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WO2019179745A1 - Procédé de traitement de fibres de kératine à l'aide de liants organiques sulfonés - Google Patents

Procédé de traitement de fibres de kératine à l'aide de liants organiques sulfonés Download PDF

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Publication number
WO2019179745A1
WO2019179745A1 PCT/EP2019/054986 EP2019054986W WO2019179745A1 WO 2019179745 A1 WO2019179745 A1 WO 2019179745A1 EP 2019054986 W EP2019054986 W EP 2019054986W WO 2019179745 A1 WO2019179745 A1 WO 2019179745A1
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WO
WIPO (PCT)
Prior art keywords
keratins
hair
treatment
cosmetically acceptable
application
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.)
Ceased
Application number
PCT/EP2019/054986
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English (en)
Inventor
Alderano Mannozzi
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.)
Jean Paul Myne' Srl
Original Assignee
Jean Paul Myne' Srl
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Jean Paul Myne' Srl filed Critical Jean Paul Myne' Srl
Priority to EP19707794.4A priority Critical patent/EP3768232A1/fr
Publication of WO2019179745A1 publication Critical patent/WO2019179745A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/002—Preparations for repairing the hair, e.g. hair cure

Definitions

  • This invention concerns treatment of keratins, and in particular of the keratins in human hair and other animal fur.
  • the invention in particular, concerns a method for improving the esthetic aspect and physical-mechanical characteristic of the keratins through the application on them of organic binders containing at least one sulfonic functional group.
  • keratins are a group of proteins with a fibrous structure and, generally, a high content of sulfur, which are created by living cells as expression of their genetic code (DNA). These proteins form fibrous macro-aggregates such as hair, nails and the surface layers of the skin. Keratins are classified by type as alpha-, beta-, and amorphous.
  • Keratin Structure, mechanical properties, occurrence in biological organisms and efforts at bioinspiration, Progress in Materials Science, Elsevier Ltd. - 2016 76 229-318.
  • the concentration of cysteic acid can be as great as or even greater than the concentration of Cysteine.
  • the document W02016100634 A2 discloses a composition for hair conditioning inclusive of one or more materials useful for improving the fibrous properties of the hair.
  • W02016100634 A2 has the scope of re-integrating the natural lipids that have an important role in the structure of the hair, where they bind the proteins that are an integral part of the cuticular membrane/outer layer of the hair.
  • Patent WO2016074986 A1 discloses a composition to be used as a shampoo or conditioner that untangles the hair making it easier to comb.
  • the composition proposed calls for the use of hydrophilic solubilizing substances, cationic and surfactant polymers, excluding the use of hydrophobic substances such as natural/synthetic oils and/or silicones.
  • the primary amine groups in the keratins (deriving from the aminoacids Arginine, Lisine and Histidine) have been - and still are - used to straighten curly hair by application of substances containing aldehyde groups (such as formic, acetic and glutaric aldehyde, etc.) as known in document US3665072 and e US9844500 B2.
  • aldehyde groups such as formic, acetic and glutaric aldehyde, etc.
  • Purpose of this invention is to provide a method for treatment of the keratins capable of:
  • this invention concerns a method for the treatment of keratins with organic binders containing one sulfonic functional group.
  • the invention consists of the discovery of the possibility of using, under cosmetically acceptable conditions, a family of organic binders to alter and improve the esthetic aspect and chemical- physical properties of keratins.
  • binders that have shown they possess these characteristics have the typical chemical structure of the family of sulfonated organic substances.
