# US 5,344,949 A · Method for the synthesis of surface-active anion-cation complexes

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- Number: US 5,344,949 A
- Document ID: US5344949A
- Status: Granted
- Kind: A
- Application number: 08/092,303
- Filed: 1993-07-14
- Granted: 1994-09-06
- Earliest claimed: 1992-07-22
- Assignees: Th. Goldschmidt AG
- Inventors: Gotz Koerner; Klaus-Dieter Klein; Dietmar Schaefer
- Web page: https://patentgrep.com/patent/US5344949A

## CPC

- C09K 23/54: Silicon compounds
- C07C 215/08: with only one hydroxy group and one amino group bound to the carbon skeleton
- C07F 7/0838: {Compounds with one or more Si-O-Si sequences (compounds with a ring containing only alternating Si and O atoms, i.e. cyclosilanes C07F7/21)}
- C07F 7/0889: {Reactions not involving the Si atom of the Si-O-Si sequence}
- C08G 77/045: {containing less than 25 silicon atoms}
- C08G 77/382: containing atoms other than carbon, hydrogen, oxygen or silicon
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS

## Abstract

Surface active anion-cation complexes are synthesized where an organic or organosilicon compound with at least one epoxide group is reacted with a quaternary ammonium hydrogen sulfite of the general formula HN.sup.+ (R.sup.1).sub.3 SO.sub.3 H.sup.- I wherein R.sup.1 within the molecule is the same or different and can be (1) an alkyl or hydroxyalkyl group with 1 to 18 carbon atoms, (2) a phenyl group, or (3) a group of the formula C.sub.n H.sub.2n+1 CONH--(CH.sub.2).sub.m --, in which n can be a number from 7 to 17 and m is 2 or 3, in the presence of a polar solvent in such amounts so that the molar ratio of the epoxide group to HN.sup.+ (R.sup.1).sub.3 SO.sub.3 H.sup.- is 2:1.

## Claims

### Claim 1

A method for the synthesis of surface active anion-cation complexes comprising the steps of reacting an organic or organosilicon compound having at least one epoxide group, wherein said organic compound is of the general formula ##STR10## Wherein R.sup.4 is a hydrogen or alkyl group with 2 to 6 carbon atronis and X is a number from 2 to 14, or the organic compound is an epoxide of an unsaturated fatty acid or its ester,
with a quaternary ammonium hydrogen sulfide of the general formula
HN.sup.+ (R.sup.1).sub.3 SO.sub.3 H I
wherein
R.sup.1 within a molecule is the same or different and can be
(1) an alkyl or hydroxyalkyl group with 1 to 18 carbon atoms;
(2) a phenyl group; or
(3) a group of the formula C.sub.n H.sub.2n+1 COHN--(CH.sub.2).sub.m --, in which n can be a number from 7 to 17 and m is 2 or 3;
in the presence of a polar solvent in such amount that the molar ratio of the epoxide group to HN.sup.+ (R.sup.1).sub.3 SO.sub.3 H is about 2:1.

### Claim 2 (depends on 1)

The method of claim 1, further comprising as organosilicon compound having at least one epoxide group, a compound of the average general formula ##STR11## is used, wherein R.sup.2 in an average molecule is the same or different and represents alkyl groups of 1 to 18 carbon atoms with the proviso that at least 90% of the groups are methyl groups;
R.sup.3 has the same meaning as the R.sup.2 group or is an epoxide group linked over a carbon atom to silicon, with the proviso that, in an average molecule, at least one R.sup.3 group is an epoxide group;
a has a value of 0 to 500; and
b has a value of 0 to 5.

### Claim 3 (depends on 2)

The method of claim 2, comprising compounds that are used having at least one R.sup.3 as an epoxide group selected from the group having the formulas ##STR12##

### Claim 4 (depends on 1)

The method of claim 1, comprising that the mixture of different organosilicon compounds or mixture of organosilicon and organic compounds used having, in each case, at least one epoxide group.

### Claim 5 (depends on 1)

The method of claim 1 comprising that the solvent used is low-boiling aliphatic alcohol.

### Claim 6 (depends on 5)

The method of claim 5, further comprising that the solvent used is isopropanol.

### Claim 7 (depends on 1)

A surface active anion-cation complex obtained by the method of claim 1.