Patent GB-870957-A (GB)
Title: Aromatic glycols and polyester and alkyd resins derived therefrom
IPC: C08G63/672
Filed: 1959-06-03
Abstract: An alkyd resin comprises the reaction -product of (1) an aromatic glycol of the formula: <FORM:0870957/IV (a)/1> wherein R is a straight or branched chain or carbocyclic alkyl substituent having from 5 to 12 carbon atoms and n is an average number lying between 1 and 2, (see Group IV(b)) and (2) at least one saturated aliphatic or aromatic dicarboxylic acid or anhydride thereof, defined above; (2) at least one saturated or aromatic dicarboxylic acid or anhydride thereof.  Carboxylic acids specified for use in preparing the alkyd resins include succinic, adipic, and sebacic and aromatic dicarboxylic acids and anhydrides such as phthalic acid, phthalic anhydride, isophthalic or terephthalic acid or mixtures thereof. Cross linking agents specified for use in the preparation of alkyd resins include further polyhydric alcohols having at least three hydroxyl groups such as glycerol, pentaerythritol, sorbitol, trimethylol propane p  and mixtures thereof.  Further glycols which may be used in admixture with the glycols of the invention include ethylene, propylene and diethylene glycols and mixtures thereof. Fatty acids which may be incorporated in the alkyd resins include saturated or unsaturated fatty acids having from 10 to 22 carbon atoms, e.g. soya-, linseed oil-, dehydrated castor oil-, coconut-, cottonseed-, tall oil- and fish oil fatty acids.  Glycerides which may be employed instead include linseed, soybean, tung, dehydrated castor, oiticica and perilla oils.  The alkyd resins may be employed in paints and varnishes.  In examples: Alkyd resins are prepared by heating an aromatic glycol, obtained by reacting a p-tert. octyl phenol with ethylene oxide, with distilled acids of dehydrated castor oil, pentaerythritol containing related solid polyhydric alcohols and phthalic anhydride (II, III, VII-XI); with a similar mixture containing in addition, diethylene glycol (XII) and by heating the aromatic glycol with a similar mixture to (II) containing soya fatty acids instead of those of dehydrated castor oil (V, VI).  The reactions are carried out in the presence of a solvent comprising mineral spirits and/or xylene.  Films are prepared by baking the resins on glass, in some cases after the addition of lead, cobalt and manganese driers.ALSO:The invention comprises an aromatic glycol which has the formula:  <FORM:0870957/IV (b)/1> wherein R is a straight or branched chain or carbocyclic alkyl substituent having from 5 to 12 carbon atoms and n is an average number lying between 1 and 2, or which is the reaction product of ethylene oxide and a bis-phenol of the formula:  <FORM:0870957/IV (b)/2> wherein R is a straight or branched chain or carbocyclic alkyl substituent having from 5 to 12 carbon atoms, the proportions of reactants being such as to provide from 1 to 2 molecules of ethylene oxide per phenolic hydroxyl group of the bis-phenol.  The products of the invention may be converted to polyester and alkyd resins (see Group IV(a)).  The aromatic glycols of the invention are prepared by reacting 1,67 to 2,0 mols of a suitable alkyl phenol with one mole of formaldehyde or equivalent amounts of paraformaldehyde or trioxane to obtain a bis-phenol and reacting the latter with ethylene oxide e.g. under elevated temperature and pressure, in the presence of an alkali hydroxide or alkali metal carbonate. Suitable alkyl phenols specified include p-amyl, tertiary amyl, hexyl, octyl, decyl and dodecyl phenols.  In an example p-tertiary octyl phenol in which the alkyl substituent is derived from diisobutylene, is reacted with trioxane in the presence of hydrochloric acid and the product is neutralised and treated with ethylene oxide in the presence of potassium carbonate.