Patent GB-340272-A (GB)
Title: Improved assistant and auxiliary agent for use in the textile and allied industry
IPC: D06M13/256
Filed: 1929-07-19
Abstract: Tall oil derivatives, which may be used for preparing fine dispersions of solid insoluble substances, are prepared by treating tall oil esters or amides with sulphonating agents, e.g. sulphuric acid, oleum, chlor-sulphonic acid, or chlorsulphonic alkyl esters. When sulphuric acid is used, temperatures above 35 DEG  C. must be employed so that true sulphonic acids, and not sulphuric esters are produced.  Dehydrating agents, e.g. acid anhydrides or halides, such as acetic and phosphoric anhydride or acetyl or phosphoric chloride may be used instead of or in addition to elevated temperatures.  The reaction is facilitated by acids, e.g. phosphoric acid and also by means of active charcoal. The sulphonation process described in Specification 306,052, [Class 2 (iii) Dyes &c.], by means of which true sulphonic acids are obtained from unsaturated acids may be employed.  In a modification of the invention, esters are formed during or after the sulphonation of tall oil by the addition of alcohols.  Alkyl, hydroxyalkyl or aralkyl groups may be introduced by esterification of the sulphonated tall oil amides or esters, e.g. with dimethylsulphate.  The products may be used as such or as salts with inorganic or organic bases, e.g. alkalies, alkylamines, alkylolamines (mono-, di- or triethanolamine or propanolamines) or aniline or with heterocyclic bases such as pyridine.  In examples: (1) tall oil n-butyl ester is sulphonated by means of gaseous sulphur trioxide in the presence of carbon tetrachloride: (2) tall oil amide is sulphonated by means of monohydrate in the presence of acetic anhydride: (3) tall oil anilide is sulphonated by means of oleum: (4) tall oil hydroxyethylester is sulphonated in carbontetrachloride by means of chlorsulphonic acid: (5) tall oil is sulphonated with chlorsulphonic acid in the presence of ether, and the resulting sulphonic acid esterified with benzyl alcohol: (6) tall oil is treated with a mixture of chlorsulphonic acid and n-butyl alcohol in the presence of ether, the n-butyl ester of tall oil sulphonic acid being obtained.  The products are stable in baths containing acids, strong alkalies or alkaline earths and may be used in dyeing, washing, carbonizing, mercerizing, dressing and milling processes. They emulsify waxes, tars, asphalts, fats, dyestuffs and other water insoluble substances and may thus be used as washing and cleansing agents, other cleansing or dispersing agents, such as cyclohexanol, alcohols, esters or other solvents, soaps, turkey red oils, saponins, protective colloids, such as vegetable mucilages, glues, gums, starch or dextrine or salts such as Glauber's salts, naphthalene sulphonates, or acids or alkalies being added if desired.ALSO:Sulphonated tall oil esters and amides; cleansing-compositions; emulsions, making.-Tall oil derivatives, which are stated to be wetting, cleansing, dispersing and emulsifying agents for use in the textile and leather industries, are prepared by treating tall oil esters or amides with sulphonating agents, e.g. sulphuric acid, oleum, chlorsulphonic acid, or chlorsulphonic alkyl esters. When sulphuric acid is used, temperatures above 35 DEG  C. must be employed so that true sulphonic acids, and not sulphuric esters are produced.  Dehydrating agents, e.g. acid anhydrides or halides, such as acetic and phosphoric anhydride or acetyl or phosphoric chloride, may be used instead of or in addition to elevated temperatures.  Diluents such as glacial acetic acid, halogenated hydrocarbons or nitrobenzene may be used and the reaction is facilitated by acids, e.g. phosphoric acid and also by means of active charcoal.  The sulphonation process described in Specification 306,052 by means of which true sulphonic acids are obtained from unsaturated acids may be employed.  In a modification of the invention, esters are formed during or after the sulphonation of tall oil by the addition of alcohols.  Alkyl, hydroxyalkyl or aralkyl groups may be introduced by esterification of the sulphonated tall oil amides or esters, e.g. with dimethylsulphate.  The products may be used as such or as salts with inorganic or organic bases, e.g. alkalies, alkylamines, alkylolamines (mono-, di- or tri-ethanolamine or propanolamines) or aniline or with heterocyclic bases such as pyridine.  In examples: (1) tall oil n-butyl ester is sulphonated by means of gaseous sulphur trioxide in the presence of carbon tetrachloride. The sodium salt of the product is used for washing wool, hard water being employed: (2) tall oil amide is sulphonated by means of monohydrate in the presence of acetic anhydride.  The sodium salt of the product, in admixture with soap and sodium carbonate is used for milling goods: (3) tall oil anilide is sulphonated by means of oleum.  Woollen yarn is degreased by means of a bath containing the sodium salt of the product and cyclohexanone: (4) tall oil hydroxyethylester (prepared from ethylene chlorhydrin and tall oil potassium salt) is sulphonated in carbontetrachloride by means of chlorsulphonic acid: (5) tall oil is sulphonated with chlorsulphonic acid in the presence of ether, and the resulting sulphonic acid esterified with benzyl alcohol: (6) tall oil is treated with a mixture of chlorsulphonic acid and n-butyl alcohol in the presence of ether, the n-butyl ester of tall oil sulphonic acid being obtained. The products are stable in baths containing acids, strong alkalies or alkaline earths and may be used in dyeing, washing, carbonizing, mercerizing, dressing and milling processes.  They emulsify waxes, tars, asphalts, fats, dyestuffs and other water insoluble substances and may thus be used as washing and cleansing agents, other cleansing or dispersing agents, such as cyclohexanol alcohols, esters or other solvents, soaps, turkey red oils, saponius, protective colloids, such as vegetable mucilages, glues, gums, starch or dextrine or salts such as Glauber's salts, naphthalene sulphonates, or acids or alkalies being added if desired.  An emulsion of oil prepared by means of the products may be used for oiling or impregnating.  Tall oil esters and amides are prepared from tall oil by treating the latter with phosphorus trichloride and condensing the resulting tall oil chloride with alcohols, ammonia or primary or secondary amines.  Tall oil may also be esterified by treatment with an alcohol in the presence of hydrochloric or sulphuric acids.  Specifications 272,967, 275,267 and 303,917, [all in Class 2 (iii), Dyes &c.], also are referred to.