WO2015089716A1 - Composition comprising cyclodextrin and its derivative, anionic surfactant and polyalkylene glycol ether of alcohol, and its use thereof - Google Patents

Composition comprising cyclodextrin and its derivative, anionic surfactant and polyalkylene glycol ether of alcohol, and its use thereof Download PDF

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Publication number
WO2015089716A1
WO2015089716A1 PCT/CN2013/089581 CN2013089581W WO2015089716A1 WO 2015089716 A1 WO2015089716 A1 WO 2015089716A1 CN 2013089581 W CN2013089581 W CN 2013089581W WO 2015089716 A1 WO2015089716 A1 WO 2015089716A1
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Prior art keywords
composition
alkyl
weight
chosen
cyclodextrin
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PCT/CN2013/089581
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French (fr)
Inventor
Haidong JIA
Jean-Michel Sturla
Dhimoy ROY
Original Assignee
L'oreal
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Priority to PCT/CN2013/089581 priority Critical patent/WO2015089716A1/en
Priority to CN201380081669.1A priority patent/CN105828801A/en
Publication of WO2015089716A1 publication Critical patent/WO2015089716A1/en

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    • 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
    • A61K8/84Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/86Polyethers
    • 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
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/46Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A61K8/463Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfuric acid derivatives, e.g. sodium lauryl sulfate
    • 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
    • A61K8/738Cyclodextrins
    • 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

Definitions

  • the present invention relates to the field of hair care. More specifically, the present invention relates to a composition for caring for keratin materials,
  • Cyclodextrins have already been used for making nacreous compositions.
  • compositions with cyclodextrins with improved stability and nacreous effect are provided.
  • composition comprising a specific cationic polymer and cyclodextrin.
  • compositions especially the shampoos, are of great interests of the consumers, especially to those having sensitized hair (i.e.
  • the object of the invention is to provide a composition comprising at least one cyclodextrin or its derivative, at least one anionic surfactant, and at least one polyalkylene glycol ether of alcohol.
  • one object of the current invention is to provide a
  • composition comprising, in an aqueous phase: a) at least one cyclodextrin or its derivative;
  • a is an integer of 4 to 14;
  • b is an integer of 2 to 30;
  • R is a alkylene group.
  • Another object of the present invention is to provide a method for caring for keratin materials, especially the hair, using the above described composition.
  • keratin material means the skin (of the body, face and around the eyes), hair, eyelashes, eyebrows, bodily hair, nails, lips or mucous membranes.
  • it means the keratin fibers, especially the hair.
  • composition as such is found to possess an improved stability, foaming, as well as conditioning effect.
  • condition effect it especially refers to the disentangling of dried hair after application of the composition as described above.
  • the composition comprises, in an aqueous phase:
  • a is an integer of 4 to 14;
  • b is an integer of 2 to 30;
  • R is an alkylene group.
  • composition of the present invention comprises an aqueous phase.
  • the aqueous phase comprises water and may comprise water-miscible organic solvents (at room temperature of 20-25°C), for instance monoalcohols containing from 2 to 6 carbon atoms, such as ethanol or isopropanol; polyols especially containing from 2 to 20 carbon atoms, preferably containing from 2 to 10 carbon atoms and preferentially containing from 2 to 6 carbon atoms, such as glycerol, propylene glycol, butylene glycol, pentylene glycol, hexylene glycol, dipropylene glycol or diethylene glycol; glycol ethers (especially containing from 3 to 16 carbon atoms) such as mono-, di- or tripropylene glycol (Ci-C 4 )alkyl ethers, mono-, di- or triethylene glycol (Ci-C 4 )alkyl ethers, and mixtures thereof.
  • monoalcohols containing from 2 to 6 carbon atoms, such as ethanol or isopropan
  • composition of the present invention comprises from 45% to 85% by weight, especially from 50% to 75% and more particularly from 55% to 65% by weight of the aqueous phase, relative to the total weight of the composition.
  • composition of the present invention comprises at least one cyclodextrin or its derivative.
  • Cyclodextrins are especially oligosaccharides of formula (I):
  • x is equal to 4 (which corresponds to a-cyclodextrin), 5 ( ⁇ -cyclodextrin) or 6 ( ⁇ -cyclodextrin).
  • a beta-cyclodextrin sold by the company Wacker under the name Cavamax ® W7, or by the company Shandong Xinda Fine Chemical under the name Beta-Cyclodextrin, a gamma-cyclodextrin sold by the company Wacker under the name Cavamax ® W8, or a mixture thereof, may especially be used.
  • cyclodextrins also means substituted cyclodextrin derivatives, for instance methyl cyclodextrins, in particular the methyl-beta-cyclodextrin sold by the company Wacker under the name Cavasol ® W7.
  • the cyclodextrins of the invention are unsubstituted.
  • a beta-cyclodextrin will be used.
  • the cyclodextrin(s) may represent from 0.5% to
  • composition of the invention comprises at least one anionic surfactant or "surface-active agent".
  • Anionic surfactant is understood to mean an amphiphilic compound in which the hydrophobic part carries an anionic hydrophilic group with a cationic counterion which is generally metallic (alkali metal, such as Na or K) or ammonium; the hydrophilic group is thus polar and capable of dissociating to give anions in aqueous solution.
  • anionic part of the anionic surfactant is belonging to the group chosen from: C(O)OH, -C(O)O " , -SO 3 H, -S(O) 2 O " , -OS(O) 2 OH,
  • the anionic part comprizing a cationic counter anion such as alkali metal such as sodium, or alkaline earth metal such as magnesium, or organic cationic counter anion such as ammonium salts, amine salts, or aminoalcohol salts.
  • the surfactants may also occur in their acid forms.
