Surfactants and compositions

Abstract

The present invention provides: a surfactant, which is suitable for obtaining a product such as a personal care product (e.g., a cosmetic) having good foaming, foam quality, and solubility even in a weakly acidic region with a pH level equivalent to that of the skin, and having a low viscosity and high handleability. More specifically, the present invention provides: a surfactant comprising an N-monounsaturated acyl acidic amino acid or a salt thereof, wherein the unsaturated acyl group is an acyl group having 10 to 16 carbon atoms.

Description

Technical Field

[0001] The present invention relates to surfactants and compositions. Background Art

[0002] Surfactants are used for various purposes such as cleaning, emulsification, solubilization, dispersion, foaming, lubrication, antistatic, and rust prevention in personal care products, household care products, pesticides, coatings, inks, lubricant additives, cutting oil additives, and rust inhibitors. For example, when used in personal care products, surfactants are usually added as body and hair cleansers.

[0003] In recent years, detergent compositions for body and hair have been required to have not only high cleaning power but also low irritation to the skin and excellent feeling of use. Among them, detergent compositions containing amino acids, such as N-acyl glutamic acid salts and N-acyl glycinate salts, etc. as active ingredients have attracted attention. Detergents for body and hair are preferably milder to the skin and are in the weakly acidic region with a pH level equivalent to that of the skin. However, in the weakly acidic region, transparency may not be maintained or sufficient foaming may not be obtained.

[0004] For N-acylglutamic acid, which is a kind of N-acyl acidic amino acid, research (Patent Documents 1 and 2) on improving the function of N-acylglutamic acid by regulating the fatty acid chain length of the acyl group has been reported. However, these reports only discuss: N-acylglutamic acid with acyl group derived from fatty acid, which can be easily obtained from natural plants.

[0005] Prior art literature

[0006] Patent Literature

[0007] Patent Document 1: Japanese Patent Application Publication No. 2009-51945

[0008] Patent Document 2: Japanese Patent Application Publication No. 2003-34670 Summary of the invention

[0009] Technical problem solved by the invention

[0010] The problem of the present invention is to find a new surfactant by adjusting the acyl group of N-acyl acidic amino acids, and use it in addition to existing N-saturated acyl acidic amino acids or their salts to solve the problems of N-saturated acyl acidic amino acids or their salts (transparency in weakly acidic regions, foaming, etc.). More specifically, a surfactant and a composition containing the surfactant that also improves the cleansing power of oil are provided, wherein the surfactant can be used to obtain products such as personal care products (such as cosmetics) with good foaming, foam quality and solubility even in a weakly acidic region with a pH equivalent to that of the skin, and low viscosity and high handling properties.

[0011] Technical means of solving problems

[0012] The present inventors have conducted intensive research on the above-mentioned problems and have found that N-monounsaturated acyl acidic amino acids or salts thereof (herein, unsaturated acyl groups are acyl groups having 10 to 16 carbon atoms) have good foaming, foam quality and solubility even in a weakly acidic pH region of the same level as that of the skin, and have a low viscosity with high handling properties, thereby completing the present invention. In addition, the present inventors have found that a composition using N-monounsaturated acyl acidic amino acids or salts thereof (herein, unsaturated acyl groups are acyl groups having 10 to 16 carbon atoms) in combination with N-saturated acyl acidic amino acids or salts thereof improves the cleansing power of oil in addition to the effect of the surfactant, thereby completing the present invention.

[0013] Since it has good foaming, foam quality and solubility even in a weakly acidic region with a pH level similar to that of the skin, it has the advantages of good applicability to the skin and excellent storage stability due to suppression of precipitation. In addition, unlike conventional anionic surfactants, it has the advantages of low viscosity with high handleability even at low pH. It is believed that surfactants having these advantages are particularly suitable for use in products such as personal care products (e.g., cosmetics) that can be directly applied to the skin.

[0014] In addition, by improving the cleaning power of oil, an advantage of being able to expect more effective cleaning power is achieved. Therefore, it is considered that a composition that achieves this advantage in addition to the effect of a surfactant is particularly suitable for use in detergents for the body including the face, hair, etc. in personal care products.

[0015] That is, the present inventors provide the following [1] to

[15] .

[0016] [1] A surfactant comprising an N-monounsaturated acyl acidic amino acid or a salt thereof, wherein the unsaturated acyl group is an acyl group having 10 to 16 carbon atoms.

[0017] [2] The surfactant according to [1], wherein the N-monounsaturated acyl acidic amino acid is a compound represented by the following general formula (1):

[0018] [Chemical formula 1]

[0019]

[0020] In the general formula (1), l is an integer of 1 or 2, and m is an integer of 0-6.

[0021] [3] The surfactant according to [1] or [2], wherein the stereochemistry of the N-monounsaturated acyl acidic amino acid is cis.

[0022] [4] The surfactant according to any one of [1] to [3] above, wherein the N-monounsaturated acyl acidic amino acid is N-monounsaturated acylglutamic acid.

[0023] [5] A composition comprising: component (A) an N-monounsaturated acyl acidic amino acid or a salt thereof, wherein the unsaturated acyl group is an acyl group having 10 to 16 carbon atoms; and component (B) an N-saturated acyl acidic amino acid or a salt thereof.

[0024] [6] A composition according to [5], wherein component (A) comprises: (A1) an N-monounsaturated acyl acidic amino acid or a salt thereof, wherein the unsaturated acyl group is an acyl group having 12 carbon atoms; and (A2) an N-monounsaturated acyl acidic amino acid or a salt thereof, wherein the unsaturated acyl group is an acyl group having 10, 14 or 16 carbon atoms.

[0025] [7] The composition according to [5] or [6], wherein component (B) comprises: (B1) N-lauroyl acidic amino acid and / or its salt.

[0026] [8] The composition according to [7], wherein component (B) further comprises: (B2) an N-saturated acyl acidic amino acid and / or a salt thereof, wherein the saturated acyl group is an acyl group having 8, 10, 14 or 16 carbon atoms.

[0027] [9] The composition according to any one of [5] to [8], further comprising: component (C) an N-unsaturated fatty acid or a salt thereof.

[0028]

[10] The composition according to any one of [5] to [9], further comprising: component (D) a water-soluble medium.

