WO2019066082A1 - A composition for treating keratinous fibers - Google Patents

A composition for treating keratinous fibers Download PDF

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Publication number
WO2019066082A1
WO2019066082A1 PCT/JP2018/036614 JP2018036614W WO2019066082A1 WO 2019066082 A1 WO2019066082 A1 WO 2019066082A1 JP 2018036614 W JP2018036614 W JP 2018036614W WO 2019066082 A1 WO2019066082 A1 WO 2019066082A1
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WIPO (PCT)
Prior art keywords
keratinous fibers
hair
composition according
composition
present
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Application number
PCT/JP2018/036614
Other languages
French (fr)
Inventor
Stephanie VALENTINA
Hidetoshi Yamada
Daisuke Ishii
Original Assignee
L'oreal
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Publication date
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Publication of WO2019066082A1 publication Critical patent/WO2019066082A1/en

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/12—Preparations containing hair conditioners
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A61K8/466—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfonic acid derivatives; Salts
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/04—Preparations for permanent waving or straightening the hair

Definitions

  • the present invention relates to a composition for treating keratinous fibers, in particular a hair care cosmetic composition comprising at least one aromatic sulfonic acid compound or a salt thereof.
  • hair treatment effects are very important properties.
  • a property that can relax the hair without causing hair damage is desirable for hair care cosmetic products.
  • some prior art documents relating to hair care cosmetic products have been published.
  • JP-A-2011-132191 discloses a hair cosmetic containing at least one aromatic sulfone compound represented by a specific formula and at least one carnitine or its salt.
  • An objective of the present invention is to provide a composition for treating keratinous fibers, preferably hair, having improved treatment efficacy, in particular being capable of imparting improved relaxation efficacy, manageability, and smoothness to keratinous fibers.
  • composition for treating keratinous fibers, preferably hair comprising at least one aromatic sulfonic acid compound represented by general formula (1) or (2):
  • each R which may be the same or different, independently represents -H, -NH 2 , or a monovalent hydrocarbon group, or forms a divalent hydrocarbon group together with an adjacent R,
  • R independently may represent -H, -NH 2 , or an alkyl group including 1 to 8 carbon atoms, preferably 1 to 6 carbon atoms, and more preferably 1 to 4 carbon atoms,
  • R may represent -NH 2 .
  • R may represent -NH 2 and the other Rs may represent -H.
  • the aromatic sulfonic acid compound may be represented by general formula (1).
  • the aromatic sulfonic acid compound may be sulfanilic acid or a salt thereof.
  • the aromatic sulfonic acid compound may be present in a content ranging from 0.01% to 15%> by weight, preferably from 0.1%) to 10%> by weight, and more preferably from 1%> to 7% by weight, relative to the total weight of the composition.
  • the . composition according to the present invention can be for caring for or conditioning keratinous fibers.
  • composition according to the present invention can be for relaxing keratinous fibers, straitening keratinous fibers, or providing good manageability and smoothness to keratinous fibers.
  • the present invention also relates to a cosmetic process for treating keratinous fibers, preferably hair, comprising the step of applying onto the keratin fibers the composition according to the present invention.
  • the cosmetic process according to the present invention can be for caring for or conditioning keratinous fibers, preferably hair.
  • the cosmetic process according to the present invention can be for relaxing keratinous fibers, straitening keratinous fibers, or providing good manageability and smoothness to keratinous fibers.
  • the present invention mainly relates to a composition for treating keratinous fibers, preferably hair, comprising at least one aromatic sulfonic acid compound represented by general formula (1) or (2):
  • each R which may be the same or different, independently represents -H, -NH 2 , or a monovalent hydrocarbon group, or forms a divalent hydrocarbon group together with an adjacent R,
  • keratinous fibers here mean fibers which include at least one keratinous substance. It is preferable that at least a part of the surface of the keratinous fibers be formed by keratinous substances. Examples of keratinous fibers include hair, eyebrows, eyelashes, and the like. It is preferable that the present invention be used for treating hair.
  • composition according to the present invention has a superior hair relaxation effect, and also provides hair with improved manageability and smoothness.
  • the composition according to the present invention is for treating keratinous fibers, for example, for caring for, conditioning, or relaxing keratinous fibers, preferably hair.
  • the composition according to the present invention also can be used to control the volume of keratinous fibers and/or to straighten curly keratinous fibers, preferably hair.
  • 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.
  • compositions for treating keratinous fibers can be used in compositions for treating keratinous fibers.
  • the composition can be formulated into shampoos, conditioners, hair treatment creams, gels, mousses, pump hair sprays, aerosol hair sprays, setting lotions, blow styling lotions, hair color lotions, hair relaxing compositions, reducers for permanent wave, neutralizers for a permanent wave treatment, coloring compositions, and a rinse-off type or leave-on type hair care treatment composition.
  • the composition according to the present invention possesses a superior hair relaxation effect, hair manageability improving effect, and an effect of imparting smoothness to hair, the composition is suitable, in particular, for hair care treatment compositions.
  • composition according to the present invention can be used, for example, so that the apparent volume of a bunch of keratinous fibers can be reduced or controlled.
  • the volume of hair, in particular naturally wavy or curly hair can be reduced or controlled.
  • the discipline of keratinous fibers can be improved such that the keratinous fibers can be easily styled with a comb or a brush.
  • the feel to the touch and running the fingers through the keratinous fibers can be improved.
  • composition according to the present invention comprises at least one aromatic sulfonic acid compound represented by general formula (1) or (2):
  • each R which may be the same or different, independently represents -H, NH 2 , or a monovalent hydrocarbon group, or forms a divalent hydrocarbon group together with an adjacent R,
