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AMPHOTERIC POLYSACCARIDE COMPOUNDS CONTAINING ALDEHYDE FUNCTION(S), COMPOSITION COMPRISING THEM AND COSMETIC USE THEREOF
5 The present invention relates to novel amphoteric polysacchande
compounds containing aldehyde function(s), to their use in cosmetics and to compositions comprising them.
In the cosmetics field, it is especially sought to improve the cosmetic properties of keratin materials, such as the hair and the skin,
10 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.
With this aim, it is common practice to use complementary
15 cosmetic agents known as 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. These conditioning agents also improve the cosmetic
20 behaviour of natural hair.
Other 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. However, these polysaccharides are not very efficient as
25 regards conditioning and rernanence.
The Applicant has found that, after several uses, the hair becomes laden and lacks lightness.
The Applicant has thus found, surprisingly and unexpectedly, novel amphoteric polysaccharide compounds containing aldehyde
30 function(s), which, when used in cosmetics, make it possible to
overcome the drawbacks described above and to obtain excellent cosmetic properties such as an excellent conditioning and protecting effect on the hair, good disentangling of the hair, softness and a smoothing effect on keratin fibres. In addition, the use of these

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amphoteric polysaccharide compounds containing aldehyde function(s) leads in particular to good remanence of these properties, even after washing the hair several times, without observing an excessive deposit that would lead to laden, non-maleable and non-supple hair.
5 These conditioning agents also give the skin cosmetic properties
such as good moisturization.
One subject of the present invention is thus novel amphoteric polysaccharide compounds containing aldehyde function(s) as described below.
10 A second subject of the invention consists of a use of such a
¦ polysaccharide compound in cosmetics, as a conditioning agent, and
especially for the cosmetic treatment of keratin materials, such as caring
for and protecting the hair, hairsryling, permanent-waving, relaxing,
dyeing or bleaching the hair, or alternatively cleansing and care of the
15 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.
Other subjects, characteristics, aspects and advantages of the
20 invention will emerge even more clearly on reading the description and
the various examples that follow.
The amphoteric polysaccharide compounds containing aldehyde
function(s) according to the invention bear, as substituents other than
the aldehyde functions, at least one anionic group and at least one
25 cationic group.
The amphoteric polysaccharide compounds containing aldehyde function(s) according to the invention may be represented by formula (I) below:
30 P—(O—(Y)p—CAT)m (I)
in which:
the oxygen atoms belong to one or more polysaccharide units of P,
P represents a polysaccharide chain, the said chain bearing

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one or more aldehyde functions (-CHO) and optionally one or more groups -COOV, this group possibly being obtained during the oxidation of certain carbon atoms, for example in position C2, C3 or C6, of a saccharide unit; in the case of an oxidation at C2 or C3, from 0.01% to 75% on a numerical basis and preferably from 0.1% to 50% on a numerical basis of the rings possibly having been opened; represents:
a linear or branched, saturated or unsaturated, optionally hydroxylated divalent Ci-Cg hydrocarbon-based group optionally comprising at least one ether and/or amine function in the hydrocarbon-based chain, or

the silicon atom being attached to the oxygen atom in the
group -O-(Y)P-CAT,
in which each R, which may be identical or different,
represents Ri or OR),
R] represents a linear or branched, saturated or
unsaturated, optionally hydroxylated Cj-Cg and
preferably C]-C4 monovalent hydrocarbon-based group
optionally comprising at least one ether and/or amine
function in the hydrocarbon-based chain,
q represents an integer ranging from 0 to 10 and
preferably from 0 to 5, q = 0 being particularly preferred,
and
Z represents a linear or branched, saturated or
unsaturated, optionally hydroxylated C1-C12 and
preferably Cj-Cs, divalent hydrocarbon-based group
optionally comprising at least one ether and/or amine

