JP2893128B2 - Cosmetic additive and cosmetic containing the same - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention provides an additive for hair and skin cosmetics, and gives a refreshing feeling without stickiness at the time of application containing the same, and The present invention relates to a cosmetic having excellent moisture retention and good emulsion stability.

[Problems to be solved by conventional technology and invention]

In general, various humectants are used in cosmetics. However, conventional humectants do not provide sufficient moisturizing effect if the amount is small, and if the amount is large enough to achieve the effect, the system becomes stable. There were problems such as impairing the performance.

On the other hand, emulsion-type cosmetics are widely used because they can provide appropriate oil and moisture to skin and hair because of their composition. By changing the type and amount of the oil component, various emulsions having different physical properties and feeling in use can be obtained.

However, since the emulsion is a thermodynamically unstable system, its stabilization is difficult, and many studies and attempts have been made so far. One of the measures is to add an emulsifying aid. Such emulsifying auxiliaries include cationic auxiliaries, anionic auxiliaries, amphoteric auxiliaries, and nonionic auxiliaries, but nonionic auxiliaries are most preferred in view of the range of oil components that can be blended.

As an example of the addition of a nonionic emulsification aid, it is known that, for example, when a higher alcohol such as cetanol or cetostearyl alcohol is added for cosmetics, a liquid crystal structure is formed, and thus the stability is improved. Although the method of adding a higher alcohol in this way is effective in preventing crystallization of high melting point fats and oils, when these are added to maintain a stable state,
There are drawbacks in that the viscosity becomes very high, the spread at the time of application is poor, the oily feeling is strong and sticky. In addition, the liquid crystal structure of higher alcohol has problems such as the precipitation of crystals having a pearl-like luster and a decrease in viscosity due to the destruction of the liquid crystal structure.

Therefore, a composition in which a nonionic auxiliary agent that forms a lamellar liquid crystal structure is blended in the composition has been developed. For example, Japanese Patent Publication No. 38-5050 discloses the following general formula (I
I) [Wherein, p represents an integer of 1 to 3]. A skin and hair care agent containing a triol represented by the following formula is disclosed. However, since this triol becomes reverse middle liquid crystal in an aqueous solution, it has a disadvantage that it has a strong oily feeling and an insufficient moisturizing effect. JP-A-63-23737 discloses an aqueous dispersion of a niosome comprising a lipid lamella using polyglycerol ether as a nonionic amphiphilic substance. This is an improvement in stability by encapsulating a water-soluble active substance in vesicles, which are aqueous compartments contained between lipid layers. However, this also requires a high-temperature treatment of 80 ° C. or more during the formation of niosomes, and thus has a drawback that it is difficult to apply it to cosmetics containing an active substance having poor stability at high temperatures. Furthermore, JP-B-58-8287, JP-B-61
JP-56016, JP-A-57-77613, JP-A-57-94
No. 326 also discloses an aqueous dispersion of lipid globules using glycerol ether.However, homogenization is required in the production, or the lipid is dissolved in an organic solvent such as chloroform-methanol, and then the solvent is evaporated. And the production process is complicated, which is disadvantageous in that it is industrially difficult.

As described above, the conventional nonionic auxiliaries have a problem that the liquid crystal formation temperature range is narrow, the liquid crystal formation temperature is high, and it is difficult to form liquid crystals industrially.

Normally, in a state where active ingredients having a high melting point are separated without being emulsified and dispersed uniformly in cosmetics, effects such as moisturizing properties cannot be sufficiently obtained. Some of the nonionic auxiliaries have a moisturizing action, but the action was not satisfactory.

For this reason, there is no change such as crystal transition over a wide concentration range at the use temperature of cosmetics, and it is uniformly stable and has no oily feeling.
The development of cosmetics having excellent moisturizing effects has been desired.

[Means for solving the problem]

Under such circumstances, the present inventors have conducted intensive studies to solve the above problems, and as a result, by using a methyl-branched fatty acid ester having a specific structure, it is possible to obtain a cosmetic excellent in moisture retention, When this is incorporated into an emulsion type cosmetic, in addition to good moisturizing properties, it contributes to stabilization of the emulsion and the like, and it is possible to widen the uniform region of the high melting point active ingredient. The present inventors have found that an excellent cosmetic which can provide a refreshing feeling of use without any problem can be obtained, and completed the present invention.

