Surfactants and compositions

Abstract

The present invention provides a surfactant which has good lathering properties, good lather quality and solubility even in a weak acidic range where the pH is equivalent to that of the skin, while having a low viscosity that leads to high handling properties, and which is applicable to personal care products (such as a cosmetic preparation) and the like. More specifically, the present invention provides a surfactant which contains an N-monounsaturated acyl acidic amino acid (wherein the unsaturated acyl is an acyl having from 10 to 16 carbon atoms) or a salt thereof.

Description

[Technical field]

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

[0002] Surfactants are used in a variety of applications, such as cleaning, emulsification, solubilization, dispersion, foaming, lubrication, antistatic, and rust prevention, in personal care, home care, agricultural chemicals, paints, inks, lubricating oil additives, cutting oil additives, rust inhibitors, etc. For example, when used in personal care applications, surfactants are often blended as cleansing agents for the body and hair.

[0003] In recent years, for body and hair use, there has been a demand for detergent compositions that not only have high detergency but also have low irritation to the skin and excellent usability. Among these, detergent compositions containing amino acid-based active ingredients, such as N-acyl glutamate and N-acyl glycine salt, have attracted attention. For body and hair detergents, a weak acid range with a pH equivalent to that of the skin is preferred so that they are more mild to the skin, but in the weak acid range, transparency may not be maintained or sufficient foaming may not be obtained.

[0004] Regarding N-acylglutamic acid, a type of N-acyl acidic amino acid, there have been reports of studies on improving the functionality of N-acylglutamic acid by adjusting the fatty acid chain length of the acyl group (Patent Documents 1 and 2). However, these reports are limited to consideration of N-acylglutamic acid having an acyl group derived from a fatty acid that is easily available from natural plants. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] JP 2009-51945 A [Patent Document 2] JP 2003-34670 A Summary of the Invention [Problem to be solved by the invention]

[0006] The object of the present invention is to find a new surfactant by adjusting the acyl group of the N-acyl acidic amino acid, and to solve the problems of N-saturated acyl acidic amino acid or its salt (such as problems of transparency and foaming in a weak acidic range) by using it in addition to an existing N-saturated acyl acidic amino acid or its salt. More specifically, the object of the present invention is to provide a surfactant that has good foaming, foam quality and solubility even in a weak acidic range that is the same pH as the skin, and has a low viscosity with high handleability, and that can be applied to products such as personal care (e.g., cosmetics), and a composition containing the surfactant that also has improved oil cleaning power. [Means for solving the problem]

[0007] As a result of intensive research into the above-mentioned problems, the present inventors have found that N-monounsaturated acyl acidic amino acid (wherein the unsaturated acyl is an acyl having 10 to 16 carbon atoms) or a salt thereof has good foaming, foam quality and solubility even in a weakly acidic region having a pH similar to that of skin, and has a low viscosity with high handleability, thereby completing the present invention. In addition, the present inventors have found that a composition using N-monounsaturated acyl acidic amino acid (wherein the unsaturated acyl is an acyl having 10 to 16 carbon atoms) or a salt thereof in combination with N-saturated acyl acidic amino acid or a salt thereof improves the detergency of oil in addition to the effect of the surfactant, thereby completing the present invention. Even in a weakly acidic region with a pH equivalent to that of the skin, the surfactant has good foaming, foam quality and solubility, which provides good applicability to the skin, as well as excellent storage stability by suppressing precipitation. In addition, unlike typical anionic surfactants, the surfactant has the advantage of being low in viscosity and easy to handle even at low pH. A surfactant with these advantages is considered to be particularly suitable for use in products such as personal care (e.g., cosmetics) that can be applied directly to the skin. In addition, the improved cleaning power of the oil has the advantage that more effective cleaning power can be expected. Therefore, in addition to the effect of the surfactant, a composition that exhibits this advantage is considered to be particularly suitable for use as a cleanser for the body, including the face, and hair, among other personal care product applications.

[0008] That is, the present inventors provide the following [1] to

[15] . [1] A surfactant comprising an N-monounsaturated acyl acidic amino acid (wherein the unsaturated acyl is an acyl having 10 to 16 carbon atoms) or a salt thereof. [2] The surfactant according to the above [1], wherein the N-monounsaturated acyl acidic amino acid is a compound represented by the following general formula (1): [ka] (In the general formula (1), l is an integer of 1 or 2, and m is an integer of 0 to 6.) [3] The surfactant according to [1] or [2] above, wherein the stereochemistry of the N-monounsaturated acyl acidic amino acid is cis. [4] The surfactant according to any one of the above [1] to [3], wherein the N-monounsaturated acyl acidic amino acid is N-monounsaturated acyl glutamic acid. [5] A composition comprising component (A) an N-monounsaturated acyl acidic amino acid (wherein the unsaturated acyl is an acyl having 10 to 16 carbon atoms) or a salt thereof, and component (B) an N-saturated acyl acidic amino acid or a salt thereof. [6] The composition according to the above [5], wherein the component (A) comprises (A1) an N-monounsaturated acyl acidic amino acid (wherein the unsaturated acyl is an acyl having 12 carbon atoms) or a salt thereof, and (A2) an N-monounsaturated acyl acidic amino acid (wherein the unsaturated acyl is an acyl having 10, 14, or 16 carbon atoms) or a salt thereof. [7] The composition according to [5] or [6] above, wherein component (B) comprises (B1) an N-lauroyl acidic amino acid and / or a salt thereof. [8] The composition according to [7] above, wherein component (B) further comprises (B2) an N-saturated acyl acidic amino acid (wherein the saturated acyl is an acyl having 8, 10, 14, or 16 carbon atoms) and / or a salt thereof. [9] The composition according to any one of the above [5] to [8], further comprising component (C) an N-unsaturated fatty acid or a salt thereof.

