WO2020002128A1 - Composition comprising a particular double salt of a diammonium and carboxylate(s), method and use thereof - Google Patents

Composition comprising a particular double salt of a diammonium and carboxylate(s), method and use thereof Download PDF

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Publication number
WO2020002128A1
WO2020002128A1 PCT/EP2019/066353 EP2019066353W WO2020002128A1 WO 2020002128 A1 WO2020002128 A1 WO 2020002128A1 EP 2019066353 W EP2019066353 W EP 2019066353W WO 2020002128 A1 WO2020002128 A1 WO 2020002128A1
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Prior art keywords
composition
compound
glycol
double salt
weight
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Richa MEHTA
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LOreal SA
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LOreal SA
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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
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41Amines
    • 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
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36Carboxylic acids; Salts or anhydrides thereof
    • A61K8/361Carboxylic acids having more than seven carbon atoms in an unbroken chain; Salts or anhydrides thereof
    • 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
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36Carboxylic acids; Salts or anhydrides thereof
    • A61K8/365Hydroxycarboxylic acids; Ketocarboxylic acids
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/002Preparations for repairing the hair, e.g. hair cure

Definitions

  • the present invention relates to a composition
  • a composition comprising a particular double salt consisting of a diammonium and carboxylate(s), and at least one cosmetically acceptable solvent.
  • the intensive and repeated brushing of the hair causes the appearance of split ends in the hair.
  • At least one cosmetically acceptable solvent at least one cosmetically acceptable solvent.
  • the compo sition according to the invention makes it possible to improve the cosmetic properties conferred on keratinous fibers, in particular on sensitized hair.
  • composition according to the invention makes it possible to improve the quality of the hair, in particular a better resistance to breakage and a better sensoriality of the hair.
  • composition according to the invention makes it po ssible to significantly repair the split ends of the hair.
  • double salt used in the present description is a salt obtained from a diamine and carboxylic acid(s) .
  • alkyl used in the present description, in particular in the expression “alkylcarboxylate Alk-COO”, is a saturated hydrocarbon radical, linear or branched, preferably a saturated linear C 2 -C i 2 hydrocarbon radical.
  • the composition comprises a double salt of the following formula (I) , consisting of a diammonium and carboxylate(s) as above defined:
  • the double salt of formula (I) is chosen from the double salts of following formula (lb) :
  • p represents an integer between 0 and 2;
  • p is an integer equal to 1 .
  • X (respectively Y ) are selected from C 2 -C g alkylcarboxylate Alk-COO optionally substituted by one or more hydroxy.
  • X (respectively Y ) represents glycolate or caprylate .
  • glycolate is also named hydroxyethanoate or hydroxyacetate.
  • the structure of the glycolate is:
  • the caprylate is also named octanoate.
  • the structure of the caprylate is :
  • the double salt of formula (I) (respectively of formula (lb)) is such that the molar ratio of the carboxylate X (respectively Y ) to the diammonium is 2.
  • One object of the present invention is the compound ( 1 ) and/or the compound (2) , as previously described.
  • the double salt of formula (I) present in the composition according to the invention represents from 0.0 1 to 20 % by weight, more preferably from 0. 1 to 15 % by weight, even more preferably from 0,5 to 10% by weight, and even better from 1 to 8 % by weight, relative to the total weight of the composition according to the invention .
  • the double salt of formula (lb) present in the composition according to the invention represents from 0.0 1 to 20 % by weight, more preferably from 0. 1 to 15 % by weight, even more preferably from 0,5 to 10% by weight, and even better from 1 to 8 % by weight, relative to the total weight of the composition according to the invention .
  • the composition comprises at least one cosmetically acceptable solvent.
  • the cosmetically acceptable solvent(s) present(s) in the composition according to the invention are preferably selected from water, organic solvents, and mixtures thereof.
  • the organic solvents that may be used are preferably water- miscible (at room temperature: 25 °C) .
  • the water-miscible organic solvents can be cho sen from 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 (C i -C 4 )alkyl ethers, mono
  • the organic solvent is chosen from propylene glycol, glycerin, and mixtures thereof.