  • anionic surfactants or surface-active agents of surfactants or surface-active agents comprising carboxylate, sulfate, sulfonate, sulfoacetate, sulfosuccinate, phosphate, isethionate, sarcosinate, glutamate, lactylate or taurate anionic groups, salts of fatty acids, salts of galactosiduronic acids, salts of ether carboxylic acids surfactants and their mixtures.
  • anionic surfactants or surface-active agents or agents according to the invention are chosen from:
  • the anionic surfactants is chosen from sulfate of ether of lauryl alcohol and alkylene oxide containing from 1 to 4 alkylene oxide groups, especially ethylene oxide groups.
  • sulfate of ether of lauryl alcohol and alkylene oxide containing from 1 to 4 alkylene oxide groups, especially ethylene oxide groups for example, sodium laureth sulfate containing in average 2.2 ethylene oxide groups that are sold by the activate Cognis (BASF) under the name Texapon ® AOS 225 UP, Rhodia under the name Rhodapex ® esb-70/fla3, and Clariant under the name Genapol ® LRO L'O, and sodium laureth sulfate containing in average 1 ethylene oxide group that is sold by the company Zhejiang Zanyu Technology under the name SLES (N1 EO).
  • BASF analog Cognis
  • Rhodia under the name Rhodapex ® esb-70/fla3
  • isethionate sodium cocoyl isthionate
  • mentiones may be made of the sodium lauroyl methyl isethionate which is sold under the trade name ISELUX ® LQ-CLR-SB by the company Innospec Active Chemicals;
  • alkyl or acyl radicals of these various anionic surfactants preferably comprise from 12 to 20 carbon atoms.
  • the oxyalkylenated or polyoxyalkylenated anionic surfactants or surface-active agents preferably comprise from 1 to 50 alkylene oxide groups, more preferably from 1 to 4 alkylene oxide groups, in particular ethylene oxide groups.
  • the present invention comprises at least one anionic surfactant chosen from (C6-C3o)alkyl sulfates, (C6-C3o)alkyl ether sulfates, (C6-C3o)alkylamido ether sulfates, alkylaryl polyether sulfates, monoglyceride sulfates, (C6-C2 4 )acyl isethionates, or a mixture thereof.
  • anionic surfactant chosen from (C6-C3o)alkyl sulfates, (C6-C3o)alkyl ether sulfates, (C6-C3o)alkylamido ether sulfates, alkylaryl polyether sulfates, monoglyceride sulfates, (C6-C2 4 )acyl isethionates, or a mixture thereof.
  • the anionic surfactant is preferably chosen from sodium laureth sulfate, sodium lauroyl methyl isethionate, sodium cocoyl isthionate, or a mixture thereof.
  • the anionic surfactant is sodium laureth sulfate containing in average 2.2 ethylene oxide groups.
  • the content of anionic surfactant(s) represents from 1 % to 50% by weight, with respect to the weight of the composition, preferably from 5% to 30% by weight, with respect to the weight of the composition, or 10% to 25% by weight, with respect to the weight of the composition,
  • composition of the present invention comprises at least one polyalkylene glycol ether of alcohol, which can be defined as the formula (II),
  • a is an integer of 4 to 14;
  • b is an integer of 2 to 30;
  • R is a alkylene group.
  • a is an integer of 6 to 12, more preferably a is 11 ;
  • R is ethylene, or propylene group, preferably ethylene group.
  • Mentions may be made of polyethylene glycol ether of lauryl alcohol, and its mixture thereof.
  • laureth-4 or laureth-12, for example the products sold by the company Evonik Goldschmidt under the name Rewopal ® 12, Ecogreen Oleochemicals under the name Ifralan L12, or Clariant under the name Genapol ® LA 120 L'O.
  • the at least one polyalkylene glycol ether of alcohol is present in the present invention in an amount ranging from 0.01 % to 10% by weight, preferably from 0.1 % to 5% by weight, more preferably from 0.2% to 2.5% by weight, relative to the total weight of the composition.
  • composition of the present invention further comprises one or more the following additional ingredients.
  • the composition further comprises at least one amphoteric surfactant or zwitterionic surfactant.
  • amphoteric or zwitterionic surfactant(s) that may be used in the present invention may be quaternized secondary or tertiary aliphatic amine derivatives containing at least one anionic group, for instance a carboxylate, sulfonate, sulfate, phosphate or phosphonate group, and in which the aliphatic group with a linear or branched chain comprising from 8 to 22 carbon atoms.
  • amphoteric or zwitteronic surfactant is chosen from cocoylamidopropylbetaine, cocoylbetaine,
  • N-cocoylamidocarboxymethyl glycinate of an alkali metal or a mixture thereof.
  • amphoteric or zwitterionic surfactants mention may be made of the compounds of respective structure (III) below: R— isf— CHjCOO
  • R represents alkyl groups derived from coconut oil.
  • cocoylbetaine example the cocoylbetaine that is sold under the name Mirataine ® BB/FLA by the company Rhodia.
  • the amphoteric surfactant is present in an amount ranging from 1 % to 15%, preferably from 3% to 12%, more preferably from 5% to 10%, by weight of the surfactant, relative to the total weight of the
  • the composition of the present invention can contain a cationic polymer.
  • cationic polymer denotes any polymer containing cationic groups and/or groups that can be ionized into cationic groups.
  • These polymers preferably have a number-average molecular mass generally of between 1000 and 100 000.
  • Polymers of this type are especially described in FR 2 320 330, FR 2 270 846, FR 2 316 271 , FR 2 336 434, FR 2 413 907, US 2 273 780, US 2 375 853, US 2 388 614, US 2 454 547, US 3 206 462, US 2 261 002, US 2 271 378, US 3 874 870, US 4 001 432, US 3 929 990, US 3 966 904, US 4 005 193, US 4 025 617, US 4 025 627, US 4 025 653, US 4 026 945 and US 4 027 020.
