EP1592393A2 - Hydrogelling cationic amide for cosmetics - Google Patents

Hydrogelling cationic amide for cosmetics

Info

Publication number
EP1592393A2
EP1592393A2 EP04700050A EP04700050A EP1592393A2 EP 1592393 A2 EP1592393 A2 EP 1592393A2 EP 04700050 A EP04700050 A EP 04700050A EP 04700050 A EP04700050 A EP 04700050A EP 1592393 A2 EP1592393 A2 EP 1592393A2
Authority
EP
European Patent Office
Prior art keywords
use according
thickening
fatty chain
hair
mol
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP04700050A
Other languages
German (de)
French (fr)
Inventor
Isabelle Rollat-Corvol
Henri Samain
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
LOreal SA
Original Assignee
LOreal SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from FR0350009A external-priority patent/FR2850566B1/en
Application filed by LOreal SA filed Critical LOreal SA
Publication of EP1592393A2 publication Critical patent/EP1592393A2/en
Withdrawn legal-status Critical Current

Links

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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
    • 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

Definitions

  • the subject of the invention is the use, in cosmetics, of cationic hydrogelling amides.
  • Thickened compositions are known, in particular hair gels, which are generally applied to the hair before shaping the hairstyle. To shape and fix the hairstyle, we then do a brushing or styling.
  • compositions in particular these gels, can contain polymer resins.
  • thickened hair cosmetic compositions also have the major drawback of giving rise to a dusting effect.
  • dusting means the ability of the material obtained by drying the hair composition to form a powder after its application to the hair.
  • aqueous cosmetic media are, in general, gelled by crosslinked hydrophilic polymers. It is difficult to produce aqueous cosmetic gels which, after drying on the hair, have good resistance to a humid climate.
  • the invention proposes the use in cosmetics of small chiral molecules with amide functions and with fatty chains, containing ionic functions. These molecules are described in the literature, and in particular in the following publications: Chemistry Letters 2002, (7), 704-705; New Journal of Chemistry 2002, 26 (7), 817-818; Chemical Communications (Cambridge, United Kingdom) 2002, (8), 884-885.
  • the subject of the invention is the use in a cosmetic composition, in aqueous medium or water + solvent, of a non-phosphorus ionic thickening molecular compound, of molecular weight less than 2,000 g / mol and comprising at least:
  • fatty chain comprising at least eight carbons.
  • molecular compound is meant, within the meaning of the present invention, any compound whose backbone does not result from a polymerization. This does not exclude that the compound may contain one or more polyoxyalkylenated or polyoxyglycerolated groups.
  • cationic molecule is meant, within the meaning of the present invention, a molecule comprising at least one quaternized nitrogen atom.
  • the ionic thickening non-phosphorous molecular compound has a molecular weight of less than 2,000 g / mol and it comprises at least:
  • the fatty chain contains between 8 and 30 carbon atoms, and more preferably between 8 and 22 carbon atoms.
  • the thickening molecular compound has a molecular weight of less than 100 g / mol, and preferably less than 800 g / mol.
  • At least one fatty chain is linked directly to the amide group, and in particular, at least one fatty chain is linked to the amide group by a carbonyl function. More preferably, the thickening molecular compound contains at least two fatty chains and, even more preferably, at least one fatty chain is part of an ester group.
  • the molecular thickening compound contains at least two sequences -CONH-.
  • the thickening compound is present in the aqueous medium at a concentration by weight of between 0.1 and 60%, and preferably between 0.25 and 25% by weight, relative to the total weight of the cosmetic composition.
  • the composition forms a film after drying.
  • the film is insoluble in pure water, at room temperature. On the other hand, it can be soluble, at acidic or alkaline pH.
  • molecular thickening compound mention may be made of 1- (11- ((((S) - 1-ethoxycarbonyl-5 - ((1-oxododecyl) amino) pentyl) amino) - 11-oxoundecyl) pyridinium bromide).
  • These molecular compounds can be applied to hair, skin, eyelashes, eyebrows and nails. They are used especially for hair.
  • Application 1 the molecule is applied to the hair in the form of a gel or a solution in a hair composition containing water, alcohol or another cosmetically acceptable solvent or a mixture thereof.
  • Application 2 the molecule is applied to the hair in the form of a solution in a hair composition containing one or more cosmetically acceptable solvents. Water is applied in a second step, to form a gel.
  • Application 3 the molecule is applied to the hair in the form of a gel or a solution in a hair composition containing water, alcohol or another cosmetically acceptable solvent or a mixture thereof. After drying, the deposit formed on the hair is removed by application:
  • a gel containing 1% of active material of bromide of 1- (11 - (((1S) -1-ethoxycarbonyl-5 - ((1-oxododecyl) amino) pentyl) amino) - 11 -oxoundecyl) pyridinium is produced.
  • this gel gives a resistance to humidity greater than that of Carbopol Ultrez 10® marketed by Noveon (crosslinked poly acrylic acid) at 1% by weight m. at..