[10] The composition according to any one of the above [5] to [9], further comprising a component (D) an aqueous medium.

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

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

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

[11] , having a pH of 3 to 9.

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

[12] , having a viscosity of 1.5 Pa·s or less.

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

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

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

[13] , which is a cleaning composition. Effect of the Invention

[0009] The surfactant of the present invention has the effect of having good foaming, foam quality and solubility even in a weakly acidic region having a pH similar to that of skin, and has a low viscosity with high handleability. Therefore, the surfactant of the present invention is particularly suitable for use in products such as personal care (e.g., cosmetics) that can be directly applied to the skin. In addition to the above effects, the composition of the present invention also has the effect of improving the detergency of oils, and therefore is particularly suitable for use as a cleanser for the body (including the face), hair, etc., among personal care product applications that can be applied directly to the skin. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0010] 1. Surfactants The surfactant of the present invention contains an N-monounsaturated acyl acidic amino acid (wherein the unsaturated acyl is an acyl having 10 to 16 carbon atoms) or a salt thereof. Since the acyl moiety of the N-monounsaturated acyl acidic amino acid is a monounsaturated acyl, the viscosity is not reduced excessively. Also, since the number of carbon atoms in the acyl moiety is 10 to 16, the viscosity is not increased too much, and the viscosity is low and easy to handle, and the solubility is good. In addition, the foaming and foam quality are good.

[0011] In the present specification, "acyl having n carbon atoms" means n-1 H m It refers to acyl represented by -CO- (hydrogen atoms may be substituted), where m is appropriately determined depending on the number of carbon atoms and the presence or absence of an unsaturated bond.

[0012] In the present specification, the term "N-monounsaturated acyl acidic amino acid (wherein acyl is an acyl having 10 to 16 carbon atoms)" refers to, in the free form, n-1 H m -CO-NH-CHR-COOH (H m may be 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 in which one hydrogen atom on the amino group of an acidic amino acid is substituted 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.

[0013] The salt of N-mono-unsaturated acyl acidic amino acid may include, for example, inorganic salt and organic salt.The inorganic salt may include, for example, salt of metal (e.g., monovalent metal such as lithium, sodium, potassium, rubidium, and cesium, and divalent metal such as calcium, magnesium, and zinc) and salt of inorganic base (e.g., ammonia).The organic salt may include, for example, salt of organic base (e.g., ethylenediamine, propylenediamine, ethanolamine, monoalkylethanolamine, dialkylethanolamine, diethanolamine, triethanolamine, lysine, arginine, histidine, and ornithine).

[0014] In this specification, N-monounsaturated acyl acidic amino acid is conveniently referred to as C n-1 H m -COOH or its derivatives. In the present specification, the "unsaturated acyl having n carbon atoms" and the fatty acid derived therefrom may be expressed 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 an acidic amino acid is replaced with 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.

[0015] When the N-monounsaturated acyl acidic amino acid is obtained from a monounsaturated fatty acid, the N-monounsaturated acyl acidic amino acid can be, for example, C n-1 H m The monounsaturated fatty acid derivative represented by -COX (X is any monovalent group, for example, a halogen atom selected from the group consisting of fluorine, chlorine, bromine, and iodine) can be obtained by reacting an acidic amino acid or a salt thereof (examples of the salt include the inorganic salts and organic salts as described above).

[0016] Examples of monounsaturated fatty acids from which N-monounsaturated acyl acidic amino acids are derived include decenoic acid (C10:1), dodecenoic acid (C12:1), tetradecenoic acid (C14:1) (e.g., myristoleic acid), and hexadecenoic acid (C16:1) (e.g., palmitoleic acid), with dodecenoic acid (C12:1) or hexadecenoic acid (C16:1) being preferred, and dodecenoic acid (C12:1) being even more preferred.

[0017] 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.

[0018] Examples of N-monounsaturated acyl acidic amino acids include N-decenoyl acidic amino acid (C10:1), N-dodecenoyl acidic amino acid (C12:1), N-tetradecenoyl acidic amino acid (C14:1), and N-hexadecenoyl acidic amino acid (C16:1). N-dodecenoyl acidic amino acid (C12:1) or N-hexadecenoyl acidic amino acid (C16:1) is preferred, N-dodecenoyl glutamic acid (C12:1) or N-hexadecenoyl glutamic acid (C16:1) is more preferred, and N-dodecenoyl glutamic acid (C12:1) is even more preferred.

