WO2015074846A1 - Procédé de mise en plis des cheveux - Google Patents

Procédé de mise en plis des cheveux Download PDF

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Publication number
WO2015074846A1
WO2015074846A1 PCT/EP2014/073226 EP2014073226W WO2015074846A1 WO 2015074846 A1 WO2015074846 A1 WO 2015074846A1 EP 2014073226 W EP2014073226 W EP 2014073226W WO 2015074846 A1 WO2015074846 A1 WO 2015074846A1
Authority
WO
WIPO (PCT)
Prior art keywords
hair
shaping
treatment composition
acid
actives
Prior art date
Application number
PCT/EP2014/073226
Other languages
English (en)
Inventor
Prem Kumar Cheyalazhagan Paul
Susan Pye
Original Assignee
Unilever Plc
Unilever N.V.
Conopco, Inc., D/B/A Unilever
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 Unilever Plc, Unilever N.V., Conopco, Inc., D/B/A Unilever filed Critical Unilever Plc
Publication of WO2015074846A1 publication Critical patent/WO2015074846A1/fr

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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
    • A61Q5/04—Preparations for permanent waving or straightening the hair
    • 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
    • A61K8/49—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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/24—Thermal properties

Definitions

  • This invention relates to a method of shaping hair, and more particularly a method of shaping hair without breaking the hair disulfide bonds.
  • Permanent hair straightening compositions that are on the market are based on chemical treatment of the hair in a two-step process using reducing agents to break hair disulfide bonds, followed by a neutralisation or oxidation step to re-establish new disulfide bonds in the desired configuration.
  • Such systems have various negatives associated with them; in that the process itself is difficult to conduct, in many instances this straightening process is undertaken by a qualified hairdresser in a professional salon. Furthermore the straightening process damages the hair, has an unpleasant odour and can cause irritation to the scalp.
  • the method of the invention does not necessarily require the use of high temperature heated implements such as straightening irons and can be accomplished by a consumer without intervention of a professional hairdresser. Furthermore, hair shaped with the method of the invention remains shaped even after subsequent washing.
  • the present invention provides a method of shaping hair comprising the following sequential steps:
  • a hair treatment composition comprising from 2 to 25 wt% of one or more uronic acid lactones, and (ii) mechanically shaping the treated hair; in which the one or more uronic acid lactones have a ring structure formed from the intramolecular esterification of uronic acids with general formula
  • n is an integer of 3 to 5.
  • Uronic acids are monocarboxylic acids derived by oxidation to a carboxylic acid group of the terminal -CH 2 OH group of an aldose.
  • aldose denotes an aldehydic parent sugar of formula HOCH 2 [CH(OH)] n CHO, in which n is an integer of 3 to 5, and/or its intramolecular hemiacetal. Preferably n is 4.
  • Lactones can be denoted in accordance with the lactone notation, i.e.
  • a - -lactone thus has a furanoid form, while a ⁇ -lactone has a pyranoid form.
  • a furanoid form in this context means a ring having five carbon atoms in which one carbon atom has been replaced by an oxygen
  • a pyranoid form in this context means a ring comprising six carbons in which one carbon atom has been replaced by an oxygen atom.
  • Uronic acids form lactones by intramolecular esterification between the carboxylic acid group and one of the hydroxyl groups in the molecule. These internal esters of uronic acids are usually spontaneously formed upon heating, and formation of a •-lactone or a ⁇ -lactone structure is possible.
  • x D,L
  • an O-bridged ring closure between the aldehyde group and the OH group of the ⁇ carbon atom is present.
