Classifications

• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
  • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
  • A61K8/04—Dispersions; Emulsions
  • A61K8/042—Gels
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
  • A61K8/34—Alcohols
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
  • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
  • A61K8/361—Carboxylic acids having more than seven carbon atoms in an unbroken chain; Salts or anhydrides thereof
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
  • A61K8/73—Polysaccharides
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
  • A61K8/73—Polysaccharides
  • A61K8/737—Galactomannans, e.g. guar; Derivatives thereof
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q19/00—Preparations for care of the skin
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q19/00—Preparations for care of the skin
  • A61Q19/007—Preparations for dry skin
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q5/00—Preparations for care of the hair
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
  • A61K2800/10—General cosmetic use
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
  • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
  • A61K2800/48—Thickener, Thickening system
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
  • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
  • A61K2800/59—Mixtures
  • A61K2800/592—Mixtures of compounds complementing their respective functions

Definitions

• the present invention relates to formulations using amino acids and carboxylic acids, organic salts, compositions containing them, and uses thereof.
• Formulations used in the fields of cosmetics and daily necessities have traditionally been required to be safe for the body and have a low environmental impact, and various studies have been conducted to achieve compatibility with functionality.
• hypochlorous acid water has problems such as poor long-term antibacterial properties due to poor storage stability and a decrease in effective chlorine concentration during use. For these reasons, there is a demand for an antibacterial agent that is excellent in safety, has a low impact on the human body, has low volatility, and has a long-lasting effect.
• cosmetics used for hair treatment, skin care, etc. contain ingredients intended for water retention and moisturizing effects.
• these ingredients sometimes worsen the feeling of use such as stickiness, and there has been a demand for a product that satisfies water retention and moisturizing properties and a feeling of use.
• the cuticle which covers the surface of the hair to prevent moisture from evaporating, gives luster to the hair, and is an important tissue for maintaining the health of the hair, easily peels off.
• the cuticle is peeled off, the hair becomes dry and, for example, loses its smoothness and becomes dry. Hair breakage is likely to occur. Therefore, in order to prevent troubles due to dryness of hair and to keep hair beautiful and healthy, it is important to retain water and moisture of hair.
• Patent Document 3 discloses organic ammonium salts such as imidazolium salts, pyrrolidinium salts, piperidinium salts, pyridinium salts, and phosphonium salts. Such organic ammonium salts have the property of retaining moisture, but have problems such as sufficient water retaining and moisturizing effects when applied to hair, safety, and the like.
• Patent Documents 4 and 5 The present applicant has proposed an organic salt (ionic liquid) having a hydrogen-bonding functional group in its cation or anion (Patent Documents 4 and 5). Application to skin care has not been specifically examined.
• Rough skin is known to be caused mainly by a decrease in moisture in the skin. For example, dry air in winter, skin washing, aging, reduction of skin secretions, etc. cause dry skin. If the skin is left in a dry state, the firmness and luster of the skin are reduced, and so-called rough skin tends to occur. In order to prevent rough skin, it is important to prevent a decrease in the moisture content of the stratum corneum and maintain normal skin functions. In order to maintain the moisture content of the stratum corneum, there have conventionally been known various skin care agents for the purpose of moisturizing the skin and imparting an appropriate amount of moisture to the skin.
• Patent Document 3 discloses organic ammonium salts such as imidazolium salts, pyrrolidinium salts, piperidinium salts, pyridinium salts, and phosphonium salts. Although such organic ammonium salts have the property of retaining moisture, they have problems such as sufficient water retaining and moisturizing effects and safety when applied to skin care applications.
• Patent Documents 4 and 5 The applicant has proposed an organic ammonium salt (ionic liquid) that is liquid at room temperature and has a hydrogen-bonding functional group in its cation or anion.
• the present invention has been made in view of the above circumstances, water retention, hygroscopicity, solubility in poorly soluble substances, antibacterial properties, low skin irritation, biodegradability, gel-forming (thickening effect ), the main object of the present invention is to provide novel formulations using amino acids and carboxylic acids, organic salts, and compositions containing them. Furthermore, another object of the present invention is to maintain the above effects for a long period of time without being volatile.
• the present invention provides the following blend of components (A) and (B).
• composition of the present invention contains the above formulation.
• formulations and compositions can be used in cosmetics to impart water retention, hygroscopicity, and/or antibacterial properties. Furthermore, it can be used as a gel composition containing a polymer compound and water.
• the novel formulation using the amino acid and carboxylic acid of the present invention and the composition containing it are water retentive, hygroscopic, soluble in poorly soluble substances, antibacterial, low skin irritation, biodegradable, and gel-forming. (thickening effect). Furthermore, it is excellent in maintaining the above effects for a long period of time without volatility.
• the term "formulation” includes blending components (A) and (B) until the final target formulation is prepared, and components (A) and (B) are used as starting materials.
• the formulation of the present invention may be a mixture consisting only of components (A) and (B) (including the case where they are salts), and components other than components (A) and (B) or their salts It may be a composition containing components, such as 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, an antiviral agent, or a cosmetic product. .
• the number of carbon atoms represents an integer.
• component (A) is an amino acid or a salt thereof.
• amino acids include compounds having an acidic carboxy group (--COOH) and a basic amino group (primary amino group, secondary amino group, tertiary amino group) in the molecule.
• Preferable typical examples include, for example, proteinogenic amino acids and in vivo free amino acids.
• amino acid salts include carboxylates in which at least one of the carboxy groups of amino acids is substituted with a cation (alkali metal cation, alkaline earth metal cation, ammonium cation, etc.).
• the component (A) is preferably represented by the following formula (I).
• R 1 represents a monovalent or divalent organic group having 1 to 22 carbon atoms
• R 2 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
• n represents 0 or 1.
• R 1 and R 2 together have 3 carbon atoms. to form a ring of 22.
• X represents a hydrogen atom or a monovalent cation.
• l is preferably 0 or 1
• m is preferably 1 or 2.
• R 1 and R 2 together to form a ring having 3 to 22 carbon atoms means that R 1 and R 2 are together in the unit of R 1 l NH m CR 2 to form R 1 , R 2 , It means that the total number of carbon atoms forming the ring of C is 3 to 22, preferably 4 to 10, and the ring contains nitrogen N.
• the ring has 1 to 22 carbon atoms, preferably 1 to 10 carbon atoms, more preferably 1 to 3 monovalent or divalent organic groups as substituents in addition to 3 to 22 carbon atoms forming the ring. may have.
• the organic group essentially contains a carbon atom and may additionally contain at least one selected from a hydrogen atom and a heteroatom.
• the heteroatom is not particularly limited, an oxygen atom, a nitrogen atom, a sulfur atom, a phosphorus atom, and a halogen atom are preferable, and an oxygen atom, a nitrogen atom, and a sulfur atom are more preferable.
• the atomic group contained in the organic group is not particularly limited, examples thereof include hydrocarbon groups, heterocyclic groups, and substituents described in the section [Substituents] below.
• a hydrocarbon group replaces a hydrogen atom of the hydrocarbon group, interrupts the hydrocarbon group, and/or is included at the base end of the hydrocarbon group. , or a group forming a condensed ring with an aromatic hydrocarbon group.
• the hydrocarbon group is not particularly limited.
• a hydrogen group and the like can be mentioned.
• it may be monovalent or polyvalent, and examples of monovalent saturated or unsaturated aliphatic hydrocarbon groups include, but are not limited to, linear or branched alkyl groups, alkenyl groups and alkynyl groups. etc.
• Alkyl groups include linear or branched chains, but are not particularly limited, and examples thereof include methyl, ethane-1-yl, propan-1-yl, 1-methylethan-1-yl, butane-1- yl group, butan-2-yl group, 2-methylpropan-1-yl group, 2-methylpropan-2-yl group, pentan-1-yl group, pentan-2-yl group, hexan-1-yl group , heptane-1-yl group, octan-1-yl group, 2-ethylhexan-1-yl group, 1,1,3,3-tetramethylbutan-1-yl group, nonan-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,
• Alkenyl groups include linear or branched chains, and are not particularly limited, but examples include vinyl, prop-1-en-1-yl, allyl, isopropenyl, but-1-en-1-yl. group, but-2-en-1-yl group, but-3-en-1-yl group, 2-methylprop-2-en-1-yl group, 1-methylprop-2-en-1-yl group, pent-1-en-1-yl group, pent-2-en-1-yl group, pent-3-en-1-yl group, pent-4-en-1-yl group, 3-methylbut-2- En-1-yl group, 3-methylbut-3-en-1-yl group, hex-1-en-1-yl group, hex-2-en-1-yl group, hex-3-en-1- yl group, hex-4-en-1-yl group, hex-5-en-1-yl group, 4-methylpent-3-en-1-yl group, 4-methylpent-3-en-1-yl group,
• Alkynyl groups include straight or branched chains, and are not particularly limited and include, but are not limited to, ethynyl, prop-1-yn-1-yl, prop-2-yn-1-yl, but-1-yn- 1-yl group, but-3-yn-1-yl group, 1-methylprop-2-yn-1-yl group, pent-1-yn-1-yl group, pent-4-yn-1-yl group , hex-1-yn-1-yl group, hex-5-yn-1-yl group, hept-1-yn-1-yl group, hept-6-yn-1-yl group, octa-1-yne -1-yl group, octa-7-yn-1-yl group, non-1-yn-1-yl group, non-8-yn-1-yl group, deca-1-yn-1-yl group, Dec-9-yn-1-yl group, undec-1-yn-1-y
• the saturated or unsaturated alicyclic hydrocarbon group is preferably a saturated alicyclic hydrocarbon group and is not particularly limited.
• monovalent groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclo Examples include a heptyl group, a cyclooctyl group, and groups containing alicyclic residues such as residues thereof.
• the aromatic hydrocarbon group is not particularly limited, but includes, for example, a phenyl group, a naphthyl group, an anthracenyl group, and groups containing aromatic ring residues such as residues thereof.
• a condensed ring may be formed together with the substituents described in [Substituent] below.
• Examples of monovalent aromatic hydrocarbon groups include, but are not limited to, phenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2,4-dimethylphenyl, 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-propyl phenyl group, 4-isopropylphenyl group, 4-butylphenyl group, 4-tert-butylphenyl group, benzyl group, ⁇ , ⁇ -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-pentylphen
• divalent hydrocarbon groups examples include groups obtained by removing one hydrogen atom from the above groups. [Substituent]
• substituents include, but are not limited to, hydrocarbon groups, oxygen-containing groups, nitrogen-containing groups, sulfur-containing groups, phosphorus-containing groups, and halogens. Substituents also include groups to which these substituents are bonded. Examples of the hydrocarbon group include those listed in the above [Hydrocarbon group].
• oxygen-containing groups include, but are not limited to, hydroxyl groups, alkoxy groups, acetoxy groups, acetyl groups, aldehyde groups, carboxyl groups, carboxylate groups, urea groups, urethane groups, amide groups, imide groups, ether groups, 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.
