Compounds using amino acids and carboxylic acids, organic salts, and compositions containing them, and their uses

Abstract

This invention provides novel formulations, organic salts, and compositions containing the same, which utilize amino acids and carboxylic acids and exhibit excellent water retention, hygroscopicity, solubility in poorly soluble substances, antibacterial properties, low skin irritation, biodegradability, and gel-forming properties (thickening effect). [Solution] The present invention is a compound of the following components (A) and (B). (A) Formula (I) below: TIFF2026090374000046.tif10143 A basic amino acid or its salt, expressed as such, where the ratio of the total number of primary or secondary amino groups to the number of carboxyl groups (total number of primary or secondary amino groups / number of carboxyl groups) is greater than 1, and the isoelectric point is greater than 7. (B) A carboxylic acid selected from saturated hydroxy monocarboxylic acids, saturated hydroxy di or tricarboxylic acids, or a salt thereof.

Description

[Technical Field]

[0001] This invention relates to formulations using amino acids and carboxylic acids, organic salts, compositions containing them, and their uses. [Background technology]

[0002] Traditionally, formulations used in cosmetics and daily necessities have been required to be safe for the body and have a low environmental impact, and various studies have been conducted to achieve this balance with functionality.

[0003] Furthermore, various antimicrobial agents have traditionally been used in various fields to prevent contamination and spoilage by microorganisms, and to prevent and treat infections caused by microorganisms. In recent years, due to the outbreak of new infectious diseases, interest in public health has been increasing. Against this backdrop, there is a growing need for agents to keep the human body and the surfaces of materials that come into contact with the human body clean. For these purposes, alcohol-based agents, including ethanol, are usually used, but they have problems such as being difficult to use for people who are sensitive to alcohol, and being highly volatile and not remaining on surfaces, resulting in poor long-term antimicrobial activity. Chlorine-based agents such as sodium hypochlorite solution and hypochlorous acid solution are also used, but sodium hypochlorite is strongly alkaline and its use on the human body is not recommended, and there are restrictions on its use, such as the generation of chlorine gas when mixed with acidic solutions. In addition, hypochlorous acid solution has problems such as poor storage stability, resulting in poor long-term antimicrobial activity, and a reduction in the effective chlorine concentration when used. For these reasons, there is a need for an antimicrobial agent that is highly safe, has low impact on the human body, is low volatility, and has long-lasting effects.

[0004] Furthermore, it is known that cosmetics used for hair treatment, skincare, etc., contain ingredients aimed at retaining moisture and providing hydration. However, these ingredients can sometimes result in a sticky or unpleasant feel, and there has been a demand for a product that satisfies both moisturizing and hydration properties while maintaining a pleasant feel.

[0005] Hair loses moisture and becomes dry due to factors such as dry air, strong shampoos, heat from hair dryers, natural drying after bathing, and damage from perms and hair coloring. When hair becomes dry and lacks moisture, the cuticle, a crucial tissue that covers the surface of the hair to prevent moisture evaporation, give hair shine, and maintain hair health, becomes more prone to peeling. When the cuticle peels off, the hair becomes dry, losing its smoothness and becoming brittle. This not only reduces the flexibility and manageability of the hair, but also makes it more prone to frizz, split ends, and breakage. Therefore, maintaining and moisturizing the hair is important to prevent problems caused by dryness and to keep hair beautiful and healthy.

[0006] Conventionally, it has been proposed to incorporate polyhydric alcohols, which are moisturizing ingredients, into hair treatment compositions such as shampoos (see Patent Documents 1 and 2, etc.). However, conventional hair treatment compositions may not have sufficient water retention and moisturizing performance in low-humidity environments such as after washing hair or during winter dryness, or they may be volatile and unable to maintain their water retention and moisturizing effects over the long term. Therefore, there has been a need for a novel hair treatment composition that can improve upon these points.

[0007] Patent Document 3 discloses organic ammonium salts such as imidazolium salt, pyrrolidinium salt, piperidinium salt, pyridinium salt, and phosphonium salt. While such organic ammonium salts have the property of retaining moisture, there are issues regarding sufficient water retention and moisturizing effects when applied to hair, as well as safety.

[0008] The applicant has proposed organic salts (ionic liquids) having hydrogen-bonding functional groups on cations or anions (Patent Documents 4 and 5), but has not specifically considered the water-retention and moisturizing effects using amino acid-based compounds, or their application to hair and skin care.

[0009] It is known that rough skin is mainly caused by a decrease in skin moisture. For example, dry winter air, skin cleansing, aging, and decreased skin secretions can cause skin dryness. If the skin is left in a dry state, its firmness and luster will decrease, making it prone to what is known as rough skin. To prevent rough skin, it is important to prevent a decrease in the moisture content of the stratum corneum and maintain normal skin function. To maintain the moisture content of the stratum corneum, various moisturizing skincare products that provide the skin with an appropriate amount of moisture have been conventionally known.

[0010] Conventionally, it has been proposed to incorporate polyhydric alcohols, which are moisturizing ingredients, into skincare products (see Patent Document 1). However, conventional skincare products may not have sufficient water retention and moisturizing performance in low-humidity environments, such as during dry winter, or they may be volatile and unable to maintain their water retention and moisturizing effects over the long term. There has been a need for a novel skincare product that can improve upon these points.

[0011] Patent Document 3 discloses organic ammonium salts such as imidazolium salt, pyrrolidinium salt, piperidinium salt, pyridinium salt, and phosphonium salt. While such organic ammonium salts have the property of retaining moisture, there are issues regarding sufficient water retention and moisturizing effects, as well as safety, when applied to skincare products.

[0012] The applicant has proposed a room-temperature liquid organic ammonium salt (ionic liquid) having a hydrogen-bonding functional group on a cation or anion (Patent Documents 4 and 5). [Prior art documents] [Patent Documents]

[0013] [Patent Document 1] Japanese Patent Publication No. 2014-131974 [Patent Document 2] Japanese Patent Publication No. 2014-131975 [Patent Document 3] Japanese Patent Publication No. 2019-023185 [Patent Document 4] International Publication No. 2020 / 166674 [Patent Document 5] International Publication No. 2020 / 166678 [Overview of the Initiative] [Problems that the invention aims to solve]

[0014] However, there is a strong demand for novel compounds that are suitable for addressing the challenges described above. Furthermore, no studies have been conducted on combinations of amines and anions that act as cations in organic ammonium salts, particularly compounds with amino acid-based cation structures, focusing on water retention, hygroscopicity, solubility in poorly soluble substances, antibacterial properties, low skin irritation, biodegradability, and gel-forming properties (thickening effect).

[0015] This invention has been made in view of the above circumstances, and its main objective is to provide novel formulations, organic salts, and compositions containing the same that use amino acids and carboxylic acids and have excellent water retention, hygroscopicity, solubility in poorly soluble substances, antibacterial properties, low skin irritation, biodegradability, and gel-forming properties (thickening effect). Furthermore, it is also objective to provide non-volatile compounds that maintain the above effects over a long period of time. [Means for solving the problem]

[0016] To solve the above problems, the present invention provides a formulation of the following components (A) and (B). (A) Amino acids or their salts (B) Carboxylic acid or salt thereof

[0017] The present invention also provides an organic salt formed by a cation derived from component (A), which may have a cationic residue of component (B), and an anion derived from an anionic residue of component (B), and a formulation containing the same.

[0018] The composition of the present invention contains the above-mentioned compound.

[0019] These formulations and compositions may be used to impart water retention, hygroscopicity, and / or antibacterial properties, and may also be used in cosmetics. Furthermore, they may be used as gel compositions containing polymer compounds and water. [Effects of the Invention]

[0020] The novel formulations using amino acids and carboxylic acids of the present invention, as well as compositions containing them, exhibit excellent water retention, hygroscopicity, solubility in poorly soluble substances, antibacterial properties, low skin irritation, biodegradability, and gel-forming properties (thickening effect). Furthermore, they are non-volatile and maintain the above effects over a long period of time. [Modes for carrying out the invention]

[0021] The present invention will be described in detail below.

[0022] In the present invention, "compound" encompasses the combination of components (A) and (B) until the final target compound is prepared, and also includes cases where components (A) and (B) are used as starting materials to synthesize a salt formed from components (A) and (B), and the salt is used as a compound, and cases where the salt is mixed with other components such as water as needed to form a compound. The compound of the present invention may be a mixture consisting only of components (A) and (B) (including cases where these are salts), or it may be a composition containing components other than components (A) and (B) or their salts, for example, a composition containing water, a composition that is an additive added when manufacturing a product, or a composition that is a product such as an antibacterial agent, antiviral agent, or cosmetic. In this invention, "number of carbon atoms" refers to an integer.

[0023] In the present invention, component (A) is an amino acid or a salt thereof. In the present invention, an amino acid includes compounds having an acidic carboxyl group (-COOH) and a basic amino group (primary amino group, secondary amino group, tertiary amino group) in the molecule. Preferred typical examples include protein constituent amino acids and free amino acids in living organisms.

[0024] Examples of the amino acid salt include carboxylate salts in which at least one of the carboxy groups of the amino acid is substituted with a cation (alkali metal cation, alkaline earth metal cation, ammonium cation, etc.).

[0025] Component (A) is preferably represented by the following formula (I).

[0026] [Chemical formula]

[0027] (In the formula, R 1 represents a monovalent or divalent organic group having 1 to 22 carbon atoms, R 2 each independently represents a hydrogen atom or a monovalent or divalent organic group having 1 to 22 carbon atoms, R 3 represents a divalent organic group having 1 to 22 carbon atoms, l represents 0 to 2, m represents 0 to 2, and n represents 0 or 1. R 1 and R 2 may together form a ring having 3 to 22 carbon atoms. X represents a hydrogen atom or a monovalent cation.) In formula (I), l is preferably 0 or 1, and m is preferably 1 or 2. Note that R 1 and R 2 together forming a ring having 3 to 22 carbon atoms means that R 1 l NH m CR 2 in the unit of R 1 and R 2 together form a ring containing nitrogen N with a total carbon number of 3 to 22, preferably 4 to 10, for R 1 and R 2 and C. In addition to the 3 to 22 carbons forming the ring, the ring may have, as a substituent, a monovalent or divalent organic group having 1 to 22 carbon atoms, preferably 1 to 10 carbon atoms, more preferably 1 to 3 carbon atoms.

[0028] [Organic group] In the present invention, the organic group is essential for a carbon atom and may also contain at least one selected from hydrogen atoms and heteroatoms. The heteroatoms are not particularly limited, but oxygen atoms, nitrogen atoms, sulfur atoms, phosphorus atoms, and halogen atoms are preferred, and oxygen atoms, nitrogen atoms, and sulfur atoms are more preferred. The atomic groups contained in the organic group are not particularly limited, but examples include hydrocarbon groups, heterocyclic groups, and substituents described in the [Substituents] section below. For example, hydrocarbon groups and substituents described in the [Substituents] section below may be substituted for hydrogen atoms of a hydrocarbon group, interrupt the hydrocarbon group, and / or included at the base end of the hydrocarbon group, or may form a fused ring with an aromatic hydroxyl group.

[0029] [Hydroxide group] In the present invention, the hydrocarbon group is not particularly limited, but examples include saturated or unsaturated aliphatic hydrocarbon groups, saturated or unsaturated alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and hydrocarbon groups that combine these. Depending on the context, it may be monovalent or polyvalent, and examples of monovalent saturated or unsaturated aliphatic hydrocarbon groups are not particularly limited, but examples include linear or branched alkyl groups, alkenyl groups, and alkynyl groups. Alkyl groups include linear or branched groups and are not particularly limited, but examples include methyl group, ethane-1-yl group, propane-1-yl group, 1-methylethane-1-yl group, butane-1-yl group, butane-2-yl group, 2-methylpropane-1-yl group, 2-methylpropane-2-yl group, pentane-1-yl group, pentane-2-yl group, hexane-1-yl group, heptane-1-yl group, octan-1-yl group, 2-ethylhexane-1-yl group, 1,1,3,3-tetramethylbutane-1 Examples include -yl group, nonane-1-yl group, decane-1-yl group, undecane-1-yl group, dodecane-1-yl group, tridecane-1-yl group, tetradecane-1-yl group, pentadecane-1-yl group, hexadecane-1-yl group, 2-hexyldecane-1-yl group, heptadecane-1-yl group, octadecane-1-yl group, nonadecane-1-yl group, eicosan-1-yl group, henicosane-1-yl group, docosane-1-yl group, 4,8,12-trimethyltridecane-1-yl group, etc.Alkenyl groups include linear or branched chains and are not particularly limited, but examples include vinyl group, propa-1-en-1-yl group, allyl group, isopropenyl group, buta-1-en-1-yl group, buta-2-en-1-yl group, buta-3-en-1-yl group, 2-methylpropa-2-en-1-yl group, 1-methylpropa-2-en-1-yl group, penta-1-en-1-yl group, penta-2-en-1-yl group, penta-3-en-1-yl group, penta-4-en-1-yl group Group, 3-methylbuta-2-en-1-yl group, 3-methylbuta-3-en-1-yl group, hexa-1-en-1-yl group, hexa-2-en-1-yl group, hexa-3-en-1-yl group, hexa-4-en-1-yl group, hexa-5-en-1-yl group, 4-methylpenta-3-en-1-yl group, 4-methylpenta-3-en-1-yl group, hepta-1-en-1-yl group, hepta-6-en-1-yl group, octa-1-en-1-yl group, octa-7-en-1 -yl group, nona-1-en-1-yl group, nona-8-en-1-yl group, deca-1-en-1-yl group, deca-9-en-1-yl group, undeca-1-en-1-yl group, undeca-10-en-1-yl group, dodeca-1-en-1-yl group, dodeca-11-en-1-yl group, trideca-1-en-1-yl group, trideca-12-en-1-yl group, tetradeca-1-en-1-yl group, tetradeca-13-en-1-yl group, pentadeca-1-en-1-yl group, Examples include pentadeca-14-en-1-yl group, hexadeca-1-en-1-yl group, hexadeca-15-en-1-yl group, heptadeca-1-en-1-yl group, heptadeca-16-en-1-yl group, octadeca-1-en-1-yl group, octadeca-9-en-1-yl group, octadeca-17-en-1-yl group, nonadeca-1-en-1-yl group, icosa-1-en-1-yl group, henicosa-1-en-1-yl group, and docosa-1-en-1-yl group.Alkynyl groups include linear or branched chains and are not particularly limited, but examples include ethinyl, propa-1-in-1-yl, propa-2-in-1-yl, buta-1-in-1-yl, buta-3-in-1-yl, 1-methylpropa-2-in-1-yl, penta-1-in-1-yl, penta-4-in-1-yl, hexa-1-in-1 -yl group, hexa-5-in-1-yl group, hepta-1-in-1-yl group, hepta-6-in-1-yl group, octa-1-in-1-yl group, octa-7-in-1-yl group, nona-1-in-1-yl group, nona-8-in-1-yl group, deca-1-in-1-yl group, deca-9-in-1-yl group, undeca-1-in-1-yl group, undeca-10 -I-1-yl group, dodeca-1-I-1-yl group, dodeca-11-I-1-yl group, trideca-1-I-1-yl group, trideca-12-I-1-yl group, tetradeca-1-I-1-yl group, tetradeca-13-I-1-yl group, pentadeca-1-I-1-yl group, pentadeca-14-I-1-yl group, hexadeca-1-I-1-yl group Examples include the group, hexadeca-15-in-1-yl group, heptadeca-1-in-1-yl group, heptadeca-16-in-1-yl group, octadeca-1-in-1-yl group, octadeca-17-in-1-yl group, nonadeca-1-in-1-yl group, icosa-1-in-1-yl group, henicosa-1-in-1-yl group, docosa-1-in-1-yl group, etc.

[0030] As for saturated or unsaturated alicyclic hydrocarbon groups, saturated alicyclic hydrocarbon groups are preferred and are not particularly limited, but examples of monovalent groups include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, and groups containing alicyclic residues such as residues of these groups.

[0031] The aromatic hydrocarbon group is not particularly limited, but examples include phenyl groups, naphthyl groups, anthracenyl groups, and groups containing aromatic ring residues such as residues thereof. It may also form a fused ring together with substituents described below in [Substituents]. The monovalent aromatic hydrocarbon group is not particularly limited, but examples include phenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 2,4-dimethylphenyl group, 2,5-dimethylphenyl group, 3,4-dimethylphenyl group, 3,5-dimethylphenyl group, 2,4,5-trimethylphenyl group, 2,4,6-trimethylphenyl group, 4-ethylphenyl group, 4-propylphenyl group, 4-isopropylphenyl group, 4-butylphenyl group, 4-tert-butylphenyl group, benzyl group, α,α-dimethylbenzyl group, 4-pentylphenyl group, 4-tert-pentylphenyl group, 2,4-bis(4-tert-pentyl)phenyl group, 1,1,3,3-tetramethylbutylphenyl group, 2-methyl-5-tert-butylphenyl group, 4-pentylphenyl group, 4-hexylphenyl group, 4-hexylphenyl group, 4-hexylphenyl group. Examples include 4-tylphenyl group, 4-octylphenyl group, 4-nonylphenyl group, 4-decanylphenyl group, 4-undecylphenyl group, 4-dodecylphenyl group, 4-tridecylphenyl group, 4-tetradecylphenyl group, 4-pentadecylphenyl group, 4-hexadecylphenyl group, 4-heptadecylphenyl group, 4-octadecylphenyl group, 4-biphenyl group, 2-methoxyphenyl group, 3-methoxyphenyl group, 4-methoxyphenyl group, 2-ethoxyphenyl group, 3-ethoxyphenyl group, 4-ethoxyphenyl group, 2-chlorophenyl group, 2-fluorophenyl group, 4-fluorophenyl group, 2-trifluoromethylphenyl group, 4-trifluoromethylphenyl group, 4-hydroxyphenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthracenyl group, 2-anthracenyl group, and 9-anthracenyl group.

[0032] Examples of divalent hydrocarbon groups include those obtained by removing one hydrogen atom from the above-mentioned groups. [Substituent]

[0033] The substituents mentioned above are not particularly limited, but examples include hydrocarbon groups, oxygen-containing groups, nitrogen-containing groups, sulfur-containing groups, phosphorus-containing groups, halogens, and the like. Substituents also include groups to which these substituents are bonded. Examples of hydrocarbon groups include those listed above under [Hydrogen Groups].

[0034] The oxygen-containing group is not particularly limited, but examples include hydroxyl group, alkoxy group, acetoxy group, acetyl group, aldehyde group, carboxyl group, carboxylate group, urea group, urethane group, amide group, imide group, ether group, carbonyl group, ester group, oxazole group, morpholine group, carbamate group, carbamic acid group, carbamoyl group, polyoxyethylene group, tocopheryl group, chroman group, dihydropyran group, glyceryl group, glyceryl ether group, and the like.

[0035] The nitrogen-containing group is not particularly limited, but examples include cyano group, cyanato group, isocyanate group, nitro group, nitroalkyl group, amide group, urea group, urethane group, imide group, carbodiimide group, azo group, pyridine group, guanidino group, imidazolyl group, indolyl group, primary amino group, secondary amino group, tertiary amino group, quaternary ammonium group, aminoalkyl group, etc.

[0036] Sulfur-containing groups are not particularly limited, but examples include sulfate groups, sulfonyl groups, sulfonic acid groups, mercapto groups, thioether groups, thiocarbonyl groups, thiourea groups, thiocarboxyl groups, thiocarboxylate groups, dithiocarboxyl groups, dithiocarboxylate groups, sulfate esters, thiophene groups, thiazole groups, thiol groups, sulfo groups, sulfide groups, disulfide groups, thioester groups, thioamide groups, thiocarbamate groups, dithiocarbamate groups, and esters thereof.

[0037] Phosphorus-containing groups are not particularly limited, but examples include phosphate groups, phosphite groups, phosphonic acid groups, phosphinic acid groups, phosphonic acid groups, phosphonitic acid groups, phosphinic acid groups, pyrophosphate groups, phosphate ester groups, phosphite ester groups, phosphonic acid ester groups, pyrophosphate groups, and their ester groups. Examples of halogens include fluorine, chlorine, bromine, and iodine.

[0038] In equation (I), R 1 , R 2 Examples of organic groups include hydrocarbon groups that may have substituents and whose hydrocarbon moiety may contain an oxygen atom. For hydrocarbon groups, refer to the information in the [Hydrogen Group] section above. Aliphatic hydrocarbon groups are preferred, and saturated aliphatic hydrocarbon groups (alkyl groups) are more preferred. Alkyl groups may be linear or branched, for example, having 1 to 22, 1 to 10, or 1 to 5 carbon atoms.

[0039] The hydrocarbon group described above may have substituents, and while the substituents are not particularly limited, examples include those listed in the [Substituents] section above. Among the substituents, those having oxygen-containing groups, nitrogen-containing groups, or sulfur-containing groups are preferred, and among these, hydroxyl groups, carboxyl groups, carboxylate groups, ester groups, ether groups, alkoxy groups, amino groups, amide groups, guanidino groups, imidazolyl groups, indolyl groups, mercapto groups, and thioether groups are preferred.

[0040] The hydrocarbon moiety described above may contain an oxygen atom. In this case, the hydrocarbon moiety contains the oxygen-containing group described above, forming or containing, for example, an ether bond, a carbonyl group, a hydroxyl group, a carboxylate group, an ester bond, an amide bond, a urea bond, or a urethane bond. Therefore, in the present invention, "the hydrocarbon moiety contains an oxygen atom" includes cases where the hydrocarbon moiety is interrupted by a group that may also contain heteroatoms such as nitrogen atoms as an atomic group containing oxygen atoms, or where the group contains such a group at its base end, or where a hydrogen atom is substituted by such a group.

[0041] The above organic group may have a hydrogen bonding functional group, and the hydrogen bonding functional group is not particularly limited, but examples include the oxygen-containing group, nitrogen-containing group, sulfur-containing group, phosphorus-containing group, and a hydrogen atom directly bonded to nitrogen.

[0042] In equation (I), R 3 Examples of organic groups include hydrocarbon groups that may have substituents and whose hydrocarbon moiety may contain an oxygen atom. The hydrocarbon groups are as described in the [Hydrogen Groups] section above, and are divalent groups obtained by removing one hydrogen atom from the hydrocarbon groups described above. Aliphatic hydrocarbon groups are preferred, and saturated aliphatic hydrocarbon groups (alkylene groups) are more preferred. The alkylene group may be linear or branched, for example, having 1 to 22, 1 to 10, or 1 to 5 carbon atoms.

[0043] The above hydrocarbon group may have substituents, and there are no particular limitations on the substituents, but examples include those listed in the [substituents] column above.

[0044] Component (A) is preferably an amino acid in which X is a hydrogen atom in (I) above.

[0045] Amino acids include compounds that have one or more amino groups (primary, secondary, or tertiary amino groups) and one or more carboxyl groups (-COOH) in a single molecule. However, amide groups are not included in the definition of amino groups.

[0046] Preferred embodiments of the amino acid include the following, from the viewpoint of the ratio of the number of amino groups to carboxyl groups and the isoelectric point (referred to as amino acids (a) to (f)).

[0047] Amino acid (a): The ratio of the total number of primary or secondary amino groups to the number of carboxyl groups in component (A) (total number of primary or secondary amino groups / number of carboxyl groups) is greater than 1. These amino acids are not limited to, but examples include arginine, histidine, lysine, and tryptophan.

[0048] Amino acid (b): The ratio of the total number of primary or secondary amino groups to the number of carboxyl groups in component (A) (total number of primary or secondary amino groups / number of carboxyl groups) is 1.

[0049] These amino acids are not particularly limited, but examples include leucine, isoleucine, phenylalanine, proline, valine, serine, alanine, threonine, glutamine, asparagine, aminobutyric acid, cysteine, glycine, and methionine.

[0050] Amino acid (c): The ratio of the total number of primary or secondary amino groups to the number of carboxyl groups in component (A) (total number of primary or secondary amino groups / number of carboxyl groups) is less than 1.

[0051] These amino acids are not particularly limited, but examples include glutamic acid and aspartic acid.

[0052] Amino acid (d): The isoelectric point of component (A) is greater than 7.

[0053] These amino acids are not particularly limited, but examples include those classified as basic amino acids, such as arginine (10.76), histidine (7.59), lysine (9.75), and aminobutyric acid (7.85). The numbers in parentheses indicate the isoelectric point of each amino acid.

[0054] Amino acid (e): The isoelectric point of component (A) is between 4 and 7.

[0055] These amino acids are not particularly limited, but examples include those classified as neutral amino acids, such as leucine (5.98), isoleucine (6.02), phenylalanine (5.48), proline (6.30), valine (5.96), tryptophan (5.89), serine (5.68), alanine (6.00), threonine (6.16), glutamine (5.65), asparagine (5.41), cysteine ​​(5.07), glycine (5.97), methionine (5.74), and tyrosine (5.66). The numbers in parentheses indicate the isoelectric point of each amino acid.

[0056] Amino acid (f): The isoelectric point of component (A) is less than 4.

[0057] These amino acids are not particularly limited, but examples include those classified as acidic amino acids, such as glutamic acid (3.22) and aspartic acid (2.77). The numbers in parentheses indicate the isoelectric point of each amino acid.

[0058] Furthermore, in equation (I) above, R 1 , R 2 , R 3 Examples of preferred combinations include the following:

[0059] In the above equation (I), R 1 is an aliphatic hydrocarbon group, R 2 R is a hydrocarbon group which may contain oxygen atoms, nitrogen atoms, and sulfur atoms. 3 The aliphatic hydrocarbon group is the amino acid. Examples of amino acids are not limited to, but include, for example, arginine, histidine, lysine, glutamic acid, aspartic acid, leucine, phenylalanine, proline, valine, tryptophan, serine, isoleucine, alanine, threonine, glutamine, asparagine, aminobutyric acid, cysteine, glycine, and methionine.

[0060] In equation (I) above, l is 0, m is 2, n is 0, and R 2This is a primary amino group or a hydrocarbon group having two or more nitrogen atoms. Examples of these amino acids are not limited to, but include, for example, arginine, histidine, and lysine.

[0061] In the above equation (I), R 1 , R 2 However, these are hydrocarbon groups having at least one carboxyl group. Examples of these amino acids are not limited to glutamic acid and aspartic acid.

[0062] In the above equation (I), R 1 , R 2 However, at least one of them is a hydrocarbon group having a hydroxyl group, an amide group, a secondary amino group, or a sulfur-containing group, or R 1 and R 2 These amino acids come together to form a ring. Examples of these amino acids, though not limited to them, include leucine, phenylalanine, proline, valine, tryptophan, serine, isoleucine, alanine, threonine, glutamine, asparagine, aminobutyric acid, cysteine, glycine, and methionine.

[0063] Furthermore, while not particularly limited, examples of amino acids include those classified as having an isoelectric point greater than 7, between 4 and 7, or less than 4.

[0064] The amino acids with an isoelectric point between 4 and 7 are not particularly limited, but for example, R 2 Examples include amino acids with alkyl chains, amino acids with hydroxyl groups, amino acids containing sulfur, amino acids with amide groups, amino acids with imino groups, amino acids with aromatic groups, and β, γ, δ, or ε-amino acids.

[0065] R 2 As for amino acids with alkyl chains, R 2 l is a hydrogen atom or a linear or branched alkyl group having 1 to 10 carbon atoms, preferably 1 to 4 carbon atoms. In this case, l is either 0 or l is 1 and R 1It is preferable that n is a linear or branched alkyl group having 1 to 3 carbon atoms. It is also preferable that n is 0. Specifically, examples include glycine, alanine, valine, leucine, isoleucine, sarcosine, and the like.