  • cationic polymer(s) are chosen from cationic
  • cyclopolymer alkyldiallylamine or dialkyldiallylammonium which may be a homopolymer or copolymer containing, as main constituent of the chain, units corresponding to formula (IV) or (V): in which formulae d and e are equal to 0 or 1 , the sum d + e being equal to 1 ;
  • R32 denotes a hydrogen atom or a methyl radical;
  • R30 and R31 independently of each other, denote a CrC 8 alkyl group, a hydroxyalkyl group in which the alkyl group is C 1 -C5, an amidoalkyl group in which the alkyl is Ci-C 4 ;
  • R30 and R31 can also denote, together with the nitrogen atom to which they are attached, a heterocyclic group such as piperidyl or morpholinyl;
  • R 3 o and R31 independently of each other, preferably denote a Ci-C 4 alkyl group;
  • Y " is
  • diallyldimethylammonium chloride and of acrylamide sold under the name Merquat 550.
  • the cationic cyclopolymer used in the present invention is in presence in the composition from 0.1 % to 5% by weight, preferably from 0.5% to 2.5%, more preferably from 0.5% to 1 % by weight relative to the total weight of the composition.
  • compositions according to the invention may naturally contain, in addition, all the standard adjuvants encountered in the field of the caring for keratin materials, especially the hair, such as, for example, silicones, perfumes, preservatives, sequestering agents, thickeners, hydrating agents, antidandruff or antiseborrhoeic agents, vitamins, sunscreen agents, suspending agents, stabilizers, for example sodium chloride, magnesium dichloride or magnesium sulfate, gelling agents, film-forming polymers, or surfactants, pH regulators, and the like.
  • standard adjuvants encountered in the field of the caring for keratin materials, especially the hair such as, for example, silicones, perfumes, preservatives, sequestering agents, thickeners, hydrating agents, antidandruff or antiseborrhoeic agents, vitamins, sunscreen agents, suspending agents, stabilizers, for example sodium chloride, magnesium dichloride or magnesium sulfate, gelling agents, film-forming polymers
  • the composition may comprise one or more silicones, volatile or non-volatile, or a mixture of volatile and non-volatile silicones.
  • Mentions may be made of, for example, non-volatile silicones selected from the linear polydialkylsiloxane family containing terminal hydroxydimethylsilyl groups, such as the oils of the 48 V series from RHONE-POULENC, product Xiameter ® PMX-200 silicone fluid 60000CS sold by Dow Corning.
  • composition according to the invention may take the form of liquid, creams or gel. They may also take the form of lotions to be rinsed.
  • Another aspect of the invention is a method for caring for keratin materials, especially the hair, using the composition as above described.
  • the method of the present invention preferably comprises a step of foaming and a step of rinsing off.
  • the method of the present invention is for washing the hair.
  • Non limiting examples illustrating the invention are given.
  • compositions were prepared (inv compo stands for invention composition, and compa compo stands for comparative compositions):
  • the stabilities of the invention composition 1 and comparative compositions 1 and 2 were evaluated by leaving the above mentioned compositions under 45°C for 2 months.
  • comparative composition 1 was not stable over time, i.e. it has the issue of phase separation and thus non-homogeneous. While comparing to the comparative composition 1 , invention composition 1 and comparative composition 2 were stable over time.
  • the foaming effects of the compositions were evaluated based on the foaming abundance and the speed of foaming of the compositions.
  • speed of foaming refers to the volume of foaming generated in 120 seconds.
  • composition shows a comparable speed of foaming effect, and an improved foaming abundance. Dry combing effect
  • composition 1 and comparative compositions 1 and 2 were applied on 6 g of natural black Chinese hair, and damaged Chinese hair, respectively. The compositions were then left on the hair for 5 minutes. Then the hair was rinsed by warm water for 10 seconds, and left to dry over night at
  • Fcontrol is the combing for of control composition
  • Fcomposition is the combing force of the invention and comparative compositions, respectively.
  • the conditioning effect especially the combing effect of dry hair of the invention composition 1 was much better comparing to the comparative composition 1 or 2.
  • the invention as such possesses an improved conditioning effect, especially on the dry hair.

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Abstract

A composition comprising cyclodextrin or its derivatives, anionic surfactants, and polyalkylene glycol ether of alcohols of alcohol of formula (II), CH 3(CH 2) a(OR) bOH (II) is provided, wherein: a is an integer of 4 to 14; b is an integer of 2 to 30; and R is an alkylene group.

Description

COMPOSITION COMPRISING CYCLODEXTRIN AND ITS DERIVATIVE, ANIONIC SURFACTANT AND POLYALKYLENE GLYCOL ETHER OF ALCOHOL, AND ITS USE THEREOF
Technical Field
The present invention relates to the field of hair care. More specifically, the present invention relates to a composition for caring for keratin materials,
especially the hair, and a method for using the same. Background of the invention
It is known that products, in particular cosmetic products, having an iridescent, moire or metallized appearance are widely appreciated by consumers for their aesthetic nature and the rich appearance. The agents that give this effect are pearlescent or nacreous agents generally comprising crystals that remain
dispersed in the compositions and that reflect light.
Cyclodextrins have already been used for making nacreous compositions.
However, nacreous compositions with cyclodextrins have poor stability over time. EP 1499280, US2009/0074698 and EP1779840 disclosed specific
compositions with cyclodextrins with improved stability and nacreous effect.
To stabilize the composition, US2009/0074698 disclosed a cosmetic
composition comprising a specific cationic polymer and cyclodextrin.
It is also known that good foaming properties as well as good conditioning
properties of a cosmetic composition, especially the shampoos, are of great interests of the consumers, especially to those having sensitized hair (i.e.
damaged and/or embrittled) of varying degrees under the action of
atmospheric agents or under the action of mechanical or chemical treatments, such as dyes, bleaches and/or permanent-waving.
