JP2013082652A - Skin cleansing agent composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a skin cleansing agent composition giving fresh sense of use, having good foam properties, and being low irritant to skin for meeting various needs of consumers.SOLUTION: The skin cleansing agent composition includes: a higher fatty acid salt represented by general formula (1): R1-COOM1, wherein R1 is a residue obtained by removing a carboxyl group from a 10-22C linear/branched aliphatic saturated/unsaturated monocarboxylic acid, and M1 is an alkali metal ion, an ammonium ion, or an organic ammonium ion; and an aspartic acid derivative represented by general formula (2), wherein R2 is a 10-22C linear/branched alkyl/alkenyl group, and two M2 are the same or different mutually and are each a hydrogen atom, an alkali metal ion, an ammonium ion, or an organic ammonium ion.

Description

  The present invention relates to a skin cleanser composition.

In recent years, skin cleansers such as facial cleansers and body soaps have been added with higher performance and higher functionality in addition to basic functions such as cleansing action for removing makeup and dirt, rinsing properties, and low irritation. It is marketed with increased value. Examples of the property for increasing the added value include foam properties (foaming property, foam quality, foam persistence, etc.), feeling of use such as skin feel after washing, and sensibility performance such as aroma.
For example, as a method for modifying the properties of foam, there is a method in which a suitable viscosity is imparted by blending various surfactants having a cleaning action with a water-soluble polymer or an alkanolamide type nonionic surfactant. Has been done. With regard to the feeling of use, higher fatty acid salts are frequently used because they provide excellent cleaning power as a skin cleanser and a refreshing feeling of use, but they tend to cause rough skin (skin irritation). As a method for improving this irritation, a method of reducing irritation to the skin by using an amphoteric surfactant or an anionic surfactant in combination has been performed. However, such a method tends to improve irritation and foaming properties, but tends to become slippery when rinsed, and tends to impair the refreshing feeling. Basic performance (low irritation and cleaning action) ) And sensibility performance (particularly imparting a refreshing feeling) is extremely difficult.
As described above, various performance improvements have been attempted by combining conventional surfactants and polymer compounds in combination. However, it is still difficult to satisfy all the basic performance and sensibility performance at the same time, and there are still proposals for improvement methods for individual needs of consumers (Patent Document 1).

JP 2001-26795 A

An object of the present invention is to provide a skin cleanser composition that provides a refreshing feeling of use and has good foam quality and low irritation to the skin in response to the diverse needs of consumers in recent years.

As a result of intensive studies, the present inventors have blended a specific higher fatty acid salt and a specific aspartic acid derivative to give a refreshed feeling of use while reducing the fineness of the foam and improving the sustainability of the foam. It has been found that there is an effect of reducing the irritation to the skin, and that the irritation to the skin is low, and surprisingly, that the effect increases in a specific range of the blending ratio of the higher fatty acid salt and the aspartic acid derivative.

That is, the present invention provides a skin cleanser composition having the following items, and the skin cleanser composition includes at least one selected from higher fatty acid salts represented by the following general formula (1): It is characterized by containing at least one selected from aspartic acid derivatives represented by the general formula (2) (that is, N-alkyl (or N-alkenyl) aspartic acid and salts thereof).

［式中、Ｒ^２は炭素数１０〜２２の直鎖状若しくは分岐鎖状のアルキル基又はアルケニル基を表す。また２個のＭ^２は、同一又は異なって、それぞれ水素原子、アルカリ金属イオン、アンモニウムイオン又は有機アンモニウムイオンを表す。］
で表されるアスパラギン酸誘導体を含有する皮膚洗浄剤組成物。 (Claim 1) General formula (1)
R ¹ -COOM ¹ (1)
[Wherein, R ¹ represents a residue obtained by removing a carboxyl group from a linear or branched aliphatic saturated or unsaturated monocarboxylic acid having 10 to 22 carbon atoms. M ¹ represents an alkali metal ion, an ammonium ion, or an organic ammonium ion. ]
The higher fatty acid salt represented by general formula (2)

[Wherein, R ² represents a linear or branched alkyl group or alkenyl group having 10 to 22 carbon atoms. Two M ^{2 s} are the same or different and each represents a hydrogen atom, an alkali metal ion, an ammonium ion, or an organic ammonium ion. ]
A skin cleanser composition containing an aspartic acid derivative represented by:

(Item 2) The skin cleanser composition according to Item 1, wherein the ratio between the higher fatty acid salt and the aspartic acid derivative is 70:30 to 30:70 by weight.

(Item 3) The skin cleanser composition according to Item 1 or Item 2, wherein the total weight of the higher fatty acid salt and the aspartic acid derivative is 50% by weight or more with respect to all the surfactants in the skin cleanser composition. object.

［式中、Ｒ^２は炭素数１０〜２２の直鎖状若しくは分岐鎖状のアルキル基又はアルケニル基を表す。また２個のＭ^２は、同一又は異なって、それぞれ水素原子、アルカリ金属イオン、アンモニウムイオン又は有機アンモニウムイオンを表す。］
で表されるアスパラギン酸誘導体を配合する工程、
（II）一般式（３）
Ｒ^１−ＣＯＯＨ （３）
［式中、Ｒ^１は一般式（１）におけると同義である。］
で表される高級脂肪酸と
一般式（４）

［式中、Ｒ^２は一般式（２）におけると同義である］
で表されるアスパラギン酸化合物とアルカリ性化合物を配合する工程、
（III）一般式（１）
Ｒ^１−ＣＯＯＭ^１ （１）
［式中、Ｒ^１は炭素数１０〜２２の直鎖状若しくは分岐鎖状の脂肪族飽和又は不飽和モノカルボン酸からカルボキシル基を除いて得られる残基を表す。またＭ^１は、アルカリ金属イオン、アンモニウムイオン又は有機アンモニウムイオンを表す。］
で表される高級脂肪酸塩と
一般式（４）

［式中、Ｒ^２は一般式（２）におけると同義である］
で表されるアスパラギン酸化合物とアルカリ性化合物を配合する工程、
（IV）一般式（３）
Ｒ^１−ＣＯＯＨ （３）
［式中、Ｒ^１は一般式（１）におけると同義である。］
で表される高級脂肪酸と
一般式（２）