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

The invention relates to the use of a cosmetic composition, in aqueous media or water and a solvent, having a non-phosphated, cationic, gelling molecular composition with a molecular weight less than 2,000 g/mol and comprising at least two amide groups, one asymmetric carbon and one fatty chain with at least eight carbon atoms.

Description

AMIDE CATIONIQUE HYDROGELIFIANT EN COSMETIQUE CATIONIC HYDROGELIFYING AMIDE IN COSMETICS
L'invention a pour objet l'utilisation, en cosmétique, d'amides cationiques hydrogélifiants.The subject of the invention is the use, in cosmetics, of cationic hydrogelling amides.
On connaît des compositions épaissies, notamment des gels capillaires, qui sont généralement appliquées sur les cheveux avant de mettre en forme la coiffure. Pour mettre en forme et fixer la coiffure, on effectue ensuite un brushing ou une mise en plis.Thickened compositions are known, in particular hair gels, which are generally applied to the hair before shaping the hairstyle. To shape and fix the hairstyle, we then do a brushing or styling.
Ces compositions épaissies, notamment ces gels, peuvent contenir des résines polymères.These thickened compositions, in particular these gels, can contain polymer resins.
Toutefois, elles présentent souvent l'inconvénient d'altérer les propriétés cosmétiques des cheveux. Ainsi, les cheveux peuvent devenir rêches, difficiles à démêler, perdre leur toucher et leur aspect agréables ou encore manquer de corps. On recherche donc de telles compositions cosmétiques capillaires procurant de bonnes propriétés cosmétiques, notamment en terme de démêlage, de douceur et de toucher.However, they often have the drawback of altering the cosmetic properties of the hair. Thus, the hair can become coarse, difficult to disentangle, lose its touch and its pleasant appearance or even lack body. We are therefore looking for such hair cosmetic compositions providing good cosmetic properties, in particular in terms of detangling, softness and feel.
En outre, les compositions cosmétiques capillaires épaissies présentent également l'inconvénient majeur de donner lieu à un effet de poudrage. Au sens de la présente invention, on entend par «poudrage », l'aptitude du matériau obtenu par séchage de la composition capillaire à former une poudre après son application sur les cheveux.In addition, thickened hair cosmetic compositions also have the major drawback of giving rise to a dusting effect. For the purposes of the present invention, the term "dusting" means the ability of the material obtained by drying the hair composition to form a powder after its application to the hair.
Les milieux cosmétiques aqueux sont, en général, gélifiés par des polymères hydrophiles réticulés. Il est difficile de réaliser des gels cosmétiques aqueux qui auraient, après le séchage sur les cheveux, une bonne résistance à un climat humide.The aqueous cosmetic media are, in general, gelled by crosslinked hydrophilic polymers. It is difficult to produce aqueous cosmetic gels which, after drying on the hair, have good resistance to a humid climate.
Il existe donc un besoin de trouver des compositions cosmétiques, notamment capillaires épaissies, notamment des gels capillaires, qui ne présentent pas l'ensemble des inconvénients indiqués ci-dessus, et qui, en particulier résistent à un climat humide.There is therefore a need to find cosmetic compositions, in particular thickened capillaries, in particular hair gels, which do not have all of the drawbacks indicated above, and which, in particular withstand a humid climate.
Pour résoudre ce problème, l'invention propose l'utilisation en cosmétique de petites molécules chirales à fonctions amides et à chaînes grasses, contenant des fonctions ioniques. Ces molécules sont décrites dans la littérature, et notamment dans les publications suivantes: Chemistry Letters 2002, (7), 704-705; New Journal of Chemistry 2002, 26 (7), 817-818; Chemical Communications (Cambridge, United Kingdom) 2002, (8), 884-885.To solve this problem, the invention proposes the use in cosmetics of small chiral molecules with amide functions and with fatty chains, containing ionic functions. These molecules are described in the literature, and in particular in the following publications: Chemistry Letters 2002, (7), 704-705; New Journal of Chemistry 2002, 26 (7), 817-818; Chemical Communications (Cambridge, United Kingdom) 2002, (8), 884-885.
