JP2001311092A - Bactericidal compound-containing composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a bactericidal compound-containing composition not only excellent in retention of a bactericidal compound having an sterilizing effect in the hair, the skin, etc., but also readily usable, excellent in mildness and improved in preservation stability, capable of improving foaming and a foam feeling. SOLUTION: This bactericidal compound-containing composition comprises an alkylethoxy sulfate in which the mass ratio of an adduct having 0 number of addition mols of ethylene oxide does not show the maximum value, the amount of ethylene oxide adduct exhibiting the maximum value is 15-35 mass % and the total amounts of the ethylene oxide adduct exhibiting the maximum value and adducts having one plus and one minus addition mols based on the ethylene oxide adduct exhibiting the maximum value is 55-75 mass % and/or its salt and a bactericidal compound and has >=10 mPa.s viscosity at 25 deg.C.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a bactericidal compound-containing composition having an improved germicidal compound retention property, and more particularly, not only to a bactericidal compound having excellent retention properties on hair, skin, etc. It has excellent usability, is mild and has good storage stability, and is suitable for use as a composition for hair and a composition for external use on the skin. In addition, it is possible to obtain good foaming and foam feeling. In particular, the present invention relates to a bactericidal compound-containing composition suitable as a body cleaning composition such as a hair cleaning agent and a skin cleaning agent.

[0002]

2. Description of the Related Art
In a composition containing a compound having a bactericidal effect used for hair or skin, a device for maximizing the effect of the compound having a bactericidal effect has been devised. For example, in a cleaning composition such as shampoo or body soap, as a prescription for enhancing the retention of bactericidal components (bactericidal compounds) on hair and skin when washed away, a high-grade composition having a film-forming property on hair and skin after rinsing. It has been practiced to incorporate a molecular compound or the like into a composition.

[0003] Further, in order to prevent acne, even in a facial cleanser intended to cleanse the skin, the amount of a cleaning base that reduces the persistence of the bactericidal compound on the skin is reduced to a minimum amount. However, such ingenuity has been a factor in reducing the degree of freedom regarding performance other than the bactericidal effect in formulating a prescription.

[0004] Particularly in the case of a hair cleansing agent such as a shampoo, a suitable washing base includes polyoxyethylene alkyl ether sulfate (AES), which is an anionic activator. Because the distribution of the number of moles of polyoxyethylene added is wide, the AES itself or the additive additive is required to be substantially smaller than the required amount in order to exhibit the specific performance originally exhibited in the AES having the specific number of moles added. It had the disadvantage that it had to be used in excess.

[0005] That is, AES generally conventionally used industrially for cleaning agents and the like has a wide distribution of oxyethylene chain lengths in the hydrophilic portion. Therefore, for example, when AES having an addition mole number of ethylene oxide of 3 moles is selected, about 63% by mass of ethylene oxide addition mole number 1 to 6, which is preferable in terms of detergency and foam performance,
On the other hand, since the content of the alkyl sulfate having no ethylene oxide addition mole number of 0 having a high detergency and a low mildness and a low film-forming property with a polymer compound is increased to about 13% by mass, the resulting detergent is obtained. Since the composition has insufficient film-forming property as compared with the amount of AES, or has too strong a detergency, and the components such as bactericidal compounds are easily washed off, the bactericidal effect during the formulation is reduced. The compound has poor retentivity to hair and skin and has insufficient mildness.

On the other hand, hair of mild or bactericidal compounds,
When AES having an ethylene oxide addition mole number of 5 mol is selected in consideration of the retention property on the skin and the usability, the ethylene oxide addition mole number which is favorable in terms of foam performance, mildness and storage stability is 1 ６6 moles of alkyl ethoxy sulphate actually contains only about 45%, most of which are of a structure that contributes little to the purpose of cleaning or to have a viscosity that is easy to use in the composition. However, if the amount of AES was increased to satisfy these requirements, it was not economically preferable.

The present invention has been made in view of the above circumstances, and not only can improve the retention of a bactericidal compound on hair, skin, etc., but also can be used when applied to hair, skin, etc. It is easy to use, mild and has good storage stability, and can be suitably used as a composition for hair or a composition for external use on the skin. An object of the present invention is to provide a bactericidal compound-containing composition suitable as a body cleaning composition such as a hair cleaning agent and a skin cleaning agent.

[0008]

Means for Solving the Problems and Embodiments of the Invention As a result of intensive studies to achieve the above object, the present inventor has found that
Attention has been paid to a specific alkyl ethoxy sulfate and / or a salt thereof having a narrow distribution width of the ethylene oxide addition mole number represented by the following general formula (1), and as a result of further intensive studies, as shown in Examples described later, By using this specific alkyl ethoxy sulfate and / or its salt in combination with a bactericidal compound having a bactericidal effect and adjusting the viscosity of the composition to a predetermined range, the retention of the bactericidal compound on hair, skin, etc. Not only can be improved, but also have excellent usability when applied to hair, skin, etc.
In addition, it has been found that a composition which is mild and has good storage stability can be obtained, and further, good foaming and foaming performance can be obtained.