  • the composition according to the invention comprises at least one cosmetically acceptable solvent chosen from water, monoalcohols containing from 2 to 6 carbon atoms, polyols, glycol ethers, and mixture thereof; more preferably chosen from water, ethanol, isopropanol, glycerol, propylene glycol, butylene glycol, pentylene glycol, hexylene glycol, dipropylene glycol, diethylene glycol, mono-, di- or tripropylene glycol (C i -C 4 )alkyl ethers, mono- , di- or triethylene glycol (C i -C 4 )alkyl ethers, and mixtures thereof; even better chosen from water, ethanol, isopropanol, glycerol, propylene glycol, butylene glycol, and mixture thereof.
  • a cosmetically acceptable solvent chosen from water, monoalcohols containing from 2 to 6 carbon atoms, polyols, glycol ethers, and mixture thereof;
  • the composition according to the invention comprises water.
  • the composition according to the invention comprises water in a total content ranging from 45 % to 99.9 % by weight, more preferably from 50% to 99% by weight, even more preferably from 60% to 98 % by weight, relative to the total weight of the composition according to the invention.
  • the composition according to the invention comprises at least one additional compound chosen from surfactants, cationic polymers, amphoteric polymers, or mixture thereof.
  • the surfactant(s) is(are) selected from nonionic surfactants, cationic surfactants, or mixture thereof.
  • the composition may optionally further comprise at least one cationic surfactant.
  • the cationic surfactants that can be used according to the invention can be chosen from polyoxyalkylenated primary, secondary or tertiary fatty amine salts, quaternary ammonium salts, and mixtures thereof.
  • tetraalkylammonium halides preferably chlorides, such as dialkyldimethylammonium or alkyltrimethylammonium chlorides in which the alkyl group comprises from 12 to 22 carbon atoms, particularly behenyltrimethylammonium, distearyldimethylammonium, cetyltrimethylammonium, and benzyldimethylstearylammonium chlorides.
  • palmitylamidopropyltrimethylammonium halides preferably chlorides
  • stearamidopropyldimethyl(myristyl acetate) -ammonium halides preferably chlorides
  • FINQUAT CT-P Quaternium 89
  • FINQUAT CT Quaternium 75
  • cationic surfactant are for examples the chloride or methyl sulfate of diacyloxyethyldimethylammonium, diacyloxyethylhydroxyethyl -methyl ammonium, mono acyloxyethyldihydroxyethylmethyl ammonium, triacyloxyethylmethylammonium or monoacyloxyethylhydroxyethyl- dimethylammonium, and mixtures thereof.
  • the acyl groups preferably contain 14 to 18 carbon atoms and are obtained more particularly from a plant oil, such as palm oil or sunflower oil. When the compound contains several acyl groups, these groups may be identical or different.
  • Such compounds are, for example, sold under the names DEHYQUART ® by the company HENKEL, STEPANQUAT ® by the company STEPAN, NOXAMIUM ® by the company CECA or
  • the composition comprises at least one surfactant; more preferably selected from cationic surfactants; more preferably still chosen from cetyltrimethylammonium salts, behenyltrimethylammonium salts, dipalmitoylethylhydroxyethyl-methylammonium salts, and mixtures thereof; better from behenyltrimethylammonium chloride or methosulfate, cetyltrimethylammonium chloride or methosulfate, dipalmitoylethylhydroxyethylmethylammonium chloride or methosulfate, and mixtures thereof; even better, the cationic surfactant is a cetyltrimethylammonium salt.
  • the cationic surfactant(s) when the cationic surfactant(s) is/are present in the composition according to the invention, represent(s) from 0.01 to 20 % by weight, more preferably from 0.05 to 15 % by weight, even more preferably from 0. 1 to 10 % by weight, and even better from 0.2 to 5 % by weight, relative to the total weight of the composition according to the invention.
  • Nonionic surfactants
  • composition may optionally further comprise at least one nonionic surfactant.
  • the nonionic surfactants may be chosen from alcohols, a-diols and (C i_ 2 o)alkylphenols, these compounds being polyethoxylated and/or polypropoxylated and/or polyglycerolated, the number of ethylene oxide and/or propylene oxide groups possibly ranging from 1 to 100, and the number of glycerol groups possibly ranging from 2 to 30 ; or alternatively these compounds comprising at least one fatty chain comprising from 8 to 30 carbon atoms and especially from 16 to 30 carbon atoms .
  • polyethoxylated fatty amides preferably
  • the composition comprises at least one nonionic surfactant; more preferably chosen from (C 6 -C 24 alkyl)polyglycosides, and more particularly (C g_ i g alkyl) (poly)glyco sides, ethoxylated C g -C 3 o fatty acid esters of sorbitan, polyethoxylated C g -C 3 o fatty alcohols and polyoxyethylenated C g -C 3 o fatty acid esters, these compounds preferably containing from 2 to 150 mol of ethylene oxide, and mixtures thereof.
  • nonionic surfactant more preferably chosen from (C 6 -C 24 alkyl)polyglycosides, and more particularly (C g_ i g alkyl) (poly)glyco sides, ethoxylated C g -C 3 o fatty acid esters of sorbitan, polyethoxylated C g -C 3 o fatty alcohol
