EP1778731A2 - Nouveaux composes polysaccharidiens amphoteres a fonction(s) sulfonate, composition les comprenant, et utilisation cosmetique correspondante - Google Patents

Nouveaux composes polysaccharidiens amphoteres a fonction(s) sulfonate, composition les comprenant, et utilisation cosmetique correspondante

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Publication number
EP1778731A2
EP1778731A2 EP05798113A EP05798113A EP1778731A2 EP 1778731 A2 EP1778731 A2 EP 1778731A2 EP 05798113 A EP05798113 A EP 05798113A EP 05798113 A EP05798113 A EP 05798113A EP 1778731 A2 EP1778731 A2 EP 1778731A2
Authority
EP
European Patent Office
Prior art keywords
group
branched
linear
polysaccharide compound
gum
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Withdrawn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
EP05798113A
Other languages
German (de)
English (en)
Inventor
Michel Philippe
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 FR0408996A external-priority patent/FR2874380B1/fr
Application filed by LOreal SA filed Critical LOreal SA
Publication of EP1778731A2 publication Critical patent/EP1778731A2/fr
Withdrawn legal-status Critical Current

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Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00Make-up preparations; Body powders; Preparations for removing make-up
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73Polysaccharides
    • A61K8/731Cellulose; Quaternized cellulose derivatives
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/91Graft copolymers
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/02Preparations for cleaning the hair
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/10Preparations for permanently dyeing the hair
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/12Preparations containing hair conditioners
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08BPOLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B15/00Preparation of other cellulose derivatives or modified cellulose, e.g. complexes
    • C08B15/05Derivatives containing elements other than carbon, hydrogen, oxygen, halogens or sulfur
    • C08B15/06Derivatives containing elements other than carbon, hydrogen, oxygen, halogens or sulfur containing nitrogen, e.g. carbamates
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L1/00Compositions of cellulose, modified cellulose or cellulose derivatives
    • C08L1/08Cellulose derivatives
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/54Polymers characterized by specific structures/properties
    • A61K2800/542Polymers characterized by specific structures/properties characterized by the charge
    • A61K2800/5428Polymers characterized by specific structures/properties characterized by the charge amphoteric or zwitterionic