[0029]

[11] The composition according to any one of [5] to

[10] above, wherein the mass ratio of component (A) to the total of component (A) and component (B) (A / (A+B)) is 0.001 to 1.

[0030]

[12] The composition according to any one of [5] to

[11] above, wherein the pH thereof is 3 to 9.

[0031]

[13] The composition according to any one of [5] to

[12] above, which has a viscosity of 1.5 Pa·s or less.

[0032]

[14] The composition according to any one of [5] to

[13] , which is a composition for external use on the skin.

[0033]

[15] The composition according to any one of [5] to

[13] , which is a detergent composition.

[0034] Effects of the Invention

[0035] The surfactant of the present invention has the effects of good foaming, foam quality and solubility even in a weakly acidic region with a pH level similar to that of the skin, and has a low viscosity with high handling properties. Therefore, the surfactant of the present invention is particularly suitable for use in products such as personal care products (e.g., cosmetics) that can be directly applied to the skin.

[0036] The composition of the present invention, in addition to the above effects, also achieves the effect of improving the cleaning power of oil. Therefore, the composition of the present invention is particularly suitable for use in personal care products that can be directly applied to the skin, such as detergents for the body including the face, hair, etc.

[0037] Specific embodiments of the present invention

[0038] 1. Surfactants

[0039] The surfactant of the present invention comprises: an N-monounsaturated acyl acidic amino acid or a salt thereof, wherein the unsaturated acyl group is an acyl group having 10 to 16 carbon atoms.

[0040] The acyl part of the N-monounsaturated acyl acidic amino acid is a monounsaturated acyl group, so the viscosity will not be extremely reduced. In addition, the number of carbon atoms in the acyl part is 10 to 16, so it will not be excessively thickened, and it can achieve the effect of having a low viscosity with high handling properties and good solubility. In addition, it has good foaming and foam quality.

[0041] In this specification, "acyl group having n carbon atoms" means n-1 H mAn acyl group represented by -CO- (the hydrogen atom may be substituted). Here, m is appropriately determined depending on the number of carbon atoms and the presence or absence of an unsaturated bond.

[0042] In the present specification, the term "N-monounsaturated acyl acidic amino acid (wherein the acyl group is an acyl group having 10 to 16 carbon atoms)" refers to a C n-1 H m -CO-NH-CHR-COOH represented by the compound (H m The hydrogen atom represented by m is optionally substituted. m is as defined above. R represents the side chain of an acidic amino acid). That is, "N-monounsaturated acyl acidic amino acid" refers to a compound obtained by replacing one hydrogen atom on the amino group of an acidic amino acid with an unsaturated acyl group. "N-monounsaturated acyl acidic amino acid" may be a free form of N-monounsaturated acyl acidic amino acid or a salt of N-monounsaturated acyl acidic amino acid.

[0043] As the salt of N-monounsaturated acyl acidic amino acid, for example, inorganic salts and organic salts can be mentioned. As the inorganic salt, for example, salts of metals (for example, monovalent metals such as lithium, sodium, potassium, rubidium and cesium, and divalent metals such as calcium, magnesium and zinc) and salts of inorganic bases (for example, ammonia) can be mentioned. As the organic salt, for example, salts of organic bases (for example, ethylenediamine, propylenediamine, ethanolamine, monoalkylethanolamine, dialkylethanolamine, diethanolamine, triethanolamine, lysine, arginine, histidine and ornithine) can be mentioned.

[0044] In this specification, N-monounsaturated acyl acidic amino acids are sometimes represented as: derived from C n-1 H m -COOH-represented fatty acid or its derivative. In addition, in this specification, "unsaturated acyl group having n carbon atoms" and fatty acid derived therefrom are sometimes described as "Cn:m". For example, "N-dodecenoyl acidic amino acid (C12:1)" refers to a compound (C12:1) in which one hydrogen atom on the amino group of the acidic amino acid is replaced by a dodecenoyl group which is an acyl group derived from dodecenoic acid (C12:1). 11 H 21 CO-NH-CHR-COOH, where R represents the side chain of an acidic amino acid).

[0045] In the case of obtaining an N-monounsaturated acyl acidic amino acid from a monounsaturated fatty acid, the N-monounsaturated acyl acidic amino acid can be obtained, for example, by: n-1 H mA monounsaturated fatty acid derivative represented by -COX (X is an arbitrary monovalent group, for example, a halogen atom selected from fluorine, chlorine, bromine and iodine) is reacted with an acidic amino acid or a salt thereof (for example, the salt includes the above-mentioned inorganic salts and organic salts).

[0046] The monounsaturated fatty acid as a source of N-monounsaturated acyl acidic amino acid is preferably, for example, decenoic acid (C10:1), dodecenoic acid (C12:1), tetradecenoic acid (C14:1) (e.g., myristic acid) and hexadecenoic acid (C16:1) (e.g., palmitoleic acid), dodecenoic acid (C12:1) or hexadecenoic acid (C16:1), and dodecenoic acid (C12:1) is further preferred.

[0047] The "acidic amino acid" in "N-monounsaturated acyl acidic amino acid" refers to an amino acid having an acidic side chain. Examples of the acidic amino acid include glutamic acid and aspartic acid, and glutamic acid is preferred.

[0048] N-monounsaturated acyl acidic amino acids include, for example, N-decenoyl acidic amino acids (C10:1), N-dodecenoyl acidic amino acids (C12:1), N-tetradecenoyl acidic amino acids (C14:1) and N-hexadecenoyl acidic amino acids (C16:1), preferably N-dodecenoyl acidic amino acids (C12:1) or N-hexadecenoyl acidic amino acids (C16:1), more preferably N-dodecenoyl glutamic acid (C12:1) or N-hexadecenoyl glutamic acid (C16:1), and further preferably N-dodecenoyl glutamic acid (C12:1).

[0049] The N-monounsaturated acyl acidic amino acid may be one N-monounsaturated acyl acidic amino acid or a salt thereof, or may contain two or more N-monounsaturated acyl acidic amino acids or salts thereof. That is, the N-monounsaturated acyl acidic amino acid may contain one or more selected from N-decenoyl acidic amino acids (C10:1), N-dodecenoyl acidic amino acids (C12:1), N-tetradecenoyl acidic amino acids (C14:1) and N-hexadecenoyl acidic amino acids (C16:1). In the case of two or more N-monounsaturated acyl acidic amino acids, a combination of N-dodecenoyl acidic amino acid (C12:1) and one or more selected from N-decenoyl acidic amino acid (C10:1), N-tetradecenoyl acidic amino acid (C14:1) and N-hexadecenoyl acidic amino acid (C16:1) is preferred. From the viewpoint of further improving foam quality, a combination of N-dodecenoyl acidic amino acid (C12:1) and N-hexadecenoyl acidic amino acid (C16:1) is more preferred.

