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
  • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
  • A61K8/41—Amines
  • A61K8/416—Quaternary ammonium compounds
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P17/00—Drugs for dermatological disorders
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P17/00—Drugs for dermatological disorders
  • A61P17/18—Antioxidants, e.g. antiradicals
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q19/00—Preparations for care of the skin
  • A61Q19/10—Washing or bathing preparations
• • 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
  • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
• • 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
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q19/00—Preparations for care of the skin
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q19/00—Preparations for care of the skin
  • A61Q19/04—Preparations for care of the skin for chemically tanning the skin
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q3/00—Manicure or pedicure preparations

Definitions

• Cationic surfactant compounds their use as conditioner, cosmetic treatment process, and cosmetic or pharmaceutical compositions comprising them
• the present invention relates to novel cationic compounds, to cosmetic compositions comprising them, and to their use in particular for cosmetically treating the hair.
• compositions according to the invention can bring about advantageous conditioning properties to the hair, in particular concerning the improvement of the flexibility of the hair when the composition is applied to the hair. wet hair, then obtaining, after rinsing, hair still having improved flexibility, the hair is therefore less stiff. This relaxation of the hair is particularly remarkable with the compositions according to the invention.
• these compositions also make it possible to improve disentangling, smoothing, combing and maneuverability of the hair; the shaping of the hair is easier, and the touch of the hair is very pleasant and fluid.
• the compounds according to the invention are easily transportable in aqueous cosmetic media, which facilitates their implementation.
• an object of the present invention is a compound of formula (I) or (II) as defined below.
• Another subject of the invention is a cosmetic or pharmaceutical composition
• a cosmetic or pharmaceutical composition comprising, in a physiologically acceptable medium, at least one compound of formula (I) or (II) as defined below.
• Another subject of the invention is the use of at least one compound of formula (I) or (II) as hereinafter defined, or a composition as defined below, as a hair conditioning agent.
• - m is an integer between 1 and 10;
• n is an integer between 0 and 10;
• X represents O, NH or S,
• R1, R2 and R3 denote, independently of one another, a linear C 1 -C 22 or branched C 3 -C 28 alkyl group, or a linear C 2 -C 22 or branched C 3 -C 28 alkenyl group, these groups being optionally substituted by one or more radicals, identical or different, chosen from hydroxyl (OH) and amino (-NRR 'radicals with R and R' chosen from, independently of each other, H and alkyl in C1-C6); or
• a linear (C4-C22) or branched (saturated) alkyl radical comprising, in interruption in the chain, one to three carbon rings each comprising 3, 4, 5 or 6 ring members, saturated or unsaturated, which are identical or different; said ring (s) being optionally substituted by an aryl itself optionally substituted by one or more radicals, which may be identical or different, chosen from C1-C6 alkyl, hydroxyl (OH) and amino (-NRR 'with R radicals).
• R4 denotes an alkyl radical containing 2 or 3 carbon rings, said rings are separated from each other by a divalent methylene -CH 2 - or ethylene radical; or a linear or branched C4-C22 alkyl or alkenyl (saturated or unsaturated) radical comprising, at the chain end, a saturated or unsaturated, non-aromatic carbon ring comprising 5 or 6 ring members;
• R 5 denotes a hydrogen atom or an OR or NRR 'radical with R and R' chosen from, independently of each other, H and C 1 -C 6 alkyl; it being understood that when m is greater than or equal to 2, the radicals R5 are identical or different;
• An- denotes an anion, or an organic or inorganic mixture of anions, to ensure the electroneutrality of the compounds of formula (II).
• n is an integer of 1 to 4, especially 1, 2 or 3, preferably 1 or 2.
• n is an integer from 0 to 4, especially O, 1, 2 or 3, preferably O or 1.
• X represents O or NH.
• R 1 denotes a linear C 1 -C 4 alkyl, branched C 3 -C 4 alkyl, linear C 2 -C 4 alkenyl or branched C 3 -C 4 alkenyl group.
• R 1 is methyl or ethyl.
