Organic compounds -- part of the class 532-570 series – Organic compounds – Silicon containing
Patent
1994-02-03
1996-07-02
Shaver, Paul F.
Organic compounds -- part of the class 532-570 series
Organic compounds
Silicon containing
C07F 708
Patent
active
055323995
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/EP92/02215 filed Sep. 26, 1992.
The invention relates to a process for the preparation of organosilicon compounds which carry at least one radical bonded to silicon via carbon and having a sulfonate group or a grouping --SO.sub.2 --O-- bonded to form a ring. The term sulfonate groups is to be understood hereafter as including sulfonic acid groups, SO.sub.3 H.
Organosilicon compounds carrying sulfonate groups are already known and can be prepared by various processes. German Offenlegungsschrift 1,495,434 (Dow Corning Corp.; published on 13th Nov. 1969) or the corresponding CA 742243 A and CA 760997 A, and U.S. Pat. No. 4,814,471 (Dow Corning Ltd.; published on 21st Mar. 1989), for example, describe processes for the preparation of organosilicon compounds containing sulfonate groups by oxidation of the corresponding thiuronium salts, thiocyano compounds and mercapto compounds with common oxidizing agents. Zwitterionic sulfonate-containing siloxanes are obtained according to M. Litt and T. Matsuda, J. Appl. Polym. Sci. 19 (1975) 1221, by the reaction of aminoalkyl-functional siloxanes with .omega.-alkylsultones. The sulfonation of epoxy- and alkenyl-functional organosilicon compounds with sodium hydrogensulfite is published in U.S. Pat. No. 4,235,638 (Minnesota Mining and Manufacturing Company; published on 25th Nov. 1980). Furthermore, European patent application A1-8,902 (The British Petroleum Company Ltd.; published on 19th Mar. 1980) describes a process for the modification of inorganic oxides carrying hydroxyl groups on their surface by reaction of these hydroxyl groups with trifunctional haloalkylorganyloxysilanes and subsequent treatment of these solid particles with an aqueous solution of an inorganic sulfite.
The object of the present invention was to provide a process by which organosilicon compounds carrying sulfur-containing organic radicals can easily be prepared. This object is achieved by the invention.
The present invention relates to a process for the preparation of organosilicon compounds carrying sulfur-containing organic radicals, wherein organosilicon compounds made up of units of the general formula monovalent organic radical, divalent hydrocarbon radical and X is a halogen atom, R.sup.2 per molecule and the sum of a, b and c is less than or equal to 4, are reacted with sulfite in the presence of water.
The organosilicon compounds obtainable by the process according to the invention contain at least one SiC-bonded group --QSO.sub.3 M.sub.v per molecule, in which Q is as defined above, M is a cation and v has the reciprocal value of the charge of M, or a grouping --SO.sub.2 --O-- bonded to form a ring. Compounds having groupings --SO.sub.2 --O-- bonded to form a ring are generally called sultones and are internal esters of compounds which carry both --SO.sub.3 H radicals and hydroxyl groups. (So-called "silasultones" contain the grouping ##STR1##
Examples of the radical M are the proton, alkali metal cations such as lithium, sodium, potassium, rubidium and cesium cations, alkaline earth metal cations such as magnesium and calcium cations, and radicals of the formula monovalent organic radical or an organosilicon radical, such as, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, n-pentyl, isopentyl, n-hexyl, benzyl, 2-hydroxyethyl and 3-hydroxypropyl radicals, as well as 3-sil(oxan)ylpropyl radicals in which the sil(oxan)yl radical can be varied at will.
The radical R is preferably a substituted or unsubstituted hydrocarbon radical having 1 to 12 carbon atoms, hydrocarbon radicals having 1 to 6 carbon atoms, especially the methyl radical, being particularly preferred.
Examples of radicals R are alkyl radicals such as the methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl and tert-pentyl radicals, hexyl radicals, for example the n-hexyl radical, heptyl radicals, for example the n-heptyl radical, octyl radicals, for example the n-octyl radical, and isooctyl radicals, for example the 2,2,4-trime
REFERENCES:
patent: 4235638 (1980-11-01), Beck et al.
patent: 4814471 (1989-03-01), Renauld
patent: 5068379 (1991-11-01), Roy
M. Litt and T. Matsuda, J. Appl. Polym. Sci. 19 (1975) 1221.
Y. Goldgerg, V. Dirnens and E. Lukevics "Journal of Organometallic Chemistry Library", vol. 20, 1988, pp. 219 to 222.
Deubzer Bernward
Hager Rudolf
Wolferseder Josef
Connaughton Martin
Shaver Paul F.
Wacker-Chemie GmbH
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