［式中、Ｒ^２は炭素数１０〜２２の直鎖状若しくは分岐鎖状のアルキル基又はアルケニル基を表す。また２個のＭ^２は、同一又は異なって、それぞれ水素原子、アルカリ金属イオン、アンモニウムイオン又は有機アンモニウムイオンを表す。］
で表されるアスパラギン酸誘導体とアルカリ性化合物を配合する工程
から選ばれる工程を一以上具備する方法により得られる皮膚洗浄剤組成物。 (Claim 4) (I) General formula (1)
R ¹ -COOM ¹ (1)
[Wherein, R ¹ represents a residue obtained by removing a carboxyl group from a linear or branched aliphatic saturated or unsaturated monocarboxylic acid having 10 to 22 carbon atoms. M ¹ represents an alkali metal ion, an ammonium ion, or an organic ammonium ion. ]
The higher fatty acid salt represented by general formula (2)

[Wherein, R ² represents a linear or branched alkyl group or alkenyl group having 10 to 22 carbon atoms. Two M ^{2 s} are the same or different and each represents a hydrogen atom, an alkali metal ion, an ammonium ion, or an organic ammonium ion. ]
A step of blending an aspartic acid derivative represented by:
(II) General formula (3)
R ¹ -COOH (3)
[Wherein, R ¹ has the same meaning as in general formula (1). ]
A higher fatty acid represented by the general formula (4)

[Wherein R ² has the same meaning as in general formula (2)]
A step of blending an aspartic acid compound and an alkaline compound represented by:
(III) General formula (1)
R ¹ -COOM ¹ (1)
[Wherein, R ¹ represents a residue obtained by removing a carboxyl group from a linear or branched aliphatic saturated or unsaturated monocarboxylic acid having 10 to 22 carbon atoms. M ¹ represents an alkali metal ion, an ammonium ion, or an organic ammonium ion. ]
The higher fatty acid salt represented by the general formula (4)

[Wherein R ² has the same meaning as in general formula (2)]
A step of blending an aspartic acid compound and an alkaline compound represented by:
(IV) General formula (3)
R ¹ -COOH (3)
[Wherein, R ¹ has the same meaning as in general formula (1). ]
A higher fatty acid represented by the general formula (2)

[Wherein, R ² represents a linear or branched alkyl group or alkenyl group having 10 to 22 carbon atoms. Two M ^{2 s} are the same or different and each represents a hydrogen atom, an alkali metal ion, an ammonium ion, or an organic ammonium ion. ]
A skin cleanser composition obtained by a method comprising at least one step selected from the step of blending an aspartic acid derivative represented by the formula and an alkaline compound.

(Item 5) The blending ratio of the higher fatty acid salt and the aspartic acid derivative is 70:30 to 30:70 by weight (the higher fatty acid salt includes a higher fatty acid salt obtained from a higher fatty acid and an alkaline compound. In addition, the aspartic acid derivative includes an aspartic acid derivative obtained from an aspartic acid compound and an alkaline compound.), The skin cleansing composition according to Item 4.

(Claim 6) The total weight of the higher fatty acid salt and the aspartic acid derivative is 50% by weight or more with respect to all the surfactants in the skin cleansing composition (in addition, the higher fatty acid salt is composed of higher fatty acid and alkaline compound). The obtained higher fatty acid salt, wherein the aspartic acid derivative includes an aspartic acid derivative obtained from an aspartic acid compound and an alkaline compound.

According to the present invention, it is possible to obtain a skin cleansing composition which gives a refreshing feeling of use, has fine foam texture, good foam persistence and low irritation to the skin.

The skin cleanser composition of the present invention comprises at least one selected from the higher fatty acid salts represented by the general formula (1) and at least one selected from the aspartic acid derivatives represented by the general formula (2). It is characterized by containing.
R ¹ in the general formula (1) is a residue obtained by removing a carboxyl group from a linear or branched saturated fatty acid or unsaturated fatty acid having 10 to 22 carbon atoms. Here, the carbon number means the total carbon number of a linear or branched saturated fatty acid or unsaturated fatty acid. Examples of the linear or branched aliphatic saturated or unsaturated monocarboxylic acid having 10 to 22 carbon atoms constituting the higher fatty acid salt include capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, and arachidin. Acids, behenic acid, palmitoleic acid, oleic acid, elaidic acid, arachidonic acid, erucic acid, linoleic acid, linolenic acid, eleostearic acid, eicosapentaenoic acid, docosahexaenoic acid, isostearic acid and mixtures thereof, coconut oil fatty acid, Examples include palm oil fatty acid, palm kernel oil fatty acid, soybean oil fatty acid, and beef tallow fatty acid. More preferably, a linear or branched aliphatic saturated or unsaturated monocarboxylic acid having 12 to 18 carbon atoms is recommended, specifically lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, isostearic acid. Acid, palm oil fatty acid, palm oil fatty acid, palm kernel oil fatty acid, soybean oil fatty acid are recommended. This description is synonymous with the description of the higher fatty acid represented by the general formula (3).
Moreover, as a counter cation constituting the higher fatty acid salt, alkali metal ions such as potassium ion and sodium ion, ammonium ion, monoethanolammonium ion, N-methylmonoethanolammonium, N-butylmonoethanolammonium, diethanolammonium ion, Organic ammonium ions such as triethanolammonium ion, isopropanolammonium ion, alkanol ammonium ion such as 2-hydroxymethyl-2-propylammonium ion, and ammonium ion of basic amino acid such as lysine and arginine, preferably potassium ion and sodium Ions, ammonium ions, and triethanolammonium ions are recommended.

