Patent GB-793741-A (GB)
Title: Film-forming composition with plasticizer of terephthalamide derivatives
IPC: C08K5/20
Filed: 1956-03-19
Abstract: Terephthalamide esters, used as plasticisers, are of general formula <FORM:0793741/IV (b)/1> where n is 1 or 2, R is a divalent radical and is either an arylene, divalent alicyclic or aralkylene radical having a chain length of 3 to 12 carbon atoms and B is either hydrogen or a group <FORM:0793741/IV (b)/2> where x is 1 or 2, are prepared by reacting a dioyl chloride or a dicarboxylic acid anhydride with N,N-bis-(beta hydroxyethyl)-terephthalamide or N,N1-tetra-(beta-hydroxyethyl) terephthalamide, which has been prepared by heating mono-ethanolamine or di-ethanolamine with terephthalic acid or acid ester in ethyl alcohol until a clear solution is obtained.  The product is then reacted with a dioyl chloride or a dicarboxylic acid anhydride to produce the corresponding ester.  Suitable dioyl chlorides are those having 5-14 carbon atoms, e.g. pentanedioyl chloride, hexanedioyl chloride, heptanedioyl chloride, octanedioyl chloride, nonanedioyl chloride, decanedioyl chloride, benzenedicarbonyl chlorides, cyclohexanedicarbonyl chlorides, naphthalenedicarbonyl chlorides, the acid chloride of carboxy-phenyl acetic acid, adipyl dichloride, suberyl chloride and the chlorides of methyl, ethyl, propyl, butyl, amyl and hexyl benzene dicarboxylic acids. Examples are given of the preparation of (1) an adipate of N,N1-bis-(beta hydroxyethyl) terephthalamide; (2) di-(acid phthalate) of N,N1-bis-(betahydroxyethyl) terephthalamide; (3) tetra (acid phthalate) of N,N1-tetra-(beta-hydroxyethyl) terephthalamide. Specification 671,141 is referred to.ALSO:Terephthalamide esters used as plasticizers are of the general formula: <FORM:0793741/IV (a)/1> where n is 1 or 2, R is an alkylene, arylene, divalent, alicyclic or aralkylene radical of 3-12 carbon atoms and B is hydrogen or <FORM:0793741/IV (a)/2> where x is 1 or 2.  They may be used as plasticizers for cellulosic films and sheets or for thermoplastic resins, e.g. polyvinyl chloride, polyvinylidene chloride, polystyrene, copolymers of vinyl chloride and vinyl acetate, copolymers of methyl methacrylate and vinyl chloride, polyvinyl butyral, polyvinyl acetal, polymethyl methacrylate, polymethyl acrylate, polyethylene, polyamides, synthetic rubbers, polypulphides, polyisobutylenes, oil modified and unmodified alkyd resins, and phenol formaldehyde resins prepared from phenols having only two reactive positions.  They may also be used to plasticize, e.g. cellulose acetate, cellulose acetate butyrate, cellulose acetate propionate, cellulose propionate, benzyl cellulose, ethyl cellulose, butyl cellulose, hydroxyethyl cellulose, cellulose nitrate, mixed esters or ether esters, e.g. cellulose acetate nitrate or ethyl cellulose nitrate, urea-formaldehyde, melamine-formaldehyde, phenol furfural, polyallyl alcohol and protein formaldehyde resins, and also mixtures such as polyvinyl chloride and urea formaldehyde ether, polyvinyl chloride and phenol formaldehyde, polymethacrylate and urea formaldehyde, polystyrene and alkyd couramone indene, and alkyd polyvinyl acetal and melamine formaldehyde.  In such compositions the terephthalamide ester of the invention may be present in 5-45 per cent by weight of the total solids.  Other plasticizers, e.g. dibutyl phthalate, dilauryl phthalate, cyclohexyl butyl phthalate, di-(methylcyclohexyl) phthalate, di-(dimethyl cyclohexyl) adipate, dicyclohexyl adipate, tricresyl phosphate, esters of o-benzoyl benzoic acid such as butyl benzoyl benzoate and derivatives of toluene sulphonamide may be used in association.  The terephthalamide esters may be incorporated in moisture-proofing compositions comprising a cellulose derivative and a wax such as japan wax, palm wax, beeswax, chinese insect wax, paraffin, petrolatum or certain chlorinated hydrocarbons; such compositions may include a blending agent such as ester gum, rosinates, hydrogenated rosins, and their esters, dammar, copal, kauri, alkyd resins, vinyl derivatives, chlorinated diphenyl resins, phenol formaldehyde resins, hydrogenated castor oil, castor oil phthalate, lanolin, ethyl abietate, methyl abietate, or diethylene glycol hydrorosinate.  Examples are given of a composition of nitrocellulose, paraffin, ester gum, blown rapeseed oil and the adipate of N,N1-bis-(beta hydroxyethyl) terephthalamide, and a composition of nitrocellulose, dibutyl phthalate, paraffin ester gum, blown rapeseed oil and the di-(acid phthalate of N,N1-bis-(beta hydroxyethyl) terephthalamide.  Specification 671,141 is referred to.ALSO:Terephthalamide esters used as plasticizers are of the general formula:  <FORM:0793741/V/1> where n is 1 or 2, R is an alkylene, arylene, divalent alicyclic or aralkylene radical of 3 to 12 carbon atoms and B is hydrogen or:  <FORM:0793741/V/2> where X is 1 or 2.  The terephthalamide esters may be used as plasticizers for natural rubber, chlorinated rubber, rubber hydrochloride, cyclized rubber and coumarone indene with rubber, preferably in a proportion of 5 to 45 per cent by weight of the total solids.  Other plasticizers may be present, e.g., dibutyl phthalate, dilauryl phthalate, cyclohexyl butyl phthalate, di(methylcyclohexyl) phthalate, di (dimethyl cyclohexyl) adipate, dicyclohexyl adipate, tricresyl phosphate, esters of o-benzoyl benzoic acid such as butyl benzoyl benzoate, or derivatives of toluene sulphonamide.  Blending agents such as ester gums, rosinates, hydrogenated rosin, hydrogenated rosin esters, dammar, copal, kauri, alkyd resins, vinyl derivatives, chlorinated diphenyl resins, phenol formaldehyde resins, hydrogenated castor oil, castor oil phthalate, lanolin, ethyl abietate, methyl abietate, diethylene glycol rosinate and dimethylene glycol rosinate, may be present in the compositions.  Examples of compounds of the invention are the adipate of N, N1 bis (beta hydroxyethyl) terephthalamide and the di (acid phthalate) of N, N1 bis (beta hydroxyethyl) terephthalamide. Specification 671,141 [Group IV(a)] is referred to.