Patent GB-850459-A (GB)
Title: New n-substituted amides of aromatic polycarboxylic acids and their production
Inventor: FULLER MAC FRANCIS
IPC: C11C5/00
Filed: 1959-02-16
Abstract: A pressure sensitive adhesive is prepared from a solution comprising polyisobutylene, a C18-C22-t-alkyl terephthalamide product, white mineral oil, and aliphatic petroleum naphtha.  The solution may be applied by brushing to paper or regenerated cellulose sheet.  After evaporation of the solvent the adhesive coating is pressure-sensitive.  The terephthalamide product is obtained by reacting terephthaloyl chloride with a mixture of tertiary alkyl primary amines composed principally of amines ranging from t-C18 H37NH2 to t-C22H45NH2 but containing 10-12% of t-C15-C17 alkyl primary amines (See Group IV(b)).ALSO:The invention comprises compounds of the general formula:  <FORM:0850459/IV(b)/1> where X is <FORM:0850459/IV(b)/2> n is 2-3, no two x radicals are in adjacent positions on the benzene ring, and each of the R's represents a C1-C19 alkyl group, the sum of the carbon atoms in R1, R2 and R3 being 10-21.  The compounds may be prepared by reacting an acid halide, e.g. the acid chloride of terephthalic, isophthalic or trimesic acid with a C11-C22 tert. alkyl primary amine, preferably in the presence of an acid acceptor.  The amine starting materials may be prepared from olefins of formula:  <FORM:0850459/IV(b)/3> in which the sum of the carbon atoms in R1 + R2 + R3 is 9-20, R1 is hydrogen or an alkyl radical and R2 and R3 are alkyl radicals, by reaction with hydrogen cyanide and sulphuric acid in the Ritter reaction.  The alkyl amines used as starting materials may be used singly or in admixture.  The molar ratio of tertiary alkyl primary amine to acid chloride group is preferably 1 : 1, and the reaction temperature preferably below about 60 DEG  C.  A reaction medium of, e.g. methylene chloride benzene or toluene, may be used, and the reaction mixture should be agitated if a heterogenous reaction medium is used. Acid acceptors specified are alkali metal carbonates and tertiary amines.  Many examples are given.ALSO:Compounds of formula: <FORM:0850459/III/1> where X is <FORM:0850459/III/2> n is 2-3, no two X radicals are in adjacent positions on the benzene ring, and each of the Rs represents a C1-C19 alkyl group, the sum of the carbon atoms in R1, R2 and R3 being 10-21, are incorporated in coating compositions, greases, lubricants, and waxes including candle wax. Compounds of the above formula include N - substituted amides of terephthalic, isophthalic, and trimesic acids.  They may be dissolved in common organic solvents and the solutions may be sprayed or otherwise applied to non-porous surfaces such as metals, plastics, paint, varnish, and lacquer finishes to give hydrophobic films serving as protective coatings.  Those compounds having t-alkyl substituents in the C11-C14 range may be used as hardening agents in candles.  The compounds may be used in preparing grafting waxes, wax crayons and graphite pencils. They may be used as thickening agents for water-repellent greases and as lubricants for rayon yarns.  The N-t-alkyl terephthalamides may be used as bases for caulking or glazing compounds.  The amide compounds may be used for coating hard surfaces, giving coatings which may be buffed to a high gloss.  In an example, a C15-C22-t-alkyl terephthalamide is mixed with raw linseed oil, white mineral oil, basic lead carbonate, and titanium dioxide to form a caulking composition which is applied to a wood board. Another example describes a coating composition comprising a C11 - C14 - t - alkyl iso - phthalamide, beeswax, mineral spirits, and aliphatic petroleum naphtha.  The solution is applied to a nitrocellulose lacquer finish and the dried coating is buffed to give a lustrous water-repellent finish.  A similar solution is applied to a steel panel finished with baked automobile enamel and the coating is buffed.