Patent GB-1018032-A (GB)
Title: Water soluble or dispersible surface coating ester resins
Inventor: HUNT THOMAS
IPC: C09D191/00
Filed: 1961-05-03
Abstract: Surface coating resin compositions are made by a process which comprises partially esterifying the reaction product of a triglyceride or other polyol ester of an unsaturated fatty acid having at least twelve carbon atoms in the carbon chain containing the unsaturation or the fatty acid of the ester and at least 5% by weight of the total reactants initially present of an acylic dicarboxylic acid having olefinic unsaturation and less than ten carbon atoms in any carbon chain, or the anhydrides or monoesters of such acids, with an alcoholic or epoxy compound to give a water dispersible product having an acid value of at least 20 mgms. potassium hydroxide per gram and dispersing the product in the presence of a base which is defined as an alkali metal hydroxide or ammonia base of the class which consists of ammonia and primary, secondary and tertiary of the type known to be used to solubilize surface coating resins containing free or potentially free carboxyl groups, in water or in water containing a water miscible solvent, characterized in that at least 10% by weight of the compounds introduced into the reaction product by the partial esterification are alcoholic or epoxy compounds containing one or more beta, gamma-ethylenically unsaturated ether groups.  Linseed oil is particularly suitable for use as the ester of an unsaturated fatty acid, maleic anhydride as the acylic dicarboxylic acid anhydride, glycerol diallyl ether or trimethylol propane dially ether as the alcoholic compound, or allyl glycidyl ether as the epoxy compound, and ammonium hydroxide as the base. The partially esterified reaction product has for preference an acid value between 55-75 mgms. of potassium hydroxide per gram. The expression "dispersing" means that the partially esterified product is dissolved in the presence of a base in water or in water containing a water miscible solvent, the solution or emulsion so formed being capable of dilution with water without precipitation. Bases specifically named include ammonia, triethylamine, or dicetylamine.  In the examples maleinized linseed oil is reacted with glycerol diallyl ether to an acid value of 60 mgms. potassium hydroxide per gram using xylol as entrainer.  After removal of xylol by distillation the product was dissolved in aqueous ammonia solution.  A water dispersible cobalt drier was added to a sample of this solution and films were prepared on glass substrate. By way of comparison unesterified maleinized linseed oil was solubilized in a similar manner and after adding driers, air dried films from this solution were dissolved instantly by cold water even after drying for 24 hours. In another example maleinized soyabean oil is partially esterified with glycerol diallyl ether using xylol as entrainer, to an acid value of 70 mgms. potassium hydroxide per gram. This product was dispersed in aqueous ammonia solution and after adding water dispersible cobalt driers, water insoluble films were produced on glass after drying overnight.  Unesterified maleinized soyabean oil treated similarly gave water soluble films.  In a further example 5% maleinized linseed oil is partially esterified with trimethylolpropane diallyl ether and the resulting product of acid value 22 was dispersed in aqueous triethylamine.  In a further example which contains comparative data a maleinized linseed oil is partially esterified with a mixture of trimethylolpropane diallyl ether and cyclohexanol and a further sample with cyclohexanol alone. Whereas the films produced from the mixed partial ester dry and are are insoluble in hot or cold water whereas the ester produced for comparison using cyclohexanol only was not satisfactory in this respect.