R ¹ O— (CH ₂ CH ₂ O) _n —SO ₃ M (1) (wherein, R ¹ is a linear or branched alkyl group having 6 to 24 carbon atoms) Or an alkenyl group, and n
Represents the average number of moles of ethylene oxide group added,
6, and M is a hydrogen atom, an alkali metal, an alkaline earth metal, an alkanolamine or ammonium. )

That is, in particular, in recent years, AES has overcome the disadvantage that the distribution of the number of moles of polyoxyethylene added is wide.
The development and application of the AES have been studied, and a method using AES having a narrow distribution as shown in Japanese Patent Application Laid-Open No. 4-72395 has been proposed. . As described above, in order to achieve the above object, the present inventor has come to pay attention to alkyl ethoxy sulfate having a narrow distribution, and as a result of earnestly studying this alkyl ethoxy sulfate, the ethylene oxide addition mole number of 1 to 6 In the case of the alkyl ethoxy sulfate of the present invention, even in the case of the ethylene oxide 5 mol addition product, the 5 mol addition product is contained in almost 80% of the whole,
In the case of the ethylene oxide 3 mole addition product, the 3 mole addition product contains about 90% or more of the whole, and in the case of the ethylene oxide 2 mole addition product, the 2 mole addition product contains nearly 90%,
On the other hand, the content of the alkyl sulfate having 0 moles of ethylene oxide added is as little as 10% or more of the total amount even in the case of 2 moles of ethylene oxide, which is advantageous only in terms of mildness and storage stability. Without finding that it is very suitable as a main base that freely adjusts the performance of the composition, using this specific alkyl ethoxy sulfate in combination with a bactericidal compound, and further adjusting the viscosity of the composition to a predetermined range As a result, they have found that the above object can be achieved, and have accomplished the present invention.

Accordingly, the present invention provides a) the following general formula (1):
Wherein the mass% occupied by those having a different ethylene oxide addition mole number and having 0 ethylene oxide addition mole number does not show the maximum value, and the mass% of the ethylene oxide adduct showing the maximum value is 15 to 35. Containing an alkyl ethoxy sulfate and / or a salt thereof having a total amount of 55 to 75% by mass with an ethylene oxide adduct having an addition mole number before and after this, and b) a bactericidal compound, and having a viscosity at 25 ° C. of 10 mPa. -A bactericidal compound-containing composition characterized by being at least s.

R ¹ O— (CH ₂ CH ₂ O) _n —SO ₃ M (1) (wherein, R ¹ is a linear or branched alkyl group having 6 to 24 carbon atoms) Or an alkenyl group, and n
Represents the average number of moles of ethylene oxide group added,
6, and M is a hydrogen atom, an alkali metal, an alkaline earth metal, an alkanolamine or ammonium. )

Here, the component (b) is a 1-hydroxy-2-pyridone compound, salicylic acid and its salts, zinc pyrithione, trichlorocarbanilide, triclosan, benzalkonium chloride, alkyldiaminoethylglycine hydrochloride, methyl One or two selected from chloroisothiazoline / methylisothiazoline fungicides and sulfur
More than one kind of fungicidal compound is more preferable, and it is particularly preferable that the composition containing a fungicidal compound is a composition for hair or a composition for external use on skin.

Hereinafter, the present invention will be described in more detail. The fungicidal compound-containing composition of the present invention comprises, as described above, a)
It contains an alkylethoxy sulfate and / or a salt thereof represented by the general formula (1) and b) a bactericidal compound, and has a viscosity at 25 ° C. of 10 mPa · s or more.

Here, the alkyl ethoxy sulfate and its salt, which are the component a) of the present invention, have the general formula R ¹ O-
(CH ₂ CH ₂ O) _n —SO ₃ M (1) wherein R ¹ is a linear or branched alkyl group having 6 to 24, preferably 10 to 18 carbon atoms. Or an alkenyl group. If the number of carbon atoms is less than 6, sufficient foam performance cannot be obtained. On the other hand, when the number of carbon atoms exceeds 24, the solubility of the activator itself decreases, so that precipitation tends to occur during storage.

Specific examples of preferred alkyl or alkenyl groups include hexyl, octyl, decyl, dodecyl, myristyl, palmityl, stearyl, oleyl, aralkyl, and behenyl. Although it is possible, the alkyl ethoxy sulfate of the present invention is not limited to these.

In the case of the present invention, these alkyl groups or alkenyl groups may be used alone or as a mixture of two or more kinds. It may be a chain alkyl group or a branched alkyl group, or an alkenyl group corresponding thereto, or may be a synthesized one. For example, commercially available synthetic alcohols such as dovanox, dovanol, diadol and neodol, and natural alcohols such as coconut oil higher alcohols can be very suitably used as raw materials.

In the above general formula (1), n represents the average number of moles of ethylene oxide group added, and is in the range of 1 to 6, more preferably 1.5 to 4, and still more preferably 2 to 3.
Range. When n is less than 1, the content of the alkyl sulfate having the ethylene oxide addition mole number of 0 is too large, the detergency is too strong, and for example, a film composed of a complex formed by the action with a cationic polymer compound is used. Since the formation property is hindered, the retentivity of the bactericidal compound on hair, skin, and the like is reduced, and the mildness and storage stability cannot be satisfied. On the contrary, when n is larger than 6, not only a problem such as inability to satisfy the foaming performance occurs, but also the effect of increasing the viscosity of the composition is small, and the viscosity of the composition of the present invention is small. In order to adjust to within the above-mentioned predetermined range, there is a restriction on the formulation design such as the necessity of adding or increasing the component having a thickening effect to the composition separately from the component a).

Further, M in the alkyl ethoxy sulfate or a salt thereof represented by the general formula (1) is a counter ion, and is a hydrogen atom, an alkali metal such as sodium or potassium, an alkaline earth metal, monoethanolamine, diethanolamine. Cation groups derived from alkanolamines or ammonium such as triethanolamine, isopropanolamine, etc.

