# US 11,077,035 B2 · Hair treatment compositions and methods > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 11,077,035 B2 - Document ID: US11077035B2 - Status: Granted - Kind: B2 - Application number: 16/059,425 - Filed: 2018-08-09 - Published: 2019-02-14 - Granted: 2021-08-03 - Earliest claimed: 2017-08-11 - Assignees: Sytheon Ltd - Applicants: Sytheon Limited - Inventors: Ratan K Chaudhuri - Web page: https://patentgrep.com/patent/US11077035B2 ## CPC - A61K 8/35: Ketones, e.g. benzophenone - A61K 8/36: Carboxylic acids; Salts or anhydrides thereof - A61K 8/37: Esters of carboxylic acids - A61Q 5/002: {Preparations for repairing the hair, e.g. hair cure} - A61Q 5/004: {Preparations used to protect coloured hair} - A61Q 5/02: Preparations for cleaning the hair - A61Q 5/08: Preparations for bleaching the hair - A61Q 5/12: Preparations containing hair conditioners - A61K 2800/4322: in preparations for temporarily coloring the hair further containing an oxidizing agent - A61K 2800/51: Chelating agents - A61K 2800/882: Mixing prior to application - A61K 2800/884: Sequential application - A61Q 5/06: Preparations for styling the hair, e.g. by temporary shaping or colouring - A61Q 5/065: {Preparations for temporary colouring the hair, e.g. direct dyes} - A61Q 5/10: Preparations for permanently dyeing the hair - A61Q 17/04: Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations - A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D) - A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS ## Abstract The present invention is directed to the hair care treatment compositions, including pre- and post-treatment compositions, containing select aryl alkanone compounds as quenching and/or chelating agents. ## Claims ### Claim 1 An improved hair care composition wherein the improvement comprises the presence of an effective amount of at least one aryl alkanone compound having the Formula I wherein R1, R2, R3, R4 and R5 which may be the same or different, are each independently H, OH, or a C1-C8 linear or branched alkyl or alkoxy group, and R6 is CH3 to prevent or reduce hair damage or hair color fading as compared to the use of the same composition without the aryl alkanone wherein the effective amount of the aryl alkanone compound is characterized as being present at a weight ratio of from 25:1 to 1:25 based on the amount of oxidizing agents in the case of hair care composition including an oxidizing agent or to be used concurrent with an oxidizing agent containing hair care composition; otherwise the effective amount is from about 0.1 to 15 percent by weight based on the total weight of the hair care composition. ### Claim 2 (depends on 1) The improved hair care composition of claim 1 wherein R1, R2, R3, R4 and R5 which may be the same or different, are each independently H or a C1-C6 linear or branched alkyl or alkoxy group. ### Claim 3 (depends on 1) The improved hair care composition of claim 1 wherein R1, R2, R3, R4 and R5 which may be the same or different, are each independently H or a C1-C4 linear or branched alkyl or alkoxy group. ### Claim 4 (depends on 1) The improved hair care composition of claim 1 wherein R1═R5═H and each of R2, R3, and R4 is independently a C1-C4 linear or branched alkoxy or a C1-C8 linear or branched alkyl. ### Claim 5 (depends on 1) The improved hair care composition of claim 1 wherein R1═R2═R5═H; and each of R3 and R4 is independently a C1-C4 linear or branched alkoxy or C1-C8 linear or branched alkyl. ### Claim 6 (depends on 1) The improved hair care composition of claim 1 wherein the aryl alkanone of Formula 1 is selected from the group consisting of: Compound 1A: R1═R3═R5═OMe and R2═R4═H; R6═CH3; Compound 1B: R1═R3═R5═H and R2═R4═OMe; R6═CH3; Compound 1C: R1═R2═R5═H and R3═R4═Me; R6═CH3; Compound 1D: R1═R2═R5═H and R3═R4═OMe; R6═CH3; Compound 1E: R1═R2═R4═R5═H; R3═OMe; R6═CH3; Compound 1F: R1═R5═H; R2═R3═R4═OMe; R6═CH3; Compound 1G: R1═R5═H; R2═R3═R4═Me; R6═CH3; Compound 1H: R1═R4═OMe; R2═R3═R5═H; R6═CH3; Compound 1I: R1═R3═R5═H; R2═R4═Me; R6═CH3; Compound 1J: R1═R2═R4═R5═H; R3═Me; R6═CH3; Compound 1K: R1═R3═R4═R5═H; R2═Me; R6═CH3; Compound 1L: R1═R3═R4═R5═H; R2═OMe; R6═CH3; Compound 1M: R1═R2═R5═H; R3═OH; R4═OCH3; R6═CH3; Compound 