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WO2025212874A1 - Systèmes de coloration durable comprenant un composé contenant du catéchol et un colorant capillaire - Google Patents

Systèmes de coloration durable comprenant un composé contenant du catéchol et un colorant capillaire

Info

Publication number
WO2025212874A1
WO2025212874A1 PCT/US2025/022937 US2025022937W WO2025212874A1 WO 2025212874 A1 WO2025212874 A1 WO 2025212874A1 US 2025022937 W US2025022937 W US 2025022937W WO 2025212874 A1 WO2025212874 A1 WO 2025212874A1
Authority
WO
WIPO (PCT)
Prior art keywords
hair
composition
catechol
total weight
dye
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
PCT/US2025/022937
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English (en)
Inventor
Zhaoxia Ji
Jingjing Zhang
Ronald P. Mclaughlin
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Living Proof Inc
Original Assignee
Living Proof Inc
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Filing date
Publication date
Application filed by Living Proof Inc filed Critical Living Proof Inc
Publication of WO2025212874A1 publication Critical patent/WO2025212874A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/35—Ketones, e.g. benzophenone
    • A61K8/355—Quinones
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/368—Carboxylic acids; Salts or anhydrides thereof with carboxyl groups directly bound to carbon atoms of aromatic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • A61K8/375—Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A61K8/415—Aminophenols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A61K8/418—Amines containing nitro groups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A61K8/466—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfonic acid derivatives; Salts
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/10—Preparations for permanently dyeing the hair

