JP6125945B2 - Moisturizing cosmetic composition - Google Patents

Description

  The present invention relates to a moisturizing cosmetic composition containing a novel polyglycerin dialkyl or alkenyl ether and water, and a cosmetic containing the moisturizing cosmetic composition.

  Moisturizing cosmetics range from creams, emulsions, oils, oily gels, etc. with a large amount of oils to lotions, water gels, etc. with no or little oils. There is something. The type containing the oil agent is excellent in the moisturizing effect, but has a sticky feeling and is inferior in terms of usability such as being easily rinsed off with water. On the other hand, a type in which no oil agent is blended or a small amount is blended is excellent in usability, but is easily peeled off from the skin surface together with sweat and the like, and it is difficult to stably maintain the moisturizing effect for a long time.

  As methods for improving usability while maintaining an excellent moisturizing effect, Patent Documents 1 and 2 describe a method of using a nonionic surfactant such as a polyoxyethylene derivative together with an oil agent. However, it is necessary to add a large amount of a surfactant, and the polyoxyethylene surfactant has a problem of safety because it has an irritating property to the skin.

  Therefore, in recent years, cosmetics containing moisturizing components and the like typified by ceramide production promoters, pseudoceramides, natural ceramides and the like have become mainstream (Patent Document 3). However, it has been difficult to stabilize the moisturizing component in the preparation. Furthermore, it is a problem that it is expensive.

Japanese Patent Laid-Open No. 4-5213 JP-A-8-143420 JP 2011-231056

Accordingly, an object of the present invention is to provide a moisturizing cosmetic composition that is excellent in safety and usability and has an effect of maintaining a high amount of moisture in the skin (= having an excellent moisturizing function) at low cost. is there.
Another object of the present invention is to provide a cosmetic containing the moisturizing cosmetic composition.

As a result of intensive studies to solve the above-mentioned problems, the present inventors have obtained glycerin dialkyl or alkenyl ether having a secondary hydroxyl group obtained by reacting alcohol and glycidyl ether, and further reacting with 2 equivalents or more of glycidol. The resulting compound has two hydrophobic groups bonded with a short spacer and has a highly water-soluble polyglycerin moiety as a hydrophilic group, so that it has excellent surface activity and can form a lamellar liquid crystal phase. It has been found that since the phase has an action of firmly holding moisture in the hydrophilic group portion, when applied to the skin surface, it exerts a barrier function that suppresses the amount of moisture transpiration on the skin surface.
The present invention has been completed based on these findings and further research.

（式中、Ｒ¹、Ｒ²は、同一又は異なって、ヒドロキシル基を有していてもよい直鎖状若しくは分岐鎖状のアルキル基又はアルケニル基である。ｎはグリセリン単位の数を示し、２以上の整数である）
で表される化合物を含むポリグリセリンジアルキル又はアルケニルエーテル、及び水を含有する保湿性化粧料用組成物を提供する。 That is, the present invention provides the following formula (1):

(In the formula, R ¹ and R ² are the same or different and each represents a linear or branched alkyl group or alkenyl group which may have a hydroxyl group. N represents the number of glycerin units; (It is an integer of 2 or more)
The composition for moisturizing cosmetics containing the polyglycerol dialkyl or alkenyl ether containing the compound represented by these, and water is provided.

In the moisturizing cosmetic composition, the content of each component is preferably as follows.
Polyglycerin dialkyl or alkenyl ether: 1 to 30 parts by weight Water: 40 to 99 parts by weight

  The HLB value of the polyglycerin dialkyl or alkenyl ether is preferably 6-20.

  The present invention also provides a cosmetic containing the moisturizing cosmetic composition.

The composition for a moisturizing cosmetic composition of the present invention has an excellent surfactant ability due to the shape in which two molecules of a monomeric surfactant (one hydrophobic group and one hydrophilic group type surfactant) are bound by a short spacer, Contains polyglycerin dialkyl or alkenyl ether which forms a lamellar liquid crystal phase. Therefore, when the moisturizing cosmetic composition of the present invention is applied to the skin surface, the ceramide or phospholipid is formed of polyglycerin dialkyl or alkenyl ether so as to form a lipid bilayer and exert a moisturizing effect. A lamellar liquid crystal phase excellent in moisture retention covers the skin surface and can exhibit a barrier function that suppresses transpiration of skin moisture.
Further, the moisturizing cosmetic composition of the present invention is excellent in storage stability.
Furthermore, the composition for moisturizing cosmetics of the present invention has an appropriate viscosity without adding a gelling agent or a thickener, and is difficult to drip from the hand during use and has good elongation.
Therefore, the composition for moisturizing cosmetics of the present invention can be suitably used for cosmetics (for example, lotion, milky lotion, cream, etc.).

