JPS6335517A - Stabilized clathrate compound and cosmetic containing same - Google Patents

Abstract

PURPOSE:To obtain a clathrate compound capable of controlling the volatility of perfumery and stably keeping the perfumery in any storage state, by coating a clathrate compound of a perfumery and cyclodextrin (CD) with an oil. CONSTITUTION:1pt.(wt.) of CD is thoroughly kneaded with 0.5-5pts. of water and the produced paste is further kneaded together with a perfumery to effect the inclusion of the perfumery. The obtained paste is dried and finely pulverized with a crusher. The resultant CD clathrate compound is added to a liquid oil (or heated oil which is solid at normal temperature) and dispersed by mixing to effect the coating of the oil to the clathrate compound. The oil is preferably a nonpolar liquid (e.g. liquid paraffin, squalane, etc.) and the weight ratio of the oil to the clathrate compound is 10:1-1:100. The coated CD-clathrate compound is preferably added at an amount of about 1-10% based on the whole cosmetic.

Description

Detailed Description of the Invention [Industrial Application Field] The present invention provides a stabilized clathrate obtained by coating an clathrate containing cyclodextrin as a host and a fragrance ingredient as a guest with an oil component, and This invention relates to cosmetics containing adhesion compounds.

[Prior Art] It has been well known that clathrate compounds obtained from fragrances and cyclodextrins suppress the volatility of fragrances, improve stability, and facilitate formulation (Japanese Patent Publication No. 52
No.-21573, JP-A No. 53-56313, 55-3
Publication No. 8338). Furthermore, examples of applications in which the clathrate compounds are blended include bath additives, creams, shampoos, etc.
Publication No.). In addition, since the clathrate compound of a perfume and cyclodextrin as it is cannot sufficiently suppress the volatility of the perfume, a method has been proposed in which the clathrate compound is coated with a hydrophilic polymer compound (Japanese Patent Publication No. 5 FLR 44905).

[Problems to be Solved by the Invention] However, these conventional techniques are limited to adding a clathrate compound of a fragrance and a cyclodextrin to a solid, powdered or paste product; When it is blended into a base, the host perfume is gradually released into the base, which has the disadvantage that the perfume cannot be stably present.

In view of these circumstances, the present inventors have conducted intensive research to obtain a fragrance-cyclodextrin clathrate compound that is stable under any storage conditions, such as in a base containing water. It has been found that by further coating the compound with oil, the volatility of the fragrance can be suppressed, and at the same time, the inclusion compound between the fragrance and cyclodextrin can stably exist under any storage conditions. Furthermore, we have found that oil-coated cyclodextrin clathrate compounds exist stably even in acidic or alkaline product systems.

The stable clathrate compound of the present invention, which is a clathrate compound of a fragrance and a cyclodextrin coated with an oil component, not only stably preserves the fragrance in the storage state, but also can be applied to the skin, rubbed on the skin, washed, washed, etc. It was discovered that fragrances are quickly volatilized by friction during hair washing and moisture such as water and sweat, and based on these findings, the present invention was completed.

[Means for Solving the Problems] That is, the present invention provides a stabilized clathrate compound obtained by including a fragrance in cyclodextrin and then coating this clathrate compound with an oil, and a stabilized clathrate compound obtained by incorporating the same. It is a cosmetic.

