JPH0739336B2 - Stabilized clathrate compound and cosmetics containing the same - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a stabilized clathrate compound obtained by coating an inclusion compound having cyclodextrin as a host and a perfume ingredient as a guest with oil, and the clathrate compound. The present invention relates to cosmetics containing a contact compound.

[Prior Art] It is well known that an inclusion compound obtained from a fragrance and cyclodextrin suppresses the volatility of the fragrance, improves the stability, and facilitates formulation (Japanese Patent Publication No. S52-52). −
21573, JP-A-53-56313, 55-38338). In addition, examples of application of the inclusion compound include bath agents, creams, shampoos, etc. (Japanese Patent Publication No. 52-21573).
No. JP-A-59-10323). Further, a method of coating the clathrate with a hydrophilic polymer compound has been proposed because it is not possible to sufficiently suppress the volatility of the flavor with the clathrate of the fragrance and cyclodextrin as it is (Japanese Patent Publication No. 56-
44905 publication).

[Problems to be Solved by the Invention] However, these conventional techniques are limited to the addition of an inclusion compound of a fragrance and cyclodextrin to a solid, powdery or paste-like product. When compounded in a base containing the fragrance, the fragrance as the host is gradually released into the base, so that the fragrance cannot be stably present.

In view of these circumstances, the present inventors have conducted intensive studies to obtain a perfume-cyclodextrin inclusion compound that is stable under any storage conditions such as a base containing water, and as a result, the inclusion of the perfume and cyclodextrin has been investigated. It has been found that when the compound is further coated with oil, the inclusion compound of the fragrance and cyclodextrin is stably present at the same time as suppressing the volatility of the fragrance. Furthermore, it was found that the cyclodextrin clathrate compound coated with oil is stable even in acidic or alkaline product systems.

A stable clathrate compound obtained by further coating the clathrate compound of the fragrance and cyclodextrin with an oil according to the present invention not only stably preserves the fragrance in a storage state, but also application to the skin, rubbing, or face washing, washing, It has been found that the fragrance is volatilized promptly by friction such as when washing hair and water such as water and sweat, and the present invention has been completed based on these findings.

[Means for Solving Problems] That is, according to the present invention, a stabilized clathrate compound obtained by encapsulating a perfume in cyclodextrin, and then coating this clathrate compound with oil, and a compound thereof Cosmetics.

The fragrance as used in the present invention refers to a mixed fragrance that is a synthetic fragrance, a natural fragrance, or a mixture thereof.