  In the present invention, the lamellar liquid crystal phase is a state in which fluidity is maintained while leaving the regularity of the molecular arrangement in which bilayers of amphiphilic molecules and water are alternately oriented, and optical anisotropy. Because of its unique optical properties, it can be easily confirmed by observation with a polarizing plate or a polarizing microscope.

It is a figure which shows the moisturizing effect of the composition for cosmetics obtained in the Example and the comparative example.

  The moisturizing cosmetic composition of the present invention contains at least a polyglycerin dialkyl or alkenyl ether containing a compound represented by the formula (1) and water.

[Polyglycerin dialkyl or alkenyl ether]
The polyglycerin dialkyl or alkenyl ether of the present invention contains a compound represented by the following formula (1). The content of the compound represented by the formula (1) in the polyglycerol dialkyl or alkenyl ether (100% by weight) of the present invention is, for example, 50% by weight or more, preferably 70% by weight or more.

In formula (1), R ¹ and R ² are the same or different and each represents a linear or branched alkyl group or alkenyl group which may have a hydroxyl group. n represents the number of glycerin units and is an integer of 2 or more.

C ₃ H ₆ O ₂ in parentheses in the formula (1) has both structures represented by the following formulas (2) and (3).
—CH ₂ —CHOH—CH ₂ O— (2)
—CH (CH ₂ OH) CH ₂ O— (3)

Examples of the linear or branched alkyl group in R ¹ and R ² include n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-lauryl (dodecyl). ), n- tridecyl, n- myristyl (tetradecyl), n- pentadecyl, n- hexadecyl, n- heptadecyl, n- stearyl, n- nonadecyl, n- eicosyl, n- heneicosyl, such as n- docosyl group C _{6- 22} linear alkyl groups; isohexyl, s-hexyl, t-hexyl, isoheptyl, s-heptyl, t-heptyl, isooctyl, s-octyl, t-octyl, isononyl, s-nonyl, t-nonyl, isodecyl, s -Decyl, t-decyl, isoundecyl, s-undecyl, t-undecyl, isolauryl, s-lauryl, t- Lauryl, isotridecyl, s-tridecyl, t-tridecyl, isomyristyl, s-myristyl, t-myristyl, isopentadecyl, s-pentadecyl, t-pentadecyl, isohexadecyl, s-hexadecyl, t-hexadecyl, isoheptadecyl, s -Heptadecyl, t-heptadecyl, isostearyl, isononadecyl, s-nonadecyl, t-nonadecyl, isoeicosyl, s-eicosyl, t-eicosyl, isohenicosyl, s-henicosyl, t-henicosyl, isodocosyl, s-docosyl, t-docosyl, etc. And a C _6-22 branched alkyl group.

Examples of the linear or branched alkyl group having a hydroxyl group in R ¹ and R ² include a group having one or more hydroxyl groups in the C _6-22 linear or branched alkyl group. Can be mentioned.

Examples of the linear or branched alkenyl group for R ¹ and R ² include n-hexenyl, n-heptenyl, n-octenyl, n-nonenyl, n-decenyl, n-undecenyl, n-dodecenyl, n C _6-22 linear alkenyl groups such as -tridecenyl, n-tetradecenyl, n-pentadecenyl, n-hexadecenyl, n-heptadecenyl, n-oleyl, n-nonadecenyl, n-eicosenyl, n-heneicosenyl, n-docosenyl Isohexenyl, s-hexenyl, t-hexenyl, isoheptenyl, s-heptenyl, t-heptenyl, isooctenyl, s-octenyl, t-octenyl, isononenyl, s-nonenyl, t-nonenyl, isodecenyl, s-decenyl, t- Decenyl, isoundecenyl, s-undecenyl, t-u Ndecenyl, isododecenyl, s-dodecenyl, t-dodecenyl, isotridecenyl, s-tridecenyl, t-tridecenyl, isotetradecenyl, s-tetradecenyl, t-tetradecenyl, isopentadecenyl, s-pentadecenyl, t-pentadecenyl, Isohexadecenyl, s-hexadecenyl, t-hexadecenyl, isoheptadecenyl, s-heptadecenyl, t-heptadecenyl, isooleyl, isononadecenyl, s-nonadecenyl, t-nonadecenyl, isoeicocenyl, s-eicocenyl, t-eicocenyl, Examples thereof include C _6-22 branched alkenyl groups such as isohenicosenyl, s-henicosenyl, t-henicosenyl, isodocosenyl, s-docosenyl and t-docosenyl.