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

Examples of oils include avocado oil, camellia oil, tardle oil, macadamia nut oil, corn oil, mink oil, olive oil, rapeseed oil, egg yolk oil, sesame oil, persic oil, wheat germ oil, sasanqua oil, castor oil, and linseed oil. oil, safflower oil, cottonseed oil, eno oil, soybean oil, peanut oil,
Liquid oils and fats such as tea seed oil, kaya oil, rice bran oil, sinensis oil, Japanese tung oil, jojoba oil, germ oil, triglycerin, glycerin trioctanoate, glycerin triisopalmitate, cacao butter, coconut oil, horse tallow, hardened Coconut oil, palm oil, beef tallow, mutton tallow, hydrogenated beef tallow, palm kernel oil, pork fat, beef bone tallow,
Solid oils and fats such as Japanese oak kernel oil, hydrogenated oil, cow leg fat, Japanese oak, hydrogenated castor oil, beeswax, candelilla wax, cotton wax,
Carnauba wax, Paberry wax, Ipotal wax, Whale wax, Montan wax, Nuka wax, Lanolin, Kapok wax,
Lanolin acetate, liquid lanolin, sugar cane wax, isopropyl lanolin fatty acid, hexyl laurate, reduced lanolin, jojoba wax, hard lanolin, shellac wax,
Waxes such as polyoxyethylene (hereinafter referred to as POE) lanolin alcohol ether, POE lanolin alcohol acetate, POE cholesterol ether, lanolin fatty acid polyethylene glycol, POE hydrogenated lanolin alcohol ether, liquid paraffin, osikelite, squalene, bristane, paraffin, montane ,
Hydrocarbons such as squalane, petrolatum, microcrystalline wax, isopropyl myristate, cetyl octoate, octyldodecyl myristate, isopropyl valmitate, butyl stearate, hexyl laurate, myristyl myristate, decyl oleate, hexyldecyl dimethyl octoate , cetyl lactate, myristyl lactate, isocetyl stearate, isocetyl isostearate, cholesteryl 12-hydroxystearate, ethylene glycol di-2-ethylhexylate, dipentaerythritol fatty acid ester, N-alkyl glycol monoisostearate, neopentyl glycol capriate, Diisostearyl malate, glyceryl di-2-hebutylundecanoate, trimethylolpropane tri-2-ethylhexylate, trimethylolpropane triisostearate, pentaneerythritol tetra-2-ethylhexylate, glyceryl tri-2-ethylhexylate, triisostearic acid Trimethylolpropane, cetyl 2-ethylhexanoate, 2-ethylhexyl palmitate, glycerin trimyristate,
tri-2-heptylundecanoic acid chrycerite, castor oil fatty acid methyl ester, oleic acid oil, cetostearyl alcohol, acetoglyceride, 2-hebutylundecyl valmitate, diisobutyl adipate, trauroyl L-glutamate-2-octyldodecyl ester, Di-2-hebutyl undecyl adipate, ethyl laurate, di-2-ethylhexyl sepatate,
Synthetic esters such as 2-hexyldecyl myristate, 2-hexyldecyl valmitate, 2-hexyldecyl adipate, diisopropyl cepatate, 2-ethylhexyl succinate, ethyl acetate, butyl acetate, amyl acetate, triethyl citrate, methylpolymer Examples include silicones such as siloxane, methylphenylpolysiloxane, methylhydrogenpolysiloxane, decamethylpolysiloxane (silicon emulsion), and methylpolysiloxane (silicon emulsion). Among these, particularly preferred are liquid non-polar oils such as liquid paraffin and squalane.

Also, cyclodextrin (hereinafter referred to as CD) is
It is a type of non-reducing maltooligosaccharide in which 6 to 12 glucose molecules are linked to a ring via α-1,4-glucosidic bonds. In the present invention, any of these may be used.

The method of preparing the oil-coated perfume-CD clathrate according to the present invention consists of two steps. 1st
The second step is to prepare a clathrate compound (hereinafter referred to as CI clathrate compound) of fragrance and CD, and the second step is to prepare a clathrate compound (hereinafter referred to as CI clathrate compound) of fragrance and CD.
This is the step of coating the D clathrate with oil.

There are various methods for preparing the CD clathrate compound in the first step, and for example, the kneading method is an industrial method. Since commercially available β-CD (molecule [1134) forms an clathrate compound in approximately equimolar amounts with the guest molecule, it is preferable to use 2 to 20 parts by weight of β-CD per 1 part by weight of the perfume. Now, regarding the actual preparation, β-CD is added at 0.5 to 5
Add about 1 part by weight of water to make a paste and mix well. Add spices and knead further. The appropriate kneading time is 5 to 60 minutes. After the clathration, the paste becomes a dry CD clathrate compound by using a spray dryer, a ventilation dryer, or leaving it overnight at room temperature. This is used by crushing it with a crusher.

In the second step, the obtained CD clathrate compound is coated with an oil. Here, a CD clathrate compound is added to a liquid oil (solid oil is heated at room temperature) and dispersed by stirring. The weight ratio of oil to CD clathrate is 1
A ratio of 0:1 to 1:100 is suitable.

According to this method, it is possible to coat the CD clathrate compound with oil very easily, and it is possible to obtain a substance that stably exists in the product during storage and quickly evaporates the six ingredients when used.

