JP5577889B2 - Skin cosmetics - Google Patents

Description

  The present invention relates to a skin cosmetic. More specifically, the present invention relates to a skin cosmetic that quickly adapts to the skin, does not feel sticky, and has excellent moisture retention effect, skin flexibility improvement effect, skin roughness improvement effect, and skin protection effect.

  Keeping skin moisture within an appropriate range is very important for skin health. Natural moisturizing factor (NMF) inherent in the skin plays an important role in moisture retention in the stratum corneum. When the amount of NMF decreases, the water retention capacity of the stratum corneum is reduced, the skin is dried, the texture is disturbed, and the skin becomes rough. In order to maintain a fresh and moist skin, many studies have been conducted to use amino acids and their derivatives, which are the main components of NMF, as cosmetic bases. Among them, basic amino acids such as arginine, lysine and histidine are known to have biological tissue repair, immune function maintenance, wound healing effect, active oxygen removal action, etc., and are suitable for dry and rough skin It is used in cosmetics as a moisturizing agent. However, there are cases where the familiarity with the skin is poor or the effect is not sufficiently obtained, and amino acid derivatives have been studied in order to solve these problems.

For example, Patent Document 1 discloses a cosmetic comprising N-acetyl basic amino acid and / or a salt thereof. However, the sustainability of the moisturizing effect, the effect of improving skin flexibility, and the effect of improving rough skin were not fully satisfactory.
Patent Document 2 discloses an external preparation for skin containing an N-glyceryl derivative of an amino acid obtained by reacting an amino acid or imino acid with glycidol or an acid addition salt thereof. However, the familiarity with the skin, the feeling of stickiness, and the skin protecting effect were not fully satisfactory. In this way, cosmetics that have good skin feel such as familiarity to the skin and lack of stickiness, as well as excellent skin improvement effects such as a long-lasting moisturizing effect and a rough skin prevention effect, have been obtained so far. It wasn't.

JP 2002-87928 A JP 2004-83453 A

  An object of the present invention is to provide a skin cosmetic that quickly adapts to the skin, does not feel sticky, and has an excellent moisturizing effect, an improved skin flexibility, an improved rough skin effect, and an excellent skin protective effect. is there.

As a result of repeated studies to solve the above problems, it was found that the above object can be achieved by combining the arginine derivative represented by the formula (I) and the water-soluble polymer compound at a specific ratio, and the present invention was completed I came to let you.
That is, the skin cosmetic of the present invention comprises (a) 0.05 to 10% by mass of an arginine derivative represented by the formula (I) and (b) 0.01 to 3% by mass of a water-soluble polymer compound. It is characterized by being.

(R ¹ and R ² are a hydrogen atom or a hydroxypropyl group, and at least ^one of R ¹ and R ² represents a hydroxypropyl group. R ³ represents a hydrogen atom or an alkali metal atom.)

  Moreover, the skin cosmetic of the present invention is further characterized by being (c) a skin cosmetic containing 0.001 to 2% by mass of an anti-inflammatory agent.

  The cosmetic of the present invention quickly adapts to the skin, does not feel sticky, and is excellent in the durability of the moisturizing effect, the skin flexibility improving effect, the skin roughness improving effect, and the skin protecting effect.

The component (a) used in the present invention is represented by the formula (I), and R ¹ and R ² in the formula (I) are a hydrogen atom or a hydroxypropyl group, and at least one of them is a hydroxypropyl group. In the formula (I), R ³ is a hydrogen atom or an alkali metal atom, and examples of the alkali metal atom include sodium, potassium, lithium and the like.

The arginine derivative represented by the above formula (I) of the present invention can be obtained by reacting arginine and propylene oxide in an aqueous solvent without a catalyst. Specifically, an arginine derivative represented by the formula (I) is obtained by preparing an aqueous arginine solution having a predetermined concentration and performing the reaction while adding propylene oxide while stirring with stirring. However, when R ³ is an alkali metal, an arginine derivative represented by the formula (I) can be obtained by reacting with arginine and propylene oxide followed by an alkali agent such as sodium hydroxide. Moreover, in this invention, it is good also as an acid addition salt of an arginine derivative with an organic acid or an inorganic acid.

  (A) The compounding quantity of a component is 0.05-10 mass% in the composition whole quantity, Preferably it is 0.05-8 mass%, More preferably, it is 0.1-6 mass%. If it is less than 0.05% by mass, stickiness may be caused, or the conformability to the skin, the skin flexibility improvement effect and the skin roughness improvement effect may not be obtained. On the other hand, if it exceeds 10% by weight, an effect commensurate with the amount added cannot be obtained, which is disadvantageous in terms of cost.