[0066] R 2 As for amino acids that have a hydroxyl group, R 2 The molecule has 1 to 5 carbon atoms, preferably 1 to 3, and is linear or branched, with 1 to 3 hydroxyl groups, preferably 1, forming a hydroxyalkyl group. In this case, l is either 0 or l is 1 and R 1 It is preferable that the element is a linear or branched alkyl group having 1 to 3 carbon atoms, and more preferably that l is 0. It is also preferable that n is 0. Specifically, examples include serine and threonine.

[0067] R 2 As for sulfur-containing amino acids, R 2 The following are some examples:

[0068] [ka]

[0069] (In the formula, R 21 R indicates a methylene group, 22 represents a methyl group or -CH2CH(NH2)(COOH). a1 represents 1 to 5, preferably 1 to 3, and a2 represents 1 to 4, preferably 1 or 2. a1 has S and a2 has R 22 The order of the elements is arbitrary.

[0070] In this case, l is either 0 or l is 1 and R 1 It is preferable that the alkyl group is a linear or branched alkyl group having 1 to 3 carbon atoms, and more preferably that l is 0. It is also preferable that n is 0. Specifically, examples include cysteine, methionine, cystathionine, etc.

[0071] R 2 As for amino acids that have an amide group, R2 The following are some examples:

[0072] [ka] (In the formula, R 23 This represents a linear or branched alkylene group having 1 to 5 carbon atoms, preferably 1 or 2 carbon atoms.

[0073] In this case, l is either 0 or l is 1 and R 1 It is preferable that the alkyl group has 1 to 3 carbon atoms and contains a secondary amino group, and it is more preferable that l is 0. It is also preferable that n is 0. Specifically, examples include asparagine, glutamine, and citrulline.

[0074] R 2 As amino acids that have an imino group, N and R 1 Examples include compounds in which these elements combine to form a heterocycle. 1 This represents a C3 or C4 alkylene group which may have a hydroxyl group, forming a pyrrolidine ring or a piperidine ring. Preferably, it forms a pyrrolidine ring. In this case, it is preferable that l is 0. It is also preferable that n is 0. Specifically, examples include proline and hydroxyproline. R 2 As for amino acids that have an aromatic group, R 2 The following are some examples:

[0075] [ka]

[0076] (In the formula, R 24 R represents a linear or branched alkylene group having 1 to 5 carbon atoms, preferably 1 or 2 carbon atoms. 25 (This represents an aromatic hydrocarbon group having 6 to 10 carbon atoms or a heterocyclic group having 6 to 10 carbon atoms, which may have substituents.) R 25Preferably, it represents a phenyl group, a hydroxyphenyl group, or an indole group.

[0077] In this case, l is either 0 or l is 1 and R 1 is a linear or branched alkyl group having 1 to 3 carbon atoms, or l is 1 and R 1 It is preferable that the group has 2 to 4 carbon atoms and contains an amide group and a secondary amino group, and it is more preferable that l is 0. It is also preferable that n is 0. Specifically, examples include phenylalanine, tyrosine, tryptophan, 1-methylhistidine, 3-methylhistidine, anserine, carnosine, and the like.

[0078] As for β, γ, δ, or ε-amino acids, R 3 Examples include linear or branched alkylene groups having 1 to 4 carbon atoms. In this case, l is either 0 or l is 1 and R 1 It is preferable that the alkyl group is a linear or branched alkyl group having 1 to 3 carbon atoms, and more preferably that l is 0. It is also preferable that n is 1. Specifically, examples include β-alanine, β-aminoisobutyric acid, γ-aminobutyric acid, ε-aminocaproic acid, etc.

[0079] Amino acids with an isoelectric point less than 4 are R 2 Examples of those that can be expressed by the following formula include:

[0080] [ka] (In the formula, R 26 (This indicates a divalent aliphatic hydrocarbon group with 1 to 10 carbon atoms.)

[0081] In this case, l is either 0 or l is 1 and R 1 It is preferable that the alkyl group is a linear or branched alkyl group having 1 to 3 carbon atoms, and more preferably that l is 0. It is also preferable that n is 0. Specifically, examples include glutamic acid, aspartic acid, and α-aminoadipic acid.

[0082] Amino acids with an isoelectric point greater than 7 are R 2 Examples of those that can be expressed by the following formula include:

[0083] [ka]

[0084] (In the formula, R 27 R represents a linear or branched alkylene group having 1 to 10 carbon atoms, which may have a hydroxyl group. 28 (This represents -NH2, -NHC(=NH)(NH2), or an imidazolyl group.)

[0085] In this case, l is either 0 or l is 1 and R 1 It is preferable that the element is a linear or branched alkyl group having 1 to 3 carbon atoms, and more preferably that l is 0. It is also preferable that n is 0. Specifically, examples include arginine, lysine, histidine, 5-hydroxylysine, omitin, and the like.

[0086] In the present invention, component (B) is a carboxylic acid or a salt thereof. Preferably, component (B) is a carboxylic acid. The carboxylic acid is an organic acid having at least one carboxyl group (-COOH) in its molecule, and may also have an oxygen-containing group, a nitrogen-containing group, a sulfur-containing group, a phosphorus-containing group, a hydrocarbon group, etc., and a carboxylic acid having a hydrocarbon group is preferred. Although not particularly limited, examples of carboxylic acids having a hydrocarbon group include saturated or unsaturated aliphatic hydrocarbon groups, saturated or unsaturated alicyclic hydrocarbon groups, aromatic hydrocarbon groups, etc., and combinations thereof having a hydrocarbon group and a carboxyl group. Examples include saturated aliphatic carboxylic acids, unsaturated aliphatic carboxylic acids, saturated or unsaturated alicyclic carboxylic acids, aromatic carboxylic acids, saturated aliphatic hydroxycarboxylic acids, unsaturated aliphatic hydroxycarboxylic acids, saturated or unsaturated alicyclic hydroxycarboxylic acids, aromatic hydroxycarboxylic acids, carbonyl carboxylic acids, alkyl ether carboxylic acids, halogen carboxylic acids, etc. (The number of carbon atoms in the carboxylic acids listed below includes the carbon atoms of the carboxyl group.)

[0087] Saturated aliphatic carboxylic acids consist of a linear or branched saturated aliphatic hydrocarbon group and one or more carboxy groups, and preferably have 1 to 22 carbon atoms. Examples of saturated aliphatic carboxylic acids include saturated aliphatic monocarboxylic acids having one carboxy group and saturated aliphatic dicarboxylic acids having two carboxy groups. Saturated aliphatic monocarboxylic acids consist of a linear or branched saturated aliphatic hydrocarbon group and one carboxy group, and preferably have 1 to 22 carbon atoms. Among them, any saturated aliphatic monocarboxylic acid selected from HCOOH and CH3(CH2) p COOH (p represents an integer from 0 to 8), and saturated aliphatic monocarboxylic acids having a branched chain are preferred. Specifically, although not particularly limited, for example, formic acid, acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, enanthic acid, caprylic acid, pelargonic acid, capric acid, lauric acid, myristic acid, pentadecanoic acid, palmitic acid, margaric acid, stearic acid, arachidic acid, heneicosylic acid, behenic acid, isobutyric acid, 2-methylbutyric acid, isovaleric acid, 2-ethylhexanoic acid, isononanoic acid, isopalmitic acid, isostearic acid, etc. can be mentioned. Saturated aliphatic dicarboxylic acids consist of a linear or branched saturated aliphatic hydrocarbon group and two carboxy groups, and preferably have 2 to 22 carbon atoms. Among them, saturated dicarboxylic acids represented by HOOC(CH2) x COOH (x represents an integer from 0 to 4) are preferred. Specifically, although not particularly limited, for example, oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, glutamic acid, etc. can be mentioned.

[0088] Unsaturated aliphatic carboxylic acids consist of a linear or branched unsaturated aliphatic hydrocarbon group and one or more carboxy groups, and preferably have 3 to 22 carbon atoms. Examples of unsaturated aliphatic carboxylic acids include unsaturated aliphatic monocarboxylic acids having one carboxy group and unsaturated aliphatic dicarboxylic acids having two carboxy groups. An unsaturated aliphatic monocarboxylic acid consists of a linear or branched unsaturated aliphatic hydrocarbon group and one carboxy group, and preferably has 1 to 22 carbon atoms. Among them, R 1 CH=CH(CH2) r COOH (R 1 is a hydrogen atom or CH3(CH2) q - (q represents an integer from 0 to 7.) and r represents an integer from 0 to 7.) is preferably an unsaturated aliphatic monocarboxylic acid represented by. Specifically, although not particularly limited, for example, acrylic acid, methacrylic acid, crotonic acid, palmitoleic acid, oleic acid, vaccenic acid, linoleic acid, linolenic acid, eleostearic acid, arachidonic acid, etc. can be mentioned. An unsaturated aliphatic dicarboxylic acid consists of a linear or branched unsaturated aliphatic hydrocarbon group and two carboxy groups, and preferably has 1 to 4 carbon atoms. Specifically, although not particularly limited, for example, maleic acid, fumaric acid, etc. can be mentioned.

[0089] A saturated or unsaturated alicyclic carboxylic acid consists of a saturated or unsaturated carbocyclic ring having no aromaticity and one or more carboxy groups, and preferably has 6 to 20 carbon atoms. Among them, a saturated alicyclic carboxylic acid having a cyclohexane ring skeleton is preferred. Examples of the saturated or unsaturated alicyclic carboxylic acid include a saturated or unsaturated alicyclic monocarboxylic acid having one carboxy group, a saturated or unsaturated alicyclic dicarboxylic acid having two carboxy groups, etc. Examples of the saturated or unsaturated alicyclic monocarboxylic acid include, but are not particularly limited to, cyclohexanecarboxylic acid, etc. Examples of the saturated or unsaturated alicyclic dicarboxylic acid include, but are not particularly limited to, cyclohexanedicarboxylic acid, etc.

[0090] An aromatic carboxylic acid consists of a monocyclic or polycyclic ring having aromaticity and one or more carboxy groups, and preferably has 6 to 20 carbon atoms. Among these, aromatic carboxylic acids having a benzene ring skeleton are preferred. Examples of aromatic carboxylic acids include aromatic monocarboxylic acids with one carboxyl group and aromatic dicarboxylic acids with two carboxyl groups. Aromatic monocarboxylic acids are not particularly limited, but examples include benzoic acid and cinnamic acid. Aromatic dicarboxylic acids are not particularly limited, but examples include phthalic acid, isophthalic acid, and terephthalic acid.

[0091] A saturated aliphatic hydroxycarboxylic acid consists of a linear or branched saturated aliphatic hydrocarbon group, one or more carboxyl groups, and one or more hydroxyl groups, preferably having 2 to 24 carbon atoms. Among these, a saturated aliphatic hydroxycarboxylic acid having 2 to 7 carbon atoms and 1 to 5 hydroxyl groups is preferred. Examples of saturated aliphatic hydroxycarboxylic acids include saturated aliphatic hydroxymonocarboxylic acids with one carboxyl group, and saturated aliphatic hydroxydi or tricarboxylic acids with two or three carboxyl groups. The saturated aliphatic hydroxy monocarboxylic acid preferably has 2 to 20 carbon atoms, and more preferably 2 to 7 carbon atoms. The number of hydroxyl groups is preferably 1 to 5. Among them, (R 2 )3C(C(R 3 )2) s COOH(s represents an integer from 1 to 4, and there are 3 R 2 and 2 × s R 3 Each of these independently represents either a hydrogen atom or a hydroxyl group, and the total number of hydroxyl groups is 1 to 5. A saturated hydroxy monocarboxylic acid represented by ) is preferred. Specifically, although not particularly limited, examples include glycolic acid, lactic acid, glyceric acid, hydroxyacetic acid, hydroxybutyric acid, 2-hydroxydecanoic acid, 3-hydroxydecanoic acid, 12-hydroxystearic acid, dihydroxystearic acid, cerebronic acid, leucic acid, mevalonic acid, pantoic acid, gluconic acid, galactonic acid, mannonic acid, arabinonic acid, fructuronic acid, tagaturonic acid, and aldonic acid. The saturated aliphatic hydroxydi or tricarboxylic acid preferably has 4 to 22 carbon atoms. The number of hydroxyl groups is preferably 1 to 3. Among them, HOOCC(R 4 R 5 )C(R 6 R 7 )C(R 8 R 9 )COO - (R 4 ~R 9 Each of these independently represents a hydrogen atom, a hydroxyl group, or a carboxyl group, with a total of 1 to 2 hydroxyl groups and a total of 1 to 2 carboxyl groups. A saturated hydroxydi or tricarboxylic acid represented by ) is preferred. Specifically, although not particularly limited, examples include tartaric acid, malic acid, tartaric acid, citramalic acid, citric acid, isocitric acid, and so on.

[0092] An unsaturated aliphatic hydroxycarboxylic acid consists of a linear or branched saturated aliphatic hydrocarbon group, one or more carboxyl groups, and one or more hydroxyl groups, preferably having 3 to 22 carbon atoms. Specifically, although not particularly limited, examples include ricinoleic acid, ricinoleic acid, and ricineradicic acid.

[0093] A saturated or unsaturated alicyclic hydroxycarboxylic acid consists of a non-aromatic saturated or unsaturated carbon ring, one or more carboxyl groups, and one or more hydroxyl groups, preferably having 4 to 20 carbon atoms. Among these, saturated alicyclic hydroxycarboxylic acids with a 6-membered ring skeleton having 1 to 4 hydroxyl groups are preferred. Specifically, although not particularly limited, examples include hydroxycyclohexanecarboxylic acid, dihydroxycyclohexanecarboxylic acid, quinic acid (1,3,4,5-tetrahydroxycyclohexanecarboxylic acid), shikimic acid, glucuronic acid, galacturonic acid, mannuronic acid, iduronic acid, and guluronic acid. Furthermore, cyclic lactones having hydroxyl groups can also be preferably used. Specifically, although not particularly limited, examples include ascorbic acid and erythorbic acid.

[0094] The aromatic hydroxycarboxylic acid is composed of a monocyclic or multiple rings having aromaticity, one or more carboxy groups, and one or more hydroxy groups, and preferably has 6 to 20 carbon atoms. Among them, aromatic carboxylic acids having a benzene ring skeleton with 1 to 3 hydroxy groups are preferred. Specifically, although not particularly limited, for example, salicylic acid, hydroxybenzoic acid, dihydroxybenzoic acid, trihydroxybenzoic acid, hydroxymethylbenzoic acid, vanillic acid, syringic acid, protocatechuic acid, gentisic acid, orsellinic acid, mandelic acid, benzoic acid, atrolactic acid, phloretic acid, coumaric acid, umbellic acid, caffeic acid, ferulic acid, sinapic acid, etc. can be mentioned.

[0095] The carbonylcarboxylic acid is a carboxylic acid having 3 to 22 carbon atoms with a carbonyl group in the molecule, and a carbonylcarboxylic acid having 3 to 7 carbon atoms with 1 to 2 carbonyl groups is preferred. Among them, CH3((CH2) p CO(CH2) q )COO - (where p and q represent integers from 0 to 2.) The carbonylcarboxylic acid represented is preferred. Specifically, although not particularly limited, for example, pyruvic acid, etc. can be mentioned.

[0096] The alkyl ether carboxylic acid is a carboxylic acid having 2 to 22 carbon atoms with an ether group in the molecule, including polyoxyalkylene alkyl ether carboxylic acids, and an alkyl carboxylic acid having 2 to 12 carbon atoms with 1 to 2 ether groups is preferred. Among them, CH3(CH2) r O(CH2) s COO - (where r and s represent integers from 0 to 4.) The alkyl ether carboxylic acid represented, polyoxyethylene alkyl ether carboxylic acid is preferred. Specifically, although not particularly limited, for example, methoxyacetic acid, ethoxyacetic acid, methoxybutyric acid, ethoxybutyric acid, etc. can be mentioned.

[0097] As the halogen carboxylic acid, a halogen carboxylic acid having 2 to 22 carbon atoms is preferred. Specifically, although not particularly limited, for example, halogen-substituted halogen carboxylic acids such as trifluoroacetic acid, trichloroacetic acid, tribromoacetic acid, pentafluoropropionic acid, pentachloropropionic acid, pentabromopropionic acid, perfluorononanoic acid, perchlorononanoic acid, perbromononanoic acid, etc. can be mentioned.

[0098] Among the carboxylic acids listed above, linear or branched saturated aliphatic monocarboxylic acids, linear or branched unsaturated aliphatic carboxylic acids, saturated aliphatic dicarboxylic acids, unsaturated aliphatic dicarboxylic acids, saturated hydroxymonocarboxylic acids, saturated hydroxy di- or tricarboxylic acids, aromatic carboxylic acids, hydroxyaromatic carboxylic acids, and cyclic lactones having a hydroxyl group are preferred. Among them, linear or branched saturated aliphatic monocarboxylic acids, linear or branched unsaturated aliphatic carboxylic acids, saturated hydroxymonocarboxylic acids, saturated hydroxy di- or tricarboxylic acids, aromatic carboxylic acids, and hydroxyaromatic carboxylic acids are more preferred.

[0099] In a preferred example, component (B) is a carboxylic acid having a hydrogen-bonding functional group in the hydrocarbon moiety. That is, it is preferable that the carboxylic acid has a hydrogen-bonding functional group in addition to one carboxy group (-COOH). The hydrogen-bonding functional group is not particularly limited, and examples thereof include the above-mentioned oxygen-containing group, nitrogen-containing group, sulfur-containing group, phosphorus-containing group, etc. Among these, in terms of expressing the effects of the formulation or composition of the present invention, it is preferable to have an oxygen-containing group, and more preferably to have a hydroxyl group and a carboxy group. Preferably, the hydrogen-bonding functional group is a hydroxyl group and / or a carboxy group. Preferably, the hydrogen-bonding functional group is a hydroxyl group. Preferably, it has both a hydroxyl group and a carboxy group as the hydrogen-bonding functional group.

[0100] In a preferred example, component (B) is an unsaturated or branched aliphatic carboxylic acid having 8 to 22 carbon atoms.

[0101] In a preferred embodiment, the formulation of the present invention contains organic salts of components (A) and (B). Preferably, it contains an organic salt formed by a cation derived from component (A) which may have a cationic residue of component (B) and an anion derived from an anionic residue of component (B).

[0102] In the present invention, the residue in component (B) refers to an atom or atomic group (radical) having no charge. Those having a charge and becoming a cation are called cationic residues, and those becoming an anion are called anionic residues.

[0103] In the present invention, the carboxylic acid or its salt of component (B) has a cationic residue and an anionic residue. The cationic residue is a hydrogen atom or a group (atomic group) that binds to the nitrogen atom of component (A) to form a hydrogen-bonding functional group or an organic group. Preferably, the acid of component (B) is a compound composed of a hydrogen that becomes a proton and an anionic residue.

[0104] The organic salt of the present invention has the following formula (II):

[0105]

Chemical formula

[0106] (In the formula, R 1 represents a monovalent organic group having 1 to 22 carbon atoms, R 2 represents a hydrogen atom or a monovalent or divalent organic group having 1 to 22 carbon atoms, R 3 represents a divalent organic group having 1 to 22 carbon atoms, R 4 represents a hydrogen atom or a monovalent organic group having 1 to 21 carbon atoms, l represents 0 to 3, m represents 0 to 3, and n represents 0 or 1. R 1 and R 2 may together form a ring having 3 to 22 carbon atoms. X represents a hydrogen atom or a monovalent cation.) It is represented by and formed from an amino acid and a carboxylic acid. In formula (II), l is preferably 0 or 1, and m is preferably 2 or 3.

[0107] In formula (II), the amino acids and carboxylic acids that form the organic salt are those listed above. For specific details and preferred examples, refer to all the descriptions above for components (A), (B) and formula (I), which are cited as explanations for formula (II). In addition, preferred examples of the organic salt of formula (II) are listed below. Preferably, X is a hydrogen atom. In one preferred example, the ratio of the total number of primary or secondary amino groups to the number of carboxyl groups in an amino acid (total number of primary or secondary amino groups / number of carboxyl groups) is greater than 1. In another preferred example, the ratio of the total number of primary or secondary amino groups to the number of carboxyl groups in an amino acid (total number of primary and secondary amino groups / number of carboxyl groups) is 1. In yet another preferred example, the ratio of the total number of primary or secondary amino groups to the number of carboxyl groups in an amino acid (total number of primary or secondary amino groups / number of carboxyl groups) is less than 1. In one preferred example, the isoelectric point of the amino acid is greater than 7. In another preferred example, the isoelectric point of the amino acid is between 4 and 7. In yet another preferred example, the isoelectric point of the amino acid is less than 4. In a preferred example, in equation (II), R 4 is a hydrocarbon group having a hydrogen bonding functional group. In this case, preferably, in formula (II), R 4 is a hydrocarbon group having a hydroxyl group and / or a carboxyl group. Alternatively, preferably in formula (II), R 4 is a hydrocarbon group having a hydroxyl group. Alternatively, preferably, in formula (II), R 4 is a hydrocarbon group having both a hydroxyl group and a carboxyl group. Another preferred example is in formula (II), R 4 This is an unsaturated or branched aliphatic hydrocarbon group having 7 to 21 carbon atoms.

[0108] The method for preparing the compound of the present invention is not particularly limited, but it can be prepared, for example, as follows. The amino acid and carboxylic acid are mixed and stirred in water. The preparation temperature and time depend on the type of raw materials, but for example, it can be done at room temperature in about 1 hour to 1 day. After that, the water is removed by distillation under reduced pressure to obtain the desired formulation.

[0109] The formulation of the present invention can exhibit the effects held by component (A) and component (B). Although not particularly limited, for example, when component (A) is arginine or histidine, a skin moisturizing effect and a hair repair effect can be obtained; when it is lysine, a stratum corneum transparency maintenance effect can be obtained; when it is γ-aminobutyric acid, a skin barrier function improvement effect and an epidermal cell proliferation effect can be obtained; when it is cysteine, a melanin production inhibitory effect can be obtained; and when it is linoleic acid as component (B), a melanin production inhibitory effect can be obtained.

[0110] The formulation of the present invention may be a mixture of component (A) and component (B), or a salt of component (A) and component (B), which may be in an anhydrous state (anhydrous substance) or a hydrate that has absorbed moisture from the air. A hydrate is a compound that, when left in the air at 25°C, absorbs water and reaches a saturated moisture content. A compound that does not absorb water when left in the air at 25°C does not have a hydrate and is an anhydrous substance.

[0111] The formulation of the present invention, a mixture of components (A) and (B) or a salt of (A) and (B), may be liquid or solid at 25°C in its anhydrous and hydrated forms. For example, when a liquid containing the formulation of the present invention is sprayed or applied to the area of ​​use, it remains as a liquid after the solvent evaporates, exhibiting its effect over a wide area without causing problems in use such as crystal precipitation or aggregation and solidification. Furthermore, if it is liquid at 25°C, it can be used as a solvent or base when used with other additives. In these respects, it is preferable that the mixture of components (A) and (B) or the organic salt of (A) and (B) be liquid at 25°C in its anhydrous and / or hydrate form, and more preferably that it be liquid at 25°C in its anhydrous or hydrate form.

[0112] Since a mixture of components (A) and (B) or a salt of (A) and (B) becomes liquid at 25°C, preferred combinations of components (A) and (B) include an amino acid with an isoelectric point greater than 7 as component (A) and a saturated hydroxymonocarboxylic acid, saturated hydroxydi, or tricarboxylic acid as component (B).

[0113] Furthermore, given that a mixture of components (A) and (B) or a salt of (A) and (B) becomes liquid at 25°C, preferred combinations of components (A) and (B) are as follows: A: A combination of the above components (A) and (B), wherein component (A) is an amino acid with an isoelectric point greater than 7, and component (B) is a saturated hydroxymonocarboxylic acid, preferably having multiple hydroxyl groups, and more preferably gluconic acid. B: A combination of the above components (A) and (B), wherein component (A) is an amino acid with an isoelectric point greater than 7, and component (B) is a saturated hydroxydi or tricarboxylic acid, preferably having three or more carboxyl groups, and more preferably citric acid. C: Component (A) is formula (I)(R 2 : An amino acid having an organic group, preferably having a substituent, more preferably a nitrogen-containing group, even more preferably having a primary amino group, particularly preferably being L-lysine (l:0, m:2, n:0), and as component (B) a saturated hydroxy monocarboxylic acid, preferably having multiple hydroxyl groups, more preferably being gluconic acid, a combination of the above components (A) and (B). D: Component (A) is formula (I)(R 2 : An amino acid having an organic group, preferably having a substituent, more preferably a nitrogen-containing group, even more preferably having a guanidino group, and particularly preferably being L-arginine (l:0, m:2, n:0), and a combination of the above components (A) and (B), where component (B) is a branched aliphatic carboxylic acid. E: Component (A) is formula (I)(R 2: An amino acid having an organic group, preferably having a substituent, more preferably a nitrogen-containing group, even more preferably a guanidino group, and particularly preferably L-arginine (l:0, m:2, n:0), and a combination of the above components (A) and (B), where component (B) is an unsaturated aliphatic carboxylic acid. F: Component (A) is given by formula (I)(R 2 : An amino acid having an organic group, preferably having a substituent, more preferably a nitrogen-containing group, even more preferably a guanidino group, and particularly preferably L-arginine (l:0, m:2, n:0), and a combination of the above components (A) and (B), where component (B) is a saturated hydroxymonocarboxylic acid, saturated hydroxydi or tricarboxylic acid. G: Component (A) is formula (I)(R 2 : An amino acid having an organic group, preferably having a substituent, more preferably a nitrogen-containing group, even more preferably an imidazolyl group, and particularly preferably L-histidine (l:0, m:2, n:0), and a saturated hydroxymonocarboxylic acid as component (B), a combination of the above components (A) and (B). H: Component (A) is given by formula (I)(R 3 : An amino acid having a hydrocarbon group with 1 to 22 carbon atoms, more preferably a hydrocarbon group with 4 to 12 carbon atoms, even more preferably a hydrocarbon group with 4 to 8 carbon atoms, and particularly preferably γ-aminobutyric acid (l:0, m:2, n:1), and a combination of the above components (A) and (B), where component (B) is an unsaturated aliphatic carboxylic acid. I: Component (A) is given by formula (I)(R 3 : An amino acid having a hydrocarbon group with 1 to 22 carbon atoms, more preferably a hydrocarbon group with 4 to 12 carbon atoms, even more preferably a hydrocarbon group with 4 to 8 carbon atoms, and particularly preferably γ-aminobutyric acid (l:0, m:2, n:1), and a saturated hydroxy monocarboxylic acid as component (B), a combination of the above components (A) and (B). J: Component (A) is formula (I)(R 2: Having an organic group, preferably having a substituent, more preferably an oxygen-containing group, even more preferably having a hydroxyl group, particularly preferably having a hydroxyl group at the hydrocarbon group terminus, most preferably being L-serine, an amino acid (l:0, m:2, n:0), preferably a saturated hydroxymonocarboxylic acid as component (B), more preferably having two or more hydroxyl groups, even more preferably being gluconic acid, a combination of the above components (A) and (B). K: Component (A) is given by formula (I)(R 2 : Having an organic group, preferably having a substituent, more preferably an oxygen-containing group, even more preferably having a hydroxyl group, particularly preferably having a hydroxyl group at the hydrocarbon group terminus, most preferably being L-serine, an amino acid (l:0, m:2, n:0), preferably a saturated hydroxydi or tricarboxylic acid as component (B), more preferably having one hydroxyl group and two or more carboxyl groups, malic acid and citric acid are even more preferred, a combination of the above components (A) and (B). L: Component (A) is given by formula (I)(R 1 and R 2 R is a hydrocarbon group, among others 1 and R 2 It is preferable that the amino acid (l:1, m:1, n:0) forms a ring, and it is more preferable that it is L-proline, and component (B) is a branched aliphatic carbone, a combination of the above components (A) and (B). M: Component (A) is formula (I)(R 1 and R 2 R is a hydrocarbon group, among others 1 and R 2 It is preferable that the amino acid (l:1, m:1, n:0) forms a ring, and it is more preferable that it is L-proline, and the component (B) is an unsaturated aliphatic carvone, a combination of the above components (A) and (B). N: Component (A) is given by formula (I)(R 1 and R 2 R is a hydrocarbon group, among others 1 and R 2It is preferable that the amino acid (l:1, m:1, n:0) forms a ring, and it is more preferable that it is L-proline, and the amino acid (l:1, m:1, n:0) is a saturated hydroxy monocarboxylic acid as component (B), and the above combination of component (A) and component (B) O: Component (A) is formula (I)(R 1 and R 2 R is a hydrocarbon group, among others 1 and R 2 It is preferable that the amino acid (l:1, m:1, n:0) forms a ring, and is more preferably L-proline, and component (B) is preferably a saturated hydroxydi or tricarboxylic acid, more preferably having one hydroxyl group and two or more carboxyl groups, and is even more preferably malic acid or citric acid, a combination of the above components (A) and (B).

