JP2003012474A - Shampoo composition - Google Patents

Abstract

(57) Abstract: A shampoo composition containing (A) an anionic surfactant, (B) an amphoteric surfactant, and (C) a diamide compound (1). Embedded image [R ¹ represents a hydrocarbon group having 1 to 12 carbon atoms which may be substituted by a hydroxyl group and / or an alkoxy group, R ² represents a divalent hydrocarbon group having 1 to 5 carbon atoms, and R ³ represents C 1-22
A divalent hydrocarbon group. [Effect] The present shampoo composition protects the hair from physical and chemical irritation and suppresses the generation of split ends and cut hairs, without impairing the cleaning properties and feeling of use, and is good for hair after washing. Feeling can be imparted.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to protecting hair from physical and chemical irritation and suppressing the generation of split ends and broken hair without impairing the cleansing property and feeling of use, and further to the hair after washing. It relates to shampoo compositions which impart a good feel.

[0002]

2. Description of the Related Art Hair is constantly exposed to physical irritation due to daily hair care behavior such as dryer heat and brushing, and chemical irritation due to perms, hair coloring, bleaching, etc. Injured with partial loss. If such a state is left as it is, it may cause split hairs and broken hairs, a dry feel, a hairstyle that is not organized, and the like, which is not preferable from the viewpoint of hair care. In general, the protection and repair of damaged hair is carried out in a form that complements the components, structures and their analogs that are lost due to the damage. It is considered that the interaction (affinity) between the protective base and the hair is important for the expression of the protective / repair function, and at present, the method of using sphingolipid or a protein derivative as the protective base is widely used as a useful technique. . However, the production of these bases requires an extremely complicated process, and although the effect is recognized, it is a fact that a sufficient amount of the base cannot be blended into the product due to cost problems.

[0003]

Therefore, the present invention is a shampoo composition which is easy to manufacture and can be supplied at a low cost, and which contains a base effective for protecting and repairing hair and which is excellent in the feel of hair after washing. The purpose is to provide.

[0004]

DISCLOSURE OF THE INVENTION The inventors of the present invention have found that a diamide compound having a specific structure, which can be produced inexpensively and easily, has an excellent effect of preventing split ends and hair breakage, and an anionic surfactant and It has been found that the shampoo composition in which an amphoteric surfactant is used in combination is excellent in the feel of the hair after washing and does not impair the cleanability and the feeling of use.

That is, the present invention provides the following components (A), (B) and
(C) (A) Anionic surfactant (B) Amphoteric surfactant (C) Diamide compound represented by the general formula (1)

[0006]

[Chemical 2]

[In the formula, R ¹ represents a linear or branched hydrocarbon group having 1 to 12 carbon atoms which may be substituted by a hydroxyl group and / or an alkoxy group, and R ² represents 1 to 5 carbon atoms. A linear or branched divalent hydrocarbon group is shown, and R ³ has 1 to 22 carbon atoms.
Is a linear or branched divalent hydrocarbon group. ] The shampoo composition containing these is provided.

[0008]

BEST MODE FOR CARRYING OUT THE INVENTION As the anionic surfactant of component (A) used in the present invention, alkyl (or alkenyl) sulfate, polyoxyalkylene alkyl (or alkenyl)
Ether sulfate, alkane sulfonate, olefin sulfonate, alkylbenzene sulfonate, alkyl
(Or alkenyl) sulfosuccinate, dialkyl (or dialkenyl) sulfosuccinate, polyoxyalkylene alkyl (or alkenyl) sulfosuccinate, alkyl (or alkenyl) ether carboxylate, polyoxyalkylene alkyl (or alkenyl) ether carboxylic acid Salt, polyoxyalkylene alkyl (or alkenyl)
Examples thereof include ether phosphates, fatty acid salts, N-acyl glutamate, N-acyl taurates and N-acyl methyl taurines. Of these, polyoxyethylene alkyl ether sulfates, polyoxyethylene alkenyl ether sulfates, and alkyl sulfates are preferable, and particularly the general formula
Those represented by (a) or (b) are preferable.

