JPH05230496A - Compound perfume and aromatic composition containing same - Google Patents

Abstract

PURPOSE:To provide a compound perfume which can maintain a constant quality of fragrance and a constant aroma titer for a long time regardless of its preparation form and application, and an aromatic composition containing the compound perfume. CONSTITUTION:A compound perfume prepared by blending one or more perfume components belonging respectively to the top note, middle note and base note, wherein the whole or part of at least one perfume component thereof is mixed with other perfume components in the form of a precursor which can be converted into the perfume component through decomposition by the action of an acid, coupled with the acid for decomposing the precursor, and an aromatic composition containing the compound perfume.

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to an improved fragrance prepared by blending various fragrance components having different volatility belonging to top note, middle note and base note, and an improved fragrance containing the fragrance. It relates to a composition.

[0002]

2. Description of the Related Art In addition to cosmetics, soaps, foods, fragrances, bath agents, detergents, etc., compounded fragrances are being used more and more widely as the culture advances, and pharmaceuticals, solvents, insecticides, deodorants,
Its use extends to paints and printing inks.

When the raw materials of the fragrance are classified according to volatility,
It is classified into the following three.

(1) Top note: The vapor pressure is high, and when it is attached to odor paper, it vaporizes within 2 hours and leaves no odor, which is necessary for improving the first impression of the odor of the prepared fragrance. thing.

(2) Middle note It has a moderate vapor pressure, and when it is attached to odor paper, it is 2-6.
The part that forms a skeletal scent of the blended fragrance, as long as it smells for a long time.

(3) Base note A part which has a low vapor pressure, is highly retainable, and has an odor remaining on odor paper for 6 hours or more, and which is characteristic of the odor of a compounded fragrance.

The blended fragrance is prepared by blending and blending a large number of fragrance components having different volatility called the above-mentioned top note, middle note and base note to give a predetermined fragrance or aroma required for each prepared fragrance. Although it is included, the easily volatile components volatilize preferentially during use, and the proportion of the fragrance component prepared changes over time, resulting in a significant change in perfume and aroma potency over time. As a result, there is a drawback in that the predetermined fragrance cannot be maintained for a long period of time.

As an attempt to solve such a problem with an aromatic agent, a gel-like aromatic agent composition in which a perfume is contained in microcapsules and dispersed in a gel-like base material has been disclosed (Japanese Patent Laid-Open No. 2000-242242). 63-260567).
However, the above method is effective only for gel preparations, and even if it is applied to liquid preparations, microcapsules float or settle in the liquid, and the desired effect cannot be obtained.

[0009]

DISCLOSURE OF THE INVENTION An object of the present invention is to provide a compounded fragrance which can maintain a constant fragrance and aroma strength for a long period of time regardless of the formulation form and application, and an aromatic composition containing the compounded fragrance. To provide.

[0010]

Means for Solving the Problems That is, the present invention provides a compounded perfume containing one or more perfume ingredients belonging to each of top note, middle note and base note, and at least one perfume in the perfume ingredient. All or a part of the components are blended in the form of a precursor substance which is decomposed by the action of an acid to become the flavor component, and an acid which decomposes the precursor substance is also blended, and The present invention relates to an aromatic composition containing a mixed fragrance.

That is, the term "prepared perfume of the present invention" means a form of a precursor substance which becomes the perfume ingredient by decomposing all or part of at least one perfume ingredient in the prepared perfume ingredient by the action of an acid. And a acid that decomposes the precursor substance.

"Combining an acid" includes being mixed and present with a perfume ingredient containing the precursor substance, and being separately present and combined so that they can come into contact with each other at the time of use.

According to the research conducted by the present inventor, as described above, at least one of all the perfume ingredients contained in the prepared perfume is mixed in the form of a precursor substance, and when this is used together with an acid, Perfume ingredients gradually evaporate as the precursor substance and acid slowly progress, and each perfume ingredient volatilizes while maintaining a predetermined blending balance to maintain a certain fragrance and aroma potency for a long period of time. It was found to get. Particularly, it is preferable to mix a readily volatile topnote component as the precursor substance, and the desired purpose can be effectively achieved.

In the present invention, the basic blending of the blended fragrance is carried out by blending one or more fragrance components belonging to the top note, the middle note and the base note in accordance with a conventional method.