[0114] In particular, since the mixture of components (A) and (B) or the salt of (A) and (B) becomes liquid at 25°C, examples of preferred combinations and molar ratios of components (A) and (B) are as follows. 1: Component (A) is lysine, component (B) is gluconic acid, molar ratio 1:1 2: Component (A) is lysine, component (B) is gluconic acid, molar ratio 1:2 3: Component (A) is lysine, component (B) is citric acid, molar ratio 1:1 4: Component (A) is lysine, component (B) is citric acid, molar ratio 3:2 5: Component (A) is arginine, component (B) is isostearic acid, molar ratio 1:1 6: Component (A) is arginine, component (B) is isostearic acid, molar ratio 1:2 7: Component (A) is arginine, component (B) is oleic acid, molar ratio 1:1 8: Component (A) is arginine, component (B) is oleic acid, molar ratio 1:2 9: Component (A) is arginine, component (B) is linoleic acid, molar ratio 1:1 10: Component (A) is arginine, component (B) is linoleic acid, molar ratio 1:2 11: Component (A) is arginine, component (B) is gluconic acid, molar ratio 1:1 12: Component (A) is arginine, component (B) is gluconic acid, molar ratio 1:2 13: Component (A) is arginine, component (B) is lactic acid, molar ratio 1:1 14: Component (A) is arginine, component (B) is lactic acid, molar ratio 1:2 15: Component (A) is arginine, component (B) is malic acid, molar ratio 1:1 16: Component (A) is arginine, component (B) is malic acid, molar ratio 1:2 17: Component (A) is arginine, component (B) is citric acid, molar ratio 1:1 18: Component (A) is arginine, component (B) is citric acid, molar ratio 3:2 19: Component (A) is arginine, component (B) is tartaric acid, molar ratio 1:1 20: Component (A) is arginine, component (B) is tartaric acid, molar ratio 1:2 21: Component (A) is arginine, component (B) is benzoic acid, molar ratio 1:1 22: Component (A) is histidine, component (B) is gluconic acid, molar ratio 1:1 23: Component (A) is histidine, component (B) is gluconic acid, molar ratio 1:2 24: Component (A) is histidine, component (B) is lactic acid, molar ratio 1:2 25: Component (A) is histidine, component (B) is citric acid, molar ratio 1:1 26: Component (A) is histidine, component (B) is citric acid, molar ratio 3:2 27: Component (A) is glycine, component (B) is citric acid, molar ratio 1:1 28: Component (A) is γ-aminobutyric acid, component (B) is oleic acid, molar ratio 1:1 29: Component (A) is γ-aminobutyric acid, component (B) is gluconic acid, molar ratio 1:1 30: Component (A) is γ-aminobutyric acid, component (B) is lactic acid, molar ratio 1:1 31: Component (A) is γ-aminobutyric acid, component (B) is citric acid, molar ratio 1:1 32: Component (A) is serine, component (B) is gluconic acid, molar ratio 1:1 33: Component (A) is serine, component (B) is malic acid, molar ratio 1:1 34: Component (A) is serine, component (B) is citric acid, molar ratio 1:1 35: Component (A) is proline, component (B) is isostearic acid, molar ratio 1:1 36: Component (A) is proline, component (B) is oleic acid, molar ratio 1:1 37: Component (A) is proline, component (B) is linoleic acid, molar ratio 1:1 38: Component (A) is proline, component (B) is gluconic acid, molar ratio 1:1 39: Component (A) is proline, component (B) is lactic acid, molar ratio 1:1 40: Component (A) is proline, component (B) is malic acid, molar ratio 1:1 41: Component (A) is proline, component (B) is citric acid, molar ratio 1:1

[0115] The formulation of the present invention has components (A) and (B), and because the amino acid of component (A) has a hydrogen-bonding functional group (carboxyl group, hydrogen atom bonded to a nitrogen atom), its affinity for water is improved, and it has excellent water retention and hygroscopic properties.

[0116] From the viewpoint of water retention, it is preferable that component (A) be an amino acid with an isoelectric point greater than 7 and component (B) be a carboxylic acid having a hydrogen bonding functional group in the hydrocarbon part, more preferably that component (A) be an amino acid with an isoelectric point greater than 7 and component (B) be a hydroxycarboxylic acid, and even more preferably that component (A) be an amino acid with an isoelectric point greater than 7 and component (B) be a hydroxytricarboxylic acid. Among these, the combinations of components (A) and (B) described above, 3, 4, 17, 18, 25-27, 31, 34, and 41, are particularly preferred.

[0117] From the viewpoint of hygroscopicity, an amino acid with an isoelectric point greater than 7 is preferred as component (A), and an unsaturated carboxylic acid as component (B). L-arginine is more preferred as component (A), and oleic acid as component (B). Among these, the combinations of components (A) and (B) described above, 7 and 8, are even more preferred.

[0118] The formulation of the present invention exhibits excellent solubility for poorly soluble substances because components (A) and (B) are amino acids and carboxylic acids, respectively. As a result, it is possible to incorporate poorly soluble substances at higher concentrations, and even if the poorly soluble substance is in solid form, it can maintain a continuously dissolved state and uniformly coat the surface of the target object, allowing the effects of the poorly soluble substance to be fully realized.

[0119] When applied to cosmetic use, the formulation of the present invention, containing components (A) and (B), provides excellent usability in terms of ease of application, moisturizing effect, and non-greasy feel when applied to the skin. In particular, due to the non-volatility of the mixture or organic salt of components (A) and (B) used in the present invention, it provides excellent sustained moisturizing effect. In particular, the mixture or organic salt of components (A) and (B) with a melting point of less than 25°C, or solutions thereof, provides excellent usability in terms of ease of application, moisturizing effect, non-greasy feel, and refreshing feel.

[0120] From the standpoint of sensory evaluation, it is preferable that component (A) is an amino acid with an isoelectric point greater than 7, or an amino acid with an isoelectric point between 4 and 7, and that component (B) has a hydrogen bonding functional group in the hydrocarbon portion, more preferably a hydroxyl group and a carboxyl group as the hydrogen bonding functional group, and even more preferably two or more carboxyl groups.

[0121] On the other hand, component (A) is preferably an amino acid with an isoelectric point greater than 7, or an amino acid with an isoelectric point between 4 and 7, and component (B) is preferably an unsaturated or branched aliphatic carboxylic acid, with arginine or proline being preferred for component (A) and an unsaturated or branched aliphatic carboxylic acid being more preferred for component (B). The molar ratio of component (A):component (B) is not particularly limited, but for example, 1:9 to 9:1 is preferred, 3:1 to 1:3 is more preferred, and 3:2 to 1:2 is even more preferred in terms of usability.

[0122] Among these, the combinations of components (A) and (B) are preferably 3-10, 15-20, 25-27, 31, and 33-37, with the combination of 6, 8, 25, 26, 31, 33-37, 40, and 41 being more preferable.

[0123] If the surface of an object to which the formulation of the present invention is used has functional groups that interact with and bond with hydrogen-bonding functional groups of the formulation of the present invention, such as oxygen-containing groups, nitrogen-containing groups, sulfur-containing groups, phosphorus-containing groups, etc., then if component (A) and / or component (B) have hydrogen-bonding functional groups, the formulation can adhere well to the object for a long period of time and exert its effect. Examples of objects to which the formulation can be used include organic substances, inorganic substances, etc., and are not particularly limited, but include biological tissues (hair, skin), resins, paper, metals, metal oxides, etc.

[0124] From the viewpoint of adhesion to hair and skin, component (B) is preferably a carboxylic acid having a hydrogen bonding functional group in the hydrocarbon part, more preferably having a hydroxyl group and / or a carboxyl group as the hydrogen bonding functional group, even more preferably having a hydroxyl group, particularly preferably having a hydroxyl group and a carboxyl group, and most preferably having a hydroxyl group and two or more carboxyl groups.

[0125] On the other hand, component (A) is preferably an amino acid with an isoelectric point greater than 7, or an amino acid with an isoelectric point between 4 and 7, and component (B) is preferably an unsaturated or branched aliphatic carboxylic acid.

[0126] Among these, the combinations of components (A) and (B) that are 1-4, 11, 12, 17, 18, 25-27, 31, 32, 34, 38, and 41 above are preferred.

[0127] The formulation of the present invention exhibits excellent antibacterial properties due to the carboxyl groups of component (A) and / or component (B). Preferably, the combination of the total number of amino groups and the total number of carboxyl groups of component (A) and component (B) is such that the total number of carboxyl groups is greater, and it is preferable that unneutralized carboxyl groups (-COOH) are present when component (A) and component (B) form an organic salt. In other words, it is preferable that the ratio of the total number of amino groups to the total number of carboxyl groups (total number of amino groups / total number of carboxyl groups) of component (A) and component (B) is 1 or less.

[0128] The formulation of the present invention, whether a mixture of component (A) and component (B) or an organic salt, is non-volatile. In particular, the liquid mixture or organic salt can be applied uniformly and at a high concentration after the volatile components have evaporated, thus providing effective and sustained antibacterial properties. Furthermore, it also acts as a solvent for existing antibacterial agents, antiviral agents, disinfectants, and other agents that are effective against bacteria and viruses. This allows for higher concentrations of existing antibacterial agents, antiviral agents, disinfectants, etc. to be incorporated, and even with solid agents, a sustained dissolved state can be maintained and a uniform coating can be applied to the surface of the target object. In addition to the antibacterial properties of the formulation of the present invention, the effects of existing antibacterial agents, antiviral agents, disinfectants, etc., can be fully exerted. Moreover, a synergistic effect can be expected between the formulation of the present invention and existing antibacterial agents, antiviral agents, and disinfectants, for example, antibacterial and antiviral properties can be obtained at lower concentrations.

[0129] From the viewpoint of antibacterial properties, component (A) is preferably an amino acid with an isoelectric point of 4 to 7, and component (B) is preferably one having a hydrogen bonding functional group in the hydrocarbon portion. It is more preferable that the hydrogen bonding functional group has a hydroxyl group and / or a carboxyl group, even more preferable that it has a hydroxyl group and a carboxyl group, and particularly preferable that it has a hydroxyl group and two or more carboxyl groups. Furthermore, it is preferable that the ratio of the total number of amino groups to the total number of carboxyl groups (total number of amino groups / total number of carboxyl groups) of components (A) and (B) is 1 or less. Among these, the combinations of components (A) and (B) that are 3, 16, 17, 20, 25, 27, 31, 33, 34, 40, and 41 are preferred.

[0130] The formulation of the present invention is highly safe, and in particular, if components (A) and (B) are compounds listed in the Japanese Pharmacopoeia (JP), the Japanese Pharmacopoeia (JP), the Japanese Pharmacopoeia (JP) Non-JP Quasi-Drugs (JP) Standards, the Japanese Pharmaceutical Additives Standards, and the Food Additives Standards, the formulation is highly safe and has suppressed skin irritation, making it suitable for use on the human body and application in cosmetics and daily necessities.

[0131] The formulations of the present invention are easily biodegradable because components (A) and (B) are amino acids and carboxylic acids, respectively. In particular, formulations containing components (A) and (B) derived from natural products are highly biodegradable and have a low environmental impact, making them useful.

[0132] The formulation of the present invention exhibits good affinity with polymer compounds and water because component (A) and / or component (B) have hydrogen-bonding functional groups when combined with a polymer compound and water, making it suitable for gel formation and thickening effects. If the polymer compound also has hydrogen-bonding functional groups, gel formation becomes even easier, which is preferable from the viewpoint of thickening effect.

[0133] The gel composition containing the compound, polymer compound, and water of the present invention is useful because it exhibits thixotropy, where the viscosity decreases when a shear force is applied, making it easy to apply to the target object, and then the viscosity increases when no shear force is applied, making it less likely for the liquid to drip from the applied surface.

[0134] The formulation of the present invention may consist only of components (A) and (B), or it may be a mixture or composition of components (A) and (B) diluted in a solvent, or other components.

[0135] In the formulation of the present invention, the molar ratio of component (A) to component (B) is not particularly limited and can be 1:99 to 99:1, preferably 1:9 to 9:1, and more preferably 1:5 to 5:1.

[0136] The content of components (A) and (B) in the formulation of the present invention is not particularly limited, but for example, it is 0.01 to 100% by mass, or 0.1 to 100% or 1 to 95% by mass, relative to the total amount of the formulation.

[0137] The solvent is not particularly limited, but examples include water, methanol, ethanol, propanol, isopropanol, butanol, ethylene glycol, propylene glycol, 1,3-butylene glycol, diethylene glycol, dipropylene glycol, isoprene glycol, hexylene glycol, glycerin, benzyl alcohol, methyl acetate, ethyl acetate, isopropyl acetate, ethyl ether, acetone, toluene, hexane, heptane, acetonitrile, etc. These may be used individually or in combination of two or more.

[0138] The aforementioned other components are not particularly limited, but include, for example, water, surfactants (anionic surfactants, cationic surfactants, nonionic surfactants, amphoteric surfactants, etc.), oils, solvents, oils, cationic polymers, water-soluble polymers, viscosity modifiers, resins, resin particles, gloss enhancers, higher alcohols, polyhydric alcohols, higher fatty acids, amidoamines, hydrocarbons, waxes, esters, silicone derivatives, physiologically active ingredients, extracts, antioxidants, metal ion sequestering agents, and preservatives. Examples include agents, UV absorbers (including organic and inorganic types), fragrances, moisturizers, carbon compounds, metal oxides, minerals, salts, neutralizing agents, pH adjusters, cooling agents, insect repellents, enzymes, dyes, organic pigments, inorganic pigments, colorants, pearl foil, pearlescent agents, anti-inflammatory agents, antioxidants, corrosion inhibitors, rust inhibitors, metal deactivators, defoaming agents, whitening agents, wrinkle-improving agents, vitamins, amino acids, hair growth agents, antibacterial agents, hormones, plant extracts, seaweed extracts, herbal medicine components, activators, blood circulation promoters, and organically modified clay minerals. These may be used individually or in combination of two or more types.

[0139] The formulations of the present invention can be used, for example, to impart water retention, hygroscopicity, and / or antibacterial properties, and can also be used in cosmetics. Furthermore, they can be used in gel compositions containing polymer compounds and water. The formulations of the present invention are excellent in water retention, hygroscopicity, usability (ease of spreadability, moisturizing effect, non-stickiness, refreshing feel, etc.), adhesion to hair, antibacterial properties, skin irritation, biodegradability, and gel formation, making them suitable for various applications, such as water retention / moisturizing agents, hygroscopic agents, conductive materials, electrolyte materials, antistatic agents, dissolving solvents, dispersion solvents, storage solvents and culture media for biomaterials, thickeners, organic or inorganic materials (not particularly limited, but including metals, metal oxides (not particularly limited, but including silica, aluminum oxide (alumina), zirconia, titanium dioxide, magnesium oxide, and aluminum oxide)). Solvents and dispersion solvents for carbon materials (such as tungsten oxide (ITO), cobalt blue (CoO·Al2O3), antimony oxide, zinc oxide, cesium oxide, zirconium oxide, yttrium oxide, tungsten oxide, vanadium oxide, cadmium oxide, tantalum oxide, niobium oxide, tin oxide, bismuth oxide, cerium oxide, copper oxide, iron oxide, indium oxide, boron oxide, calcium oxide, barium oxide, thorium oxide, indium tin oxide, ferrite, etc.), and carbon materials. Surface treatment agents, cosmetics (lotions, toners, lipsticks, etc.), fragrances (softeners, detergents, etc.) Hygiene and sanitary supplies, pharmaceuticals, topical agents, transdermal absorbents, soil conditioners, soil water retention agents, soil modifiers, water-stopping agents, roadbed agents, concrete treatment agents, water retention agents for greening, civil engineering and construction materials (flame retardants, heat insulating agents, etc.), food packaging materials, food additives (freshness preservatives, etc.), sheets, concrete admixtures and modifiers, sealing materials, water-repellent agents, shock absorbers, adsorbents, extractants, medical and pharmaceutical materials (medical sensors, mouthwashes, etc.), drug delivery systems, lubricants, reaction solvents, heat transfer fluids, refrigerants, food products, agricultural materials (seed coating agents, etc.), pesticides, fertilizers, insecticides, pigments, dyes It can be suitably used as a base material for paints, dyes, ink pigment treatment agents, adhesives, swelling agents, wetting agents, antibacterial agents, paper treatment agents (agents for lotion tissues, paper coating liquids, etc.), textile materials (textile treatment agents, etc.), fresh flower transport agents, electronic materials (electronic material cleaning agents, etc.), biomaterials (artificial skin, etc.), sanitary materials, deodorizers, fragrances, heating materials (hand warmers, etc.), cold storage agents, cooling sheets, pet supplies (absorbent sheets), daily necessities (sleepwear and bedding, etc.), glass materials (glass treatment agents (anti-condensation agents, etc.), etc.), and industrial products (gas detection agents, desiccants, adhesives, resin modifiers, etc.).

[0140] (composition) The composition of the present invention comprises the formulations described above. The composition of the present invention may also contain the organic salts described above. These formulations and compositions may be used to impart water retention, hygroscopicity, and / or antibacterial properties, and may also be used as cosmetics. Furthermore, they may be used as gel compositions containing polymer compounds and water. The composition containing the compound of the present invention is not particularly limited in form, but can be, for example, liquid, solid, gel, etc.

[0141] The preferred combinations of components (A) and (B) of a composition containing the formulation of the present invention refer to the above combinations depending on the application.

[0142] In a composition used to impart antibacterial properties, which contains the formulation of the present invention, components other than components (A) and (B) are not particularly limited, but include, for example, the above-mentioned solvent, antibacterial agents, antiviral agents, disinfectants and other agents that have an effect on bacteria and viruses, surfactants (anionic surfactants, cationic surfactants, nonionic surfactants, amphoteric surfactants, etc.), resins, ultraviolet absorbers (including organic and inorganic types), fragrances, humectants, metal oxides, neutralizing agents, pH adjusters, colorants, antioxidants, corrosion inhibitors, rust inhibitors, metal deactivators, defoamers, etc. These may be used individually or in combination of two or more.

[0143] In a composition used in cosmetics containing the formulation of the present invention, components other than components (A) and (B) are not particularly limited, but examples include water, surfactants, oils, solvents, surfactants, oils, cationic polymers, water-soluble polymers, viscosity modifiers, resins, resin particles, gloss enhancers, higher alcohols, polyhydric alcohols, higher fatty acids, amidoamines, hydrocarbons, waxes, esters, silicone derivatives, physiologically active ingredients, extracts, antioxidants, metal ion chelating agents, preservatives, UV absorbers (including organic and inorganic types), fragrances, humectants, carbons, metal oxides, minerals, salts, neutralizing agents, pH adjusters, cooling agents, insect repellents, enzymes, dyes, organic pigments, inorganic pigments, colorants, pearl foil, pearlescent agents, anti-inflammatory agents, antioxidants, whitening agents, wrinkle-improving agents, vitamins, amino acids, hair growth agents, antibacterial agents, hormones, plant extracts, seaweed extracts, herbal medicine components, activators, blood circulation promoters, organically modified clay minerals, and the like.

[0144] The composition used in the cosmetic of the present invention provides a moisturizing sensation and a non-sticky feel when applied to the skin, due to the short- and long-term water retention, moisturizing, and antistatic (anti-static) effects resulting from the non-volatility of the mixture of components (A) and (B) or the organic salt. Furthermore, due to the safety of the formulation, affinity to the skin, permeability, and low irritation, it is highly safe for skincare compositions, resulting in skincare compositions that blend well with the skin, have good skin elasticity, and cause low irritation to the skin. Moreover, the formulation of the present invention is useful as a base material for skincare compositions due to its high solubility of the active ingredient, and its excellent permeability to the skin provides excellent water retention and moisturizing effects, and it can also be used as a carrier for the active ingredient. In addition to use on the skin, it can also be used for applications where the effects of the present invention are desired, such as on the stratum corneum, nails, oral cavity, and nasal cavity. Furthermore, it is a formulation with low environmental impact due to its excellent biodegradability.

[0145] The gel composition containing the formulation of the present invention includes, in addition to the formulations of components (A) and (B), a polymer compound and water. The polymer compound is not particularly limited, but examples include synthetic polymer compounds, semi-synthetic polymer compounds, and natural polymer compounds. Among these, polymer compounds having hydrogen-bonding functional groups are preferred because they can interact with water, component (A) and / or component (B), thereby increasing their affinity. Polymer compounds containing at least one of hydroxyl groups, carbonyl groups, carboxyl groups, and carboxylate groups are particularly preferred. Semi-synthetic polymer compounds and natural polymer compounds are preferred, and natural polymer compounds are more preferred, especially from the viewpoint of safety. These may be used individually or in combination of two or more.

[0146] The synthetic polymer compounds are not particularly limited, but examples include polyacrylic acid-based, vinyl acetate copolymer-based, maleic anhydride copolymer-based, polyvinyl alcohol-based, polyvinylpyrrolidone-based, polyethylene glycol-based, polyethylene oxide-based, polyester-based, polyacrylonitrile-based, polyamide-based, polyimide-based, polyamideimide-based, polymaleimide-based, polyurethane-based, polycarbonate-based, and polyarylate-based polymer compounds.

[0147] Examples of semi-synthetic polymer compounds include, but are not limited to, cellulose derivatives (carboxymethylcellulose sodium, hydroxyethylcellulose, methylcellulose, ethylcellulose, nitrocellulose, hydroxypropylcellulose, hydroxypropylmethylcellulose, crystalline cellulose), sodium alginate, ester gum, soluble starch, etc. Examples of natural polymer compounds include, but are not limited to, polysaccharides, cellulose, nucleic acids or their salts, ribonucleic acid or its salts, water-soluble proteins (casein, collagen, gelatin, albumin, fibroin, elastin, keratin, sericin, etc.), hyaluronic acid or its salts, mucopolysaccharides (chondroitin sulfate, etc.), etc., with polysaccharides being particularly preferred.

[0148] Polysaccharides are not particularly limited, but examples include natural polysaccharides such as xanthan gum, carrageenan, tamarind sea gum, gellan gum, guar gum, pectin, gum arabic, karaya gum, locust bean gum, dieutan gum, sodium alginate, agarose, hyaluronic acid, and polygalacturonic acid; carboxyalkyl polysaccharides such as carboxymethyl pullulan, carboxymethyl chitin, carboxymethyl chitosan, carboxymethyl mannan, carboxymethyl starch, carboxymethyl dextran, carboxyethyl cellulose, and carboxymethyl pullulan; oxidized polysaccharides such as oxidized cellulose and oxidized starch; and polysaccharides containing sulfate groups such as chondroitin sulfate, dermatan sulfate, heparin, and heparan sulfate.

[0149] Among these, polymer compounds having hydrogen-bonding functional groups are preferred, and water-soluble polymer compounds are more preferred. Preferred polymer compounds include xanthan gum, carrageenan, gellan gum, guar gum, dieutan gum, and sodium alginate; xanthan gum, carrageenan, gellan gum, guar gum, and dieutan gum are more preferred, and xanthan gum and guar gum are even more preferred.

[0150] In the gel composition of the present invention, component (A), component (B), polymer compound, and water are blended in any proportion, and the amounts blended are not particularly limited. However, for example, from the viewpoint of suitability for gel formation or imparting viscosity, the total amount of component (A) and component (B) in the composition is preferably 90% by mass or less, more preferably 50% by mass or less, even more preferably 30% by mass or less, and particularly preferably 10% by mass or less. On the other hand, the amount of polymer compound in the composition is preferably 0.01% by mass or more, more preferably 0.1% by mass or more, and even more preferably 1% by mass or more.

[0151] Although embodiments of the present invention have been described above, the present invention is not limited to these embodiments, and various modifications are possible without departing from the spirit of the invention. Furthermore, at least one combination of the above preferred examples shown in formula (I), the above preferred examples shown in component (B), and the above preferred examples shown in formula (II) may be more preferred based on the results of the examples. Moreover, the combination of these with the properties of a mixture of components (A) and (B) or a salt of (A) and (B), and furthermore, the combination of these with the above preferred examples of polymer compounds may be more preferred based on the results of the examples. [Examples]

[0152] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples.

[0153] 1. Preparation of formulations (organic salts) 1-427 The formulations (salts) 1 to 427 shown in Tables 1A to 1D were prepared by the following method. The following reagents were used for components (A) and (B). L-lysine, gamma-aminobutyric acid, hexanoic acid, linoleic acid, fumaric acid, citric acid, benzoic acid, and ascorbic acid are manufactured by Tokyo Chemical Industry Co., Ltd. L-arginine, L-histidine, glycine, L-valine, L-asparagine, L-glutamine, L-cysteine, L-tryptophan, L-aspartic acid, formic acid, acetic acid, propionic acid, gluconic acid, L-malic acid, tartaric acid, and cinnamic acid are manufactured by Fujifilm Wako Pure Chemical Industries, Ltd. L-alanine, L-leucine, L-isoleucine, L-serine, L-threonine, L-methionine, L-phenylalanine, and L-glutamic acid are manufactured by Peptide Laboratory Co., Ltd. L-proline is manufactured by Sigma-Aldrich Japan. Isostearic acid and oleic acid are manufactured by Miyoshi Oil & Fat Co., Ltd. Lactic acid, butyric acid, adipic acid, and succinic acid are manufactured by Kanto Chemical Co., Ltd.