  • the nonionic surfactant(s) when the nonionic surfactant(s) is/are present in the composition according to the invention, represent(s) from 0.0 1 to 20 % by weight, more preferably from 0.05 to 15 % by weight, even more preferably from 0. 1 to 10 % by weight, and even better from 0.2 to 5 % by weight, relative to the total weight of the composition according to the invention.
  • the composition may optionally further comprise at least one cationic polymer.
  • cationic polymer means any polymer comprising cationic groups and/or groups that can be ionized to cationic groups .
  • the cationic polymer is hydrophilic or amphiphilic.
  • the preferred cationic polymers are chosen from those that contain units comprising primary, secondary, tertiary and/or quaternary amine groups that may either form part of the main polymer chain or may be borne by a side substituent directly connected thereto .
  • the cationic polymers that may be used preferably have a weight-average molar mass (Mw) of between 500 and 5x l 0 6 approximately and preferably between 10 3 and 3x l 0 6 approximately.
  • Mw weight-average molar mass
  • the composition comprises at least one cationic polymer; more preferably the cationic polymer(s) is/are chosen from cationic polysaccharides, especially cationic celluloses and galactomannan gums, and in particular quaternary cellulose ether derivatives such as the products sold under the name“JR 400” by the company Amerchol, cationic cyclopolymers, in particular dimethyldiallylammonium salt (for example chloride) homopolymers or copolymers, sold under the names Merquat 100 , Merquat 550 and Merquat S by the company Nalco, quaternary polymers of vinylpyrrolidone and of vinylimidazole, optionally crosslinked homopolymers or copolymers of methacryloyloxy(C i - C 4 )alkyltri(C i -C 4 )alkylammonium salts, and mixtures thereof.
  • cationic polymer(s) is/are chosen from cationic polysaccharides
  • the cationic polymer(s) when the cationic polymer(s) is/are present in the composition according to the invention, represent(s) from 0.01 to 5 % by weight, more preferably from 0.05 to 3 % by weight, even more preferably from 0. 1 to 2% by weight, relative to the total weight of the composition according to the invention .
  • the composition may optionally further comprise at least one amphoteric polymer.
  • amphoteric polymers that can be used according to the invention are preferably chosen from amphoteric polymers comprising a repetition of:
  • the said amphoteric polymers consist solely of units derived from monomers (i) of (meth)acrylamide type, (ii) of (meth)acrylamidoalkyltrialkylammonium type and (iii) of (meth)acrylic acid type.
  • amphoteric polymers that are particularly preferred, mention may be made of acrylamide/methacrylamidopropyltrimethyl ammonium chloride/acrylic acid terpolymers .
  • Such polymers are listed in the CTFA Dictionary (International Co smetic Ingredient Dictionary) under the name Polyquaternium 53.
  • Corresponding products are especially sold under the names Merquat 2003 and Merquat 2003 PR by the company Nalco .
  • amphoteric polymer As another type of amphoteric polymer that may be used, mention may also be made of copolymers based on (meth)acrylic acid and on a dialkyldiallylammonium salt, such as copolymers of
  • (meth)acrylic acid and of dimethyldiallylammonium chloride are examples.
  • An example that may be mentioned is Merquat 280 sold by the company Nalco .
  • the composition comprises at least one amphoteric polymer; more preferably the amphoteric polymer(s) is/are chosen from acrylamide/methacrylamidopropyltrimethyl ammonium chloride/acrylic acid terpolymers, cocobetaine, cocoamidopropylbetaine, sodium cocoamphoacetate, sodium cocoamphopropionate, disodium cocoamphodiacetate, disodium cocoamphodipropionate, sodium lauroamphoacetate, sodium cocoylisethionate, and mixtures thereof.
  • the amphoteric polymer(s) is/are chosen from acrylamide/methacrylamidopropyltrimethyl ammonium chloride/acrylic acid terpolymers, cocobetaine, cocoamidopropylbetaine, sodium cocoamphoacetate, sodium cocoamphopropionate, disodium cocoamphodiacetate, disodium cocoamphodipropionate, sodium lauroamphoacetate, sodium cocoylisethionate, and mixtures
  • the amphoteric polymer(s) when the amphoteric polymer(s) is/are present in the composition according to the invention, the amphoteric polymer(s) represent(s) from 0.01 to 5 % by weight, more preferably from 0.05 to 3 % by weight, even more preferably from 0. 1 to 2% by weight, relative to the total weight of the composition according to the invention .
  • composition according to the invention optionally comprises any auxiliary ingredient usually used in the co smetic field.
  • auxiliary ingredient usually used in the co smetic field.
  • Such ingredients may be selected, for example, from emulsifying agents, conditioning agents, stabilizers such as sodium chloride, magnesium dichloride or magnesium sulfate, moisturizing agents, shine agents, fillers, colorants, pigments, chelating compounds, sequestering agents, fragrances, preservatives, stabilizers, and mixtures thereof.