• R 2 denotes a C 1 -C 4 linear alkyl group, branched alkyl in
• R2 is methyl or ethyl.
• R 3 denotes a C 1 -C 22 linear alkyl group, branched alkyl in
• R3 represents a linear C1-C18 alkyl group.
• R4 denotes: either a linear C4-C22 alkyl radical comprising, as an interruption in the chain, one to three carbon rings each comprising 3, 4, 5 or 6 links, saturated or unsaturated, identical or different; preferentially a linear C12-C21 alkyl radical, comprising in interruption in the chain, one to three carbon rings each comprising 3, 4, 5 or 6-membered, saturated and identical; more particularly, said alkyl radical comprising interrupting one to three cyclopropyl rings, it being understood that when 2 or 3 rings are present, they are separated from each other by a divalent methylene -CH 2 - radical;
• R4 may be a linear or branched C4-C22 alkyl radical comprising, as an interruption in the chain, one of the following divalent sequences:
• R5 denotes a hydrogen atom or a hydroxyl radical (OH).
• An denotes an anion, or a mixture of anions, chosen from acetate, lactate, tartrate, citrate, halogen, SO 4 2" , HSO 4 " , MeSO 4 “ , EtSO 4 “ , mesylate, tosylate, and especially CI “ , Br “ , MeSO 4 “ , EtSO 4 “ , mesylate and tosylate, as well as mixtures thereof.
• the compounds of formula (II) may be used as such or in the form of solvates, in particular hydrates.
• the compounds of formula (I) or (II) may be used alone or as a mixture.
• a mixture of compounds according to the invention and in particular the following mixtures: - mixture of 3- (dimethylamino) propyl13 - [(1R) -cyclopent-2-en-1-yl ] thdecanoate + 3- (dimethylamino) propyl] - [(1R) -cyclopent-2-en-1-yl] undecanoate + 3- (dimethylamino) propyl (6E) -13 - [(1R) -cyclopent-2 -en-1-yl] tridec-6-enoate, especially proportion 40/55/5;
• An- especially in proportion 50/50;
• An- is preferably methylsulfate;
• An- is preferably bromide; especially in proportion 50/50;
• An- is preferably chloride; in particular in proportion 50/50;
• the quaternized ester (II) can be obtained by reacting on the amine (I), an alkylating agent such as, for example, methyl iodide, dimethyl sulphate, ethyl iodide, diethyl sulphate or a haloalkane, such as bromohexadecyl.
• an alkylating agent such as, for example, methyl iodide, dimethyl sulphate, ethyl iodide, diethyl sulphate or a haloalkane, such as bromohexadecyl.
• the tertiary amine (I) and the alkylating agent can be mixed and heated at 15 ° C to 140 ° C for 2 to 80 hours. After cooling, the excess of alkylating agent can be removed by washing with diisopropyl ether.
• the solid obtained can be filtered, preferably under an inert atmosphere, washed and dried under reduced pressure, optionally in the presence of P 2 O 5 .
• An ion exchange can be carried out at the end of the reaction, by contact with an ion exchange resin chosen according to the desired exchanges. These resins are, for example, IRA 402 (alkyl sulphate exchange in chlorides) or IRA 400 (iodide exchange in chloride).
• the anion can be exchanged by treating an aqueous or (hydro) alcohol solution of the compound with the ion exchange resin.
• the solvent can be removed, the product washed for example with diisopropyl ether, then filtered and dried under reduced pressure, optionally in the presence of P 2 O 5 .
• the compounds of formula (I) or (II) in which R4 denotes a C4-C22 linear or branched (saturated or unsaturated) alkyl or alkenyl radical comprising at the end of the chain a saturated or unsaturated carbon ring 5-membered, non-aromatic, can be prepared by saponification, then ester activation and condensation, from Chaulmoogra oil.
• Chaulmoogra oil is an oil mainly extracted from the seeds of tropical woody plants belonging to the family Flacourtiaceae, including a tree of variety such as Hydnocarpus wightiana and Taraktengenos ontoii. These plants are mainly of Asian origin, including India, Vietnam and the Philippines, as well as Central and South America, including Brazil.