[0019] The N-monounsaturated acyl acidic amino acid may be one type of N-monounsaturated acyl acidic amino acid or a salt thereof, or may contain two or more types of 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 the group consisting of N-decenoyl acidic amino acid (C10:1), N-dodecenoyl acidic amino acid (C12:1), N-tetradecenoyl acidic amino acid (C14:1), and N-hexadecenoyl acidic amino acid (C16:1). When two or more types of N-monounsaturated acyl acidic amino acids are used, a combination of N-dodecenoyl acidic amino acid (C12:1) and one or more selected from the group consisting of N-decenoyl acidic amino acid (C10:1), N-tetradecenoyl acidic amino acid (C14:1), and N-hexadecenoyl acidic amino acid (C16:1) is preferred, and from the viewpoint of improving foam quality, a combination of N-dodecenoyl acidic amino acid (C12:1) and N-hexadecenoyl acidic amino acid (C16:1) is more preferred.

[0020] The unsaturated bond site of the N-monounsaturated acyl acidic amino acid is not particularly limited, and may be the carbon chain terminal of the acyl moiety, between carbon atoms several carbon atoms away from the carbon chain terminal of the acyl moiety, or the α-position of the carbonyl group of the acyl moiety. Among them, it is preferable that the unsaturated bond is between carbon atoms 6 to 7 carbon atoms away from the carbon chain terminal of the acyl moiety. That is, the N-monounsaturated acyl acidic amino acid is preferably a compound represented by the following general formula (1).

[0021] [ka] (In general formula (1), l is an integer of 1 or 2, and m is an integer of 0 to 6.)

[0022] The stereochemistry (unsaturated double bond site) of the N-monounsaturated acyl acidic amino acid may be either cis or trans, but from the viewpoint of suppressing an increase in viscosity and achieving a low viscosity with good handleability, cis is preferred.

[0023] 2. Composition The composition of the present invention comprises component (A) an N-monounsaturated acyl acidic amino acid (wherein the unsaturated acyl is an acyl having 10 to 16 carbon atoms) or a salt thereof, and component (B) an N-saturated acyl acidic amino acid or a salt thereof. The composition of the present invention contains component (A), and therefore has good foaming, foam quality and solubility even in a weakly acidic region that is the same pH as that of the skin, and has low viscosity with good handling properties. In addition, the composition of the present invention also contains component (B), and therefore has a variety of acyl groups, and therefore has the effect of improving the cleaning power of oil.

[0024] (Component (A)) Details of component (A) are as described above in relation to the N-monounsaturated acyl acidic amino acid of the surfactant.

[0025] (Component (B)) As used herein, the term "N-saturated acyl acidic amino acid" refers to, in the free form, n-1 H m -CO-NH-CHR-COOH (H m may be substituted. m is as defined above. R represents the side chain of an acidic amino acid. ). In other words, "N-saturated acyl acidic amino acid" refers to a compound in which one hydrogen atom on the amino group of an acidic amino acid is substituted with a saturated acyl group. "N-saturated acyl acidic amino acid" may be a free form of N-saturated acyl acidic amino acid or a salt of N-saturated acyl acidic amino acid. The salts of N-saturated acyl acidic amino acids may be similar to the salts of N-monounsaturated acyl acidic amino acids.

[0026] In this specification, N-saturated acyl acidic amino acids are conveniently referred to as C n-1 H m-COOH or its derivatives. In the present specification, "saturated acyl having n carbon atoms" and the fatty acid derived therefrom may be expressed 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 an acidic amino acid is replaced with 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.

[0027] When the N-saturated acyl acidic amino acid is obtained from a saturated fatty acid, the N-saturated acyl acidic amino acid can be, for example, C n-1 H m The saturated fatty acid derivative represented by -COX (X is any monovalent group, for example, a halogen atom selected from the group consisting of fluorine, chlorine, bromine, and iodine) can be obtained by reacting an acidic amino acid or a salt thereof (examples of the salt include the inorganic salts and organic salts as described above).

[0028] Examples of N-saturated acyl acidic amino acids include N-capryloyl acidic amino acids (C8), N-caproyl 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).

[0029] The "acidic amino acid" in "N-saturated acyl acidic amino acid" refers to an amino acid having an acidic side chain. Examples of acidic amino acids include glutamic acid and aspartic acid, with glutamic acid being preferred.

[0030] The N-saturated acyl acidic amino acid is preferably N-capryloyl acidic amino acid (C8), N-caproyl 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 even more preferably N-lauroyl glutamic acid (C12).

[0031] Component (B) may be one type of N-saturated acyl acidic amino acid or a salt thereof, or may contain two or more types of N-saturated acyl acidic amino acids or salts thereof. That is, component (B) may contain one or more selected from the group consisting of N-capryloyl acidic amino acid (C8), N-caproyl 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 kinds of N-saturated acyl acidic amino acids, it is preferable to include N-lauroyl acidic amino acid (C12), and more preferably to include a combination of N-lauroyl acidic amino acid (C12) with one or more selected from the group consisting of N-capryloyl acidic amino acid (C8), N-caproyl acidic amino acid (C10), N-myristoyl acidic amino acid (C14), and N-palmitoyl acidic amino acid (C16).