  • hydrocarbon group means an aliphatic radical composed of carbon atoms and of hydrogen atoms. Unless otherwise indicated, such a radical can comprise from 1 to 30 carbon atoms, preferably 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms, and in particular 1 to 8 carbon atoms, and can be linear, branched, or cyclic and can be saturated or unsaturated.
  • the monovalent hydrocarbon group herein can be chosen from, for example, an alkyl, alkenyl, alkynyl, cycloalkyl, and aryl group.
  • the alkyl group can be linear or branched.
  • the alkyl group includes 1 to 20, 1 to 12, 1 to 8, 1 to 6, or 1 to 4 carbon atoms.
  • Examples of the alkyl group may include a methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, isopentyl, hexyl, isohexyl, heptyl, octyl, nonyl, and decyl group.
  • the alkenyl group can be linear or branched and includes at least one carbon-carbon double bond.
  • the alkenyl group includes 2 to 18, 2 to 14, 2 to 10, or 2 to 6 carbon atoms.
  • Examples of the alkenyl group may include an ethenyl, propenyl, and butenyl group.
  • the alkynyl group can be linear or branched and includes at least one carbon-carbon triple bond.
  • the alkyl group includes 2 to 18, 2 to 14, 2 to 10, or 2 to 6 carbon atoms.
  • Examples of the alkynyl group may include an ethynyl, propynyl, and butynyl group.
  • the cycloalkyl group can be cyclic alkyl groups, which may be fused or non-fused.
  • the cycloalkyl group includes 3 to 12, 3 to 10, 3 to 8, or 3 to 6 carbon atoms.
  • Examples of the cycloalkyl group may include a cyclopropyl, cyclopentyl, and cyclohexyl group.
  • the cycloalkyl group can be optionally substituted with one or more acyclic hydrocarbon groups, such as alkyl, alkenyl, and/or alkynyl groups as explained above.
  • the aryl group can be fused or non-fused mono- or polycyclic groups comprising at least one aromatic ring.
  • the aryl group includes 6 to 22, 6 to 16, or 6 to 10 carbon atoms.
  • Examples of the aryl group may include a phenyl, biphenyl, naphthyl, indenyl, anthracenyl, or tertahydronapthyl group.
  • the aryl group can be optionally substituted with one or more acyclic hydrocarbon groups, such as alkyl, alkenyl, and/or alkynyl groups as explained above.
  • the divalent hydrocarbon group herein can be saturated or unsaturated, and may be chosen from, for example, an alkylene, alkenylene, and alkylidene group.
  • the alkylene group can be linear or branched.
  • the alkylene group includes 2 to 18, 2 to 14, 2 to 10, or 2 to 6 carbon atoms.
  • Examples of the alkylene group may include an ethylene, propylene, and butylene group.
  • the alkenylene group can be linear or branched and includes at least one carbon-carbon double bond.
  • the alkenylene group includes 2 to 18, 2 to 14, 2 to 10, or 2 to 6 carbon atoms.
  • Examples of the alkenylene group may include a vinylene, propenylene, and butenylene group.
  • the alkylidene group can be linear or branched.
  • the alkylidene group includes 2 to 18, 2 to 14, 2 to 10, or 2 to 6 carbon atoms.
  • Examples of the alkylidene group may include an ethylidene and isopropylidene group.
  • R independently represents -H, -NH 2 , or an alkyl group including 1 to 8 carbon atoms, preferably 1 to 6 carbon atoms, and more preferably 1 to 4 carbon atoms.
  • the aromatic sulfonic acid compound is represented by general formula (1).
  • the aromatic sulfonic acid compound is 4-aminobenzenesulfonic acid, which is also called sulfanilic acid, as represented by the general formula below, or its salt.
  • the aromatic sulfonic acid compound of the present invention can be in the form of a salt.
  • the salts of the aromatic sulfonic acid compound include conventional non-toxic salts of said compounds, such as those formed from a base.
  • the salt may be an organic or inorganic salt, or a mixture thereof.
  • the salts of the aromatic sulfonic acid compound may include the salts obtained by addition of the aromatic sulfonic acid compound to a mineral base, such as aqueous sodium hydroxide and potassium hydroxide, calcium hydroxide, ammonium hydroxide, magnesium hydroxide, lithium hydroxide, and sodium, potassium or calcium carbonates or hydrogencarbonates, for example;
  • a mineral base such as aqueous sodium hydroxide and potassium hydroxide, calcium hydroxide, ammonium hydroxide, magnesium hydroxide, lithium hydroxide, and sodium, potassium or calcium carbonates or hydrogencarbonates, for example;
  • a primary, secondary or tertiary alkylamine for example triethylamine or butylamine.
  • This primary, secondary or tertiary alkylamine may comprise one or more nitrogen and/or oxygen atoms and may therefore comprise, for example, one or more alcohol functions; included more particularly are 2-amino-2-methylpropanol, ethanolamine, triethanolamine, 2-dimethylamino propanol,
  • the salts of the aromatic sulfonic acid compound may advantageously be selected from alkali metal salts or alkaline earth metal salts such as sodium, potassium, calcium and magnesium salts; and ammonium salts.
  • 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 in a content of 0.01% by weight or more, preferably 0.1% by weight or more, and more preferably 1% by weight or more, relative to the total weight of the composition.
  • the aromatic sulfonic acid compound of the present invention may be present in a content of 15% by weight or less, preferably 10% by weight or less, and more preferably 7% by weight or less, relative to the total weight of the composition.
  • the aromatic sulfonic acid compound may be present in a content ranging from 0.01% to 15% by weight, preferably from 0.1% to 10% by weight, and more preferably from 1% to 7% by weight, relative to the total weight of the composition.
  • the composition according to the present invention may further contain all the customary ingredients encountered in the field of compositions for treating keratinous fibers, especially hair, for example, water, cosmetically acceptable hydrophilic organic solvents, oils, surfactants or emulsifiers, natural extracts derived from animals or vegetables, anionic, cationic, nonionic or amphoteric polymers, fillers, waxes, protein hydrolyzates, swelling agents, penetrating agents, acidifying agents, neutralizing agents, perfumes, fragrances, thickeners, preservatives, sequestrants, colorants, moisturizing agents, antidandruff agents, antiseborrhoeic agents, sunscreens and the like, within a range which does not impair the effects of the present invention.
  • the amount of water in the composition according to the present invention may be from 10 to 99% by weight, preferably from 20 to 95% by weight, relative to the total weight of the composition.
  • the cosmetically acceptable hydrophilic organic solvent(s) may include, for example, substantially linear or branched lower mono-alcohols having from 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, ethylene glycol monomethyl, monoethyl and monobutyl ethers, propylene glycol ethers, such as propylene glycol monomethylether, diethylene glycol alkyl ethers, such as diethylene glycol