R'O (CH ₂ CH ₂ O) _m SO ₃ M (b) R ″ OSO ₃ M (b)

[In the formula, R'represents an alkyl group or an alkenyl group having 10 to 18 carbon atoms, R "represents an alkyl group having 10 to 18 carbon atoms, M is an alkali metal, an alkaline earth metal, ammonium, Represents an alkanolamine or a basic amino acid, and m represents a weight average number of 1 to 5.]

The anionic surfactant as the component (A) may be used in one kind or more, and the content thereof is 5 to 5 in the whole composition.
40% by weight, preferably 10-35% by weight, especially 15-30%
Weight percent is preferred.

The amphoteric surfactant of the component (B) used in the present invention includes carbobetaine-based, amidobetaine-based, sulfobetaine-based, hydroxysulfone having an alkyl group, an alkenyl group or an acyl group having 8 to 24 carbon atoms. Examples include betaine-based, amidosulfobetaine-based, and phosphobetaine-based surfactants. As the counter ion of the anionic group of these amphoteric surfactants, alkali metal ions such as sodium ion and potassium ion, ammonium ion,
Examples thereof include alkanolamines having 1 to 3 alkanol groups having 2 to 3 carbon atoms (for example, monoethanolamine, diethanolamine, triethanolamine, triisopropanolamine), and the like, and the counterion of the cationic residue is chloride. Ion, bromide ion, halide ion such as iodide ion, methosulfate ion, saccharinate ion and the like can be mentioned. Other amphoteric surfactants include imidazolinium derivatives represented by the general formula (2) and amidoamine derivatives represented by the general formula (3) or (4).

[0013]

[Chemical 3]

[Wherein R ⁴ represents a linear or branched alkyl or alkenyl group having 7 to 24 carbon atoms, R ⁵ represents a hydrogen atom or a group —CH ₂ Z, and each Z independently represents based -CO ₂
M ¹ or —CH ₂ CO ₂ M ¹ is shown, and M ¹ is a hydrogen atom, an alkali metal, an alkaline earth metal, an alkanolamine or ammonium. ]

[0015]

[Chemical 4]

[0016]

[Chemical 5]

[Wherein R⁶And R⁸Is a straight chain having 7 to 24 carbon atoms
Or a branched chain alkyl group or alkenyl group, R⁷
And R⁹Is a group -CH₂COOM¹Or -CH₂CH₂COO
M¹(M¹Is the same as above), and R^TenIs a hydrogen atom or group
-CH₂COOM¹Or -CH ₂CH₂COOM¹(M¹
Indicates the same as above). ]

Examples of the imidazolinium derivative (2) include 2-
Examples thereof include cocoyl-N-carboxymethyl-N-hydroxyethylimidazolinium betaine, 2-cocoyl-N-carboxyethyl-N-hydroxyethylimidazolinium betaine, and salts thereof.

Examples of the amidoamine derivative (3) include N-lauroyl-N'-carboxymethyl-N '-(2-hydroxyethyl).
Ethylenediamine, N-lauroyl-N'-carboxyethyl
-N '-(2-hydroxyethyl) ethylenediamine, N-myristoyl-N'-carboxymethyl-N'-(2-hydroxyethyl)
Ethylenediamine, N-myristoyl-N'-carboxyethyl-N '-(2-hydroxyethyl) ethylenediamine, N-palmitoyl-N'-carboxymethyl-N'-(2-hydroxyethyl) ethylenediamine, N-palmitoyl-N ' Examples include -carboxyethyl-N '-(2-hydroxyethyl) ethylenediamine and salts thereof.