Examples of oil include avocado oil, camellia oil, turtle oil, macadamia nut oil, corn oil, mink oil, olive oil, rapeseed oil, egg yolk oil, sesame oil, persic oil, wheat germ oil, southern oil, castor oil, linseed oil. , Safflower oil, cottonseed oil, eno oil, soybean oil, peanut oil, teaseed oil, kaya oil, rice bran oil, cinnamon oil, Japanese tung oil, jojoba oil, germ oil, triglycerin, glycerin trioctanoate, triisopalmitic acid Liquid oils and fats such as glycerin, cocoa butter, coconut oil, horse fat, hardened coconut oil, palm oil, beef tallow, mutton fat, hardened beef tallow, palm kernel oil, pork fat, beef bone fat, sorghum kernel oil, hardened oil, beef leg Solid fats and oils such as fat, syrup, hydrogenated castor oil, beeswax, candelilla wax, cotton wax, carnauba wax, bayberry wax, ivorot wax, spermaceti wax, monta wax, nu Wax, lanolin, kapok wax, lanolin acetate, liquid lanolin, sugar cane wax, lanolin fatty acid isopropyl, hexyl laurate, reduced lanolin, jojoba wax, hard lanolin, shellac wax, polyoxyethylene (hereinafter referred to as POE) lanolin alcohol ether, POE lanolin alcohol Waxes such as acetate, POE cholesterol ether, lanolin fatty acid polyethylene glycol, POE hydrogenated lanolin alcohol ether, liquid paraffin, ozokerite,
Hydrocarbons such as squalene, pristane, paraffin, ceresin, squalane, petrolatum, microcrystalline wax, isopropyl myristate, cetyl octanoate, octyldodecyl myristate, isopropyl palmitate, butyl stearate, hexyl laurate,
Myristyl myristate, decyl oleate, hexyldecyl dimethyloctanoate, cetyl lactate, myristyl lactate, isocetyl stearate, isocetyl isostearate, cholesteryl 12-hydroxystearate, di-
2-ethylhexyl ethylene glycol, dipentaerythritol fatty acid ester, monoisostearate N
-Alkyl glycol, neopentyl glycol dicaprate, diisostearyl malate, glycerine di-2-heptylundecanoate, trimethylolpropane tri-2-ethylhexylate, trimethylolpropane triisostearate, pentane-erythritol tetra-2-ethylhexylate , Glycerin tri-2-ethylhexylate, trimethylolpropane triisostearate, cetyl-2-ethylhexanoate, 2-ethylhexyl palmitate, glyceryl trimyristate, tri-2-heptylundecanoic acid glyceride, castor oil fatty acid methyl ester , Oleic acid oil, cetostearyl alcohol, acetoglyceride, palmitic acid 2
-Heptyl undecyl, diisobutyl adipate, N-
Lauroyl-L-glutamic acid-2-octyldodecyl ester, di-2-heptylundecyl adipate, ethyl laurate, di-2-ethylhexyl sebacate,
Synthetic esters of 2-hexyldecyl myristate, 2-hexyldecyl palmitate, 2-hexyldecyl adipate, diisopropyl sebacate, 2-ethylhexyl succinate, ethyl acetate, butyl acetate, amyl acetate, triethyl citrate, etc., methyl poly Silicon such as siloxane, methylphenylpolysiloxane, methylhydrogenpolysiloxane, decamethylpolysiloxane (silicone emulsion), methylpolysiloxane (silicone emulsion) and the like can be mentioned. Among them, liquid and non-polar oil components, such as liquid paraffin and squalane, are particularly preferable.

In addition, cyclodextrin (hereinafter referred to as CD) is 6
It is a type of non-reducing maltooligosaccharide in which ~ 12 glucose molecules are cyclically linked by α-1,4-glucoside bonds. Any of these may be used in the present invention.

The process for preparing the oil-coated perfume and CD inclusion compounds according to the present invention comprises two steps. The first stage is the inclusion compound of fragrance and CD (hereinafter referred to as CD inclusion compound)
And the second step is a step of coating the obtained CD inclusion compound with an oil component.

There are various methods for preparing the first-stage CD inclusion compound, and for example, the kneading method is an industrial method. Since commercially available β-CD (molecular weight: 1134) forms an inclusion compound in almost equimolar amounts with guest molecules, it is preferable to use 2 to 20 parts by weight of β-CD per 1 part by weight of the fragrance. Now, in the actual preparation, about 0.5 to 5 parts by weight of β-CD is added to 1 part by weight of water to form a paste, and the mixture is well kneaded. Add fragrance to it and knead further. A suitable kneading time is 5 to 60 minutes. The clathrated paste becomes a dried CD clathrate compound by allowing it to stand overnight at a spray drier, a ventilation drier, or room temperature. This is crushed with a crusher and used.

In the second step, the obtained CD inclusion compound is coated with oil. Here, the CD inclusion compound is added to a liquid oil component (a solid oil component is heated at room temperature), and the mixture is stirred and dispersed. The weight ratio of oil to CD inclusion compound is 10: 1 to 1:10.
0 is appropriate.

According to this method, the CD inclusion compound can be coated with an oil component very easily, and a substance that stably exists in the product during storage and that volatilizes the fragrance component promptly during use can be obtained. In the following, for example, a liquid-crystal paraffin, a CD inclusion compound coated with a weight ratio of 1:10 is used as a coating CD-inclusion compound (liquid paraffin; 1: 1).
Represented as 0).

In the present invention, the coating CD inclusion compound is blended in a total amount of 0.1 to 90% by weight (hereinafter referred to as%) in the total amount of the cosmetic, but 1 to 10% in terms of no stickiness as a cosmetic. A degree is preferable.

In addition to the above-mentioned essential components, the cosmetic of the present invention, if necessary, depending on the type of cosmetic, oil, water, surfactant, humectant, lower alcohol, thickener, fragrance, antioxidant, Ingredients usually used in cosmetics such as chelating agents, pigments, antiseptic and antifungal agents can be added.

