Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
  • C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
  • C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
  • C07C229/26—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having more than one amino group bound to the carbon skeleton, e.g. lysine
• • 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
  • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
  • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
  • A61K8/88—Polyamides
• • 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
  • A61Q5/02—Preparations for cleaning the hair
• • 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
  • A61Q5/12—Preparations containing hair conditioners
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
  • C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
  • C08G69/08—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from amino-carboxylic acids

Definitions

• Cosmetic composition comprising at least one fatty-chain polylysine intended to improve the surface state of the keratinous fibers.
• the present invention relates to novel cosmetic compositions, comprising at least one fatty-chain polylysine intended to improve the surface state of keratinous fibers, as well as processes for the synthesis of fatty-chain polylysines.
• N- ⁇ -polylysines with a fatty chain has been described in the patent application JP05246963, in the food industry as a bacterial emulsifier.
• the use of N- ⁇ -fatty-chain polylysines (amide junction) has also been described in the patent application JP2001-191521, as a bactericidal detergent.
• Urethane analogues have been described in patent application JP2002-147360.
• the preparation of amide-functional derivatives and their interest as surfactants have been described in patent application JP11255892.
• composition comprising at least one fatty-chain polylysine makes it possible to improve the surface state of the keratin materials.
• the subject of the invention is therefore a cosmetic composition intended for the protection and / or repair of keratin materials, characterized in that it comprises, in a cosmetically acceptable medium, at least one fatty-chain polylysine of formula (I) below :
• R 1 represents a linear or branched, saturated or unsaturated C 5 -C 30 hydrocarbon-based chain, optionally interrupted by N, S, or O, and optionally substituted with one or more hydroxyl groups and / or one or more fluorine atoms
• R 2 represents H, or a linear or branched, saturated or unsaturated C 1 to C 8 alkyl group
• n 2 to 10,000 and preferably 5 to 1000, and with the proviso that in the polylysine of formula (I), at least one of radicals R is different from H.
• keratinous material is intended to mean skin appendages and in particular hair, eyelashes, hair and nails.
• hair, eyelashes, hair and nails Preferably, it is human keratin material and preferably hair.
• the cosmetic composition described above makes it possible to restore a hydrophobic coating to an abraded keratin material that has become hydrophilic.
• This hydrophobic coating allows the damaged fiber to find a hydrophobic surface state close to that of natural hair and this in a sustainable manner.
• the appearance of the hair is improved by the treatment with a cosmetic composition of the invention.
• the hair treated with the composition of the invention is also softer, brighter, easier to disentangle and to comb.
• the radical R represents H or a group of formula (II) or (IV) as defined above in which R1 represents a C5-hydrocarbon chain. C24 linear or branched, saturated or unsaturated and R2 represents a hydrogen atom, it being understood that at least one of the radicals R is different from H.
• the radical R represents H or a group of formula (VI), (VII), (VIII) OR (IX):
• the invention also relates to the organic or inorganic salts of the compounds (I), the lysine unit being also racemic or isomerically pure.
• organic or inorganic salts that can be used according to the invention are the physiologically acceptable salts of the compounds of formula (I).
• the addition salts with an acid are, for example, the hydrochloric or hydrobromic acid or sulfuric acid or citric or succinic or tartaric or lactic acid or para-toluenesulphonic or phosphoric or acetic salts or the fatty acid salts such as linoleic acid, oleic acid. palmitic, stearic, behenic and 18-methylicosanoic.
• the addition salts with a base are, for example, sodium, calcium and hydroxyalkylamine salts, for example
• R 1 represents a linear or branched, saturated or unsaturated C 5 -C 30 hydrocarbon-based chain, optionally interrupted by N, S, or O, and optionally substituted with one or more hydroxyl groups and / or one or more fluorine atoms
• R 2 represents H, or a linear or branched, saturated or unsaturated C 1 to C 8 alkyl group, and (b) in which n is 2 to 10,000 and preferably 5 to 1000, with the proviso that in the polylysine of formula (x), at least one of the radicals R is different from H.
• the radical R represents H or a group of formula (IV) or (V) as defined above in which R1 represents a C5-hydrocarbon chain. C24 linear or branched, saturated or unsaturated and R2 represents a hydrogen atom, it being understood that at least one of the radicals R is different from H.
• the radical R represents a radical of formula (IV) in which R 2 represents a hydrogen atom and R 1 represents a CH 3 - (CH 2) 7 -CH chain. CH- (CH2) 8 -
• the cosmetic composition according to the invention may comprise from 0.01 to 50%, and preferably from 0.05 to 20% by weight, of polylysine with a fatty chain, relative to the total weight of the composition.
• compositions according to the invention comprise, besides said compounds of formula (I), a physiologically acceptable medium, in particular a cosmetically acceptable medium, that is to say a medium that is compatible with the keratin materials as defined above.
• the physiologically acceptable medium may contain various components conventionally used in the treatment of keratinous fibers such as the hair among which mention may be made of water, organic solvents such as alcohols such as ethanol or alcohol. benzyl, perfumes, preservatives, sequestering agents, acidifying agents, alkalizing agents, UV filters, pigments, pearlescent agents, fillers, dyes, polymers other than the compounds of formula (I), thickeners, anionic or amphoteric or nonionic surfactants, emulsifiers, co-emulsifiers, gums, conditioning agents, oligomers and the like.
• organic solvents such as alcohols such as ethanol or alcohol.