Examples of the amidoamine derivative (4) include N-lauroyl-N- (2-hydroxyethyl) -N'-carboxymethylethylenediamine and N-lauroyl-N- (2-hydroxyethyl) -N ', N'-bis. (Carboxymethyl) ethylenediamine,
N-lauroyl-N- (2-hydroxyethyl) -N ', N'-bis (carboxyethyl) ethylenediamine, N-myristoyl-N-
(2-hydroxyethyl) -N'-carboxymethylethylenediamine, N-myristoyl-N- (2-hydroxyethyl) -N ',
N'-bis (carboxymethyl) ethylenediamine, N-myristoyl-N- (2-hydroxyethyl) -N ', N'-bis (carboxyethyl) ethylenediamine, N-palmitoyl-N- (2-
Hydroxyethyl) -N'-carboxymethylethylenediamine, N-palmitoyl-N- (2-hydroxyethyl) -N ', N'-
Examples thereof include bis (carboxymethyl) ethylenediamine, N-palmitoyl-N- (2-hydroxyethyl) -N ′, N′-bis (carboxyethyl) ethylenediamine and salts thereof.

The amphoteric surfactant as the component (B) may be used in one kind or more, and the content thereof is 0.1 to 30 in the whole composition.
% By weight, more preferably 0.5 to 25% by weight, especially 1 to 20
Weight percent is preferred.

In the general formula (1) showing the diamine compound of the component (C) used in the present invention, R ¹ is substituted with 1 to 3 selected from a hydroxyl group and an alkoxy group having 1 to 6 carbon atoms. It is preferably a linear or branched alkyl group having 1 to 12 carbon atoms. Among them, an unsubstituted alkyl group having 1 to 12 carbon atoms, or 1 to 2 hydroxyl groups, 1 alkoxy group having 1 to 6 carbon atoms, or 1 hydroxyl group and 1 alkoxy group having 1 to 6 carbon atoms A substituted alkyl group having 2 to 12 carbon atoms is more preferable. Specifically, a methyl group, an ethyl group, a propyl group, a butyl group, a hexyl group, a dodecyl group,
2-methylpropyl group, 2-ethylhexyl group, 2-hydroxyethyl group, 9-hydroxynonyl group, 2,3-dihydroxypropyl group, 2-methoxyethyl group, 2-hydroxy-3-methoxypropyl group, 9-methoxy Examples include nonyl groups,
Of these, a 2-hydroxyethyl group, a methyl group, a dodecyl group, and a 2-methoxyethyl group are preferable.

In the general formula (1), R ² is preferably a linear or branched alkylene group having 2 to 5 carbon atoms, particularly 2 to 3 carbon atoms. Specifically, ethylene group, trimethylene group, tetramethylene group, pentamethylene group, 1-methylethylene group, 2-methylethylene group, 1-methyltrimethylene group, 2-methyltrimethylene group, 1,1-dimethyl Examples thereof include an ethylene group and a 2-ethyltrimethylene group, and among them, an ethylene group and a trimethylene group are preferable.

In the general formula (1), R ³ is preferably a linear or branched divalent hydrocarbon group having 2 to 22 carbon atoms,
Particularly, a linear or branched alkylene group having 11 to 22 carbon atoms and an alkenylene group having 1 to 4 double bonds are preferable. Specifically, ethylene group, trimethylene group, tetramethylene group, hexamethylene group, heptamethylene group, octamethylene group, decamethylene group, undecamethylene group, dodecamethylene group, tridecamethylene group, tetradecamethylene group, hexa Decamethylene group, octadecamethylene group, 1-methylethylene group, 2-ethyltrimethylene group, 1-methylheptamethylene group, 2-methylheptamethylene group, 1-butylhexamethylene group, 2-methyl-5-ethyl Heptamethylene group, 2,3,6-trimethylheptamethylene group, 6-ethyldecamethylene group, 7-methyltetradecamethylene group, 7-ethylhexadecamethylene group, 7,12-dimethyloctadecamethylene group, 8, 11-dimethyloctadecamethylene group, 7,10-dimethyl-7-ethylhexadecamethylene group, 1-octadecylethylene group, ethenylene group, 1- Octadecenyl ethylene group, 7,11-octadecadienylene group, 7-ethenyl-9-hexadecamethylene group, 7,12-dimethyl-7,11-octadecadienylene group, 8,11-dimethyl- 7,11
-Octadecadienylene group and the like. this house,
7,12-Dimethyloctadecamethylene group, 7,12-Dimethyl-
A 7,11-octadecadienylene group, an octadecamethylene group, an undecamethylene group, and a tridecamethylene group are particularly preferable.