Examples of the linear or branched alkenyl group having a hydroxyl group in R ¹ and R ² include a group having one or more hydroxyl groups in the C _6-22 linear or branched alkenyl group. Can be mentioned.

R ¹ and R ² in the present invention include, among others, a C8 to C22 (more preferably a C9 to C20, particularly preferably) point in that a lamellar liquid crystal layer excellent in water retention can be formed. Is preferably a linear or branched alkyl group or alkenyl group (particularly preferably a linear alkyl group or alkenyl group).

  n represents the number of glycerin units and is an integer of 2 or more, for example, 2 to 25, preferably 5 to 15, particularly preferably 7 to 13, and most preferably 8 to 13. When n is less than the above range, the HLB value tends to decrease and the hydrophilicity tends to decrease, and when n is excessive, the HLB value becomes too large and the lipophilicity tends to decrease. In either case, it becomes difficult to form a lamellar liquid crystal phase, and the moisture retention tends to decrease.

The polyglycerin dialkyl or alkenyl ether of the present invention has an HLB (Hydrophile-Lipophile Balance) value of, for example, 6 to 20, preferably 10 to 15. When the HLB value of polyglycerin dialkyl or alkenyl ether is below the above range, the hydrophilicity tends to decrease. On the other hand, when the HLB value exceeds the above range, the lipophilicity tends to decrease. The HLB value can be calculated by the following formula using an organic conceptual diagram, for example. As for the physicochemical properties of the compound, the degree of physical properties mainly due to Van Der Waals force is called “organic”, and the degree of physical properties mainly due to electric affinity is called “inorganic”. "Organic value" and "inorganic value" can be calculated as the combined value of each part of the structure from the structure of the compound etc. (Synthesis and application of surfactants / Ryohei Oda, Kazuhiro Teramura (Tokyo:槙 Bookstore, 1957.3)). Further, the calculation formula of the HLB value is not limited to the following formula.
HLB value = (inorganic value / organic value) × 10

  Examples of the compound represented by the formula (1) of the present invention include triglycerin dioctyl ether, triglycerin didecyl ether, triglycerin dilauryl ether, triglycerin dimyristyl ether, triglycerin dioleyl ether, and triglyceryl distearyl. Ether, triglycerin diisostearyl ether, tetraglycerin dioctyl ether, tetraglycerin didecyl ether, tetraglycerin dilauryl ether, tetraglycerin dimyristyl ether, tetraglycerin dioleyl ether, tetraglycerin distearyl ether, tetraglycerin diisostearyl ether , Pentaglycerin didecyl ether, pentaglycerin dilauryl ether, pentaglycerin dimyristyl ether, Tag glycerin dioleyl ether, pentaglyceryl distearyl ether, pentaglycerin diisostearyl ether, hexaglycerin dioctyl ether, hexaglycerin didecyl ether, hexaglycerin dilauryl ether, hexaglycerin dimyristyl ether, hexaglycerin diolyl ether, hexaglycerin Distearyl ether, hexaglycerin diisostearyl ether, heptaglycerin dioctyl ether, heptaglycerin didecyl ether, heptaglycerin dilauryl ether, heptaglycerin dimyristyl ether, heptaglycerin dirailyl ether, heptaglycerin distearyl ether, heptaglycerin diisoyl ether Stearyl ether, octaglycerin dioctylate , Octaglycerin didecyl ether, octaglycerin dilauryl ether, octaglycerin dimyristyl ether, octaglycerin dioleyl ether, octaglycerin distearyl ether, octaglycerin diisostearyl ether, nonaglycerin dioctyl ether, nonaglycerin didecyl ether, nona Glycerin dilauryl ether, nonaglycerin dimyristyl ether, nonaglycerin dioleyl ether, nonaglycerin distearyl ether, nonaglycerin diisostearyl ether, decaglycerin dioctyl ether, decaglycerin didecyl ether, decaglycerin dilauryl ether, decaglycerin di Myristyl ether, decaglycerin dioleyl ether, decaglycerin distearies Ether, decaglycerin diisostearyl ether, undecaglycerin dioctyl ether, undecaglycerin didecyl ether, undecaglycerin dilauryl ether, undecaglycerin dimyristyl ether, undecaglycerin dioleyl ether, undecaglycerin distearyl ether, Examples include undecaglycerin diisostearyl ether.

