AU2004201433B2

AU2004201433B2 - Hair treatment process and use of the process for smoothing the hair

Info

Publication number: AU2004201433B2
Application number: AU2004201433A
Authority: AU
Inventors: Priscille Devin-Baudoin; Anne Sabbagh
Original assignee: LOreal SA
Current assignee: LOreal SA
Priority date: 2003-04-16
Filing date: 2004-04-05
Publication date: 2006-06-15
Anticipated expiration: 2024-04-05
Also published as: RU2294681C2; EP1468667A1; PL367256A1; CN1245937C; JP4046237B2; DE602004006794D1; RU2004111591A; EP1468667B1; AU2004201433A1; JP2004315533A; ATE363889T1; FR2853832B1; PT1468667E; BRPI0401599A; KR20040090720A; DK1468667T3; CN1550229A; FR2853832A1; DE602004006794T2; ES2286570T3

Abstract

Hair treatment comprises applying a ceramide composition, heating the hair above 60[deg]C with a flat or round iron, and optionally rinsing the hair before or after heating.

Description

P/00/011 Regulation 3.2

AUSTRALIA

Patents Act 1990 COMPLETE SPECIFICATION STANDARD PATENT Invention Title: the hair Hair treatment process and use of the process for smoothing The following statement is a full description of this invention, including the best method of performing it known to us: iA- Hair treatment process and use of the process for smoothing the hair The present invention relates to a hair treatment process and to a use of the said process for smoothing the hair.

It is known that the most common technique for permanently reshaping the hair consists, in a first stage, in opening the disulphide bonds of keratin (cystine) using a composition containing a suitable reducing agent (reduction step), followed, after the hair thus treated has been rinsed, by reconstituting the said disulphide bonds in a second stage, by applying to the hair, which has been placed under tension beforehand (rollers and the like), an oxidizing composition (oxidation step, also known as the fixing step), so as to finally give the hair the desired shape. This technique thus makes it possible either to make the hair wavy or to relax or straighten it. The new shape given to the hair by a chemical treatment such as above is eminently long-lasting and especially withstands the action of washing with water or with shampoo, as opposed to standard simple techniques of temporary reshaping, such as hairsetting.

The problem of the permanent-waving techniques known to date is that they cause long-term impairment in the quality of the hair when they are applied thereto. The essential causes of this impairment in the quality of the hair are a reduction in its cosmetic properties, such as its sheen, and degradation of its mechanical properties, more particularly degradation of its mechanical strength due to swelling of the hair during the rinsing between the reduction step and the oxidation step, which may also be reflected by an increase in the porosity of the hair.

The hair is weakened and may become brittle during subsequent treatments such as blow-drying.

To solve this problem of impairment of the quality of the hair, it is known practice to use 004816206 -2conditioners such as silicones, for example, as taught in international cI patent application WO 99/17719, a dimethicone polyol ester combined with a polypeptide containing silanol end functions, as in international patent application WO 00/44337, or alternatively peptides and/or amino oo acids, as in international patent application WO 02/41857.

These solutions are found to be unsatisfactory since they do not entirely solve the problem of the impairment of the hair and of it properties. In particular, in the case of a permanent-reshaping treatment of the said hair has an unsatisfactory feel.

S 10 Reference to any prior art in the specification is not, and should not be taken as, an acknowledgment or any form of suggestion that this prior art forms part of the common general knowledge in Australia or any other jurisdiction or that this prior art could reasonably be expected to be ascertained, understood and regarded as relevant by a person skilled in the art.

The Applicant has now found, surprisingly, that a hair treatment process comprising the application of a composition containing at least one ceramide in a cosmetically acceptable vehicle, the composition being not rinsed out before the treating with an iron and the raising of the temperature of the hair to above 60'C, using a flat or round iron. This process affords long-lasting cosmetic properties, for instance excellent smoothing of the hair, tonicity and regeneration of the hair fibre, volumizing (or texturizing) of the fibre, and good disentangling and softness results.

The use of a flat or round iron especially helps the ceramide compound to penetrate better into the hair fibres and also increase its remanence with respect to shampooing.

