Detergent composition, method for producing same, and detergent product containing detergent composition

Abstract

The present invention relates to a detergent composition comprising (A) at least one selected from the group consisting of N-acyl alanine having a C8-22 acyl group and salts thereof, (B) at least one selected from the group consisting of C8-22 fatty acids and salts thereof, and (C) at least one selected from the group consisting of alanine and salts thereof, wherein the content ratio [(A):(B):(C)] by weight between the component (A), the component (B), and the component (C) is 100:45-245:10-150.　The present invention makes it possible to provide a detergent composition which contains an N-acyl neutral amino acid or a salt thereof and which has excellent lather formation and lather quality and provides excellent sensation when used, makes it possible to impart a favorable moisturized feel to skin and hair after washing and drying, and further improves a rough feeling caused after washing.

Description

Detergent composition, its manufacturing method, and cleaning agent containing said detergent composition

[0001] The present invention relates to a detergent composition containing an N-long-chain acyl neutral amino acid or a salt thereof, a method for producing the same, and a cleaning agent containing the detergent composition.

[0002] N-long-chain acyl neutral amino acids or their salts have excellent surfactant and bacteriostatic properties and are low in irritation, and therefore are used as detergent components in various cleanser compositions. However, when N-long-chain acyl neutral amino acids or their salts are used alone as cleansers, there are problems such as insufficient foam volume and foam persistence, and an unsatisfactory feel in use, such as a dry and moist feeling on the skin and hair after washing and drying. Therefore, various studies have been conducted to improve these problems.

[0003] For example, a detergent composition containing an N-long-chain acyl dipeptide, an N-long-chain acyl glycylglycine salt, an N-long-chain acyl β-alanyl β-alanine salt, and an N-long-chain acyl glycine salt or an N-long-chain acyl β-alanine salt, in a specific content ratio (Patent Document 1), and a detergent composition containing an N-long-chain acyl alanyl alanine salt (Patent Document 2) have been proposed. The detergent composition described in Patent Document 1 was excellent in foaming and foam durability, and had good foam rinse-off during rinsing, but left hair feeling tight and lacking in moisturized feeling after washing. In addition, the detergent composition described in Patent Document 2 was excellent in foaming and foam durability, and had improved resistance to hard water and squeaky feeling during use, but left hair with an insufficient smooth feeling after washing.

[0004] Furthermore, a detergent composition has been proposed that contains an N-acyl neutral amino acid or its salt, an N-long-chain acyl neutral amino acid dipeptide or its salt, and an N-long-chain acyl neutral amino acid tripeptide or its salt in a specific content ratio, as a detergent composition that has excellent foaming and foam persistence and can impart a smooth and moist feeling to skin and hair after washing and drying (Patent Document 3). Patent Document 3 also proposes a production method that reduces the environmental impact compared to the conventional Schotten-Baumann reaction using fatty acid chloride, in which a long-chain fatty acid, a neutral amino acid, and an alkaline substance are mixed and heated to cause a direct dehydration condensation reaction. However, a new problem has been found with the detergent composition described in Patent Document 3: a squeaky feeling after washing.

[0005] Therefore, there is a need for a cleanser composition containing an N-acyl neutral amino acid or a salt thereof, which has excellent foaming, foam quality, and usability, can impart a good moist feeling to the skin and hair after washing and drying, and further has an improved squeaky feeling after washing.

[0006] JP-A-5-078693 JP-A-7-188694 International Publication No. 2005 / 033255

[0007] Therefore, an object of the present invention is to provide a cleanser composition containing an N-acyl neutral amino acid or a salt thereof, which has excellent foaming, foam quality and usability, can impart a good moist feeling to the skin and hair after washing and drying, and further has an improved squeaky feeling after washing.

[0008] As a result of intensive research aimed at solving the above-mentioned problems, the present inventors have found that a cleanser composition containing (A) one or more members selected from the group consisting of N-acylalanines having an acyl group containing 8 to 22 carbon atoms and salts thereof, (B) one or more members selected from the group consisting of fatty acids having 8 to 22 carbon atoms and salts thereof, and (C) one or more members selected from the group consisting of alanine and salts thereof, in a weight ratio [(A):(B):(C)] of 100:45 to 245:10 to 150, can improve foaming, foam quality, usability, moist feeling after washing and drying, and also improve the squeaky feeling after washing. Further research led to the completion of the present invention.

[0009] That is, the present invention relates to the following: [1] A detergent composition containing (A) one or more selected from the group consisting of N-acylalanines having an acyl group containing 8 to 22 carbon atoms and salts thereof, (B) one or more selected from the group consisting of fatty acids having 8 to 22 carbon atoms and salts thereof, and (C) one or more selected from the group consisting of alanine and salts thereof, wherein the content ratio of the components (A), (B), and (C) [(A):(B):(C)] is 100:45 to 245:10 to 150 by weight. [2] The detergent composition according to [1], further containing (D) one or more selected from the group consisting of N-acylalanylalanines having an acyl group containing 8 to 22 carbon atoms and salts thereof. [3] The detergent composition according to [2], wherein the content ratio of the component (D) to the component (A) [(A):(D)] is 100:1 to 10 by weight. [4] The cleaning composition according to any one of [1] to [3], containing two or more N-acylalanines or salts thereof having acyl groups with different carbon numbers as the one or more species selected from the group consisting of N-acylalanines having an acyl group with a carbon number of 8 to 22 and salts thereof. [5] The cleaning composition according to any one of [1] to [4], containing two or more fatty acids or salts thereof having different carbon numbers as the one or more species selected from the group consisting of fatty acids having a carbon number of 8 to 22 and salts thereof. [6] The cleaning composition according to any one of [2] to [5], containing two or more N-acylalanines or salts thereof having acyl groups with different carbon numbers as the one or more species selected from the group consisting of N-acylalanylalanines having an acyl group with a carbon number of 8 to 22 and salts thereof. [7] A method for producing a detergent composition, comprising reacting (a) a fatty acid having 8 to 22 carbon atoms, (b) alanine, and (c) one or more selected from the group consisting of alkali metal hydroxides and amines at 147° C. to 190° C. [8] The method according to [7], wherein 0.5 to 1.5 moles of (a) a fatty acid having 8 to 22 carbon atoms are used per mole of (b) alanine. [9] The method according to [7] or [8], wherein 0.5 to 1.5 moles of (c) one or more selected from the group consisting of alkali metal hydroxides and amines are used per mole of (b) alanine.

[10] The manufacturing method according to any one of [7] to [9], wherein (a) the fatty acid having 8 to 22 carbon atoms is a mixture of two or more fatty acids having different carbon atoms.

[11] The manufacturing method according to any one of [7] to

[10] , wherein (b) the alanine is L-alanine or DL-alanine.

[12] The manufacturing method according to any one of [7] to

[11] , wherein (c) the one or more selected from the group consisting of alkali metal hydroxides and amines is sodium hydroxide.

[13] A cleaning agent containing the cleaning composition according to any one of [1] to [6] as a cleaning agent ingredient.

[14] The cleaning agent according to

[13] , wherein the viscosity measured at 25°C using a Brookfield viscometer is 500 mPa·s to 60,000 mPa·s.

[15] A cleaning agent containing the cleaning composition according to any one of [1] to [6] as a cleaning auxiliary.

[16] The cleanser according to

[15] , having a viscosity of 500 mPa·s to 60,000 mPa·s as measured at 25°C using a Brookfield viscometer.

[17] A cleanser comprising the cleanser composition according to any one of [1] to [6] as a cleanser ingredient, and further comprising a thickener.

[18] The cleanser according to

[17] , wherein the thickener is one or more selected from the group consisting of hydroxypropyl starch phosphate, fatty acid alkanolamide, glycine-type amphoteric surfactant, aminoacetic acid betaine-type amphoteric surfactant, sulfobetaine-type amphoteric surfactant, and amidoamine oxide-type amphoteric surfactant.

[19] The cleanser according to

[17] or

[18] , wherein the content of the thickener is 1 wt% to 5 wt% based on the total amount of the cleanser.

[20] The cleanser according to any one of

[17] to

[19] , having a viscosity of 500 mPa·s to 400,000 mPa·s as measured at 25°C using a Brookfield viscometer.

[21] A cleanser comprising the cleanser composition according to any one of [1] to [6] as a cleaning aid, and further comprising a thickener.

[22] The cleanser according to

[21] , wherein the thickener is one or more selected from the group consisting of hydroxypropyl starch phosphate, fatty acid alkanolamide, glycine-type amphoteric surfactant, aminoacetic acid betaine-type amphoteric surfactant, sulfobetaine-type amphoteric surfactant, and amidoamine oxide-type amphoteric surfactant.

[23] The cleanser according to

[21] or

[22] , wherein the content of the thickener is 1 to 5% by weight based on the total amount of the cleanser.

[24] The cleanser according to any one of

[21] to

[23] , which has a viscosity of 500 mPa·s to 400,000 mPa·s as measured at 25°C using a Brookfield viscometer.

