WO2013117770A2 - Cosmetic treatment method, and composition comprising a glyoxylic acid ester - Google Patents
Cosmetic treatment method, and composition comprising a glyoxylic acid ester Download PDFInfo
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- WO2013117770A2 WO2013117770A2 PCT/EP2013/052710 EP2013052710W WO2013117770A2 WO 2013117770 A2 WO2013117770 A2 WO 2013117770A2 EP 2013052710 W EP2013052710 W EP 2013052710W WO 2013117770 A2 WO2013117770 A2 WO 2013117770A2
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- 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
- A61K8/37—Esters of carboxylic acids
- A61K8/375—Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
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- 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
- A61Q5/002—Preparations for repairing the hair, e.g. hair cure
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Abstract
The invention relates to a method for the cosmetic treatment of keratinous substances, comprising the application, to the said keratinous substances, of a cosmetic composition comprising at least one compound of formula (I) and also its salts; its hydrates; its acyclic or cyclic (thio)acetals; its (thio)hemiacetals and its optical and geometrical isomers: in which formula (I) R represents a radical resulting from a mono-or polyalcohol, and n denotes an integer ranging from 1 to 100, the composition comprising neither a colouring agent nor a reducing agent.
Description
COSMETIC TREATMENT METHOD, AND COMPOSITION COMPRISING A
GLYOXYLIC ACID ESTER The present invention relates to a cosmetic treatment method, in particular a hair cosmetic treatment method, capable of being employed in order to introduce a long-lasting change to keratinous substances, and to a composition which can be used in the said method. In the hair field, consumers wish to have available compositions which make it possible to introduce a temporary change to their hair and to do this while targeting a good wear property for the effect produced. In general, it is desirable for the change to withstand shampooing operations for a minimum of 15 days, indeed even more, depending on the nature of the said change.
Treatments already exist for modifying the colour or the shape of the hair and also, to some extent, the texture of the hair. One of the known treatments for modifying the texture of the hair consists of the combination of heat and of a formaldehyde- comprising composition. This treatment is especially effective in conferring a better appearance on damaged hair and/or in treating long hair and curly hair.
The action of formaldehyde is associated with its ability to cross-link proteins by reaction with its nucleophilic sites. The heat use can be that of the iron (flat tongs or crimping iron), the temperature of which can generally reach 200°C or more. However, there is an increasing desire to avoid the use of such substances, which can prove to be aggressive to the hair and other keratinous substances.
Application WO201 1/104282 has thus provided a novel method for semipermanently smoothing the hair which consists in applying an a-aceto acid solution to the hair for from 15 to 120 minutes, in then drying and, finally, in smoothing the hair with an iron at a temperature of approximately 200°C. The a-aceto acid employed is preferably glyoxylic acid.
However, it has been found that the use of glyoxylic acid can result in some significant limitations; in particular, its pH of action is acidic, in particular of the order of 4, indeed even less, which may not always be well tolerated, in particular when the scalp is sensitive and/or irritated.
Nor is it desirable either to employ it at high concentrations, due to its intrinsic acidic nature. Its volatility, enhanced by the use of heat (iron), can also present a problem.
Furthermore, cosmetic formulations having an acidic pH can detrimentally affect
the hair and/or detrimentally affect the colour thereof. In point of fact, the desired treatment is very particularly intended to repair artificially dyed hair. It is therefore preferable to avoid the use of active agents capable of introducing a reinforcing effect but while contributing to detrimentally affecting the hair and/or its artificial colour.
It is already known to use glyoxylic acid esters in hair compositions, in particular in hair dyeing compositions, such as described in the document DE19859722, and in reducing compositions, such as described in the document DE19860239.
In another field, documents US201 1/0081393 and US201 1/001 17147 mention the use of menthyl glyoxylate in a refreshing composition.
In point of fact, the Applicant Company has now discovered, unexpectedly and surprisingly, that some very specific compounds make it possible to introduce the desired properties into keratinous substances.
In particular, the method according to the invention will not bring about a change in the colour of the hair and will not cause a problem of breaking of the individual hair. The composition will not detrimentally affect the integrity of the fibre, in particular its cuticle. In addition, it will improve the mechanical properties of the hair, such as the resistance to moisture, and the sheen, and will reduce frizz.
