WO2014208399A1 - Humectant and cosmetic preparation containing same - Google Patents

Humectant and cosmetic preparation containing same Download PDF

Info

Publication number
WO2014208399A1
WO2014208399A1 PCT/JP2014/065989 JP2014065989W WO2014208399A1 WO 2014208399 A1 WO2014208399 A1 WO 2014208399A1 JP 2014065989 W JP2014065989 W JP 2014065989W WO 2014208399 A1 WO2014208399 A1 WO 2014208399A1
Authority
WO
WIPO (PCT)
Prior art keywords
formula
salt
compound represented
acid
skin
Prior art date
Application number
PCT/JP2014/065989
Other languages
French (fr)
Japanese (ja)
Inventor
坂西裕一
Original Assignee
株式会社ダイセル
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 株式会社ダイセル filed Critical 株式会社ダイセル
Publication of WO2014208399A1 publication Critical patent/WO2014208399A1/en

Links

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
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
    • 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
    • A61Q5/12—Preparations containing hair conditioners

Definitions

  • the present invention relates to a moisturizing agent used for cosmetics and the like, and a cosmetic containing the moisturizing agent.
  • a moisturizer is one of the important components of skin cosmetics and hair cosmetics.
  • 1,3-butylene glycol, propylene glycol, polyethylene glycol, glycerin, amino acids, polypeptides, and the like have been used as moisturizers for reasons such as excellent usability and safety.
  • many of these moisturizers have poor moisturizing functions, and when applied to the skin, a satisfactory moist feeling cannot be obtained.
  • stickiness was a problem. When applied to hair, it was not fully satisfactory in terms of functions such as imparting gloss, moisture, smoothness, and improving comb-through properties.
  • Patent Document 1 describes that an N-glyceryl derivative of an amino acid such as glycine or a salt thereof is used as a moisturizing agent. However, it was not yet satisfactory in terms of moisture retention.
  • an object of the present invention is to provide a moisturizing agent having safety and excellent moisturizing properties.
  • Another object of the present invention is to provide a cosmetic that is excellent in safety and can significantly improve the moisture content of the skin and hair when applied to the skin and hair.
  • the present inventor has found that the following compounds are excellent in safety and can significantly improve the moisture content of the skin and hair when applied to the skin and hair.
  • the present invention has been completed based on these findings.
  • the present invention provides the following formula (I-1) or (I-2) (In the formula, n is an integer of 0 to 3, X, Y, and Z are the same or different and each represents a hydrogen atom or a —CH 2 CH (OH) CH 2 OH group.
  • n is an integer of 0 to 3
  • X, Y, and Z are the same or different and each represents a hydrogen atom or a —CH 2 CH (OH) CH 2 OH group.
  • At least one of X, Y and Z is a —CH 2 CH (OH) CH 2 OH group.
  • at least one of X and Y is —CH 2 CH (OH) CH 2 OH.
  • Base A humectant containing a compound represented by the formula:
  • the present invention also provides the following formula (I-1) or (I-2) (In the formula, n is an integer of 0 to 3, X, Y, and Z are the same or different and each represents a hydrogen atom or a —CH 2 CH (OH) CH 2 OH group.
  • n is an integer of 0 to 3
  • X, Y, and Z are the same or different and each represents a hydrogen atom or a —CH 2 CH (OH) CH 2 OH group.
  • At least one of X, Y and Z is a —CH 2 CH (OH) CH 2 OH group.
  • at least one of X and Y is —CH 2 CH (OH) CH 2 OH.
  • Base The cosmetics containing the compound represented by these, or its salt are provided.
  • the present invention also provides the above-mentioned makeup containing 0.05 to 20% by weight of the compound represented by the formula (I-1) or (I-2) or a salt thereof in the total amount (100% by weight) of the cosmetic. Provide a fee.
  • the moisturizing agent of the present invention contains the above compound, it has excellent safety and moisturizing properties, excellent affinity to the skin and hair, does not become sticky when applied to the skin, and can give a moist feeling. When applied to, it can give gloss, moist feeling and smoothness, and can improve combing property. Therefore, it is useful as an additive for cosmetics and the like.
  • the cosmetic of the present invention contains the above compound, it is not sticky when applied to the skin, can significantly improve the moisture content of the skin, and can give a moist feeling. The moisture content of hair can be significantly improved to give gloss, moisturization and smoothness, and to improve combability.
  • the humectant of the present invention contains one or more compounds represented by the above formula (I-1) or (I-2) or a salt thereof.
  • n is an integer of 0 to 3
  • X, Y, and Z are the same or different and each represents a hydrogen atom or a —CH 2 CH (OH) CH 2 OH group.
  • X, Y and Z is a —CH 2 CH (OH) CH 2 OH group.
  • at least one of X and Y is —CH 2 CH (OH) CH 2 OH group.
  • Examples of the salt of the compound represented by the above formula (I-1) or (I-2) include acid addition salts and base addition salts.
  • Examples of the acid addition salt include organic acid salts such as acetate, lactate, glycolate, citrate, malate, tartrate, succinate, and adipate; hydrochloride, sulfate, phosphorus And inorganic acid salts such as acid salts.
  • Examples of the base addition salt include alkali metal salts such as sodium salt and potassium salt; ammonium salt; triethanolamine salt, monoethanolamine salt, 2-amino-2-methyl-1,3-propanediol salt, 2 -Organic ammonium salts such as methyl-1-propanolamine salt and arginine salt.
  • Examples of the compound represented by the above formula (I-1) or (I-2) include a compound represented by the following formula (II-1) or (II-2), glycidol and / or 3-halo- It can be produced by reacting 1,2-propanediol.
  • the compound represented by the above formula (II-1) or (II-2) is dissolved in a solvent, and under stirring, glycidol and / or Alternatively, it can be produced by performing a reaction by dropping 3-halo-1,2-propanediol.
  • the salt of the compound represented by the above formula (I-1) or (I-2) includes, for example, the compound represented by the above formula (II-1) or (II-2), glycidol and / or It can be obtained by reacting a compound represented by the formula (I-1) or (I-2) obtained by reacting 3-halo-1,2-propanediol with an acid or a base.
  • Examples of the compound represented by the formula (II-1) or (II-2) include tranexamic acid.
  • the compounds represented by the formula (II-1) or (II-2) can be used singly or in combination of two or more.
  • 3-halo-1,2-propanediol examples include 3-chloro-1,2-propanediol and 3-bromo-1,2-propanediol. These can be used individually by 1 type or in combination of 2 or more types.
  • the amount of glycidol and / or 3-halo-1,2-propanediol used is 1 mol of the compound represented by the formula (II-1) or (II-2) For example, it is about 1 to 6 mol, preferably 1 to 3 mol.
  • Examples of the acid used to form the salt include organic acids such as acetic acid, lactic acid, glycolic acid, citric acid, malic acid, tartaric acid, succinic acid, and adipic acid; inorganic acids such as hydrochloric acid, sulfuric acid, and phosphoric acid.
  • Examples of the base include hydroxides of alkali metals such as sodium hydroxide and potassium hydroxide; ammonia; triethanolamine, monoethanolamine, 2-amino-2-methyl-1,3-propanediol, 2-amino Examples include amines such as -2-methyl-1-propanol; basic amino acids such as arginine.
  • the reaction of the compound represented by the above formula (II-1) or (II-2) with glycidol and / or 3-halo-1,2-propanediol is preferably performed in the presence of a solvent.
  • a solvent include water, hydrous lower alcohol, hydrous acetone, hydrous dimethylformamide, hydrous dimethyl sulfoxide, hydrous methylcellosolve, hydrous N-methylpyrrolidone and the like. These can be used alone or in combination of two or more. In the present invention, it is particularly preferable from the viewpoint of safety to use a solvent having a water content of 20% or more.
  • the pH during the reaction is, for example, about 8 to 11.
  • the reaction rate tends to be slow.
  • the pH exceeds the above range the reaction rate is increased, but there is a tendency that off-flavors and coloring are likely to occur.
  • a base or acid can be used to adjust the pH.
  • the base include potassium hydroxide, sodium hydroxide, lithium hydroxide, sodium carbonate, potassium carbonate and the like.
  • the acid include organic acids such as acetic acid, lactic acid, glycolic acid, citric acid, malic acid, tartaric acid, succinic acid, and adipic acid; inorganic acids such as hydrochloric acid, sulfuric acid, and phosphoric acid.
  • the reaction temperature is, for example, about 30 to 90 ° C.
  • the reaction rate tends to be slow.
  • the reaction temperature exceeds the above range, the generation of a strange odor or coloring tends to occur.