Definitions

  • Novel amphoteric polysaccharide compounds containing sulfonate function(s), composition comprising them and cosmetic use thereof comprising them and cosmetic use thereof
  • the present invention relates to novel amphoteric polysaccharide compounds containing sulfonate function(s), to their use in cosmetics and to compositions comprising them.
  • keratin materials such as the hair and the skin, and more particularly sensitized hair, i.e. hair that has become damaged or embrittled, especially due to the chemical action of atmospheric agents and/or of hair treatments such as permanent-waving, dyeing or bleaching.
  • conditioning agents for example cationic polymers or silicones, which are intended mainly to repair or limit the harmful or undesirable effects induced by the various treatments or attacking factors to which hair fibres are more or less repeatedly subjected.
  • conditioning agents also improve the cosmetic behaviour of natural hair.
  • conditioning agents such as the amphoteric polysaccharides described in documents US 4 803 071 , US 4 464 523 , WO 90/03779 and FR 2 883 599 may be used in cosmetic hair compositions.
  • these polysaccharides are not very efficient as regards conditioning and remanence.
  • the Applicant has found that, after several uses, the hair becomes laden and lacks lightness.
  • One subj ect of the present invention is thus novel amphoteric polysaccharide compounds containing sulfonate function(s) as described below.
  • a second subj ect of the invention consists of a use of such a polysaccharide compound in cosmetics and especially for the cosmetic treatment of keratin materials, such as caring for and protecting the hair, hairstyling, permanent-waving, relaxing, dyeing or bleaching the hair, or alternatively cleansing and care of the skin, or makeup of the skin, the lips or the nails.
  • a subject of the invention is also a cosmetic composition comprising at least one polysaccharide compound according to the invention, in a cosmetically acceptable medium.
  • amphoteric polysaccharide compounds containing sulfonate function(s) according to the invention bear, as substituents other than the sulfonate functions, at least one anionic group and at least one cationic group, the said groups being linked to the polysaccharide chain via the oxygen atoms of the saccharide units.
  • amphoteric polysaccharide compounds containing sulfonate function(s) according to the invention may be represented by formula (I) below:
  • X, Y and Z represent, independently of each other:
  • each R which may be identical or different, represents Ri or -ORi ,
  • Ri represents a linear or branched, saturated or unsaturated, optionally hydroxylated C i -C 8 and preferably Ci -C 4 monovalent hydrocarbon-based group optionally comprising at least one ether and/or amine function in the hydrocarbon-based chain
  • A represents a linear or branched, saturated or unsaturated, optionally hydroxylated C i -C i 2 divalent hydrocarbon-based group optionally comprising at least one ether and/or amine function in the hydrocarbon-based chain, r is equal to 0 or 1 , r being 0 when CAT represents a cationic polymer chain obtained by grafting and polymerization of ethylenic monomers bearing an ammonium group,
  • An represents an anionic group chosen from:
  • V representing a hydrogen atom or an alkali metal or alkaline-earth metal, for example a sodium or potassium atom
  • CAT represents: - an ammonium group
  • R 2 , R 3 and R 4 represent, independently of each other, a hydrogen atom or a linear or branched, saturated or unsaturated, optionally hydroxylated C 1 -C 22 and preferably C i -C i 8 monovalent hydrocarbon-based group optionally comprising at least one ether and/or amine function in the hydrocarbon-based chain
  • Q " represents a mineral or organic anion, for example a halogen atom such as a chlorine or bromine atom, the chlorine atom being particularly preferred, or an acetate, a citrate, a lactate, an oleate or a behenate, or - a cationic polymer chain obtained by grafting and polymerization of ethylenic monomers bearing an ammonium group, for example of formula:
  • R 5 , R 6 and R 7 represent, independently of each other, a hydrogen atom, a linear or branched C 1 -C 22 and preferably C i -C i 8 alkyl group, or a linear or branched C 2 -C 22 and preferably C 2 -C] 8 alkenyl group,
  • Sulfo represents a sulfonic or sulfonate group, such as -SO 3 V, V having the same meaning as above
  • n is such that the degree of substitution of the poly ⁇ saccharide compound with an anionic group -CO 2 V and/or -PO 3 V 2 (DS(-)i ), is within the range from 0.01 to 1.5 and preferably from 0.05 to 1
  • m is such that the degree of substitution of the poly ⁇ saccharide compound with a cationic group (DS(+)) is within the range from 0.01 to 1.5 and preferably from 0.05 to 1
  • p is such that the degree of substitution of the poly- saccharide compound with a sulfonic or sulfonate group
  • (DS(-) 2 ) is within the range from 0.01 to 1.5 and preferably from 0.02 to 1 , the total degree of substitution of the polysaccharide compound not exceeding 3 , and it is preferably within the range from 0.05 to 2.5.
  • degree of substitution DS(-) i of the amphoteric polysaccharide compounds means the ratio of the number of hydroxyl groups substituted with an anionic group -CO 2 V and/or -PO 3 V 2 in the repeating unit to the number of elementary monosaccharides constituting the unit.
  • degree of substitution DS(-) 2 of the amphoteric polysaccharide compounds means the ratio of the number of hydroxyl groups substituted with a sulfonic or sulfonate group in the repeating unit to the number of elementary monosaccharides constituting the unit.