• the seeds from which Chaulmoogra oil is extracted contain a high proportion of lipid content, generally between 30 and 50% depending on the species, 15 to 20% of protides and 4 to 6% of mineral material, as well as 1 to 3% unsaponifiable, glycerides of unsaturated fatty acids with a pentenic ring , consisting essentially of chaulmoogric acid, hydnocarpic acid and gorlic acid, of formula:
• Chaulmoogra oil also contains fatty acids such as palmitic, oleic, palmitoleic, stearic, myristic, and traces of aleptic and aleprylic acid.
• the Chaulmoogra oil used in the compositions of the present invention can be extracted from the seeds of plants of varieties such as:
• the three main acids contained in the Chaulmoogra oil can be hydrogenated under usual catalytic hydrogenation conditions, to yield the corresponding totally hydrogenated acids, which correspond to certain compounds of formula (I) according to the present invention:
• the amount of compound (I) or (I), alone or as a mixture, present in the compositions depends, of course, on the type of composition and the desired properties, and can vary within a very wide range, generally between 0.01 and 50% by weight, preferably between 0.1 and 30% by weight, in particular between 0.5 and 25% by weight, or even between 1 and 20% by weight, more preferably between 1, 5 and 10% by weight, relative to the total weight of the composition.
• the compositions according to the invention may of course comprise a mixture of compounds of formula (I) or (II).
• compositions according to the invention can be in any of the galenical forms conventionally used, and especially in the form of an aqueous, alcoholic or aqueous-alcoholic solution or suspension or oily; a solution or dispersion of the lotion or serum type; an emulsion, in particular of liquid or semi-liquid consistency, of the O / W, W / O or multiple type; a suspension or emulsion of soft consistency of cream (O / W) or (W / O) type; an aqueous or anhydrous gel, or any other cosmetic form.
• compositions may be packaged in pump bottles or in aerosol containers, in order to ensure application of the composition in vaporized form (lacquer) or in the form of foam.
• vaporized form lacquer
• foam vaporized form
• Such forms of packaging are indicated, for example, when it is desired to obtain a spray or a mousse, for hair treatment.
• the composition preferably comprises at least one propellant.
• the composition is in the form of an emulsion comprising the compound of formula (I) or (II) dispersed in an aqueous phase or in solution in a fatty phase.
• compositions according to the invention comprise a physiologically acceptable medium, that is to say a medium compatible with keratinous substances, in particular the skin of the face or of the body, the lips, the hair, the eyelashes, the eyebrows and nails.
• a physiologically acceptable medium is preferably a cosmetically acceptable medium, the composition then being a cosmetic composition intended in particular for topical application.
• Said physiologically acceptable medium preferably comprises at least one usual cosmetic ingredient, especially chosen from C1-C40 alcohols, carbonaceous oils, water, C8-C40 esters, C8-C40 acids, surfactants and the like.
• Said medium can of course include several cosmetic ingredients listed above.
• the usual cosmetic ingredients may be present in customary amounts, easily determinable by those skilled in the art, and which may be included, for each ingredient, between 0.01 to 80% by weight .
• the composition may in particular comprise water and / or one or more C1-C40 alcohols; there may be mentioned aliphatic or aromatic monoalcohols C1-C7, polyols and polyol ethers, which can be used alone or in admixture with water; advantageously, the composition comprises a water / ethanol, water / isopropanol or water / benzyl alcohol mixture.
• the carbonaceous oils, in particular hydrocarbon oils, and / or the silicone oils may be present in a proportion of 0.01 to 20% by weight, especially 0.02 to 10% by weight relative to the total weight of the composition.
• the synthetic oils linear or branched, saturated or unsaturated hydrocarbonic, cyclic or aliphatic theaters, such as, for example, polyalpha-olefins, in particular polydecenes and polyisobutenes; silicone oils, volatile or not, organic-modified or not, water-soluble or not; fluorinated or perfluorinated oils; their mixtures.