Thus, a subject-matter of the present invention is a method for the cosmetic treatment of hair, comprising the application, to the said hair, of a cosmetic composition comprising at least one compound of formula (I) and also its salts; its hydrates; its acyclic or cyclic (thio)acetals; its (thio)hemiacetals and its optical and geometrical isomers:
in which formula (I):
• R represents a radical resulting from a mono- or polyalcohol,
R representing a radical chosen from:
i) C1-C30 alkyl radicals, in particular C1-C10 alkyl radicals; or C2-C30 alkenyl radicals, in particular C2-C10 alkenyl radicals; the said alkyl or alkenyl radicals being optionally interrupted by one or more heteroatoms, divalent groups or their combinations chosen from -O-, -S-, -C(O)- or -N(R1)-; with R1 denoting a hydrogen atom or a C1-C10 alkyl radical, preferably interrupted by an amido -C(O)-N-(R2)- group with R2 representing a hydrogen atom or a C1-C4 alkyl group;
ii) C6-C30 aryl radicals, in particular C6-Ci4 aryl radicals, such as phenyl;
iii) non-aromatic mono- or polycyclic heterocyclic radicals which comprise from 3 to 50 ring members, preferably from 3 to 14 ring members, which are unsaturated or saturated and which optionally comprise one or more heteroatoms chosen from O, S or N;
it being possible for these different radicals to be optionally substituted by one or more groups chosen from hydroxyl, mercaptan, aldehyde, amino, (di)(Ci- Cio)alkylamino, (di)hydroxy(Ci-Cio)alkylamino, C2-C10 acyl, amido: R1-C(O)- N(R1)-, (C2-C10 acyl)amido: R1-C(O)-N(R1)-C(O)-, halogen, sulfo, carboxyl, cyano or (Ci-Cio)alkoxy groups, with R1, which are identical or different, being as defined above, it being possible for the aryl and non-aromatic mono- or polycyclic radicals in addition to be substituted by C1-C10 alkyl radicals
• and n denotes an integer ranging from 1 to 100,
the composition comprising neither a colouring agent nor a reducing agent. It has been found that the method according to the invention makes it possible to obtain a solution for the reinforcement and/or repair of the hair in a way which is lasting and compatible with any type of past or future hair treatment.
In that which follows, the expression "at least one" is equivalent to the expression "one or more".
The term "mono- or polyalcohoP' is understood to mean an organic compound comprising a hydroxyl group (monoalcohol) or at least two hydroxyl groups (polyalcohol or polyol), it being possible for the said hydroxylated organic compound to be aliphatic, acyclic, linear or branched, or (hetero)cyclic, such as sugars (mono- or polysaccharides) or sugar alcohols.
More particularly, the polyalcohol comprises from 2 to 100 hydroxyl groups, preferably from 2 to 20 hydroxyl groups, more preferably still from 2 to 10 hydroxyl groups and better still 2 or 3 hydroxyl groups.
Preferably, n denotes an integer ranging from 1 to 3.
The term "aryf radical is understood to mean a monocyclic or fused or non-fused polycyclic carbon-based group comprising from 6 to 22 carbon atoms, at least one ring of which is aromatic; preferably, the aryl radical is a phenyl, biphenyl, naphthyl, indenyl, anthracenyl or tetrahydronaphthyl.
The term "alkyf radical is understood to mean a linear or branched hydrocarbon radical, preferably a Ci-Cs hydrocarbon radical.
The term "alkoxy" radical is understood to mean an alkyloxy radical for which the alkyl radical is a linear or branched hydrocarbon radical, preferably a Ci-Cs
hydrocarbon radical.
The term "alkenyP' radical is understood to mean a linear or branched hydrocarbon radical which is unsaturated, in particular by one or more double bonds, such as 1 to 3 double bonds, which are conjugated or non-conjugated, preferably a C2-C8 hydrocarbon radical.
According to a specific embodiment of the invention, the compound or compounds of formula (I) are such that R is a radical resulting from a mono- or polyalcohol comprising between 1 and 10 hydroxyl groups, such as from a mono- or polyalcohol chosen from methanol, ethanol, propanol, isopropanol, butanol, hexanol, ethylene glycol, glycerol, dihydroxyacetone, glucose or sorbitol.
Mention may be made, among the compounds of formula (I), of methyl glyoxylate, ethyl glyoxylate, 2-hydroxyethyl glyoxylate, 3-hydroxypropyl glyoxylate, glyceryl glyoxylate, dihydroxyacetone glyoxylate, glyceryl diglyoxylate or triglyoxylate, sorbitol mono-, di- or triglyoxylate, glucose mono-, di- or triglyoxylate, 1 ,3- propanediol glyoxylate, 1 ,2-ethanediol glyoxylate and the compounds having the following formulae:
(1 ) (2) in which formulae (1 ) and (2) R2 is an ethyl group or the two R2 groups form a ring with the two oxygen atoms connected via an ethylene -(CH2)2- or propylene -(CH2)3- group.
In an alternative form of the invention, n is equal to 1 .