Definitions

  • Hair coloring has a long history as one of the most important branches of the beauty industry.
  • Current hair coloring products can be categorized as temporary, semipermanent, demi-permanent and permanent based on color durability.
  • Temporary and semipermanent products are generally considered safe and only involve application of direct dyes to hair, but commonly suffer low color durability due to weak interactions between dyes and hair.
  • Demi-permanent and permanent hair dye products containing oxidative dyes can generate long-lasting colors in hair through oxidative reactions by using strong oxidative reagents like hydrogen peroxide in a highly alkaline environment containing ammonia or other alkaline agents like monoethanolamine (MEA).
  • MEA monoethanolamine
  • oxidative coloring processes not only can cause extensive hair damage, but also have potential safety and regulatory concerns. Additionally, while oxidative dyes can provide longer lasting color, they don’t usually achieve the same level of vibrancy and intensity as direct dyes. Therefore, it’s desirable to develop a direct dye-based coloring system that not only provides vibrant long-lasting colors but also is safe and convenient.
  • FIG. la shows Level 9/10 bleached hair tresses treated with an aqueous solution containing 0.05 wt% Acid Violet 43 (AV43) hair dye and 0.02 wt% rosmarinic acid (Rosmarinic Acid 90% (RA90)) for 5 min at pH of 4.5, 5.5, and 6.5.
  • AV43 Acid Violet 43
  • RA90 rosmarinic Acid 90%
  • FIG. 2 shows the water contact angles of Level 9/10 bleached hair fibers treated with 0.05 wt% AV43 aqueous solutions at pH of 5.5 for 5 minutes at room temperature.
  • FIG. 3a shows Level 9/10 bleached hair tresses treated with 0.05 wt% AV43 solutions with 0.01, 0.02, or 0.03 wt% RA90.
  • FIG. 3b shows the b values of Level 9/10 bleached hair tresses treated with 0.05 wt% AV43 solutions with 0.01, 0.02, or 0.03 wt% RA90.
  • FIG. 4 shows b values of Level 9/10 bleach hair tresses treated with 0.05 wt% AV43 aqueous solutions with or without 0.02 wt% RA immediately after the treatment as well as after 1, 3, and 5 shampoo & conditioner washes.
  • FIG. 5a shows Level 9/10 bleached hair tresses treated with commercial purple shampoos (CS #1, 2, 3, 4) containing 0.02 wt% RA (+RA) vs. the shampoo alone (As is).
  • FIG. 6a shows Level 9/10 bleached hair tresses treated with a commercial inshower toner with 0.02 wt% RA (+RA) vs. the toner alone (As is) immediately after toning and throughout washing test.
  • FIG. 6b shows b values of Level 9/10 bleached hair tresses treated with a commercial in-shower toner with 0.02 wt% RA vs. the toner alone immediately after toning and throughout washing test.
  • FIG. 7a shows Level 9/10 bleached hair tresses treated with AV43 aqueous solutions at various concentrations.
  • FIG. 7b shows the b values Level 9/10 bleached hair tresses treated with AV43 aqueous solutions at various concentrations.
  • FIG. 8a shows Level 9/10 bleached hair tresses treated with 0.05 wt% AV43 aqueous solutions w/ or w/o 0.34 wt% P6-RA during a washing test.
  • FIG. 8b shows the b values of Level 9/10 bleached hair tresses treated with 0.05 wt% AV43 aqueous solutions w/ or w/o 0.34 wt% P6-RA during a washing test.
  • FIG. 9a shows Level 9/10 bleached hair tresses treated with 0.05 wt% AV43 aqueous solutions containing 0.02 wt% RA90, or 0.4 wt% HBO vs. the dye solution alone, during a washing test.
  • FIG. 9b shows the b values of Level 9/10 bleached hair tresses treated with 0.05 wt% AV43 aqueous solutions containing 0.02 wt% RA90, or 0.4 wt% HBO vs. the dye solution alone, during a washing test.
  • FIG. 10a shows Level 9/10 bleached hair tresses treated with 0.05 wt% AV43 aqueous solutions w/ dye alone, 0.5 wt% Inovel CAFA, or 2.5 wt% Endothelyol.
  • FIG. 10b shows the b values of Level 9/10 bleached hair tresses treated with 0.05 wt% AV43 aqueous solutions w/ dye alone, 0.5 wt% Inovel CAFA, or 2.5 wt% Endothelyol.
  • FIG. Ila shows 3x bleached Level 9/10 hair tresses treated with 1 wt% BB17 solution w/ dye alone or in the presence of 1 wt% RA90 or 1 wt% ChA during washing test.
  • FIG. 11b shows 3x bleached Level 9/10 hair tresses treated with 1 wt% BR76 solution w/ dye alone, or in the presence of 1 wt% RA90 or 1 wt% ChA during washing test.
  • FIG. 12 shows 3x bleached Level 9/10 hair tresses treated with 5 wt% Az or Pur aqueous solutions containing dye alone (top panel) or with 4 wt% CA (bottom panel) after color treatment and multiple washes.
  • FIG. 13a shows AE of 3x bleached Level 9/10 hair tresses treated for 20 mins with
  • FIG. 13b shows AE of 3x bleached Level 9/10 hair tresses treated for 30 mins with
  • FIG. 13c shows AE of 3x bleached Level 9/10 hair tresses treated for 45 mins with
  • FIG. 14c shows AE of 3x bleached Level 9/10 hair tresses treated for 45 mins with
  • FIG. 18a shows images of 3x bleached tresses treated with Teluca® CORE ash blonde and 0.5 wt% ChA (AB+ChA) vs. a commercial oxidative permanent hair color (Wella® 7/7 medium blonde, brown, MBB) immediately after colored and up to 25 washes.
  • FIG. 18b shows images AE values of 3x bleached tresses treated with AB+ChA vs. MBB after up to 25 washes as compared to immediately after colored.
  • FIG. 20 shows images of bleached hair tresses treated with catechol and direct dye-based toning system, which closely resemble the shades of oxidative dye based ShadesEQ demi-permanent tonners.