  • monoethylether or monobutylether examples include monoethylether or monobutylether; and polyethylene glycols, such as PEG-4, PEG-6, and PEG-8, and their derivatives.
  • the amount of the hydrophilic organic solvent(s) in the composition according to the present invention may be from 1 to 50% by weight, preferably from 2 to 40% by weight, and more preferably from 5 to 30%» by weight, relative to the total weight of the composition.
  • oil here means a fatty compound or substance which is in the form of a liquid or a paste (non-solid) at room temperature (25°C) under atmospheric pressure (760 mmHg).
  • Oils that can be contained in the composition of the present invention include oils of animal or plant origin, mineral oils, synthetic glycerides, esters of fatty alcohols and/or fatty acids other than animal or plant 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, and more preferably 30% by weight or less, relative to the total weight of the composition.
  • the surfactant(s) or emulsifier(s) may be selected from nonionic, anionic, amphoteric, zwitterionic, cationic emulsifiers, and mixtures thereof.
  • emulsifiers also include natural or synthetic polymeric emulsifiers.
  • the amount of the surfactant(s) or emulsifier(s) in the composition according to the present invention may be from 0.01 to 15% by weight, preferably from 0.05 to 10% by weight, and more preferably from 0.1 to 5% by weight, relative to the total weight of the composition.
  • the pH of the composition according to the present invention may be adjusted to the desired value using acidifying or basifying agents commonly used in cosmetics.
  • the composition according to the present invention is preferably acidic. Therefore, it is preferable that the pH of the composition be from 2 to 9, more preferably from 3 to 8.
  • acidifying agents mention may be made, by way of example, of mineral or organic acids such as hydrochloric acid, ortho-phosphoric acid, sulfuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid, glycolic acid and lactic acid, and sulfonic acids.
  • mineral or organic acids such as hydrochloric acid, ortho-phosphoric acid, sulfuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid, glycolic acid and lactic acid, and sulfonic acids.
  • basifying agents mention may be made, by way of example, of ammonium hydroxide, alkali metal carbonates, alkanolamines such as mono-, di- and triethanolamines and also their derivatives, sodium or potassium hydroxide and compounds of the general formula below:
  • W denotes an alkylene such as propylene optionally substituted by a hydroxyl or a Ci-C 4 alkyl radical
  • Ra, Rb, Rc and Rd independently denote a hydrogen atom, an alkyl radical or a C1-C4 hydroxyalkyl radical, which may be exemplified by 1,3-propanediamine and derivatives thereof.
  • Sodium or potassium hydroxide is preferable, because this can also function to form in situ a buffering agent.
  • the acidifying or basifying agent may be used in an amount ranging from 0.001 to 15% by weight, preferably from 0.01 to 10% by weight, and more preferably from 0.1 to 5% by weight, relative to the total weight of the composition.
  • composition according to the present invention can be manufactured through any usual techniques in the art, for example, by mixing the aromatic sulfonic acid compound of the present invention with a cosmetically acceptable medium, such as water. Said other ingredients can be mixed with the aromatic sulfonic acid compound. While mixing these ingredients, they can be heated, if necessary.
  • the present invention also relates to a process, preferably a cosmetic process for treating keratinous fibers, preferably for conditioning or caring for hair, comprising a step of applying the composition according to the present invention to keratinous fibers, preferably 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 or the composition may be rinsed-off after it is applied, as a rinsed-off-type treatment.
  • the composition can be used as a hair care or hair conditioning composition. Therefore, the present invention also relates to the use of a combination including the aromatic sulfonic acid compound of the present invention as a hair care or hair conditioning composition.
  • the composition can be used for relaxing keratinous fibers, straitening keratinous fibers, or providing good manageability and smoothness to keratinous fibers.
  • the cosmetic process according to the present invention can provide an attractive appearance to the hair.
  • the cosmetic process of the present invention is for relaxing keratinous fibers, straitening keratinous fibers, or providing good manageability and smoothness to keratinous fibers.
  • compositions according to Example 1 and Comparative Examples 1 to 5 were prepared by mixing different sulfonic acid compounds and deionized water. The amount of each of the sulfonic acid compounds was set to 5% by weight. Comparative Example 6 is only for reference and included no sulfonic acid compounds. The pH of each of the compositions was adjusted to 3.3 with hydrochloric acid and/or sodium hydroxide. Table 1 shows the species of sulfonic acid compounds included in each of the compositions.
  • the relaxation effect of each of the compositions was evaluated with the following C-curl test.
  • Five C-shaped curly strands of hair were prepared from a curly hair mesh for each of the compositions.
  • the length of curly strands was set to about 15 mm.
  • the strands were immersed in 20 mL of each of the compositions in an evaporating dish at room temperature.
  • the diameters of five curls were measured in each of the compositions just after the immersion started, i.e. at initial time, and at 10 and 60 minutes after the immersion started.
  • the relaxation efficacy (%) was measured by calculating the increase of the curvature of each of the strands with the equation below.
  • composition according to Example 1 including the aromatic sulfonic acid compound of the present invention exhibited a superior relaxation effect in the compositions according to Comparative Examples 1 to 6, which do not include the aromatic sulfonic acid compound of the present invention.
  • composition according to the present invention 5 exhibited improved straightening efficacy on the hair, and provided the hair with good
  • Comparative Example 3 which includes p-Toluene sulfonic acid monohydrate instead of the aromatic sulfonic acid compound of the present invention did not show good straightening efficacy on the hair and did not provide good manageability and smoothness to the hair.
  • the reference example of Comparative Example 6 showed poor straightening efficacy, manageability, and smoothness.
  • composition according to the present invention can exhibit improved relaxation and straightening efficacy on keratinous fibers, and also can 5 provide hair with good manageability and smoothness to the keratinous fibers, such as hair.
  • composition according to the present invention is very preferable for use in caring for and/or conditioning keratinous fibers.