Specific examples of the higher fatty acid salt according to the present invention include sodium caprate, sodium laurate, sodium myristate, sodium palmitate, sodium stearate, sodium arachidate, sodium behenate, sodium palmitate, sodium oleate , Sodium elaidate, sodium arachidonate, sodium erucate, sodium linoleate, sodium linolenate, sodium eleostearate, sodium eicosapentaenoate, sodium docosahexaenoate, sodium isostearate, sodium palm oil fatty acid, palm oil fatty acid sodium, Palm kernel oil fatty acid sodium, soybean oil fatty acid sodium, beef tallow fatty acid sodium, potassium caprate, potassium laurate, potassium myristate , Potassium palmitate, potassium stearate, potassium arachidate, potassium behenate, potassium palmitate, potassium oleate, potassium elaidate, potassium arachidate, potassium erucate, potassium linoleate, potassium linolenate, eleostearic acid Potassium, potassium eicosapentaenoate, potassium docosahexaenoate, potassium isostearate, palm oil fatty acid potassium, palm oil fatty acid potassium, palm kernel oil fatty acid potassium, soybean oil fatty acid potassium, beef tallow fatty acid potassium, ammonium caprate, ammonium laurate, myristic acid Ammonium, ammonium palmitate, ammonium stearate, ammonium arachidate, ammonium behenate, ammonium oleate, error Ammonium diate, ammonium arachidonate, ammonium erucate, ammonium linoleate, ammonium linolenate, ammonium eleostearate, ammonium eicosapentaenoate, ammonium docosahexaenoate, ammonium isostearate, palm oil fatty acid ammonium, palm oil fatty acid ammonium, palm Nuclear oil fatty acid ammonium, soybean oil fatty acid ammonium, beef tallow fatty acid ammonium, capric acid triethanolamine, lauric acid triethanolamine, myristic acid triethanolamine, palmitic acid triethanolamine, stearic acid triethanolamine, arachidic acid triethanolamine, Behenic acid triethanolamine, oleic acid triethanolamine, elaidic acid triethanol Amine, arachidonic acid triethanolamine, erucic acid triethanolamine, linoleic acid triethanolamine, linolenic acid triethanolamine, eleostearic acid triethanolamine, eicosapentaenoic acid triethanolamine, docosahexaenoic acid triethanolamine, isostearic acid triethanolamine Examples include ethanolamine, coconut oil fatty acid triethanolamine, palm oil fatty acid triethanolamine, palm kernel oil fatty acid triethanolamine, soybean oil fatty acid triethanolamine, and beef tallow fatty acid triethanolamine.
Among these, more preferably, sodium laurate, sodium myristate, sodium palmitate, sodium stearate, sodium oleate, sodium isostearate, sodium palm oil fatty acid, palm oil fatty acid sodium, palm kernel oil fatty acid sodium, soybean oil Fatty acid sodium, potassium laurate, potassium myristate, potassium palmitate, potassium stearate, potassium oleate, potassium isostearate, palm oil fatty acid potassium, palm oil fatty acid potassium, palm kernel oil fatty acid potassium, soybean oil fatty acid potassium, lauric acid Ammonium, ammonium myristate, ammonium palmitate, ammonium stearate, ammonium oleate, ammonium isostearate, coconut oil Ammonium fatty acid, palm oil fatty acid ammonium, palm kernel fatty acid ammonium, soybean oil fatty acid ammonium, lauric acid triethanolamine, myristic acid triethanolamine, palmitic acid triethanolamine, stearic acid triethanolamine, oleic acid triethanolamine, Isostearic acid triethanolamine, palm oil fatty acid triethanolamine, palm oil fatty acid triethanolamine, palm kernel oil fatty acid triethanolamine, soybean oil fatty acid triethanolamine are recommended.
These can be contained alone or in appropriate combination of two or more.

Further, the higher fatty acid salt is not particularly limited, and a commercially available product or a product produced by a known method can be used. Commercially available products include, for example, “2011 Chemical Products of 15911 (Issuing Office; Chemical Industry Daily, Published January 25, 2011)” and “Nippon Cosmetic Raw Materials 2007 (Issuing Office; Pharmaceutical Daily, Japan Cosmetic Industry Association) (Compilation edition) "etc. and are marketed from many manufacturers.

The aspartic acid derivative according to the present invention is a compound represented by the general formula (2). R ² in the general formula (2) is a linear or branched alkyl group or alkenyl group having 10 to 22 carbon atoms, preferably 12 to 22, more preferably 12 to 18 linear or branched. A chain alkyl or alkenyl group is recommended.
Specifically, n-decyl group, lauryl group, myristyl group, palmityl group, stearyl group, arachidyl group, behenyl group, oleyl group, linole group, linolenyl group, isostearyl group, coconut oil alkyl group, palm kernel oil alkyl Groups, palm oil alkyl groups, soybean oil alkyl groups, etc., preferably lauryl group, myristyl group, palmityl group, stearyl group, oleyl group, palm oil alkyl group, palm oil alkyl group, palm kernel oil alkyl group are recommended Is done.

Two M ² constituting the aspartic acid derivative are the same or different and each represents a hydrogen atom, an alkali metal ion, an ammonium ion, or an organic ammonium ion.
Examples of the alkali metal ion include lithium ion, sodium ion, potassium ion and the like, preferably sodium ion and potassium ion are recommended.
Organic ammonium ions include monoethanolammonium ion, N-methylmonoethanolammonium ion, N-butylmonoethanolammonium ion, diethanolammonium ion, triethanolammonium ion, isopropanolammonium ion, 2-hydroxymethyl-2-propylammonium ion Examples include alkanol ammonium ions such as ammonium ions of basic amino acids such as lysine and arginine, and sodium ions, potassium ions, triethanolammonium ions, and ammonium ions are preferred.

