JP2019073443A - Composition for treating keratin fibers - Google Patents

Abstract

To provide a composition for treating keratin fibers, preferably hair.SOLUTION: A composition comprises at least one aromatic sulfonic acid compound represented by general formula (1) or (2) in the figure, where at least one R is -NH, or a salt thereof.SELECTED DRAWING: None

Description

  The present invention relates to a composition for treating keratinous fibers, in particular to a hair care cosmetic composition comprising at least one aromatic sulfonic acid compound or a salt thereof.

  In the field of hair cosmetics, the hair treatment effect is a very important property. In particular, properties that can reduce hair frizz without damaging the hair are desirable in hair care cosmetics. Heretofore, some prior art documents on hair care cosmetics have been published.

  JP 2011-132191 discloses a hair cosmetic comprising at least one aromatic sulfone compound represented by a specific formula, and at least one carnitine or a salt thereof.

JP 2011-132191 A

  However, there is still a need for hair care cosmetics with improved hair treatment efficacy, in particular the relaxation properties of the hair.

  The object of the present invention is a composition for treating keratin fibers, preferably hair, which has an improved treatment efficacy, in particular an improved hair straightening effectiveness (straightened crimped hair straightens It is an object of the present invention to provide a composition capable of imparting to keratin fibers a property to be alleviated, also referred to as relaxation properties), ease of handling and smoothness.

  The above object of the present invention is a composition for treating keratin fibers, preferably hair, which comprises the general formula (1) or (2)

(Wherein each R may be the same or different, and independently represents -H, -NH ₂ , or a monovalent hydrocarbon group, or, together with the adjacent R, it is divalent) Form a hydrocarbon group,
Provided that at least one R is -NH ₂ )
And at least one aromatic sulfonic acid compound represented by or a salt thereof.

In the general formula (1) or (2),
R independently represents —H, —NH ₂ or an alkyl group containing 1 to 8 carbon atoms, preferably 1 to 6 carbon atoms, more preferably 1 to 4 carbon atoms Often,
Provided that at least one R is -NH _2.

In the general formula (1) or (2), only one R may represent -NH ₂ .

In the general formula (1) or (2), only one R may represent -NH ₂ and the other R may represent -H.

  The aromatic sulfonic acid compound may be represented by the general formula (1).

  The aromatic sulfonic acid compound may be sulfanilic acid or a salt thereof.

  In one embodiment of the present invention, the aromatic sulfonic acid compound is contained in an amount of 0.01 to 15% by mass, preferably 0.1 to 10% by mass, more preferably 1 to 7% by mass, based on the total mass of the composition. It may be present in quantities.

  The composition according to the present invention may be a composition for care or conditioning of keratin fibers.

  The composition according to the invention may be a composition for hair straightening keratin fibers, straightening keratin fibers, or providing keratin fibers with good handling and smoothness.

  The invention also relates to a cosmetic method for treating keratinous fibres, preferably hair, which comprises applying to the keratinous fibers a composition according to the invention.

  The cosmetic process according to the invention may be a cosmetic process for caring or conditioning keratin fibers, preferably hair.

  The cosmetic method according to the present invention may be a cosmetic method for hair straightening keratin fibers, straightening keratin fibers, or providing keratin fibers with good handling and smoothness.

  As a result of intensive studies, the present inventors have surprisingly found that the use of a specific aromatic sulfonic acid compound can improve the ability to care or condition keratin fibers, such as improving the hair straightening effect, keratin fibers, It has been found that preferably the hair can be given manageability and smoothness, and the present invention has been completed.

  Thus, the present invention is mainly a composition for treating keratinous fibers, preferably hair, which comprises the general formula (1) or (2)

(Wherein each R may be the same or different, and independently represents -H, -NH ₂ , or a monovalent hydrocarbon group, or, together with the adjacent R, it is divalent) Form a hydrocarbon group,
Provided that at least one R is -NH ₂ )
And at least one aromatic sulfonic acid compound represented by or a salt thereof.

