Patent GB-490764-A (GB)
Title: Manufacture of water-soluble condensation products
Filed: 1937-02-22
Abstract: An aromatic compound, containing more than one halogenmethyl group linked directly to the aromatic nucleus, is condensed with an aromatic hydrocarbon or a partly hydrogenated aromatic hydrocarbon or a halogen, alkyl or amino substitution product thereof, and one or more sulphonic acid groups are introduced into the product before, during or after the condensation. Water-soluble products useful as dispersing agents are obtained. In the examples, (1) naphthalene is sulphonated and the product is condensed, in the presence of sulphuric acid, with a reaction product of commercial xylene, formaldehyde, and hydrochloric acid, this product containing at least two chloromethyl groups; (2) solvent naphtha is condensed, in the presence of oleum, with a poly (chloromethyl)-naphthalene obtained by treating naphthalene with at least two mols. of formaldehyde solution saturated with hydrochloric acid; (3) a dibutyl-naphthalene sulphonic acid is condensed with a di(chloromethyl)-toluene; (4) a mixture of a - and b -chloronaphthalene is sulphonated, and the crude product is treated with a poly(chloromethyl)-phenol, obtained by treating phenol with a large excess of formaldehyde and hydrochloric acid; the use of the neutralized product for dispersing dyes for acetate silk is mentioned; (5) tetrahydro-b -naphthyl-amine is sulphonated, and the product is condensed with a side-chain dichlorination product of xylene.  Other specified starting materials with which the halogenmethyl compounds may be condensed are xylene, aniline, ethylnaphthalene, tetrahydronaphthalene, phenanthrene and anthracene. A sample has been furnished under Sect. 2 (5), of a product prepared by condensing xylene with di(o -chloro-methyl) naphthalene, and sulphonating the resinous product with chlorosulphonic acid.ALSO:An aromatic compound, containing more than one halogenmethyl group linked directly to the aromatic nucleus, is condensed with an aromatic hydrocarbon or a partly hydrogenated aromatic hydrocarbon or a halogen, alkyl or amino substitution product thereof, and one or more sulphonic acid groups are introduced into the product before, during or after the condensation. Water-soluble products useful as tanning-agents or as wetting or dispersing agents, e.g. in the dyeing industry, are obtained.  In the examples, (1) naphthalene is sulphonated and the product is condensed, in the presence of sulphuric acid, with a reaction product of commercial xylene, formaldehyde, and hydrochloric acid, this product containing at least two chloromethyl groups; (2) solvent naphtha is condensed, in the presence of oleum, with a poly(chloromethyl)-naphthalene obtained by treating naphthalene with at least two mols. of formaldehyde solution saturated with hydrochloric acid; (3) a dibutylnaphthalenesulphonic acid is condensed with a di(chloromethyl)-toluene; (4) a mixture of a - and b -chloronaphthalene, obtained by chlorinating naphthalene, is sulphonated, and the crude product is treated with a poly(chloromethyl)-phenol, obtained by treating phenol with a large excess of formaldehyde and hydrochloric acid; the use of the neutralized product for dispersing dyes for acetate silk is mentioned; (5) tetrahydro-b -naphthylamine is sulphonated, and the product is condensed with a side-chain dichlorination product of xylene.  Other specified starting materials with which the halogenmethyl compounds may be condensed are xylene, aniline, ethylnaphthalene, tetrahydronaphthalene, phenanthrene and anthracene. A sample has been furnished under Sect. 2 (5) of a product prepared by condensing xylene with di(w-chloromethyl)naphthalene, and sulphonating the resinous product with chlorosulphonic acid; the di(chloromethyl) naphthalene is prepared by treating naphthalene with at least 2 mols. of hot aqueous formaldehyde solution saturated with hydrogen chloride.