Specific examples of the aspartic acid derivative according to the present invention include Nn-decylaspartate monosodium, Nn-decylaspartate monopotassium, Nn-decylaspartate monoammonium, Nn-decyl. Aspartate monotriethanolamine, N-laurylaspartate monosodium, N-laurylaspartate monopotassium, N-laurylaspartate monoammonium, N-laurylaspartate monotriethanolamine, N-myristylaspartate monosodium, N -Myristyl aspartate monopotassium, N-myristyl aspartate monoammonium, N-myristyl aspartate monotriethanolamine, N-palmityl aspartate monosodium, N-palmityl aspartate monopotassium, N- Lumithyl aspartate monoammonium, N-palmityl aspartate monotriethanolamine, N-stearyl aspartate monosodium, N-stearyl aspartate monopotassium, N-stearyl aspartate monoammonium, N-stearyl aspartate monotriethanol Amine, N-oleyl aspartate monosodium, N-oleyl aspartate monopotassium, N-oleyl aspartate monoammonium, N-oleyl aspartate monotriethanolamine, N-isostearyl aspartate monosodium, N-isostearyl asparagine Monopotassium acid, N-isostearyl aspartate monoammonium, N-isostearyl aspartate monotriethanolamine, N-arachidyl aspartate monona Lithium, monopotassium N-arachidylaspartate, monoammonium N-arachidylaspartate, monotriethanolamine N-arachidylaspartate, monosodium N-behenylaspartate, monopotassium N-behenylaspartate, N-behenyl Aspartate monoammonium, N-behenyl aspartate monotriethanolamine, N-coconut oil alkylaspartate monosodium, N-coconut oil alkylaspartate monopotassium, N-coconut oil alkylaspartate monoammonium, N-coconut oil alkyl Aspartate monotriethanolamine, N-palm kernel oil alkyl sodium aspartate, N-palm kernel oil alkyl potassium aspartate, N-palm kernel oil alkyl ammonium aspartate, N-par Nuclear oil alkyl aspartate monotriethanolamine, N-palm oil alkylaspartate monosodium, N-palm oil alkylaspartate monopotassium, N-palm oil alkylaspartate monoammonium, N-palm oil alkylaspartate monotri Ethanolamine, Nn-decylaspartic acid, N-laurylaspartic acid, N-myristylaspartic acid, N-palmitylaspartic acid, N-stearylaspartic acid, N-oleylaspartic acid, N-arachidylaspartic acid, N -Behenyl aspartic acid, N-isostearyl aspartic acid, N-coconut oil alkylaspartic acid, N-palm kernel oil alkylaspartic acid, N-palm oil alkylaspartic acid, Nn-decylaspartic acid dinatri N-lauryl aspartate, disodium N-myristyl aspartate, disodium N-palmityl aspartate, disodium N-stearyl aspartate, disodium N-oleyl aspartate, disodium N-arachidyl aspartate Sodium, disodium N-behenyl aspartate, disodium N-isostearyl aspartate, disodium N-coconut oil alkylaspartate, disodium N-palm kernel oil alkylaspartate, disodium N-palmoil alkylaspartate, N-n-decyl aspartate dipotassium, N-lauryl aspartate dipotassium, N-myristyl aspartate dipotassium, N-palmityl aspartate dipotassium, N-stearyl aspartate Dipotassium acid, dipotassium N-oleyl aspartate, dipotassium N-arachidyl aspartate, dipotassium N-behenyl aspartate, dipotassium N-isostearyl aspartate, dipotassium N-coconut alkyl aspartate, N- Palm kernel oil alkyl aspartate dipotassium, N-palm oil alkyl aspartate dipotassium, Nn-decyl aspartate diammonium, N-lauryl aspartate diammonium, N-myristyl aspartate diammonium, N-palmityl asparagine Diammonium acid, diammonium N-stearyl aspartate, diammonium N-oleyl aspartate, diammonium N-arachidyl aspartate, diammonium N-behenyl aspartate, N-iso Stearyl aspartate diammonium, N-coconut oil alkylaspartate diammonium, N-palm kernel oil alkylaspartate diammonium, N-palm oil alkylaspartate diammonium, Nn-decylaspartate bis (triethanolamine) N-lauryl aspartate bis (triethanolamine), N-myristylaspartate bis (triethanolamine), N-palmitylaspartate bis (triethanolamine), N-stearylaspartate bis (triethanolamine), N-oleyl aspartate bis (triethanolamine), N-arachidyl aspartate bis (triethanolamine), N-behenyl aspartate bis (triethanolamine), N-isostearyl Bisparaginate (triethanolamine), N-coconut oil alkyl bis-aspartate (triethanolamine), N-palm kernel oil bis (triethanolamine) alkylaspartate, N-palm oil bis (triethanolamine) ), Nn-decylaspartic acid (sodium / potassium), N-laurylaspartic acid (sodium / potassium), N-myristylaspartic acid (sodium / potassium), N-palmitylaspartic acid (sodium / potassium), N Stearyl aspartic acid (sodium / potassium), N-oleyl aspartic acid (sodium / potassium), N-arachidyl aspartic acid (sodium / potassium), N-behenyl aspartic acid (sodium / potassium), N- Sostearyl aspartic acid (sodium / potassium), N-palm oil alkylaspartic acid (sodium / potassium), N-palm kernel oil alkylaspartic acid (sodium / potassium), N-palm oil alkylaspartic acid (sodium / potassium), etc. Is exemplified.
In addition, from the viewpoint of foamability, foam quality, water solubility and storage stability, monosodium N-laurylaspartate, monopotassium N-laurylaspartate, monotriethanolamine N-laurylaspartate, N-laurylaspartic acid Monoammonium, monosodium N-myristylaspartate, monopotassium N-myristylaspartate, monotriethanolamine N-myristylaspartate, monoammonium N-myristylaspartate, monosodium N-palmitylaspartate, N-palmityl Monopotassium aspartate, N-palmitylaspartate monotriethanolamine, N-palmitylaspartate monoammonium, N-oleylaspartate monosodium, N-oleylaspartate monopotassium, N-olei Aspartate monotriethanolamine, N-oleylaspartate monoammonium, N-coconut oil alkylaspartate monosodium, N-coconut oil alkylaspartate monopotassium, N-coconut oil alkylaspartate monotriethanolamine, N-coconut Oil alkylaspartate monoammonium, N-palm kernel oil alkylaspartate monosodium, N-palm kernel oil alkylaspartate monopotassium, N-palm kernel oil alkylaspartate monotriethanolamine, N-palm kernel oil alkylaspartate Monoammonium, N-palm oil alkylaspartate monosodium, N-palm oil alkylaspartate monopotassium, N-palmoil alkylaspartate monotriethanolamine, N-palmoil alkylaspartate Monoammonium phosphate, is recommended.
These may be used alone or in combination of two or more in the skin cleanser composition of the present invention.
In addition, the said description overlaps as description of the aspartic acid compound represented by General formula (4).