  • the uronic acid lactones as described above are formulated into a hair treatment composition for use in the method of the invention.
  • the one or more uronic acid lactones as described above may be used as the sole hair shaping active in the formulated hair treatment composition.
  • the total level of uronic acid lactone preferably ranges from 3 to 20 wt% and more preferably from 4 to 15 wt%, by weight based on the total weight of the hair treatment composition.
  • x-glucuronic acid-* -lactone may be used as the sole hair shaping active in the formulated hair treatment composition, at a level which preferably ranges from 3 to 20 wt% and more preferably from 4 to 15 wt%, by weight based on the total weight of the hair treatment composition.
  • the one or more uronic acid lactones as described above may be combined with one or more additional hair shaping actives in the formulated hair treatment composition.
  • additional hair shaping actives which may be used in this context include aliphatic carboxylic acids having a molecular weight (M w ) ranging from 60 to 300 g/mol, and a pK a (measured at 25°C in water) ranging from 2 to 8.5.
  • M w molecular weight
  • pK a measured at 25°C in water
  • the aliphatic carboxylic acid has a pK a (measured at 25 °C in water) ranging from 2 to 4.5, more preferably from 2.1 to 4.2.
  • Aliphatic monocarboxylic acids which may be used as additional hair shaping actives in the method of the invention have a structure corresponding to the following general formula (I):
  • R 1 is a monovalent saccharide residue or a monovalent saturated alkyl radical of formula R 3 -(A)- ;
  • R 3 is a monovalent radical selected from H-, HOCH 2 - and saturated linear alkyl radicals of formula X(CH 2 ) n - ;
  • X is a monovalent radical selected from H-, HO- , H 2 N- , H 2 NC(O)- , (HOCH 2 ) 3 C- NH- , (HOCH 2 CH 2 ) 2 N- and H 3 CC(O)- ;
  • n is an integer ranging from 1 to 8;
  • A is a divalent radical selected from -C(O)- and -C(R 4 )(R 5 )-;
  • R 4 is a monovalent radical selected from -H, -OH, -CH 2 OH and -NH 2, and
  • R 5 is a monovalent radical selected from -H, -CH 2 OH,
  • R 1 in general formula (I) above is a monovalent monosaccharide residue (such as a glucose or galactose residue), or a monovalent saturated linear alkyl radical of formula R 3 -(A) - ;
  • R 3 is selected from H-, HOCH 2 - and H 3 C- ;
  • A is a divalent radical selected from -C(O)- , -CH(OH)-,
  • Such monocarboxylic acids include lactic acid, glyoxylic acid, glycolic acid, glucuronic acid, 2,2-k/s(hydroxymethyl)propionic acid, lysine, 2-hydroxyoctanoic acid, acetic acid, glycine, serine, succinamic acid, levulinic acid, galacturonic acid, tricine, bicine and 2,2-k/s(hydroxymethyl)butyric acid.
  • Aliphatic dicarboxylic acids which may be used as additional hair shaping actives in the method of the invention have a structure corresponding to the following general formula (II):
  • R 1 is a divalent, saturated or unsaturated, linear or branched hydrocarbyl radical having from 1 to 4 carbon atoms, and which may optionally be substituted with one or more hydroxyl groups.
  • R 1 in general formula (II) above is a divalent saturated linear alkyl radical of formula -[CH(X)] n - in which n is an integer ranging from 1 to 3 and each X is independently selected from -H and -OH.
  • dicarboxylic acids include malonic acid and tartaric acid.
  • Aliphatic tricarboxylic acids which may be used as additional hair shaping actives in the method of the invention have a structure corresponding to the following general formula (III):
  • R 1 is a divalent, saturated or unsaturated, linear or branched hydrocarbyl radical having from 1 to 3 carbon atoms, which is substituted with one -COOH group and which may optionally be substituted with one or more hydroxyl groups.
  • tricarboxylic acids include citric acid, aconitic acid and tricarballylic acid.