The compound represented by the formula (1) of the present invention has two hydrophobic groups (R ¹ , R ² ) bonded with a short spacer, so that they are closely associated without repelling and have excellent water retention. A lamella liquid crystal layer can be formed. Therefore, when it is applied to the skin surface, the lamellar liquid crystal phase can prevent moisture transpiration from the skin, and can exhibit excellent moisture retention.

  The compound represented by the formula (1) is obtained by reacting, for example, an aliphatic alcohol with alkyl or alkenyl glycidyl ether in the presence of a catalyst to obtain glycerin dialkyl or alkenyl ether, and then obtaining glycerin dialkyl or alkenyl ether with glycidol. It can manufacture by the method of reacting.

More specifically, the compound represented by Formula (1) can be manufactured through the following step (1) and step (2), for example. In the following formula, R ¹ , R ² and n are the same as described above.
Step (1): Glycerin dialkyl having a secondary hydroxyl group represented by the following formula (6) by reacting the glycidyl ether represented by the following formula (5) with the alcohol represented by the following formula (4) Obtaining an alkenyl ether Step (2): By reacting 1 equivalent of glycerin dialkyl or alkenyl ether having a secondary hydroxyl group represented by the following formula (6) obtained in Step (1) with n equivalents of glycidol. A compound represented by the formula (1) is obtained.

R ¹ in the alcohol represented by the formula (4) corresponds to R ¹ in the compound represented by the formula (1), and may be a linear or branched alkyl group which may have a hydroxyl group. Or an alkenyl group.

  Examples of the alcohol represented by the formula (4) include saturated alcohols such as decyl alcohol, undecyl alcohol, lauryl alcohol, tridecyl alcohol, myristyl alcohol, stearyl alcohol, and isostearyl alcohol; oleyl alcohol, isooleyl alcohol, and linoleic alcohol. Examples thereof include unsaturated alcohols such as rualcohol and linolenyl alcohol. These can be used individually by 1 type or in mixture of 2 or more types.

R ² in the glycidyl ether represented by the formula (5) corresponds to R ² in the compound represented by the formula (1), and may be a linear or branched alkyl which may have a hydroxyl group. Group or alkenyl group.

Examples of the glycidyl ether represented by the formula (5) include R ² such as decyl glycidyl ether, undecyl glycidyl ether, lauryl glycidyl ether, tridecyl glycidyl ether, myristyl glycidyl ether, stearyl glycidyl ether, and isostearyl glycidyl ether. A glycidyl ether which is a linear or branched alkyl group; R ² such as oleyl glycidyl ether, isooleyl glycidyl ether, linolyl glycidyl ether (= linolenyl glycidyl ether) is a linear or branched alkenyl group; A certain glycidyl ether etc. can be mentioned. These can be used individually by 1 type or in mixture of 2 or more types.

  As usage-amount of the glycidyl ether represented by Formula (5) in reaction of the said process (1), it is about 3-10 equivalent with respect to 1 equivalent of alcohol represented by Formula (4), Preferably it is 6- 8 equivalents. When the usage-amount of the glycidyl ether represented by Formula (5) remove | deviates from the said range, there exists a tendency for the yield of the compound represented by the said Formula (1) to fall.

