# US 4,394,517 A · Quaternary ammonium functional silicon compounds > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 4,394,517 A - Document ID: US4394517A - Status: Granted - Kind: A - Application number: 06/380,487 - Filed: 1982-05-21 - Granted: 1983-07-19 - Earliest claimed: 1982-05-21 - Assignees: SWS Silicones Corporation - Inventors: Eugene R. Martin; Jeffrey A. Tripp - Web page: https://patentgrep.com/patent/US4394517A ## CPC - D06M 13/51: Compounds with at least one carbon-metal or carbon-boron, carbon-silicon, carbon-selenium, or carbon-tellurium bond - C07F 7/1804: {Compounds having Si-O-C linkages (Si-O-acyl linkages C07F7/1896)} - C07F 7/1892: {by reactions not provided for in C07F7/1876 - C07F7/1888} - C08G 77/388: containing nitrogen - C08G 77/42: Block-or graft-polymers containing polysiloxane sequences (polymerising aliphatic unsaturated monomers on to a polysiloxane C08F283/12) - D06M: TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS - 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 Quaternary ammonium functional silicon compounds are prepared by reacting carboxylic acid functional quaternary ammonium compounds with aminofunctional silicon compounds. These quaternary ammonium functional silicon compounds are antistatic finishes for textiles. ## Claims ### Claim 1 A process for preparing quaternary ammonium functional silicon compounds which comprises reacting a carboxylic acid functional quaternary ammonium compound selected from the group consisting of compounds having the formulas ##STR10## with an aminofunctional silicon compound selected from the group consisting of (a) Silanes having the formula ##STR11## (b) Siloxanes having at least one unit of the formula ##STR12## (c) and mixtures thereof, at a temperature of from 0.degree. up to about 175.degree. C., in which R is a monovalent hydrocarbon radical having from 1 to 22 carbon atoms, R.sup.1 is a hydrocarbonoxy radical having the formula --(C.sub.n H.sub.2n O).sub.r, R.sup.2 is a divalent hydrocarbon radical selected from the group consisting of (CH.sub.2).sub.y, CH.dbd.CH and cyclic divalent hydrocarbon radicals selected from the group consisting of C.sub.6 H.sub.4, C.sub.6 H.sub.8, C.sub.6 H.sub.10, and C.sub.10 H.sub.6, R.sup.3 is a divalent hydrocarbon radical having from 2 to 10 carbon atoms, R.sup.4 is selected from the group consisting of a saturated divalent hydrocarbon radical having up to 10 carbon atoms, a divalent hydrocarbonoxy radical in which the oxygen is in the form of an ether linkage and an unsaturated divalent hydrocarbon radical having from 3 to 10 carbon atoms, X is an anionic radical, a is a number of from 1 to 4, b is 0, 1 or 2, c is 0, 1, 2 or 3, e is a number of from 1 to 3, f is a number of from 0 to 3, in which the sum of a+f cannot exceed 4, g is a number of from 0 to 2, in which the sum of e+g cannot exceed 3, n is 2, 3 or 4, r is a number of from 1 to 50 and y is a number of from 0 to 10. ### Claim 2 (depends on 1) The process of claim 1, wherein the reaction is conducted in the presence of a non-protic solvent. ### Claim 3 (depends on 1) The process of claim 1, wherein the aminofunctional silicon compound is a silane having the formula ##STR13## where R is a monovalent hydrocarbon radical having from 1 to 22 carbon atoms, R.sup.4 is selected from the group consisting of a saturated divalent hydrocarbon radical having up to 10 carbon atoms, a divalent hydrocarbonoxy radical in which the oxygen is in the form of an ether linkage and an unsaturated divalent hydrocarbon radical having from 3 to 10 carbon atoms, b is 0, 1 or 2, and c is 0, 1, 2 or 3. ### Claim 4 (depends on 1) The process of claim 1, wherein the aminofunctional silicon compound is a siloxane having at least one unit of the formula ##STR14## where R is a monovalent hydrocarbon radical having from 1 to 22 carbon atoms, R.sup.4 is selected from the group consisting of a saturated divalent hydrocarbon radical having up to 10 carbon atoms, a divalent hydrocarbonoxy radical in which the oxygen is in the form of an ether linkage and an unsaturated divalent hydrocarbon radical having from 3 to 10 carbon