The term "iron" means a heating device that brings the hair to a temperature generally above 004816206 -2A- The end of the iron that comes into contact with the hair may have different shapes. It may have a flat surface ("flat iron") or a rounded surface ("round iron").

oo One subject of the present invention is thus a hair treatment process as described below t' A subject of the present invention is also the use of the said process for smoothing the hair.

Other characteristics, aspects and advantages of the invention will (-i emerge even more clearly on N 3 reading the description and the various examples that follow.

According to the present invention, the hair treatment process comprises the steps consisting in: applying to the hair a composition containing at least one ceramide in a cosmetically acceptable vehicle, and then raising the temperature of the hair, using a flat or round iron, heating to above 60°C, preferably to a temperature of between 60 and 220°C and better still between 120 and 200°C, this step taking place before or after the optional rinsing of the composition.

Preferably, the said composition containing at least one ceramide is not rinsed out before treating with the iron.

The ceramide that may be contained in the said composition is preferably a compound of formula (I) below:

RI-C-N-C-CH-CH-O-R

2 R4 Rs in which: RI denotes either a saturated or unsaturated, linear or branched C9-C30 hydrocarbon radical, this radical possibly being substituted with one or more hydroxyl groups, these hydroxyl groups optionally being esterified with a saturated or unsaturated C16-C30 fatty acid; or a radical in which R denotes a hydrogen atom or a monohydroxylated or polyhydroxylated, preferably monohydroxylated, hydrocarbon radical, and R' and R" are hydrocarbon radicals, the sum of the carbon atoms of these radicals being between 9 and 30, R' being a divalent radical;

R

2 denotes a hydrogen atom or a (glycosyl)n, (galactosyl)m or sulphogalactosyl radical, in which n 4 is an integer ranging from 1 to 4 inclusive and m is an integer ranging from 1 to 8 inclusive;

R

3 denotes a hydrogen atom or a saturated or unsaturated C 16

-C

27 hydrocarbon radical, this radical possibly being substituted with one or more C 1

-C

14 alkyl radicals; R 3 may also denote a C 15

-C

26 a-hydroxyalkyl .radical, the hydroxyl group of which may optionally be esterified with a C 16

-C

30 a-hydroxy acid;

R

4 denotes a hydrogen atom, a saturated or unsaturated C 16

-C

27 hydrocarbon radical or a radical

-CH

2

-CHOH-CH

2

-O-R

6 in which R 6 denotes a Clo-C26 hydrocarbon radical; Rs denotes a hydrogen atom or a monohydroxylated or polyhydroxylated C 1

-C

4 hydrocarbon radical.

The ceramides preferably used in the process of the present invention especially correspond to formula in which Ri denotes an optionally hydroxylated saturated or unsaturated alkyl radical derived from

C

1 6-C 22 fatty acids; R 2 denotes a hydrogen atom; and R 3 denotes an optionally hydroxylated saturated linear C 1 radical, and they are more particularly chosen from N-linoleoyldihydrosphingosine, N-oleoyldihydrosphingosine, N-palmitoyldihydrosphingosine, N-stearoyldihydrosphingosine, N-behenoyldihydrosphingosine, N-2-hydroxypalmitoyldihydrosphingosine, N-stearoylphytosphingosine, or mixtures thereof, and more preferably from N-oleoyldihydrosphingosine, N-2-hydroxypalmitoyldihydrosphingosine and N-stearoylphytosphingosine.

The said ceramide is contained in a concentration within the range from 0.001% to 20% by weight, preferably from 0.01% to 10% by weight and even more preferably from 0.1% to 0.5% by weight relative to the total weight of the composition. A concentration of the invention that is particularly preferred is 0.5% by weight relative to the weight of the composition.

The cosmetically acceptable vehicle used in the present invention preferably consists of water or of a water/solvent mixture and even more preferably of an aqueous-alcoholic solution of a C 1 4 lower alcohol such as ethanol, isopropanol or butanol.

In the process according to the present invention, the composition containing at least one ceramide may be applied, in particular, before or after a reducing composition containing a reducing agent, the application of this reducing composition optionally being followed by rinsing.

Another embodiment of the process of the invention consists in that the composition containing at least one ceramide further contains a reducing agent.