[0032] 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, even more preferably 40% by mass or more, and even more 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, even more preferably 40 to 100% by mass, and even more preferably 50 to 100% by mass.

[0033] The mass ratio of component (A) to the total of components (A) and (B) (A / (A+B)) is usually 0.001 or more, preferably 0.002 or more, more preferably 0.003 or more, and even more preferably 0.004 or more, from the viewpoint of improving solubility at low pH by component (A), etc. The mass ratio of component (A) to the total of components (A) and (B) (A / (A+B)) can also be 1 or less, preferably less than 1, more preferably 0.8 or less, even more preferably 0.6 or less, and even more preferably 0.5 or less, from the viewpoint of the contribution of a high content of component (B) to the detergency of oil, etc. More specifically, the mass ratio of component (A) to the total of components (A) and (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, even more preferably 0.003 to 0.6, and even more preferably 0.004 to 0.5.

[0034] The composition of the present invention may further comprise component (C) an N-unsaturated fatty acid or a salt thereof. When the composition of the present invention contains component (C), the foam quality is improved and the detergency for oil is further improved.

[0035] (Component (C)) The number of carbon atoms of the unsaturated fatty acid is preferably 6 to 22, and more preferably 8 to 18. Examples of the unsaturated fatty acid include hexenoic acid (C6:1), octenoic acid (C8:1), decenoic acid (C10:1), dodecenoic acid (C12:1), tetradecenoic acid (C14:1) (e.g., myristoleic acid), hexadecenoic acid (C16:1) (e.g., palmitoleic acid), octadecenoic acid (C18:1) (e.g., oleic acid), icosenoic acid (C20:1) (e.g., eicosenoic acid), and docosenoic acid (C22:1), with dodecenoic acid (C12:1) being preferred.

[0036] Examples of salts of unsaturated fatty acids 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 these, triethanolamine salts, sodium salts, and potassium salts are preferred.

[0037] Component (C) may be one type of unsaturated fatty acid or its salt, or may contain two or more types of unsaturated fatty acids or their salts. That is, component (C) may contain one or more selected from the group consisting of hexenoic acid (C6:1), octenoic acid (C8:1), decenoic acid (C10:1), dodecenoic acid (C12:1), tetradecenoic acid (C14:1) (e.g., myristoleic acid), hexadecenoic acid (C16:1) (e.g., palmitoleic acid), octadecenoic acid (C18:1) (e.g., oleic acid), icosenoic acid (C20:1) (e.g., eicosenoic acid), and docosenoic acid (C22:1). In the case of two or more kinds of unsaturated fatty acids or salts thereof, it is preferable to include dodecenoic acid (C12:1), and it is more preferable to include a combination of dodecenoic acid (C12:1) with one or more selected from the group consisting of octenoic acid (C8:1), decenoic acid (C10:1), tetradecenoic acid (C14:1), and hexadecenoic acid (C16:1).

[0038] When component (C) contains 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, even more preferably 60% by mass or more, even more 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, even more preferably 60 to 100% by mass, even more preferably 70 to 100% by mass, and particularly preferably 80 to 100% by mass.

[0039] The mass ratio (C / (A+B)) of component (C) to the total of component (A) and component (B) may be 0 or more. 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 of the contribution of component (C) to the improvement of foam quality (density), it can be 0.001 or more, preferably 0.01 or more, more preferably 0.1 or more, even more preferably 0.2 or more, even more preferably 0.4 or more, and particularly preferably 0.5 or more. The mass ratio (C / (A+B)) of component (C) to the total of component (A) and component (B) is also usually 20 or less, preferably 15 or less, more preferably 13 or less, even more preferably 11 or less, and even more preferably 10 or less, from the viewpoint of the contribution of the effects of component (A) and component (B). More specifically, the mass ratio of component (C) to the total of components (A) and (B) (C / (A+B)) is usually 0.001 to 20, preferably 0.01 to 20, more preferably 0.1 to 15, even more preferably 0.2 to 13, even more preferably 0.4 to 11, and particularly preferably 0.5 to 10.

[0040] The composition of the present invention may contain component (A), component (B), and optional component (C) in (D) an aqueous medium. Any aqueous solvent can be used as the aqueous medium. Examples of the aqueous medium include aqueous solutions. The aqueous solution may or may not have a buffering capacity. Examples of the aqueous solution include water (e.g., distilled water, sterilized distilled water, purified water, physiological saline, tap water such as city water), phosphate buffer, Tris-hydrochloric acid buffer, TE (Tris-EDTA) buffer, carbonate buffer, borate buffer, tartrate buffer, glycine buffer, citrate buffer, and acetate buffer.

[0041] The content of component (A) is not particularly limited because it varies depending on various conditions such as the type and concentration of other components contained in the composition of the present invention, and pH. When the composition of the present invention is in the form of an aqueous solution, from the viewpoint of improving solubility at low pH, the content is, for example, 0.001% by mass or more, preferably 0.002% by mass or more, and more preferably 0.003% by mass or more. The content of component (A) can also be, for example, 60% by mass or less, and preferably 40% by mass or less. More specifically, the content of component (A) is, for example, 0.001 to 60% by mass, preferably 0.001 to 40% by mass, more preferably 0.002 to 40% by mass, and even more preferably 0.003 to 40% by mass.