Hereinafter, for example, a CD clathrate compound coated with liquid paraffin at a weight ratio of 1:10 is coated with coating C
It is expressed as D clathrate compound (liquid paraffin; 1:10).

In the present invention, the coating CD clathrate compound is blended in a total of 0.1 to 90% by weight (hereinafter referred to as %) of the total amount of the cosmetic, but it is 1. About 10% is preferable.

In addition to the above-mentioned essential ingredients, the cosmetics of the present invention may optionally contain oil, water, surfactants, humectants, lower alcohols, thickeners, fragrances, antioxidants, etc., depending on the type of cosmetics. Ingredients commonly used in cosmetics, such as chelating agents, pigments, and preservatives and fungicides, can be blended.

The dosage form of the cosmetic of the present invention is arbitrary, such as solid, solution,
Any dosage form may be used, such as a solubilized system, an emulsified system, a powder dispersion system, a water-oil two-layer system, a water-oil one-powder three-layer system, etc.

In addition, the cosmetics of the present invention can be used in any manner, including facial cosmetics such as lotions, milky lotions, creams, and bags, hair cosmetics such as hair tonics, hair creams, shampoos, and hair rinses, as well as foundations and lipsticks. It can be used in makeup cosmetics such as eye shadow, body cosmetics, aromatic cosmetics, and the like.

[Examples] Next, examples and comparative examples will be given to specifically clarify the present invention. The present invention is not limited thereby. The blending amount is in 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 the mixture was mixed until it became paste-like.
Knead for 0 minutes. The CD clathrate compound obtained by this treatment is left to dry at room temperature overnight. The amount of CD clathrate compound obtained was 120 g. Grind this using a grinder.

Then 120 g f! of CD inclusion compound ground into 100 g of liquid paraffin. : Add and knead for 10 minutes until the CD clathrate is evenly dispersed. The coated CD clathrate compound (liquid paraffin; 10:12) obtained by this treatment was 220 g.

Note that hereinafter, unless otherwise specified, β-CD will be referred to as CD.

Example 2 After adding 80 g of water to 100 g of CD and kneading, 1415 g of mixed incense was further added and kneaded for 20 minutes until it became paste-like. The CD clathrate compound obtained by this treatment is left to dry at room temperature overnight. The amount of CD clathrate compound obtained was 110 g. Grind this using a grinder.

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

Example 3 (comparison when left at room temperature) After adding 100 g of water to 100 g of CD and kneading, 20 g and 1 of orange oil were further added, and the mixture was stirred until it became paste-like.
Knead for 0 minutes. The CD clathrate compound obtained by this treatment is left to dry at room temperature overnight. The amount of CD clathrate compound obtained was 118 g. Grind this using a grinder.

Next, the CD clathrate compound 5 was ground into 5 g of liquid paraffin.
Add 0 g and knead for 10 minutes until the CD clathrate is evenly dispersed. The amount of coated CD clathrate compound (referred to as Powder A) obtained by this treatment was 55 g. Therefore, changes in the orange oil content were investigated when an uncoated CD clathrate compound (referred to as Powder B) and Powder A were left at room temperature. Changes in content were investigated by dispersing each powder in ethyl ether, stirring well, extracting the clathrated orange oil, and measuring the weight excluding ethyl ether. Note that liquid paraffin was removed from Powder A in advance by dispersing it in hexane. The results are shown in Table 1 (the content immediately after standing was set as 100).

Table 1 From Table 1, it is clear that Powder A retains the clathrated fragrance components more reliably than Powder B.

Example 4 (Cleansing foam) (1) Beef tallow 40.0
(2) Coconut oil 15.0 (
3) Setanol 1.0 (4
) Oleyl alcohol 0.8 (5)
Purified lanolin 1.1 (6) Preservative appropriate amount (7) Sodium hydroxide 2.0 (8) Potassium hydroxide 6.5 (9) Purified water
Remaining (10) Coating C
D clathrate compound 5.0 (Lemon oil, liquid paraffin: 1) Production method Sodium hydroxide and potassium are added to purified water, heated and maintained at 70'C. Other components other than (10) at 70°
The mixture is heated and melted and mixed with C, and the aqueous phase kept at 70°C is added thereto with stirring to carry out a saponification reaction. A creamy cleansing foam was obtained by adding the coating CD clathrate compound to this while stirring and cooling it thereafter.