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Abstract

The present invention relates to a composition comprising a particular double salt consisting of a diammonium and carboxylate(s), and at least one cosmetically acceptable solvent. The present invention also relates to particular double salts, a method for treatment of keratin fibers, and the use of the said composition for treatment of keratin fibers.

Description

COMPOSITION COMPRISING A PARTICULAR DOUBLE SALT OF A DIAMMONIUM AND CARBOXYLATE(S), METHOD AND
USE THEREOF
The present invention relates to a composition comprising a particular double salt consisting of a diammonium and carboxylate(s), and at least one cosmetically acceptable solvent.
The present invention also relates to particular double salts, a method for treatment of keratin fibers, and the use of the said composition for treatment of keratin fibers .
External atmospheric agents such as pollution and weather, as well as mechanical or chemical treatments such as brushing, combing, dyeing, bleaching, perms, straightening, repeated washing, can damage and / or weaken the hair. The hair is damaged and can become dry, rough, brittle, dull, split and / or soft.
More particularly, the intensive and repeated brushing of the hair, especially wet, causes the appearance of split ends in the hair.
To overcome these drawbacks, it is customary to cut split ends with scissors or to use hair compositions comprising silicones, intended to condition the hair by providing them with co smetic properties and good shaping .
However, the conditioning effect obtained by these silicone hair compositions does not present a good repair of split ends .
There is therefore a real need to develop care/repair compositions for keratin fibers that are capable of improving the quality of the fiber such as softness, disentangling, smoothing, discipline, volume, strength of the fibers, control of the volume and of the hairstyle, for example by repairing the split ends of the hair.
This aim is achieved by the present invention, one subj ect of which is a composition comprising:
a double salt of the following formula (I) , consisting of a diammonium and carboxylate:
Figure imgf000003_0001
L (I) in which:
n represents an integer ranging from 1 to 10 ; preferably n=2; m is an integer selected from 1 or 2, preferably m= l ; X represents a carboxylate compound associated with a(the) cationic charge(s) of the double salt of formula (I) , selected from C2 -C 1 2 alkyl carboxylate (Alk-COO ) optionally substituted by one or more hydroxy;
at least one cosmetically acceptable solvent.
The applicant has found, surprisingly, that the compo sition according to the invention makes it possible to improve the cosmetic properties conferred on keratinous fibers, in particular on sensitized hair.
It has also been found that the composition according to the invention makes it possible to improve the quality of the hair, in particular a better resistance to breakage and a better sensoriality of the hair.
In particular, it has been found that the composition according to the invention makes it po ssible to significantly repair the split ends of the hair.
Other objects, characteristics and advantages of the invention will emerge more clearly on reading the description and the examples that follow.
In the present description and unless otherwise indicated:
- the limits of a range of values are included within this range, in particular in the expressions "of between ... and ... " and "ranging from - the expression "at least one" used in the present description is equivalent to the expression " one or more " and may be substituted for it.
- The expression “double salt” used in the present description is a salt obtained from a diamine and carboxylic acid(s) .
- The expression “alkyl” used in the present description, in particular in the expression “alkylcarboxylate Alk-COO”, is a saturated hydrocarbon radical, linear or branched, preferably a saturated linear C2 -C i2 hydrocarbon radical.
A double salt of formula (I)
According to the invention, the composition comprises a double salt of the following formula (I) , consisting of a diammonium and carboxylate(s) as above defined:
Figure imgf000004_0001
Preferably, the double salt of formula (I) is chosen from the double salts of following formula (lb) :
Figure imgf000004_0002
in which:
p represents an integer between 0 and 2;
Y represents a carboxylate compound associated with a(the) cationic charge(s) of the double salt of formula (lb), selected from C2 -C i2 alkylcarboxylate Alk-COO optionally sub stituted by one or more hydroxy.
Preferably, p is an integer equal to 1 . Preferably, X (respectively Y ) are selected from C 2-C g alkylcarboxylate Alk-COO optionally substituted by one or more hydroxy.
More preferably, X (respectively Y ) represents glycolate or caprylate .
The glycolate is also named hydroxyethanoate or hydroxyacetate. The structure of the glycolate is:
Figure imgf000005_0001
The caprylate is also named octanoate. The structure of the caprylate is :
Figure imgf000005_0002
Preferably, the double salt of formula (I) (respectively of formula (lb)) is such that the molar ratio of the carboxylate X (respectively Y ) to the diammonium is 2.
According to a preferred embodiment of the invention, the double salt of formula (I) (respectively of formula (lb)) is selected from the following compound ( 1 ) or compound (2) , or mixture thereof.
The compound ( 1 ) and the compound (2) are defined as follows :
Figure imgf000005_0003
compound ( 1 )
Figure imgf000006_0001
compound (2)
The compound ( 1 ) correspond to a double salt of 4,7 , l O-trioxa-
1. 13 -tridecane diamine diglycol ate.
The compound (2) correspond to a double salt of 4,7 , l O-trioxa-
1. 13 -tridecanediamine dicaprylate.
One object of the present invention is the compound ( 1 ) and/or the compound (2) , as previously described.
Preferably, the double salt of formula (I) present in the composition according to the invention, represents from 0.0 1 to 20 % by weight, more preferably from 0. 1 to 15 % by weight, even more preferably from 0,5 to 10% by weight, and even better from 1 to 8 % by weight, relative to the total weight of the composition according to the invention .
Preferably, the double salt of formula (lb) present in the composition according to the invention, represents from 0.0 1 to 20 % by weight, more preferably from 0. 1 to 15 % by weight, even more preferably from 0,5 to 10% by weight, and even better from 1 to 8 % by weight, relative to the total weight of the composition according to the invention .
Cosmetically acceptable solvent
According to the invention, the composition comprises at least one cosmetically acceptable solvent.