That is, the present invention provides the following general formula (I) [Wherein, m and n each represent an integer of 0 to 20;
And the sum of n is from 10 to 16]. An additive for hair and skin cosmetics comprising a methyl-branched fatty acid ester represented by the formula: and a cosmetic containing the same.

In the general formula (I), the sum of m and n is 10 to 16,
Above all, 14 is preferable. Further, it is particularly preferable that the branched methyl group is located near the center of the alkyl main chain.

The methyl-branched fatty acid ester (I), which is an additive for hair and skin cosmetics of the present invention, is produced according to the following reaction formula.

[Wherein m and n have the same meaning as described above, and R represents a lower alkyl group.] That is, the compound (I) is reacted by reacting pentaerythritol (III) with a lower alkyl ester (II) of a methyl-branched fatty acid. ) Is manufactured.

The lower alkyl ester (II) of a methyl-branched fatty acid used in this reaction is obtained by esterifying the corresponding carboxylic acid by a conventional method. Among the corresponding carboxylic acids, those obtained industrially are usually mixtures in which the total number of carbon atoms of the alkyl group and the position of the branched methyl group have a certain distribution, for example, by-products during the production of oleic acid dimer Isostearic acid having a methyl branch obtained as a compound having a total carbon number of 18 (sum of m and n is 14)
Containing at least 75%, with the balance being 14, 16 or 20 carbon atoms in total, and the branched methyl group is located almost at the center of the alkyl main chain [Journal of the American Oil Chemistry Society (J. Amer. Oil Che
m.Soc.) Vol. 51, 522, (1974)].

In this reaction, the ratio of the lower alkyl ester (II) of methyl-branched fatty acid to pentaerythritol (III) used is preferably (III) / (II) = 1/1 to 10/1 in molar ratio.

The solvent used in the reaction is not particularly limited, but is preferably one that dissolves both the lower alkyl ester of methyl-branched fatty acid (II) and pentaerythritol (III). For example, dimethylformamide or the like is suitably used.

As a catalyst for the reaction, an alkali catalyst is usually used, and sodium methylate or the like is preferably used. The amount of the catalyst is not particularly limited, but is preferably used in the range of 0.1 to 20 mol% based on the lower alkyl ester (II) of the methyl-branched fatty acid.

The reaction temperature of this reaction is selected from the range of 60 to 150 ° C.

The compound (I) can be isolated from the reaction mixture by a conventional method, for example, solvent evaporation, recrystallization, chromatography, etc., alone or in combination.

The methyl branched fatty acid ester (I) thus obtained has unique properties. That is, it is a lamellar liquid crystal at room temperature, has excellent compatibility with most solvents, and has properties such as being almost uniformly dispersed when mixed with water.

When compound (I) is used as a compounding material in cosmetics, one or more compounds of compound (I) can be used in combination, and the amount of the compound (I) in cosmetics of the present invention is not particularly limited. 0.01 to 80% by weight (hereinafter simply referred to as%), particularly preferably 0.1 to 50%.

In order to further increase the effects of the present invention, a surfactant can be used in combination. As such a surfactant, any of a nonionic surfactant, a cationic surfactant, an anionic surfactant and an amphoteric surfactant can be used. Particularly, for a skin cosmetic, the nonionic surfactant is used for the hair. For cosmetics, cationic surfactants are preferred. Examples of the nonionic surfactant include polyoxyethylene alkyl ether, polyoxyethylene alkyl phenyl ether, polyoxyethylene fatty acid ester, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, fatty acid monoglyceride, glyceryl ether, and the like. As the cationic surfactant,
Representative examples include quaternary ammonium salts,
Any of those usually used in cosmetics can be used, but branched alkyl quaternary ammonium salts described in JP-A-61-267505 are particularly preferable. These surfactants constitute 0.01 to 30% of the total composition, preferably 0.1 to 10%.
%.

