Patent GB-961023-A (GB)
Title: Epoxide resin compositions
Inventor: SMITH KEITH BEADSMORE
IPC: C08G59/40
Filed: 1959-09-28
Abstract: Betaines of the general formula: <FORM:0961023/C1/1> or salts thereof, in which x is a whole number from 0 to 9, Y is a carboxylic, sulphonic or phosphoric acid group, R is alkyl, aryl or heterocyclic (or the 3R's with the N from an unsaturated heterocyclic group), R1 is H, alkyl, aryl or a heterocyclic group and R2 is H, alkyl aryl, a heterocyclic group or Y, may be made:-(1) by heating sodium chloracetate with a tertiary amine in alcohol or aqueous alcohol. This method is suitable for N:N:N-trimethyl acetobetaine; N:N:N-triethyl acetobetaine; N-cetyl-N:N-dimethyl acetobetaine; N-octadecyl-N:N-dimethyl acetobetaine; N-phenyl-N-N:dimethylacetobetaine; pyridine acetobetaine; and the acetobetaine from the tertiary amine made by reducing the dimethylamide of coconut fatty acids.  (2) by reacting b -propiolactone with a tertiary amine in water, ether or acetonitrile. This method is suitable for N-octadecyl-N:N-dimethyl propiobetaine; N:N:N-trimethyl propiobetaine; N-benzyl - N : N-dimethylpropiobetaine; N-hexyl-N:N-dimethyl propiobetaine; N:N-dimethyl-N-dodecyl propiobetaine; and the propiobetaine from the tert. amine made by reduction of the dimethylamide of coconut fatty acids.  In other methods of preparation (1) a -bromostearic acid or 11-bromundecanoic acid was neutralized with sodium carbonate and refluxed with trimethylamine in ethanol. (2) Mono sodium-2-bromoethane sulphonic acid was refluxed with dodecyl dimethyl amine in ethanol.  The N-dodecyl-N:N-dimethylammonium ethane-2-sulphonate was precipitated out with acetone. N-dodecyl-N:N-dimethylammonium propane-3-sulphonate was similarly prepared.ALSO:A heat-curable composition comprises an epoxide resin and a betaine having the general formula: <FORM:0961023/C3/1> or a salt thereof, in which X represents a whole number from 0 to 9, Y a carboxylic, sulphonic or phosphoric acid group, R an alkyl, aryl or heterocyclic group (or the three R's together with the N represent an unsaturated heterocyclic group), R1 represents H, an alkyl, aryl or heterocyclic group, and R2 represents H, an alkyl, aryl or heterocyclic group or  Y.  Coating compositions according to the invention may also contain alkyl resins(e.g. as in Specifications 870,278 and 903,774), aminoplasts, phenol-aldehyde resins, polyamides, or acrylic-vinyl copolymers which contain free carboxyl groups.  The compositions may also include pigments, and solvents. Curing of the composition is assisted by small amounts of water or alcohols. Salts of a betaine with an organic acid (e.g. a copolymer of 2-vinyl toluene and acrylic acid with or without ethyl acrylate) are particularly useful, and can stability is still further improved if a mixture of organic acid and of betaine is used in place of the preformed salt.  In the examples the epoxide resins are polyhydrin phenolepichlorhydrin condensates known as "Epikotes" (Registered Trade Mark).  The examples describe the use of the following hardeners:-N:N:N-trimethyl acetobetaine; N-octadecyl-N:N-dimethylacetobetaine; N-octadecyl-N:N-dimethylpropiobetaine; dimethylaniline acetobetaine; pyridine acetobetaine; N-octadecyl-N-methyl-N-undecyl aceto betaine; N-benzyl-N:N-di-2-methyl isopropyl acetobetaine; N:N:N-trimethyl propiobetaine; N-benzyl-N:N-dimethyl propiobetaine; N-dodecyl-N:N-dimethylammonium ethane-2-sulphonate; N-dodecyl-N:N-dimethylammonium propane-3-sulphonate; Some examples use mixtures of two of the above hardeners.  Others use salts, e.g. a hydrochloride, acetate, phosphate or oxalate.  The examples of pigmented coating compositions contained in addition to the resin, a betaine containing a COOH group, TiO2 and a xylol-butanol solvent mixture, in one case a co-polymer of vinyl toluene, ethyl acrylate and acrylic acid, and in the other a copolymer of styrene, ethyl acrylate and acrylic acid.  Specification 904,559 also is referred to.