The reaction in the above step (1) is preferably performed in the presence of an acid catalyst. As the acid catalyst, either a protonic acid or a Lewis acid can be used. Examples of the protonic acid include super strong acids (for example, SbF ₅ , SbF ₅ —HF, SbF ₅ —FSO ₃ H, SbF ₅ —CF ₃ SO ₃ H, etc.), sulfuric acid, hydrochloric acid, phosphoric acid, boron fluoride acid, Examples thereof include organic acids and inorganic acids such as p-toluenesulfonic acid, chloroacetic acid, picric acid, and heteropolyacid. Examples of Lewis acids include BF ₃ , BF ₃ O (C ₂ H ₅ ) ₂ , AlCl ₃ , FeCl ₃ , tin alkoxide (for example, tin tetraisopropoxide), tin halide (for example, tin tetrachloride (for example) = Tin (IV) chloride, tin tetrabromide, etc.).

  As the usage-amount of the said acid catalyst, it is about 0.5-6 mol% with respect to the alcohol represented by Formula (4), Preferably it is 1-5 mol%. When the usage-amount of an acid catalyst exceeds the said range, since the production | generation of a by-product is accelerated | stimulated, there exists a tendency for the purity of the compound represented by the said Formula (1) to fall. On the other hand, when the usage-amount of an acid catalyst is less than the said range, there exists a tendency for the yield of the compound represented by the said Formula (1) to fall.

  As reaction temperature of a process (1), it is about 50-150 degreeC, for example, Preferably it is 60-100 degreeC. The reaction time is, for example, about 30 minutes to 5 hours, preferably 30 minutes to 2 hours.

  The atmosphere of the reaction in step (1) is not particularly limited as long as it does not inhibit the reaction, and may be any of an air atmosphere, a nitrogen atmosphere, an argon atmosphere, and the like. Further, 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 means such as filtration, concentration, distillation, extraction and the like, or a separation means combining these.

  The reaction in step (2) is preferably performed in the presence of a basic catalyst.

  Examples of the basic catalyst include alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, and cesium hydroxide; alkali metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, and cesium carbonate; Alkali metal hydrogen carbonates such as sodium hydrogen carbonate, potassium hydrogen carbonate, cesium hydrogen carbonate; alkaline earth metal hydroxides such as magnesium hydroxide, calcium hydroxide, barium hydroxide; magnesium carbonate, calcium carbonate, barium carbonate, etc. Alkaline earth metal carbonates; alkali metal alkoxides such as sodium methoxide, sodium ethoxide and potassium t-butoxide; alkali metal organic acid salts such as sodium acetate; amines such as triethylamine, piperidine, N-methylpiperidine and pyridine ( Tertiary amine) It can be mentioned a nitrogen-containing heterocyclic compound and the like.

  Among them, it is preferable to use an alkali metal alkoxide such as sodium methoxide because the production cost can be suppressed.

  The amount of the basic catalyst used is, for example, about 20 to 100 mol%, preferably 90 to 100 mol%, based on the glycerin dialkyl or alkenyl ether having a secondary hydroxyl group represented by the formula (6). . When the usage-amount of a basic catalyst exceeds the said range, there exists a tendency which promotes the production | generation of the polyglycerol which is a by-product. On the other hand, when the usage-amount of a basic catalyst is less than the said range, there exists a tendency for the glycerol dialkyl or alkenyl ether which has a secondary hydroxyl group represented by Formula (6) to remain unreacted.

  The atmosphere of the reaction in step (2) is not particularly limited as long as the reaction is not inhibited, and may be any of an air atmosphere, a nitrogen atmosphere, an argon atmosphere, and the like. Further, the reaction can be carried out by any method such as batch, semi-batch and continuous methods.

  As reaction temperature of a process (2), it is about 50-150 degreeC, for example, Preferably it is 60-120 degreeC. The reaction time is, for example, about 30 minutes to 24 hours, preferably 5 hours to 15 hours, particularly preferably 7 hours to 12 hours. The reaction in the step (2) can be stopped by adding, for example, an aqueous phosphoric acid solution, sulfuric acid, hydrochloric acid, acetic acid and the like.

  After completion of the reaction, the reaction product can be separated and purified by, for example, separation means such as filtration, concentration, distillation, extraction and the like, or a separation means combining these.