  By "keratin fiber" is meant herein a fiber comprising at least one keratinous substance. Preferably, at least a portion of the surface of keratinous fibers is formed by keratinous material. Examples of keratin fibers include hair, eyebrows, eyelashes and the like. Preferably the invention is used to treat hair.

  In particular, the composition according to the invention has an excellent hair-clipping-correction effect and also imparts to the hair improved manageability and smoothness.

  Hereinafter, the composition according to the present invention will be described in detail.

[Composition]
The composition according to the invention is a composition for treating keratin fibers, for example for treating, conditioning or hair straightening keratin fibers, preferably hair. The composition according to the invention can also be used to control the volume of keratinous fibers and / or to straighten curled keratinous fibers, preferably the hair.

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

  The composition according to the invention can be used in a composition for treating keratinous fibers. For example, the composition may be a shampoo, conditioner, hair treatment cream, gel, mousse, pump hair spray, aerosol hair spray, set lotion, blow styling lotion, hair color lotion, hair frothing composition, permanent wave reduction It can be formulated into an agent, a permanent wave treatment neutralizing agent, a coloring composition, and a rinse-off or leave-on-type hair care treatment composition.

  In particular, the compositions according to the invention are particularly suitable for hair care treatment compositions, since they have an excellent hair-clipping-correction effect, an effect of improving the manageability of the hair, and a smoothness-imparting effect on the hair. Thus, the composition according to the invention can be used, for example, to reduce or control the apparent volume of keratin fiber bundles. In particular, the volume of hair, in particular the volume of natural wavy or curled hair can be reduced or managed. Also, the keratin fibers can be easily styled with a comb or brush, improving the discipline of the keratin fibers. Furthermore, the feel and the fingering of keratin fibers can be improved.

  The composition according to the invention has the general formula (1) or (2)

(Wherein each R may be the same or different, and independently represents -H, -NH ₂ , or a monovalent hydrocarbon group, or, together with the adjacent R, it is divalent) Form a hydrocarbon group,
Provided that at least one R is -NH ₂ )
And at least one aromatic sulfonic acid compound represented by or a salt thereof.

  In the context of the present invention "hydrocarbon group" means an aliphatic group consisting of carbon atoms and hydrogen atoms. Unless otherwise indicated, such groups have 1 to 30 carbon atoms, preferably 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms, especially 1 to 8 carbon atoms. It may be contained, may be linear, branched or cyclic, and may be saturated or unsaturated.

  The monovalent hydrocarbon group may be selected herein, for example, from alkyl, alkenyl, alkynyl, cycloalkyl and aryl groups.

  The alkyl group may be linear or branched. Preferably, the alkyl group contains 1 to 20, 1 to 12, 1 to 8, 1 to 6, or 1 to 4 carbon atoms. Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, isopentyl, hexyl, isohexyl, heptyl, octyl, nonyl and decyl groups.

  Alkenyl groups may be linear or branched and contain at least one carbon-carbon double bond. Preferably, the alkenyl group contains 2 to 18, 2 to 14, 2 to 10, or 2 to 6 carbon atoms. Examples of alkenyl groups include ethenyl, propenyl and butenyl groups.

  Alkynyl groups may be linear or branched and contain at least one carbon-carbon triple bond. Preferably, alkynyl groups contain 2 to 18, 2 to 14, 2 to 10, or 2 to 6 carbon atoms. Examples of alkynyl groups include ethynyl, propynyl and butynyl groups.

  The cycloalkyl group may be a cyclic alkyl group and may be fused or unfused. Preferably, the cycloalkyl group contains 3 to 12, 3 to 10, 3 to 8 or 3 to 6 carbon atoms. Examples of cycloalkyl groups include cyclopropyl, cyclopentyl and cyclohexyl groups. Furthermore, the cycloalkyl group may optionally be substituted with one or more non-cyclic hydrocarbon groups, such as the alkyl, alkenyl and / or alkynyl groups described above.

