Patent GB-978851-A (GB)
Title: Sulphato-esters of sulphones and sulphoxides and their use in cellulosic fibre treatment
IPC: D06M13/248
Filed: 1960-12-30
Abstract: 978,851. Sulphato-esters of sulphones and sulphoxides; sulphides, sulphomides, sulphones, sulphinic acids. DEERING MILLIKEN RESEARCH CORPORATION. Dec. 30, 1960 [Dec. 31, 1959], No. 42133/60. Heading C2C. [Also in Division D1] The invention comprises compounds of the general formula X<SP>1</SP>(CHR <SP>1</SP>-CHR<SP>2</SP>-O-SO 3 Y <SP>1</SP>) 2 - in which R<SP>1</SP> and R<SP>2</SP> are hydrogen atoms or saturated alkyl groups having 1 to 3 carbon atoms, Y<SP>1</SP> is a metal or a nitrogen base such that said agent is soluble in water, n is 1 or 2, and X<SP>1</SP> is is -SO 2 -R-SO 2 -, -SO- or -SO-R-SO- wherein R is (a) a saturated aliphatic divalent radical consisting of 1 to 10 carbon atoms, hydrogen, 0 to 4 oxygen atoms, and 0 to 2 sulphur atoms, said oxygen being present in no form other than ether, sulphonate or carboxylate groups, said sulphur being present in no form other than thioether or sulphonate groups, (b) a cycloaliphatic radical consisting of 4 to 7 carbon atoms, hydrogen, 0 to 3 oxygen atoms, and 0 or I sulphur atoms, said oxygen being present in ether, sulphonate, or carboxylate groups, said sulphur being present in thioether or sulphonate groups, the sulphone or sulphoxide groups of said radical X<SP>1</SP>. being attached directly to -CH- groups in the cycloaliphatic ring, or (c) an aromatic group which is a meta- or para-phenylene group optionally substituted with hydrocarbon groups having 1 to 3 carbon atoms, or is where the six groups Z in aggregate contain only hydrogen, 0 to 3 carbon atoms, 0 to 2 sulphur atoms, and 0 to 6 oxygen atoms, said carbon atoms being in an alkyl group, said oxygen and sulphur atoms being in sulphonate groups, the valence bonds * being linked to the sulphoxide or sulphone groups of the radical X<SP>1</SP>, and no two -SO 2 - and -SO- groups being ortho to each other in the naphthalene ring, any sulphonate or carboxylate groups present in the group R as defined in (a), (b) and (c) above being optionally present in the form of salts. The compounds of Formula (2) above are prepared by heating the acid form of the corresponding bissulphatoethyl sulphone with the elimination of H 2 SO 4 . The compounds of formula (I) above wherein X<SP>1</SP> is -SO- can be prepared by the reaction followed by oxidation with about I equivalent of an oxidizing agent such as H 2 O 2  or KMnO 4  to give the sulphoxide OS-(CHR <SP>1</SP>-CHR<SP>2</SP>-OH) 2  which is treated with sulphuric acid to give OS-(CHR<SP>1</SP>-CHR<SP>2</SP>-O-SO 3 H) 2  which may then be treated with the oxide or hydroxide of the metal Y <SP>1</SP>. The metal salts may also be obtained by passing a solution of the corresponding acid through an ion exchange bed containing the appropriate metallic ion. Compounds of Formula (I) above in which X<SP>1</SP> is -SO 2 -R-SO 2 - or -SO-R-SO- may be formed by reactions similar to those used for compounds wherein X <SP>1</SP> is -SO- by using a bis-mercaptan HS-R-SH in place of H 2 S. Compounds of Formula (1) in which X<SP>1</SP> is -SO 2 -R-SO 2 - and R is. aromatic may be prepared by treating m-benzene disulphonyl chloride with sodium sulphite in aqueous sodium hydroxide to give the disodium salt of the corresponding disulphinic acid. This is treated with ethylene chlorohydrin to give phenylene-1, 3-bis-(#-hydroxyethyl sulphone) which is then treated with fuming sulphuric acid to give the bis-sulphate ester. Compounds in which R is 1, 5-naphthylene and 1, 3-cyclopentylene are prepared similarly. Examples are given.