WO2018105268A1

WO2018105268A1 - A composition containing glutaric acid and at least one aromatic alcohol for treating keratin fiber

Info

Publication number: WO2018105268A1
Application number: PCT/JP2017/039020
Authority: WO
Inventors: Dhimoy ROY; Amer Alkahwaji; Isaac Eng Ting LEE; Tomotaka Michitsuji
Original assignee: L'oreal
Priority date: 2016-12-07
Filing date: 2017-10-20
Publication date: 2018-06-14
Also published as: JP6983505B2; JP2018090550A

Abstract

The present invention relates to a composition for treating keratin fibers, preferably hair, comprising (a) glutaric acid and (b) at least one aromatic alcohol.

Description

DESCRIPTION

A COMPOSITION CONTAINING GLUTARIC ACID AND AT LEAST ONE AROMATIC ALCOHOL FOR TREATING KERATIN FIBER

TECHNICAL FIELD

The present invention relates to a composition for treating keratin fibers, in particular a hair care and/or hair permanent wave composition comprising glutaric acid and at least one aromatic alcohol.

BACKGROUND ART In the field of hair cosmetics, a hair treatment effect is a very important property. To date, some prior art documents relating to hair care cosmetic products have been published.

WO 2014/104340 discloses a rinse-off-type hair cosmetic composition including: component (A) a cationic polymer having a cationic charge density in the range of 4 meq/g to 10 meq/g inclusive; component (B) a fatty acid; component (C) a cationic surface active agent;

component (D) a silicone; and component (E) an organic acid or an inorganic acid, wherein the mass ratio ((A)/(B)) of component (A) to component (B) is in the range of 0.1 to 9 inclusive, component (A) and component (B) form a water-insoluble composite, and the pH (at 25 ^°C) of the composition when diluted 20-fold is in the range of 2 to 5 inclusive.

WO 2015/017768 discloses a composition for repairing bonds, for example, disulfide bonds, in hair or on the skin, comprising a specific binding agent comprising at least two reactive moieties capable of reacting with free thiol groups, an aqueous solvent, and one or more preservatives, stabilizers, or combinations thereof.

However, there is still a demand for hair care cosmetic products with improved performance of hair treatment efficiency.

DISCLOSURE OF INVENTION

An objective of the present invention is to provide a composition for treating keratin fibers, preferably hair, having improved treatment efficiency on keratin fibers, in particular improved relaxation and volume down efficiency on keratin fibers, as well as an effect of imparting smoothness to keratin fibers.

The above objective of the present invention can be achieved by a composition for treating keratin fibers, preferably hair, comprising:

(a) glutaric acid, and

(b) at least one aromatic alcohol.

The aromatic alcohol may be represented by general formula (I):

wherein,

- a indicates an integer of 0 to 5, preferably 0 to 2, and more preferably 0 or 1 ;

- b indicates an integer of 0 or 1 ;

- R indicates H, halogen, a Ci to C₆ alkyl, a Ci to C₆ alkoxy, or a d to C₆ alkenyl group;

- X indicates a Ci to C₄ alkylene or a Ci to C₄ alkynylene group; and

- Y indicates single bond, a Ci to C₄ alkylene, or a Ci to C₄ alkynylene group. Preferably, in the general formula (I),

- a indicates an integer of 0 or 1 ;

- b indicates an integer of 0 or 1 ; :

- R indicates H, halogen, a Ci to C₆ alkyl group;

- X indicates a Ci to C₄ alkylene group; and

- Y indicates single bond or a d to C₄ alkylene group.

More preferably, in the general formula (I),

- a is 0;

- b is 1 ;

- X indicates a Ci to C₄ alkylene group; and

- Y indicates single bond.

In one preferred embodiment of the present invention, the aromatic alcohol is

phenoxyethanol.

The glutaric acid may be present in a content ranging from 0.05% to 20% by weight, preferably from 0.1 % to 15% by weight, and more preferably from 0.5% to 10% by weight, with respect to the total weight of the composition. The aromatic alcohol may be present in a content ranging from 0.005% to 10% by weight, preferably from 0.01% to 5% by weight, and more preferably from 0.02% to 3% by weight, with respect to the total weight of the composition.

The composition according to the present invention may further comprise at least one surfactant selected from cationic, anionic, nonionic, and and amphoteric surfactants.

The composition according to the present invention may further comprise at least one oxidizing agent.

The composition according to the present invention may further comprise at least one cationic polymer. The present invention also relates to a cosmetic process for caring for or conditioning keratin fibers, comprising the step of applying onto the keratin fibers the composition according to the present invention.

The present invention also relates to a cosmetic process for perming keratin fibers, preferably hair, comprising the step of applying onto the keratin fibers the composition according to the present invention after the keratin fibers are reduced.

BEST MODE FOR CARRYING OUT THE INVENTION

After diligent research, the inventors have surprisingly found that a combination of glutaric acid and at least one aromatic alcohol can provide a compositions for treating keratin fibers, preferably hair, having improved performance of treatment effect on keratin fibers, such as relaxation effect, volume down effect, and an effect of imparting smoothness on keratin fibers, preferably hair, and thus they have completed the present invention.