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function in the hydrocarbon-based chain, is equal to 0 or 1, p being 0 when CAT represents a cationic polymer chain obtained by grafting and polymerization of ethylenic monomers bearing an ammonium group, represents:
an ammonium group

in which R2, R3 and R4 represent, independently of each other, a hydrogen aiom or a linear or branched, saturated o"r unsaturated, optionally hydroxylated C,-C22 and preferably Ci-Cig rnonovalent hydrocarbon-based group optionally comprising at least one ether and/or amine function in the hydrocarbon-based chain, and 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:

in which R5, R6 and R7 represent, independently of each other, a hydrogen atom, a linear or branched C1-C22 and preferably Cj-Cjg alky] group, or a linear or branched C2-C22 and preferably CT-CU alkenyl group, ; such that the degree of substitution of the poly-

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saccharide compound with a cationic group (DS(+)) is within the range from 0.02 to 1.5 and preferably from 0.05 to 1.
The term "degree of substitution DS(+) of the amphoteric polysaccharide compounds" according to the invention means the ratio between the number-of hydroxyl groups substituted with a cationic group for all the repeating, units and the number of elementary monosaccharides (even opened by pre-oxidation) constituting the unit.
The polysaccharide chain containing aldehyde function(s), represented by P, is preferably a polysaccharide chain obtained by oxidation of a cellulose, a starch, inulin, guar gum, xanthan gum, pullulan, agar-agar, sodium, potassium or ammonium alginate, carrageenan, dextran, furcellaran, gellan gum, gum arabic, gum tragacanth, hyaluronic acid, konjac mannan, lignin sulfonate, carob gum, partially N-acetylated chitin, pectin, polydextrose, rhamsan gum or welan gum.
The oxidation may be performed according to a process known in the art, for example according to the process described in FR 2 842 200 or in the article "Hydrophobic films from maize bran hemicelluloses" by E. Fredon et al. Carbohydrate Polymers 49, 2002, pages 1 to 12.
More preferably, the polysaccharide chain containing aldehyde function(s) is obtained by oxidation of cellulose, carboxy-methyl cellulose, hydroxyethyl cellulose, hydroxypropy] cellulose, hydroxypropylmethylcellulose, methylcellulose, starch, starch acetate, hydroxyethyl starch, hydroxypropyl starch, inulin, guar gum, carboxymethylguar gum, carboxymethylhydroxypropylguar gum, hydroxyethylguar gum, hydroxypropylguar gum or xanthan gum.
The polysaccharide chain containing aldehyde function(s) preferably has a weight-average molecular mass between 500 and 15 000 000 and better still between 1000 and 10 000 000.
Examples of linear or branched, saturated or unsaturated Ci-Cs and preferably C]-C6 divalent hydrocarbon-based groups Y or Z that may especially be mentioned include linear or branched Ci-C& alkylene groups, such as methylene, ethylene, n-propylene, isopropylene,

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n-butylene, tert-butylene or hexylene; linear or branched C2-C& alkylene groups, such as vinylene, aUylene, crotonyjene, 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.
Examples of linear or branched, saturated or unsaturated CJ-CR and preferably Cj-C4 monovalent hydrocarbon-based groups R, that may especially be mentioned include linear or branched C1-C4 alkyl groups, such as methyl, ethyl, n-propyl, isopropyl, n-butyl or tert-butyl; linear or branched C2-C4 alkenyl groups, such' as vinyl, allyl, crotonyl, butenyl, isobutenyl or tert-butenyl; the said groups possibly bearing at least one hydroxyl substituent and/or possibly comprising at least one ether and/or amine function.
Examples of RT to R7 that may especially be mentioned include linear or branched C1-C4 alky] groups, such as methyl, ethyl, n-propyl. isopropyl, n-butyl or tert-butyl groups, and linear or branched Cn-Cig alkyl groups, such as lauryl, myristyl, cetyl or stearyl groups. Examples of linear or branched CT-CIS and preferably C?-C6 alkenyl groups that may especially be mentioned include vinyl, allyl, crotonyl and butenyl groups.
The amphoteric polysaccharide compounds that are most particularly preferred in the invention are those corresponding to formula (I) in which:
P represents a polymer chain obtained by oxidation of cellulose, carboxymethylcellulose, hydroxyethylcellulose, hydroxypropylcellulose, hydroxypropylmethylcellulose, methylcellulose, starch, starch acetate, hydroxyethyl starch, hydroxypropyl starch, inulin, guar gum, carboxymethylguar gum, carboxymethylhydroxypropylguar gum, hydroxyethylguar gum, hydroxypropylguar gum or xanthan gum; Y represents a linear or branched C1-C6 alkylene group, such as methylene, ethylene, n-propylene, isopropylene, n-butylene, tert-butylene or hexylene; or a linear or branched C?-Cg alkenylene group, such as vinylene, allylene, crotonylene, butenylene, isobutenylene, tert-

