JP5804995B2 - Lamella liquid crystal cosmetic composition - Google Patents

Description

  The present invention relates to a lamellar liquid crystal cosmetic composition containing a novel polyglycerin dialkyl or alkenyl ether, a polyhydric alcohol, an oily component, and water. The lamellar liquid crystal cosmetic composition is useful as a cleansing agent for makeup cosmetics.

  In the cosmetics field, cleansing agents for makeup removal include creams, emulsions, oils, oily gels, etc. with lots of oils, lotions with little or no oil, and aqueous There are various types such as gel type. The oil-blended type is superior in terms of detergency, but it has a sticky feeling and cannot be easily rinsed off with water, so it must be washed again with a facial cleanser, etc. It was difficult to become familiar with makeup stains, and in particular, it was inferior in terms of usability, such as being difficult to use in the bathroom. On the other hand, the type in which no oil agent is blended or a small amount is blended is excellent in usability but has a problem of weak cleaning power.

  Therefore, in recent years, an oily cleansing agent (cleansing oil) that is familiar with makeup stains and can be easily washed away with water has become the mainstream (Patent Document 1). Cleansing oil is a self-emulsifying oily liquid composition obtained by mixing an oily component and a surfactant. However, cleansing oil has a low viscosity, and it has been a problem that it may sag during the time it is picked up and applied to the skin. A general gelling agent or thickener can be used to increase the viscosity and make it difficult to sag. However, in that case, the problem is that the elongation on the skin is deteriorated.

  On the other hand, cleansing gel technology containing a nonionic surfactant such as polyoxyethylene, sucrose aliphatic carbon ester, polyhydric alcohol, oil, water, etc. is also disclosed (Patent Documents 2 and 3). . 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.

Japanese Examined Patent Publication No. 6-99275 Japanese Patent Laid-Open No. 4-5213 JP-A-8-143420

  Therefore, the object of the present invention is to have an appropriate viscosity and good elongation, easily adapt to make-up stains, quickly raise the stain components, and without leaving a clean and oily feeling by rinsing with water. The object is to provide a lamellar liquid crystal cosmetic composition that can be washed away.

  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 obtained compound has two hydrophobic groups bonded with a short spacer and further has a highly water-soluble polyglycerin moiety as a hydrophilic group, so that it has excellent surface activity, the compound, polyhydric alcohol, oil component and water. Can be used to form a lamellar liquid crystal, has an appropriate viscosity without using a gelling agent or thickener, has good elongation, and easily adjusts to make-up dirt. It was found that rinsing with water can be washed away without leaving a clean oily feeling. 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、又は直鎖状若しくは分岐鎖状の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、多価アルコール、油性成分及び水を含有するラメラ液晶型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 which may have a hydroxyl group, or a linear or branched alkenyl group. n represents the number of glycerin units and is an integer of 2 or more)
A lamellar liquid crystal cosmetic composition containing polyglycerin dialkyl or alkenyl ether, a polyhydric alcohol, an oily component, and water containing the compound represented by the formula:

In the lamellar liquid crystal cosmetic composition, the content of each component is as follows, and the viscosity at 25 ° C. is preferably 100 to 5000 mPa · s.
Polyglycerin dialkyl or alkenyl ether: 5 to 30 parts by weight Polyhydric alcohol: 5 to 30 parts by weight Oil component: 40 to 90 parts by weight Water: 0.1 to 20 parts by weight

  The HLB value of the polyglycerin dialkyl or alkenyl ether is preferably 6-12.

  The present invention also provides a cosmetic containing the lamellar liquid crystal cosmetic composition.

The lamellar liquid crystal cosmetic composition of the present invention has a shape in which two molecules of a monomeric surfactant (one hydrophobic group and one hydrophilic group type surfactant) are bound by a short spacer, and has an excellent surface active ability. A specific polyglycerin dialkyl or alkenyl ether having a polyhydric alcohol, an oily component and water.
Therefore, the lamellar liquid crystal cosmetic composition according to the present invention has an appropriate viscosity and good elongation without using a gelling agent or a thickener, and is easily adapted to makeup stains. It can be washed away without leaving a clean and oily feeling by floating and rinsing with water. The composition for lamellar liquid crystal cosmetics according to the present invention can be suitably used for cosmetics (for example, cleansing of makeup cosmetics, etc.).

