Patent GB-930371-A (GB)
Title: Food additive substances and compositions
Inventor: BECKER EWALD GEORG
IPC: A23D7/01
Filed: 1958-09-19
Abstract: Surface active substances for addition to margarine, etc., comprise esters composed of carbon hydrogen and oxygen alone, each molecule of each ester containing at least 2 ester linkages, 1 to 3 free carboxyl groups, aliphatic or cycloaliphatic groups comprising at least two lepophilic groups each containing 12 to p  30 carbon atoms, and each ester molecule having a ratio of total carbon atoms to free carboxyl groups of between 45 : 1 to 80 : 1, and a molecular weight of between 600 and 2000.  Instead of 1 to 3 carboxyl groups there may be a single anhydride group.  The substances are suitably triglycerides, e.g. adducts formed by Diels-Alder addition of an unsaturated mono- or di-carboxylic acid, or mono- or half-esters thereof, to conjugated olefinic double bonds in isomerised oils, e.g. soyabean, cottonseed (elaidinised), safflower, sunflower, or in fats or fatty acids, e.g. linoleic or sorbic acid, or esters thereof.  The unsaturated mono- or di-carboxylic acid is preferably sorbic, maleic, acrylic, or propiolic acid or maleic anhydride, anhydride adducts being esterified, if desired, with alcohols, e.g. stearyl alcohol, or, after permanganate oxidation, esterified with a diglyceride, e.g. or rapeseed oil.  Adducts may also be formed by reacting fatty acids or glyceride oils containing epoxy or hydroxy fatty acid groups, e.g. castor oil, or castor oil interesterified with oils free from such groups, e.g. ground nut and palm oils, with saturated or unsaturated acids or anhydrides, e.g. maleic, succinic, thereafter further esterifying the product, if desired, with alcohols, e.g. stearoyl alcohol, n-octadecyl alcohol.  In a further method of forming suitable adducts, glycerol is interesterified with a diglyceride, e.g. or rapeseed esters, e.g. oleic, stearic, sebacic, acids or with fatty oils, e.g. refined rapeseed oil, and the products further esterified, e.g. with acids such as sebacic or succinic, or oxidised to form esters.  Adducts may also be obtained by reacting citric acid with molten stearyl alcohol, and reacting the product with stearoyl chloride or succinic anhydride.  The Specification includes lists of other similar reactants which can be combined in the manner described to form suitable substances for addition to margarine. Specification 801,118 is referred to.ALSO:Margarine suitable for use in frying incorporates as anti-spattering and emulsion-stabilizing agent one or more auxiliary surface-active substances which are esters composed of carbon, hydrogen and oxygen alone, the molecules of each substance containing at least 2 ester linkages, 1 to 3 free carboxyl groups, aliphatic or cycloaliphatic groups comprising at least 2 lipophilic groups each containing 12 to 30 carbon atoms, and having a ratio of total carbon atoms to free carboxyl groups of between 45 : 1 and 80 : 1, and a molecular weight between 600 and 2000.  Instead of 1 to 3 carboxyl groups there may be a single anhydride group.  The substances are added in amounts of 0.01 to 5% of the weight of the fat in the water and fat emulsion forming the bases of the margarine or like foodstuff.  The margarine may contain milk, skimmed milk proteins, egg-yolk, monoglycerides, salt, flavouring, and lecithin. Suitable surface-active substances are triglycerides, e.g. adducts formed by Diels Alder addition of an unsaturated mono- or di-carboxylic acid, or mono- or half-esters thereof, to conjugated olefinic bonds in isomerized oils such as soyabean, cottonseed (elaidinized), safflower and sunflower, or in fats or fatty acids, e.g. linoleic and sorbic acids, or esters thereof.  Preferred acids for the Diels Alder addition include sorbic, maleic, acrylic, propiolic acids and maleic acid anhydride.  Anhydride adducts may be esterified with alcohols, e.g. stearyl alcohol, if desired, or after permanganate oxidation, esterified with a diglyceride, e.g. of rape seed oil.  Suitable adducts may also be formed by reacting fatty acids or triglyceride oils containing epoxy or hydroxy fatty acid groups, e.g. castor oil, if desired interesterified beforehand with oils, e.g. ground-nut and palm oils, free from such groups, with saturated or unsaturated acids or anhydrides, e.g. maleic succinic, further esterifying the product, if desired, with alcohols, e.g. stearyl alcohol and n-octadecyl alcohol.  In a further method of forming suitable adducts glycerol is interesterified with one or more fatty acids or esters, e.g. oleic, stearic, sebacic, or with fatty oils, e.g. refined rapeseed oil, and the products further esterified, e.g. with acids such as sebacic or succinic, or oxidized, to form esters.  In other examples citric acid is reacted with molten stearyl alcohol and the product reacted with stearoyl chloride or succinic anhydride. The Specification includes further long lists of similar reactants and methods of combining them to form suitable surface-active substances.  The Provisional Specifications include the preparation of suitable nitrogen-containing esters. Specification 801,118 is referred to.