  The content of polyglycerin dialkyl or alkenyl ether in the moisturizing cosmetic composition of the present invention is not particularly limited and can be appropriately adjusted. For example, the total amount of moisturizing cosmetic composition (100% by weight) 1) to 30% by weight. The upper limit of the content of polyglycerin dialkyl or alkenyl ether is about 30% by weight, preferably 25% by weight, particularly preferably 20% by weight, and most preferably 10% by weight. The lower limit is about 1% by weight, preferably 3% by weight, particularly preferably 5% by weight. The composition for moisturizing cosmetics containing polyglycerin dialkyl or alkenyl ether in the above range can form a lamellar liquid crystal phase in which polyglycerin dialkyl or alkenyl ether is excellent in water retention. Therefore, when applied to the skin surface, an excellent barrier function can be exhibited, and moisture evaporation from the skin surface can be prevented.

[water]
The water may be hard water or soft water, and for example, industrial water, tap water, ion exchange water, distilled water and the like can be used.

  As a compounding quantity of water, it is about 40 to 99 weight% of the whole composition for moisturizing cosmetics (100 weight%), for example. The lower limit of the water content is about 40% by weight, preferably 50% by weight, particularly preferably 60% by weight. The upper limit is about 99% by weight, preferably 97% by weight, particularly preferably 96% by weight.

[Other ingredients]
The moisturizing cosmetic composition of the present invention can contain other components as required in addition to the polyglycerin dialkyl or alkenyl ether and water. Examples of other components include polyhydric alcohols, oil components, and fragrances. These can be used alone or in combination of two or more.

  Examples of the polyhydric alcohol include propylene glycol, glycerin, diglycerin, 1,3-butylene glycol, isoprene glycol, dipropylene glycol, polyethylene glycol, pentaerythritol, neopentyl glycol, sorbitol, sorbitan, maltitol, trehalose, and the like. Can be mentioned. These can be used individually by 1 type or in mixture of 2 or more types.

  The moisturizing cosmetic composition of the present invention contains a polyhydric alcohol (in particular, at least one compound selected from 1,3-butylene glycol, sorbitol, maltitol, and glycerin). However, the formation of aggregates (water clusters) with water increases the molecular weight and suppresses the water's molecular motion, thus suppressing moisture transpiration for a longer period due to the synergistic effect with the lamellar liquid crystal phase. It is preferable in that it can be performed.

  The blending amount of the polyhydric alcohol is, for example, about 1 to 30% by weight of the total amount (100% by weight) of the moisturizing cosmetic composition. The upper limit of the content of the polyhydric alcohol is about 30% by weight, preferably 20% by weight, particularly preferably 10% by weight.

  The oily component is usually an oily component that can be used in cosmetics, and liquid and / or pasty oily components can be used at normal temperature (15 to 25 ° C.) without any particular limitation. Moreover, even if it is a solid oily component, it can be mix | blended if it is a grade which does not have influence on liquid state maintenance. Examples of the oil component include natural animal and vegetable oils, semi-synthetic oils and fats, hydrocarbons, higher fatty acids, glyceride oils, ester oils, silicone oils, essential oil components (derived or synthesized from animals and plants), fat-soluble vitamins, and the like. . These can be used individually by 1 type or in mixture of 2 or more types.

  Examples of the natural animal and vegetable oils and semi-synthetic oils and fats include avocado oil, linseed oil, almond oil, olive oil, wheat germ oil, sesame oil, rice germ oil, rice bran oil, safflower oil, soybean oil, evening primrose oil, corn oil Rapeseed oil, horse fat, palm oil, palm kernel oil, castor oil, sunflower oil, jojoba oil, macadamia nut oil, coconut oil, hydrogenated coconut oil, peanut oil, lanolin and the like.

  Examples of the hydrocarbon include squalane, squalene, liquid paraffin, and petroleum jelly.

  Examples of the higher fatty acid include oleic acid, tall oil, and isostearic acid.

  Examples of the glyceride oil include glyceryl triisostearate, glyceryl triisopalmitate, glyceryl tri-2-ethylhexanoate, glyceryl tritetradecanoate, diparamethoxycinnamic acid / glyceryl monoisooctylate, and the like. it can.

  Examples of the ester oil include diisobutyl adipate, 2-hexyldecyl adipate, di-2-heptylundecyl adipate, isostearyl isostearate, trimethylolpropane triisostearate, cetyl 2-ethylhexanoate, di- 2-ethylhexanoic acid neopentyl glycol, tri-2-ethylhexanoic acid trimethylolpropane, tetra-2-ethylhexanoic acid pentaerythritol, cetyl octoate, oleyl oleate, octyl lauryl oleate, decyl oleate, neocapric dicaprate Pentyl glycol, 2-ethylhexyl succinate, isocetyl stearate, butyl stearate, diisopropyl sebacate, cetyl lactate, myristyl lactate, octyl palmitate, 2-ethyl palmitate Xyl, 2-hexyldecyl palmitate, 2-heptylundecyl palmitate, cholesteryl 12-hydroxystearate, phytosteryl oleate, diisostearyl malate, paramethoxycinnamate, pentaerythritol tetrarosinate, etc. Can do.