  • the dripping time of glycidol and / or 3-halo-1,2-propanediol varies depending on the amount of dripping and can be appropriately adjusted.
  • stirring is preferably continued for about 3 to 15 hours while maintaining the reaction temperature.
  • the reaction can be carried out by any method such as batch, semi-batch and continuous methods.
  • the reaction product can be separated and purified by, for example, separation / purification means such as filtration, concentration, distillation, extraction, crystallization, recrystallization, adsorption, column chromatography, or a combination of these.
  • reaction product obtained by the above reaction contains an aqueous solvent
  • the reaction product contains an organic solvent
  • the organic solvent is preferably removed by vacuum distillation or the like and then added to the cosmetic.
  • the reaction product obtained by the above reaction includes the following formula (III-1) or (III -2) [Wherein, n is an integer of 0 to 3, X ′, Y ′, and Z ′ are the same or different and represent a hydrogen atom, a —CH 2 CH (OH) CH 2 OH group, or — [CH 2 CH (OH)] CH 2 O] m —CH 2 CH (OH) CH 2 OH group (m is an integer of 1 or more), and at least one of X ′, Y ′ and Z ′ in formula (III-1), At least one of X ′ and Y ′ in III-2) is — [CH 2 CH (OH) CH 2 O] m —CH 2 CH (OH) CH 2 OH group] Or a salt thereof may be included.
  • these compounds may be contained together with the compound represented by the above formula (I-1) or (I-2) or a salt thereof.
  • the proportion of the compound represented by (I-1) or (I-2) or a salt thereof is, for example, 2% by weight or more, preferably 5% by weight or more, more preferably 30% by weight or more, and particularly preferably 50% by weight. % Or more, most preferably 70% by weight or more.
  • the compound represented by the above formula (I-1) or (I-2) or a salt thereof can retain water in the hydrophilic group portion and can exert a strong intermolecular interaction. It is possible to reduce the amount of moisture transpiration, or it has excellent moisture retention.
  • the moisturizing agent of the present invention contains one or more compounds represented by the above formula (I-1) or (I-2) or a salt thereof.
  • the humectant of the present invention preferably contains at least the compound represented by the above formula (I-1), and Z in the compound represented by the above formula (I-1) is a hydrogen atom. It is particularly preferred to contain at least a compound, and most preferred to contain at least a compound represented by the following formula (I-1-1).
  • the compound represented by the following formula (I-1-1) has a hydrogen atom bonded to a cyclohexyl structure and a nitrogen atom, and thereby can exert a particularly strong intermolecular interaction, and extremely reduces the amount of water transpiration. Can be small.
  • X and Y are the same or different and each represents a hydrogen atom or a —CH 2 CH (OH) CH 2 OH group, and at least one of X and Y is —CH 2 CH (OH ) CH 2 OH group.
  • the moisturizing agent of the present invention has excellent moisturizing properties, when it is blended in skin cosmetics and hair cosmetics, skin cosmetics and hair cosmetics having an excellent moisturizing effect can be obtained. Furthermore, the moisturizing agent of the present invention is excellent in usability, stability, safety, and rough skin improvement effect. Therefore, when used in skin cosmetics, in addition to moisturizing properties, the usability (non-sticky, moisturizing) Skin cosmetics excellent in stability, safety, and rough skin improvement. Also, when used in hair cosmetics, in addition to moisture retention, it is excellent in usability (non-sticky, moist, etc.), imparts gloss, moisturization and smoothness, and improves combability A hair cosmetic material having an effect is obtained.
  • the cosmetic of the present invention is characterized by containing one or more compounds represented by the above formula (I-1) or (I-2) or a salt thereof as a humectant.
  • the cosmetic of the present invention contains two or more compounds represented by the above formula (I-1) or (I-2), or salts thereof, the above formula (I-1) or ( A compound represented by I-2) or a salt thereof may be added, and contains two or more compounds represented by the above formula (I-1) or (I-2) or a salt thereof in advance. You may manufacture a mixture and mix
  • the cosmetics of the present invention include cosmetics, pharmaceuticals, and quasi-drugs applied to the outer skin (including the scalp) and hair, such as facial cosmetics such as lotions, emulsions, creams, packs, etc.
  • facial cosmetics such as lotions, emulsions, creams, packs, etc.
  • Skin cosmetics such as makeup cosmetics such as foundations, lipsticks and eye shadows; shampoos, hair rinses, hair conditioners, hair creams, hair dyes, hair dyes, pre- and post-treatments for hair dyes, split hair coats, etc. Can be mentioned.
  • the content of the compound represented by the above formula (I-1) or (I-2) or a salt thereof in the total amount of the cosmetic of the present invention is, for example, 0.05. It is ⁇ 20.00% by weight, preferably 0.1 to 10.0% by weight.
  • the content of the compound represented by the above formula (I-1) or (I-2) or a salt thereof is below the above range, it may be difficult to obtain effects such as moisturizing property and improvement in use feeling.
  • the content of the compound represented by the above formula (I-1) or (I-2) or a salt thereof exceeds the above range, an effect corresponding to the content cannot be obtained and it is only uneconomical. In addition, there may be problems in formulation and a sticky feeling when applied to skin and hair.
  • the cosmetic of the present invention includes components used in normal skin cosmetics and hair cosmetics (for example, Water, oily raw materials, surfactants, thickeners, polymer substances, powders, drugs, antioxidants, UV absorbers, fragrances, chelating agents, animal and plant extracts, hydrolyzed peptides that hydrolyze animal and plant derived proteins And derivatives thereof) can be appropriately blended.
  • components used in normal skin cosmetics and hair cosmetics for example, Water, oily raw materials, surfactants, thickeners, polymer substances, powders, drugs, antioxidants, UV absorbers, fragrances, chelating agents, animal and plant extracts, hydrolyzed peptides that hydrolyze animal and plant derived proteins And derivatives thereof
  • the dosage form of the cosmetic of the present invention is not particularly limited, and any of a solution system, a solubilization system, an emulsification system, a gel system, a powder dispersion system, a water-oil two-layer system, and the like can be used. It can be appropriately selected depending on the case.
  • the cosmetic of the present invention can be produced by blending the compound represented by the above formula (I-1) or (I-2), or a salt thereof, and, if necessary, the above optional blending components.
  • the cosmetic of the present invention contains the compound represented by the above formula (I-1) or (I-2) or a salt thereof, the moisturizing property, usability, stability, safety, and skin roughening effect are improved. Excellent.
  • the cosmetic composition of the present invention is applied to the skin, it is not sticky, and the moisture content of the skin can be significantly improved to give a moist feeling.
  • the moisture content of the hair is significantly improved. It can give gloss, moisture, smoothness, and can improve combability.
  • Example 1 Synthesis of moisturizer (N-glyceryl tranexamate)
  • a 3 liter three-necked round bottom flask was charged with 10.0 g (0.064 mol) of tranexamic acid and 100 g of water, adjusted to pH 9.5 by adding an aqueous sodium hydroxide solution, and then heated to about 60 ° C. While stirring, 4.7 g (0.064 mol) of glycidol was gradually added dropwise over about 1 hour, and after completion of the addition, stirring was continued for 6 hours to complete the reaction.
  • N-glyceryl tranexamate a viscous substance.
  • the structure of the obtained N-glyceryl tranexamate was confirmed by 1 H-NMR.
  • the moisture content was measured using a skin surface horn layer water content measuring apparatus (trade name “Skicon 200-EX”, manufactured by IBI Co., Ltd.) and the moisture retention was evaluated according to the following criteria. Criteria for skin moisturizing effect ⁇ : Conductance value change rate is 20% or more ⁇ : Conductance value change rate is 10% or more and less than 20% ⁇ : Conductance value change rate is less than 10%
  • the compound represented by the formula (I-1) or (I-2) of the present invention, or a salt thereof is superior in moisture retention as compared with a compound conventionally used as a moisturizing agent. all right.
  • the moisturizing agent of the present invention is excellent in safety and moisturizing property, excellent in affinity to skin and hair, does not sticky when applied to the skin, can give a moist feeling, gloss when applied to hair, A moist feeling and smoothness can be imparted and combing ability can be improved. Therefore, it is useful as an additive for cosmetics and the like.