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in which each R, which may be identical or different, represents Ri or OR,,
Ri represents a linear or branched Cj-C4 alkyl group, such as methyl, ethyl, n-propyl, isopropyl, n-butyl or tert-butyl; or a linear or branched C2-C4 alkenyl group, such as vinyl, aliyl, crotonj'l, butenyl, isobutenyl or tert-butenyl;
q represents an integer ranging from 0 to 5,
Z represents a linear or branched Ci-Cg alkylene group, such as methylene, ethylene, n-propylene,- isopropylene, n-butylene, tert-butylene or hexylene; or a linear or branched C2-C8 alkenylene group, such as vinylene, allylene, crotonylene, butenylene, isobutenylene, terf-butenylene, hexenylene or octenylene,
p, CAT and m having the same meanings as those above, and R2 to R7 represent a hydrogen atom, an optionally hydroxylated Cj.4 alky] group such as methyl, ethyl, n-propyl, isopropyl, n-butyl, or tert-butyl, or an optionally hydroxylated Cu-Cis alkyl group such as lauryl, myristyl, cetyl or stearyl, or a linear or branched C2-C6 alkenyl group such as vinyl, allyl, crotonyl or butenyl.
The amphoteric polysaccharide compounds containing aldehyde function(s) as described above may be used in cosmetics, as conditioning agents, 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 comprising, in a cosmetically acceptable medium, at least one amphoteric polysaccharide compound containing aldehyde function(s) according to the invention, preferably in an amount ranging from 0.05% to 50% by weight and better still from 0.5% to 25% by weight relative

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to the total weight of the composition.
The term "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 C1-C4 lower alcohol, such as ethanol, isopropanol, lert-butanol or n-butanol; alkylene polyols, for instance propylene glycol; polyol ethers; and mixtures thereof.
The 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-soreening 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.
A person skilled in the art will take care to select the optional additives and the amount thereof such that they do not harm the properties of the compositions of the present invention.
These additives 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.
The compositions in accordance with the invention may be used as hair products, especially rinse-out or leave-m 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.
The compositions of the invention may also be used as care or

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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 examples below are given as illustrations of the invention.
EXAMPLES
Example 1: Grafting of 3-epoxypropyltrimethylammonium chloride onto oxidized starch.
24 g of oxidized starch (acid number: 1.4 mmol/g, carbonyl number 1.08 mmol/g) are dispersed in 500 ml of acetonitrile with stirring.
62.5 mmol of 50% sodium hydroxide and 0.2 mol of 3-epoxy-propyltrimethylammonium chloride are successively added. The mixture is heated at 50°C for 5 hours and then neutralized with 12 ml of acetic acid.
A brown gum is obtained, which is reslurried twice in acetonitrile: the acetonitrile penetrates the gum and allows certain impurities to be extracted, which are then removed by suction-filtering the gum, this manipulation being repeated twice.
The solid is dried under vacuum at 50°C until a constant weight is obtained. A degree of grafting of 78% is determined by measuring the chloride number on the filtrates and the solid.
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:

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¦ —— .Sodium lauryl ether sulfate (Texapon N702 from Cognis) 12.5%
Cocoylbetaine (Dehyton AB 30 from Goldschmidt) 2.5%
Dimethicone (DC200 Fluid from Dow Corning) 2.0%
Compound of Example 1 0.5%
Cocamide monoisopropanolamine 0.4%
Carbomer 0.2%
Preserving agent qs
Fragrance qs
Citric acid/sodium hydroxide qs pH 6.5
Water qs 100
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:

