WO2006018327A2 - 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 Download PDFInfo
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- WO2006018327A2 WO2006018327A2 PCT/EP2005/009991 EP2005009991W WO2006018327A2 WO 2006018327 A2 WO2006018327 A2 WO 2006018327A2 EP 2005009991 W EP2005009991 W EP 2005009991W WO 2006018327 A2 WO2006018327 A2 WO 2006018327A2
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- WIPO (PCT)
- Prior art keywords
- group
- branched
- linear
- polysaccharide compound
- gum
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- -1 polysaccharide compounds Chemical class 0.000 title claims abstract description 68
- 239000000203 mixture Substances 0.000 title claims abstract description 57
- 239000005017 polysaccharide Substances 0.000 title claims abstract description 43
- 229920001282 polysaccharide Polymers 0.000 title claims abstract description 42
- 239000002537 cosmetic Substances 0.000 title claims abstract description 27
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical group [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 title claims abstract description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 22
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 22
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 22
- 150000001412 amines Chemical group 0.000 claims abstract description 12
- 238000006467 substitution reaction Methods 0.000 claims abstract description 12
- 125000000129 anionic group Chemical group 0.000 claims abstract description 11
- 150000004676 glycans Polymers 0.000 claims abstract description 11
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 11
- 150000004804 polysaccharides Polymers 0.000 claims abstract description 8
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims abstract description 7
- 229920006317 cationic polymer Polymers 0.000 claims abstract description 6
- 239000000178 monomer Substances 0.000 claims abstract description 6
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 5
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims abstract description 5
- 210000004209 hair Anatomy 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 239000000975 dye Substances 0.000 claims description 10
- 230000003750 conditioning effect Effects 0.000 claims description 9
- 125000002091 cationic group Chemical group 0.000 claims description 8
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 7
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 7
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
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- 229940029339 inulin Drugs 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
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- 238000011282 treatment Methods 0.000 claims description 5
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- 239000000230 xanthan gum Substances 0.000 claims description 5
- 229940082509 xanthan gum Drugs 0.000 claims description 5
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 4
- XNMQEEKYCVKGBD-UHFFFAOYSA-N 2-butyne Chemical group CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 claims description 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
- DLRVVLDZNNYCBX-UHFFFAOYSA-N Polydextrose Polymers OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(O)O1 DLRVVLDZNNYCBX-UHFFFAOYSA-N 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 4
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 claims description 4
- 125000005569 butenylene group Chemical group 0.000 claims description 4
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
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- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
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- 229920001612 Hydroxyethyl starch Polymers 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 210000000720 eyelash Anatomy 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 2
- 229940071826 hydroxyethyl cellulose Drugs 0.000 description 2
- 229940071676 hydroxypropylcellulose Drugs 0.000 description 2
- 235000011929 mousse Nutrition 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 238000005956 quaternization reaction Methods 0.000 description 2
- 230000002040 relaxant effect Effects 0.000 description 2
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
- 238000006277 sulfonation reaction Methods 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- FSSPGSAQUIYDCN-UHFFFAOYSA-N 1,3-Propane sultone Chemical compound O=S1(=O)CCCO1 FSSPGSAQUIYDCN-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical group [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 210000004709 eyebrow Anatomy 0.000 description 1
- 230000001815 facial effect Effects 0.000 description 1
- 150000002193 fatty amides Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- PUVAFTRIIUSGLK-UHFFFAOYSA-M trimethyl(oxiran-2-ylmethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1CO1 PUVAFTRIIUSGLK-UHFFFAOYSA-M 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
-
- 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
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/73—Polysaccharides
- A61K8/731—Cellulose; Quaternized cellulose derivatives
-
- 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
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/91—Graft copolymers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/10—Preparations for permanently dyeing the hair
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/12—Preparations containing hair conditioners
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B15/00—Preparation of other cellulose derivatives or modified cellulose, e.g. complexes
- C08B15/05—Derivatives containing elements other than carbon, hydrogen, oxygen, halogens or sulfur
- C08B15/06—Derivatives containing elements other than carbon, hydrogen, oxygen, halogens or sulfur containing nitrogen, e.g. carbamates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L1/00—Compositions of cellulose, modified cellulose or cellulose derivatives
- C08L1/08—Cellulose derivatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/54—Polymers characterized by specific structures/properties
- A61K2800/542—Polymers characterized by specific structures/properties characterized by the charge
- A61K2800/5428—Polymers 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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- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
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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.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP05798113A EP1778731A2 (fr) | 2004-08-19 | 2005-08-19 | Nouveaux composes polysaccharidiens amphoteres a fonction(s) sulfonate, composition les comprenant, et utilisation cosmetique correspondante |
| JP2007526408A JP2008514736A (ja) | 2004-08-19 | 2005-08-19 | スルホネート基を含む新規な両性多糖類化合物、それを含む組成物及びその化粧品における使用 |
| US11/660,379 US20080124294A1 (en) | 2004-08-19 | 2005-08-19 | Novel Amphoteric Polysaccharide Compounds Containing Sulfonate Function(s), Composition Comprising Them and Cosmetic Use Thereof |
Applications Claiming Priority (4)
| 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 |
| FR04/08996 | 2004-08-19 | ||
| US61217804P | 2004-09-23 | 2004-09-23 | |
| US60/612,178 | 2004-09-23 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO2006018327A2 true WO2006018327A2 (fr) | 2006-02-23 |
| WO2006018327A3 WO2006018327A3 (fr) | 2006-05-04 |
Family
ID=35735390
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| 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 |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP1778731A2 (fr) |
| JP (1) | JP2008514736A (fr) |
| WO (1) | WO2006018327A2 (fr) |
Cited By (1)
| 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 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Citations (3)
| 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 |
| FR2833599A1 (fr) * | 2001-12-18 | 2003-06-20 | Oreal | Polysaccharide amphotere, composition et utilisation |
-
2005
- 2005-08-19 EP EP05798113A patent/EP1778731A2/fr not_active Withdrawn
- 2005-08-19 WO PCT/EP2005/009991 patent/WO2006018327A2/fr active Application Filing
- 2005-08-19 JP JP2007526408A patent/JP2008514736A/ja active Pending
Patent Citations (3)
| 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 |
| FR2833599A1 (fr) * | 2001-12-18 | 2003-06-20 | Oreal | Polysaccharide amphotere, composition et utilisation |
Cited By (1)
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1778731A2 (fr) | 2007-05-02 |
| WO2006018327A3 (fr) | 2006-05-04 |
| JP2008514736A (ja) | 2008-05-08 |
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