JPH08218089A - Sustained release aroma composition - Google Patents

Abstract

PURPOSE: To obtain an aroma composition, containing a polyvalent carboxylic acid derivative of a perfume, capable of sustainedly decomposing and emitting the aroma in spite of no aroma possessed by itself and excellent in persistence of the aroma and useful for human bodies, etc., such as a hair tonic. CONSTITUTION: This composition comprises a perfume which is an active ingredient contained as a polyvalent carboxylic acid derivative thereof. Furthermore, an ester derivative, etc., prepared by adding, e.g. potassium carbonate and reacting triethyl citrate, etc., as a polyvalent carboxylic acid part with alcohols corresponding to a perfume ingredient such as phenylethyl alcohol while heating the mixture.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a sustained release fragrance composition, and more particularly to a sustained release fragrance composition containing a polycarboxylic acid derivative.

[0002]

2. Description of the Related Art Conventionally, when a fragrance is blended with a sustained-release fragrance composition, a liquid composition is a water-soluble fragrance dissolved in an alcohol, propylene glycol, carbitol or other appropriate solvent or suspending agent. Add fragrance,
Alternatively, a method has been adopted in which an oily fragrance is directly solubilized in these liquid cosmetics using a surfactant or added in the form of an emulsion. In a powder or solid composition, these oily flavors are generally blended in the form of powder or granules by adsorption, an inclusion compound, encapsulation or coating using an appropriate excipient. is there.

[0003]

The fragrances have the problem that they start to volatilize from the moment they are used, and they decay over time, eventually losing their scent effect. A retention agent has been added as a method for preventing such fragrance dissipation, but its effect is insufficient.
Further, the clathrate compound and the encapsulated product are excellent in durability, but the expression of the fragrance is extremely suppressed, so that it is not always satisfactory as a perfume, and a suitable fragrance is used for the sustained-release aroma composition to be used. The technical problem of stable release over a long period of time has not yet been solved. On the other hand, it is becoming clear that the unpleasant odors emitted from the human body, such as bad breath, axillary odor, scalp and rancid odor, are produced by the decomposition of excreted liquid from sebum lines and various organic substances by indigenous fungi. There is.

Therefore, one or more glycosides selected from thymol glycosides, cis-3-hexenol glycosides and methyl salicylate glycosides are blended in the oral composition, and these oral compositions are prepared. An oral composition has been proposed in which the glycoside is hydrolyzed by the action of glucosidase in saliva when used, and thymol, cis-3-hexenol, and methyl salicylate are released to develop a flavor (Japanese Patent Application Laid-Open No. HEI-3). -90016).

Further, a sustained-release active ingredient releasing agent comprising an ester of a polyhydric alcohol having a carboxyl group or an oxyalkylene derivative of a polycarboxylic acid and an active ingredient having a hydroxyl group has been proposed (JP-A-3-17025). However, since the amount of the fragrance component to be replaced as the active ingredient becomes small, the amount of the fragrance component generated is not satisfactory.

Furthermore, after the fragrance is made into any one of a saccharide derivative, a phosphoric acid ester derivative, an amino acid derivative and a carboxylic acid derivative, it is incorporated into a sustained release fragrance composition for human body, and these are treated by indigenous bacteria on the skin. The present inventors have already proposed that the derivative is decomposed to generate fragrance gradually and stably over a long period of time (Japanese Patent Application No. Hei.
No. 307309) specifically described quinic acid, caffeic acid and the like as carboxylic acid of the carboxylic acid derivative to be used, this time, a new polyvalent carboxylic acid derivative such as citric acid and malic acid was examined.

Some polyvalent carboxylic acid derivatives are commercially available, such as citrate monoalkyl ester and citrate trialkyl ester as emollients in cosmetics, and perfume diluting agents such as triethyl citrate. Nothing has been investigated for use as a sustained-release aroma composition. Furthermore, in order to use it as a sustained-release aroma composition because the aroma of the substituent is not considered,
These compounds are not sufficient.

The inventors of the present invention have conducted diligent research to solve the above problems, and as a result, have found polyvalent carboxylic acid derivatives of fragrances,
It has been found that the above problems can be solved all at once by blending the composition into a sustained-release aroma composition, and the present invention has been completed.

[0009] That is, an object of the present invention is to provide a sustained-release aroma composition having excellent fragrance durability.

[0010]

That is, the present invention provides a sustained-release aroma composition containing a fragrance as an active ingredient,
The fragrance is a sustained-release fragrance composition characterized by being a polyvalent carboxylic acid derivative of the fragrance, which will be described in detail below.

In the present invention, the sustained-release aroma composition containing the polyvalent carboxylic acid derivative of the fragrance to be used is used to prepare a carboxylic acid of the fragrance as described above by fungi including various skin-resident bacteria. The derivative is gradually decomposed, and the aroma inherent in the fragrance component is stably released over a long period of time, and as a result, a sustained-release aroma composition having extremely excellent sustainability can be obtained.