Examples of top note perfume ingredients include linalool, ethyl acetate, octyl aldehyde, benzaldehyde, phenylacetaldehyde, green leaf alcohol, phenylethyl formate, camphor, terpinolene,
d-limonene, l-menthol (el-menthol),
3-octenol, tetrahydrolinalool, borneol, isobregol, benzyl alcohol, dimethylbenzylcarbinol, methylphenylcarbinol,
Examples include dimethylphenyl carbinol.

Examples of middle note fragrance ingredients include terpineol, geraniol, citronellol, citronellal, decylaldehyde, benzyl acetate, citral, eugenol, phenylethyl acetate, citronellyl acetate, geranyl acetate,
Terpinyl acetate, acetophenone, thymol, isoeugenol, bornyl acetate, benzyl propionate, 9-decenol, nerol, rosinol, dimethyloctanol, lavandulol, mugol, myrcenol, tetrahydromugol, β-phenylethyldimethyl carbyl And β-phenylethylmethylethylcarbinol and phenoxyethyl alcohol.

Examples of the base note perfume ingredients include γ-undecalactone, ethylmethylphenylglycidate, hexylcinnamic aldehyde, phenylethyl alcohol, muscone, civetone, methylionone,
Yonone, cis-jasmone, vanillin, cinnamic alcohol, cyclamen aldehyde, farnesol, hydroxycitronellol, bornyl methoxycyclohexanol, nobor, nerolidol, santalol, sandalol, cedrol, beticerol, patchouli alcohol, indole, skatole, anise. Alcohol, γ-phenylpropyl alcohol, α-amylcinnamic alcohol, phenyl glycol, tertiary butyl cyclohexanol, benzoic acid, cinnamic acid, hydrocinnamic acid, phenylacetic acid, 2-methyltetrahydroquinoline, 6-methylquinoline, etc. Can be mentioned.

Generally, a compounded fragrance is prepared by a conventional method in which a large number of one or more kinds of fragrance components belonging to the above-mentioned top note, middle note and base note are mixed so as to obtain a predetermined odor or odor. It

In the present invention, a precursor for decomposing, with an acid, all or part of at least one of the perfume ingredients used in the basic formulation of the prepared perfume, preferably the perfume ingredients belonging to the top notes. In the form of, is compounded with an acid.

The precursor substance in the present invention is not particularly limited as long as it decomposes with an acid to produce a perfume component, and known glycosides of perfume components, glycerides, amino acid or peptide derivatives, cyclic acetal compounds, etc. Can be widely used.

As the glycoside, for example, a glycoside of an alcoholic flavor component can be used. When the alcoholic flavor component is represented by the formula R-OH, a general formula: G-O-R (1) (in the formula, G represents a glycosyl residue).

As the glycosyl residue represented by G in the general formula (1), any of various known saccharides such as monosaccharides, oligosaccharides and polysaccharides can be used.

Examples of the above-mentioned monosaccharides include glucose,
Examples thereof include hexoses such as galactose, mannose, glucosamine, galactosamine and mannosamine, and pentacarbon sugars such as arabinose, xylose and ribose.

Examples of oligosaccharides include hydrolysates of sucrose, lactose, trehalose, maltose, cellobiose, isomaltose, gentiobiose, laminaribiose, chitobiose, xylobiose, mannobiose, sophorose, mantotriose, starch, cellulose and the like. Can be illustrated.

As the polysaccharide, for example, starch,
Cellulose etc. can be illustrated.

Of these, glucose, galactose, mannose, glucosamine, maltose and lactose are particularly preferable.

Examples of the alcoholic fragrance component include green leaf alcohol, 3-octenol, 9-decenol, linalool, geraniol, nerol, citronellol,
Rosinol, dimethyloctanol, hydroxycitronellol, tetrahydrolinalool, lavandulol, mugol, myrcenol, terpineol, 1-menthol (el-menthol), borneol, isobregol, tetrahydromugol, bornylmethoxycyclohexanol, nobor, farnesol, nerolidol. , Santalol, sandalol, cedrol, vetiverol, patchouli alcohol, benzyl alcohol, β-phenylethyl alcohol, γ-phenylpropyl alcohol, cinnamic alcohol, anis alcohol, α-amylcinnamic alcohol, dimethylbenzylcarbinol, methylphenyl Carbinol,
Examples thereof include dimethylphenylcarbinol, β-phenylethyldimethylcarbinol, β-phenylethylmethylethylcarbinol, phenoxyethyl alcohol, phenyl glycol, and tert-butylcyclohexanol.