• benzyl perfumes, preservatives, sequestering agents, acidifying agents, alkalizing agents, UV filters, pigments, pearlescent agents, fillers, dyes, polymers other than the compounds of formula (I), thickeners, anionic or amphoteric or nonionic surfactants, emulsifiers, co-emul
• anti-hair loss agents anti-dandruff agents
• ceramides agents for shaping hair, waxes, mineral, organic or plant oils, polar or apolar, volatile or nonvolatile silicones, vitamins or provitamins, anti-radical agents, antioxidants, oxidants and mixtures thereof.
• the cosmetically acceptable medium comprising the fatty-chain polylysines of the invention comprises:
• aliphatic or aromatic alcohols preferably ethanol, benzyl alcohol, fatty alcohols, modified or unmodified polyols, such as glycerol, glycol, propylene glycol, dipropylene glycol, butylene glycol, butyl diglycol, and / or silicones, whether volatile or not, and / or
• oxyethylenated waxes or not paraffins, alkanes and preferably Cs to C10 alkanes, and / or
• fatty acids fatty amines, fatty esters and more particularly benzoates or salicylates of fatty alcohol, and / or
• the pH of the composition according to the invention can be adjusted to the desired value by means of acidifying or alkalizing agents well known in the state of the art.
• alkalinizing agents for example, ammonia, alkali carbonates, alkanolamines such as mono-, di- and triethanolamines and their derivatives, hydroxyalkylamines and ethylene diamines ethoxylated and / or oxypropylenated, the hydroxides of sodium or potassium and the compounds of formula (Xl) below:
• R is a propylene residue optionally substituted by a hydroxyl group or a C 1 -C 4 alkyl radical
• R 4 , R 5, R ⁇ and R 7 which may be identical or different, represent a hydrogen atom, an alkyl radical in dC 4 or hydroxyalkyl in dC 4 .
• the acidifying agents are conventionally, for example, inorganic or organic acids such as hydrochloric acid, orthophosphoric acid, carboxylic acids such as tartaric acid, citric acid, lactic acid, or acids. sulfonic.
• the cosmetically acceptable medium may be present as it is or in emulsified or encapsulated form.
• the cosmetic composition described above may be rinsed or not rinsed, and may be in various galenic forms.
• the cosmetic composition may be a composition for hair application, in the form of a lotion, an aerosol spray or not, a mousse, a gel, a cream, a
• This composition can be a shampoo, a conditioner, a temporary or permanent coloring composition or a composition for shaping the hair such as permanent or straightening or smoothing.
• the subject of the invention is also the processes for the synthesis of fatty-chain polylysines of formula (I), described below.
• the invention relates to a process for the synthesis of a fatty-chain polylysine of formula (I) consisting in reacting: (i) a compound of formula:
• Ri represents a chain linear or branched, saturated or unsaturated C 5 -C 30 hydrocarbon-based hydrocarbon, optionally interrupted by N, S, or O, and optionally substituted by one or more hydroxyl groups and / or one or more fluorine atoms
• R 3 represents a linear or branched C1 to C8 alkyl group, saturated or in saturated, allowing the compounds of formula (II) to be obtained as defined above
• R1 has the same meaning as in a) and R2 is H, or a C1-C8 alkyl group linear or branched, saturated or unsaturated. allowing to obtain compounds of formula (IV) as defined above
• N- ⁇ -Poly-lysine is solubilized between 20 and 80 ° C. in a protic solvent such as alcohols.
• the activated species (compound of formula defined in a, b, c, d or e above) in solution in an organic solvent such as THF is added dropwise to the reaction medium, and left stirring at room temperature between 1 H and
• 0.74 g of oleic acid (techn.) And 0.24 g of triethylamine are diluted in 5 ml of THF. This solution is added, by a very slow drop on a solution comprising 0.27 g of ethyl chloroformate and 2 ml of THF, cooled to -10 0 C. The addition is done so that the temperature is between -10 0 C and -5 ° C. The generated triethylamine hydrochloride precipitates instantly. Once the addition is complete, it is allowed to return to room temperature, and then the solution is filtered. The filtrate containing the mixed anhydride is immediately used as it is in the next step.
• N- ⁇ -Poly-L-lysine (Chisso) are solubilized at 60 ° C. in 100 ml of 96% ethanol. It is allowed to return to room temperature. As soon as the preparation of the mixed anhydride is complete, the solution containing it is added dropwise. Once the addition is complete, let it shake for 15 minutes. The reaction medium is then concentrated and then diluted in 90 ml of water. The residual free acid is extracted with 3 times 300 ml of ethyl acetate. The aqueous phase is then evaporated to dryness. The compound obtained is characterized by 2D NMR, GC and functional assays. It is consistent with the expected product.
• the fatty-chain level of the polylysine can be modulated by varying the [mixed anhydride] / [N- ⁇ -Poly-L-lysine] molar ratio.
• Beechenic chain polylysines and 18-methylicosanoic chain-chain polylysines may be synthesized according to the same procedure.
• This reaction medium is added dropwise to a solution containing 10 g of anhydrous N- ⁇ -Poly-L-lysine (Chisso) (2.13 mmol 0.9 eq) in 10OmL of 95% EtOH; the resulting medium is then left stirring at room temperature for 48 hours.
• the reaction medium is then concentrated to dryness on a rotary evaporator under reduced pressure.
• the pale yellow powder obtained is suspended in 10OmL of CH 2 Cl 2 and brought to reflux for 1 h 30 and then filtered. The operation is repeated 2 times.
• the finished product is obtained in the form of a pale yellow powder (9.69 g) with a yield of 90%.
• the lotion is sprayed on wet hair after rinsing and wringing the shampoo.
• the hair is combed after spraying the lotion and blow-drying is done directly afterwards.
• the lotion is sprayed on wet hair after rinsing and wringing the shampoo.
• the hair is combed after spraying the lotion and blow-drying is done directly afterwards.
• the hair is washed with one of the compositions of Examples 5 to 10 and rinsed with water.
• the hair thus treated has excellent cosmetic properties (softness, natural touch). Examples 11 to 14
• Belsil DM 300 000 ( ⁇ acker) [10] Lanette O OR (CognisS) [11] Miraceti (Laserson) [12] Genamin KDMP (Clariant) [13] Dow Corning 939 emulsion (Dow corning) Washing is carried out the hair, followed by rinsing with water and then applying a composition of Examples 11 to 14 and then rinsing with water.
• the hair thus treated has excellent cosmetic properties (softness, natural touch).