  • degree of substitution D S(+) of the amphoteric polysaccharide compounds means the ratio of the number of hydroxyl groups substituted with a cationic group in the repeating unit to the number of elementary monosaccharides constituting the unit.
  • the polysaccharide chain represented by P is preferably a cellulose, a starch, an inulin, a guar gum, a xanthan gum, a pullulan, an agar-agar, a sodium, potassium or ammonium alginate, a carrageenan, a dextran, a furcellaran, a gellan gum, a gum arabic, a gum tragacanth, a hyaluronic acid, a konjac mannan, a lignin sulfonate, a carob gum, a partially N-acetylated chitin, a pectin, a polydextrose, a rhamsan gum or a welan gum.
  • the polysaccharide chain is a cellulose, a carboxymethylcellulose, a hydroxyethylcellulose, a hydroxypropyl- cellulose, a hydroxypropylmethylcellulose, a methylcellulose, a starch, a starch acetate, a hydroxyethyl starch, a hydroxypropyl starch, an inulin, a guar gum, a carboxymethylguar gum, a carboxymethylhydroxy- propylguar gum, a hydroxyethylguar gum, a hydroxypropylguar gum or a xanthan gum.
  • the polysaccharide chain containing sulfonate function(s) preferably has a weight-average molecular mass within the range from 500 to 15 000 000 and better still from 1000 to 10 000 000.
  • Examples of linear or branched, saturated or unsaturated Ci -C i 2 and preferably C i -C 8 divalent hydrocarbon-based groups X, Y, Z or A that may especially be mentioned include linear or branched C i -C 8 alkylene groups, such as methylene, ethylene, n-propylene, isopropylene, n-butylene, tert-butylene, hexylene or octylene; linear or branched C 2 -C 8 alkylene groups, such as vinylene, allylene, crotonylene, butenylene, isobutenylene, tert-butenylene, hexenylene or octenylene. These groups may also bear at least one hydroxyl substituent and/or may comprise at least one ether and/or amine function in the alkylene or alkenylene chain.
  • linear or branched, saturated or unsaturated C i -C 8 and preferably C i -C 4 monovalent hydrocarbon-based groups Ri that may especially be mentioned include linear or branched Ci -C 4 alkyl groups, such as methyl, ethyl, n-propyl, isopropyl, n-butyl or tert-butyl; linear or branched C 2 -C 4 alkenyl groups, such as vinyl, allyl, crotonyl, butenyl, isobutenyl or tert-butenyl; the said groups possibly bearing at least one hydroxyl substituent and possibly comprising at least one ether and/or amine function in the alkyl or alkenyl chain.
  • Ci -C 4 alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl or tert-butyl
  • R 2 to R 7 examples include linear or branched C i -C 4 alkyl groups, such as methyl, ethyl, n-propyl, isopropyl, n-butyl or tert-butyl groups, and linear or branched Ci 2 -Ci 8 alkyl groups, such as lauryl, myristyl, cetyl or stearyl groups.
  • linear or branched C 2 -C i 8 and preferably C 2 -C 6 alkenyl groups examples include vinyl, allyl, crotonyl and butenyl groups.
  • amphoteric polysaccharide compounds that are most particularly preferred in the invention are those corresponding to formula (I) in which: P represents a cellulose, a carboxymethylcellulose, a hydroxyethyl- cellulose, a hydroxypropylcellulose, a hydroxypropylmethylcellulose, a methylcellulose, a starch, a starch acetate, a hydroxyethyl starch, a hydroxypropyl starch, an inulin, a guar gum, a carboxymethylguar gum, a carboxymethylhydroxypropylguar gum, a hydroxyethylguar gum, a hydroxypropylguar gum or a xanthan gum,
  • X, Y and Z represent, independently of each other, a linear or branched C i -C 8 alkylene group, such as methylene, ethylene, n-propylene, isopropylene, n-butylene, tert-butylene, hexylene or octylene; or a linear or branched C 2 -C 8 alkenylene group, such as vinylene, allylene, crotonylene, butenylene, isobutenylene, tert-butenylene, hexenylene or octenylene, or in which each R, which may be identical or different, represents Ri or OR 1 ,
  • Ri represents a linear or branched C 1 -C4 alkyl group, such as methyl, ethyl, n-propyl, isopropyl, n-butyl or tert-butyl; or a linear or branched
  • C 2 -C 4 alkenyl group such as vinyl, allyl, crotonyl, butenyl, isobutenyl or tert-butenyl; q represents an- integer ranging from 0 to 5
  • A represents a linear or branched C i -C 8 alkylene group, such as methylene, ethylene, n-propylene, isopropylene, n-butylene, tert- butylene, hexylene or octylene; or a linear or branched C 2 -C 8 alkenylene group, such as vinylene, allylene, crotonylene, butenylene, isobutenylene, tert-butenylene, hexenylene or octenylene, r, An, CAT, Sulfo, m, n and p have the same meanings as those above, and
  • R 2 to R 7 represent a hydrogen atom, a C i -4 alkyl group such as methyl, ethyl, n-propyl, isopropyl, n-butyl, or tert-butyl, or a Ci 2 -C i 8 alkyl group such as lauryl, myristyl, cetyl or stearyl, or a linear or branched C 2 -C 6 alkenyl group such as vinyl, allyl, crotonyl or butenyl.
  • amphoteric polysaccharide compounds containing sulfonate function(s) as described above may be used in cosmetics, as conditioning agents, and especially for the cosmetic treatment of keratin materials, such as caring for and protecting the hair, hold and discipline of the hairstyle, but also for cleansing and caring for the skin and for making up the skin, the lips and the nails.
  • a subject of the present invention is also a cosmetic composition
  • a cosmetic composition comprising, in a cosmetically acceptable medium, at least one amphoteric polysaccharide compound containing sulfonate function(s) according to the invention, preferably in an amount ranging from 0.01 % to 50% by weight and better still from 0.03 % to 25% by weight relative to the total weight of the composition.
