Patent GB-611210-A (GB)
Title: Improvements in or relating to detergents and processes of preparing the same
IPC: C07C309/58
Filed: 1944-09-19
Abstract: Emulsifying agents comprise compounds having the general formula <FORM:0611210/III/1> wherein R is an alkyl radical having from 8 to 18 carbon atoms, Ar is a monocyclic aromatic hydrocarbon residue, X is hydrogen, a halogen or an hydroxyl group, Y is an alkali metal, calcium or magnesium and m and n are integers.  The examples describe salts of sulpho-benzoic and sulpho-salicylic acid esters of such alcohols as octyl, decyl, tetradecyl and octadecyl alcohols. Their preparation is given (see Group IV (c)).  The Specification as open to inspection under Sect. 91 refers also to compounds of the above formula, wherein Y is hydrogen.  This subject-matter does not appear in the Specification as accepted.ALSO:Surface-active materials are prepared by heating an aliphatic alcohol having from 8 to 18 carbon atoms with a sulphonated monocyclic aromatic monocarboxylic acid of the general formula <FORM:0611210/IV(b)/1> wherein Ar is a monocyclic aromatic hydrocarbon nucleus, X is hydrogen, a halogen or a hydroxyl group and m and n are integers, or with the corresponding carboxylic acid anhydride, in the presence of an organic solvent which forms an azeotrope with water, azeotropically distilling to remove the water formed in the reaction mixture during the esterification reaction and neutralizing the resulting sulphocarboxylic ester with an oxide, hydroxide or a carbonate of an alkali metal, calcium or magnesium. Preferably, the reaction mixture is extracted with water and the aqueous extract neutralized with the hydroxide of the desired metal. Numerous applications of the surface-active salts are mentioned (see Groups IV (c) and VI).  The acid sulpho-esters themselves are stated to have foaming, wetting and deterging properties.  Examples describe the preparation of the following salts, the processes being effected in a flask fitted with a Stark and Dean moisture trap and condenser using benzene, toluene or xylene as liquid entrained in the presence of phosphoric acid (catalyst), the salts being isolated from their aqueous extracts by drum drying or crystallization: (1) octyl-, dodecyl, tetradecyl- and Loralkyl-o-sodium-sulpho-benzoates from o-sulpho-benzoic acid anhydride and 2-ethyl hexanol and appropriate fractions or whole mixtures of the alcohols known commercially as "Lorol" (a Registered Trade Mark) respectively; (2) dodecyl- and Loralkyl-m-sodium sulphobenzoate; (3) dodecyl-p-sodium sulpho-benzoate, and (4) octyl-, dodecyl- and Loralkyl sulpho-salicylates from the appropriate acids and alcohols.  Their wetting and washing properties are compared with those of other wetting agents.  Additional starting materials comprise n-octyl alcohol, nonyl alcohol, decyl alcohol and like alcohols up to octa-decyl alcohol.  Specification 519,072 is referred to.  The Specification as open to inspection under Sect. 91 includes the use of any sulphonated monocyclic aromatic monocarboxylic acid, its anhydride or acid chloride as starting material and, in an additional example, describes the preparation of octyl-o-sulphobenzoate according to the method of (1) above followed by acidification with a strong mineral acid or, alternatively, by proceeding according to (1) above, omitting the neutralization step.  It is indicated that the free-sulpho esters have the same uses as stated above in connection with the salts. This subject-matter does not appear in the Specification as accepted.ALSO:Surface-active materials prepared by heating an aliphatic alcohol having from 8 to 18 carbon atoms with a sulphonated monocyclic aromatic monocarboxylic acid of the general formula <FORM:0611210/IV (c)/1> wherein Ar is a monocyclic aromatic hydrocarbon nucleus, X is hydrogen, a halogen or a hydroxyl group and m and n are integers, or with the corresponding carboxylic acid anhydride, in the presence of an organic solvent which forms an azeotrope with water, azeotropically distilling to remove the water formed in the reaction mixture during the esterification reaction and neutralizing the resulting sulphocarboxylic ester with an oxide, hydroxide or a carbonate of an alkali metal, calcium or magnesium may be used as wetting agents, detergents with or without detergent builders such as sodium sulphate, magnesium sulphate and sodium carbonate, as foaming and emulsifying agents, as dispersing agents for insecticides and germicides; in ore flatation; in dyeing and textile processes; for breaking petroleum emulsions; in plastic, cement and ceramic mixes and in printing inks; and especially in dentifrices (see Group VI).  The acid sulphoesters themselves are stated to have foaming, wetting and deterging properties.  Examples describe the preparation of the following salts: (1) octyl-, dodecyl-, tetradecyl- and Loralkyl-o-sodium-sulpho-benzoates from o-sulphobenzoic acid anhydride and 2-ethyl hexanol and appropriate fractions or whole mixtures of the alcohols known commercially as " Lorol " (Registered Trade Mark) respectively; (2) dodecyl- and Loralkyl - m - sodium sulpho - benzoate, (3) dodecyl-p-sodium sulpho-benzoate and (4) octyl-, dodecyl- and Lotalkyl sulphosalicylates from the appropriate acids and alcohols.  Their wetting and washing properties are compared with those of other wetting agents.  Additional starting materials comprise n-octyl alcohol, nonyl alcohol, decyl alcohol and like alcohols up to octa-decyl alcohol.  Specification 519,072 is referred to.ALSO:Compounds having the general formula <FORM:0611210/VI/1> wherein R is an alkyl radical having 8 to 18 carbon atoms, Ar is a monocyclic aromatic hydrocarbon nucleus, X is hydrogen, halogen or an hydroxyl group, Y is an alkali metal, calcium or magnesium and m and n are integers, may be used in dentrifices for the complete or partial substitution of the conventional detergent or emulsifying ingredients such as soap, sulphonated oils, saponins, sulphonated higher alcohols, alkylated aromatic sulphonic acids and the commercial products known as "Nacconol" and "Santomerse."  The composition may also comprise an abrasive or polishing base such as chalk, calcium sulphate, di- and tricalcium phosphate, magnesium oxide and carbonate, talc, kaolin, bolus alba, silica gel, aluminium silicate or bentonite; a binding agent such as gum tragacanth, gum arabic, gum karaya, starch or dextrin; an excipient such as water or glycerol; a flavouring material such as oil of peppermint, oil of cloves, oil of wintergreen, methyl salicylate, phenyl salicylate, lemon oil, sugar or saccharine with or without flavouring materials having a disinfecting action such as thymol, menthol and eucalyptol; and benzoic acid, calcium chloride, and alkali metal salts or mucin solvents such as sodium phosphates, pyrophosphates and carbonates and borax.  The Specification as open to inspection under Sect. 91 includes the use of compounds having the above general formula wherein Y is hydrogen.  This subject-matter does not appear in the Specification as accepted.