Particularly preferred diamide compound as component (C)
The product is R in the general formula (1).¹, R²And R ³As each
It is a compound in which the preferable groups listed above are combined. Special
Specific examples of the preferred diamide compound (1) are as follows.
Compounds of

[0026]

[Chemical 6]

[0027]

[Chemical 7]

As the diamide compound (1) of the component (C), one or more kinds can be used, and the content thereof is 0.01 to the total composition.
20% by weight is preferable, 0.1 to 20% by weight, particularly 0.5 to
15% by weight is preferred. In addition, these diamide compounds
(1) can be synthesized by the method described in WO 00/61097.

The shampoo composition of the present invention may contain proteins or ceramides which are usually used as a hair protecting component for the purpose of further improving the effect of suppressing split ends and hair breakage.

The proteins include any of proteins, protein hydrolysates and their derivatives, and can be obtained by extracting or inducing them from animals or plants. Animal-derived proteins include keratin, elastin,
Examples thereof include collagen, lactoferrin, casein, α (β) -lactalbumin, globulins, ovalbumin and hydrolysates thereof, and among them, keratin, elastin, collagen, casein and hydrolysates thereof are preferable. Examples of plant-derived proteins include those extracted from wheat, malt, oats, barley, corn, rice, soybeans, fava beans, silk, lupine seeds, potatoes, apricot kernels, and their hydrolysates. Of these, wheat protein, soy protein, silk protein and hydrolysates thereof are preferable. One or more kinds of proteins can be used, and the content thereof is 0.01 to 5% by weight, more preferably 0.05 to 4% by weight, based on the total composition.
Particularly, 0.1 to 3% by weight is preferable.

Examples of the ceramides include N-acylated sphingosines, N-acylated phytosphingosines, and N-acylated dihydrosphingosines obtained synthetically or by extraction from natural products. The substituent that is acyl-substituted to sphingosine, dihydrosphingosine, or phytosphingosine is a linear or branched alkyl group or alkenyl group having 8 to 22 carbon atoms, and 1 to 5 of the hydrogen atoms of the group are replaced by a hydroxyl group. It may be substituted. For example, ceramide 1, ceramide 2, ceramide 3,
In addition to ceramide 1A, ceramide 6II, hydroxycaproyl phytosphingosine, sphingolipid EX (JP-A-11-209248), sphingolipid E (Japanese Patent Publication)
No. 01-042934), and synthetic pseudo-ceramides can also be used. One or more ceramides may be used, and the content thereof is preferably 0.01 to 5% by weight, more preferably 0.05 to 4% by weight, and particularly preferably 0.1 to 3% by weight based on the total composition.

The shampoo composition of the present invention may contain a silicone derivative or a cationic polymer which is usually used as a feel-improving component for the purpose of further improving the feeling of use.

Examples of the silicone derivative include dimethylpolysiloxane, methylphenylpolysiloxane, amino-modified silicone, polyether-modified silicone, epoxy-modified silicone, fluorine-modified silicone, cyclic silicone, alkyl-modified silicone and oxazoline-modified silicone. But dimethyl polysiloxane,
Methylphenylpolysiloxane, amino-modified silicone, polyether-modified silicone, oxazoline-modified silicone and cyclic silicone are preferred. One or more kinds of silicone derivatives can be used, and the content thereof is 0.01 to 20% by weight, more preferably 0.05 to 10% by weight, especially 0.1% by weight based on the total composition.
1-5% by weight is preferred.

Examples of the cationic polymer include polydimethyldiallylammonium chloride, acrylamidopropyltrimethylammonium chloride / acrylate copolymer, acrylamide / dimethyldiallylammonium chloride copolymer, methylvinylimidazolinium chloride / vinylpyrrolidone copolymer, hydroxyethylcellulose / diallyldimethylammonium chloride. Copolymer, vinylpyrrolidone / dimethylaminoethylmethacrylate copolymer diethylsulfate, vinylpyrrolidone / dimethylaminoethylmethitalylate copolymer, vinylpyrrolidone / alkylaminoacrylate / vinylcaprolactam copolymer, vinylpyrrolidone / dimethylaminopropylmethacrylamide copolymer, chloride O- [2-hi Proxy-3- (trimethylammonio)
Propyl] hydroxycellulose, guar hydroxypropyltrimonium chloride and the like. One or more kinds of cationic polymers can be used, and the content thereof is 0.01 to 20% by weight in the total composition as solid content, and further 0.05.
-10% by weight, particularly 0.1-5% by weight is preferred.

