NEW HAIR COMPOSITIONS AND THEIR USES

Abstract

The present invention relates to the field of everyday necessities and more particularly to the field of hair care. More specifically, it concerns ceramide derivatives of general formula I: wherein R and R' represent, distinctly or simultaneously, a saturated fatty acid chain having from 6 to 26 carbon atoms, branched or unbranched, and preferably compounds in which R and R' are a stearyl or a behenyl. These compounds are used in hair care compositions to improve hair strength or shine.

Description

The present invention relates to the field of life necessities and more particularly to the field of hair care. We know that hair is constantly exposed to chemical and physical aggressors such as UV rays, pollution, dust, and surfactants. For centuries, numerous molecules and plant extracts have been used to improve hair protection and strength. It is known that certain compounds possess the property of protecting hair. In this category, we can mention ceramides or some of their derivatives (International Congress Series 1996, 1111, 117). Numerous scientific publications and patents mention, to varying degrees, the use of ceramides for hair care. For example, patent JP 2006199633 can be cited. This effect can be enhanced by combining it with molecules such as phytantriol, which also possesses hair-protective properties (Patent WO0015181). Ceramide derivatives have also found applications in hair treatment (US Patent 005-863-945). Glucosyl ceramides also provide molecules of interest for this type of application (French Patent 2,718,960). In the category of ceramide derivatives, it should be noted that these molecules - or amido lipids - are very often combined with other compounds to obtain a synergistic effect in hair care. (Patent JP 2005272393). Pseudo-ceramides are also used to promote hair elasticity (Patent KR 20010119411). They are similarly found in phenomena that reduce the coefficient of friction (Int. Journal of Cosmetic Science 1995, 17, 133). Aminoalkyl amides have already been cited as having potential applications in hair care (US Patent 20020182164). Lipophilic amino acid derivatives also show promise in limiting keratin degradation following hair coloring (WO Patent 2009024362). Sugar derivatives such as lipids derived from mannosylerythritol have recently been used in a hair care study with very good results (Journal of Oleo Science 2010, 59, 267). Sugars possessing a carboxylic acid group have also been transformed into ester amides for this type of application (French Patent DE 19523479). In the field of hair regrowth, amide-type compounds are mentioned (French Patent FR 2849773). In the same area of ​​application, derivatives of 2-amino alkane 1,3-diol, which induce or stimulate hair growth, are also reported (French Patent FR 2744916). However, in screening various new compounds, the Applicant unexpectedly discovered that certain molecules with the general formula I: R' NH₂O, in which R and R' distinctly or simultaneously represent a saturated fatty acid chain of 6 to 26 carbon atoms, branched or unbranched, are of great interest in hair care applications, particularly in hair treatment. These active principles constitute the active element and the defining characteristic of the cosmetic and / or dermatological compositions of the invention, in combination or in mixture with one or more dermatologically acceptable, non-toxic, inert excipients. Such molecules are produced by the company Solabia. They were manufactured according to the enzymatic process described in patent FR2855823, starting from 1-amino 2,3-propane dios and a saturated fatty acid derivative. Another process using chemical catalysis can also be employed, as there is no particular risk of oxidation with saturated molecules. The concentrations used range from 0.05% to 5%, and preferably from 0.1% to 2% by weight in this series. OH(I) Different molecules were produced with varying carbon chain lengths, but the best results were obtained with compounds in which R and R' represent the acyl remainder of behenic acid or stearic acid, namely 22 carbon atoms or 18 carbon atoms, respectively. The preferred product is a compound of general formula I' in which R and R' each represent the acyl remainder of stearic acid and / or behenic acid: NH OH R~ O / If o (1" Product P 1: R = R' = stearic or behenic carbon chain and in particular 1-stearoylamino, 2-hydroxy, 