  • the most preferred additional hair shaping actives which may be used in the method of the invention are the aliphatic tricarboxylic acids described above, and in particular citric acid.
  • the total level of uronic acid lactones and additional hair shaping actives preferably ranges from 3 to 20 wt% and more preferably from 4 to 15 wt%, by weight based on the total weight of the hair treatment composition.
  • the weight ratio of the lactone to the acid in such a mixture preferably ranges from 5:1 to 1 :2, more preferably from 3:1 to 2:3, and is most preferably from about 1 :1 .
  • Preferred hair treatment compositions for use in the invention have a conditioning gel phase, which may be generally characterized as a gel ( ⁇ _ ⁇ ) surfactant mesophase consisting of surfactant bilayers.
  • a conditioning gel phase may be formed from a cationic surfactant, a high melting point fatty compound and an aqueous carrier. Typically these components are heated to form a mixture, which is cooled under shear to room temperature. The mixture undergoes a number of phase transitions during cooling, normally resulting in a gel (L. ) surfactant mesophase consisting of surfactant bilayers.
  • Suitable cationic surfactants which are useful for forming the conditioning gel phase include quaternary ammonium cationic surfactants corresponding to the following general formula:
  • R 1 , R 2 , R 3 , and R 4 are each independently selected from (a) an aliphatic group of from 1 to 22 carbon atoms, or (b) an aromatic, alkoxy, polyoxyalkylene, alkylamido, hydroxyalkyl, aryl or alkylaryl group having up to 22 carbon atoms; and X is a salt-forming anion such as those selected from halide, (e.g. chloride, bromide), acetate, citrate, lactate, glycolate, phosphate nitrate, sulphate, and alkylsulphate radicals.
  • the aliphatic groups can contain, in addition to carbon and hydrogen atoms, ether linkages, and other groups such as amino groups.
  • the longer chain aliphatic groups e.g., those of about 12 carbons, or higher, can be saturated or
  • quaternary ammonium cationic surfactants of the above general formula are cetyltrimethylammonium chloride,
  • BTAC behenyltrimethylammonium chloride
  • cetylpyridinium chloride cetylpyridinium chloride
  • octyltrimethylammonium chloride dodecyltrimethylammonium chloride, hexadecyltrimethylammonium chloride, octyldimethylbenzylammonium chloride, decyldimethylbenzylammonium chloride, stearyldimethylbenzylammonium chloride, didodecyldimethylammonium chloride, dioctadecyldimethylammonium chloride, tallowtrimethylammonium chloride, cocotrimethylammonium chloride, dipalmitoylethyldimethylammonium chloride, PEG-2 oleylammonium chloride and salts of these, where the chloride is replaced by other halide (e.g., bromide), acetate, citrate, lactate, glycolate, phosphate nitrate, sulphate, or alkylsulphate.
  • halide e.g., bromide
  • R 1 is a d 6 to C22 saturated or unsaturated, preferably saturated, alkyl chain and R 2 , R 3 and R 4 are each independently selected from CH 3 and CH 2 CH 2 OH, preferably CH 3 .
  • quaternary ammonium cationic surfactants for use in forming the conditioning gel phase are cetyltrimethylammonium chloride (CTAC), behenyltrimethylammonium chloride (BTAC) and mixtures thereof. Mixtures of any of the above-described cationic surfactants may also be suitable.
  • the level of cationic surfactant suitably ranges from 0.1 to 10 wt%, preferably from 0.2 to 5 wt% and more preferably from 0.25 to 4 wt% (by total weight of cationic surfactant based on the total weight of the hair treatment composition).
  • high melting point in the context of this invention is generally meant a melting point of 25 °C or higher. Generally the melting point ranges from 25 °C up to 90°C, preferably from 40 °C up to 70° C and more preferably from 50 °C up to about 65 °C.
  • the high melting point fatty compound can be used as a single compound or as a blend or mixture of at least two high melting point fatty compounds.