The alkyl ethoxy sulfate which is the component a) of the present invention includes those having different moles of ethylene oxide added, that is, alkyl ethoxy sulfates having a distribution of moles of ethylene oxide added,
It has a narrow distribution of the number of moles of ethylene oxide added, which has the characteristics described below in detail.

First, in the above distribution, the mass% occupied by the case where the ethylene oxide addition mole number is 0 does not show the maximum value. That is, it is characterized in that the alkyl sulfate having disadvantages in mildness and storage stability is not most contained.

The ratio of the ethylene oxide adduct having the maximum value in the above distribution to the total alkyl ethoxy sulfate is 15 to 35% by mass, preferably 20 to 3% by mass.
0% by mass, and the ethylene oxide adduct,
If the addition mole number before and after that, that is, for example, the ethylene oxide addition mole number of the ethylene oxide adduct is P,
It is characterized by a narrow distribution of alkyl ethoxy sulfate and a salt thereof having a total amount of an ethylene oxide adduct having an addition mole number of P ± 1 of 55 to 75% by mass, preferably 60 to 70% by mass.

In other words, the alkyl ethoxy sulfate of the present invention has a structure suitable as a main base of a composition containing a bactericidal compound, particularly a main base of a composition for hair and a composition for external use on the skin. It is an aggregated, so-called purified alkyl ethoxy sulfate.

The alkyl ethoxy sulfate or its salt, which is the component a) of the present invention, is not particularly limited by other elements as long as it satisfies the above-mentioned characteristics. For example, the production method is also not particularly limited. And JP-A 1-1
It may be manufactured using a specific Lewis acid solid catalyst as disclosed in Japanese Patent No. 64437 or the like, may be manufactured in the presence of an acidic liquid catalyst such as sulfuric acid, or may be generally used industrially. In the presence of an alkali catalyst such as sodium hydroxide or the like, a compound having a broad distribution may be first synthesized and purified by distillation or the like.

The amount of the component (a) in the composition of the present invention is not particularly limited, but when one type is used alone or two or more types are used in combination as appropriate, The content is preferably 5 to 25% (mass%, the same applies hereinafter), particularly 6 to 20%, based on the whole product. If the amount is less than 5%, the foaming of the main base of the composition tends to be insufficient, and the foam feel becomes watery, so that sufficient satisfaction may not be obtained during use. In addition, the compounding amount is 25
When the amount is more than%, the retention of the bactericidal compound may be significantly impaired, the mildness of the composition may be reduced, and the storage stability of the composition at low temperatures may not be maintained.

The component (b), which is the second essential component of the present invention, is usually used in cosmetic compositions and the like, and any compound that imparts a bactericidal effect to hair, skin and the like can be used. Can be used.

Examples of such compounds include 1-hydroxy-2-pyridone compounds, salicylic acid and salts thereof, zinc pyrithione, trichlorocarbanilide, triclosan, benzalkonium chloride, alkyldiaminoethylglycine hydrochloride, methylchloroform An isothiazoline / methyl isothiazoline fungicide and sulfur can be mentioned, and these can be used alone or in an appropriate combination of two or more. The methylchloroisothiazoline / methylisothiazoline fungicides are 5-chloro-2-methyl-4-isothiazolin-3-one and 2-
It is a mixture with methyl-4-isothiazolin-3-one. In the case of the present invention, among these, a 1-hydroxy-2-pyridone-based compound represented by the following general formula (2) is particularly preferably used.

[0028]

Embedded image

(Wherein R ² is an alkyl group having 1 to 17 carbon atoms, an alkenyl group having ² to 17 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms) A cycloalkyl-alkyl group having from 7 to 9 carbon atoms, a cycloalkyl group having from 5 to 8 carbon atoms, and an alkyl group having from 1 to 4 carbon atoms (provided that A cycloalkyl group is
A part of the hydrogen atoms may be substituted by an alkyl group having 1 to 4 carbon atoms), an aryl group having 6 to 14 carbon atoms, and the aryl group having 6 to 14 carbon atoms; Wherein the alkyl group is an aralkyl group having 1 to 4 carbon atoms, the aryl group is an arylalkenyl group having 6 to 14 carbon atoms, and the alkenyl group is an arylalkenyl group having 2 to 4 carbon atoms. An aryloxyalkyl or arylmercaptoalkyl group having from 6 to 14 carbon atoms and an alkyl group each having from 1 to 4 carbon atoms, a benzhydryl group, an alkyl group having from 1 to 4 carbon atoms A phenylsulfonylalkyl group, a furyl group or an alkenyl group represents a furylalkenyl group having 2 to 4 carbon atoms. However, in the above-mentioned aryl group, a part of the hydrogen atoms is substituted by an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a nitro group, a cyano group or a halogen atom. May be. R ³ represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkenyl group having 2 to 4 carbon atoms, an alkynyl group having 2 to 4 carbon atoms, a halogen atom, a phenyl group or benzyl. Represents a group. X represents an organic base, an alkali metal ion, an ammonium ion or a divalent to tetravalent cation. )

Specific examples of the compound represented by the general formula (2) include the following compounds and salts thereof.