Behenyltrimethylammonium chloride (Genamin KDMP from Clariant) 1.2%
PEG/PPG Dimethicone (Abil B885 1 from Goldschmidt) 0.5%
Cyclopentasiloxane (Dow Corning 245 Fluid) 15.0%
Compound of Example 1 1.0%
Propylene glycol 2.5%,
Preserving agent qs
Fragrance qs
Citric acid/sodium hydroxide qs pH 6.5
Water qs 100
Examples 4-6
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:

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Ex. 4 Ex. 5 Ex. 6
para-Phenylenediamine ' 0.24 0.24 0.24
para-Aminophenol 0.44 0.44 0.44
2-Aminophenol 0.028 0.028 O.028
1,3-Dihydroxybenzene 0.192 0.192 0.192
3-Aminopbeno] 0.019 0.019 0.019
5-N-(j3-HydroxyethyI)amino-2-methyl phenol 0.021 0.021 0.021
1.3-Dihydroxy-2-methylbenzene 0.055 0.055 0.055
Anhydrous sodium metasilicate 1 2 ¦ 2
Monoethanolamine 5.45 5.45 5.45
Reducing agent, antioxidant. sequestering agent, fragrance qs qs qs
Propylene glyco] ¦ 10 10 10
Crosslinked acrylic acid polymer 0.4 0.4 0.4
Compound of Example 1 1.5 1.5 2.8
Cationic polymer: bexadimethnne chloride (CTFA name) Mexomer PO sold by the company Chimex 3 3
Powdered sodium lauryl sulfate 3
LauryJ alcohol oxyethylenated with 12 mol of ethylene oxide - 7.5 7.5
Oleocetyl alcohol oxyethylenated with 30 mol of etbylene oxide - 4 4
Decyl alcohol oxyethylenated with 3 mol of ethylene oxide 10 10 10
Decyl alcohol oxyethylenaied with 5 mol of ethylene oxide » 8 - -
Laurie acid 2.5 2.5 2.5
50/50 cetylstearyl alcohol 11.5 11.5 13.5
Nacreous agent: bydrophobic fumed silica 1.2 1.2 1.2
Nacreous agent: glyceryl monostearate 2 2 2

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Ex. 4 Ex. 5 Ex. 6
Demineralized water qs 100 100 100
At the time of use, 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.
The hair was dyed in a golden-blond shade for each of the Examples 4 to 6.
Example 7
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:

Mixture of C18 to C24 linear alcohols (C18/C20/C22/C24: 7/57/30/6 - alcohol content > 95%)
Oxyethylenated stearyl alcoho] (2 mol of ethylene oxide) 4.5
Oxyethylenated stearyl alcohol (21 mol of ethylene oxide) 1.75
Oleic acid 2.6
Cationic polyurethane obtained by condensation of 1,3-bis-(isocyanatomethylcyclohexane), N,N-dim ethyl ethanolamine quaternized with bromododecane, N,N-dimethylethanolamine and polyoxyethylene of molecular-weight 10 000 0.2
Crosslinked poly(acrylic acid) (product sold under the name Carbopol 980 by the company Noveon) 0.4
Hydroxypropylmethyl cellulose 0.2
Coconut acid monoisopropanolamide 3
Merquat 100 as an aqueous 40% solution 1.6
Compound of Example 1 2
Sodium metabisulfite 0.71

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EDTA (ethylenediaminetetraacetic acid) 0.2
tert-Butylhydroquinone 0.3
1,4-Diaminobenzene 0.2
para-Aminopheno! 1.2
1,3-Dihydroxybenzene 0.1
1 -Hydroxy-3-aminobenzene 0.2
1-Methyl-2-hydroxy-4-P-hydroxyethylammobenzene 0.8
Monoethanolamine 1
Aqueous ammonia containing 20% NH3 11
Fragrance qs
Demineralized water qs 100
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.
Example 8
The following compositions were prepared, the percentages indicated being weight percentages relative to the total weight of the composition:
Oxidizing composition:

Fatty alcohol 2.3%
Oxyethylenated fatty alcohol 0.6%
Fatty amide 0.9%
Glycerol 0.5%