Abstract

Provided is a humectant which has excellent moisture retaining properties and safety. A humectant according to the present invention contains a compound represented by formula (I-1) or (I-2), or a salt thereof. In the formulae, n represents an integer of 0-3; and X, Y and Z may be the same or different, and each represents a hydrogen atom or a -CH2CH(OH)CH2OH group. In this connection, in formula (I-1), at least one of X, Y and Z represents a -CH2CH(OH)CH2OH group; and in formula (I-2), at least one of X and Y represents a -CH2CH(OH)CH2OH group.

Description

保湿剤、及びそれを含有する化粧料Moisturizer and cosmetic containing the same
　本発明は、化粧料等に使用する保湿剤、及び前記保湿剤を含有する化粧料に関する。本願は、２０１３年６月２６日に日本に出願した、特願２０１３－１３３７９２号の優先権を主張し、その内容をここに援用する。 The present invention relates to a moisturizing agent used for cosmetics and the like, and a cosmetic containing the moisturizing agent. This application claims the priority of Japanese Patent Application No. 2013-133792 for which it applied to Japan on June 26, 2013, and uses the content here.
　皮膚化粧料や毛髪化粧料の重要な構成成分の１つに保湿剤が挙げられる。従来、保湿剤としては、使用性、安全性に優れる等の理由から、１，３－ブチレングリコール、プロピレングリコール、ポリエチレングリコール、グリセリン、アミノ酸、ポリペプチド等が用いられてきた。しかしながら、これらの保湿剤の多くは保湿機能に乏しく、皮膚に塗布した場合、満足できるしっとり感が得られなかった。その上、べたつく点も問題であった。毛髪に塗布した場合は、艶、潤い感、なめらかさを付与したり、櫛通り性を改善する等の機能面で十分に満足できるものでなかった。 A moisturizer is one of the important components of skin cosmetics and hair cosmetics. Conventionally, 1,3-butylene glycol, propylene glycol, polyethylene glycol, glycerin, amino acids, polypeptides, and the like have been used as moisturizers for reasons such as excellent usability and safety. However, many of these moisturizers have poor moisturizing functions, and when applied to the skin, a satisfactory moist feeling cannot be obtained. In addition, stickiness was a problem. When applied to hair, it was not fully satisfactory in terms of functions such as imparting gloss, moisture, smoothness, and improving comb-through properties.
　特許文献１には、グリシン等のアミノ酸のＮ－グリセリル誘導体又はその塩を保湿剤として使用することが記載されている。しかし、保湿性の点で未だ満足できるものではなかった。 Patent Document 1 describes that an N-glyceryl derivative of an amino acid such as glycine or a salt thereof is used as a moisturizing agent. However, it was not yet satisfactory in terms of moisture retention.
特許第４３９１４７３号公報Japanese Patent No. 4391473
　従って、本発明の目的は、安全性と優れた保湿性を有する保湿剤を提供することにある。
　本発明の他の目的は、安全性に優れ、皮膚や毛髪に適用することにより、皮膚や毛髪の水分量を有意に向上することができる化粧料を提供することにある。 Accordingly, an object of the present invention is to provide a moisturizing agent having safety and excellent moisturizing properties.
Another object of the present invention is to provide a cosmetic that is excellent in safety and can significantly improve the moisture content of the skin and hair when applied to the skin and hair.
　本発明者は上記課題を解決するため鋭意検討した結果、下記化合物は安全性に優れ、皮膚や毛髪に適用することにより、皮膚や毛髪の水分量を有意に向上することを見いだした。本発明はこれらの知見に基づいて完成させたものである。 As a result of intensive studies to solve the above problems, the present inventor has found that the following compounds are excellent in safety and can significantly improve the moisture content of the skin and hair when applied to the skin and hair. The present invention has been completed based on these findings.
　すなわち、本発明は、下記式（I-1）若しくは（I-2）
Figure JPOXMLDOC01-appb-C000003
 （式中、ｎは０～３の整数、Ｘ、Ｙ、Ｚは同一又は異なって、水素原子又は－ＣＨ2ＣＨ（ＯＨ）ＣＨ2ＯＨ基を示す。尚、式（I-1）中、Ｘ、Ｙ、Ｚの少なくとも１つは－ＣＨ2ＣＨ（ＯＨ）ＣＨ2ＯＨ基であり、式（I-2）中、Ｘ、Ｙの少なくとも１つは－ＣＨ2ＣＨ（ＯＨ）ＣＨ2ＯＨ基である）
で表される化合物、又はその塩を含有する保湿剤を提供する。 That is, the present invention provides the following formula (I-1) or (I-2)
Figure JPOXMLDOC01-appb-C000003
 (In the formula, n is an integer of 0 to 3, X, Y, and Z are the same or different and each represents a hydrogen atom or a —CH 2 CH (OH) CH 2 OH group. In the formula (I-1), At least one of X, Y and Z is a —CH 2 CH (OH) CH 2 OH group. In the formula (I-2), at least one of X and Y is —CH 2 CH (OH) CH 2 OH. Base)
A humectant containing a compound represented by the formula:
　本発明は、また、下記式（I-1）若しくは（I-2）
Figure JPOXMLDOC01-appb-C000004
 （式中、ｎは０～３の整数、Ｘ、Ｙ、Ｚは同一又は異なって、水素原子又は－ＣＨ2ＣＨ（ＯＨ）ＣＨ2ＯＨ基を示す。尚、式（I-1）中、Ｘ、Ｙ、Ｚの少なくとも１つは－ＣＨ2ＣＨ（ＯＨ）ＣＨ2ＯＨ基であり、式（I-2）中、Ｘ、Ｙの少なくとも１つは－ＣＨ2ＣＨ（ＯＨ）ＣＨ2ＯＨ基である）
で表される化合物、又はその塩を含有する化粧料を提供する。 The present invention also provides the following formula (I-1) or (I-2)
Figure JPOXMLDOC01-appb-C000004
 (In the formula, n is an integer of 0 to 3, X, Y, and Z are the same or different and each represents a hydrogen atom or a —CH 2 CH (OH) CH 2 OH group. In the formula (I-1), At least one of X, Y and Z is a —CH 2 CH (OH) CH 2 OH group. In the formula (I-2), at least one of X and Y is —CH 2 CH (OH) CH 2 OH. Base)
The cosmetics containing the compound represented by these, or its salt are provided.
　本発明は、また、式（I-1）若しくは（I-2）で表される化合物、又はその塩を、化粧料全量（１００重量％）の０．０５～２０重量％含有する前記の化粧料を提供する。 The present invention also provides the above-mentioned makeup containing 0.05 to 20% by weight of the compound represented by the formula (I-1) or (I-2) or a salt thereof in the total amount (100% by weight) of the cosmetic. Provide a fee.
　本発明の保湿剤は上記化合物を含有するため、安全性及び保湿性に優れ、皮膚や毛髪への親和性に優れ、皮膚に適用した場合はべたつかず、しっとり感を付与することができ、毛髪に適用した場合は艶、潤い感、なめらかさを付与し、櫛通り性を改善することができる。そのため、化粧料等の添加剤として有用である。
　また、本発明の化粧料は上記化合物を含有するため、皮膚に適用した場合はべたつかず、皮膚の水分量を有意に向上して、しっとり感を付与することができ、毛髪に適用した場合は、毛髪の水分量を有意に向上して、艶、潤い感、なめらかさを付与し、櫛通り性を改善することができる。 Since the moisturizing agent of the present invention contains the above compound, it has excellent safety and moisturizing properties, excellent affinity to the skin and hair, does not become sticky when applied to the skin, and can give a moist feeling. When applied to, it can give gloss, moist feeling and smoothness, and can improve combing property. Therefore, it is useful as an additive for cosmetics and the like.
In addition, since the cosmetic of the present invention contains the above compound, it is not sticky when applied to the skin, can significantly improve the moisture content of the skin, and can give a moist feeling. The moisture content of hair can be significantly improved to give gloss, moisturization and smoothness, and to improve combability.
　［保湿剤］
　本発明の保湿剤は、上記式（I-1）若しくは（I-2）で表される化合物、又はその塩を１種又は２種以上含有する。式中、ｎは０～３の整数、Ｘ、Ｙ、Ｚは同一又は異なって、水素原子又は－ＣＨ2ＣＨ（ＯＨ）ＣＨ2ＯＨ基を示す。尚、式（I-1）中、Ｘ、Ｙ、Ｚの少なくとも１つは－ＣＨ2ＣＨ（ＯＨ）ＣＨ2ＯＨ基であり、式（I-2）中、Ｘ、Ｙの少なくとも１つは－ＣＨ2ＣＨ（ＯＨ）ＣＨ2ＯＨ基である。 [Humectant]
The humectant of the present invention contains one or more compounds represented by the above formula (I-1) or (I-2) or a salt thereof. In the formula, n is an integer of 0 to 3, and X, Y, and Z are the same or different and each represents a hydrogen atom or a —CH 2 CH (OH) CH 2 OH group. In the formula (I-1), at least one of X, Y and Z is a —CH 2 CH (OH) CH 2 OH group. In the formula (I-2), at least one of X and Y is —CH 2 CH (OH) CH 2 OH group.
　上記式（I-1）若しくは（I-2）で表される化合物の塩としては酸付加塩又は塩基付加塩を挙げることができる。前記酸付加塩としては、例えば、酢酸塩、乳酸塩、グリコール酸塩、クエン酸塩、リンゴ酸塩、酒石酸塩、コハク酸塩、アジピン酸塩等の有機酸塩；塩酸塩、硫酸塩、リン酸塩等の無機酸塩等を挙げることができる。前記塩基付加塩としては、例えば、ナトリウム塩、カリウム塩等のアルカリ金属塩；アンモニウム塩；トリエタノールアミン塩、モノエタノールアミン塩、２－アミノ－２－メチル－１，３－プロパンジオール塩、２－メチル－１－プロパノールアミン塩、アルギニン塩等の有機アンモニウム塩等を挙げることができる。 Examples of the salt of the compound represented by the above formula (I-1) or (I-2) include acid addition salts and base addition salts. Examples of the acid addition salt include organic acid salts such as acetate, lactate, glycolate, citrate, malate, tartrate, succinate, and adipate; hydrochloride, sulfate, phosphorus And inorganic acid salts such as acid salts. Examples of the base addition salt include alkali metal salts such as sodium salt and potassium salt; ammonium salt; triethanolamine salt, monoethanolamine salt, 2-amino-2-methyl-1,3-propanediol salt, 2 -Organic ammonium salts such as methyl-1-propanolamine salt and arginine salt.