1-hydroxy-2-pyridone, 1-hydroxy-4-methyl-2-pyridone, 1-hydroxy-
6-methyl-2-pyridone, 1-hydroxy-4,6-
Dimethyl-2-pyridone, 1-hydroxy-4-methyl-6-heptyl-2-pyridone, 1-hydroxy-4-
Methyl-6- (1-ethylpentyl) -2-pyridone,
1-hydroxy-4-methyl-6- (2,4,4-trimethylpentyl) -2-pyridone, 1-hydroxy-4
-Methyl-6-undecyl-2-pyridone, 1-hydroxy-4-methyl-6-propenyl-2-pyridone, 1
-Hydroxy-4-methyl-6-octenyl-2-pyridone, 1-hydroxy-4-methyl-6- (2,2-dibutyl-vinyl) -2-pyridone, 1-hydroxy-4
-Methyl-6- (cyclohexenylidene-methyl) -2
-Pyridone, 1-hydroxy-4-methyl-6-cyclohexyl-2-pyridone, 1-hydroxy-4-methyl-6- (methyl-cyclohexyl) -2-pyridone,
-Hydroxy-4-methyl-6- (2-bicyclo [2,
2,1] heptyl) -2-pyridone, 1-hydroxy-
4-methyl-6- [2- (dimethylcyclohexyl)-
Propyl] -2-pyridone, 1-hydroxy-4-methyl-6- (4-methyl-phenyl) -2-pyridone,
-Hydroxy-4-methyl-6- (3-methyl-phenyl) -2-pyridone, 1-hydroxy-4-methyl-6
-(4-tert-butyl-phenyl) -2-pyridone, 1-
Hydroxy-4-methyl-6- (3-methyl-4-chloro-phenyl) -2-pyridone, 1-hydroxy-4-
Methyl-6- (3,5-dichloro-phenyl) -2-pyridone, 1-hydroxy-4-methyl-6- (3-bromo-4-chloro-phenyl) -2-pyridone, 1-hydroxy-4- Methyl-6- (4-methoxystyryl)-
2-pyridone, 1-hydroxy-4-methyl-6- [1
-(4-nitrophenoxy) -butyl] -2-pyridone, 1-hydroxy-4-methyl-6- (4-cyanophenoxymethyl) -2-pyridone, 1-hydroxy-4
-Methyl-6- (phenylsulfonylmethyl) -2-pyridone, 1-hydroxy-4-methyl-6- [1- (4
-Chlorophenylsulfonyl) -butyl] -2-pyridone, 1-hydroxy-4-methyl-6-benzyl-2-
Pyridone, 1-hydroxy-4-methyl-6- (2,4
-Dimethylbenzyl) -2-pyridone, 1-hydroxy-4-methyl-6- (tert-butyl-benzyl) -2-pyridone, 1-hydroxy-4-methyl-6- (2-chloro-benzyl) -2 -Pyridone, 1-hydroxy-4-
Methyl-6- (4-chlorobenzyl) -2-pyridone,
1-hydroxy-4-methyl-6- (2,5-dichloro-benzyl) -2-pyridone, 1-hydroxy-4-methyl-6- (4-bromo-benzyl) -2-pyridone,
1-hydroxy-4-methyl-6- (phenoxymethyl) -2-pyridone, 1-hydroxy-4-methyl-6
-(3-methylphenoxy-methyl) -2-pyridone,
1-hydroxy-4-methyl-6- (4-secondary-butylphenoxy-methyl) -2-pyridone, 1-hydroxy-
4-methyl-6- (2,4,5-trichlorophenoxy-methyl) -2-pyridone, 1-hydroxy-4-methyl-6- (4-bromophenoxy-methyl) -2-pyridone, 1-hydroxy- 4-methyl-6- (4-chlorophenylmercapto-methyl) -2-pyridone, 1-hydroxy-4-methyl-6- (4-methylphenylmercapto-methyl) -2-pyridone, 1-hydroxy-4
-Methyl-6- (2-naphthyl) -2-pyridone, 1-
Hydroxy-4-methyl-6-benzhydryl-2-pyridone, 1-hydroxy-4-methyl-6-furyl-2
-Pyridone, 1-hydroxy-4-methyl-6- (furylvinyl) -2-pyridone, 1-hydroxy-4-methyl-6-styryl-2-pyridone, 1-hydroxy-4
-Methyl-6- (phenylbutadienyl) -2-pyridone, 1-hydroxy-4-phenyl-6-methyl-2-
Pyridone, 1-hydroxy-4,6-diphenyl-2-
Pyridone and the like can be mentioned.

The above compound is used as a salt, and can be suitably used, for example, as a salt with an organic amine.
Specifically, for example, ethanolamine, diethanolamine, N-ethylethanolamine, N-methyl-diethanolamine, triethanolamine, diethylamino-ethanol, 2-amino-2-methyl-n-propanol, dimethylaminopropanol, 2-amino -2
-Methyl-propanediol, tri-isopropanolamine, ethylenediamine, hexamethylenediamine,
Morpholine, piperidine, cyclohexylamine, tributylamine, dodecylamine, N, N-dimethyl-dodecylamine, stearylamine, oleylamine, benzylamine, dibenzylamine, N-ethylbenzylamine, dimethylstearylamine, N-methyl-morpholine, N-methylpiperazine, 4-methylcyclohexylamine, N-hydroxyethyl-morpholine and the like can be mentioned.

The 1-hydroxy-2-pyridone compound used in the present invention may be a salt with an inorganic ion, for example, an alkali metal salt such as a sodium salt and a potassium salt, an ammonium salt and a magnesium salt. Alkaline earth metal salts such as calcium salts can be used. Further, salts with divalent to tetravalent cations such as zinc salts, aluminum salts and zirconium salts can also be used.

The amount of the component (b) in the composition of the present invention is not particularly limited, but when one of these compounds is used alone or in an appropriate combination of two or more, the composition is usually used. 0.01 to 3% of the whole, especially 0.0
It is preferable to set it to 5 to 2%. If the compounding amount of the bactericidal compound is too small, a sufficient bactericidal effect may not be obtained.On the other hand, if the amount is too large, for example, the dissolution of the bactericidal compound is insufficient, and the composition is preserved at a low temperature. May not be good, or the compounded amount may not be used effectively due to adsorption to a container or the like during storage.