[0154] <Example 48> Composition (Salt) 48 L-arginine (11.78 g, 0.10 mol) and isostearic acid (28.45 g, 0.10 mol) were stirred in 50 mL of water and 50 mL of ethanol at room temperature for 3 hours, and the solvent was removed by distillation under reduced pressure to obtain a colorless liquid. By washing the obtained liquid, a compound (salt) consisting of colorless liquid L-arginine and isostearic acid was obtained. Ingredients (salt) 48 FT-IR (KBr): 3165 cm -1 , 2925 cm -1 , 1854 cm -1 , 1653 cm -1 , 1406 cm -1 . 1 HNMR (MeOD, 400MHz): 0.86-0.94 (m, 6H, Isostearic acid, -C H 3), 1.69-1.79 (m, 2H, Arg, -CH2C H 2CH2-), 1.87-1.94 (m, 2H, Arg, -C H 2CH(NH2)COOH), 3.11-3.14 (t, 2H, Arg, -C H 2NH-), 3.32-3.40 (m, 1H, Isostearic acid, -C H (COOH)-), 3.58-3.61 (t, 1H, Arg, -C H (NH2)COOH). 1.31 (m, 22H), 1.59-1.63 (m, 2H), 2.17-2.21 (t, 2H), 3.21-3.25 (t, 2H): (Isostearic acid, CH3(C H 2) 8CH((C H 2)6CH3)COOH). 13 CNMR (MeOD, 100MHz): 25.8 (Arg, -CH2 C H2CH2-), 27.6 (Arg, - CH2CH(NH2)COOH), 41.9 (Arg, - C H2NH-), 55.6 (Arg, - C H(NH2)COOH), 56.2 (Isostearic acid, - C H(COOH)-), 158.8 (Arg, - C (NH)NH2), 174.7 (Arg, C OOH), 182.6 (Isostearic acid, C (Out of the Home) 29.5, 30.8, 38.8, 48.4, 48.6, 48.8, 49.0, 49.2, 49.5 (Isostearic acid, C H3( C H2)8CH(( C H2)6 C H3)COOH).

[0155] <Examples 1-6, 22-27, 43-48, 64-69, 85-90, 106-111> Composition (salt) 1-6, 22-27, 43-48, 64-69, 85-90, 106-111 Similarly, using components (A) and (B) in the mixing ratios listed in Table 1A, preparations were made under the same conditions as in Example 48, yielding formulations (salts) 1-6, 22-27, 43-48, 64-69, 85-90, and 106-111. The spectral data for representative formulations (salts) are shown below. Ingredients (salt) 69 FT-IR (KBr): 2925 cm -1 , 2854 cm -1 , 1677 cm -1 , 1542 cm -1 , 1464 cm -1 , 1405 cm -1 . 1 HNMR (MeOD, 400MHz): 0.87-0.94 (m, 12H, Isostearic acid, -C H 3), 1.70-1.81 (m, 2H, Arg, -CH2C H2CH2-), 1.87 - 1.94 (m, 2H, Arg, -C H 2CH(NH2)COOH), 3.11 - 3.14 (t, 2H, Arg, -C H 2NH-), 3.32 - 3.34 (m, 2H, Isostearic acid, -C H (COOH)-), 3.59 - 3.63 (t, 1H, Arg, -C H (NH2)COOH). 1.32 (m, 44H), 1.58 - 1.65 (m, 4H), 2.21 - 2.25 (t, 4H), 3.21 - 3.26 (t, 4H): (Isostearic acid, CH3(C H 2)8CH((C H 2)6CH3)COOH). 13 CNMR (MeOD, 100MHz): 27.0 (Arg, -CH2 C H2CH2-), 30.6 (Arg, - C H2CH(NH2)COOH), 41.8(Arg, - C H2NH-), 49.7 (Arg, - C H(NH2)COOH), 158.8 (Arg, - C (NH)NH2), 174.3 (Arg, C OOH), 180.5 (Isostearic acid, C OOH). 30.8, 31.5, 37.2, 48.4, 48.6, 49.0, 49.2, 49.5 :(Isostearic acid, C H3( C H2)8CH(( C H2)6 C H3)COOH).

[0156] <Example 49> Complex (salt) 49 L-arginine (11.78 g, 0.10 mol) and oleic acid (28.25 g, 0.10 mol) were stirred in 50 mL of water and 50 mL of ethanol at room temperature for 3 hours, and the solvent was removed by distillation under reduced pressure to obtain a yellow liquid. By washing the obtained liquid, a compound (salt) consisting of the yellow liquid L-arginine and oleic acid was obtained. Ingredients (salt) 49 FT-IR (KBr): 3347 cm -1 , 2925 cm -1 , 1737 cm -1 , 1636 cm -1 , 1404 cm -1 . 1 HNMR (MeOD, 400MHz): 0.90-0.94 (t, 3H, Oleic acid, -C H 3), 1.71-1.78 (m, 2H, Arg, -CH2C H 2CH2-), 1.88-1.94 (m, 2H, Arg, -C H 2CH(NH2)COOH), 3.21-3.25 ((t, 2H, Oleic Acid, -C H 2COOH), (t, 2H, Arg, -C H 2NH-)), 3.59-3.62 (t, 1H, Arg, -C H (NH2)COOH), 5.35-5.37 (t, 2H, Oleic acid, -C H =C H -). 1.31-1.35 (m, 20H), 1.59-1.62 (m, 2H), 2.01-2.05 (m, 2H), 2.17-2.20 (t, 2H): (Oleic acid, CH3(C H 2) 7CH=CH(C H 2) 7COOH). 13 CNMR (MeOD, 100MHz): 14.5 (Oleic acid CH3-), 23.8, (Arg, -CH2 C H2CH2-), 25.7 (Oleic acid), 27.7 (Arg, -C H2CH(NH2)COOH), 41.9 (- C H2NH-), 55.5 (Arg, - C H(NH2)COOH), 130.8, 130.9 (Oleic acid, - C H= C H-), 158.9 (Arg, - C (NH)NH2), 174.9 (Arg, C OOH), 182.9 (Oleic acid, C (Out of the Home) 25.7, 28.1, 28.2, 29.5, 30.4, 30.47, 30.57, 30.64, 30.8, 30.9, 32.7, 33.1, 39.1 (Oleic acid, CH3( C H2)7CH=CH( C H2)7COOH).

[0157] <Examples 7, 8, 28, 29, 49, 50, 70, 71, 91, 92, 112, 113> Composition (salt) 7, 8, 28, 29, 49, 50, 70, 71, 91, 92, 112, 113 Similarly, using components (A) and (B) in the mixing ratios listed in Table 1A, preparations were made under the same conditions as in Example 49 to obtain formulations (salts) 7, 8, 28, 29, 49, 50, 70, 71, 91, 92, 113, and 114. The spectral data for representative formulations (salts) are shown below. Ingredients (salt) 50 FT-IR (KBr): 3346 cm -1 , 3166 cm -1 , 2926 cm -1 , 1645 cm -1 , 1404 cm -1 . 1 HNMR (MeOD, 400MHz): 0.90-0.95 (m, 3H, Linoleic acid, -C H 3), 1.68-1.80 (m, 2H, Arg, -CH2C H 2CH2-), 1.84-1.93 (m, 2H, Arg, -C H2CH(NH2)COOH), 3.11-3.14 (t, 2H, Arg, -C H 2NH-), 3.57-3.60 (t, 1H, Arg, -C H (NH2)COOH), 5.30-5.42 (m, 4H, Linoleic acid, -C H =C H -). 1.30-1.41 (m, 12H), 1.59-1.64 (m, 2H), 2.05-2.11 (q, 4H), 2.78-2.81 (t, 2H), 3.21-3.25 (t, 2H), 3.31-3.34(t, 2H): (Linoleic acid, CH3(C H 2)4(CH=CHC H 2)2(C H 2)6COOH). 13 CNMR (MeOD, 100MHz): 14.7 (Linoleic acid, - C H3), 23.7 (Arg, -CH2 C H2CH2-), 27.7 (Arg, - C H2CH(NH2)COOH), 41.9 (Arg, - C H2NH-), 55.6 (Arg, - C H(NH2)COOH), 56.3 (Linoleic acid, - C H2COOH), 129.7 (Linoleic acid, - C H= C H-), 130.9 (Linoleic acid, - C H= C H-), 158.8 (Arg, - C (NH)NH2), 174.8 (Arg, C OOH), 182.7 (Linoleic acid, C OOH). 26.6, 28.2, 30.5, 30.8, 38.9, 48.6, 48.8, 49.0, 49.2, 49.5, 49.7 (Linoleic acid, CH3( CH2)4(CH=CH C H2)2( C H2)6COOH). Complex (salt) 70 FT-IR (KBr): 3411 cm -1 , 2924 cm -1 , 1762 cm -1 , 1635 cm -1 , 1063 cm -1 , 963 cm -1 . 1 HNMR (MeOD, 400MHz): 0.80 - 0.89 (t, 6H, Oleic acid, -C H 3), 1.60 - 1.70 (m, 2H, Arg, -CH2C H 2CH2-), 1.78 - 1.84 (m, 2H, Arg, -C H 2CH(NH2)COOH), 3.11 - 3.14 (t, 2H, Arg, -C H 2NH-), 3.50 - 3.55 (m, 1H, Arg, -C H (NH2)COOH), 5.25 - 5.27 (t, 4H, Oleic acid,-C H =C H -). 1.21 - 1.24 (m, 40H) 1.49 - 1.53 (m, 4H), 1.92 - 1.99 (m, 8H), 2.12 - 2.15 (t, 4H): (Oleic acid, CH3(C H 2)7CH=CH(C H 2)7COOH). 13 CNMR (MeOD, 100MHz): 14.5 (Oleic acid -C H 3), 23.8 (Arg, -CH2 C H2CH2-), 27.0 (Arg, - C H2CH(NH2)COOH), 41.9 (Arg, - C H2NH-), 55.5 (Arg, - C H(NH2)COOH), 130.9, 131.0 (Oleic acid, -C H= C H-), 158.8 (Arg, - C (NH)NH2), 174.4 (Arg, C OOH), 180.6 (Oleic acid, C OOH). 25.7, 28.1, 28.2, 29.3, 30.3, 30.4, 30.5, 30.6, 30.7, 30.8, 32.7, 33.1, 37.2, 58.0 (Oleic acid, CH3( C H2)7CH=CH( C H2)7COOH). Complex (salt) 71 FT-IR (KBr): 3347 cm -1 , 2927 cm -1 , 2855 cm -1 , 2361 cm -1 , 1680 cm -1 , 1405 cm -1 . 1 1H NMR (MeOD, 400 MHz): 0.91 - 0.95 (t, 6H, Linoleic acid, -CH3), 1.71 - 1.80 (m, 2H, Arg, -CH2C H 2CH2-), 1.88 - 1.97 (m, 2H, Arg, -C H 2CH(NH2)COOH), 3.21 - 3.26 (t, 2H, Arg, -C H 2NH-), 3.60 - 3.63 (t, 1H, Arg, -C H (NH2)COOH), 5.31 - 5.42 (m, 8H, Linoleic acid, -C H =C H -). 1.30 - 1.42 (m, 24H), 1.60 - 1.64 (m, 4H), 2.06 - 2.11 (q, 8H), 2.23 - 2.30 (m, 4H), 3.21 - 3.25 (t, 4H), 3.31 - 3.34 (t, 4H): (Linoleic acid, CH3(C H 2)4(CH=CHC H2)2(C H 2) 6COOH). 13 CNMR (MeOD, 100MHz): 14.7 (Linoleic acid, - C H3), 23.8 (Arg, -CH2 C H2CH2-), 27.8 (Arg, - C H2CH(NH2)COOH), 41.9 (Arg, - C H2NH-), 49.7 (Linoleic acid, -C H 2COOH), 55.5 (Arg, - C H(NH2)COOH), 129.1, 130.9 (Linoleic acid, - C H= C H-), 158.8 (Arg, - C (NH)NH2), 174.3 (Arg, C OOH), 180.0 (Linoleic acid, C (Out of the Home) 26.8, 28.2, 28.6, 29.9, 30.5, 30.8, 31.1, 32.0, 32.7, 36.5, 36.8, 37.1 (Linoleic acid, CH3( C H2)4(CH=CH C H2)2( C H2)6COOH).

[0158] <Example 52> Composition (Salt) 52 L-arginine (11.78 g, 0.10 mol) and 30% by mass lactic acid (30.01 g, 0.10 mol) were stirred in 50 ml of water at room temperature for 1 hour, and then the water was removed by distillation under reduced pressure to obtain a colorless liquid. By washing the obtained liquid, a compound (salt) consisting of colorless liquid L-arginine and lactic acid was obtained. Ingredients (salt) 52 FT-IR (KBr): 3366 cm -1 , 3189 cm -1 , 1718 cm -1 , 1141 cm -1 , 863 cm -1 . 1 HNMR (D2O, 400MHz): 1.20-1.22 (d, 3H, Lactic acid, -C H 3), 1.49-1.61 (m, 2H, Arg, -CH2C H 2CH2-), 1.77-1.83 (m, 2H, Arg, -C H 2CH(NH2)COOH), 3.11-3.14 (t, 2H, Arg, -C H 2NH-), 3.64-3.67 (t, 1H, Arg, -C H (NH2)COOH), 3.97-4.02 (q, 1H, Lactic acid, -C H OH-). 13 CNMR (D2O, 100MHz): 20.0 (Lactic acid, - C H3), 23.8 (Arg, -CH2 C H2CH2-), 27.5 (Arg, -CH2 C H2CH(NH2)COOH), 40.4 (Arg, - C H2NH-), 54.3 (Arg, - C H(NH2)COOH), 68.4 (Lactic acid, - C HOH-), 156.8 (Arg, - C (NH)NH2), 174.3 (Arg, C OOH), 182.4 (Lactic acid, - C (Out of the Home)

[0159] <Examples 9, 10, 30, 31, 51, 52, 72, 73, 93, 94, 115, 116> Composition (salt) 9, 10, 30, 31, 51, 52, 72, 73, 93, 94, 114, 115 Similarly, using components (A) and (B) in the mixing ratios listed in Table 1A, preparations were made under the same conditions as in Example 52 to obtain formulations (salts) 9, 10, 30, 31, 51, 52, 72, 73, 93, 94, 114, and 115. The spectral data for representative formulations (salts) are shown below. Ingredients (salt) 9 FT-IR (KBr): 3392 cm -1 , 2954 cm -1 , 1720 cm -1 , 1155 cm -1 , 903 cm -1 . 1 HNMR (D2O, 400MHz): 1.25-1.44 (m, 2H, Lys, -C H 2CH2NH2), 1.56-1.63 (m, 2H, Lys, -C H 2CH2CH(NH2)COOH), 1.75-1.83 (m, 2H, Lys, -C H 2CH(NH2)COOH), 2.88-2.92 (t, 2H, Lys, -C H 2NH2), 3.52-3.55 (t, 1H, Lys, -C H (NH2)COOH). 3.63-3.72 3.52-3.72 (m, 4H), 3.92-3.93 (d, 1H), 4.00-4.02 (d, 1H): (Gluconic acid, HOC H 2C H (OH)C H (OH)C H (OH)C H (OH)COOH). 13 CNMR (D2O, 100MHz): 21.4 (Lys, - C H2CH2NH2), 26.4 (Lys, - C H2CH2CH(NH2)COOH), 29.8 (Lys, - C H2NH2), 38.6 (Lys, - C H2CH(NH2)COOH), 54.5 (Lys, - C H(NH2)COOH), 174.6 (Lys, C OOH), 178.5 (gluconic acid, C OOH). 62.6, 70.9, 71.1, 72.5, 74.0 (Gluconic acid, HO CH2 C H(OH) C H(OH) C H(OH) C H(OH)COOH). Complex (salt) 30 FT-IR (KBr): 3394 cm -1 , 1811 cm -1 , 1687 cm -1 , 1590 cm -1 , 1160 cm -1 . 1 HNMR (D2O, 400MHz): 1.31 - 1.48 (m, 2H, Lys, -C H 2CH2NH2), 1.60 - 1.69 (m, 2H, Lys, -C H 2CH2CH(NH2)COOH), 1.81 - 1.88 (m, 2H, Lys, -C H 2CH(NH2)COOH), 2.93 - 2.97 (t, 2H, Lys, -C H 2NH2), 3.56 - 3.60 (t, 1H, Lys, -C H (NH2)COOH). 3.68 - 3.81 (m, 8H), 3.98 - 4.01 (m, 2H), 4.17 - 4.19 (m, 2H): (Gluconic acid, HOC H 2C H (OH)C H (OH)C H (OH)C H (OH)COOH). 13 CNMR (D2O, 100MHz): 21.3 (Lys, - C H2CH2NH2), 26.2 (Lys, - C H2CH2CH(NH2)COOH), 29.9 (Lys, - C H2NH2), 39.1 (Lys, - C H2CH(NH2)COOH), 54.7 (Lys, - C H(NH2)COOH), 174.5 (Lys, COOH), 177.5 (Gluconic acid, C OOH). 62.3, 70.4, 71.9, 72.4, 73.7 (Gluconic acid, HO C H2 C H(OH) C H(OH) C H(OH) C H(OH)COOH), Complex (salt) 51 FT-IR (KBr): 3365 cm -1 , 1720 cm -1 , 1149 cm -1 , 836 cm -1 . 1 HNMR (D2O, 400MHz): 1.47 - 1.63 (m, 2H, Arg, -CH2C H 2CH2-), 1.74 - 1.80 (m, 2H, Arg, C H 2CH(NH2)COOH), 3.09 - 3.13 (t, 2H, Arg, -C H 2NH-), 3.63 - 3.66 (m, 1H, Arg, -C H (NH2)COOH). 3.51 - 3.71 (m, 4H), 3.89 - 3.90 (d, 1H), 3.99 - 4.00 (d, 1H): (Gluconic acid, HOC H 2C H (OH)C H (OH)C H (OH)C H (OH)COOH). 13 CNMR (D2O, 100MHz): 23.8 (Arg, -CH2 C H2CH2-), 27.6 (Arg, - C H2CH(NH2)COOH), 40.4 (Arg, - C H2NH-), 54.2 (Arg, - C H(NH2)COOH), 156.7 (Arg, - C (NH)NH2), 174.6 (Arg,C OOH), 178.5 (Gluconic acid, C OOH). 62.5, 70.9, 71.1, 72.5, 74.0 (Gluconic acid, HO C H2 C H(OH) C H(OH) C H(OH) C H(OH)COOH). Complex (salt) 72 FT-IR (KBr): 3365 cm -1 ,1795 cm -1 , 1153 cm -1 , 835 cm -1 . 1 HNMR (D2O, 400MHz): 1.45 - 1.62 (m, 2H, Arg, -CH2C H 2CH2-), 1.73 - 1.81 (m, 2H, Arg, -C H 2CH(NH2)COOH), 3.08 - 3.11 (t, 2H, Arg, -C H 2NH-), 3.63 - 3.66 (m, 1H, Arg, -C H (NH2)COOH). 3.49 - 3.69 (m, 8H) 3.93 - 3.94 (d, 2H), 4.12 - 4.13 (d, 2H) :(Gluconic acid, HOC H 2C H (OH)C H (OH)C H (OH)C H (OH)COOH). 13 CNMR (D2O, 100MHz): 23.8 (Arg, -CH2 C H2CH2-), 27.5 (Arg, - C H2CH(NH2)COOH), 40.4 (Arg, - C H2NH-), 54.2 (Arg, - C H(NH2)COOH), 156.7 (Arg, - C(NH)NH2), 174.3 (Arg, C OOH), 177.5 (gluconic acid, C OOH). 62.6, 70.8, 71.0, 72.1, 73.3 (Gluconic acid, HO C H2 C H(OH) C H(OH) C H(OH) C H(OH)COOH). Complex (salt) 73 FT-IR (KBr): 3366 cm -1 , 3203 cm -1 , 1763 cm -1 , 1149 cm -1 , 866 cm -1 . 1 HNMR (D2O, 400MHz): 1.23 - 1.25 (d, 6H, Lactic acid, -C H 3), 1.48 - 1.69 (m, 2H, Arg, -CH2C H 2CH2-), 1.75 - 1.81 (m, 2H, Arg, -C H 2CH(NH2)COOH), 3.09 - 3.13 (t, 2H, Arg, -C H 2NH-), 3.63 - 3.66 (t, 1H, Arg, -C H (NH2)COOH), 4.09 - 4.15 (q, 2H, Lactic acid, -C H OH-). 13 CNMR (D2O, 100MHz): 19.6 (Lactic acid, - C H3), 23.8 (Arg, -CH2 C H2CH2-), 27.5 (Arg, - C H2CH(NH2)COOH), 40.4 (Arg, - C H2NH-), 54.2 (Arg, - C H(NH2)COOH), 67.4 (Lactic acid, - CHOH-), 156.7 (Arg, - C (NH)NH2), 174.2 (Arg, C OOH), 180.5 (Lactic acid, C OOH). Complex (salt) 93 FT-IR (KBr): 3373 cm -1 , 3159 cm -1 , 1735 cm -1 , 1082 cm -1 . 1 HNMR (D2O, 400MHz): 3.89 (s, 2H, His, -C H 2-), 3.87 - 3.90 (t, 1H, His, -C H (NH2)COOH). 3.20 - 3.70 (m, 5H), 4.00 (s, 1H): (Gluconic acid, HOC H 2C H (OH)C H (OH)C H (OH)C H (OH)COOH). 7.23 (s, 1H), 8.47 (s, 1H): (His, Imidazole). 13 CNMR (D2O, 100MHz): 25.9 (His, - C H2-), 53.6 (His, - C H(NH2)COOH), 172.6 (His, C OOH), 178.5 (Gluconic acid, C OOH). 62.5, 70.9, 71.1, 72.5, 74.0 (Gluconic acid, HO C H2 C H(OH) C H(OH) C H(OH) C H(OH)COOH). 117.6, 127.7, 134.1 (His, Imidazole). Complex (salt) 114 FT-IR (KBr): 3378 cm -1 , 2928 cm -1 , 1677 cm -1 , 1152 cm -1 , 894 cm -1 . 1 HNMR (D2O, 400MHz): 3.21 - 3.33 (d, 2H, His, -C H 2-), 3.88 - 3.89 (t, 1H, His, -C H (NH2)COOH). 3.51 - 3.65 (m, 8H), 3.92 - 3.94 (m, 2H), 4.09 - 4.10 (m, 2H): (Gluconic acid, HOC H 2C H (OH)C H (OH)C H (OH)C H (OH)COOH). 7.26 (s, 1H), 8.54 (s, 1H): (His, Imidazole). 13 CNMR (D2O, 100MHz): 25.7 (His, - C H2-), 53.5 (His, - C H(NH2)COOH), 172.5 (His, C OOH), 177.4 (Gluconic acid, C OOH). 62.5, 71.8, 72.0, 73.2 (Gluconic acid, HO C H2 C H(OH) C H(OH) C H(OH) C H(OH)COOH). 117.6, 127.3, 133.9 (His, Imidazole). Complex (salt) 115 FT-IR (KBr): 3384 cm -1 , 3155 cm -1 , 1775 cm -1, 1125 cm -1 , 875 cm - . 1 HNMR (D2O, 400MHz): 1.21-1.22 (d, 6H, Lactic acid, -C H 3), 3.19-3.21 (d, 2H, His, -C H 2-), 3.87-3.90 (t, 1H, His, -C H (NH2)COOH), 4.07-4.11 (q, 2H, Lactic acid, -C H OH-). 7.24 (s, 1H), 8.52 (s, 1H): (His, Imidazole). 13 CNMR (D2O, 100MHz): 19.6 (Lactic acid, C H3-), 25.7 (His, - C H2-), 53.5 (His, - C H(NH2)COOH), 67.4 (Lactic acid, - C HOH-), 172.5 (His, C OOH), 180.5 (Lactic acid, - C (Out of the Home) 117.6, 127.3, 133.9 (His, Imidazole).

[0160] <Example 53> Composition (Salt) 53 L-arginine (11.78 g, 0.10 mol) and adipic acid (14.61 g, 0.10 mol) were stirred in 50 ml of water at room temperature for 1 hour, and then the water was removed by distillation under reduced pressure to obtain a white solid compound (salt) consisting of L-arginine and adipic acid. Ingredients (salt) 53 FT-IR (KBr): 3131 cm -1 , 2940 cm -1 , 1752 cm -1 , 1427 cm -1 , 857 cm -1 . 1 HNMR (D2O, 400MHz): 1.47-1.66 (m, 4H, Adipic acid, -C H 2-), 1.48-1.69 (m, 2H, Arg, -CH2C H 2CH2-), 1.76-1.82 (m, 2H, Arg, -C H 2CH(NH2)COOH), 2.18-2.20 (t, 4H, Adipic acid, -C H 2COOH), 3.10-3.13 (t, 2H, Arg, -C H 2NH-), 3.64-3.66 (t, 1H, Arg, -C H (NH2)COOH). 13 CNMR (D2O, 100MHz): 23.8 (Arg, -CH2 C H2CH2-), 24.6 (Adipic acid, - C H2-), 27.5 (Arg, - C H2CH(NH2)COOH), 35.3 (Adipic acid, - C H2COOH), 40.4 (Arg, - C H2NH-), 54.2 (Arg, - C H(NH2)COOH), 156.7 (Arg, - C (NH)NH2), 174.3 (Arg, C OOH), 181.1 (Adipic acid, C (Out of the Home)

[0161] <Examples 11-13, 32-34, 53-55, 74-76, 95-97, 116-118> Composition (salt) 11-13, 32-34, 53-55, 74-76, 95-97, 116-118 Similarly, using components (A) and (B) in the mixing ratios listed in Table 1A, preparations were made under the same conditions as in Example 53 to obtain formulations (salts) 11-13, 32-34, 53-55, 74-76, 95-97, and 116-118. <Example 56> Composition (Salt) 56

[0162] L-arginine (11.78 g, 0.10 mol) and fumaric acid (11.60 g, 0.10 mol) were stirred in 50 ml of water at room temperature for 1 hour, and then the water was removed by distillation under reduced pressure to obtain a white solid compound (salt) consisting of L-arginine and fumaric acid. Ingredients (salt) 56 FT-IR (KBr): 3147 cm -1 , 1749 cm -1 , 1632 cm -1 , 1555 cm -1 , 1375 cm -1 . 1 HNMR (D2O, 400MHz): 1.47-1.65 (m, 2H, Arg, -CH2C H 2CH2-), 1.76-1.83 (m, 2H, Arg, - -C H 2CH(NH2)COOH), 3.10-3.13 (t, 2H, Arg, -C H 2NH-), 3.65-3.68 (t, 1H, Arg, -C H (NH2)COOH), 6.56 (s, 2H, Fumaric acid, -C H =C H -). 13 CNMR (D2O, 100MHz): 23.6 (Arg, -CH2 C H2CH2-), 27.5 (Arg, - C H2CH(NH2)COOH), 40.4 (Arg, - C H2NH-), 54.2 (Arg, - C H(NH2)COOH), 134.7 (Fumaric acid, - C H= C H-), 156.7 (Arg, - C (NH)NH2), 171.7 (Fumaric acid, C OOH), 174.2 (Arg, C OOH)

[0163] <Examples 14, 35, 56, 77, 98, 119> Composition (salt) 14, 35, 56, 77, 98, 119 Similarly, using components (A) and (B) in the mixing ratios listed in Table 1A, preparations were made under the same conditions as in Example 56 to obtain formulations (salts) 14, 35, 56, 77, 98, and 119.

