GB1032365A - Improvements in or relating to glycol esters of tribasic organic compounds and to polyurethanes obtainable therefrom - Google Patents

Improvements in or relating to glycol esters of tribasic organic compounds and to polyurethanes obtainable therefrom

Info

Publication number
GB1032365A
GB1032365A GB1299663A GB1299663A GB1032365A GB 1032365 A GB1032365 A GB 1032365A GB 1299663 A GB1299663 A GB 1299663A GB 1299663 A GB1299663 A GB 1299663A GB 1032365 A GB1032365 A GB 1032365A
Authority
GB
United Kingdom
Prior art keywords
esters
adducts
conjugated
acids
glycol
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
GB1299663A
Inventor
Raymond Vincent Crawford
Patrick Arthur Toseland
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.)
J Bibby and Sons Ltd
Original Assignee
J Bibby and Sons 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
Application filed by J Bibby and Sons Ltd filed Critical J Bibby and Sons Ltd
Priority to GB1299663A priority Critical patent/GB1032365A/en
Priority to DE19641495170 priority patent/DE1495170A1/en
Publication of GB1032365A publication Critical patent/GB1032365A/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
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/36—Hydroxylated esters of higher fatty acids
    • 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
    • C08G18/676—Low-molecular-weight compounds containing the unsaturation at least partially in a non-aromatic carbocyclic ring
    • 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
    • C08G18/68—Unsaturated polyesters
    • C08G18/683—Unsaturated polyesters containing cyclic groups
    • C08G18/686—Unsaturated polyesters containing cyclic groups containing cycloaliphatic groups
    • 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
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/52—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
    • C08G63/54—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation the acids or hydroxy compounds containing carbocyclic rings
    • C08G63/553—Acids or hydroxy compounds containing cycloaliphatic rings, e.g. Diels-Alder adducts

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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Glycol esters are prepared by esterifying a tribasic Diels-Alden adduct obtained from a reactive dienophile comprising maleic or fumaric acids or their anhydrides or alkyl esters, and a conjugated or non-conjugated unsaturated fatty acid or ester, with glycol in excess of 3 moles of glycol to 1 mole of tribasic compound and with alcoholysis if necessary. The fatty acids forming the adducts include conjugated polyunsaturated vegetable oils, or monounsaturated compounds, e.g. oleic acid, methyl oleate, commercial olein and monomeric by-products of the polymerization of unsaturated fatty acids or esters. A catalyst for both alcoholysis and esterification, e.g. sodium hydroxide, or for esterification e.g. zinc, stannic chloride, p-toluene sulphonic acid and alcoholysis, e.g. tetra-isopropyl-titanate, sodium methoxide and litharge or triphenyl phosphite are mentioned. Additional compounds such as dibasic acids or esters (adipic or dimerized fatty acids) up to 70%, and/or monobasic fatty acids or esters up to 40%, may be present. Ethylene and diethylene glycols are specified and the products may be reacted with isocyanates to give polyurethanes (see Division C3) which may be prepared as a foam. Examples describe the preparation of esters from adducts with soya bean acids, which may include oleates and palmitates.ALSO:Polyurethanes are prepared by reacting glycol esters of organic tribaric adducts with di- or poly-isocyanates, if desired in the presence of a catalyst. The adducts are Diels-Alder adducts obtained from maleic or fumaric acid or their anhydrides, or alkyl esters and a conjugated or non-conjugated unsaturated fatty acid or ester (see Division C3). Ethylene and diethylene glycols are used and the isocyanates include toluene di-isocyanate, di-phenyl methane di-isocyanate, polymethylene polyphenylino-cyanate or adducts of an isocyanate with a low M.W. polyol, and catalysts may be triethylene diamine, N-methyl morpholine, triethylamine or stannous octoate. The products may include mineral fillers and oils and be in the form of rigid or semi-rigid foams, or as films or coatings.
GB1299663A 1963-04-02 1963-04-02 Improvements in or relating to glycol esters of tribasic organic compounds and to polyurethanes obtainable therefrom Expired GB1032365A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
GB1299663A GB1032365A (en) 1963-04-02 1963-04-02 Improvements in or relating to glycol esters of tribasic organic compounds and to polyurethanes obtainable therefrom
DE19641495170 DE1495170A1 (en) 1963-04-02 1964-04-01 Process for the production of polyurethanes

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1299663A GB1032365A (en) 1963-04-02 1963-04-02 Improvements in or relating to glycol esters of tribasic organic compounds and to polyurethanes obtainable therefrom

Publications (1)

Publication Number Publication Date
GB1032365A true GB1032365A (en) 1966-06-08

Family

ID=10014925

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1299663A Expired GB1032365A (en) 1963-04-02 1963-04-02 Improvements in or relating to glycol esters of tribasic organic compounds and to polyurethanes obtainable therefrom

Country Status (2)

Country Link
DE (1) DE1495170A1 (en)
GB (1) GB1032365A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3644237A (en) * 1968-03-08 1972-02-22 Bibby Chemicals Ltd Polyurethane foam materials
WO2001070842A2 (en) * 2000-03-20 2001-09-27 Kt Holdings, Llc Polyurethane foams
WO2023002449A1 (en) * 2021-07-23 2023-01-26 Equus Uk Topco Limited Reversible polyol and products containing the same

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3644237A (en) * 1968-03-08 1972-02-22 Bibby Chemicals Ltd Polyurethane foam materials
WO2001070842A2 (en) * 2000-03-20 2001-09-27 Kt Holdings, Llc Polyurethane foams
WO2001070842A3 (en) * 2000-03-20 2002-01-31 Kt Holdings Llc Polyurethane foams
WO2023002449A1 (en) * 2021-07-23 2023-01-26 Equus Uk Topco Limited Reversible polyol and products containing the same

Also Published As

Publication number Publication date
DE1495170A1 (en) 1969-02-20

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