  The aryl group may be a fused or unfused monocyclic or polycyclic group comprising at least one aromatic ring. Preferably, the aryl group contains 6 to 22, 6 to 16, or 6 to 10 carbon atoms. Examples of aryl groups include phenyl, biphenyl, naphthyl, indenyl, anthracenyl or tetrahydronaphthyl groups. Furthermore, the aryl group may be optionally substituted by one or more non-cyclic hydrocarbon groups, such as the alkyl, alkenyl and / or alkynyl groups described above.

  The divalent hydrocarbon group herein may be saturated or unsaturated, and may be selected from, for example, alkylene, alkenylene and alkylidene groups.

  The alkylene group may be linear or branched. Preferably, the alkylene group contains 2 to 18, 2 to 14, 2 to 10, or 2 to 6 carbon atoms. Examples of alkylene groups include ethylene, propylene and butylene groups.

  Alkenylene groups may be linear or branched and contain at least one carbon-carbon double bond. Preferably, the alkenylene group contains 2 to 18, 2 to 14, 2 to 10, or 2 to 6 carbon atoms. Examples of the alkenylene group include vinylene, propenylene and butenylene groups.

  The alkylidene group may be linear or branched. Preferably, the alkylidene group contains 2 to 18, 2 to 14, 2 to 10, or 2 to 6 carbon atoms. Examples of alkylidene groups include ethylidene and isopropylidene groups.

In one embodiment of the present invention, in the general formula (1) or (2), R is independently, -H, -NH _2, or one to eight carbon atoms, preferably 1 to 6 carbon atoms More preferably, it represents an alkyl group containing 1 to 4 carbon atoms.

  In a preferred embodiment of the present invention, the aromatic sulfonic acid compound is represented by the general formula (1).

In a preferred embodiment of the invention, in the general formulas (1) or (2), only two R's represent -NH ₂ . In another preferred embodiment of the present invention, in general formula (1) or (2), only one R represents -NH ₂ .

In a particular embodiment of the invention, in general formula (1) or (2), in particular in general formula (1), only one R represents -NH ₂ and the other R represents -H.

  In the most preferred embodiment of the present invention, the aromatic sulfonic acid compound has the general formula

Or 4-aminobenzenesulfonic acid (also referred to as sulfanilic acid) or a salt thereof.

  The aromatic sulfonic acid compound of the present invention may be in the form of a salt. Salts of aromatic sulfonic acid compounds include conventional non-toxic salts of said compounds, such as those formed from bases. The salts may be organic or inorganic salts, or mixtures thereof.

Examples of salts of aromatic sulfonic acid compounds include aromatic sulfonic acid compounds such as mineral bases such as aqueous sodium hydroxide and potassium hydroxide, calcium hydroxide, ammonium hydroxide, magnesium hydroxide, lithium hydroxide, and sodium; Potassium or calcium carbonate or bicarbonate,
Or salts obtained by addition to organic bases such as primary, secondary or tertiary alkylamines such as triethylamine or butylamine. The primary, secondary or tertiary alkylamines may contain one or more nitrogen atoms and / or oxygen atoms and thus may for example contain one or more alcohol functional groups; Specifically, 2-amino-2-methylpropanol, ethanolamine, triethanolamine, 2-dimethylaminopropanol, 2-amino-2- (hydroxymethyl) -1,3-propanediol and 3- (dimethylamino) propyl Amines can be mentioned.

  The salts of the aromatic sulfonic acid compounds can advantageously be selected from alkali metal salts or alkaline earth metal salts, such as sodium salts, potassium salts, calcium salts and magnesium salts; and ammonium salts.

  In certain embodiments of the present invention, the aromatic sulfonic acid compound is selected from alkali metal salts, alkaline earth metal salts, and ammonium salts of sulfanilic acid.

  The aromatic sulfonic acid compound of the present invention may be present at a content of 0.01% by mass or more, preferably 0.1% by mass or more, more preferably 1% by mass or more, based on the total mass of the composition. The aromatic sulfonic acid compound of the present invention may be present at a content of 15% by mass or less, preferably 10% by mass or less, more preferably 7% by mass or less, based on the total mass of the composition.