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Hydrogen peroxide 7.5%
Fragrance qs
Demineralized water qs 1 00%
Dve composition:

Mixture of CIS to C24 linear alcohols [C18/C20/C22/C24, 7/58/30/6, alcohol content > 95%] (Nafol 20-22) 3%
Mixture of CIS to C24 linear alcohols [C18/C20/C22/C24, 7/58/30/6, alcohol content > 95%] in oxyethylenated form (30 mol of ethylene oxide) (Nafolox 20-22) 1 .3 5%
Oxyethylenated stearyl alcohol (2 mol of ethylene oxide) 4%
Oxyethylenated stearyl alcohol (21 mol of ethylene oxide) 2%
Oleic acid 2.6%
Glycol distearate 2%
Propylene glycol 5%
Coconut acid monoisopropanolamide 2%
Aculyn 44 sold by the company Rohm & Haas 1.4% AM*
Crosslinked poly(acrylic acid) 0.6%
Compound of Example 1 3% AM*
Merquat 100 sold by the company Calgon 0.4% AM*
Reducing agents 0.7%
Sequestering agents 0.2%
1,3-Dihydroxybenzene (resorcinol) 0.6%)
1,4-Diaminobenzene 0.5%
1 -Hydroxy-3-aminobenzene 0.1%
1 -Hydroxy-2-aminobenzene 0.05%
1 -Hydroxy-4-aminobenzene 0.09%
6-Hydroxybe:nzomorpholine 0.017%
l-P-Hydroxyethyloxy-2,4-diaminobenzene 0.03 9%

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dihydrochloride
Propylene glycol monobutyl ether 2.5%
Pure monoethanolamine 1.06%
Aqueous ammonia (containing 20.5% ammonia) 11.1%
Water qs 1 00%
AM*= Active Material
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
90% white hairs, and was left to act for 30 minutes.
The locks were then rinsed with water, washed with shampoo, rinsed
again with water and then dried and disentangled.
The hair was then dyed in a strong light-chestnut shade.
Example 9
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:

Oleocetyl alcohol oxyethylenated with 30 mol of ethylene oxide (nCA=17 - HLB = 16.5) 7%
Lauryl alcohol (C12-C1 4/55-45%) oxyethylenated with 12 mol of ethylene oxide (nCA=12.5 - HLB=14) 8%
CetylstearyJ alcohol (CJ 6/C1 8-50/50)(nCB = l 7- HLB = 1) 5%
Decyl alcohol (Cl 0-C1 2-C1 4/85-8.5-6.5) oxyethylenated with 3.5 mol of ethylene oxide, sold under the name Mergital BL 309 by the company Henkel (nCB=10.4 -HLB = 8.5) 22%
Copolymer of diallyldimethylammonium chloride and of acrylic acid, sold under the name Merquat 280 by the company Calgon, containing 3 5% AM 3% AM
Compound of Example 1 1%

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Crosslinked poly(acrylic acid) sold under the name Carbopol 934 (MW 3 000 000) by the company Goodrich 0.4%
Propylene glycol 8%
Monoethanolamine 8.3 %
Hydroquinone 0.1 %
1 -Pheny]-3-methy]-5-pyrazo]one 0.1 %
Aqueous sodium bisulfite solution.containing 35% AM 1.3 %
para-Phenylenediamme 0.5 %
m-Dihydroxybenzene 0.4 %
Fragrance, sequestering agent qs
Eau qs 1 00%
pH = 11.0
AM: Active Material

