JPH1077498A - Detergent composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a detergent which is lowly irritating to the skin and also has excellent antimicrobial activity by incorporating a glycolic acid N- alkylamide sulfate and an antimicrobial agent in a detergent. SOLUTION: This detergent composition comprises (A) 0.1 to 95wt.% glycolic acid N-alkylamide sulfate and (B) 0.01 to 5wt.% antimicrobial agent. As a glycolic acid N-alkylamide sulfate to be used, there can be mentioned, for example, a compound represented by the formula:, wherein R<1> represents a 6-22C linear or branched alkyl or alkenyl group; R<2> represents a hydrogen atom, or a 1-22C alkyl or alkenyl group; M represents a hydrogen atom, an alkali metal, an alkaline earth metal, ammonium, a 2-9C alkanolammonium, a 1-22C alkyl or alkenylammonium or the like. As an antimicrobial agent to be used, there can be mentioned, for example, a metal salt of 2-mercaptopyridine N-oxide wherein the metal is calcium, magnesium, barium, strontium, zinc or the like.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a detergent composition, and more particularly, to a detergent having a low irritating property to the skin and an excellent antibacterial activity, and particularly has a high dandruff and deodorant effect when used for washing the scalp and hair. Composition.

[0002]

2. Description of the Related Art
Skin and hair cleaning compositions generally use anionic surfactants such as alkyl sulfates and ethoxylated alkyl sulfates, and these anionic surfactants are excellent in terms of detergency, foaming power, and the like. However, it has the drawback of being highly irritating to the skin and hair. The irritancy of these surfactants is closely related to the decrease in skin barrier function and the cell division of skin basal cells, and the more irritating surfactants reduce the skin barrier function, or Has already been reported to promote cell division in cells (Gibson WT et al., Food Ch.
em. Toxic., 23, 103 (1985)).

[0003] On the other hand, the greatest causes of dandruff are said to be abnormal exfoliation of keratinocytes and increased secretion of sebum, and the growth of microorganisms has been pointed out as a cause of further deterioration.
Therefore, an anionic surfactant and an antibacterial agent are usually added to a dandruff shampoo for the purpose of washing secreted sebum and suppressing the growth of microorganisms. However, even though such conventional dandruff removing shampoo users have a large number of times of shampooing, there are cases where dandruff occurs relatively early after shampooing. This means that the more frequent the hair wash, the more irritating surfactant comes into contact with the scalp, irritates the skin, reduces the barrier function of the skin, and promotes cell division of skin basal cells Conversely, it is considered to promote the occurrence of dandruff.

[0004] Even in the case of body cleansing agents, most of the current body cleansing agents use highly irritating active agents, and if the effect on the skin barrier function is considered, these cleansing agents can be used to clean the skin. Is believed to reduce the skin's resistance to external stimuli, such as microbial infection of the skin.

[0005] Accordingly, there has been a demand for a detergent composition which is less irritating to the skin, suppresses dandruff, and does not weaken the resistance of the skin.

[0006]

Under such circumstances, the present inventors have conducted intensive studies and found that glycolic acid N-
The present inventors have found that a detergent composition containing an alkylamide sulfate ester salt and an antibacterial agent solves the above problems and further increases the antibacterial effect, thereby completing the present invention.

That is, the present invention comprises the following components (A) and (B): 0.1 to 95% by weight of (A) glycolic acid N-alkylamide sulfate ester salt; and (B) 0.01 to 5% by weight of an antibacterial agent. It is intended to provide a cleaning composition characterized by containing.

[0008]

BEST MODE FOR CARRYING OUT THE INVENTION Examples of the glycolic acid N-alkylamide sulfate used in the present invention include those represented by the following general formula (1).

[0009]

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Wherein R ¹ represents a linear or branched alkyl or alkenyl group having 6 to 22 carbon atoms, R ² represents a hydrogen atom or an alkyl or alkenyl group having 1 to 22 carbon atoms, M is a hydrogen atom, an alkali metal, an alkaline earth metal, ammonium, an alkanol ammonium having 2 to 9 carbon atoms, an alkyl ammonium or alkenyl ammonium having 1 to 22 carbon atoms, an alkyl or alkenyl substituted pyridinium having 1 to 18 carbon atoms, or a base Shows amino acids)

In the general formula (1), R ¹ has 6 to 6 carbon atoms.
22 linear or branched alkyl or alkenyl groups, specifically, a hexyl group, an octyl group, a decyl group,
Examples include a dodecyl group, a tetradecyl group, a hexadecyl group, an octadecyl group, an isostearyl group, an eicosyl group, and a docosyl group. Among these, a straight-chain or branched-chain alkyl group having 6 to 22 carbon atoms is preferable, and a straight-chain alkyl group having 8 to 18 carbon atoms is particularly preferable in terms of foaming properties. R ² represents an alkyl group or alkenyl group having 1 to 22 carbon atoms or a hydrogen atom, among which,
Examples of the alkyl group or alkenyl group include a methyl group, an ethyl group, a propyl group, and a butyl group, as well as the same alkyl groups or alkenyl groups as those exemplified above for R ¹ . As R ² , a hydrogen atom is preferable from the viewpoint of foaming properties and detergency.