The reducing agents that may be used in the process of the present invention are especially chosen from those generally used in processes for permanently reshaping the hair, such as alkali metal or alkalineearth metal or ammonium sulphites and/or bisulphites or, preferably, thiols. Among these reducing agents, the ones most commonly used are cysteine and its various derivatives (especially N-acetylcysteine), cysteamine and its various derivatives (especially its C1-C 4 acyl derivatives such as N-acetylcysteamine or N-propionyl cysteamine), thiolactic acid and its esters (especially glyceryl monothiolactate), thioglycolic acid and its esters, especially glyceryl or glycol monothioglycolate, diammonium dithiodiglycolate or ammonium thioglycolate, and thioglycerol. Mention may also be made of the following reducing compounds: N-mercaptoalkylamides of sugars such as N-(2-mercaptoethyl)gluconamide, 8-mercaptopropionic acid and its derivatives, thiomalic acid, pantethine, the N-(mercaptoalkyl)-o)-hydroxyalkyamides described in patent application EP-A-354 835 and the N-mono- or N,N-dialkylmercapto-4-butyramides described in patent application EP-A-368 763, the aminomercaptoalkylamides described in patent application EP-A-432 000 and the 6 alkylaminomercaptoalkylamides described in patent application EP-A-514 282, and the mixture of 2-hydroxypropyl thioglycolate and of 2-hydroxy-lmethylethyl thioglycolate (67/33) described in patent application FR-A-2 679 448.

The preferred reducing compounds are especially chosen from thioglycolic acid and its esters, cysteamine and cysteine. The reducing agent that is particularly preferred in the invention is thioglycolic acid and its esters, such as, especially, glyceryl or glycol monothioglycolate, ammonium thioglycolate or cysteine.

The amount of reducing agent is generally between 0.1% and 25% by weight and preferably between 1% and 15% by weight relative to the total weight of the composition.

The reducing composition that may be used in the process of the present invention preferably has a pH of between 5 and 11 and more preferably between and The pH of the reducing compositions may optionally be adjusted by adding acidifying agents, for instance hydrochloric acid, acetic acid, lactic acid or boric acid, or basifying agents such as ammonia, monoethanolamine or ammonium bicarbonate.

The compositions used in the process according to the invention may also contain other ingredients such as linear or cyclic, volatile or non-volatile silicones, cationic polymers, peptides and derivatives thereof, protein hydrolysates, waxes, .swelling agents, penetrating agents or agents for reinforcing the efficacy of the reducing agent, such as the Si02/PDMS (polydimethylsiloxane) mixture, dimethylisosorbitol, urea and its derivatives, pyrrolidone, N-alkylpyrrolidones, thiamorpholinone, alkylene glycol or dialkylene glycol alkyl ethers, for instance propylene glycol monomethyl ether, dipropylene glycol monomethyl ether, ethylene glycol monoethyl ether and diethylene glycol monoethyl ether, C 3

-C

6 alkanediols, for instance 7 1,2-propanediol and 1,2-butanediol, 2-imidazolidinone, and also other compounds such as pantothenic acid, anionic, cationic, nonionic, amphoteric or zwitterionic surfactants, agents for preventing hair loss, antidandruff agents, natural or synthetic, associative or non-associative thickeners, suspension agents, sequestering agents, opacifiers, dyes, sunscreens, vitamins or provitamins, and also fragrances and preserving agents, and mixtures thereof.

Preferably, the reducing composition used in the process of the present invention contains at least one cationic agent. This cationic agent is preferably polymeric. Cationic polymers that may be mentioned include the products known under the INCI names Polyquaternium 10 and Hexadimethrine Chloride.

The composition used in the process of the invention may be in the form of a thickened or nonthickened lotion, a cream, a gel or any other suitable form.

The iron may be applied by successive separate touches for a few seconds, or by gradual movement or sliding along locks.

As examples of irons that may be used according to the invention, mention may be made of flat or round irons of all types and in particular, in a non-limiting manner, those described in patents US 4 103 145, US 4 308 878, US 5 983 903, US 5 957 140, US 5 494 058 and US 5 046 516.