The cosmetic composition of the present invention may be any of the dosage forms, solid-based, solution-based,
Any formulation such as a solubilizing system, an emulsifying system, a powder dispersion system, a water-oil two-layer system, a water-oil-powder three-layer system, etc. may be used.

Further, the application of the cosmetics of the present invention is also arbitrary, such as lotion, emulsion, cream, facial cosmetics such as packs and hair cosmetics such as hair tonic, hair cream, shampoo, hair rinse, as well as foundation, lipstick, eye It can be used for makeup cosmetics such as shadows, body cosmetics, and aromatic cosmetics.

[Examples] The present invention will be specifically described with reference to Examples and Comparative Examples. The present invention is not limited to this. The blending amount is% by weight.

Example 1 After adding 100 g of water to 100 g of β-CD and kneading, 25 g of lemon oil was further added and kneading was continued for 10 minutes until a paste was formed. The CD inclusion compound obtained by this treatment is left to dry overnight at room temperature. The obtained clathrate of CD was 120 g. This is crushed with a crusher.

Next, 120 g of CD inclusion compound ground to 100 g of liquid paraffin
And kneading for 10 minutes until the CD inclusion compound is evenly dispersed. Coated CD obtained by this treatment
The inclusion compound (liquid paraffin; 10:12) was 220 g.

In addition, β-CD is referred to as CD unless otherwise specified.

Example 2 80 g of water was added to 100 g of CD and kneaded, and then 15 g of a mixed fragrance was added.
And knead for 20 minutes until it becomes a paste. The CD inclusion compound obtained by this treatment is left to dry overnight at room temperature. The obtained clathrate of CD was 110 g. This is crushed with a crusher.

Next, 110 g of the pulverized CD inclusion compound is added to 110 g of an equal mixture of petrolatum and liquid paraffin, and the mixture is kneaded for 10 minutes until the CD inclusion compound is evenly dispersed. The coated CD inclusion compound (Vaseline-liquid paraffin; 1: 1) obtained by this treatment was 220 g.

Example 3 (comparison at room temperature) 100 g of CD was mixed with 100 g of water and kneaded, and then orange oil was added.
Add 20 g and knead for 30 minutes until a paste is formed.
The CD inclusion compound obtained by this treatment is left to dry overnight at room temperature. The obtained clathrate of CD was 118 g. This is crushed with a crusher.

Next, 50 g of the crushed CD inclusion compound is added to 5 g of liquid paraffin and kneaded for 10 minutes until the CD inclusion compound is evenly dispersed. The coated CD inclusion compound (referred to as powder A) obtained by this treatment was 55 g. Therefore, the change in the content of orange oil after the uncoated CD inclusion compound (referred to as powder B) and the powder A was left at room temperature was examined. The change in the content was examined by dispersing each powder in ethyl ether and stirring well to extract the encapsulated orange oil, and measuring the weight excluding the ethyl ether. The powder A was previously dispersed in hexane to remove liquid paraffin. The results are shown in Table 1 (note that the content immediately after standing was set to 100).

From Table 1, it has been clarified that the powder A more reliably retains the included fragrance component than the powder B.

Example 4 (Cleansing Foam) (1) Beef tallow 40.0 (2) Coconut oil 15.0 (3) Cetanol 1.0 (4) Oleyl alcohol 0.8 (5) Purified lanolin 1.1 (6) Preservative proper amount (7) Sodium hydroxide 2.0 (8) ) Potassium hydroxide 6.5 (9) Purified water Residue (10) Coating CD inclusion compound 5.0 (lemon oil, liquid paraffin; 1: 1) Manufacturing method Add sodium and potassium hydroxide to purified water and keep at 70 ℃ . Components other than (10) are heated and melt-mixed at 70 ° C, and an aqueous phase portion kept at 70 ° C is added thereto with stirring to carry out a saponification reaction. The coating CD inclusion compound was added to this with stirring, and then cooled to obtain a cream-like cleansing foam.