In the aspartic acid derivative according to the present invention, when two M ² in the general formula (2) are substantially a single derivative or a main component represented by a combination of a hydrogen atom and an ion other than a hydrogen atom However, this is a preferred embodiment that is recommended because it has a pH close to neutral that is suitable for a skin cleansing composition, and is easy to obtain moderate water solubility and low-temperature storage stability.
The mode when the main component is used is that the composition ratio of two M ² , that is, the ratio of hydrogen atom to ion other than hydrogen atom is preferably hydrogen atom: ion other than hydrogen atom (equivalent ratio) = 3: 1 to It is an embodiment in the range of 1: 3, more preferably 2: 1 to 1: 2, especially 1.5: 1 to 1: 1.5. In this case, the aspartic acid derivative is one in which one of two M ² is a hydrogen atom and the other is an ion other than a hydrogen atom, two M ² are both hydrogen atoms, and two M ² are both It is presumed that ions other than hydrogen atoms are mixed.

The aspartic acid derivative according to the present invention is not particularly limited, and a commercially available product or a product produced by a known method can be used. For example, as a manufacturing method, it can manufacture by the method as described in Unexamined-Japanese-Patent No. 5-140059 and Unexamined-Japanese-Patent No. 2001-26795. As an example, maleic acid or a salt thereof and water and / or an organic solvent having an affinity for water are mixed to obtain a relatively high concentration state, and then a desired aliphatic primary amine is added and heated. After completion of the reaction, the reaction solvent is distilled off under reduced pressure and dried.The dried crude product is pulverized, and the remaining unreacted aliphatic primary amine is washed by heating with a solvent, and finally dried under reduced pressure. The method of manufacturing is illustrated.

The total content of the higher fatty acid salt and the aspartic acid derivative in the skin cleansing composition according to the present invention is 1% by weight or more, preferably 2% by weight in order to stably exhibit the effects of the present invention. More preferably, 5% by weight or more is recommended.
The total weight of the higher fatty acid salt and the aspartic acid derivative is preferably 50% by weight or more, more preferably 60% by weight or more, based on the total surfactant in the skin cleansing composition according to the present invention. Is done.

The blending ratio (weight ratio) of the higher fatty acid salt and the aspartic acid derivative in the skin cleansing composition according to the present invention is preferably 70:30 to 30:70, more preferably 60:40 to 40:60. The Within the range of the blending ratio, skin irritation is low, and superiority is recognized in terms of foam stability and foam quality.

The form of the skin cleanser composition can be arbitrarily selected depending on the desired purpose / target, such as an aqueous solution, paste, solid or powder. Examples of the method for preparing the form include a method of appropriately adjusting the types of higher fatty acid salts, aspartic acid derivatives and other components described later, and their blending amounts.

As a method for preparing the skin cleansing composition of the present invention, (i) a predetermined amount of a higher fatty acid salt represented by the above general formula (1) and an aspartic acid derivative represented by the above general formula (2) are necessary. Depending on the method of blending and preparing the desired amount of other ingredients described below,
(Ii) a higher fatty acid represented by the above general formula (3), an aspartic acid compound and an alkaline compound represented by the above general formula (4) so that the desired amounts of the higher fatty acid salt and the aspartic acid derivative are the same. A method of preparing each of the blended amounts of higher fatty acids, aspartic acid compounds and alkaline compounds and, if necessary, other components described later in desired amounts,
(Iii) In the preparation method of the above (i), a method in which any one or a part of a higher fatty acid salt and / or an aspartic acid derivative is replaced with a higher fatty acid, an aspartic acid compound, or an alkaline compound. ) A method of preparing by blending a higher fatty acid salt, an aspartic acid compound and an alkaline compound and, if necessary, other components described later in a desired amount, b) an aspartic acid derivative, a higher fatty acid and an alkaline compound, and optionally desired A method of preparing by blending the amount of other components described later, c) a higher fatty acid salt, an aspartic acid derivative, a higher fatty acid, an aspartic acid compound and an alkaline compound, and optionally a desired amount of the other components described later. Examples are a method of blending and preparing (a method by partial substitution), and the like.
The skin cleanser composition obtained by the preparation methods (i) to (iii) also corresponds to the explanation of the invention described in item 4 above. The steps (I) to (IV) described in the above item 4 are usually carried out by selecting one step, but two or more steps can be selected and carried out. In that case, two or more steps are sequentially performed (split preparation), but it is also possible to simultaneously perform two or more steps. Implementing simultaneously means, for example, an operation of simultaneously blending a higher fatty acid salt and an aspartic acid derivative, and a higher fatty acid, an aspartic acid compound and an alkaline compound, and corresponds to the above (iii) c).

As an example, more specifically, using the preparation method of (i) above, when a liquid (aqueous solution) or paste-like skin cleansing composition is desired, for example, a predetermined amount of higher fatty acid salt and aspartic acid Examples include a method in which a derivative and, if necessary, other components as desired are added to water and dissolved. In this case, the total amount of the surfactants including the higher fatty acid salt and the aspartic acid derivative is preferably 2 to 50% by weight, more preferably 5 to 40% by weight as the active ingredient.
When a powdery skin cleanser composition is desired, for example, a method of dry blending a predetermined amount of a higher fatty acid salt and an aspartic acid derivative with other components (powder) in a desired amount as required, Examples include a method in which a fatty acid salt and an aspartic acid derivative and other components as necessary are added to an appropriate amount of water and mixed to form a high-concentration paste, which is then spray-dried. When a solid skin cleansing composition is desired, for example, a small amount of water is added to a composition of a predetermined amount of higher fatty acid salt and aspartic acid derivative and other components (powder) as desired. There is a method of preparing by kneading into a neat soap shape and putting it in a mold or the like and molding it. In these cases, the total blending amount of all the surfactants including the higher fatty acid salt and the aspartic acid derivative is preferably 1 to 100% by weight as an active ingredient.

The aspartic acid compound according to the present invention is a compound represented by the general formula (4). The description of the aspartic acid compound overlaps with the description of the aspartic acid derivative.
The aspartic acid compound is not particularly limited, and a commercially available product or a product produced by a known method can be used. For example, an aspartic acid derivative (wherein M ² is represented by other than a hydrogen atom) is treated with an acidic compound such as hydrochloric acid and then subjected to post-treatment (purification) by a general method of organic synthetic chemistry. Can be prepared.