The compounds of formula (I) can be used in the form of salts. They can also be provided in the form of hydrates, of acyclic or cyclic (thio)acetals, of hemi(thio)acetals resulting from the interaction of an oxo group and in particular of the aldehyde functional group with water, a (poly)alcohol or a (poly)thiol which is preferably aliphatic (see "Protective Groups in Organic Synthesis", Theodora W. Greene, Wiley, NY, 1981 , chap. 4). The process of synthesis described in Patent US 5 015 760 can be used for the ester syntheses.
Preferably, the radical R is acyclic.
As indicated above, the composition used in the method according to the invention comprises neither colouring agent nor reducing agent.
The term "colouring agents" is understood to mean, according to the present invention, agents for colouring keratinous fibres, such as direct dyes, pigments or oxidation dye precursors (bases and couplers). If they are present, their content does not exceed 0.001 % by weight, with respect to the total weight of the composition. This is because, at such a content, only the composition would be dyed, that is to say that an effect of dyeing the keratinous fibres would not be observed.
It should be remembered that oxidation dye precursors, oxidation bases and couplers are colourless or only slightly coloured compounds which, by a condensation reaction in the presence of an oxidizing agent, give a coloured entity. With regard to direct dyes, these compounds are coloured and exhibit a degree of affinity for the keratinous fibres. The term "reducing agent" is understood to mean, according to the present invention, an agent capable of reducing the disulfide bonds of the hair, such as the compounds chosen from thiols, alkali metal sulfites, hydrides or phosphines.
The compound or compounds of formula (I) are preferably present in the cosmetic composition at a concentration ranging from 0.01 % to 50% by weight, in particular from 0.1 % to 20% by weight and preferably from 1 % to 15% by weight, with respect to the total weight of the composition.
The compositions used according to the invention can be provided in any formulation form conventionally used and in particular in the form of an aqueous, alcoholic or aqueous/alcoholic solution or suspension or oily solution or suspension; of a solution or a dispersion of the lotion or serum type; of an emulsion, in particular having a liquid or semi-liquid consistency, of the O/W, W/O or multiple type; of a suspension or emulsion having a soft consistency of (O/W) or (W/O) cream type; of an aqueous or anhydrous gel, or of any other cosmetic form.
These compositions can be packaged in pump-action sprays or in aerosol containers, in order to provide for application of the composition in the vaporized (lacquer) form or in the form of a mousse. Such packaging forms are indicated, for example, when it is desired to obtain a spray or a mousse, for the treatment of the hair. In these cases, the composition preferably comprises at least one propellant.
The compositions of the invention can be aqueous or anhydrous. They are
preferably aqueous and then comprise water at a concentration ranging from 5% to 98%, better still from 20% to 95% and even better still from 50% to 95% by weight, with respect to the total weight of the composition. The composition used in the method of the invention can additionally comprise at least one normal cosmetic ingredient chosen in particular from propellants; oils; solid fatty substances and in particular Cs-C4o esters, Cs-C4o acids or Cs-C4o alcohols; non-ionic surfactants, cationic surfactants, anionic surfactants, amphoteric surfactants or zwitterionic surfactants; sunscreens; moisturizing agents; antidandruff agents; antioxidants; chelating agents; pearlescent and opacifying agents; plasticizing or coalescing agents; hydroxy acids; fillers; silicones and in particular polydimethylsiloxanes; polymeric or non-polymeric thickeners; gelling agents; emulsifiers; polymers, in particular conditioning or styling polymers; fragrances; basifying or acidifying agents; silanes; or crosslinking agents. The composition can very obviously comprise several cosmetic ingredients appearing in the above list.
Depending on their nature and the purpose of the composition, the normal cosmetic ingredients can be present in normal amounts which can be easily determined by a person skilled in the art and which can be, for each ingredient, between 0.01 % and 80% by weight.
The composition can in particular comprise one or more organic solvents, in particular water-soluble solvents, such as C1-C7 alcohols; mention may in particular be made of aliphatic Ci-C7 monoalcohols, aromatic C6-C7 monoalcohols, C3-C7 polyols or C3-C7 polyol ethers, which can be employed alone or as a mixture with water.
Advantageously, the composition comprises a water/ethanol, water/isopropanol, water/benzyl alcohol or water/glycerol mixture.