  The aromatic sulfonic acid compound may be present at a content in the range of 0.01 to 15% by mass, preferably 0.1 to 10% by mass, more preferably 1 to 7% by mass, based on the total mass of the composition. .

(Other ingredients)
The composition according to the invention further comprises all customary ingredients used in the field of compositions for treating keratin fibers, in particular hair, such as water, cosmetically acceptable hydrophilic organic solvents, oils, interfaces. Active agents or emulsifiers, natural extracts derived from animals or plants, anionic, cationic, nonionic or amphoteric polymers, fillers, waxes, protein hydrolysates, swelling agents, penetrating agents, acidifying agents, among Japanese agents, perfumes, perfumes, thickeners, preservatives, sequestering agents, sequestering agents, coloring agents, moisturizers, antidandruff agents, antiseborrhoic agents, sunscreen agents, etc., within the scope not impairing the effects of the present invention May be contained.

  In particular, when the composition according to the invention is in the form of an O / W or W / O emulsion, the composition may also comprise water, a cosmetically acceptable hydrophilic organic solvent, an oil, and a surfactant or an emulsifier. Good.

  The amount of water in the composition according to the invention may be from 10 to 99% by weight, preferably from 20 to 95% by weight, based on the total weight of the composition.

  Cosmetically acceptable hydrophilic organic solvents include, for example, substantially linear or branched lower monoalcohols having 1 to 8 carbon atoms, such as ethanol, propanol, butanol, isopropanol, and isobutanol. Aromatic alcohols such as benzyl alcohol and phenylethyl alcohol; polyols or polyol ethers such as propylene glycol, dipropylene glycol, isoprene glycol, butylene glycol, glycerol, sorbitol, monomethyl, monoethyl and monobutyl ethers of ethylene glycol, propylene glycol ether, For example, propylene glycol monomethyl ether, diethylene glycol alkyl ether, such as monoethyl ether or monobutyl diethylene glycol And polyethylene glycols such as PEG-4, PEG-6, and PEG-8, and derivatives thereof.

  The amount of the hydrophilic organic solvent in the composition according to the present invention is 1 to 50% by mass, preferably 2 to 40% by mass, more preferably 5 to 30% by mass, based on the total mass of the composition. Good.

  The term "oil" as used herein means a fatty compound or substance which is in the form of a liquid or paste (non-solid) at room temperature (25 ° C.) and atmospheric pressure (760 mm Hg). Examples of oils that can be contained in the composition of the present invention include oils of animal or vegetable origin, mineral oils, synthetic glycerides, esters of fatty alcohols and / or fatty acids other than animal or vegetable oils and synthetic glycerides, fatty alcohols, fatty acids, silicone oils And aliphatic hydrocarbons.

  The oil may be present in the composition in an amount of 50% by weight or less, preferably 40% by weight or less, more preferably 30% by weight or less, based on the total weight of the composition.

  The surfactant or emulsifier can be selected from nonionic, anionic, amphoteric, zwitterionic, cationic emulsifiers and mixtures thereof. Examples of emulsifiers also include natural or synthetic polymeric emulsifiers.

  The amount of surfactant or emulsifier in the composition according to the invention is from 0.01 to 15% by weight, preferably from 0.05 to 10% by weight, more preferably from 0.1 to 5% by weight, based on the total weight of the composition. It is also good.

  The pH of the composition according to the invention can be adjusted to the desired value using acidifying or basifying agents commonly used in cosmetics.

  The composition according to the invention is preferably acidic. Therefore, the pH of the composition is preferably 2 to 9, more preferably 3 to 8.

  Among the acidifying agents which may be mentioned by way of example are mineral acids or organic acids such as hydrochloric acid, orthophosphoric acid, sulfuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid, glycolic acid and lactic acid, and sulfonic acids .