So there still exists a need for a novel composition, having a nacreous
appearance, with an improved stability, and providing a good foaming and conditioning effect (i.e., disentangling of the hair, especially the dry hair) to the hair after application.
Summary of the invention
The object of the invention is to provide a composition comprising at least one cyclodextrin or its derivative, at least one anionic surfactant, and at least one polyalkylene glycol ether of alcohol.
More specifically, one object of the current invention is to provide a
composition comprising, in an aqueous phase: a) at least one cyclodextrin or its derivative;
b) at least one anionic surfactant; and
c) at least one polyalkylene glycol ether of alcohol of formula (II),
CH3(CH2)a(OR)bOH (II)
wherein:
a is an integer of 4 to 14;
b is an integer of 2 to 30; and
R is a alkylene group.
Another object of the present invention is to provide a method for caring for keratin materials, especially the hair, using the above described composition. The term "keratin material" means the skin (of the body, face and around the eyes), hair, eyelashes, eyebrows, bodily hair, nails, lips or mucous membranes. Preferably, it means the keratin fibers, especially the hair.
The composition as such is found to possess an improved stability, foaming, as well as conditioning effect.
According to the present invention, by "conditioning effect" it especially refers to the disentangling of dried hair after application of the composition as described above. Detailed Description of the Present Invention
According to the present invention, the composition comprises, in an aqueous phase:
a) at least one cyclodextrin or its derivative;
b) at least one anionic surfactant; and
d) at least one polyalkylene glycol ether of alcohol of formula (II),
CH3(CH2)a(OR)bOH (II)
wherein:
a is an integer of 4 to 14;
b is an integer of 2 to 30; and
R is an alkylene group.
Aqueous phase
The composition of the present invention comprises an aqueous phase.
The aqueous phase comprises water and may comprise water-miscible organic solvents (at room temperature of 20-25°C), for instance monoalcohols containing from 2 to 6 carbon atoms, such as ethanol or isopropanol; polyols especially containing from 2 to 20 carbon atoms, preferably containing from 2 to 10 carbon atoms and preferentially containing from 2 to 6 carbon atoms, such as glycerol, propylene glycol, butylene glycol, pentylene glycol, hexylene glycol, dipropylene glycol or diethylene glycol; glycol ethers (especially containing from 3 to 16 carbon atoms) such as mono-, di- or tripropylene glycol (Ci-C4)alkyl ethers, mono-, di- or triethylene glycol (Ci-C4)alkyl ethers, and mixtures thereof.
In particular, the composition of the present invention comprises from 45% to 85% by weight, especially from 50% to 75% and more particularly from 55% to 65% by weight of the aqueous phase, relative to the total weight of the composition. Cyclodextrin and its derivatives
The composition of the present invention comprises at least one cyclodextrin or its derivative.
Cyclodextrins are especially oligosaccharides of formula (I):
Figure imgf000005_0001
in which x is equal to 4 (which corresponds to a-cyclodextrin), 5 (β-cyclodextrin) or 6 (γ-cyclodextrin).
A beta-cyclodextrin sold by the company Wacker under the name Cavamax® W7, or by the company Shandong Xinda Fine Chemical under the name Beta-Cyclodextrin, a gamma-cyclodextrin sold by the company Wacker under the name Cavamax® W8, or a mixture thereof, may especially be used.
For the purposes of the present invention, the term "cyclodextrins" also means substituted cyclodextrin derivatives, for instance methyl cyclodextrins, in particular the methyl-beta-cyclodextrin sold by the company Wacker under the name Cavasol® W7.
Preferably, the cyclodextrins of the invention are unsubstituted.
Even more preferably, a beta-cyclodextrin will be used.
According to the invention, the cyclodextrin(s) may represent from 0.5% to
15% by weight, preferably from 1 % to 10% by weight, preferentially from 1 % to 5% by weight and better still from 1 % to 2.5% by weight relative to the total weight of the final composition.
Anionic surfactant
The composition of the invention comprises at least one anionic surfactant or "surface-active agent". Anionic surfactant is understood to mean an amphiphilic compound in which the hydrophobic part carries an anionic hydrophilic group with a cationic counterion which is generally metallic (alkali metal, such as Na or K) or ammonium; the hydrophilic group is thus polar and capable of dissociating to give anions in aqueous solution.
More particularly the anionic part of the anionic surfactant is belonging to the group chosen from: C(O)OH, -C(O)O", -SO3H, -S(O)2O", -OS(O)2OH,
-OS(O)2O", -P(O)OH2, -P(O)2O", -P(O)O2 ", -P(OH)2, =P(O)OH, -P(OH)O", =P(O)O", =POH, =PO", the anionic part comprizing a cationic counter anion such as alkali metal such as sodium, or alkaline earth metal such as magnesium, or organic cationic counter anion such as ammonium salts, amine salts, or aminoalcohol salts. The surfactants may also occur in their acid forms. Mention may be made, as anionic surfactants or surface-active agents, of surfactants or surface-active agents comprising carboxylate, sulfate, sulfonate, sulfoacetate, sulfosuccinate, phosphate, isethionate, sarcosinate, glutamate, lactylate or taurate anionic groups, salts of fatty acids, salts of galactosiduronic acids, salts of ether carboxylic acids surfactants and their mixtures.
More particularly, the anionic surfactants or surface-active agents or agents according to the invention are chosen from:
· (C6-C3o)alkyl sulfates, (C6-C3o)alkyl ether sulfates, (C6-C30)alkylannido ether sulfates, alkylaryl polyether sulfates or monoglyceride sulfates; preferably for this type of anionic surfactants, (C6-C3o)alkyl ether sulfates, alkylaryl polyether sulfates, or a mixture is used. Mentions may be made of sulfate of ether of lauryl alcohol and alkylene oxide, containing from 1 to 50 alkylene oxide groups.