Thus, the composition for treating keratin fibers, preferably hair, according to the present invention comprises:

(a) glutaric acid, and

(b) at least one aromatic alcohol.

The "keratin fibers" here mean fibers which include at least one keratin substance. It is preferable that at least a part of the surface of the keratin fibers be formed by keratin substances. Examples of keratin fibers include hair, eyebrows, eyelashes, and the like. It is preferable that the present invention be used for treating hair.

Especially, the composition according to the present invention has a superior hair relaxation effect, hair volume down effect, and an effect of imparting smoothness to a hair.

Furthermore, the composition can provide softness and flexibility with the hair. In addition, the composition of the present composition can provide improved hair wave performance.

Hereafter, the composition according to the present invention will be described in a detailed manner.

[Composition]

The composition for treating keratin fibers, preferably hair, according to the present invention comprises (a) glutaric acid and (b) at least one aromatic alcohol.

(Glutaric Acid)

The composition according to the present invention comprises (a) glutaric acid.

Glutaric acid may be presented by general formula below:

The inventors surprisingly found that the combination of glutaric acid and aromatic alcohol can provide superior hair caring and/or conditioning effect as well as hair wave performance in a hair permanent wave treatment compared to any other combinations using another dicarboxylic acid instead of glutaric acid.

The glutaric acid may be present in a content of 0.05% by weight or more, preferably 0.1% by weight or more, and more preferably 0.5% by weight or more, relative to the total weight of the composition. The glutaric acid may be present in a content of 20% by weight or less, preferably 15% by weight or less, and more preferably 10% by weight or less, relative to the total weight of the composition.

The glutaric acid may be present in a content ranging from 0.05% to 20% by weight, preferably from 0.1% to 15% by weight, and more preferably from 0.5% to 10% by weight, relative to the total weight of the composition.

(Aromatic Alcohol)

The composition according to the present invention comprises (b) at least one aromatic alcohol. Two or more (b) aromatic alcohols may be used in combination. Thus, a single type of aromatic alcohol or a combination of different types of aromatic alcohols may be used.

The term "aromatic alcohol" used herein means any compound comprising at least one aromatic ring and at least one alcohol functional group, i.e. -OH group, directly linked to the aromatic ring or linked to at least one substituent on the ring.

The aromatic alcohol may be mono-alcohol having one -OH group or polyol having two or more -OH groups such as di-alcohol. Preferably, the aromatic alcohol is a mono-alcohol.

The aromatic alcohol preferably includes one or more benzene ring(s), naphthalene ring(s), or furan rings. More preferably, the aromatic alcohol includes one or more benzene rings. In particular, the aromatic alcohol may include one benzene ring. In one preferable embodiment of the present invention, the aromatic alcohol includes one benzene ring and one -OH group linked to a substituent on the ring.

The aromatic alcohol can be a primary alcohol, a secondary alcohol, or a tertiary alcohol. Preferentially, the aromatic alcohol is a primary alcohol.

In one preferred embodiment of the present invention, the aromatic alcohol can be presented by the following general formula (I):

(I) wherein,

- b indicates an integer of 0 or 1 ;

- R indicates H, halogen, a Ci to C₆ alkyl, a Ci to C₆ alkoxy, or a Ci to C₆ alkenyl group;

- X indicates a Ci to C₄ alkylene or a d to C₄ alkynylene group; and

- Y indicates a single bond, a Ci to C₄ alkylene, or a d to C₄ alkynylene group.

Each of said alkyl, alkoxy, alkenyl, alkylene, and alkynylene groups can be linear or branched and can be substituted with one or more substituents selected from halogen, amine group (-NH₂), and oxo group (=0).

The halogen can be selected from F, CI, Br, and I, and preferably the halogen is CI. According to one preferred embodiment of the present invention, in general formula (I),

- a indicates an integer of 0 or 1 ;

- b indicates an integer of 0 or 1 ;

- R indicates H, halogen, or a Ci to C₆ alkyl group;

- X indicates a Ci to C₄ alkylene group; and

- Y indicates a single bond or a Ci to C₄ alkylene group.

According to one particularly preferred embodiment of the present invention, in general formula (I),

- a is 0;

- b is 1 ;

- X indicates a Ci to C₄ alkylene group; and

- Y indicates a single bond.

In another embodiment of the present invention, the aromatic alcohol used herein can be selected from benzyl alcohol, benzyl glycol, phenoxyethanol, dichlorobenzyl alcohol, methylphenylbutanol, phenoxyisopropanol, 1 -phenyl- 1-propanol, l-phenyl-2-propanol, 2-phenyl-l-propanol, 2-phenyl-2-propanol, 3 -phenyl- 1-propanol, 1-phenylethyl alcohol, 2-phenylethyl alcohol, benzyloxy ethanol, cinnamyl alcohol, 4-methoxybenzyl alcohol, 4-methylbenzyl alcohol, and mixtures thereof. Particularly preferably, the aromatic alcohol is phenoxyethanol.