Abstract

The present invention relates to a composition for treating keratinous fibers, preferably hair, comprising at least one aromatic sulfonic acid compound represented by general formula (1) or (2): in which, each R, which may be the same or different, independently represents -H, -NH2, or a monovalent hydrocarbon group, or forms a divalent hydrocarbon group together with an adjacent R, with the proviso that at least one R is -NH2, or a salt thereof.

Description

DESCRIPTION
A COMPOSITION FOR TREATING KERATINOUS FIBERS
TECHNICAL FIELD
The present invention relates to a composition for treating keratinous fibers, in particular a hair care cosmetic composition comprising at least one aromatic sulfonic acid compound or a salt thereof.
BACKGROUND ART
In the field of hair cosmetics, hair treatment effects are very important properties. In particular, a property that can relax the hair without causing hair damage is desirable for hair care cosmetic products. To date, some prior art documents relating to hair care cosmetic products have been published.
JP-A-2011-132191 discloses a hair cosmetic containing at least one aromatic sulfone compound represented by a specific formula and at least one carnitine or its salt.
DISCLOSURE OF INVENTION
However, there is still a demand for hair care cosmetic products with improved hair treatment efficacy, in particular hair relaxing efficacy.
An objective of the present invention is to provide a composition for treating keratinous fibers, preferably hair, having improved treatment efficacy, in particular being capable of imparting improved relaxation efficacy, manageability, and smoothness to keratinous fibers.
The above objective of the present invention can be achieved by a composition for treating keratinous fibers, preferably hair, comprising at least one aromatic sulfonic acid compound represented by general formula (1) or (2):
Figure imgf000002_0001
in which, each R, which may be the same or different, independently represents -H, -NH2, or a monovalent hydrocarbon group, or forms a divalent hydrocarbon group together with an adjacent R,
with the proviso that at least one R is -NH2,
or a salt thereof. In general formula (1) or (2),
R independently may represent -H, -NH2, or an alkyl group including 1 to 8 carbon atoms, preferably 1 to 6 carbon atoms, and more preferably 1 to 4 carbon atoms,
with the proviso that at least one R is -NH2.
In general formula (1) or (2), only one R may represent -NH2.
In general formula (1) or (2), only one R may represent -NH2 and the other Rs may represent -H.
The aromatic sulfonic acid compound may be represented by 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 may be present in a content ranging from 0.01% to 15%> by weight, preferably from 0.1%) to 10%> by weight, and more preferably from 1%> to 7% by weight, relative to the total weight of the composition.
The . composition according to the present invention can be for caring for or conditioning keratinous fibers.
The composition according to the present invention can be for relaxing keratinous fibers, straitening keratinous fibers, or providing good manageability and smoothness to keratinous fibers.
The present invention also relates to a cosmetic process for treating keratinous fibers, preferably hair, comprising the step of applying onto the keratin fibers the composition according to the present invention.
The cosmetic process according to the present invention can be for caring for or conditioning keratinous fibers, preferably hair. The cosmetic process according to the present invention can be for relaxing keratinous fibers, straitening keratinous fibers, or providing good manageability and smoothness to keratinous fibers.
BEST MODE FOR CARRYING OUT THE INVENTION
After diligent research, the inventors have surprisingly found that the use of a specific aromatic sulfonic acid compound can produce improved performance of caring for or conditioning keratinous fibers, such as improved relaxation effect and imparting
manageability and smoothness on keratinous fibers, preferably hair, and thus they have completed the present invention. Thus, the present invention mainly relates to a composition for treating keratinous fibers, preferably hair, comprising at least one aromatic sulfonic acid compound represented by general formula (1) or (2):
Figure imgf000004_0001
in which, each R, which may be the same or different, independently represents -H, -NH2, or a monovalent hydrocarbon group, or forms a divalent hydrocarbon group together with an adjacent R,
with the proviso that at least one R is -NH2,
or a salt thereof.
The "keratinous fibers" here mean fibers which include at least one keratinous substance. It is preferable that at least a part of the surface of the keratinous fibers be formed by keratinous substances. Examples of keratinous 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, and also provides hair with improved manageability and smoothness.
Hereafter, the composition according to the present invention will be described in a detailed manner.
[Composition]
The composition according to the present invention is for treating keratinous fibers, for example, for caring for, conditioning, or relaxing keratinous fibers, preferably hair. The composition according to the present invention also can be used to control the volume of keratinous fibers and/or to straighten curly keratinous fibers, preferably hair.
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 composition according to the present invention can be used in compositions for treating keratinous fibers. For example, the composition can be formulated into shampoos, conditioners, hair treatment creams, gels, mousses, pump hair sprays, aerosol hair sprays, setting lotions, blow styling lotions, hair color lotions, hair relaxing compositions, reducers for permanent wave, neutralizers for a permanent wave treatment, coloring compositions, and a rinse-off type or leave-on type hair care treatment composition.
