GB1108812A - Polyamides - Google Patents

Abstract

1,108,812. Polyamides; polyalkylene oxides. IMPERIAL CHEMICAL INDUSTRIES Ltd. 13 July, 1965 [12 May, 1964; 10 Aug., 1964; 15 March, 1965], Nos. 10769/65, 32449/64 and 10768/65. Divided out of 1,108,811. Heading C3R. A polyamide may be produced by condensation of a dicarboxylic acid with a mixture of a polyoxyalkylene diamine of M.W. 300-6000 and an aliphatic, cycloaliphatic or alkyl cycloaliphatic amino acid and/or lactam. The dicarboxylic acid may be of formula where n = 0-10 or may be cycloaliphatic, alkylcycloaliphatic, aromatic or alkylaromatic. The cycloaliphatic acids have the carboxyl groups linked directly to different, non-adjacent carbon atoms of a C 5-16 polymethylene ring. In the case of aromatic acids the carb- oxyl groups must not be on adjacent carbon atoms. The acids may be replaced by their esters or halides. Acids specified include adipic, sebacic and terephthalic acids. The polyoxyalkylene diamine may be of formula where X is a direct link and Y an alkylene group, X is a 2-methylenetetrahydropyran-6-yloxy group and Y a 2-methylenetetrahydropyran-6-yl group or is an alkylene oxy group and Y is an alkylene group. All the alkylene groups may be the same or more than 1 type may be present. They may contain 2-12 carbon atoms. These compounds may be prepared from the corresponding polyoxyalkylene diol by either (a) chlorination with thionyl chloride followed by treatment with NH 3 , (b) treatment with acrylonitrile followed by reduction of the nitrile group or (c) treatment with 2-aminomethyl-3,4-dihydro-2H-pyran. The polyoxyalkylene diols may in turn be prepared either from alkylene oxide, e.g. ethylene oxide or propylene oxide optionally in the presence of a compound containing 2 reactive hydrogen atoms, e.g. H 2 O, a dihydric alcohol or phenol, a dicarboxylic acid, a primary amine, e.g. octadeoamethylene diamine, a primary amide or a bis(secondary amine) or from glycols, e.g. tetramethylene glycol. The amino acid or lactam may be an acid of formula NH 2 (CH 2 ) n COOH, where n= 5-11, a cycloaliphatic amino acid in which the amino and carboxyl groups are linked directly to different non-adjacent carbon atoms in a C 5-16 polymethylene ring or the corresponding lactam. Lactams and acids specified include #-caprolactam. The condensation mixture may also contain an aliphatic, cycloaliphatic, aromatic, alkylcycloaliphatic or alkylaromatic diamine. The diamine may be of formula NH 2 (CH 2 )NH 2 where n=2-12 or may have 2-amino-groups linked directly to different non- adjacent carbon atoms of a C 5-16 polymethylene ring. In the case of aromatic diamines the two amino-groups must not be on adjacent carbon atoms. Diamines specified include hexamethylene diamine. Where a diamine is present it may be in the form of its salt with the dicarboxylic acid. More than one dicarboxylic acid, amino acid, lactam, polyoxyalkylene diamine or other diamine may be used. The ratio of reactants may be such that the dicarboxylic acid and total diamine content are stoichiometrically equivalent and the polyoxyalkylene diamine is 10-95% of the total weight of diamine, amino acid and lactam. The condensation mixture may also contain antioxidants, heat stabilizers, pigments, fillers, a solvent, e.g. water, and a material which dissolves the reactants at the condensation temperature, e.g. o-hydroxydiphenyl. The condensation may be carried out at 150-300‹ C., under an inert atmosphere and superatmospheric pressure.