Patent GB-420545-A (GB)
Title: Process for the manufacture of acid amide derivatives
Filed: 1933-02-28
Abstract: Textile assistants are prepared by treating acid amides having the formula <FORM:0420545/IV/1> wherein R stands for a radicle having at least eight carbon atoms directly connected together, R1 for hydrogen, alkyl, aryl or mono or polyhydroxyalkyl and R2 for a mono or polyhydroxyalkyl radicle, with from above one to at the most three molecular proportions of alkylene oxide per reactive hydrogen atom in R1 and R2.  The products which may be treated with polybasic oxygen containing mineral acids may be used for improving the wetting, emulsifying, cleaning and levelling properties of aqueous liquors employed in the textile industry, e.g. washing, dyeing, mercerizing, carbonizing and fulling baths. The products improve the fastness of dyeings to rubbing and may be used as solvents, and for pasting dyestuffs.  Oils, fats and hydrocarbon may be emulsified, and the lipoid soluble products find employment in the preparation of oiling, sizing, greasing, stuffing and metal protecting agents.  The use of the products in pharmaceutical preparations, salves, cosmetics, consistent fats, cutting and boring oils, polishes, lacquers, varnishes and caoutchouc is mentioned.  Soaps, turkey red oils, mineral oil and fatty alcohol sulphonates, alkylated naphthalene sulphonic acids, sulphite cellulose waste liquor, soluble gums, mucilages, alcohols, ketones, hydrocarbons and halogenated hydrocarbons may be used with the products.  In examples: (1) the acid amide obtained according to Specification 384,665 from coconut oil fatty acids and ethanolamine is treated with ethyleneoxide to give a product which with alkali phosphates and borates may be used for washing wool in hard water; acid amides derived from 1-amino-2 : 3-propanediol and hydroxyethyldihydroxypropylamine may be similarly treated with ethyleneoxide; (2) ethylene oxide is reacted with the acid amide derived from tallow and mono ethanolamine, and the acid amide treated with sulphuric acid; palm kernal fatty acid chloride and diethanol amine may also be condensed and treated with ethyleneoxide; (3) a product which may be made into a paste with sodium oleylmethyltauride and added to a dyeing, finishing or softening bath for viscose artificial silk is prepared by treating with ethyleneoxide the acid amide derived from hardened train oil and ethanolamine.  The sample furnished under Sect. 2 (5) comprises a product obtained by treating with ethyleneoxide, stearylhydroxyethylaniline which is prepared from hydroxyethylaniline and stearic acid chloride in the presence of pyridine.  The acid amides may be derived from the acids obtained by the oxidation of paraffin, resin and montan wax acids, lauric, undecylenic, oleic, dihydroxystearic, phthalic, phthalamic, cyclohexylpropionic and 1 : 8-naphthalenedicarboxylic acid, and also the acids obtained from palm oil, poppy seed oil, rape seed oil, cotton seed oil, linseed oil, soya bean oil, china wood oil and castor oil.  Substituted acids such as dichlorstearylhydroxyethylamide, obtained by chlorinating stearic acid chloride and condensing with ethanolamine, may be employed. N - butyl - N - hydroxyethylamine and di-(propanediol) amine are specified hydroxyalkylamines.  The Specification as open to inspection under Sect. 91 comprises also the treatment with alkyleneoxide, acid amides, including sulphonamides, containing aralkyl and cycloalkyl radicles attached to the nitrogen.  In an additional example, the product of the first example is mixed with benzines, terpenes, hydrogenated hydrocarbons and aliphatic, aromatic, aromatic-aliphatic or hydroaromatic alcohols or ketones.  A purifying, wetting, fat-dissolving and emulsifying agent is obtained by mixing the said product with benzyl alcohol or hydrogenated xylenol and ethylene glycolmonocresyl or monoxylenyl ether.  Crude acid amides obtained by aminolysis of glycerides may be used as starting materials and also acid amides derived from a :b -dihydroxyethylamine.  The use of phosphoric acid and phosphorus trichloride for the treatment of the products is mentioned and sulphonation may be effected in the presence of edeleanu extracts, aromatic or halogenated hydrocarbons or chlorides or anhydrides of lower fatty acids.  The sulphonated products may be chlorinated and used for weighting fibres.  