[0042] The content of component (B) is not particularly limited because it varies depending on various conditions such as the type and concentration of other components contained in the composition of the present invention, and pH. When the composition of the present invention is in the form of an aqueous solution, from the viewpoint of improving solubility at low pH, it is, for example, 0.01% by mass or more, preferably 0.02% by mass or more, and more preferably 0.03% by mass or more. The content of component (B) can also be, for example, 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.

[0043] The content of component (C) is not particularly limited because it varies depending on various conditions such as the type and concentration of other components contained in the composition of the present invention, and pH, but may be 0% by mass or more. When the content of component (C) is 0% by mass, component (C) is not contained. When the composition of the present invention is in the form of an aqueous solution, from the viewpoint of contributing to improving foam quality (density), it is, for example, 0.001% by mass or more, preferably 0.002% by mass or more, and more preferably 0.003% by mass or more. The content of component (C) can also be, for example, 5% by mass or less, preferably 3% by mass or less, and more preferably 1% by mass or less, from the viewpoint of inhibiting the effects of the present invention when contained in a large amount. 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.

[0044] The composition of the present invention is preferably weakly acidic from the viewpoint of storage stability due to inhibition of bacterial proliferation (antiseptic action) and low irritation to the skin due to 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 3 to 8 or 3 to 7. The upper limit of the pH is preferably 8 or less, more preferably 7 or less. The lower limit is preferably 4 or more, more preferably 4.5 or more. From the viewpoint of having a pH equivalent to that of the skin, 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, more preferably 4.5 to 7. The composition of the present invention has excellent solubility even at low pH, and therefore precipitation is suppressed, and in this respect it can be said to have excellent storage stability. Furthermore, generally, anionic surfactants tend to foam less when the pH is low, but the composition of the present invention has good foaming even at low pH. The pH can be adjusted using a pH adjuster. Examples of pH adjusters include the above-mentioned aqueous solutions (buffer solutions), acidic substances (e.g., hydrochloric acid, sulfuric acid, nitric acid, citric acid), and alkaline substances (e.g., hydroxides of alkali metals such as sodium and potassium, and alkaline earth metals such as calcium).

[0045] From the viewpoint of handling, the viscosity of the composition of the present invention is preferably low. 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, even more preferably 0.7 Pa·s or less, and even more preferably 0.5 Pa·s or less. Since the composition of the present invention has excellent handling properties, it can be said to be useful as a cosmetic material for personal care. In this specification, the viscosity is a value measured by using an aqueous solution of the composition having a concentration of 10% by mass using a Brookfield viscometer (DVB-10 Brookfield viscometer manufactured by Toyo Seiki Seisakusho Co., Ltd., rotor No. 20-23, 6-30 rpm, 25°C, 30 seconds later).

[0046] The composition of the present invention may also contain other components such as additional cleaning components, polyhydric alcohols, thickeners, stabilizers, preservatives, fragrances, colorants, etc. The specific types and amounts of these components can be appropriately determined.

[0047] Examples of additional cleaning components include surfactants such as anionic surfactants, amphoteric surfactants, and nonionic surfactants, and fine solids (eg, microspheres, scrubs).

[0048] Anionic surfactants contain 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-acyl amino 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.

[0049] The amphoteric surfactant contains one or more anionic groups as described above, and one or more cationic groups. Examples of the cationic group include ammonium groups, primary amino groups, secondary amino groups, tertiary amino groups, and quaternary amino groups. Examples of the amphoteric surfactant include amidobetaine amphoteric surfactants, acetate betaine amphoteric surfactants, sulfobetaine amphoteric surfactants, and imidazoline amphoteric surfactants (e.g., lauroamphoacetic acid or its salt).

[0050] Examples of nonionic surfactants include ester-type surfactants such as glycerin fatty acid esters, sorbitan fatty acid esters, and sucrose fatty acid esters; ether-type surfactants such as alkyl polyethylene glycols and polyoxyethylene alkyl phenyl ethers; and alkyl glycosides and alkyl polyglycosides in which a sugar and a higher alcohol are glycosidicly bonded.

[0051] Examples of polyhydric alcohols include dihydric alcohols (e.g., ethylene glycol, propylene glycol, 1,3-propanediol, 1,2-butylene glycol, 1,3-butylene glycol, 2,3-butylene glycol, 1,4-butanediol, 2-butene-1,4-diol, 1,5-pentanediol, 1,2-pentanediol, isoprene glycol, hexylene glycol, diethylene glycol, dipropylene glycol, monoglycerides (monoacylglycerols)), trihydric alcohols (e.g., glycerin, trimethylolpropane, 1,2,6-hexanetriol), tetrahydric alcohols (e.g., diglycerin, pentaerythritol), alcohols with higher valences, and salts thereof (e.g., inorganic salts and organic salts as described above). Examples of higher hydric alcohols include sugar alcohols which may be substituted (e.g., monosaccharide alcohols such as sorbitol, mannitol, sucrose, glucose, mannose, etc., disaccharide alcohols such as trehalose, etc., and polysaccharide alcohols such as hyaluronic acid, xanthan gum, etc.), as well as polymers of dihydric to tetrahydric alcohols as described above (e.g., polyglycols, polyglycerins), and salts thereof (e.g., inorganic salts and organic salts as described above). The polyhydric alcohol is preferably a dihydric to tetrahydric alcohol, more preferably a dihydric or trihydric alcohol.