  • the melting point means the melting point of the blend or mixture.
  • Suitable fatty compounds of this type have the general formula R-X, wherein R is an aliphatic carbon chain and X is a functional group (e.g. alcohol or carboxylic acid or a derivative thereof such as ester or amide).
  • R is preferably a saturated aliphatic carbon chain comprising from 8 to 30 carbon atoms, preferably from 14 to 30 carbon atoms, more preferably from 16 to 22 carbon atoms.
  • R can contain, in addition to carbon and hydrogen atoms, ether linkages, and other groups such as amino groups.
  • R is a linear alkyl chain comprising from 8 to 30 carbon atoms, preferably from 14 to 30 carbon atoms, more preferably from 16 to 22 carbon atoms.
  • X is preferably an -OH group.
  • the fatty compound is a fatty alcohol of general formula
  • n is an integer from 7 to 29, preferably from 15 to 21 .
  • Suitable fatty alcohols are cetyl alcohol, stearyl alcohol, behenyl alcohol, and mixtures thereof. Cetyl alcohol, stearyl alcohol and mixtures thereof are particularly preferred.
  • the level of fatty compound suitably ranges from 0.01 to 10 wt%, preferably from 0.1 to 8 wt%, more preferably from 0.2 to 7 wt% and most preferably from 0.3 to 6 wt% (by weight based on the total weight of the hair treatment composition).
  • the weight ratio of cationic surfactant to fatty compound is suitably from 1 :1 to 1 :10, preferably from 1 :1 .5 to 1 :8, optimally from 1 :2 to 1 :5.
  • the method of the invention does not require the breakage of hair disulfide bonds, and hair treatment compositions for use in the invention do not require the incorporation of reducing agents. It is preferred that such materials, if included at all, are present in minor quantities only.
  • reducing agent in the context of this invention means an agent which is effective to break hair disulfide bonds when applied to hair for a period ranging from about 3 to 15 minutes and at a temperature ranging from about 20 to 30 Q C.
  • reducing agents are ammonium thioglycolate (in a solution having a pH of between about 7 and 10.5), glyceryl monothioglycolate (employed at a pH of less than 7), thioglycolic acid, dithioglycolic acid, mercaptoethyl amine, mercaptopropionic acid, dithioglycolate and alkali metal or ammonium sulfites or bisulfites.
  • a hair treatment composition for use in the method of the invention will preferably include from 0 to 0.1 wt%, more preferably from 0 to 0.01 wt%, and most preferably from 0 to 0.001 wt% reducing agents as defined above (by weight based on the total weight of the hair treatment composition).
  • the pH of the hair treatment composition ranges from 1 to 4, more preferably from 1 .5 to 3.
  • Hair treatment compositions for use in the invention will generally comprise at least 60 wt%, preferably at least 70 wt% and more preferably at least 80 wt% water (by weight based on the total weight of the hair treatment composition).
  • the hair treatment composition comprises no more than 95 wt% and more preferably no more than 90 wt% water (by weight based on the total weight of the hair treatment composition).
  • Other organic solvents may also be present, such as lower alkyl alcohols and polyhydric alcohols.
  • lower alkyl alcohols include Ci to C 6 monohydric alcohols such as ethanol and isopropanol.
  • polyhydric alcohols include propylene glycol, hexylene glycol, glycerin, and propanediol.
  • the hair treatment composition may also incorporate other optional ingredients to enhance performance and/or consumer acceptability. Suitable optional ingredients include: preservatives, colouring agents, chelating agents, antioxidants, fragrances, antimicrobials, antidandruff agents, cationic conditioning polymers, styling ingredients, sunscreens, proteins and hydrolysed proteins.
  • the hair treatment composition is a single dose composition.
  • single dose in the context of this invention means that the hair treatment composition is to be applied to the hair in one go.