• Alcohols, esters and acids, having 8 to 40 carbon atoms can be present in a proportion of 0.01 to 50% by weight, especially 0.1 to 20% by weight relative to the total weight of the composition.
• Mention may in particular be made of C12-C32 linear or branched chain fatty alcohols, in particular C12-C26, and in particular cetyl alcohol, stearyl alcohol, cetylstearyl alcohol, isostearyl alcohol, octyldodecanol, 2-butyloctanol, 2-hexyldecanol, 2-undecylpentadecanol, oleic alcohol or linoleic alcohol.
• C8-C40 fatty alcohols in particular C16-C20, which are oxyalkylenated, in particular oxyethylenated, preferably comprising from 10 to 50 moles of ethylene oxide and / or propylene oxide, such as olethoxide. -12, ce-teareth-12 and ceteareth-20, oxypropylene stearyl alcohol in particular comprising 15 moles of propylene oxide, oxyethylenated lauryl alcohol, including more than 7 oxyethylene groups, and mixtures thereof.
• Mention may also be made of C16-C40 linear or branched chain fatty acids, and in particular 18-methyl eicosanoic acid, coconut oil acids or hydrogenated coconut oil acids; stearic acid, lauric acid, palmitic acid and oleic acid, behenic acid, and mixtures thereof; Mention may also be made of linear or branched chain fatty esters containing in total 8 to 40 carbon atoms, such as esters of monoalcohols or polyols of fatty acids containing from 8 to 30 carbon atoms, and their derivatives.
• the polyols being preferably chosen from sugars, C2-C6-alkylene glycols, glycerol, polyglycerols, sorbitol, sorbitan, polyethylene glycols, polypropylene glycols and mixtures thereof. Mention may be made, as monoalcohol esters, of myristate or isopropyl palmitate, as well as myristates, palmitates and stearates of myristyl, cetyl and stearyl, alone or as a mixture.
• the composition may also include as carbonaceous oils, vegetable oils such as avocado oil, olive oil, apricot oil, argan oil, jojoba oil, butter shea, which may be present in a proportion of 0.1 to 10% by weight in the composition, in particular 0.2 to 5% by weight.
• vegetable oils such as avocado oil, olive oil, apricot oil, argan oil, jojoba oil, butter shea, which may be present in a proportion of 0.1 to 10% by weight in the composition, in particular 0.2 to 5% by weight.
• the composition according to the invention comprises C 8 -C 40 fatty alcohols, which may be present especially in an amount of 1 to 15% by weight, in particular 2.5 to 10% by weight, or even 3 to 8% by weight, in the cosmetic composition.
• These fatty alcohols can be saturated or unsaturated, linear or branched; mention may be made in particular of cetyl alcohol, stearyl alcohol, isostearyl alcohol, oleic alcohol, ricinoleic alcohol, linoleic alcohol, alone or as a mixture; saturated fatty alcohols, alone or as a mixture, are preferred.
• the surfactants nonionic, cationic, anionic, amphoteric or zwitterionic, other than those of formula (I), and mixtures thereof, may be present in a proportion of from 0.01% to 50% by weight, in particular 0.1% to 40% by weight, or even 0.5 to 30% by weight, more preferably 1 to 15% by weight, relative to the total weight of the composition.
• the weight ratio between the amount of fatty alcohols and the amount of surfactants in the composition is preferably greater than or equal to 1, 5, in particular between 1, 5 and 10, or even between 1, 6 and 8, even better between 1, 7 and 6.
• the propellants may be present in a proportion of 5 to 90% by weight relative to the total weight of the composition, and more particularly in a proportion of 10 to 60% by weight.
• the sunscreens may be present in a proportion of 0.01 to 20% by weight, especially 0.5 to 10% by weight relative to the total weight of the composition.
• the moisturizing agents may be present in a proportion of 0.01 to 20% by weight, especially 0.1 to 7% by weight relative to the total weight of the composition.
• the anti-dandruff agents may be present in a proportion of 0.001 to 20% by weight, especially 0.01 to 10% by weight relative to the total weight of the composition, preferably 0.1 to 5% by weight.
