Patent GB-1128807-A (GB)
Title: Aromatic polyamides
Inventor: JONES MICHAEL EDWARD BENET
IPC: C08G69/32
Filed: 1965-05-21
Abstract: 1,128,807. Aromatic polyamides. IMPERIAL CHEMICAL INDUSTRIES Ltd. 13 May, 1966 [21 May, 1965 (2); 24 Aug., 1965], Nos. 21621/65, 21622/65 and 36258/65. Heading C3R. A non-crystallizable polyamide is derived from a bis(aminophenyl) sulphone and either (i) isophthalic acid; (ii) a naphthalene dicarboxylic acid, having not more than one axis of symmetry; (iii) a compound having a single benzene ring carrying two carboxylic acid groups on non-adjacent carbon atoms and at least one halogen atom on a further carbon atom, other than a monohaloterephthalic acid or a 5-haloisophthalic acid; (iv) a compound containing a single benzene ring carrying two carboxylic acid groups on non-adjacent carbon atoms and on a further carbon atom a group RO- where R is a substituted or unsubstituted hydrocarbon radical; or (v) a compound containing two benzene rings each carrying a carboxylic acid group attached directly to it and linked by -CO-, -O-, a diol residue or a single carbon atom, the other valencies of which are satisfied by H or other carbon atoms, in which not more than 90% of the recurring units being derived from 4,4<SP>1</SP>-diaminodiphenyl sulphone and isophthalic acid. Bis(aminophenyl)sulphones specified include bis(3-aminophenyl) sulphone and bis(4-aminophenyl) sulphone. Up to 50% of another diamine may also be present. Diamines specified include: m-phenylene diamine and bis(4-aminophenyl) ether. Acids (ii) specified include naphthalene-1,4-dicarboxylic acid. Acids (iii) may be alkyl or alkoxy substituted. Examples include: 4- chloroisophthalic acid, 2,5-dichloroisophthalic acid, and 2,5-dichloroterephthalic acid. In acids (iv) R may be an aryl group or alkyl group of 1-6 carbon atoms. Acids specified include: a monoalkoxyterephthalic acid or a 2-, 4- or 5-alkoxyisophthalic acid, e.g. methoxyterephthalic acid, 4-n-propoxyisophthalic acid, 5 - methoxyisophthalic acid, 2 - methoxyisophthalic acid. Acids (v) may be of formula where X is O, CO, a diol residue -O(KO) x -, CYY<SP>1</SP>, where Y and Y<SP>1</SP> are H or hydrocarbon radicals or together represent a divalent organic radical, R and R<SP>1</SP> are either halogen, C 1-6  alkyl or alkoxy, or halogenated alkyl or alkoxy, m and n are 0-4, x is an integer, e.g. 1 or 2, and K is a polymethylene radical optionally having O and S atoms in the chain, an alkylene or phenylene radical or a radical of formula where L is O, S, SO, SO 2 , CO or a divalent hydrocarbon residue, e.g. CH 2  or C(CH 3 ) 2 . Acids specified include: benzophenone - 4,4<SP>1</SP>- dicarboxylic acid, diphenylmethane - 4,41- dicarboxylic acid, diphenylmethane - 3,3<SP>1</SP> dicarboxylic acid, 2,2 - diphenylpropane - 4,4<SP>1</SP>- dicarboxylic acid and 1,1-diphenylcyclohexane- 4,4<SP>1</SP> - dicarboxylic acid, diphenylether - 4,41- dicarboxylic acid, diphenoxyethane - 4,4<SP>1</SP>- dicarboxylic acids, diphenoxybenzene-3,3<SP>1</SP>-dicarboxylic acids. Mixtures of these acids may be used and up to 50% of another dicarboxylic acid, e.g. terephthalic acid, may be present. The reactants may be polymerized by reacting the diamine and dicarboxylic acid directly or via their salt. Alternatively the diamine or its hydrochloride may be reacted with the dihalide of the dicarboxylic acid. Either the diamine in an organic solvent may be treated with the dicarboxylic acid chloride in a second immiscible solvent, or the diacid halide may be added to an organic solvent solution of the amine or amine salt at - 20‹ C. and under N 2 . In either case a base and/or surface active agent may be present. Solvents specified include methyl ethyl ketone, acetonitrile, propionitrile, cyclic tetramethylene sulphone, 2,4-dimethyl cyclic tetramethylene sulphone, tetramethyl urea, hexamethyl phosphoramide, N,N-dimethyl acetamide and CH 2 Cl 2 . Bases specified include pyridine, sodium bicarbonate and sodium carbonate. Surface active agents specified include sodium lauryl sulphate. The products may be shaped into fibres and films and may be used for coatings.