  Among the basifying agents which may be mentioned by way of example are ammonium hydroxide, alkali metal carbonates, alkanolamines such as mono-, di- and triethanolamine, and also derivatives thereof, sodium hydroxide or water Potassium oxide and the following general formula

(In the formula,
W represents an alkylene such as propylene which is optionally substituted with a hydroxyl or a C _{1 to} C ₄ alkyl group, and R _a , R _b , R _c and R _d independently represent a hydrogen atom, an alkyl group or C ₁ -C ₄ hydroxyalkyl group is shown)
The compound of formula (I) can be exemplified by 1,3-propanediamine and derivatives thereof. Sodium hydroxide or potassium hydroxide is preferred because it can also function to form a buffer in situ.

  The acidifying agent or basifying agent can be used in an amount ranging from 0.001 to 15% by weight, preferably 0.01 to 10% by weight, more preferably 0.1 to 5% by weight, based on the total weight of the composition.

  The compositions according to the invention can be prepared by any conventional technique in the art, for example by mixing the aromatic sulfonic acid compounds of the invention with a cosmetically acceptable medium such as water. . The other components may be mixed with the aromatic sulfonic acid compound. While mixing these components, it may be heated if necessary.

[Beauty method]
The present invention is a method, preferably a cosmetic method, for treating keratin fibers, preferably for conditioning or care of the hair, comprising the step of applying the composition according to the present invention to keratin fibers, preferably hair. It also relates to the method.

  The composition can be applied to the hair by first applying it to the hand and then contacting the hair with the hand, and in other embodiments applying the composition directly to the hair by spraying etc. it can. The composition can also be delivered to the hair by use of an applicator or device. The composition may be applied to the hair as a non-rinsing treatment, or as a rinse-off treatment, the composition may be rinsed off after application.

  In one embodiment of the present invention, the composition can be used as a hair care composition or a hair conditioning composition. Accordingly, the present invention also relates to the use of the combination comprising the aromatic sulfonic acid compound of the present invention as a hair care composition or a hair conditioning composition.

  In one embodiment of the present invention, the composition may be used to hair straighten keratin fibers, straighten keratin fibers, or to provide keratin fibers with good handling and smoothness.

  The cosmetic method according to the invention can give the hair an attractive appearance in view of the excellent hair-clipping-correction effect of the composition according to the invention and the effect of giving the hair its handling and smoothness.

  In one embodiment, the cosmetic method of the present invention is a method for hair straightening keratin fibers, straightening keratin fibers, or providing keratin fibers with good handling and smoothness.

  The invention will be explained in more detail by means of examples. However, these examples should not be construed as limiting the scope of the present invention.

[Composition]
The compositions according to Example 1 and Comparative Examples 1 to 5 were prepared by mixing various sulfonic acid compounds and deionized water. The amount of each sulfonic acid compound was set to 5% by mass. Comparative Example 6 was for reference only and did not contain a sulfonic acid compound. The pH of each composition was adjusted to 3.3 with hydrochloric acid and / or sodium hydroxide. Table 1 (Table 1) shows the chemical species of the sulfonic acid compound contained in each composition.

[Evaluation]
(Hair straightening effect)
The hair straightening effect of each composition was assessed in the C-Curl test described below. Five C-shaped curled strands of hair were prepared from the curled hair mesh for each composition. The length of the curled strand was set to about 15 mm. The strands were immersed in 20 mL of each composition in an evaporating dish at room temperature. The diameter of the five curls was measured for each composition immediately after the start of immersion, ie at the beginning, and 10 and 60 minutes after the start of immersion. By calculating the increase in curvature of each strand, the hair reduction efficacy (%) was determined by the following equation.

Hair straightening effectiveness (%) = (T _1- T ₀ ) / T ₀ × 100%
T ₀ : Initial diameter of C-curl
T ₁ : final diameter of C-curl

  The hair straightening effect of the composition was determined according to the following evaluation criteria.

Good: Hair straightening effectiveness was higher than 30%.
Fair: The hair straightening effectiveness was 20% or more and less than 30%.
Poor: Hair straightening effectiveness was less than 20%.

  The results are shown in Table 1 (Table 1).

