Patent GB-581985-A (GB)
Title: Manufacture of sulphonated ethers containing at least one aralkyl residue
IPC: C11D1/22
Filed: 1943-01-08
Abstract: Sulphonated ethers, stated to be dispersing agents, are obtained by (a) treating a sulphonated aromatic hydroxy compound with a chlormethyl compound which contains at least 11 carbon atoms and is derived from an aromatic or partly hydrogenated aromatic compound or (b) sulphonating an ether which contains at least one aliphatically bound hydroxyl group and is derived from an aliphatic polyhydroxy compound or 1 : 2-oxide thereof and a chlormethyl compound which contains at least 11 carbon atoms and is derived from an aromatic or partly hydrogenated aromatic compound.  In examples: (1) ar: -2-chlormethyl tetrahydronaphthalene is condensed with 2-hydroxynaphthalene-6-sulphonic acid, 2 : 4-dihydroxynaphthalene-6-sulphonic acid and with p-phenolsulphonate; (2) 2-chlormethylcymene is condensed with 2-hydroxynaphthalene-6-sulphonic acid, 1-hydroxynaphthalene -5-sulphonic acid and with 2 : 8-dihydroxynaphthalene-6-sulphonic acid.  The following components are also mentioned:- chlorphenol sulphonic acids, cresol sulphonic acids, 2-hydroxy-1-methylbenzenesulphonic acid, xylenolsulphonic acid, thymolsulphonic acids, resorcinolsulphonic acids, 2-hydroxynaphthalenedisulphonic acid, 1 : 8-dihydroxynaphthalenedisulphonic acid, 2-hydroxynaphthalene-3-carboxylic acid-6-sulphonic acid, ar: - tetrahydro-a-naphthol-4-sulphonic acid and hydroxysulphonic acids of diphenyl, anthracene, phenanthrene and acenaphthene. Methoxy, amino and acylamino groups may also be present.  Among the chlormethyl compounds mentioned are:-1-chlormethylnaphthalene, chlormethyl anthracene, chlormethyl octahydroanthracene, chlormethyloctahydrophenanthrene and chlormethylcyclohexylbenzene. The chlormethyl compounds of addition products of dipentene with phenol and with b -naphthol are mentioned.ALSO:Sulphonated ethers are obtained by (a) treating a sulphonated aromatic hydroxy compound with a chlormethyl compound which contains at least 11 carbon atoms and is derived from an aromatic or partly hydrogenated aromatic compound, or (b) sulphonating an ether which contains at least one aliphatically bound hydroxyl group and is derived from an aliphatic polyhydroxy compound or 1 : 2-oxide thereof and a chlormethyl compound which contains at least 11 carbon atoms and is derived from an aromatic or partly hydrogenated aromatic compound.  In examples: (1) ar-2-chlormethyltetrahydronaphthalene is condensed with 2-hydroxynaphthalene-6-sulphonic acid, 2 : 4 - dihydroxynaphthalene - 6 - sulphonic acid and with p-phenolsulphonate-; (2) 2-chlormethylcymene is condensed with 2-hydroxynaphthalene - 6 - sulphonic acid, 1 - hydroxynaphthalene-5-sulphonic acid and with 2 : 8 - dihydroxynaphthalene - 6 - sulphonic acid.  The following components are also mentioned: chlorphenolsulphonic acids, cresolsulphonic acids, 2 - hydroxy - 1 - methylbenzenesulphonic acid, xylenolsulphonic acid, thymolsulphonic acids, resorcinolsulphonic acids, 2-hydroxynaphthalenedisulphonic acid, 1 : 8-dihydroxynaphthalenedisulphonic acid, 2-hydroxynaphthalene - 3 - carboxylic acid - 6 - sulphonic acid, ar-tetrahydro-a -naphthol-4-sulphonic acid and hydroxysulphonic acids of diphenyl, anthracene, phenanthrene and acenaphthene. Methoxy, amino and acylamino groups may also be present.  Among the chlormethyl compounds mentioned are: 1 - chlormethylnaphthalene, chlormethyl anthracene, chlormethyloctahydroanthracene, chlormethyloctahydrophenanthrene and chlormethylcyclohexylbenzene. The chlormethyl compounds of addition products of dipentene with phenol and with b -naphthol are mentioned.  The products, which may be used alone or with textile assistants such as inorganic salts in the textile industry are stated to be wetting, foaming, dispersing, softening, washing and levelling agents.  An example is given of a process for washing wool yarn.  A sample has been furnished under Sect. 2 (5) of a product obtained by sulphonating an ether prepared from 2-chlormethyl-1-methyl-4-isopropylbenzene and glycide. Chlormethyl compounds mentioned above may be made by treating the parent material in aqueous hydrochloric acid solution with formaldehyde and gaseous hydrochloric acid if required with addition of zinc chloride.