　上記式（I-1）若しくは（I-2）で表される化合物は、例えば、下記式（II-1）又は（II-2）で表される化合物と、グリシドール及び／又は３－ハロ－１，２－プロパンジオールを反応させることにより製造することができ、例えば、上記式（II-1）又は（II-2）で表される化合物を溶媒中に溶解し、撹拌下、グリシドール及び／又は３－ハロ－１，２－プロパンジオールを滴下して反応を行うことにより製造することができる。 Examples of the compound represented by the above formula (I-1) or (I-2) include a compound represented by the following formula (II-1) or (II-2), glycidol and / or 3-halo- It can be produced by reacting 1,2-propanediol. For example, the compound represented by the above formula (II-1) or (II-2) is dissolved in a solvent, and under stirring, glycidol and / or Alternatively, it can be produced by performing a reaction by dropping 3-halo-1,2-propanediol.
Figure JPOXMLDOC01-appb-C000005
Figure JPOXMLDOC01-appb-C000005
　また、上記式（I-1）若しくは（I-2）で表される化合物の塩は、例えば、上記式（II-1）又は（II-2）で表される化合物と、グリシドール及び／又は３－ハロ－１，２－プロパンジオールを反応させて得られる式（I-1）若しくは（I-2）で表される化合物に酸や塩基を反応させることにより得ることができる。その他、上記式（II-1）又は（II-2）で表される化合物に酸や塩基を反応させて得られる上記式（II-1）又は（II-2）で表される化合物の塩と、グリシドール及び／又は３－ハロ－１，２－プロパンジオールを反応させることにより得ることもできる。 Further, the salt of the compound represented by the above formula (I-1) or (I-2) includes, for example, the compound represented by the above formula (II-1) or (II-2), glycidol and / or It can be obtained by reacting a compound represented by the formula (I-1) or (I-2) obtained by reacting 3-halo-1,2-propanediol with an acid or a base. In addition, a salt of the compound represented by the above formula (II-1) or (II-2) obtained by reacting the compound represented by the above formula (II-1) or (II-2) with an acid or a base And glycidol and / or 3-halo-1,2-propanediol.
　上記式（II-1）又は（II-2）で表される化合物としては、例えば、トラネキサム酸等を挙げることができる。上記式（II-1）又は（II-2）で表される化合物は１種を単独で、又は２種以上を組み合わせて使用することができる。 Examples of the compound represented by the formula (II-1) or (II-2) include tranexamic acid. The compounds represented by the formula (II-1) or (II-2) can be used singly or in combination of two or more.
　前記３－ハロ－１，２－プロパンジオールとしては、例えば、３－クロロ－１，２－プロパンジオールや３－ブロモ－１，２－プロパンジオール等を挙げることができる。これらは、１種を単独で、又は２種以上を組み合わせて使用することができる。 Examples of the 3-halo-1,2-propanediol include 3-chloro-1,2-propanediol and 3-bromo-1,2-propanediol. These can be used individually by 1 type or in combination of 2 or more types.
　グリシドール及び／又は３－ハロ－１，２－プロパンジオールの使用量（２種以上使用する場合はその総量）としては、式（II-1）又は（II-2）で表される化合物１モルに対して、例えば１～６モル程度、好ましくは１～３モルである。 The amount of glycidol and / or 3-halo-1,2-propanediol used (the total amount when two or more are used) is 1 mol of the compound represented by the formula (II-1) or (II-2) For example, it is about 1 to 6 mol, preferably 1 to 3 mol.
　前記塩の形成に使用する酸としては、例えば、酢酸、乳酸、グリコール酸、クエン酸、リンゴ酸、酒石酸、コハク酸、アジピン酸等の有機酸；塩酸、硫酸、リン酸等の無機酸等を挙げることができる。塩基としては、例えば、水酸化ナトリウム、水酸化カリウム等のアルカリ金属の水酸化物；アンモニア；トリエタノールアミン、モノエタノールアミン、２－アミノ－２－メチル－１，３－プロパンジオール、２－アミノ－２－メチル－１－プロパノール等のアミン；アルギニン等の塩基性アミノ酸等を挙げることができる。 Examples of the acid used to form the salt include organic acids such as acetic acid, lactic acid, glycolic acid, citric acid, malic acid, tartaric acid, succinic acid, and adipic acid; inorganic acids such as hydrochloric acid, sulfuric acid, and phosphoric acid. Can be mentioned. Examples of the base include hydroxides of alkali metals such as sodium hydroxide and potassium hydroxide; ammonia; triethanolamine, monoethanolamine, 2-amino-2-methyl-1,3-propanediol, 2-amino Examples include amines such as -2-methyl-1-propanol; basic amino acids such as arginine.
　上記式（II-1）又は（II-2）で表される化合物と、グリシドール及び／又は３－ハロ－１，２－プロパンジオールの反応は、溶媒の存在下で行うことが好ましい。前記溶媒としては、例えば、水、含水低級アルコール、含水アセトン、含水ジメチルホルムアミド、含水ジメチルスルホキシド、含水メチルセルソルブ、含水Ｎ－メチルピロリドン等を挙げることができる。これらは１種を単独で、又は２種以上を組み合わせて使用することができる。本発明においては、なかでも含水率２０％以上の溶媒を使用することが、安全性の点で好ましい。 The reaction of the compound represented by the above formula (II-1) or (II-2) with glycidol and / or 3-halo-1,2-propanediol is preferably performed in the presence of a solvent. Examples of the solvent include water, hydrous lower alcohol, hydrous acetone, hydrous dimethylformamide, hydrous dimethyl sulfoxide, hydrous methylcellosolve, hydrous N-methylpyrrolidone and the like. These can be used alone or in combination of two or more. In the present invention, it is particularly preferable from the viewpoint of safety to use a solvent having a water content of 20% or more.
　前記反応時のｐＨは、例えば８～１１程度である。ｐＨが上記範囲を下回ると、反応速度が遅くなる傾向がある。一方、ｐＨが上記範囲を上回ると、反応速度は速くなるが、異臭の発生や着色が起こり易くなる傾向がある。 The pH during the reaction is, for example, about 8 to 11. When the pH is below the above range, the reaction rate tends to be slow. On the other hand, when the pH exceeds the above range, the reaction rate is increased, but there is a tendency that off-flavors and coloring are likely to occur.
　また、前記反応により得られる反応生成物（＝保湿剤）の最終ｐＨとしては、化粧料に含有させて保湿剤として使用するため、例えば４～９程度が好ましい。 Also, the final pH of the reaction product (= humectant) obtained by the above reaction is preferably about 4 to 9, for example, because it is contained in cosmetics and used as a moisturizer.
　ｐＨの調整には塩基や酸を用いることができる。前記塩基としては、例えば、水酸化カリウム、水酸化ナトリウム、水酸化リチウム、炭酸ナトリウム、炭酸カリウム等を挙げることができる。前記酸としては、例えば、酢酸、乳酸、グリコール酸、クエン酸、リンゴ酸、酒石酸、コハク酸、アジピン酸等の有機酸；塩酸、硫酸、リン酸等の無機酸等を挙げることができる。 A base or acid can be used to adjust the pH. Examples of the base include potassium hydroxide, sodium hydroxide, lithium hydroxide, sodium carbonate, potassium carbonate and the like. Examples of the acid include organic acids such as acetic acid, lactic acid, glycolic acid, citric acid, malic acid, tartaric acid, succinic acid, and adipic acid; inorganic acids such as hydrochloric acid, sulfuric acid, and phosphoric acid.
　反応温度は、例えば３０～９０℃程度である。反応温度が上記範囲を下回ると、反応速度が遅くなる傾向がある。一方、反応温度が上記範囲を上回ると、異臭の発生や着色が起こり易くなる傾向がある。 The reaction temperature is, for example, about 30 to 90 ° C. When the reaction temperature is below the above range, the reaction rate tends to be slow. On the other hand, when the reaction temperature exceeds the above range, the generation of a strange odor or coloring tends to occur.
　グリシドール及び／又は３－ハロ－１，２－プロパンジオールの滴下時間はこれらの滴下量により異なり、適宜調整することができる。滴下終了後は、反応を完結させるために、前記反応温度を維持しつつ３～１５時間程度撹拌を続けることが好ましい。 The dripping time of glycidol and / or 3-halo-1,2-propanediol varies depending on the amount of dripping and can be appropriately adjusted. After completion of the dropwise addition, in order to complete the reaction, stirring is preferably continued for about 3 to 15 hours while maintaining the reaction temperature.
　前記反応はバッチ式、セミバッチ式、連続式などの何れの方法で行うこともできる。反応終了後、反応生成物は、例えば、濾過、濃縮、蒸留、抽出、晶析、再結晶、吸着、カラムクロマトグラフィー等の分離精製手段やこれらを組み合わせた手段により分離精製できる。 The reaction can be carried out by any method such as batch, semi-batch and continuous methods. After completion of the reaction, the reaction product can be separated and purified by, for example, separation / purification means such as filtration, concentration, distillation, extraction, crystallization, recrystallization, adsorption, column chromatography, or a combination of these.
