Patent GB-775326-A (GB)
Title: Epoxidized fatty acid diacetoglycerides
IPC: C07D303/42
Filed: 1955-04-12
Abstract: Polyvinyl chloride, copolymers of vinyl chloride with vinyl esters of saturated aliphatic acids having 2-18 carbon atoms or with vinylidene chloride, and cellulose esters, including nitrocellulose, are plasticised and stabilized by the epoxidation product of fatty acid di-acetoglycerides consisting of 100 to 75 per cent of unsaturated fatty acid di-aceto glycerides and 0 to 25 per cent by weight of saturated fatty acid diaceto-glycerides, the fatty acids containing at least 16 carbon atoms in the molecule (see Group IV (b)).  The term "fatty acid di-aceto glycerides" denotes mixtures of compounds which contain an average of about 2 aceto groups in the molecule; minor amounts of glycerides containing more or fewer than 2 aceto groups in the molecule may be present.  The plasticiser preferably constitutes 20-40 per cent by weight of the plasticised composition. Examples describe the plasticisation of a vinyl chloride-vinyl acetate copolymer with the epoxidation products of a di-acetylated cottonseed oil monoglyceride, di-acetylated soya bean oil monoglyceride and di-acetylated oleic acid mono-glyceride.ALSO:The invention comprises the epoxidation product of fatty acid diaceto-glycerides consisting of 100 to 75 per cent of unsaturated fatty acid diaceto-glycerides and 0 to 25 per cent by weight of saturated fatty acid di-aceto glycerides, the fatty acids containing at least 16 carbon atoms in the molecule.  The term "fatty acid di-aceto glycerides" is used to denote mixtures of compounds which contain an average of about 2 aceto groups per molecule; minor amounts of glycerides containing more or fewer than 2 aceto groups in the molecule may be present.  The epoxidation may be effected by means of an organic peracid such as per-formic, per-acetic or per-benzoic acid in a suitable solvent at about room temperature. The products are plasticizer-stabilizers for various resins (see Groups IV (a) and V).  In examples: (1) cottonseed oil is converted into the monoglyceride by heating with glycerol and NaOH catalyst, and acetylated with acetic anhydride; the di-aceto monoglyceride is then epoxidized with a solution of per-acetic acid in acetic acid and the product is purified by ethereal extraction and water-washing; (2) soya bean oil is reacted with triacetin in presence of sodium methylate and resulting di-aceto mono glyceride is epoxidized as in (1); (3) oleic acid is reacted with glycerol to form the monoglyceride which is diacylated and the product epoxidized as in (1).  Olive oil, corn oil, tall oil and fish oils are also mentioned as suitable sources of unsaturated fatty acid di-aceto glycerides.ALSO:Chlorinated rubber is plasticized and stabilized by the epoxidation product of fatty acid di-aceto glycerides consisting of 100 to 75 per cent of unsaturated fatty acid di-aceto glycerides and 0 to 25 per cent by weight of saturated fatty acid di-aceto glycerides, the fatty acids containing at least 16 carbon atoms in the molecule (see Group IV(b)).  The term "fatty acid di-aceto glycerides" denotes mixtures of compounds which contain an average of about 2 aceto groups per molecule; minor amounts of glycerides containing more or fewer than 2 aceto groups in the molecule may be present.  Specified plasticizers, which preferably constitute 20-40 per cent by weight of the plasticized composition are the epoxidation products of di-acetylated cotton seed or soya bean oil monoglycerides and of diacetylated oleic acid monoglyceride.