[0010] The present invention can provide a detergent composition that has excellent foaming and foam quality, a good feel in use, imparts a moist feeling after washing and drying, and further reduces the squeaky feeling after washing. The detergent composition can be used as a detergent component and cleaning aid in skin or hair cleansers. The present invention also can provide a method for producing a detergent composition that is environmentally friendly, allows the reaction to proceed under relatively mild conditions, and allows the reaction mixture to be used as is as a detergent composition. Furthermore, the present invention can provide a detergent that contains the above detergent composition, has excellent foaming and foam quality, imparts a moist feeling to skin or hair after washing and drying, reduces the squeaky feeling after washing, and has an excellent feel in use.

[0011] The present invention provides a cleanser composition. As used herein, the term "cleaner composition" refers to a composition contained in a skin or hair cleanser as a cleanser component or cleaning aid, as described below. The cleanser composition of the present invention contains (A) one or more N-acylalanines having an acyl group having 8 to 22 carbon atoms and salts thereof, (B) one or more fatty acids having 8 to 22 carbon atoms and salts thereof, and (C) one or more alanines selected from the group consisting of alanine and salts thereof.

[0012] The alanine constituting the N-acylalanine contained as component (A) in the detergent composition of the present invention is 2-aminopropanoic acid, a neutral aliphatic amino acid, and may be in the L-, D-, or DL-configuration, with the L- and DL-configurations being preferred.

[0013] The acyl group in the N-acylalanine contained as component (A) in the detergent composition of the present invention is a long-chain acyl group having 8 to 22 carbon atoms, and examples thereof include octanoyl (capryloyl), 6-methylheptanoyl (isooctanoyl), 2-ethylhexanoyl, decanoyl (caprinoyl), dodecanoyl (lauroyl), tetradecanoyl (myristoyl), 12-methyltridecanoyl (isomyristoyl), hexadecanoyl (palmitoyl), and the like. linear or branched saturated acyl groups having 8 to 22 carbon atoms, such as octenoyl, 14-methylpentadecanoyl (isopalmitoyl), octadecanoyl (stearoyl), 16-methylheptadecanoyl (isostearoyl), eicosanoyl (arachidoyl), and docosanoyl (behenoyl); octenoyl, 6-methylheptenoyl (isooctenoyl), decenoyl, dodecenoyl, tetradecenoyl, and 9-hexadecenoyl (palmitoyl); cis,cis-9,12-octadecadienoyl (linoleoyl), 9,12,15-octadecatrienoyl (9,12,15-linolenoyl), 6,9,12-octadecatrienoyl (6,9,12-linolenoyl), 5,8,11,14-eicosatetraenoyl (arachidonoyl), cis-13-docosenoyl, etc. Examples of such an acyl group include linear or branched unsaturated acyl groups having 8 to 22 carbon atoms. The acyl group may be a mixture of saturated acyl groups and unsaturated acyl groups derived from a fatty acid mixture containing mainly fatty acids having 8 to 18 carbon atoms, or a mixture of saturated acyl groups and unsaturated acyl groups derived from fatty acids derived from vegetable oils containing mainly fatty acids having 8 to 18 carbon atoms, such as coconut oil fatty acid acyl (cocoyl), palm oil fatty acid acyl, and palm kernel oil fatty acid acyl.

[0014] In the cleanser composition of the present invention, a salt of the above-described N-acylalanine can also be used as component (A). The salt of N-acylalanine is not particularly limited as long as it is a pharmaceutically acceptable salt suitable for use in a skin composition, and examples thereof include acid addition salts and salts with bases. Specific examples include salts with inorganic bases, organic bases, inorganic acids, organic acids, and amino acids. Examples of salts with inorganic bases include salts with alkali metals such as lithium, sodium, and potassium, salts with alkaline earth metals such as magnesium and calcium, and ammonium salts. Examples of salts with organic bases include salts with alkanolamines such as monoethanolamine, diethanolamine, and triethanolamine, and salts with heterocyclic amines such as morpholine and piperidine. Examples of salts with inorganic acids include salts with hydrohalic acids (hydrochloric acid, hydrobromic acid, hydroiodic acid, etc.), sulfuric acid, nitric acid, phosphoric acid, etc. Examples of salts with organic acids include salts with monocarboxylic acids such as formic acid, acetic acid, and propanoic acid; salts with saturated dicarboxylic acids such as oxalic acid, malonic acid, and succinic acid; salts with unsaturated dicarboxylic acids such as maleic acid and fumaric acid; salts with tricarboxylic acids such as citric acid; and salts with keto acids such as α-ketoglutaric acid. Examples of salts with amino acids include salts with aliphatic amino acids such as glycine; salts with aromatic amino acids such as tyrosine; salts with basic amino acids such as lysine; and salts with acidic amino acids such as aspartic acid and glutamic acid. The above-mentioned salts may each be a hydrate (hydrate salt), and examples of such hydrates include monohydrates to hexahydrates. From the viewpoints of availability, ease of handling, and the like, preferred salts of N-acylalanine include alkali metal salts such as sodium salts and potassium salts, and salts with alkanolamines such as monoethanolamine, diethanolamine, and triethanolamine, with sodium salts, potassium salts, and triethanolamine salts being more preferred, and sodium salts and potassium salts being even more preferred.

[0015] In the detergent composition of the present invention, the above-mentioned N-acylalanines and salts thereof may be selected and used alone, or two or more may be selected and used in combination. For the purposes of the present invention, it is preferable to select and use, as component (A), two or more N-acylalanines or salts thereof having acyl groups with different numbers of carbon atoms. As the one or more N-acylalanines or salts thereof having an acyl group with 8 to 22 carbon atoms contained as component (A) in the detergent composition of the present invention, a mixture of N-acylalanines or salts thereof having a linear or branched saturated acyl group with 8 to 22 carbon atoms is preferably used. A mixture of N-acylalanines or salts thereof having a saturated acyl group with 10 to 14 carbon atoms, or a mixture of N-acylalanines or salts thereof, such as a mixture of N-decanoyl(caprinoyl)alanine or a salt thereof, N-dodecanoyl(lauroyl)alanine or a salt thereof, and N-tetradecanoyl(myristoyl)alanine or a salt thereof is more preferably used. Also preferably used is an N-acylalanine or a salt thereof having an acyl group derived from a fatty acid mixture containing a large amount of saturated fatty acids having 8 to 18 carbon atoms, and even more preferably used is an N-acylalanine or a salt thereof having an acyl group derived from a fatty acid derived from a vegetable oil containing a large amount of saturated fatty acids having 8 to 18 carbon atoms, such as N-coconut oil fatty acid acylalanine or a salt thereof, N-palm oil fatty acid acylalanine or a salt thereof, or N-palm kernel oil fatty acid acylalanine or a salt thereof.

[0016] The above-mentioned N-acylalanine and its salt can be produced by a thermal dehydration condensation reaction of alanine, a fatty acid having 8 to 22 carbon atoms, and a basic substance in the method for producing the detergent composition of the present invention described below, or by other known production methods. Alternatively, commercially available products provided by Ajinomoto Co., Inc. and other companies can be used.

[0017] Examples of fatty acids having 8 to 22 carbon atoms contained as component (B) in the detergent composition of the present invention include linear or branched saturated fatty acids such as octanoic acid (caprylic acid), 2-ethylhexanoic acid, nonanoic acid, decanoic acid (capric acid), dodecanoic acid (lauric acid), tetradecanoic acid (myristic acid), 12-methyltridecanoic acid (isomyristic acid), hexadecanoic acid (palmitic acid), 14-methylpentadecanoic acid (isopalmitic acid), octadecanoic acid (stearic acid), 16-methylheptadecanoic acid (isostearic acid), eicosanoic acid (arachidic acid), and docosanoic acid (behenic acid); Examples of straight-chain or branched-chain unsaturated fatty acids include butenoic acid (isooctenoic acid), decenoic acid, 10-undecenoic acid, dodecenoic acid, tetradecenoic acid, 9-hexadecenoic acid (palmitoleic acid), cis-9-octadecenoic acid (oleic acid), 11-octadecenoic acid (vaccenic acid), cis,cis-9,12-octadecadienoic acid (linoleic acid), 9,12,15-octadecatrienoic acid (9,12,15-linolenic acid), 6,9,12-octadecatrienoic acid (6,9,12-linolenic acid), 5,8,11,14-eicosatetraenoic acid (arachidonic acid), and cis-13-docosenoic acid (erucic acid). In addition, a fatty acid mixture containing mainly fatty acids having 8 to 18 carbon atoms can also be used, and fatty acids derived from vegetable oils containing mainly fatty acids having 8 to 18 carbon atoms, such as coconut oil fatty acids, palm oil fatty acids, and palm kernel oil fatty acids, can also be used.