The aromatic alcohol may be present in a content of 0.005% by weight or more, preferably 0.01% by weight or more, and more preferably 0.02% by weight or more, relative to the total weight of the composition. The aromatic alcohol may be present in a content of 10% by weight or less, preferably 5% by weight or less, and more preferably 3% by weight or less, relative to the total weight of the composition.

The aromatic alcohol may be present in a content ranging from 0.005% to 10% by weight, preferably from 0.01% to 5% by weight, and more preferably from 0.02% to 3% by weight, relative to the total weight of the composition.

(Other Ingredients) - Surfactants

The composition according to the present invention may preferably include at least one surfactant. The surfactants used in the present invention include cationic, anionic, nonionic, and amphoteric surfactants.

As the nonionic surfactants, mention may be made of:

- polyethoxylated fatty alcohols or polyglycerolated fatty alcohols, such as the adducts of ethylene oxide with lauryl alcohol, especially those containing from 9 to 50 oxyethylene units (Laureth-9 to Laureth-50, as the CTFA names); the adducts of ethylene oxide with behenyl alcohol, especially those containing from 9 to 50 oxyethylene units (Beheneth-9 to

Beheneth-50, as the CTFA names); the adducts of ethylene oxide with cetyl alcohol, especially those containing from 10 to 30 oxyethylene units (Ceteth-10 to Ceteth-30, as the CTFA names); the adducts of ethylene oxide with stearyl alcohol, especially those containing from 2 to 20 oxyethylene units (Steareth-2 to Steareth-20, as the CTFA names); the adducts of ethylene oxide with oleyl alcohol, especially those containing from 10 to 30 oxyethylene units (Oleth-10 to Oleth-30, for example Oleth-20, as the CTFA names); and mixtures thereof

- esters of sugar and of a C_8-C₂₄ fatty acid and their oxyalkylenated derivatives, such as polyethoxylated sorbitol esters of C₈-C₂₄ fatty acids, in particular Polysorbate 80, such as the product marketed under the name "T WEEN 80" by Croda; ethers of a sugar and of C_8-C₂4 fatty alcohols, such as caprylyl/capryl glucoside such as the product marketed under the name "ORAMIX CG 110" by SEPPIC;

- esters of fatty acids, especially of C₈-C₂₄ and preferably of Ci₆-C₂₂, and of polyol, especially of glycerol or sorbitol, such as glyceryl stearate, sold, for example, under the name Tegin M® by the company Goldschmidt, polyglyceryl diisostearate, polyglyceryl isostearate, polyglyceryl monostearate, diglyceryl tetraisostearate, polyethylene glycol diisostearate, polyglyceryl- 10 pentastearate, glyceryl monooleate, glyceryl laurate, such as the product Imwitor 312® by the company Hills, diethyl ene glycol (di)laurate, decaglyceryl pentaoleate, decaglyceryl pentadiisostearate, glyceryl caprate/caprylate, polyglyceryl-2 (iso)stearate and (poly)ricinoleate;

- oxyalkylenated alcohols, in particular oxyethylenated and/or oxypropylenated alcohols, which may comprise from 1 to 15 oxy ethylene and/or oxypropylene units, in particular ethoxylated C₈-C₂₄ and preferably Ci₂-C₁₈ fatty alcohols such as stearyl alcohol ethoxylated with 2 oxy ethylene units (CTFA name: Steareth-2 such as Brij 72 sold by the company Uniqema), or oxyethylenated oleyl alcohol;

- fatty alcohols such as cetylstearyl alcohol.

As the anionic surfactants, mention may be made of:

- salts of Ci₆-C₃o fatty acids, especially amine salts, such as triethanolamine stearate or 2-amino-2-methylpropane-l,3-diol stearate; - polyoxyethylenated fatty acid salts, especially animated salts or salts of alkali metals, and mixtures thereof;

- phosphoric esters and salts thereof, such as DEA oleth-10 phosphate (Crodafos N ION from the company Croda) or monopotassium monocetyl phosphate (Amphisol K from Givaudan or Arlatone MAP 160K from the company Uniqema);

- sulfosuccinates such as Disodium PEG- 5 citrate lauryl sulfo succinate and Disodium ricinoleamido MEA sulfo succinate;

- alkyl ether sulfates such as sodium lauryl ether sulfate;

- isethionates;

- acylglutamates such as Disodium hydrogenated tallow glutamate (Ami soft HS-21 R® sold by the company Ajinomoto), and mixtures thereof.

As the cationic surfactants, mention may be made of:

- alkylimidazolidiniums such as isostearylethylimidonium ethosulfate,

- ammonium salts such as (C 12-30 alky l)tri(Ci-4 alkyl)ammonium halides, for instance

N,N,N-trimethyl-l-docosanaminium chloride or behentrimonium chloride.

As the amphoteric surfactants, mention may be made of N-acylamino acids such as N-alkyl aminoacetates and disodium cocoamphodi acetate, and amine oxides such as stearamine oxide and lauramine oxide.

