Patent GB-380851-A (GB)
Title: Improvements in the manufacture and production of assistants in the textile and related industries and dispersing agents
IPC: D06P1/607
Filed: 1931-04-10
Abstract: Products which may be used as assistants in the textile and related industries are produced by treating insoluble amines or carboxy or sulphonic amides containing at least one hydrogen atom connected to nitrogen but no hydroxy groups, with polyethyleneglycols containing a chain of at least six --CH2.CH2.O--groups or with mono ethers or esters thereof.  In modifications, (a) the corresponding quantity of ethyleneoxide or ethylenehalogenhydrin is used in place of the polyethyleneglycol, (b) when a polyethyleneglycol or ethyleneoxide is used and the products contain free hydroxy groups, the latter are esterified or etherified, (c) when the products contain a halogen or a halogen has been introduced, the latter is treated with an amine, an amide or a hydroxy compound.  The products are stated to be wetting, emulsifying, cleansing and foaming agents and may be used alone or in association with alkali, ammonia or amine soaps, aliphatic or aromatic sulphonic acids, sulphuric esters of high molecular alcohols, vegetable and animal oils or fats, natural or synthetic waxes, cellulose esters or ethers, turkey red oils, saponine, glue, vegetable mucilages, dextrine or other colloids, solvents, Glauber's salt, magnesium sulphate, sodium chloride or bleaching agents such as perborates.  In examples: (1) 1 mol. of octodecylamine is treated with 18 mols. of ethyleneoxide in an autoclave; the product is a wetting and levelling agent: (2) natural silk is dyed in a bath containing the product obtained by condensing 9 mols. of ethyleneoxide with 1 mol. of octodecylamine, Diamond Green GX or Victoria pure blue B and acetic acid, and the fabric finished in a solution of formic or acetic acid: (3) wool yarn is dyed in a bath containing the condensation product used in the last example, a chromium salt of the dyestuff obtained by coupling diazotized picramic acid with 1-naphthylamine-4-sulphonic acid and sulphuric acid: (4) the mixed amides of coco nut oil acids are fused with the product obtained by condensing 10-30 mols. of ethyleneoxide with 1 mol. of oleyl alcohol; the pastes or emulsions obtained by adding water to the product may be used for finishing or sizing textiles. Products are also obtained as follows: (a) octodecylamine is condensed in the presence of potassium carbonate with the bromide of the polyethyleneglycol obtained by treating with red phosphorus and bromine the condensation product of diethyleneglycol with 20 mols. of ethyleneoxide: (b) dodecylamine is condensed with hexaethyleneglycolmonochloraceticester, which is obtained by treating monochloracetic acid with ethyleneoxide: (c) dodecanesulphamide is heated with ethyleneoxide: (d) p-toluene sulphamide is heated with ethyleneoxide.  The products containing free hydroxy groups may be esterified or etherified with carboxylic acids e.g. higher fatty acids or phthalic acid, sulphuric acid, phosphoric acid, acid halides, sulphuric esters, and alkyl diaryl halides, e.g. halogenated paraffin wax.  The products containing halogen, e.g. those obtained by means of halogen hydrins, or with monohalogenhydracid esters of the polyethyleneglycols, or by substituting hydroxy groups by means of iodine or bromine may be treated with amine,a acid amides or hydroxy compounds.  The amides derived from caproic, lauric, oleic, linoleic, palmitic, stearic, montanic, and naphthenic acids and those obtained from beeswax and by the destructive oxidation of paraffin and similar hydrocarbons may be used as starting materials.  The following amines are specified: decyl, undecyl, tetradecyl, cetyl, pentadecyl, diheptyl, dibutyl and diphenyl amines.  Diluents and the following condensing agents may be used, surface acting substances, e.g. bleaching earths or active charcoal, sulphuric or phosphoric acid, sodium or potassium bisulphates, caustic soda, and alkali metal alcoholates.  