[0052] Examples of thickeners 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.

[0053] Stabilizers include, for example, ascorbic acid, sodium pyrosulfite, and EDTA.

[0054] Examples of preservatives include ethyl paraoxybenzoate, sodium benzoate, salicylic acid, sorbic acid, parabens (methylparaben, propylparaben, etc.), and sodium bisulfite.

[0055] Examples of the fragrance include natural fragrances and synthetic fragrances. Examples of the natural fragrances include rose oil, jasmine oil, neroli oil, lavender oil, ylang-ylang oil, tuberose oil, clary sage 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, opoponax oil, vetiver oil, orris oil, and oakmoss oil. Examples of synthetic fragrances include limonene (orange), β-caryophyllene (woody), cis-3-hexenol (fresh green young leaves), linalool (lily of the valley), farnesol (fresh green notes and floral), β-phenylethyl alcohol (rose), 2,6-nonadienal (violet, cucumber), citral (lemon), α-hexylcinnamic aldehyde (jasmine), β-ionone (violet when diluted), and ι-carvone (spearmint). ), cyclopentadecanone (musk), linalyl acetate (bergamot, lavender), benzyl benzoate (balsam), gamma-undecalactone (peach), eugenol (clove), rose oxide (green floral), indole (when diluted becomes jasmine), phenylacetaldehyde dimethyl acetal (hyacinth), auranthiol (orange flower), and menthol (peppermint) (the names in parentheses indicate the fragrance).

[0056] Examples of colorants 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 pearl pigments such as mica).

[0057] The composition of the present invention can be provided in various forms, for example, powder, liquid, gel, paste, cream, foam, etc. The composition of the present invention can be produced according to a conventional method.

[0058] The composition of the present invention can be made into any form of cosmetic that can be applied to, for example, the skin, hair, scalp, etc., according to a conventional method. The cosmetic is suitable for use as, for example, a cleansing agent for animals such as humans, in the form of a body shampoo, hand soap, face wash, cleansing lotion, cleansing cream, massage cream, hair shampoo, etc. The preferred properties (e.g., pH) of the cosmetic are the same as those of the composition of the present invention described above. The composition of the present invention may also be used as an additive such as a vehicle. EXAMPLES

[0059] The present invention will now be described in more detail with reference to examples. The following examples are provided to suitably explain the present invention and are not intended to limit the present invention.

[0060] Synthesis Example 1: (Production Example of N-Dodecenoylglutamic Acid (C12:1)) 3.0 g of cis-5-dodecenoic acid was dissolved in 30 ml of methylene chloride and cooled on ice. Three drops of N,N-dimethylformamide (DMF) and 2.0 ml of oxalyl chloride were added and stirred at room temperature for 2 hours. The methylene chloride in the reaction solution was removed by vacuum concentration, and 25 ml of methylene chloride was added again and concentrated under reduced pressure. This operation was repeated three times to obtain cis-5-dodecenoic acid chloride. 2.4 g of L-glutamic acid was dissolved by adding 30 ml of 1M aqueous sodium hydroxide solution and 15 ml of acetone, and cooled on ice. The acid chloride was dissolved in 15 ml of acetone and slowly dropped into the aqueous solution of glutamic acid. During this time, 1M aqueous sodium hydroxide solution was added to adjust the pH to 10-11. After the pH no longer fluctuated, 15 ml of hexane was added to wash the reaction solution, and the layers were separated to obtain an aqueous layer. 100 mL of methylene chloride was added, and the pH was adjusted to 2 or less with sulfuric acid and extracted. The methylene chloride layer was dried with anhydrous magnesium sulfate. The methylene chloride was removed by vacuum concentration, and 25 ml of methylene chloride was added to the residue and concentrated under reduced pressure. This operation was repeated twice, and 50 ml of methylene chloride was added to the residue and dissolved by heating. After dissolution, the mixture was cooled on ice to crystallize. 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 the reaction was sufficient.

[0061] Synthesis Example 2: (Production Example of N-Hexadecenoylglutamic Acid (C16:1)) Using 1.7 g of cis-9-hexadecenoic acid, the same procedure was followed to obtain 1.4 g of the target compound. It was confirmed by HPLC that the reaction had proceeded satisfactorily.

[0062] Synthesis Example 3: (Production Example of N-Saturated C8-C16 Sodium Acyl Glutamate) The fatty acid chlorides of the corresponding fatty chain lengths were reacted sufficiently with the reaction amount of glutamate under basic conditions. After the reaction was completed, acid was added to cause crystallization, followed by filtration, neutralization, and drying to obtain powdered N-saturated sodium acyl glutamate. The obtained N-saturated sodium acyl glutamate was confirmed to have reacted sufficiently by HPLC.