Especially, since the composition according to the present invention possesses a superior hair relaxation effect, hair manageability improving effect, and an effect of imparting smoothness to hair, the composition is suitable, in particular, for hair care treatment compositions.
Therefore, the composition according to the present invention can be used, for example, so that the apparent volume of a bunch of keratinous fibers can be reduced or controlled.
Especially, the volume of hair, in particular naturally wavy or curly hair, can be reduced or controlled. Also, the discipline of keratinous fibers can be improved such that the keratinous fibers can be easily styled with a comb or a brush. Furthermore, the feel to the touch and running the fingers through the keratinous fibers can be improved.
The composition according to the present invention comprises at least one aromatic sulfonic acid compound represented by general formula (1) or (2):
Figure imgf000005_0001
in which, each R, which may be the same or different, independently represents -H, NH2, or a monovalent hydrocarbon group, or forms a divalent hydrocarbon group together with an adjacent R,
with the proviso that at least one R is -NH2,
or a salt thereof.
In the context of the present invention, "hydrocarbon group" means an aliphatic radical composed of carbon atoms and of hydrogen atoms. Unless otherwise indicated, such a radical can comprise from 1 to 30 carbon atoms, preferably 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms, and in particular 1 to 8 carbon atoms, and can be linear, branched, or cyclic and can be saturated or unsaturated.
The monovalent hydrocarbon group herein can be chosen from, for example, an alkyl, alkenyl, alkynyl, cycloalkyl, and aryl group. The alkyl group can be linear or branched. Preferably, the alkyl group includes 1 to 20, 1 to 12, 1 to 8, 1 to 6, or 1 to 4 carbon atoms. Examples of the alkyl group may include a methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, isopentyl, hexyl, isohexyl, heptyl, octyl, nonyl, and decyl group.
The alkenyl group can be linear or branched and includes at least one carbon-carbon double bond. Preferably, the alkenyl group includes 2 to 18, 2 to 14, 2 to 10, or 2 to 6 carbon atoms. Examples of the alkenyl group may include an ethenyl, propenyl, and butenyl group.
The alkynyl group can be linear or branched and includes at least one carbon-carbon triple bond. Preferably, the alkyl group includes 2 to 18, 2 to 14, 2 to 10, or 2 to 6 carbon atoms. Examples of the alkynyl group may include an ethynyl, propynyl, and butynyl group.
The cycloalkyl group can be cyclic alkyl groups, which may be fused or non-fused.
Preferably, the cycloalkyl group includes 3 to 12, 3 to 10, 3 to 8, or 3 to 6 carbon atoms. Examples of the cycloalkyl group may include a cyclopropyl, cyclopentyl, and cyclohexyl group. Furthermore, the cycloalkyl group can be optionally substituted with one or more acyclic hydrocarbon groups, such as alkyl, alkenyl, and/or alkynyl groups as explained above.
The aryl group can be fused or non-fused mono- or polycyclic groups comprising at least one aromatic ring. Preferably, the aryl group includes 6 to 22, 6 to 16, or 6 to 10 carbon atoms. Examples of the aryl group may include a phenyl, biphenyl, naphthyl, indenyl, anthracenyl, or tertahydronapthyl group. Furthermore, the aryl group can be optionally substituted with one or more acyclic hydrocarbon groups, such as alkyl, alkenyl, and/or alkynyl groups as explained above.
The divalent hydrocarbon group herein can be saturated or unsaturated, and may be chosen from, for example, an alkylene, alkenylene, and alkylidene group.
The alkylene group can be linear or branched. Preferably, the alkylene group includes 2 to 18, 2 to 14, 2 to 10, or 2 to 6 carbon atoms. Examples of the alkylene group may include an ethylene, propylene, and butylene group.
The alkenylene group can be linear or branched and includes at least one carbon-carbon double bond. Preferably, the alkenylene group includes 2 to 18, 2 to 14, 2 to 10, or 2 to 6 carbon atoms. Examples of the alkenylene group may include a vinylene, propenylene, and butenylene group.
The alkylidene group can be linear or branched. Preferably, the alkylidene group includes 2 to 18, 2 to 14, 2 to 10, or 2 to 6 carbon atoms. Examples of the alkylidene group may include an ethylidene and isopropylidene group.
In one embodiment of the present invention, in general formula (1) or (2), R independently represents -H, -NH2, or an alkyl group including 1 to 8 carbon atoms, preferably 1 to 6 carbon atoms, and more preferably 1 to 4 carbon atoms.
In one preferred embodiment of the present invention, the aromatic sulfonic acid compound is represented by general formula (1).
In one preferred embodiment of the present invention, in general formula (1) or (2), only two Rs represent -NH2. In another preferred embodiment of the present invention, in general formula (1) or (2), only one R represents -NH2.
In one particular embodiment of the present invention, in general formula (1) or (2), especially in general formula (1), only one R represents -NH2 and the other Rs represent -H. In the most preferred embodiment of the present invention, the aromatic sulfonic acid compound is 4-aminobenzenesulfonic acid, which is also called sulfanilic acid, as represented by the general formula below, or its salt.
Figure imgf000007_0001
The aromatic sulfonic acid compound of the present invention can be in the form of a salt. The salts of the aromatic sulfonic acid compound include conventional non-toxic salts of said compounds, such as those formed from a base. The salt may be an organic or inorganic salt, or a mixture thereof.