The cosmetically acceptable solvent(s) present(s) in the composition according to the invention are preferably selected from water, organic solvents, and mixtures thereof. The organic solvents that may be used are preferably water- miscible (at room temperature: 25 °C) . The water-miscible organic solvents can be cho sen from 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 (C i -C4)alkyl ethers, mono- , di- or triethylene glycol (C i -C4)alkyl ethers, and mixtures thereof.
In certain embodiments of the present invention, the organic solvent is chosen from propylene glycol, glycerin, and mixtures thereof.
According to a preferred embodiment of the invention, the composition according to the invention comprises at least one cosmetically acceptable solvent chosen from water, monoalcohols containing from 2 to 6 carbon atoms, polyols, glycol ethers, and mixture thereof; more preferably chosen from water, ethanol, isopropanol, glycerol, propylene glycol, butylene glycol, pentylene glycol, hexylene glycol, dipropylene glycol, diethylene glycol, mono-, di- or tripropylene glycol (C i -C4 )alkyl ethers, mono- , di- or triethylene glycol (C i -C4 )alkyl ethers, and mixtures thereof; even better chosen from water, ethanol, isopropanol, glycerol, propylene glycol, butylene glycol, and mixture thereof.
Preferably, the composition according to the invention comprises water.
More preferably, the composition according to the invention comprises water in a total content ranging from 45 % to 99.9 % by weight, more preferably from 50% to 99% by weight, even more preferably from 60% to 98 % by weight, relative to the total weight of the composition according to the invention. Preferably, the composition according to the invention comprises at least one additional compound chosen from surfactants, cationic polymers, amphoteric polymers, or mixture thereof.
More preferably, the surfactant(s) is(are) selected from nonionic surfactants, cationic surfactants, or mixture thereof.
Cationic surfactants
According to the invention, the composition may optionally further comprise at least one cationic surfactant.
The cationic surfactants that can be used according to the invention can be chosen from polyoxyalkylenated primary, secondary or tertiary fatty amine salts, quaternary ammonium salts, and mixtures thereof.
Mention may be made of tetraalkylammonium halides, preferably chlorides, such as dialkyldimethylammonium or alkyltrimethylammonium chlorides in which the alkyl group comprises from 12 to 22 carbon atoms, particularly behenyltrimethylammonium, distearyldimethylammonium, cetyltrimethylammonium, and benzyldimethylstearylammonium chlorides.
Mention may also be made of palmitylamidopropyltrimethylammonium halides, preferably chlorides, or stearamidopropyldimethyl(myristyl acetate) -ammonium halides, preferably chlorides, such as the product sold under the name CERAPHYL® 70 by the company VAN DYK.
- imidazoline quaternary ammonium salts for example under the name REWOQUAT® W 75 by the company REWO.
- quaternary di- or triammonium salts for example, FINQUAT CT-P (Quaternium 89) and FINQUAT CT (Quaternium 75) sold by the company FINETEX .
Other cationic surfactant are for examples the chloride or methyl sulfate of diacyloxyethyldimethylammonium, diacyloxyethylhydroxyethyl -methyl ammonium, mono acyloxyethyldihydroxyethylmethyl ammonium, triacyloxyethylmethylammonium or monoacyloxyethylhydroxyethyl- dimethylammonium, and mixtures thereof. The acyl groups preferably contain 14 to 18 carbon atoms and are obtained more particularly from a plant oil, such as palm oil or sunflower oil. When the compound contains several acyl groups, these groups may be identical or different.
Such compounds are, for example, sold under the names DEHYQUART® by the company HENKEL, STEPANQUAT® by the company STEPAN, NOXAMIUM® by the company CECA or
REWOQUAT® WE 1 8 by the company REWO-WITCO.
According to a preferred embodiment of the invention, the composition comprises at least one surfactant; more preferably selected from cationic surfactants; more preferably still chosen from cetyltrimethylammonium salts, behenyltrimethylammonium salts, dipalmitoylethylhydroxyethyl-methylammonium salts, and mixtures thereof; better from behenyltrimethylammonium chloride or methosulfate, cetyltrimethylammonium chloride or methosulfate, dipalmitoylethylhydroxyethylmethylammonium chloride or methosulfate, and mixtures thereof; even better, the cationic surfactant is a cetyltrimethylammonium salt.
Preferably, when the cationic surfactant(s) is/are present in the composition according to the invention, the cationic surfactant(s) represent(s) from 0.01 to 20 % by weight, more preferably from 0.05 to 15 % by weight, even more preferably from 0. 1 to 10 % by weight, and even better from 0.2 to 5 % by weight, relative to the total weight of the composition according to the invention. Nonionic surfactants
According to the invention, the composition may optionally further comprise at least one nonionic surfactant.
According to the invention, the nonionic surfactants may be chosen from alcohols, a-diols and (C i_2o)alkylphenols, these compounds being polyethoxylated and/or polypropoxylated and/or polyglycerolated, the number of ethylene oxide and/or propylene oxide groups possibly ranging from 1 to 100, and the number of glycerol groups possibly ranging from 2 to 30 ; or alternatively these compounds comprising at least one fatty chain comprising from 8 to 30 carbon atoms and especially from 16 to 30 carbon atoms .
Mention may also be made of condensates of ethylene oxide and of propylene oxide with fatty alcohols ; polyethoxylated fatty amides preferably having from 2 to 30 ethylene oxide units, polyglycerolated fatty amides comprising on average from 1 to 5 , and in particular from 1 .5 to 4, glycerol groups; ethoxylated fatty acid esters of sorbitan preferably containing from 2 to 40 ethylene oxide units, fatty acid esters of sucrose, polyoxyalkylenated and preferably polyoxyethylenated fatty acid esters containing from 2 to 150 mol of ethylene oxide, including oxyethylenated plant oils, N- (C6-24 alkyl)glucamine derivatives, amine oxides such as (C io-i4 alkyl)amine oxides or N - (C I O- I 4 acyl)aminopropylmorpholine oxides. Mention may also be made of nonionic surfactants of alkyl(poly)glycoside type, preferably, the alkyl(poly)glycoside surfactant is an alkyl(poly)glucoside surfactant. C g/C i6 alkyl(poly)glycosides 1 ,4, and especially decyl glucosides and caprylyl/capryl glucosides, are most particularly preferred.
Among the commercial products, mention may be made of the products sold by the company COGNIS under the names PLANTAREN® (600 CS/U, 1200 and 2000) or PLANTACARE® (8 18 , 1200 and 2000) ; the products sold by the company SEPPIC under the names ORAMIX CG 1 10 and ORAMIX NS 10 ; the products sold by the company BASF under the name LUTENSOL GD 70, or else the products sold by the company CHEM Y under the name AG 10 LK.