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CLAIMS
1. Amphoteric polysaccharide compound containing aldehyde function(s) corresponding to formula (I):
P-(O-(Y)p-CAT)n, (I)
in which:
the oxygen atoms belong to one or more polysaccharide units of P,
P represents a polysaccharide chain, the said chain bearing
one or more aldehyde functions and optionally one or more
groups -COOV, this group possibly being obtained during
the oxidation of certain carbon atoms of a saccharide unit,
Y represents:
- a linear or branched, saturated or unsaturated, optionally hydroxylated divalent C]-C& hydrocarbon-based group optionally comprising at least one ether and/or amine function in the hydrocarbon-based chain, or

the silicon atom being attached to the oxygen atom in the
group -O-(Y)P-CAT,
in which each R, which may be identical or different,
represents R] or-OR},
Ri represents a linear or branched, saturated or
unsaturated, optionally hydroxylated C\-Cs monovalent
hydrocarbon-based group optionally comprising at least
one ether and/or amine function in the hydrocarbon-based
chain,
q represents an integer ranging from 0 to 10, and
Z represents a linear or branched, saturated or

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unsaturated, optionally hydroxylated C1-C12 -divalent hydrocarbon-based group optionally comprising at least one ether and/or amine function in the hydrocarbon-based chain,
is equal to 0 or 1. p being 0 when CAT represents a
cationic polymer chain obtained by grafting and
polymerization of ethylenic monomers bearing an
ammonium group,
represents:
- an ammonium group

in which R2, R.3 and R.4 represent, independently of each other, a hydrogen atom or a linear or branched, saturated or unsaturated, optionally hydroxylated C1-C22 monovalent hydrocarbon-based group optionally comprising at least one ether and/or amine function in the hydrocarbon-based chain, and Q" represents a mineral or organic anion, or
- a cationic polymer chain obtained by grafting and polymerization of ethylenic monomers bearing an ammonium group,
is such that the degree of substitution of the polysaccharide
compound with a cationic group is within the range from 0.02
to 1.5.
2. Amphoteric polysaccharide compound according to Claim 1,
characterized in that P represents a polysaccharide chain containing
aldehyde function(s) obtained by oxidation of a cellulose, a starch,
inulin, guar gum, xanthan gum, pullulan, agar-agar, sodium, potassium
or ammonium alginate, carrageenan, dextran, furcellaran, gellan gum,
gum-arabic, gum tragacanth, hyaluronic acid, konjac mannan, lignin
sulfonate, carob gum, partially N-acetylated chitin, pectin, polydextrose,
rhamsan gum or welan gum.
3. Amphoteric polysaccharide compound according to Claim 2,

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characterized in that P represents a polysaccharide chain containing aldehyde function(s) obtained by oxidation of a cellulose, carboxymethyl cellulose,- hydroxyethylcellulose, hydroxypropyl cellulose, hydroxypropylmethylcellulose, methylcellulose, starch, starch acetate, hydroxyethyl starch, hydroxypropyl starch, inulin, guar gum, carboxy-methylguar gum, carboxymethylhydroxypropylguar gum, hydroxy-ethylguar gum, hydroxypropylguar gum or xanthan gum.
4. Amphoteric polysaccharide compound according to any one
of the preceding claims, characterized in that the divalent hydrocarbon-
based group Y or Z is chosen from linear or branched Ci-C$ alkylene
groups and linear or branched C2-C8 alkenylene groups, optionally
bearing at least one hydroxyl group and/or optionally comprising at least
one ether and/or amine function in the alkylene or alkenylene chain.
5. Amphoteric polysaccharide compound according to Claim 4,
characterized in that the divalent hydrocarbon-based group Y or Z is
chosen from methylene, ethylene, n-propylene, isopropylene,
n-butylene, tert-butylene, hexylene, vinylene, allylene, crotonylene,
butenylene, isobutenylene, tert-butenylene, hexenylene and octenylene
groups.
6. Amphoteric polysaccharide compound according to. any one
of the preceding claims, characterized in that Ri represents a linear or
branched C1-C4 alkyl group or a linear or branched C2-C4 alkenyl group.
7. Amphoteric polysaccharide compound according to Claim 6,
characterized in that Ri is chosen from methyl, ethyl, n-propyl,
isopropyl, n-butyl, tert-butyl, vinyl, allyl, crotonyl, butenyl, isobutenyl
and tert-butenyl groups.
8. Amphoteric polysaccharide compound according to any one
of the preceding claims, characterized in that Q represents a halogen
atom, an acetate, a citrate, a lactate, an oleate or a behenate.
9. Amphoteric polysaccharide compound according to any one
of the preceding claims, characterized in that R2, R3 and R4 represent,
independently of each other, a hydrogen atom, a linear or branched
C1-C4 alkyl group, a linear or branched Ci2-C]g alkyl group or a linear
or branched C2-C6 alkenyl group.