atoms, and b is 0, 1 or 2. ### Claim 5 (depends on 1) The process of claim 1, wherein the aminofunctional silicon compound is a siloxane having units of the formulas ##EQU3## where R is a monovalent hydrocarbon radical having from 1 to 22 carbon atoms, R.sup.4 is selected from the group consisting of a saturated divalent hydrocarbon radical having up to 10 carbon atoms, a divalent hydrocarbonoxy radical in which the oxygen is in the form of an ether linkage and an unsaturated divalent hydrocarbon radical having from 3 to 10 carbon atoms, b is 0, 1 or 2 and c is 0, 1, 2 or 3. ### Claim 6 (depends on 1) The process of claim 1, wherein the mole ratio of the carboxylic acid groups of the carboxylic acid quaternary ammonium compound to amine groups of the aminofunctional silicon compound is in the range of from 4:1 to 1:3 with the proviso that at least one carboxylic acid group is reacted with one amine group. ### Claim 7 (depends on 1) The process of claim 1, wherein the carboxylic acid functional quaternary ammonium compound is represented by the formula ##STR15## ### Claim 8 (depends on 1) The process of claim 1, wherein the carboxylic acid functional quaternary ammonium compound is represented by the formula ##STR16## ### Claim 9 (depends on 1) The process of claim 1, wherein the aminofunctional siloxanes have at least one unit of the formula ##EQU4## where b is 0, 1 or 2. ### Claim 10 (depends on 1) The process of claim 1, wherein the aminofunctional siloxanes have at least one unit of the formula ##EQU5## where b is 0, 1 or 2. ### Claim 11 (depends on 1) The process of claim 1, wherein the aminofunctional siloxanes have at least one unit of the formula ##EQU6## where b is 0, 1 or 2. ### Claim 12 (depends on 1) The composition prepared in accordance with the process of claim 1. ### Claim 13 (depends on 3) The composition prepared in accordance with the process of claim 3. ### Claim 14 (depends on 4) The composition prepared in accordance with the process of claim 4. ### Claim 15 A process for imparting antistatic properties to textile materials which comprises applying to the textile materials a composition obtained from the reaction of a carboxylic acid functional quaternary ammonium compound selected from the group consisting of compounds having the formulas ##STR17## with an aminofunctional silicon compound selected from the group consisting of (a) Silanes having the formula ##STR18## (b) Siloxanes having at least one unit of the formula ##STR19## (c) and mixtures thereof, at a temperature of from 0.degree. up to about 175.degree. C., in which R is a monovalent hydrocarbon radical having from 1 to 22 carbon atoms, R.sup.1 is a hydrocarbonoxy radical having the formula --(C.sub.n H.sub.2n O).sub.2, R.sup.2 is a divalent hydrocarbon radical selected from the group consisting of (CH.sub.2).sub.y, CH.dbd.CH and a cyclic divalent hydrocarbon radical selected from the group consisting of C.sub.6 H.sub.4, C.sub.6 H.sub.8, C.sub.6 H.sub.10, and C.sub.10 H.sub.6, R.sup.3 is a divalent hydrocarbon radical having from 2 to 10 carbon atoms, R.sup.4 is selected from the group consisting of a saturated divalent hydrocarbon radical having up to 10 carbon atoms, a divalent hydrocarbonoxy radical in which the oxygen is in the form of an ether linkage and an unsaturated divalent hydrocarbon radical having from 3 to 10 carbon atoms, X is an anionic radical, a is a number of from 1 to 4, b is 0, 1 or 2, c is 0, 1, 2 or 3, e is a number of from 1 to 3, f is a number of from 0 to 3, in which the sum of a+f cannot exceed 4, g is a number of from 0 to 2, in which the sum of e+g cannot exceed 3, n is 2, 3 or 4, r is a number of from 1 to 50 and y is a number of from 0 to 10 and thereafter heating the treated textile material at an elevated temperature. ### Claim 16 (depends on 15) The process of claim 15, wherein the composition contains a non-protic solvent. ### Claim 17 (depends on 15) The process of claim 15, wherein the composition is dispersed in water. ### Claim 18 (depends on 15) The process of claim 15, wherein the treated textile material is heated to a temperature up to about 200.degree. C.