[0018] In the cleanser composition of the present invention, the above-mentioned salts of fatty acids having 8 to 22 carbon atoms can be used as component (B). The salts of fatty acids having 8 to 22 carbon atoms are not particularly limited as long as they are pharmaceutically acceptable salts suitable for use in skin compositions, and examples thereof include salts with inorganic or organic bases. Examples of salts with inorganic bases include salts with alkali metals such as lithium, sodium, and potassium; salts with alkaline earth metals such as magnesium and calcium; and ammonium salts. Examples of salts with organic bases include salts with alkanolamines such as monoethanolamine, diethanolamine, and triethanolamine; and salts with heterocyclic amines such as morpholine and piperidine. From the standpoints of availability, ease of handling, and the like, preferred salts of fatty acids having 8 to 22 carbon atoms include alkali metal salts such as sodium salts and potassium salts, and salts with alkanolamines such as monoethanolamine, diethanolamine, and triethanolamine. Sodium salts, potassium salts, and triethanolamine salts are more preferred, with sodium salts and potassium salts being even more preferred.

[0019] In the detergent composition of the present invention, the above-mentioned fatty acids and salts having 8 to 22 carbon atoms may be used singly or in combination. For the purposes of the present invention, it is preferable to select and use in combination two or more fatty acids or salts thereof having different carbon atoms as component (B). As the one or more fatty acids selected from the group consisting of fatty acids and salts having 8 to 22 carbon atoms contained as component (B) in the detergent composition of the present invention, a mixture of linear or branched saturated fatty acids or salts thereof having 8 to 22 carbon atoms is preferably used. A mixture of saturated fatty acids or salts thereof having 10 to 14 carbon atoms, such as a mixture of decanoic acid (capric acid) or salts thereof, dodecanoic acid (lauric acid) or salts thereof, and tetradecanoic acid (myristic acid) or salts thereof, is more preferably used. Furthermore, a mixture of fatty acids or salts thereof rich in saturated fatty acids having 8 to 18 carbon atoms is also preferably used. Fatty acids or salts thereof derived from vegetable oils rich in saturated fatty acids having 8 to 18 carbon atoms, such as coconut oil fatty acids, palm oil fatty acids, and palm kernel oil fatty acids, are also more preferably used.

[0020] The above-mentioned fatty acids having 8 to 22 carbon atoms and salts thereof may be extracted from animals or plants containing them, purified, and used, or may be produced by a known production method. Alternatively, commercially available products provided by various companies may also be used.

[0021] The alanine contained as component (C) in the detergent composition of the present invention is as described above for the alanine constituting component (A). Examples of salts of alanine include the same salts as those described above for the salts of N-acylalanine, i.e., salts with inorganic bases, organic bases, inorganic acids, organic acids, and salts with amino acids. In the detergent composition of the present invention, alanine and its salts may be used singly or in combination of two or more. Alanine and its salts may be extracted and purified from plants or animals containing them, or may be produced by known production methods. Alternatively, commercially available products available from various companies may also be used.

[0022] In the detergent composition of the present invention, (A) one or more selected from the group consisting of N-acylalanines having an acyl group having 8 to 22 carbon atoms and salts thereof, (B) one or more selected from the group consisting of fatty acids having 8 to 22 carbon atoms and salts thereof, and (C) one or more selected from the group consisting of alanine and salts thereof are contained in a weight ratio [(A):(B):(C)] of 100:45 to 245:10 to 150, preferably 100:60 to 200:10 to 120, and more preferably 100:85 to 200:10 to 80. When the ratio of the content of the component (B) to the content of the component (A) [(B) / (A)] is 0.45 to 2.45 by weight, and the ratio of the content of the component (C) to the content of the component (A) [(C) / (A)] is 0.1 to 1.5 by weight, the foaming properties and foam quality are good, the moist feeling on the skin and hair after washing and drying is improved, and the squeaky feeling during washing is reduced.

[0023] In addition to the above components (A) to (C), the detergent composition of the present invention preferably contains (D) one or more selected from the group consisting of N-acylalanylalanine having an acyl group having 8 to 22 carbon atoms and salts thereof. The alanylalanine constituting the N-acylalanylalanine contained as component (D) in the detergent composition of the present invention may be a dipeptide of any of L-alanine, D-alanine, and DL-alanine, but is preferably a dipeptide of L-alanine and DL-alanine. The acyl group having 8 to 22 carbon atoms is as described above for the acyl group having 8 to 22 carbon atoms in component (A). Examples of salts of N-acylalanylalanine include the same salts as those described above for the salt of N-acylalanine (A).

[0024] In the detergent composition of the present invention, one N-acylalanylalanine or its salt having an acyl group with 8 to 22 carbon atoms may be selected and used alone, or two or more may be selected and used in combination. For the purposes of the present invention, it is preferable to select and use two or more N-acylalanylalanine or its salts having acyl groups with different numbers of carbon atoms as component (D) and use them in combination. The one or more members selected from the group consisting of N-acylalanylalanines having an acyl group of 8 to 22 carbon atoms and salts thereof, which are contained as component (D) in the detergent composition of the present invention, are preferably a mixture of N-acylalanylalanines having a linear or branched saturated acyl group of 8 to 22 carbon atoms or salts thereof, and more preferably a mixture of N-acylalanylalanines having a saturated acyl group of 10 to 14 carbon atoms or salts thereof, such as a mixture of N-decanoyl(caprinoyl)alanylalanine or salts thereof, N-dodecanoyl(lauroyl)alanylalanine or salts thereof, and N-tetradecanoyl(myristoyl)alanylalanine or salts thereof. Also preferably used is N-acylalanyl alanine or a salt thereof having an acyl group derived from a fatty acid mixture containing a large amount of saturated fatty acids having 8 to 18 carbon atoms, and more preferably used is N-acylalanyl alanine or a salt thereof having an acyl group derived from a fatty acid derived from a vegetable oil containing a large amount of saturated fatty acids having 8 to 18 carbon atoms, such as N-coconut oil fatty acid acylalanyl alanine or a salt thereof, N-palm oil fatty acid acylalanyl alanine or a salt thereof, or N-palm kernel oil fatty acid acylalanyl alanine or a salt thereof.

[0025] N-acylalanylalanine and its salts may be produced by a known production method, or may be produced by a thermal dehydration condensation reaction of a fatty acid having 8 to 22 carbon atoms, alanine, and a basic substance by the production method of the detergent composition of the present invention described below.

[0026] In the cleanser composition of the present invention, the content of (D) one or more selected from the group consisting of N-acylalanylalanines having an acyl group containing 8 to 22 carbon atoms and salts thereof is preferably such that the content ratio to component (A) [(A):(D)] is 100:1 to 10 by weight, more preferably 100:1 to 3 by weight. The inclusion of component (D) improves the squeaky feeling and feel when washing hair with the cleanser composition.

[0027] In addition to the components (A) to (D), the cleaning composition of the present invention may contain general additives such as a solvent (e.g., water), a thickener, a pH adjuster, a chelating agent, and a preservative, provided that the additives do not impair the characteristics of the present invention.

[0028] The cleaning composition of the present invention can be prepared by mixing the above components (A) to (C) or the above components (A) to (D) and, if necessary, adding a solvent such as water or additives to form a homogeneous mixture. Alternatively, the reaction product obtained by the method for producing the cleaning composition of the present invention described below can be used as is as the cleaning composition of the present invention. The cleaning composition of the present invention can be provided in various forms, such as a liquid, a paste, a gel, or a solid.

[0029] The cleanser composition of the present invention has excellent foaming properties and foam quality, is pleasant to use, can impart a moist feeling after washing and drying, and further reduces the squeaky feeling after washing. Therefore, the cleanser composition of the present invention can be suitably used as a cleanser component in a skin or hair cleanser and can also be suitably used as a cleaning auxiliary.

[0030] The present invention also provides a method for producing a detergent composition (hereinafter also referred to as the "production method of the present invention" in this specification). The production method of the present invention comprises reacting (a) a fatty acid having 8 to 22 carbon atoms, (b) alanine, and (c) one or more members selected from the group consisting of alkali metal hydroxides and amines at 147°C to 190°C.

[0031] The (a) fatty acid having 8 to 22 carbon atoms used in the production method of the present invention is as described above for the fatty acid having 8 to 22 carbon atoms contained as component (B) in the detergent composition of the present invention. In the production method of the present invention, it is preferable to select and mix two or more fatty acids having different carbon chain lengths as the (a) fatty acid having 8 to 22 carbon atoms, and more preferably use a mixture of linear or branched saturated fatty acids having 8 to 22 carbon atoms. In particular, a mixture of fatty acids having 10 to 14 carbon atoms, such as a mixture of decanoic acid (capric acid), dodecanoic acid (lauric acid), and tetradecanoic acid (myristic acid), or a fatty acid derived from a vegetable oil containing a large amount of fatty acids having 8 to 18 carbon atoms, such as coconut oil fatty acid, palm oil fatty acid, or palm kernel oil fatty acid, is preferably used.

[0032] The alanine (b) used in the production method of the present invention is the same as that described above for the alanine constituting the N-acylalanine contained as component (A) in the detergent composition of the present invention. In the production method of the present invention, L-alanine and DL-alanine are preferably used as the alanine (b).