3-hydroxy stearyl propane and 1-behenylamino, 2-hydroxy, 3-hydroxy stearyl propane. Various tests against placebo were carried out on hair resistance or repair. The latter are greatly improved, but the compounds of general formula I also act on the aesthetic appearance of the hair such as shine. The cosmetic and / or dermatological compositions according to the invention are presented in one of the forms suitable for hair application and in particular in the form of creams, oil-in-water or water-in-oil emulsions, lotions, soaps, butters, serums, masks, or styling waxes. The compositions are used at a rate of 1 to 4 applications per day, preferably in cream form at a rate of 2 to 3 applications per day, using a hazelnut-sized amount on the scalp or hair. To prepare the cosmetic compositions of the invention, the compound of general formula I is mixed or dispersed with a lipid phase, which is then emulsified in an aqueous phase. The mixture is then diluted with a thickening agent, and the final preparation is perfumed or flavored with a fragrance or aroma. The compositions according to the invention may also be enhanced with a coloring agent, a preservative, a texture-enhancing agent, an antibacterial agent, an emulsifying agent, and / or an agent that imparts a pearlescent appearance. The product may also contain another active ingredient with a similar or synergistic action. Among the perfumes that can be used for such compositions, we can mention the Parfum 40119-01 preparation from Synarome, the Flashy perfume from Synarome, the orange or mandarin aroma, the floral aroma from Robertet, the lilac aroma from Expressions parfumées, the rose aroma from Robertet, the Divine perfume from Robertet. Among the flavorings that can be added to the compositions of the invention are citronella, violet, rose geranium, and Oriental Flower fragrance (MLW). Examples of coloring agents that can be added include VDC Red 40 (LCW) and DC Yellow 6 (LCW). Alternatively, no coloring agent may be incorporated. Preservatives include, in particular, Germabens, parabens (methyl ester, ethyl ester, butyl ester, or propyl ester), and Dermosoft, specifically Dermosoft 13388eco, Dermosoft GMCY, and Dermosoft 700B. Among the compositions that improve touch, silicones, siliconols, or silicone oils, such as the product DC 1403 (Dow Corning) made from a mixture of Dimethicone and Dimethiconol, the product DC 1501 (mixture of Cyclopenta siloxane and dimethiconol) or Amodimethicone, are particularly noteworthy. Examples of emulsifying agents include polyethylene glycol stearates, propyl stearates, Brij, Span, self-emulsifying products, Saponins and similar compounds. Examples of thickening agents include mucilage, vegetable gums, acrylic polymers, polyacrylamide, Fucogel, guar gum derivatives and similar products. The concentration of active ingredient of formula I ranges from 0.05% to 5% by weight and preferably from 0.1% to 2% by weight in the composition. EXPERIMENTAL SECTION Example of tests performed with product P1 for hair applications. Basic formula for the tests: Isofo120 (Sasol) Octyldodecanol 5.00 Product Pl according to the invention 0.2 Demineralized water Aqua Qsp 100 Phenonip (Clariant) Phenoxyethanol / methylparaben / 0.50 ethylparaben / butylparaben / propylparaben / isobutylparaben Germall 115 (ISP) Imidazolidinyl urea 0.20 Sepigel 305 (Seppic) Polyacrylamide / C13-14 isoparaffin / 1.50 Laureth-7 Citric acid or Triethanolamine Qs pH 1. Anti-split end effect: Purpose of the Study: The purpose of this study is to demonstrate the anti-split end and anti-breakage potential of the product. Various tests are performed, and the best results are obtained with compounds where R = R' = stearic acid (18 carbon atoms) and / or behenic acid (22 carbon atoms). The test is carried out on hair strands after automatic combing. Hair is weakened by its environment, by cleaning products, and, of course, by the mechanical stress of combing. 