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

  The lamellar liquid crystal cosmetic composition of the present invention contains at least polyglycerin dialkyl or alkenyl ether.

[Polyglycerin dialkyl or alkenyl ether]
The polyglycerin dialkyl or alkenyl ether of the present invention contains at least a compound represented by the following formula (1).

In formula (1), R ¹ and R ² are the same or different and each represents a linear or branched alkyl group which may have a hydroxyl group, or a linear or branched alkenyl group. is there. 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, tridecyl, s-tridecyl, t-tridecyl, isomyristyl, s-myristyl, t-myristyl, isopentadecyl, s-pentadecyl, t-pentadecyl, hexyldecyl, 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 _-C6-22 branched alkyl groups such as _-docosyl .

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

As R ¹ and R ² in the present invention, among others, a strong fence layer (palisade layer) can be formed on the interface, and thereby a lamellar liquid crystal phase can be formed. To 20 (more preferably 8 to 18 carbon atoms, particularly preferably 10 to 18, most preferably 12 to 18) linear or branched alkyl group or alkenyl group (particularly preferably linear alkyl group). Group or alkenyl group) is preferred.

  n shows the number of glycerol units and is an integer greater than or equal to 2, for example, 2-25, preferably 5-15, more preferably 8-13. When n is less than the above range, the HLB value decreases (hydrophilicity decreases), the solubility in aqueous components decreases, and for example, when used as a cleansing cosmetic, it tends to be difficult to wash away with water. . On the other hand, if n is excessive, the HLB value becomes too large (lipophilicity is reduced), the solubility in oily components is reduced, and for example, when used as a cleansing cosmetic, the detergency of makeup stains is reduced. Tend to.

  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 is represented by the above formula (1) such as undecaglycerin dioleyl ether, undecaglycerin dimyristyl ether, undecaglycerin dilauryl ether, among others. Among the compounds, n is 8 to 13, R ¹ and R ² are the same or different, and a compound having a linear or branched alkyl group or alkenyl group having 12 to 18 carbon atoms is It is particularly preferable because of its high solubility and high affinity for oil components.

The compound represented by the formula (1) of the present invention can adsorb closely to the interface without repulsion because two hydrophobic groups (R ¹ , R ² ) are bonded by a short spacer, thereby Extremely excellent surface activity can be exhibited. Therefore, the amount used can be reduced to less than half of the conventional amount, the environmental load is small, and the irritation to the skin and the like can be suppressed to a very small level. In addition, polyglycerin dialkyl or alkenyl ether has high solubility in water because the secondary hydroxyl group of polyglycerin, which is a hydrophilic group, can form a hydrogen bond with water, and has a low Kraft point (for example, 10 ° C. or less, Preferably 0 to 5 ° C.). Therefore, excellent solubility and solubilizing power can be exhibited even at low temperatures.

  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): Reacting n equivalents of glycidol with 1 equivalent of glycerin dialkyl or alkenyl ether having a secondary hydroxyl group represented by the following formula (6) obtained in Step (1)

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 a linear or branched alkenyl group having 8 to 20 carbon atoms (more preferably 8 to 18 carbon atoms, particularly preferably 10 to 18 carbon atoms, most preferably 12 to 18 carbon atoms). A chain alkyl group or an alkenyl group (particularly preferably, a linear alkyl group or alkenyl group) is preferred.

  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 alone or in admixture of two or more.

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. A linear or branched alkenyl group having 8 to 20 carbon atoms (more preferably 8 to 18 carbon atoms, particularly preferably 10 to 18 carbon atoms, most preferably 12 to 18 carbon atoms). A chain alkyl group or an alkenyl group (particularly preferably, a linear alkyl group or alkenyl group) is preferred.

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 alone or in admixture of two or more.