  • - X can consist of one or more polyfunctional molecules (for example bifunctional, trifunctional, tetrafunctional, etc.) that do not interfere with the reactive properties of the functional binding group (-S0 3 H).
  • binding functional groups (-SO 3 H) can be bound to X at any point of its structure.
  • - X includes, but is not limited to including, a single atom, such as Hydrogen, Oxygen, Sulfur, Carbon, Boron, Nitrogen, Halogen, or a group of atoms, such as alcoxy, alkyl, alkenyl, cycloalkenyl, aryl, etherocycloalkyl, etheroaryl, formyl, hydroxy, ether, cyan.
  • a single atom such as Hydrogen, Oxygen, Sulfur, Carbon, Boron, Nitrogen, Halogen, or a group of atoms, such as alcoxy, alkyl, alkenyl, cycloalkenyl, aryl, etherocycloalkyl, etheroaryl, formyl, hydroxy, ether, cyan.
  • binding substances containing at least one sulfonic functional group are the following sulfonated organic substances: METHANESULFONIC ACID (CAS no. 75-75-2),
  • PROPANEDISULFONIC ACID (CAS no. 21668-77-9)
  • organic binders with at least one sulfonic group, according to the structure represented by Formula I and the subject of this patent application, are used dissolved or dispersed in a “cosmetically acceptable medium” (meaning by this a mixture of substances commonly used in the manufacture of cosmetic products) in a concentration between 0.1% and 99.9% by weight/weight.
  • a “cosmetically acceptable medium” meaning by this a mixture of substances commonly used in the manufacture of cosmetic products
  • Example 1 Comparison between the traditional permanent wave and a permanent wave performed using the sulfonated organic binder methanesulfonic acid (CAS no. 75-75-2).
  • Samples of hair were obtained from a human subject and cut in two locks of about 1 cm width and weight of about 5 grams.
  • kit for permanents the kit used, produced by Cosmec srl of Milan (Italy), contained in step 1 the reducing substances based on thioglycolates of ammonium dispersed in a“cosmetically acceptable medium” and as oxidizing agent (step 2) hydrogen peroxide, also dispersed in a“cosmetically acceptable medium”.
  • Organic binder used methanesulfonic acid (CAS no. 75-75-2) dissolved in a“cosmetically acceptable medium”.
  • the cosmetically acceptable medium containing the organic binding substance with other substances commonly used in cosmetics is defined as the“binding mixture”.
  • the “binding mixture” used had the composition indicated in Table (I) hereafter.
  • a second “cosmetically acceptable medium” was likewise prepared, containing all the ingredients listed in Table (I) with the exception of the sulfonated organic binder methanesulfonic acid.
  • the locks of hair were washed with shampoo, dried with a towel and then wound around a curler for permanents (a tool with which persons expert in the sector is thoroughly familiar).
  • Step 1 of the commercial kit was applied to the two locks of hair and left in contact for 20 minutes.
  • The“binding mixture” detailed in Table (I) was applied on the first lock of hair, mixing 20 grams of binding mixture and 30 grams of step 2. The mixture was then left on the hair for 15 minutes.
  • the lock of hair was then rinsed with warm water for about 1-2 minutes and unrolled from the curler.
  • the lock was dehydrated by heating it with a special hair curling iron (with which experts in the sector are familiar) at the temperature of 150°C.
  • a second lock of hair was treated in the same way described for the first lock of hair, using the mixture detailed in Table (I) without the sulfonated organic binder methanesulfonic acid.
  • Both permanents exhibited good resistance of the wave produced by the permanent after a first washing and conditioning. After 10 cycles of washing and drying with the same shampoo and conditioner, a marked reduction of the wave compared with the situation obtained after the first washing with shampoo and conditioner was observed.
  • Example 2 Test of the sheen and consistency of hair after treatment with a “binding mixture” containing the sulfonated organic binder methanesulfonic acid (CAS no. 55-98-1).
