# US 11,110,041 B2 · Process for permanent shaping hair > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 11,110,041 B2 - Document ID: US11110041B2 - Status: Granted - Kind: B2 - Application number: 15/757,839 - Filed: 2016-03-15 - Published: 2018-11-29 - Granted: 2021-09-07 - Earliest claimed: 2015-09-08 - Assignees: Kao Germany GmbH - Applicants: Kao Germany GmbH - Inventors: Bernd Nöcker; Steven Breakspear; Peter Bauer; Jonathan Wood - Web page: https://patentgrep.com/patent/US11110041B2 ## CPC - A61K 8/19: containing inorganic ingredients - A45D 7/04: chemical - A61K 8/20: Halogens; Compounds thereof - A61K 8/22: Peroxides; Oxygen; Ozone - A61K 8/23: Sulfur; Selenium; Tellurium; Compounds thereof - A61K 8/362: Polycarboxylic acids - A61K 8/365: Hydroxycarboxylic acids; Ketocarboxylic acids - A61K 8/44: Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof - A61Q 5/04: Preparations for permanent waving or straightening the hair - 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) - A45D: HAIRDRESSING OR SHAVING EQUIPMENT (wigs, toupees or the like A41G3/00, A41G5/00; hairdressers' chairs A47C1/04; hair cutting appliances, razors B26B); EQUIPMENT FOR COSMETICS OR COSMETIC TREATMENTS, e.g. FOR MANICURING OR PEDICURING - A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS ## Abstract The present invention relates to a process for improved and milder permanent shaping of hair, especially human hair. It has been found that when commonly used permanent shaping compositions are mixed with another composition comprising predominantly carboxylic acids, the permanent shaping effect of the composition is improved, homogeneous permanent shaping of hair fibers is achieved and natural cosmetic properties of hair are maintained. ## Claims ### Claim 1 A process for permanent shaping hair, the process comprising: a—optionally washing hair with a cleansing composition and towel drying the hair; b—mixing a composition A and a composition B immediately before application onto the hair at a weight ratio of composition A to composition B in the range of 10:0.1 to 10:1 to obtain a ready-to-use composition having an alkaline pH in the range from 7.3 to 11; c—applying the obtained ready-to-use composition onto the hair, and leaving the applied ready-to-use composition on the hair for 1 to 45 min; d—optionally rinsing the applied ready-to-use composition off the hair with water; e—optionally applying, onto the hair, an intermediate treatment composition comprising one or more inorganic salts and having a pH from 2 to 7; f—applying, onto the hair, a fixing composition comprising one or more oxidizing agents and having a pH in the range of 1.5 to 5 and leaving the applied fixing composition on the hair for 1 to 15 min; g—optionally rinsing the applied fixing composition off the hair; and h—optionally drying the hair, wherein the composition A is an aqueous composition comprising one or more reducing agents, one or more alkalizing agents, and has a pH in the range of 7.5 to 12, the composition B comprises; i) one or more carboxylic acids having three or more carboxyl groups and/or their salts; and ii) one or more additional organic acids and/or their salts having one or two carboxyl groups, the composition B comprises the acids of i) and ii) and/or their salts at a total concentration from 10% to 100% by weight, based on a total of the composition B, the obtained ready-to-use composition comprises the acids of i) and ii) and/or their salts at a total concentration in the range of 1% to 10% by weight, based on a total of the obtained ready-to-use composition, the composition B comprises the acids of (i) and (ii) at a weight ratio (i)/(ii) ranging from 10:1 to 1:250, the hair is put under tension before, during, or after application of the obtained ready-to-use composition, and the tension is released from the hair before or during application of the fixing composition or prior to rinsing off the applied fixing composition off the hair. ### Claim 2 (depends on 1) The process of claim 1, wherein the hair is put under tension before application of the obtained ready-to-use composition. ### Claim 3 (depends on 2) The process of claim 2, wherein the tension is released from the hair after rinsing off the applied fixing composition off the hair. ### Claim 4 (depends on 1) The process of claim 1, wherein the one or more carboxylic acids having three or more carboxyl groups are selected from citric acid, ethylene diamine tetra acetic acid (EDTA), pyromellitic acid, and glutamate diacetate, and the one or more additional organic acids with one or two carboxyl groups are selected from acetic acid, malic acid, lactic acid, glycolic acid, tartaric acid, formic acid, oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, maleic acid, and fumaric acid, the composition B comprises the acids of (i) and (ii) at a weight ratio (i)/(ii) ranging from 5:1 to 1:150, and the obtained ready-to-use composition has an alkaline pH in the range from 7.5 to 10.5. ### Claim 5 (depends on 1) The process of claim 1, wherein the composition B is a powder, a dispersion, an emulsion, a