• nitrogen-containing groups include, but are not limited to, cyano groups, cyanato groups, isocyanate groups, nitro groups, nitroalkyl groups, amide groups, urea groups, urethane groups, imide groups, carbodiimide groups, azo groups, pyridine groups, guanidino group, imidazolyl group, indolyl group, primary amino group, secondary amino group, tertiary amino group, quaternary ammonium group, aminoalkyl group and the like.
• sulfur-containing groups include, but are not limited to, sulfuric acid group, sulfonyl group, sulfonic acid group, mercapto group, thioether group, thiocarbonyl group, thiourea group, thiocarboxy group, thiocarboxylate group, dithiocarboxy group, Dithiocarboxylate group, sulfate ester, thiophene group, thiazole group, thiol group, sulfo group, sulfide group, disulfide group, thioester group, thioamide group, thiocarbamate group, dithiocarbamate group and esters thereof.
• Examples of phosphorus-containing groups include, but are not limited to, phosphoric acid group, phosphorous acid group, phosphonic acid group, phosphinic acid group, phosphonous acid group, phosphinic acid group, pyrophosphate group, phosphate ester group, Examples include a phosphate group, a phosphonate group, a pyrophosphate group, and ester groups thereof.
• Halogen includes fluorine, chlorine, bromine and iodine.
• the organic groups represented by R 1 and R 2 include hydrocarbon groups which may have a substituent and whose hydrocarbon moiety may contain an oxygen atom.
• hydrocarbon group the contents described in the above [Hydrocarbon group] column are referred to.
• the hydrocarbon group is preferably an aliphatic hydrocarbon group, more preferably a saturated aliphatic hydrocarbon group (alkyl group).
• Alkyl groups may have, for example, 1 to 22, 1 to 10 or 1 to 5 carbon atoms and may be linear or branched.
• the hydrocarbon group may have a substituent, and the substituent is not particularly limited, but includes, for example, those described in the above [Substituent] column.
• substituents those having an oxygen-containing group, a nitrogen-containing group, or a sulfur-containing group are preferred.
• An imidazolyl group, an indolyl group, a mercapto group and a thioether group are preferred.
• the hydrocarbon moiety may contain an oxygen atom.
• the hydrocarbon moiety contains the oxygen-containing group described above, for example, an ether bond, a carbonyl group, a hydroxyl group, a carboxylate group, an ester bond, an amide bond, a urea Forms or contains a bond or a urethane bond. Therefore, in the present invention, "the hydrocarbon moiety contains an oxygen atom” means that the hydrocarbon moiety is interrupted by a group that may also contain a heteroatom such as a nitrogen atom as an atomic group containing an oxygen atom, or the group is It includes the case where it is included at the base end or where a hydrogen atom is substituted by the group.
• the organic group may have a hydrogen-bonding functional group, and the hydrogen-bonding functional group is not particularly limited. A hydrogen atom directly bonded to nitrogen and the like can be mentioned.
• examples of the organic group for R 3 include hydrocarbon groups which may have a substituent and whose hydrocarbon moiety may contain an oxygen atom.
• the hydrocarbon group is a divalent group obtained by removing one hydrogen atom from the above hydrocarbon group, with reference to the contents described in the above [Hydrocarbon group] column.
• the hydrocarbon group is preferably an aliphatic hydrocarbon group, more preferably a saturated aliphatic hydrocarbon group (alkylene group).
• the alkylene group may have, for example, 1 to 22, 1 to 10 or 1 to 5 carbon atoms and may be linear or branched.
• the hydrocarbon group may have a substituent, and the substituent is not particularly limited, but includes, for example, those described in the above [Substituent] column.
• Component (A) is preferably an amino acid in which X is a hydrogen atom in (I) above.
• Amino acids include compounds having one or more amino groups (primary amino group, secondary amino group, tertiary amino group) and one or more carboxy groups (-COOH) in one molecule. However, amide groups are not included in amino groups.
• amino acids include the following from the viewpoint of the number ratio of amino groups to carboxy groups and the isoelectric point (referred to as amino acids (a) to (f)).
• Amino acid (a) the ratio of the total number of primary or secondary amino groups to the number of carboxy groups contained in the component (A) (total number of primary or secondary amino groups/number of carboxy groups) is , greater than one.
• these amino acids include, but are not limited to, arginine, histidine, lysine, tryptophan, and the like.
• Amino acid (b) the ratio of the total number of primary or secondary amino groups to the number of carboxy groups contained in the component (A) (total number of primary or secondary amino groups/number of carboxy groups) is , 1.
• amino acids include, but are not limited to, leucine, isoleucine, phenylalanine, proline, valine, serine, alanine, threonine, glutamine, asparagine, aminobutyric acid, cysteine, glycine, methionine, and the like.
• Amino acid (c) the ratio of the total number of primary or secondary amino groups to the number of carboxy groups contained in the component (A) (total number of primary or secondary amino groups/number of carboxy groups) is , less than one.
• amino acids examples include, but are not limited to, glutamic acid, aspartic acid, and the like.
• Amino acid (d) The isoelectric point of component (A) is greater than 7.
• amino acids are not particularly limited, but include, for example, those classified as basic amino acids, arginine (10.76), histidine (7.59), lysine (9.75), aminobutyric acid (7 .85) and the like.
• the numbers in parentheses indicate the isoelectric point of each amino acid.
• Amino acid (e) The isoelectric point of the component (A) is 4 or more and 7 or less.
• amino acids are not particularly limited, but include, for example, 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), tyrosine (5.66) and the like.
• 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),
• Amino acid (f) The isoelectric point of the component (A) is less than 4.
• amino acids are not particularly limited, but include, for example, those classified as acidic amino acids, such as glutamic acid (3.22) and aspartic acid (2.77).
• 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.
• examples of preferred combinations of R 1 , R 2 and R 3 include the following.
• R 1 is an aliphatic hydrocarbon group
• R 2 is a hydrocarbon group which may contain an oxygen atom, a nitrogen atom, or a sulfur atom
• R 3 is an aliphatic hydrocarbon group.
• amino acids include, but are not limited to, arginine, histidine, lysine, glutamic acid, aspartic acid, leucine, phenylalanine, proline, valine, tryptophan, serine, isoleucine, alanine, threonine, glutamine, asparagine, aminobutyric acid, cysteine. , glycine, methionine, and the like.
• l is 0, m is 2, n is 0, and R 2 is a primary amino group or a hydrocarbon group having two or more nitrogen atoms.
• these amino acids include, but are not limited to, arginine, histidine, lysine, and the like.
• R 1 and R 2 are hydrocarbon group having a carboxy group.
• these amino acids include, but are not particularly limited to, glutamic acid, aspartic acid, and the like.
• R 1 and R 2 are hydrocarbon groups having at least one of a hydroxy group, an amido group, a secondary amino group, and a sulfur-containing group, or R 1 and R 2 are Together they form a ring.
• these amino acids include, but are not limited to, leucine, phenylalanine, proline, valine, tryptophan, serine, isoleucine, alanine, threonine, glutamine, asparagine, aminobutyric acid, cysteine, glycine, methionine, and the like.
• amino acid is not particularly limited, but includes, for example, those classified as amino acids having an isoelectric point of more than 7, 4 or more and 7 or less, or less than 4.
• the amino acid having an isoelectric point of 4 or more and 7 or less is not particularly limited. Examples include amino acids, amino acids having an aromatic group, ⁇ -, ⁇ -, ⁇ -, or ⁇ -amino acids.
• R 2 is a hydrogen atom or a linear or branched alkyl group having 1 to 10 carbon atoms, preferably 1 to 4 carbon atoms.
• l is preferably 0, or l is 1 and R 1 is preferably a linear or branched alkyl group having 1 to 3 carbon atoms.
• n is 0.
• Specific examples include glycine, alanine, valine, leucine, isoleucine, sarcosine and the like.
• R 2 is a linear or branched hydroxyalkyl group having 1 to 5, preferably 1 to 3 carbon atoms and 1 to 3, preferably 1, hydroxy group. is.
• l is preferably 0, or l is 1 and R 1 is a linear or branched alkyl group having 1 to 3 carbon atoms, and l is more preferably 0.
• n is 0. Specific examples include serine, threonine, and the like.
• Amino acids containing sulfur as R 2 include the following for R 2 .
• R 21 represents a methylene group
• R 22 represents a methyl group or --CH 2 CH(NH 2 )(COOH)
• a1 represents 1 to 5, preferably 1 to 3
• a2 represents 1 to 4, preferably 1 or 2.
• the arrangement order of a1 S and a2 R 22 is arbitrary.
• l is preferably 0, or l is 1 and R 1 is a linear or branched alkyl group having 1 to 3 carbon atoms, and l is more preferably 0. Moreover, it is preferable that n is 0. Specific examples include cysteine, methionine, cystathionine, and the like.
• Amino acids having an amide group as R 2 include the following for R 2 .
• R 23 represents a linear or branched alkylene group having 1 to 5 carbon atoms, preferably 1 or 2 carbon atoms.
• l is preferably 0, or l is 1 and R 1 is a linear or branched alkyl group having 1 to 3 carbon atoms and containing a secondary amino group, and l is 0. is more preferable. Moreover, it is preferable that n is 0. Specific examples include asparagine, glutamine, citrulline and the like.
• Amino acids having an imino group as R 2 include compounds in which N and R 1 together form a heterocyclic ring.
• R 1 represents an alkylene group having 3 or 4 carbon atoms which may have a hydroxy group and forms a pyrrolidine ring or a piperidine ring. Preferably, it forms a pyrrolidine ring. In this case l is preferably zero. Moreover, it is preferable that n is 0. Specific examples include proline, hydroxyproline, and the like.
• Amino acids having an aromatic group as R 2 include the following for R 2 .
• R 24 represents a linear or branched alkylene group having 1 to 5 carbon atoms, preferably 1 or 2
• R 25 represents an optionally substituted aromatic group having 6 to 10 carbon atoms. group hydrocarbon group or a heterocyclic group having 6 to 10 carbon atoms.
• R 25 preferably represents a phenyl group, a hydroxyphenyl group or an indole group.
• n 0.
• Specific examples include phenylalanine, tyrosine, tryptophan, 1-methylhistidine, 3-methylhistidine, anserine, carnosine and the like.
• ⁇ -, ⁇ -, ⁇ -, or ⁇ -amino acids include those in which R 3 is a linear or branched alkylene group having 1 to 4 carbon atoms.
• l is preferably 0, or l is 1 and R 1 is a linear or branched alkyl group having 1 to 3 carbon atoms, and l is more preferably 0.
• n is 1.
• Specific examples include ⁇ -alanine, ⁇ -aminoisobutyric acid, ⁇ -aminobutyric acid, ⁇ -aminocaproic acid and the like.
• amino acids having an isoelectric point of less than 4 include those in which R 2 is represented by the following formula.
• R 26 represents a divalent aliphatic hydrocarbon group having 1 to 10 carbon atoms.
• l is preferably 0, or l is 1 and R 1 is a linear or branched alkyl group having 1 to 3 carbon atoms, and l is more preferably 0. Moreover, it is preferable that n is 0. Specific examples include glutamic acid, aspartic acid, ⁇ -aminoadipic acid and the like.