  • FIG. 24b shows AE of 3x bleached Level 9/10 hair tresses treated with Pravan Sunstone and the product with or without 2wt% ChA after up to 10 washes as compared to immediately after colored.
  • FIG. 26a shows tress images from washing test of 3x bleached tresses post-treated with 0.1 wt% RA90 or 0.2wt% ChA solution immediately after the application of Ion Intensive Shine Red but before rinsing, as compared to the control without any posttreatment.
  • FIG. 26b shows AE during washing test of 3x bleached tresses post-treated with 0.1 wt% RA90 or 0.2wt% ChA solution immediately after the application of Ion Intensive Shine Red but before rinsing, as compared to the control without any post-treatment.
  • FIG. 27b shows AE during washing test of tresses post-treated with 0.1 wt% RA90 or 0.2wt% ChA solution after the application of Ion Intensive Shine Red and water rinse, as compared to the control without any post-treatment.
  • FIG. 28a shows images of hair tresses colored with Ion Intense Red 7RR with or without post-treatment, immediately after coloring and up to 10 washes.
  • the post-treatments include: 0.5 wt% ChA, 1 wt% Citropol T, or a combination of 0.5 wt% ChA and 1 wt% Citropol T.
  • catechol containing compounds for use in the described methods include, but are not limited to, caffeic acid (CA), rosmarinic acid (RA), and chlorogenic acid (ChA), protocatechuic acid catechin, epicatechin, pyrocatechol, 3-methylcatechol, 4- methylcatechol, 4-nitrocatechol, 4-chlorocatechol, 4-bromocatechol, 4-ethylcatechol, 4- hydroxy-3-methoxycatechol, procyanidin B2, and ellagic acid.
  • CA caffeic acid
  • RA rosmarinic acid
  • ChA chlorogenic acid
  • protocatechuic acid catechin epicatechin
  • pyrocatechol 3-methylcatechol
  • 4- methylcatechol 4-nitrocatechol
  • 4-chlorocatechol 4-bromocatechol
  • 4-ethylcatechol 4- hydroxy-3-methoxycatechol
  • procyanidin B2 and ellagic acid.
  • a hair dye may be demipermanent. Demi-permanent hair dye compositions also contain oxidative dyes and involve similar chemistry as permanent hair dyes except that lower levels of hydrogen peroxide and alkalizer (e.g., monoethanolamine, not ammonia) are used.
  • a hair dye may be semi-permanent or temporary. Semi-permanent and temporary hair dyes contain a mixture of preformed dyes, so called direct dyes or non-oxidative dyes, which are directly applied to hair to achieve a meaningful color change without lightening the hair. Semi-permanent and temporary dyes do not contain ammonia or peroxide.
  • the effective amount of the at least one catechol containing compound in the hair composition is from about 0.0001% to about 5% of the total weight of the composition e.g., from about 0.0001% to about 4% of the total weight of the composition, from about 0.0001% to about 3% of the total weight of the composition, from about 0.0001% to about 2% of the total weight of the composition, from about 0.0001% to about 1% of the total weight of the composition, from about 0.001% to about 5% of the total weight of the composition, from about 0.001% to about 4% of the total weight of the composition, from about 0.001% to about 3% of the total weight of the composition, from about 0.001% to about 2% of the total weight of the composition, from about 0.001% to about 1% of the total weight of the composition, from about 0.005% to about 5% of the total weight of the composition, from about 0.005%
  • the amount of the at least one hair dye in the hair composition is from about 0.0001% to about 5% of the total weight of the composition e.g., from about 0.0001% to about 4% of the total weight of the composition, from about 0.0001% to about 3% of the total weight of the composition, from about 0.0001% to about 2% of the total weight of the composition, from about 0.0001% to about 1% of the total weight of the composition, from about 0.001% to about 5% of the total weight of the composition, from about 0.001% to about 4% of the total weight of the composition, from about 0.001% to about 3% of the total weight of the composition, from about 0.001% to about 2% of the total weight of the composition, from about 0.001% to about 1% of the total weight of the composition, from about 0.005% to about 5% of the total weight of the composition, from about 0.005% to about 4% of the total weight of the composition, from about 0.005% to about 3% of the total weight of the composition, from about 0.005% to about 4% of the total weight of
  • the at least one hair dye is selected from a permanent, a demipermanent, a semi-permanent, and a temporary dye.
  • the at least one hair dye is a permanent dye.
  • the at least one hair dye is a semi-permanent dye.
  • the at least one hair dye is a demi-permanent dye.
  • the at least one hair dye is a temporary dye.
  • the at least one catechol containing compound is derived from synthetic or natural sources.
  • the at least one catechol containing compound is selected from caffeic acid (CA), rosmarinic acid (RA), and chlorogenic acid (ChA), protocatechuic acid catechin, epicatechin, pyrocatechol, 3-methylcatechol, 4-methylcatechol, 4-nitrocatechol, 4-chlorocatechol, 4-bromocatechol, 4-ethylcatechol, 4-hydroxy-3- methoxycatechol, procyanidin B2, and ellagic acid.
  • the at least one catechol containing compound is selected from caffeic acid (CA), rosmarinic acid (RA), and chlorogenic acid (ChA).