　上記反応で得られた反応生成物が水溶媒を含む場合はそのままの状態（＝水溶液の状態）、或いは水を留去した状態で化粧料に添加することができる。一方、反応生成物が有機溶媒を含む場合は、減圧蒸留等によって有機溶媒を除去した後、化粧料に添加することが好ましい。 When the reaction product obtained by the above reaction contains an aqueous solvent, it can be added to the cosmetic as it is (= in the form of an aqueous solution) or in a state where water is distilled off. On the other hand, when the reaction product contains an organic solvent, the organic solvent is preferably removed by vacuum distillation or the like and then added to the cosmetic.
　また、上記反応で得られた反応生成物には、上記式（I-1）若しくは（I-2）で表される化合物、又はその塩以外にも、下記式（III-1）又は（III-2）
Figure JPOXMLDOC01-appb-C000006
 ［式中、ｎは０～３の整数、Ｘ’、Ｙ’、Ｚ’は同一又は異なって、水素原子、－ＣＨ2ＣＨ（ＯＨ）ＣＨ2ＯＨ基、又は－［ＣＨ2ＣＨ（ＯＨ）ＣＨ2Ｏ］m－ＣＨ2ＣＨ（ＯＨ）ＣＨ2ＯＨ基（ｍは１以上の整数）を示し、式（III-1）中のＸ’、Ｙ’、Ｚ’の少なくとも１つ、式（III-2）中のＸ’、Ｙ’の少なくとも１つは－［ＣＨ2ＣＨ（ＯＨ）ＣＨ2Ｏ］m－ＣＨ2ＣＨ（ＯＨ）ＣＨ2ＯＨ基である］
で表される化合物、又はその塩も含まれる場合がある。本発明の保湿剤には、これらの化合物が、上記式（I-1）若しくは（I-2）で表される化合物、又はその塩と共に含まれていてもよいが、保湿剤全量における上記式（I-1）若しくは（I-2）で表される化合物、又はその塩の割合は、例えば２重量％以上、好ましくは５重量％以上、より好ましくは３０重量％以上、特に好ましくは５０重量％以上、最も好ましくは７０重量％以上である。 In addition to the compound represented by the above formula (I-1) or (I-2) or a salt thereof, the reaction product obtained by the above reaction includes the following formula (III-1) or (III -2)
Figure JPOXMLDOC01-appb-C000006
 [Wherein, n is an integer of 0 to 3, X ′, Y ′, and Z ′ are the same or different and represent a hydrogen atom, a —CH 2 CH (OH) CH 2 OH group, or — [CH 2 CH (OH)] CH 2 O] m —CH 2 CH (OH) CH 2 OH group (m is an integer of 1 or more), and at least one of X ′, Y ′ and Z ′ in formula (III-1), At least one of X ′ and Y ′ in III-2) is — [CH 2 CH (OH) CH 2 O] m —CH 2 CH (OH) CH 2 OH group]
Or a salt thereof may be included. In the humectant of the present invention, these compounds may be contained together with the compound represented by the above formula (I-1) or (I-2) or a salt thereof. The proportion of the compound represented by (I-1) or (I-2) or a salt thereof is, for example, 2% by weight or more, preferably 5% by weight or more, more preferably 30% by weight or more, and particularly preferably 50% by weight. % Or more, most preferably 70% by weight or more.
　上記式（I-1）若しくは（I-2）で表される化合物、又はその塩は、親水基部分に水を保持することができると共に、強い分子間相互作用を発揮することができ、それにより水分蒸散量を低減することができるためか、優れた保湿性を有する。 The compound represented by the above formula (I-1) or (I-2) or a salt thereof can retain water in the hydrophilic group portion and can exert a strong intermolecular interaction. It is possible to reduce the amount of moisture transpiration, or it has excellent moisture retention.
　本発明の保湿剤は上記式（I-1）若しくは（I-2）で表される化合物、又はその塩を１種又は２種以上含有する。本発明の保湿剤としては、なかでも、上記式（I-1）で表される化合物を少なくとも含有することが好ましく、上記式（I-1）で表される化合物におけるＺが水素原子である化合物を少なくとも含有することが特に好ましく、下記式（I-1-1）で表される化合物を少なくとも含有することが最も好ましい。 The moisturizing agent of the present invention contains one or more compounds represented by the above formula (I-1) or (I-2) or a salt thereof. The humectant of the present invention preferably contains at least the compound represented by the above formula (I-1), and Z in the compound represented by the above formula (I-1) is a hydrogen atom. It is particularly preferred to contain at least a compound, and most preferred to contain at least a compound represented by the following formula (I-1-1).
　下記式（I-1-1）で表される化合物は、シクロヘキシル構造と窒素原子に結合する水素原子を有し、それにより特に強い分子間相互作用を発揮することができ、水分蒸散量を極めて小さくすることができる。式（I-1-1）中、Ｘ、Ｙは同一又は異なって、水素原子又は－ＣＨ2ＣＨ（ＯＨ）ＣＨ2ＯＨ基を示し、Ｘ、Ｙの少なくとも１つは－ＣＨ2ＣＨ（ＯＨ）ＣＨ2ＯＨ基である。 The compound represented by the following formula (I-1-1) has a hydrogen atom bonded to a cyclohexyl structure and a nitrogen atom, and thereby can exert a particularly strong intermolecular interaction, and extremely reduces the amount of water transpiration. Can be small. In formula (I-1-1), X and Y are the same or different and each represents a hydrogen atom or a —CH 2 CH (OH) CH 2 OH group, and at least one of X and Y is —CH 2 CH (OH ) CH 2 OH group.
Figure JPOXMLDOC01-appb-C000007
Figure JPOXMLDOC01-appb-C000007
　本発明の保湿剤は優れた保湿性を有するため、皮膚化粧料や毛髪化粧料に配合すると、優れた保湿効果を有する皮膚化粧料や毛髪化粧料を得ることができる。さらに、本発明の保湿剤は、使用性、安定性、安全性、及び肌荒れ改善効果にも優れるので、皮膚化粧料に使用した場合には、保湿性に加えて、使用性（べたつかず、しっとりしている等）、安定性、安全性、及び肌荒れ改善性に優れた皮膚化粧料が得られる。また、毛髪化粧料に使用した場合には、保湿性に加えて、使用性（べたつかず、しっとりしている等）に優れ、艶、潤い感、なめらかさを付与し、櫛通り性を改善する効果を有する毛髪化粧料が得られる。 Since the moisturizing agent of the present invention has excellent moisturizing properties, when it is blended in skin cosmetics and hair cosmetics, skin cosmetics and hair cosmetics having an excellent moisturizing effect can be obtained. Furthermore, the moisturizing agent of the present invention is excellent in usability, stability, safety, and rough skin improvement effect. Therefore, when used in skin cosmetics, in addition to moisturizing properties, the usability (non-sticky, moisturizing) Skin cosmetics excellent in stability, safety, and rough skin improvement. Also, when used in hair cosmetics, in addition to moisture retention, it is excellent in usability (non-sticky, moist, etc.), imparts gloss, moisturization and smoothness, and improves combability A hair cosmetic material having an effect is obtained.
　［化粧料］
　本発明の化粧料は保湿剤として上記式（I-1）若しくは（I-2）で表される化合物、又はその塩を１種又は２種以上含有することを特徴とする。本発明の化粧料が上記式（I-1）若しくは（I-2）で表される化合物、又はその塩を２種以上含有する場合、各々別個に製造した上記式（I-1）若しくは（I-2）で表される化合物、又はその塩を配合してもよく、予め２種以上の上記式（I-1）若しくは（I-2）で表される化合物、又はその塩を含有する混合物を製造し、これを化粧料に配合してもよい。 [Cosmetics]
The cosmetic of the present invention is characterized by containing one or more compounds represented by the above formula (I-1) or (I-2) or a salt thereof as a humectant. When the cosmetic of the present invention contains two or more compounds represented by the above formula (I-1) or (I-2), or salts thereof, the above formula (I-1) or ( A compound represented by I-2) or a salt thereof may be added, and contains two or more compounds represented by the above formula (I-1) or (I-2) or a salt thereof in advance. You may manufacture a mixture and mix | blend this with cosmetics.
　本発明の化粧料には、外皮（頭皮を含む）及び毛髪に適用される化粧料、医薬品及び、医薬部外品が含まれ、例えば、化粧水、乳液、クリーム、パック等のフェーシャル化粧料やファンデーション、口紅、アイシャドー等のメーキャップ化粧料等の皮膚化粧料；シャンプー、ヘアリンス、ヘアコンディショナー、ヘアクリーム、染毛剤、染毛料、染毛の前処理剤や後処理剤、枝毛コート剤等の毛髪化粧料を挙げることができる。 The cosmetics of the present invention include cosmetics, pharmaceuticals, and quasi-drugs applied to the outer skin (including the scalp) and hair, such as facial cosmetics such as lotions, emulsions, creams, packs, etc. Skin cosmetics such as makeup cosmetics such as foundations, lipsticks and eye shadows; shampoos, hair rinses, hair conditioners, hair creams, hair dyes, hair dyes, pre- and post-treatments for hair dyes, split hair coats, etc. Can be mentioned.