• Amino acids having an isoelectric point of more than 7 include those in which R 2 is represented by the following formula.
• R 27 represents a linear or branched alkylene group having 1 to 10 carbon atoms which may have a hydroxy group
• l is preferably 0, or l is 1 and R 1 is a linear or branched alkyl group having 1 to 3 carbon atoms, and l is more preferably 0. Moreover, it is preferable that n is 0. Specific examples include arginine, lysine, histidine, 5-hydroxylysine, omitine and the like.
• component (B) is a carboxylic acid or a salt thereof.
• component (B) is a carboxylic acid.
• the carboxylic acid is an organic acid having at least one carboxy group (--COOH) in the molecule, and has an oxygen-containing group, a nitrogen-containing group, a sulfur-containing group, a phosphorus-containing group, a hydrocarbon group, and the like.
• carboxylic acid having a hydrocarbon group is preferred.
• the carboxylic acid having a hydrocarbon group includes, for example, a saturated or unsaturated aliphatic hydrocarbon group, a saturated or unsaturated alicyclic hydrocarbon group, an aromatic hydrocarbon group, etc., and combinations thereof.
• 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, carbonylcarboxylic acids, alkyl ether carboxylic acids, halogen carboxylic acids, etc. (the carbon atoms of the carboxylic acids listed below The number includes the carbon of the carboxy group.).
• the saturated aliphatic carboxylic acid is composed of a linear or branched saturated aliphatic hydrocarbon group and one or more carboxy groups, and preferably has 1 to 22 carbon atoms.
• saturated aliphatic carboxylic acids include saturated aliphatic monocarboxylic acids having one carboxy group and saturated aliphatic dicarboxylic acids having two carboxy groups.
• the saturated aliphatic monocarboxylic acid is composed of a linear or branched saturated aliphatic hydrocarbon group and one carboxy group, and preferably has 1 to 22 carbon atoms.
• saturated aliphatic monocarboxylic acids selected from HCOOH and CH 3 (CH 2 ) p COOH (where p is an integer of 0 to 8) and saturated aliphatic monocarboxylic acids having a branched chain are preferred.
• formic acid acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, enanthic acid, caprylic acid, pelargonic acid, capric acid, lauric acid, myristic acid, pentadecyl acid, palmitic acid , margaric acid, stearic acid, arachidic acid, henicosyl acid, behenic acid, isobutyric acid, 2-methylbutyric acid, isovaleric acid, 2-ethylhexanoic acid, isononanoic acid, isopalmitic acid, isostearic acid and the like.
• the saturated aliphatic dicarboxylic acid is composed of a linear or branched saturated aliphatic hydrocarbon group and two carboxy groups, and preferably has 2 to 22 carbon atoms.
• a saturated dicarboxylic acid represented by HOOC(CH 2 ) x COOH (where x is an integer of 0 to 4) is preferred.
• Specific examples include, but are not limited to, oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, and glutamic acid.
• the unsaturated aliphatic carboxylic acid is composed of a linear or branched unsaturated aliphatic hydrocarbon group and one or more carboxy groups, preferably having 3 to 22 carbon atoms.
• unsaturated aliphatic carboxylic acids include unsaturated aliphatic monocarboxylic acids having one carboxy group and unsaturated aliphatic dicarboxylic acids having two carboxy groups.
• the unsaturated aliphatic monocarboxylic acid is composed of a linear or branched unsaturated aliphatic hydrocarbon group and one carboxy group, and preferably has 1 to 22 carbon atoms.
• R 1 CH CH(CH 2 ) r COOH
• R 1 is a hydrogen atom or CH 3 (CH 2 ) q ⁇ (q is an integer of 0 to 7)
• r is an integer of 0 to 7
• Specific examples include, but are not limited to, acrylic acid, methacrylic acid, crotonic acid, palmitoleic acid, oleic acid, vaccenic acid, linoleic acid, linolenic acid, eleostearic acid, and arachidonic acid.
• the unsaturated aliphatic dicarboxylic acid is composed of a linear or branched unsaturated aliphatic hydrocarbon group and two carboxy groups, preferably having 1 to 4 carbon atoms. Specific examples include, but are not particularly limited to, maleic acid and fumaric acid.
• the saturated or unsaturated alicyclic carboxylic acid is composed 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.
• Saturated or unsaturated alicyclic carboxylic acids include saturated or unsaturated alicyclic monocarboxylic acids having one carboxy group and saturated or unsaturated alicyclic dicarboxylic acids having two carboxy groups. Examples of the saturated or unsaturated alicyclic monocarboxylic acid include, but are not particularly limited to, cyclohexanecarboxylic acid. Examples of the saturated or unsaturated alicyclic dicarboxylic acid include, but are not particularly limited to, cyclohexanedicarboxylic acid.
• the aromatic carboxylic acid is composed of a single ring or a plurality of aromatic rings and one or more carboxyl groups, and preferably has 6 to 20 carbon atoms. Among them, aromatic carboxylic acids having a benzene ring skeleton are preferred. Examples of aromatic carboxylic acids include aromatic monocarboxylic acids having one carboxy group and aromatic dicarboxylic acids having two carboxy groups. Examples of the aromatic monocarboxylic acid include, but are not limited to, benzoic acid, cinnamic acid, and the like. Examples of the aromatic dicarboxylic acid include, but are not limited to, phthalic acid, isophthalic acid, terephthalic acid, and the like.
• the saturated aliphatic hydroxycarboxylic acid is composed of a linear or branched saturated aliphatic hydrocarbon group, one or more carboxyl groups and one or more hydroxyl groups, and preferably has 2 to 24 carbon atoms. Among them, saturated aliphatic hydroxycarboxylic acids having 2 to 7 carbon atoms and having 1 to 5 hydroxyl groups are preferred. Examples of saturated aliphatic hydroxycarboxylic acids include saturated aliphatic hydroxymonocarboxylic acids having one carboxy group and saturated aliphatic hydroxydi- or tricarboxylic acids having two or three carboxy groups.
• the saturated aliphatic hydroxymonocarboxylic acid preferably has 2 to 20 carbon atoms, more preferably 2 to 7 carbon atoms.
• the number of hydroxyl groups is preferably 1-5.
• (R 2 ) 3 C(C(R 3 ) 2 ) s COOH (s is an integer of 1 to 4, and 3 R 2 and 2 ⁇ s R 3 are each independently a hydrogen atom or a hydroxyl group and the total number of hydroxyl groups is 1 to 5.) is preferred.
• 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, aldonic acid and the like.
• the saturated aliphatic hydroxy di- or tricarboxylic acid preferably has 4-22 carbon atoms.
• the number of hydroxyl groups is preferably 1-3.
• HOOCC(R 4 R 5 )C(R 6 R 7 )C(R 8 R 9 )COO ⁇ R 4 to R 9 each independently represents a hydrogen atom, a hydroxyl group, or a carboxy group, and the total number of hydroxyl groups is 1 to 2 and the total number of carboxyl groups is 2 to 1.
• Specific examples include, but are not particularly limited to, tartronic acid, malic acid, tartaric acid, citramaric acid, citric acid, isocitric acid, and the like.
• the unsaturated aliphatic hydroxycarboxylic acid is composed of a linear or branched saturated aliphatic hydrocarbon group, one or more carboxyl groups and one or more hydroxyl groups, preferably having 3-22 carbon atoms. Specific examples include, but are not particularly limited to, ricinoleic acid, ricinoleic acid, ricineraidic acid, and the like.
• a saturated or unsaturated alicyclic hydroxycarboxylic acid is composed of a saturated or unsaturated carbocyclic ring having no aromaticity, one or more carboxyl groups and one or more hydroxyl groups, and preferably has 4 to 20 carbon atoms. Among them, a saturated alicyclic hydroxycarboxylic acid having a 6-membered ring skeleton having 1 to 4 hydroxyl groups is preferred.
• hydroxycyclohexanecarboxylic acid hydroxycyclohexanecarboxylic acid, dihydroxycyclohexanecarboxylic acid, quinic acid (1,3,4,5-tetrahydroxycyclohexanecarboxylic acid), shikimic acid, glucuronic acid, galacturonic acid, mannurone acid, iduronic acid, guluronic acid and the like.
• a cyclic lactone having a hydroxyl group can also be preferably used, and specific examples thereof include, but are not limited to, ascorbic acid and erythorbic acid.
• the aromatic hydroxycarboxylic acid is composed of a single ring or a plurality of aromatic rings, one or more carboxyl groups and one or more hydroxyl groups, and preferably has 6 to 20 carbon atoms.
• aromatic carboxylic acids having a benzene ring skeleton having 1 to 3 hydroxyl groups are preferred.
• salicylic acid hydroxybenzoic acid, dihydroxybenzoic acid, trihydroxybenzoic acid, hydroxymethylbenzoic acid, vanillic acid, syringic acid, protocatechuic acid, gentisic acid, orselic acid, mandelic acid, benzilic acid, atrolactinic acid, phlorethic acid, coumaric acid, umberic acid, caffeic acid, ferulic acid, sinapinic acid and the like.
• the carbonylcarboxylic acid is a carboxylic acid having 3 to 22 carbon atoms and having a carbonyl group in the molecule, preferably a carbonylcarboxylic acid having 3 to 7 carbon atoms and having 1 to 2 carbonyl groups.
• a carbonylcarboxylic acid represented by CH 3 ((CH 2 ) p CO(CH 2 ) q )COO - (p and q are integers of 0 to 2) is preferred.
• pyruvic acid and the like can be mentioned, for example.
• the alkyl ether carboxylic acid is a carboxylic acid having 2 to 22 carbon atoms having an ether group in the molecule, including polyoxyalkylene alkyl ether carboxylic acid, and an alkyl having 2 to 12 carbon atoms having 1 to 2 ether groups.
• Carboxylic acids are preferred.
• alkyl ether carboxylic acids and polyoxyethylene alkyl ether carboxylic acids represented by CH 3 (CH 2 ) r O(CH 2 ) s COO - (r and s are integers of 0 to 4) are preferred. Specific examples include, but are not particularly limited to, methoxyacetic acid, ethoxyacetic acid, methoxybutyric acid, ethoxybutyric acid, and the like.
• halogen carboxylic acid a halogen carboxylic acid having 2 to 22 carbon atoms is preferable. Specifically, but not particularly limited, for example, trifluoroacetic acid, trichloroacetic acid, tribromoacetic acid, pentafluoropropionic acid, pentachloropropionic acid, pentabromopropionic acid, perfluorononanoic acid, perchlorononanoic acid, perbromonanoic acid, etc. and halogen-substituted halogen carboxylic acids.
• linear or branched saturated aliphatic monocarboxylic acids linear or branched unsaturated aliphatic carboxylic acids, saturated aliphatic dicarboxylic acids, unsaturated aliphatic dicarboxylic acids Acids, saturated hydroxy monocarboxylic acids, saturated hydroxy di- or tricarboxylic acids, aromatic carboxylic acids, hydroxy aromatic carboxylic acids, cyclic lactones having a hydroxyl group are preferred, and among them linear or branched saturated aliphatic monocarboxylic acids, Linear or branched unsaturated aliphatic carboxylic acids, saturated hydroxy monocarboxylic acids, saturated hydroxy di- or tricarboxylic acids, aromatic carboxylic acids, and hydroxyaromatic carboxylic acids are more preferred.
