Patent GB-1484714-A (GB)
Title: Sulphur-containing isopropanol derivatives
IPC: B24B11/00
Filed: 1974-09-27
Abstract: 1484714 Antistatic agents; polyoxyalkylenes SANDOZ Ltd 27 Sept 1974 [28 Sept 1973] 42022/74 Headings C3P and C3R [Also in Division C2] Antistatic properties are imparted to polymers by means of compounds of formula wherein R 1  is alkyl (C 1 -C 22 ) or alkyl (C 2 -C 22 ) interrupted once or twice by S, SO or SO 2 , and/or once by COO, no two interrupting moieties being in adjacent positions and any alkyl or alkylene being unsubstituted or substituted by -OH; cycloalkyl (C 5  or C 6 ) or alkyl (C 1 -C 6 ) cycloalkyl (C 5  or C 6 ); or a radical -(R 5 O) x -R 4 , wherein R 4  is alkyl (C 1 -C 22 ), phenyl, phenyl substituted by 1 or 2 alkyl (C 1 -C 12 ) radicals, or phenylalkyl (C 7 -C 9 ), each R 5  is, independently, -(CH 2 ) 2 -, -(CH 2 ) 3 - or -CH(CH 3 )CH 2 - and x is an integer 1 to 180, n is 1 or 2, m is an integer 1 to 7, R 2  is a group R 12 , wherein R 12  is an (m + 1) valent saturated aliphatic hydrocarbon (C 2 - C 15 ) radical or an (m+1) valent saturated aliphatic hydrocarbon (C 2 -C 15 ) radical interrupted once or twice by O, S, SO or SO 2 , no two interrupting moieties being in adjacent positions; a bivalent radical of benzene, cyclohexane, biphenyl, diphenyloxide, diphenylsulphide, diphenylsulphoxide, diphenylsulphone, diphenylmethane, 2,2-diphenylpropane, bis - cyclohexylmethane or 2,2 - bis - cyclohexylpropane, or a group R 12  R 12 -[-(OR 5 ) p -] q  wherein R 12  and R 5  are as defined above, p is an integer 1 to 500, and q is an integer 1 to (m+ 1), provided that when q is greater than 1, each moiety in square brackets is independent of each other such moiety, and the total number, y, of radicals OR 5  does not exceed 500, and each R 3  has, independently, one of the significances of R 1  other than -(R 5 O) x -R 4 , or is hydrogen, phenyl, naphthyl or phenylalkyl (C 7 -C 1 ) or phenyl, naphthyl or phenylalkyl (C 7 -C 12 ) substituted on the aromatic nucleus thereof by 1 to 3 alkyl (C 1 -C 12 ), 1 cycloalkyl (C 5  to C 12 ), 1 or 2 alkoxy (C 1 -C 18 ), 1 or 2 halogen, 1 phenyl and/ or 1 phenoxy substituent, with 1 to 3 substituents and 1 to 18 carbon atoms in the aggregate of such substituents, a group wherein R 1  and n are as defined above, or a group wherein R 6  is alkyl (C 1 -C 21 ), perfluoroalkyl (C 3 -C 10 ), phenyl or naphthyl, or phenyl or naphthyl substituted by 1 to 3 halogen, 1 or 2 alkyl (C 1 -C 12 ) or 1 or 2 alkoxy (C 1 -C 12 ) substituents, with 1 to 3 substituents and 1 to 18 carbon atoms in the aggregate of such substituents with the proviso that the sum of x and y is a maximum of 500. The compounds may be applied by surface treatment or incorporated into the body of the polymer either during or after polymerization. Examples treat polystyrene and polycaprolactam. Novel polyethers falling within the first formula above are prepared by (a) condensing R 1 S(O) n CH 2 X where X is oxiranyl or with HOR 2 (OR 3 ) m ; (b) condensing R 1 SO 2 H with XCH 2 OR 2 (OR 7 ) m  where R 7  is as R 3  or is XCH 2 -; (c) oxidizing -S- linkage(s) or (d) esterifying to convert at least one R 3  = H group to R 3 =-COR 6 .