More preferably, the anionic surfactants is chosen from sulfate of ether of lauryl alcohol and alkylene oxide containing from 1 to 4 alkylene oxide groups, especially ethylene oxide groups. For example, sodium laureth sulfate containing in average 2.2 ethylene oxide groups that are sold by the companie Cognis (BASF) under the name Texapon® AOS 225 UP, Rhodia under the name Rhodapex® esb-70/fla3, and Clariant under the name Genapol® LRO L'O, and sodium laureth sulfate containing in average 1 ethylene oxide group that is sold by the company Zhejiang Zanyu Technology under the name SLES (N1 EO).
• (C6-C3o)alkyl sulfonates, (C6-C3o)alkylamidesulfonates, (C6-C3o)alkylaryl sulfonates, α-olefin sulfonates, paraffin sulfonates;
• (C6-C3o)akyl phosphates;
• (C6-C3o)alkyl sulfosuccinates, (C6-C3o)alkyl ether sulfosuccinates or (C6-C3o)alkylamido sulfosuccinates;
• (C6-C3o)alkyl sulfoacetates;
• (C6-C24)acylsarcosinates;
• (C6-C24)acylglutamates;
• (C6-C3o)alkylpolyglycoside carboxylic ethers;
• (C6-C3o)alkylpolyglycoside sulfosuccinates;
• (C6-C3o)alkyl sulfosuccinamates;
• (C6-C24)acyl isethionates, for example sodium lauroyl methyl
isethionate, sodium cocoyl isthionate; mentiones may be made of the sodium lauroyl methyl isethionate which is sold under the trade name ISELUX® LQ-CLR-SB by the company Innospec Active Chemicals;
• N-[(C6-C24)acyl] taurates;
• salts of fatty acids;
• (C8-C2o)acyl lactylates;
• salts of (C6-C3o)alkyl-D-galactosiduronic acids;
• salts of (C6-C3o)alkyl polyoxyalkylenated ether carboxylic acids, of
(C6-C3o)alkylaryl polyoxyalkylenated ether carboxylic acids or of (C6-C3o)alkylamido polyoxyalkylenated ether carboxylic acids;
• and their mixtures.
The alkyl or acyl radicals of these various anionic surfactants preferably comprise from 12 to 20 carbon atoms.
Furthermore, the oxyalkylenated or polyoxyalkylenated anionic surfactants or surface-active agents preferably comprise from 1 to 50 alkylene oxide groups, more preferably from 1 to 4 alkylene oxide groups, in particular ethylene oxide groups.
Advantageously, according to an embodiment, the present invention comprises at least one anionic surfactant chosen from (C6-C3o)alkyl sulfates, (C6-C3o)alkyl ether sulfates, (C6-C3o)alkylamido ether sulfates, alkylaryl polyether sulfates, monoglyceride sulfates, (C6-C24)acyl isethionates, or a mixture thereof.
According to an embodiment of the present invention, the anionic surfactant is preferably chosen from sodium laureth sulfate, sodium lauroyl methyl isethionate, sodium cocoyl isthionate, or a mixture thereof.
More preferably the anionic surfactant is sodium laureth sulfate containing in average 2.2 ethylene oxide groups.
Advantageously, the content of anionic surfactant(s) represents from 1 % to 50% by weight, with respect to the weight of the composition, preferably from 5% to 30% by weight, with respect to the weight of the composition, or 10% to 25% by weight, with respect to the weight of the composition,
polyalkylene glycol ether of alcohol
The composition of the present invention comprises at least one polyalkylene glycol ether of alcohol, which can be defined as the formula (II),
CH3(CH2)a(OR)bOH (II)
wherein:
a is an integer of 4 to 14;
b is an integer of 2 to 30; and
R is a alkylene group.
More preferably, according to an embodiment of the present invention, a is an integer of 6 to 12, more preferably a is 11 ;
b is an integer of 4 to 12; R is ethylene, or propylene group, preferably ethylene group.
Mentions may be made of polyethylene glycol ether of lauryl alcohol, and its mixture thereof.
More particularly, mentions may be made of laureth-4, or laureth-12, for example the products sold by the company Evonik Goldschmidt under the name Rewopal® 12, Ecogreen Oleochemicals under the name Ifralan L12, or Clariant under the name Genapol® LA 120 L'O.
Preferably, the at least one polyalkylene glycol ether of alcohol is present in the present invention in an amount ranging from 0.01 % to 10% by weight, preferably from 0.1 % to 5% by weight, more preferably from 0.2% to 2.5% by weight, relative to the total weight of the composition.
Additional ingredients
The composition of the present invention further comprises one or more the following additional ingredients.
Amphoteric surfactant or zwitterionic surfactant
According to an embodiment of the invention, the composition further comprises at least one amphoteric surfactant or zwitterionic surfactant.
The amphoteric or zwitterionic surfactant(s) that may be used in the present invention may be quaternized secondary or tertiary aliphatic amine derivatives containing at least one anionic group, for instance a carboxylate, sulfonate, sulfate, phosphate or phosphonate group, and in which the aliphatic group with a linear or branched chain comprising from 8 to 22 carbon atoms.
Mention may be made in particular of (C8-C2o)alkylbetaines, sulfobetaines, (C8-C20 alkyl)amido(C2-C8 alkyl)betaines and (C8-C20 alkyl)amido(C2-C8 alkyl)sulfobetaines. For example the amphoteric or zwitteronic surfactant is chosen from cocoylamidopropylbetaine, cocoylbetaine,
N-cocoylamidocarboxymethyl glycinate of an alkali metal, or a mixture thereof.
Among the amphoteric or zwitterionic surfactants, mention may be made of the compounds of respective structure (III) below: R— isf— CHjCOO
CH3 (III)
in which R represents alkyl groups derived from coconut oil.