La Demanderesse a maintenant découvert qu'après le séchage sur les cheveux, ces gels forment des dépôts ayant une excellente tenue à l'humidité.The Applicant has now discovered that after drying on the hair, these gels form deposits having excellent resistance to humidity.
L'invention a pour objet l'utilisation dans une composition cosmétique, en milieu aqueux ou eau+solvant, d'un composé moléculaire épaississant ionique non phosphore, de poids moléculaire inférieur à 2 000 g/mol et comprenant au moins:The subject of the invention is the use in a cosmetic composition, in aqueous medium or water + solvent, of a non-phosphorus ionic thickening molecular compound, of molecular weight less than 2,000 g / mol and comprising at least:
- deux groupements amide,- two amide groups,
- un carbone asymétrique,- an asymmetric carbon,
- une chaîne grasse comportant au moins huit carbones.- a fatty chain comprising at least eight carbons.
Par "composé moléculaire", on entend, au sens de la présente invention, tout composé dont le squelette ne résulte pas d'une polymérisation. Ceci n'exclut pas que le composé puisse contenir un ou plusieurs groupement polyoxyalkylénés ou polyoxyglycérolés.By "molecular compound" is meant, within the meaning of the present invention, any compound whose backbone does not result from a polymerization. This does not exclude that the compound may contain one or more polyoxyalkylenated or polyoxyglycerolated groups.
Par "molécule cationique", on entend, au sens de la présente invention, une molécule comprenant au moins un atome d'azote quaternisé.By "cationic molecule" is meant, within the meaning of the present invention, a molecule comprising at least one quaternized nitrogen atom.
COMPOSE MOLECULAIRE EPAISSISSANTTHICKENING MOLECULAR COMPOUND
Conformément à l'invention, le composé moléculaire épaississant ionique, non phosphore, est de poids moléculaire inférieur à 2 000 g/mol et il comprend au moins:In accordance with the invention, the ionic thickening non-phosphorous molecular compound has a molecular weight of less than 2,000 g / mol and it comprises at least:
- deux groupements amide,- two amide groups,
- un carbone asymétrique, - une chaîne grasse comportant au moins huit carbones.- an asymmetric carbon, - a fatty chain comprising at least eight carbons.
Plus avantageusement encore, la chaîne grasse comporte entre 8 et 30 atomes de carbone, et plus préférentiellement entre 8 et 22 atomes de carbone. Selon une version préférée, le composé moléculaire épaississant est de poids moléculaire inférieur à lOOOg/mol, et de préférence, inférieur à 800 g/mol.More advantageously still, the fatty chain contains between 8 and 30 carbon atoms, and more preferably between 8 and 22 carbon atoms. According to a preferred version, the thickening molecular compound has a molecular weight of less than 100 g / mol, and preferably less than 800 g / mol.
Avantageusement, au moins une chaîne grasse est liée directement au groupement amide, et en particulier, au moins une chaîne grasse est liée au groupement amide par une fonction carbonyle. Plus préférentiellement, le composé moléculaire épaississant contient au moins deux chaînes grasses et, encore plus préférentiellement, au moins une chaîne grasse fait partie d'un groupement ester.Advantageously, at least one fatty chain is linked directly to the amide group, and in particular, at least one fatty chain is linked to the amide group by a carbonyl function. More preferably, the thickening molecular compound contains at least two fatty chains and, even more preferably, at least one fatty chain is part of an ester group.
Selon on mode préféré de l'invention, le composé moléculaire épaississant contient au moins deux enchaînements -CONH-.According to a preferred embodiment of the invention, the molecular thickening compound contains at least two sequences -CONH-.
