JP2000327551A - Humectant - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a humectant having actions of improving the moisture retaining ability of a horny layer and further permeating into hair and enhancing actions on protective effects thereof by including a specific amide derivative as an active ingredient. SOLUTION: This humectant is obtained by including an amide derivative represented by formula I (R is a 5-23C alkyl or a 5-23C alkenyl) as an active- ingredient. The derivative represented by formula I can be produced by a method, etc., for condensing, e.g. a carboxylic acid represented by formula II or its reactive derivative (an acid halide, an ester, an acid anhydride or the like) with a diglycolamine represented by the formula H2N-(CH2CH2O)2-H, as necessary, in the presence of a basic catalyst, etc., at room temperature to 250 deg.C under atmospheric pressure or a reduced pressure of 0.01 mmHg while preferably removing water or an alcohol produced by the reaction. The derivative represented by formula I is useful as the humectant, a skin preparation for external use for improving skin roughening and a hair cosmetic. Furthermore, the hair cosmetic is the one except a shampoo such as a hair rinse or a hair styling agent.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a humectant having an effect of improving rough skin and protecting hair.

[0002]

2. Description of the Related Art Conventionally, to improve or prevent rough skin, free amino acids, organic acids,
Cosmetics containing a water-soluble component contained in the stratum corneum, such as urea or inorganic ions, or a highly hydrophilic moisturizing substance have been used. However, such water-soluble components and moisturizing substances cannot be said to essentially prevent and treat rough skin, and their moisturizing effects are also temporary. On the other hand, application of natural ceramide, which is an intercellular lipid of the stratum corneum, to the skin has been studied for the purpose of improving the water retention ability, but it is expensive, and also has a low compoundability and formulation stability in external preparations. There was a problem that it was not desirable.

In view of such circumstances, the present inventors have found that some amide derivatives have an effect of fundamentally improving the water retention ability of the stratum corneum, and an effect of penetrating hair to enhance its protective effect. Found that there is
No. 34, JP-A-64-29347, JP-A-Hei-8
JP-A-319263 and JP-A-64-9913).

[0004] However, it has been difficult to keep the compoundability and compounding stability of such an amide derivative in the case of compounding it as an external preparation. In addition, in terms of production, there is also a problem that a multi-stage reaction is required, which is economically unfavorable.

[0005]

SUMMARY OF THE INVENTION Accordingly, an object of the present invention is to improve the water-retaining ability of the stratum corneum and to enhance the protective effect by penetrating into the hair. An object of the present invention is to provide a humectant which has good solubility in an agent, is excellent in compoundability and compounding stability, and can be manufactured efficiently and at low cost.

[0006]

The present inventors have studied various amide derivatives, and as a result, have found that the amide derivative represented by the following general formula (1) achieves the above object.

That is, the present invention provides the following general formula (1)

[0008]

Embedded image [In formula, R shows a C5-C23 linear or branched alkyl or alkenyl group. And a humectant comprising an amide derivative represented by the formula (1) as an active ingredient.

The amide derivative represented by the general formula (1) is
Although its use as a cleaning agent has been reported (Japanese Unexamined Patent Publication No.
No. 71893), it has not been known until now that it has an effect of improving the water retention ability of the stratum corneum of the skin.

[0010]

BEST MODE FOR CARRYING OUT THE INVENTION In the formula of the amide derivative represented by the general formula (1) in the present invention, R represents a linear or branched alkyl or alkenyl group having 5 to 23 carbon atoms. For example, pentyl, heptyl, nonyl,
Undecyl, tridecyl, pentadecyl, heptadecyl, nonadecyl, heneicosyl, tricosyl, isoheptadecyl, 1-ethylheptyl, 1-heptyldecyl, isoheptadecyl, methyl-branched isoheptadecyl,
Examples include 2,4,4-trimethylpentyl, 8-heptadecenyl, and 8,11-heptadecadienyl groups.
Among them, a linear or branched alkyl group having 11 to 23, particularly 13 to 17 carbon atoms is particularly preferred.

The amide derivative (1) in the present invention can be synthesized by a known amide synthesis method. For example, according to the following method, it can be produced safely and efficiently.

