agent, with a hydroxyl containing polymeric material having a hydroxyl number of between 30 and 650 which is either a polyester comprising the reaction product of a polyhydric alcohol and a polycarboxylic compound, or a polyether comprising the reaction product of a monomeric 1,2-epoxide and a polyhydric alcohol or polycarboxylic acid, or mixtures of the polyester and polyether. The polyhydroxy compound may be the reaction product of an adduct of a hexahalocyclopentadiene and a polycarboxylic compound containing aliphatic carbon to carbon unsaturation with a polyhydric alcohol or with the 1,2-epoxide. Foaming agents are low boiling solvents such as fluorochlorocarbons; water; a tertiary alcohol and concentrated acid; polymethylol phenols; dimethylol ureas, polycarboxylic compounds and formic acid. Catalysts for the foaming reaction are triethylamine, N-methylmorpholine, triethanolamine; antimony caprylate or naphthenate; antimonous chloride; dibutyl tin dilaurate, tri-n-octyl tin oxide hexabutyltin, tributyltin phosphate or stannic chloride. Monomeric 1,2-epoxide may be added to the polyisocyanate prior to its reaction with the hexahalocyclopentadiene adduct. Antimony oxide, clay, calcium sulphate, ammonium phosphate, dyes, fibrous glass asbestos and synthetic fibres may be incorporated. In typical Examples, (1) 1,4,5,6,7,7-hexachloro-2,3-bis-hydroxymethyl-bicyclo-(2.2.1) -5-heptane and 2,4-and 2,6-tolylene diisocyanates are reacted to give a liquid resin which (Example 3) is reacted with a mixture of polypropylene glycol, 1.2.6-hexanetriol, water, dibutyltin dilaurate and silicone oil to give a foamed product; (2) and (4) a foam is obtained by reacting the liquid resin from the butane triol adduct of decachloro-tetrahydro-4,7-methanoindenedione and toluene 2,4 and 2,6-diisocyanates with polypropylene glycol, silicone oil and water.ALSO:A process for preparing a liquid resinous reaction product comprises reacting (1) one mole of a halogen containing polyhydric alcohol which is the reaction product of (A) a hexahalocyclopentadiene and a dihydric alcohol containing aliphatic carbon to carbon unsaturation, wherein the halogen is chlorine, bromine or fluorine or a mixture thereof, or (B) decachlorotetrahydro -4, 7- methanoindenone and a polyhydric alcohol containing at least three hydroxyl groups, and (2) at least four moles of an organic polyisocyanate. To prepare a foam the liquid resinous reaction product is reacted, together with a foaming agent, with a hydroxyl containing polymeric material having a hydroxyl number of between 30 and 650 which is either a polyester comprising the reaction product of a polyhydric alcohol and a polycarboxylic compound, or a polyether comprising the reaction product of a monomeric 1, 2- epoxide and a polyhydric alcohol or polycarboxylic acid, or mixtures of the polyester and polyether. The polyhydroxy compound may be the reaction product of an adduct of a hexahalocyclopentadiene and a polycarboxylic compound containing aliphatic carbon to carbon unsaturation with a polyhydric alcohol or with the 1, 2- epoxide. Foaming agents are low boiling solvents such as fluorochloro carbons; water; a tertiary alcohol and concentrated acid; polymethylol phenols; dimethylol ureas, polycarboxylic compounds and formic acid. Catalysts for the foaming reaction are triethylamine, N-methylmorpholine, triethanolamine; antimony caprylate or naphthenate; antimonous chloride; dibutyl tin dilaurate, tri-n-octyl tin oxide, hexabutyl tin, tributyl tin phosphate or stannic chloride. Monomeric 1, 2- epoxide may be added to the polyisocyanate prior to its reaction with the hexahalocyclopentadiene adduct. Antimony oxide, clay calcium sulphate, ammonium phosphate, dyes, fibrous glass, asbestos and synthetic fibres may be incorporated. In typical examples (1) 1, 4, 5, 6, 7, 7- hexachloro -2, 3-bis-hydroxymethylbicyclo -(2.2.1) -5-heptene and 2, 4- and 2, 6- tolylene diisocyanates are reacted to give a liquid resin which (Example 3) is reacted with a mixture of polypropylene glycol, 1, 2, 6-hexanetriol water, dibutyltin dilaurate and silicone oil to give a foamed product; (2) and (4) a foam is obtained by reacting the liquid resin from the butane triol adduct of decachlorotetrahydro -4, 7- methano - indenedione and tolune 2, 4 and 2, 6- diisocyanates with polypropylene glycol, silicone oil and water.
GB2086060A 1959-06-22 1960-06-14 Halogen-containing polyurethane foams and method of preparation Expired GB904700A (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US821722A US3036999A (en) 1959-06-22 1959-06-22 Reaction product of a polyisocyanate and a 1, 4, 5, 6, 7, 7-hexahalobicyclo-(2.2.1)-5-heptene-2, 3-dicarboxylic acid
US853689A US3055850A (en) 1959-11-18 1959-11-18 Halogen containing polyurethane foams and preparation of same
US853688A US3055849A (en) 1959-11-18 1959-11-18 Halogen containing polyurethane foams and process for preparing same
US853687A US3146220A (en) 1959-11-18 1959-11-18 Halogen containing polyurethane resins

Publications (1)

Publication Number Publication Date
GB904700A true GB904700A (en) 1962-08-29

Family

ID=31982602

Family Applications (2)

Application Number Title Priority Date Filing Date
GB2086160A Expired GB899805A (en) 1959-06-22 1960-06-14 Halogen-containing polyurethane foams and method of preparation
GB2086060A Expired GB904700A (en) 1959-06-22 1960-06-14 Halogen-containing polyurethane foams and method of preparation

Family Applications Before (1)

Application Number Title Priority Date Filing Date
GB2086160A Expired GB899805A (en) 1959-06-22 1960-06-14 Halogen-containing polyurethane foams and method of preparation

Country Status (5)

Country Link
BE (1) BE591938A (en)
DE (3) DE1136484B (en)
FR (2) FR1260399A (en)
GB (2) GB899805A (en)
NL (2) NL252894A (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IL22629A (en) * 1963-12-23 1968-07-25 Allied Chem Method for making rigid cellular polyurethanes containing antimonates (iii)
DE3224001A1 (en) * 1982-06-26 1983-12-29 Schock & Co Gmbh, 7060 Schorndorf Fire-protection building component

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE908071C (en) * 1941-04-22 1954-04-01 Phrix Werke Ag Process for the production of polycondensation products
DE880486C (en) * 1944-03-12 1953-06-22 Bayer Ag Process for the production of high molecular weight products
US2621168A (en) * 1949-09-27 1952-12-09 Sprague Electric Co Condensation resins of halogenated benzene compounds
GB791852A (en) * 1953-06-30 1958-03-12 Du Pont Elastomeric polyurethanes
NL92169C (en) * 1955-09-20
DE1027394B (en) * 1956-10-22 1958-04-03 Bayer Ag Process for the production of foams

Also Published As

Publication number Publication date
DE1158247B (en) 1963-11-28
NL252865A (en)
BE591938A (en)
FR1260399A (en) 1961-05-05
DE1141782B (en) 1962-12-27
FR1260469A (en) 1961-05-05
NL252894A (en)
DE1136484B (en) 1962-09-13
GB899805A (en) 1962-06-27

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