[0033] In the production method of the present invention, the basic substance used is (c) one or more selected from the group consisting of alkali metal hydroxides and amines. Examples of alkali metal hydroxides include lithium hydroxide, sodium hydroxide, and potassium hydroxide, and examples of amines include monoethanolamine, diethanolamine, and triethanolamine. From the viewpoint of the progress and efficiency of the condensation reaction between a fatty acid having 8 to 22 carbon atoms and alanine, alkali metal hydroxides are preferably used as the basic substance, sodium hydroxide and potassium hydroxide are more preferably used, and sodium hydroxide is even more preferably used.

[0034] In the production method of the present invention, (a) a fatty acid having 8 to 22 carbon atoms is preferably used in an amount of 0.5 to 1.5 moles, more preferably 0.7 to 1.2 moles, even more preferably 0.8 to 1.0 moles, and particularly preferably 0.82 to 0.89 moles, per mole of (b) alanine. In the production method of the present invention, (c) one or more selected from the group consisting of alkali metal hydroxides and amines is preferably used in an amount of 0.5 to 1.5 moles, more preferably 0.8 to 1.3 moles, per mole of (b) alanine.

[0035] In the production method of the present invention, (a) a fatty acid having 8 to 22 carbon atoms, (b) alanine, and (c) one or more selected from the group consisting of alkali metal hydroxides and amines are mixed and reacted at 147°C to 190°C to thermally dehydrate and condense (a) the fatty acid having 8 to 22 carbon atoms and (b) the alanine. The thermal dehydration and condensation reaction is preferably carried out at 160°C to 180°C, more preferably at 160°C to 170°C. The thermal dehydration and condensation reaction is preferably carried out at the above temperature for 15 to 30 hours, more preferably for 18 to 28 hours.

[0036] In the production method of the present invention, the above-mentioned thermal dehydration condensation reaction is preferably carried out under an inert gas atmosphere such as nitrogen or helium to prevent coloration of the reaction mixture due to heating. Furthermore, in the production method of the present invention, it is preferable to allow the reaction to proceed while removing water generated during the reaction, i.e., water generated by neutralization with a basic substance and water generated by the condensation reaction. The water generated during the reaction can be removed by removing it with an inert gas stream or by reducing the pressure.

[0037] The production method of the present invention provides a reaction mixture containing the product of the thermal dehydration condensation reaction, which is an N-acylalanine or its salt having an acyl group having 8 to 22 carbon atoms, an unreacted fatty acid or its salt having 8 to 22 carbon atoms, and unacylated alanine or its salt. In the reaction mixture, the N-acylalanine salt and the fatty acid salt are in the form of an alkali metal salt or an amine salt, depending on the basic substance used. By using (a) a fatty acid having 8 to 22 carbon atoms, (b) alanine, and (c) one or more selected from the group consisting of alkali metal hydroxides and amines in the above-mentioned usage ratio and reacting them under the above-mentioned reaction conditions, a reaction mixture can be obtained containing the N-acylalanine or its salt having an acyl group having 8 to 22 carbon atoms, the fatty acid or its salt having 8 to 22 carbon atoms, and alanine or its salt in the above-mentioned weight ratio of 100:45 to 245:10 to 150, and the reaction mixture can be used as is as the cleaning composition of the present invention.

[0038] The reaction mixture can be neutralized with a mineral acid such as hydrochloric acid or sulfuric acid to convert the N-acylalanine salt and the fatty acid salt into free N-acylalanine and fatty acid, respectively, and then neutralized with an appropriate base to obtain the desired N-acylalanine salt and fatty acid salt.

[0039] Furthermore, in the production method of the present invention, a reaction mixture containing N-acylalanylalanine or a salt thereof having an acyl group having 8 to 22 carbon atoms can be obtained depending on the ratio of the amounts used of (a) a fatty acid having 8 to 22 carbon atoms, (b) alanine, and (c) one or more selected from the group consisting of alkali metal hydroxides and amines, as well as the reaction conditions.

[0040] In the production method of the present invention, the reaction can proceed under relatively mild conditions with little environmental impact, and the resulting reaction mixture can be used as is as a cleaning composition.

[0041] The present invention also provides a cleanser. As used herein, "cleaner" refers to a composition used for cleansing skin or hair. The cleanser of the present invention contains the above-described cleanser composition of the present invention. In the cleanser of the present invention, the above-described cleanser composition of the present invention may be contained as a cleanser component or a cleansing aid. As used herein, "cleaner component" refers to a component used for cleansing skin or hair, and "cleaning aid" refers to a component added for the purpose of enhancing the detergency of the cleanser component. When the cleanser composition of the present invention contains the above-described cleanser component as a cleanser component, the total content of (A) one or more N-acylalanines having an acyl group containing 8 to 22 carbon atoms and salts thereof, (B) one or more fatty acids having 8 to 22 carbon atoms and salts thereof, and (C) one or more selected from the group consisting of alanine and salts thereof [(A) + (B) + (C)] is preferably 1% by weight to 50% by weight, more preferably 1% by weight to 30% by weight, and even more preferably 10% by weight to 30% by weight. When the detergent composition of the present invention is contained as a cleaning aid, the content thereof in the detergent of the present invention is preferably 0.5% by weight to 10% by weight, more preferably 1% by weight to 7% by weight, as the total amount [(A) + (B) + (C)] of (A) one or more types selected from the group consisting of N-acylalanines having an acyl group of 8 to 22 carbon atoms and salts thereof, (B) one or more types selected from the group consisting of fatty acids having 8 to 22 carbon atoms and salts thereof, and (C) one or more types selected from the group consisting of alanine and salts thereof.

[0042] When the cleanser composition of the present invention contains (D) one or more selected from the group consisting of N-acylalanines having an acyl group of 8 to 22 carbon atoms and salts thereof, the content of the cleanser composition of the present invention when contained as a cleanser component in the cleanser of the present invention is preferably 1 to 50% by weight, more preferably 1 to 30% by weight, and even more preferably 10 to 30% by weight, as the total amount [(A) + (B) + (C) + (D)] of (A) one or more selected from the group consisting of N-acylalanines having an acyl group of 8 to 22 carbon atoms and salts thereof, (B) one or more selected from the group consisting of fatty acids having 8 to 22 carbon atoms and salts thereof, (C) one or more selected from the group consisting of alanine and salts thereof, and (D) one or more selected from the group consisting of N-acylalanylalanines having an acyl group of 8 to 22 carbon atoms and salts thereof. Furthermore, when the detergent composition of the present invention contains the compound as a cleaning auxiliary, the content of the compound in the detergent composition of the present invention is preferably 0.5% by weight to 10% by weight, and more preferably 1% by weight to 7% by weight, in terms of the total amount [(A) + (B) + (C) + (D)] of (A) one or more selected from the group consisting of N-acylalanines having an acyl group of 8 to 22 carbon atoms and salts thereof, (B) one or more selected from the group consisting of fatty acids having 8 to 22 carbon atoms and salts thereof, (C) one or more selected from the group consisting of alanines and salts thereof, and (D) one or more selected from the group consisting of N-acylalanylalanines having an acyl group of 8 to 22 carbon atoms and salts thereof.

[0043] To the cleanser of the present invention, general additives such as solvents (water, ethanol, etc.), various surfactants (anionic surfactants other than the above components (A), (B), and (D), cationic surfactants, amphoteric surfactants, and nonionic surfactants), oils, emollients, moisturizers, thickeners, hair conditioning agents, anti-inflammatory agents, ultraviolet absorbers, preservatives, antioxidants, chelating agents, pH adjusters, colorants, and fragrances may be added as needed, provided the features of the present invention are not impaired.

[0044] The cleanser of the present invention can be provided in the form of a liquid, milk, gel, paste, cream, powder, solid, or the like, and can be provided as cleansers for facial skin such as face washing foam, face washing powder, cleansing lotion, and cleansing cream; body cleansers such as hand soap, body soap, and bath soap; and hair cleansers such as shampoo and rinse-in shampoo. The cleanser of the present invention can be produced according to a conventional formulation method depending on its form. For example, a liquid cleanser can be produced by mixing the cleanser composition of the present invention and, if necessary, general additives into a solvent such as water and blending them to form a homogeneous mixture. A milky or creamy cleanser can be produced by adding and dissolving the cleanser composition of the present invention and, if necessary, a hydrophilic additive into a solvent such as water, and then mixing and dissolving the mixture with an optional lipophilic additive such as oil, and then emulsifying the mixture.

[0045] From the viewpoints of usability, handling, etc., the cleanser of the present invention preferably has a moderate viscosity, and for example, the viscosity measured at 25°C using a Brookfield viscometer is preferably 500 mPa·s to 60,000 mPa·s, more preferably 1,000 mPa·s to 60,000 mPa·s, and even more preferably 2,000 mPa·s to 60,000 mPa·s. The above viscosity can be imparted to the cleanser of the present invention by containing the cleanser composition of the present invention as a cleanser component or cleaning aid, or by further containing a thickener.

[0046] From the viewpoint of low irritation to the skin, the cleanser of the present invention is preferably weakly acidic to weakly basic, and has a pH at 25°C of preferably 5 to 8.5, more preferably 5 to 7.5. The pH of the cleanser of the present invention can be measured by the glass electrode method as is for liquid cleansers, or after dissolving or suspending the solid cleansers in water. The pH of the cleanser of the present invention can be adjusted to the above range by containing the cleanser composition of the present invention as a cleansing component or cleansing aid, or by further containing a pH adjuster.