　本発明の化粧料全量における上記式（I-1）若しくは（I-2）で表される化合物、又はその塩の含有量（２種以上含有する場合はその総量）としては、例えば０．０５～２０．００重量％、好ましくは０．１～１０．０重量％である。上記式（I-1）若しくは（I-2）で表される化合物、又はその塩の含有量が上記範囲を下回ると、保湿性、使用感触向上等の効果が得られ難くなる場合がある。一方、上記式（I-1）若しくは（I-2）で表される化合物、又はその塩の含有量が上記範囲を上回ると、含有量に見合うだけの効果が得られず不経済であるだけでなく、製剤上の問題や、皮膚や毛髪に適用した場合にべたつき感を生じる場合がある。 The content of the compound represented by the above formula (I-1) or (I-2) or a salt thereof in the total amount of the cosmetic of the present invention (when two or more types are contained, the total amount thereof) is, for example, 0.05. It is ˜20.00% by weight, preferably 0.1 to 10.0% by weight. When the content of the compound represented by the above formula (I-1) or (I-2) or a salt thereof is below the above range, it may be difficult to obtain effects such as moisturizing property and improvement in use feeling. On the other hand, if the content of the compound represented by the above formula (I-1) or (I-2) or a salt thereof exceeds the above range, an effect corresponding to the content cannot be obtained and it is only uneconomical. In addition, there may be problems in formulation and a sticky feeling when applied to skin and hair.
　本発明の化粧料には、上記式（I-1）若しくは（I-2）で表される化合物、又はその塩の他に、通常の皮膚化粧料や毛髪化粧料に用いられる成分（例えば、水、油性原料、界面活性剤、増粘剤、高分子物質、粉末類、薬剤、酸化防止剤、紫外線吸収剤、香料、キレート剤、動植物抽出物、動植物由来の蛋白質を加水分解した加水分解ペプチド及びその誘導体類等）を適宜配合することができる。 In addition to the compound represented by the above formula (I-1) or (I-2) or a salt thereof, the cosmetic of the present invention includes components used in normal skin cosmetics and hair cosmetics (for example, Water, oily raw materials, surfactants, thickeners, polymer substances, powders, drugs, antioxidants, UV absorbers, fragrances, chelating agents, animal and plant extracts, hydrolyzed peptides that hydrolyze animal and plant derived proteins And derivatives thereof) can be appropriately blended.
　本発明の化粧料の剤型は特に制限されることがなく、溶液系、可溶化系、乳化系、ゲル系、粉末分散系、水－油二層系等のいずれも可能であり、用途に応じて適宜選択することができる。 The dosage form of the cosmetic of the present invention is not particularly limited, and any of a solution system, a solubilization system, an emulsification system, a gel system, a powder dispersion system, a water-oil two-layer system, and the like can be used. It can be appropriately selected depending on the case.
　本発明の化粧料は、上記式（I-1）若しくは（I-2）で表される化合物、又はその塩と、必要に応じて上記任意配合成分を配合して製造することができる。 The cosmetic of the present invention can be produced by blending the compound represented by the above formula (I-1) or (I-2), or a salt thereof, and, if necessary, the above optional blending components.
　本発明の化粧料は、上記式（I-1）若しくは（I-2）で表される化合物、又はその塩を含有するため、保湿性、使用性、安定性、安全性、肌荒れ改善効果に優れる。本発明の化粧料を皮膚に適用した場合はべたつかず、皮膚の水分量を有意に向上して、しっとり感を付与することができ、毛髪に適用した場合は、毛髪の水分量を有意に向上することができ、艶、潤い感、なめらかさを付与し、櫛通り性を改善することができる。 Since the cosmetic of the present invention contains the compound represented by the above formula (I-1) or (I-2) or a salt thereof, the moisturizing property, usability, stability, safety, and skin roughening effect are improved. Excellent. When the cosmetic composition of the present invention is applied to the skin, it is not sticky, and the moisture content of the skin can be significantly improved to give a moist feeling. When applied to the hair, the moisture content of the hair is significantly improved. It can give gloss, moisture, smoothness, and can improve combability.
　以下、実施例により本発明をより具体的に説明するが、本発明はこれらの実施例により限定されるものではない。 Hereinafter, the present invention will be described more specifically with reference to examples, but the present invention is not limited to these examples.
　実施例１［保湿剤（トラネキサム酸Ｎ－グリセリル）の合成］
　３リットルの三口丸底フラスコにトラネキサム酸１０．０ｇ（０．０６４モル）と水１００ｇを仕込み、水酸化ナトリウム水溶液を加えてｐＨを約９．５に調整した後、約６０℃に加温し、撹拌しながらグリシドール４．７ｇ（０．０６４モル）を約１時間かけて徐々に滴下し、滴下終了後、さらに６時間撹拌を続けて反応を完結させた。室温まで冷却後、希塩酸を加えてｐＨを約６．５に調整し、減圧下に水分を留去して粘稠な物質であるトラネキサム酸Ｎ－グリセリルを１５ｇ得た。
　得られたトラネキサム酸Ｎ－グリセリルの構造確認は1Ｈ－ＮＭＲにより行った。
　1H-NMR (270MHz, DMSO-d6): δ0.62-0.97(m,2H), 1.05-1.20(m,2H), 1.65-2.06(m,3H), 2.08-2.61(m,5H), 3.2-4.0(m,4H), 4.2-5.2 (m,3H) Example 1 [Synthesis of moisturizer (N-glyceryl tranexamate)]
A 3 liter three-necked round bottom flask was charged with 10.0 g (0.064 mol) of tranexamic acid and 100 g of water, adjusted to pH 9.5 by adding an aqueous sodium hydroxide solution, and then heated to about 60 ° C. While stirring, 4.7 g (0.064 mol) of glycidol was gradually added dropwise over about 1 hour, and after completion of the addition, stirring was continued for 6 hours to complete the reaction. After cooling to room temperature, dilute hydrochloric acid was added to adjust the pH to about 6.5, and water was distilled off under reduced pressure to obtain 15 g of N-glyceryl tranexamate, a viscous substance.
The structure of the obtained N-glyceryl tranexamate was confirmed by 1 H-NMR.
1 H-NMR (270 MHz, DMSO-d6): δ 0.62-0.97 (m, 2H), 1.05-1.20 (m, 2H), 1.65-2.06 (m, 3H), 2.08-2.61 (m, 5H), 3.2-4.0 (m, 4H), 4.2-5.2 (m, 3H)
　比較例１［保湿剤（Ｎ－グリセリルグリシン）の合成］
　トラネキサム酸に代えてグリシンを使用した以外は実施例１と同様にしてＮ－グリセリルグリシンを得た。 Comparative Example 1 [Synthesis of humectant (N-glyceryl glycine)]
N-glyceryl glycine was obtained in the same manner as in Example 1 except that glycine was used instead of tranexamic acid.
　評価
　実施例及び比較例で得られた保湿剤の保湿性を下記方法で評価した。また、参考例として、化粧品に保湿剤として多用される１，３－ブチレングリコール、グリセリン、トラネキサム酸、及びグリシンについても同様の方法でその吸湿性を評価した。
　＜保湿性の評価方法＞
　男女１０人のパネリストによって保湿性を評価した。
　前腕部を洗浄した後、保湿剤の濃度が５％になるように水で希釈して得られたサンプル１００μＬを塗布し、サンプル塗布前の肌コンダクタンス値及び塗布後２０分後の肌コンダクタンス値を、皮表角層水分量測定装置（商品名「スキコン２００－ＥＸ」、アイ・ビイ・エス（株）製）を用いて測定し下記基準に従って保湿性を評価した。
　肌保湿効果の判定基準
　○：コンダクタンス値変化率が２０％以上
　△：コンダクタンス値変化率が１０％以上、２０％未満
　×：コンダクタンス値変化率が１０％未満 Evaluation The moisturizing properties of the moisturizing agents obtained in Examples and Comparative Examples were evaluated by the following methods. As reference examples, the hygroscopicity of 1,3-butylene glycol, glycerin, tranexamic acid, and glycine, which are frequently used as a moisturizing agent in cosmetics, was also evaluated in the same manner.
<Method for evaluating moisture retention>
Moisturizing properties were evaluated by panelists of 10 men and women.
After washing the forearm, apply 100 μL of the sample obtained by diluting with water so that the concentration of the moisturizing agent is 5%, and determine the skin conductance value before application of the sample and the skin conductance value after 20 minutes after application. The moisture content was measured using a skin surface horn layer water content measuring apparatus (trade name “Skicon 200-EX”, manufactured by IBI Co., Ltd.) and the moisture retention was evaluated according to the following criteria.
Criteria for skin moisturizing effect ○: Conductance value change rate is 20% or more △: Conductance value change rate is 10% or more and less than 20% ×: Conductance value change rate is less than 10%
　上記結果を下記表にまとめて示す。
Figure JPOXMLDOC01-appb-T000008
 The above results are summarized in the following table.
Figure JPOXMLDOC01-appb-T000008
　上記結果から、本発明の式（I-1）若しくは（I-2）で表される化合物、又はその塩は、従来、保湿剤として使用されてきた化合物と比べて、保湿性に優れることがわかった。 From the above results, the compound represented by the formula (I-1) or (I-2) of the present invention, or a salt thereof, is superior in moisture retention as compared with a compound conventionally used as a moisturizing agent. all right.
　本発明の保湿剤は安全性及び保湿性に優れ、皮膚や毛髪への親和性に優れ、皮膚に適用した場合はべたつかず、しっとり感を付与することができ、毛髪に適用した場合は艶、潤い感、なめらかさを付与し、櫛通り性を改善することができる。そのため、化粧料等の添加剤として有用である。 The moisturizing agent of the present invention is excellent in safety and moisturizing property, excellent in affinity to skin and hair, does not sticky when applied to the skin, can give a moist feeling, gloss when applied to hair, A moist feeling and smoothness can be imparted and combing ability can be improved. Therefore, it is useful as an additive for cosmetics and the like.