[0012]

Embedded image

[Wherein, R has the same meaning as described above. ]

That is, by condensing the corresponding carboxylic acid (2) or its reactive derivative (acid halide, ester, acid anhydride, etc.) with diglycolamine (3), the amide derivative (1) can be efficiently converted. Obtainable. Conditions for this condensation include a dehydrating agent such as dicyclohexylcarbodiimide or an alkali metal hydroxide such as potassium hydroxide or sodium hydroxide, an alkaline earth metal hydroxide such as calcium hydroxide, or an alkali metal carbonate such as potassium carbonate. , Alkaline earth metal carbonates such as calcium carbonate, sodium methoxide, sodium ethoxide, potassium
In the presence or absence of a basic catalyst such as an alkali metal alcoholate such as tert-butoxide or the like, at normal pressure to 0.
The reaction is preferably carried out at room temperature to 250 ° C. under a reduced pressure of 01 mmHg. At this time, it is preferable to use the diglycolamine (3) in excess with respect to the carboxylic acid (2) or a reactive derivative thereof. It is preferable because it proceeds. The amide derivative (1) thus obtained can be purified by a known method such as washing with water, column chromatography, distillation, crystallization, recrystallization and powder treatment.

The amide derivative (1) thus obtained is
For the skin, as shown in Test Example 1, it shows the effect of improving and preventing skin inflammation and rough skin by improving (maintaining and reinforcing) the water retention ability of the stratum corneum by penetrating into the lipid membrane between the stratum corneum cells. I do. In addition, as shown in Test Example 2, it exerts an effect of improving the feel of hair by having a protective effect on hair.

Accordingly, the amide derivative (1) of the present invention is useful as a humectant, a skin external preparation for improving rough skin, and a hair cosmetic. Here, the hair cosmetics refer to hair cosmetics excluding shampoos such as hair rinse, hair treatment, hair conditioner, and hair styling agent.

Such humectants, skin external preparations for improving rough skin, and hair cosmetics are bases (carriers) usually used in external preparations.
And an amide derivative (1).

The compound to which the amide derivative (1) is blended as a moisturizing agent and a skin external preparation for improving skin roughness includes not only cosmetics but also external medicines. Such external medicines, for example, various ointments containing a medicinal ingredient are included. May be based on an oil-based base, or based on an oil-in-water or water-in-oil emulsified base. The oil base is not particularly limited and includes, for example, vegetable oil, animal oil, synthetic oil, fatty acid, and natural or synthetic glyceride.
Although there is no particular limitation on the medicinal component, for example, an analgesic anti-inflammatory agent, an antipruritic agent, a bactericidal disinfectant, an astringent, an emollient, a hormonal agent and the like can be used as needed.

When used as a skin cosmetic, in addition to the amide derivative (1), oils, surfactants, ultraviolet absorbers, whitening agents, wrinkle improvers, alcohols commonly used as cosmetic components, Chelating agents, pH adjusters, preservatives, thickeners, pigments, fragrances, and the like can be arbitrarily combined and blended.

When used as a hair cosmetic, in addition to the amide derivative (1), for example, oils, cationic surfactants, silicones, cationic polymers, ultraviolet absorbers, alcohols, chelating agents, pH adjusters , Preservatives, thickeners, pigments, fragrances and the like can be combined in any combination.

The skin cosmetics can be, for example, water-in-oil or oil-in-water emulsified cosmetics, creams, cosmetic emulsions, lotions, oily cosmetics, lipsticks, foundations, baths, etc., and hair cosmetics. Can be, for example, a hair tonic, a hairdressing agent, a hair styling agent, a hair rinse, a hair treatment, a hair conditioner, a hair restorer, a hair restorer, and the like.

The amount of the amide derivative (1) in the skin cosmetic or hair cosmetic is not particularly limited, but is usually
In the case of emulsified cosmetics, the content is preferably 0.001 to 50% by weight (hereinafter simply referred to as%) of the total composition, and in the case of oily cosmetics based on liquid hydrocarbons such as squalane, The composition is preferably 0.01 to 50%, particularly preferably 0.1 to 20% in each case.

[0023]

Example 1 Production of N- [2- (2-hydroxyethoxy) ethyl] octadecanamide (where R is a heptadecyl group) (Compound 1) 500 ml equipped with a stirrer, a nitrogen inlet tube and a distillation apparatus Methyl stearate 103 in a three-necked flask
g, 73 g of diglycolamine and 3 g of sodium methoxide, and stirred at 140 ° C. under reduced pressure (20 torr) for 3 hours. After completion of the reaction, excess diglycolamine was distilled off under reduced pressure to obtain 128 g (yield: 100%) of the title compound.

Properties: white crystal Melting point: 87 ° C. ¹ H-NMR (CDCl ₃ , δ); 0.87 (t, J = 7.2 Hz, 3H), 1.17-1.41 (m, 28H), 1.51-1.78 (m,
2H), 2.18 (t, J = 7.2Hz, 2H), 3.40-3.53 (m, 2H), 3.53-3.65
(m, 4H), 3.70-3.86 (m, 2H), 5.86-6.11 (m, 1H).