M represents a hydrogen atom, an alkali metal, an alkaline earth metal, ammonium, an alkanolammonium having 2 to 9 carbon atoms, an alkylammonium or alkenylammonium having 1 to 22 carbon atoms, or an alkyl or alkenyl substituted with 1 to 18 carbon atoms. The term "pyridinium" or "basic amino acid" refers to ammonium, sodium, potassium, or alkanol ammonium having 2 to 9 carbon atoms in terms of foamability. Particularly, ammonium, sodium, and triethanol ammonium are preferable.

According to the present invention, the compound represented by the general formula (1)
Preferred of N-alkyl amide sulphate salt
As a specific example, CH_Three(CH_Two)₁₁NHCOCH_TwoO
SO_ThreeNH_Four, CH_Three(CH_Two)₉NHCOCH_TwoOSO_ThreeN
H_Four, CH_Three(CH_Two)₁₁NHCOCH_TwoOSO_ThreeNa, C
H_Three(CH_Two)₉NHCOCH_TwoOSO_ThreeNa, CH_Three(CH
_Two)₁₁NHCOCH_TwoOSO_ThreeK, CH_Three(CH_Two)₉NHC
OOSO_ThreeK.

Among these compounds, CH ₃ (C
H ₂ ) ₁₁ NHCOCH ₂ OSO ₃ Na is particularly preferred in terms of foaming properties, detergency and the like. These glycolic acid N-alkylamide sulfates can be produced by the method described in JP-A-7-267917, which has already been proposed by the present applicant.

The antimicrobial agents used in the present invention include, for example, the following. (B-1) calcium, magnesium, barium, strontium of 2-mercaptopyridine-N-oxide;
Zinc, cadmium, tin or zirconium salts. (B-2) The following general formula (2)

[0016]

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Wherein R ⁶ 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 bicycloalkyl group having 7 to 9 carbon atoms,
A cycloalkyl-alkyl group having 1 to 4 carbon atoms in the alkyl group portion (however, the cycloalkyl group may be further substituted by an alkyl group having 1 to 4 carbon atoms);
An aryl group, an aralkyl group having an alkyl group portion having 1 to 4 carbon atoms, an arylalkenyl group having an alkenyl group portion having 2 to 4 carbon atoms, and an aryl having an alkyl group portion having 1 to 4 carbon atoms. An oxyalkyl or arylmercaptoalkyl group, a benzhydryl group, a phenylsulfonylalkyl group having an alkyl moiety having 1 to 4 carbon atoms, and a furyl or alkenyl moiety having a furylalkenyl group having 2 to 4 carbon atoms; May be 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;
R ⁷ represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, an alkenyl group having 2 to 4 carbon atoms, a halogen, a phenyl group or a benzyl group; X ⁺ represents an organic base, an alkali metal ion,
Ammonium ion, alkaline earth metal ion or 2-
Which represents a tetravalent cation].
2-pyrrolidone derivatives.

A specific example of the compound (2) is disclosed in
-50142. That is, for example, 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
6-alkyl system such as (2,4,4-trimethylpentyl) -2-pyridone; 1-hydroxy-4-methyl-6
Cyclohexyl-2-pyridone, 1-hydroxy-4-
6-cyclohexanes such as methyl-6- (methyl-cyclohexyl) -2-pyridone, 1-hydroxy-4-methyl-6- (2-bicyclo [2,2,1] heptyl) -2-pyridone; Hydroxy-4-methyl-6- (4
-Methyl-phenyl) -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, -Hydroxy-4-
Examples include 6-phenyl compounds such as methyl-6- (4-bromo-benzyl) -2-pyridone, among which 6-alkyl compounds are particularly preferable.

The compound (2) can be used as a salt with various organic or inorganic bases. For example, as the organic base, low molecular weight alkanolamines such as ethanolamine, diethanolamine, N-ethylethanolamine, triethanolamine, diethylamino-ethanol, 2-amino-2-methyl-propanediol; ethylenediamine, hexamethylenediamine, cyclohexylamine , Benzylamine, N-methylpiperazine and the like; non-volatile bases; quaternary ammonium hydroxides such as trimethylbenzyl hydroxide; guanidine and its derivatives, especially its alkylated products. ,
Alkali metal salts such as sodium and potassium; ammonium salts, alkaline earth metal salts such as magnesium and calcium; salts with divalent to tetravalent cations such as zinc, aluminum and zirconium; Organic salts, that is, inorganic salts such as low molecular weight alkanolamines, ethylenediamines, and alkali metal salts are preferred.