  • cosmetically acceptable medium means a medium that is compatible with any keratin material, such as the skin, the hair, the nails, the eyelashes, the eyebrows and the lips and any other area of body or facial skin.
  • the cosmetically acceptable medium may consist solely of water or of a mixture of water and of a cosmetically acceptable solvent such as a C i -C 4 lower alcohol, such as ethanol, isopropanol, tert-butanol or n-butanol; alkylene polyols, for instance propylene glycol; polyol ethers; and mixtures thereof.
  • a cosmetically acceptable solvent such as a C i -C 4 lower alcohol, such as ethanol, isopropanol, tert-butanol or n-butanol
  • alkylene polyols for instance propylene glycol
  • polyol ethers and mixtures thereof.
  • composition according to the invention may also comprise one or more standard additives that are well known in the art, such as anionic, cationic, nonionic, amphoteric or zwitterionic surfactants, anionic, cationic, nonionic, amphoteric or zwitterionic polymers, thickeners, nacreous agents, opacifiers, UV-screening agents, fragrances, mineral, plant and/or synthetic oils, fatty acid esters, dyes, volatile or non-volatile, organomodified or non-organomodified, cyclic or acyclic, branched or unbranched silicones, mineral or organic, natural or synthetic particles, preserving agents and pH stabilizers.
  • standard additives that are well known in the art, such as anionic, cationic, nonionic, amphoteric or zwitterionic surfactants, anionic, cationic, nonionic, amphoteric or zwitterionic polymers, thickeners, nacreous agents, opacifiers, UV
  • compositions according to the invention are generally present in the composition according to the invention in an amount ranging from 0 to 20% by weight relative to the total weight of the composition.
  • the cosmetic compositions in accordance with the invention may be in the form of a mousse, a gel, a spray or a lacquer and may be used in rinse-out or leave-in application.
  • compositions in accordance with the invention may be used as hair products, especially rinse-out or leave-in products, and in particular for washing, caring for and/or conditioning the hair, holding the hairstyle, and shaping, dyeing, bleaching, permanently reshaping or relaxing the hair.
  • compositions of the invention may also be used as care or hygiene products such as protective, treating or care creams for the face, the hands or the body, protective or care body milks, gels or mousses for caring for or cleansing the skin, or alternatively as products for making up or for removing makeup from the skin, the lips, the nails and the eyelashes.
  • care or hygiene products such as protective, treating or care creams for the face, the hands or the body, protective or care body milks, gels or mousses for caring for or cleansing the skin, or alternatively as products for making up or for removing makeup from the skin, the lips, the nails and the eyelashes.
  • the mixture is heated at 5O 0 C for 5 hours. After cooling to room temperature, a light-brown powder is collected by filtration and reslurried twice in 200 ml of acetonitrile: the acetonitrile penetrates the gum and allows certain impurities to be extracted, which are then removed by suction-filtering the gum, this operation being repeated twice.
  • the product is dried under vacuum at 50°C.
  • Example 2 Shampoo
  • a shampoo was prepared using the following ingredients, the amounts of which are given as weight percentages of active material relative to the total weight of the composition:
  • Example 3 Conditioner
  • a conditioner was prepared using the following ingredients, the amounts of which are given as weight percentages of active material relative to the total weight of the composition:
  • Dye compositions were prepared using the following ingredients, the amounts of which are given as weight percentages of active material relative to the total weight of the composition:
  • each dye composition described above was mixed weight-for-weight with a 20-volumes hydrogen peroxide solution (6% by weight).
  • the mixtures thus prepared were applied for 30 minutes to locks of natural or permanent-waved grey hair containing 90% white hairs.
  • the locks were then rinsed, washed with a standard shampoo, rinsed again and then dried.
  • Example 7 The hair was dyed in a golden-blond shade for each of the Examples 4 to 6.
  • Example 7 The hair was dyed in a golden-blond shade for each of the Examples 4 to 6.
  • Another dye composition was prepared using the following ingredients, the amounts of which are given as weight percentages of active material relative to the total weight of the composition:
  • This composition is mixed at the time of use with an oxidizing composition in emulsion form containing as oxidizing agent 7.5% hydrogen peroxide, in a proportion of 1 part by weight of dye composition per 1.5 parts by weight of oxidizing composition.
  • the mixture obtained is applied to locks of natural hair containing 90% white hairs, and is left to act for 30 minutes. After rinsing, washing with shampoo and drying, hair dyed in a strong coppery-red light-chestnut shade is obtained.
  • compositions were prepared, the percentages indicated being weight percentages relative to the total weight of the composition:
  • the dye composition was mixed, at the time of use, in a plastic bowl and for 2 minutes, with the oxidizing composition given above, in a proportion of 1 part of dye composition per 1.5 parts of oxidizing composition.
  • the mixture obtained was applied to locks of natural hair containing
  • the hair was then -dyed in a strong light-chestnut shade.
  • Another dye composition was prepared using the following ingredients, the amounts of which are given as weight percentages of active material relative to the total weight of the composition:

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Materials Engineering (AREA)
  • Cosmetics (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)

Abstract

La présente invention concerne de nouveaux composés polysaccharidiens amphotères à fonction(s) sulfonate représentés par la formule générale (I). Dans cette formule, p est une chaîne polysaccharide. X, Y et Z représentent chacun un groupe à base d'hydrocarbure divalent en C1-C12 linéaire ou ramifié, saturé ou insaturé, éventuellement hydroxylé, comprenant éventuellement au moins une fonction éther et/ou amine dans la chaîne à base d'hydrocarbure, ou un groupe -Si(R)2-[O-Si(R)2]q-A-. 'r' vaut 0 ou 1. 'An' est un groupe anionique choisi dans la formule spécifique (II). CAT est un groupe ammonium quaternaire ou une chaîne polymère cationique résultant de la greffe et de la polymérisation de monomères éthyléniques portant une fonction ammonium quaternaire. 'Sulfo' est un groupe sulfonique ou sulfonate. Enfin, n, m et p sont tels que le degré total de substitution du polysaccharide n'excède pas 2. L'invention concerne également des composition les comprenant et leur utilisation en cosmétique.
EP05798113A 2004-08-19 2005-08-19 Nouveaux composes polysaccharidiens amphoteres a fonction(s) sulfonate, composition les comprenant, et utilisation cosmetique correspondante Withdrawn EP1778731A2 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR0408996A FR2874380B1 (fr) 2004-08-19 2004-08-19 Nouveaux composes polysaccharides amphoteres a fonction(s) sulfonate, composition les comprenant et leur utilisation en cosmetique
US61217804P 2004-09-23 2004-09-23
PCT/EP2005/009991 WO2006018327A2 (fr) 2004-08-19 2005-08-19 Nouveaux composes polysaccharidiens amphoteres a fonction(s) sulfonate, composition les comprenant, et utilisation cosmetique correspondante

Publications (1)

Publication Number Publication Date
EP1778731A2 true EP1778731A2 (fr) 2007-05-02

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ID=35735390

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Application Number Title Priority Date Filing Date
EP05798113A Withdrawn EP1778731A2 (fr) 2004-08-19 2005-08-19 Nouveaux composes polysaccharidiens amphoteres a fonction(s) sulfonate, composition les comprenant, et utilisation cosmetique correspondante

Country Status (3)

Country Link
EP (1) EP1778731A2 (fr)
JP (1) JP2008514736A (fr)
WO (1) WO2006018327A2 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110845640A (zh) * 2019-11-25 2020-02-28 中南大学 一种类肝素物质磺化柠檬酸改性壳聚糖及其制备方法

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102007037345A1 (de) 2007-08-08 2009-02-12 Wacker Chemie Ag Quaternäre Ammoniumgruppen aufweisende Organosiliciumverbindungen und deren Herstellung

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1135693A (en) * 1966-03-10 1968-12-04 Scholten Chemische Fab Polysaccharide derivatives
US4803071A (en) * 1980-02-11 1989-02-07 National Starch And Chemical Corporation Hair care compositions
FR2833599B1 (fr) * 2001-12-18 2004-01-30 Oreal Polysaccharide amphotere, composition et utilisation

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2006018327A3 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110845640A (zh) * 2019-11-25 2020-02-28 中南大学 一种类肝素物质磺化柠檬酸改性壳聚糖及其制备方法
CN110845640B (zh) * 2019-11-25 2022-02-01 中南大学 一种类肝素物质磺化柠檬酸改性壳聚糖及其制备方法

Also Published As

Publication number Publication date
WO2006018327A2 (fr) 2006-02-23
JP2008514736A (ja) 2008-05-08
WO2006018327A3 (fr) 2006-05-04

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