[0063] (Evaluation of foaming, foam quality, dissolution state, viscosity) Aqueous solutions of 0.3% by mass and 10% by mass of the compositions in Tables 1 to 3 were prepared using an aqueous sodium hydroxide solution and an aqueous citric acid solution.

[0064] [Foaming measurement]: 20 g of a 0.3% by mass aqueous solution having the composition shown in Tables 1 to 3 was weighed into a 100 mL glass vial and heated to 35° C. Then, the foaming was measured as the foaming height immediately after shaking for 10 seconds using a vortex (Scientific Industries, VORTEX-GENIE2, 3000 rpm), and evaluated according to the following evaluation criteria.

[0065] (Evaluation Criteria) A: The bubble height is 35mm or more. B: Bubble height is 30mm or more but less than 35mm C: Bubble height is less than 30 mm

[0066] [Foam quality evaluation]: 20 g of a 0.3 mass % aqueous solution having the composition shown in Tables 1 to 3 was weighed into a 100 mL glass vial and heated to 35° C. Then, the foam quality immediately after shaking for 10 seconds using a vortex (Scientific Industries, VORTEX-GENIE2, 3000 rpm) was evaluated by five expert panelists according to the following evaluation criteria.

[0067] (Evaluation Criteria) 5 points: The foam felt thick. 4 points: The foam felt rather thick. 3 points: Neither 2 points: The foam felt a little thin. 1 point: The foam felt thin.

[0068] The scores of the five expert panelists were added up and the foam quality was evaluated based on the following criteria. (Evaluation Criteria) AA: 5 people with a total score of 23 points or more A: The total score of 5 people is between 20 and 23 points. B: The total score of 5 people is between 10 and 20 points. C: The total score of 5 people is less than 10 points

[0069] [Solution state]: 10 g of a 10% by mass aqueous solution having the composition shown in Tables 1 to 3 was weighed into a 30 mL glass vial. The solution was then stored at 25° C., and the state of crystal precipitation after one week was visually confirmed and evaluated according to the following evaluation criteria.

[0070] (Evaluation Criteria) A: It is a transparent solution. B: Precipitation was observed at the bottom of the glass vial, or the entire solution became cloudy. C: Precipitation was observed throughout the glass vial.

[0071] [Viscosity]: 10 g of a 10% by mass aqueous solution having the composition shown in Tables 1 to 3 was weighed into a 30 mL glass vial. The solution was then stored at 25° C., and the viscosity at 25° C. after one week was visually confirmed by five expert panelists and evaluated according to the following evaluation criteria.

[0072] (Evaluation Criteria) 5 points: Lower viscosity than tap water 4 points: Rather low viscosity compared to tap water 3 points: Viscosity is similar to tap water 2 points: Rather high viscosity compared to tap water 1 point: High viscosity compared to tap water

[0073] The scores of the five expert panelists were added up and the viscosity was evaluated based on the following evaluation criteria. A: The total score of 5 people is 19 points or more B: The total score of 5 people is 10 points or more but less than 19 points C: The total score of 5 people is less than 10 points

[0074] [Overall evaluation]: For the above four tests, the evaluation criteria were A = 5 points, B = 4 points, and C = 1 point. The overall evaluation was based on the following evaluation criteria.

[0075] (Evaluation Criteria) A: 18 points or more B: 16 points or more and 17 points or less C: 15 points or less

[0076] [Table 1]

[0077] As can be seen from the above results, the surfactant of the present invention had good foaming, foam quality and solubility even in the weakly acidic region, which is the same pH as that of the skin, and had low viscosity with high handleability. On the other hand, sodium N-lauroyl glutamate (C12GluNa) had good foaming and foam quality at low pH, but poor solubility and handleability (Comparative Examples 1 to 3). Moreover, at neutral pH, it had good solubility and handleability, but poor foaming and foam quality (Comparative Example 4). In Table 1, "C12:1Glu" is N-dodecenoyl glutamic acid, and "C12GluNa" is N-sodium lauroyl glutamate.

[0078] [Table 2]

[0079] As can be seen from the above results, it was shown that the use of N-dodecenoyl glutamic acid in combination with sodium N-lauroyl glutamate (C12GluNa) solves the problems of 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 region that is the same pH as the skin, and has low viscosity with high handleability. In Table 2, "C12:1Glu" is N-dodecenoyl glutamic acid, and "C12GluNa" is N-sodium lauroyl glutamate.

[0080] [Table 3]

[0081] As can be seen from the above results, the composition of the present invention had good foaming, foam quality and solubility even in a weakly acidic region that is the same pH as that of skin, and also had a low viscosity that allowed for easy handling. The combination of two or more N-saturated acyl acidic amino acids was superior to the examples shown in Table 2 in which only one type was used. Furthermore, when two N-monounsaturated acyl acidic amino acids were used, the foam quality was rated as "AA," which was an even better result. In contrast, the product without the N-monounsaturated acyl acidic amino acid was inferior in overall evaluation. In Table 3, "C12:1Glu" is N-dodecenoyl glutamic acid, "C16:1Glu" is N-hexadecenoyl glutamic acid, "C18:1Glu" is N-oleoyl glutamic acid, "C8GluNa" is N-sodium capryloyl glutamate, "C10GluNa" is N-sodium caproyl glutamate, "C12GluNa" is N-sodium lauroyl glutamate, "C14GluNa" is N-sodium myristoyl glutamate, and "C16GluNa" is N-sodium palmitoyl glutamate.