The oils can preferably be present in a proportion of 0.01 % to 80% by weight, in particular 0.02% to 40% by weight, indeed even 0.5% to 20% by weight, with respect to the total weight of the composition. They can be carbon-based oils. Mention may in particular be made of vegetable, animal or mineral oils, which may or may not be hydrogenated; saturated or unsaturated, linear or branched, cyclic or aliphatic, synthetic hydrocarbon oils, such as, for example, poly-a-olefins, in particular polydecenes and polyisobutenes; liquid fatty alcohols, such as isostearyl alcohol, octyldodecanol, 2-butyloctanol, 2-hexyldecanol, 2-undecylpentadecanol, oleyl alcohol or linoleyl alcohol; or liquid esters, such as isopropyl myristate or isopropyl palmitate. Mention may also be made of silicone oils, which may or may not be volatile, which may or may not be organomodified and which may or may not be water-soluble; fluorinated or perfluorinated oils; and their mixtures.
The composition can also comprise one or more solid fatty substances and in particular one or more fatty alcohols, fatty esters and/or fatty acids, other than the above oils, having from 8 to 40 carbon atoms; these solid fatty substances can preferably be present in a proportion of 0.01 % to 50% by weight, in particular 0.1 % to 20% by weight, with respect to the total weight of the composition. Mention may in particular be made of fatty alcohols comprising linear C12-C32 chains, in particular C12-C26 chains, and especially cetyl alcohol, stearyl alcohol or cetearyl alcohol. Mention may also be made of fatty acids comprising linear or branched Ci6-C4o chains and in particular 18-methyleicosanoic acid, coconut oil or hydrogenated coconut oil acids, stearic acid, lauric acid, palmitic acid, oleic acid, behenic acid and their mixtures. Preferably, the fatty acids are non-salified. Mention may also be made of fatty esters comprising linear chains, comprising in total between 8 and 40 carbon atoms, such as myristyl, cetyl or stearyl myristates, palmitates and stearates, alone or as a mixture.
A person skilled in the art will take care to choose the ingredients participating in the composition and their amounts so that they are not harmful to the properties of the compositions of the present invention.
The pH of the composition can be acidic, neutral or alkaline.
The composition can additionally comprise glyoxylic acid. When it comprises it, the composition preferably comprises less than 10% by weight of glyoxylic acid, with respect to the weight of compound(s) of formula (I).
The cosmetic composition used in the method according to the invention can be provided in the form of a hair product, in particular a hair care, cleaning, styling or shaping product.
The composition especially finds a particularly advantageous application in the hair field, in particular for the retention of the hairstyle or the shaping of the hair, or the care, cosmetic treatment or cleaning of the hair. The hair compositions are preferably shampoos, conditioners, styling or care gels, care lotions or creams, masks, serums, hairsetting lotions, blow-drying lotions, fixing and styling compositions, such as lacquers or sprays, hair restructuring lotions, lotions or gels for combating hair loss, antiparasitic shampoos, antidandruff lotions or shampoos, or antiseborrhoeic treating shampoos. The lotions can be packaged in various forms, in particular in vaporizers, pump-action sprays or aerosol containers, in order to provide for application of the composition in vaporized form or in the form of a mousse.
More particularly still, the composition used in the method according to the
invention has an advantageous application in the care and the cosmetic treatment, in particular the protection, of the hair, especially of hair which has been weakened and/or damaged, for example by chemical or mechanical treatments; use may in particular be made of the compounds according to the invention in post-treatment, after a hair dyeing, bleaching or straightening stage.
The composition used in the method according to the invention can also result from the mixing, for example at the time of use, of at least one composition comprising at least one compound of formula (I), the said composition preferably being anhydrous, with at least one second composition preferably comprising water and optionally other ingredients, in particular at least one agent which enhances the reactivity of the compound of formula (I). This is because it is possible to prepare the composition to be used at the time of use, for example by mixing, at the time of use, several compositions, in particular two compositions, one of which comprises the compound or compounds of formula (I) and is preferably anhydrous. For example, it is possible to mix a first composition comprising the compound or compounds of formula (I), for example in the powder form, with a second composition comprising water and optionally other ingredients, in particular at least one agent which enhances the reactivity of the compound of formula (I). It is also possible to mix a first composition comprising the compound or compounds of formula (I), in solution or dispersion in an anhydrous solvent, for example ethanol, propylene glycol, glycerol or a PDMS, with a second composition comprising water and optionally other ingredients. A subject-matter of the invention is thus a method for the cosmetic treatment, in particular for making up, caring for, cleansing or shaping, of the hair, comprising the application, to the hair, of a cosmetic composition comprising at least one compound according to the invention. Preferably, it is a cosmetic treatment method for the conditioning, shaping, reinforcing and/or repairing of the hair, in particular for introducing or improving the disentangling, smoothing, combability, manageability or softness of the hair.
Very particularly, it can be a cosmetic treatment method for the care and cosmetic treatment, in particular the protection, of the hair, especially of hair which has been weakened and/or damaged, for example by chemical or mechanical treatments.