The surfactant(s) may be present in a content ranging from 0.01% to 20% by weight, preferably from 0.1% to 10% by weight, and more preferably from 1% to 5% by weight relative to the total weight of the composition.

- pH adjusters

The composition according to the present invention may preferably include at least one pH adjuster. The adjustment of the pH to the desired value may be carried out conventionally by addition of the pH adjuster, such as an organic or inorganic base or an organic or inorganic acid or salts thereof to the composition. The base includes, for example, ammonium hydroxide, sodium hydroxide, sodium carbonate or a primary, secondary or tertiary (poly) amine, such as monoethanolamine, diethanolamine, triethanolamine, isopropanolamine or 1, 3- propanediamine. The organic acid includes, for example, a carboxyli c acid, a citric acid, a tartaric acid, and a lactic acid. The inorganic acid includes, for example, a hydrochloric acid, a nitric acid, orthophosphoric acid and a sulphonic acid. The salt includes, for example, sodium phosphate and trisodium phosphate.

The pH adjuster(s) may be present in a content enough to adjust the pH of the composition to the desired value, for example, ranging from 0.01% to 10% by weight, preferably from 0.1% to 5% by weight, and more preferably from 0.5% to 3% by weight relative to the total weight of the composition.

- Oxidizing agents

If the composition according to the present invention is used as a second agent for a hair permanent wave treatment, the composition may preferably include at least one oxidizing agent. The oxidizing agent may be chosen from hydrogen peroxide, alkali metal bromates, ferricyanides peroxygenated salts, and compounds capable of producing hydrogen peroxide by hydrolysis. For example, the oxidizing agent can be chosen from aqueous hydrogen peroxide solution, urea peroxide, alkali metal bromates, such as sodium bromate, and persalts such as perborates and persulphates.

The oxidizing agent(s) may be present in a content ranging from 0.1 % to 30% by weight, preferably from 0.5% to 20% by weight, and more preferably from 1% to 10% by weight relative to the total weight of the composition.

- Other conditioning agents The compositions according to the invention may also optionally contain other conditioning agents which have the effect of improving the cosmetic properties of keratin fibers, such as hair. There may be mentioned, in this respect, for example, cationic polymers such as cyclopolymers of alkyldiallylamine or of dialkyldiallylammonium, for example

polyquaternium-6 and polyquaternium-7, amphoteric polymers such as polyquaternium-22, anionic or nonionic polymers, proteins, protein hydrolysates, amino acids such as tyrosine, glycine, and arginine acid, ceramides, pseudoceramides, fatty acids with linear or branched (Ci<5-C₄o) chains such as 18-methyleicosanoic acid, hydroxy acids, vitamins, and panthenol.

As the other cationic polymers, mention may be made of:

(1) homopolymers or copolymers derived from acrylic or methacrylic esters or amides and comprising at least one of the units of formula (I), (II), (III) or (IV) below:

in which:

R₃, which may be identical or different, denote a hydrogen atom or a CH₃ radical;

A, which may be identical or different, represent a linear or branched d-C6 alkyl group or a Ci-C₄ hydroxyalkyl group;

R4, R₅ and R₆, which may be identical or different, represent a d-C₁₈ alkyl group or a benzyl radical;

Ri and R₂, which may be identical or different, represent hydrogen or a Ci-C₆ alkyl group;

(2) cellulose ether comprising quaternary ammonium groups;

(3) cellulose or cellulose copolymers grafted with a water-soluble quaternary ammonium monomer;

(4) non-cellulose cationic polysaccharides;

(5) polymers consisting of piperazinyl units and of divalent alkylene or hydroxyalkylene radicals containing straight or branched chains, interrupted or not interrupted by oxygen, sulfur or nitrogen atoms or by aromatic or heterocyclic rings, and also the oxidation and/or quaternization products of these polymers;

(6) water-soluble polyamino amides prepared by polycondensation of an acidic compound with a polyamine;

(7) polymers obtained by reaction of a polyalkylene polyamine containing two primary amine groups and at least one secondary amine group with a dicarboxylic acid chosen from diglycolic acid and saturated C₃-C₈ aliphatic dicarboxylic acids; (8) the quaternary diammonium polymers containing repeating units corresponding to the formula (V):

in which formula:

Rio, Rii, Ri₂ and Ri₃, which may be identical or different, represent O-C20 aliphatic, alicyclic or arylaliphatic radicals or hydroxyalkylaliphatic radicals in which the alkyl radical is Ci-C₄, or alternatively Rio, Rn, Ri₂ and R13, together or separately, constitute, with the nitrogen atoms to which they are attached, heterocycles containing or not containing a second heteroatom other than nitrogen, or alternatively Rio, Rn, R12 and Ri₃ represent a linear or branched Ci-C₆ alkyl radical substituted with a nitrile, ester, acyl or amide group or a group -CO-O-R14-D or -CO-NH-R14-D where R₁₄ is an alkylene and D is a quaternary ammonium group;