[0050] The unsaturated bond site of the N-monounsaturated acyl acidic amino acid is not particularly limited, and may be the carbon chain end of the acyl site, may be between carbon atoms several carbon atoms away from the carbon chain end of the acyl site, or may be the α position of the carbonyl group of the acyl site. Among them, it is preferred that the unsaturated bond is between carbon atoms 6 to 7 carbon atoms away from the carbon chain end of the acyl site. That is, the N-monounsaturated acyl acidic amino acid is preferably a compound represented by the following general formula (1).

[0051] [Chemical formula 2]

[0052]

[0053] (In the general formula (1), l is an integer of 1 or 2, and m is an integer of 0 to 6)

[0054] The stereochemistry (unsaturated double bond site) of the N-monounsaturated acyl acidic amino acid may be either cis or trans, but the cis form is preferred from the viewpoint of suppressing the increase in thickening property and having a low viscosity with high handling properties.

[0055] 2. Composition

[0056] The composition of the present invention comprises: component (A) an N-monounsaturated acyl acidic amino acid or a salt thereof, wherein the unsaturated acyl group is an acyl group having 10 to 16 carbon atoms; and component (B) an N-saturated acyl acidic amino acid or a salt thereof.

[0057] The composition of the present invention contains component (A), and therefore has good foaming, foam quality and solubility even in a weakly acidic region with a pH equivalent to that of the skin, and has a low viscosity with high handling properties. In addition, the composition of the present invention is a composition containing component (B) and having a variant in the acyl group, and therefore achieves an effect of improving the cleansing power of oil.

[0058] (ingredient (A))

[0059] The details of the component (A) are as described in the N-monounsaturated acyl acidic amino acid of the surfactant.

[0060] (Component (B))

[0061] In this specification, "N-saturated acyl acidic amino acid" refers to a free form of C n-1 H m -CO-NH-CHR-COOH represented by the compound (H mThe hydrogen atom represented by m is optionally substituted. m is as defined above. R represents the side chain of an acidic amino acid). That is, "N-saturated acyl acidic amino acid" refers to a compound obtained by replacing one hydrogen atom on the amino group of an acidic amino acid with a saturated acyl group. "N-saturated acyl acidic amino acid" may be a free form of an N-saturated acyl acidic amino acid or a salt of an N-saturated acyl acidic amino acid.

[0062] In addition, as a salt of an N-saturated acyl acidic amino acid, it can be said that it is the same as the salt of an N-monounsaturated acyl acidic amino acid.

[0063] In this specification, N-saturated acyl acidic amino acids are sometimes represented as derived from C n-1 H m -COOH-denoted fatty acid or its derivative. In addition, in this specification, "a saturated acyl group having n carbon atoms" and the fatty acid from which it is derived are sometimes described as "Cn". For example, "N-lauroyl acidic amino acid (C12)" refers to a compound (C12) in which one hydrogen atom on the amino group of the acidic amino acid is replaced by a lauroyl group which is an acyl group derived from lauric acid (C12). 11 H 23 CO-NH-CHR-COOH, where R represents the side chain of an acidic amino acid).

[0064] In the case of obtaining N-saturated acyl acidic amino acids from saturated fatty acids, the N-saturated acyl acidic amino acids can be obtained, for example, by the following method: n-1 H m A saturated fatty acid derivative represented by -COX (X is an arbitrary monovalent group, for example, a halogen atom selected from fluorine, chlorine, bromine and iodine) is reacted with an acidic amino acid or a salt thereof (for example, the above-mentioned inorganic salts and organic salts can be mentioned as the salt).

[0065] Examples of the N-saturated acyl acidic amino acid include N-octanoyl acidic amino acid (C8), N-hexanoyl acidic amino acid (C10), N-lauroyl acidic amino acid (C12), N-myristoyl acidic amino acid (C14), N-palmitoyl acidic amino acid (C16) and N-stearoyl acidic amino acid (C18).

[0066] The "acidic amino acid" in the "N-saturated acyl acidic amino acid" refers to an amino acid having an acidic side chain. Examples of the acidic amino acid include glutamic acid and aspartic acid, and glutamic acid is preferred.

[0067] The N-saturated acyl acidic amino acid is preferably N-octanoyl acidic amino acid (C8), N-hexanoyl acidic amino acid (C10), N-lauroyl acidic amino acid (C12), N-myristoyl acidic amino acid (C14) or N-palmitoyl acidic amino acid (C16), more preferably N-lauroyl acidic amino acid (C12), and further preferably N-lauroyl glutamic acid (C12).

[0068] Component (B) may be one N-saturated acyl acidic amino acid or its salt, or may contain two or more N-saturated acyl acidic amino acids or their salts. That is, component (B) may contain one or more selected from N-octanoyl acidic amino acid (C8), N-hexanoyl acidic amino acid (C10), N-lauroyl acidic amino acid (C12), N-myristoyl acidic amino acid (C14), N-palmitoyl acidic amino acid (C16) and N-stearoyl acidic amino acid (C18). In the case of two or more N-saturated acyl acidic amino acids, it is preferred to contain N-lauroyl acidic amino acid (C12), and it is more preferred to contain N-lauroyl acidic amino acid (C12) and one or more selected from N-octanoyl acidic amino acid (C8), N-hexanoyl acidic amino acid (C10), N-myristoyl acidic amino acid (C14) and N-palmitoyl acidic amino acid (C16) in combination.

[0069] When component (B) contains N-lauroyl acidic amino acid (C12), the content of N-lauroyl acidic amino acid (C12) in component (B) is, for example, 20% by mass or more, preferably 30% by mass or more, more preferably 35% by mass or more, further preferably 40% by mass or more, and further preferably 50% by mass or more. More specifically, the content of N-lauroyl acidic amino acid in component (B) is, for example, 20 to 100% by mass, preferably 30 to 100% by mass, more preferably 35 to 100% by mass, further preferably 40 to 100% by mass, and further preferably 50 to 100% by mass.

