Patent GB-420903-A (GB)
Title: Process for the manufacture of new reaction products of aliphatic hydroxy compounds
IPC: D06M11/38
Filed: 1933-03-02
Abstract: Materials useful as auxiliary agents in the textile and other industries are prepared by reacting glycide with a water-insoluble aliphatic compound containing more than eight carbon atoms directly connected together and containing as reactive groups only a hydroxyl group or groups, at least two molecular proportions of glycide being present for each of the hydroxyl groups.  The said aliphatic compounds do not include polyvinyl alcohols or carbohydrates.  The products may subsequently be etherified or esterified, e.g. with inorganic or organic acids or their acid chlorides and anhydrides, chlorethane sulphonic acid, benzyl chloride sulphonic acid, ethylene sulphonic acid, alkylene oxides and epichlorhydrin.  The products are useful as emulsifying, cleansing, wetting, dispersing, impregnating and softening agents in the textile, leather, caoutchouc, lacquer and paper industries, as protective colloids in the dye industry, and in the cosmetic and pharmaceutical industries for preparing creams and salves.  An example is given of the treatment of dodecyl alcohol with glycide to give a material useul as a washing agent in aqueous solution.  Octadecyl and oleyl alcohols, and castor oil, may be similarly treated.  The samples are prepared by heating the reaction product of dodecyl alcohol and glycide with either ethylene oxide at 180 DEG  C. or concentrated sulphuric acid at 35 DEG  C.  The Specification as open to inspection under Sect. 91 describes also the interaction of glycide with organic compounds containing amino and/or carboxylic and/or carboxylic acid amide and/or sulphonamide groups, in so far as they contain reactive hydrogen atoms.  Amino compounds specified are butylamine, octadecylamine, benzylamine, hexahydroaniline, dibutylamine, cyclohexylethylaniline, dicyclohexylaniline, piperidine, morpholine, diethanolamine, diethylenediamine, aniline, diphenylamine, aminophenols, amino-alcohols, naphthylamine, arylene diamines, naphthylene diamine and ethylaniline.  As carboxylic acids, butyric, lauric, palmitic, oleic, linoleic, ricinoleic, lactic, maleic, tartaric, adipic, benzoic, phenylacetic and anthranilic acids are mentioned; also coconut oil fatty acid, oleylglycocoll and stearylsarcosine.  Acid amides referred to are butylethylamide, lactic acid hydroxyethylamide, oleylamide, palmitic acid hydroxyethylamide, linoleic acid anilide, ricinoleic acid dihydroxypropylamide, benzoic acid butylamide, salicylic acid phthalide, phthalimide, phthalamic acid, toluene sulphonic acid cyclohexylamide and laurylethylenediamine.  The reaction of glycide with other hydroxy compounds than water-insoluble aliphatic compounds containing more than eight carbon atoms directly connected together is also described; such hydroxy compounds are butyl alcohol, glycerine, sorbite, starch, phenol, cresol, xylenol, naphthol, dihydroxyphenols and the esters of salicylic acid.  The quantity of glycide employed depends upon the desired properties of the products, quantities varying from those giving incomplete conversion to relatively large amounts being mentioned.  Instead of glycide, a mixture of monochlorhydrin and alkali lye in equimolecular quantities may be used.  The products may subsequently be etherified or esterified as before.  Examples are given of (1) the treatment with glycide of isobutyl alcohol, undecylamine, linseed oil fatty acid and coconut oil fatty acid hydroxyethylamide; (2) the condensation of glycide with itself and the treatment of the polymerized product with oleic acid chloride or coconut oil fatty acid chloride; (3) the treatment of aniline with monochlorhydrin and caustic soda solution.  The products are useful for the same purposes as before and may be used in conjunction with other substances such as soaps, turkey red oil, sulphonates of mineral oil and fatty alcohols, alkylated naphthalene sulphonic acids, glue, gelatine, lysalbinic acid, sulphite liquor, water-soluble gums, mucilages, alcohols, glycols, phenols, ketones, hydrocarbons and halogenated hydrocarbons. This subject-matter does not appear in the Specification as accepted.  Reference has been directed by the Comptroller to Specifications 313,892, [Class 2 (iii)], and 368,530 (as open to inspection under Sect. 91 of the Acts).ALSO:Materials stated to be useful as emulsifying, cleansing, and dispersing agents in the textile, leather, caoutchouc, lacquer and paper industries and as protective colloids in the dye industry, are prepared by reacting glycide with a water-insoluble aliphatic compound containing more than eight carbon atoms directly connected together and containing as reactive groups only a hydroxyl group or groups, at least two molecular proportions of glycide being present for each of the hydroxyl groups.  The said aliphatic compounds do not include polyvinyl alcohols or carbohydrates.  