Ai and Bi represent C₂-C₂o polymethylene groups which may be linear or branched, saturated or unsaturated, and which may contain, linked to or intercalated in the main chain, one or more aromatic rings or one or more oxygen or sulfur atoms or sulfoxide, sulfone, disulfide, amino, alkylamino, hydroxyl, quaternary ammonium, ureido, amide or ester groups, and X^" denotes an anion derived from a mineral or organic acid;

Ai, Rio and R12 can form, with the two nitrogen atoms to which they are attached, a piperazine ring;

in addition, if Ai denotes a linear or branched, saturated or unsaturated alkylene or

hydroxyalkylene radical, Bi can also denote a group -(CH₂)_n-CO-D-OC-(CH₂)_n- in which n is between 1 and 100, and D denotes:

a) a glycol residue of formula: -O-Z-O-, where Z

represents -(CH₂-CH₂-0)_x-CH₂-CH₂-; -[CH₂-CH(CH₃)-0]_y-CH₂-CH(CH₃)-, where x and y denote an integer from 1 to 4, representing a defined and unique degree of polymerization or any number from 1 to 4 representing an average degree of polymerization;

b) a bis-secondary diamine residue;

c) a bis-primary diamine residue of formula: -NH-Y-NH-, where Y denotes a linear or branched hydrocarbon-based radical, or alternatively the radical

-CH₂-CH₂-S-S-CH₂-CH₂-;

d) a ureylene group of formula: -NH-CO-NH-;

(9) poly quaternary ammonium polymers consisting of repeating units of formula (VI):

in which p denotes an integer ranging from 1 to 6 approximately, D may be zero or may represent a group -(CH₂)_r-CO- in which r denotes a number equal to 4 or 7, and X^" is an anion;

(10) quaternary polymers of vinylpyrrolidone and of vinylimidazole;

(11) vinylamide homopolymers or copolymers;

(12) cationic polyurethane;

(13) cationic protein hydrolysates, polyalkyleneimines, polymers containing vinylpyridine or vinylpyridinium units.

The other conditioning agent(s) may be present in a content ranging from 0.01% to 30% by weight, preferably from 0.1% to 20% by weight, and more preferably from 1% to 10% by weight relative to the total weight of the composition.

- Additives

,

The compositions according to the present invention may further contain all the customary adjuvants encountered in the field of compositions for treating keratin fibers, for example, hydrophilic solvents, perfumes, flagrances, thickeners, preservatives such as chlorhexidine digluconate, sequestrants such as EDTA(ethylenediaminetetraacetic acid) and its salts, foam modifiers, colorants, moisturizing agents, antidandruff agents, antiseborrhoeic agents, sunscreens and the like.

The amount of the additives included in the composition according to the present invention is not limited, but may be from 0.01 to 30% by weight relative to the total weight of the composition according to the present invention.

The composition according to the present invention may exist in any form such as a lotion, a gel, a W/O or O/W emulsion, thickened or not, a foam, or a cream. The composition according to the present invention may be contained in any container such as a spray bottle, a pump bottle or an aerosol can.

The compositions according to the present invention can be used as compositions for treating keratin fiber. For example, the compositions can be formulated into shampoos, conditioners, hair treatment creams, gels, mousses, pump hair sprays, aerosol hair sprays, set lotions, blow styling lotions, hair color lotions, hair relaxing compositions, reducers for permanent wave, neutralized for a permanent wave treatment, and coloring compositions.

Especially, since the composition according to the present invention possesses a superior hair relaxation effect, a hair volume down effect, and an effect of imparting smoothness to hair, and also provides flexibility and softness to hair, the composition is suitable for hair care treatment compositions. Besides these effects, since the composition has a property of improving wave performance in a hair permanent wave treatment, the composition is very useful in a permanent wave treatment, especially as a neutralizer in a hair permanent wave treatment.

The pH of the composition according to the present invention may generally be, for example, from 2 to 12. When the composition is used as a hair care treatment composition, the composition may have a pH ranging from 3.0 to 6.0, and preferably from 3.5 to 5.0. When the composition is used as a neutralizer for a permanent wave treatment, the composition may have a pH ranging from 2.0 to 10.0, and preferably from 2.5 to 9.0.

The composition according to the present invention can be manufactured through an usual techniques in the art, for example, by mixing the (a) glutaric acid and the (b) aromatic alcohol. Said other ingredients can be mixed with the glutaric acid and the aromatic alcohol. While mixing these ingredients, they can be heated, if necessary.

[Cosmetic Process]

The present invention also relates to a process, preferably a cosmetic process for treating keratin fibers, preferably for conditioning, caring for or perming hair, comprising a step of applying the composition according to the present invention to keratin fibers, preferably the hair.