The salts of the aromatic sulfonic acid compound may include the salts obtained by addition of the aromatic sulfonic acid compound to a mineral base, such as aqueous sodium hydroxide and potassium hydroxide, calcium hydroxide, ammonium hydroxide, magnesium hydroxide, lithium hydroxide, and sodium, potassium or calcium carbonates or hydrogencarbonates, for example;
or to an organic base such as a primary, secondary or tertiary alkylamine, for example triethylamine or butylamine. This primary, secondary or tertiary alkylamine may comprise one or more nitrogen and/or oxygen atoms and may therefore comprise, for example, one or more alcohol functions; included more particularly are 2-amino-2-methylpropanol, ethanolamine, triethanolamine, 2-dimethylamino propanol,
2-amino-2-(hydroxymethyl)-l ,3 -propanediol and 3-(dimethylamino)propylamine.
The salts of the aromatic sulfonic acid compound may advantageously be selected from alkali metal salts or alkaline earth metal salts such as sodium, potassium, calcium and magnesium salts; and ammonium salts.
In a particular embodiment 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 in a content of 0.01% by weight or more, preferably 0.1% by weight or more, and more preferably 1% by weight or more, relative to the total weight of the composition. The aromatic sulfonic acid compound of the present invention may be present in a content of 15% by weight or less, preferably 10% by weight or less, and more preferably 7% by weight or less, relative to the total weight of the composition.
The aromatic sulfonic acid compound may be present in a content ranging from 0.01% to 15% by weight, preferably from 0.1% to 10% by weight, and more preferably from 1% to 7% by weight, relative to the total weight of the composition. (Other Ingredients) The composition according to the present invention may further contain all the customary ingredients encountered in the field of compositions for treating keratinous fibers, especially hair, for example, water, cosmetically acceptable hydrophilic organic solvents, oils, surfactants or emulsifiers, natural extracts derived from animals or vegetables, anionic, cationic, nonionic or amphoteric polymers, fillers, waxes, protein hydrolyzates, swelling agents, penetrating agents, acidifying agents, neutralizing agents, perfumes, fragrances, thickeners, preservatives, sequestrants, colorants, moisturizing agents, antidandruff agents, antiseborrhoeic agents, sunscreens and the like, within a range which does not impair the effects of the present invention. Especially, when the composition according to the present invention is in the form of an O/W or W/O emulsion, the composition may comprise water, cosmetically acceptable hydrophilic organic solvents, oils, and surfactants or emulsifiers.
The amount of water in the composition according to the present invention may be from 10 to 99% by weight, preferably from 20 to 95% by weight, relative to the total weight of the composition.
The cosmetically acceptable hydrophilic organic solvent(s) may include, for example, substantially linear or branched lower mono-alcohols having from 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, ethylene glycol monomethyl, monoethyl and monobutyl ethers, propylene glycol ethers, such as propylene glycol monomethylether, diethylene glycol alkyl ethers, such as diethylene glycol
monoethylether or monobutylether; and polyethylene glycols, such as PEG-4, PEG-6, and PEG-8, and their derivatives.
The amount of the hydrophilic organic solvent(s) in the composition according to the present invention may be from 1 to 50% by weight, preferably from 2 to 40% by weight, and more preferably from 5 to 30%» by weight, relative to the total weight of the composition.
The term "oil" here means a fatty compound or substance which is in the form of a liquid or a paste (non-solid) at room temperature (25°C) under atmospheric pressure (760 mmHg). Oils that can be contained in the composition of the present invention include oils of animal or plant origin, mineral oils, synthetic glycerides, esters of fatty alcohols and/or fatty acids other than animal or plant 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, and more preferably 30% by weight or less, relative to the total weight of the composition.
The surfactant(s) or emulsifier(s) may 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 the surfactant(s) or emulsifier(s) in the composition according to the present invention may be from 0.01 to 15% by weight, preferably from 0.05 to 10% by weight, and more preferably from 0.1 to 5% by weight, relative to the total weight of the composition.
The pH of the composition according to the present invention may be adjusted to the desired value using acidifying or basifying agents commonly used in cosmetics.
The composition according to the present invention is preferably acidic. Therefore, it is preferable that the pH of the composition be from 2 to 9, more preferably from 3 to 8.
Among the acidifying agents, mention may be made, by way of example, of mineral or organic acids such as hydrochloric acid, ortho-phosphoric 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, mention may be made, by way of example, of ammonium hydroxide, alkali metal carbonates, alkanolamines such as mono-, di- and triethanolamines and also their derivatives, sodium or potassium hydroxide and compounds of the general formula below:
Figure imgf000009_0001
R R
c o
wherein
W denotes an alkylene such as propylene optionally substituted by a hydroxyl or a Ci-C4 alkyl radical, and Ra, Rb, Rc and Rd independently denote a hydrogen atom, an alkyl radical or a C1-C4 hydroxyalkyl radical, which may be exemplified by 1,3-propanediamine and derivatives thereof. Sodium or potassium hydroxide is preferable, because this can also function to form in situ a buffering agent.