In the shampoo composition of the present invention, in addition to the above components, nonionic surfactants such as fatty acid alkanolamides, polyoxyethylene alkyl ethers and polyoxyethylene alkylamine oxides; higher alcohols,
Oily components such as lanolin derivatives and fatty acid esters of polyethylene glycol; hydroxypropylmethyl cellulose, hydroxy cellulose, polyvinyl alcohol,
Water-soluble polymers such as polyethylene glycol; polyhydric alcohols such as sorbitol; humectants; chelating agents such as ethylenediaminetetraacetic acid (EDTA); drugs such as vitamins; amino acids and their derivatives; polyethylene, polystyrene, polymethylmethacrylate, nylon, Polymer fine powder such as silicone and hydrophobized products thereof; animal and plant derived extract; UV absorber; pearling agent; antiseptic; bactericide; pH adjuster; pigment; fragrance etc. depending on the purpose be able to.

[0036]

[Examples] Examples 1 and 2, Comparative Examples 1 and 2, shampoos shown in Table 1 were prepared, and the feel given to hair and the occurrence of split ends and broken hair were evaluated. The results are shown in Table 1.

<Evaluation method> ・ Feeling (finger during rinsing and moist feeling of hair after drying) ・ Five specialized panelists shampoo like ordinary shampoo, remove moisture from hair with a towel, and use a dryer. Dry with warm air. Sensory evaluation was performed according to the following criteria with respect to finger feel during rinsing and moist feeling of hair after drying, and the average value thereof was shown. 5: good, 4: good, 3: neither can be said,
2: Slightly bad, 1: Bad

Occurrence rate of split ends and broken hair 1) A plate-shaped hair tress of 100 pieces having a length of 16 cm is prepared. 2) Apply an appropriate amount of each shampoo (bath ratio 1: 0.2 = hair: agent) to the hair tress, lather it for 30 seconds, rinse the excess agent for 30 seconds, and dry naturally. The above was treated once, and this was repeated 14 times (corresponding to 2 weeks in real life). 3) The treated tress is given a brushing stimulus for about 60 minutes at a rotation speed of 100 rpm by a rotating brush linked to a motor. 4) Visually observe the state of the tip of the tress to confirm the number of split ends and broken hairs that have occurred. 5) As the standard tress (Comparative Example 2),
Based on 100%, the split hair / breakage suppression rate for each shampoo is calculated according to the following formula. Split ends and broken hair occurrence rate (%) = (number of hairs generated in treated hair / number of hairs generated in standard tress) x 100

[0039]

[Table 1]

Example 3 Conditioning Shampoo (pH 5.0) (wt%) Polyoxyethylene (2.5) lauryl ether Sodium sulfate ^{* 1} 35.0 Lauramide amidopropyl betaine ^{* 2} 10.0 Coconut oil fatty acid monoethanolamide 1.0 Polyoxyethylene (23 ) Lauryl ether 0.5 Diamide compound (F) 2.0 Chlorinated O- [2-hydroxy-3- (trimethylammonio) propyl] hydroxyethyl cellulose 0.1 Malic acid (50% by weight) Appropriate amount sodium benzoate 0.2 Diethylene glycol monoethyl ether 1.0 Ethanol 1.0 Fragrance Appropriate amount of purified water Balance 100.0 * 1: Kao Company, Emar 20CM-S (25% by weight) * 2: Kao Company, Anchor 20AB (30% by weight)