The alkaline compound according to the present invention neutralizes the higher fatty acid represented by the above general formula (3) and / or the aspartic acid compound represented by the above general formula (4), respectively, in the skin cleansing composition. In order to form the higher fatty acid salt represented by the general formula (1) and / or the aspartic acid derivative represented by the general formula (2), the blending amount is at least higher. It is necessary to adjust the amount of the fatty acid salt and the aspartic acid derivative so that a predetermined amount can be formed. The alkaline compound may be used for the purpose of a pH adjuster and differs in appearance from the purpose of forming the higher fatty acid salt and / or aspartic acid derivative, but even if it is the former purpose or recognition. The formation purpose can be achieved.
The alkaline compound is not particularly limited as long as it is a compound showing basicity capable of forming a cation of M ¹ in the general formula (1) and / or M ² in the general formula (2), but preferably used as a skin cleanser. The compounds usually formulated in are recommended.
Specifically, inorganic alkaline compounds such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, trisodium phosphate, tripotassium phosphate, tetrasodium pyrophosphate, ammonia (water), monoethanol Examples include organic alkaline compounds such as amine, N-methylmonoethanolamine, N-butylmonoethanolamine, diethanolamine, triethanolamine, isopropanolamine, 2-hydroxymethyl-2-propylamine, lysine, and arginine. Sodium hydroxide, potassium hydroxide, triethanolamine and ammonia (water) are recommended.
These alkaline compounds can be used alone or in combination of two or more.

In addition to the higher fatty acid salt and the aspartic acid derivative according to the present invention, the skin cleansing composition of the present invention contains other components that are generally blended in skin cleansing agents within the scope of the effects of the present invention. Can be blended. Other components include, for example, anionic surfactants other than the higher fatty acid salt according to the present invention, amphoteric surfactants other than the aspartic acid derivative according to the present invention, semipolar surfactants, nonionic surfactants, Various surfactants such as cationic surfactants, polyols, inorganic salts, thickeners, thickeners, chelating agents, preservatives, bactericides, dyes (colorants), fragrances, refreshing agents, moisturizers, oily agents , Conditioning agents, ultraviolet absorbers, animal and plant extracts, hydrotropes, antioxidants, pearlizing agents and the like.

More specifically, for example, an alkyl (or alkenyl) sulfate having an alkyl group (or alkenyl group) having 8 to 18 carbon atoms, a polyoxyethylene having an alkyl group (or alkenyl group) having 8 to 18 carbon atoms ( 1-5) Alkyl (or alkenyl) ether sulfate [in the above () represents the average number of added moles of oxyethylene groups, and the same applies hereinafter. ], Polyoxyethylene (1-5) fatty acid monoethanolamide ether sulfate having an aliphatic acyl group having 8 to 18 carbon atoms, polyoxyethylene having an alkyl group (or alkenyl group) having 8 to 18 carbon atoms (1 ˜5) sulfosuccinic acid monoalkyl (or alkenyl) ether ester salt, alkane sulfonate having an alkyl group having 8 to 18 carbon atoms, α-olefin sulfonate having an oleophilic group having 8 to 20 carbon atoms, carbon number Polyoxyethylene (1-7) alkyl (or alkenyl) ether acetate having 8-18 alkyl group (or alkenyl group), polyoxyethylene fatty acid monoethanolamide ether having aliphatic acyl group having 8-18 carbon atoms Acetic acid salt, aliphatic acylamino acid salt derived from fatty acid having 8 to 18 carbon atoms (N-acylglycine salt) N-acyl sarcosine salt, N-acyl alanine salt, N-acyl-N-methyl alanine salt, N-acyl-L-glutamate, N-acyl-L-aspartate), aliphatic having 8 to 18 carbon atoms N-aliphatic acyl-N-methyltaurine salt having an acyl group, isethionate ester salt having an aliphatic acyl group having 8 to 18 carbon atoms, monoalkyl phosphate ester salt having an alkyl group having 8 to 18 carbon atoms, An anionic surfactant such as polyoxyethylene (1-7) monoalkyl ether phosphate ester salt having an alkyl group having 8 to 18 carbon atoms,

Alkyldimethylaminoacetic acid betaine having an alkyl group having 8 to 18 carbon atoms, alkyldimethylaminohydroxysulfobetaine having an alkyl group having 8 to 18 carbon atoms, fatty acid amidopropyl betaine having an aliphatic acyl group having 8 to 18 carbon atoms, Amidopropylaminohydroxysulfobetaine having an aliphatic acyl group having 8 to 18 carbon atoms, imidazolinium betaine type amphoteric surfactant derived from a fatty acid having 8 to 18 carbon atoms, N having an alkyl group having 8 to 18 carbon atoms -Amphoteric surfactants such as N-alkylamino acid type amphoteric surfactants such as alkylaminodiacetate, N-alkylaminopropionate, N-alkylaminodipropionate, N-alkyldiaminoethylglycine salt,

Semipolar surfactants such as alkyldimethylamine oxide having an alkyl group having 8 to 18 carbon atoms and fatty acid amidopropylamine oxide having an acyl group having 8 to 18 carbon atoms;

An alkanolamide having an aliphatic acyl group having 8 to 18 carbon atoms, a polyoxyethylene (1-10) fatty acid alkanolamide having an aliphatic acyl group having 8 to 18 carbon atoms, a poly having an alkyl group having 8 to 18 carbon atoms Nonionic surfactants such as alkyl polyglycosides having an oxyethylene (1-20) alkyl ether, an alkyl group having 8 to 14 carbon atoms or a polyoxyethylene (1-7) alkyl ether group,

Polyether type thickeners such as polyoxyethylene (60) cetostearyl hydroxymyristyl ether, polyoxyethylene (60) cetyl stearyl diether, polyethylene glycol distearate (150), polyoxyethylene (150) pentastearate Elyslit, polyetherester type thickeners such as polyoxyethylene (160) sorbitan triisostearate, methyl glucoside polyoxyethylene (120), water-soluble such as hydroxyethyl cellulose, hydroxypropyl methylcellulose, sodium polyacrylate, xanthan gum Functional polymeric thickeners, inorganic salt thickeners such as sodium sulfate and sodium chloride,

Examples include humectants such as propylene glycol, ethylene glycol, butylene glycol, sorbitol, and glycerin, oily agents such as hydrocarbons and esters, conditioning agents such as methylpolysiloxane and derivatives thereof, cationized cellulose, and cationized guar gum. .