In the present invention, the sustained-release fragrance composition is particularly preferable if it is used for the purpose of masking various odors generated from the human body due to the growth of bacteria and positively wearing a pleasant fragrance. It is not limited. In general, for example, liquid, spray or powder cosmetics, body wash for nursing, sanitary napkins, socks and the like which are applied by being impregnated or applied to clothes directly in contact with the human body are exemplified. You can

The polyvalent carboxylic acid derivative of the fragrance used in the present invention may be any one as long as the fragrance is suppressed by converting the fragrance into an ester derivative with a polyvalent carboxylic acid.

Specifically, as the polyvalent carboxylic acid moiety,
Examples thereof include succinic acid, tartaric acid and citric acid. Further, it is also possible to use a polycarboxylic acid in which a part of carboxylic acid groups is substituted with an ethyl group or the like.

Alcohols corresponding to perfume ingredients include pentanol, 3-methylbutanol, 3-methylpentanol, 2-hexanol, 2-heptanol,
Undecanol, cis-3-hexenol, cis-6-
Nonenol, 2,6-nonadien-1-ol, 9-decenol, geraniol, linalool, nerol, citronellol, hydroxycitronellol, myrcenol, 3,7-dimethyloctanol, farnesol,
Aliphatic alcohols such as nerolidol and lavandurol; menthol, terpineol, piperitol, perilla alcohol, carveol, myrtenol,
Alicyclic alcohols such as Santalol, cedrol, patchouli alcohol, ionol, and hydroxydamascon; benzyl alcohol, cumin alcohol, 2
-Aromatic alcohols such as phenylethyl alcohol, phenylpropyl alcohol, cinnamyl alcohol, α-amylcinnamyl alcohol; eugenol, vanillin, anise alcohol, raspberry ketone,
Examples thereof include piperonyl alcohol and phenols such as sesamol.

The polyvalent carboxylic acid derivative of the fragrance used in the present invention can be easily obtained in the same manner as the citric acid monoalkyl ester form and the citric acid trialkyl ester form. Further, it can be easily synthesized by reacting a polyvalent carboxylic acid with the above alcohols in the presence of acids. Further, it can be synthesized by using a transesterification reaction of a lower alkyl ester such as triethyl citrate with a perfume ingredient. The polyvalent carboxylic acid derivatives of these fragrances can be purified by using means such as distillation or column chromatography.

The sustained-release fragrance composition of the present invention can be produced by blending one or more of the polyvalent carboxylic acid derivatives of the above fragrances.

As a method of solubilizing the polyvalent carboxylic acid derivative of the above-mentioned fragrance, the fragrance derivative is treated with an alcohol and a polyhydric alcohol such as ethanol, glycerin, propylene glycol, carbitol, diacetin, triacetin, sorbit, or alkylbenzene sulfonic acid. Soluble in surfactants such as salt, higher alcohol sulfate ester salt, alkyl trimethyl ammonium chloride, betaine type, polyoxyethylene nonyl phenyl ether, polyoxyethylene lauryl ether, polyoxyethylene polyoxypropylene block polymer, sucrose fatty acid ester Then, a method of diluting with water as necessary and the like can be mentioned.

As a method of emulsifying the polyvalent carboxylic acid derivative of the fragrance, the fragrance derivative is used as a sucrose fatty acid ester, fatty acid monoglyceride, sorbitan fatty acid ester, propylene glycol fatty acid ester, polyoxyethylene sorbitan fatty acid ester, gum arabic, Tragacanth gum, methyl cellulose, casein, soybean lecithin, egg yolk lecithin, starch, sodium alginate, locust bean gum, guar gum, carrageenan, sorbit, propylene glycol, glycerin,
Xanthan gum, pectin, cellulose derivative, starch derivative, cyclodextrin, polyglycerin fatty acid ester, saponin, sucrose and other emulsifiers, emulsification stabilizers or surfactants in an appropriate combination, and homogenized by a colloid mill or homogenizer. Etc.

If desired, suitable excipients such as dextrin, starch, modified starch and the like are added to the above-mentioned solubilized flavor derivative or emulsified polycarboxylic acid derivative, and then spray drying, vacuum drying, etc. It is also possible to dry and powder by the means of.

Further, the solubilized product, emulsion and powder obtained as described above are mixed with an appropriate solvent or carrier as exemplified above, and then filled in a container together with carbon dioxide gas, nitrogen gas, flon gas and the like. It can also be made into an aerosol type sustained release fragrance composition.

The compounding concentration of the polyvalent carboxylic acid derivative of the fragrance with respect to the sustained-release aroma composition of the present invention varies depending on various conditions such as the type of the composition and the threshold value of the fragrance constituting the fragrance derivative. However, in general, the concentration of the perfume derivative is preferably in the range of about 0.001 to about 20% by weight, more preferably about 0.005 to about 10% by weight.