  The water-soluble polymer compound (b) used in the present invention forms a hydrogel containing a large amount of water when dissolved in water, and has the property of significantly increasing the viscosity of the aqueous solution. It has the same properties as surfactants such as protective colloid action, gelling action, emulsifying action, etc. adsorbed on the interface. Examples of water-soluble polymers having such properties include natural polymer compounds derived from plants, microorganisms, animals, etc. (polysaccharides, proteins, etc.), semi-synthetic polymer compounds (cellulose-based, starch-based, alginic acid-based, etc.). And synthetic polymer compounds (such as vinyl), and inorganic polymers (such as bentonite). Specifically, natural polymer compounds include gum arabic, guar gum, quince seed gum, quince, agar, xanthan gum, fructan, pullulan, sodium hyaluronate, sodium chondroitin sulfate, and proteins such as gelatin and casein. Is mentioned. Examples of the semi-synthetic polymer compound include cellulose compounds such as carboxymethyl cellulose and hydroxyethyl cellulose, starch compounds such as soluble starch and carboxymethyl starch, and alginic acid polymer compounds such as sodium alginate and propylene glycol alginate. Synthetic polymer compounds include polyvinyl alcohol, sodium polyacrylate, carboxyvinyl polymer and modified products thereof, methacryloyloxyethyl phosphorylcholine polymer and copolymers with copolymerizable monomers, such as vinyl-based polymers such as polyethylene glycol, and the like. Examples include ether-based polymer compounds. These polymer compounds are classified into anionic, cationic, amphoteric and nonionic depending on the electrical properties. Among these, anionic or amphoteric polymer compounds are preferable from the viewpoint of lack of skin stickiness, skin flexibility improvement effect, skin roughness improvement effect, and skin protection effect. Specifically, xanthan gum, sodium hyaluronate, sodium chondroitin sulfate, sodium polyacrylate, carboxyvinyl polymer, alkyl-modified carboxyl vinyl polymer, polymethacryloyloxyethyl phosphorylcholine, copolymer of methacryloyloxyethyl phosphorylcholine and alkyl methacrylate Xanthan gum, sodium hyaluronate, carboxyvinyl polymer, and a copolymer of methacryloyloxyethyl phosphorylcholine and alkyl methacrylate are particularly preferable.

  (B) The compounding quantity of a component is 0.01-3 mass% in a composition whole quantity, Preferably it is 0.02-2.5 mass%, More preferably, it is 0.05-2 mass%. When the amount is less than 0.01% by mass, the conformability to the skin is deteriorated, and the durability of the moisturizing effect, the skin flexibility improving effect, the rough skin improving effect and the skin protecting effect are weakened. If it exceeds 3% by mass, blending may become difficult or stickiness may occur, which is also disadvantageous in terms of cost. (B) A component may be used individually by 1 type and may use 2 or more types together.

  The skin cosmetic of the present invention can further contain an anti-inflammatory agent as component (c) in order to further improve the skin softness improving effect and the rough skin improving effect. The anti-inflammatory agent (c) is a drug used for the purpose of suppressing inflammation such as redness and swelling and reducing tissue damage associated with inflammation. Examples of the compound having such an action include steroidal and non-steroidal compounds. Steroidal anti-inflammatory agents indirectly inhibit phospholipase A2, resulting in an anti-inflammatory effect by suppressing the synthesis of prostaglandins and leukotrienes. On the other hand, non-steroidal anti-inflammatory drugs inhibit the action of cyclosoxygenase (COX), a prostaglandin synthase, and suppress pain-inducing substances (substances that induce pain), thereby providing anti-inflammatory, analgesic and antipyretic effects. Effect, antithrombotic effect. Specifically, there are plant extracts containing steroid saponins such as steroid saponins and barley winter extract in addition to prednisolone, beclomethasone, betamethasone, fluticasone, dexamethasone, hydrocortisone and the like as steroidal anti-inflammatory agents. In addition, as non-steroidal anti-inflammatory agents, allantoin, guaiazulene, indomethacin, ketoprofen, piroxicam, acetaminophen, aspirin, salicylic acid, bufemaxac, suprofen, ibuprofen piconol, flurbiprofen, pranoprofen, diclofenac sodium, sodium salicylate, Plant extracts and propolis extracts containing triterpenoid saponins such as triterpenoid saponins and licorice extracts such as glycyrrhizic acid, glycyrrhetinic acid and their salts and esterified in addition to methyl salicylate, benzadac, felbinac, ufernamate, diphenhydramine hydrochloride, etc. is there. Among these, non-steroidal anti-inflammatory agents are preferable in consideration of safety due to continuous use, and glycyrrhizic acid and its salt, glycyrrhetinic acid and its salt are considered in consideration of skin softness improving effect and improvement in feeling of use. Or esterified products, allantoin, and guaiazulene are more preferable, and glycyrrhizinate is more preferable.