The method can also comprise at least one rinsing stage and/or one heat treatment stage. Thus, the application of the composition can optionally be followed by a rinsing stage and/or by a heat treatment stage, for example a treatment at a temperature of between 150°C and 250°C.
The composition can in particular be used with or without temperature, preferably
with temperature, for example by using flat tongs or a crimping iron capable of raising the temperature to a value of between 150°C and 250°C.
It should be noted that the treatment method can also comprise an additional treatment stage intended to enhance the reactivity of the keratin. In particular, such a stage can be carried out prior to the stage of application of the composition comprising the compound or compounds of formula (I).
It can be an additional stage intended to modify the ionization of the proteins, or else a stage of a reducing treatment intended to bring about the appearance of the thiol or thiosulfate functional groups (treatment with sulfites, thiols, phosphines or hydrides, for example).
Another subject-matter of the invention consists of a cosmetic composition comprising at least one compound of formula (I) and also its salts; its hydrates; its cyclic (thio)acetals; its (thio)hemiacetals and its optical and geometrical isomers:
in which formula (I):
• R represents a radical resulting from a mono- or polyalcohol,
R representing a radical chosen from:
i) C2-C30 alkyl radicals, in particular C2-C10 alkyl radicals; or C2-C30 alkenyl radicals, in particular C2-C10 alkenyl radicals; the said alkyl or alkenyl radicals being optionally interrupted by one or more heteroatoms, divalent groups or their combinations chosen from -O-, -S-, -C(O)- or -N(R1)-; with R1 denoting a hydrogen atom or a C1-C10 alkyl radical, preferably interrupted by an amido -C(O)-N-(R2)- group with R2 representing a hydrogen atom or a Ci-C4 alkyl group;
ii) C6-C30 aryl radicals, in particular C6-Ci4 aryl radicals, such as phenyl;
iii) non-aromatic mono- or polycyclic heterocyclic radicals which comprise from 3 to 50 ring members, preferably from 3 to 14 ring members, which are unsaturated or saturated and which optionally comprise one or more heteroatoms chosen from O, S or N;
it being possible for these different radicals to be optionally substituted by one or more groups chosen from hydroxyl, mercaptan, aldehyde, amino, (di)(Ci- Cio)alkylamino, (di)hydroxy(Ci-Cio)alkylamino, C2-C10 acyl, amido: R1-C(O)- N(R1)-, (C2-C10 acyl)amido: R1-C(O)-N(R1)-C(O)-, halogen, sulfo, carboxyl, cyano or (Ci-Cio)alkoxy groups, with R1, which are identical or different, being as defined above, it being possible for the aryl and non-aromatic mono- or polycyclic radicals in addition to be substituted by C1-C10 alkyl radicals
• and n denotes an integer ranging from 1 to 100.
The following examples serve to illustrate the invention without, however, exhibiting a limiting nature. The following compositions are prepared at the time of use:
The 2 compositions are applied to grey hair dyed with a lightening oxidation dye of Majirel 6.1 type.
The quality of the feel of the hair on which the composition 1 has been applied is improved in comparison with the hair on which the composition 2 has been applied.
We have al position comprising 10% of a compound
of formula
, 30% of glycerol and water at a pH of 4 or 7. Another composition comprising 10% of a compound of formula
, 10% of propylene carbonate and water, at a pH of 4 or 7 has been applied on hair locks.
We have also applied another composition comprising 10% of a compound of
formula 10% of propylene carbonate and water, at a pH of 7.
The compositions are left on hair for 30 minutes. A brushing is performed and the hair locks are treated by using a flat iron. A shampoo is then applied on the hair
locks which are then rinsed.
We obtain a good smoothing which is durable after at least one shampoo.