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10. Amphoteric polysaccharide compound according to Claim 9,
characterized in that R2, R3 and R4 represent, independently of each
other, a hydrogen atom or a methyl, ethyl, n-propyl, isopropyl, n-butyl,
tert-butyl, lauryl, myristyl, cetyl, ¦ stearyl, vinyl, allyl, crotonyl or
butenyl group.
11. Amphoteric polysaccharide compound according to any one
of the preceding claims, characterized in that the ethylenic monomers
bearing a quaternary ammonium group correspond to the formula:

in which R5, R6 and R7 represents, independently of each other, a hydrogen atom, a linear or branched Cj-C22 alkyl group or a linear or branched C2-C22 alkenyl group.
12. Amphoteric polysaccharide compound according to Claim 1 1,
characterized in that R5, R6 and R7 represent, independently of each
other, a hydrogen atom, a linear or branched C1-C4 alkyl group, a linear
or branched C12-C1S alkyl group or a linear or branched C2-C6 alkenyl
group.
13. Amphoteric poiysaccharide compound according to Claim 12,
characterized in that R5, Rg and R7 represent, independently of each
other, a hydrogen atom or a methyl, ethyl, n-propyl, isopropyl, n-butyl,
tert-butyl, lauryl, myristyl, cetyl, stearyl, vinyl, allyl, crotonyl or
butenyl group.
14. Use of at least one amphoteric polysaccharide compound
containing aldehyde function(s) according to any one of the preceding
claims, in cosmetics, as a conditioning agent.
15. Use according to Claim 14, for the cosmetic treatment of
keratin materials.
16. Use according 1o Claim 15, for caring for and protecting the
hair.
17. Use according to Claim 15, for cleansing and caring for the
skin.
18. Use according to Claim 15, for making up the skin, the lips

WO 2006/018324 PCT/EP2005/009987
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and the nails.
19. Cosmetic composition comprising, in a cosmetically
acceptable medium, at least one ampho.teric polysaccharide compound
containing aldehyde function(s) accordingto any one of Claims 1 to 1-3.
20. Cosmetic composition according to Claim 19, characterized
in that it comprises the said amphoteric polysaccharide compound
containing aldehyde function(s) in an amount ranging from 0.05% to
50% by weight relative to the total weight of the composition.
21. Cosmetic composition according to Claim 20, characterized
in that it comprises the said amphoteric polysaccharide compound
containing aldehyde function(s) in an amount ranging from 0.5% to 25%
by weight relative to the total weight of the composition.
22. Cosmetic composition according to any one of Claims 19 to
21, characterized in that the cosmetically acceptable medium comprises
water or a mixture of water and of at least one organic solvent.
23. Cosmetic composition according to Claim 22, characterized
in that the organic solvent is chosen from C1-C4 lower alcohols, alkylene
polyols, polyol ethers, and mixtures thereof.
24. Cosmetic composition according to any one of Claims 19
to 23, characterized in that it comprises at least one additive chosen
from 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.

The present invention relates to novel ampnoteric polysaccharide compounds containing aldehyde function(s) corresponding to the formula (I): P-(O-(Y)p-CAT)m in which: P represents a polysaccharide chain, the said chain bearing one or more aldehyde functions and optionally one or more groups -COOV, this group possibly being obtained during the oxidation of certain carbon atoms of a saccharide unit, Y represents a linear or branched, saturated or unsaturated, optionally hydroxylated divalent C,-Cs divalent hydrocarbon-based group comprising at least one ether and/or amine function in the hydrocarbon-based chain, or a group -Si(R)2-[O-Si(R)1]q-Z-; p is O or 1, and CAT represents an ammonium group or a canonic polymer chain obtained by grafting and polymerization of ethylenic monomers bearing an ammonium function. The invention also relates to their use in cosmetics and to compositions comprising them.