The products may be used in the textile, leather, paper, wax, and polish industries, for example in carbonizing, mercerizing, dressing, bucking, washing, finishing, dyeing, printing, and stripping, and they dissolve or disperse vegetable or animal fats or oils, natural and artificial resins and waxes, dyestuffs and pigments, e.g. carbon black.  They may also be used as softening agents, e.g. in films, bands, and artificial resin or cellulose ester or ether lacquers, and in enzymatic processes such as the degradation of proteins or carbohydrates in degumming or desizing. The use of the products as textile and drilling oils and in dyeing with vat dyestuffs and azo dyestuffs from b -naphthoic acid arylides on the fibre is also mentioned.  Specifications 312,523, 317,770, 328,190, [all in Class 2 (iii), Dyes &c.], 346,438, 358,114, 364,000, 364,323, and 380,431 are referred to.  Dodecanesulphamide is prepared by treating the sodium dodecanesulphonate obtained according to example 1 of Specification 360,539 with phosphorus pentachloride and reacting the product with ammonia.ALSO:Products which may be used as emulsifying agents or lubricants are produced by treating insoluble amines or carboxy or sulphonic amides containing at least one hydrogen atom connected to nitrogen but no hydroxy groups, with polyethyleneglycols containing a chain of at least six -CH2.CH2.O- groups or with mono ethers or esters thereof.  In modifications, (a) the corresponding quantity of ethyleneoxide or ethylenehalogenhydrin is used in place of the polyethyleneglycol, (b) when a polyethyleneglycol or ethyleneoxide is used and the products contain free hydroxy groups, the latter are esterified or etherified, (c) when the products contain halogen or a halogen has been introduced, the latter is treated with an amine, an amide or a hydroxy compound. The products are stated to be emulsifying and cleansing agents and may be used alone or in association with alkali, ammonia or amine soaps, aliphatic or aromatic sulphonic acids, sulphuric esters of high molecular alcohols, vegetable and animal oils or fats, natural or synthetic waxes, cellulose esters or ethers, turkey red oils, saponine, glue, vegetable mucilages, dextrine or other colloids, solvents, Glauber's salt, magnesium sulphate, sodium chloride or bleaching agents such as perborates.  In examples: (1) 1 mol. of octodecylamine is treated with 18 mols. of ethyleneoxide in an autoclave; the product is a wetting and levelling agent: (2) the mixed amides of coco-nut oil acids are fused with the product obtained by condensing 10-30 mols. of ethyleneoxide with 1 mol. of oleyl alcohol; the pastes or emulsions obtained by adding water to the product may be used for finishing or sizing textiles.  Products are also obtained as follows: (a) octodecylamine is condensed in the presence of potassium carbonate with the bromide of the polyethyleneglycol obtained by treating with red phosphorus and bromine the condensation product of diethyleneglycol with 20 mols. of ethyleneoxide, (b) dodecylamine is condensed with hexaethyleneglycolmonochloraceticester which is obtained by treating monochloracetic acid with ethyleneoxide, (c) ethyleneoxide is condensed with dodecanesulphamide and with p-toluenesulphamide.  The products containing free hydroxy groups may be esterified or etherified with carboxylic acids e.g. higher fatty acids or phthalic acid, sulphuric acid, phosphoric acid, acid halides, sulphuric esters, or alkyl or aryl halides, e.g. halogenated paraffin wax.  The products containing halogen e.g. those obtained by means of halogen hydrins, or with monohalogenhydracid esters of the polyethyleneglycols, or by substituting hydroxy groups by means of iodine or bromine may be treated with amines, acid amides or hydroxy compounds.  The following amines are specified: decyl, undecyl, tetradecyl, cetyl, pentadecyl, diheptyl, dibutyl and diphenyl amines. The products dissolve or disperse vegetable or animal fats or oils, natural and artificial resins and waxes, and pigments e.g. carbon black.  They may also be used as textile, lubricating and drilling oils.ALSO:A fine dispersion of copper hydroxide, which may be used as a pest destroying agent is obtained by mixing with an aqueous suspension of lime and copper sulphate, a product prepared by condensing 18 mols. of ethylene oxide with 1 mol. of octodecylamine.