[0070] The mass ratio of component (A) to the total of component (A) and component (B) (A / (A+B)) is usually 0.001 or more, preferably 0.002 or more, more preferably 0.003 or more, and further preferably 0.004 or more, from the viewpoint of improving the solubility at low pH based on component (A). In addition, the mass ratio of component (A) to the total of component (A) and component (B) (A / (A+B)) can be 1 or less, preferably less than 1, more preferably 0.8 or less, further preferably 0.6 or less, and further preferably 0.5 or less, from the viewpoint that the content of component (B) is relatively large and contributes to the cleaning power of the oil. More specifically, the mass ratio of component (A) to the total of component (A) and component (B) (A / (A+B)) is usually 0.001 to 1, preferably 0.001 or more and less than 1, more preferably 0.002 to 0.8, further preferably 0.003 to 0.6, and further preferably 0.004 to 0.5.

[0071] The composition of the present invention may further comprise: ingredient (C) N-unsaturated fatty acid or a salt thereof.

[0072] When the composition of the present invention contains the component (C), the foam quality is further improved and the detergency of the oil is further enhanced.

[0073] (ingredient (C))

[0074] The number of carbon atoms of the unsaturated fatty acid is preferably 6 to 22, more preferably 8 to 18. Examples of the unsaturated fatty acid include hexenoic acid (C6:1), octenic acid (C8:1), decenoic acid (C10:1), dodecenoic acid (C12:1), tetradecenoic acid (C14:1) (e.g., myristic acid), hexadecenoic acid (C16:1) (e.g., palmitic acid), octadecenoic acid (C18:1) (e.g., oleic acid), eicosenoic acid (C20:1) (e.g., arachidic acid), and docosenoic acid (C22:1), preferably dodecenoic acid (C12:1).

[0075] Examples of the salt of unsaturated fatty acid include inorganic salts such as sodium salts, potassium salts, calcium salts, magnesium salts, and aluminum salts; organic amine salts such as ammonium salts, monoethanolamine salts, diethanolamine salts, and triethanolamine salts; and organic salts such as basic amino acid salts such as arginine salts and lysine salts. Among them, triethanolamine salts, sodium salts, and potassium salts are preferred.

[0076] Component (C) may be one unsaturated fatty acid or its salt, or may contain two or more unsaturated fatty acids or their salts. That is, component (C) may contain one or more selected from hexenoic acid (C6:1), octenic acid (C8:1), decenoic acid (C10:1), dodecenoic acid (C12:1), tetradecenoic acid (C14:1) (e.g., myristic acid), hexadecenoic acid (C16:1) (e.g., palmitoleic acid), octadecenoic acid (C18:1) (e.g., oleic acid), eicosenoic acid (C20:1) (e.g., arachidic acid), and docosenoic acid (C22:1). In the case of two or more unsaturated fatty acids or their salts, it is preferred to contain dodecenoic acid (C12:1), and it is more preferred to contain dodecenoic acid (C12:1) in combination with one or more selected from octenic acid (C8:1), decenoic acid (C10:1), tetradecenoic acid (C14:1) and hexadecenoic acid (C16:1).

[0077] When component (C) includes dodecenoic acid (C12:1), the content of dodecenoic acid (C12:1) in component (C) is, for example, 30% by mass or more, preferably 40% by mass or more, more preferably 50% by mass or more, further preferably 60% by mass or more, further preferably 70% by mass or more, and particularly preferably 80% by mass or more. More specifically, the content of dodecenoic acid (C12:1) in component (C) is, for example, 30 to 100% by mass, preferably 40 to 100% by mass, more preferably 50 to 100% by mass, further preferably 60 to 100% by mass, further preferably 70 to 100% by mass, and particularly preferably 80 to 100% by mass.

[0078] The mass ratio (C / (A+B)) of component (C) to the total of component (A) and component (B) may be greater than 0. When the mass ratio (C / (A+B)) of component (C) to the total of component (A) and component (B) is 0, component (C) is not included. From the viewpoint that component (C) helps to improve the foam quality (density), it can be set to be greater than 0.001, preferably greater than 0.01, more preferably greater than 0.1, further preferably greater than 0.2, further preferably greater than 0.4, and particularly preferably greater than 0.5. In addition, from the viewpoint of contributing to the effects of component (A) and component (B), the mass ratio (C / (A+B)) of component (C) to the total of component (A) and component (B) is generally less than 20, preferably less than 15, more preferably less than 13, further preferably less than 11, and further preferably less than 10. More specifically, the mass ratio of component (C) to the total of component (A) and component (B) (C / (A+B)) is usually 0.001 to 20, preferably 0.01 to 20, more preferably 0.1 to 15, further preferably 0.2 to 13, further preferably 0.4 to 11, and particularly preferably 0.5 to 10.

[0079] The composition of the present invention may contain component (A), component (B) and any component (C) in (D) a water-soluble medium. As the water-soluble medium, any water-soluble solvent may be used. As the water-soluble medium, for example, an aqueous solution may be mentioned. The aqueous solution may or may not have a buffering capacity. As the aqueous solution, for example, water (e.g., distilled water, sterile distilled water, purified water, physiological saline, tap water such as city water), phosphate buffer, Tris-hydrochloric acid buffer, TE (Tris-EDTA) buffer, carbonate buffer, boric acid buffer, tartaric acid buffer, glycine buffer, citrate buffer, acetate buffer.

[0080] The content of component (A) varies according to the types and concentrations of other components contained in the composition of the present invention, as well as various conditions such as pH, and is therefore not particularly limited. In the case where the composition of the present invention is an aqueous solution, from the viewpoint of improving solubility at low pH, for example, it is 0.001% by mass or more, preferably 0.002% by mass or more, and more preferably 0.003% by mass or more. In addition, the content of component (A) may be, for example, set to 60% by mass or less, preferably 40% by mass or less. More specifically, the content of component (A) may be, for example, 0.001 to 60% by mass, preferably 0.001 to 40% by mass, more preferably 0.002 to 40% by mass, and further preferably 0.003 to 40% by mass.