Preferably, use is made of C g/C i6-alkyl(poly)glycosides 1 ,4, especially as an aqueous 53 % solution, such as those sold by Cognis under the reference Plantacare® 8 18 UP . According to a preferred embodiment of the invention, the composition comprises at least one nonionic surfactant; more preferably chosen from (C 6-C24 alkyl)polyglycosides, and more particularly (C g_ i g alkyl) (poly)glyco sides, ethoxylated C g -C 3o fatty acid esters of sorbitan, polyethoxylated C g -C 3o fatty alcohols and polyoxyethylenated C g -C 3o fatty acid esters, these compounds preferably containing from 2 to 150 mol of ethylene oxide, and mixtures thereof. Preferably, when the nonionic surfactant(s) is/are present in the composition according to the invention, the nonionic surfactant(s) represent(s) from 0.0 1 to 20 % by weight, more preferably from 0.05 to 15 % by weight, even more preferably from 0. 1 to 10 % by weight, and even better from 0.2 to 5 % by weight, relative to the total weight of the composition according to the invention.
Cationic polymers
According to the invention, the composition may optionally further comprise at least one cationic polymer.
The term "cationic polymer" means any polymer comprising cationic groups and/or groups that can be ionized to cationic groups . Preferably, the cationic polymer is hydrophilic or amphiphilic. The preferred cationic polymers are chosen from those that contain units comprising primary, secondary, tertiary and/or quaternary amine groups that may either form part of the main polymer chain or may be borne by a side substituent directly connected thereto .
The cationic polymers that may be used preferably have a weight-average molar mass (Mw) of between 500 and 5x l 06 approximately and preferably between 103 and 3x l 06 approximately.
According to an embodiment of the invention, the composition comprises at least one cationic polymer; more preferably the cationic polymer(s) is/are chosen from cationic polysaccharides, especially cationic celluloses and galactomannan gums, and in particular quaternary cellulose ether derivatives such as the products sold under the name“JR 400” by the company Amerchol, cationic cyclopolymers, in particular dimethyldiallylammonium salt (for example chloride) homopolymers or copolymers, sold under the names Merquat 100 , Merquat 550 and Merquat S by the company Nalco, quaternary polymers of vinylpyrrolidone and of vinylimidazole, optionally crosslinked homopolymers or copolymers of methacryloyloxy(C i - C4)alkyltri(C i -C4 )alkylammonium salts, and mixtures thereof.
Preferably, when the cationic polymer(s) is/are present in the composition according to the invention, the cationic polymer(s) represent(s) from 0.01 to 5 % by weight, more preferably from 0.05 to 3 % by weight, even more preferably from 0. 1 to 2% by weight, relative to the total weight of the composition according to the invention .
Amphoteric polymers
According to the invention, the composition may optionally further comprise at least one amphoteric polymer.
The amphoteric polymers that can be used according to the invention are preferably chosen from amphoteric polymers comprising a repetition of:
(i) one or more units derived from a monomer of
(meth)acrylamide type,
(ii) one or more units derived from a monomer of (meth)acrylamidoalkyltrialkylammonium type, and
(iii) one or more units derived from an acidic monomer of (meth)acrylic acid type.
However, according to a preferred embodiment of the invention, the said amphoteric polymers consist solely of units derived from monomers (i) of (meth)acrylamide type, (ii) of (meth)acrylamidoalkyltrialkylammonium type and (iii) of (meth)acrylic acid type.
As examples of amphoteric polymers that are particularly preferred, mention may be made of acrylamide/methacrylamidopropyltrimethyl ammonium chloride/acrylic acid terpolymers . Such polymers are listed in the CTFA Dictionary (International Co smetic Ingredient Dictionary) under the name Polyquaternium 53. Corresponding products are especially sold under the names Merquat 2003 and Merquat 2003 PR by the company Nalco .
As another type of amphoteric polymer that may be used, mention may also be made of copolymers based on (meth)acrylic acid and on a dialkyldiallylammonium salt, such as copolymers of
(meth)acrylic acid and of dimethyldiallylammonium chloride. An example that may be mentioned is Merquat 280 sold by the company Nalco .
According to a preferred embodiment of the invention, the composition comprises at least one amphoteric polymer; more preferably the amphoteric polymer(s) is/are chosen from acrylamide/methacrylamidopropyltrimethyl ammonium chloride/acrylic acid terpolymers, cocobetaine, cocoamidopropylbetaine, sodium cocoamphoacetate, sodium cocoamphopropionate, disodium cocoamphodiacetate, disodium cocoamphodipropionate, sodium lauroamphoacetate, sodium cocoylisethionate, and mixtures thereof. Preferably, when the amphoteric polymer(s) is/are present in the composition according to the invention, the amphoteric polymer(s) represent(s) from 0.01 to 5 % by weight, more preferably from 0.05 to 3 % by weight, even more preferably from 0. 1 to 2% by weight, relative to the total weight of the composition according to the invention .
The composition according to the invention optionally comprises any auxiliary ingredient usually used in the co smetic field. Such ingredients may be selected, for example, from emulsifying agents, conditioning agents, stabilizers such as sodium chloride, magnesium dichloride or magnesium sulfate, moisturizing agents, shine agents, fillers, colorants, pigments, chelating compounds, sequestering agents, fragrances, preservatives, stabilizers, and mixtures thereof.
It is a matter of routine operations for a person skilled in the art to adjust the nature and amount of the additives present in the compositions in accordance with the invention such that the desired cosmetic properties and stability properties thereof are not thereby affected.
The pH of the composition according to the invention can vary between 4 and 12, more preferably between 5 and 1 1 , and even better between 6 and 7.
According to a particular embodiment of the invention, the composition according to the invention may be further prepared as follows :
Step 1 :
- either add the 4,7 , l 0-trioxa- l , l 3 -tridecanediamine in free diamine form,
- or add a salt of 4,7 , l 0-trioxa- l , l 3-tridecanediamine of formula (I) (respectively of formula (lb ) ) such as defined thereafter;
Step 2:
- either add the carboxylic acid(s) chosen from the glycolic acid, the caprylic acid, and mixture thereof,
- or add the carboxylic acid(s) salt(s) cho sen from the glycolic acid salt, the caprylic acid salt, and mixture thereof;
in at least one cosmetically acceptable solvent as previously described.