The skin cleanser composition thus obtained is extremely useful for applications such as body soaps, hand soaps, and facial cleansers, and the form is arbitrarily selected from liquid (aqueous solution), paste, solid, powder, etc. Is also possible.

Hereinafter, the present invention will be specifically described with reference to examples, but the present invention is not limited thereto. In addition, the analysis and evaluation in each Example and a comparative example were performed with the following method. As the compounds used in the examples, commercially available products, reagents, or compounds obtained in the following production examples were used.

[Foaming]
10 ml of an aqueous solution of a skin cleanser composition diluted with artificial hard water (American hardness: 50 ppm) to a concentration of 2.5% by weight in a 100 ml measuring cylinder with a stopper (JIS R3550-1994) The sample was shaken by hand 60 times at a constant speed for 30 seconds at a measurement temperature of 25 ° C. Subsequently, after leaving still for 1 minute, the volume (ml) of the foam after leaving still for 1 minute was measured visually. This measurement was performed three times, and the average of those measured values was determined to an integer, and the average value was defined as “the volume of the foam after standing for 1 minute”. The volume of the foam was used as an index of foamability. It shows that it is excellent in foaming property, so that the numerical value of the volume of foam is large. If the foam volume after standing for 1 minute is 65 ml or more, it is judged to have good foaming properties.

[Foam quality]
In the evaluation of the foaming property, the volume (ml) of the cleaning composition aqueous solution after being allowed to stand at the same time for 1 minute was measured. This measurement was performed three times, and the average of the measured values was obtained up to an integer. The average value was defined as “volume of aqueous solution of skin cleanser composition after standing for 1 minute”. The foam density (g / ml) was calculated using the following formula (1) from the volume of the above-mentioned skin cleanser composition aqueous solution and the numerical value of the volume of foam evaluated for foamability. The larger the foam density value, the finer the foam. The foam density was calculated by regarding the specific gravity of the aqueous skin cleanser composition solution as 1.

Foam density (g / ml) = (10−volume of skin cleanser composition aqueous solution) / (volume of foam) (1)

[Stability of foam]
In the evaluation of the foaming property, the mixture was further allowed to stand for 5 minutes, and the volume (ml) of the foam after standing for 5 minutes and the volume (ml) of the aqueous solution of the skin cleanser composition after standing for 5 minutes were measured. did. This measurement is performed three times, and the average of each measured value is obtained up to an integer. The average value is “volume of foam after standing for 5 minutes” and “volume of aqueous cleaning composition solution after standing for 5 minutes”, respectively. " From these numerical values, the foam density after standing for 5 minutes was calculated using the above formula (1). The foam retention (%) was calculated from the foam density after standing for 1 minute and standing for 5 minutes using the following formula (2). The foam retention rate was used as an index of foam stability. It shows that it is excellent in foam stability (persistence of foam), so that the numerical value of foam retention is large.

Foam retention rate (%) = (bubble density after standing for 5 minutes / bubble density after standing for 1 minute) × 100 (2)

[Skin irritation]
9 ml of pH 7 phosphate buffer solution containing 0.025% by weight of ovalbumin and 1 ml of an aqueous solution of a skin cleansing composition diluted with ion-exchanged water so as to have a surfactant content of 10% by weight. And immediately analyzed using aqueous high performance liquid chromatography (column; Tosoh TSKG3000SWXL (30 cm), measuring temperature; room temperature, eluent; 0.05M phosphate buffer solution (pH 7) containing 0.15M sodium sulfate, detector; UV) Then, the 220 nm absorption peak height of ovalbumin was determined. In addition, it analyzed similarly using ion-exchange water instead of the said skin cleaning composition as a reference value.
As a result of the analysis, the protein denaturation rate (%) was calculated from the obtained peak height of 220 nm using the following formula (3). Skin irritation was evaluated by the rate of protein denaturation. The smaller the protein denaturation rate, the smaller the skin irritation, and a protein denaturation rate of 30% or less is a guideline for determining low irritation.

Protein denaturation rate (%) = ((Ho−Hs) / Ho) × 100 (3)
Ho; height of absorption peak when analyzed as reference value Hs; height of absorption peak when analyzing skin cleansing composition

[Usage feeling]
About the refreshing feeling after rinsing, sensory evaluation by 20 panelists was performed. The evaluation method totaled the presence or absence of a refreshing feeling after rinsing when each panel was actually used, and judged according to the following evaluation criteria. Judgment standard A is judged to have a high effect of giving a refreshing feeling after rinsing.
<Evaluation criteria>
◎: More than 16 out of 20 people evaluated that they feel refreshed after rinsing ○: 11 to 15 out of 20 people evaluated that they feel refreshed after rinsing △: 6 to 10 out of 20 people felt refreshed after rinsing When there is evaluation x: It is evaluated that 5 or less of 20 people have a refreshing feeling after rinsing

[Production example]
A four-necked flask (volume: 1 L) equipped with a stirrer, thermometer, nitrogen inlet tube, and decanter with a cooling tube that can be connected to a vacuum pump is charged with 137.3 g (1.4 mol) of maleic anhydride and 113 g of ion-exchanged water. The mixture was stirred and hydrated for 1 hour without heating. Next, 59.0 g of sodium hydroxide (purity 95%, 1.4 mol) was gradually added while cooling with water to obtain monosodium maleate. Next, 259.5 g (1.4 mol) of laurylamine was added, and the temperature was raised in a hot water bath while slightly bubbling nitrogen, heated to 90 to 97 ° C., and reacted for 10 hours. The semi-solid reaction crude was once cooled and then gradually switched to vacuum and dehydrated under reduced pressure while raising the temperature to 90 ° C. to obtain a dry crude. The reaction rate determined from the unreacted amine content of this product was 93%. This was pulverized in a mortar, heated and washed in 59.5 times the amount of 99.5% ethanol, cooled to room temperature, separated by filtration, further dried under reduced pressure, and N-lauryl aspartic acid according to the present invention. Monosodium (powder to lump) was obtained. The purification yield was 88.8%, and the unreacted amine content was 0.7%.
In addition, the other aspartic acid derivatives described in Table 1 were also prepared in the same procedure as in Production Example 1, and N-myristylaspartate monosodium, N-laurylaspartate monopotassium, and N-laurylaspartate Triethanolamine was obtained. The ion exchange water used for the hydration of maleic anhydride was adjusted to an amount necessary for the final concentration of the target product in the reaction system to be about 80%.