The process according to the invention may comprise an additional step of predrying the hair with a dryer before using the iron, so as to avoid substantial release of steam that might burn the hairstylist's hands and the model's scalp.

The process according to the present invention may also include an additional fixing step that consists in applying an oxidizing composition to the dried hair, i.e. after the iron has been used.

This oxidizing (or fixing) composition comprises an oxidizing agent that may be chosen from 8 hydrogen peroxide or aqueous hydrogen peroxide solution, and urea peroxide; alkali metal bromates; persalts such as perborates and persulphates; and enzymes such as peroxidases and 2-electron oxidoreductases. The use of hydrogen peroxide or of the said bromates is particularly preferred.

The concentration of aqueous hydrogen peroxide solution may range from 1 to 10 volumes but is preferably between 6,and 8 volumes.

The bromate concentration is generally between 1% and 12% by weight and the persalt concentration is generally between 0.1% and 15% by weight relative to the total weight of the oxidizing composition.

Another subject of the invention is the use of the process of the present invention for smoothing the hair.

The examples that follow are given as illustrations of the present invention.

EXAMPLES

Example 1 The smoothing cream having the composition below was prepared, the proportions being expressed as percentages by weight.

N-Oleyldihydrosphingosine Ammonium thioglycolate as an aqueous 71% solution 8 Diammonium dithiodiglycolate as an aqueous 48% solution 2-Octyldodecanol 2 Ethylenediaminepentaacetic acid, pentasodium salt, 0.4 as an aqueous 40% solution Cetylstearyl alcohol (50/50) 8 Aqueous ammonia (20% NH 3 3.3 Oxyethylenated cetyl alcohol (containing 2 mol of 3 ethylene oxide) Cetyltrimethylammonium chloride as an aqueous 25% 4 solution 9 Behenyltrimethylammonium chloride as an 80% 4 solution in water/isopropanol Cetyl palmitate 2 Polydimethylsiloxane containing aminoethylamino- 2.85 propyl and a,o-silanol groups, as an aqueous cationic emulsion Fragrance 0.3 Deionized water qs 100 Smoothing operations were performed on 9 asiatic models with coloured hair, using the smoothing cream whose composition is given above.

The smoothing cream is applied to clean, wet hair, left in contact with the head of hair for a time that is sufficient to reduce the hair, and is then rinsed out. The hair is then towel-dried, predried using a dryer and then smoothed lock by lock using a flat iron heated to 180 0 C. The fixing agent (12-volumes aqueous hydrogen peroxide solution, pH 3) is then applied directly to the dry hair, left in contact with the head of hair so as to fix the given shape, and then rinsed out. The head of hair is then dried using a dryer.

The relaxing and disentangling are very good on wet hair and on dried hair.

Hair that is smooth from the root to the end and manageable is obtained. The hair is coated, treated and tonic. This treatment affords good cosmetic qualities without softening the hair and amplifies the smoothing effect.

Example 2 A lotion was prepared from the following compounds in the proportions indicated in percentages by weight: N-Oleyldihydrosphingosine 0.25 Methyl p-hydroxybenzoate 0.2 Methylalkylalkylamidoethylimidazolinium 4.2 10 methosulphate as a 75% solution in propylene glycol Behenyltrimethylammonium chloride as an 80% 1.4 solution in water/isopropanol Chlorhexidine hydrochloride 0.02 Deionized water qs 100 This lotion is applied to hair that has just been relaxed. After predrying using a hair dryer, the hair is smoothed lock by lock using a flat iron heated to 180 0 C. Manageable, tonic hair is thus obtained.

Claims

1. A hair treatment process comprising the steps consisting of: applying to the hair a composition containing at least one ceramide in a 0_ 5 cosmetically acceptable vehicle, the composition being not rinsed out before the treating with an iron raising the temperature of the hair, using Sa flat or round iron, heating to above 60C

2. Process according to claim 1, characterized in that the N temperature is between 60 to 220°C and preferably between 120 to 200 0 C.

3. Process according to claim 1 or 2 characterized in that it comprises an additional step of predrying the hair with a dryer before using the iron.