• the antioxidants may be present in a proportion of 0.05 to 1.5% by weight, relative to the total weight of the composition.
• the reducing agents may be present in a proportion of from 0.1 to 30% by weight, in particular 0.5 to 20% by weight relative to the total weight of the composition.
• the oxidation bases may be present in an amount between
• the couplers may be present in an amount of from 0.001 to 10% by weight, preferably from 0.005 to 6% by weight, of the total weight of the composition.
• the oxidizing agents may be present in an amount of between 1 and 40% by weight, preferably between 1 and 20% by weight, relative to the weight of the composition.
• the direct dyes may be present in an amount of from 0.001 to 20% by weight, preferably from 0.01 to 10% by weight, relative to the total weight of the composition.
• the relaxing agents may be present in a proportion of 0.01 to 3.5% by weight, especially 0.05 to 1.5% by weight relative to the total weight of the composition.
• the pearlescent and opacifying agents may be present in a proportion of 0.01 to 3% by weight, especially 0.05 to 2.5% by weight relative to the total weight of the composition.
• the plasticizing or coalescing agents may be present in a proportion of 0.1 to 25% by weight, especially 1 to 10% by weight relative to the total weight of the composition.
• the hydroxy acids may be present in a proportion of 1 to 10% by weight, in particular 2 to 5% by weight relative to the total weight of the composition.
• the pigments and fillers may be present in a proportion of 0.01 to 50% by weight, especially 0.02 to 30% by weight relative to the total weight of the composition.
• Silicones can be volatile or not; polyorganosiloxanes, which may or may not be modified, namely oils, gums and resins of polyorganosiloxanes, as such or in the form of solutions in organic solvents, or in the form of emulsions or microemulsions, may especially be mentioned. They may be present in an amount of 0.01 to 40% by weight, especially 0.05 to 20% by weight, relative to the total weight of the composition.
• the thickeners may be present in a proportion of from 0.01 to 10% by weight, in particular from 0.1 to 5% by weight relative to the total weight of the composition.
• the polymers in particular water-soluble or soluble in carbonaceous and / or silicone oils, can be present in a proportion of 0.01 to 20% by weight, especially 0.1 to 10% by weight relative to the total weight of the composition.
• compositions of the present invention will take care to choose the ingredients in the composition, as well as their amounts, so that they do not adversely affect the properties of the compositions of the present invention.
• the cosmetic composition according to the invention may be in the form of a product for the care, cleaning and / or make-up of the skin of the body or of the face, the lips, the eyebrows, the eyelashes, the nails and the hair , a sunscreen or self-tanning product, a personal hygiene product, a hair product, especially care, cleaning, styling, shaping, hair dyeing.
• the hair compositions are preferably shampoos, conditioners, styling or care gels, lotions or care creams, conditioners, styling lotions, blow-dry lotions, fixing compositions and the like. styling such as lacquers or spray; of restructuring for hair; anti-hair loss lotion or gel, anti-parasitic shampoo, anti-dandruff lotion or shampoo, anti-seborrhoeic shampoo.
• the lotions may be packaged in various forms, such as in sprays, pump bottles or in aerosol containers to ensure application of the composition in vaporized form or in foam form.
• a hair coloring product in particular oxidation dyeing or direct dyeing, optionally in the form of a coloring shampoo; in the form of a composition of permanent, de-waxing or discoloration, or in the form of a composition to be rinsed, to be applied before or after a coloring, a discoloration, a permanent or a straightening or between the two stages of a permanent or a straightening.
• composition according to the invention may also be in the form of a care composition, in particular a moisturizer, for the skin of the body or of the face, the lips and / or the integuments, in particular of a care product intended to treat cosmetically the skin and in particular to moisturize it, smooth it, depigment it, nourish it, protect it from the sun's rays, or give it a specific cosmetic treatment.
• a care composition in particular a moisturizer, for the skin of the body or of the face, the lips and / or the integuments
• a care product intended to treat cosmetically the skin and in particular to moisturize it, smooth it, depigment it, nourish it, protect it from the sun's rays, or give it a specific cosmetic treatment.