[0082] The compositions of Examples 11 and 15 and Comparative Example 6 were subjected to the following oil detergency evaluation test. The results are shown in Table 4.

[0083] [Oil cleaning power]: The cleaning power of oil (Vaseline, Sunwhite P-200, Nikko Rika Corporation) applied to artificial leather was evaluated. The cleaning power of oil was evaluated by the following method. First, the artificial leather was weighed with a precision balance, and 0.10 g of Vaseline was applied on it. 0.30 g of each sample was dropped onto the applied Vaseline, and the Vaseline and each sample were blended in a circular motion with a rubber gloved finger for 20 seconds. Then, the artificial leather was placed in a 500 mL beaker containing 300 mL of tap water, and stirred at a rotation speed of 100 rpm for 30 seconds to rinse off the oil. Finally, the artificial leather was dried for 3 days in a room with controlled temperature and humidity, the weight was measured, and the cleaning power of the oil was calculated from the following formula (1). The cleaning power of the oil was evaluated according to the following criteria, and the results are shown in Table 4. Formula (1): Cleansing rate = ((weight of Vaseline washed off) / (weight of Vaseline applied)) x 100

[0084] (Evaluation Criteria) A: Cleaning rate is 23% or more B: Cleaning rate is 17.5% or more but less than 23% C: Cleaning rate is less than 17.5%

[0085] [Table 4]

[0086] As can be seen from the above results, the oil detergency of the compositions of the present invention was rated "A" or "B". In particular, when N-monounsaturated fatty acids were included, the results were particularly good, with an "A" rating. In contrast, the oil detergency of the compositions of the comparative examples was rated "C", and they did not mix well with oil.

[0087] The compositions of Examples 17 and 18 and Comparative Example 7 were subjected to the following viscosity measurements.

[0088] [Viscosity]: Viscosity was measured using a B-type viscometer manufactured by Toyo Seiki Seisakusho Co., Ltd. The aqueous solution diluted to a concentration of 10% was filled into a 50 mL glass vial and the viscosity was measured. The measurement conditions were set as follows: rotor No. 20 or 21, rotation speed: 12 or 30 rpm, measurement time: 30 seconds, and the measurement was performed. The results are shown in Table 5. Measurement was also attempted for the 10% by mass aqueous solution of Comparative Example 1, but precipitation was observed, making it impossible to measure with the viscometer.

[0089] [Table 5]

[0090] As can be seen from the above results, the compositions of the examples had low viscosity, measured values ​​of 23 or 12 mPa s, whereas the composition of the comparative example had a high viscosity, measured values ​​of 1992 mPa s (1.992 Pa s). In Table 5, "C12:1Glu" is N-dodecenoyl glutamic acid, "C16:1Glu" is N-hexadecenoyl glutamic acid, "C18:1Glu" is N-oleoyl glutamic acid, "C8GluNa" is N-sodium capryloyl glutamate, "C10GluNa" is N-sodium caproyl glutamate, "C12GluNa" is N-sodium lauroyl glutamate, "C14GluNa" is N-sodium myristoyl glutamate, and "C16GluNa" is N-sodium palmitoyl glutamate.

Claims

1. Component (A) an N-monounsaturated acyl acidic amino acid (wherein the unsaturated acyl is an acyl having 10 to 16 carbon atoms) or a salt thereof, and Component (B) an N-saturated acyl acidic amino acid or a salt thereof; The N-monounsaturated acyl acidic amino acid is a compound represented by the following general formula (1): the weight ratio (A / (A+B)) of component (A) to the total weight of component (A) and component (B) is 0.001 or more and less than 1; composition. 【Chemistry 1】 (In the general formula (1), l is an integer of 1 or 2, and m is an integer of 0 to 6.)

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

3. The composition described in claim 1 or 2, wherein the N-monounsaturated acyl acidic amino acid is an N-monounsaturated acyl glutamic acid.

4. Component (A) is (A1) an N-monounsaturated acyl acidic amino acid (wherein the unsaturated acyl is an acyl having 12 carbon atoms) or a salt thereof, and The composition according to any one of claims 1 to 3, comprising (A2) an N-monounsaturated acyl acidic amino acid (wherein the unsaturated acyl is an acyl having 10, 14, or 16 carbon atoms) or a salt thereof.

5. Component (B) is The composition according to any one of claims 1 to 4, comprising (B1) an N-lauroyl acidic amino acid and / or a salt thereof.

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

7. The composition according to any one of claims 1 to 6, further comprising component (C) an N-unsaturated fatty acid or a salt thereof.

8. The composition of any one of claims 1 to 7, further comprising component (D) an aqueous medium.

9. The composition according to any one of claims 1 to 8, having a pH of from 3 to 9.

10. The composition according to any one of claims 1 to 9, having a viscosity of 1.5 Pa·s or less.

11. The composition according to any one of claims 1 to 10, which is a composition for external use on the skin.

12. The composition according to any one of claims 1 to 10, which is a cleaning composition.

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