The products may subsequently be etherified or esterified, e.g. with inorganic or organic acids or their acid chlorides and anhydrides, chlorethane sulphonic acid, benzyl chloride sulphonic acid, ethylene sulphonic acid, alkylene oxides and epichlorhydrin.  An example is given of the treatment of dodecyl alcohol with glycide to give a material useful as a washing agent in aqueous solution.  Octadecyl and oleyl alcohols, and castor oil, may be similarly treated.  The samples are prepared by heating the reaction product of dodecyl alcohol and glycide with either ethylene oxide at 180 DEG  C. or concentrated sulphuric acid at 35 DEG  C.  The Specification as open to inspection under Sect. 91 described also the interaction of glycide with organic compounds containing amino and/or carboxylic and/or carboxylic acid amide and/or sulphonamide groups, in so far as they contain reactive hydrogen atoms.  Amino compounds specified are butylamine, octadecylamine, benzylamine, hexahydroaniline dibutylamine, cyclohexylethylaniline, dicyclohexylaniline, piperidine, morpholine, diethanolamine, diethylenediamine, amiline, diphenylamine, aminophenols, amino-alcohols, naphthylamine, arylene diamines, naphthylene diamine and ethylaniline.  As carboxylic acids, butyric, lauric, palmitic, oleic, linoleic, ricinoleic, lactic, maleic, tartaric, adipic, benzoic, phenylacetic and anthranilic acids are mentioned; also coconut oil and fatty acid, oleylglycocoll and stearylsarcosine.  Acid amides referred to are butylethylamide, lactic acid hydroxyethylamide, oleylamide, palmitic acid hydroxyethylamide, linoleic acid anilide, ricinoleic acid dihydroxypropylamide, benzoic acid butylamide, salicylic acid phthalide, phthalimide, phthalamic acid, toluene sulphonic acid cyclohexylamide and laurylethylene diamine.  The reaction of glycide with other hydroxy compounds than water-insoluble atiphatic compounds containing more than eight carbon atoms directly connected together is also described; such hydroxy compounds are butyl alcohol, glycerine, sorbite, starch, phenol, cresol, xylenol, naphthol, dihydroxyphenols and the esters of salicylic acid.  The quantity of glycide employed depends upon the desired properties of the products, quantities varying from those giving incomplete conversion to relatively large amounts being mentioned.  Instead of glycide, a mixture of monochlorhydrin and alkali lye in equimolecular quantities may be used.  The products may subsequently be etherified or esterified as before.  Examples are p  given of (1) the treatment with glycide of isobutyl alcohol, undecylamine, linseed oil fatty acid and coconut oil fatty acid hydroxyethylamide; (2) the condensation of glycide with itself and the treatment of the polymerised product with oleic acid chloride or coconut oil fatty acid chloride; (3) the treatment of aniline with monochlorhydrin and caustic soda solution.  The products are useful for the same purposes as before and may be used in conjunction with other substances such as soaps, turkey red oil, sulphonates of mineral oil and fatty alcohols, alkylated naphthalene sulphonic acids, glue, gelatine, lysalbinic acid, sulphite liquor, water-soluble gums, mucilages, alcohols, glycols, phenols, ketones, hydrocarbons and halogenated hydrocarbons. This subject-matter does not appear in the Specification as accepted.  Reference has been directed by the Comptroller to Specifications 313,892, [Class 2 (iii)], and 368,530, (as open to inspection under Sect. 91 of the Acts), [Group IV].ALSO:Materials useful in the manufacture of salves are prepared by reacting glycide with a water-insoluble aliphatic compound containing more than eight carbon atoms directly connected together and containing as reactive groups only a hydroxyl group or groups, at least two molecular proportions of glycide being present for each of the hydroxyl groups.  The said aliphatic compounds do not include polyvinyl alcohols or carbohydrates.  The products may subsequently be etherified or esterified, e.g. with inorganic or organic acids or their acid chlorides and anhydrides, chlorethane sulphonic acid, benzyl chloride sulphonic acid, ethylene sulphonic acid, alkylene oxides and epichlorhydrin.  As example is given of the treatment of dodecyl alcohol with glycide; octadecyl and oleyl alcohols, and castor oil, may be similarly treated.  The samples are prepared by heating the reaction product of dodecyl alcohol and glycide with either ethylene oxide at 180 DEG  C. or concentrated sulphuric acid at 35 DEG  C.  The Specification as open to inspection under Sect. 91 described also the interaction of glycide with organic compounds containing amine and/or carboxylic and/or carboxylic acid amide and/or sulphonamide groups, in so far as they contain reactive hydrogen atoms.  Amino compounds specified are butylamine, octadecylamine, benzylamine, hexahydroaniline, dibutylamine, cyclohexylethylaniline, dicyclohexylaniline, piperidine, morpholine, diethanolamine, diethylenediamine, aniline, diphenylamine, aminophenols, amino-alcohols, naphthyl