  Examples of the silicone oil include higher alkoxy modified silicones such as dimethylpolysiloxane, methylphenylpolysiloxane, methylhydrogenpolysiloxane, octamethylcyclopentasiloxane, decamethylcyclohexasiloxane, stearoxysilicone, alkyl modified silicone, and higher Examples thereof include aliphatic carbon group ester-modified silicone.

  Examples of the fat-soluble vitamin include tocopherol and derivatives thereof, retinol and derivatives thereof, and the like.

  The blending amount of the oil component is about 55% by weight or less of the total amount (100% by weight) of the moisturizing cosmetic composition. If the content of the oil component exceeds the above range, the stickiness tends to be severe.

  The moisturizing cosmetic composition of the present invention can be prepared by mixing the above components. The pH of the moisturizing cosmetic composition of the present invention is, for example, about 6 to 8 (preferably 6 to 7). Moreover, the composition for moisturizing cosmetics of the present invention has a transparent appearance and is excellent in beauty.

[Cosmetics]
The cosmetic of the present invention is characterized by containing the moisturizing cosmetic composition.

  In addition to the above-described moisturizing cosmetic composition, other ingredients can be appropriately blended in the cosmetic composition of the present invention within the range where the object of the present invention can be achieved. Other components include, for example, surfactants other than those described above, lower alcohols, functional beads, capsules, salts, powders (eg, titanium oxide, talc, ventsite, cation, mica, etc.), bactericides, Examples include pigments, fragrances, preservatives, antioxidants, antioxidant assistants, ultraviolet absorbers, moisturizers, flame retardants, pH adjusters, extracts derived from animals, plants, fish shells, and microorganisms. These can be used individually by 1 type or in combination of 2 or more types.

  The blending amount of the other components is about 5% by weight or less of the total amount of the cosmetic (100% by weight).

  The cosmetic of the present invention contains a polyglycerin dialkyl or alkenyl ether having an effect of suppressing the transpiration of moisture from the skin surface by forming a lamellar liquid crystal phase, and thus has excellent moisture retention. Moreover, it has an appropriate viscosity without adding a gelling agent or a thickening agent, hardly drops from the hand during use, and has a good elongation. Therefore, the cosmetic of the present invention can be suitably used as a coating-type cosmetic (for example, lotion, emulsion, beauty cream, moisturizing gel, etc.).

  EXAMPLES Hereinafter, although an Example demonstrates this invention more concretely, this invention is not limited by these Examples.

Production Example 1 (Production of dilaurylglycerol)
After charging lauryl alcohol (reagent manufactured by Wako Pure Chemical Industries, Ltd., 886 g) in an amount of 8 equivalents to 1 equivalent of the following lauryl glycidyl ether, 1 mol% tin chloride (IV) (1.82 g) was added in a nitrogen atmosphere. 1 mol% of lauryl alcohol) was added, and lauryl glycidyl ether (manufactured by Yokkaichi Synthesis Co., Ltd., 150 g) was added dropwise over 1 hour while maintaining the reaction temperature at 80 ° C. After completion of the dropwise addition, aging was performed for 1 hour, and water was added to stop the reaction.
Potassium carbonate (Wako Pure Chemical Industries, Ltd., 9.67 g) was added to the resulting reaction crude liquid to remove water, and then diluted with heptane (Wako Pure Chemical Industries, Ltd., 259 g). .
Suction filtration was performed using a Buchner funnel, and the reactor was rinsed with a small amount of heptane to obtain a filtrate.
The heptane in the filtrate was distilled off with an evaporator, and then unreacted lauryl glycidyl ether was distilled off at 150 ° C. under reduced pressure of 2 mmHg to obtain 372 g of dilaurylglycerol.

Production Example 2 (Production of didecylglycerol)
Didecylglycerol was obtained in the same manner as in Production Example 1 except that decyl glycidyl ether was used instead of lauryl glycidyl ether and decyl alcohol was used instead of lauryl alcohol.