  • the hair treatment composition is applied to the hair in the form of a 100 to 300 ml single dose, more preferably a 150 to 250 ml single dose.
  • the hair treatment composition is applied to the hair at a temperature from 15 to 40 Q C, and more preferably at a temperature from 20 to 30 Q C.
  • the hair treatment composition is applied to dry hair.
  • dry hair in the context of this invention generally means hair from which free water (i.e. water disposed as a film or droplets on the cuticle surface) has been substantially removed. Hair may be dried by exposure to air, by use of a heated hair drying appliance, by rubbing with a water-absorbent article, or by a
  • the dry hair will not have been washed or actively wetted, (such as by shampooing, conditioning, rinsing or otherwise treating with an aqueous composition) in the preceding 2 hours and more preferably in the preceding 3 hours prior to topical application of the hair treatment composition in accordance with step (i) of the method of the invention, and will have been permitted to acclimatise to atmospheric conditions. In such circumstances there is substantially no free water present which interferes with the adsorption of the hair treatment composition on application.
  • a suitable indicator of dry hair in the context of this invention would be a hair fibre whose calculated water content does not exceed 25 wt% by weight based on the total weight of the hair fibre.
  • the hair treatment composition is worked through the hair after topical application.
  • the hair treatment composition is then left to penetrate the hair for a period of at least 5 up to about 90 minutes, more preferably for at least 10 up to about to 60 minutes and most preferably for at least 15 up to about 40 minutes.
  • the hair treated in accordance with step (i) of the method of the invention is preferably dried prior the commencement of step (ii).
  • the hair may be dried by exposure to air, by use of a heated hair drying appliance, by rubbing with a water- absorbent article, or by a combination of any of these methods.
  • the hair is mechanically straightened.
  • the hair may be pulled, combed, smoothed, pressed or flattened into a straightened configuration.
  • a hot tool such as an electrically heated flat hair iron or hand-held hair dryer, may be used in the mechanical shaping step.
  • Such tools apply high levels of heat directly to the hair.
  • Particularly good results have been obtained when the hair is mechanically straightened in step (ii) of the method of the invention with a hot tool such as an electrically heated flat hair iron.
  • the operating temperature of the hot tool ranges from 120 to 220 Q C, more preferably from 150 to 220 Q C, and most preferably from 170 to 220 Q C.
  • the invention also provides a method for re-shaping hair in which hair which has been treated and shaped in accordance with steps (i) and (ii) as described above is rinsed, and mechanically re-shaped before and/or after drying.
  • Hair to be mechanically re-shaped as described above may be rinsed with water alone or with shampoo.
  • the hair is mechanically re-straightened by combing it into a straightened configuration at a temperature from 20 to 30 Q C.
  • One or more (e.g. two or three) cycles of rinsing, mechanical re-shaping and drying as described above may be carried out.
  • hair may be durably shaped by the method of the invention.
  • durably shaped in the context of this invention means that the hair shape persists after washing. Preferably more than 50% of the hair shape persists after 3 washes.
  • the switches were left to dry at 20 °C and 50%RH. When dry the switches were straightened 7 times with GHD irons. After 2 days on the bench the switches were washed with shampoo and
  • the volume of the switches after combing is given in the table below (expressed as a projection of the switch on the image area).