  • Organic binder used 1 ,4-butanedisulfonic acid (CAS no. 55-98-1) dissolved in a“cosmetically acceptable medium”.
  • the cosmetically acceptable medium containing the organic binding substance with other substances commonly used in cosmetics is defined as the“binding mixture”.
  • the “binding mixture” used had the composition indicated in Table (II) hereafter.
  • a second “cosmetically acceptable medium” was likewise prepared, containing all the ingredients listed in Table (II) with the exception of the sulfonated organic binder methanesulfonic acid.
  • Both mixtures were blended in a 1:3 ratio with a conditioner (Jean Paul Myne® Ocrys Bandha Conditioner) to make a uniform creamy paste.
  • a conditioner Jean Paul Myne® Ocrys Bandha Conditioner
  • the two locks of hair were washed with Jean Paul Myne® Ocrys Bandha shampoo, then dried with a towel.
  • the hair was combed using a comb with wide teeth, then using one with fine teeth for 2 minutes.
  • the creamy paste containing the binding mixture detailed in Table (II) was applied manually, using a paintbrush, to the lock of hair, which was then combed for about 1 minute.
  • the sample of hair was left in contact with the creamy paste containing the sulfonated organic binder 1 ,4-butandisulfonic acid for about 15 minutes, then rinsed with water and washed with Jean Paul Myne® Ocrys Bandha Shampoo and Conditioner.
  • the same hair sample was washed and conditioned five more times with the same shampoo and conditioner.
  • a second lock of hair was treated the same way described above, however using the second creamy paste containing all the ingredients listed in Table (II) except the sulfonated organic binder 1,4-butanedisulfonic acid. Both locks were dehydrated by heating with a special hair curling iron (with which experts in the sector are familiar) at the temperature of 180°C.
  • the sample of hair treated with the“binding mixture” containing the sulfonated organic binder 1 ,4-butanedisulfonic acid was softer to the touch than the sample treated with the creamy paste lacking the sulfonated organic binder 1 ,4-butanedisulfonic acid.
  • the hair sample treated with the“binding mixture” detailed in Table (II) was esthetically“better looking” than the other.
  • the shinier aspect and better consistency remained unchanged after five treatments with shampoo and conditioner.
  • Example 3 Test of the sheen and consistency of hair after treatment with a “binding mixture” containing the sulfonated organic binder propanedisulfonic acid (CAS no. 21668-77-9).
  • Organic binder used propanedisulfonic acid (CAS no. 21668-77- 9) dissolved in a“cosmetically acceptable medium”.
  • the cosmetically acceptable medium containing the organic binding substance with other substances commonly used in cosmetics is defined as the“binding mixture”.
  • the “binding mixture” used had the composition indicated in Table (III) hereafter.
  • a second “cosmetically acceptable medium” was likewise prepared, containing all the ingredients listed in Table (III) with the exception of the sulfonated organic binder propanedisulfonic acid.
  • the two mixtures were then mixed with Jean Paul Myne ® Ashana Conditioner in a ratio of 1:2 to obtain a uniform creamy paste containing the above ingredients dispersed in it.
  • the lock was then combed for about 2 minutes.
  • the sample of hair was left in contact with the“binding mixture” detailed in Table (III) for about 10 minutes.
  • the hair was then treated again with about 5 grams of the“binding mixture” of Table (PI).
  • the hair sample was combed for about 10 seconds and left undisturbed for another 5 minutes.
  • the hair sample was then rinsed with water and subsequently washed with Jean Paul Myne® Ashana shampoo and conditioner and dried with a hand-held hairdryer.
  • the sample was washed and conditioned two more times with the same shampoo and conditioner.
  • a second lock of hair was treated the same way described above, however using the second creamy paste containing all the ingredients listed in Table (III) except the sulfonated organic binder propanedisulfonic acid.