Further, the composition of the present invention has a viscosity of 10 m at 25 ° C.
It is necessary to have a viscosity of Pa · s or more, preferably 10 to 10000 mPa · s, more preferably 15 mPa · s.
８8000 mPa · s. If the viscosity is too low, if it is picked up during use, it will spill, or if it is used as a shampoo, for example, it will run down the scalp and enter the eyes, causing inconvenience,
It may not be desirable for safety.

In order to keep the viscosity of the composition of the present invention within the above range, the viscosity of the composition can be obtained by blending the above-mentioned a) alkyl ethoxy sulfate.
In order to obtain the desired viscosity, a known thickening agent can be used in combination as necessary, and as such a thickening agent,
The type thereof is not particularly limited, and nonionics such as fatty acid alkanolamides, alkyl ethers and esters, sugar-based activators, polymer compounds, betaines and the like can be suitably used.

When the composition of the present invention is used as a hair composition such as a hair cleansing agent or a skin external composition such as a skin cleansing agent, the anionic surfactant usually contained in these cleansing agents is used. Agents, amphoteric surfactants and one or more surfactants selected from semipolar surfactants can be contained in a range that does not impair the effects of the present invention,
This makes it possible to obtain a composition that is more excellent in foaming and foam feeling, detergency, rinse and finish feeling, and mild and has good storage stability.

Specifically, as anionic surfactants, for example, conventional polyoxyethylene alkyl ether sulfates and alkyl sulfates having a wide distribution of ethylene oxide addition moles can be used. ,
The amount of the component a), which has a narrow distribution of ethylene oxide addition moles, which is a feature of the composition of the present invention, must be used in such an amount that the feature of the component a) is not erased, and must be determined in consideration of the balance with other components. is there. In addition to these, α-olefin sulfonate, acylmethyltaurine salt, amide ether sulfate, ether carboxylate, alkane sulfonate, amino acid-based anion activator, and the like,
These can be used alone or in an appropriate combination of two or more, but are not particularly limited thereto. When these anionic surfactants are used in combination, their total amount is 0 to the total composition.
It is preferred to be about 40%.

The type of the amphoteric surfactant is not particularly limited. For example, one or more amphoteric surfactants such as betaine type, imidazoline type and aminocarboxylic acid type may be used. Can be. Specific examples include alkyl betaine, alkylamidopropyl betaine, sulfobetaine, imidazolinium betaine, aminocarboxylic acid, aminopropionic acid, and salts thereof. Usually, the content of the amphoteric surfactant is preferably 0 to 15%, more preferably 0 to 6%, of the whole composition.

Further, the kind of the semipolar surfactant is not particularly limited, but for example, an amine oxide type nonionic surfactant can be mentioned as a typical example. Specific examples include lauryl dimethylamine oxide and polyoxyethylene lauryl dimethylamine oxide. These amine oxides can be used alone or in combination of two or more. The amount is from 0 to the total composition.
15%, preferably 0 to 6% is suitable.

When the composition of the present invention is used as a hair composition or a composition for external use on the skin, a film-forming polymer compound is used in combination with the compound, particularly for the purpose of increasing the retention of a bactericidal compound on hair or skin. be able to. Examples of such a polymer compound include cationic polymer compounds such as cationized cellulose and cationized guar gum, amphoteric polymers such as betaine-containing dialkylaminoalkyl (meth) acrylate and dialkylaminoalkyl (meth) acrylamide, and polybetaine-based polymers. And the like. An amphoteric polymer compound such as, for example, an acrylic anionic polymer compound, and a nonionic polymer compound such as hydroxyethyl cellulose can be used. These may be used alone or in combination of two or more. Can be.

The composition of the present invention may be optionally added, if necessary, in addition to the above components, for example, a hair composition or a skin external composition, as long as the effects of the present invention are not hindered. It can also contain cationic surfactants, which are common components of products, hydrophobic nonionic surfactants, etc., as well as solid or liquid oils, higher alcohols, ester oils, polyhydric alcohols, preservatives, hydrotropes , Inorganic salts, thickeners, fragrances, extracts of animals and plants, anti-dandruff agents, medicinal agents, emulsifiers, pearling agents, ultraviolet absorbers, ultraviolet scattering agents, tonic agents, pH adjusters, pigments, antioxidants Agents, lower alcohols, vitamins, volatile oils,
A hydrophobic solvent, a diluting solvent and the like can be contained, but these are not particularly limited and may be blended according to the purpose.

[0043]

The composition containing a bactericidal compound of the present invention not only has excellent retention properties of the bactericidal compound on hair and skin, but also has excellent usability, is mild and has good storage stability. Therefore, it can be used for various purposes such as hair, general cosmetics used for external use on the skin, tableware such as kitchen cleaners, cleaning agents for furniture, disinfectants, etc. It is useful as a skin external composition. Further, the composition of the present invention can further improve foaming and foam feel, and therefore, among the compositions for hair or the composition for external use on the skin, in particular, the hair cleansing composition and the skin cleansing composition. The effect is remarkably exhibited in a body cleansing composition such as a skin care composition.

[0044]

EXAMPLES Hereinafter, the present invention will be described more specifically by showing Examples and Comparative Examples of the present invention, but the present invention is not limited to the following Examples. The percentages shown below are all percentages by mass.