• a skin cleansing composition for example a makeup remover or a bath or shower gel, or a cleansing bar or bar
• a personal hygiene composition including a deodorant product, antiperspirant, or a depilatory composition, a gel or aftershave lotion.
• a makeup product for the skin of the body or the face, lips, eyelashes, nails or hair especially a foundation, a blush, a blush, an eyeliner, an eyeliner, a mascara, a lipstick, a lip gloss, a lip liner; nail polish, nail care; a temporary tattoo product of the body skin.
• the composition according to the invention finds an interesting application for the care and the cosmetic treatment, in particular the protection, of hair, in particular weakened and / or damaged hair, for example by chemical or mechanical treatments;
• the compounds according to the invention can be used after the treatment, after a step of coloring, bleaching or straightening the hair.
• the subject of the invention is therefore a process for the cosmetic treatment, in particular of makeup, care, cleaning, coloring, shaping, keratin materials, in particular of the skin of the body or of the face, lips, nails , hair and / or eyelashes, comprising the application on said materials of a cosmetic composition comprising at least one compound according to the invention.
• it is a cosmetic treatment method for conditioning the hair, in particular to provide or improve the flexibility, disentangling, smoothing and / or combability of the hair.
• the application of the composition may optionally be followed by a rinsing step and / or optionally a heat treatment step.
• R6 C1 to C4 alkane
• R7 unsaturated cat alkene
• the carboxylic acid A, the aminoalcohol A 'and a catalyst are stirred, under an inert atmosphere, in an organic solvent, for example anhydrous dichloromethane, at a temperature of 100.degree. - temperature between -5 ° C and 10 ° C.
• a coupling agent for example, 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride, may be added slowly.
• the reaction medium is preferably stirred for one hour at this temperature before being brought back to ambient temperature.
• the reaction medium is hydrolyzed and then, after extraction with an organic solvent, for example dichloromethane, the organic phase is washed with an aqueous solution, dried over metal sulphate (for example sodium or magnesium) and concentrated under reduced pressure.
• the compound obtained is of formula (I), it can be dried under vacuum in the presence of P 2 O 5
• the quaternized compound of formula (II) can be obtained by reacting the compound (I) and an alkylating agent as per for example, methyl iodide, dimethyl sulphate, ethyl iodide, diethyl sulphate, or a haloalkane.
• An ion exchange can be carried out if necessary at the end of the reaction, by contact with an ion exchange resin selected according to the desired exchanges.
• ion exchange resins selected according to the desired exchanges.
• resins are, for example, IRA 402 (alkyl sulphate exchange in chlorides), IRA 400 (iodide exchange in chloride).
• the mixture of D acids derived from Chaulmoogra oil is obtained by saponification of said oil.
• Step 1 Synthesis of the ⁇ - ⁇ -octylcyclopropyl) octahydroxy acid chromate
• Step 1 Synthesis of the mixture of acids derived from Chaulmooqra oil (mixture essentially consisting of hvdnoc irpic, qorlic and chaulmogamic acids)
• Step 2 Synthesis of the Mixture of Acyl Cellulose Chloride + Hydrochloric Acid Chloride + Acidic Acid Chloride
• Step 3 Synthesis of the mixture of 3- (dimethylamino) propyl 13 -f (1R) -cyclopent-2-en-1-ylitridecanoate + • 3- (dimethylamino) proplyl 11- [(1 R) -cyclopent-2-en 1- (1RV-CVC) opent-2-en-1-ylitridec-6-enoate 1-yllundecanoate + S-methylethylaminotoroDyl
• Step 2 Synthesis of the mixture of ac-chloride chlorides 11-cvc [opentylundecanoic and 13-cyclopentvtridecanoic (50/50))
• ac-chloride chlorides 11-cvc opentylundecanoic and 13-cyclopentvtridecanoic (50/50)
• reaction medium was then returned to ambient temperature and then kept at room temperature for 3 hours.