  • the two locks after being dried with a hand-held hairdryer, were dehydrated by heating with a special flat iron (with which experts in the sector are familiar) at the temperature of 180°C.
  • the sample of hair treated with the“binding mixture” containing the sulfonated organic binder propanedisulfonic acid was softer to the touch than the sample treated with the creamy paste lacking the sulfonated organic binder propanedisulfonic acid.
  • the hair sample treated with the“binding mixture” detailed in Table (III) was esthetically“better looking” than the other.
  • the shinier aspect and better consistency remained unchanged after two treatments with shampoo and conditioner.
  • Example 4 Test of the color retention and consistency of hair after treatment with a“binding mixture” containing the sulfonated organic binder methanesulfonic acid (CAS no. 75-75-2).
  • Color formulation commercial kit for the permanent coloring of hair consisting of: Jean Paul Myne® permanent color DOC COLOR (grade#4) + Jean Paul Myne ® bleaching agent DOC
  • Organic binder used methanesulfonic acid (CAS no. 75-75-2) dissolved in a“cosmetically acceptable medium”.
  • the cosmetically acceptable medium containing the organic binding substance with other substances commonly used in cosmetics is defined as the“binding mixture”.
  • the “binding mixture” used had the composition indicated in Table (IV) hereafter.
  • a second “cosmetically acceptable medium” was likewise prepared, containing all the ingredients listed in Table (IV) with the exception of the sulfonated organic binder methanesulfonic acid.
  • the hair samples were washed with a Jean Paul Myne® Treasure Enhancing shampoo then dried with a towel.
  • the cosmetic coloring paste without the sulfonated organic binder methanesulfonic acid was applied on one lock of hair, massaging with the fingers to facilitate its absorption by the keratin fibers, and leaving it in contact for 15 minutes.
  • the cosmetic coloring paste containing the sulfonated organic binder methanesulfonic acid was applied in the same way, massaging with the fingers to facilitate its absorption by the keratin fibers.
  • the locks treated with the sulfonated organic binder methanesulfonic acid had a significantly shinier aspect and greater tensile strength than the lock treated with the cosmetic mixture lacking the sulfonated organic binder methanesulfonic acid.
  • Example 5 Comparison between hair treated with a bleaching cosmetic product applied simultaneously with the “binding mixture” containing the sulfonated organic substance butanedisulfonic acid (CAS. No. 55-98-1) and hair treated with the bleaching cosmetic product alone.
  • Organic binder used butanedisulfonic acid (CAS no. 55-98-1) dissolved in a “cosmetically acceptable medium”.
  • the cosmetically acceptable medium containing the organic binding substance with other substances commonly used in cosmetics, is defined as the“binding mixture”.
  • the “binding mixture” used had the composition indicated in Table (V) hereafter.
  • the commercial bleaching kit used was marketed by Jean Paul Myne® and consisted of the following products: DOC OLEODEC
  • the first lock was bleached with the creamy paste containing the sulfonated organic binder 1,4-butanedisulfonic acid, applied with an applicator brush to the hair resting on a sheet of aluminum foil.
  • the foil sheet was then folded around the lock leaving it in contact with the creamy paste for 30 minutes.
  • the lock was then washed with Jean Paul Myne® OCRYS Bandha and rinsed with warm water for 2 minutes.
  • the second lock was bleached with the portion of bleaching paste without the sulfonated organic binder 1,4-butanedisulfonic acid.
  • the bleaching paste was applied with an applicator brush on the hair resting on a sheet of aluminum foil. The foil sheet was then folded around the lock leaving it in contact with the creamy paste for 30 minutes.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • Cosmetics (AREA)