• component (B) is a carboxylic acid having a hydrogen-bonding functional group on the hydrocarbon moiety. That is, the carboxylic acid preferably has a hydrogen-bonding functional group in addition to one carboxy group (--COOH).
• the hydrogen-bonding functional group include, but are not particularly limited to, the above oxygen-containing groups, nitrogen-containing groups, sulfur-containing groups, phosphorus-containing groups, and the like. Among these, it is preferable to have an oxygen-containing group, and it is more preferable to have a hydroxyl group or a carboxyl group in terms of expressing the effects of the formulation or composition of the present invention.
• the hydrogen-bonding functional groups are hydroxyl groups and/or carboxy groups.
• the hydrogen-bonding functional group is a hydroxyl group. Preferably, it has both a hydroxyl group and a carboxy group as hydrogen-bonding functional groups.
• component (B) is an unsaturated or branched aliphatic carboxylic acid having 8 to 22 carbon atoms.
• the formulation of the present invention contains organic salts of components (A) and (B).
• 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 the anionic residue of component (B).
• the residue in the component (B) refers to an uncharged atom or atomic group (group), a cationic residue having a charge that becomes a cation, and an anionic residue that becomes an anion.
• 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 combines with the nitrogen atom of component (A) to form a hydrogen-bonding functional group or an organic group.
• the acid of component (B) is a compound composed of protonated hydrogen and an anionic residue.
• the organic salt of the present invention has the following formula (II):
• 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 1 carbon atom.
• R 4 is a hydrogen atom or a monovalent organic group having 1 to 21 carbon atoms
• l is 0 to 3
• m is 0 to 3
• n is 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.
• l is preferably 0 or 1
• m is preferably 2 or 3.
• formula (II) reference is made to those listed above for amino acids and carboxylic acids that form organic salts. For specific details and preferred examples, reference is made to all the descriptions given above for components (A), (B) and formula (I), which are cited as explanations for formula (II). In addition, preferred examples of organic salts of formula (II) are appended below.
• X is a hydrogen atom.
• the ratio of the total number of primary or secondary amino groups to the number of carboxy groups contained in the amino acid is greater than 1. .
• the ratio of the total number of primary or secondary amino groups to the number of carboxy groups contained in the amino acid is 1. be. In another preferred example, the ratio of the total number of primary or secondary amino groups to the number of carboxy groups contained in the amino acid (total number of primary or secondary amino groups/number of carboxy groups) is less than 1 is. 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 4 or more and 7 or less. In another preferred example, the isoelectric point of the amino acid is less than 4. In one preferred example, in formula (II), R 4 is a hydrocarbon group having a hydrogen-bonding functional group.
• R 4 is a hydrocarbon group having a hydroxyl group and/or a carboxyl group.
• R 4 is a hydrocarbon group having a hydroxyl group.
• R 4 is a hydrocarbon group having both a hydroxyl group and a carboxy group.
• R 4 is an unsaturated or branched aliphatic hydrocarbon group having 7 to 21 carbon atoms.
• the preparation method of the formulation of the present invention is not particularly limited, it can be prepared, for example, as follows.
• An amino acid and a carboxylic acid are mixed and stirred in water.
• the preparation temperature and time depend on the type of raw material and the like, but for example, it can be carried out at room temperature for about 1 hour to 1 day. After that, the desired compound can be obtained by distilling off the water under reduced pressure.
• the formulation of the present invention is capable of exhibiting the effects held by component (A) and component (B).
• component (A) when arginine or histidine is used as component (A), it has a skin moisturizing effect and hair repair effect, when lysine has a stratum corneum transparency retention effect, and when ⁇ -aminobutyric acid has a skin barrier function. Improvement action, epidermal cell proliferation action, melanogenesis inhibitory effect can be obtained when cysteine is used, and melanin production inhibitory effect can be obtained when linoleic acid is used as the component (B).
• the mixture of component (A) and component (B) or the salt of component (A) and component (B) may be in an anhydrous state (anhydrous), and the moisture in the air may be removed. It may be an absorbed hydrate.
• a hydrate refers to a compound that, when left in the air at 25°C, absorbs water and has a saturated moisture content. Compounds that do not absorb water when left in air at 25° C. are non-hydrated and anhydrous.
• the formulations of the present invention contain mixtures of components (A) and (B) or salts of (A) and (B), whether the anhydrides and hydrates are liquids or solids at 25°C.
• the liquid containing the compound of the present invention is sprayed or applied to the part to be used, when the solvent evaporates, it remains as a liquid, and the effect is exhibited in a wide range, crystals are precipitated or aggregated and solidified. There is no problem in use such as falling off. Also, if it is liquid at 25° C., it can be used as a solvent or base when used with other additives.
• the mixture of components (A) and (B) or the organic salt of (A) and (B) is preferably an anhydride and/or hydrate that is liquid at 25°C. It is more preferred that the compound or hydrate is liquid at 25°C.
• a preferred combination of components (A) and (B) is Amino acids with isoelectric points greater than 7 and component (B) include saturated hydroxy monocarboxylic acids, saturated hydroxy di- or tricarboxylic acids.
• preferred combinations of components (A) and (B) include the following.
• A An amino acid having an isoelectric point of more than 7 as component (A), and a saturated hydroxymonocarboxylic acid as component (B), preferably having a plurality of hydroxyl groups, and more preferably gluconic acid.
• Combination B of (A) and component (B) an amino acid having an isoelectric point of more than 7 as component (A), a saturated hydroxy di- or tricarboxylic acid as component (B), preferably having 3 or more carboxy groups
• Combination C of component (A) and component (B) which is more preferably citric acid: formula (I) as component (A) (R 2 : having an organic group, preferably having a substituent, more preferably a nitrogen-containing group, more preferably a primary amino group, particularly preferably L-lysine, l:0, m:2, n:0) amino acids, saturated hydroxy as component (B) carboxylic acid, preferably having a plurality of hydroxyl groups, and more preferably gluconic acid.
• component (B) is a branched aliphatic carboxylic acid
• component (B) is a branched aliphatic carboxylic acid
• Combination I Formula (I) as component (A) (R 3 : a hydrocarbon group having 1 to 22 carbon atoms, more preferably a hydrocarbon group having 4 to 12 carbon atoms, and a carbonized Hydrogen radicals are more preferred, gamma-aminobutyric acid being particularly preferred, an amino acid of l:0, m:2, n:1), component (A) above which is a saturated hydroxy monocarboxylic acid as component (B).
• Component (B) J Formula (I) as Component (A) (R 2 : Having an organic group, preferably having a substituent, more preferably an oxygen-containing group, and still more preferably having a hydroxyl group , particularly preferably having a hydroxyl group at the end of the hydrocarbon group, most preferably L-serine, an amino acid of l: 0, m: 2, n: 0), saturated hydroxy monocarboxylic acid as component (B) Among them, it is more preferable to have two or more hydroxyl groups, and it is more preferable to be gluconic acid.
• a preferred combination of components (A) and (B) and examples of molar ratios include the following: 1: lysine as component (A), gluconic acid as component (B), molar ratio 1:1 2: Lysine as component (A), gluconic acid as component (B), molar ratio 1:2 3: lysine as component (A), citric acid as component (B), molar ratio 1:1 4: Lysine as component (A), citric acid as component (B), molar ratio 3:2 5: arginine as component (A), isostearic acid as component (B), molar ratio 1:1 6: Arginine as component (A), isostearic acid as component (B), molar ratio 1:2 7: Arginine as component (A), oleic acid as component (B), molar ratio 1:1 8: Arginine as component (A),
• the formulation of the present invention has components (A) and (B), and the amino acid of component (A) has a hydrogen-bonding functional group (a carboxy group, a hydrogen atom bonded to a nitrogen atom), so that it has an affinity for water. It has excellent water retention and hygroscopicity.
• a hydrogen-bonding functional group a carboxy group, a hydrogen atom bonded to a nitrogen atom
• an amino acid having an isoelectric point of more than 7 as the component (A), and a carboxylic acid having a hydrogen-bonding functional group at the hydrocarbon moiety as the component (B). More preferred are amino acids of greater than 7 and hydroxycarboxylic acids as component (B), more preferred are amino acids having an isoelectric point of greater than 7 as component (A) and hydroxytricarboxylic acids as component (B).
• amino acids having an isoelectric point of greater than 7 as component (A) and hydroxytricarboxylic acids as component (B).
• combinations of the above 3, 4, 17, 18, 25 to 27, 31, 34 and 41 are particularly preferable as the combination of components (A) and (B).
• an amino acid having an isoelectric point of more than 7 is preferable as the component (A), and an unsaturated carboxylic acid is preferable as the component (B).
• L-arginine is more preferable as the component (A)
• oleic acid is more preferable as the component (B).
• the combination of components (A) and (B) the combination of 7 and 8 above is more preferable.
• component (A) and component (B) are amino acids and carboxylic acids, respectively, so they have excellent solubility in poorly soluble substances.
• component (A) and component (B) are amino acids and carboxylic acids, respectively, so they have excellent solubility in poorly soluble substances.
• the formulation of the present invention When the formulation of the present invention is applied to cosmetics, it has components (A) and (B), so it is excellent in terms of ease of use, moisturizing feeling, and non-stickiness when applied to the skin. Due to the non-volatility of the mixture of components (A) and (B) or the organic salt used in the invention, the feeling of water retention is particularly excellent over a long period of time.
• a mixture of components (A) and (B) having a melting point of less than 25° C., an organic salt, or a solution thereof is excellent in ease of use, moisturizing feeling, non-stickiness, refreshing feeling, and the like.
• component (A) an amino acid with an isoelectric point of more than 7 as component (A), an amino acid with an isoelectric point of 4 or more and 7 or less, and a hydrogen-bonding functional group at the hydrocarbon moiety as component (B).
• hydrogen-bonding functional groups it is more preferable to have a hydroxyl group or a carboxy group, and more preferably to have two or more carboxy groups.
• an amino acid having an isoelectric point of more than 7 as the component (A), an amino acid having an isoelectric point of 4 or more and 7 or less, and an unsaturated or branched aliphatic carboxylic acid as the component (B) are preferable, and the component ( More preferred are arginine and proline as A) and unsaturated or branched aliphatic carboxylic acids as component (B).
• the blending molar ratio of component (A) and component (B) (component (A):component (B)) is not particularly limited. 1 to 1:3 is more preferred, and 3:2 to 1:2 is even more preferred.
• the above 3 to 10, 15 to 20, 25 to 27, 31, 33 to 37 are preferable, and 6, 8, 25, 26, 31, 33 to A combination of 37, 40, 41 is more preferred.
• Objects include organic substances, inorganic substances, and the like, and are not particularly limited, but examples thereof include biological tissues (hair, skin), resins, paper, metals, metal oxides, and the like.