Preferably mention is made of cocoylbetaine, example the cocoylbetaine that is sold under the name Mirataine® BB/FLA by the company Rhodia.
Advantageously, if present, the amphoteric surfactant is present in an amount ranging from 1 % to 15%, preferably from 3% to 12%, more preferably from 5% to 10%, by weight of the surfactant, relative to the total weight of the
composition.
Cationic polymer
According to one embodiment, the composition of the present invention can contain a cationic polymer.
For the purposes of the present invention, the term "cationic polymer" denotes any polymer containing cationic groups and/or groups that can be ionized into cationic groups.
These polymers preferably have a number-average molecular mass generally of between 1000 and 100 000.
Polymers of this type are especially described in FR 2 320 330, FR 2 270 846, FR 2 316 271 , FR 2 336 434, FR 2 413 907, US 2 273 780, US 2 375 853, US 2 388 614, US 2 454 547, US 3 206 462, US 2 261 002, US 2 271 378, US 3 874 870, US 4 001 432, US 3 929 990, US 3 966 904, US 4 005 193, US 4 025 617, US 4 025 627, US 4 025 653, US 4 026 945 and US 4 027 020.
More particularly, the cationic polymer(s) are chosen from cationic
cyclopolymer alkyldiallylamine or dialkyldiallylammonium, which may be a homopolymer or copolymer containing, as main constituent of the chain, units corresponding to formula (IV) or (V):
Figure imgf000011_0001
in which formulae d and e are equal to 0 or 1 , the sum d + e being equal to 1 ; R32 denotes a hydrogen atom or a methyl radical; R30 and R31 , independently of each other, denote a CrC8 alkyl group, a hydroxyalkyl group in which the alkyl group is C1 -C5, an amidoalkyl group in which the alkyl is Ci-C4; R30 and R31 can also denote, together with the nitrogen atom to which they are attached, a heterocyclic group such as piperidyl or morpholinyl; R3o and R31 , independently of each other, preferably denote a Ci-C4 alkyl group; Y" is an organic or mineral anion such as bromide, chloride, acetate, borate, citrate, tartrate, bisulfate, bisulfite, sulfate or phosphate. These polymers are described in particular in FR 2 080 759 and FR 2 190 406.
Among the polymers defined above, mention may be made more particularly of the dimethyldiallylammonium chloride homopolymer sold under the name "Merquat 100" by the company Nalco (and its homologues of low
weight-average molecular mass) and the copolymers of
diallyldimethylammonium chloride and of acrylamide, sold under the name Merquat 550.
Advantageously, the cationic cyclopolymer used in the present invention is in presence in the composition from 0.1 % to 5% by weight, preferably from 0.5% to 2.5%, more preferably from 0.5% to 1 % by weight relative to the total weight of the composition.
Adjuvant
The compositions according to the invention may naturally contain, in addition, all the standard adjuvants encountered in the field of the caring for keratin materials, especially the hair, such as, for example, silicones, perfumes, preservatives, sequestering agents, thickeners, hydrating agents, antidandruff or antiseborrhoeic agents, vitamins, sunscreen agents, suspending agents, stabilizers, for example sodium chloride, magnesium dichloride or magnesium sulfate, gelling agents, film-forming polymers, or surfactants, pH regulators, and the like.
In particular, the composition may comprise one or more silicones, volatile or non-volatile, or a mixture of volatile and non-volatile silicones. Mentions may be made of, for example, non-volatile silicones selected from the linear polydialkylsiloxane family containing terminal hydroxydimethylsilyl groups, such as the oils of the 48 V series from RHONE-POULENC, product Xiameter® PMX-200 silicone fluid 60000CS sold by Dow Corning.
Galenic form
The composition according to the invention may take the form of liquid, creams or gel. They may also take the form of lotions to be rinsed.
Another aspect of the invention is a method for caring for keratin materials, especially the hair, using the composition as above described.
The method of the present invention preferably comprises a step of foaming and a step of rinsing off.
More specifically, the method of the present invention is for washing the hair. Non limiting examples illustrating the invention are given.
Examples Preparation of invention and comparative compositions
The following compositions were prepared (inv compo stands for invention composition, and compa compo stands for comparative compositions):
% by weight of active ingredient
Compa
INCI name Inv Compa
compo 2 compo 1 compo 1
SODIUM LAURETH SULFATE 70%
containing 2.2 mol of ethylene oxide 15 15
15 (Texapon® AOS 225 UP from BASF)
COCOYLBETAINE
(Cocoylbetaine, Mirataine® BB/FLA 3 3
3 from Rhodia)
POLYQUATERNIUM-6 (Polydiallyl
dimethyl ammonium chloride,
0.3 0.3 0.3
Merquat 100 polymer from Nalco
(Lubrizol))
DIMETHICONE
(Polydimethylsiloxanes, Xiameter®
3 3 3
PMX-200 silicone fluid 60000CS from
Dow Corning)
CARBOMER ( Carbomer,
CARBOPOL® 980 POLYMER from 0.2 0.2 0.2 LUBRIZOL) CYCLODEXTRIN (CAVAMAX® W7 2
2 2
PHARMA from WACKER)
POLYSORBATE 21 (TWEEN
0 0 0.48 21 -LQ-(MV) from Croda)
LAURETH-12 (Rewopal® 12 from
0.48 0 0
Evonik Goldschmidt)
CITRIC ACID qs pH 5,2 5,2 5,2
SODIUM CHLORIDE 0.3 0.3
0.3
WATER qs 100 qs 100 qs 100
Protocol of preparation:
100 g of each of the comparative compositions 1 and 2, as well as the invention composition 1 were prepared following the steps of:
a) mixing 2.8g sodium laureth sulfate, 0.6 g laureth-12 (if present) with water, melting at a temperature of 80°C, till the mixture is well dissolved; and then mixing with 2 g cyclodextrin till it is well dissolved, and then cooling down the mixture to room temperature, mixing with 0.3 g of sodium chloride (if present), b) mixing 18.6 g of sodium laureth sulfate, 10 g of cocobetaine, 0.75 g of polyquaternium-6 with water under room temperature (25°C), then mixing with 0.2 g of carbomer and 3 g of dimethicone; and then mixing with mixture obtained from step a).