Example 2 Preparation of N- [2- (2-hydroxyethoxy) ethyl] -methyl-branched isostearoylamide (where R is a methyl-branched isoheptadecyl group) (Compound 2)
In Example 1, except that methyl stearate was used instead of methyl stearate, the production was carried out in the same manner as in Example 1 to obtain the title compound.

Properties: colorless paste ¹ H-NMR (CDCl ₃ , δ); 0.66-0.97 (m, 6H), 1.00-1.49 (m, 25H), 1.49-1.77 (m, 2
H), 2.18 (t, J = 7.2Hz, 2H), 2.70-2.94 (m, 1H), 3.35-3.52
(m, 2H), 3.52-3.66 (m, 4H), 3.66-3.81 (m, 2H), 6.18-6.35
(m, 1H).

Example 3 N- [2- (2-hydroxyethoxy) ethyl] -2-
Preparation of heptylundecanamide (R is 1-heptyldecyl group) (Compound 3)
Example 1 except that methyl heptylundecanoate was used.
The title compound was obtained in the same manner as in the above.

Properties: colorless paste ¹ H-NMR (CDCl ₃ , δ); 0.70-1.00 (m, 6H), 1.05-1.48 (m, 26H), 1.48-1.71 (m, 2
H), 1.90-2.10 (m, 1H), 2.25-2.64 (m, 1H), 3.37-3.67 (m, 6
H), 3.67-3.87 (m, 2H), 5.96-6.14 (m, 1H).

Test Example 1 Compositions of the present invention comprising 33% of Compounds 1 to 3 produced in Examples 1 to 3 and 67% of Vaseline were prepared, and each was evaluated for skin conductance and skin roughness by the following methods. In addition, the same test and evaluation were performed using a comparison product consisting of only petrolatum. Table 1 shows the results.

(Test Method) Ten women, aged 20 to 50, who have rough skin on their cheeks in winter, are applied with different compositions on the left and right cheeks for two weeks. The following items were tested on the day after the two-week application was completed.

(1) Skin Conductance After washing the face with warm water of 37 ° C. and resting in a room at a temperature of 20 ° C. and a humidity of 40% for 20 minutes, the water content of the stratum corneum was measured with a skin conductance meter (manufactured by IBS). Measured. The skin becomes rougher as the conductance value becomes smaller, and the skin becomes heavier when the conductance value is 5 or less. On the other hand, if this value is 20
Above this, skin roughness is hardly recognized.

(2) Rough Skin Score Rough skin was observed with the naked eye and judged according to the following criteria. The score was shown as an average value.

0: No rough skin is recognized 1: Slight rough skin is recognized 2: Skin rough is recognized 3: Severe rough skin is recognized 4: Severe rough skin is recognized

[0034]

[Table 1]

Test Example 2 A hair rinse having the composition shown in Table 2 below was prepared, and the feel of the hair after the treatment with the hair rinse was evaluated by five expert panelists according to the following criteria, and the average value of the five hair rinses was shown. The results are shown in Table 2.

-2: Bad -1: Somewhat bad 0: Neither can be said +1: Somewhat good +2: Good

[0037]

[Table 2]

As is clear from the results shown in Tables 1 and 2, the compositions containing the amide derivative (1) are all excellent in the effect of increasing the water content of the stratum corneum and the effect of improving the rough skin, It is excellent in improving the feel of hair.

[0039]

The humectant of the present invention can be produced efficiently and inexpensively, has excellent stability, essentially improves the water retention capacity of the stratum corneum, and improves and prevents skin inflammation and rough skin. It exerts an effect and has an effect of improving the feel of the hair by a protective action on the hair. Furthermore, it has good solubility in a base and is excellent in compoundability and compounding stability.

Continuing from the front page (72) Inventor Kameyama Akiyo 2606 Kabane-cho, Akaga-cho, Haga-gun, Tochigi Prefecture Inside the Kao Co., Ltd. research institute (72) Inventor Hiroei Saito 2606, Kaiga-cho, Akabane-cho, Haga-gun, Tochigi prefecture Kao Corporation's research institute (72) Inventor Yoshinori Nishizawa 2606 Akabane, Kaiga-cho, Haga-gun, Tochigi Prefecture F-term in the Kao Corporation Research Laboratory 4C083 AC012 AC122 AC641 AC642 AC692 CC02 CC39 DD21 DD23 DD27 EE06 EE12

Claims (1)

[Claims] 1. The following general formula (1): [In the formula, R represents a linear or branched alkyl or alkenyl group having 5 to 23 carbon atoms. ] A humectant comprising an amide derivative represented by the formula (1) as an active ingredient.