According to a preferred embodiment of the invention, a method for preparing a composition according to the invention as previously described, comprises at least one step of mixing compound ( 1 ) and/or compound (2) such as defined previously, with at least one cosmetically acceptable solvent as previously described. Another object of the present invention is a method of treatment of keratin fibers comprising at least one step of applying onto the keratin fibers of a composition according to the invention as previously described.
Preferably, the method of treatment of keratin fibers according to the invention is a method for the care and/or repair of keratin fibers .
More preferably, the method of treatment of keratin fibers according to the invention is a method for caring and/or repairing the hair split ends .
According to a preferred embodiment of the invention, the method of treatment of keratin fibers according to the invention comprises a step of rinsing the keratin fibers. More preferably, the said step of rinsing is implemented after the said step (s) of applying onto the keratin fibers of a composition as previously described.
Another object of the present invention is a composition according to the invention as previously described, for use in the treatment, preferably the care and/or repair, of keratin fibers, in particular human keratin fibers such as the hair.
Another obj ect of the present invention relates to the use of a composition according to the invention as previously described, for the treatment, preferably for the care and/or repair, of keratin fibers, preferably the hair split ends .
The following examples are given by way of illustration of the present invention and shall not be interpreted as limiting the scope. EXAMPLES:
Example 1: Synthesis of the double salt of 4710-trioxa- 113 -tridecanediamine dislycolate - compound (1)
Figure imgf000016_0001
compound (1)
Synthesis scheme of compound (1)
To a stirred solution of 3,3’-(2,2’-oxybis(ethane-2,l- diyl)bis(oxy))dipropan- 1 -amine (al) (75.0 g, 340mmol, 1 equivalent) in an apolar aprotic solvent (1.5 L) such as chloroform or dichloromethane and preferably in chloroform, is added glycolic acid (bl) (52.0 g, 682mmol, 2 equivalents). Then the mixture is stirred at room temperature (l5-35°C) and at atmospheric pressure, for 5 minutes to 20 hours, preferably for 10 to 20 hours, for example 16 hours; and finally the solvent is evaporated under vacuum to obtain the desired compound (1) as a pale brown liquid. NMR spectra confirm structure of compound (1).
Example 2: Synthesis of the double salt of 4710-trioxa- 113 -tridecanediamine dicaprylate - compound (2)
Figure imgf000017_0001
compound (2)
Synthesis scheme of compound (2)
To a stirred solution of 3,3’-(2,2’-oxybis(ethane-2,l- diyl)bis(oxy))dipropan- 1 -amine (al) (75.0 g, 340mmol, 1 equivalent) in an apolar aprotic solvent (1.5 L) such as chloroform or dichloromethane and preferably in chloroform, is added caprylic acid (b2) (98.3 g, 682mmol, 2 equivalents). Then the mixture is stirred at room temperature (l5-35°C) and at atmospheric pressure, for 5 minutes to 20 hours, preferably for 10 to 20 hours, for example 16 hours; and finally the solvent is evaporated under vacuum to obtain the desired compound (2) as a pale yellow liquid. NMR spectra confirm structure of compound (2).
Figure imgf000017_0002
Composition A (Invention): 3.72g of salt of 4,7,l0-trioxa-l,l3- tridecanediamine diglycolate has been added in lOOmL of water.
Composition B (Invention): 5.08g of salt of 4,7,l0-trioxa-l,l3- tridecanediamine dicaprylate has been added in lOOmL of water. Composition C (Comparative): 4.52g of salt of 4,7,l0-trioxa-l,l3- tridecanediamine dimaleate has been added in lOOmL of water.
Composition D (Comparative): A 0.1M mix of 2 4,7,l0-trioxa-l,l3- tridecanediamine and glycolic acid was prepared from 2.l9g of 4,7,10- trioxa-l,l3-tridecanediamine and l.53g of glycolic acid.
The analyses by liquid chromatography coupled to a mass spectrometer confirm the stability and the presence in the compositions according to the invention of the corresponding double salt.
Protocol
Beforehand, hair locks which were used for this protocol, were placed in a combing machine holder and were subjected to 10000 comb passages at the rate of 50 comb passages per minute. The room conditions were set to 20-23°C and 50-60% humidity.
This protocol was applied on three hair locks, that is to say each composition A, B, C or D was applied on one separate hair lock.
Step 1. In a watch glass, weigh 0.15 g of composition A, B, C or D for each gram of hair.
Step 2. Spread the composition along the lock from the roots to the ends in a homogenous manner.
Step 3. Gently massage the composition onto the hair, passing the lock between two fingers five times (without creating knots).
Step 4. Comb the lock if required.
Step 5. Keep the hair lock aside for 10 to 15 minutes at room temperature (20-25°C).
Step 6. Wash the hair lock with water Step 7. Repeat the steps 1 to 6 for 5 times. Evaluation
The composition A, B , C and D were tested on their capability to repair split ends of hair.
The evaluation was carried out using a microscopic camera with optical zoom CASELITE NOVA .
The numbers of split ends or broken ends were counted for 100 hair fibers per lock before and after the implementation of the protocol as previously described.
The extent of hair damage was further categorized based on the type of split end as :
• Single split end
· Double split end
• Multiple split or“Brush like structure”
• Broken end.
The results of this evaluation before and after the treatment with composition A, B , C or D are summarized in the table hereafter. M A represents the hair lock treated with composition A (Invention) .
M B represents the hair lock treated with composition B (Invention) .
Mc represents the hair lock treated with composition C (Comparative)
M D represents the hair lock treated with composition D (Comparative) .
Figure imgf000020_0001
We notice that hair locks treated with composition A or composition B according to the invention present less split ends than hair lock treated with comparative composition C or D .
We notice therefore that hair locks treated with composition A or composition B according to the invention present a better reparation of split ends than hair lock treated with comparative composition C or D .
Example 4:
The compositions E and F according to the invention, have been prepared from the following ingredients who se contents are indicated, as a percentage by weight of active ingredient relative to the total weight of the composition, in the table below.
Figure imgf000021_0001
Figure imgf000021_0002
Hair locks treated with composition E or composition F according to the invention present good cosmetic properties and a better resistance to breakage and sensoriality of the hair, in particular less split ends, than hair lock treated only with water.