[Examples 1 to 6, Comparative Examples 1 to 3] Using the a) component (sodium polyoxyethylene alkyl ether sulfate) shown in Table 1, according to the composition shown in Table 2, washes for hair according to a conventional method. Preparations for preparations and skin cleansers, compounds with foaming performance and bactericidal effect of each composition (bactericidal compounds)
Residue on hair or skin, mildness, storage stability,
The viscosity of the composition was evaluated according to the following evaluation method. The results are also shown in Table 2.

The method for preparing the alkyl ethoxy sulfate shown in Table 1 will be described below. <Narrow Distribution Alkylethoxy Sulfate: Sample A-1> Narrow distribution lauryl ethoxy sulfate used in Examples of the present invention was prepared by the following method.

A 4-liter autoclave was charged with 400 g of lauryl alcohol and 0.4 g of a solid metal oxide Lewis acid sintered catalyst composed of Al / Mg / Mn (aluminum / magnesium / manganese). This was replaced and the temperature was raised while stirring. Next, while maintaining the temperature at 180 ° C. and the pressure at 0.3 mPa, 54 g of ethylene oxide was introduced to obtain a reaction product.
Next, the thus obtained alcohol ethoxylate 2
74 g was placed in a 500 ml flask equipped with a stirrer, and after purging with nitrogen, 81 g of liquid sulfuric anhydride (sulfan) was slowly added dropwise while maintaining the reaction temperature at 40 ° C. After completion of the dropwise addition, stirring was continued for 1 hour to obtain the desired alkyl ethoxy sulfate (lauryl ethoxy sulfate).
The properties and distribution of the oxyethylene chain length of the obtained alkyl ethoxy sulfate were as shown in Table 1. The preparation of sample A-2 was performed in the same manner.

<Alkylethoxy Sulfate with Wide Distribution: Sample AES-1> Also, the usual preparation of lauryl ethoxy sulfate having a wide distribution used in Comparative Examples is as follows.
The following method was used.

In a 4 liter autoclave, 400 g of lauryl alcohol and 0.8 g of potassium hydroxide catalyst
Was charged, the inside of the autoclave was replaced with nitrogen, and the temperature was raised while stirring. Next, at a temperature of 180 ° C. and a pressure of 0.3 mP
While maintaining at a, 54 g of ethylene oxide is introduced,
A reaction was obtained. Next, 274 g of the alcohol ethoxylate thus obtained was placed in a 500-ml flask equipped with a stirrer, and after purging with nitrogen, 81 g of liquid sulfuric anhydride (sulfan) was slowly added dropwise while maintaining the reaction temperature at 40 ° C. After completion of the dropwise addition, stirring was continued for 1 hour to obtain the desired alkyl ethoxy sulfate (lauryl ethoxy sulfate). The properties and distribution of the oxyethylene chain length of the obtained alkyl ethoxy sulfate were as shown in Table 1. The preparation of sample AES-2 was performed in the same manner.

(1) Method of Evaluating Foam Performance Foaming, the feel of foam, and the like were comprehensively evaluated by sensory evaluation by a trained expert, and evaluated according to the following criteria. Criteria基準: good foam performance. ×: Poor foam performance.

(2) Method of evaluating the retention of a compound having a bactericidal effect on hair or skin (bactericidal compound) A bactericidal component adsorbed on hair or skin after using each of the formulated compositions for hair or skin. Is extracted with a solvent that dissolves each bactericidal component well, and liquid chromatography is used to determine the amount of each bactericidal component remaining in the hair or skin by quantifying according to the quantification method for each bactericidal component. In comparison, those having a large residual amount were evaluated as having good retention (性), and those having the same or small residual amount were evaluated as having poor retention (×).

The standard composition used here is 10% of polyoxyethylene (3 mol) lauryl ether sulfate sodium salt, which is AES-1 in Table 1 having a wide distribution of the number of moles of ethylene oxide added. Cuton olamine (Clariant; Octopirox)
0.1% and the balance of purified water are 100% in total.

(3) Mildness evaluation method Ten sensational panelists used the composition to compare and evaluate the irritability when the composition was used with the above-mentioned standard composition, and evaluated the evaluation according to the following evaluation criteria. Judgment criterion 〇: Irritation was small compared to the standard composition. Δ: Irritation is equivalent to that of the standard composition. X: The irritability is large as compared with the standard composition.

(4) Method of evaluating storage stability As a result of storage at 40 ° C. for one month under high-temperature conditions and -5 ° C. for one month under low-temperature conditions, the results were compared with those immediately after preparation by visual observation. The storage stability was evaluated as "O" when little change was observed, and the storage stability was evaluated as "X" when remarkable discoloration, precipitation and separation were observed.

(5) Method of Evaluating Viscosity of Composition The viscosity of the composition was measured using a Brookfield BL viscometer.
C. and the viscosity was evaluated according to the following criteria. Judgment standard : Viscosity is moderate (10 mPa · s or more). ×: Low viscosity (less than 10 mPa · s).

[0056]

[Table 1]

[0057]

[Table 2]

As is clear from the results shown in Table 2, the compositions of the present invention all have excellent foaming performance, retention on hair or skin, mildness, storage stability, and viscosity during use. Is good.

The compounds having a bactericidal effect indicated by B-1 to B-6 in Table 2 are as follows.

[0060]

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[0061]

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B-3 Salicylic acid B-4 Triclosan B-5 Benzalkonium chloride B-6 Isothiazoline liquid ("Caisson CG", manufactured by Rohm & Haas) These compounds are listed in Table 2 and the following Examples. It is common.

