WO2014208399A1 - Humectant et préparation cosmétique le contenant - Google Patents

Humectant et préparation cosmétique le contenant Download PDF

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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
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WO
WIPO (PCT)
Prior art keywords
formula
salt
compound represented
acid
skin
Prior art date
Application number
PCT/JP2014/065989
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English (en)
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/fr

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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.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Dermatology (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention concerne un humectant qui a d'excellentes propriétés de rétention d'humidité et une excellente sécurité. Un humectant selon la présente invention contient un composé représenté par la formule (I-1) ou (I-2), ou un sel de celui-ci. Dans les formules, n représente un entier de 0 à 3 ; et X, Y et Z peuvent être identiques ou différents, et chacun représente un atome d'hydrogène ou un groupe -CH2CH(OH)CH2OH. Dans ce contexte, dans la formule (I-1), au moins l'un de X, Y et Z représente un groupe -CH2CH(OH)CH2OH ; et dans la formule (I-2), au moins l'un de X et Y représente un groupe -CH2CH(OH)CH2O.
PCT/JP2014/065989 2013-06-26 2014-06-17 Humectant et préparation cosmétique le contenant WO2014208399A1 (fr)

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 (fr) 2014-12-31

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0853337A (ja) * 1994-08-11 1996-02-27 Shiseido Co Ltd 皮脂抑制剤
JPH11193207A (ja) * 1997-12-26 1999-07-21 Shiseido Co Ltd 皮膚外用剤
JPH11193212A (ja) * 1997-12-26 1999-07-21 Shiseido Co Ltd 皮膚ｐＨ緩衝能維持強化用皮膚外用剤
WO2004052318A1 (fr) * 2002-12-06 2004-06-24 Seiwa Kasei Company, Limited Preparation cosmetique contenant des derives d'acide glycerylamine
JP2013014633A (ja) * 2012-10-24 2013-01-24 Daiichi Sankyo Healthcare Co Ltd 皮膚外用剤
JP2013053130A (ja) * 2011-08-05 2013-03-21 Shiseido Co Ltd 液状皮膚外用剤組成物

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0853337A (ja) * 1994-08-11 1996-02-27 Shiseido Co Ltd 皮脂抑制剤
JPH11193207A (ja) * 1997-12-26 1999-07-21 Shiseido Co Ltd 皮膚外用剤
JPH11193212A (ja) * 1997-12-26 1999-07-21 Shiseido Co Ltd 皮膚ｐＨ緩衝能維持強化用皮膚外用剤
WO2004052318A1 (fr) * 2002-12-06 2004-06-24 Seiwa Kasei Company, Limited Preparation cosmetique contenant des derives d'acide glycerylamine
JP2013053130A (ja) * 2011-08-05 2013-03-21 Shiseido Co Ltd 液状皮膚外用剤組成物
JP2013014633A (ja) * 2012-10-24 2013-01-24 Daiichi Sankyo Healthcare Co Ltd 皮膚外用剤

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