Patent GB-608027-A (GB)
Title: Improvements in or relating to the manufacture of resinous condensation products
IPC: C08G16/00
Filed: 1946-06-04
Abstract: Synthetic resinous condensation products are produced by heating cyclohexanone or a lower alkyl substituted cyclohexanone not containing a substituent group in the positions a  to the carbonyl group with maleic acid, maleic anhydride or acetylene dicarboxylic acid under conditions facilitating removal of water. A little water may be added at the beginning of the process. Water may be removed by use of an open vessel, by use of reduced pressure, by continuous azeotropic distillation or by using dehydrating agents.  Part of the cyclohexanone may be replaced by aldehydes or ketones mentioned in Specifications 600,408, 607,031 and 608,023.  The products may be esterified, the esterification being modified with fatty oils, fatty acids or their partial esters by various methods.  Suitable alcohols for the esterification are pentaerythritol, glycerol, ethylene glycol, propylene glycol, butyl, allyl or cetyl alcohol.  Other polycarboxylic acids which may be included in the esterification mixture are phthalic, sebacic, adipic, succinic, maleic and fumaric. Natural resins, fossil gums or synthetic resins may be included at any stage of the process.  Carbonyl groups in the adduct may be reacted with phenols, amines, urea or sulphonamides or these substances may be present during adduct formation. Polymerizable substances such as styrene, di-isobutylene, methyl methacrylate or vinyl acetate may be present during adduct formation or may be copolymerized with the adducts.  The adducts may form salts and insoluble metal salts may be precipitated, e.g. on textiles from aqueous solutions of the alkali metal or ammonium salts.  The aqueous solutions may also be used if desired with other film-forming materials in water-paints or adhesives, as binders for linoleum or felt or for treating fibrous materials. Solutions in volatile solvents may be used as coating or impregnating compositions.  Drying of the products may be hastened by benzoyl peroxide or in the case of oil or fatty acid modified materials by metallic driers.  The adducts may be incorporated in cellulosic lacquers.  In the examples, a cyclohexanone sold under the Registered Trade Mark "Sextone" is used, and a methyl cyclohexanone sold under the Registered Trade Mark "Sextone B." The products generally are soluble in xylol, methylated spirits and acetone and compatible with nitrocotton and, on heating with drying oils.  Examples describe (1)-(4) adducts from cyclohexanone and maleic acid or anhydride; (5) an adduct from methyl cyclohexanone and maleic anhydride; (6) an adduct from cyclohexanone and acetylene dicarboxylic acid; (7) an adduct from cyclohexanone, maleic anhydride and phenol and subsequent reaction in alkaline solution with formaldehyde; (8) cyclohexanone and maleic anhydride were heated together with addition of styrene during the heating; (9) cyclohexanone, maleic anhydride and linseed oil were heated together. The product was esterified with glycerol; (10) gum rosin was added to the mixture of cyclohexanone and maleic anhydride; (11) the product of example (1) was esterified with glycerol; (12) the product of example (1) was esterified with n-butyl alcohol; (13) the product of example (8) was esterified with glycerol; (14) the product of example (1) was esterified with a partial glyceride of linseed oil acids; (15) the product of example (1) was esterified with glycerol and linseed oil acids; (16) the product of example (1) was esterified with glycerol and castor oil; (17) the product of example (1) was esterified with glycerol, in presence of phthalic anhydride and a partial glyceride of linseed oil acids.  The product of example (1) was dissolved in caustic soda and the aluminium salt of the resin was precipitated on to cotton cloth from the aqueous sodium salt solution.