• carboxylic acid having a hydrogen-bonding functional group in the hydrocarbon moiety is preferable as component (B), and it is more preferable to have a hydroxyl group and/or a carboxyl group as the hydrogen-bonding functional group. It is more preferable to have a hydroxyl group, particularly preferably to have a hydroxyl group and a carboxyl group, and most preferably to have a hydroxyl group and two or more carboxyl groups.
• component (A) an amino acid with an isoelectric point of more than 7, an amino acid with an isoelectric point of 4 or more and 7 or less, and an unsaturated or branched aliphatic carboxylic acid as component (B) are preferable.
• combinations of the above 1 to 4, 11, 12, 17, 18, 25 to 27, 31, 32, 34, 38, and 41 are preferable as the combination of components (A) and (B).
• the composition of the present invention has excellent antibacterial properties due to the carboxy groups of component (A) and/or component (B).
• the total number of amino groups and the total number of carboxy groups of component (A) and component (B) are a combination with a large total number of carboxy groups, and component (A) and component (B) are organic salts.
• an unneutralized carboxyl group (--COOH) is present when forming That is, the ratio of the total number of amino groups to the total number of carboxy groups (total number of amino groups/total number of carboxy groups) of component (A) and component (B) is preferably 1 or less.
• the mixture of component (A) and component (B) or the organic salt is non-volatile, and above all, the liquid mixture or organic salt is highly concentrated and uniformly coated after the volatile components evaporate. As a result, effective and long-lasting antibacterial properties can be obtained.
• it since it is effective as a solvent for drugs that are effective against bacteria and viruses such as existing antibacterial agents, antiviral agents, and disinfectants, it is possible to use existing antibacterial agents, antiviral agents, disinfectants, etc. at higher concentrations.
• component (A) is preferably an amino acid having an isoelectric point of 4 or more and 7 or less
• component (B) preferably has a hydrogen-bonding functional group in the hydrocarbon moiety. It is more preferable to have a hydroxyl group and/or a carboxy group as a hydrogen-bonding functional group, more preferably to have a hydroxyl group and a carboxy group, and particularly preferably to have a hydroxyl group and two or more carboxy groups.
• a combination in which the ratio of the total number of amino groups to the total number of carboxy groups (total number of amino groups/total number of carboxy groups) of component (A) and component (B) is 1 or less is preferred. Among these, combinations of the above 3, 16, 17, 20, 25, 27, 31, 33, 34, 40 and 41 are preferable as the combination of components (A) and (B).
• the formulation of the present invention has good safety. ), the Japanese Pharmacopoeia Standards for Quasi-drugs (external regulations), Pharmaceutical Additives Standards (medicine additives), and the compounds listed in the Food Additives Standards (food additives), It is highly safe and suppresses skin irritation, so it can be used on the human body and applied to cosmetics and daily necessities.
• composition of the present invention is easily biodegradable because component (A) and component (B) are amino acids and carboxylic acids, respectively.
• formulations containing components (A) and (B) derived from natural products are useful because they are excellent in biodegradability and have a low environmental load.
• the formulation of the present invention has a hydrogen-bonding functional group in component (A) and/or component (B) in combination with a polymer compound and water, and thus has good affinity with the polymer compound and water. Suitable for gel formation, thickening effect. If the polymer compound also has a hydrogen-bonding functional group, it becomes easier to form a gel, which is preferable from the point of thickening effect.
• the gel composition containing the formulation of the present invention, a polymer compound, and water has a reduced viscosity when a shearing force is applied, making it easy to apply to an object, and then increases in viscosity when the shearing force is not applied. It is useful from the point of exhibiting thixotropic property that dripping on the surface is difficult to occur.
• the formulation of the present invention may be a formulation of only components (A) and (B), a solution diluted with components (A) and (B) and a solvent, a mixture with other components, a composition may be
• the blending molar ratio of component (A) and 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.
• components (A) and (B) in the formulation of the present invention is not particularly limited, but for example, 0.01 to 100% by mass, or 0.1 to 100% by mass, relative to the total amount of the formulation, 1 to 95% by mass.
• the solvent examples include, but are not limited to, 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., and these may be used singly or in combination of two or more. You may be used singly or in combination of two or more. You may be used singly or in combination of two or more. You may be used singly or in combination of two or more. You may be used singly or in combination of two or more. You may be used singly or in combination of two or more. You may be used singly or in combination
• Examples of the other components include, but are not limited to, water, surfactants (anionic surfactants, cationic surfactants, nonionic surfactants, amphoteric surfactants, etc.), oils, solvents, Oils, cationic polymers, water-soluble polymers, viscosity modifiers, resins, resin particles, glossing agents, higher alcohols, polyhydric alcohols, higher fatty acids, amidoamines, hydrocarbons, waxes, esters, silicone derivatives, bioactive Ingredients, extracts, antioxidants, sequestering agents, preservatives, UV absorbers (including organic and inorganic), fragrances, moisturizers, carbons, metal oxides, minerals, salts, neutralization agents, pH adjusters, cooling agents, insect repellents, enzymes, dyes, organic pigments, inorganic pigments, colorants, pearlescent agents, pearlescent agents, anti-inflammatory agents, antioxidants, corrosion inhibitors, rust inhibitors, metals Deactivator, antifoaming agent, whitening agent, wrinkle improving agent
• the formulations of the present invention can be used in cosmetics, for example, to impart water retention, to impart hygroscopicity and/or to impart antibacterial properties. Further, it can be used in gel compositions containing polymeric compounds and water.
• the formulation of the present invention has water retention, hygroscopicity, feeling of use (ease of use, moisturizing, non-stickiness, refreshing feeling, etc.), adhesion to hair, antibacterial properties, skin irritation, biodegradability, and gel formation.
• organic Materials or inorganic materials including but not limited to metals, metal oxides (including but not limited to silica, aluminum oxide (alumina), zirconia, titanium oxide, magnesium oxide, indium tin 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, oxide Iron, indium oxide, boron oxide, calcium oxide, barium oxide, thorium oxide, indium tin oxide, ferrite, etc.), dissolving solvent, dispersing
• compositions of the present invention include formulations as described above.
• the composition of the present invention may contain the organic salts described above. These formulations and compositions can be used to impart water retention, hygroscopicity, and/or antimicrobial properties, and as cosmetics. Furthermore, it can be used as a gel composition containing a polymer compound and water.
• the form of the composition containing the compound of the present invention is not particularly limited, and may be, for example, liquid, solid, gel, or the like.
• ingredients other than ingredients (A) and (B) are not particularly limited, but examples include the above solvents, antibacterial agents, Bacteria such as antiviral agents, disinfectants, agents that are effective against viruses, surfactants (anionic surfactants, cationic surfactants, nonionic surfactants, amphoteric surfactants, etc.), resins, ultraviolet rays Absorbents (including organic and inorganic), fragrances, moisturizers, metal oxides, neutralizers, pH adjusters, colorants, antioxidants, corrosion inhibitors, rust inhibitors, metal deactivators , antifoaming agents, and the like. These may be used individually by 1 type, and may be used in combination of 2 or more type.
• the components other than components (A) and (B) are not particularly limited. Active agents, oils, cationic polymers, water-soluble polymers, viscosity modifiers, resins, resin particles, glossing agents, higher alcohols, polyhydric alcohols, higher fatty acids, amidoamines, hydrocarbons, waxes, esters, silicone derivatives , bioactive ingredients, extracts, antioxidants, sequestering agents, preservatives, UV absorbers (including organic and inorganic), fragrances, moisturizers, carbons, metal oxides, minerals, salts , neutralizer, pH adjuster, cooling agent, insect repellent, enzyme, dye, organic pigment, inorganic pigment, colorant, pearl foil, pearlescent agent, anti-inflammatory agent, antioxidant, whitening agent, wrinkle-improving agent , vitamins, amino acids, hair growth agents, antibacterial agents, hormone agents, plant extracts, seaweed extracts, herbal medicines, activators, blood circulation promoters, organic modified clay minerals, and the like.
• the composition used in the cosmetic of the present invention has a short- and long-term water-retaining/moisturizing and antistatic (antistatic) effect due to the nonvolatile nature of the mixture of components (A) and (B) or the organic salt.
• it When applied to the skin or the like, it can provide a moisturizing feeling and provide a good feeling without stickiness.
• affinity to the skin, permeability, and low irritation it is highly safe even in skin care compositions, has good compatibility with the skin, has good skin elasticity, and is less irritating to the skin. A composition is obtained.
• the formulation of the present invention is useful as a base material for skin care compositions in view of the high solubility of active ingredients, and is excellent in water retention and moisturizing effects on the skin due to its excellent permeability into the skin and the like. It can also be used as a carrier for active ingredients. In addition to use on the skin, it can also be used for keratin, nails, the oral cavity, and the intranasal cavity where the effects of the present invention are desired. In addition, it can be said that it is a low environmental load compound because of its excellent biodegradability.
• the gel composition containing the formulation of the present invention contains a polymer compound and water in addition to the formulation of components (A) and (B).
• the polymer compound include, but are not limited to, synthetic polymer compounds, semi-synthetic polymer compounds, and natural polymer compounds. , water, and component (A) and/or component (B) to interact with each other and have a high affinity.
• a polymer compound containing at least one selected from groups is preferred.
• semi-synthetic polymer compounds and natural polymer compounds are preferred, and natural polymer compounds are more preferred. These may be used individually by 1 type, and may be used in combination of 2 or more type.
• Examples of synthetic polymer compounds include, but are not limited to, polyacrylic acid, vinyl acetate copolymer, maleic anhydride copolymer, polyvinyl alcohol, polyvinylpyrrolidone, polyethylene glycol, polyethylene oxide, and polyester. , polyacrylonitrile-based, polyamide-based, polyimide-based, polyamideimide-based, polymaleimide-based, polyurethane-based, polycarbonate-based, and polyarylate-based high molecular compounds.
• semisynthetic polymer compounds include, but are not limited to, cellulose derivatives (sodium carboxymethylcellulose, hydroxyethylcellulose, methylcellulose, ethylcellulose, nitrocellulose, hydroxypropylcellulose, hydroxypropylmethylcellulose, crystalline cellulose), sodium alginate, ester gum, Soluble starch etc. are mentioned.
• natural polymer compounds include, but are not limited to, polysaccharides, cellulose, nucleic acids or salts thereof, ribonucleic acids or salts thereof, water-soluble proteins (casein, collagen, gelatin, albumin, fibroin, elastin, keratin, sericin, etc.), hyaluronic acid or its salts, mucopolysaccharides (such as chondroitin sulfate), etc., and polysaccharides are particularly preferred.
• polysaccharides include, but are not limited to, xanthan gum, carrageenan, tamarind sea gum, gellan gum, guar gum, pectin, gum arabic, karaya gum, locust bean gum, daiutang gum, sodium alginate, agarose, hyaluronic acid, polygalactose.
• Natural polysaccharides such as uronic acid, carboxymethyl pullulan, carboxymethyl chitin, carboxymethyl chitosan, carboxymethyl mannan, carboxymethyl starch, carboxymethyl dextran, carboxyethyl cellulose, carboxy alkyl polysaccharides such as carboxymethyl pullulan, oxidized cellulose and oxidized starch and polysaccharides containing sulfate groups such as chondroitin sulfate, dermatan sulfate, heparin and heparan sulfate.