  • the hair coloring compositions described herein further comprise cosmetically acceptable carriers, surfactants, solvents, or other hair benefit ingredients.
  • the hair coloring compositions described herein is a hair dye, shampoo, conditioner, or color toner. In some aspects, the hair coloring compositions described herein is a shampoo or color toner.
  • the hair coloring compositions described herein are used to color human hair. Therefore, provided are methods for coloring hair comprising applying to the hair a hair coloring composition as described herein.
  • color shampoo, color conditioner, or color toner and an effective amount of at least one catechol containing compound on hair to improve the initial color deposition and/or color longevity of a hair dye.
  • Also provided is a method for coloring hair comprising applying to the hair an effective amount of at least one catechol containing compound and at least one hair dye.
  • a method for improving the initial color deposition and/or color longevity of a hair dye comprising applying to hair at least one hair dye and an effective amount of at least one catechol containing compound.
  • a method for improving the initial color deposition and/or color longevity of a color shampoo, color conditioner, or color toner on hair comprising applying to the hair the color shampoo or color toner and at least one catechol containing compound.
  • the at least one catechol containing compound used in the described methods may be applied prior to, after, or concurrently with the hair dye, color shampoo, color conditioner, or color toner.
  • the at least one catechol containing compound used in the described methods is applied prior to the hair dye, color shampoo, color conditioner, or color toner.
  • the at least one catechol containing compound used in the described methods is applied after the hair dye, color shampoo, color conditioner, or color toner. In some aspects of the present methods, the at least one catechol containing compound used in the described methods is be applied concurrently with the hair dye, color shampoo, color conditioner, or color toner. [0090] In some aspects of the present methods, the at least one catechol containing compound is applied to the hair in the form of an aqueous solution comprising the at least one catechol containing compound.
  • the at least one catechol containing compound is applied to the hair in the form of an aqueous solution comprising from about 0.0001% to about 5% of the at least one catechol, from about 0.0001% to about 4% of the at least one catechol, from about 0.0001% to about 3% of the at least one catechol, from about 0.0001% to about 2% of the at least one catechol, from about 0.0001% to about 1% of the at least one catechol, from about 0.001% to about 5% of the at least one catechol, from about 0.001% to about 4% of the at least one catechol, from about 0.001% to about 3% of the at least one catechol, from about 0.001% to about 2% of the at least one catechol, from about 0.001% to about 1% of the at least one catechol, from about 0.005% to about 5% of the at least one catechol, from about 0.005% to about 4% of the at least one catechol, from about 0.005% to about 3% of the at least one catechol, from about 0.005% to about
  • the at least one catechol containing compound is applied to the hair in the form of an aqueous solution comprising from about 0.005 wt% to about 5 wt% of the at least one catechol containing compound, from about 0.005 wt% to about 4 wt% of the at least one catechol containing compound, or from about 0.01 wt% to about 1 wt% of the at least one catechol containing compound.
  • the at least one catechol containing compound is applied to the hair in the form of an aqueous solution comprising from about 0.005 wt% to about 5 wt% of the at least one catechol containing compound.
  • the at least one catechol containing compound is applied to the hair in the form of an aqueous solution comprising from about 0.005 wt% to about 4 wt% of the at least one catechol containing compound.
  • the at least one catechol containing compound is applied to the hair in the form of an aqueous solution comprising from about 0.01 wt% to about 1 wt% of the at least one catechol containing compound.
  • the at least one hair dye is applied to the hair in the form of an aqueous solution comprising from about 0.0001% to about 5% of the at least one hair dye, from about 0.0001% to about 4% of the at least one hair dye, from about 0.0001% to about 3% of the at least one hair dye, from about 0.0001% to about 2% of the at least one hair dye, from about 0.0001% to about 1% of the at least one hair dye, from about 0.001% to about 5% of the at least one hair dye, from about 0.001% to about 4% of the at least one hair dye, from about 0.001% to about 3% of the at least one hair dye, from about 0.001% to about 2% of the at least one hair dye, from about 0.001% to about 1% of the at least one hair dye, from about 0.005% to about 5% of the at least one hair dye, from about 0.005% to about 4% of the at least one hair dye, from about 0.005% to about 3% of the at least one hair dye
  • the at least one hair dye is applied to the hair in the form of an aqueous solution comprising from about 0.01 wt% to about 5 wt% hair dye.
