GB604074A - Manufacture of new highly polymeric linear esters and the production of filaments, fibres and the like therefrom - Google Patents

Abstract

Alkyd resins are prepared by heating, preferably in the absence of oxygen (e.g. in a stream of nitrogen), acids of the formula <FORM:0604074/IV(a)/1> where R is <FORM:0604074/IV(a)/2> or ester-forming derivatives thereof with ethylene or tri-,tetra-, penta- or hexa-methylene glycol under conditions such that during the later stages of the reaction volatile byproducts and excess of glycol are removed and continuing the heating until filaments extruded or spun from molten or re-melted resin can be permanently extended by cold-drawing to form fibres. Suitable derivatives are esters and half-esters such as low alkyl (e.g. methyl, ethyl, propyl, butyl, amyl, hexyl and heptyl) cycloalkyl, and aryl (e.g. phenyl) esters; acid halides; and ammonium or amine salts. When the acid itself is used a large excess (e.g. 4 to 5 molar proportions) and when an ester is used about 1 1/2 molar proportions of glycol are preferably used. When a dihalide is used a diluent such as an inert organic liquid and a base such as a tertiary organic base (e.g. pyridine, N-methyl-pyridine, N-dimethyl-aniline, or N-diethylaniline) are preferably present. Specified ester-interchange catalysts which may be present are lithium, sodium, and potassium or their carbonates or borates, calcium, magnesium or its oxide, the alcoholates (e.g. methylates or ethylates) or glycolates of the foregoing, beryllium, zinc, cadmium, aluminium, chromium, molybdenum, manganese, iron, cobalt, nickel, copper, silver, mercury, tin, lead, bismuth, antimony, platinum, and palladium. Filaments extruded or spun from the molten or re-melted resin may be cold-drawn to form fibres and the resin may also be used for films, mouldings, hot-melt coatings, adhesives, e.g. for bonding laminated fabrics such as doubled fabric collars, plasticizers, and binders for coating compositions. In examples: ethylene glycol and (1) ethyl 1 : 4-diphenoxybenzene-4 : 41-dicarboxylate; (2) ethyl 1 : 4-bis-(phenoxymethyl)-benzene-4 : 41-dicarboxylate; (3) ethyl (phenoxymethyl)-benzene-4 : 41-dicarboxylate; (4) methyl phenoxybenzene-4 : 41-dicarboxylate; (5) (phenoxymethyl)-benzene-4 : 41-dicarboxylic acid are condensed by heating in an atmosphere of nitrogen in the presence of lithium and magnesium. The products may be formed into filaments which can be cold-drawn to form fibres. Ethyl 1 : 4-diphenoxybenzene-4 : 41-dicarboxylate is prepared by heating sodium ethyl p-hydroxybenzoate with p-dibromobenzene in the presence of copper-bronze. Ethyl 1 : 4-bis-(phenoxymethyl)-benzene-4 : 41-dicarboxylate is prepared by boiling sodium ethyl p-hydroxybenzoate with p-xylylene dichloride in ethyl alcohol. Ethyl (phenoxymethyl)-benzene-4 : 41-dicarboxylate is prepared by boiling sodium ethyl p-hydroxybenzoate with ethyl p-chloromethylbenzoate in ethyl alcohol.ALSO:Ethyl 1 : 4 - diphenoxybenzene - 4 : 41 - dicarboxylate is prepared by heating sodium ethyl p - hydroxybenzoate with p - dibromobenzene in the presence of copper-bronze. Ethyl 1 : 4 - bis - (phenoxymethyl) - benzene - 4 : 41 - dicarboxylate is prepared by boiling sodium ethyl p-hydroxybenzoate with p-xylylene dichloride in ethyl alcohol. Ethyl (phenoxymethyl( - benzene - 4 : 41 - dicarboxylate is prepared by boiling sodium ethyl p-hydroxybenzoate with ethyl p-chloromethylbenzoate in ethyl alcohol.