• the reaction mixture was then poured into 300 ml of slightly acidic water (pH 5) and then ex- treated with 3 times 100 ml of dichloromethane. After washing the organic phase with 100 ml of a saturated solution of ammonium chloride, the organic phase was dried over sodium sulphate, filtered on sintered glass and then evaporated under reduced pressure to obtain 3.7 g of the expected product under form of a white powder with a yield of 85%
• Example 8 Synthesis of the mixture of 3 - [(1 1 -cyclopentylundecanoyl) amino] -N, N, N-trimethylpropan-1-aminium methyl sulfate + 3 - [(13-cyclopentyltridecanoyl) amino] -N, N, N-trimethylpropan-1-aminium methyl sulfate
• reaction mixture was then poured into 300 ml of slightly acidic water (pH 5) and then extracted with 3 times 100 ml of dichloromethane. After washing the organic phase with 100 ml of a saturated solution of ammonium chloride, the organic phase was dried over sodium sulphate, filtered on sintered glass and then evaporated under reduced pressure to obtain 4.26 g of the expected product under form of a brown paste with a yield of 82%.
• Example 10 Synthesis of 2- (2-r (11-cyclopentylundecanoyl) oxy] ethoxy) -N, N, N-triethylethanaminiumethyl sulfate + 2- [2 - [(13-cyclopentyltri-decanoyl) oxylethoxy) -N N, N-triethylethanaminium ethyl sulfate
• Example 1 1 Synthesis of the mixture of 13 - [(1R) -cyclopent-2-en-1-yl-N- [3- (di methylamino) propyl] -tridecanamide + 1 1 - [(1R) -cyclopent-2- ⁇ -1- ⁇ -N- [3- (di methylamino) propyl) -undecanamide + (6E) -13-r (1 R) -cyclopent-2-en-1-yl-N- [3- (dimethylamino) propyl] -tridec-6 -enamide
• Example 12 Synthesis of the mixture of 3 - ((13-r (1 R) -cyclopent-2-en-1-tri-decanoylamino) -N, N, N-trimethylpropan-1-aminium methyl sulfate + 3-Cl 1 - [(1R) -cyclopent-2-en-1-yl-dialecanoyl) amino) -N, N, N-trimethylpropan-1-aminium methyl sulfate + 3 - (((6E) -13-r (1 R)) -cyclopent-2-en-1-ethyltridec-6-enoyllamino) -N, N, N-trimethylpropan-1-aminium methyl sulfate
• the following hair cosmetic composition (% by weight) is prepared:
• a lock of discolored hair is treated by immersion in the hair cosmetic composition at a rate of 15 g of solution per 0.5 g of hair.
• the treatment is carried out at 30 ° C. for 15 minutes and is followed by rinsing with water. It is observed that the wet wick has a smooth feel, it is flexible and easy to disentangle.

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• 2008
  • 2008-02-04 FR FR0850662A patent/FR2926979B1/fr not_active Expired - Fee Related
• 2009
  • 2009-02-03 EP EP09711498A patent/EP2249780A2/fr not_active Withdrawn
  • 2009-02-03 BR BRPI0905927-0A patent/BRPI0905927A2/pt not_active IP Right Cessation
  • 2009-02-03 EP EP09709684A patent/EP2249779A2/fr not_active Withdrawn
  • 2009-02-03 CN CN2009801040554A patent/CN103179945A/zh active Pending
  • 2009-02-03 MX MX2010008017A patent/MX2010008017A/es unknown
  • 2009-02-03 BR BRPI0905932-6A patent/BRPI0905932A2/pt not_active IP Right Cessation
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  • 2009-02-03 WO PCT/FR2009/050164 patent/WO2009101322A2/fr active Application Filing
  • 2009-02-03 US US12/865,829 patent/US20110052513A1/en not_active Abandoned
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  • 2009-02-03 WO PCT/FR2009/050165 patent/WO2009101323A2/fr active Application Filing
  • 2009-02-03 JP JP2010544768A patent/JP2011525475A/ja active Pending
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