Patent GB-535376-A (GB)
Title: Complex phenolic ester bases and salts thereof
IPC: C08G8/10
Filed: 1939-09-07
Abstract: 535,376. Ester-bases ; emulsifying agents ; mothproofing. RESINOUS PRODUCTS & CHEMICAL CO. Sept. 7, 1939, No. 25371. Convention date, Nov. 12, 1938. [Classes 2 (iii)] and 15 (ii)] [Also in Groups III and VIII] A carboxylic acid halide of the aliphatic, arylaliphatic, alicyclic or heterocyclic series is used to esterify a condensation product from a phenol, formaldehyde and a non-aromatic secondary amine. A hydrohalide of an ester base is formed which may be converted into the free base by means of alkali and then into a quaternary ammonium salt. The products are stated to have wetting, cleansing, emulsifying, softening, flotation and bactericidal properties and may be used in the following processes : bleaching, dyeing, foaming, mordanting, mothproofing, corrosion-preventing, crease-proofing and emulsion breaking. The treatment of cotton, cellulose, artificial silk, wool, silk, paper, feathers, hair and leather is mentioned. In examples: (1) a condensation product from phenol, dimethylamine and formaldehyde is esterified with coconut fatty acid chlorides in the presence of methylethylketone ; the quaternary ammonium salt prepared by means of benzylchloride from the free base derived from the product may be used for preparing lakes of direct dyestuffs or fixing the latter on fibres ; (2) the same condensation product as that used in example 1 is esterified with stearoylchloride, oleic acid chloride, naphthenic acid chloride and with cinnamoylchloride; allylbromide and sodium chloracetate may be used for the formation of quaternary ammonium salts ; (3) p-tert. butylphenol is condensed with dimethylamine and formaldehyde and the condensation product esterified with n-dodecanoylchloride ; the lactate and acetate of the base derived from the product are mentioned ; (4) acetylchloride is used to esterify the condensation products from α : α : γ : y -tetramethylbutylphenol, formaldehyde and dimethylamine and from n hexylresorcinol, formaldehyde and morpholine ; (5) 2 ethylbutyrylchloride is used to esterify the products from α : α : y : γ-tetramethylbutylphenol, formaldehyde and di-. methylamine and from 2: 4-dichlorphenol, formaldehyde and dicyclohexylamine; (6) α : α : y : y - tetramethylbutylphenol is condensed with formaldehyde and dimethylamine and the product esterified with n,caproylchloride and succinylchloride ; (7) phenol is condensed, with diethanolamine and formaldehyde and the product esterified with lauroylchloride ; (8) α : α : y : γ- tetramethylbutylphenol is condensed with formaldehyde and piperidine and the product esterified with propionylchloride : (9)1:3: 5-xylenol is condensed with formaldehyde and dimethylamine and the product esterified with sec: octyloxyacetylchloride ; (10) bis-(morpholinometho) resorcinol is esterified with 2-ethylbutyrylchloride. The following acid chlorides are also specified : crotonylchloride, acrylylchloride, methacrylylchloride, phenylacetylchloride, tetrahydrofuroylchloride, oxalyl chloride, chlorsuccinylchloride, adipylchloride, sebacylchloride, linoleic acid chloride, 4-ketostearoylchloride, p-tert: octylphenoxyacetylchloride, campholic acid chloride, abietic acid chloride, α-bromstearic acid chloride and the corresponding acid bromides. Diamylamine, methyldodecylamine, methyloleylamine, piperazine, diethanolamine and triethylenetetramine may be used as the secondary bases and the following phenols may also be used : α- and #-naphthols, o, m, and p-cresol, ethylphenol, n-propyl and iso-propyl-phenol, octadecylphenol, cyclohexylphenol, bornylphenol, phenylphenol, guaiacol, p-benzoylphenol, pyrocatechol, pyro-gallol, hydroquinone, p-acetylaminophenol, o-, m-, and p-chlorphenol, o-, m- and p-bromphenol, p : p<SP>1</SP> - dihydroxydiphenyldimethylmethane, p-hydroxystearophenone, pdodecanoylphenol, p : p<SP>1</SP>-dihydroxydiphenylsulphone, p : p<SP>1</SP> - dihydroxydiphenylsulphide, p : p<SP>1</SP> - dihydroxydiphenylsulphoxide, hydroxyanthracenes, hydroxyphenanthrenes and phenolic-formaldehyde resins in the "A" stage.