Patent GB-495414-A (GB)
Title: Manufacture of aromatic sulphonic acids having capillary-active properties
Filed: 1937-05-14
Abstract: Products for use in the textile and leather industries as wetting agents are obtained by the sulphonation of ethers and esters having either of the formulae: RXArXR1 or RArXR1 wherein Ar is a mono or bicyclic aromatic ring system, which may be linked to one or both groups X either directly or through an alkylene radicle or radicles, R and R1 are aliphatic or cycloaliphatic radicles containing altogether at least 8 carbon atoms of which R contains at least 4 and X is an ether or COO bridge of which the carbon atom is not directly linked to the aromatic ring Ar.  In modifications, (a) R stands for a plurality of aliphatic radicles or cycloaliphatic radicles together containing at least 4 carbon atoms and R1 at least 8 carbon atoms, and (b) R1 stands for an aliphatic or cycloaliphatic hydrocarbon radicle substituted by a further group XArR.  The ethers used as starting materials may be prepared by etherifying alkylated or cycloalkylated derivatives of phenols such as cresol, xylenol, pyrocatechol, resorcinol, naphthols and dihydroxynaphthalenes and by etherifying substituted aralkylalcohols such as menaphthyl alcohol and dihydroxymethylbenzenes.  The esters used as starting material may be prepared by esterifying alkylated or cycloalkylated phenols with carboxylic acids such as acetic, butyric, caproic, caprylic, capric, undecylic, lauric, palmitic, stearic, and montanic acids. Acids obtained by the oxidation of mineral oils or alcohols prepared by condensing aldehydes with ketones or by aldol condensation of aldehydes with subsequent hydrogenation are also specified.  Esters may also be derived from pyrocatechol, resorcinol, hydroquinone, di-iso-amylhydroquinone and polyhydroxymethyl benzenes and naphthalenes.  Esterification may be effected by reacting salts of the carboxylic acids with hydrogen halide esters of the polyhydric phenols and aromatic alcohols.  In examples, the following ethers and esters are sulphonated: (1) phenol is alkylated in the nucleus by means of a chlorinated middle oil obtained from carbon by hydrogenation under pressure, and the resulting phenol methylated by means of dimethylsulphate to give an ether; (2) isooctylphenol is etherified with diisobutylenechloride; (3) di-n-dodecylhydroquinone; (4) isobutylphenol lauric acid ester; (5) diisooctylphenol-a : b -glycolether; (6) sodium octylate is condensed with 1 : 2-dichlormethylbenzene to form an ether; (7) phenol is condensed with a mixture of isododecylene and isotetradecylene (prepared from alcohols resulting as bye-products in the manufacture of methylalcohol by hydrogenation of carbon monoxide) and ethylated with diethylsulphate; (8) pyrocatechol is esterified with the chlorides of acids obtained by the oxidation of paraffin; (9) dodecylphenyl-n-propylether, which may be obtained from n-propylbromide and potassium dodecyl phenolate; (10) the esters derived from isohexylphenol and carboxylic acids obtained by the oxidation of paraffin containing from 12 to 14 carbon atoms.  For the nuclear alkylation and cycloalkylation of phenols which are used in the preparation of the starting materials tertiary butyl alcohol, menthol, borneol, monobutylglycol, methylisopentylcarbinol, dipentylcarbinol, naphthene alcohol and abietinol may be used.  The following products are also specified: sodium sulphonate of isooctylphenolisooctylic acid ester, potassium sulphonate of isobutylphenollauric acid ester, ammonium sulphonate of the dia -ethyl hexylic acid ester of hydroquinone and sodium sulphonate of cyclohexylphenylisododecylether.  The products, which may be used in mercerizing processes and as levelling agents in dyeing, may be used in association with soap, mucilage, glue, cellulose derivatives, starch, bentonite, butanol, xylenylglycol, Glauber's salt, sodium carbonate, ortho, pyro or meta phosphates, sodium borate, sodium perpyrophosphate and sodium hypochlorite.