Evaluation of invention and comparative compositions
Evaluations on the stability, foaming effect, as well as dry combing effect of the invention composition 1 and comparative compositions 1 and 2 were performed.
Stability
The stabilities of the invention composition 1 and comparative compositions 1 and 2 were evaluated by leaving the above mentioned compositions under 45°C for 2 months.
Result
It was observed that the comparative composition 1 was not stable over time, i.e. it has the issue of phase separation and thus non-homogeneous. While comparing to the comparative composition 1 , invention composition 1 and comparative composition 2 were stable over time.
Foaming effect
The foaming effects of the compositions were evaluated based on the foaming abundance and the speed of foaming of the compositions.
For the purpose of the present invention, speed of foaming refers to the volume of foaming generated in 120 seconds.
The foaming abundance of the invention composition 1 and the comparative compositions 1 and 2 were evaluated following the steps of:
weighing 4 g of the invention composition 1 and comparative compositions 1 and 2, respectively, into the kitchen blender produced by Philips with the model reference HR2004;
diluting the invention composition 1 and comparative compositions 1 and 2, respectively, with water by 20 times of the volume of the composition;
mixing the diluted compositions for 1 minute at speed 1 ;
immediately transferring the produced foam and liquid into a graduate cylinder;
measuring the total volume.
The speed of foaming of the compositions was evaluated according to the steps of:
weighting 20 g of the invention example 1 and comparative examples 1 and 2, respectively, and placing them into kitchen blender produced by Philips with the model reference HR2004, respectively;
diluting the invention composition 1 and comparative compositions 1 and 2, respectively, with water by 1 .25 times of the volume of the composition;
evaluating the speed of foaming of the diluted composition using the device Teclis FOAMSCAN under airflow of 15 ml/min, for 200 seconds.
Result
The results of the foaming effects of the compositions were shown as below: Comparing to the comparative compositions 1 and 2, the invention
composition shows a comparable speed of foaming effect, and an improved foaming abundance. Dry combing effect
0.4 g of the invention composition 1 and comparative compositions 1 and 2 were applied on 6 g of natural black Chinese hair, and damaged Chinese hair, respectively. The compositions were then left on the hair for 5 minutes. Then the hair was rinsed by warm water for 10 seconds, and left to dry over night at
Figure imgf000016_0001
room temperature. After 5 times repeated application using the process described herein, the combing force between the hair stress and a comb was measured by the device named Combing Tester JC45A-001 , sold by JAU CHUNG. The reduction of combing force was measured based on the following formula (control is 9% of sodium laureth sulfate water solution): Fcontrol Fcomposition
Reduction (%) = χ 100%
Fcontrol
wherein:
Reduction (%) is the reduction of combing force;
Fcontrol is the combing for of control composition;
Fcomposition is the combing force of the invention and comparative compositions, respectively.
Result
The results of the conditioning effects, especially the reduction of combing force of dry hair of the compositions were shown below:
Figure imgf000017_0001
As shown in the table, the conditioning effect, especially the combing effect of dry hair of the invention composition 1 was much better comparing to the comparative composition 1 or 2. The invention as such possesses an improved conditioning effect, especially on the dry hair.

Claims

What is claimed is
1 . A composition comprising, in an aqueous phase: a) at least one cyclodextrin or its derivative;
b) at least one anionic surfactant; and
c) at least one polyalkylene glycol ether of alcohol of formula (II),
CH3(CH2)a(OR)bOH (II)
wherein:
a is an integer of 4 to 14;
b is an integer of 2 to 30; and
R is a alkylene group.
2. Composition of claim 1 , wherein the aqueous is present in an amount ranging from 45% to 85% by weight, especially from 50% to 75% and more particularly from 55% to 65% by weight, relative to the total weight of the composition.
3. Composition of claim 1 or 2, wherein the cyclodextrin or its derivative is chosen from a-cyclodextrin, β-cyclodextrin, γ-cyclodextrin, methyl derivatives thereof, or a mixture thereof, preferably the cyclodextrin is chosen from β-cyclodextrin.
4. Composition of any one of the preceding claims 1 to 3, wherein the cyclodextrin is present in an amount ranging from 0.5% to 15% by weight, preferably from 1 % to 10% by weight, more preferably from 1 % to 5% by weight, and even more preferably from 1 % to 2.5% by weight, relative to the total weight of the composition.
5. Composition of any one of the preceding claims 1 to 4, wherein the at least one anionic surfactant is chosen from the group consisting of carboxylate, sulfate, sulfonate, sulfoacetate, sulfosuccinate, phosphate, isethionate, sarcosinate, glutamate, lactylate or taurate anionic groups, their salts, salts of fatty acids, salts of galactosiduronic acids, salts of ether carboxylic acids, or a mixture thereof.