  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 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.

The polyglycerin dialkyl or alkenyl ether of the present invention has an HLB (Hydrophile-Lipophile Balance) value of, for example, 6 to 12, and preferably 8 to 10. 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

  The content of polyglycerin dialkyl or alkenyl ether in the lamellar liquid crystal cosmetic composition of the present invention (the total amount when containing two or more kinds) can be appropriately adjusted without any particular limitation, for example, It is about 5 to 30% by weight of the total amount (100% by weight) of the composition for lamellar liquid crystal cosmetics. The upper limit of the content of polyglycerin dialkyl or alkenyl ether is preferably 25% by weight, particularly preferably 20% by weight. The lower limit is preferably 7% by weight, particularly preferably 10% by weight. When the content of polyglycerin dialkyl or alkenyl ether is below the above range, the detergency tends to decrease. On the other hand, when the content of polyglycerin dialkyl or alkenyl ether exceeds the above range, the viscosity tends to be too high and it tends to be difficult to take out from the container.

[Polyhydric alcohol]
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 alone or in admixture of two or more.

  In the present invention, among them, at least one compound selected from 1,3-butylene glycol, sorbitol, maltitol, and glycerin is preferable in terms of excellent retention of a lamellar liquid crystal structure.

  The blending amount of the polyhydric alcohol is, for example, about 5 to 30% by weight of the total amount (100% by weight) of the lamellar liquid crystal cosmetic composition. The upper limit of the content of the polyhydric alcohol is preferably 25% by weight, particularly preferably 20% by weight. The lower limit is preferably 10% by weight, particularly preferably 15% by weight. When the content of the polyhydric alcohol is below the above range, the fluidity tends to decrease. On the other hand, when the content of the polyhydric alcohol exceeds the above range, it tends to be difficult to maintain the lamellar liquid crystal structure.

[Oil component]
As the oily component, an oily component that can be used in cosmetics is usually used, and a liquid and / or pasty oily component 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 oily component of the present invention include natural animal and vegetable oils and fats, 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 alone. , Or a mixture of two or more.

  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. These can be used alone or in admixture of two or more.

  Examples of the hydrocarbon include squalane, squalene, liquid paraffin, and petroleum jelly. These can be used alone or in admixture of two or more.

  Examples of the higher fatty acid include oleic acid, tall oil, and isostearic acid. These can be used alone or in admixture of two or more.

  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. These can be used alone or in admixture of two or more.

  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. These can be used alone or in admixture of two or more.

  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. These can be used alone or in admixture of two or more.

  Examples of the fat-soluble vitamin include tocopherol and derivatives thereof, retinol and derivatives thereof, and the like. These can be used alone or in admixture of two or more.

  As a compounding quantity of an oil-based component, it is about 40 to 90 weight% of the composition total amount (100 weight%) for lamellar liquid crystal type cosmetics, for example. The lower limit of the content of the oil component is preferably 45% by weight, particularly preferably 55% by weight. The upper limit is preferably 85% by weight, particularly preferably 80% by weight and most preferably 75% by weight. When the content of the oil component is below the above range, the cleaning power tends to decrease, or the amount of moisture transpiration tends to increase and the barrier property-imparting performance to the skin tends to decrease. On the other hand, when the content of the oil component exceeds the above range, the stickiness tends to be severe.

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

  The amount of water is, for example, about 0.1 to 20% by weight of the total amount (100% by weight) of the lamellar liquid crystal cosmetic composition. The lower limit of the water content is preferably 0.5% by weight, particularly preferably 3% by weight, and most preferably 5% by weight. The upper limit is preferably 15% by weight, particularly preferably 10% by weight. When the water content is below the above range, the refreshed feeling of use tends to decrease. On the other hand, when the content of water exceeds the above range, the detergency is reduced, or the amount of moisture transpiration is increased, which tends to lower the performance of imparting barrier properties to the skin.