  • the at least one catechol containing compound and the at least one hair dye are applied to the hair in the form of an aqueous solution comprising both the at least one catechol containing compound and the at least one hair dye.
  • the at least one catechol containing compound is applied to the hair prior to applying the hair dye, color shampoo, color conditioner, or color toner. [00100] In some aspects of the present methods, the at least one catechol containing compound is applied to the hair after applying the hair dye, color shampoo, color conditioner, or color toner.
  • the at least one catechol containing compound is applied to the hair concurrently with the hair dye, color shampoo, color conditioner, or color toner.
  • the at least one hair dye or hair dye is selected from a permanent, a demi-permanent, a semi-permanent, and a temporary dye.
  • the at least one hair dye or hair dye is a permanent dye.
  • the at least one hair dye or hair dye is a demi-permanent dye.
  • the at least one hair dye or hair dye is a semi-permanent dye.
  • the at least one hair dye or hair dye is selected from an anionic (also known as acid dyes), cationic (also known as basic dyes), and non-ionic hair dye (e.g., nitro dyes).
  • the at least one hair dye or hair dye is selected from Acid Violet 43 (AV43), basis brown 17 (BB17), basic red 76 (BR76), alizarin (Az) and purpurin (Pur).
  • AV43 Acid Violet 43
  • BB17 basis brown 17
  • BR76 basic red 76
  • Az alizarin
  • Pur purpurin
  • the at least one hair dye or hair dye is Acid Violet 43 (AV43).
  • the at least one catechol containing compound is derived from synthetic or natural sources.
  • FIG. 10a shows the tresses treated with AV43 aqueous solution containing Inovel CAFA or Endothelyol at a supplier recommended concentration for the assessment of their efficacy.
  • the darker appearance of the tresses treated with these two actives compared to the dye-alone treatment indicates the enhanced dye deposition by both actives.
  • the b value is further reduced by 29% when using Inovel CAFA and 74% when using Endothelyol as compared to the dye alone.
  • FIG. 12 shows the images of 3x bleached tresses treated with 5 wt% Az or Pur aqueous solutions containing dye alone or with 4 wt% caffeic acid.
  • the tresses were treated for 20, 30, or 45 mins. In general, the longer treatment time leads to more color deposition. But for all tested treatment times, the presence of CA shows clear improvements in both initial dye deposition and color longevity during the washing test.
  • the AE values of the tresses treated with CA are significantly lower than that of the tresses treated with dye alone for up to 15 washes.
  • FIG. 15 shows the images of 3x bleached tresses treated with a set of mixture dyes including Teluca® CORE natural black, dark chocolate blonde, ash blonde, and platinum with or without 0.5 wt% ChA.
  • Teluca® CORE dye mixtures were prepared according to the supplier’s use instructions. The total dye concentration in these Teluca® CORE dye mixtures vary from about 0.005 wt% to about 2 wt%.
  • 1 wt% ChA was added. All dye mixtures were further diluted with deionized water in a 1:1 dilution ratio before application.
  • the tresses were treated with 1 ml of the diluted dye solution at room temperature for 30 minutes. All tresses treated in the presence of ChA showed much more vibrant colors, suggesting more effective dye deposition achieved with the addition of ChA.
  • FIG. 21 and FIG. 22 show hair tresses treated with the catechol and Teluca® CORE direct dye mixtures (Teluca+ChA) compared to ShadesEQ oxidative dye -based demi- permanent toners. While the initial shades and tones appear similar, tresses treated with Teluca+ChA showed more effective color deposition and remained more vibrant throughout the washing process (FIG. 21a and FIG. 22a). As shown in FIG. 21b and FIG. 22b, the AE values of the tresses treated with Teluca+ChA are consistently lower than those with the ShadesEQ tonners, confirming the superior color longevity provided by the Teluca+ChA toning systems.
  • a catechol compound such as CA, RA90, or ChA was directly added to a commercial semi-permanent, non-oxidative direct dye-based hair color product.
  • Several color products are selected here, including Pravana Suntone, Ion Magenta, and Ion Warm Brown.
  • the catechols were added at a 1-2 wt% concentration and manually mixed into with the color product using a disposable spatula. 1.2 g of the color mixture was then applied to 0.75 g of 3x bleached hair and left for 30 mins at room temperature. The treated tress was rinsed with tap water at 40 °C for 30 s and air dried.
  • FIG. 25a shows the images of the tresses pre-treated with about 0.4 g of 0.1 wt% RA90 or 0.2 wt% ChA solution to the application of Ion Intensive Shine Red vs. the control with no pre-treatment.
  • the tress pre-treated with ChA shows deeper and more uniform color compared to the counterpart with no catechol pre-treatment.
  • the AE values of the tresses pre-treated with RA90 or ChA are also consistently lower than the control through the entire washing test, indicating improvements in the color longevity.
  • FIG. 27a and FIG. 27b show another example of tresses colored with or without catechol post-treatment.
  • a catechol solution was applied after the color treatment was complete and rinsed out.
  • the tresses colored with a catechol post-treatment showed better color retention throughout the washing process.