Claims
1 . Method for the cosmetic treatment of hair, comprising the application, to the said hair, of a cosmetic composition comprising at least one compound of formula (I) and also its salts; its hydrates; its acyclic or cyclic (thio)acetals; its (thio)hemiacetals and its optical and geometrical isomers: 
in which formula (I):
· R represents a radical resulting from a mono- or polyalcohol,
R representing a radical chosen from:
i) C1-C30 alkyl radicals, in particular C1-C10 alkyl radicals; or C2-C30 alkenyl radicals, in particular C2-C10 alkenyl radicals; the said alkyl or alkenyl radicals being optionally interrupted by one or more heteroatoms, divalent groups or their combinations chosen from -O-, -S-, -C(O)- or -N(R1)-; with R1 denoting a hydrogen atom or a C1-C10 alkyl radical, preferably interrupted by an amido -C(O)-N-(R2)- group with R2 representing a hydrogen atom or a C1-C4 alkyl group;
ii) C6-C30 aryl radicals, in particular C6-Ci4 aryl radicals, such as phenyl;
iii) non-aromatic mono- or polycyclic heterocyclic radicals which comprise from 3 to 50 ring members, preferably from 3 to 14 ring members, which are unsaturated or saturated and which optionally comprise one or more heteroatoms chosen from O, S or N;
it being possible for these different radicals to be optionally substituted by one or more groups chosen from hydroxyl, mercaptan, aldehyde, amino, (di)(Ci- Cio)alkylamino, (di)hydroxy(Ci-Cio)alkylamino, C2-C10 acyl, amido: R1-C(O)- N(R1)-, (C2-C10 acyl)amido: R1-C(O)-N(R1)-C(O)-, halogen, sulfo, carboxyl, cyano or (Ci-Cio)alkoxy groups, with R1, which are identical or different, being as defined above, it being possible for the aryl and non-aromatic mono- or polycyclic radicals in addition to be substituted by C1-C10 alkyl radicals
· and n denotes an integer ranging from 1 to 100,
the composition comprising neither a colouring agent nor a reducing agent.
2. Method according to Claim 1 , in which n denotes an integer ranging from 1 to 3 and is preferably equal to 1 .
3. Method according to any one of Claims 1 to 2, in which the compound or compounds of formula (I) are such that R is a radical resulting from a mono- or polyalcohol comprising between 1 and 10 hydroxyl groups, such as from a mono- or polyalcohol chosen from methanol, ethanol, propanol, isopropanol, butanol, hexanol, ethylene glycol, glycerol, dihydroxyacetone, glucose or sorbitol.
4. Method according to any one of Clainns 1 to 3, in which the compound or compounds of formula (I) are chosen from methyl glyoxylate, ethyl glyoxylate, 2- hydroxyethyl glyoxylate, 3-hydroxypropyl glyoxylate, glyceryl glyoxylate, dihydroxyacetone glyoxylate, glyceryl diglyoxylate or triglyoxylate, sorbitol mono-, di- or triglyoxylate, glucose mono-, di- or triglyoxylate, 1 ,3-propanediol glyoxylate, 1 ,2-ethanediol glyoxylate and the compounds having the following formulae:
5. Method according to one of the preceding claims, in which n is equal to 1 .
6. Method according to one of the preceding claims, in which the compound or compounds of formula (I) are present in the cosmetic composition at a concentration ranging from 0.01 % to 50% by weight, in particular from 0.1 % to 20% by weight and preferably from 1 % to 15% by weight, with respect to the total weight of the composition.
7. Method according to one of the preceding claims, the said composition being aqueous and preferably comprising water at a concentration of between 5% and 98% by weight, in particular 20% and 95% by weight and better still 50% and 90% by weight, with respect to the total weight of the composition.
8. Method according to one of Claims 1 to 6, the said composition being anhydrous.
9. Method according to one of the preceding claims, comprising at least one cosmetic ingredient chosen from propellants; oils; solid fatty substances and in particular Cs-C4o esters, Cs-C4o acids or Cs-C4o alcohols; non-ionic surfactants, cationic surfactants, anionic surfactants, amphoteric surfactants or zwitterionic surfactants; sunscreens; moisturizing agents; antidandruff agents; antioxidants; chelating agents; pearlescent and opacifying agents; plasticizing or coalescing agents; hydroxy acids; fillers; silicones and in particular polydimethylsiloxanes; polymeric or non-polymeric thickeners; gelling agents; emulsifiers; polymers, in particular conditioning or styling polymers; fragrances; basifying or acidifying agents; silanes; or crosslinking agents.
10. Method according to one of the preceding claims, which is provided in the form of a product for caring for, cleansing and/or making up the skin of the body or face, the lips, the eyebrows, the eyelashes, the nails and the hair, of an anti-sun or self- tanning product, of a body hygiene product or of a hair product, in particular for caring for, cleaning, styling or shaping the hair.
1 1 . Method according to any one of the preceding claims, for the conditioning, shaping, reinforcing and/or repairing of the hair, in particular for introducing or improving the disentangling, smoothing, combability, manageability or softness of the hair.
12. Method according to any one of the preceding claims, comprising a rinsing stage and/or a heat treatment stage, in particular with a crimping or smoothing iron, at a temperature of between 150°C and 250°C.
13. Method according to one of the preceding claims, for the care and/or protection of the hair, especially of hair which has been weakened and/or damaged, for example by chemical or mechanical treatments.
14. Use of a compound of formula (I) according to any one of Claims 1 to 5 for caring for, cleaning, styling or shaping the hair.
