GB604073A - 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), 1 : 5-, 2 : 6-, or 2 : 7-naphthalene dicarboxylic acid or an ester-forming derivative thereof with ethylene or tri-, tetra-, penta-, or hexa-methylene under conditions such that during the later stages of the reaction volatile by-products and excess of glycol are p removed and continuing the heating until filaments formed from the melted resin can be permanently extended by cold-drawing to useful 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 is preferably used. When a dihalide is used a diluent such as an inert organic liquid and a base, e.g. a tertiary organic base such as pyridine, N-methyl-piperidine, N-dimethylaniline 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, beryllium, magnesium or its oxide, the alcoholates (e.g. methylates and ethylates) or glycolates of the foregoing, 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 useful 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: (1) methyl naphthalene-1 : 5-dicarboxylate; (2) methyl naphthalene-2 : 6-dicarboxylate; (3) methyl naphthalene-2 : 7-dicarboxylate; (5) naphthalene-2 : 6-dicarboxylic acid are heated with ethylene glycol in the presence of lithium and magnesium in a stream of nitrogen; (4) methyl naphthalene-2 : 6 - dicarboxylate is heated with hexamethylene glycol under similar conditions.