6. Composition of any one of the preceding claims 1 to 5, wherein the at least one anionic surfactant is chosen from (C6-C3o)alkyl sulfates,
(C6-C3o)alkyl ether sulfates, (C6-C3o)alkylamido ether sulfates, alkylaryl polyether sulfates, monoglyceride sulfates, (C6-C3o)alkyl sulfonates, (C6-C3o)alkylamidesulfonates, (C6-C3o)alkylaryl sulfonates, a-olefin sulfonates, paraffin sulfonates, (C6-C3o)akyl phosphates, (C6-C3o)alkyl sulfosuccinates, (C6-C3o)alkyl ether sulfosuccinates (C6-C3o)alkylamido sulfosuccinates, (C6-C30)alkyl sulfoacetates, (C6-C24)acylsarcosinates, (C6-C24)acylglutamates, (C6-C3o)alkylpolyglycoside carboxylic ethers, (C6-C3o)alkylpolyglycoside sulfosuccinates, (C6-C3o)alkyl
sulfosuccinamates, (C6-C24)acyl isethionates, N-[(C6-C24)acyl] taurates, salts of fatty acids, (C8-C2o)acyl lactylates, salts of
(C6-C3o)alkyl-D-galactosiduronic acids, salts of (C6-C3o)alkyl
polyoxyalkylenated ether carboxylic acids, salts of (C6-C30)alkylaryl polyoxyalkylenated ether carboxylic acids, salts of (C6-C3o)alkylamido polyoxyalkylenated ether carboxylic acids, or a mixture thereof.
7. Composition of any one of the claims 1 to 6, wherein the anionic surfactant is chosen from (C6-C3o) alkyl sulfates, (C6-C3o)alkyl ether sulfates, (C6-C30)alkylamido ether sulfates, alkylaryl polyether sulfates, monoglyceride sulfates, (C6-C24)acyl isethionates, or a mixture thereof; preferably from sodium laureth sulfate, sodium lauroyl methyl isethionate, sodium cocoyi isthionate, or a mixture thereof, more preferably the anionic surfactant is sodium laureth sulfate containing in average from 1 to 4 ethylene oxide groups, more preferably containing in average 2.2 ethylene oxide groups.
8. Composition of any one of the preceding claims 1 to 7, wherein the anionic surfactant is present in an amount ranging from 1 % to 50% by weight, preferably from 5% to 30% by weight, more preferably from 10% to 25% by weight, relative to the total weight of the composition
9. Composition of any one of the preceding claimsl to 8, wherein the at least one polyalkylene glycol ether of fatty alcohol of formula (II),
CH3(CH2)a(OR)bOH (II)
wherein, preferably, a is an integer of 6 to 12, more preferably a is 1 1 ; b is an integer of 4 to 12;
R is ethylene, or propylene group, preferably ethylene group.
10. Composition of any one of the preceding claims 1 to 9, wherein the at least one polyalkylene glycol ether of fatty alcohol is chosen from
polyethylene glycol ether of lauryl alcohol or its mixture; more preferably laureth-12, laureth-4, or a mixture thereof, more preferably laureth-12.
1 1 . Composition of any one of the preceding claims 1 to 10, wherein the polyalkylene glycol ether of fatty alcohol is present in an amount ranging from 0.01 % to 10% by weight, from 0.1 % to 5% by weight, more preferably from 0.2% to 2.5% by weight, relative to the total weight of the composition.
12. Composition of any one of the preceding claims 1 to 1 1 further comprises at least one amphoteric surfactant or zwitterionic surfactant chosen from (C8-C2o)alkylbetaines, sulfobetaines, (C8-C20
alkyl)amido(C2-C8 alkyl)betaines, (C8-C2o alkyl)amido(C2-C8
alkyl)sulfobetaines, or a mixture thereof, preferably chosen from
cocoylamidopropylbetaine, cocoylbetaine, N-cocoylamidocarboxymethyl glycinate of an alkali metal, more preferably the amphoteric surfactant or zwitterionic surfactant is cocoylbetaine.
13. Composition of any one of the preceding claims 1 to 12, wherein the amphoteric surfactant or zwitterionic surfactant is present in an amount ranging from 1 % to 15%, preferably from 3% to 12%, more preferably from 5% to 10% by weight, relative to the total weight of the composition.
14. Composition of any one of the preceding claims 1 to 13 comprises at least one cationic polymer chosen from: cationic cyclopolymer alkyldiallylamine or dialkyldiallylammonium, homopolymer or copolymer containing, as a main constituent of the chain, units of formula (IV) or (V):
Figure imgf000021_0001
wherein,
d and e, same or different, are equal to 0 or 1 , and the sum d + e being equal to 1 ,
R32 denotes a hydrogen atom or a methyl radical,
R30 and R31 , independently of each other, denote a d-Cs alkyl group, a hydroxyalkyi group in which the alkyl group is C1-C5, an amidoalkyl group in which the alkyl is Ci-C4; R30 and R31 can also denote, together with the nitrogen atom to which they are attached, a heterocyclic group such as piperidyl or morpholinyl; R3o and R31 , independently of each other, preferably denote a Ci-C4 alkyl group,
Y- is an organic or mineral anion such as bromide, chloride, acetate, borate, citrate, tartrate, bisulfate, bisulfite, sulfate or phosphate,
; preferably the cationic polymer is chosen from dialkyldiallylammonium, more preferably dimethyldiallylammonium chloride homopolymer.
15. Composition of any one of the preceding claims 1 to 14 comprises at least one adjuvant chosen from silicones, perfumes, preservatives, sequestering agents, thickeners, hydrating agents, antidandruff or antiseborrhoeic agents, vitamins, sunscreen agents, suspending agents, stabilizers, for example sodium chloride, magnesium dichloride or magnesium sulfate, gelling agents, film-forming polymers, or surfactants, pH regulators, or a mixture thereof, wherein the silicone is preferably chosen from non-volatile silicones selected from the linear
polydialkylsiloxane family containing terminal hydroxydimethylsilyl groups, more preferably polydimethylsiloxanes.
16. A method for caring for keratin materials, especially the hair, comprising the step of applying to the said keratin material the
composition of any one of the preceding claims 1 to 15, preferably the method comprises steps of foaming and rinsing off, more preferably the method comprising washing the keratin materials, preferably the hair.
PCT/CN2013/089581 2013-12-16 2013-12-16 Composition comprising cyclodextrin and its derivative, anionic surfactant and polyalkylene glycol ether of alcohol, and its use thereof WO2015089716A1 (en)

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