4. Process according to any one of the preceding claims, characterized in that the ceramide is a compound of formula below: 0 R3 R I -C-N-CH-CH-O-R 2 I I R4 (I) in which: Ri denotes either a saturated and unsaturated, linear or branched Cs- C3o hydrocarbon radical, this radical possibly being substituted with one or more hydroxyl groups, these hydroxyl groups optionally being esterified with a saturated and unsaturated C16-C3o fatty acids; or a radical which R denotes hydrogen atom or a monohydroxylated or polyhydroxylated, preferably monohydroxylated, Ci-Cio hydrocarbon radical, and R' and R" are hydrocarbon radicals, the sum of the carbon atoms of these radicals being between 9 to 30, R' being a divalent radical; Rz denotes a hydrogen, atom or a (glycosyl)n, (galactosyl)m, and sulphogalactosyl radical, in which n is an integer -12- N0 ranging from 1 to 4 inclusive and m is an integer ranging from 1 to 8 Sinclusive; R denotes a hydrogen atom or a saturated and unsaturated C16-C27 hydrocarbon radical, this radical possibility being substituted with one or oo 5 more C1-C14 alkyl radicals; and R3 may also denote a Cis-C26 a-hydroxyalkyl radical, the hydroxyl group of which may optionally be esterified with a SC1 6-C3oa-hydroxy acid; R4 denotes a hydrogen atom, a saturated or unsaturated C16-C27 hydrocarbon radical or a radical -CHz-CHOH-CH2-O-R6 in which R6 denotes a Clo-C26 hydrocarbon radical; Rs denotes a hydrogen atom or a monohydroxylated or polyhydroxylated Ci-C4 hydrocarbon radical. Process according to claim 4, characterized in that the ceramide is a compound of formula in which Ri denotes an optionally hydroxylated saturated or unsaturated alkyl radical derived from C16-C22 fatty acids; Rz denotes a hydrogen atom; and R3 denotes an optionally hydroxylated saturated linear Cis radical.

6. Process according to claim 5, characterized in that the ceramide is chosen from: N-linoleoyldihydrosphingosine, N-oleoyldihydrosphingosine, N-palmitoyldihydrosphingosine, N-stearoyldihydrosphingosine, N-behenoyldihydrosphingosine, N-2-hydroxypalmitoyldihydrosphingosine, N-stearoylphytosphingosine, or mixtures thereof.

7. The process according to claim 6, characterized in that the ceramide is chosen from N-oleoyldihydrosphingosine, N-2- hydroxypalmitoyldihydrosphingosine, and N-stearoylphytosphingosine. -13- I8. Process according to any one of the preceding claims, 0 Scharacterized in that the ceramide is present in a concentration within the range from 0.001% to 20% by weight, preferably from 0.01% to 10% by weight and even more preferably from 0.1% to 5% by weight, relative to the oO 5 total weight of the composition.

9. Process according to any one of claims 1 to 8, characterized in Sthat the composition containing at least one ceramide is applied before or after a reducing composition comprising a reducing agent. Process according to claim 9 wherein a rinsing step follows the 10 application of the reducing composition.

11. Process according to any one of claims 1 to 9, characterized in that the composition containing at least one ceramide also comprises a reducing agent. 1 2. Process according to claim 9, 10 or 11, characterized in that the reducing agent is chosen from the group formed by thioglycolic acid and its esters, cysteamine, and cysteine.

13. Process according to claim 12, characterized in that the reducing agent is thioglycolic acid, glyceryl monothioglycolate, glycol monothioglycolate, ammonium thioglycoloate, and cysteine.

14. Process according to claim 9 to 13, characterized in that the reducing agent is contained in an amount ranging from 0.1% to 25% by weight and preferably from 1% to 15% by weight, relative to the total weight of the composition. Process according to claim 9 to 14, characterized in that the pH of the composition is between 5 and 11 and preferably between 6.5 and

16. Process according to any one of claims 9 to 15, characterized in that it comprises an additional fixing step that consists in applying an oxidizing composition to dry hair.

17. Use of the process according to any one of the preceding claims, for smoothing hair.

18. Hair treatment process of claim 1 having the steps substantially as hereinbefore described with reference to the examples. -14- O 00 O By its Registered Patent Attorneys S 5 Freehills Patent Trade Mark Attorneys L'OREAL