The clarification of the products with peroxides, hypochlorites, fuller's earth and decolourizing carbon and their use for stabilizing azo dyes are referred to.  Albuminous substances and degradation products thereof, lipolytical and proteolytical enzymes, enzymes for degrading carbohydrates and condensation products of fatty, naphthenic and resinic acids with hydroxy and aminoalkylsulphonic acids may be used with the products. This subject-matter does not appear in the Specification as accepted.ALSO:Textile assistants are prepared by treating acid amides having the formula RCONR<1>R2 wherein R stands for a radicle having at least eight carbon atoms directly connected together, R1 for hydrogen, alkyl, aryl or mono or polyhydroxyalkyl and R2 for a mono or polyhydroxyalkyl radicle, with from above one to at the most three molecular proportions of alkylene oxide per reactive hydrogen atom in R1 and R2.  The products, which may be treated with polybasic oxygen containing mineral acids, may be used for improving the emulsifying and cleaning properties of aqueous liquors employed in the textile industry.  Oils, fats and hydrocarbons may be emulsified, and the use of the products in pharmaceutical preparations, salves, cosmetics, consistent fats, cutting and boring oils, polishes, lacquers, varnishes and caoutchouc is mentioned.  Soaps, turkey red oils, mineral oil and fatty alcohol sulphonates, alkylated naphthalene sulphonic acids, sulphite cellulose waste liquor, soluble gums, mucilages, alcohols, ketones, hydrocarbons and halogenated hydrocarbons may be used with the products.  In examples: (1) the acid amide obtained according to Specification 384,665, [Group IV], from coconut oil fatty acids and ethanolamine is treated with ethylene oxide: acid amides derived from 1-amino-2 : 3-propanediol and hydroxyethyldihydroxypropylamine may be similarly treated with ethyleneoxide: (2) ethylene oxide is reacted with the acid amide derived from tallow and monoethanolamine, and the acid amide treated with sulphuric acid; palm kernel fatty acid chloride and diethanol amine may also be condensed and treated with ethyleneoxide: (3) a product which may be made into a paste with sodium oleylmethyltauride is prepared by treating with ethyleneoxide the acid amide derived from hardened train oil and ethanolamine.  The sample furnished under Sect. 2 (5) comprises a product obtained by treating with ethyleneoxide, stearylhydroxyethylaniline.  The acid amides may be derived from the acids obtained by the oxidation of paraffin, resin and montan wax acids, lauric, undecylenic, oleic, dihydroxystearic, phthalic, phthalamic, cyclohexylpropionic and 1 : 8-naphthalene-dicarboxylic acid, and also the acids obtained from palm oil, poppy seed oil, rape seed oil, cotton seed oil, linseed oil, soya bean oil, china wood oil and castor oil. Substituted acids such as dichlorstearylhydroxyethylamide may be employed. N-butyl-N-hydroxyethylamine and di (propanediol) amine are specified hydroxyalkylamines.  The Specification as open to inspection under Sect. 91 comprises also the treatment with alkyleneoxide, acid amides, including sulphonamides, containing aralkyl and cycloalkyl radicles attached to the nitrogen.  In an additional example, the product of example (1) is mixed with benzines, terpenes, hydrogenated hydrocarbons and aliphatic, aromatic, aromaticaliphatic or hydroaromatic alcohols or ketones.  A purifying, fat-dissolving and emulsifying agent is obtained by mixing the said product with benzyl alcohol or hydrogenated xylenol and ethylene glycolmonocresyl or monoxylenyl ether.  Crude acid amides obtained by aminolysis of glycerides may be used as starting materials and also acid amides derived from a  : b -dihydroxyethylamine.  The use of phosphoric acid and phosphorus trichloride for the treatment of the products is mentioned and sulphonation may be effected in the presence of edeleanu extracts, aromatic or halogenated hydrocarbons or chlorides or anhydrides of lower fatty acids.  The sulphonated products may be chlorinated.  Albuminous substances and degradation products thereof, lipolytical and proteolytical enzymes, enzymes for degrading carbohydrates and condensation products of fatty, naphthenic and resinic acids with hydroxy and amino alkylsulphonic acids may be used with the products.  This subject-matter does not appear in the Specification as accepted.