solution, or an aqueous composition. ### Claim 6 (depends on 1) The process of claim 1, wherein the pH of composition B ranges from 1 to 5 and the composition B further comprises an alkalizing agent. ### Claim 7 (depends on 1) The process of claim 1, wherein the one or more carboxylic acids having three or more carboxyl groups is EDTA and/or its salts. ### Claim 8 (depends on 1) The process of claim 1, wherein the one or more organic acids having one or two carboxyl groups is malic acid and/or its salts. ### Claim 9 (depends on 1) The process of claim 1 wherein the one or more reducing agents of the composition A are selected from thioglycolic acid, cysteamine and/or its salts, thioglycerin and/or its salts, glycerin esters of thioglycolic acid and/or its salts, thiolactic acid and/or its salts, and cysteine or its derivatives and/or its salts, wherein the one or more reducing agents are present at a concentration ranging from 1 to 15% by weight, based on a total of composition A. ### Claim 10 (depends on 6) The process of claim 6, wherein at least one of the one or more alkalizing agents of the Composition A and at least one alkalizing agent of the composition B is selected from ammonia, alkyl- or alkanolamines according to the general structure wherein R1, R2, and R3 are same or different and are selected from H, C3 to C4 unsaturated alkyl, C3 to C4 branched alkyl, C1 to C4 hydroxyl alkyl, C3 to C4 unsaturated hydroxyl alkyl, and C3 to C4 branched hydroxyl alkyl, with the condition that at least one of R1, R2, or R3 is different from H. ### Claim 11 (depends on 1) The process of claim 1, wherein at least one of the composition A and the composition B comprise(s) one or more ingredients selected from fatty alcohols, surfactants selected from anionic surfactants, nonionic surfactants, cationic surfactants, and amphoteric surfactants, ubiquinones, reducing agents, organic solvents, linear polysiloxanes, aminated silicones, cyclic silicones, arylated silicones, antioxidants, preservatives, amino acids, and polyols. ### Claim 12 (depends on 1) The process of claim 1, wherein the composition B comprises one or more thickening polymers selected from anionic, nonionic, cationic and amphoteric polymers, with a viscosity of at least 500 mPa·s measured at a polymer concentration of 1% by weight in water and at 20° C. with a Brookfield viscometer, with an appropriate spindle. ### Claim 13 (depends on 12) The process of claim 12, wherein the one or more thickening polymers are selected from hydroxypropyl xanthan gum, dehydroxanthan gum, xanthan gum, and polymeric anionic thickeners. ### Claim 14 (depends on 1) The process of claim 1, wherein the one or more carboxylic acids having three or more carboxyl groups of composition B is EDTA and/or its salts, and the one or more additional organic acids having one or two carboxyl groups is malic acid and/or its salt. ### Claim 15 (depends on 1) The process of claim 1, wherein the weight ratio (i)/(ii) ranges from 1:13 to 1:250. ### Claim 16 A process for permanent shaping hair, the process comprising: a—applying a ready-to-use composition onto the hair, wherein the ready-to-use composition is obtained by mixing a composition A and a composition B immediately before application onto the hair at a weight ratio of composition A to composition B in the range of 10:0.1 to 10:1, and leaving the applied ready-to-use composition on the hair for 1 to 45 min; b—applying, onto the hair, a fixing composition comprising one or more oxidizing agents and having a pH in the range of 1.5 to 5 and leaving the applied fixing composition on the hair for 1 to 15 min; wherein the composition A is an aqueous composition comprising one or more reducing agents, one or more alkalizing agents, and has a pH in the range of 7.5 to 12, the composition B comprises; i) one or more carboxylic acids having three or more carboxyl groups and/or their salts selected from citric acid, ethylene diamine tetra acetic acid (EDTA), pyromellitic acid, glutamate diacetate, and their salts; and ii) one or more additional organic acids and/or their salts having one or two carboxyl groups selected from acetic acid, malic acid, lactic acid, glycolic acid, tartaric acid, formic acid, oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, maleic acid, fumaric acid, and their salts, the composition B comprises the acids of i) and ii) and/or their salts at a total concentration from 10% to 100% by weight, based on a total of the composition B, the ready-to-use composition has an alkaline pH in the range from 7.3 to 11 and comprises the acids of i) and ii) and/or their salts at a total concentration in the range of 1% to 10% by weight, based on a total of the ready-to-use composition, the composition B comprises the acids of (i) and (ii) at a weight ratio (i)/(ii) ranging from 10:1 to 1:250, the hair is put under tension before, during, or after application of the ready-to-use composition, and the tension is released from the hair before or during application of the fixing composition or prior to rinsing off the applied fixing composition off the hair.