  (C) The compounding quantity of a component is 0.001-2 mass% in a composition whole quantity, Preferably it is 0.01-1.5 mass%, More preferably, it is 0.05-1 mass%. (C) A component may be used individually by 1 type and may use 2 or more types together.

  Furthermore, you may mix | blend the component normally used for cosmetics with the skin cosmetics of this invention in the range which does not impair the performance of this invention.

Next, the present invention will be described in more detail with reference to examples.
<Synthesis example of arginine derivative>
<Compound 1>
174 g (1 mol) of L-arginine was dissolved in 406 g of ion exchange water and charged into the autoclave, and the air in the autoclave was replaced with dry nitrogen. Next, the temperature was raised to 60 ° C., and 64 g (1.1 mol) of propylene oxide was added dropwise over 1 hour, and the reaction was further continued for 6 hours while maintaining the temperature at 60 ° C. After completion of the reaction, unreacted propylene oxide was removed by bubbling with dry nitrogen for 30 minutes, the reaction solution was taken out from the autoclave, and the solvent was distilled off under reduced pressure to obtain a reaction product. The ¹ H-NMR spectrum of the reaction product was measured, and the propylene oxide average addition mole number of the reaction product was calculated based on the following calculation method. As a result, the average number of moles of propylene oxide added in Compound 1 was 1.02 moles. Ion exchange water was added to the reaction product to prepare a 25% by mass aqueous solution of an arginine derivative, which was used for the following studies.

^<1 H-NMR measurement conditions>
Model used: ECA-600 (600 MHz) manufactured by JEOL Ltd.
Measuring solvent: D ₂ O
Internal standard: DSS (2,2-dimethyl-2-silapentane-5-sulfonic acid sodium salt)
<Calculation method of average added mole number of hydroxypropyl group>
S1: cumulative intensity of peaks attributed to hydrogen bonded to β-carbon and γ-carbon of arginine at δ = 1.5 to 1.7 ppm,
S2: δ = 2.5 to 2.8 ppm as the integrated intensity of the peak attributed to hydrogen bonded to the 1-position carbon of the hydroxypropyl group added to the α-amino group,
The average number of moles of hydroxypropyl group added was calculated by (S2 / S1) × 2.

<Compound 2>
The reaction was conducted under the same conditions as for Compound 1 except that 174 g (1 mol) of L-arginine and 116 g (2 mol) of propylene oxide were used. The average addition mole number of propylene oxide of Compound 2 obtained from the ¹ H-NMR spectrum of the obtained reaction product was 1.84 mol. Ion exchange water was added to this reaction product to prepare a 25% by mass aqueous solution of an arginine derivative, which was used for the following studies.
(Evaluation method)
The skin cosmetics shown in Table 1 (skin lotion) and Table 3 (oil-in-water emulsion) were prepared. (1) Skin conformability, (2) Stickiness, (3) Sustained moisturizing effect, (4 The following methods were used to evaluate the effects of improving skin flexibility, (5) improving skin roughness, and (6) protecting skin.

(1) Familiarity with skin 20 females (22 to 40 years old) were panelists, and the prepared skin cosmetic was applied after washing their face. And the conformability to the skin at the time of use was determined as follows.
2 points: When familiar with skin.
1 point: When familiar with skin, feels slightly worse.
0 point: When it is felt that the familiarity with the skin is bad.
The total score of 20 people was calculated and evaluated as follows.
A: The total score is 30 points or more (and there is no 0 point evaluation): a skin cosmetic that is excellent in conformity to the skin.
X: The total score is less than 30: skin cosmetics that are not well-familiar with the skin.

(2) Stickiness 20 women (22 to 40 years old) were panelists, and the prepared skin cosmetic was applied after washing their face. And the stickiness of the skin at the time of application | coating and 10 minutes after application | coating was determined as follows.
2 points: At the time of application, when no stickiness was felt 10 minutes after application.
1 point: When a sticky feeling is felt either during application or 10 minutes after application.
0 point: When a sticky feeling was felt at the time of application and 10 minutes after application.
The total score of 20 people was calculated and evaluated as follows.
◯: Total score of 30 points or more (and no score of 0): Skin cosmetics that do not feel sticky.
X: The total score is less than 30: It is a skin cosmetic with a sticky feeling.