[0047] In one embodiment of the present invention, a thickener can be added to the cleanser composition of the present invention to provide a more thickened cleanser. Examples of suitable thickeners include modified starch such as hydroxypropyl starch phosphate, and nonionic surfactants such as fatty acid alkanolamides, glycine-type surfactants, aminoacetic acid betaine-type surfactants, sulfobetaine-type surfactants, and amidoamine oxide-type surfactants. Hydroxypropyl starch phosphate is a hydroxypropyl ether diester of phosphoric acid and starch. Fatty acid alkanolamides are obtained by condensing alkanolamines with fatty acids having approximately 8 to 22 carbon atoms, preferably 8 to 18 carbon atoms, and examples thereof include lauric acid monoethanolamide, lauric acid diethanolamide, myristic acid monoethanolamide, myristic acid diethanolamide, palmitic acid monoethanolamide, palmitic acid diethanolamide, stearic acid monoethanolamide, stearic acid diethanolamide, coconut oil fatty acid monoethanolamide, and coconut oil fatty acid diethanolamide. From the viewpoint of the thickening effect of the cleanser, lauric acid diethanolamide, coconut oil fatty acid monoethanolamide, coconut oil fatty acid diethanolamide, etc. are preferably used. Examples of glycine-type amphoteric surfactants include 2-alkyl-N-carboxymethyl-N-hydroxyethylimidazolinium betaine, N-coconut oil fatty acid acyl-N-carboxymethoxyethyl-N-carboxymethylethylenediamine disodium, N-lauroyl-N'-carboxymethyl-N'-hydroxyethylethylenediamine sodium, etc. Examples of aminoacetic acid betaine-type amphoteric surfactants include fatty acid amidopropyl betaines such as lauric acid amidopropyl betaine, myristic acid amidopropyl betaine, coconut oil fatty acid amidopropyl betaine, and palm kernel oil fatty acid amidopropyl betaine, and alkyldimethylaminoacetic acid betaines such as lauryl dimethylaminoacetic acid betaine and coconut oil alkyldimethylaminoacetic acid betaine. Examples of sulfobetaine-type amphoteric surfactants include lauryl hydroxysulfobetaine, lauric acid amidopropyl hydroxysulfobetaine, and fatty acid amidopropyl hydroxysulfobetaine.Examples of amidoamine oxide type amphoteric surfactants include lauric acid amidopropyl dimethylamine oxide.

[0048] The cleanser of the present invention may contain, as the thickener, one selected from the group consisting of the above-mentioned hydroxypropyl starch phosphate, fatty acid alkanolamide, glycine-type amphoteric surfactant, aminoacetic acid betaine-type amphoteric surfactant, sulfobetaine-type amphoteric surfactant, and amidoamine oxide-type amphoteric surfactant, either alone or in combination. From the viewpoint of the thickening effect of the cleanser of the present invention, hydroxypropyl starch phosphate, fatty acid alkanolamide, and fatty acid amidopropyl betaine are preferably used, and hydroxypropyl starch phosphate, coconut oil fatty acid monoethanolamide, and coconut oil fatty acid amidopropyl betaine are more preferably used.

[0049] In one embodiment of the present invention, a cleanser may contain the cleanser composition of the present invention as a cleanser component and further contain a thickener. The content of the cleanser composition of the present invention in the cleanser of this embodiment of the present invention is preferably 1% by weight to 50% by weight, more preferably 1% by weight to 30% by weight, and even more preferably 10% by weight to 30% by weight, based on the total amount of the above-mentioned components (A), (B), and (C), or the total amount of the above-mentioned components (A), (B), (C), and (D). In the cleanser of this embodiment of the present invention, the thickener is preferably one or more selected from the group consisting of the above-mentioned hydroxypropyl starch phosphate, fatty acid alkanolamide, glycine-type amphoteric surfactant, aminoacetic acid betaine-type amphoteric surfactant, sulfobetaine-type amphoteric surfactant, and amidoamine oxide-type amphoteric surfactant. The content of the thickener in the cleanser of this embodiment of the present invention is preferably 1% by weight to 5% by weight, more preferably 2% by weight to 5% by weight.

[0050] Furthermore, in another embodiment of the present invention, a cleanser can be prepared that contains the cleanser composition of the present invention as a cleaning aid and further contains a thickener. The content of the cleanser composition of the present invention in the cleanser of this embodiment of the present invention is preferably 0.5 to 10% by weight, more preferably 1 to 7% by weight, of the total amount of the above-mentioned components (A), (B), and (C) or the total amount of the above-mentioned components (A), (B), (C), and (D). In the cleanser of this embodiment of the present invention, the thickener is preferably one or more selected from the group consisting of the above-mentioned hydroxypropyl starch phosphate, fatty acid alkanolamide, glycine-type amphoteric surfactant, aminoacetic acid betaine-type amphoteric surfactant, sulfobetaine-type amphoteric surfactant, and amidoamine oxide-type amphoteric surfactant. The content of such thickener is also the same as in the cleanser of the above embodiment.

[0051] The viscosity of the above-described detergents, i.e., detergents containing the detergent composition of the present invention as a detergent component or cleaning aid and further containing a thickener, can be adjusted to an appropriate range depending on their form by appropriately setting the content of the detergent composition of the present invention, the type and content of the thickener, or by combining them with other detergent components, cleaning aids, or general additives. The viscosity of the detergents of the above-described aspects of the present invention, as measured at 25°C using a Brookfield viscometer, can be adjusted preferably to a range of 500 mPa·s to 400,000 mPa·s, and they can be in the form of a liquid, paste, cream, or the like. In the cleansing agent of the above-described embodiment of the present invention, the viscosity measured at 25°C using a Brookfield viscometer is preferably 500 mPa·s or more, 1,000 mPa·s or more, 2,000 mPa·s or more, 10,000 mPa·s or more, 30,000 mPa·s or more, or may be 100,000 mPa·s or more, or may be 1,000 mPa·s to 60,000 mPa·s, 2,000 mPa·s to 60,000 mPa·s, 10,000 mPa·s to 60,000 mPa·s, 30,000 mPa·s to 400,000 mPa·s, or 100,000 mPa·s to 300,000 mPa·s. For example, a cleanser containing the cleanser composition of the present invention as a cleanser component or cleaning aid and further containing a fatty acid alkanolamide and a fatty acid amidopropyl betaine as a thickener can have a viscosity measured at 25°C using a Brookfield viscometer of 500 mPa·s or more. The viscosity of such a cleanser measured at 25°C using a Brookfield viscometer is preferably 1,000 mPa·s to 60,000 mPa·s, more preferably 2,000 mPa·s to 60,000 mPa·s, and even more preferably 10,000 mPa·s to 60,000 mPa·s. The cleanser of this embodiment of the present invention is in the form of a viscous liquid to a cream and can be suitably provided as a hair shampoo, body shampoo, etc.Furthermore, for example, a cleanser containing the cleanser composition of the present invention as a cleanser component or cleaning aid and further containing hydroxypropyl starch phosphate as a thickener preferably has a viscosity measured at 25° C. using a Brookfield viscometer of 30,000 mPa·s to 400,000 mPa·s, more preferably 100,000 mPa·s to 300,000 mPa·s. The cleanser of this embodiment of the present invention is in the form of a paste or cream, and can be suitably provided as a facial cleanser foam, facial cleansing cream, cleansing cream, etc.

[0052] The present invention will now be described in more detail with reference to examples.

[0053] Examples 1 to 3, Reference Examples 1 to 3: Preparation of Detergent Compositions 50 g (0.56 mol) of L-alanine, 9 g (0.05 mol) of decanoic acid (capric acid), 76 g (0.38 mol) of dodecanoic acid (lauric acid), 15 g (0.07 mol) of tetradecanoic acid (myristic acid), and 18 g (0.45 mol) of sodium hydroxide were mixed and reacted for 23 hours under a nitrogen gas atmosphere at temperatures of 162°C, 170°C, and 147°C while removing the generated water. The reaction mixture was cooled to obtain the detergent compositions of Examples 1 to 3. Decanoic acid, dodecanoic acid, and tetradecanoic acid were each used alone as the fatty acid, and the reaction was carried out in the same manner as above at a reaction temperature of 162°C. The resulting reaction mixture was cooled to obtain the detergent compositions of Reference Examples 1 to 3. Commercially available L-alanine, decanoic acid, dodecanoic acid, tetradecanoic acid, and sodium hydroxide were used. Specifically, L-alanine was supplied by Anhui Huaheng Biotechnology Co., Ltd., decanoic acid, dodecanoic acid, and tetradecanoic acid were supplied by Fujifilm Wako Pure Chemical Industries, Ltd., and sodium hydroxide was supplied by Showa Denko KK.