(B-3) The following equation (3)

[0021]

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2,2'-dithio-bis- represented by the formula
(Pyridine-N-oxide).

The compound (3) may be present in the detergent composition of the present invention as a complex salt with an inorganic salt. Examples of the inorganic salt include magnesium sulfate.

(B-4) The following equation (4)

[0025]

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The trichlorocarbanide represented by the formula (TC
C).

(B-5) The following equation (5)

[0028]

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Triclosan represented by the formula:

(B-6) The following general formula (6)

[0031]

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(In the formula, R ^{8 to} R ¹¹ are groups in which 1 or 2 represents a hydrocarbon group having 8 to 24 carbon atoms, and the remaining groups represent 1 to 2 carbon atoms.)
It indicates to 3 alkyl or hydroxyalkyl group, X ^-
Is an anionic residue of a halogen, an amino acid, a fatty acid, a phosphate ester, a phosphonate ester, a sulfonic acid or a sulfate ester having a branched or linear alkyl or alkenyl group having 1 to 30 carbon atoms, and a styrene sulfonic acid having a polymerization degree of 3 or more. Or an anionic oligomer or polymer selected from a formalin condensate of a sulfonated polycyclic aromatic compound that may have a hydrocarbon group as a substituent or a substituent.) Dialkyl quaternary ammonium salts.

(B-7) The following general formula (7)

[0034]

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(Wherein, R ¹² represents a hydrocarbon group having 8 to 24 carbon atoms; Y ⁻ represents a halogen, an amino acid, a fatty acid, a phosphoric acid having a branched or straight-chain alkyl or alkenyl group having 1 to 30 carbon atoms) Ester, phosphonic acid ester, anionic residue of sulfonic acid or sulfuric acid ester, styrenesulfonic acid having a degree of polymerization of 3 or more as an essential constituent unit, or a polycyclic aromatic compound which may have a hydrocarbon group as a substituent An anionic oligomer or polymer selected from a formalin condensate of a sulfonate).

Antibacterial agents such as sulfur, selenium sulfide, cadmium sulfide, allantoin, menthols, salicylic acid, and undecylenic acid may be used in addition to those shown in the above (B-1) to (B-7).

The antibacterial agents shown above may be used alone or in combination of two or more. The amount of these antibacterial agents is 0.01 to 5% in the composition of the present invention, but 0.1 to 1.5%.
% Is preferable.

If it is less than 0.01%, the effect of preventing dandruff and deodorant is insufficient, and if it exceeds 5%, the effect of addition does not change, and the irritation of the antibacterial agent itself becomes a problem, which is not preferable.

According to the present invention, the amount of the antibacterial agent exhibiting an effect can be suppressed lower than that of a conventional cleaning agent.

As the antibacterial agent used in the present invention, any antibacterial agent can be used as long as it has an antibacterial effect and can be applied to the body. Examples of the deodorant detergent include mercaptopyridine oxide salts represented by (B-1) and 1-hydroxy-2-pyridones represented by (B-2); and trichlorobenzene represented by (B-4) as a detergent for deodorants. Carbanides, triclosan shown in (B-5) and the like are preferable.

In the cleaning composition of the present invention, in addition to the above essential components, components usually used in the cleaning composition, for example, alkyl sulfate, polyoxyethylene alkyl sulfate, α-olefin alkyl sulfate, sulfosuccinic acid Surfactants such as half alkyl esters, acylated glutamic acid, monoalkyl phosphoric acid and soap; water; humectants such as glycerin and propylene glycol; conditioning agents such as cationized cellulose;
Viscosity modifiers such as ethanol, hydroxyethylcellulose and methylcellulose; preservatives such as methylparaben and urea; anti-inflammatory agents such as potassium glycyrrhizinate; ultraviolet absorbers such as oxybenzone; dibutylhydroxytoluene;
Antioxidants such as tocopherol acetate; pearlizing agents;
Dyes and the like can be blended within a range that does not impair the effects of the present invention.

If necessary, the pH of the detergent composition of the present invention can be adjusted by using an alkaline or acidic agent, whereby the pH is preferably adjusted to 2 to 10, more preferably 4 to 8.

The dosage form of the cleaning composition of the present invention may be a dosage form which is generally used, such as a solid form, a powder form, a cream form, and a liquid form.

[0044]

Next, the present invention will be described in more detail with reference to examples, but the present invention is not limited to these examples.

