Patent GB-924895-A (GB)
Title: Fatty esters and their use in the manufacturing of cellular polyurethanes
Inventor: BATTY JOHN WOOLLEY
IPC: C11C3/00
Filed: 1958-09-22
Abstract: The invention comprises fatty acid or bodied hydroxy fatty acid esters, said acids containing a chain of at least 7 carbon atoms, of condensates of ethylene oxide with the hydroxyl and carboxyl groups of a bodied hydroxy fatty acid containing a chain of at least 7 carbon atoms.  The esters may be prepared by heating the condensate with the fatty acid or bodied fatty acid in the presence of an esterification catalyst for example sulphuric or toluene sulphonic acid and, suitably, with the aid of toluene as a water-entrainer. The condensate is made by heating the bodied acid with ethylene oxide in the presence of an alkaline catalyst as described in Specifications 640,464 and 874,550.  The bodied fatty acids are prepared, for example, by heating the hydroxy acid under atmospheric or reduced pressure with or without an alkaline catalyst, preferably until the product has an acid value below 120 mgm. of KOH/gm., and, if desired, while passing a stream of oxygen or inert gas through the heated acid.  In examples, castor oil fatty acids are bodied and then condensed with ethylene oxide and the product is esterified with bodied castor oil fatty acids or oleic acid.  Other acids specified for the final esterification are lauric and ricinoleic acids. Cellular polyurethane products are prepared by interacting an organic polyisocyanate with a hydroxyl-containing polymer containing at least two hydroxyl groups per molecule for example a polyester, polyesteramide or a polyether, in the presence of an ester condensate of the above class and, as desired, a catalyst and water.  Suitably, the ester condensate is used in amounts of from 0,1% to 2,5% on the weight of the hydroxy polymer and is mixed with water, an emulsifier and catalyst and the mixture added to the hydroxy polymer and polyisocyanate.  The polyisocyanates may be partially polymerized or modified by treatment with polyhydric alcohols such as trimethylolpropane.  Many aromatic di- and tri-isocyanates are named. The hydroxy poly-esters and ester-amides are prepared from dicarboxylic acids and glycols, in admixture if desired with polyhydric alcohols, and, as necessary, diamines or aminoalcohols, many suitable reactants being listed. The hydroxy polyethers mentioned include the polymers and co-polymers of cyclic ethers such as ethylene oxide, propylene oxide, epichlorhydrin and oxacyclobutanes and tetrahydrofuran, obtainable as described in Specification 733,624.  They may be co-polymerized with small amounts of polyfunctional compounds such as glycidol, glycerol, trimethylolpropane and 3-hydroxymethyloxy-cyclobutanes.  Catalysts for the polyurethane reaction are tertiary amines, a number being specified.  Examples describe the preparation of a foamed material by condensation of toluene di-isocyanates with a liquid polyester derived from diethylene glycol, pentaerythritol and adipic acid, in an aqueous solution of dimethyl cyclohexylamine, an ethylene oxide condensate of octyl cresol, and a minor amount of the above mentioned oleic acid or bodied castor oil fatty acid ester of the ethylene oxide-bodied castor oil fatty acid condensate.ALSO:The invention comprises fatty acid or bodied hydroxy fatty acid esters, said acids containing a chain of at least 7 carbon atoms, of condensates of ethylene oxide with the hydroxyl and carboxyl groups of a bodied hydroxy fatty acid containing a chain of at least 7 carbon atoms. The esters may be prepared by heating the condensate with the fatty acid or bodied fatty acid in the presence of an esterification catalyst for example sulphuric or toluene sulphonic acid and, suitably, with the aid of toluene as a water-entrainer.  The condensate is made by heating the bodied acid with ethylene oxide in the presence of an alkaline catalyst as described in Specifications 874,550 and 640,464.  The bodied fatty acids are prepared, for example, by heating the hydroxy acid under atmospheric or reduced pressure with or without an alkaline catalyst, preferably until the product has an acid value below 120 mgm. of KOH/gm., and, if desired, while passing a stream of oxygen or inert gas through the heated acid.  In examples, castor oil fatty acids are bodied and then condensed with ethylene oxide and the product is esterified with bodied castor oil fatty acids or p  oleic acid.  Other acids specified for the final esterification are lauric acid and ricinoleic acid.  The esters may be used in the preparation of cellular polyurethane products (see Group IV(a)).ALSO:Cellular polyurethane products are prepared by interacting an organic polyisocyanate with a polymer containing at least two hydroxyl groups per molecule, for example, a polyester, polyester amide or polyether, in the presence of a fatty acid or bodied hydroxy fatty acid ester of a condensate of ethylene oxide with a bodied hydroxy fatty acid (the fatty acids and bodied hydroxy fatty acids containing a chain of at least 7 carbon atoms) and also in the presence as desired of a catalyst for the reaction, e.g. a tertiary amine, and water.  Suitably, the ester-condensate is used in amounts of from 0,1 to 2,5% by weight of the hydroxy polymer.  Numerous aromatic di- and tri-isocyanates are specified; they may be partially polymerised or modified by treatment with polyhydric alcohols.  Many suitable hydroxy polymers are described.  Examples describe the preparation of a foamed material by condensation of toluene di-isocyanates with a liquid polyester derived from diethylene glycol, adipic acid and penta erythritol in an aqueous solution containing an oleic acid or bodied castor oil fatty acid ester of an ethylene oxide condensate of bodied castor oil fatty acids, dimethylcyclohexylamine and an ethylene oxide condensate of octyl cresol.  The use of the lauric and ricinoleic esters is also mentioned.  Specifications 640,464, 733,624 and 874,550 are referred to.