The acidifying or basifying agent may be used in an amount ranging from 0.001 to 15% by weight, preferably from 0.01 to 10% by weight, and more preferably from 0.1 to 5% by weight, relative to the total weight of the composition.
The composition according to the present invention can be manufactured through any usual techniques in the art, for example, by mixing the aromatic sulfonic acid compound of the present invention with a cosmetically acceptable medium, such as water. Said other ingredients can be mixed with the aromatic sulfonic acid compound. 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 keratinous fibers, preferably for conditioning or caring for hair, comprising a step of applying the composition according to the present invention to keratinous fibers, preferably 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 or the composition may be rinsed-off after it is applied, as a rinsed-off-type 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 the use of a combination including the aromatic sulfonic acid compound of the present invention as a hair care or hair conditioning composition.
In one embodiment of the present invention, the composition can be used for relaxing keratinous fibers, straitening keratinous fibers, or providing good manageability and smoothness to keratinous fibers.
In consideration of the superior hair relaxation effect and the effect of imparting
manageability and 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.
In one embodiment, the cosmetic process of the present invention is for relaxing keratinous fibers, straitening keratinous fibers, or providing good manageability and smoothness to keratinous fibers.
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.
[Composition] The compositions according to Example 1 and Comparative Examples 1 to 5 were prepared by mixing different sulfonic acid compounds and deionized water. The amount of each of the sulfonic acid compounds was set to 5% by weight. Comparative Example 6 is only for reference and included no sulfonic acid compounds. The pH of each of the compositions was adjusted to 3.3 with hydrochloric acid and/or sodium hydroxide. Table 1 shows the species of sulfonic acid compounds included in each of the compositions.
[Evaluation] (Relaxation Effect)
The relaxation effect of each of the compositions was evaluated with the following C-curl test. Five C-shaped curly strands of hair were prepared from a curly hair mesh for each of the compositions. The length of curly strands was set to about 15 mm. The strands were immersed in 20 mL of each of the compositions in an evaporating dish at room temperature. The diameters of five curls were measured in each of the compositions just after the immersion started, i.e. at initial time, and at 10 and 60 minutes after the immersion started. The relaxation efficacy (%) was measured by calculating the increase of the curvature of each of the strands with the equation below.
Relaxation Efficacy (%) = (Ti - To) / To x 100% To : initial diameter of C-curl
Ti : final diameter of C-curl The relaxation effect of the composition was determined in accordance with the evaluation criteria shown below.
Good: relaxation efficacy was more than 30%
Fair: relaxation efficacy was 20% or more and less than 30%
Poor: relaxation efficacy was less than 20%
The results are shown in Table 1.
Table 1
Figure imgf000011_0001
As can be seen from the results of Table 1, the composition according to Example 1 including the aromatic sulfonic acid compound of the present invention exhibited a superior relaxation effect in the compositions according to Comparative Examples 1 to 6, which do not include the aromatic sulfonic acid compound of the present invention.
(Straightening Efficacy, Manageability, and Smoothness)
Straightening efficacy, the effect of improving manageability and smoothness on the hair of each of the compositions according to Example 1, and Comparative Examples 3 and 6 were evaluated with the following mesh test. Hair mesh (1 g, 27 cm, Indian virgin hair type III) was immersed in 150 g of the composition overnight at room temperature. The hair mesh was then rinsed under running water and excessive solution was wiped with a paper towel once. The hair mesh was then tap dried with a paper towel carefully so that each curly strand was not influenced with adjacent strands. The cosmetic properties of the composition were evaluated by observation and sensory examination by six panelists. Specifically, the straightening efficacy was assessed by observation on the extent of relaxation on the hair mesh just after the tap dry. The manageability was assessed by observation of the volume of the hair mesh after one combing of the dried hair mesh by fingers. The smoothness was assessed by sensory examination on the hair surface of the dried hair.
The results are shown in Table 2. Table 2
Figure imgf000012_0001
As can be seen from the results of Table 2, the composition according to the present invention 5 exhibited improved straightening efficacy on the hair, and provided the hair with good
manageability and smoothness. On the other hand, the composition according to
Comparative Example 3, which includes p-Toluene sulfonic acid monohydrate instead of the aromatic sulfonic acid compound of the present invention did not show good straightening efficacy on the hair and did not provide good manageability and smoothness to the hair. As 0 well, the reference example of Comparative Example 6 showed poor straightening efficacy, manageability, and smoothness.
Therefore, it can be concluded that the composition according to the present invention can exhibit improved relaxation and straightening efficacy on keratinous fibers, and also can 5 provide hair with good manageability and smoothness to the keratinous fibers, such as hair.
Accordingly, the composition according to the present invention is very preferable for use in caring for and/or conditioning keratinous fibers.

