Patent GB-607031-A (GB)
Title: Improvements in or relating to the manufacture of resinous condensation products
IPC: C08G16/02
Filed: 1946-06-04
Abstract: Synthetic resinous condensation products are prepared by heating an aldehyde or mixture of aldehydes containing not less than 3 carbon atoms in the molecule and containing the group -CH2-CH=O with maleic acid, maleic anhydride or acetylene dicarboxylic acid under conditions which facilitate removal of water from the reaction at least during the later stages of the reaction.  A little water may be added at the beginning of the reactions.  Water may be removed by using an open vessel, by use of reduced pressure, by continous azeotropic distillation or by use of dehydrating agents.  Suitable aldehydes are propionaldehyde, n-butyraldehyde and n-heptaldehyde. The products may be esterified, the esterification being modified with fatty oils and/or acids or partial esters thereof.  The fatty oil or fatty acid may be present during the additional reaction; or the products may be dissolved in a fatty oil of fatty acid and exterified.  Preferably the adduct is reacted with a partial ester from a fatty acid containing free hydroxyl groups with or without further alcohol to complete esterification.  Suitable alcohols are glycerol, pentaerythritol, ethylene and propylene glycols, butyl, allyl or cetyl alcohol.  Other polycarboxylic acids, e.g. phthalic, sebacic, adipic, succinic, maleic or fumaric may be present during esterification.  Natural resins, fossil gums or synthetic resins may be added at any stage.  The adduct if it contains a group capable of reacting with an aldehyde, e.g. a phenolic hydroxyl group, may be reacted with an aldehyde.  If it contains residual carboxyl groups it may be subjected to an alchol condensation or reacted with phenols, amines, urea or sulphonamides, or these may be present during formation of the adduct.  Polymerisable substances such as styrene, diisobutylene, methylmethacrylate or vinyl acetate may be present during adduct formation, or may be copolymerized with the adduct. Such copolymers may be used as the polybasic acid component of alkyd resins.  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 salt solutions may be used for water paints or adhesives if desired with other film-forming materials, or as binding compositions for linoleum or felt or for treating fibrous materials.  Solutions of the adducts in organic solvents may be used for coating or impregnating. Drying of films of the adducts may be hastened by addition of benzoyl peroxide or in the case of oil or fatty acid modified adducts by means of metallic driers.  The adducts may be incorporated in cellulose lacquers. Generally speaking, the products are soluble in methylated spirit, acetone and mineral spirits.  In examples: (1) to (4) n-butyraldehyde and maleic anhydride or condensed together.  In example (5) propionaldehyde is used and in example (6) n-heptaldehyde.  (7) n-Butyraldehyde, phenol and maleic anhydride are condensed together and the product condensed in alkaline solution with formaldehyde. (8) n-Butyraldehyde is condensed with maleic anhydride with addition of styrene during the reaction.  The product is compatible with nitrocotton and, on heating, with tung oil.  (9) Linseed oil, n-butyraldehyde and maleic anhydride are condensed together and the product esterified with glycerol.  (10) n-Butyraldehyde and acetylene dicarboxylic acid were reacted together.  (11) Gum rosin n-butyraldehyde and maleic anhydride were condensed together.  (12) The product of example (1) was esterified with glycerol.  (13) The product of example (7) was esterified with glycerol.  (14) The product of example (1) esterified with n-butyl alcohol.  (15) The product of example 1 was esterified with glycerol and a partial glyceride of linseed oil acids.  (16) The product of example (1) was esterified with glycerol in presence of stearic acid.  (17) The product of example 1 was esterified with glycerol and castor oil. This product and that of example 16 formed a plasticizer for nitrocellulose or butyrated urea formaldehyde resin.  (18) The product of example 1 was esterified with glycerol, a partial glyceride of linseed oil acids and phthalic anhydride.  (19) The product of example (1) was dissolved in caustic soda and the aluminium salt of the resin precipitated from the solution on to cloth (see Group VIII).  Specifications 600,408 and 600,618 are referred to.