1N: R1═R3═R5═H; R2═R4═Me; R6═CH3; Compound 1P: R1═R2═R4═R5═H; R3═Me; R6═CH3; and Compound 1Q: R1═R2═R4═R5═H; R3═OMe; R6═CH3. ### Claim 7 (depends on 1) The improved hair care composition of claim 1 wherein the hair care composition comprises other agents or ingredients which are oxidizing agents and the one or more aryl alkanones is present in an amount whereby the weight ratio of the aryl alkanone to the oxidizing agents is from 25:1 to 1:25. ### Claim 8 (depends on 1) The improved hair care composition of claim 1 wherein the hair care composition comprises other agents or ingredients which are oxidizing agents and the one or more aryl alkanones is present in an amount whereby the weight ratio of the aryl alkanone to the oxidizing agents is from 15:1 to 1:15. ### Claim 9 (depends on 1) The improved hair care composition of claim 1 wherein the hair care composition is a hair treatment composition selected from hair coloring products, shampoos, conditioners, hair restorative treatments, perming products, alcohol based hair sprays, gel hair sprays, and hair bleaching compositions. ### Claim 10 (depends on 1) The improved hair care composition of claim 1 wherein the hair care composition is a hair coloring product which comprises one or more components that are individually packaged and combined and/or used concurrently or sequentially in the hair coloring process and the aryl alkanone is present in at least one of the components thereof. ### Claim 11 (depends on 1) The improved hair care composition of claim 1 wherein the aryl alkanone is free of phenolic hydroxy groups. ### Claim 12 (depends on 1) The improved hair care composition of claim 1 wherein the composition is a pretreatment composition or a post treatment composition and the composition comprises from about 0.1 to about 15 wt percent of the aryl alkanone. ### Claim 13 (depends on 1) The improved hair care composition of claim 1 wherein the composition is a pretreatment composition or a post treatment composition and the composition comprises from about 0.5 to about 10 wt percent of the aryl alkanone. ### Claim 14 (depends on 1) The improved hair care composition of claim 1 wherein the composition is a pretreatment composition or a post treatment composition and the composition comprises from about 1 to about 4 wt percent of the aryl alkanone in a carrier suitable for application to the hair. ### Claim 15 (depends on 1) The improved hair care composition of claim 1 wherein the aryl alkanone compound is acetyl zingerone. ### Claim 16 (depends on 1) The improved hair care composition of claim 1 wherein at east one of R2, R3, and R4 is a C1-C8 linear or branched alkoxy or alkyl. ### Claim 17 A method of preventing or protecting hair from photo-, thermal- or oxidative damage comprising applying to the hair a composition comprising an effective amount of at least one aryl alkanone compound having the Formula I wherein R1, R2, R3, R4 and R5 which may be the same or different, are each independently H, OH, or a C1-C8 linear or branched alkyl or alkoxy group, and R6 is CH3 prior to exposing the hair to conditions which effect or promote photo-, thermal- or oxidative damage, whereby less hair damage is found as compared to the hair exposed to those conditions without the application of the composition wherein the effective amount of the aryl alkanone compound is characterized as being from about 0.1 to 15 percent by weight of the composition. ### Claim 18 A method of reducing the damage caused by hair treatment compositions comprising either (i) incorporating into the hair treatment composition an effective amount of at least one aryl alkanone compound having the Formula I wherein R1, R2, R3, R4 and R5 which may be the same or different, are each independently H, OH, or a C1-C8 linear or branched alkyl or alkoxy group, and R6 is CH3 prior to or concurrent with its application to the hair or (ii) treating the hair with a composition comprising at least one of the aforementioned aryl alkanones in an effective amount prior to or following the application of the hair treatment composition to the hair, whereby less hair damage is found as compared to the treated hair which has not also been