[0164] <Example 16> Composition (Salt) 16 L-lysine (14.63 g, 0.10 mol) and citric acid (19.39 g, 0.10 mol) were stirred in 50 ml of water at room temperature for 3 hours, and then the water was removed by distillation under reduced pressure to obtain a yellow liquid. By washing the obtained liquid, a compound (salt) consisting of the yellow liquid L-lysine and citric acid was obtained. Ingredients (salt) 16 FT-IR (KBr): 3432 cm -1 , 3148 cm -1 , 1764 cm -1 , 1217 cm -1 , 848 cm -1 . 1 HNMR (D2O, 400MHz): 1.26-1.44 (m, 2H, Lys, -C H 2CH2NH2), 1.55-1.63 (m, 2H, Lys, -C H 2CH2CH(NH2)COOH), 1.74-1.81 (m, 2H, Lys, -C H 2CH(NH2)COOH), 2.62-2.65 (d, 2H, Citric acid, -C H 2COOH), 2.75-2.78 (d, 2H, Citric acid, -C H 2COOH), 2.86-2.90 (t, 2H, Lys, -C H 2NH2), 3.62-3.65 (t, 1H, Lys, -C H (NH2)COOH). 13 CNMR (D2O, 100MHz): 21.4 (Lys, - C H2CH2NH2), 26.3 (Lys, - CH2CH2CH(NH2)COOH), 29.8 (Lys, - C H2NH2), 39.0 (Lys, - C H2CH(NH2)COOH), 43.7 (Citric acid, - C H2COOH), 54.4 (Lys, - C H(NH2)COOH), 73.8 (Citric acid, - C (OH)(COOH)-), 174.4 (Lys, C OOH) 174.7 (Citric acid, -CH2 C OOH), 178.6 (Citric acid, -C(OH)( C OOH)-).

[0165] <Examples 15-17, 36-38, 57-59, 78-80, 99-101, 120-122> Composition (salt) 15-17, 36-38, 57-59, 78-80, 99-101, 120-122 Similarly, using components (A) and (B) in the mixing ratios listed in Table 1A, preparations were made under the same conditions as in Example 16, yielding formulations (salts) 15-17, 36-38, 57-59, 78-80, 99-101, and 120-122. The spectral data for representative formulations (salts) are shown below. Ingredients (salt) 37 FT-IR (KBr): 3400 cm -1 , 1762 cm -1 , 1575 cm -1 , 853 cm -1 . 1 HNMR (D2O, 400MHz): 1.33-1.48 (m, 6H, Lys, -C H 2CH2NH2), 1.62-1.70 (m, 6H, Lys, -C H 2CH2CH(NH2)COOH), 1.81-1.88 (m, 6H, Lys, -C H 2CH(NH2)COOH), 2.62-2.78 (d, 8H, Citric acid, C H2(COOH)-), 2.94 - 2.98 (t, 6H, Lys, -C H 2NH2), 3.71 - 3.74 (t, 3H, Lys, -C H (NH2)COOH). 13 CNMR (D2O, 100MHz): 21.4 (Lys, - C H2CH2NH2), 26.4 (Lys, - C H2CH2CH(NH2)COOH), 29.8 (Lys, - C H2NH2), 39.1 (Lys, - C H2CH(NH2)COOH), 43.6 (Citric acid, C H2(COOH)-), 54.6 (Lys, - C H(NH2)COOH), 73.5 (Citric acid, - C (OH)(COOH)-), 174.0 (Lys, C OOH), 174.3 (Citric acid, -CH2 C OOH), 177.8 (Citric acid, -C(OH)( C OOH)-). Complex (salt) 57 FT-IR (KBr): 3368 cm -1 , 3203 cm -1 , 1763 cm -1 , 1398 cm -1 , 918 cm -1 . 1 HNMR (D2O, 400MHz): 1.47 - 1.64 (m, 2H, Arg, -CH2C H 2CH2-), 1.76 - 1.82 (m, 2H, Arg, - -C H 2CH(NH2)COOH), 2.48 - 2.72 (m, 2H, Malic acid, -C H 2COOH), 3.10 - 3.14 (t, 2H, Arg, -C H 2NH-), 3.64 - 3.67 (t, 1H, Arg, -C H(NH2)COOH), 4.25 - 4.28 (t, 1H, Malic acid, -C H (OH)COOH). 13 13C NMR (D2O, 100 MHz): 23.8 (Arg, -CH2 C H2CH2-), 27.5 (Arg, - C H2CH(NH2)COOH), 40.1 (Malic acid, - C H2-), 40.4 (Arg, - C H2NH-), 54.2 (Arg, - C H(NH2)COOH), 68.6 (Malic acid, - C HOH-), 156.7 (Arg, - C (NH)NH2), 174.3 (Arg, C OOH), 176.4 (Malic acid, -CH2 C OOH), 179.1 (Malic acid, -CH(OH) C OOH). Complex (salt) 58 FT-IR (KBr): 3365 cm -1 , 3207 cm -1 , 1763 cm -1 , 1217 cm -1 , 850 cm -1 . 1 1H NMR (D2O, 400 MHz): 1.47 - 1.66 (m, 2H, Arg, -CH2C H 2CH2-), 1.76 - 1.81 (m, 2H, Arg, -C H 2CH(NH2)COOH), 2.62 - 2.79 (d, 4H, Citric acid, -C H 2COOH), 3.10 - 3.13 (t, 2H, Arg, -C H 2NH-), 3.64 - 3.67 (t, 1H, Arg, -C H (NH2)COOH). 13CNMR (D2O, 100MHz): 23.8 (Arg, -CH2 C H2CH2-), 27.5 (Arg, - C H2CH(NH2)COOH), 40.4 (Arg, - C H2NH-), 43.7 (Citric acid, - C H2COOH), 54.2 (Arg, - C H(NH2)COOH), 73.8 (Citric acid, - C (OH)(COOH)-), 156.7 (Arg, - C (NH)NH2), 174.3 (Arg, C OOH), 174.8 (Citric acid, -CH2 C OOH), 178.7(Citric acid, -C(OH)( C OOH)-). Complex (salt) 59 FT-IR (KBr): 3364 cm -1 , 3211 cm -1 , 1764 cm -1 , 1154 cm -1 , 854 cm -1 . 1 HNMR (D2O, 400MHz): 1.49 - 1.66 (m, 2H, Arg, -CH2C H 2CH2-), 1.77 - 1.82 (m, 2H, Arg, -C H 2CH(NH2)COOH), 3.11 - 3.14 (t, 2H, Arg, -C H 2NH-), 3.65 - 3.68 (t, 1H, Arg, -C H (NH2)COOH), 4.40 (s, 2H, Tartaric acid, -C H (OH)COOH). 13 CNMR (D2O, 100MHz): 23.8 (Arg, -CH2 C H2CH2-), 27.5 (Arg, - C H2CH(NH2)COOH), 40.4 (Arg, -C H2NH-), 54.2 (Arg, - C H(NH2)COOH), 72.8 (Tartaric acid, - C H(OH)COOH), 156.7 (Arg, - C (NH)NH2), 174.2(Arg, C OOH), 176.5 (Tartaric acid, C OOH). Complex (salt) 78 FT-IR (KBr): 3368 cm -1 , 3203 cm -1 , 1763 cm -1 , 1128 cm -1 , 918 cm -1 . 1 HNMR (D2O, 400MHz): 1.48 - 1.64 (m, 2H, Arg, -CH2C H 2CH2-), 1.76 - 1.82 (m, 2H, Arg, -C H 2CH(NH2)COOH-), 2.60 - 2.78 (d, 4H, Malic acid, C H 2COOH-), 3.10 - 3.13 (t, 2H, Arg, -C H 2NH-), 3.65 - 3.68 (t, 1H, Arg, -C H (NH2)COOH), 4.35 - 4.37 (t, 2H, Malic acid, -C H (OH)COOH). 13 CNMR (D2O, 100MHz): 23.8 (Arg, -CH2 C H2CH2-), 27.4 (Arg, - C H2CH(NH2)COOH), 39.1 (Malic acid, - C H2COOH), 40.4 (Arg, - C H2NH-), 54.2 (Arg, - C H(NH2)COOH), 67.6 (Malic acid, - CH(OH)COOH), 156.7 (Arg, - C (NH)NH2), 174.2 (Arg, C OOH), 175.3 (Malic acid, CH2 C OOH), 177.9 (Malic acid, CH(OH) C OOH). Complex (salt) 79 FT-IR (KBr): 3365 cm -1 , 3194 cm -1 , 1764 cm -1 , 1213 cm -1 . 1 HNMR (D2O, 400MHz): 1.48 - 1.65 (m, 6H, Arg, -CH2C H 2CH2-), 1.76 - 1.82 (m, 6H, Arg, CH(COOH)(NH2)C H 2-), 2.57 - 2.61 (d, 4H, Citric acid, -C H 2COOH), 2.69 - 2.72 (d, 4H, Citric acid, -C H 2COOH), 3.10 - 3.13 (t, 6H, Arg, -C H 2NH-), 3.63 - 3.67 (t, 3H, Arg, -C H (NH2)COOH). 13 CNMR (D2O, 100MHz): 23.8 (Arg, -CH2 C H2CH2-), 27.4 (Arg, - C H2CH(NH2)COOH), 39.1 (Citric acid, - C H2COOH), 40.4 (Arg, - C H2NH-), 54.2 (Arg, - C H(NH2)COOH), 67.6 (Citric acid, - C (OH)COOH), 156.7 (Arg, - C (NH)NH2), 174.2 (Arg, COOH), 175.3 (Citric acid, -CH2 C OOH), 177.9 (Citric acid, -C(OH)( C OOH)-). Complex (salt) 80 FT-IR (KBr): 3365 cm -1 , 3215 cm -1 , 1693 cm -1 , 1150 cm -1 , 725 cm -1 . 1 HNMR (D2O, 400MHz): 1.46 - 1.65 (m, 2H, Arg, -CH2C H 2CH2-), 1.76 - 1.82 (m, 2H, Arg, -C H 2CH(NH2)COOH), 3.09 - 3.12 (t, 2H, Arg, -C H 2NH-), 3.66 - 3.69 (t, 1H, Arg, -C H (NH2)COOH), 4.49 (s, 4H, Tartaric acid, -C H (OH)COOH). 13 CNMR (D2O, 100MHz): 23.8 (Arg, -CH2 C H2CH2-), 27.4 (Arg, - C H2CH(NH2)COOH), 40.4 (Arg, - C H2NH-), 54.0 (Arg, - C H(NH2)COOH), 72.3 (Tartaric acid, - C H(OH)COOH), 156.7 (Arg, C (NH)NH2), 174.0 (Arg, C OOH), 175.5 (Tartaric acid, C OOH). Complex (salt) 100 FT-IR (KBr): 3408 cm -1 , 3149 cm -1 , 1715 cm-1 , 1225 cm -1 , 828 cm -1 . 1 HNMR (D2O, 400MHz): 2.62 - 2.66 (d, 2H, Citric acid, -C H 2COOH), 2.74 - 2.78 (d, 2H, Citric acid, -C H 2COOH), 3.21 - 3.23 (d, 2H, His, -C H 2-), 3.89 - 3.92 (t, 1H, His, -C H (NH2)COOH). 7.23 (s, 1H), 8.54 (s, 1H): (His, Imidazole). 13 CNMR (D2O, 100MHz): 25.7 (His, - C H2-), 43.6 (Citric acid, - C H2COOH), 53.5 (His, - C H(NH2)COOH), 73.8 (Citric acid, - C (OH)(COOH)-), 172.5 (His, C OOH), 174.7 (Citric acid, -CH2 C OOH), 178.7 (Citric acid, -C(OH)( C OOH)-). 117.6, 127.7, 134.1 (His, Imidazole). Complex (salt) 121 FT - IR (KBr): 3387 cm -1 , 3249 cm -1 , 1710 cm -1 , 924 cm -1 . 1 HNMR (D2O, 400MHz): 2.50 - 2.54 (d, 4H, Citric acid, -C H 2COOH), 2.63 - 2.67 (d, 4H, Citric acid, -CH 2COOH), 3.16-3.18 (d, 6H, His, -C H 2-), 3.84-3.87 (t, 3H, His, -C H (NH2)COOH). 7.23 (s, 3H), 8.47 (s, 3H): (His, Imidazole). 13 CNMR (D2O, 100MHz): 25.6 (His, - C H2-), 43.6 (Citric acid, - C H2COOH), 53.5 (His, - C H(NH2)COOH), 73.8 (Citric acid, - C (OH)(COOH)-), 172.6 (His, C OOH), 175.8 (Citric acid, -CH2 C OOH), 179.5 (Citric acid, -C(OH)( C OOH)-). 117.6, 127.7, 134.1 (His, Imidazole).

[0166] <Example 60> Composition (salt) 60 L-arginine (11.78 g, 0.10 mol) and benzoic acid (12.21 g, 0.10 mol) were stirred in 50 ml of water at room temperature for 1 hour, and then the water was removed by distillation under reduced pressure to obtain a colorless liquid. By washing the obtained liquid, a compound (salt) consisting of the colorless liquid L-arginine and benzoic acid was obtained. Ingredients (salt) 60 FT-IR (KBr): 3366 cm -1 , 3189 cm -1 , 1718 cm -1 , 1191 cm -1 , 848 cm -1 , 738 cm -1 . 1 HNMR (D2O, 400MHz): 1.41-1.59 (m, 2H, Arg, -CH2CH 2CH2-), 1.70-1.76 (m, 2H, Arg, - -C H 2CH(NH2)COOH), 2.99-3.03 (t, 2H, Arg, -C H 2NH-), 3.59-3.61 (t, 1H, Arg, -C H (NH2)COOH), 7.31-7.35 (t, 2H, Benzoic acid, Ph), 7.38-7.42 (t, 1H, Benzoic acid, Ph), 7.72-7.74 (d, 2H, Benzoic acid, Ph). 13 CNMR (D2O, 100MHz): 23.8 (Arg, -CH2 C H2CH2-), 27.5 (Arg, - C H2CH(NH2)COOH), 40.4 (Arg, -NH C H2CH2-), 54.3 (Arg, - C H2NH-), 128.3 (Benzoic acid, Ph), 128.6 (Benzoic acid, Ph), 131.2 (Benzoic acid, Ph), 136.1 (Benzoic acid, Ph), 156.6 (Arg, - C (NH)NH2), 174.3 (Arg, C OOH), 175.6 (Benzoic acid, C (Out of the Home)

[0167] <Examples 18, 39, 60, 81, 102, 123> Composition (salt) 18, 39, 60, 81, 102, 123 Similarly, using components (A) and (B) in the mixing ratios listed in Table 1A, preparations were made under the same conditions as in Example 60 to obtain formulations (salts) 18, 39, 60, 81, 102, and 123.

[0168] <Example 61> Composition (Salt) 61 L-arginine (11.78 g, 0.10 mol) and cinnamic acid (14.81 g, 0.10 mol) were stirred in 50 ml of water at room temperature for 1 hour, and then the water was removed by distillation under reduced pressure to obtain a white solid compound (salt) consisting of L-arginine and cinnamic acid. Ingredients (salt) 61 FT-IR (KBr): 3088 cm -1 , 1637 cm -1 , 1532 cm -1 , 1381 cm -1 . 1 HNMR (D2O, 400MHz): 1.44-1.63 (m, 2H, Arg, -CH2C H 2CH2-), 1.74-1.80 (m, 2H, Arg, - -C H 2CH(NH2)COOH), 3.05-3.08 (t, 2H, Arg, -C H 2NH-), 3.61-3.64 (t, 1H, Arg, -C H (NH2)COOH), 6.37-6.42 (d, 2H, Cinnamic acid, -C H =C H -), 7.25-7.33 (m, 3H, Cinnamic acid, Ph), 7.49-7.51 (d, 2H, Cinnamic acid, Ph). 13 CNMR (D2O, 100MHz): 23.8 (Arg, -CH2 C H2CH2-), 27.5 (Arg, - C H2CH(NH2)COOH), 40.5 (Arg, -NH C H2CH2-), 54.3 (Arg, - C H2NH-), 124.1, 127.7, 129.0, 129.6, 135.1, 140.8 (Cinnamic acid, Ph, - C H= C H-), 156.6 (Arg, - C (NH)NH2), 174.3 (Arg, COOH), 175.7 (Cinnamic acid, C (Out of the Home)

[0169] <Examples 19, 40, 61, 82, 103, 124> Composition (salt) 19, 40, 61, 82, 103, 124 Similarly, using components (A) and (B) in the mixing ratios listed in Table 1A, preparations were made under the same conditions as in Example 61 to obtain formulations (salts) 19, 40, 61, 82, 103, and 124.

[0170] <Example 62> Composition (Salt) 62 L-arginine (11.78 g, 0.10 mol) and L-ascorbic acid (17.61 g, 0.10 mol) were stirred in 50 ml of water at room temperature for 1 hour, and then the water was removed by distillation under reduced pressure to obtain a colorless liquid. By washing the obtained liquid, a white solid compound (salt) consisting of L-arginine and L-ascorbic acid was obtained. Ingredients (salt) 62 FT-IR (KBr): 3161 cm -1 , 1559 cm -1 , 1342 cm -1 , 1108 cm -1 , 900cm -1 . 1 HNMR (D2O, 400MHz): 1.50-1.68 (m, 2H, Arg, -CH2C H 2CH2-), 1.77-1.84 (m, 2H, Arg, -C H 2CH(NH2)COOH), 3.12-3.16 (t, 2H, Arg, -C H 2NH-), 3.89-3.94 (t, 1H, Arg, -C H (NH2)COOH). 3.61-3.69 (m, 3H), 4.41-4.42 (d, 1H): (Ascorbic acid, C H cyclo , -C H (OH)C H 2OH). 13CNMR (D2O, 100MHz): 23.8 (Arg, -CH2 C H2CH2-), 27.5 (Arg, - C H2CH(NH2)COOH), 40.4 (Arg, - C H2NH-), 54.4 (Arg, - C H(NH2)COOH), 156.7 (Arg, - C (NH)NH2), 174.3 (Arg, C (Out of the Home) 62.5, 69.1, 78.3, 113.1, 177.8: (Ascorbic acid, C H cyclo , - C H(OH) C H2OH.

[0171] <Examples 20, 21, 41, 42, 62, 63, 83, 84, 104, 105, 125, 126> Composition (salt) 20, 21, 41, 42, 62, 63, 83, 84, 104, 105, 125, 126 Similarly, using components (A) and (B) in the mixing ratios listed in Table 1A, preparations were made under the same conditions as in Example 62 to obtain formulations (salts) 20, 21, 41, 42, 62, 63, 83, 84, 104, 105, 125, and 126.

[0172] <Example 170> Composition (Salt) 170 γ-aminobutyric acid (10.31 g, 0.10 mol) and acetic acid (6.01 g, 0.10 mol) were stirred in 50 ml of water at room temperature for 1 hour, and then the water was removed by distillation under reduced pressure to obtain a white solid compound (salt) consisting of γ-aminobutyric acid and acetic acid. Ingredients (salt) 170 FT-IR (KBr): 2931 cm -1 , 2209 cm -1 , 1653 cm -1 , 1574 cm -1 , 1029 cm -1 , 659 cm -1 . 1HNMR (D2O, 400MHz): 1.77 - 1.87 ((m, 3H, Acetic acid, -C H 3), (m, 2H, γ - Aminobutyric acid, -CH2C H 2CH2 -)), 2.19 - 2.23 (quin, 2H, γ - Aminobutyric acid, -C H 2NH2), 2.90 - 2.94 (t, 2H, γ - Aminobutyric acid, -C H 2COOH). 13 CNMR (D2O, 100MHz): 23.4 (γ - Aminobutyric acid, -CH2 C H2CH2 -), 34.1 (γ - Aminobutyric acid, - C H2NH2), 39.2 (Acetic acid, - C H3), 39.4 (γ - Aminobutyric acid, - C H2COOH), 180.2 (γ - Aminobutyric acid, C OOH), 181.3 (Acetic acid, C OOH).

[0173] <Examples 127 - 132, 147 - 152, 167 - 172, 187 - 191, 204 - 208, 221 - 225, 238 - 242, 255 - 259, 272 - 276, 289 - 293, 306 - 310, 323 - 327, 340 - 345, 360 - 364, 377 - 381> Complexes (salts) 127 - 132, 147 - 152, 167 - 172, 187 - 191, 204 - 208, 221 - 225, 238 - 242, 255 - 259, 272 - 276, 289 - 293, 306 - 310, 323 - 327, 340 - 345, 360 - 364, 377 - 381 Similarly, using components (A) and (B) in the mixing ratios listed in Tables 1B and C, preparations were made under the same conditions as in Example 170, yielding formulations (salts) 127-132, 147-152, 167-172, 187-191, 204-208, 221-225, 238-242, 255-259, 272-276, 289-293, 306-310, 323-327, 340-345, 360-364, and 377-381. The spectral data for representative formulations (salts) are shown below. Ingredients (salt) 345 FT-IR (KBr): 2925 cm -1 , 2855 cm -1 , 1712 cm -1 , 1616 cm -1 , 1463 cm -1 . 1 HNMR (MeOD, 400MHz): 0.86-0.94 (m, 6H, Isostearic acid, -C H 3), 3.32-3.40 (m, 1H, Isostearic acid, -C H (COOH)-). 1.31 (s, 22H), 1.59-1.63 (m, 2H), 2.17-2.21 (t, 2H), 3.21-3.25 (t, 2H): (Isostearic acid, CH3(C H 2) 8CH((C H 2)6CH3)COOH). 1.89-2.27 (m, 4H), 3.19-3.34 (m, 2H), 4.00-4.06 (t, 1H): (Pro, C H 2 hetero , C H hetero ). 13 CNMR (MeOD, 100MHz): 56.2 (Isostearic acid, - C H(COOH)-), 174.1 (Pro, C OOH), 182.6 (Isostearic acid, C (Out of the Home) 29.5, 30.8, 38.8, 48.4, 48.8, 49.0, 49.5 (Isostearic acid, C H3( C H2)8CH(( C H2)6 C H3)COOH). 23.6, 28.9, 46.0, 61.0: (Pro, C H 2 hetero , C H hetero ).

[0174] <Example 173> Composition (Salt) 173 γ-aminobutyric acid (10.31 g, 0.10 mol) and oleic acid (28.25 g, 0.10 mol) were stirred in 50 mL of water and 50 mL of ethanol at room temperature for 3 hours, and the solvent was removed by distillation under reduced pressure to obtain a colorless liquid. By washing the obtained liquid, a compound (salt) consisting of the colorless liquid γ-aminobutyric acid and oleic acid was obtained. Ingredients (salt) 173 FT-IR (KBr): 2925 cm -1 , 2854 cm -1 , 1711 cm -1 , 1552 cm -1 , 1406 cm -1 , 1244 cm -1 . 1 HNMR (MeOD, 400MHz): 0.90-0.94 (m, 3H, Oleic acid, -C H 3), 1.86-1.93 (quin, 2H, γ-Aminobutyric acid, -CH2C H 2CH2-), 2.35-2.39 (t, 2H, γ-Aminobutyric acid, -C H 2NH2), 2.97-3.00 (t, 2H, γ-Aminobutyric acid, -C H 2COOH), 3.32-3.34 (m, 2H, Oleic acid, -C H 2COOH), 5.35-5.38 (m, 2H, Oleic acid, -CH =C H -). 1.31-1.35 (m, 20H), 1.58-1.66 (m, 2H), 2.03-2.10 (m, 2H), 2.25-2.29 (m, 2H): (Oleic acid, CH3(C H 2) 7CH=CH(C H 2) 7COOH). 13 CNMR (MeOD, 100MHz): 14.5 (Oleic acid, -C H 3), 23.7 (γ-Aminobutyric acid, -CH2 C H2CH2-), 32.7 (γ-Aminobutyric acid, - C H2NH2), 40.9 (γ-Aminobutyric acid, - C H2COOH), 130.9 (Oleic acid, - C H= C H-), 178.8 (γ-Aminobutyric acid, C OOH), 179.8 (Oleic acid, C (Out of the Home) 24.7, 26.4, 28.2, 30.3, 30.37, 30.39, 30.48, 30.52, 30.6, 30.8, 33.1, 35.4, 35.9 (Oleic acid, CH3( C H2)7CH=CH( C H2)7COOH).

[0175] <Examples 133, 134, 153, 154, 173, 174, 346, 347> Composition (salt) 133, 134, 153, 154, 173, 174, 346, 347 Similarly, using components (A) and (B) in the mixing ratios listed in Tables 1B and C, preparations were made under the same conditions as in Example 173, yielding formulations (salts) 133, 134, 153, 154, 173, 174, 346, and 347. The spectral data for representative formulations (salts) are shown below. Ingredients (salt) 346 FT-IR (KBr): 2938 cm -1 , 2855 cm -1 , 1711 cm -1 , 1616 cm -1 , 1410 cm -1 , 1291 cm -1 . 1 HNMR (MeOD, 400MHz): 0.90-0.94 (t, 3H, Oleic acid, -C H 3), 5.32-5.41 (t, 2H, Oleic acid, -C H =C H -). 1.31-1.35 (m, 20H), 1.60-1.64 (t, 2H), 1.96-2.17 (m, 4H), 2.27-2.37 (m, 2H): (Oleic acid, CH3(C H 2)7CH=CH(C H 2)7COOH). 1.96-2.37 (m, 4H), 3.23-3.39 (m, 2H), 3.98-4.00 (t, 1H): (Pro, C H 2 hetero , C H hetero ). 13 CNMR (MeOD, 100MHz): 14.7 (Oleic acid, -C H 3), 63.1 (Oleic acid, -C H 2COOH), 130.8, 130.9 (Oleic acid, - C H= C H-), 174.1 (Pro, C OOH), 177.8 (Oleic acid, C OOH). 25.2, 26.2, 27.7, 29.7, 30.3, 30.5, 30.7, 30.8, 33.1, 34.8, 35.1 (Oleic acid, CH3( C H2)7CH=CH( C H2)7COOH). 23.8, 28.2, 48.4, 62.2: (Pro, C H 2 hetero , C H hetero ). Complex (salt) 347 FT-IR (KBr): 2927 cm -1 , 2856 cm -1 , 1711 cm -1 , 1617 cm -1 , 1410 cm -1 , 1252 cm -1 . 1 HNMR (MeOD, 400MHz): 0.91 - 0.95 (t, 3H, Linoleic acid, -C H 3), 5.31 - 5.42 (m, 4H, Linoleic acid, -C H =C H -). 1.31 - 1.41 (m, 12H), 1.59 - 1.64 (m, 2H), 1.95 - 2.18 (q, 4H), 2.78 - 2.81 (t, 2H), 3.23 - 3.29 (t, 2H), 3.30 - 3.33 (t, 2H): (Linoleic acid, CH3(C H 2)4(CH=CHC H 2)2(C H 2)6COOH). 1.89 - 2.38 (m, 4H), 3.23 - 3.39 (m, 2H), 3.98 - 4.06 (t, 1H): (Pro, C H 2 hetero , C H hetero ). 13 CNMR (MeOD, 100MHz): 14.7 (Linoleic acid, - C H3), 129.1, 130.9(Linoleic acid, - C H= C H-), 174.0 (Pro, C OOH), 177.8 (Linoleic acid, C OOH). 26.6, 27.8, 28.6, 29.6, 30.1, 30.3, 30.5, 30.7, 32.7, 34.8, 35.1, 35.3, 47.1 (Linoleic acid, CH3( C H2)4(CH=CH C H2)2( C H2)6COOH). 26.2, 28.2, 48.4, 62.2: (Pro, C H 2 hetero , C H hetero ).