15. Use of a compound of formula (I) according to any one of Claims 1 to 5 for the conditioning, shaping, reinforcing and/or repairing of the hair, in particular for introducing or improving the disentangling, smoothing, combability, manageability and/or softness of the hair.
16. Composition for the cosmetic treatment of keratinous substances comprising at least one compound of formula (I) and also its salts; its hydrates; its cyclic
(thio)acetals; its (thio)hemiacetals and its optical and geometrical isomers: 
in which formula (I):
• R represents a radical resulting from a mono- or polyalcohol,
R representing a radical chosen from:
i) C2-C30 alkyl radicals, in particular C2-C10 alkyl radicals; or C2-C30 alkenyl radicals, in particular C2-C10 alkenyl radicals; the said alkyl or alkenyl radicals being optionally interrupted by one or more heteroatoms, divalent groups or their combinations chosen from -O-, -S-, -C(O)- or -N(R1)-; with R1 denoting a hydrogen atom or a C1-C10 alkyl radical, preferably interrupted by an amido -C(O)-N-(R2)- group with R2 representing a hydrogen atom or a Ci-C4 alkyl group;
ii) C6-C30 aryl radicals, in particular C6-Ci4 aryl radicals, such as phenyl;
iii) non-aromatic mono- or polycyclic heterocyclic radicals, which comprise from 3 to 50 ring members, preferably from 3 to 14 ring members, which are unsaturated or saturated and which optionally comprise one or more heteroatoms chosen from O, S or N;
it being possible for these different radicals to be optionally substituted by one or more groups chosen from hydroxyl, mercaptan, aldehyde, amino, (di)(Ci- Cio)alkylamino, (di)hydroxy(Ci-Cio)alkylamino, C2-C10 acyl, amido: R1-C(O)- N(R1)-, (C2-C10 acyl)amido: R1-C(O)-N(R1)-C(O)-, halogen, sulfo, carboxyl, cyano or (Ci-Cio)alkoxy groups, with R1, which are identical or different, being as defined above, it being possible for the aryl and non-aromatic mono- or polycyclic radicals in addition to be substituted by C1-C10 alkyl radicals
· and n denotes an integer ranging from 1 to 100.
17. Composition according to the preceding claim, resulting from the mixing at the time of use of at least two compositions, one of which comprising one or more compounds of formula (I), the composition comprising one or more compounds of formula (I) preferably being anhydrous.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR1251235A FR2986704B1 (en) | 2012-02-09 | 2012-02-09 | COSMETIC TREATMENT PROCESS AND COMPOSITION COMPRISING A GLYOXYLIC ACID ESTER |
| FR1251235 | 2012-02-09 | ||
| US201261640251P | 2012-04-30 | 2012-04-30 | |
| US61/640,251 | 2012-04-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO2013117770A2 true WO2013117770A2 (en) | 2013-08-15 |
| WO2013117770A3 WO2013117770A3 (en) | 2014-07-03 |
Family
ID=46489336
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP2013/052710 WO2013117770A2 (en) | 2012-02-09 | 2013-02-11 | Cosmetic treatment method, and composition comprising a glyoxylic acid ester |
Country Status (2)
| Country | Link |
|---|---|
| FR (1) | FR2986704B1 (en) |
| WO (1) | WO2013117770A2 (en) |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015094760A1 (en) * | 2013-12-19 | 2015-06-25 | The Procter & Gamble Company | Shaping keratin fibres using carbonate ester |
| US20180344619A1 (en) * | 2017-06-05 | 2018-12-06 | Momentive Performance Materials Inc. | Aqueous compositions for the treatment of hair |
| US10434051B2 (en) | 2014-12-19 | 2019-10-08 | The Procter And Gamble Company | Shaping keratin fibers using arabinose and ethylene carbonate |
| US10568826B2 (en) | 2014-12-19 | 2020-02-25 | The Procter And Gamble Company | Shaping keratin fibres using a pretreatment and a protein crosslinking composition |
| US10729630B2 (en) | 2013-12-19 | 2020-08-04 | The Procter & Gamble Company | Shaping keratin fibres using an active agent comprising at least two functional groups selected from: —C(OH)- and —C(=O)OH |
| US10912726B2 (en) | 2013-12-19 | 2021-02-09 | The Procter And Gamble Company | Shaping keratin fibres using a reducing composition and a fixing composition |
| US10945931B2 (en) | 2015-06-18 | 2021-03-16 | The Procter And Gamble Company | Shaping keratin fibres using dialdehyde compounds |