Example 7 Composition A-1 15.0 Amidopropyl betaine laurate 2.0 Alkyl dimethylamine oxide 2.0 Palm oil fatty acid diethanolamide 3.0 POE Methyl glucoside dioleate 0.8 Laurylpyrrolidone 3. 0 B-1 0.5 Coleus extract 0.2 POE hydrogenated castor oil (HLB9) 1.5 POE (15 mol) alkyl ether 0.5 Sodium sulfate 2.0 Sodium benzoate 1.0 Ethylene glycol distearate 2. 0 Glycerin fatty acid ester 0.2 Glycine 0.5 1,3-butylene glycol 1.0 Dibutylhydroxytoluene 0.005 Oxybenzone 0.5 B-6 0.03 Yellow No. 203 0.001 Orange No. 205 0.002 Fragrance 0 .7 citric acid 0.5 purified water remaining balance 100%

A shampoo composition having the above composition was prepared according to a conventional method. This shampoo composition has a viscosity at 25 ° C. of 10 mPa · s or more, is excellent in foaming, foam feeling, mild, has excellent retention of B-1 and B-6 compounds on hair, and is stable in storage. The properties were good, and the viscosity during use was moderate without being too low.

Example 8 Composition A-2 15.0 Sodium α-Olefin Sulfonate 2.0 Sodium Alkane Sulfonate 5.0 Amidopropyl Betaine Laurate 3.0 Alkyl Carboxyethyl Hydroxyethyl Imidazolinium Betaine 1. 0 POE sodium lauroyl sulfosuccinate 0.5 alkyldimethylamine oxide 0.2 POE (20) lauryl ether 2.0 B-3 0.2 wax 0.5 sodium chloride 0.2 trimethylglycine 0.2 calophyllis extract 5 Isopropylmethylphenol 1.0 Disodium edetate 2.0 Alkyldimethylammonium chloride / acrylic acid / acrylamide terpolymer 0.6 Glycerin 0.1 2-Ethylhexyl methoxycinnamate 0.5 Dye 0.1 Aroma 0.3 Citric acid 3.0 glycolic acid 3.0 Purified water balance Total 100%

According to the above composition, a shampoo composition was prepared according to a conventional method. This shampoo composition has a viscosity at 25 ° C. of 10 mPa · s or more, has excellent foaming performance, mild properties, and a property of retaining the B-3 compound on the scalp, has excellent storage stability, and has a moderate storage stability. It had viscosity.

Example 9 Composition A-1 7.0 Potassium myristate 15.0 Palmitic acid 8.0 Stearic acid 8.0 B-1 0.5 B-3 0.2 Oleyl alcohol 1.0 Glycerin 10 0.0 Polyethylene glycol 5.0 Coconut oil fatty acid monoethanolamide 0.1 Propylene glycol 1.0 Vegetable squalane 0.5 Edetate tetrasodium tetrahydrate 0.2 POE hydrogenated castor oil (HLB9) 1.5 Glycerin fatty acid ester 0.2 Benclay 0.8 Isoprene glycol 1.0 Blue No. 403 0.001 Fragrance 0.2 Purified water Remainder 100%

According to the above composition, a face wash composition was prepared according to a conventional method. This facial cleansing composition has a viscosity at 25 ° C. of 10 mPa · s or more, good foaming performance,
-1 and B-3 compounds are excellent in retention in skin, mild and have good storage stability, have appropriate viscosity,
The usability was good.

Example 10 Composition A-1 5.0 Sodium Acylmethyl Taurine 5.5 Alkyl Betaine 3.0 POE Alkyl Ether 6.5 Alkyl Glyceroglucoside 1.0 Co-Polymerization of Dimethyl Diallylammonium Chloride and Acrylic Acid Merged 0.7 POE methyl glucoside dioleate 1.0 Coconut fatty acid diethanolamide 3.0 Coconut fatty acid monoethanolamide 1.0 B-1 0.5 B-2 0.2 Zinc pyrithione 1.0 Ethylene glycol distearate 2.0 laurylpyrrolidone 5.0 cetyl isooctanoate 1.0 dibutylhydroxytoluene 0.002 glycyrrhetinic acid 0.5 mallow extract 0.5 highly polymerized dimethylpolysiloxane 3.0 cetostearyl alcohol 0.1 tocopherol acetate 0.5 Containing 0.002 Perfume 0.2 Purified water balance Total 100%

According to the above composition, a shampoo composition was prepared according to a conventional method. This shampoo composition has a temperature of 25 ° C.
Is 10 mPa · s or more, foaming performance, excellent in mildness, B-1 and B-2 compounds and zinc pyrithione have good retention properties on the skin, and the viscosity is moderate, The composition had good usability.

Example 11 Composition A-2 5.0 Acylmethyl-β-alanine triethanolamine 10.0 Triethanolamine acylglutamate 5.0 Sodium ether carboxylate 1.0 Alkylaminopropionic acid 0.05 Lauryldimethyl Amine oxide 0.8 Stearyl trimethylammonium chloride 1.0 Palm kernel oil fatty acid diethanolamide 2.0 POE hydrogenated castor oil (HLB9) 3.0 Propylene glycol 0.2 Ethanol 3.0 Dipotassium glycyrrhizinate 0.3 B-11 .5 Liquid paraffin 0.2 Glycerin fatty acid ester 0.8 Sodium benzoate 0.7 Hydrolyzed protein 0.5 Magnesium sulfate 1.5 Cationized cellulose 0.2 Alkyl dimethyl ammonium chloride / acrylic acid copolymer Combined 0.4 Dibutylhydroxytoluene 0.2 Fragrance 0.3 Citric acid 0.1 Edetic acid 1.0 Purified water Remainder 100%

According to the above composition, a shampoo composition was prepared according to a conventional method. This shampoo composition has a viscosity at 25 ° C. of 10 mPa · s or more, foams, has an excellent foam feeling, is mild, has excellent retention of the B-1 compound on hair, and has good storage stability. The viscosity during use was moderate without being too low.