The composition may be applied to the hair by first applying to the hands, and then contacting the hair with the hands; in other embodiments, the composition may be applied directly onto the hair, such as by spraying. The composition may also be delivered onto the hair by use of an applicator or device. The compositions may be applied to the hair as a leave-on treatment. In one embodiment of the present invention, the composition can be used as a hair care or hair conditioning composition. Therefore, the present invention also relates to a use of the combination of the glutaric acid and the aromatic alcohol as a hair care or hair conditioning composition. In consideration of the superior hair relaxation effect, the hair volume down effect, and the effect of imparting smoothness to the hair of the composition according to the present invention, the cosmetic process according to the present invention can provide an attractive appearance to the hair. The present invention also relates to a cosmetic process for perming hair, comprising a step of applying onto the hair the composition according to the present invention after the hair is reduced.

In one embodiment of the present invention, the composition can be used in a hair permanent wave treatment, especially as a neutralizer. Therefore, the present invention also relates to a use of the combination of the glutaric acid and the aromatic alcohol in a hair permanent wave treatment, in particular as the neutralizer.

When the composition according to the present invention can be used as the neutralizer, the hair is treated with a conventional reducer for a hair permanent wave before the composition according to the present invention is applied. Therefore, when the composition according to the present invention is used as the neutralizer for a hair permanent wave, the cosmetic process of the present invention can be performed by:

(i) applying onto the hair the reducer;

(ii) optionally rinsing the hair;

(iii) applying onto the hair the composition according to the present invention; and

(iv) optionally rinsing and/or drying the hair.

The reducer used in step (i) preferably comprises at least one alkaline agent, such as ammonium hydroxide, and other components which are commonly used in this field, such as conditioning agents, silicones, and surfactants. The reducer may comprise an acidic agent such as lactic acid, citric acid and phosphoric acid. In step (i), disulfide bonds in the hair are reduced. The application of the reducer may be performed by any means, such as an applicator, a brush and a comb. It may be possible that the hair after the application of the reducer be left as it is for a certain amount of time typically from 1 minute to 1 hour. Hair may be subjected to mechanical tension which is typically used for permanent deformation of the hair before and/or after step (i).

The mechanical tension can be applied to the hair by any means to deform the hair to the intended shape. For example, the mechanical tension may be provided by at least one reshaping means selected from the group consisting of a curler, a roller, a clip, a plate and an iron. The reshaping means may comprise at least one heater. If the hair is rolled around a curler, this rolling-up may be performed on the entire length of the hair or, for example, on half the length of the hair. Depending on, for example, the desired hairstyle shape and amount of curls, the rolling-up may be performed with more or less thick locks.

In step (ii), the hair may be rinsed preferably with water. If necessary, the hair is provided with heat, for deforming or reshaping the hair, preferably after step (i) or step (ii) if present. For example, the hair which may or may not be under mechanical tension is heated with a heating means such as a heating iron (when straightening) or a heating rod (when waving) at typically from 30 to 240°C for typically 5 seconds to 2 hours.

In step (iii), the hair is oxidized by the neutralizer corresponding to the composition according to the present invention. In this way, the present invention may comprise at least one oxidizing agent, explained in detail previously in the context of the composition. According to the present invention, it is preferable that step (iii) perform mild oxidation by applying an oxidizing composition with a short, or with no, standing time on the hair. As the standing time, mention may be made of 1 minute to 30 minutes, preferably 5 minutes to 15 minutes. In step (iv), the hair may be rinsed preferably with water, and/or may be dried. The drying of the hair can be performed with a conventional drying means such as a hair drier.

In consideration of improved wave performance in a hair permanent wave treatment of the present invention, the cosmetic process also can provide an attractive permanent wave appearance.

EXAMPLES

The present invention will be described in a more detailed manner by way of examples. However, these examples should not be construed as limiting the scope of the present invention. In the examples, the glutaric acid used was obtained from Tokyo Chemical Industry (reagent grade) and the phenoxyethanol used was obtained from SEPPIC.

< Example 1 and Comparative Examples 1 to 15 >

[Composition]

The compositions according to Example 1 and Comparative Examples 1 to 15 were prepared by mixing different dicarboxylic acids and deionized water with or without phenoxyethanol. The amount of each of the dicarboxylic acids was set to 0.0053 moles. The amount of phenoxyethanol was 1 wt% when it was included. The pH of each of compositions was adjusted to 4.0 with hydrochloric acid and/or sodium hydroxide. Table 1 shows the species of active ingredients, i.e. dicarboxylic acids and phenoxyethanol, included in each of the compositions.

[Evaluation]

(Denaturation Temperature)

4 mg of keratin powder, which was obtained from Shinshu University, was treated with 1.5 mL of each of the compositions according Example 1 and Comparative Examples 1 to 15 by agitating them in an Eppendorf tube continuously at room temperature for one hour. The keratin powder was recovered by filtration and dried under vacuum overnight at room temperature to obtain the treated keratin powder. The denaturation temperature of the treated keratin powder, corresponding to a temperature upon a change from oc-structure to β-structure of the keratin protein, was measured with a differential scanning calorimetry (DSC, HITACH High-Tech Science Corporation, X-DSC7000) using an alodined aluminium sealed pan and cover. Heating using DSC was carried out from 20°C to 280°C at 10°C/min heating rate. The changes of the denaturation temperature of each of the treated keratin powders compared with untreated keratin powder are summarized in Table 1. It can be said that keratin powder having a lower denaturation temperature has a more flexible or softer keratin protein structure due to breaking of chemical interactions.