Further, the cosmetic of the present invention may contain, if necessary, components usually used for cosmetics, medicines, foods, etc., for example, higher alcohols having a linear or branched alkyl or alkenyl group; liquid paraffin, Hydrocarbons such as petrolatum and solid paraffin; lanolin derivatives such as liquid lanolin and lanolin fatty acids; silicon derivatives such as dimethylpolysiloxane, polyether-modified polysiloxane and amino-modified polysiloxane; higher alcohol higher fatty acid esters and higher fatty acids Fats and oils such as long-chain amidoamines having an alkyl or alkenyl group; animal and vegetable fats and oils such as mink oil and olive oil; Thickeners such as molecules; coloring agents such as dyes and pigments; ultraviolet absorbers; astringents; It can be blended water, perfumes and the like; Lumpur, glycerine, carbitol, 3-methyl-1,3-butanediol, other humectants such as sugars,.

The cosmetic of the present invention can be produced according to a usual method. For example, basic cosmetics such as an oil-in-water type, a water-in-oil type emulsified cosmetic, and an oily cosmetic: makeup cosmetics such as a lipstick and a foundation; Detergent; can be applied to hair cosmetics such as hair rinses, treatments, and hair styling agents.

[Action and effect of the invention]

Methyl-branched fatty acid ester (I) used in the present invention
Is excellent as a moisturizing component, has low oiliness and good spreadability because it forms a thermotropic liquid crystal at room temperature, and further incorporates a high melting point substance into the liquid crystal, thereby improving the stability of the system and effectively using the active ingredient. It has a function of working effectively and is extremely useful as a compounding material for hair and skin cosmetics.

Therefore, the cosmetic of the present invention has good spreadability at the time of application, gives a refreshing feeling without stickiness, is excellent in moisture retention, and has good emulsion stability.

〔Example〕

Hereinafter, the present invention will be described in more detail with reference to Examples, but the present invention is not limited thereto.

Example 1 29.9 g of methyl isostearate was placed in one reaction vessel equipped with a distillation condenser equipped with a thermometer, a stirrer, and a decompression device.
(0.1 mol), 68 g (0.5 mol) of pentaerythritol, 28
% Sodium metalate / methanol solution (1.9 g) and dimethylformamide (450 ml) were charged at 100 ° C. and the degree of vacuum was 100 to 120.
The reaction was performed for 2.5 hours under the condition of mmHg. During this reaction, about 100 ml of dimethylformamide was distilled from the reaction system. After cooling the contents of the reaction, about 400 ml of water was added and the layers were separated. After ether was added to the lower layer for extraction, the ether layer was added to the upper layer that was first separated, and washed three times with 200 ml of water each time. After removing ether under reduced pressure, purity 77%
Of pentaerythritol monoisostearate was obtained (70% yield). This was purified by silica gel chromatography (ethyl acetate / ethanol) to give a single spot by thin layer chromatography to obtain 21 g of pentaerythritol monoisostearate (yield 50%) (purity 94%). This was a thermotropic liquid crystal at room temperature.

IR (liquid film) cm ^-1 : (FIG. 1) 3450 (OH), 2840 to 2950 (CH), 1720 (C =
O), 1640 (CH), 1040 (CO) Test Example 1 Properties of the compound obtained in Example 1 and a conventionally known similar compound (comparative compound) at room temperature and compatibility with water were examined. The results are shown in Table 1.

Example 2 A hair rinse having the composition shown in Table 2 was prepared using the compound produced in Example 1, and the rinse performance was examined.

Production method; Second water dissolved in water heated to 70 ° C at the same temperature
The components shown in the table were added, mixed with stirring, and then cooled to room temperature with stirring to obtain a hair rinse composition.

Evaluation method of rinsing performance; Bundle 20 g (15 cm length) of Japanese female hair that has never been subjected to beauty treatment such as cold perm or bleach, and use this hair bundle as a main component with an anionic activator The hair was rinsed with shampoo, 2 g of the hair rinse shown in Table 2 was applied uniformly, then rinsed with running water for 30 seconds, and then towel dried. The hair bundle in the wet state was organoleptically evaluated for flexibility, smoothness and oiliness. The evaluation criteria were rated as 特 に when particularly excellent, 特 に for good, △ for equivalent, and × for poor. The results are shown in Table 2.