[0081] The content of component (B) varies according to various conditions such as the type and concentration of other components contained in the composition of the present invention, as well as pH, and is therefore not particularly limited. In the case where the composition of the present invention is an aqueous solution, from the viewpoint of improving solubility at low pH, for example, it is 0.01% by mass or more, preferably 0.02% by mass or more, and more preferably 0.03% by mass or more. In addition, the content of component (B) may be, for example, set to 60% by mass or less, preferably 40% by mass or less, and more preferably 10% by mass or less. More specifically, the content of component (B) is, for example, 0.01 to 60% by mass, preferably 0.02 to 40% by mass, and more preferably 0.03 to 10% by mass.

[0082] The content of component (C) varies according to the types and concentrations of other components contained in the composition of the present invention, and various conditions such as pH, and is therefore not particularly limited, but may be 0% by mass or more. In the case where the content of component (C) is 0% by mass, component (C) is not included. In the case where the composition of the present invention is an aqueous solution, from the viewpoint of helping to improve the foam quality (density), for example, it is 0.001% by mass or more, preferably 0.002% by mass or more, and more preferably 0.003% by mass or more. In addition, with regard to the content of component (C), from the viewpoint that a large amount of inclusion may hinder the effect of the present invention, for example, it may be set to 5% by mass or less, preferably 3% by mass or less, and more preferably 1% by mass or less. More specifically, the content of component (C) is, for example, 0.001 to 5% by mass, preferably 0.002 to 3% by mass, and more preferably 0.003 to 1% by mass.

[0083] The composition of the present invention is preferably weakly acidic from the viewpoint of storage stability based on the inhibition of bacterial growth (antiseptic effect) and low irritation to the skin based on a pH equivalent to that of the skin (weakly acidic). The pH of the composition of the present invention is, for example, 3 to 9, and can be set to 3 to 8 or 3 to 7. The upper limit of the pH is preferably 8 or less, and more preferably 7 or less. In addition, the lower limit is preferably 4 or more, and more preferably 4.5 or more. The pH of the composition of the present invention is preferably 4 to 8, more preferably 4 to 7, or preferably 4.5 to 8, and more preferably 4.5 to 7 from the viewpoint of having a pH equivalent to that of the skin. The composition of the present invention is also excellent in solubility at low pH, so precipitation is suppressed, and from this point of view, it can be considered that the storage stability is excellent. In addition, generally, anionic surfactants tend to reduce foaming when the pH becomes low, and the composition of the present invention foams well even at low pH. The pH can be adjusted by using a pH adjuster. Examples of the pH adjuster include the above-mentioned aqueous solutions (buffer solutions), acidic substances (eg, hydrochloric acid, sulfuric acid, nitric acid, citric acid), and alkaline substances (eg, hydroxides of alkali metals such as sodium and potassium, and alkaline earth metals such as calcium).

[0084] The viscosity of the composition of the present invention is preferably low from the viewpoint of handling. The viscosity of the composition of the present invention is, for example, 1.5 Pa·s or less, preferably 1 Pa·s or less, more preferably 0.8 Pa·s or less, further preferably 0.7 Pa·s or less, and further preferably 0.5 Pa·s or less. The composition of the present invention is excellent in handling and can be used as a cosmetic as a personal care product.

[0085] In this specification, the viscosity is a value obtained by measuring an aqueous solution of a composition having a concentration of 10% by mass using a B-type viscometer (DVB-10 (manufactured by Toyo Seiki Seisaku-sho, Ltd.), rotor No. 20 to 23, 6 to 30 rpm, 25° C., after 30 seconds).

[0086] Furthermore, the composition of the present invention may contain other components such as additional cleaning components, polyols, thickeners, stabilizers, preservatives, fragrances, pigments, etc. The specific types and amounts of these components can be appropriately set.

[0087] Examples of the additional cleaning component include surfactants such as anionic surfactants, amphoteric surfactants, and nonionic surfactants, and fine solids (such as microbeads and scrubs).

[0088] Anionic surfactants include one or more anionic groups. Examples of anionic groups include carboxyl groups, sulfonic acid groups, sulfate groups, and phosphoric acid groups. Examples of anionic surfactants include higher fatty acids, N-acylamino acids, N-acyltaurine, alkyl ether carboxylic acids, alkyl phosphoric acids, polyoxyethylene alkyl ether phosphoric acids, alkyl sulfuric acids, polyoxyethylene alkyl ether sulfuric acids, sulfonic acid compounds having alkyl chains, and salts thereof.

[0089] The amphoteric surfactant comprises one or more of the above-mentioned anionic groups and one or more of the above-mentioned cationic groups. Examples of the cationic group include an ammonium group, a primary amino group, a secondary amino group, a tertiary amino group, and a quaternary amino group. Examples of the amphoteric surfactant include amidobetaine type amphoteric surfactants, acetic acid betaine type amphoteric surfactants, sulfobetaine type amphoteric surfactants, and imidazoline type amphoteric surfactants (e.g., lauroylamphoacetic acid or its salt).

[0090] Examples of the nonionic surfactant include ester-type surfactants such as glycerol fatty acid esters, sorbitan fatty acid esters, and sucrose fatty acid esters; ether-type surfactants such as alkyl polyethylene glycols and polyoxyethylene alkylphenyl ethers; and alkyl glycosides and alkyl polyglycosides formed by combining sugars and higher alcohol glycosides.

[0091] Examples of the polyhydric alcohol include dihydric alcohols (e.g., ethylene glycol, propylene glycol, 1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 2,3-butanediol, 1,4-butanediol, 2-butene-1,4-diol, 1,5-pentanediol, 1,2-pentanediol, isoprene diol, hexanediol, diethylene glycol, dipropylene glycol, and glycerol monoesters (monoacylglycerols)), trihydric alcohols (e.g., glycerol, trimethylolpropane, and 1,2,6-hexanetriol), tetrahydric alcohols (e.g., dipropylene glycol and pentaerythritol), higher alcohols, and salts thereof (e.g., the above-mentioned inorganic salts and organic salts). As the polyhydric alcohol, for example, there can be mentioned: optionally substituted sugar alcohols (for example, monosaccharide alcohols such as sorbitol, mannitol, sucrose, glucose, and mannose, disaccharide alcohols such as trehalose, and polysaccharide alcohols such as hyaluronic acid and xanthan gum), and polymers of the above-mentioned divalent to tetravalent alcohols (for example, polyglycol, polyglycerol), and salts thereof (for example, the above-mentioned inorganic salts and organic salts). The polyhydric alcohol is preferably a divalent to tetravalent alcohol, and more preferably a divalent or trivalent alcohol.

