# US 11,299,692 B2 · Fabric softener active compositions > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 11,299,692 B2 - Document ID: US11299692B2 - Status: Granted - Kind: B2 - Application number: 16/063,365 - Filed: 2016-12-16 - Published: 2018-12-27 - Granted: 2022-04-12 - Earliest claimed: 2015-12-18 - Assignees: Kao Corporation - Applicants: KAO Corporation S.A. - Inventors: Blanca Nogues Lopez; Carmen M. Pey Gutierrez; Miquel Mundo Blanch; Jaume Sobrevias Alabau - Web page: https://patentgrep.com/patent/US11299692B2 ## CPC - C11D 3/0015: {liquid} - C11D 1/62: Quaternary ammonium compounds - C11D 3/2013: {fatty or with at least 8 carbon atoms in the alkyl chain} - C11D 3/2079: {Monocarboxylic acids-salts thereof} - C11D 3/2093: {Esters; Carbonates} - C11D 3/30: Amines; Substituted amines {; Quaternized amines} - C11D 3/43: Solvents - C11D 11/0094: {Process for making liquid detergent compositions, e.g. slurries, pastes or gels} - C11D: DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL ## Abstract The present invention relates to fabric softener active compositions comprising a combination of a quaternary ester ammonium compound and fatty solvents (a fatty acid ester, a fatty acid, a fatty alcohol and mixtures thereof) and methods of making and using the same. The invention also proposes fabric softener compositions, comprising the previously described active compositions, and methods of making and using the same. ## Claims ### Claim 1 A fabric softener active composition comprising: a component (a), said component comprising: at least one quaternary mono-ester ammonium compound, at least one quaternary di-ester ammonium compound and at least one quaternary tri-ester ammonium compound, and being obtainable by a process comprising at least the following steps: i) reacting a fatty acid, a methyl ester or a triglyceride thereof with an alkanolamine, wherein the molar ratio of fatty acid to alkanolamine is 1.4-2.5, to obtain a mixture containing an esteramine; and ii) quaternizing the mixture with an alkylating agent; a component (b), said component being a fatty acid ester or a mixture of fatty acid esters, wherein the component (b) content is in the range from 5 to 30% wt. based on the total weight of the fabric softener active composition; a component (c), said component being a fatty acid or a mixture of fatty acids, wherein the component (c) content is in the range from 0.5 to 15% wt. based on the total weight of the fabric softening active composition; wherein less than 3% by wt. of the total weight of the fabric softener active composition is a solvent; and wherein the composition has a dropping point below 60° C. ### Claim 2 (depends on 1) The fabric softener active composition according to claim 1, wherein the content of nitrogenated species in the component (a) is 65% wt. or more based on the total weight of the fabric softener active composition. ### Claim 3 (depends on 1) The fabric softener active composition according to claim 1, wherein in step i), the fatty acid, methyl ester or triglyceride thereof is/are reacted with an alkanolamine until the acid value is below 2 mg KOH/g. ### Claim 4 (depends on 1) The fabric softener active composition according to claim 1, wherein component (a) comprises at least one quaternary mono-ester ammonium compound of formula (I1), at least one quaternary di-ester ammonium compound of formula (I2), and at least one quaternary tri-ester ammonium compound of formula (I3), wherein m=n=p=2; R1—C(O)— is a linear acyl group, wherein R1 is a linear alkyl or a linear alkenyl containing from 11 to 21 carbon atoms; R2 and R3 each represent —OH, q is 0; X1 is a methyl group; and A− is selected from a halide, phosphate or alkylsulphate. ### Claim 5 (depends on 1) The fabric softener active composition according to claim 1, wherein the component (b) content is in the range from 8 to 30% wt. based on the total weight of the fabric softener active composition. ### Claim 6 (depends on 1) The fabric softener active composition according to claim 1 wherein either the component (b) is a fatty acid methyl ester or a mixture of fatty acid methyl esters, or a fatty acid ethyl ester or a mixture of fatty acid ethyl esters; or the component (b) is a fatty acid ester or a mixture of fatty acid esters derived from a C12-C18 fatty alcohol or a mixture of C12-C18 fatty alcohols. ### Claim 7 (depends on 1) The fabric softener active composition according to claim 1 wherein the component (c) is a C12-C18 fatty acid or a mixture of C12-C18 fatty acids. ### Claim 8 (depends on 1) The fabric softener active composition according to claim 1 wherein the component (a), the component (b), the component (c) are derived from the same fatty acid. ### Claim 9 (depends on 1) The fabric softener composition of claim 1, wherein the solvent content is less than 2% by weight of the total weight of the fabric softener active composition. ### Claim 10 (depends on 1) A method to obtain a fabric softener active composition as defined in claim 1 comprising: i) an esterification step, wherein a fatty acid or a methyl ester or a triglyceride thereof is reacted with an alkanolamine, wherein the molar ratio of fatty acid to alkanolamine is from 1.4:1 to 2.5:1, to obtain a mixture containing an esteramine; and ii) a quaternization step, wherein the mixture obtained after the esterification step is reacted with an alkylating agent. ### Claim 11 (depends on 10) The method according to claim 10, wherein in step i), the fatty acid, methyl ester or triglyceride thereof is/are reacted with an alkanolamine until the acid value is below 2 mg KOH/g. ### Claim 12 (depends on 10) The method according to claim 10, wherein the quaternization reaction takes place in a degree from 60 to 95% of the totality of the reaction. ### Claim 13 (depends on 10) The method according to claim 10, wherein the component (b) present in the fabric softener active composition is intentionally added and/or generated in situ in the esterification step, after the esterification step, in the quaternization step or after the quaternization step. ### Claim 14 (depends on 10) The method according to claim 10 wherein the fabric softener active composition further comprises a component (d), said component being a fatty alcohol or a mixture of fatty alcohols, wherein the component (d) content is higher than 0% wt. and lower than 20% wt. based on the total weight of the fabric softener active composition, and wherein the component (b) is generated in situ by reaction with the component (d) which is added in the esterification step, after the esterification step, in the quaternization step or after the quaternization step. ### Claim 15 (depends on 10) The method according to claim 10, wherein component (c) present in the fabric softener active composition is intentionally added in the esterification step, after the esterification step, in the quaternization step or after the quaternization step. ### Claim 16 (depends on 1) A fabric softener composition comprising a fabric softener active composition as defined in claim 1, further comprising at least water, wherein the fabric softener active composition is present in an amount from 1 to 30% wt. based on the total weight of the fabric softener composition. ### Claim 17 (depends on 16) A method of conditioning a textile fabric, comprising the step of immersing the textile fabric in an aqueous bath comprising the fabric softener composition as defined in claim 16. ### Claim 18 (depends on 16) A method to obtain the fabric softener composition as defined in the claim 16, comprising the steps: i) adding the fabric softener active composition mixture to water; ii) stirring to obtain a homogeneous dispersion. ### Claim 19 (depends on 18) The method according to claim 18, comprising the steps: i) mixing in the molten state of the fabric softener active composition with the further components: from 0 to 2% of an electrolyte concentration aid; and/or from 0.01 to 3% of a thickening polymer; and/or from 0.01 to 5% of a perfume; ii) adding the obtained mixture to water; iii) stirring to obtain a homogeneous dispersion; and iv) cooling down.