| US11090255B2 (en) | 2018-12-04 | 2021-08-17 | Momentive Performance Materials Inc. | Use of polycarboxylic acid compounds for the treatment of fibrious amino acid based substrates, especially hair |
| US11096879B2 (en) | 2013-12-19 | 2021-08-24 | The Procter And Gamble Plaza | Shaping keratin fibres using an active agent comprising a functional group selected from the group consisting of: -C(=O)-, -C(=O)-H, and -C(=O)-O- |
| US11103434B2 (en) | 2013-12-19 | 2021-08-31 | The Procter And Gamble Company | Shaping keratin fibres using carbonate ester |
| US11110046B2 (en) | 2013-12-19 | 2021-09-07 | The Procter And Gamble Company | Shaping keratin fibres using 2-hydroxypropane-1,2,3-tricarboxylic acid and/or 1,2,3,4-butanetetracarboxylic acid |
| US11129784B2 (en) | 2013-12-19 | 2021-09-28 | The Procter And Gamble Company | Shaping keratin fibres using oxoethanoic acid and/or derivatives thereof |
| US11154480B2 (en) | 2013-12-19 | 2021-10-26 | The Procter And Gamble Company | Shaping keratin fibres using a sugar |
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| DE19853842C2 (en) * | 1998-11-23 | 2000-09-14 | Erich Ruf | Water-soluble allantoin compound and method for producing a water-soluble allantoin compound |
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| US11103434B2 (en) | 2013-12-19 | 2021-08-31 | The Procter And Gamble Company | Shaping keratin fibres using carbonate ester |
| US10729630B2 (en) | 2013-12-19 | 2020-08-04 | The Procter & Gamble Company | Shaping keratin fibres using an active agent comprising at least two functional groups selected from: —C(OH)- and —C(=O)OH |
| US10912726B2 (en) | 2013-12-19 | 2021-02-09 | The Procter And Gamble Company | Shaping keratin fibres using a reducing composition and a fixing composition |
| US11154480B2 (en) | 2013-12-19 | 2021-10-26 | The Procter And Gamble Company | Shaping keratin fibres using a sugar |
| US11129784B2 (en) | 2013-12-19 | 2021-09-28 | The Procter And Gamble Company | Shaping keratin fibres using oxoethanoic acid and/or derivatives thereof |
| JP2016540005A (en) * | 2013-12-19 | 2016-12-22 | ザ プロクター アンド ギャンブル カンパニー | Molding of keratin fiber using carbonate ester |
| US11110046B2 (en) | 2013-12-19 | 2021-09-07 | The Procter And Gamble Company | Shaping keratin fibres using 2-hydroxypropane-1,2,3-tricarboxylic acid and/or 1,2,3,4-butanetetracarboxylic acid |
| WO2015094760A1 (en) * | 2013-12-19 | 2015-06-25 | The Procter & Gamble Company | Shaping keratin fibres using carbonate ester |
| US10064799B2 (en) | 2013-12-19 | 2018-09-04 | The Procter & Gamble Company | Shaping keratin fibres using carbonate ester |
| US11096879B2 (en) | 2013-12-19 | 2021-08-24 | The Procter And Gamble Plaza | Shaping keratin fibres using an active agent comprising a functional group selected from the group consisting of: -C(=O)-, -C(=O)-H, and -C(=O)-O- |
| US10568826B2 (en) | 2014-12-19 | 2020-02-25 | The Procter And Gamble Company | Shaping keratin fibres using a pretreatment and a protein crosslinking composition |
| US10434051B2 (en) | 2014-12-19 | 2019-10-08 | The Procter And Gamble Company | Shaping keratin fibers using arabinose and ethylene carbonate |
| US10945931B2 (en) | 2015-06-18 | 2021-03-16 | The Procter And Gamble Company | Shaping keratin fibres using dialdehyde compounds |
| CN110996889A (en) * | 2017-06-05 | 2020-04-10 | 莫门蒂夫性能材料股份有限公司 | Aqueous composition for hair treatment |
| US20180344619A1 (en) * | 2017-06-05 | 2018-12-06 | Momentive Performance Materials Inc. | Aqueous compositions for the treatment of hair |
| US11179312B2 (en) | 2017-06-05 | 2021-11-23 | Momentive Performance Materials Inc. | Aqueous compositions for the treatment of hair |
| US11090255B2 (en) | 2018-12-04 | 2021-08-17 | Momentive Performance Materials Inc. | Use of polycarboxylic acid compounds for the treatment of fibrious amino acid based substrates, especially hair |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2986704B1 (en) | 2015-08-21 |
| FR2986704A1 (en) | 2013-08-16 |
| WO2013117770A3 (en) | 2014-07-03 |
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