En particulier, le composé épaississant est présent dans le milieu aqueux à une concentration en poids comprise entre 0,1 et 60 %, et de préférence entre 0,25 et 25 % en poids, par rapport au poids total de la composition cosmétique.In particular, the thickening compound is present in the aqueous medium at a concentration by weight of between 0.1 and 60%, and preferably between 0.25 and 25% by weight, relative to the total weight of the cosmetic composition.
Préférentiellement, la composition forme un film après séchage. Dans un mode préféré, le film est insoluble dans l'eau pure, à la température ambiante. Il peut, par contre, être soluble, à pH acide ou alcalin.Preferably, the composition forms a film after drying. In a preferred mode, the film is insoluble in pure water, at room temperature. On the other hand, it can be soluble, at acidic or alkaline pH.
En tant que composé moléculaire épaississant, on peut citer le bromure de 1-(11- ((( 1 S)- 1 -éthoxycarbonyl-5-(( 1 -oxododécyl)amino)pentyl)amino)- 11 -oxoundécyl) pyridinium.As molecular thickening compound, mention may be made of 1- (11- ((((S) - 1-ethoxycarbonyl-5 - ((1-oxododecyl) amino) pentyl) amino) - 11-oxoundecyl) pyridinium bromide).
Ces composés moléculaires peuvent être appliqués sur les cheveux, la peau, les cils, les sourcils et les ongles. On les emploie tout particulièrement pour les cheveux.These molecular compounds can be applied to hair, skin, eyelashes, eyebrows and nails. They are used especially for hair.
II existe différents modes d'application du composé moléculaire épaississant sur les cheveux. On peut citer ceux-ci: Application 1 : la molécule est appliquée sur les cheveux sous forme de gel ou de solution dans une composition capillaire contenant de l'eau, de l'alcool ou un autre solvant cosmétiquement acceptable ou leur mélange.There are different modes of application of the thickening molecular compound on the hair. We can cite these: Application 1: the molecule is applied to the hair in the form of a gel or a solution in a hair composition containing water, alcohol or another cosmetically acceptable solvent or a mixture thereof.
Application 2 : la molécule est appliquée sur les cheveux sous forme de solution dans une composition capillaire contenant un ou plusieurs solvants cosmétiquement acceptables. L'eau est appliquée en deuxième temps, pour former un gel.Application 2: the molecule is applied to the hair in the form of a solution in a hair composition containing one or more cosmetically acceptable solvents. Water is applied in a second step, to form a gel.
Application 3 : la molécule est appliquée sur les cheveux sous forme de gel ou de solution dans une composition capillaire contenant de l'eau, de l'alcool ou un autre solvant cosmétiquement acceptable ou leur mélange. Après séchage, le dépôt formé sur les cheveux est éliminé par application:Application 3: the molecule is applied to the hair in the form of a gel or a solution in a hair composition containing water, alcohol or another cosmetically acceptable solvent or a mixture thereof. After drying, the deposit formed on the hair is removed by application:
- d'eau chaude- hot water
- d'une solution aqueuse à pH acide ou basique - d'un solvant ou d'un mélange de plusieurs solvants.- an aqueous solution at acidic or basic pH - a solvent or a mixture of several solvents.
L'invention pourra être mieux comprise à l'aide de l'exemple non limitatif qui suit et qui constitue un mode d'utilisation préférentiel des amides ioniques hydrogélifiés.The invention can be better understood with the aid of the nonlimiting example which follows and which constitutes a preferred mode of use of the hydrogelified ionic amides.
EXEMPLE:EXAMPLE:
On réalise un gel contenant 1 % en matière active de bromure de 1-(11-(((1S)-1- éthoxycarbonyl-5-(( 1 -oxododécyl)amino)pentyl)amino)- 11 -oxoundécyl) pyridinium.A gel containing 1% of active material of bromide of 1- (11 - (((1S) -1-ethoxycarbonyl-5 - ((1-oxododecyl) amino) pentyl) amino) - 11 -oxoundecyl) pyridinium is produced.
Après l'application sur cheveux, on a remarqué que ce gel donne une tenue à l'humidité supérieure à celle du Carbopol Ultrez 10 ® commercialisé par Noveon (poly acide acrylique réticulé) à 1% en poids m. a.. After application to hair, it has been noted that this gel gives a resistance to humidity greater than that of Carbopol Ultrez 10® marketed by Noveon (crosslinked poly acrylic acid) at 1% by weight m. at..