Example 12 Composition A-2 7.0 Potassium myristate 15.0 Lauroylmethyl-β-alanine potassium salt 2.0 Monopotassium lauroylglutamate 2.0 Lauryldimethylamine oxide 1.0 B-1 0.5 B-4 0.2 Oleyl alcohol 1.0 Polyethylene glycol 5.0 Coconut oil fatty acid diethanolamide 3.0 Propylene glycol 6.0 Hydroxypropyl methylcellulose ^{* 1} 0.5 Vegetable squalane 0.5 Sodium edetate Tetrahydrate 0.2 POE hydrogenated castor oil (HLB9) 1.5 Benclay 0.8 Potassium hydroxide trace amount Blue 403 0.001 Fragrance 0.2 Purified water Remainder 100% * 1 Shin-Etsu Chemical Co., Ltd. Metroose 65SH -1500

According to the above composition, a skin cleansing composition was prepared according to a conventional method. This skin cleansing composition is at 25 ° C.
Is 10 mPa · s or more, the foaming performance is good, the retention of B-1 and B-4 compounds on the skin is excellent, mild and has good storage stability, and has an appropriate viscosity. And the usability was good.

Example 13 A-1 4.0 A-2 2.0 Potassium myristate 16.0 Palmitic acid 5.0 Stearic acid 5.0 B-1 0.8 B-5 0.3 Pharmacopoeia Sulfur 5.0 Oleyl alcohol 1.0 Glycerin 15.0 Polyethylene glycol 4000 5.0 Coconut oil fatty acid diethanolamide 1.1 Propylene glycol 1.0 Carophyllis extract 0.5 Edeoic acid tetrasodium tetrahydrate 0.2 Benclay 0 .8 Perfume 0.3 Purified water Remainder 100%

According to the above composition, a face wash composition was prepared according to a conventional method. This facial cleansing composition has a viscosity at 25 ° C. of 10 mPa · s or more, good foaming performance,
-1 and B-5 compounds and sulfur were excellent in staying in the skin, mild, had good storage stability, had appropriate viscosity, and were easy to use.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat ゛ (Reference) A01N 43/80 102 A01N 43/80 102 4H011 A61K 7/06 A61K 7/06 7/075 7/075 7 / 50 7/50 31/085 31/085 31/14 31/14 31/198 31/198 31/425 31/425 31/44 31/44 31/4418 31/4418 31/60 31/60 31/67 31 / 67 33/04 33/04 47/20 47/20 A61P 31/04 A61P 31/04 C11D 3/48 C11D 3/48 F term (reference) 4C076 AA17 BB31 CC18 DD37A DD37R DD38A DD39F DD43Z DD46F DD47 DD51F DD52F DD55F DD57F EE51A 4C083 AA112 AB032 AB112 AB332 AB352 AB362 AB442 AC022 AC072 AC092 AC112 AC122 AC172 AC182 AC212 AC242 AC302 AC312 AC342 AC352 AC392 AC422 AC432 AC471 AC472 AC532 AC552 AC562 AC581 AC582 AC642 AC662 AC691 AC692 AC712 AC781 AC782 AC1 AC8212 AC782 AC1 AD412 AD532 AD662 BB48 CC02 CC23 CC31 CC38 DD23 DD31 EE01 EE06 EE07 4C086 AA01 BC17 MA16 MA63 NA14 ZA89 ZA92 ZB35 4C206 AA01 CA28 MA03 MA05 MA36 MA83 NA14 ZA89 ZA92 ZB35 4H003 AB05 AB10 AC14 AB15 AC23 AC29 DA02 EA12 EB04 EB07 EB08 EB09 EB13 EB19 EB20 EB21 EB40 EB43 ED02 FA02 FA16 FA17 FA18 FA21 FA30 FA34 4H011 AA02 BA01 BB04 BB06 BB09 BB10 BB18 BC07 DG16

Claims (3)

[Claims] 1. a) Including a compound represented by the following general formula (1) having a different number of moles of ethylene oxide added and having 0 moles of ethylene oxide added, the mass% occupied by the polymer does not show the maximum value, (B) sterilization, wherein the mass% of the ethylene oxide adduct having the following formula is from 15 to 35, and the total amount of the ethylene oxide adduct having an addition mole number before and after the alkyl ethoxy sulfate is from 55 to 75 mass%; A bactericidal compound-containing composition comprising a bactericidal compound and having a viscosity at 25 ° C. of 10 mPa · s or more. R ¹ O— (CH ₂ CH ₂ O) _n —SO ₃ M (1) (where R ¹ is a linear or branched alkyl or alkenyl group having 6 to 24 carbon atoms) And n
Represents the average number of moles of ethylene oxide group added,
6, and M is a hydrogen atom, an alkali metal, an alkaline earth metal, an alkanolamine or ammonium. ) 2. The component (b) is a 1-hydroxy-2-pyridone compound, salicylic acid and a salt thereof, zinc pyrithione, trichlorocarbanilide, triclosan, benzalkonium chloride, alkyldiaminoethylglycine hydrochloride, methylchloroisothiazoline. The fungicidal compound-containing composition according to claim 1, which is one or more fungicidal compounds selected from a methylisothiazoline fungicide and sulfur. 3. The bactericidal compound-containing composition according to claim 1, which is a composition for external use on hair or skin.