Abstract

La présente invention concerne le traitement des kératines, et en particulier des kératines dans les cheveux humains et d'autres poils d'animaux. L'invention concerne en particulier un procédé d'amélioration de l'aspect esthétique et de la caractéristique physique-mécanique des kératines par l'application sur ceux-ci de liants organiques contenant au moins un groupe fonctionnel sulfonique.
PCT/EP2019/054986 2018-03-22 2019-02-28 Procédé de traitement de fibres de kératine à l'aide de liants organiques sulfonés Ceased WO2019179745A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP19707794.4A EP3768232A1 (fr) 2018-03-22 2019-02-28 Procédé de traitement de fibres de kératine à l'aide de liants organiques sulfonés

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IT102018000003878 2018-03-22
IT102018000003878A IT201800003878A1 (it) 2018-03-22 2018-03-22 Trattamento cosmetico per il miglioramento dell’aspetto estetico e delle caratteristiche fisico-meccaniche delle cheratine tramite l’uso di sostanze organiche leganti sulfonate.

Publications (1)

Publication Number Publication Date
WO2019179745A1 true WO2019179745A1 (fr) 2019-09-26

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PCT/EP2019/054986 Ceased WO2019179745A1 (fr) 2018-03-22 2019-02-28 Procédé de traitement de fibres de kératine à l'aide de liants organiques sulfonés

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EP (1) EP3768232A1 (fr)
IT (1) IT201800003878A1 (fr)
WO (1) WO2019179745A1 (fr)

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2631965A (en) 1950-05-24 1953-03-17 Ernst O Schnell Permanent waving of hair
US3665072A (en) 1965-07-29 1972-05-23 Oreal Method of improving the cosmetic properties of hair by using aldehyde solution
US20060104928A1 (en) 2004-11-12 2006-05-18 Lucimar Furtado Thermal hair straightening and conditioning composition
WO2011104282A2 (fr) 2010-02-24 2011-09-01 Alderan S.A.S. Di D'ottavi Adele & C. Procédé de lissage semi-permanent de cheveux frisés, ondulés ou bouclés
CN105177982A (zh) * 2015-10-15 2015-12-23 绍兴文理学院 一种黑发漂色方法
WO2016074986A1 (fr) 2014-11-13 2016-05-19 Basf Se Shampooings et après-shampooings à action démêlante
WO2016100634A2 (fr) 2014-12-19 2016-06-23 The Procter & Gamble Company Composition pour l'amélioration des propriétés des fibres capillaires

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2631965A (en) 1950-05-24 1953-03-17 Ernst O Schnell Permanent waving of hair
US3665072A (en) 1965-07-29 1972-05-23 Oreal Method of improving the cosmetic properties of hair by using aldehyde solution
US20060104928A1 (en) 2004-11-12 2006-05-18 Lucimar Furtado Thermal hair straightening and conditioning composition
WO2011104282A2 (fr) 2010-02-24 2011-09-01 Alderan S.A.S. Di D'ottavi Adele & C. Procédé de lissage semi-permanent de cheveux frisés, ondulés ou bouclés
US9844500B2 (en) 2010-02-24 2017-12-19 Kao Corporation Process for semi-permanent straightening of curly, frizzy or wavy hair
WO2016074986A1 (fr) 2014-11-13 2016-05-19 Basf Se Shampooings et après-shampooings à action démêlante
WO2016100634A2 (fr) 2014-12-19 2016-06-23 The Procter & Gamble Company Composition pour l'amélioration des propriétés des fibres capillaires
CN105177982A (zh) * 2015-10-15 2015-12-23 绍兴文理学院 一种黑发漂色方法

Non-Patent Citations (10)

* Cited by examiner, † Cited by third party
Title
BOGA C. ET AL.: "Curly or smooth?", OLD AND NEW ANSWERS - HOUSEHOLD AND PERSONAL CARE TODAY: HAIR CARE MONOGRAPHIC SUPPLEMENT, vol. 10, March 2015 (2015-03-01)
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 21668-77-9
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 55-98-1
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 75-75-2
DATABASE WPI Week 201605, Derwent World Patents Index; AN 2016-002958, XP002785907 *
ISTRATE D.V., THESIS ON HEAT INDUCED DENATURATION OF FIBROUS HARD A-KERATINS AND THEIR REACTION WITH VARIOUS CHEMICAL REAGENTS, 2011
QUADFLIEG J.M., THESIS ON FUNDAMENTAL PROPERTIES OF AFRO-AMERICAN HAIR AS RELATED TO THEIR STRAIGHTENING / RELAXING BEHAVIOR, 2003
ROBBINS C.R., CHEMICAL AND PHYSICAL BEHAVIOR OF HUMAN HAIR, 2012
TATE M.L. ET AL.: "Quantification and prevention of hair damage", J. SOC. COSMET. CHEM., vol. 44, 1993, pages 347 - 3 71
WANG B.: "Materials Science", vol. 76, 2016, ELSEVIER LTD., article "Keratin: Structure, mechanical properties, occurrence in biological organisms and efforts at bioinspiration", pages: 229 - 318

Also Published As

Publication number Publication date
IT201800003878A1 (it) 2019-09-22
EP3768232A1 (fr) 2021-01-27

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