[0176] <Example 176> Composition (Salt) 176 γ-aminobutyric acid (10.31 g, 0.10 mol) and 30% by mass lactic acid (30.01 g, 0.10 mol) were stirred in 50 ml of water at room temperature for 3 hours, and then the water was removed by distillation under reduced pressure to obtain a colorless liquid. By washing the obtained liquid, a compound (salt) consisting of the colorless liquid γ-aminobutyric acid and lactic acid was obtained. Ingredients (salt) 176 FT-IR (KBr): 3406 cm -1 , 2984 cm -1 , 1764 cm -1 , 878 cm -1 . 1 HNMR (D2O, 400MHz): 1.22-1.24 (d, 3H, Lactic acid, -C H 3), 1.76-1.84 (quin, 2H, γ-Aminobutyric acid, -CH2C H 2CH2-), 2.28-2.34 (t, 2H, γ-Aminobutyric acid, -C H 2NH2), 2.88-2.91 (t, 2H, γ-Aminobutyric acid, -C H 2COOH), 4.06-4.11 (q, 1H, Lactic acid, -C H OH-). 13CNMR (D2O, 100MHz): 19.7 (Lactic acid, - C H3), 22.6 (γ-Aminobutyric acid, -CH2 C H2CH2-), 32.0 (γ-Aminobutyric acid, - C H2NH2), 38.9 (γ-Aminobutyric acid, - C H2COOH), 67.6 (Lactic acid, - C HOH-), 178.7 (γ-Aminobutyric acid, C OOH), 180.9 (Lactic acid, C (Out of the Home)

[0177] <Examples 135, 136, 155, 156, 175, 176, 192, 193, 209, 210, 226, 227, 243, 244, 260, 261, 277, 278, 294, 295, 311, 312, 328, 329, 348, 349, 365, 366, 382, ​​383> Composition (Salt) 135, 136, 155, 156, 175, 176, 192, 193, 209, 210, 226, 227, 243, 244, 260, 261, 277, 278, 294, 295, 311, 312, 328, 329, 348, 349, 365, 366, 382, ​​383 Similarly, using components (A) and (B) in the mixing ratios listed in Tables 1B and C, preparations were made under the same conditions as in Example 176, yielding formulations (salts) 135, 136, 155, 156, 175, 176, 192, 193, 209, 210, 226, 227, 243, 244, 260, 261, 277, 278, 294, 295, 311, 312, 328, 329, 348, 349, 365, 366, 382, ​​and 383. The spectral data for representative formulations (salts) are shown below. Ingredients (salt) 175 FT-IR (KBr): 3378 cm -1 , 2971 cm -1 , 1672 cm -1 , 1157 cm -1 , 904 cm -1 . 1 HNMR (D2O, 400 MHz): 1.75 - 1.85 (quin, 2H, γ - Aminobutyric acid, -CH2C H 2CH2-), 2.27 - 2.35 (t, 2H, γ - Aminobutyric acid, -C H 2NH2), 2.90 - 2.94 (t, 2H, γ - Aminobutyric acid, -C H 2COOH). 3.20 - 3.70 (m, 5H), 4.00 (s, 1H): (Gluconic acid, 13 CNMR (D2O, 100 MHz): 22.6 (γ - Aminobutyric acid, -CH2 C H2CH2-), 32.1 (γ - Aminobutyric acid, - C H2NH2), 38.9 (γ - Aminobutyric acid, - C H2COOH), 177.7 (gluconic acid, C OOH), 178.8 (γ - Aminobutyric acid, C OOH). 62.6, 70.8, 71.1, 72.2, 73.5 (Gluconic acid, HO C H2 C H(OH) C H(OH) C H(OH) C H(OH)COOH). Complex (salt) 243 FT - IR (KBr): 3385 cm -1 , 2958 cm -1 , 1684 cm -1 , 1162 cm -1 , 833 cm -1 . 1 HNMR (D2O, 400 MHz): 3.47 - 3.52 (qd, 2H, Ser, -C H2OH), 3.93 - 3.95 (t, 1H, Ser, -C H (NH2)COOH). 3.59 - 3.81 (m, 5H), 4.22 (s, 1H): (Gluconic acid, HOC H 2C H (OH)C H (OH)C H (OH)C H (OH)COOH). 13 CNMR (D2O, 100MHz): 56.0 (Ser, - C H2OH), 59.9 (Ser, - C H(NH2)COOH), 172.0 (Ser, C OOH), 176.4 (Gluconic acid, C OOH). 60.0, 62.5, 70.6, 71.0, 72.5 (Gluconic acid, HO C H2 C H(OH) C H(OH) C H(OH) C H(OH)COOH). Complex (salt) 348 FT - IR (KBr): 3404 cm -1 , 1685 cm -1 , 1156 cm -1 , 899 cm -1 . 1 HNMR (D2O, 400MHz): 3.53 - 3.68 (m, 4H), 4.00 - 4.06 (d, 2H), 4.22 (s, 1H): (Gluconic acid, HOC H 2C H (OH)C H (OH)C H (OH)C H (OH)COOH). 1.89 - 2.27 (m, 4H), 3.19 - 3.34 (m, 2H) 3.98 - 4.06 (t, 1H): (Pro, C H 2 hetero , CH hetero ). 13 CNMR (D2O, 100MHz): 174.4 (Pro, C OOH), 176.2 (Gluconic acid, C OOH). 62.6, 70.6, 70.8, 71.0, 72.5 (Gluconic acid, HO C H2 C H(OH) C H(OH) C H(OH) C H(OH)COOH). 23.6, 28.9, 46.0, 61.0: (Pro, C H 2 hetero , C H hetero ). Complex (salt) 349 FT-IR (KBr): 3404 cm -1 , 1685 cm -1 , 1156 cm -1 , 899 cm -1 . 1 HNMR (D2O, 400MHz): 1.22 - 1.24 (d, 3H, Lactic acid, -C H 3), 4.06 - 4.11 (q, 1H, Lactic acid, -C H OH-). 1.89 - 2.27 (m, 4H), 3.19 - 3.34 (m, 2H), 4.00 - 4.06 (t, 1H): (Pro, C H 2 hetero , C H hetero ). 13 CNMR (D2O, 100MHz): 19.7 (Lactic acid, - C H3), 67.6 (Lactic acid, - C HOH-),174.4 (Pro, C OOH), 180.9 (Lactic acid, C OOH). 23.6, 28.9, 46.0, 61.0: (Pro, C H 2 hetero , C H hetero ).

[0178] <Example 157> Composition (Salt) 157 L-alanine (8.91 g, 0.10 mol) and adipic acid (14.61 g, 0.10 mol) were stirred in 50 ml of water at room temperature for 1 hour, and then the water was removed by distillation under reduced pressure to obtain a white solid compound (salt) consisting of arginine and adipic acid. Ingredients (salt) 157 FT-IR (KBr): 3076 cm -1 , 2692 cm -1 , 1735 cm -1 , 1693 cm -1 , 1475 cm -1 , 1025 cm -1 . 1 HNMR (D2O, 400MHz): 1.35-1.37 (m, 4H, Adipic acid, -C H 2-), 1.50-1.53 ​​(d, 3H, Ala, -C H 3), 2.27-2.30 (m, 4H, Adipic acid, -C H 2COOH), 3.64-3.71 (q, 1H, Ala, -C H (NH2)COOH). 13 CNMR (D2O, 100MHz): 16.0 (Ala, - C H3), 23.7 (Adipic acid, - C H2-), 33.6 (Adipic acid, - C H2COOH), 50.4 (Ala, - C H(NH2)COOH), 175.6 (Ala, C OOH), 178.9 (Adipic acid, C (Out of the Home)

[0179] <Examples 137-139, 157-159, 177-179, 194-196, 211-213, 228-230, 245-247, 262-264, 279-281, 296-298, 313-315, 330-332, 350-352, 367-369, 384-386> Composition (Salt) 137-139, 157-159, 177-179, 194-196, 211-213, 228-230, 245-247, 262-264, 279-281, 296-298, 313-315, 330-332, 350-352, 367-369, 384-386 Similarly, using components (A) and (B) in the mixing ratios listed in Tables 1B and C, preparations were made under the same conditions as in Example 157, yielding formulations (salts) 137-139, 157-159, 177-179, 194-196, 211-213, 228-230, 245-247, 262-264, 279-281, 296-298, 313-315, 330-332, 350-352, 367-369, and 384-386.

[0180] <Example 160> Composition (Salt) 160 L-alanine (8.91 g, 0.10 mol) and fumaric acid (11.61 g, 0.10 mol) were stirred in 50 ml of water at room temperature for 1 hour, and then the water was removed by distillation under reduced pressure to obtain a white solid compound (salt) consisting of arginine and adipic acid. Ingredients (salt) 160 FT-IR (KBr): 3081 cm -1 , 1735 cm -1 , 1588 cm -1 , 1025 cm -1 , 658 cm -1 . 1 HNMR (D2O, 400MHz): 1.39-1.43 (d, 3H, Ala, -C H 3), 3.76-3.82 (q, 1H, Ala, C H (NH2)COOH), 6.71 (s, 2H, Fumaric acid, -C H =C H -). 13CNMR (D2O, 100MHz): 15.5 (Ala, - C H3), 50.3 (Ala, - C H(NH2)COOH), 134.6 (Fumaric acid, - C H= C H-), 169.7 (Fumaric acid, C OOH), 174.8 (Ala, C (Out of the Home)

[0181] <Examples 140, 160, 180, 197, 214, 231, 248, 265, 282, 299, 316, 333, 353, 370, 387> Composition (salt) 140, 160, 180, 197, 214, 231, 248, 265, 282, 299, 316, 333, 353, 370, 387 Similarly, using components (A) and (B) in the mixing ratios listed in Tables 1B and C, preparations were made under the same conditions as in Example 160, yielding formulations (salts) 140, 160, 180, 197, 214, 231, 248, 265, 282, 299, 316, 333, 353, 370, and 387.

[0182] <Example 182> Composition (Salt) 182 γ-aminobutyric acid (10.31 g, 0.10 mol) and citric acid (19.21 g, 0.10 mol) were stirred in 50 ml of water at room temperature for 3 hours, and then the water was removed by vacuum distillation to obtain a colorless liquid. By washing the obtained liquid, a compound (salt) consisting of the colorless liquid γ-aminobutyric acid and citric acid was obtained. Ingredients (salt) 182 FT-IR (KBr): 3441 cm -1 , 3207 cm -1 , 1708 cm -1 , 1213 cm -1 , 844 cm -1 . 1 HNMR (D2O, 400MHz): 1.72-1.85 (quin, 2H, γ-Aminobutyric acid, -CH2C H2CH2-), 2.32 - 2.36 (t, 2H, γ - Aminobutyric acid, -C H 2NH2), 2.63 - 2.66 (d, 2H, Citric acid, -C H 2COOH), 2.77 - 2.80 (d, 2H, Citric acid, -C H 2COOH), 2.89 - 2.92 (t, 2H, γ - Aminobutyric acid, -C H 2COOH). 13 CNMR (D2O, 100MHz): 22.2 (γ - Aminobutyric acid, -CH2 C H2CH2-), 31.2 (γ - Aminobutyric acid, - C H2NH2), 38.8 (γ - Aminobutyric acid, - C H2COOH), 43.5 (Citric acid, - C H2COOH), 73.7 (Citric acid, - C (OH)COOH), 174.4 (Citric acid, -CH2 C OOH), 177.7 (γ - Aminobutyric acid, C OOH), 178.3 (Citric acid, -C(OH)( C OOH)-).

[0183] <Examples 141 - 143, 161 - 163, 181 - 183, 198 - 200, 215 - 217, 232 - 234, 249 - 251, 266 - 268, 283 - 285, 300 - 302, 317 - 319, 334 - 336, 354 - 256, 371 - 373, 388 - 390> Complexes (salts) 141 - 143, 161 - 163, 181 - 183, 198 - 200, 215 - 217, 232 - 234, 249 - 251, 266 - 268, 283 - 285, 300 - 302, 317 - 319, 334 - 336, 354 - 256, 371 - 373, 388 - 390 Similarly, using components (A) and (B) in the mixing ratios listed in Tables 1B and C, preparations were made under the same conditions as in Example 182, yielding formulations (salts) 141-143, 161-163, 181-183, 198-200, 215-217, 232-234, 249-251, 266-268, 283-285, 300-302, 317-319, 334-336, 354-256, 371-373, and 388-390. The spectral data for representative formulations (salts) are shown below. Ingredients (salt) 142 FT-IR (KBr): 3450 cm -1 , 3171 cm -1 , 1713 cm -1 , 1215 cm -1 , 950 cm -1 . 1 HNMR (D2O, 400MHz): 2.66-2.70 (d, 2H, Citric acid, -C H 2COOH), 2.82-2.86 (d, 2H, Citric acid, -C H 2COOH), 3.52 (s, 2H, Gly, C H 2(NH2)COOH). 13 CNMR (D2O, 100MHz): 40.9 (Gly, C H2(NH2)COOH), 43.3 (Citric acid, - C H2COOH), 73.4 (Citric acid, - C (OH)COOH), 171.5 (Gly, CH2(NH2) C OOH), 173.7 (Citric acid, -CH2 C OOH), 177.3 (Citric acid, -C(OH)( C OOH)-). Ingredients (salt) 249 FT-IR (KBr): 3423 cm -1 , 3228 cm -1 , 1715 cm -1 , 1236 cm -1 , 854 cm-1 . 1 HNMR (D2O, 400 MHz): 2.68 - 2.81 (qd, 2H, Ser, -C H 2OH), 3.78 - 3.80 (t, 1H, Ser, -C H (NH2)COOH), 3.85 - 3.86 (d, 2H, Malic acid, -C H 2COOH), 4.43 - 4.46 (t, 1H, Malic acid, -C H (OH)COOH). 13 CNMR (D2O, 100 MHz): 38.6 (Malic acid, - C H2COOH), 56.0 (Ser, - C H2OH), 59.9 (Ser, - C H(NH2)COOH), 67.0 (Malic acid, - C H(OH)COOH), 171.8 (Ser, C OOH), 174.7 (Malic acid, CH2 C OOH), 177.0 (Malic acid, -CH(OH) C OOH). Complex (salt) 250 FT-IR (KBr): 3477 cm -1 , 3211 cm -1 , 1717 cm -1 , 1217 cm -1 , 845 cm -1 . 1 HNMR (D2O, 400 MHz): 2.71 - 2.74 (d, 2H, Citric acid, -C H 2COOH), 2.87 - 2.91 (d, 2H, Citric acid, -C H 2COOH), 3.82 - 3.83 (t, 1H, Ser, -C H (NH2)COOH), 3.66 - 3.80 (d, 2H, Ser, -C H 2OH). 13 CNMR (D2O, 100MHz): 43.3 (Citric acid, - C H2COOH), 55.8 (Ser, - C H2OH), 59.9 (Ser, - C H(NH2)COOH), 73.4 (Citric acid, - C (OH)(COOH)-), 171.7 (Ser, C OOH), 173.4 (Citric acid, - C H2COOH), 177.2 (Citric acid, -C(OH)( C OOH)-). Complex (salt) 354 FT-IR (KBr): 3424 cm -1 , 3203 cm -1 , 1775 cm -1 , 1126 cm -1 , 807 cm -1 . 1 HNMR (D2O, 400MHz): 2.68 - 2.82 (m, 2H, Malic acid, -C H 2COOH), 4.43 - 4.46 (t, 1H, Malic acid, -C H (OH)COOH). 1.87 - 2.28 (m, 4H), 3.18 - 3.31 (m, 2H), 4.03 - 4.07 (t, 1H): (Pro, C H 2 hetero , C H hetero ). 13 CNMR (D2O, 100MHz): 38.6 (Malic acid, - C H2-), 67.0 (Malic acid, - C HOH-), 174.1(Malic acid, -CH2 C OOH), 174.6 (Pro, C OOH), 176.8 (Malic acid, -CH(OH) C OOH). 23.6, 28.9, 46.0, 61.0: (Pro, C H 2 hetero , C H hetero ). Complex (salt) 355 FT-IR (KBr): 3449 cm -1 , 3203 cm -1 , 1716 cm -1 , 1218 cm -1 , 845 cm -1 . 1 HNMR (D2O, 400MHz): 2.71 - 2.75 (d, 2H, Citric acid, -C H 2COOH), 2.88 - 2.92 (d, 2H, Citric acid, -C H 2COOH). 1.86 - 2.29 (m, 4H), 3.19 - 3.34 (m, 2H), 4.05 - 4.09 (t, 1H): (Pro, C H 2 hetero , C H hetero ). 13 CNMR (D2O, 100MHz): 43.3 (Citric acid, - C H2-), 73.4 (Citric acid, - C (OH)(COOH)-), 173.6 (Citric acid, -CH2 C OOH), 174.0 (Pro, C OOH), 177.1(Citric acid, -C(OH)( C OOH)-). 23.6, 28.9, 46.0, 61.0: (Pro, C H 2 hetero , C H hetero ).

[0184] <Example 184> Complex (salt) 184 γ-aminobutyric acid (10.31 g, 0.10 mol) and benzoic acid (12.12 g, 0.10 mol) were stirred in 50 ml of water at room temperature for 3 hours, and then the water was removed by distillation under reduced pressure to obtain a white solid compound (salt) consisting of γ-aminobutyric acid and benzoic acid. Ingredients (salt) 184 FT-IR (KBr): 2953 cm -1 , 1752 cm -1 , 1518 cm -1 , 1388 cm -1 , 1282 cm -1 . 1 HNMR (D2O, 400MHz): 1.76-1.83 (quin, 2H, γ-Aminobutyric acid, -CH2C H 2CH2-), 2.23-2.27 (t, 2H, γ-Aminobutyric acid, -C H 2NH2), 2.89-2.93 (d, 2H, citric acid, -C H 2COOH), 7.37-7.41 (d, 2H, Benzoic acid, Ph), 7.47-7.50 (t, 1H, Benzoic acid, Ph), 7.81-7.83 (t, 2H, Benzoic acid, Ph). 13 CNMR (D2O, 100MHz): 23.1 (γ-Aminobutyric acid, -CH2 C H2CH2-), 33.2 (γ-Aminobutyric acid, - C H2NH2), 39.1 (γ-Aminobutyric acid, - C H2COOH), 128.9, 129.1, 131.8, 134.1 (Benzoic acid, Ph), 174.2 (γ-Aminobutyric acid, C OOH), 180.2 (Benzoic acid, C (Out of the Home)

[0185] <Examples 144, 164, 184, 201, 218, 235, 252, 269, 286, 303, 320, 337, 357, 374, 391> Composition (salt) 144, 164, 184, 201, 218, 235, 252, 269, 286, 303, 320, 337, 357, 374, 391 Similarly, using components (A) and (B) in the mixing ratios listed in Tables 1B and 1C, preparations were made under the same conditions as in Example 184, yielding formulations (salts) 144, 164, 184, 201, 218, 235, 252, 269, 286, 303, 320, 337, 357, 374, and 391.

[0186] <Example 165> Composition (Salt) 165 L-alanine (8.91 g, 0.10 mol) and L-ascorbic acid (17.61 g, 0.10 mol) were stirred in 50 ml of water at room temperature for 1 hour, and then the water was removed by distillation under reduced pressure to obtain a white solid compound (salt) consisting of L-alanine and L-ascorbic acid. Ingredients (salt) 165 FT-IR (KBr): 3157 cm -1 , 1791 cm -1 , 1591 cm -1 , 1110 cm -1 . 1 HNMR (D2O, 400MHz): 1.37-1.39 (d, 3H, Ala, -C H 3), 3.95-3.99 (q, 1H, Ala, -C H (NH2)COOH). 3.64-3.74 (m, 3H), 4.81 (s, 1H): (Ascorbic acid, C H arom , -C H (OH)C H 2OH). 13 CNMR (D2O, 100MHz): 15.6 (Ala, -C H 3), 50.5 (Ala, - C H(NH2)COOH), 175.4 (Ala, C (Out of the Home) 62.3, 68.5, 76.1, 117.2, 157.8, 173.8: (Ascorbic acid, C H cyclo , - C H(OH) C H2OH.

[0187] <Examples 145, 146, 165, 166, 185, 186, 202, 203, 219, 220, 236, 237, 253, 254, 270, 271, 287, 288, 304, 305, 321, 322, 338, 339, 358, 359, 375, 376, 392, 393> Composition (Salt) 145, 146, 165, 166, 185, 186, 202, 203, 219, 220, 236, 237, 253, 254, 270, 271, 287, 288, 304, 305, 321, 322, 338, 339, 358, 359, 375, 376, 392, 393 Similarly, using components (A) and (B) in the mixing ratios listed in Tables 1B and C, preparations were made under the same conditions as in Example 165 to obtain formulations (salts) 145, 146, 165, 166, 185, 186, 202, 203, 219, 220, 236, 237, 253, 254, 270, 271, 287, 288, 304, 305, 321, 322, 338, 339, 358, 359, 375, 376, 392, and 393.

[0188] <Example 414> Composition (Salt) 414 L-glutamic acid (14.71 g, 0.10 mol) and hexanoic acid (11.61 g, 0.10 mol) were stirred in 50 ml of water at room temperature for 1 hour, and then the water was removed by distillation under reduced pressure to obtain a white solid compound (salt) consisting of L-glutamic acid and hexanoic acid. Ingredients (salt) 414 FT-IR (KBr): 3197 cm -1 , 1685 cm -1 , 1509 cm -1 , 1271 cm -1 , 817 cm -1 . 1HNMR (D2O, 400MHz): 0.75-0.78 (t, 3H, Hexanoic acid, -C H 3), 1.18-1.22 (m, 4H, Hexanoic acid, -C H 2-), 1.48-1.52 (m, 2H, Hexanioc acid, -C H 2-), 2.01-2.08 (m, 2H, Glu, -C H 2-), 2.25-2.29 (t, 2H, Hexanoic acid, -C H 2COOH), 2.44-2.48 (m, 2H, Glu, -C H 2COOH), 3.69-3.72 (t, 1H, Glu, -C H (NH2)COOH). 13 CNMR (D2O, 100MHz): 21.6 (Hexanoic acid), 24.0 (Hexanoic acid), 25.5 (Glu, - C H2-), 29.9 (Glu, - C H2COOH), 31.1, 33.8, (Hexanoic acid), 54.0 (Glu, C H(NH2)COOH), 173.7 (Glu, -CH(NH2) C OOH), 177.0 (Glu, C OOH), 179.5 (Hexanoic acid, C (Out of the Home)

[0189] <Examples 394-398, 411-415> Composition (salt) 394-398, 411-415 Similarly, using components (A) and (B) in the mixing ratios listed in Table 1D, preparations were made under the same conditions as in Example 414 to obtain formulations (salts) 394-398 and 411-415.

[0190] <Example 416> Composition (Salt) 416 L-glutamic acid (14.71 g, 0.10 mol) and 50% by mass gluconic acid (38.32 g, 0.10 mol) were stirred in 50 ml of water at room temperature for 1 hour, and then the water was removed by distillation under reduced pressure to obtain a white solid compound (salt) consisting of L-glutamic acid and gluconic acid. Ingredients (salt) 416 FT-IR (KBr): 3411 cm -1 , 3065 cm -1 , 1734 cm -1 , 1514 cm -1 , 1353 cm -1 , 1127 cm -1 . 1 HNMR (D2O, 400MHz): 2.01-2.14 (m, 2H, Glu, -C H 2-), 2.47-2.52 (m, 2H, Glu, -C H 2COOH), 3.69-3.80 (t, 1H, Glu, -C H (NH2)COOH). 3.53-3.68 (m, 4H), 4.03-4.05 (d, 1H), 4.31-4.34 (s, 1H): (Gluconic acid, HOC H 2C H (OH)C H (OH)C H (OH)C H (OH)COOH). 13 CNMR (D2O, 100MHz): 25.4 (Glu, - C H2-), 29.8 (Glu, - C H2COOH), 53.7 (Glu, C H(NH2)COOH), 173.6 (Glu, CH(NH2) C OOH), 176.3 (Gluconic acid, C OOH), 176.9 (Glu, C (Out of the Home) 62.3, 70.6, 71.0, 72.5, 79.6 (Gluconic acid, HO C H2 CH(OH) C H(OH) C H(OH) C H(OH)COOH).

[0191] <Examples 399, 400, 416, 417> Composition (salt) 399, 400, 416, 417 Similarly, using components (A) and (B) in the mixing ratios listed in Table 1D, preparations were made under the same conditions as in Example 416 to obtain formulations (salts) 399, 400, 416, and 417.

[0192] <Example 418> Composition (Salt) 418 L-glutamic acid (14.71 g, 0.10 mol) and adipic acid (14.61 g, 0.10 mol) were stirred in 50 ml of water at room temperature for 1 hour, and then the water was removed by distillation under reduced pressure to obtain a white solid compound (salt) consisting of L-glutamic acid and adipic acid. Ingredients (salt) 418 FT-IR (KBr): 3031 cm -1 , 2951 cm -1 , 1756 cm -1 , 1692 cm -1 , 1508 cm -1 , 1256 cm -1 . 1 HNMR (D2O, 400MHz): 1.47-1.50 (m, 4H, Adipic acid, -C H 2-), 1.97-2.11 (m, 2H, Glu, -C H 2-), 2.27-2.31 (t, 4H, Adipic acid, -C H 2COOH), 2.42-2.47 (m, 2H, Glu, -C H 2COOH), 3.68-3.72 (t, 1H, Glu, -C H (NH2)COOH). 13 CNMR (D2O, 100MHz): 23.6 (Adipic acid, - C H2-), 25.5 (Glu, - CH2-), 29.9 (Glu, C H2COOH), 33.4 (Adipic acid, - C H2COOH), 53.8 (Glu, - C H(NH2)COOH), 173.7 (Glu, -CH(NH2) C OOH), 177.0 (Glu, C OOH), 178.7 (Adipic acid, C (Out of the Home)

[0193] <Examples 401-403, 418-420> Composition (salt) 401-403, 418-420 Similarly, using components (A) and (B) in the mixing ratios listed in Table 1D, preparations were made under the same conditions as in Example 418 to obtain formulations (salts) 401-403 and 418-420.

[0194] <Example 421> Composition (Salt) 421 L-glutamic acid (14.71 g, 0.10 mol) and fumaric acid (11.61 g, 0.10 mol) were stirred in 50 ml of water at room temperature for 1 hour, and then the water was removed by distillation under reduced pressure to obtain a white solid compound (salt) consisting of L-glutamic acid and fumaric acid. Ingredients (salt) 421 FT-IR (KBr): 3040 cm -1 , 1748 cm -1 , 1510 cm -1 , 1444 cm -1 , 727 cm -1 . 1 HNMR (D2O, 400MHz): 1.98-2.12 (m, 2H, Glu, -C H 2-), 2.44-2.49 (m, 2H, Glu, -C H 2COOH), 3.73-3.77 (t, 1H, Glu, -C H (NH2)COOH), 6.69 (s, 2H, Fumaric acid, -C H =C H -). 13CNMR (D2O, 100MHz): 25.3 (Glu, - C H2-), 29.7 (Glu, - C H2COOH), 53.5 (Glu, - C H(NH2)COOH), 134.2 (Fumaric acid, - C H= C H-), 169.6 (Fumaric acid, C OOH), 173.4 (Glu, - C H(NH2)COOH), 176.7 (Glu, C (Out of the Home)

[0195] <Examples 404, 421> Formulation (salt) 404, 421 Similarly, using components (A) and (B) in the mixing ratios listed in Table 1D, preparations were made under the same conditions as in Example 421 to obtain formulations (salts) 404 and 421.