[0054] The appearance of each of the detergent compositions prepared in Examples 1 to 3 and Reference Examples 1 to 3 was observed when diluted with water to a solid content of 30% by weight. The components contained in the detergent compositions prepared in Examples 1 to 3 and Reference Example 1 that were observed to have a liquid appearance were analyzed by high-performance liquid chromatography (HPLC) (HPLC: "Chromaster," Hitachi High-Tech Corporation; column: reverse-phase column (C18 column) "Inertsil ODS-3, particle size = 5 μm, 4.6 mm × 250 mm," GL Sciences Inc.). Shampoos containing the detergent compositions prepared in Examples 1 to 3 and Reference Example 1 were prepared according to the formulations shown in Table 5 below, and evaluated for foaming ability and foam quality (foam fineness) as follows. The content of each of the detergent compositions prepared in Examples 1 to 3 and Reference Example 1 was 30% by weight in terms of solid content. (1) Foaming Ability A shampoo containing each of the detergent compositions prepared above was diluted with water so that the content of the detergent components was 1.5% by weight in terms of solid content, and then stirred at 25°C for 20 seconds using a dynamic foam analyzer ("DFA100", KRUESS). The foam volume after 60 seconds was measured and evaluated according to the following evaluation criteria. <Evaluation Criteria> A: 55 mL or more B: 40 mL or more and less than 55 mL C: Less than 40 mL (2) Foam Fineness As in the evaluation of foaming ability described above, a shampoo containing each of the detergent compositions was diluted with water so that the content of the detergent components was 1.5% by weight in terms of solid content, and then stirred using a dynamic foam analyzer. The particle size of the foam after 10 seconds was calculated by image analysis of a two-dimensional image and evaluated according to the following evaluation criteria. <Evaluation Criteria> A: 2,250 μm ２ Below B; 2,250 μm ２ Exceeding 3,500 μm ２ Below C: 3,500μm ２ The results of the above-mentioned observation of the appearance of the detergent compositions produced in Examples 1 to 3 and Reference Examples 1 to 3, and the results of the above-mentioned analysis and evaluation of the foaming ability and foam quality of the detergent compositions produced in Examples 1 to 3 and Reference Example 1 are shown in Table 1.

[0055]

[0056] As shown in Table 1, when a mixture of decanoic acid, dodecanoic acid, and tetradecanoic acid, which have different carbon chain lengths, was used as the fatty acid to be reacted with L-alanine (Examples 1 to 3), the resulting detergent compositions had good solubility in water, and shampoos containing the resulting detergent compositions exhibited good foaming properties and the formed foam was of good quality, with fine foam being observed. On the other hand, when dodecanoic acid or tetradecanoic acid was used alone as the fatty acid to be reacted with L-alanine (Reference Examples 2 and 3), the resulting detergent compositions had poor solubility in water, and when decanoic acid was used (Reference Example 1), the resulting detergent compositions were soluble in water, but the shampoos containing the detergent compositions had poor foaming properties and foam quality. Therefore, the above evaluation results suggest that the detergent composition of the present invention preferably contains a reaction mixture obtained by reacting a mixture of two or more fatty acids having different carbon chain lengths with L-alanine in the presence of a basic substance, and further suggests that a composition containing N-acyl-DL-alanine and its salt, N-acyl-DL-alanylalanine and its salt, fatty acid and its salt, and unacylated DL-alanine and its salt, obtained by reacting the mixture of fatty acids with L-alanine at 147°C to 170°C in the presence of a basic substance, is preferable from the viewpoint of foaming ability and foam quality.

[0057] Next, the low-temperature stability of the cleaning compositions produced in Examples 1 to 3 was evaluated. Each of the cleaning compositions in Examples 1 to 3 was diluted with water to a solids content of 30% by weight. 5 g of each diluted solution was dispensed into a 10 mL glass vial and left to stand in an incubator at 0°C. After 24 hours, the vial was removed and its appearance was observed and evaluated according to the following evaluation criteria. <Evaluation criteria> A: Transparent, liquid appearance, no change in appearance from before storage at 0°C B: Changes in appearance, such as cloudiness and precipitation of solid matter, were observed after storage at 0°C The results of the evaluation of the low-temperature stability of the cleaning compositions produced in Examples 1 to 3 are shown in Table 2.

[0058]

[0059] As shown in Table 2, when L-alanine, a fatty acid, and sodium hydroxide were reacted at 162° C. and 170° C., respectively, the resulting detergent compositions (Examples 1 and 2) showed no change in appearance after 24 hours of storage at 0° C. On the other hand, when L-alanine, a fatty acid, and sodium hydroxide were reacted at 147° C., the resulting detergent composition (Example 3) became cloudy due to precipitation of the fatty acid after 24 hours of storage at 0° C.

[0060] [Examples 4 to 8, Comparative Examples 1 to 4] Detergent Compositions The detergent composition of Comparative Example 1 was prepared by reacting L-alanine with coconut oil fatty acid chloride by a conventional method (Schotten-Baumann method). Furthermore, L-alanine (Junsei Chemical Co., Ltd.) and coconut oil fatty acid (NOF Corporation) were added to the detergent composition of Comparative Example 1 to prepare the detergent compositions of Comparative Examples 2 to 4 with the compositions shown in Table 3. The detergent composition produced in Example 1 and the detergent composition of Comparative Example 1 were mixed, and coconut oil fatty acid (NOF Corporation) and L-alanine (Junsei Chemical Co., Ltd.) were added to prepare the detergent compositions of Examples 4 and 7 with the compositions shown in Table 3. The detergent composition of Example 5 or 6 was prepared by adding coconut oil fatty acid (NOF Corporation) or L-alanine (Junsei Chemical Co., Ltd.) to the detergent composition produced in Example 1 to prepare the detergent composition with the compositions shown in Table 3. Furthermore, coconut oil fatty acid (NOF Corporation) and L-alanine (Junsei Chemical Co., Ltd.) were added to the detergent composition of Comparative Example 1 to prepare the detergent composition of Example 8 with the composition shown in Table 3. Each of the detergent compositions produced in Examples 1 to 3, as well as each of the detergent compositions of Examples 4 to 8 and each of the detergent compositions of Comparative Examples 1 to 4, was dissolved in water to a solid content of 20% by weight to prepare an aqueous solution, which was then further diluted with water to a solid content of 1.5% by weight. (1) Foaming Ability The diluted aqueous solutions of each detergent composition prepared above were stirred at 25°C for 20 seconds using a dynamic foam analyzer ("DFA100", KRUESS), and the foam volume after 30 seconds was measured and evaluated according to the following evaluation criteria. <Evaluation Criteria> AA: 50 mL or more A: 40 mL or more but less than 50 mL B: 35 mL or more but less than 40 mL C: Less than 35 mL (2) Foam Fineness The diluted aqueous solutions of each cleanser composition prepared above were stirred at 25°C for 20 seconds using a dynamic foam analyzer, and the particle size of the foam after 30 seconds was calculated by image analysis of a two-dimensional image and evaluated according to the following evaluation criteria. <Evaluation Criteria> AA: 5,500 μm ２ Below A: 5,500μm ２ Exceeding 6,500 μm ２ Below B: 6,500μm ２ Over 7,000 μm ２ Below C: 7,000μm２ The evaluation results of foaming ability and foam fineness are also shown in Table 3.

[0061]

[0062] As shown in Table 3, the aqueous solutions of the detergent compositions produced in Examples 1 to 3 and diluted solutions of the aqueous solutions of the detergent compositions in Examples 4 to 8 were rated "A" or higher for both foaming ability and foam fineness. On the other hand, the diluted solutions of the detergent composition of Comparative Example 1, which did not contain unacylated L-alanine, DL-alanine, or sodium salts thereof and contained less than 45 parts by weight of fatty acid and its sodium salt relative to 100 parts by weight of N-acyl-DL-alanine and its sodium salt, and the detergent composition of Comparative Example 2, which contained less than 45 parts by weight of fatty acid and its sodium salt relative to 100 parts by weight of N-acyl-DL-alanine and its sodium salt, were rated "C" for both foaming ability and foam quality (foam fineness). Furthermore, in the diluted aqueous solutions of the detergent compositions of Comparative Examples 3 and 4, in which the content of fatty acids and their sodium salts was less than 45 parts by weight per 100 parts by weight of N-acyl-DL-alanine and its sodium salt, and the content of unacylated L-alanine, DL-alanine, and their sodium salts was far more than 150 parts by weight per 100 parts by weight of N-acyl-DL-alanine and its sodium salt, the former was rated "B" for foam quality (foam fineness), and the latter was rated "B" for foaming ability.