Claims

1 . Composition comprising :
a double salt of the following formula (I) , consisting of a diammonium and carboxylate(s) :
Figure imgf000022_0001
in which:
n represents an integer ranging from 1 to 10 ;
m is an integer selected from 1 or 2;
X represents a carboxylate compound associated with a(the) cationic charge(s) of the double salt of formula
(I) , selected from C 2-C i2 alkylcarboxylate Alk-COO optionally substituted by one or more hydroxy;
at least one cosmetically acceptable solvent.
2. The composition according to the preceding claim, characterized in that X represents glycolate or caprylate.
3. The compo sition according to any one of the preceding claims, characterized in that n is an integer equal to 2.
4. The compo sition according to any one of the preceding claims, wherein the double salt has the following formula (lb) :
Figure imgf000022_0002
in which: p represents an integer between 0 and 2; preferably p is an integer equal to 1 ;
Y represents a carboxylate compound associated with a(the) cationic charge(s) of the double salt of formula (lb), selected from C 2 -C i2 alkylcarboxylate Alk-COO optionally substituted by one or more hydroxy; preferably Y represents glycolate or caprylate.
5. The compo sition according to any one of the preceding claims, characterized in that the double salt is such that the molar ratio of the carboxylate to the diammonium is 2.
6. The compo sition according to any one of the preceding claims, characterized in that the double salt represents from 0.0 1 to 20% by weight, more preferably from 0. 1 to 15 % by weight, even more preferably from 0,5 to 10% by weight, and even better from 1 to 8 % by weight, relative to the total weight of the composition.
7. The compo sition according to any one of the preceding claims, characterized in that the cosmetically acceptable solvent(s) is/are chosen from water, monoalcohols containing from 2 to 6 carbon atoms, polyols, glycol ethers, and mixture thereof; more preferably cho sen from water, ethanol, isopropanol, glycerol, propylene glycol, butylene glycol, pentylene glycol, hexylene glycol, dipropylene glycol, diethylene glycol, mono-, di- or tripropylene glycol (C i - C4)alkyl ethers, mono- , di- or triethylene glycol (C i -C4 )alkyl ethers, and mixtures thereof; even better chosen from water, ethanol, isopropanol, glycerol, propylene glycol, butylene glycol, and mixture thereof.
8. The compo sition according to any one of the preceding claims, characterized in that it comprises at least one additional compound selected from surfactants, cationic polymers, amphoteric polymers, or mixture thereof.
9. The composition according to the preceding claim, characterized in that the surfactant(s) is(are) selected from nonionic surfactants, cationic surfactants, or mixture thereof.
10. The composition according to any of the preceding claims characterized in that the double salt is selected from the following compound ( 1 ) or compound (2), or mixture thereof:
Figure imgf000024_0001
compound (2)
1 1 . Compound ( 1 ) and/or compound (2) , as follows :
Figure imgf000024_0002
compound (2)
12. Method of treatment of keratin fibers comprising at least one step of applying onto the keratin fibers of a composition as defined in any one of claims 1 to 10.
13. The method according to the preceding claim, characterized in that it is a method for the care and/or repair of keratin fibers .
14. The method according to Claim 12 for caring and/or repairing the hair split ends .
15. Use of the composition as defined in any one of claims 1 to 10, for the treatment, preferably for the care and/or repair, of keratin fibers .
PCT/EP2019/066353 2018-06-25 2019-06-20 Composition comprising a particular double salt of a diammonium and carboxylate(s), method and use thereof Ceased WO2020002128A1 (en)

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WO2024194599A1 (en) * 2023-03-17 2024-09-26 The University Of Warwick Ionic liquids
US12551423B2 (en) 2023-01-23 2026-02-17 CrossChem Limited Compounds for use in keratin treatment

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US20100203000A1 (en) * 2009-02-09 2010-08-12 L'oreal Clear carrier compositions for lipophilic compounds, and method of treating keratinous substrates using such compositions
US20150034117A1 (en) * 2013-08-01 2015-02-05 Liqwd, Inc. Methods for fixing hair and skin
WO2016179017A1 (en) * 2015-05-01 2016-11-10 L'oreal Use of active agents during chemical treatments

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Publication number Priority date Publication date Assignee Title
US20100203000A1 (en) * 2009-02-09 2010-08-12 L'oreal Clear carrier compositions for lipophilic compounds, and method of treating keratinous substrates using such compositions
US20150034117A1 (en) * 2013-08-01 2015-02-05 Liqwd, Inc. Methods for fixing hair and skin
WO2016179017A1 (en) * 2015-05-01 2016-11-10 L'oreal Use of active agents during chemical treatments

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Publication number Priority date Publication date Assignee Title
US12551423B2 (en) 2023-01-23 2026-02-17 CrossChem Limited Compounds for use in keratin treatment
WO2024194599A1 (en) * 2023-03-17 2024-09-26 The University Of Warwick Ionic liquids

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