Linear polyamides from bis-(omega-aminoalkyl) phosphines and dicarboxylic acids

摘要

A method of making a linear polyamide comprises effecting a condensation reaction between substantially equimolar proportions of (a) a diamine and (b) a dicarboxylic acid or anhydride or an amide-forming derivative thereof, one and/or the other of the reactants containing a phosphine group of the formula FORM:0897680/IV (a)/1 and the other, when it does not contain said phosphine group having a divalent hydrocarbon radical containing from 1 to 18 carbon atoms, R1 and R2 each representing a divalent hydrocarbon radical containing from 2 to 12 carbon atoms and R being a hydrocarbon radical. Many hydrocarbon radicals represented by R, R1, R2 and R1 are specified. The condensation may be effected in the absence or presence of an inert solvent or diluent, e.g. phenols, cresols, dimethyl formamide, aliphatic or aromatic hydrocarbons or diphenyl ether or by the "interfacial" technique employing two different immiscible solvents. In the examples, polyamides are made from:-(1) bis-(3-aminopropyl)phenylphosphine and adipic acid (2) bis(3-aminopropyl)phenylphosphine and terephthalic acid (3) bis(3-aminopropyl)-b -phenethylphosphine and adipic acid (4) tetradecamethylene dicarboxylic acid and bis(3-aminopropyl)phenylphosphine (5) bis(3-aminopropyl)-phenylphosphine and quadric acid (6) adipic acid and bis(o -aminododecyl)phenylphosphine (7) bis(p-aminophenyl)octadecylphosphine and adipic acid (8) bis(p-aminophenyl)methylphosphine and adipic acid (9) bis(3-aminopropyl)-phenylphosphine and sebacyl chloride (10) bis-(3-aminopropyl)-p-tolylphosphine and sebacyl chloride (11) bis(3-aminopropyl)isobutylphosphine and sebacyl chloride (12) bis(3-aminoethyl)cyclohexylphosphine and sebacyl chloride (13) bis(3-aminopropyl)-2-butenylphosphine and sebacyl chloride (14) bis(3-aminopropylisobutylphosphine and quadryl chloride (15) bis(p-aminophenyl)octadecylphosphine and succinic acid (16) bis(2-cyanoethyl)phenylphosphine and hexamethylene diamine (17) hexamethylene diamine and bis(2-cyanoethyl)-methylphosphine (18) piperazine and bis(2-cyanoethyl)-phenylphosphine (19) ethylene diamine and bis(2-cyanoethyl)phenylphosphine (20) bis(2-cyanoethyl)phenylphosphine and bis(3-aminopropyl)-phenylphosphine (21) bis(2-cyanoethyl)ethylphosphine and formaldehyde and (22) bis(2-cyanoethyl)phenylphosphine and formaldehyde. U.S.A. Specifications 2,071,250, 2,071,251, 2,071,253, 2,130,523, 2,130,948 and 2,646,420 are referred to.ALSO:Bis(3-aminopropyl)phenylphosphine used in the production of a linear polyamide (see Group IV(a)) is made by reacting phenylphosphine with allyl amine in the presence of benzene and azobisisobutyronitrile under an atmosphere of nitrogen. U.S.A. Specifications 2,071,250, 2,071,251, 2,071,253, 2,130,523, 2,130,948 and 2,646,420 are referred to.