[0092] Examples of the thickener include carrageenan, dextrin, methyl cellulose, ethyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, hydroxypropyl methyl cellulose, polyacrylic acid, polymethacrylic acid, carboxyvinyl polymer (carbomer), (acrylic acid / alkyl acrylate (C10-30)) copolymer, and xanthan gum.

[0093] Examples of the stabilizer include ascorbic acid, sodium pyrosulfite, and EDTA.

[0094] Examples of the preservative include ethyl p-hydroxybenzoate, sodium benzoate, salicylic acid, sorbic acid, p-hydroxybenzoic acid esters (such as methyl p-hydroxybenzoate and propyl p-hydroxybenzoate), and sodium hydrogen sulfite.

[0095] Examples of the fragrance include natural fragrances and synthetic fragrances. Examples of the natural fragrance include rose oil, jasmine oil, orange blossom oil, lavender oil, ylang-ylang oil, tuberose oil, clarified oil, clove oil, peppermint oil, geranium oil, patchouli oil, sandalwood oil, cinnamon oil, coriander oil, nutmeg oil, pepper oil, lemon oil, orange oil, bergamot oil, poppy oil, vetiver oil, iris oil, and oakmoss oil. Examples of synthetic fragrances include limonene (orange), β-caryophyllene (woody scent), sis-3-hexenol (fresh green leaves), linalool (lily of the valley), farnesol (fresh green floral scent), β-phenylethyl alcohol (rose), 2,6-nonadiene (violet, cucumber), citral (lemon), α-hexylcinnamaldehyde (jasmine), β-ionone (violet is obtained by dilution), ι-carvone (spearmint), cyclopentadecanone (musk), linalyl acetate (bergamot, lavender), benzyl benzoate (balsam), γ-undecanolactone (peach), eugenol (clove), rose oxide (green leaf and floral scent), indole (jasmine is obtained by dilution), phenylacetaldehyde dimethyl acetal (hyacinth), orlanthiol (neroli), and menthol (mint) (fragrance is indicated in parentheses).

[0096] Examples of the pigment include organic pigments (e.g., red pigments such as Red No. 201, blue pigments such as Blue No. 404, orange pigments such as Orange No. 203, yellow pigments such as Yellow No. 205, green pigments such as Green No. 3, organic lake pigments such as zirconium lake, and natural pigments such as chlorophyll) and inorganic pigments (e.g., white pigments such as titanium oxide, colored pigments such as iron oxide, extender pigments such as talc, and pearlescent pigments such as mica).

[0097] The composition of the present invention can be provided in various forms, such as powder, liquid, gel, paste, cream, foam, etc. It should be noted that the composition of the present invention can be produced by a conventional method.

[0098] The composition of the present invention can be made into any form of cosmetics that can be applied to skin, hair, scalp, etc. by conventional methods. As cosmetics, for example, as detergents for humans and other animals, they are suitable for use in body washes, hand soaps, facial cleansers, cleansing lotions, cleansing creams, massage creams, and hair shampoos. The preferred properties of cosmetics (e.g., pH) are the same as the preferred properties of the composition of the present invention.

[0099] In addition, the composition of the present invention can also be used as an additive such as an excipient. Example

[0100] Hereinafter, the present invention will be described in more detail based on Examples. The following Examples are examples for appropriately describing the present invention and are not intended to limit the present invention.

[0101] Synthesis Example 1: (Production Example of N-dodecenoylglutamic acid (C12:1))

[0102] Dissolve 3.0 g of cis-5-dodecenoic acid in 30 ml of dichloromethane and cool on ice. Add 3 drops of N,N-dimethylformamide (DMF) and 2.0 ml of oxalyl chloride, and stir at room temperature for 2 hours. Distill off the dichloromethane in the reaction solution by vacuum concentration, add 25 ml of dichloromethane again and concentrate under reduced pressure. Repeat this operation 3 times to obtain cis-5-dodecenoyl chloride. Add 30 ml of 1M sodium hydroxide aqueous solution and 15 ml of acetone to 2.4 g of L-glutamic acid and dissolve, and cool on ice. Dissolve the previous acid chloride in 15 ml of acetone, and slowly drop glutamic acid aqueous solution. During this period, add 1M sodium hydroxide aqueous solution to adjust to pH 10-11. After the pH does not change, add 15 ml of hexane to wash the reaction solution, separate the layers to obtain the aqueous layer. Add 100 mL of dichloromethane, adjust to pH 2 or less with sulfuric acid and extract. Dry the dichloromethane layer with anhydrous magnesium sulfate. The dichloromethane was removed by distillation under reduced pressure and concentration, and 25 ml of dichloromethane was added to the residue again and concentrated under reduced pressure. This operation was repeated twice, and 50 ml of dichloromethane was added to the residue and heated to dissolve. After dissolution, it was cooled on ice and crystallized. The precipitated solid was separated and dried under reduced pressure at 40°C to obtain 3.4 g of the target product. It was confirmed by HPLC that sufficient reaction had occurred.

[0103] Synthesis Example 2: (Production Example of N-hexadecenoylglutamic acid (C16:1))

[0104] The target product (1.4 g) was obtained by the same method as above using 1.7 g of cis-9-hexadecenoic acid. The reaction was confirmed to be complete by HPLC.

[0105] Synthesis Example 3: (Production Example of N-saturated C8-C16 acyl glutamate sodium)

[0106] Under alkaline conditions, the fatty acid chlorides of the corresponding fatty chain lengths are fully reacted with the reaction amount of glutamate. After the reaction is completed, acid is added and crystallized, and then filtered. After a neutralization step and a drying step, a powdery N-saturated acyl sodium glutamate is obtained. It should be noted that HPLC confirmed that the obtained N-saturated acyl sodium glutamate was fully reacted.

[0107] (Evaluation of foaming, foam quality, dissolution and viscosity)

[0108] A 0.3 mass % aqueous solution and a 10 mass % aqueous solution concentration of the composition of Tables 1 to 3 were prepared using an aqueous sodium hydroxide solution and an aqueous citric acid solution.