Comparative Example 1 Comparison was made in the same manner as in Example 4 except that the same uncoated CD clathrate compound (blending amount 2.5) was used instead of the coated CD clathrate compound (10) in Example 4. Example 1 was obtained.

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

The results are shown in Table 2.

Table 2 As is clear from Table 2, the retention ability of CD is maintained only after coating in product systems containing water. Moreover, when using Example 4, one could enjoy the scent of fresh lemon.

Example 5 (Soap) (1) Soap base 95.0 (
2) Coating CD clathrate compound 5.0 (compounded fragrance F4A, petrolatum; 2:3) (3) Color M
After adding appropriate amounts of manufacturing methods (2) and (3) to the soap base, soap was manufactured by mechanical kneading or border forming.

Example 6 (Soap) (1) Soap base 95.0 (
2) Coating CD clathrate compound (citral) 5.0
(Citral, Vaseline; 2:3) (3) Pigment
Appropriate amount according to manufacturing method Example 5.

Comparative Example 2 Comparison was made in the same manner as in Example 6 except that the same uncoated CD clathrate (formulation [3,0)] was used instead of the coated CD clathrate in (2) in Example 6. Example 2 was obtained.

The stability over time of Example 6 and Comparative Example 2 was determined by the following test. Generally, citral causes significant odor and discoloration in alkaline bases.

Therefore, if odor or discoloration is confirmed in this test,
It was determined that the CD clathrate released citral. The soap was wrapped in plastic wrap and left in a thermostat at 50°C for 30 days, and then the scent and color of the soap were judged by an expert.

The results are shown in Table 3.

Table 3 As is clear from Table 3, the retention ability of CD is exhibited in soaps only after they are coated with oil.

Moreover, when using Example 6, one could enjoy the fresh scent of citral.

Example 7 (shampoo) (1) Alkyl sulfate triethanolamine salt 15.0
(2) Coconut fatty acid monoethanolamide 5.0 (
3) Ethylene glycol monostearate 2.0 (・1
) Anti-IIπ agent appropriate amount (5
) Pigment Appropriate amount (6) Fragrance 0.1 (7) Coating CD clathrate compound 3.0 (Mixed fragrance B, Vaseline; C1) (8) Box ice making Add remaining manufacturing methods (1) to (6) into (8) Stir and dissolve, and then (7)
were mixed and dissolved to obtain a shampoo.

Example 8 (hair rinse) (1) Salt (hyalkyltrimethylammonium 3.0 (2) Cetyl alcohol 1.0 (3) Preservative
0.1(4) Glycerin
5.0 (5) Fragrance
0.1(6) Pigment
Appropriate amount (7) POE (8 mo) Ii) Suf')) tf--fL 0.6 (8) Purified water Remaining (9) Coating CD clathrate compound 2.0 (Mixed fragrance C, petrolatum; 3: 2) Production methods (1) to (8) were mixed and dissolved at 80°C, allowed to cool to room temperature, and (9) was further mixed and dissolved to obtain a hair rinse.

Example 9 (bath powder) (1) Talc 80.0
(2) Coating CD clathrate compound 20.0 (
Mixed fragrance D, liquid paraffin; 1:20) Production methods (1) and (2) were mixed and stirred to obtain a bath powder.

Example 10 (line perfume) (1) Coating CD clathrate compound 90.0 (
Mixed fragrance E, Vaseline; 5:4) (2) Glycerin trimyristate 8.0 (
3) Incense R2,0 Manufacturing method (1) to (3) f! : A line perfume was obtained by mixing and stirring.

"Effects of the Invention" The coated CD clathrate compound of the present invention not only does not release the clathrated fragrance even when left at room temperature for a long period of time, but also does not release the clathrated fragrance even in acidic or alkaline product systems containing moisture. It does not release the fragrance that it comes in contact with.Therefore, the fragrance can be stably present during the period when the product is stored.Furthermore, when it is used, it does not release the fragrance, which is not the case with conventional technology. It has characteristics.

Claims (2)

[Claims] (1) A stabilized clathrate compound obtained by including a fragrance in cyclodextrin and then coating this clathrate compound with an oil. (2) A cosmetic containing a stabilized clathrate compound obtained by including a fragrance in cyclodextrin and then coating the clathrate compound with an oil.