• polymer compounds having hydrogen-bonding functional groups are preferred, and water-soluble polymer compounds are more preferred.
• Such polymer compounds are preferably xanthan gum, carrageenan, gellan gum, guar gum, diutane gum and sodium alginate, more preferably xanthan gum, carrageenan, gellan gum, guar gum and diutane gum, and still more preferably xanthan gum and guar gum.
• the component (A), the component (B), the polymer compound, and water are blended in an arbitrary ratio, and the blending amount is not particularly limited.
• 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, still more preferably 30% by mass or less, and 10% by mass or less.
• the 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.
• each of the above preferred examples shown in formula (I), combinations thereof with each of the above preferred examples shown in component (B), and each of the above preferred examples shown in formula (II) a combination of at least one of them can be a more preferable embodiment based on the results of the examples.
• the combination of them with the properties of the mixture of components (A) and (B) or the salt of (A) and (B), and further the combination of them with each preferred example of the polymer compound Based on the results of the examples, it can be a more preferable mode.
• Formulations (Organic Salts) 1-427 shown in Tables 1A-1D were prepared in the following manner. The following reagents were used for component (A) and component (B). L-lysine, ⁇ -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 Institute.
• L-proline is made by Sigma-Aldrich Japan. Isostearic acid and oleic acid are manufactured by Miyoshi Oil Co., Ltd. Lactic acid, butyric acid, adipic acid, and succinic acid are manufactured by Kanto Kagaku Co., Ltd.
• Example 48 Formulation (salt) 48 L-arginine (11.78 g, 0.10 mol) and isostearic acid (28.45 g, 0.10 mol) in 50 mL of water and 50 mL of ethanol were stirred at room temperature for 3 hours, and the solvent was distilled off under reduced pressure to obtain a colorless liquid. rice field. By washing the resulting liquid, a colorless liquid mixture (salt) consisting of L-arginine and isostearic acid was obtained.
• Formulation (salt) 48 FT-IR (KBr): 3165 cm -1 , 2925 cm -1 , 1854 cm -1 , 1653 cm -1 , 1406 cm -1 .
• Examples 1-6, 22-27, 43-48, 64-69, 85-90, 106-111 Formulations (salts) 1-6, 22-27, 43-48, 64-69, 85- 90, 106-111 Similarly, using the component (A) and the component (B) in the compounding ratio described in Table 1A, prepared under the same conditions as in Example 48, formulations (salts) 1 to 6, 22 to 27, 43 to 48 , 64-69, 85-90, 106-111. Spectral data for representative formulations (salts) are shown below.
• Example 49 Formulation (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 then the solvent was distilled off under reduced pressure to obtain a yellow liquid. rice field. By washing the resulting liquid, a yellow liquid mixture (salt) of L-arginine and oleic acid was obtained.
• Formulation (salt) 49 FT-IR (KBr): 3347 cm -1 , 2925 cm -1 , 1737 cm -1 , 1636 cm -1 , 1404 cm -1 .
• Example 52 Formulation (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 the water was distilled off under reduced pressure to obtain a colorless liquid. By washing the resulting liquid, a colorless liquid mixture (salt) consisting of L-arginine and lactic acid was obtained.
• Formulation (salt) 52 FT-IR (KBr): 3366 cm -1 , 3189 cm -1 , 1718 cm -1 , 1141 cm -1 , 863 cm -1 .
• Example 53 Formulation (salt) 53 In 50 ml of water, L-arginine (11.78 g, 0.10 mol) and adipic acid (14.61 g, 0.10 mol) were stirred at room temperature for 1 hour. A formulation (salt) consisting of Formulation (salt) 53 FT-IR (KBr): 3131 cm -1 , 2940 cm -1 , 1752 cm -1 , 1427 cm -1 , 857 cm -1 .
• Example 16 Formulation (salt) 16 After stirring L-lysine (14.63 g, 0.10 mol) and citric acid (19.39 g, 0.10 mol) in 50 ml of water at room temperature for 3 hours, the water was distilled off under reduced pressure to obtain a yellow liquid. By washing the resulting liquid, a yellow liquid mixture (salt) composed of L-lysine and citric acid was obtained.
• Formulation (salt) 16 FT-IR (KBr): 3432 cm -1 , 3148 cm -1 , 1764 cm -1 , 1217 cm -1 , 848 cm -1 .
• Example 60 Formulation (salt) 60
• L-arginine (11.78 g, 0.10 mol) and benzoic acid (12.21 g, 0.10 mol) were stirred at room temperature for 1 hour, and the water was distilled off under reduced pressure to obtain a colorless liquid. By washing the resulting liquid, a colorless liquid mixture (salt) of L-arginine and benzoic acid was obtained.
• Compound (salt) 60 FT-IR (KBr): 3366 cm -1 , 3189 cm -1 , 1718 cm -1 , 1191 cm -1 , 848 cm -1 , 738 cm -1 .
• Example 61 Formulation (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. A formulation (salt) consisting of cinnamic acid was obtained. Formulation (salt) 61 FT-IR (KBr): 3088 cm -1 , 1637 cm -1 , 1532 cm -1 , 1381 cm -1 .
• Example 62 Formulation (salt) 62
• L-arginine (11.78 g, 0.10 mol) and L-ascorbic acid (17.61 g, 0.10 mol) were stirred at room temperature for 1 hour, and the water was distilled off under reduced pressure to obtain a colorless liquid. By washing the resulting liquid, a white solid compound (salt) composed of L-arginine and L-ascorbic acid was obtained.
• Formulation (salt) 62 FT-IR (KBr): 3161 cm -1 , 1559 cm -1 , 1342 cm -1 , 1108 cm -1 , 900 cm -1 .
• Example 170 Formulation (salt) 170 ⁇ -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.
• a formulation (salt) consisting of Compound (salt) 170 FT-IR (KBr): 2931 cm -1 , 2209 cm -1 , 1653 cm -1 , 1574 cm -1 , 1029 cm -1 , 659 cm -1 .
• Example 173 Formulation (salt) 173 ⁇ -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. Obtained. By washing the resulting liquid, a colorless liquid mixture (salt) of ⁇ -aminobutyric acid and oleic acid was obtained.
• Formulation (salt) 173 FT-IR (KBr): 2925 cm -1 , 2854 cm -1 , 1711 cm -1 , 1552 cm -1 , 1406 cm -1 , 1244 cm -1 .
• Examples 133, 134, 153, 154, 173, 174, 346, 347 Formulations (salts) 133, 134, 153, 154, 173, 174, 346, 347 Similarly, using the component (A) and component (B) in the compounding ratios described in Tables 1B and C, prepared under the same conditions as in Example 173, formulations (salts) 133, 134, 153, 154, 173 , 174, 346, 347 were obtained. Spectral data for representative formulations (salts) are shown below.
• Example 157 Formulation (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. A compound (salt) was obtained.
• Example 160 Formulation (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. A compound (salt) was obtained. Compound (salt) 160 FT-IR (KBr): 3081 cm -1 , 1735 cm -1 , 1588 cm -1 , 1025 cm -1 , 658 cm -1 .
• Example 140, 160, 180, 197, 214, 231, 248, 265, 282, 299, 316, 333, 353, 370, 387 Formulations (salts) 140, 160, 180, 197, 214, 231, 248, 265, 282, 299, 316, 333, 353, 370, 387 Similarly, using the component (A) and component (B) in the blending ratios described in Tables 1B and C, prepared under the same conditions as in Example 160, formulations (salts) 140, 160, 180, 197, 214 , 231, 248, 265, 282, 299, 316, 333, 353, 370, 387.
• Example 182 Formulation (salt) 182 ⁇ -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 the water was distilled off under reduced pressure to obtain a colorless liquid. By washing the resulting liquid, a colorless liquid mixture (salt) composed of ⁇ -aminobutyric acid and citric acid was obtained.
• Formulation (salt) 182 FT-IR (KBr): 3441 cm -1 , 3207 cm -1 , 1708 cm -1 , 1213 cm -1 , 844 cm -1 .
• Example 184 Formulation (salt) 184 ⁇ -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 benzoic acid (salt).
• Formulation (salt) 184 FT-IR (KBr): 2953 cm -1 , 1752 cm -1 , 1518 cm -1 , 1388 cm -1 , 1282 cm -1 .
• Example 165 Formulation (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 L-ascorbic acid (salt).
• Compound (salt) 165 FT-IR (KBr): 3157 cm -1 , 1791 cm -1 , 1591 cm -1 , 1110 cm -1 .
• Example 414 Formulation (salt) 414 In 50 ml of water, L-glutamic acid (14.71 g, 0.10 mol) and hexanoic acid (11.61 g, 0.10 mol) were stirred at room temperature for 1 hour. A formulation (salt) consisting of Formulation (salt) 414 FT-IR (KBr): 3197 cm -1 , 1685 cm -1 , 1509 cm -1 , 1271 cm -1 , 817 cm -1 .
• Examples 394-398, 411-415 Formulations (salts) 394-398, 411-415 Similarly, using the component (A) and component (B) in the compounding ratio shown in Table 1D, preparation was performed under the same conditions as in Example 414 to obtain formulations (salts) 394-398 and 411-415.
• Example 416 Formulation (salt) 416 L-glutamic acid (14.71 g, 0.10 mol) and 50 mass% gluconic acid (38.32 g, 0.10 mol) were stirred in 50 ml of water at room temperature for 1 hour, and water was distilled off under reduced pressure to give a white solid of L- A formulation (salt) consisting of glutamic acid and gluconic acid was obtained.
• Formulation (salt) 416 FT-IR (KBr): 3411 cm -1 , 3065 cm -1 , 1734 cm -1 , 1514 cm -1 , 1353 cm -1 , 1127 cm -1 .
• Examples 399, 400, 416, 417 Formulations (salts) 399, 400, 416, 417 Similarly, formulations (salts) 399, 400, 416, and 417 were obtained by preparing under the same conditions as in Example 416 using component (A) and component (B) in the compounding ratios shown in Table 1D.
• Example 418 Formulation (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. A formulation (salt) consisting of the acid was obtained.
• Compound (Salt) 418 FT-IR (KBr): 3031 cm -1 , 2951 cm -1 , 1756 cm -1 , 1692 cm -1 , 1508 cm -1 , 1256 cm -1 .
• Examples 401-403, 418-420 Formulations (salts) 401-403, 418-420 Similarly, using the component (A) and component (B) in the compounding ratio shown in Table 1D, preparation was performed under the same conditions as in Example 418 to obtain formulations (salts) 401-403 and 418-420.
• Example 421 Formulation (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. A formulation (salt) consisting of the acid was obtained.
• Formulation (salt) 421 FT-IR (KBr): 3040 cm -1 , 1748 cm -1 , 1510 cm -1 , 1444 cm -1 , 727 cm -1 .
• Example 404, 421 Formulations (salts) 404, 421 Similarly, formulations (salts) 404 and 421 were obtained by preparing under the same conditions as in Example 421 using component (A) and component (B) in the compounding ratios shown in Table 1D.