2. Treatment Protocol: Hair strands are prepared and calibrated. They must weigh 5 g and be 25 cm long. The test uses 6 hair strands per condition. All strands are washed for one minute with a 10% sodium lauryl ether sulfate solution. After rinsing, the strands are either untreated (control) or treated with the product at 0.2% or with the excipient, massaging for one minute and then the strands are rinsed.The wicks are then dried in a standardized atmosphere for 24 hours. Automatic Combing: After treatment, the hair strands are combed five times before being placed in the automatic combing device. Within this machine, the hair strands undergo the following five cycles: Combing for 5 minutes at 25 rpm (rotations per minute) at a temperature of 40°C; Combing for 5 minutes at 25 rpm at a temperature of 27°C. The automatic combing device is shown in Appendix 1. The combing phases at 40°C correspond to a blow-drying action, and the combing phases at 27°C correspond to classic combing. The strands are then removed from the device. One hundred hairs are taken, and the number of breaks and split ends is determined by counting. The presentation of the automatic combing apparatus is shown in Appendix I. Statistics: Statistical analysis was performed using a one-way ANOVA with a 95% confidence interval. Results Anti-breakage potential (Plate 1) Number of breaks Plate 1: graphical representation of the number of breaks (+ week) The use of the product formulated at 0.2% allows a significant decrease (p<0.05) in the number of breaks of 62% compared to the excipient and of 71% compared to the untreated control. Anti-frog potential number of forks 25 20 15 -1 * 10 0 Control Placebo Product P1 at 0.2% Figure 2: graphical representation of the number of forks (+ week) 7 The use of the product formulated at 0.2% allows a significant decrease (p<0.05) in the number of forks of 43% compared to the excipient and of 55% compared to the untreated control. Hair treatment with a hair product P1 according to the invention, formulated with 0.2% of the product, therefore reduces the appearance of breakage and split ends. The product thus strengthens the hair's resistance to mechanical damage. II. Shine Effect on Hair The Applicant Company verified, after validating the product's protective potential, its ability to improve hair shine. Hair shine is one of the most important desired parameters in the field of hair products. It is reflected by the reflection of incident light on the hair. This reflection depends on the smoothness of the surface, its color, and the characteristics of the incident light. In this study, the diffuse reflection of hair, and therefore its shine, was measured using the Glossmeter (BYK Gardner®). This device measures reflected light at an angle of incidence of 85°. The device is calibrated with a perfectly smooth surface for its zero value and with other reference surfaces (shown below in Appendix 2). The intensity of light reflection is measured in units of brightness. Protocol Strands of dark brown Caucasian hair are prepared and calibrated. They must weigh 5 g and be 25 cm long. Five strands of hair are used per condition. All strands are washed for one minute with a 10% sodium lauryl ether sulfate solution. After rinsing, the strands are either untreated (control) or treated with product P1 at 0.2% or with the excipient, massaging for one minute. The strands are then rinsed with clean water and dried in a standardized atmosphere. The strands are spread out and held in this position to allow their glossiness to be measured with the Glossmeter. Five consecutive gloss readings are taken for each measurement. (The hair spreading device is shown in Appendix 3) Results Plate graph 3 ..G..~...~.. ~r~ ~.. ~ ~ ~..~. , 16 T 14 T 12 10 8 T 6 4 Control Placebo Product P1 Plate 3: Shine evaluated by specular reflection (+ sem) The use of product P1 according to the invention formulated at 0.2% allows a significant increase (p<0.05) in hair shine of 9% compared to the excipient and of 124% compared to untreated controls. Examples of cosmetic formulation with product P1 for hair applications. Example 1 r4 d MATERIALS 1 PHASE A Water cep 100 Aqua Preservative qsp Plantapon 611C (Cognis) 22.00 Sodium laureth sulfate / Abil T quat 60 (Evonik) 1.50 cocamidopropyl betaine / coco glucoside _ Silicone quaternium-22 Dehyquart CC7 BZ (Cognis) 3.00 Polyquaternium-7 Tego pearl N100 (Evonik) 2.00 Glycol distearate / steareth-4 I':~~ 5 ~ 13 Lamesoft TM Benz (Cognis) 4.00 Glycol distearate / coco glucoside / glyceryl oleate / glyceryl distearate Product Pl 0.10 I'II:A~SL Parfum Divine (Robertet) _ 0.30 Fragrance NaCl 1.00 Sodium chloride Citric acid, soil 10% Qs pH Citric acid __.. .__..._ __.__. . _ PEG-200 hydrogenated glyceryl Rewoderm LIS 80 (Evonik) 4.00 . almitate / PEG-7 glyceryl cocoate OE s 1' . 