[Examples 1-14 and Comparative Examples 1-3]
These are mixed according to the blending components and blending ratios described in Table 1 or 2, and the concentration is adjusted by adding ion-exchanged water so that the total content of the surfactant is 25% by weight. A skin cleanser composition was prepared. By the above method, foaming property, foam quality, foam stability, skin irritation and feeling of use were analyzed and evaluated. The analysis and evaluation results are shown in Table 1 or Table 2.

[Examples 15 to 17]
These are mixed according to the blending components and blending ratios shown in Table 3, and ion-exchanged water is added so that the total of higher fatty acid salts and aspartic acid derivatives theoretically generated from the surfactant components is 25% by weight. After adjustment, an aqueous skin cleansing composition was prepared. By the above method, foaming property, foam quality, foam stability, skin irritation and feeling of use were analyzed and evaluated, and the results of analysis and evaluation are shown in Table 3.

The compounds used in Tables 1 to 3 are as follows.
Palm oil fatty acid potassium; Alhome K-100 (product name, manufactured by Shin Nippon Chemical Co., Ltd.)
Coconut oil fatty acid sodium; prepared by neutralizing the following palm oil fatty acid with sodium hydroxide.
Palm oil fatty acid; palm fatty acid DH (product name, manufactured by Shin Nippon Rika Co., Ltd.)
Sodium Cocoyl Glutamate; Amino Surfact ACDS-L (product name, manufactured by Asahi Kasei Chemicals Corporation)
Sodium cocoamphoacetate; Softazoline CL (Product name, Kawaken Fine Chemical Co., Ltd.)
Palm oil fatty acid monoethanolamide; Amizole CME (Product name, Kawaken Fine Chemical Co., Ltd.)
Sodium hydroxide, potassium hydroxide, triethanolamine, sodium chloride, glycerin; reagent special grade N-lauryl aspartic acid; the above-mentioned monosodium N-lauryl aspartate was treated with hydrochloric acid in excess of the equivalent of sodium, and the precipitated solid was It was washed with water and dried under reduced pressure.

  From Table 1 to Table 3, by using a higher fatty acid salt and an aspartic acid derivative in combination, the skin irritation is low, the foam texture is fine, and the foam stability is improved while providing a refreshing feeling after rinsing. I know that. In particular, when the blending ratio of the higher fatty acid salt and the aspartic acid derivative is in the range of 70:30 to 30:70, it can be seen that these effects are high.

The skin cleanser composition of the present invention gives a refreshing feeling after rinsing, has good foam quality and foam stability, and has low irritation to the skin. It is possible to design end products with added value (hand soap, body soap, face wash, etc.).

Claims (3)

General formula (1)
R ¹ -COOM ¹ (1)
[Wherein, R ¹ represents a residue obtained by removing a carboxyl group from a linear or branched aliphatic saturated or unsaturated monocarboxylic acid having 10 to 22 carbon atoms. M ¹ represents an alkali metal ion, an ammonium ion, or an organic ammonium ion. ]
The higher fatty acid salt represented by general formula (2)

[Wherein, R ² represents a linear or branched alkyl group or alkenyl group having 10 to 22 carbon atoms. Two M ^{2 s} are the same or different and each represents a hydrogen atom, an alkali metal ion, an ammonium ion, or an organic ammonium ion. ]
A skin cleanser composition containing an aspartic acid derivative represented by: The skin cleansing composition according to claim 1, wherein the ratio of the higher fatty acid salt to the aspartic acid derivative is 70:30 to 30:70 by weight. (I) General formula (1)
R ¹ -COOM ¹ (1)
[Wherein, R ¹ represents a residue obtained by removing a carboxyl group from a linear or branched aliphatic saturated or unsaturated monocarboxylic acid having 10 to 22 carbon atoms. M ¹ represents an alkali metal ion, an ammonium ion, or an organic ammonium ion. ]
The higher fatty acid salt represented by general formula (2)

[Wherein, R ² represents a linear or branched alkyl group or alkenyl group having 10 to 22 carbon atoms. Two M ^{2 s} are the same or different and each represents a hydrogen atom, an alkali metal ion, an ammonium ion, or an organic ammonium ion. ]
A step of blending an aspartic acid derivative represented by:
(II) General formula (3)
R ¹ -COOH (3)
[Wherein, R ¹ has the same meaning as in general formula (1). ]
A higher fatty acid represented by the general formula (4)

[Wherein R ² has the same meaning as in general formula (2)]
A step of blending an aspartic acid compound and an alkaline compound represented by:
(III) General formula (1)
R ¹ -COOM ¹ (1)
[Wherein, R ¹ represents a residue obtained by removing a carboxyl group from a linear or branched aliphatic saturated or unsaturated monocarboxylic acid having 10 to 22 carbon atoms. M ¹ represents an alkali metal ion, an ammonium ion, or an organic ammonium ion. ]
The higher fatty acid salt represented by the general formula (4)

[Wherein R ² has the same meaning as in general formula (2)]
A step of blending an aspartic acid compound and an alkaline compound represented by formula (IV):
R ¹ -COOH (3)
[Wherein, R ¹ has the same meaning as in general formula (1). ]
A higher fatty acid represented by the general formula (2)

[Wherein, R ² represents a linear or branched alkyl group or alkenyl group having 10 to 22 carbon atoms. Two M ^{2 s} are the same or different and each represents a hydrogen atom, an alkali metal ion, an ammonium ion, or an organic ammonium ion. ]
A skin cleanser composition obtained by a method comprising at least one step selected from the step of blending an aspartic acid derivative represented by the formula and an alkaline compound.