  The lamellar liquid crystal cosmetic composition of the present invention is, for example, stirring essential components other than the above water at 40 to 80 ° C. while heating and dissolving and mixing, adding water while stirring, or further mixing. Alternatively, after all the essential components are blended, the mixture can be easily prepared by stirring at 60 to 80 ° C., heating and dissolving and mixing, and cooling with stirring until 20 to 30 ° C.

  The pH of the lamellar liquid crystal cosmetic composition of the present invention is, for example, about 6 to 8 (preferably 6 to 7).

  The viscosity at 25 ° C. of the lamellar liquid crystal cosmetic composition of the present invention is, for example, about 100 to 5000 mPa · s. The upper limit of the viscosity of the cosmetic of the present invention at 25 ° C. is preferably 3000 mPa · s, more preferably 2500 mPa · s, particularly preferably 2100 mPa · s, and most preferably 2000 mPa · s. The lower limit is preferably 200 mPa · s, more preferably 500 mPa · s, particularly preferably 700 mPa · s, and most preferably 820 mPa · s. If the viscosity is less than 100 mPa · s, it tends to sag from the hand, and the usability tends to decrease. On the other hand, when the viscosity exceeds 5000 mPa · s, it tends to be difficult to take out from the container (for example, a pump container). The viscosity of the lamellar liquid crystal cosmetic composition can be measured using a B-type viscometer.

  In addition, the lamellar liquid crystal cosmetic composition of the present invention contains the above-described polyglycerin dialkyl or alkenyl ether having excellent surface activity as a surfactant, so that even if it contains a large amount of oily components, it is transparent. The appearance is excellent.

[Cosmetics]
The cosmetic of the present invention is characterized by containing the lamellar liquid crystal cosmetic composition.

  In addition to the lamellar liquid crystal type cosmetic composition described above, other components can be appropriately blended in the cosmetic composition of the present invention within a range in which the object of the present invention can be achieved. Examples of other components include surfactants other than those described above, lower alcohols other than those described above, functional beads, capsules, salts, powders (for example, titanium oxide, talc, bentsite, cations, mica, etc.), Examples include bactericides, pigments, fragrances, preservatives, antioxidants, antioxidant aids, UV absorbers, humectants, flame retardants, pH adjusters, extracts derived from animals, plants, fish shells, and microorganisms. These can be used alone or in combination of two or more.

  As a compounding quantity of the said other component, it is 5 weight% or less of cosmetics whole quantity (100 weight%), for example.

  Since the cosmetic of the present invention has the above-described configuration, it has an appropriate viscosity without adding a gelling agent or a thickener, and does not easily drip from the hand during use and has good elongation. Further, the cosmetic of the present invention is excellent in detergency, easily adapts to and floats on makeup stains, and can be washed away by rinsing with water. The cosmetics of the present invention can be suitably used for cleansing of makeup cosmetics and the like, and application type cosmetics (for example, beauty creams, moisturizing gels, etc.).

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

Production Example 1 (Production of Dioleyl Glycerol)
After charging oleyl alcohol (reagent manufactured by Wako Pure Chemical Industries, Ltd., 2147 g) in an amount of 8 equivalents to 1 equivalent of the following oleyl glycidyl ether, 1 mol% tin (IV) chloride (2 g) was added in a nitrogen atmosphere. The oleyl glycidyl ether (manufactured by Yokkaichi Synthesis Co., Ltd., 325 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 (manufactured by Wako Pure Chemical Industries, Ltd., 2 g) was added to the resulting reaction crude liquid to remove moisture, and then diluted with heptane (manufactured by Wako Pure Chemical Industries, Ltd., 800 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 the unreacted oleyl glycidyl ether was distilled off at 230 ° C. under reduced pressure of 2 mmHg to obtain 470 g of dioleylglycerol.

Production Example 2 (Production of dimyristylglycerol)
Dimyristylglycerol was obtained in the same manner as in Production Example 1 except that myristyl glycidyl ether was used instead of oleyl glycidyl ether and myristyl alcohol was used instead of oleyl alcohol.