[0196] <Example 422> Composition (Salt) 422 L-glutamic acid (14.71 g, 0.10 mol) and L-malic acid (13.41 g, 0.10 mol) were stirred in 50 ml of water at room temperature for 1 hour, and then the water was removed by distillation under reduced pressure to obtain a white solid compound (salt) consisting of L-glutamic acid and L-malic acid. Ingredients (salt) 422 FT-IR (KBr): 3041 cm -1 , 1722 cm -1 , 1511 cm -1 , 1257 cm -1 , 1102 cm -1 . 1 HNMR (D2O, 400MHz): 2.10-2.16 (m, 2H, Glu, -C H 2-), 2.48-2.52 (m, 2H, Glu, -C H 2COOH), 2.72-2.86 (m, 2H, Malic acid, -C H 2COOH), 3.77-3.80 (t, 1H, Glu, -C H(NH2)COOH), 4.47-4.50 (t, 1H, Malic acid, -C H (OH)COOH). 13 CNMR (D2O, 100MHz): 25.3 (Glu, - C H2-), 29.8 (Glu, - C H2COOH), 38.7 (Malic acid, - C H2COOH), 53.9 (Glu, - C H(NH2)COOH), 67.1 (Malic acid, - C H(OH)COOH), 173.4 (Glu, -CH(NH2) C OOH), 174.7 (Malic acid -CH2 C OOH), 176.6 (Glu, C OOH), 176.9 (Malic acid, -CH(OH) C (Out of the Home)

[0197] <Examples 405-407, 422-424> Composition (salt) 405-407, 422-424 Similarly, using components (A) and (B) in the mixing ratios listed in Table 1D, preparations were made under the same conditions as in Example 422 to obtain formulations (salts) 405-407 and 422-424.

[0198] <Example 425> Composition (Salt) 425 L-glutamic acid (14.71 g, 0.10 mol) and benzoic acid (12.12 g, 0.10 mol) were stirred in 50 ml of water at room temperature for 1 hour, and then the water was removed by distillation under reduced pressure to obtain a white solid compound (salt) consisting of L-glutamic acid and benzoic acid. Ingredients (salt) 425 FT-IR (KBr): 3030 cm -1 , 1637cm -1 , 1509 cm -1 , 1258 cm -1 . 1HNMR (D2O, 400MHz): 2.04-2.14 (m, 2H, Glu, -C H 2-), 2.47-2.51 (m, 2H, Glu, -C H 2COOH), 3.72-3.75 (t, 1H, Glu, -C H (NH2)COOH), 7.46-7.50 (t, 2H, Benzoic acid, Ph), 7.60-7.62 (t, 1H, Benzoic acid, Ph), 7.95-7.97 (d, 2H, Benzoic acid, Ph). 13 CNMR (D2O, 100MHz): 25.5 (Glu, - C H2-), 30.1 (Glu, - C H2COOH), 53.6 (Glu, - C H(NH2)COOH), 128.1, 128.9, 129.5, 129.7 (Benzoic acid, Ph), 173.8 (Glu, -CH(NH2) C OOH), 175.6 (Benzoic acid, C OOH), 177.1 (Glu, C (Out of the Home)

[0199] <Examples 408, 425> Composition (salt) 408, 425 Similarly, using components (A) and (B) in the mixing ratios listed in Table 1D, preparations were made under the same conditions as in Example 425 to obtain formulations (salts) 408 and 425.

[0200] <Example 426> Composition (Salt) 426 L-glutamic acid (14.71 g, 0.10 mol) and L-ascorbic acid (17.61 g, 0.10 mol) were stirred in 50 ml of water at room temperature for 1 hour, and then the water was removed by distillation under reduced pressure to obtain a white solid compound (salt) consisting of L-glutamic acid and L-ascorbic acid. Ingredients (salt) 426 FT-IR (KBr): 3055 cm -1 , 1805 cm -1, 1509 cm -1 , 1268 cm -1 , 815 cm -1 . 1 HNMR (D2O, 400MHz): 1.96-2.10 (m, 2H, Glu, -C H 2-), 2.42-2.47 (m, 2H, Glu, -C H 2COOH), 3.72-3.75(m, 1H, Glu, -C H (NH2)COOH). 3.62-3.97 (m, 3H), 4.82 (s, 1H): (Ascorbic acid, C H cyclo , -C H (OH)C H 2OH). 13 CNMR (D2O, 100MHz): 25.4 (Glu, - C H2-), 29.9 (Glu, - C H2COOH), 53.7 (Glu, - C H(NH2)COOH), 173.7 (Glu, -CH(NH2) C OOH), 176.9 (Glu, C (Out of the Home) 62.0, 68.9, 76.3, 117.4, 173.6: (Ascorbic acid, C H cyclo , - C H(OH) C H2OH.

[0201] <Examples 409, 410, 426, 427> Formulation (organic salt) 409, 410, 426, 427 Similarly, using components (A) and (B) in the mixing ratios listed in Table 1D, preparations were made under the same conditions as in Example 426 to obtain formulations (organic salts) 409, 410, 426, and 427.

[0202] 2. Appearance of the compound (organic salt) Formulas 1 to 427 shown in Tables 1A to 1D were prepared using the above method with components (A) and (B) shown in the table in the molar ratios shown in the table, and their condition at 25°C was confirmed.

[0203] [Table 1A-1]

[0204] [Table 1A-2]

[0205] [Table 1A-3]

[0206] [Table 1B-1]

[0207] [Table 1B-2]

[0208] [Table 1B-3]

[0209] [Table 1C-1]

[0210] [Table 1C-2]

[0211] [Table 1C-3]

[0212] [Table 1D]

[0213] Based on the results in Tables 1A to 1D, it was confirmed that Examples 9, 16, 30, 37, 48-52, 57-60, 69-73, 78-80, 93, 100, 114, 115, 121, 142, 173, 175, 176, 182, 243, 249, 250, 345-349, 354, and 355 become liquid at 25°C.

[0214] This suggests that the combination of A to O in the above specification is likely to result in a liquid.

[0215] 3. Water retention evaluation 80% by mass aqueous solutions of the formulations (organic salts) from Examples 428-459 and Comparative Examples 1-5 in Tables 2A and 2B were prepared, and the moisture content was confirmed to be 20.0% by mass using a Karl Fischer moisture meter (CA-200, Mitsubishi Chemical Analytec Co., Ltd.) (moisture content before test: A). 1.0 g of each sample was added to a screw-top tube and left uncovered for 24 hours in a constant temperature and humidity chamber (KCL-2000W, Tokyo Rikakikai Co., Ltd.) set to 35°C and 25% RH. The moisture content was measured again after 24 hours (moisture content after test: B), and the water retention rate was calculated using the following formula to evaluate the water retention. Furthermore, the solution was left to stand until no further change in moisture content occurred, and the hydrate was identified and the number of waters of hydration determined from the final moisture content. Pre-test moisture content: A (%) Post-test moisture content: B (%) Moisture reduction rate (%)=[(A(%)-B(%)) / A(%)]×100

[0216] [Table 2A]

[0217] [Table 2B]

[0218] The results in Tables 2A and 2B show that, in an 80% by mass aqueous solution, the formulations (organic salts) of Examples 428 to 459 exhibited a smaller water loss rate and superior water retention compared to Comparative Examples 1 to 5.

[0219] When comparing Examples 433, 439, and 446, which use the same formulation (organic salt) with component (B) lactic acid, with Comparative Example 1, the formulations (organic salt) of the examples showed higher water retention, confirming the superiority of component (A).

[0220] By comparing the formulations (organic salts) of Examples 428-431, which have the same formulation (organic salt) with component (A) L-lysine, with Comparative Example 2, the superiority of having a carboxylic acid as component (B) was confirmed.

[0221] In comparison with Comparative Example 5, which is a general water-retaining agent, Examples 428 to 459 were found to have superior water-retaining properties, suggesting that the combination of components (A) and (B) contributes to water retention.

[0222] Furthermore, in comparison with comparative examples 3 and 4 of the salt structure, Examples 428 to 459 were confirmed to have excellent water retention properties, suggesting that components (A) and (B) are useful for water retention as a combination that can form a salt structure.

[0223] In a comparison of formulations containing amino acids with an isoelectric point greater than 7 and a common component (B), it was confirmed that amino acids with an isoelectric point greater than 7 (Examples 428, 429, 432, 435, 443, 444, 450, 452) and amino acids with an isoelectric point between 4 and 7 (Examples 449, 453, 455, 456, 459) exhibit superior water retention. Among amino acids with an isoelectric point above 7, those containing two or more nitrogen atoms were suggested to exhibit superior water retention properties.

[0224] Furthermore, when L-lysine was used as the common component (A), a comparison between the formulations (organic salts) of Examples 428-431 and the formulation (organic salt) of Example 448 confirmed the superiority of component (B) being a carboxylic acid that retains hydrogen bonding functional groups (hydroxyl groups and / or carboxyl groups). In addition, when an amino acid with an isoelectric point greater than 7 was used as the common component (A), a comparison between Examples 429, 431, 435, 441, 444, 447, and 452, where component (B) was citric acid, and Examples 428, 430, 432-434, 436-440, 442, 443, 445, 446, 450, and 451, where component (B) was a carboxylic acid other than citric acid, confirmed that citric acid, which is a hydroxytricarboxylic acid, exhibits superior water retention as component (B). This suggests that the formulation of the present invention is suitable as a water-retaining agent for use in cosmetics and the like, for example, because of its excellent water-retention properties.

[0225] 4. Evaluation of hygroscopic properties Examples 460-470 and Comparative Example 6 in Table 3 were completely dried in a vacuum dryer at 60°C for 18 hours, and then left to stand at room temperature for one month. The moisture content was measured using a Karl Fischer moisture meter (CA-200, manufactured by Mitsubishi Chemical Analytec Co., Ltd.) to evaluate their hygroscopicity.

[0226] [Table 3] As shown in Table 3, Examples 460-470 had a higher moisture content in the saturated state and superior hygroscopic properties compared to Comparative Example 6.

[0227] When Comparative Example 6 was compared with the formulations (organic salts) of Examples 460, 462, 465, 467, and 469, which have the same formulation (organic salt) with component (B) being oleic acid, it was confirmed that the advantage of having an amino acid as component (A) is that it is suitable as a hygroscopic agent.

[0228] Among these, when comparing component (A) with component (B) (amino acids with an isoelectric point greater than 7: Examples 460, 462, 465, 467 and amino acids with an isoelectric point between 4 and 7: Example 469, amino acids with an isoelectric point greater than 7: Examples 461, 464 and amino acids with an isoelectric point between 4 and 7: Example 468, amino acids with an isoelectric point greater than 7: Examples 463, 466 and amino acids with an isoelectric point between 4 and 7: Example 470), amino acids with an isoelectric point greater than 7 exhibited superior hygroscopic properties. Furthermore, among amino acids with an isoelectric point greater than 7, L-arginine was confirmed to be particularly superior.

[0229] This suggests that a formulation containing an amino acid with an isoelectric point greater than 7 as component (A) exhibits excellent hygroscopic properties. Because the formulation of the present invention exhibits excellent hygroscopic properties, it is suggested that it is suitable as a hygroscopic agent used, for example, in cosmetics.

[0230] 5. Sensory Evaluation 1 Each formulation (organic salt) described in Examples 471-502 and Comparative Examples 7-9 in Tables 4A and 4B was diluted to a concentration of 20% by mass, placed in a spray bottle, and a fixed amount was sprayed onto the skin. The ease of application, moisturizing effect, and non-stickiness were evaluated. Five individuals of any age or gender were randomly selected as the panel, and the average value was calculated and used as the evaluation value.

[0231] Regarding the ease of spreading after application, aqueous solutions of each compound (organic salt) were applied and evaluated on a 5-point scale based on the feel on the skin when spreading them. A score of 5 indicated that it was very easy to spread, a score of 3 indicated that it was easy to spread, and a score of 1 indicated that it was not easy to spread.

[0232] Regarding the moisturizing effect after application, aqueous solutions of each compound (organic salt) were applied and spread on the skin, and evaluated on a 5-point scale based on the feel. A score of 5 indicated a strong moisturizing effect, a score of 3 indicated a moisturizing effect, and a score of 1 indicated no moisturizing effect.

[0233] Regarding the non-stickiness after application, aqueous solutions of each compound (organic salt) were applied and spread, and evaluated on a 5-point scale based on the feel on the skin. A score of 5 indicated no stickiness, a score of 3 indicated slight stickiness, and a score of 1 indicated sticky.

[0234] [Table 4A]

[0235] [Table 4B]

[0236] Tables 4A and 4B show that Examples 471 to 502, which used the formulation (organic salt) of the present invention, were found to be superior to Comparative Examples 7 to 9 in terms of ease of application, moisturizing effect, and non-stickiness.

[0237] When comparing Comparative Example 7 with the same formulations (organic salts) in Examples 476, 482, 489, 494, and 500, where component (B) is lactic acid, the superiority of having an amino acid as component (A) was confirmed.

[0238] Furthermore, comparing the formulations (organic salts) of Examples 471-474, where component (A) is L-lysine, with Comparative Example 8, the formulation with carboxylic acid as component (B) showed a better user experience.

[0239] Furthermore, the structural advantages of the formulations (organic salts) of Examples 471 to 502, which consist of a component (A) having a cationic residue and a component (B) having an anionic residue, were confirmed when compared with Comparative Example 9, which is used as a general water-retaining agent.

[0240] Furthermore, by comparing the formulations (organic salts) of Examples 471-474 and Example 491, where component (A) is L-lysine, we confirmed the advantage of component (B) being a carboxylic acid that retains hydrogen-bonding functional groups (hydroxyl groups and / or carboxyl groups).

[0241] Furthermore, the formulations of Examples 472, 474, 477, 478, 483, 484, 487, 490, 492, 495, 497, 498, 501, and 502, which consist of an amino acid with an isoelectric point greater than 7 and an amino acid with an isoelectric point between 4 and 7 as component (A), and L-malic acid and citric acid as component (B), provided a good user experience. This suggests that the formulation of the present invention has excellent usability when applied to the skin and is suitable as a cosmetic or the like.

[0242] 6. Sensory Evaluation 2 For each formulation (organic salt) described in Examples 503-514 and Comparative Examples 10 and 11 in Table 5, the formulation (organic salt) obtained in Section 4, Hygroscopicity Evaluation (after being left standing at room temperature for one month), was used as the evaluation sample. The evaluation concentration was calculated from the moisture content obtained in the above test. As an evaluation method, a fixed amount of the evaluation sample was applied to the skin, and the ease of application, refreshing feeling, and non-stickiness were evaluated. Five people of any age or gender were randomly selected as the panel, and the average value was calculated and used as the evaluation value.

[0243] Regarding the ease of spreading after application, the evaluation sample was applied and rated on a 5-point scale based on the feel on the skin when spreading it. A score of 5 indicated that it was very easy to spread, a score of 3 indicated that it was easy to spread, and a score of 1 indicated that it was not easy to spread.

[0244] Regarding the refreshing feeling after application, the evaluation sample was applied and spread, and the feel on the skin was evaluated on a 5-point scale. A rating of 5 indicated a very refreshing feeling, 3 indicated a refreshing feeling, and 1 indicated no refreshing feeling.

[0245] Regarding the non-stickiness after application, the evaluation was conducted on a 5-point scale based on the feel on the skin after applying and spreading the sample. A score of 5 indicated no stickiness, a score of 3 indicated slight stickiness, and a score of 1 indicated sticky.

[0246] [Table 5]

[0247] Table 5 shows that Examples 503 to 514, which use the formulation (organic salt) of the present invention, were found to be superior to Comparative Example 10 and Example 11, which is commonly used as an oily base material for cosmetics, in terms of ease of application, refreshing feel, and non-stickiness.

[0248] When comparing Comparative Example 10 with the same formulations (organic salts) of Examples 503, 505, 508, 511, and 513, where component (B) is oleic acid, the superiority of having an amino acid as component (A) was confirmed.

[0249] Furthermore, the formulations in Examples 507, 508, and 512-514, in particular, exhibited a good user experience. In addition, a comparison between Example 504 and Example 507, and between Example 505 and Example 508, showed that formulations of components (A) and (B) with a molar ratio of 1:2 exhibited superior user experience. This suggests that the formulation (organic salt) of the present invention has excellent feel when applied to the skin and is suitable as a cosmetic. 7. Adhesion to hair 1

[0250] 80% by mass aqueous solutions were prepared for Examples 515-544 and Comparative Examples 12-16 in Tables 6A and 6B, and the moisture content was confirmed to be 20.0% by mass using a Karl Fischer moisture meter (KF-200, Mitsubishi Chemical Analytec). Healthy hair was provided as untreated, healthy hair (black human hair, manufactured by Beaulux Co., Ltd.).

[0251] 0.05 g of hair (pre-test hair weight A) was immersed for 60 minutes in 3.0 g of 80% by mass aqueous solutions of Examples 515-544 and Comparative Examples 12-16, respectively. After immersion, the hair was removed, the formulation (organic salt) was wiped off with a Kimwipe until there was no change in weight, and the weight was measured (post-test hair weight B).

[0252] The adhesion rate of the compound (organic salt) to the hair was calculated using the following formula. Adhesion rate of compound (organic salt) (%) = [(Hair weight B (g) after testing - Hair weight A (g) before testing) / Hair weight A (g) before testing] × 100

[0253] [Table 6A]

[0254] [Table 6B] The results in Tables 6A and 6B show that the formulations (organic salts) of Examples 515 to 544 exhibited superior adhesion to healthy hair compared to Comparative Examples 12 to 16.

[0255] When comparing Comparative Example 12 with the same formulations (organic salts) in Examples 518, 524, 531, 536, and 542, where component (B) is lactic acid, the superiority of having an amino acid as component (A) was confirmed.

[0256] By comparing the formulations (organic salts) of Examples 515 and 516, which have the same composition (organic salt) with component (A) L-lysine, with Comparative Example 13, the superiority of having a carboxylic acid as component (B) was confirmed.

[0257] In comparison with Comparative Example 16, Examples 515-544 were found to have excellent adhesion to hair, suggesting that the combination of components (A) and (B) contributes to their adhesion to hair.

[0258] Furthermore, in comparison with comparative examples 14 and 15 of the salt structure, Examples 515 to 544 were confirmed to have excellent adhesion to hair, suggesting that components (A) and (B) are useful for hair adhesion as a combination that can form a salt structure.

[0259] Furthermore, by comparing the formulations (organic salts) of Examples 515 and 516, which have the same composition (organic salt) with component (A) L-lysine, with the formulation (organic salt) of Example 533, we confirmed the superiority of component (B) being a carboxylic acid having hydrogen-bonding functional groups (hydroxyl group and / or carboxyl group).

[0260] Furthermore, a comparison of formulations (organic salt) Example 517 and Example 518, and formulations (organic salt) Example 523 and Example 524, all of which contain L-arginine as component (A), suggests the advantage of component (B) being a carboxylic acid that retains multiple hydroxyl groups in its hydrocarbon portion.

[0261] When comparing the same formulation (organic salt) with component (A) L-arginine in Examples 518-520 and 524-526, the superiority of citric acid, which retains multiple carboxyl groups in component (B), was suggested.

[0262] This suggests that formulations (organic salts) containing functional groups (such as hydroxyl groups and carboxyl groups) that interact with the hydrogen-bonding functional groups of proteins on the hair surface exhibit superior adhesion.

[0263] 8. Adhesion to hair 2 For Examples 545-555 and Comparative Examples 17 and 18 in Table 7, the adhesion was evaluated using the formulations (organic salts) prepared according to "4. Hygroscopicity Evaluation" in the same manner as in "Adhesion to Hair 1".

[0264] [Table 7]

[0265] As shown in Table 7, the formulations (organic salts) of Examples 545 to 555 exhibited superior adhesion to healthy hair compared to Comparative Example 17 and Comparative Example 18, which is commonly used as an oily base material for cosmetics.

[0266] When comparing Comparative Example 17 with the same formulations (organic salts) of Examples 545, 547, 550, and 552, where component (B) is oleic acid, the superiority of having an amino acid as component (A) was confirmed.

[0267] 9. Antibacterial The following reagents were used for measuring the minimum inhibitory concentration (MIC) and performing the halo test. Staphylococcus aureus NBRC15035 strain: NITE Escherichia coli NBRC 15035 strain:NITE Potassium lactate: Manufactured by Fujifilm Wako Pure Chemical Industries. Culture medium: Muller-Hinton broth, manufactured by Becton, Dickinson and Company. Culture medium L - Dried product regeneration medium "Daigo": Manufactured by Fujifilm Wako Pure Chemical Industries. Calcium chloride: Manufactured by Fujifilm Wako Pure Chemical Industries. Magnesium chloride: Manufactured by Fujifilm Wako Pure Chemical Industries. Skim milk: Manufactured by Snow Brand Megmilk Meat extract: Manufactured by Solabia Biokar Diagnostics Peptone: Manufactured by Solabia Biokar Diagnostics Sodium chloride: Manufactured by Fujifilm Wako Pure Chemical Industries. Agar: Manufactured by Fujifilm Wako Pure Chemical Industries.

[0268] 9-1. Antimicrobial activity evaluation of compound (organic salt) 1 (minimum inhibitory concentration) The minimum inhibitory concentrations (MICs) for Staphylococcus aureus and Escherichia coli in Examples 556-583 and Comparative Example 19, shown in Tables 8A and 8B, were measured using the microdilution method (as described in the Japanese Society of Chemotherapy Standards) to confirm the antibacterial activity of each formulation (organic salt). The MICs for formulation (organic salt) concentrations of 250, 200, 150, 100, 50, 25, 12.5, 8, 4, 2, 0.8, 0.4, 0.2, 0.1, and 0.05 mg / mL were evaluated, and the MICs are shown in Tables 8A and 8B.

[0269] [Table 8A]

[0270] [Table 8B]

[0271] Based on the results in Tables 8A and 8B, Examples 556-583 showed greater antibacterial activity than Comparative Example 19, with MICs ranging from 2 mg / mL to 50 mg / mL.

[0272] When comparing Comparative Example 19 with the same formulations (organic salts) in Examples 564, 570, 573, and 579, where component (B) is lactic acid, the superiority of having an amino acid as component (A) was confirmed.

[0273] Furthermore, when comparing the same formulation (organic salt) with component (B) being citric acid in Examples 556, 558, 560, 566, 568, 571, 572, 574, 577, and 581, it was confirmed that component (A) tends to exhibit superior antibacterial properties when using amino acids with an isoelectric point between 4 and 7 rather than amino acids with an isoelectric point greater than 7.

[0274] Focusing on the ratio of the total number of amino groups to the total number of carboxyl groups in components (A) and (B) (total number of amino groups / total number of carboxyl groups) (Tables 8A and 8B), it was confirmed that formulations with this value of 1 or less exhibit superior antibacterial properties.

[0275] 9-2. Antimicrobial activity evaluation of compound (organic salt) 2 (Halo test 1) A halo test was performed using Staphylococcus aureus, following JIS L1902. A 21φ mm / mm Kiriyama funnel filter paper (manufactured by Kiriyama Seisakusho) was used as the test specimen. The filter paper was placed on a culture medium containing bacterial cells, and 100 μL of aqueous solutions of the formulations (organic salts) at the concentrations listed in Table 9 (Examples 584, 585, Comparative Examples 20, 21) was dropped onto it. The cells were then cultured, and the presence or absence of a halo was visually confirmed. Table 9 shows the results of the halo test.

[0276] 9-3. Evaluation of Adhesion and Antimicrobial Properties of Compounds (Organic Salts) 3 (Halo Test 2) 9-3-1. Adhesion Evaluation 100 μL of aqueous solutions of the formulations (organic salts) at the concentrations listed in Table 9 (Examples 584-585) were dropped onto 21 mm diameter Kiriyama funnel filter paper and vacuum-dried at 60°C for 8 hours. The adhesion rate of the sample was calculated from the weight change of the filter paper (Table 9). As a blank test, the weight change before and after the procedure when 100 μL of water was dropped onto the filter paper and vacuum-dried was measured and used as a correction value. A: Weight of attached sample = Weight of filter paper after drying (mg) - Weight of filter paper before testing (mg) + Correction value (1.15 mg) B: Weight of the applied sample = Weight of 100 μL of aqueous solution (mg) × Concentration (mass%) / 100 Adhesion rate (%)=100×A / B 9-3-2. Harrow Test 2

[0277] A halo test was performed using Staphylococcus aureus, following JIS L1902, by dropping an aqueous solution of the formulation described in 9-3-1 onto filter paper, followed by vacuum drying at 60°C for 8 hours. After the test, the presence or absence of a halo was visually confirmed, and the presence or absence of a halo is shown in Table 9.

[0278] [Table 9]

[0279] Halo Test 1 showed that ethanol, which is widely known for its bactericidal and antibacterial effects, could not exhibit its antibacterial effect because it evaporated during culture, and no halo was observed. On the other hand, a halo was observed with the formulation of the example. This suggests that the formulation of the present invention, being non-volatile, can remain attached to the filter paper without volatilizing and can exhibit its antibacterial effect for a long period of time.

[0280] In Halo Test 2, ethanol evaporated and did not adhere to the filter paper, whereas the formulation in the example, which has hydrogen-bonding functional groups, adhered well to the filter paper which also has hydrogen-bonding functional groups. It was confirmed that it remained non-volatile and maintained its antibacterial properties for a long period even after heating and vacuum drying.

[0281] 9-4. Evaluation of solubility and stability of formulations with respect to poorly soluble substances Antimicrobial compositions were prepared by dissolving 1.0, 0.5, and 0.25% by mass of 4-methylparaben (manufactured by Tokyo Chemical Industry Co., Ltd., hereinafter referred to as "paraben"), a poorly water-soluble antimicrobial agent, in 20% by mass aqueous solutions of the formulations (organic salts) shown in Table 10 (Examples 586-596, Comparative Examples 22-26) at 80°C. The compositions were then left to stand at 25°C for 24 hours under sealed conditions, and the appearance of each antimicrobial composition was visually inspected. Solubility was evaluated according to the following criteria. (Table 10) ◎: 1.0 mass% or more, no crystal precipitation. ○: 0.5% by mass or more and less than 1.0% by mass; no crystal precipitation. △: 0.25% by mass or more and less than 0.5% by mass - No crystal precipitation. ×: Less than 0.25 mass%, no crystal precipitation.

[0282] The same procedure was performed on polyoxyethylene alkyl ethers (hereinafter referred to as AEs), antiviral substances whose effectiveness against viruses has been recognized, and their solubility was evaluated according to the above criteria. Pelletex 2465 manufactured by Miyoshi Oil & Fat Co., Ltd. was used as the AE. (Table 10)

[0283] [Table 10]

[0284] The formulation (organic salt) of the present invention dissolves poorly water-soluble antibacterial agents and other antiviral substances well, and it was confirmed that a stable solution was obtained without crystal precipitation even after standing at 25°C for 24 hours. Therefore, it is suggested that the formulation of the present invention can be used to impart antibacterial or antiviral properties by the addition of antibacterial agents, etc., to obtain an antibacterial composition.

[0285] When comparing the formulation (organic salt) of Example 590, in which component (B) is lactic acid, with that of Comparative Example 22, it was confirmed that using amino acids as component (A) tended to result in higher solubility of parabens.