• Example 422 Formulation (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. A formulation (salt) consisting of L-malic acid was obtained.
• Formulation (salt) 422 FT-IR (KBr): 3041 cm -1 , 1722 cm -1 , 1511 cm -1 , 1257 cm -1 , 1102 cm -1 .
• Examples 405-407, 422-424 Formulations (salts) 405-407, 422-424 Similarly, using the component (A) and component (B) in the compounding ratio shown in Table 1D, preparation was performed under the same conditions as in Example 422 to obtain formulations (salts) 405-407 and 422-424.
• Example 425 Formulation (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. A formulation (salt) consisting of the acid was obtained. Compound (salt) 425 FT-IR (KBr): 3030 cm -1 , 1637 cm -1 , 1509 cm -1 , 1258 cm -1 .
• Examples 408, 425 Formulations (salts) 408, 425 Similarly, formulations (salts) 408 and 425 were obtained by preparing under the same conditions as in Example 425 using component (A) and component (B) in the compounding ratios shown in Table 1D.
• Example 426 Formulation (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 L-ascorbic acid (salt).
• Formulation (salt) 426 FT-IR (KBr): 3055 cm -1 , 1805 cm -1 , 1509 cm -1 , 1268 cm -1 , 815 cm -1 .
• Examples 409, 410, 426, 427 Formulations (organic salts) 409, 410, 426, 427 Similarly, preparation was performed under the same conditions as in Example 426 using the component (A) and component (B) in the compounding ratios shown in Table 1D to obtain formulations (organic salts) 409, 410, 426, and 427. .
• Formulations 1 to 427 shown in Tables 1A to 1D were prepared by the method described above using the molar ratios of components (A) and (B) shown in the table, and heated at 25°C. I checked the status.
• Comparative Example 5 which is a general water retention agent, it was confirmed that Examples 428 to 459 are excellent in water retention, and the combination of component (A) and component (B) contributes to water retention. was suggested.
• Component (A) is an amino acid with an isoelectric point of greater than 7, and in comparison of formulations with common component (B), amino acids with an isoelectric point of greater than 7 (Examples 428, 429, 432, 435, 443, 444, 450 , 452) and amino acids with an isoelectric point of 4 or more and 7 or less (Examples 449, 453, 455, 456, 459), it was confirmed that amino acids with an isoelectric point of more than 7 are excellent in water retention. It was suggested that among amino acids having an isoelectric point of more than 7, amino acids having two or more nitrogen atoms are excellent in water retention.
• Hygroscopic evaluation Examples 460 to 470 and Comparative Example 6 in Table 3 were completely dried in a vacuum dryer at 60 ° C. for 18 hours, and then left at room temperature for 1 month. The moisture content was measured with a meter (CA-200 manufactured by Mitsubishi Chemical Analytech Co., Ltd.) to evaluate the hygroscopicity.
• Examples 460 to 470 had a higher moisture content in a saturated state than Comparative Example 6 and were excellent in hygroscopicity.
• Component (B) is oleic acid and the same formulation (organic salt)
• an amino acid is used as component (A). It was confirmed that it is superior in this and that it is suitable as a moisture absorbent.
• composition containing an amino acid with an isoelectric point of over 7 as component (A) has excellent hygroscopicity. It was suggested that the composition of the present invention is suitable as a hygroscopic agent used in cosmetics, for example, because of its excellent hygroscopicity.
• the spreadability after application was evaluated on a 5-point scale based on the feel of the skin when an aqueous solution of each formulation (organic salt) was applied and spread. Evaluated as 3 when feeling easy, and as 1 when not feeling easy to spread.
• the moisturizing feeling after application was evaluated on a 5-point scale based on the feel of the skin when an aqueous solution of each formulation (organic salt) was applied and spread. 3 was given to those who felt moisturizing, and 1 was given to those who did not feel moisturizing.
• an aqueous solution of each formulation is applied and evaluated on a 5-point scale based on the feel of the skin when spread. 3 was evaluated as 3, and 1 was evaluated as sticky.
• Examples 471 to 502 using the formulation (organic salt) of the present invention are superior to Comparative Examples 7 to 9 in ease of application, moisturizing, and non-stickiness. was also confirmed to be excellent.
• Component (B) is lactic acid and the same formulation (organic salt)
• the component (A) is an amino acid. confirmed the superiority of
• Examples 472, 474, 477, 478, and 483 comprising an amino acid having an isoelectric point of more than 7 as a component (A), an amino acid having an isoelectric point of 4 or more and 7 or less, and L-malic acid and citric acid as a component (B) , 484, 487, 490, 492, 495, 497, 498, 501 and 502 felt good.
• the formulation of the present invention has excellent usability when applied to the skin and is suitable as a cosmetic or the like.
• the spreadability after application was evaluated on a 5-point scale based on the feel of the skin when the evaluation sample was applied and spread. , was evaluated as 1 when the stretchability was not felt.
• the feeling of refreshment after application was evaluated on a 5-point scale based on the feel of the skin when the evaluation sample was applied and spread. A value of 1 was given to those that felt a feeling and those that did not feel a feeling.
• the evaluation sample was applied and evaluated on a 5-point scale based on the feel of the skin when it was spread.
• Examples 503 to 514 using the formulation (organic salt) of the present invention are compared to Comparative Example 10 and 11, which is used as a general cosmetic oily base material, for ease of spreadability during application and freshness. It was confirmed that both feeling and non-stickiness during use were excellent.
• Component (B) is oleic acid and the same formulation (organic salt)
• an amino acid is used as component (A). confirmed its superiority.
• Examples 507, 508, and 512-514 had a good feeling during use. Furthermore, by comparing Examples 504 and 507, and Examples 505 and 508, it was found that the blending of components (A) and (B) in which the blending molar ratio of components (A) and (B) was 1:2 was superior. It showed a feeling of use. From this, it was suggested that the composition (organic salt) of the present invention has excellent usability when applied to the skin and is suitable as a cosmetic. 7. Adhesion to hair 1
• hair weight A before test was immersed in 3.0 g of 80% by mass aqueous solutions of Examples 515 to 544 and Comparative Examples 12 to 16 for 60 minutes. After the immersion, the hair was taken out, the composition (organic salt) was wiped off with a Kimwipe until the weight did not change, and the weight was measured (hair weight B after the test).
• the adhesion rate of the formulation (organic salt) to hair was calculated using the following formula.
• Formulation (organic salt) adhesion rate (%) [(hair weight after test B (g) - hair weight before test A (g)) / hair weight before test A (g)] x 100
• Component (B) is lactic acid and the same formulation (organic salt)
• the component (A) is an amino acid. confirmed the superiority of
• component (A) is L-lysine. From the comparison of the formulation (organic salt) of Examples 515 and 516 and Comparative Example 13, the superiority of carboxylic acid as component (B) was confirmed. confirmed.
• Examples 515 to 544 were confirmed to have excellent adhesion to hair, and as a combination capable of forming a salt structure, component (A) and component (B ) is useful for adhesion to hair.
• component (B) confirmed the superiority of being a carboxylic acid having a hydrogen-bonding functional group (hydroxyl group and/or carboxyl group).
• component (A) is L-arginine and the same formulation (organic salt) Example 517 and formulation (organic salt) Example 518, formulation (organic salt) Example 523 and formulation (organic salt) Example A comparison with 524 suggested that component (B) is superior in that it is a carboxylic acid having a plurality of hydroxyl groups in the hydrocarbon moiety.
• Adhesion to hair 2 For Examples 545 to 555 and Comparative Examples 17 and 18 in Table 7, using the formulation (organic salt) prepared according to "4. Hygroscopic evaluation", in the same manner as in "Adhesion to hair 1" , to evaluate adhesion.
• Component (B) is oleic acid and the same formulation (organic salt)
• the component (A) was an amino acid. Confirmed superiority.
• Staphylococcus aureus strain NBRC15035 NITE Escherichia coli NBRC 15035 strain: NITE Potassium lactate: Fuji Film Wako Pure Chemical Medium Muller-Hinton broth: Becton, Dickinson and Company Medium L-Dry Product Restoration Medium "Daigo”: Fuji Film Wako Pure Chemical Calcium Chloride: Fuji Film Wako Pure Chemical Magnesium Chloride : Fuji Film Wako Pure Chemical Skim Milk: Snow Brand Megmilk Meat Extract: Solabia Biokar Diagnostics Peptone: Solabia Biokar Diagnostics Sodium Chloride: Fuji Film Wako Pure Chemical Agar: Fuji Film Wako Pure Chemical
• Antibacterial evaluation 1 minimum inhibitory concentration of formulation (organic salt) Examples 556 to 583 shown in Tables 8A and 8B, Staphylococcus aureus of Comparative Example 19, the minimum inhibitory concentration (MIC) against Escherichia coli was measured by the liquid microdilution method (described in the standard method of the Japanese Society of Chemotherapy), and various formulations The antibacterial activity of the substance (organic salt) was confirmed.
• Formulation (organic salt) concentration 250, 200, 150, 100, 50, 25, 12.5, 8, 4, 2, 0.8, 0.4, 0.2, 0.1, 0.05 mg/mL was evaluated, and the MICs are shown in Tables 8A and 8B.
• component (B) is lactic acid
• the advantage of being an amino acid as component (A) confirmed the gender.
• component (A) is isoelectric. It was confirmed that using an amino acid with an isoelectric point of 4 or more and 7 or less tends to be more excellent in antibacterial properties than an amino acid with a point of more than 7.
• halo test 1 Antibacterial evaluation 2 of compound (organic salt) (halo test 1)
• a halo test was performed using Staphylococcus aureus with reference to JISL1902.
• a 21 ⁇ m / m filter paper for Kiriyama funnel manufactured by Kiriyama Seisakusho was used as a test piece, and the filter paper was placed on a medium containing bacterial cells. 584, 585, Comparative Examples 20, 21) was dropped in an amount of 100 ⁇ L. After that, culture was performed, and the presence or absence of halos was visually confirmed. Table 9 shows the presence or absence of halos.
• Adhesion evaluation and antibacterial evaluation 3 (halo test 2) of formulation (organic salt) 9-3-1 were evaluated. Evaluation of Adhesion 100 ⁇ L of the compound (organic salt) aqueous solution (Examples 584 to 585) having the concentration shown in Table 9 was dropped onto a 21 ⁇ m/m filter paper for Kiriyama funnel, 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, 100 ⁇ L of water was dropped onto the filter paper and the filter paper was dried in a vacuum.
• Weight of attached sample weight of filter paper after drying (mg) - weight of filter paper before test (mg) + correction value (1.15 mg)
• AE polyoxyethylene alkyl ether
• the formulation (organic salt) of the present invention dissolves sparingly water-soluble antibacterial agents and other antiviral substances well, and even after standing at 25°C for 24 hours, no crystals precipitate and a stable solution can be obtained. It was confirmed. Accordingly, the formulation of the present invention was imparted with antibacterial properties or antiviral properties by adding an antibacterial agent or the like. It was suggested that an antibacterial composition was obtained.
• Component (B) is lactic acid and the same formulation (organic salt).