Comparative Example 1 Comparative Example 1 was carried out in the same manner as in Example 4 except that the coated CD inclusion compound of (10) in Example 4 was replaced with the same uncoated CD inclusion compound (compounding amount 2.5). Got

The stability with time of Example 4 and Comparative Example 1 was evaluated by the following test. Lemon oil generally causes a significant odor on alkaline bases. Therefore, if a strange odor was confirmed in this test, it was determined that the CD inclusion compound released lemon oil. After placing 10 cc of the sample in a 50 ml screw tube and leaving it in a constant temperature bath of 50 ° C. for 30 days, the scent from the bottle mouth was judged by an expert's olfactory test.

The results are shown in Table 2.

As is clear from Table 2, the retention capacity of CD is maintained only in the product system containing water only after coating. Moreover, in Example 4, the scent of fresh lemon could be enjoyed during use.

Example 5 (soap) (1) Soap substrate 95.0 (2) Coating CD inclusion compound 5.0 (prepared fragrance A, Vaseline; 2: 3) (3) Dye in appropriate amount The production methods (2) and (3) were added to the soap substrate. Then, it was mechanically kneaded or frame kneaded to produce soap.

Example 6 (soap) (1) Soap substrate 95.0 (2) Coating CD inclusion compound (citral) 5.0 (citral, vaseline; 2: 3 (3) Dye suitable amount Production method As in Example 5.

Comparative Example 2 Comparative Example 2 was carried out in the same manner as in Example 6 except that the coated CD inclusion compound of (2) in Example 6 was replaced with the same uncoated CD inclusion compound (compounding amount 3.0). Got

The stability with time of Example 6 and Comparative Example 2 was evaluated by the following test. In general, citral causes significant odor and discoloration in an alkaline base. Therefore, if odor and discoloration were confirmed in this test, it was judged that the CD inclusion compound released citral. Wrap the soap in wrap, 50
After leaving it in a constant temperature bath for 30 days, the scent and color of soap was judged by an expert.

The results are shown in Table 3.

As is clear from Table 3, the retention capacity of CD is exhibited in soap only after coating with oil. Moreover, in Example 6, the scent of fresh citral could be enjoyed during use.

Example 7 (shampoo) (1) Alkyl sulfate triethanolamine salt 15.0 (2) Coconut fatty acid monoethanolamide 5.0 (3) Ethylene glycol monostearate 2.0 (4) Preservative proper amount (5) Dye proper amount (6) Perfume 0.1 (7) Coating CD inclusion compound 3.0 (prepared fragrance B, petrolatum; 1: 1) (8) Purified water Residual production methods (1) to (6) were dissolved by stirring in (8), and further (7)
Were mixed and dissolved to obtain shampoo.

Example 8 (Hair rinse) (1) Alkyltrimethylammonium chloride 3.0 (2) Cetyl alcohol 1.0 (3) Preservative 0.1 (4) Glycerin 5.0 (5) Perfume 0.1 (6) Dye Appropriate amount (7) POE (8 mol) Stearyl Ether 0.6 (8) Purified water Residual (9) Coating CD inclusion compound 2.0 (Prepared fragrance C, Vaseline; 3: 2) Preparation methods (1) to (8) were mixed and dissolved at 80 ° C, and allowed to cool to room temperature. Further, (9) was mixed and dissolved to obtain a hair rinse.

Example 9 (bath powder) (1) talc 80.0 (2) coating CD inclusion compound 20.0 (prepared fragrance D, liquid paraffin; 1:20) The production methods (1) and (2) were mixed and stirred to obtain a bath powder. It was

Example 10 (Kneading perfume) (1) Coating CD inclusion compound 90.0 (Prepared perfume E, Vaseline; 5: 4) (2) Glycerin trimyristate 8.0 (3) Perfume 2.0 Mix the manufacturing methods (1) to (3) Stirring gave a perfume.

[Effects of the Invention] The coated CD inclusion compound of the present invention not only does not release the included fragrance even when left at room temperature for a long time,
Even in acidic or alkaline product systems containing water, the clathrate is not released. Therefore, the perfume can be stably present during the period of storage as a product. Moreover, it has a characteristic of releasing a fragrance when it is used, which is not present in the prior art.

Claims (1)

[Claims] 1. An inclusion compound in which a fragrance is included in cyclodextrin in an amount of 1/100 to 10 times (weight ratio)
Cosmetics characterized by containing 0.1 to 20% by weight of a stabilized clathrate compound obtained by coating with the oil content.