The hair rinse composition containing the compound (I) was excellent in flexibility and smoothness, and less oily.

Example 3 A hair rinse composition having the composition shown in Table 3 was prepared according to a conventional method, and its rinsing performance was examined. The results are shown in Table 3.

Each of the obtained hair rinsing agent compositions exhibited good rinsing performance and also had good stability.

 The sensory evaluation was performed in the same manner as in Example 2.

(Storage stability)

The sample was placed in a 100 ml transparent glass container, and after storage, the appearance was visually observed. The evaluation was shown based on the following criteria.

：: The whole is uniform, and no abnormality such as dispersion and aggregation is observed.

×: Non-uniform, separation and aggregation were observed.

Example 4 Hair treatment composition: (%) 2-dodecylhexadecyltrimethylammonium chloride 1.5 stearyltrimethylammonium chloride 1.0 dimethylpolysiloxane (500cs) 1.0 cetostearyl alcohol 3.0 Compound (I) (Example 1) 3.0 Liquid paraffin 3.0 Hydroxyethyl cellulose (1% aqueous solution viscosity 8,000c
p) 0.5 Polyoxyethylene oleyl ether (E0 = 5) 0.5 Methyl paraben 0.2 Perfume 0.4 Purified water Balance meter 100.0 Smooth, flexible, less oily, light and moisturizing hair treatment composition I got something.

Example 5 Hair cream composition: (%) di-2-dohexyldecyldimethylammonium chloride 2.0 cetyltrimethylammonium chloride 1.0 dimethylpolysiloxane (1000cs) 0.5 Compound (I) (Example 1) 1.0 cetyl alcohol 5.0 diproprene glycol 6.0 Glycerin 10.0 Liquid paraffin 3.5 Perfume 0.4 Purified water Balance meter 100.0 A hair cream composition having excellent smoothness and flexibility, no stickiness, and imparting a good feel was obtained.

Example 6 Conditioning mousse composition: (%) dialkyldimethylammonium chloride ^{* 1} 0.5 methylphenylpolysiloxane (300 cs) 1.0 isotridecyl myristate 1.0 3-methyl-1,3-butanediol 1.0 glycerin 2.5 liquid paraffin 2.5 Compound (I) (Example 1) 0.2 95% ethyl alcohol 5.0 Methyl paraben 0.1 Perfume 0.1 Propellant (LPG) 10.0 Purified water Balance meter 100.0 * 1: Same as Example 3 A conditioning mousse composition giving good feeling was obtained.

Example 7 Cream: Oil phase component: (%) Cetanol 2.0 Stearic acid 3.0 Trimethylol isoheptadecane 3.0 Compound (I) (Example 1) 2.0 Lipid (cholesteryl isostearate) 8.0 Monolauryl glycerin 2.0 Polyoxyethylene (20) ) Sorpitan monolaurate 2.0 Water phase component: dipropylene glycol 10.0 1,3-butylene glycol 5.0 Ethyl paraben 0.1 Methyl paraben 0.2 Perfume 0.1 Purified water Balance meter 100.0 The cream of the present invention has a good feeling in use and an excellent moisturizing effect. showed that.

[Brief description of the drawings]

1 and 2 are diagrams showing the results of IR and NMR of pentaerythritol monoisostearate obtained in Example 1, respectively.

──────────────────────────────────────────────────続 き Continuation of the front page (56) References JP-A-54-35220 (JP, A) JP-B-52-31020 (JP, B2) Bull. Jap. Petrol. Inst. , 1973, 15 (1), p. 1-6 (58) Field surveyed (Int. Cl. ⁶ , DB name) A61K 7/00 CA (STN) REGISTRY (STN)

Claims (3)

(57) [Claims] 1. The following general formula (I) [Wherein, m and n each represent an integer of 0 to 20, and the sum of m and n is 10 to 16.] An additive for hair and skin cosmetics comprising a methyl-branched fatty acid ester represented by the formula: 2. The hair and skin cosmetic additive according to claim 1, wherein in formula (I), the sum of m and n is 14. 3. A hair or skin cosmetic comprising one or more of the hair and skin cosmetic additives according to claim 1 or 2.