Claims

REVENDICATIONS
1. Utilisation dans une composition cosmétique, en milieu aqueux ou eau+solvant, d'un composé moléculaire épaississant cationique non phosphore, de poids moléculaire inférieur à 2 000 g/mol et comprenant au moins:1. Use in a cosmetic composition, in aqueous medium or water + solvent, of a non-phosphorous cationic thickening molecular compound, of molecular weight less than 2,000 g / mol and comprising at least:
- deux groupements amide,- two amide groups,
- un carbone asymétrique,- an asymmetric carbon,
- une chaîne grasse comportant au moins huit carbones. 2. Utilisation selon la revendication 1, caractérisée par le fait que le composé moléculaire épaississant contient au moins deux enchaînements - CONH-.- a fatty chain comprising at least eight carbons. 2. Use according to claim 1, characterized in that the thickening molecular compound contains at least two sequences - CONH-.
3. Utilisation selon l'une quelconque des revendications précédentes, caractérisée par le fait que la chaîne grasse comporte entre 8 et 30 atomes de carbone, et plus préférentiellement entre 8 et 22 atomes de carbone.3. Use according to any one of the preceding claims, characterized in that the fatty chain contains between 8 and 30 carbon atoms, and more preferably between 8 and 22 carbon atoms.
4.Utilisation selon l'une quelconque des revendications précédentes, caractérisée par le fait que le composé moléculaire épaississant est de poids moléculaire inférieur à lOOOg/mol, et de préférence, inférieur à 800 g/mol.4.Use according to any one of the preceding claims, characterized in that the thickening molecular compound is of molecular weight less than lOOOg / mol, and preferably less than 800 g / mol.
5. Utilisation selon l'une quelconque des revendications précédentes, caractérisée par le fait qu'au moins une chaîne grasse est liée directement au groupement amide.5. Use according to any one of the preceding claims, characterized in that at least one fatty chain is linked directly to the amide group.
6. Utilisation selon l'une quelconque des revendications 1 à 4, caractérisée par le fait qu'au moins une chaîne grasse est liée au groupement amide par une fonction carbonyle. 7.Utilisation selon l'une quelconque des revendications précédentes, caractérisée par le fait que le composé moléculaire épaississant contient au moins deux chaînes grasses.6. Use according to any one of claims 1 to 4, characterized in that at least one fatty chain is linked to the amide group by a carbonyl function. 7.Use according to any one of the preceding claims, characterized in that the thickening molecular compound contains at least two fatty chains.
8. Utilisation selon l'une quelconque des revendications précédentes, caractérisée par le fait qu'au moins une chaîne grasse fait partie d'un groupement ester.8. Use according to any one of the preceding claims, characterized in that at least one fatty chain is part of an ester group.
9.Utilisation selon l'une quelconque des revendications précédentes, caractérisée par le fait que le composé épaississant est présent dans le milieu aqueux à une concentration en poids comprise entre 0,1 et 60 %, et de préférence entre 0,25 et 25 % en poids, par rapport au poids total de la composition cosmétique. lO.Utilisation selon l'une quelconque des revendications précédentes, caractérisée par le fait que la composition forme un film après séchage.9.Use according to any one of the preceding claims, characterized in that the thickening compound is present in the aqueous medium at a concentration by weight of between 0.1 and 60%, and preferably between 0.25 and 25% by weight, relative to the total weight of the cosmetic composition. 10. Use according to any one of the preceding claims, characterized in that the composition forms a film after drying.
11. Utilisation selon la revendication 9, caractérisée par le fait que le film est insoluble dans l'eau pure à la température ambiante.11. Use according to claim 9, characterized in that the film is insoluble in pure water at room temperature.
12. Utilisation selon la revendication 10, caractérisée par le fait que le film est soluble à pH acide ou alcalin. 12. Use according to claim 10, characterized in that the film is soluble at acidic or alkaline pH.
EP04700050A 2003-02-03 2004-01-02 Hydrogelling cationic amide for cosmetics Withdrawn EP1592393A2 (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
FR0350009 2003-02-03
FR0350009A FR2850566B1 (en) 2003-02-03 2003-02-03 HYDROGENIFYING CATIONIC AMIDE IN COSMETICS
US47779503P 2003-06-10 2003-06-10
US477795P 2003-06-10
PCT/FR2004/000225 WO2004068995A2 (en) 2003-02-03 2004-01-02 Hydrogelling cationic amide for cosmetics

Publications (1)

Publication Number Publication Date
EP1592393A2 true EP1592393A2 (en) 2005-11-09

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP04700050A Withdrawn EP1592393A2 (en) 2003-02-03 2004-01-02 Hydrogelling cationic amide for cosmetics

Country Status (3)

Country Link
EP (1) EP1592393A2 (en)
JP (1) JP2006516555A (en)
WO (1) WO2004068995A2 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2813488B1 (en) 2012-02-09 2018-05-16 Ajinomoto Co., Inc. Amphoteric ion-type basic amino acid derivative

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2004068995A3 *

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Publication number Publication date
JP2006516555A (en) 2006-07-06
WO2004068995A3 (en) 2004-10-21
WO2004068995A2 (en) 2004-08-19

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