[0109] [Foaming measurement]: 20 g of a 0.3 mass % aqueous solution of the composition of Tables 1 to 3 was weighed into a 100 mL glass vial container and heated to 35° C. Then, after shaking for 10 seconds using a Vortex (Scientific Industries, VORTEX-GENIE2, 3000 rpm), the height of the bubbles was immediately measured as foaming and evaluated based on the following evaluation criteria.

[0110] (Evaluation Criteria)

[0111] A: The bubble height is more than 35mm

[0112] B: Bubble height is 30 mm or more and less than 35 mm

[0113] C: Bubble height less than 30mm

[0114] [Evaluation of foam quality]: 20 g of a 0.3 mass % aqueous solution of the composition of Tables 1 to 3 was weighed into a 100 mL glass vial container and heated to 35° C. After being shaken for 10 seconds using a Vortex (Scientific Industries, VORTEX-GENIE2, 3000 rpm), foam quality was immediately evaluated by five professionals based on the following evaluation criteria.

[0115] (Evaluation Criteria)

[0116] 5 points: The foam feels very thick

[0117] 4 points: The foam feels slightly thick

[0118] 3 points: It’s hard to say whether it’s thick or not

[0119] 2 points: The foam doesn’t feel too thick

[0120] 1 point: The foam doesn’t feel thick enough

[0121] The scores of the five experts were totaled, and the foam quality was evaluated based on the following evaluation criteria.

[0122] (Evaluation Criteria)

[0123] AA: The total score of the 5 players is 23 points or more

[0124] A: The total score of the five contestants is 20 points or more but less than 23 points.

[0125] B: The total score of the five participants is 10 points or more but less than 20 points

[0126] C: The total score of the 5 players is less than 10 points

[0127] [Dissolution]: Into a 30 mL glass vial container, 10 g of a 10 mass % aqueous solution of the composition of Tables 1 to 3 was weighed, and then stored at 25°C. The state of crystal precipitation after one week was confirmed by visual observation and evaluated based on the following evaluation criteria.

[0128] (Evaluation Criteria)

[0129] A: It is a transparent solution

[0130] B: Precipitation is observed at the bottom of the glass vial or the entire solution is cloudy

[0131] C: Precipitation was observed throughout the glass vial

[0132] [Viscosity]: Into a 30 mL glass vial container, 10 g of a 10 mass % aqueous solution of the composition of Tables 1 to 3 was weighed and stored at 25°C. The viscosity at 25°C after one week was confirmed by visual observation by 5 experts and evaluated based on the following evaluation criteria.

[0133] (Evaluation Criteria)

[0134] 5 points: Low viscosity compared to tap water

[0135] 4 points: Slightly lower viscosity than tap water

[0136] 3 points: The viscosity is similar to tap water

[0137] 2. Slightly higher viscosity than tap water

[0138] 1 point: High viscosity compared to tap water

[0139] The scores of the five experts were totaled, and the viscosity was evaluated based on the following evaluation criteria.

[0140] A: The total score of the 5 players is 19 points or more

[0141] B: The total score of the five participants is 10 points or more and less than 19 points

[0142] C: The total score of the 5 players is less than 10 points

[0143] [Comprehensive evaluation]: For the above four tests, the evaluation criteria were A = 5 points, B = 4 points, and C = 1 point. Comprehensive evaluation was performed based on the following evaluation criteria.

[0144] (Evaluation Criteria)

[0145] A: 18 points or more

[0146] B: 16 or more but less than 17

[0147] C: 15 points or less

[0148] [Table 1]

[0149]

[0150] The above results show that the surfactant of the present invention has good foaming, foam quality and solubility even in the weakly acidic region with a pH equivalent to that of the skin, and has a low viscosity with high handling properties. On the other hand, sodium N-lauroyl glutamate (C12GluNa) has good foaming and foam quality at low pH, but poor solubility and handling properties (Comparative Examples 1 to 3). In addition, at neutral pH, the solubility and handling properties are good, but the foaming and foam quality are poor (Comparative Example 4).

[0151] It should be noted that in Table 1, "C12:1Glu" is N-dodecenoyl glutamate, and "C12GluNa" is sodium N-lauroyl glutamate.

[0152] [Table 2]

[0153]

[0154] The above results show that the use of N-dodecenoyl glutamic acid and sodium N-lauroyl glutamate (C12GluNa) in combination solves the problems of using sodium N-lauroyl glutamate (C12GluNa) alone. That is, the composition of the present invention has good foaming, foam quality and solubility even in a weakly acidic pH region of the same degree as that of the skin, and has a low viscosity with high handling properties.

[0155] It should be noted that in Table 2, "C12:1Glu" is N-dodecenoyl glutamate, and "C12GluNa" is sodium N-lauroyl glutamate.

[0156] [Table 3]

[0157]

[0158] The above results show that the composition of the present invention has good foaming, foam quality and solubility even in a weakly acidic pH region similar to that of the skin, and has a low viscosity with high handling properties.

[0159] When two or more N-saturated acyl acidic amino acids were used in combination, the results were superior to those of the examples described in Table 2 in which only one was used. In addition, when two N-monounsaturated acyl acidic amino acids were used, the foam quality was evaluated as "AA", which was a better result. In contrast, when no N-monounsaturated acyl acidic amino acids were used, the overall evaluation was poor.

[0160] It should be noted that in Table 3, "C12:1Glu" is N-dodecenoylglutamate, "C16:1Glu" is N-hexadecenoylglutamate, "C18:1Glu" is N-oleoylglutamate, "C8GluNa" is sodium N-octanoyl glutamate, "C10GluNa" is sodium N-hexanoyl glutamate, "C12GluNa" is sodium N-lauroyl glutamate, "C14GluNa" is sodium N-myristoyl glutamate, and "C16GluNa" is sodium N-palmitoyl glutamate.

[0161] The following oil detergency evaluation test was conducted on the compositions of Examples 11 and 15 and Comparative Example 6. The results are shown in Table 4.

[0162] [Oil cleaning power]: The cleaning power of oil (vaseline, Sun White P-200, NIKKO-RICA Co., Ltd.) applied to artificial leather was evaluated. The oil cleaning power was evaluated by the following method.