[0286] Furthermore, by comparing the formulations (organic salts) of Examples 594-596, which have the same composition (organic salt) with component (A) L-proline, with Comparative Example 23, the superiority of having a carboxylic acid as component (B) was confirmed.

[0287] Furthermore, in comparison with comparative examples 24-26 of the salt structure, it was confirmed that Examples 586-596 exhibited excellent solubility of sparingly soluble substances, suggesting that components (A) and (B) are useful for dissolving sparingly soluble substances as a combination capable of forming a salt structure.

[0288] 9-5. Evaluation of antibacterial activity of antibacterial compositions (minimum inhibitory concentration) Antimicrobial compositions (Examples 597-612) prepared to contain equal amounts of the components (A) and (B) shown in Table 11, along with parabens (paraben concentration 1.0 mg / mL, concentration for Examples 597-612 1.0 mg / mL, total 2.0 mg / mL), Comparative Example 27 containing only water and parabens (paraben concentration 1.0 mg / mL), and Reference Example 1 containing L-lysine and citric acid (concentration 1.0 mg / mL) were evaluated for antimicrobial activity by the presence or absence of bacterial growth using the same test method as described in 9-1. above.

[0289] [Table 11]

[0290] While the parabens or formulations (organic salts) alone in Comparative Example 27 and Reference Example 1, which contained 1 mg / mL of paraben, did not exhibit antibacterial properties, Examples 597-612, which mixed 1 mg / mL each of parabens and formulations (organic salts) to create an antibacterial composition totaling 2 mg / mL, demonstrated antibacterial properties as a composition, as the antibacterial effect of the parabens was added to the antibacterial effect of the formulations (organic salts).

[0291] In other words, by adding other additives to the formulation (organic salt) of the present invention, the effects of those additives can be imparted to the composition containing the formulation (organic salt) of the present invention. For example, a composition obtained by adding (dissolving) the antiviral substance described in 9-4. is given antiviral properties in addition to antibacterial properties.

[0292] 9-6. Stability evaluation of antimicrobial compositions A 50% by mass aqueous solution of formulations 597-612, as well as a 0.25% by mass solution of parabens (additives) in water, were prepared and placed in open-top sample bottles, then left to stand at 50°C for 48 hours. The appearance of each antimicrobial composition was visually inspected.

[0293] In the case of water alone, the water evaporated and paraben crystals precipitated. On the other hand, in a 50% by mass aqueous solution of formulations 597-612, the liquid did not evaporate completely, and no crystal precipitation was observed. The composition of the present invention maintains the solubility of the additive due to the non-volatility of the formulation (organic salt) of the present invention, resulting in good stability and allowing the effects of the formulation (organic salt) and additives to be efficiently exerted over a long period of time. 10. Evaluation of skin irritation

[0294] The skin irritation tests for Examples 613-619 in Table 12 were conducted in accordance with the skin irritation test method (OECD TG439 method: in vitro skin irritation test) using the human 3D cultured epidermis LabCyte EPIMODEL24 manufactured by Japan Tissue Engineering Co., Ltd. (J-TEC). The measurement concentration was 50% by mass. Furthermore, the irritation was determined from the obtained spermatocyte percentage (%) according to the following criteria. Viable cell rate: ≦50% Irritation Viable cell rate:>50% non-irritating

[0295] [Table 12] The results in Table 12 indicate that the skin irritation tests for Examples 613-619 were non-irritating, suggesting that the formulations of the present invention are highly safe for the skin. Therefore, it was suggested that the formulation of the present invention is suitable for use in cosmetics and daily necessities because it is safe when applied to the skin.

[0296] 11. Biodegradability evaluation The biodegradability tests for Examples 620-623 in Table 13 were conducted in accordance with the OECD Test Guideline 301C method. General activated sludge was used as the microbial source for these tests. 300 ml of prepared standard test culture solution was mixed with the microbial source at a concentration of 30 mg / L and the test substance at a concentration of 100 mg / L. The tests were conducted at 25±1°C for 28 days, using aniline as the standard substance. The degradation rate was calculated by measuring the biochemical oxygen demand (BOD) using an Actac BOD sensor, and determining the degree of degradation from the calculated theoretical oxygen demand. Specifically, a BOD degradation rate of 60% or higher over 28 days was evaluated as ○ (easily degradable), and a BOD degradation rate of less than 60% was evaluated as × (not easily degradable).

[0297] [Table 13]

[0298] The results in Table 13 indicate that Examples 620-623 were easily biodegradable, suggesting that the formulations (organic salts) of the present invention have excellent biodegradability and low environmental impact.

[0299] 12. Preparation of the gel composition As high molecular weight compounds, xanthan gum (Echo Gum T: manufactured by DSP Gokyo Food & Chemical), carrageenan (CP Gum FA: manufactured by DSP Gokyo Food & Chemical), gellan gum (Kelco Gel: manufactured by San-Ei Gen F.F.I.), guar gum (SUPERGEL CSA 200 / 50: manufactured by Sansho), and dieutan gum (KELCO-VIS DG: manufactured by Sansho) were used. As amino acids for component (A), L-arginine, γ-aminobutyric acid, and L-serine were used, and as component (B), benzoic acid, citric acid, and L-malic acid were used.

[0300] Each composition was prepared using the method described below (Table 14). Furthermore, after mixing components (A) and (B) listed in Table 14 in water, the water was removed by distillation, and the resulting mixture or salt was a hydrate that was liquid at 25°C.

[0301] <Example 624> Composition 1 0.059 g of L-arginine (amine compound (component (A))), 0.041 g of benzoic acid (acid (component (B))) (molar ratio of component (A):component (B) = 1:1, concentration of (component (A) + component (B)) in the composition: 1% by mass), 0.1 g of xanthan gum (polymer compound concentration in the composition: 1% by mass), and 9.8 g of water were mixed, heated and stirred at 50°C for 30 minutes to dissolve, and then cooled to room temperature over 60 minutes to obtain gel-like composition 1.

[0302] <Examples 625-651> Compositions 2-28 Similarly, predetermined amounts of amino acids (component (A)), carboxylic acids (component (B)), and polymer compounds listed in Table 14 were prepared under the same conditions as in Example 624 to obtain gel-like compositions 2 to 28.

[0303] Furthermore, it was confirmed that a similar gel-like composition could be obtained by pre-mixing each amino acid (component (A)), acid (component (B)), and water described in Examples 625 to 651 in the same amounts as above, synthesizing an organic salt, then adding a polymer compound, and heating, stirring, dissolving, and cooling under the same conditions as in Example 624. From this, a thickening effect was observed.

[0304] [Table 14]

[0305] 13. Evaluation of the solubility of the active ingredient The solubility of the active ingredients in the formulations listed in Table 15 was evaluated. The active ingredients used were gallic acid, which has poorly soluble antioxidant properties, and glutamic acid, which has moisturizing properties. Comparative Example 28 (ion-exchanged water), in which glutamic acid was dissolved, had a solubility of <1.0g, while Examples 652-659 showed high solubility of ≥1.0g. A similar trend was observed for gallic acid. Formulations 182, 354, and 355 were particularly excellent in solubility of gallic acid, while formulations 100, 121, and 182 were particularly excellent in solubility of glutamic acid.

[0306] A comparison of Examples 653-659 and Example 652 showed that using hydroxycarboxylic acid as component (B) resulted in higher solubility.

[0307] A comparison of Examples 656 and 657 with Examples 658 and 659 showed that when gallic acid is dissolved, using L-proline instead of L-serine when using a hydroxycarboxylic acid as component (B) increases solubility. A comparison of Examples 655 and 659 with Example 657 showed that when citric acid is used as component (B), using L-proline and γ-aminobutyric acid instead of L-serine increases solubility.

[0308] A comparison of Examples 653-655 and Examples 657 and 659 showed that when dissolving glutamic acid, using γ-aminobutyric acid and L-histidine, which have an isoelectric point of 7.0 or higher, as component (A) increased solubility. Examples 653 and 654 showed that solubility was high regardless of the mixing ratio. These results suggest that the formulation of the present invention dissolves a larger amount of the active ingredient. Therefore, the formulation of the present invention can be used as a carrier, a base for formulations, or a solvent to penetrate poorly soluble active ingredients, which were previously difficult to formulate at high concentrations, into the hair and skin at high concentrations.

[0309] [Table 15]

[0310] 14. Evaluation of skin surface improvement The skin penetration tests for Examples 660-667 in Table 16 were evaluated by the following stratum corneum microscopy observations. Note that formulation 439 in Comparative Example 31 was prepared using the same preparation method as formulation (salt) 52.

[0311] For the evaluation method, 1.0% by mass aqueous solutions of Examples 660-667 and Comparative Examples 30 and 31 were used as sample solutions. In Comparative Example 29, water was used as the sample solution. A fixed amount of the obtained sample solution was applied to the inner upper arm of 10 subjects once a day for one month. After that, the stratum corneum was peeled off the inner upper arm of the 10 subjects, who had been resting for 30 minutes under constant temperature and humidity conditions, using cellophane tape (registered trademark) (manufactured by Nichiban Co., Ltd.). The cellophane tape with the stratum corneum attached was adhered to a glass slide that had been thinly coated with vinyl cement (manufactured by Cemedyne Co., Ltd.) with the stratum corneum side and resin side facing each other. This was immersed in ethanol for 10 minutes, then immersed in xylene for 2 hours, and after peeling only the tape from the glass slide with tweezers, it was immersed in xylene for another hour to evaporate the xylene on the removed glass slide. Subsequently, the samples were stained in a staining solution (0.5 wt% brilliant green, 1.0 wt% gentian violet) for 4 minutes, washed with running water, and dried to prepare specimens for observation. Based on the observation results of the specimens, the specimens were examined under an optical microscope (ZEISS Axio Image.A2m) and evaluated using the following criteria for four items to comprehensively assess the improvement of the skin surface.

[0312] 1: Degree of layer peeling Good: Compared to before application, the shedding of layers of keratinocytes has decreased. No change: There is no change in the layered exfoliation of keratinocytes compared to before application. Poor: Compared to before application, there is an increase in the shedding of layers of keratinocytes.

[0313] 2: Arrangement Regularity Good: The arrangement of keratinocytes is more organized compared to before application. No change: There is no change in the arrangement of keratinocytes compared to before application. Defect: The arrangement of keratinocytes is disorganized compared to before application.

[0314] 3: Area uniformity Good: Compared to before application, the surface area of ​​keratinocytes is more uniform. No change: There is no change in the uniformity of the surface area of ​​keratinocytes compared to before application. Poor: The surface area of ​​keratinocytes is not uniform compared to before application.

[0315] 4: Presence or absence of nucleated cells Good: The number of keratinocytes with nuclei has decreased compared to before application. No change: There is no change in keratinocytes with nuclei compared to before application. Poor: There is an increase in keratinocytes with nuclei compared to before application.

[0316] comprehensive evaluation ○: Skin surface condition has improved compared to before application. △: No change in skin surface condition compared to before application. ×: Skin surface condition has worsened compared to before application.

[0317] [Table 16]

[0318] As shown in Table 16, Examples 660-667 demonstrated a superior skin surface improvement effect compared to Comparative Examples 29-31. This result suggests that the skin surface improvement effect is superior to that of Comparative Example 30 (petrolatum), which is generally used to suppress skin dryness, and Comparative Example 31, which uses an organic base instead of an amino acid as component (A). This is presumed to be because the amino acids in the formulation are the main components of "NMF (Natural Moisturizing Factor)," a moisturizing component present in the stratum corneum. The formulation penetrates into the skin, replenishes the skin's NMF, promotes moisturizing, and as a result, improves the balance of the skin surface. NMF is a component that plays an important role in retaining moisture in the stratum corneum through hydrogen bonding with water in the skin. Therefore, it was suggested that the formulation of the present invention has a skin surface improvement effect.

[0319] 15. Evaluation of skin permeability The skin penetration tests for Examples 668-675 in Table 17 were evaluated using the following tape stripping method.

[0320] For the evaluation method, first, ascorbyl glucoside was added to 10% by mass aqueous solutions of Examples 668-675 and Comparative Example 32 to make a sample solution at a concentration of 5% by mass. For Comparative Example 33, ascorbyl glucoside was added to water to make a sample solution at a concentration of 5% by mass. Next, cotton impregnated with 750 μL of the prepared sample solution was applied to a 1 cm x 3 cm area on the inner side of the upper arm of five subjects who had been at rest for 30 minutes under constant temperature and humidity conditions, and left to stand for 5 minutes. After removing the cotton, any remaining sample on the skin surface was removed with a new cotton, and left to stand for 30 minutes. After that, the stratum corneum from the 1st to the 8th layer was collected from the application site using cellophane tape (registered trademark) (manufactured by Nichiban Co., Ltd.), and all layers of the obtained tape were used as specimens for measurement.

[0321] The obtained sample was extracted with 2 ml of deionized water for 10 minutes. The amount of ascorbyl glucoside (μg / cm³) was measured from the extract solution after removing impurities using a 0.2 μm syringe filter (ADVANTEC). 2 The osmotic volume (μg / cm³) was measured by HPLC. The results were obtained by averaging the measured values ​​of sample taken from 5 subjects. 2 The total amount of penetration from the 1st to the 8th layer was compared. Finally, the values ​​for Examples 668-675 and Comparative Examples 32 and 33, which were evaluated in this study, were compared and evaluated as the relative penetration rate.

[0322] The quantification of ascorbyl glucoside was performed using a high-performance liquid chromatograph (HPLC, Thermo Scientific Ultimate 3000) under the following conditions. Column: Trinity P1 (100 × 2.1 mm, 3 μm) Solvent: A: Water, B: Acetonitrile, C: 200 mM ammonium formate (pH=4) Mobile phase: B: 70%, C: 30% Detection: UV (270nm) Flow rate: 0.3 mL / min. Column temperature: 30℃ Syringe washing: 200 mM ammonium formate (pH=4) Injection: 10 μL

[0323] [Table 17]

[0324] As shown in Table 17, a comparison of Examples 668-675 and Comparative Examples 32 and 33 revealed that Examples 668-675 had a slower penetration rate than Comparative Examples 32 and 33. In particular, Examples 668-671 and 673-675 showed slow penetration rates, suggesting they are effective in cases where a slow-acting effect of the active ingredient is required, allowing the active ingredient to penetrate the skin slowly. On the other hand, Example 672 was similar to Comparative Examples 32 and 33, showing a fast penetration rate, suggesting it is effective in cases where a rapid effect of the active ingredient is required, allowing the active ingredient to penetrate the skin quickly. Furthermore, since the penetration rate of the formulation of the present invention differs depending on the combination of component (A) and component (B), it is presumed that it is useful as a material for controlling the penetration rate of the active ingredient.

[0325] 16. Sensory Evaluation 3 For each formulation described in Examples 676-687 and Comparative Examples 34 and 35 in Table 18, the formulation (organic salt) obtained in Section 4, Hygroscopicity Evaluation (after being left standing at room temperature for one month) was used as the evaluation sample. The evaluation concentration was calculated from the moisture content obtained in the above test. Furthermore, formulation 440 (dimethicone) was manufactured by Fujifilm Wako Pure Chemical Industries.

[0326] As part of the evaluation method, a fixed amount of the evaluation sample was applied to hair, and its spreadability during application and the manageability of the hair after application were evaluated. Five individuals of any age or gender were randomly selected for the panel, and the average value was calculated and used as the evaluation score.

[0327] Regarding ease of application, the evaluation sample was applied and spread, and evaluated on a 5-point scale based on the feel on the skin. A score of 5 indicated that it was very easy to spread, a score of 3 indicated that it was easy to spread, and a score of 1 indicated that it was not easy to spread.

[0328] Regarding hair manageability after application, the evaluation sample was applied, and the manageability of the hair after it had blended in was evaluated on a 5-point scale. A score of 5 indicated that the hair was well-managed, a score of 3 indicated that it was well-managed, and a score of 1 indicated that it was not well-managed.

[0329] [Table 18]

[0330] Table 18 shows that Examples 676-687 were superior to Comparative Examples 34 and 35 in terms of ease of application and manageability of hair after application. In particular, Examples 676, 678, 681, 684, and 686, which used oleic acid as component (B), showed excellent usability. Furthermore, since components (A) and (B) in Examples 676-687 are listed in the External Standards for Pharmaceuticals and are therefore suggested to be highly safe, it is inferred that the formulations of the present invention are suitable as hair treatment agents.

[0331] 17. Evaluation of hair surface improvement The hair surface improvement tests for Examples 688-731 in Tables 20A-C were conducted using the following evaluation method. The following formulations were prepared for formulations 441-445. Composition 441 (L-arginine): Manufactured by Fujifilm Wako Pure Chemical Corporation. Formula 442 was prepared using the same preparation method as Formula (salt) 52. Composition 443 (L-proline): Manufactured by Sigma-Aldrich Japan. Composition 444 (Lactic Acid): Manufactured by Kanto Chemical Co., Ltd.

[0332] As an evaluation method, first, as a bleaching procedure, 1 g of bleaching agent (Table 19) was applied to 1 g of untreated black hair bundle (10 cm, manufactured by Beaulux Co., Ltd.), left to stand for 30 minutes, and then thoroughly rinsed with 40°C warm water. This bleaching procedure was repeated 5 times to create damaged hair. Next, the formulations of Examples 688-731 and Comparative Examples 36-40 were dissolved in a 50% by mass ethanol aqueous solution to a concentration of 1% by mass to prepare samples. 1 g of the prepared damaged hair was immersed in the sample for 15 minutes, then rinsed with 40°C warm water for 30 seconds, towel-dried, and air-dried. The surface condition of the hair bundles before and after treatment was observed using a scanning electron microscope (SEM, Hitachi High-Technologies Corporation S-3400N), and the improvement effect on the hair surface was evaluated according to the following criteria.

[0333] ◎: No cuticle lifting at all ○: There is almost no cuticle lifting. △: The cuticle is partially lifted. ×: The cuticle is almost completely lifted.

[0334] [Table 19]

[0335] [Table 20A]

[0336] [Table 20B]

[0337] [Table 20C]

[0338] Tables 20A-C show that, comparing Examples 688-731 and Comparative Examples 36-39, cuticle lifting was suppressed in Examples 688-731, confirming an improvement in the hair surface. In particular, formulations 30, 58, 72, 100, and 114 were found to have superior hair surface improvement effects.

[0339] From the comparison of Examples 692-702, 721-727 with Comparative Example 36 (arginine), Examples 715-717, 729-731 with Comparative Example 38, and Examples 693, 699, 706, 710, 716 with Comparative Example 39, it became clear that the coexistence of component (A) and component (B) is more effective than component (A) alone or component (B) alone. From the comparison of Examples 692-702, 721-727 with Comparative Example 37, it became clear that the improvement effect on the hair surface is obtained when component (B) is an organic acid. From the comparison of Examples 692-702, 721-726 with Example 727, it became clear that the improvement effect on the hair surface is superior when the formulation is liquid.

[0340] In particular, Examples 690, 695, 698, 704, and 705 revealed that formulations in which component (A) is a basic amino acid and the ratio of the total number of primary or secondary amino groups in component (A) to the number of carboxyl groups in component (B) (total number of primary or secondary amino groups / number of carboxyl groups) is 1 or less exhibit superior hair surface improvement effects.

[0341] In other words, the formulation of the present invention exhibits excellent surface improvement effects when used in hair treatment agents, suggesting its high usefulness in hair treatment agents.

[0342] 18. Evaluation of the stabilization of hair and skin proteins (keratin) To 2 g of 10 wt% aqueous solutions of Examples 732-749, 1 g of powdered keratin (manufactured by Tokyo Chemical Industry Co., Ltd.) (pre-test keratin) was added and stirred at 25°C for 24 hours. After stirring, the solution was filtered, and the resulting powdered keratin was dried to obtain treated keratin (post-test keratin). For Comparative Example 41, the same procedure was performed with 2 g of water.

[0343] The resulting 0.3 g of treated keratin was left standing in a 130°C incubator for 7 days. After 7 days, the IR spectrum of the obtained keratin was measured, and the stabilizing effect of the hair treatment agent on the keratin structure was evaluated by measuring the absorption derived from the α-helix secondary structure of the amide.

[0344] When keratin powder before heating was measured by infrared radiation, it was found to have a concentration of 1654 cm², derived from the α-helix secondary structure of the amide. -1 Absorption was observed. Next, IR measurements were performed after a 130°C heating test, and the peaks derived from each amide and their intensity ratios with the reference peak (reference peak (derived from CN) 1086 cm) were observed. -1 , a peak of 1654 cm² originating from the α-helix secondary structure of the amide. -1 The intensity ratio (X) was calculated by reading the absorption intensity of the reference peak and the intensity of the amide-derived peak, and evaluating it as "reference peak intensity: amide-derived peak intensity = 1:X", and comparing it according to the following criteria.

[0345] ◎: 0.6 <X≦1.0 ○:0.3 <X≦0.6 △:0 <X≦0.3 ×:X=0

[0346] [Table 21]

[0347] The results in Table 21 show that in Comparative Example 41, the peak derived from the α-helix secondary structure of the amide disappeared, confirming that the water did not retain the α-helix secondary structure of keratin. On the other hand, in Examples 732-749, the peak derived from the α-helix secondary structure of the amide was observed, confirming that the water retained the α-helix secondary structure of keratin.

[0348] A comparison of Examples 734, 735, 737, and 738 with Examples 741, 746, and 747 showed that using L-arginine as component (A) was superior to using γ-aminobutyric acid and L-proline in stabilizing the α-helix secondary structure of keratin. A comparison of Examples 732, 734, 735, 736, and 738 with Examples 733, 736, 746, 747, and 743 confirmed that using aromatic carboxylic acids or unsaturated fatty acids as component (B) was superior to using saturated fatty acids in stabilizing the α-helix secondary structure of keratin. Furthermore, Examples 734, 735 and Examples 736, and 738 showed that when unsaturated fatty acids were used as component (B), the stabilizing effect of the α-helix secondary structure of keratin was superior regardless of the molar ratio.

[0349] A comparison of Example 741 and Example 742 showed that using an unsaturated fatty acid as component (B) was superior to using a hydroxycarboxylic acid in stabilizing the α-helix secondary structure of keratin.

[0350] A comparison of Examples 743 and 744 with Examples 748 and 749 showed that when a hydroxycarboxylic acid was used as component (B), L-serine was superior to L-proline in stabilizing the α-helix secondary structure of keratin.

[0351] A comparison of Examples 739, 742, 748 and Example 743 revealed that when citric acid was used as component (B), L-serine was superior to L-histidine, γ-aminobutyric acid, and L-proline in stabilizing the α-helix secondary structure of keratin. This result suggests that using an amino acid with an isoelectric point of 6.0 or less, or an amino acid containing a hydroxyl group, as component (A) is superior in stabilizing the α-helix secondary structure of keratin.

[0352] A comparison of Example 739 and Example 740 showed that when hydroxycarboxylic acid is used as component (B), a blending ratio in which the molar ratio is equal to the total number of primary or secondary amino groups is superior to a blending ratio in which the number of carboxyl groups is equal, resulting in a better stabilization effect on the α-helix secondary structure of keratin.

[0353] Thus, the formulation of the present invention has a keratin stabilizing effect, which allows for moisture retention and hydration of hair, maintenance of hair health and quality, suppression of hair damage caused by heat such as hair dryers, and furthermore, moisture retention and maintenance of the health of skin proteins such as keratin and nails.

[0354] 19. Evaluation of metal oxide dispersibility For Examples 750-756 and Comparative Example 41 (poly(oxyethylene) nonylphenyl ether: Pelletex 1225, manufactured by Miyoshi Oil & Fat Co., Ltd.) shown in Table 22, the dispersion state was visually confirmed after mixing 0.5 g of an 80% aqueous solution of each formulation with 0.5 g of zirconium(IV) oxide (manufactured by Fujifilm Wako Pure Chemical Industries, reagent grade, approximately 5-30 μm) in a rotary-orbit mixer (Sinky Co., Ltd., ARE-310) at 2000 rpm for 1 minute x 5 times.

[0355] [Table 22]

[0356] As shown in the results in Table 22, when comparing Examples 750-756 with Comparative Example 41, aggregation and precipitation of zirconium(IV) oxide were observed in Comparative Example 41. However, all of the formulations in the examples dispersed zirconium(IV) oxide well, and dispersions were obtained. In other words, it is thought that the formulation of the present invention, by utilizing the structural characteristics of being composed of cations with hydrogen-bonding functional groups (having hydrogen bond-donating and coordinating properties), has a high affinity for the oxygen atom of hydrogen-bond-accepting zirconium(IV) oxide, and thus dispersed zirconium(IV) oxide well. In short, the formulation of the present invention has excellent affinity for inorganic oxides and is suggested to be useful in fields that utilize dispersions of such materials, such as cosmetics, paints, inks, electronic components, and batteries.

Claims

1. A compound comprising the following ingredients (A) and (B). (A) Formula (I) below: 【Chemistry 1】 (In the formula, R 1 R represents a monovalent or divalent organic group having 1 to 22 carbon atoms. 2 Each independently represents a hydrogen atom or a monovalent or divalent organic group having 1 to 22 carbon atoms, R 3 R represents a divalent organic group with 1 to 22 carbon atoms, where l is 0 to 2, m is 0 to 2, and n is 0 or 1. 1 and R 2 These may combine to form a ring having 3 to 22 carbon atoms. X represents a hydrogen atom or a monovalent cation.) A basic amino acid or salt thereof is represented as such, where the ratio of the total number of primary or secondary amino groups to the number of carboxyl groups (total number of primary or secondary amino groups / number of carboxyl groups) is greater than 1, and the isoelectric point is greater than 7. (B) Saturated hydroxy monocarboxylic acids, saturated hydroxy di or tricarboxylic acids, HCOOH and CH 3 (CH 2 ) p A carboxylic acid or salt thereof selected from saturated aliphatic monocarboxylic acids selected from COOH (where p is an integer from 0 to 8), linear or branched unsaturated aliphatic carboxylic acids, saturated aliphatic dicarboxylic acids, unsaturated aliphatic dicarboxylic acids, aromatic carboxylic acids, hydroxyaromatic carboxylic acids, and cyclic lactones having a hydroxyl group.

2. The formulation according to claim 1, wherein component (A) is arginine and component (B) is a carboxylic acid selected from citric acid, lactic acid, tartaric acid, and malic acid.

3. The formulation according to claim 1, comprising an organic salt formed by a cation derived from component (A), which may have a cationic residue of component (B), and an anion derived from an anionic residue of component (B).

4. The formulation according to claim 1, wherein the mixture of components (A) and (B) or the organic salt of (A) and (B) is a liquid in its anhydrous and / or hydrate form at 25°C.

5. A composition comprising the compound according to any one of claims 1 to 4.

6. A gel composition comprising a polymer compound and water, as described in claim 5.

7. The gel composition according to claim 6, wherein the polymer compound is a polysaccharide.

8. The composition according to claim 5, used to impart water retention properties.

9. The composition according to claim 5, used to impart hygroscopic properties.

10. The composition according to claim 5, used to impart antibacterial properties.

11. The composition according to claim 5, for use in cosmetics.

12. The composition according to claim 5, used as a water-retaining / moisturizing agent, a solvent for dissolving biomaterials, a dispersion solvent, a storage solvent or culture medium, a thickener, a solvent for dissolving organic or inorganic materials, a dispersion solvent or surface treatment agent, cosmetics, fragrances, hygiene and cleaning products, pharmaceuticals, transdermal absorbents, civil engineering and construction materials, or antibacterial agents.

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