Patent GB-1075291-A (GB)
Title: Water dispersible reaction products of adducts of long chain aliphatic compounds
IPC: C08G12/22
Filed: 1963-12-11
Abstract: Resins are prepared by forming an adduct of an a ,b  - unsaturated dicarboxy compound ("maleyl compound") and an ethylenically unsaturated compound containing a chain of 10-24 carbon atoms, and treating this first with ammonia or an amine, to give an "amide adduct", and then with formaldehyde.  The "maleyl compound" may be, e.g. maleic, fumaric, citraconic, or itaconic acid, or an anhydride, amide, or mono- or di-ester thereof.  Maleic anhydride is preferred. The long-chain unsaturated compound may contain carboxyl, halo, acyloxy, alkoxy, aroxy or tertiary or quaternary amine groups, but is preferably a polyunsaturated glyceride oil, or a related fatty acid or ester. Soybean and linseed oils, and oleic, linoleic and linolenic acids, salts, esters and amides are specified.  The amide-forming agent is preferably ammonia but may be a primary amine or a primary or secondary polyamine. The formaldehyde is preferably used in the free form, but may derive from a formaldehyde polymer or hexamethylene tetramine. The methylol amide adducts are neutralized with inorganic or nitrogenous organic bases, preferably volatile, e.g. ammonia, in order to redisperse the precipitated material. Aqueous solutions of the products may be used as yarn sizing compositions, non-woven binders, tyre cord adhesives and coating compositions.  For sizing, e.g. polyester, nylon, polypropylene or glass fibres there may be added to the composition starch or a polyvinyl latex, and a lubricant.  In examples products are prepared from various proportions of maleic anhydride and soybean oil treated after adduct formation with ammonium hydroxide and formalin.  In variant processes are used: itaconic acid for maleic anhydride; linseed oil, tall oil, tall oil/soybean oil mixture, isomerized soybean oil or pentaerythritol tetra-ester of soybean fatty acids as the oil; ethanolamine for ammonium hydroxide.  The adduct in Example 16 is treated with 1:3-dichloro-5:5-dimethylhydantoin, and in Examples 23-25 trimethylamine or NaOH or Na2CO3 or K2CO3 is added as buffer to the amide adduct.  The product aqueous solutions are applied to glass panels as coating compositions; or made into paints by mixing with red iron oxide, barytes and Mg silicate (Example 11) or zinc chromate (Example 26) or red lead, zinc yellow, red iron oxide, Mg silicate, mica and Al stearate (Example 27) and applied to steel panels; or mixed with various addition polymers (Example 28) including acrylate, P.V.C., polyethylene, polyvinyl acetate, styrene-butadiene, polyvinyl butyral and acrylonitrile polymers, "dry" and in solution, in 1:4, 1:1 and 4:1 ratios.ALSO:Coating compositions contain resins prepared by forming an adduct from an a ,b -unsaturated dicarboxy compound and an ethylenically unsaturated compound containing a chain of 10-24 C atoms, then forming an "amide adduct" from this with ammonia or an amine, then treating this with formaldehyde.  Resins in examples are derived from maleic anhydride or itaconic acid; soybean or linseed or tall oil or modified soybean oil; ammonia or ethanolamine; and formalin (see Division C3).  The aqueous solutions are used directly to coat glass plates, or is made into a paint by adding iron oxide, barytes, and Mg silicate (Ex. 11); zinc chromate, zinc potassium chromate or ammonium zincate (Ex. 26); or red lead, red iron oxide, zinc yellow, Mg silicate, Al stearate and mica (Ex. 27).  These are sprayed or coated onto steel plates.