Therefore, the present invention can remarkably reduce the amount of the fragrance added in the sustained release fragrance composition, which has been apt to be added in an unnecessarily large amount in order to maintain the fragrance intensity over a long period of time. In addition, since the fragrance itself is also incorporated in the form of a derivative, the change over time is significantly improved compared to conventional products, and the fragrance lasts longer. It can also be used for aroma enhancement and fragrance modulation. You can also

In the sustained-release aroma composition of the present invention, as a matter of course, in addition to the above-mentioned fragrance derivatives, those generally used, such as peppermint oil, spearmint oil,
Natural essential oils such as rose oil, patchouli oil, orange oil, neroli oil and lemon oil; terpene hydrocarbons such as α-pinene, β-pinene, terpinolene and p-cymene; cis-3-hexenol, n-undecylene alcohol ,
Aliphatic alcohols such as n-octyl alcohol; terpene alcohols such as linalool, geraniol, citronellol, l-menthol, nerolidol and santalol; phenylethyl alcohol, cinnamic alcohol, methylphenylcarbinol, t-butylcyclohexanol Such as aromatic alcohols or derivatives thereof; phenols such as anisole, anethole, eugenol or derivatives thereof; aliphatic aldehydes such as n-heptylaldehyde, undecylenaldehyde, 2,6-nonadienal; citral, citronellal, hydroxycitronone Terpene aldehydes such as lal and perilaldehyde; benzaldehyde, phenylacetaldehyde, cinnamic aldehyde, anisaldehyde, kumi Aromatic aldehydes such as aldehydes, heliotropin, cyclamenaldehyde, vanillin; Aliphatic ketones such as methyl n-amyl ketone, methylheptenone and diacetyl; Terpene cyclic ketones such as l-carvone, menthone, piperiton and camphor; Benzophenone , Cyclic ketones such as Ionone, Methylionone, Iron, Maltol, Jasmon; Macrocyclic musks such as Muscon, Cyclopentadecanone, Ethylene brushate, Musk-type fragrance compounds such as Nitromusk, Indan Musk; Rose oxide, Linalool oxide, etc. Oxides; esters of aliphatic or aromatic acids with terpene alcohols, aliphatic alcohols, aromatic alcohols, phenols, etc .; nitrogen-containing flavor compounds; sulfur-containing flavors Compound and such natural essential oils and these examples can be blended blended fragrance obtained by mixing appropriate fragrance compounds.

The present invention will be described in more detail below with reference to examples.

[0026]

【Example】

Synthesis Example 1 Method for synthesizing phenyl ethyl citrate derivative (hereinafter abbreviated as CAPE) After adding 300 mg of potassium carbonate to 10 g of triethyl citrate and 13.3 g of phenylethyl alcohol, 6 hours under heating while removing generated ethanol. It was stirred. After completion of the reaction, the ether layer was washed with 50 ml of diethyl ether and 50 ml of purified water. The ether layer was dried over magnesium sulfate and then concentrated under reduced pressure. Further, vacuum distillation was performed to remove unreacted phenylethyl alcohol and triethyl citrate. As a distillation residue, 7.4 g of citric acid phenylethyl ester derivative was obtained. As a result of GC-MS analysis, formation of monophenylethyl citrate citrate and diphenylethyl monoethyl citrate as its main components was confirmed.

Synthesis Example 2 Synthesis Method of Citric Acid Rose Base Ester Derivative (hereinafter abbreviated as CARE) The same treatment was carried out by using 10 g of rose base according to the formulation of Table 1 instead of the phenylethyl alcohol used in Synthesis Example 1, Citric acid rose base ester derivative 6.8
g was obtained as a distillation residue part.

[0028]

[Table 1]

Comparative Example 1, Example 1 and Example 2 (Heartnick)

Hearth nicks were prepared according to the formulations shown in Table 2 and evaluated.

[0031]

[Table 2]

(Evaluation method) 10 panelists (24 to 45
(Aged male) was subjected to unscented shampoo treatment, and the hair artic of Examples and Comparative Examples were applied to the left and right sides of the head. The scent intensity of the applied part after 3 hours, 8 hours, and 1 day after the sensory treatment was expressed by the number of persons who were sensory judged. The results are shown in Table 3.

[0033]

[Table 3]

As shown in Table 3, in the comparative examples, almost no fragrance was felt after 8 hours, whereas in the examples, the fragrance was felt until one day later.

[0035]

The sustained-release aroma composition containing the polyvalent carboxylic acid derivative of the fragrance obtained according to the present invention has no fragrance per se, but gradually decomposes to generate an fragrance and thus has a long-lasting fragrance. It is possible to provide a very unique sustained-release aroma composition having excellent properties.

 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Minor Iwamoto 335, Kayajuku, Nakahara-ku, Kawasaki-shi, Kanagawa Hasegawa Kaori Co., Ltd.Kawasaki Research Institute Co., Ltd. (72) Akira Fujita, 335, Kayajuku, Nakahara-ku, Kawasaki, Kanagawa Kawasaki Institute Co., Ltd.

Claims (2)

[Claims] 1. A sustained-release fragrance composition containing a fragrance as an active ingredient, wherein the fragrance is a polyvalent carboxylic acid derivative of the fragrance. 2. A sustained release fragrance composition for human body, which comprises using the sustained release fragrance composition according to claim 1 for human body.