The results are shown in Table 1.

Table 1

From the results of the measurement of changes of the denaturation temperature of the keratin powders in Table 1, the keratin powder treated with the composition according to Example 1 including glutaric acid and aromatic alcohol exhibited a lower denaturation temperature compared to the keratin powders treated with the compositions according to Comparative Examples 1 to 15, which do not include glutaric acid and/or aromatic alcohol. Therefore, it can be concluded that the composition according to the present invention can impart softness and flexibility to the hair more than the compositions according to Comparative Examples 1 to 15.

(Relaxation Efficiency and Volume Down Efficiency)

Hair swatch (lg, 27cm) was washed with clarifying shampoo and then placed on a hot plate at 30°C. 1 mL of the composition comprising glutaric acid and phenoxyethanol (Example 1) or only glutaric acid (Comparative Example 1) was applied on the swatch by a brush. The hair swatch was then wrapped and shaped for 5 minutes at 30°C, rinsed off under running water, and then dried naturally under ambient conditions to obtain the treated hair swatch.

The length and width of the hair swatch before and after the treatment were measured by a Vernier caliper. The length was measured from the root to tip of the hair swatch, whereas the width was measured at a position of 20 cm from the root of the hair swatch by placing the Vernier caliper perpendicular to the axis of the hair swatch that was hung down vertically. The relaxation efficiency and the volume down efficiency were determined according to the following equations, respectively.

Relaxation efficiency = (Lbefore-L_after)/Lbefore x 100%

Lbefore : length of hair swatch before treatment

Lafter : length of hair swatch after treatment

A higher value (%) of relaxation efficiency means that the composition possesses superior relaxation efficiency.

Volume down efficiency = (Wbefore-Wafter)/Wbefore x 100%

Wbefore : width of hair swatch before treatment

Waiter : width of hair swatch after treatment

The lower value (%) of the volume down efficiency means that the composition possesses superior volume down efficiency.

The results are shown in Table 2.

Table 2

As can be seen from the results of the measurements of relaxation efficiency and volume down efficiency in Table 2, the composition according to the present invention exhibits improved relaxation efficiency and volume down efficiency compared to the composition according to Comparative Example 1 which includes glutaric acid but does not include aromatic alcohol.

< Examples 2 and 3 and Comparative Examples 16 to 24 > [Composition] Neutralizing compositions for a permanent wave according to Examples 2 and 3 and

Comparative Examples 16 to 24 were prepared in accordance with the following preparation protocol. The compositions are shown in the following Tables 3 and 4. In Tables 3 and 4, the formulations are based on "parts by weight" as active raw materials. In each of the compositions, if dicarboxylic acid was included, its amount was adjusted so as to be 0.0461 moles. [Preparation Protocol]

1) Trisodium phosphate, sodium phosphate, and sodium bromate were added to deionized water and the resulting mixture was mixed so that these ingredients completely dissolved in water.

2) Polyquaternium-6 and lauramine oxide were added to the mixture.

3) A pre-mix of Oleth-20, phenoxyethanol, and fragrance was prepared and added to the mixture, and then blended so as to be completely dissolved.

4) A premix of deionized water, dicarboxylic acid ingredients, and sodium hydroxide with pH 7.5 was prepared and added to the mixture.

5) The pH of the obtained mixture was adjusted to 7.5 with sodium hydroxide, if necessary. The total amount was adjusted with deionized water. The obtained mixture was mixed to be homogenous

- Preparation protocol for the reducer composition

The reducer composition for a hair permanent wave treatment in these evaluations was prepared in accordance with the following preparation protocol.

1) 1.47 wt% of ammonium hydroxide, 0.05 wt% of tyrosine, 0.05 wt% of glycine, and 0.2 wt% of EDTA were added into deionized water and they were mixed so as to be completely dissolved in water.

2) 0.6 wt% of ammonium thioglycolate and 3.95 wt% of cysteamine HCl were added to the mixture and mixed so as to be completely dissolved.

3) 0.06 wt% of hexadimethrine chloride, 0.12 wt% of polyquaternium-6, 0.1 wt% of pentylene glycol, and 0.42 wt% of cocamidopropyl betaine (and) glyceryl laurate were added to the mixture and mixed so as to be completely dissolved.

4) A premix of 1 wt% of Oleth-20 and 0.4 wt% of fragrance was prepared and then added to the mixture, and mixed so as to be completely dissolved.

5) 0.62 wt% of amodimethicone and deionized water in an amount of qs 100 were added to the mixture and mixed so as to be homogenous.

[Evaluation]

(Permanent Wave Efficiency)

A hair swatch of 20 hair fibers having a length of 150 mm long was prepared. The obtained hair swatch was wound on a 10 mm diameter rod. 100 iL of a reducer composition for a hair permanent wave was applied on the wound hair swatch with a pipette. The hair swatch was shaped for 15 minutes at 30°C, and rinsed off with 300 ml tap water for 30 seconds.