Claims

A composition for treating keratinous fibers, preferably hair, comprising at least aromatic sulfonic acid compound represented by general formula (1) or (2):
Figure imgf000013_0001
in which, each R, which may be the same or different, independently represents -H,
-NH2, or a monovalent hydrocarbon group, or forms a divalent hydrocarbon group together with an adjacent R,
with the proviso that at least one R is -NH2,
or a salt thereof.
The composition according to Claim 1 , wherein in general formula (1) or (2), R independently represents -H, -NH2, or an alkyl group including 1 to 8 carbon atoms, preferably 1 to 6 carbon atoms, and more preferably 1 to 4 carbon atoms,
with the proviso that at least one R is -NH2.
The composition according to Claim 1 or 2, wherein in general formula (1) or (2), only one R represents -NH2.
The composition according to any one of the preceding claims, wherein in general formula (1) or (2), only one R represents -NH2 and the other Rs represent -H.
The composition according to any of the preceding claims, wherein the aromatic sulfonic acid compound is represented by general formula (1).
The composition according to any one of the preceding claims, wherein the aromatic sulfonic acid compound is sulfanilic acid or a salt thereof.
The composition according any one of the preceding claims, wherein the aromatic sulfonic acid compound is present in a content ranging from 0.01% to 15% by weight, preferably from 0.1% to 10% by weight, and more preferably from 1% to 7% by weight, relative to the total weight of the composition.
The composition according to any one of the preceding claims, which is for caring for or conditioning keratinous fibers.
The composition according to any one of the preceding claims, which is for relaxing keratinous fibers, straitening keratinous fibers, or providing good manageability and smoothness to keratinous fibers. A cosmetic process for treating keratinous fibers, preferably hair, comprising the step of applying onto the keratin fibers the composition according to any one of the preceding claims.
The cosmetic process according to Claim 10, which is for caring for or conditioning keratinous fibers, preferably hair.
The cosmetic process according to Claim 10, which is for relaxing keratinous fibers, straitening keratinous fibers, or providing good manageability and smoothness to keratinous fibers.
PCT/JP2018/036614 2017-09-27 2018-09-21 A composition for treating keratinous fibers WO2019066082A1 (en)

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Citations (4)

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JP2011132191A (en) 2009-12-25 2011-07-07 Kao Corp Hair cosmetic
WO2018183880A1 (en) * 2017-03-31 2018-10-04 L'oreal Methods for treating hair

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JPH1029917A (en) * 1996-07-16 1998-02-03 Kao Corp Hair-treating agent composition
ATE281147T1 (en) 1998-12-01 2004-11-15 Novozymes As HAIR TREATMENT PROCEDURE
JP6387249B2 (en) 2014-05-26 2018-09-05 花王株式会社 Hair cosmetics
US20190038532A1 (en) 2015-12-25 2019-02-07 Kao Corporation Method for treating hair

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Publication number Priority date Publication date Assignee Title
WO1999058013A1 (en) * 1998-05-07 1999-11-18 Novo Nordisk A/S Re-formation of keratinous fibre cross links
EP1844762A2 (en) * 2006-04-11 2007-10-17 Henkel Kommanditgesellschaft auf Aktien Cosmetic medium with at least 2 silicones
JP2011132191A (en) 2009-12-25 2011-07-07 Kao Corp Hair cosmetic
WO2018183880A1 (en) * 2017-03-31 2018-10-04 L'oreal Methods for treating hair

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