Preparation Example 1 (Production of undecaglycerin dilauryl ether)
Add 28% sodium methoxide methanol solution (20 g, 100 mol% of dilaurylglycerol) to dilaurylglycerol (45 g) obtained in Production Example 1 and distill under reduced pressure at 100 ° C., 2 mmHg, 10 hours. The methanol was distilled off.
Thereafter, glycidol (78 g) in an amount of 10 equivalents relative to 1 equivalent of the dilaurylglycerol was added dropwise over 10 hours while maintaining 70 ° C., and after aging for 1 hour, an 85% aqueous phosphoric acid solution ( The reaction was stopped by adding 8 g).
To the resulting reaction crude liquid, methanol (100 g) was added for dilution.
Then, after removing the phosphate in the crude liquid by pressure filtration, methanol was distilled off at 150 ° C. and normal pressure, and other low boiling components were further distilled off at 2 mmHg. 123 g of lauryl ether (HLB: 14.3) was obtained.

Preparation Example 2 (Production of undecaglycerin didecyl ether)
Undecaglycerin didecyl ether (HLB: 12.6) was prepared in the same manner as in Preparation Example 1 except that didecylglycerol obtained in Production Example 2 was used instead of dilaurylglycerol obtained in Production Example 1. 120 g was obtained.

Examples 1-3, Comparative Examples 1-4
Each component is blended in the proportions (wt%) shown in Table 1 below, heated and dissolved and mixed at a temperature of 80 ° C. or higher using an anchor mixer, and then cooled with stirring until 35 ° C. or lower to make up. A material composition was obtained. The obtained cosmetic composition was evaluated by the following method.

※ジラウロイルグルタミン酸リシンＮａ：ジラウロイルグルタミン酸リシンナトリウム水溶液（２９：７１）
テトラグリセリンモノラウリルエーテル：ＨＬＢ１２．１、商品名「セルモリスＡＭＬ０４」、（株）ダイセル製

* Dilauroyl glutamate lysine Na: dilauroyl glutamate lysine sodium aqueous solution (29:71)
Tetraglycerin monolauryl ether: HLB12.1, trade name “Cermorris AML04”, manufactured by Daicel Corporation

[Moisturizing effect confirmation]
The cosmetic compositions (about 0.5 g) obtained in the examples and comparative examples were applied to the forearm and allowed to penetrate for 2 minutes to become familiar. Immediately thereafter (0 minutes), 10 minutes, 20 minutes, 30 minutes, 60 minutes, 90 minutes, and 120 minutes using a portable moisture transpiration meter (manufactured by Keystone Scientific Co., Ltd.), the amount of moisture transpiration on the skin surface The moisturizing effect was evaluated by measuring (g / m ² · h). Moreover, as a reference example, the moisture transpiration amount of the bare skin to which the cosmetic composition was not applied was measured by the same method as described above.

The above results are summarized in the following table.

  As is apparent from Table 2, the cosmetic composition of the present invention can significantly suppress the amount of moisture transpiration as compared with a conventional representative humectant (= comparative example), and has excellent moisture retention. Have. That is, the cosmetic composition of the present invention is effective as a cosmetic composition having an excellent moisturizing effect and can be suitably used as a moisturizing cosmetic composition.

Claims (4)

Po Li glycerine dialkyl or alkenyl ether, and a composition containing water, the polyglycerol dialkyl or alkenyl ether 70 wt% or more the following formula of the total amount (1 ')

(In the formula, R ¹ and R ² are the same or different, and are a linear or branched alkyl group or alkenyl group having 8 to 22 carbon atoms which does not have a hydroxyl group. N is the number of glycerol units. Represents an integer of 5 to 15)
The composition for moisturizing cosmetics which is a compound represented by these. The moisturizing cosmetic composition according to claim 1, wherein the content of each component is as follows.
Polyglycerin dialkyl or alkenyl ether: 1 to 30 parts by weight Water: 40 to 99 parts by weight   The composition for moisturizing cosmetics according to claim 1 or 2, wherein the polyglycerin dialkyl or alkenyl ether has an HLB value of 6 to 20.   Cosmetics containing the composition for moisturizing cosmetics of any one of Claims 1-3.

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