Preparation Example 1 (Production of undecaglycerin dioleyl ether)
A 28% sodium methoxide methanol solution (4 g) was added to the dioleylglycerol (32 g) obtained in Production Example 1, and methanol was distilled off under reduced pressure at 100 ° C., 2 mmHg, 10 hours.
Thereafter, glycidol (74 g) in an amount of 10 equivalents relative to 1 equivalent of the dioleylglycerol 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 4 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 another low boiling point component was further distilled off at 2 mmHg, thereby undecaglycerin diio. 81 g of rail ether (HLB: 10.9) was obtained.

Preparation Example 2 (Production of undecaglycerin dimyristyl ether)
Undecaglycerin dimyristyl ether (HLB: 12.3) was prepared in the same manner as in Preparation Example 1 except that dimyristylglycerol obtained in Production Example 2 was used instead of dioleylglycerol obtained in Production Example 1. Got.

Examples 1-8, Comparative Examples 1-8
The ingredients are blended in the proportions (% by weight) shown in the following table, heated and dissolved and mixed at a temperature of 80 ° C. or higher using an anchor mixer, and then cooled with stirring until the temperature becomes 35 ° C. or lower. A composition was obtained. The obtained cosmetic composition was evaluated by the following method.

[transparency]
About the external appearance of the composition for cosmetics obtained by the Example and the comparative example, it observed visually.

[Extension]
The cosmetic compositions (2 g) obtained in Examples and Comparative Examples were stretched on the back of the hand, and the ease of extension was subjected to sensory evaluation according to the following criteria.
Evaluation criteria Very good: ◎
Good: ○
Normal: △
Bad: ×

[viscosity]
The viscosity at 25 ° C. of the cosmetic compositions obtained in Examples and Comparative Examples was measured using a B-type viscometer.

[Detergency and feeling after use]
Lipstick (trade name “Makiage Superior Rouge RD759”, manufactured by Shiseido Co., Ltd., 0.2 g) was applied to the forearm, and the cosmetic compositions (about 0.5 g) obtained in Examples and Comparative Examples were obtained. I took 10 massages to get familiar with the lipstick. Thereafter, it was washed off with water, the degree of lipstick dropping was visually observed, and evaluated according to the following criteria. Moreover, sensory evaluation was carried out according to the following reference | standard for the skin feel (usability) after washing | cleaning.
Detergency criteria:
Fell completely: ◎
Almost fell: ○
A little left: △
Almost did not fall: ×
Usability evaluation criteria:
Very refreshing: ○
There is a little null: △
There is a null: x

The above results are summarized in the following table.

  As apparent from the examples, the cosmetic composition according to the present invention is transparent and has an appropriate viscosity, so that it can be prevented from dripping from the hand during use, and may further extend. In addition, it can be easily adapted to the makeup stains and lifted, and can be washed away without leaving a clean oily feeling by rinsing with water. That is, it is excellent in appearance, usability and cleaning power. Therefore, the cosmetic composition of the present invention can be suitably used as a cleansing agent for makeup cosmetics.

Claims (4)

Following formula (1)

(In the formula, R ¹ and R ² are the same or different and each has a C 8-20 linear or branched alkyl group which may have a hydroxyl group, or a linear or branched chain. And n represents the number of glycerin units and is an integer of 2 or more)
The composition for lamellar liquid crystal type cosmetics containing the polyglycerol dialkyl or alkenyl ether containing the compound represented by these, a polyhydric alcohol, an oil-based component, and water. The lamellar liquid crystal cosmetic composition according to claim 1, wherein the content of each component is as follows, and the viscosity at 25 ° C is 100 to 5000 mPa · s.
Polyglycerin dialkyl or alkenyl ether: 5 to 30 parts by weight Polyhydric alcohol: 5 to 30 parts by weight Oil component: 40 to 90 parts by weight Water: 0.1 to 20 parts by weight   The composition for lamellar liquid crystal cosmetics according to claim 1 or 2, wherein the polyglycerol dialkyl or alkenyl ether has an HLB value of 6 to 12.   Cosmetics containing the composition for lamellar liquid crystal type cosmetics of any one of Claims 1-3.