[0063] Next, the feel during use of the detergent composition produced in Example 1 and the detergent compositions of Examples 4, 6, and 8 was evaluated. At the same time, evaluations were also performed on the detergent composition of Comparative Example 5, which was prepared by adding coconut oil fatty acids (NOF Corporation) to the detergent composition of Comparative Example 1 to give the composition shown in Table 4, and the detergent composition of Comparative Example 6, which was prepared by adding coconut oil fatty acids (NOF Corporation) and L-alanine (Junsei Kagaku Co., Ltd.) to the detergent composition of Comparative Example 1 to give the composition shown in Table 4. The feel during use was evaluated by five panelists using an aqueous solution prepared by dissolving each detergent composition in water to a solids content of 20% by weight. Five panelists washed their skin and hair with the aqueous solution, and performed sensory evaluations of the lathering, creaminess of the lather, moist finish, smoothness upon application to skin, and combability upon application to hair according to the following evaluation criteria. The average score of the five panelists was calculated for each evaluation item, and the results, judged according to the following evaluation criteria, are also shown in Table 4. <Evaluation criteria> Very good: 5 points Good: 4 points Average: 3 points Fair: 2 points Poor: 1 point <Judgment criteria> AA: 3.5 points or more A: 3 points or more but less than 3.5 points B: 2 points or more but less than 3 points C: Less than 2 points

[0064]

[0065] As shown in Table 4, the detergent composition produced in Example 1 and the detergent compositions of Examples 4, 6, and 8 were rated "AA" or "A" in all of the following categories: foaming when an aqueous solution of each detergent composition was used, creaminess of the foam, moist feeling after application, smoothness when applied to skin, and combing ease when applied to hair. On the other hand, the detergent compositions of Comparative Examples 5 and 6, which do not contain N-acylated L-alanine, DL-alanine, and sodium salts thereof, or in which the content of N-acyl-DL-alanine and its sodium salt is less than 10 parts by weight per 100 parts by weight of N-acyl-DL-alanine and its sodium salt, and in which the content of fatty acid and its sodium salt is much more than 245 parts by weight per 100 parts by weight of N-acyl-DL-alanine and its sodium salt, were evaluated as "C" for foaming when either aqueous solution was used. The creaminess of the foam when the aqueous solution of the detergent composition of Comparative Example 5 was used and the moist finish when the detergent composition of Comparative Example 6 was used were both evaluated as "A", but the usability when the aqueous solution of each detergent composition was used was evaluated as "B".

[0066] The above evaluation results of foaming, foam quality, and usability for the cleanser compositions produced in Examples 1 to 3, Examples 4 to 8, and Comparative Examples 1 to 6 demonstrate that the cleanser compositions of the present invention containing components (A) to (D) have excellent foaming and foam quality, and also provide an excellent usability when used to cleanse skin and hair. Furthermore, the results suggest that good foaming and foam quality can be obtained when the contents of component (B) and component (C) in the cleanser composition are 45 to 245 parts by weight and 10 to 150 parts by weight, respectively, per 100 parts by weight of component (A).

[0067] [Example 9, Comparative Examples 7 to 12] Shampoo The ingredients shown in Table 5 were added sequentially to water, mixed uniformly, and dissolved to prepare shampoos of Example 9 and Comparative Examples 7 to 12. For the shampoos of Example 9 and Comparative Examples 7 to 12, pH was measured at 25°C using the glass electrode method, and the foam quality (foam fineness) was evaluated, the coefficient of friction of the hair bundle after washing was measured, and the feel of the hair bundle after washing was evaluated as described below. The measurement results and evaluation results are also shown in Table 5. (1) Evaluation of Foam Quality (foam fineness) Each shampoo of the Examples and Comparative Examples was diluted with hard water (hardness = 300 ppm) so that the content of the detergent components was 1.5 wt% in terms of solid content, and then stirred for 20 seconds at 25°C using a dynamic foam analyzer ("DFA100", KRUESS). The particle sizes of the foam after 10 seconds and 180 seconds were calculated by image analysis of two-dimensional images and evaluated according to the following evaluation criteria. <Evaluation criteria for foam fineness after 10 seconds> AA: 2,500 μm ２ Below A: 2,500μm ２ Exceeding 4,000 μm ２ Below B: 4,000μm ２ Exceeding 5,000 μm ２ Below C; 5,000μm ２ <Evaluation criteria for foam fineness after 180 seconds> AA: 7,500 μm or more ２ Below A: 7,500μm ２ Exceeding 10,000 μm ２ Below B: 10,000μm ２ Exceeding 12,500 μm ２ Below C; 12,500μm ２(2) Measurement of coefficient of friction of hair bundle after washing Each shampoo of the Examples and Comparative Examples was diluted 7 times with hard water (hardness = 300 ppm), and a hair bundle (10 g, 30 cm) was immersed in 98 g of the diluted solution at 25 ° C. for 5 minutes. Furthermore, the hair bundle was immersed in 800 g of hard water (hardness = 300 ppm) for 30 seconds, and this was repeated twice. Thereafter, the hair bundle was towel-dried for 10 seconds, and the coefficient of friction of the hair bundle was measured three times using a friction sensation measuring device ("TL201Ts", Trinity Lab Co., Ltd.). The average of the measured values ​​was calculated and evaluated according to the following evaluation criteria. <Evaluation criteria> AA: Coefficient of friction is 0.225 or less A: Coefficient of friction is more than 0.225 and less than 0.25 B: Coefficient of friction is more than 0.25 and less than 0.275 C: Coefficient of friction is more than 0.275 (3) Evaluation of feel of hair bundle after washing Each shampoo of the Examples and Comparative Examples was diluted 7 times with hard water (hardness = 300 ppm), and a hair bundle (10 g, 30 cm) was immersed in 98 g of the diluted solution at 25 ° C for 5 minutes. Furthermore, the hair bundle was immersed in 800 g of hard water (300 ppm) for 30 seconds, and this was repeated twice, and then the hair bundle was dried in a thermostatic chamber (25 ° C). One panelist evaluated the feel of the hair bundle after drying according to the following evaluation criteria. <Evaluation criteria> Very good: AA Good: A Fair: B Poor: C

[0068]

[0069] As shown in Table 5, the shampoo of Example 9, which contained the detergent composition produced in Example 1 as a detergent component, was superior in foam quality and smoothness represented by the coefficient of friction after washing a hair strand, and was also evaluated as having a good feel to the hair strand, compared to the detergent composition of Comparative Example 1 and the shampoos of Comparative Examples 7 to 12, which used commercially available anionic surfactants (sodium polyoxyethylene lauryl ether sulfate, sodium α-olefin sulfonate, sodium N-cocoyl methyl taurate, sodium cocoyl isethionate, and sodium N-lauroyl sarcosinate) as detergent components. The above evaluation results suggest that cleansers containing the detergent composition of the present invention as a detergent component have good foam quality, can impart a smooth and pleasant feel to hair, and can reduce the squeaky feeling after washing.

[0070] Examples 10 to 14, Comparative Examples 13 to 17 Shampoos In the shampoo of Example 9 shown in Table 5, the detergent composition produced in Example 1 was replaced with 10 wt % of the detergent components shown in Table 6 (sodium polyoxyethylene lauryl ether sulfate, sodium N-cocoyl methyl taurate, sodium N-lauroyl sarcosinate, sodium α-olefin sulfonate, and alkyl polyglucoside) in terms of solid content, respectively, and 5 wt % of the detergent composition produced in Example 1 and the detergent composition of Comparative Example 1 as cleaning auxiliaries in terms of solid content, respectively, to prepare shampoos named Examples 10 to 14 and Comparative Examples 13 to 17. The viscosity of each shampoo of Examples 10 to 14 and Comparative Examples 13 to 17 was measured at 25°C using a Brookfield viscometer and evaluated according to the following evaluation criteria. The evaluation results are shown in Table 6. <Evaluation Criteria> AA: Viscosity of 10,000 mPa s or more. A: Viscosity is 2,000 mPa·s or more and less than 10,000 mPa·s. B: Viscosity is 1,000 mPa·s or more and less than 2,000 mPa·s. C: Viscosity is 500 mPa·s or more and less than 1,000 mPa·s. D: Viscosity is less than 500 mPa·s.

[0071]

[0072] As shown in Table 6, the shampoos of Examples 10 to 14, which contained sodium polyoxyethylene lauryl ether sulfate, sodium N-cocoyl methyl taurate, sodium N-lauroyl sarcosine, sodium α-olefin sulfonate, and alkyl polyglucoside as cleansing ingredients, the cleansing composition produced in Example 1 as a cleaning aid, and coconut oil fatty acid monoethanolamide and coconut oil fatty acid amidopropyl betaine as thickeners, all showed a good thickening of 1,000 mPa·s or more, demonstrating excellent handleability as cleansers. On the other hand, the shampoos of Comparative Examples 13 to 17, which contained coconut oil fatty acid monoethanolamide and coconut oil fatty acid amidopropyl betaine as thickeners but the cleansing composition of Comparative Example 1 as a cleaning aid, did not show a thickening of 500 mPa·s or more, except for the shampoo of Comparative Example 16. The viscosity of the shampoo of Comparative Example 16 was also less than 1,000 mPa·s.

[0073] Next, other examples of the cleansing agent of the present invention are shown below. The pH of the cleansing agent in each of the following examples was measured by the glass electrode method in accordance with the Japanese Pharmacopoeia, 18th Edition, General Test Method 2.54 pH Measurement Method, etc.

[0074] [Example 15] Shampoo In Table 7, (1) to (8) were added to (10) in order, mixed, and dissolved uniformly, and the pH was adjusted to 6.5 with (9).