• the use of an amino acid as component (A) tends to increase the solubility of parabens. It was confirmed.
• Examples 586 to 596 are excellent in the solubility of the sparingly soluble substances, and components (A) and ( It was suggested that B) is useful for dissolving sparingly soluble substances.
• Antibacterial evaluation of antibacterial composition (minimum inhibitory concentration)
• Antibacterial compositions (Examples 597 to 612) prepared so as to contain equal amounts of the formulation of components (A) and (B) shown in Table 11 and paraben (concentration of paraben: 1.0 mg/mL, Example 597 ⁇ 612 concentration 1.0 mg/mL, total 2.0 mg/mL), Comparative Example 27 containing only water and paraben (concentration of paraben 1.0 mg/mL), Reference Example 1 containing L-lysine and citric acid (concentration 1.0 mg/mL) as described in 9-1. The presence or absence of antibacterial properties was evaluated from the presence or absence of growth of bacterial cells by the same test method as in .
• the effect of that additive can be imparted to the composition containing the formulation (organic salt) of the present invention, e.g. 9-4.
• the composition obtained by adding (dissolving) the antiviral substance in (1) is endowed with antiviral properties in addition to antibacterial properties.
• the skin irritation test of Examples 613 to 619 in Table 12 is a skin irritation test method (OECD TG439 method: in in vitro skin irritation test). In addition, the measurement concentration was 50% by mass. Further, from the obtained sperm cell rate (%), the irritation was determined according to the following criteria. Viable cell rate: ⁇ 50% Stimulated viable cell rate: >50% Non-stimulatory
• gel composition As polymer compounds, xanthan gum (Echo Gum T: manufactured by DSP Gokyo Food & Chemical), carrageenan (Sheep Gum FA: manufactured by DSP Gokyo Food & Chemical), gellan gum (Kelcogel: manufactured by Saneigen FFI ), guar gum (SUPERGEL CSA 200/50: manufactured by Sankei), daiutan gum (KELCO-VIS DG: manufactured by Sankei), and L-arginine, ⁇ -aminobutyric acid, and L-serine as amino acids of component (A). , benzoic acid, citric acid, and L-malic acid were used as the component (B).
• composition was prepared by the following method (Table 14). After the components (A) and (B) described in Table 14 were mixed in water, the water was distilled off, and the resulting mixture or salt was a hydrate and liquid at 25°C.
• compositions 2-28 Similarly, predetermined amounts of amino acid (component (A)), carboxylic acid (component (B)), and polymer compound shown in Table 14 were prepared under the same conditions as in Example 624, and gel compositions 2 to 2 were prepared. 28 was obtained.
• each amino acid (component (A)), acid (component (B)) and water described in Examples 625 to 651 were premixed in the same charging amount as described above to synthesize an organic salt, and then a polymer compound was added. Then, it was confirmed that a gel composition was similarly obtained by heating, stirring, dissolving, and cooling under the same conditions as in Example 624. From this, a thickening effect was recognized.
• Active Ingredient Solubility Evaluation The formulations described in Table 15 were evaluated for active ingredient solubility. Gallic acid, which has a poorly soluble antioxidant effect, and glutamic acid, which has a moisturizing effect, were used as active ingredients. Comparative Example 28 (ion-exchanged water) in which glutamic acid was dissolved had a solubility of ⁇ 1.0 g, whereas Examples 652 to 659 had a high solubility of ⁇ 1.0 g. A similar tendency was also obtained for gallic acid. Formulations 182, 354 and 355 were particularly superior in dissolving gallic acid, and formulations 100, 121 and 182 were particularly superior in dissolving glutamic acid.
• composition of the present invention can be used as a carrier, base or solvent for formulations, which penetrates into the hair or skin at a high concentration a sparingly soluble active ingredient, which has been difficult to formulate at a high concentration.
• the cellophane tape with the stratum corneum adhered was adhered to a slide glass that had been thinly coated with Cemedine for vinyl (manufactured by Cemedine), with the stratum corneum surface and the resin surface facing each other. This was immersed in ethanol for 10 minutes and then immersed in xylene for 2 hours. After peeling off only the tape from the slide glass with tweezers, it was further immersed in xylene for 1 hour to evaporate the xylene on the removed slide glass. Thereafter, the specimen was stained in a staining solution (0.5% by weight of brilliant green, 1.0% by weight of gentian violet) for 4 minutes, washed with running water, and dried to obtain a specimen for observation. Based on the observation results of the specimens, the specimens were observed with an optical microscope (Axio Image.A2m manufactured by ZEISS), and the four items were evaluated according to the following judgment criteria to comprehensively evaluate the improvement of the skin surface.
• Examples 660-667 had a good effect of improving the skin surface compared to Comparative Examples 29-31. From this result, compared to Comparative Example 30 (Vaseline), which is generally used to suppress dryness of the skin, and Comparative Example 31, which uses an organic base other than an amino acid as the component (A), the skin surface is excellent. It was suggested that it is an improvement effect.
• the amino acid in the formulation is the main component of the moisturizing ingredient "NMF (Natural Moisturizing Factor)" that exists in the stratum corneum, and the formulation penetrates into the skin and supplements the skin's NMF to promote moisturization. , and as a result, it is speculated that the balance of the skin surface was improved. NMF is a component that plays an important role in retaining moisture in the stratum corneum through hydrogen bonding with moisture in the skin. Therefore, it was suggested that the formulation of the present invention has the effect of improving the skin surface.
• NMF Natural Moisturizing Factor
• ascorbyl glucoside was added to 5% by mass to the 10% by mass aqueous solutions of Examples 668 to 675 and Comparative Example 32 to prepare sample solutions.
• ascorbyl glucoside was added so as to be 5% by mass with respect to water to prepare a sample solution.
• cotton impregnated with 750 ⁇ L of the prepared sample solution was applied to the inner side of the upper arm of 1 cm ⁇ 3 cm of five subjects who had rested for 30 minutes under constant temperature and humidity conditions, and allowed to stand for 5 minutes. After removing the cotton, the sample remaining on the skin surface was removed with new cotton, and left to stand for 30 minutes.
• the obtained sample for measurement was extracted with 2 ml of deionized water for 10 minutes.
• the permeation amount ( ⁇ g/cm 2 ) of ascorbyl glucoside was measured by HPLC from the extracted solution after removing foreign matter with a 0.2 ⁇ m syringe filter (manufactured by ADVANTEC).
• the values obtained by averaging the measured values of the measurement specimens collected from 5 subjects were taken as the permeation amount ( ⁇ g/cm 2 ), and the total amount of permeation amount from the 1st to 8th layers was compared.
• the values of Examples 668 to 675 and Comparative Examples 32 and 33 evaluated this time were compared and evaluated as a relative permeation rate.
• Ascorbyl glucoside was quantified using a high-performance liquid chromatograph (HPLC, Thermo Scientific Ultimate 3000) under the following conditions.
• Solvent: A: water, B: acetonitrile, C: 200 mM ammonium formate (pH 4)
• Column temperature: 30°C Syringe wash: 200 mM ammonium formate (pH 4)
• Example 668-675 had slower permeation rates than Comparative Examples 32 and 33.
• Examples 668 to 671 and 673 to 675 had a slow permeation rate, allowing the active ingredient to slowly permeate into the skin, suggesting that it is effective in cases where delayed action of the active ingredient is required.
• Example 672 similar to Comparative Examples 32 and 33, had a high permeation rate, allowing the active ingredient to quickly permeate the skin, suggesting that it is effective in cases where immediate action of the active ingredient is required.
• the composition of the present invention has different permeation rates depending on the combination of component (A) and component (B), it is presumed to be useful as a material for controlling the permeation rate of active ingredients.
• the spreadability during application was evaluated on a 5-point scale based on the feel of the skin when the evaluation sample was applied and spread. , was evaluated as 1 when the stretchability was not felt.
• the manageability of the hair after application was evaluated on a 5-point scale based on the amount of manageability of the hair when the sample was applied and blended into the hair. , and evaluated as 1 if not organized.
• Examples 676 to 687 were superior to Comparative Examples 34 and 35 in terms of ease of use during application and hair manageability after application. Among them, Examples 676, 678, 681, 684 and 686, which used oleic acid as the component (B), gave excellent feeling during use. In Examples 676 to 687, the components (A) and (B) are described in the Japanese Standards, and it is suggested that they are highly safe. Therefore, the formulation of the present invention is suitable as a hair treatment agent. It is assumed that there is.
• the hair surface improvement tests of Examples 688-731 in Tables 20A-C were performed by the following evaluation methods.
• the formulations 441 to 445 were prepared as follows.
• Formulation 441 (L-arginine): manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.
• Formulation 442 Prepared in the same manner as formulation (salt) 52.
• Formulation 443 (L-proline): manufactured by Sigma-Aldrich Japan.
• Compound 444 (lactic acid): manufactured by Kanto Kagaku Co., Ltd.
• a bleaching agent (Table 19) was applied to an untreated black hair bundle (10 cm, manufactured by Beaulux Co., Ltd.) having a mass of 1 g, left to stand for 30 minutes, and then heated at 40 ° C. Rinse thoroughly with warm water. This bleaching operation was repeated 5 times to produce damaged hair.
• samples were prepared by dissolving the formulations of Examples 688 to 731 and Comparative Examples 36 to 40 in a 50% by mass ethanol aqueous solution so as to have a concentration of 1% by mass. After immersing 1 g of the prepared damaged hair in the sample for 15 minutes, it was rinsed with hot water at 40° C.
• component (A) is a basic amino acid
• the total number of primary or secondary amino groups contained in component (A) and the total number of amino groups contained in component (B) It was found that formulations in which the ratio of the number of carboxyl groups (the total number of primary or secondary amino groups/the number of carboxyl groups) is 1 or less than 1 is highly effective in improving the hair surface.
• composition of the present invention in a hair treatment agent exhibited an excellent effect of improving the hair surface, suggesting that it is highly useful as a hair treatment agent.
• Examples 734 and 735 and Examples 736 and 738 show that when an unsaturated fatty acid is used as the component (B), the effect of stabilizing the ⁇ -helical secondary structure of keratin is excellent regardless of the blending molar ratio. was done.
• Examples 741 and 742 showed that using an unsaturated fatty acid as the component (B) was more effective in stabilizing the ⁇ -helix secondary structure of keratin than using a hydroxycarboxylic acid.
• the formulation of the present invention has a keratin stabilizing effect, so that it can retain water and moisture of the hair, maintain health and hair quality, suppress hair damage due to heat from a dryer, etc., and furthermore, for example, It can retain water and moisture in skin proteins such as keratin and nails, and maintain health.
• the compounding agent of the present invention utilizes the structural characteristics of a cation having a hydrogen-bonding functional group (having hydrogen-bonding and coordinating properties) to take advantage of the hydrogen-bond-accepting zirconium oxide (IV) It is thought that zirconium (IV) oxide was well dispersed.
• the formulation of the present invention has excellent affinity with inorganic oxides, and is used in fields that utilize dispersions of such materials, such as cosmetics, paints, inks, electronic components, and batteries. It was suggested that it is useful.

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