100 iL of the neutralizer composition according to each of Examples 2 and Comparative Examples 16 to 23 was then applied on the hair swatch. After the hair swatch was shaped for 10 minutes at 30°C, the rod was removed, and then the hair swatch was rinsed off with running water. The length of the treated hair swatch was measured and the permanent wave efficiency was assessed according to the following equation.

Permanent wave efficiency = (150 - [length (mm)]) / 150 x 100 A higher score represents a better property of permanent wave efficiency. The results of the evaluation are shown in Table 3.

Table 3

(Smoothness)

5 A hair swatch ( 1 g, 27cm) was wound on a 20mm diameter rod. 2 ml of a reducer

composition for a hair permanent wave treatment was applied on the wounded hair swatch with a pipette. The hair swatch was shaped for 15 minutes at 30 °C, and rinsed off with running water for 30 seconds. 2 ml of the neutralizer composition according to each of Examples 3 and 4 and Comparative Examples 16 to 24 was then applied on the wound hair

10 swatch. After the hair swatch was shaped for 10 minutes at 30 °C, the rod was removed, and then the hair swatch was rinsed off with running water and dried to obtain the treated hair swatch. The treated hair swatch was placed on a plate, and its root side was fixed on the plate with a hair clip. The smoothness of the treated hair swatch was measured by scanning the swatch from root to tip with a sensor (Handy Rub Tester (type TL701) from Trinity Lab).

15 The measurement was carried out 3 times for one treated hair swatch. The same procedure was conducted with two more hair swatches for one composition to obtain 9 results in total for one composition, and the mean values were calculated for each composition. A lower score represents that a better smoothness effect was exerted.

20 The results of the evaluation are shown in the following Table 4. Table 4

As can be seen from the results of the measurements of permanent wave efficiency in Table 3, the compositions according to Example 3, which comprise a combination of glutaric acid and aromatic alcohol, exhibit significantly improved permanent wave efficiency compared to each of the compositions according to Comparative Examples 16 to 23 which do not include the inventive combination.

Furthermore, as can be seen from the results shown in Table 4, the hair swatch treated with the compositions according to Examples 3 and 4 became smoother than those treated with each of the compositions according to Comparative Examples 16 to 24. Therefore, the compositions comprising the combination of glutaric acid and aromatic alcohol can significantly impart smoothness to the hair more effectively than each of the compositions according to Comparative Examples 16 to 24 which do not include the inventive combination.

Therefore, it can be concluded that the composition according to the present invention can provide better permanent wave efficiency as well as better smoothness to the keratin fibers, such as hair. Accordingly, the composition according to the present invention can be very preferable for use in a hair permanent wave treatment.

Claims

1. A composition for treating keratin fibers, preferably hair, comprising:

(a) glutaric acid, and

(b) at least one aromatic alcohol.

2. The composition according to Claim 1, wherein the aromatic alcohol is represented b general formula (I):

wherein,

- b indicates an integer of 0 or 1 ;

- R indicates H, halogen, a d to C₆ alkyl, a d to C₆ alkoxy, or a Ci to C₆ alkenyl group;

- X indicates a Ci to C₄ alkylene or a d to C₄ alkynylene group; and

- Y indicates a single bond, a d to C₄ alkylene, or a Ci to C₄ alkynylene group.

The composition according to Claim 2, wherein in general formula (I),

- a indicates an integer of 0 or 1 ;

- b indicates an integer of 0 or 1 ;

- R indicates H, halogen, or a d to C₆ alkyl group;

- X indicates a d to C₄ alkylene group; and

- Y indicates a single bond or a d to C₄ alkylene group.

The composition according to Claim 3 wherein in general formula (I),

- a is O;

- b is 1;

- X indicates a Ci to C₄ alkylene group; and

- Y indicates a single bond.

The composition according to Claim 1 , wherein the aromatic alcohol is phenoxyethanol.

The composition according any one of the preceding claims, wherein the glutaric acid is present in a content ranging from 0.05% to 20% by weight, preferably from 0.1%) to 15% by weight, and more preferably from 0.5% to 10% by weight, with respect to the total weight of the composition.

The composition according any one of the preceding claims, wherein the aromatic alcohol is present in a content ranging from 0.005%) to 10%) by weight, preferably from 0.01 ) to 5% by weight, and more preferably from 0.02%> to 3%> by weight, with respect to the total weight of the composition.

8. The composition according to any one of the preceding claims, further comprising at least one surfactant selected from cationic, anionic, nonionic, and and amphoteric surfactants.

9. The composition according to any one of the preceding claims, further comprising at least one cationic polymer.

10. The composition according to any one of the preceding claims, further comprising at least one oxidizing agent.

11. A cosmetic process for caring for or conditioning keratin fibers, preferably hair, comprising the step of applying onto the keratin fibers the composition according to any one of the preceding claims.

12. A cosmetic process for perming keratin fibers, preferably hair, comprising the step of applying onto the keratin fibers the composition according to Claim 10 after the keratin fibers are reduced.