(3) Sustainability of moisturizing effect 20 females (22 to 40 years old) were panelists, and the prepared skin cosmetic was applied after washing their face. Then, after 2 hours, the skin was moistened and judged as follows.
2 points: When the skin feels sufficiently moistened just after use.
1 point: When the skin feels slightly moisturized compared to immediately after use.
0 points: When the skin feels that the skin is not sufficiently moistened immediately after use.
The total score of 20 people was calculated and evaluated as follows.
A: The total score is 30 points or more (and there is no evaluation of 0 points): a skin cosmetic with a good moisturizing effect.
X: The total score is less than 30 points: skin cosmetics having no moisturizing effect.

(4) Skin flexibility improvement effect 20 women (22 to 40 years old) were used as panelists, and the prepared skin cosmetics were used twice a day for 2 weeks. The skin condition after 2 weeks was determined as follows.
2 points: When the skin clearly feels soft and soft.
1 point: When the skin feels soft and soft.
0 point: When it feels that there is no skin softness improvement effect at all.
The total score of 20 people was calculated and evaluated as follows.
A: The total score is 30 points or more (and there is no 0 point evaluation): a skin cosmetic excellent in the effect of improving skin flexibility.
X: The total score is less than 30: skin cosmetics that do not have an effect of improving skin flexibility.

(5) Rough skin improvement effect 10 women (28 to 40 years old) who feel rough skin were used as panelists, and the prepared skin cosmetics were used twice a day for 2 weeks. The skin condition after 2 weeks was determined as follows.
2 points: When it is felt that rough skin has been cured.
1 point: When it feels that the rough skin has been cured somewhat.
0 point: When it feels that there is no skin roughening effect at all.
The total score of 10 people was calculated and evaluated as follows.
A: The total score is 15 points or more (and there is no evaluation of 0 points): a skin cosmetic excellent in rough skin improvement effect.
X: The total score is less than 15: It is a skin cosmetic that does not have a rough skin improvement effect.

(6) Skin protection effect 20 females (22 to 40 years old) were used as panelists, and the prepared skin cosmetics were used twice a day for 2 weeks. Then, the skin barrier properties after 2 weeks were evaluated using Vapo meter. When the barrier ability improvement rate was 20% or more, it was evaluated as a skin lotion having an excellent skin protection effect.
○: Barrier ability improvement rate of 20% or more: A skin cosmetic excellent in skin protecting effect.
X: Barrier ability improvement rate is less than 20%: It is a skin cosmetic having no skin protecting effect.

The results are shown in Tables 1 and 3.

The skin cosmetic (skin lotion) of the present invention quickly adapts to the skin from Examples 1 to 3, and does not feel a sticky feeling. It maintains the moisturizing effect, improves the skin flexibility, improves the rough skin, and Excellent skin protection effect.
On the other hand, in Comparative Examples 1-3, sufficient performance was not obtained. In Comparative Example 1, since the component (a) was not contained, the familiarity with the skin was poor, the skin was sticky, and the effect of improving the skin flexibility was not sufficient. In Comparative Example 2, since L-arginine was contained instead of the component (a), the familiarity with the skin was bad and sticky. In Comparative Example 3, since the component (b) was not contained, the familiarity with the skin was poor, and the durability of the moisturizing effect, the skin flexibility improving effect, the skin roughness improving effect and the skin protecting effect were not sufficient.
In addition, the skin cosmetics (oil-in-water emulsion) of the present invention, from Examples 4 to 6, quickly adapt to the skin and do not feel sticky, maintain the moisturizing effect, improve skin flexibility, Excellent skin roughening effect and skin protection effect.
On the other hand, in Comparative Example 4, sufficient performance was not obtained. In Comparative Example 4, the familiarity with the skin was bad, and stickiness was felt.

  The skin cosmetic of the present invention quickly adapts to the skin, does not feel sticky, and has excellent moisturizing effect, skin flexibility improvement effect, skin roughness improvement effect and skin protection effect. Can be used as

Claims (2)

(A) A skin cosmetic containing 0.05 to 10% by mass of an arginine derivative represented by the formula (I) and (b) 0.01 to 3% by mass of a water-soluble polymer compound.

(R ¹ and R ² are a hydrogen atom or a hydroxypropyl group, and at least ^one of R ¹ and R ² represents a hydroxypropyl group. R ³ represents a hydrogen atom or an alkali metal atom.) The skin cosmetic according to claim 1, further comprising (c) 0.001 to 2% by mass of an anti-inflammatory agent.