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
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  • Veterinary Medicine (AREA)
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  • Epidemiology (AREA)
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Abstract

La présente invention concerne un procédé de mise en plis des cheveux comprenant les étapes séquentielles suivantes : (i) traitement des cheveux par application topique d'une composition de traitement capillaire comprenant de 2 à 25 % en poids d'un ou plusieurs principes actifs de mise en plis des cheveux ; et (ii) mise en plis mécanique des cheveux traités ; le ou les principes actifs de mise en plis des cheveux étant sélectionnés dans le groupe constitué des lactones de l'acide uronique avec une structure cyclique formée par l'estérification intramoléculaire des acides uroniques répondant à la formule générale HOOC[CH(OH)]n CHO, dans laquelle n est un nombre entier de 3 à 5.
PCT/EP2014/073226 2013-11-21 2014-10-29 Procédé de mise en plis des cheveux WO2015074846A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP13193938.1 2013-11-21
EP13193938 2013-11-21

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WO2015074846A1 true WO2015074846A1 (fr) 2015-05-28

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017013034A1 (fr) * 2015-07-21 2017-01-26 Unilever Plc Composition de mise en forme des cheveux
WO2017129300A1 (fr) * 2016-01-28 2017-08-03 Unilever Plc Composition de mise en forme des cheveux
US10449136B2 (en) 2015-07-21 2019-10-22 Conopco, Inc. Hair shaping composition
WO2020002522A1 (fr) * 2018-06-29 2020-01-02 L'oreal Procédé de mise en forme des cheveux comprenant une étape d'application d'une composition comprenant une lactone, une étape de mise en forme et une longue durée pendant laquelle le produit est laissé sur les cheveux

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2438534A1 (de) * 1974-08-10 1976-02-19 Valentin Dr Med Koehler Kopfhautpflegemittel und dessen verwendung
US5015470A (en) * 1986-12-23 1991-05-14 Gibson Walter T Cosmetic composition
US5635168A (en) * 1994-09-21 1997-06-03 Business Resources Group, Inc. Composition for treating hair
EP1066019A1 (fr) * 1999-01-21 2001-01-10 Wella Aktiengesellschaft Procede et agent pour le permanentage des cheveux avec reduction de l'effet d'ondulation en fonction du temps
JP2006182702A (ja) * 2004-12-27 2006-07-13 Lion Corp 毛髪化粧料
US20080019938A1 (en) * 2004-03-08 2008-01-24 Elliott Rebecca J Hair Treatment Composition Comprising Sugar Lactone
US20100202994A1 (en) * 2007-09-28 2010-08-12 Masahiro Kasai Hair treatment compositions

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2438534A1 (de) * 1974-08-10 1976-02-19 Valentin Dr Med Koehler Kopfhautpflegemittel und dessen verwendung
US5015470A (en) * 1986-12-23 1991-05-14 Gibson Walter T Cosmetic composition
US5635168A (en) * 1994-09-21 1997-06-03 Business Resources Group, Inc. Composition for treating hair
EP1066019A1 (fr) * 1999-01-21 2001-01-10 Wella Aktiengesellschaft Procede et agent pour le permanentage des cheveux avec reduction de l'effet d'ondulation en fonction du temps
US20080019938A1 (en) * 2004-03-08 2008-01-24 Elliott Rebecca J Hair Treatment Composition Comprising Sugar Lactone
JP2006182702A (ja) * 2004-12-27 2006-07-13 Lion Corp 毛髪化粧料
US20100202994A1 (en) * 2007-09-28 2010-08-12 Masahiro Kasai Hair treatment compositions

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017013034A1 (fr) * 2015-07-21 2017-01-26 Unilever Plc Composition de mise en forme des cheveux
JP2018520194A (ja) * 2015-07-21 2018-07-26 ユニリーバー・ナームローゼ・ベンノートシヤープ 毛髪成形組成物
US10300003B2 (en) 2015-07-21 2019-05-28 Conopco, Inc. Hair shaping composition
EA032810B1 (ru) * 2015-07-21 2019-07-31 Юнилевер Н.В. Композиция для придания формы волосам
US10449136B2 (en) 2015-07-21 2019-10-22 Conopco, Inc. Hair shaping composition
WO2017129300A1 (fr) * 2016-01-28 2017-08-03 Unilever Plc Composition de mise en forme des cheveux
WO2020002522A1 (fr) * 2018-06-29 2020-01-02 L'oreal Procédé de mise en forme des cheveux comprenant une étape d'application d'une composition comprenant une lactone, une étape de mise en forme et une longue durée pendant laquelle le produit est laissé sur les cheveux
FR3083104A1 (fr) * 2018-06-29 2020-01-03 L'oreal Procede de mise en forme des cheveux comprenant une etape d’application d’une composition comprenant une lactone, une etape de mise en forme et un long temps de pause

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