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  • Cosmetics (AREA)

Abstract

L'invention concerne des compositions de coloration capillaire contenant du catéchol ainsi que leur utilisation, et l'utilisation de composés contenant du catéchol à des fins de coloration capillaire.
PCT/US2025/022937 2024-04-04 2025-04-03 Systèmes de coloration durable comprenant un composé contenant du catéchol et un colorant capillaire Pending WO2025212874A1 (fr)

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US202463574623P 2024-04-04 2024-04-04
US63/574,623 2024-04-04

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WO2025212874A1 true WO2025212874A1 (fr) 2025-10-09

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WO (1) WO2025212874A1 (fr)

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4169703A (en) * 1978-08-03 1979-10-02 Syntex (U.S.A.) Inc. Oxidative red hair dye
US4212645A (en) * 1974-01-18 1980-07-15 Lever Brothers Company Hair dyeing composition containing an aryldiamine and a substituted catechol
US4746322A (en) * 1984-04-09 1988-05-24 Repligen Corporation Hair dye composition and process for using the same
EP0271186A1 (fr) * 1986-11-21 1988-06-15 Repligen Corporation Hydroxyindoles et leur application comme colorant
EP2938321B1 (fr) * 2012-12-27 2017-08-23 L'oreal Procédé pour la coloration de cheveux utilisant un colorant chromène ou chromane et un acide polyphénolique particulier
WO2020264257A1 (fr) * 2019-06-28 2020-12-30 Living Proof, Inc. Additifs pour agents de coloration et leurs procédés d'utilisation
CN117298013A (zh) * 2023-09-11 2023-12-29 西北农林科技大学 一种提高核桃青皮染液染发性能的方法

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4212645A (en) * 1974-01-18 1980-07-15 Lever Brothers Company Hair dyeing composition containing an aryldiamine and a substituted catechol
US4169703A (en) * 1978-08-03 1979-10-02 Syntex (U.S.A.) Inc. Oxidative red hair dye
US4746322A (en) * 1984-04-09 1988-05-24 Repligen Corporation Hair dye composition and process for using the same
EP0271186A1 (fr) * 1986-11-21 1988-06-15 Repligen Corporation Hydroxyindoles et leur application comme colorant
EP2938321B1 (fr) * 2012-12-27 2017-08-23 L'oreal Procédé pour la coloration de cheveux utilisant un colorant chromène ou chromane et un acide polyphénolique particulier
WO2020264257A1 (fr) * 2019-06-28 2020-12-30 Living Proof, Inc. Additifs pour agents de coloration et leurs procédés d'utilisation
CN117298013A (zh) * 2023-09-11 2023-12-29 西北农林科技大学 一种提高核桃青皮染液染发性能的方法

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
DATABASE GNPD [online] MINTEL; 23 May 2018 (2018-05-23), ANONYMOUS: "Instant Hair Color", XP093295993, retrieved from https://www.gnpd.com/sinatra/recordpage/5662109/ Database accession no. 5662109 *
DATABASE GNPD [online] MINTEL; 27 October 2022 (2022-10-27), ANONYMOUS: "Black Boosting Treatment", XP093295990, retrieved from https://www.gnpd.com/sinatra/recordpage/10307568/ Database accession no. 10307568 *

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