11 Prepare phase A at room temperature, with slow stirring. Melt product Pl in the Lamesoft, then add this premix to phase A.Incorporate the elements of phase C one by one. PHYSICO-CHEMICAL CHARACTERISTICS OF THE PREPARATION pH = 5.30 + / - 0.30 at 20°C Viscosity: 5,500 cps + / - 1,000 at 20°C, at 24h, LVT 3, 12 rpm Example 2 INGREDIENTS F- NAME IN ,l PHASE A Tego care 450 (Degussa) 3.00 Polyglyceryl-3 Methylglucose distearate Nacol 22 98 (Sasol) 3.00 Behenyl alcohol 2.00 Coco caprylate / caprate Dub 810C (Stearinerie Dubois) Dub PPH1 (Stearinerie Dubois) 2.00 Hydrogenated palm kernel glycerides / Hydrogenated palm glycerides Product P 1 0.20 PHASE B Water Demineralized qs 100 Aqua Glycerin 3.00 Glycerin Keltrol CG-SFT (Kelco) 0.4-0- Xanthan gum PHASE C _. .. _.. 0.50 Mica / Titanium dioxide Prestige bright silver (Eckart) PHASE D Demineralized water 5.00 Aqua Calcidone (UCIB) 0.20 Calcium PCA PHASE E Oriental Flower Perfume (MLW) 0.20 Fragrance _ qs Citric acid Citric acid, solution at 0% Preservative qs PROCEDURE. Prepare phases A and B separately at 75°C. Make the emulsion by pouring A into B while stirring. At 65°C.At 45°C, add phase C and continue cooling. At 35°C, incorporate phase D. At 45°C, incorporate the elements of phase E. PHYSICO-CHEMICAL CHARACTERISTICS OF THE PREPARATION pH = 5.50 + / - 0.50 at 20°C Viscosity: 6,000 + / - 2,000 cps at 20°C, LVT 3, speed 12 rpm Example 3 RAW MATERIALS NAME 1 PHASE A Nikkomulese 61 H (Nikko) 5.00 Polyglyceryl-10 pentastearate / behenyl alcohol / stearamidopropyl dimethylamine lactate Nacol 16 98 (Sasol) 3.00 Cetyl alcohol P1_ 0.30 _product PHASE B Demineralized water ~Qsp 100A~ua __..._ _.._._._.____..._.._ __..____.___..____.._...__ 1.50 Butylene glycol Butylene glycol Esaflor EC 3 (Lambert) 0.30 Guar hydroxypropyltrimonium chloride PHASE C _ _-_. ._---..___. ~__ ____ 1.00 Amodimethicone DC Q2-8220 (Dow Coming) Saboquat CTA 25 (Sabo) 1.50 Cetrimonium chloride Cosmedia CTH(E) (Cognis) 1.25 Polyquaternium-37 / propylene glycol dicaprylate / dicaprate / PPG-1 trideceth-6 PHASE D Parfum Divine (Robertet) 0.20 Fragrance Bamboo leaf glycolysate 3.00 Propylene glycol / Aqua / Bambusa (CEP, Solabia group) vulgaris PROCEDURE Heat the components of phase A to 70°C. Add product P1 when the temperature is reached. Heat the water to 70°C. Moisten the Esaflor in the Butylene glycol and add this mixture to the aqueous phase while stirring. Prepare the emulsion by pouring A into B while stirring. At 45°C, add the components of phase C. At 35°C, add the components of phase D. PHYSICO-CHEMICAL CHARACTERISTICS OF THE PREPARATION pH = 5.50 + / - 0.30 at 20°C Viscosity: 50,000 cps + / - 10,000 at 20°C, at 24h, LVT 4, 12 rpm Example 4 TI PHASE A % Hydrogenated coconut oil 32 / 34 18.00 Hydrogenated coconut oil (Interchemin) Isofo120 (Sasol) 7.50 Octyldodecanol Dub TG 12 (Stéarinerie Dubois) 10.00 Trilaurin Sonnenatural (Sooneborn) 10.00 Olus oil Te_osoft CR (Evonik 15.00 Cet 1 ricinoleate Comprito1888 (Gattefossé) 12.00 Glyceryl dibehenate / Tribehenin / Glyceryl behenate Naco122 98 (Sasol) 8.00 Behenyl alcohol Stearic acid (Interchimie) 9.00 _.a_ _ Stearic acid ____. ._...___._.._._.._.__..._ ___..._.. ..__....ee.._e_ _.~ ~.__ _ Glyceryl stearate citrate Axol C62 (Evonik) 2.00 Product Pl 0.10 Pl ï:?~SF S Sensoil Cumaru (CEP, Solabia group) 8.00 Bertholletia excelsa seed oil / Dipteryx odorata _...__ Preservative q.s. D,L a tocopherol (Roche) 0.10 (D,L) a tocopherol Heat the components of phase A to 70°C. Add product P1 when the temperature is reached. Allow to cool and add the components of phase B.

Claims

14 DEMANDS 1. Hair compositions characterized in that they contain, as an active ingredient, a ceramide derivative of general formula I 0 (D in which R and R' are identical and are the acyl remainder of stearic acid or behenic acid in association or mixture with an inert, non-toxic, skin-compatible diluent or vehicle.

2. Hair compositions according to claim 1 in which the content of active ingredient ranges from 0.05 to 5% by weight.

3. Hair compositions according to any one of the preceding claims wherein the content of the active ingredient ranges from 0.1 to 2% by weight.

4. Hair compositions according to any one of the preceding claims wherein the content of the active ingredient ranges from 0.1 to 0.3% by weight.

5. Use of the hair compositions according to any one of the preceding claims to obtain an anti-split end effect, an anti-breakage effect and an effect on the hair shine.

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