Example 4 Anti-dandruff shampoo (pH 6.0) (wt%) polyoxyethylene (2.5) lauryl ether sodium sulfate ^{* 1} 35.0 2-alkyl-N-carboxymethyl-N-hydroxyethyl imidazolinium betaine ^{* 2} 5.0 Lauric acid diethanolamide 1.0 Diamide compound (D) 3.0 Aqueous suspension of zinc pyrithione ^{* 3} 1.0 Sodium benzoate 0.3 Hydroxyethylcellulose 0.15 Disodium edetate 0.1 Amount of citric acid Amount of perfume Amount of purified water Balance 100.0 * 1: Kaosha, Emal 20CM-S (25% by weight) * 2: Kao, Amphitol 20Y (58% by weight) * 3: Yoshitomi Pharmaceutical, Domicide ZPT-50

Example 5 Cleansing Shampoo (pH 5.0) (wt%) Polyoxyethylene lauryl ether sulfate triethanolamine ^{* 1} 55.0 2-alkyl-N-carboxymethyl-N-hydroxyethyl imidazolinium betaine ^{* 2} 1.0 Palm Oil fatty acid monoethanolamide 2.5 Polyoxyethylene (23) lauryl ether 0.5 Diamide compound (A) 1.0 Diamide compound (F) 1.0 Lactic acid (90% by weight) Suitable amount Disodium edetate 0.1 Sodium benzoate 0.2 Perfume Suitable amount Purified water Balance total 100.0 * 1: Kao company, Emar 20T (40% by weight) * 2: Kao company, Amhitor 20Y (58% by weight)

Example 6 Conditioning Shampoo (pH 5.0) (wt%) Polyoxyethylene (2.5) lauryl ether Sodium sulfate ^{* 1} 30.0 Sodium lauryl sulfate 4.0 Amidopropyl betaine laurate ^{* 2} 3.0 Lauric acid diethanolamide 1.0 Diamide compound ( F) 1.5 Diamide compound (N) 0.5 Ceramide 3 ^{* 3} 0.2 Collagen hydrolyzate ^{* 4} 0.5 Cetanol 1.0 Methylpolysiloxane ^{* 5} 0.2 Methylcyclopolysiloxane ^{* 6} 0.1 Sodium benzoate 0.2 Perfume Amount of purified water Balance 100.0 * 1: Kao, Emar 20CM-S (25% by weight) * 2: Kao, Amphitol 20AB (30% by weight) * 3: Gist-brocades / Cosmoferm, Ceramide III * 4: Seiwa Kasei Co., Promois E-118D * 5 : Shin-Etsu Chemical, Silicone KF-96A * 6: Toray Dow Corning, Silicone DC-345

[0044]

The shampoo composition of the present invention has a detergency
It is possible to protect the hair from physical and chemical irritation, suppress the generation of split ends and broken hair, and to impart a good feel to the hair after washing without impairing the feeling of use.

   ─────────────────────────────────────────────────── ─── Continued front page    F-term (reference) 4C083 AC072 AC102 AC182 AC302                       AC312 AC532 AC641 AC642                       AC712 AC782 AC932 AD112                       AD132 AD152 AD282 AD432                       BB05 BB07 CC38 DD23 EE06                       EE23 EE28 EE29                 4H003 AB31 AC08 AC13 AD04 DA02                       EB04 EB06 EB07 EB08 EB17                       EB37 EB42 ED02 FA02 FA33

Claims (2)

[Claims] 1. The following components (A), (B) and (C) (A) anionic surfactant (B) amphoteric surfactant (C) diamide compound represented by the general formula (1): ] [In the formula, R ¹ represents a linear or branched hydrocarbon group having 1 to 12 carbon atoms which may be substituted with a hydroxyl group and / or an alkoxy group, and R ² represents a linear or branched hydrocarbon group having 1 to 5 carbon atoms or A branched chain divalent hydrocarbon group is shown, and R ³ is a straight chain or branched chain divalent hydrocarbon group having 1 to 22 carbon atoms. ] The shampoo composition containing this. 2. As the component (C), R ³ in the general formula (1) is a linear or branched alkylene group having 11 to 22 carbon atoms or 1
The shampoo composition according to claim 1, which contains a diamide compound which is an alkenylene group having 4 to 4 double bonds.