[0075]

[0076] [Example 16] Shampoo In Table 8, (1) to (7) were added to (9) in order, mixed, and dissolved uniformly, and the pH was adjusted to 7.0 with (8).

[0077]

[0078] [Example 17] Shampoo In Table 9, (1) to (7) were added to (9) in order, mixed, and dissolved uniformly, and the pH was adjusted to 7.0 with (8).

[0079]

[0080] Example 18 Body Shampoo In Table 10, (1) to (8) were added to (10) in order, mixed, and dissolved uniformly, and the pH was adjusted to 7.0 with (9).

[0081]

[0082] [Example 19] Facial cleansing foam In Table 11, (1) to (7) were added in order to (9), mixed, and dissolved uniformly, and the pH was adjusted to 6.5 with (8).

[0083]

[0084] [Example 20] Facial cleansing foam In Table 12, (1) to (13) were added to 30 g of (15), dispersed, and heated to 70 to 80°C to dissolve. Separately, (14) was dissolved in the remaining (15) and gradually added with stirring. After the saponification reaction was completed, the mixture was cooled to room temperature.

[0085]

[0086] [Examples 21 to 24, Comparative Examples 18 and 19] Facial cleansing foams In Table 13, (1), (3) to (5) were added to (10) and dissolved by heating to 70 to 80°C. Separately, (7) was dispersed in (6) heated to 80°C, and the mixture was added to the solution while stirring and mixed until homogenous. After that, (8) was added, cooled to 45°C, and (9) was added and mixed to prepare the facial cleansing foams of Examples 21 to 24. Furthermore, the facial cleansing foams of Comparative Examples 18 and 19 were prepared in the same manner as in Table 13, except that (2) was used instead of (1).

[0087] The viscosity of each of the facial cleansing foams of Examples 21 to 24 and Comparative Examples 18 to 19 was measured at 25°C using a Brookfield viscometer and evaluated according to the following evaluation criteria. <Evaluation criteria> A: Viscosity of 100,000 mPa·s or more. B: Viscosity of 30,000 mPa·s or more and less than 100,000 mPa·s. C: Viscosity of less than 30,000 mPa·s. Furthermore, the appearance of each of the facial cleansing foams of Examples 21 to 24 and Comparative Examples 18 to 19 was observed at room temperature and evaluated according to the following evaluation criteria. <Evaluation criteria> A: Presents a uniform white paste. B: Presents a uniform white liquid. C: Separation of two layers, an aqueous layer and an oily layer, is observed. The evaluation results are also shown in Table 13.

[0088]

[0089] As shown in Table 13, the facial cleansing foams of Examples 21 to 24, which contained the cleanser composition produced in Example 1 as a cleanser ingredient, exhibited favorable thickening by the addition of hydroxypropyl starch phosphate. The facial cleansing foams of Examples 23 and 24, in which hydroxypropyl starch phosphate was added in amounts of 3.0 wt % and 4.0 wt %, respectively, produced uniform paste-like facial cleansing foams. On the other hand, the facial cleansing foams of Comparative Examples 18 and 19 contained the cleanser composition of Comparative Example 1, which did not contain unacylated L-alanine, DL-alanine, or their sodium salts, and in which the content of fatty acids and their sodium salts was less than 45 parts by weight per 100 parts by weight of N-acyl-DL-alanine and its sodium salt. However, no thickening by the addition of hydroxypropyl starch phosphate was observed, and no uniform paste-like facial cleansing foams were produced. These results suggest that the addition of hydroxypropyl starch phosphate can produce favorable thickening in the cleansing agents of the present invention, which contain the cleanser composition of the present invention as a cleanser ingredient.

[0090] As described above in detail, the present invention can provide a detergent composition that has excellent foaming and foam quality, a good feel in use, can impart a moist feeling after washing and drying, and further has an improved squeaky feeling after washing. The detergent composition of the present invention can be used as a detergent component and cleaning aid in skin and hair cleansers. The present invention also can provide a method for producing a detergent composition that has a low environmental impact and allows the reaction to proceed under relatively mild conditions. According to the production method of the present invention, the reaction product mixture can be used as a detergent composition as is. Furthermore, the present invention can provide a detergent that contains the above detergent composition, has excellent foaming and foam quality, can impart a moist feeling to skin and hair after washing and drying, has an improved squeaky feeling after washing, and has an excellent feel in use.

[0091] This application is based on patent application No. 2023-156575 filed in Japan, the contents of which are incorporated in their entirety herein.

Claims

1. A detergent composition comprising: (A) one or more components selected from the group consisting of N-acylalanines having an acyl group having 8 to 22 carbon atoms and salts thereof; (B) one or more components selected from the group consisting of fatty acids having 8 to 22 carbon atoms and salts thereof; and (C) one or more components selected from the group consisting of alanine and salts thereof, wherein the content ratio of the components (A), (B) and (C) [(A):(B):(C)] is 100:45-245:10-150 by weight.

2. The cleaning composition according to claim 1, further comprising (D) one or more members selected from the group consisting of N-acylalanylalanine having an acyl group having 8 to 22 carbon atoms and salts thereof.

3. The cleaning composition according to claim 2, wherein the ratio of the content of the component (D) to the content of the component (A) [(A):(D)] is 100:1 to 10 by weight.

4. The cleaning composition according to any one of claims 1 to 3, comprising two or more types of N-acylalanines or salts thereof having acyl groups with different numbers of carbon atoms as (A) one or more types selected from the group consisting of N-acylalanines having an acyl group with a carbon number of 8 to 22 and salts thereof.

5. The cleaning composition according to any one of claims 1 to 3, wherein (B) the one or more selected from the group consisting of fatty acids having 8 to 22 carbon atoms and salts thereof contains two or more fatty acids or salts thereof having different carbon numbers.

6. The cleaning composition according to claim 2 or 3, wherein (D) the one or more members selected from the group consisting of N-acylalanyl alanines having an acyl group with 8 to 22 carbon atoms and salts thereof, comprises two or more members having acyl groups with different carbon numbers or salts thereof.

7. A method for producing a cleaning composition, comprising reacting (a) a fatty acid having 8 to 22 carbon atoms, (b) alanine, and (c) one or more members selected from the group consisting of alkali metal hydroxides and amines at 147°C to 190°C.

8. The method according to claim 7, wherein 0.5 to 1.5 moles of (a) fatty acid having 8 to 22 carbon atoms are used per mole of (b) alanine.

9. The method according to claim 7 or 8, wherein (c) one or more members selected from the group consisting of alkali metal hydroxides and amines are used in an amount of 0.5 to 1.5 moles per mole of (b) alanine.

10. The method according to claim 7 or 8, wherein (a) the fatty acid having 8 to 22 carbon atoms is a mixture of two or more fatty acids having different carbon numbers.

11. The method according to claim 7 or 8, wherein (b) the alanine is L-alanine or DL-alanine.

12. The method according to claim 7 or 8, wherein (c) one or more selected from the group consisting of alkali metal hydroxides and amines is sodium hydroxide.

13. A cleaning agent comprising the cleaning composition according to any one of claims 1 to 3 as a cleaning agent component.

14. The cleansing agent according to claim 13, which has a viscosity of 500 mPa·s to 60,000 mPa·s as measured at 25° C. using a Brookfield viscometer.

15. A cleaning agent comprising the cleaning composition according to any one of claims 1 to 3 as a cleaning auxiliary.

16. The cleansing agent according to claim 15, which has a viscosity of 500 mPa·s to 60,000 mPa·s as measured at 25° C. using a Brookfield viscometer.

17. A cleaning agent comprising the cleaning composition according to any one of claims 1 to 3 as a cleaning agent component, and further comprising a thickener.

18. The cleansing agent according to claim 17, wherein the thickener is one or more selected from the group consisting of hydroxypropyl starch phosphate, fatty acid alkanolamide, glycine type amphoteric surfactant, aminoacetic acid betaine type amphoteric surfactant, sulfobetaine type amphoteric surfactant, and amidoamine oxide type amphoteric surfactant.

19. The cleansing agent according to claim 17, wherein the thickener content is 1% to 5% by weight based on the total weight of the cleansing agent.

20. The cleansing agent according to claim 17, which has a viscosity of 500 mPa·s to 400,000 mPa·s as measured at 25° C. using a Brookfield viscometer.

21. A cleaning agent comprising the cleaning composition according to any one of claims 1 to 3 as a cleaning auxiliary and further comprising a thickener.

22. The cleansing agent according to claim 21, wherein the thickener is one or more selected from the group consisting of hydroxypropyl starch phosphate, fatty acid alkanolamide, glycine type amphoteric surfactant, aminoacetic acid betaine type amphoteric surfactant, sulfobetaine type amphoteric surfactant, and amidoamine oxide type amphoteric surfactant.

23. The cleansing agent according to claim 21, wherein the thickener content is from 1% to 5% by weight based on the total weight of the cleansing agent.

24. The cleansing agent according to claim 21, which has a viscosity of 500 mPa·s to 400,000 mPa·s as measured at 25° C. using a Brookfield viscometer.

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