Claims (3)

  1. 　下記式（I-1）若しくは（I-2）
    Figure JPOXMLDOC01-appb-C000001
     （式中、ｎは０～３の整数、Ｘ、Ｙ、Ｚは同一又は異なって、水素原子又は－ＣＨ2ＣＨ（ＯＨ）ＣＨ2ＯＨ基を示す。尚、式（I-1）中、Ｘ、Ｙ、Ｚの少なくとも１つは－ＣＨ2ＣＨ（ＯＨ）ＣＨ2ＯＨ基であり、式（I-2）中、Ｘ、Ｙの少なくとも１つは－ＣＨ2ＣＨ（ＯＨ）ＣＨ2ＯＨ基である）
    で表される化合物、又はその塩を含有する保湿剤。     The following formula (I-1) or (I-2)
    Figure JPOXMLDOC01-appb-C000001
     (In the formula, n is an integer of 0 to 3, X, Y, and Z are the same or different and each represents a hydrogen atom or a —CH 2 CH (OH) CH 2 OH group. In the formula (I-1), At least one of X, Y and Z is a —CH 2 CH (OH) CH 2 OH group. In the formula (I-2), at least one of X and Y is —CH 2 CH (OH) CH 2 OH. Base)
    A humectant containing a compound represented by the formula:
  2. 　下記式（I-1）若しくは（I-2）
    Figure JPOXMLDOC01-appb-C000002
     （式中、ｎは０～３の整数、Ｘ、Ｙ、Ｚは同一又は異なって、水素原子又は－ＣＨ2ＣＨ（ＯＨ）ＣＨ2ＯＨ基を示す。尚、式（I-1）中、Ｘ、Ｙ、Ｚの少なくとも１つは－ＣＨ2ＣＨ（ＯＨ）ＣＨ2ＯＨ基であり、式（I-2）中、Ｘ、Ｙの少なくとも１つは－ＣＨ2ＣＨ（ＯＨ）ＣＨ2ＯＨ基である）
    で表される化合物、又はその塩を含有する化粧料。     The following formula (I-1) or (I-2)
    Figure JPOXMLDOC01-appb-C000002
     (In the formula, n is an integer of 0 to 3, X, Y, and Z are the same or different and each represents a hydrogen atom or a —CH 2 CH (OH) CH 2 OH group. In the formula (I-1), At least one of X, Y and Z is a —CH 2 CH (OH) CH 2 OH group. In the formula (I-2), at least one of X and Y is —CH 2 CH (OH) CH 2 OH. Base)
    Cosmetics containing the compound represented by these, or its salt.
  3. 　式（I-1）若しくは（I-2）で表される化合物、又はその塩を、化粧料全量（１００重量％）の０．０５～２０重量％含有する請求項２に記載の化粧料。 The cosmetic according to claim 2, comprising 0.05 to 20% by weight of the total amount (100% by weight) of the compound represented by the formula (I-1) or (I-2) or a salt thereof.
PCT/JP2014/065989 2013-06-26 2014-06-17 Humectant and cosmetic preparation containing same WO2014208399A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2013133792 2013-06-26
JP2013-133792 2013-06-26