[0163] First, artificial leather was weighed by a precision balance and 0.10 g of vaseline was applied thereon. 0.30 g of each sample was dripped from the applied vaseline and vaseline was mixed with each sample for 20 seconds in a circle with a finger wearing a rubber glove. Then, the artificial leather was put into a 500 mL beaker filled with 300 mL of tap water and stirred at a speed of 100 rpm for 30 seconds to rinse the oil content. Finally, the artificial leather was dried for 3 days in a room where temperature and humidity were managed, and the weight was measured and the cleaning power of the oil was calculated according to the following formula (1). The cleaning power of the oil was evaluated according to the following benchmark, and the result is shown in Table 4.

[0164] Formula (1): Cleaning rate = ((weight of vaseline rinsed) / (weight of vaseline applied)) × 100

[0165] (Evaluation Criteria)

[0166] A: Cleaning rate is more than 23%

[0167] B: Cleaning rate is 17.5% or more and less than 23%

[0168] C: Cleaning rate less than 17.5%

[0169] [Table 4]

[0170]

[0171] The above results show that the detergency of the oil in the composition of the present invention is evaluated as "A" or "B". In particular, when N-monounsaturated fatty acids are included, the evaluation of "A" is a particularly good result. In contrast, the detergency of the oil in the composition of the comparative example is "C", that is, it is difficult to be compatible with oil.

[0172] For the compositions of Examples 17 and 18 and Comparative Example 7, the following viscosity measurement was performed.

[0173] [Viscosity]: A B-type viscometer manufactured by Toyo Seiki Seisaku-sho (Co., Ltd.) was used for the viscosity measurement. A 50 mL glass vial container was filled with an aqueous solution diluted to a concentration of 10%, and the viscosity was measured. The measurement conditions were set to rotor number 20 or 21, rotation speed: 12 or 30 rpm, and measurement time: 30 seconds. The measurement was carried out, and the results are shown in Table 5.

[0174] In addition, although the measurement was attempted for the 10 mass % aqueous solution of Comparative Example 1, precipitation was observed, and thus the measurement by the viscometer could not be performed.

[0175] [Table 5]

[0176]

[0177] The above results show that the viscosity of the composition of the example is 23 or 12 mPa·s, which is a low viscosity, while the viscosity of the composition of the comparative example is 1992 mPa·s (1.992 Pa·s), which is a high viscosity.

[0178] It should be noted that in Table 5, "C12:1Glu" is N-dodecenoylglutamate, "C16:1Glu" is N-hexadecenoylglutamate, "C18:1Glu" is N-oleoylglutamate, "C8GluNa" is sodium N-octanoyl glutamate, "C10GluNa" is sodium N-hexanoyl glutamate, "C12GluNa" is sodium N-lauroyl glutamate, "C14GluNa" is sodium N-myristoyl glutamate, and "C16GluNa" is sodium N-palmitoyl glutamate.

Claims

1. A composition comprising: Component (A): two or more N-monounsaturated acyl acidic amino acids or salts thereof, wherein the unsaturated acyl group is an acyl group having 10 to 16 carbon atoms, and the N-monounsaturated acyl acidic amino acids are compounds represented by the following general formula (1): In the general formula (1), l is an integer of 1 or 2, and m is an integer of 0 to 6; and Component (B): one or more N-saturated acyl acidic amino acids selected from the group consisting of N-octanoyl acidic amino acids (C8), N-hexanoyl acidic amino acids (C10), N-lauroyl acidic amino acids (C12), N-myristoyl acidic amino acids (C14), N-palmitoyl acidic amino acids (C16) and N-stearoyl acidic amino acids (C18), or salts thereof; The two or more N-monounsaturated acyl acidic amino acids in component (A) include: (A1) an N-monounsaturated acyl acidic amino acid or a salt thereof, wherein the unsaturated acyl group is an acyl group having 12 carbon atoms; and (A2) an N-monounsaturated acyl acidic amino acid or a salt thereof, wherein the unsaturated acyl group is an acyl group having 10, 14 or 16 carbon atoms, The weight ratio (A / (A+B)) of the component (A) to the total of the component (A) and the component (B) is 0.001 to 1.

2. The composition according to claim 1, wherein The stereochemistry of the N-monounsaturated acyl acidic amino acid is cis.

3. The composition according to claim 1, wherein The N-monounsaturated acyl acidic amino acid is N-monounsaturated acyl glutamic acid.

4. The composition according to claim 1, wherein Ingredient (A) comprises: (A1) an N-monounsaturated acyl acidic amino acid or a salt thereof, wherein the unsaturated acyl group is an acyl group having 12 carbon atoms; and (A2) N-monounsaturated acyl acidic amino acid or a salt thereof, wherein the unsaturated acyl group is an acyl group having 16 carbon atoms.

5. The composition according to claim 1, wherein Ingredient (B) comprises: (B1) N-lauroyl acidic amino acid and / or its salt.

6. The composition according to claim 5, wherein Component (B) further comprises: (B2) N-saturated acyl acidic amino acid and / or its salt, wherein the saturated acyl group is an acyl group having 8, 10, 14 or 16 carbon atoms.

7. The composition according to claim 1, further comprising: Component (C) N-unsaturated fatty acid or a salt thereof.

8. The composition according to claim 1, further comprising: Component (D) Aqueous medium.

9. The composition according to claim 5, wherein In the component (B), the content of (B1) N-lauroyl acidic amino acid and / or its salt is 20% by mass or more.

10. The composition according to claim 6, wherein (B2) is one or more selected from the group consisting of N-hexanoyl acidic amino acid (C10), N-myristoyl acidic amino acid (C14) and N-palmitoyl acidic amino acid (C16).

11. The composition according to claim 7, wherein Component (C) contains dodecenoic acid or a salt thereof.

12. The composition according to claim 11, wherein The content of dodecenoic acid in the component (C) is 30% by mass or more.

13. The composition according to claim 11, wherein The mass ratio of the component (C) to the total of the component (A) and the component (B) (C / (A+B)) is 0.001 or more. The composition according to claim 1 , which has a pH of 3 to 9. The composition according to claim 1 , which has a viscosity of 1.5 Pa·s or less. The composition according to claim 1 , which is a composition for external use on skin.

17. The composition according to any one of claims 1 to 16, which is a detergent composition.

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