# US 5,705,663 A · Quaternized triethanolamine difatty acid esters > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 5,705,663 A - Document ID: US5705663A - Status: Granted - Kind: A - Application number: 08/568,569 - Filed: 1995-12-07 - Granted: 1998-01-06 - Earliest claimed: 1994-12-23 - Assignees: Servo Delden B.V. - Inventors: Michael Brock; Meinolf Enneking; Kurt Kosswig - Web page: https://patentgrep.com/patent/US5705663A ## CPC - C11D 1/62: Quaternary ammonium compounds - C07C 213/06: from hydroxy amines by reactions involving the etherification or esterification of hydroxy groups - C07C 219/06: having the hydroxy groups esterified by carboxylic acids having the esterifying carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms of an acyclic saturated carbon skeleton - C07C 219/08: having at least one of the hydroxy groups esterified by a carboxylic acid having the esterifying carboxyl group bound to an acyclic carbon atom of an acyclic unsaturated carbon skeleton - C11D: DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS ## Abstract The invention relates to quaternized triethanolamine difatty acid esters prepared from triethanolamine, fatty acid, fatty acid ester and a quaternizing agent and to a process for their preparation and to their use. The quaternized triethanolamine difatty acid esters thus prepared can be used to produce particularly storage-, temperature- and viscosity-stable rinse cycle laundry softeners having a high active content. ## Claims ### Claim 1 A mixture of quaternized triethanolamine difatty acid esters comprising the combination of: A) 70-90% by wt. of the reaction product, which is quaternized, of triethanolamine with 1.5 to 2.5 equivalents of fatty acid; and B) 10-30% by wt. of the reaction product, which is quaternized, of triethanolamine with 1.5 to 2.5 equivalents of fatty acid esters, the percent by weight of each of A) and B) based on the total amount of reaction product of triethanolamine with fatty acid and of reaction product of triethanolamine with fatty acid ester. ### Claim 2 (depends on 1) The mixture of quaternized triethanolamine difatty acid esters of claim 1, wherein said fatty acids and a fatty acid radical of said fatty acid esters contain 6 to 24 carbon atoms. ### Claim 3 (depends on 1) The mixture of quaternized triethanolamine difatty acid esters of claim 1, wherein an alcohol of said fatty acid esters are 1- to 6-hydric alcohols having 1 to 8 carbon atoms. ### Claim 4 (depends on 1) The mixture of quaternized triethanolamine difatty acid esters of claim 1, wherein said fatty acid is tallow fatty acid or partially hydrogenated tallow fatty acid. ### Claim 5 (depends on 1) The mixture of quaternized triethanolamine difatty acid esters of claim 1, wherein said fatty acid ester is the methyl ester of tallow fatty acid or partially hydrogenated tallow fatty acid. ### Claim 6 (depends on 1) A rinse cycle laundry softener comprising the mixture of quaternized triethanolamine difatty acid esters of claim 1 and a solvent. ### Claim 7 (depends on 6) The rinse cycle laundry softener of claim 6, wherein said solvent is selected from the group consisting of (i) compounds of formula I C.sub.1 -C.sub.4 --alkyl--OH, (I) (ii) compounds of formula II ##STR2## wherein R.dbd.H or CH.sub.3 and a=1 to 4, (iii) alkoxylated natural oils and fats, and (iv) a mixture thereof. ### Claim 8 A mixture of quaternized triethanolamine difatty acid esters obtained by: 1) reacting triethanolamine with 1.5 to 2.5 equivalents of a mixture of 70 to 90% by weight of fatty acid and 10 to 30% by weight of fatty acid esters, each based on the total amount of fatty acid and fatty acid ester, and subsequent quaternization of the reaction product with a quaternizing agent, or 2) a separate reaction of triethanolamine with 1.5 to 2.5 equivalents of fatty acid and fatty acid ester and mixing of the respectively obtained triethanolamine difatty acid esters before quaternization in a weight ratio of 70 to 90%:10 to 30% and subsequent quaternization; or 3) a separate reaction of triethanolamine with 1.5 to 2.5 equivalents of fatty acid and fatty acid ester and quaternization with a quaternizing agent and mixing in a weight ratio of 70 to 90%:10 to 30%. ### Claim 9 A process for preparing a mixture of quaternized triethanolamine difatty acid esters from triethanolamine, fatty acid, fatty acid esters and a quaternizing agent, comprising 1) reacting triethanolamine with 1.5 to 2.5 equivalents of a mixture of: i) 70 to 90% by weight of fatty acid; and ii) 10 to 30% by weight of fatty acid ester, each based on the total amount of fatty acid and fatty acid ester; and 2) quaternizing the reaction product. ### Claim 10 A process for preparing a mixture of quaternized triethanolamine difatty acid esters from triethanolamine, fatty acid, fatty acid esters and a quaternizing agent, comprising: 1) separately reacting triethanolamine with: i) 1.5 to 2.5 equivalents of fatty acid; and ii) 1.5 to 2.5 equivalents of fatty acid ester, 2) mixing the respectively obtained triethanolamine difatty acid esters in a weight ratio of triethanolamine difatty acid ester from fatty acid, to triethanolamine difatty acid ester from fatty acid ester of from 70 to 90%: 10 to 30%; and 3) quaternizing the mixture of step 2). ### Claim 11 A process for preparing a mixture of quaternized triethanolamine difatty acid esters from triethanolamine, fatty acid, fatty acid esters and a quaternizing agent, comprising: 1) separately reacting triethanolamine with: i) 1.5 to 2.5 equivalents of fatty acid; and ii) 1.5 to 2.5 equivalents of fatty acid ester, 2) quaternizing each reaction mixture of step 1); and 3) mixing the respectively obtained quaternized triethanolamine difatty acid esters in a weight ratio of quaternized triethanolamine difatty acid ester from fatty acid, to quaternized triethanolamine difatty acid ester from fatty acid ester of from 70 to 90%: 10 to 30%.