Publications (1)

Publication Number Publication Date
WO2014208399A1 true WO2014208399A1 (en) 2014-12-31

Family

ID=52141741

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2014/065989 WO2014208399A1 (en) 2013-06-26 2014-06-17 Humectant and cosmetic preparation containing same

Country Status (1)

Country Link
WO (1) WO2014208399A1 (en)

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0853337A (en) * 1994-08-11 1996-02-27 Shiseido Co Ltd Sebum suppressing agent
JPH11193212A (en) * 1997-12-26 1999-07-21 Shiseido Co Ltd Skin preparation for external use for keeping and enhancing skin ph buffering ability
JPH11193207A (en) * 1997-12-26 1999-07-21 Shiseido Co Ltd Preparation for external use for skin
WO2004052318A1 (en) * 2002-12-06 2004-06-24 Seiwa Kasei Company, Limited Cosmetic preparation containing glycerylamino acid derivative
JP2013014633A (en) * 2012-10-24 2013-01-24 Daiichi Sankyo Healthcare Co Ltd Skin care preparation for external use
JP2013053130A (en) * 2011-08-05 2013-03-21 Shiseido Co Ltd Liquid skin care composition

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0853337A (en) * 1994-08-11 1996-02-27 Shiseido Co Ltd Sebum suppressing agent
JPH11193212A (en) * 1997-12-26 1999-07-21 Shiseido Co Ltd Skin preparation for external use for keeping and enhancing skin ph buffering ability
JPH11193207A (en) * 1997-12-26 1999-07-21 Shiseido Co Ltd Preparation for external use for skin
WO2004052318A1 (en) * 2002-12-06 2004-06-24 Seiwa Kasei Company, Limited Cosmetic preparation containing glycerylamino acid derivative
JP2013053130A (en) * 2011-08-05 2013-03-21 Shiseido Co Ltd Liquid skin care composition
JP2013014633A (en) * 2012-10-24 2013-01-24 Daiichi Sankyo Healthcare Co Ltd Skin care preparation for external use

Similar Documents

Publication Publication Date Title
JP4695383B2 (en) Increased wetting efficacy using hydroxyalkylureas
KR101635239B1 (en) Alginine derivative and cosmetic comprising same
JP2000355531A (en) Oily raw material composition
JP2017218419A (en) Cosmetic base and cosmetic product containing amide alcohol
JP2003089623A (en) New quaternary ammonium compound composition
JP5821420B2 (en) Polysaccharide derivative composition
JP2021161064A (en) Discoloration-suppressing composition of ferulic acid
EP3176150B1 (en) Medium-chain acyl basic amino acid derivative
JP2003176210A (en) Emulsion type cosmetic
WO2014208399A1 (en) Humectant and cosmetic preparation containing same
JP4689393B2 (en) Hair tension / scrubbing improver and hair cosmetics
KR102006951B1 (en) Cosmetics compositions for prevention and improvement of dandruff or itching
WO2015037419A1 (en) Moisturizing agent and cosmetic preparation containing same
KR101886140B1 (en) Composition for Stabilizing Cosmetic Composition Using Pentaerythritol and Derivatives thereof
JP6686902B2 (en) Cosmetic composition containing acyl basic amino acid derivative and basic amino acid
JPH06247836A (en) Basic cosmetic
JPH11236319A (en) Composition for scalp and hair
JP7361488B2 (en) Solubilized composition for water-soluble compounds and oil-soluble compounds
JP2003104877A (en) Skin care preparation
JPWO2017069128A1 (en) Moisturizer and cosmetics containing the same
JP2000247910A (en) External preparation composition
WO2016104695A1 (en) Cosmetic composition containing acyl basic amino acid derivative and anionic water-soluble polymer
JP5148456B2 (en) Moisturizer
JPH05163129A (en) Cosmetic
JP3388928B2 (en) Hair restoration and hair restoration

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 14818042

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 14818042

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: JP