  As can be understood from the results in Table 1 (Table 1), the composition according to Example 1 containing the aromatic sulfonic acid compound of the present invention is a compound according to Comparative Examples 1 to 6 which does not contain the aromatic sulfonic acid compound of the present invention. It exhibited a hair straightening effect superior to that of the composition.

(Straightening effectiveness, ease of handling, and smoothness)
The straightening efficacy, ease of handling and smoothness of each composition according to Example 1 and Comparative Examples 3 and 6 were evaluated in the following mesh test. Hair mesh (1 g, 27 cm, Indian Virgin Hair Type III) was soaked in 150 g of the composition overnight at room temperature. The hair mesh was then rinsed with running water and excess solution was wiped once with a paper towel. The hair mesh was then carefully tap dried with a paper towel so that each curled strand was not affected by the adjacent strands. The cosmetic properties of the composition were evaluated by observation and sensory examination by six panelists. Specifically, the straightening effectiveness was assessed by observing the degree of hair straightening of the hair mesh immediately after tap drying. The ease of handling was assessed by observation of the volume of the hair mesh after a single pass of the dried hair mesh. The smoothness was assessed by sensory examination of the hair surface of the dried hair.

  The results are shown in Table 2 (Table 2).

  As can be understood from the results of Table 2, the composition according to the present invention exhibited improved straightening efficacy with the hair and gave the hair good handleability and smoothness. On the other hand, the composition according to Comparative Example 3 containing p-toluenesulfonic acid monohydrate instead of the aromatic sulfonic acid compound of the present invention does not show good straightening efficacy on the hair and is easy to handle Did not give the hair size and smoothness. Similarly, the reference example of Comparative Example 6 also showed low straightening effectiveness, ease of handling and smoothness.

  Thus, it is concluded that the composition according to the invention can exhibit improved hair straightening and straightening efficacy with keratinous fibers and that good manageability and smoothness can also be imparted to keratinous fibers, such as the hair. be able to. Thus, the composition according to the invention is highly preferred for use in the care and / or conditioning of keratin fibres.

Claims (12)

A composition for treating keratinous fibers, preferably hair, which comprises the general formula (1) or (2)

(Wherein each R may be the same or different, and independently represents -H, -NH ₂ , or a monovalent hydrocarbon group, or, together with the adjacent R, it is divalent) Form a hydrocarbon group,
Provided that at least one R is -NH ₂ )
A composition comprising at least one aromatic sulfonic acid compound represented by or a salt thereof. In the general formula (1) or (2), R is independently -H, -NH ₂ or 1 to 8 carbon atoms, preferably 1 to 6 carbon atoms, more preferably 1 to 4 Represents an alkyl group containing a carbon atom of
Provided that at least one R is -NH _2, The composition of claim 1. In the general formula (1) or (2), only one R represents -NH _2, A composition according to claim 1 or 2. In the general formula (1) or (2), only one R represents -NH _2, the other R represents -H, composition according to any one of claims 1 to 3.   The composition according to any one of claims 1 to 4, wherein the aromatic sulfonic acid compound is represented by the general formula (1).   The composition according to any one of claims 1 to 5, wherein the aromatic sulfonic acid compound is sulfanilic acid or a salt thereof.   The aromatic sulfonic acid compound is present in a content ranging from 0.01 to 15 wt%, preferably 0.1 to 10 wt%, more preferably 1 to 7 wt%, relative to the total weight of the composition. The composition according to any one of 1 to 6.   The composition according to any one of claims 1 to 7, which is a composition for care or conditioning of keratin fibers.   A composition according to any one of the preceding claims, which is a composition for relieving the crimp of keratinous fibers, straightening the keratinous fibers, or imparting to the keratinous fibers good handling and smoothness. .   A cosmetic method for treating keratinous fibers, preferably hair, comprising the step of applying to said keratinous fibers a composition according to any one of the preceding claims.   11. A cosmetic method according to claim 10, which is a cosmetic method for caring or conditioning keratinous fibers, preferably hair.   11. A cosmetic method according to claim 10, for relieving the crimp of keratinous fibers, straightening the keratinous fibers, or providing the keratinous fibers with good handling and smoothness.