Patent GB-938113-A (GB)
Title: Polyalkyleneamides, their derivatives and polymers
Inventor: SMITH GEORGE HENRY
IPC: C07D203/18
Filed: 1959-10-23
Abstract: Coatings for surfaces of, for example, wood, glass, copper, steel and aluminium, are prepared from polymers or copolymers of polyalkylenamides (Group IV(b)).  The compounds, for example, N,N1-dis-1,2-ethylenadipamide in powder form may be melted and cured on to the surface, or in admixture with an aqueous solution of a methylol urea and melamine resin may be partially copolymerized and coated and further cured on the substrate. Other examples include mixtures of N,N1-bis2-1,2-ethylenadipamide and N-methyl cyclohexylamine or N(2-aminoethyl) piperazine and a water-based texture paint with thixotropic properties is obtained by adding N,N1-bis-1,2-ethyleneadipamide to rubberized paint containing carboxymethyl cellulose.ALSO:Polymers or copolymers of stable polyalkyleneamides of polycarboxylic acids of general formula <FORM:0938113/IV(a)/1> where R is an n-valent straight or branched chain alkylene radical, preferably with 4 to 50 carbon atoms, or an oxy- or thio-polyalkylene radical, or a benzene or naphthalene nucleus which may be substituted by an alkyl group containing not more than 8 carbon atoms or by a halogen or by a cyano group, or by a 1,2-alkylene carboxamide group, n is 2, 3 or 4 and R1 and R11 are hydrogen or alkyl groups containing not more than 8 carbon atoms (see Group IV(b)) are prepared by heating at up to 150 DEG C. alone or in the presence of an acidic or basic or an active hydrogen containing promotor such as zinc or lead chlorides, mineral acids, p-toluene sulphonic acids, boron trifluoride-monoethylamine addition products, amines and hydrazides.  Copolymers may be prepared by heating with compounds having at least two active hydrogen atoms such as epoxy monomers, amines, polycarboxylic acids, polymercaptans, polyalcohols, or by cross-linking with resins such as urea-formaldehyde, phenolic, polysulphide, polyamide, epoxy and polyester resins.  The homopolymers vary from flexible to hard scratch resistant polymers of linear or cross-linked structure of average molecular weight above 25,000.  Polymers of N,N1-bis-ethylenadipamide, N,N1-bisethylene thiodipropionamide, N,N1-bis-1,2-ethylene sebacamide and isosebacamide, N,N1-bisethylenisophthalamide, N,N1-bis-1,2-butylenisophthalamide, N,N1,N11-tris-2-methylethylene- and 2-ethylethylene-trimesamides, and copolymers of N,N1-bis-ethylenisophthalimide with a polyester resin, and a modified castor oil, N,N1,N11-tris-2-methylethylenetrimesamide with a diethlene-adipate polyester, N,N1,N11-tris-2,2-dimethylethylenetrimesamide with hexamethylenediamine, and N,N1,N11-tris-ethylenetrimesamide with a diethylene-adipate polyester are described in the examples.  The products may be used as curable melt coatings on steel, copper, wood, paper and aluminium, as pressure sensitive adhesives on paper or wood, as impregnants on wood or fabric, in the preparation of texture-type water-based latex paint with or without pigments and fillers, for electrical insulation in the casting and potting fields, for optical cement, and as formed films or sheets which may be further shaped, as a transparent rubbery sealant, and as a waterproofing agent for cloth.ALSO:The invention comprises stable polyalkylene amides of polycarboxylic acids, of general formula <FORM:0938113/IV(a)/1> where R is an n-valent straight or branched chain, alkylene radical, (preferably with 4 to 50 carbon atoms) or an oxy, or thiopolyalkylene radical, or a benzene or naphthalene nucleus which may be substituted by an alkyl group containing not more than 8 carbon atoms or by halogen or by a monofunctional group which does not contain active hydrogen, e.g. cyano, or by a 1,2-alkylene carboxamide group, n is 2, 3 or 4, and R1 and R11 are hydrogen or alkyl groups containing not more than 8 carbon atoms. The polycarboxylic acids have 6 to 55 carbon atoms per molecule and the products have at least 85% of the theoretical azirane ring content.  The compounds are prepared by the reaction of a polycarboxylic polyhalide with an alkylenimine or a mixture of two or more alkylenimines, in the presence of an aqueous and a water-immiscible phase comprising an organic liquid solvent for the polyalkylenamide, and preferably in the presence of an acid acceptor such as an ammonium or alkali metal carbonate or bicarbonate. Examples describe the preparation of N,N1-bis - ethylenadipamide, N,N1-bis-ethylenethio dipropionamide, N,N1 - bis-1,2-ethylenenonadecanediamide, N,N1-bis-1,2-ethylenepentadecyladipamide, N,N1-bis-1,2-ethylene, butylene, and propyleneisosebacamide, N,N1-bis-1,2-ethylene and propylenesebacamide, N,N1-bis-1,2-ethylenazelamide, N,N1 - bis-1,2-ethylenedodecane dicarboxylic acid amide, N,N1-bis-1,2-ethylene, butylene and propylene isophthalamide, N,N1-bis-1,2-ethylene and propylene chloroisophthalamide, N,N1,N11-tris ethylene, 2-methylethylene and 1-ethylethylene trimesamide, and N,N1,N11, - tris-2,2-dimethylethylene trimesamide. Polymers and copolymers may be prepared by the action of heat, or acidic or basic promotors such as sulphonic or p-toluenesulphonic acids, or amines to form clear transparent thermosetting resins.ALSO:Fabric, e.g. cotton cloth is waterproofed by immersing in a benzene solution of N,N1,N11,-tris-2-methylethylenetrimesamide, an example of a polyalkyleneamide (see Group IV(b)) which is air dried and polymerized in situ.