Example 1 Shampoo composition: n-CH as glycolic acid N-alkylamide sulfate
₃ (CH ₂ ) ₁₁ NHCOCH ₂ OSO ₃ Na (sodium salt of glycolic acid-n-lauryl amide sulfate) 2
A shampoo composition containing 0% of zinc salt of 2-mercaptopyridine-N-oxide (abbreviation: Zpt) 1% as an antibacterial agent was prepared, and its dandruff preventing effect was tested by the following method. As a control, a shampoo containing 20% of anionic surfactant lauryl sulfate triethanolamine salt and 1% of zinc salt of 2-mercaptopyridine-N-oxide (Zpt) was used. Table 1 shows the results.

<Test Method> 20 to 32 test subjects
We selected four men who had a relatively large amount of dandruff and had no dandruff-preventing effect with normal dandruff shampoo.
As a control period, Zp for all four test subjects
Hair washing was performed for 2 weeks with a shampoo based on lauryl sulfate triethanolamine salt without addition of t, and the state of dandruff was visually observed. Subsequently, all four test subjects were asked to use the above two types of shampoo by the half-head method for one month, and the state of dandruff after one month of use was visually observed on the left and right of the scalp, at the end of the control period. The dandruff prevention effect was evaluated according to the following evaluation criteria by comparing with the scalp condition.

Evaluation criteria ：: High dandruff prevention effect △: Slight dandruff prevention effect ×: No dandruff prevention effect

[0048]

[Table 1]

As is evident from the results in Table 1, it was confirmed that the shampoo composition of the present invention exhibited a significantly higher antidandruff effect than the conventional shampoo containing an antibacterial agent.

Example 2 Body Shampoo Composition:

(%) N-CH ₃ (CH ₂ ) ₁₁ NHCOCH ₂ OSO ₃ NH ₄ 10 triethanolamine lauryl phosphate 10 lauryl hydroxysulfobetaine 3 potassium glycyrrhizinate 0.3 oxybenzone 0.2 triclosan 0.5 perfume fine amount water balance total 100.0

The above-mentioned body shampoo composition had an extremely low skin irritation and an excellent deodorant effect.

Example 3 Shampoo composition:

Table 3 (%) n-CH ₃ (CH ₂ ) ₁₁ NHCOCH ₂ OSO ₃ Na 15 Lauryl phosphoric acid diethanolamide 2 Cationic polymer (Polymer JR400 (manufactured by Union Carbide)) 0.1 2-Dodecylhexadecyltrimethyl ammonium chloride 0.2 zinc salt of 2-mercaptopyridine--N- oxide 1.0 polyvinyl alcohol 0.5 preservative 0.1 perfume, dye qs water balance total 100.0

The shampoo composition described above was extremely weak in skin irritation and had a good antidandruff effect.

Example 4 Shampoo composition:

TABLE 4 _{(%) n-CH 3 (} CH 2) 11 NHCOCH 2 OSO 3 Na 10 n-CH 3 (CH 2) 11 NHCOCH 2 OSO 3 NH 4 5 lauryl phosphoric acid diethanolamide 2 cationic polymer (Merquat 550 (Manufactured by Merck)) 0.1 2-dodecylhexadecyltrimethylammonium chloride 0.2 pyrocdon olamine [chemical name: 1-hydroxy-4-methyl-6- (2,4,4-trimethylpentyl)- 2-(1H-pyridone monoethanolamine salt] 1.0 preservative 0.1 perfume, dye qs water balance total 100.0

The shampoo composition described above was extremely weak in skin irritation and had a good antidandruff effect.

[0056]

The cleaning composition of the present invention is extremely mild on the skin and has a high antibacterial effect without changing the metabolic reaction of the skin or reducing the barrier function of the skin itself. Therefore, when used as a cleaning agent for scalp and hair, dandruff that occurs early after hair washing can be effectively suppressed, and when used as a cleaning agent for the body, a high antibacterial effect can be obtained.

Claims (2)

[Claims] 1. The following components (A) and (B): (A) 0.1 to 95% by weight of a glycolic acid N-alkylamide sulfate (B) 0.01 to 5% by weight of an antibacterial agent A cleaning composition comprising: 2. The glycolic acid N-alkylamide sulfate salt of the component (A) is represented by the following general formula (1): ## STR1 ## [Wherein, R ¹ represents a linear or branched alkyl group or alkenyl group having 6 to 22 carbon atoms, R ² represents a hydrogen atom or an alkyl group or alkenyl group having 1 to 22 carbon atoms, and M represents hydrogen. Atoms, alkali metals, alkaline earth metals,
Ammonium, alkanol ammonium having 2 to 9 carbon atoms, alkyl ammonium or alkenyl ammonium having 1 to 22 carbon atoms, alkyl or alkenyl substituted pyridinium having 1 to 18 carbon atoms or a basic amino acid]. The cleaning composition according to claim 1.