treated with the aryl alkanone wherein the effective amount of the aryl alkanone compound is characterized as being present at a weight ratio of from 25:1 to 1:25 based on the amount of oxidizing agents in the case of hair care composition including an oxidizing agent or to be used concurrent with an oxidizing agent containing hair care composition; otherwise, the effective amount is from about 0.1 to 15 percent by weight based on the total weight of the hair care composition. ### Claim 19 (depends on 18) The method of claim 18 wherein the composition containing the aryl alkanone is applied to the hair prior to application of a hair treatment composition comprising oxidizing agents. ### Claim 20 (depends on 18) The method of claim 18 wherein the composition containing the aryl alkanone is applied before bleaching, perming or coloring the hair. ### Claim 21 (depends on 18) The method of claim 18 wherein the composition containing the aryl alkanone is applied to the hair prior to exposure to oxidizing conditions other than a hair treatment composition. ### Claim 22 (depends on 21) The method of claim 21 wherein the composition containing the aryl alkanone is applied prior to exposure to the sun or air pollutants and/or prior to participation in an aquatic activity in which the hair is exposed to water chemicals. ### Claim 23 (depends on 18) The method of claim 18 wherein the composition containing the aryl alkanone is applied to the hair following the treatment of the hair with a hair treatment composition comprising oxidizing agents. ### Claim 24 (depends on 18) The method of claim 18 wherein the composition containing the aryl alkanone is applied to the hair following exposure to oxidizing conditions other than a hair treatment composition. ### Claim 25 (depends on 24) The method of claim 24 wherein the composition containing the aryl alkanone is applied to the hair following exposure to the sun or air pollutants and/or participation in an aquatic activity in which the hair is exposed to water chemicals. ### Claim 26 (depends on 17) The method of claim 17 wherein the aryl alkanone compound is acetyl zingerone. ### Claim 27 (depends on 18) The method of claim 18 wherein the aryl alkanone compound is acetyl zingerone. ### Claim 28 (depends on 17) The method of claim 17 wherein at least one of R2, R3, and R4 is a C1-C8 linear or branched alkoxy or alkyl. ### Claim 29 (depends on 18) The method of claim 18 wherein at east one of R2, R3, and R4 is a C1-C8 linear or branched alkoxy or alkyl. ### Claim 30 (depends on 17) The method of claim 17 wherein the aryl alkanone of Formula 1 is selected from the group consisting of: Compound 1A: R1═R3═R5═OMe and R2═R4═H; R6═CH3; Compound 1B: R1═R3═R5═H and R2═R4═OMe; R6═CH3; Compound 1C: R1═R2═R5═H and R3═R4═Me; R6═CH3; Compound 1D: R1═R2═R5═H and R3═R4═OMe; R6═CH3; Compound 1E: R1═R2═R4═R5═H; R3═OMe; R6═CH3; Compound 1F: R1═R5═H; R2═R3═R4═OMe; R6═CH3; Compound 1G: R1═R5═H; R2═R3═R4═Me; R6═CH3; Compound 1H: R1═R4═OMe; R2═R3═R5═H; R6═CH3; Compound 1I: R1═R3═R5═H; R2═R4═Me; R6═CH3; Compound 1J: R1═R2═R4═R5═H; R3═Me; R6═CH3; Compound 1K: R1═R3═R4═R5═H; R2═Me; R6═CH3; Compound 1L: R1═R3═R4═R5═H; R2═OMe; R6═CH3; Compound 1M: R1═R2═R5═H; R3═OH; R4═OCH3; R6═CH3; Compound 1N: R1═R3═R5═H; R2═R4═Me; R6═CH3; Compound 1P: R1═R2═R4═R5═H; R3═Me; R6═CH3; and Compound 1Q: R1═R2═R4═R5═H; R3═OMe; R6═CH3. ### Claim 31 (depends on 18) The method of claim 18 wherein the aryl alkanone of Formula 1 is selected from the group consisting of: Compound 1A: R1═R3═R5═OMe and R2═R4═H; R6═CH3; Compound 1B: R1═R3═R5═H and R2═R4═OMe; R6═CH3; Compound 1C: R1═R2═R5═H and R3═R4═Me; R6═CH3; Compound 1D: R1═R2═R5═H and R3═R4═OMe; R6═CH3; Compound 1E: R1═R2═R4═R5═H; R3═OMe; R6═CH3; Compound 1F: R1═R5═H; R2═R3═R4═OMe; R6═CH3; Compound 1G: R1═R5═H; R2═R3═R4═Me; R6═CH3; Compound 1H: R1═R4═OMe; R2═R3═R5═H; R6═CH3; Compound 1I: R1═R3═R5═H; R2═R4═Me; R6═CH3; Compound 1J: R1═R2═R4═R5═H; R3═Me; R6═CH3; Compound 1K: R1═R3═R4═R5═H; R2═Me; R6═CH3; Compound 1L: R1═R3═R4═R5═H; R2═OMe; R6═CH3; Compound 1M: R1═R2═R5═H; R3═OH; R4═OCH3; R6═CH3; Compound 1N: R1═R3═R5═H; R2═R4═Me; R6═CH3; Compound 1P: R1═R2═R4═R5═H; R3═Me; R6═CH3; and Compound 1Q: R1═R2═R4═R5═H; R3═OMe; R6═CH3.