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• Health & Medical Sciences (AREA)
• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Life Sciences & Earth Sciences (AREA)
• Public Health (AREA)
• General Health & Medical Sciences (AREA)
• Veterinary Medicine (AREA)
• Animal Behavior & Ethology (AREA)
• Epidemiology (AREA)
• Birds (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Medicinal Chemistry (AREA)
• Polymers & Plastics (AREA)
• Dermatology (AREA)
• Cosmetics (AREA)
• Polyamides (AREA)

Applications Claiming Priority (2)

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• 2005
  • 2005-08-05 FR FR0552449A patent/FR2889448B1/fr not_active Expired - Fee Related
• 2006
  • 2006-08-03 JP JP2008524559A patent/JP2009503043A/ja not_active Withdrawn
  • 2006-08-03 US US11/997,922 patent/US20080213206A1/en not_active Abandoned
  • 2006-08-03 WO PCT/FR2006/050780 patent/WO2007017610A2/fr not_active Ceased
  • 2006-08-03 CN CNA200680036965XA patent/CN101282764A/zh active Pending
  • 2006-08-03 BR BRPI0614533A patent/BRPI0614533A2/pt not_active IP Right Cessation
  • 2006-08-03 EP EP06794521A patent/EP1909914A2/de not_active Withdrawn

Non-Patent Citations (1)

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