As the glyceride, for example, monoglyceride, diglyceride or triglyceride of glycerin and a carboxylic acid type perfume component can be used.

Examples of the carboxylic acid type fragrance component include benzoic acid, cinnamic acid, phenylacetic acid and hydrocinnamic acid.

As the amino acid or peptide derivative, for example, an amino acid or peptide derivative such as alcohol-based, carboxylic acid-based, amine-based perfume ingredient, etc. can be used.

[0031]

[Chemical 1]

The alcohol-based flavor component, the carboxylic acid-based flavor component and the amine-based flavor component are each represented by the formula: R
When represented by —OH, R—COOH and R—NH ₂ , they can be represented by the following general formula.

[0033]

[Chemical 2]

,

[0035]

[Chemical 3]

And

[0037]

[Chemical 4]

Any known amino acid or peptide can be used. Examples of amino acids include glycine, alanine, valine, leucine, isoleucine, serine, threonine, cysteine, cystine, methionine,
Aspartic acid, glutamic acid, lysine, arginine,
Examples thereof include tyrosine, phenylalanine, histidine, tryptophan, proline, oxyproline and the like. A peptide in which two or more of these amino acids are bound can also be used.

Examples of the alcohol-based and carboxylic acid-based flavor components are the same as those mentioned above, and examples of the amine-based flavor component include indole, skatole, 2-methyltetrahydroquinoline and 6-methylquinoline. it can.

The above cyclic acetal compound

[0041]

[Chemical 5]

Is a carbonyl compound type perfume ingredient such as aldehyde and ketone

[0043]

[Chemical 6]

And a polyol compound having a plurality of hydroxyl groups adjacent to each other in the molecule

[0045]

[Chemical 7]

It is obtained by reacting with (n is 2 or more).

As the aldehyde-based fragrance component, n-
Heptyl aldehyde, n-octyl aldehyde, n-nonyl aldehyde, n-decyl aldehyde, n-undecyl aldehyde, undecylene aldehyde, dodecyl aldehyde, methyl nonyl acetaldehyde, n-tridecyl aldehyde, n-tetradecyl aldehyde, n-hexadecyl Aldehyde, nonadienal, citral, citronellal, hydroxycitronellal, perilaldehyde, benzaldehyde, phenylacetaldehyde, phenylpropylaldehyde, cinnamic aldehyde, α-amyl cinnamic aldehyde, α-hexyl cinnamic aldehyde, anisaldehyde, cumin aldehyde, helio. Tropine, helional, cyclamenaldehyde, p-tertiary butyl-α-methylhydrocinnamic aldehyde , Salicylaldehyde, hydro Toro Pas aldehyde, vanillin, ethyl vanillin, 4-
(4-Hydroxy-4-methylpenter) -3-cyclohexene-1-carboxaldehyde, miracaldehyde, citronenyloxyacetaldehyde and the like can be mentioned.

As the above-mentioned ketone-based fragrance component, methyl-
n-amyl ketone, ethyl-n-amyl ketone, methyl-n-hexyl ketone, methyl-n-nonyl ketone, methylheptenone, diacetyl, 1-carvone (el-carvone), d-carvone, menthone, d-pregon, piperiton, camphor, Methyl cedrilone, acetophenone,
p-methylacetophenone, p-methoxyacetophenone, benzophenone, benzylideneacetone, methylnaphthylketone, yonone, damascon, damacenone, iron, ethylmaltol, hydroxyfuranone, neron,
Hydroxyphenylbutanone, anisylacetone, jasmon, dihydrojasmon, nootkatone and the like can be mentioned.

Examples of the polyol compound include various known monosaccharides, oligosaccharides, saccharides such as polysaccharides, polyhydric alcohols and the like.

Examples of the monosaccharides include glucose,
Examples thereof include hexoses such as galactose, mannose, glucosamine, galactosamine and mannosamine, and pentacarbon sugars such as arabinose, xylose and ribose.

Examples of oligosaccharides include hydrolyzates such as sucrose, lactose, trehalose, maltose, cellobiose, isomaltose, gentiobiose, laminaribiose, chitobiose, xylobiose, mannobiose, sophorose, mantotriose, starch and cellulose. Can be illustrated.

As the polysaccharide, for example, starch,
Cellulose etc. can be mentioned.

As the polyhydric alcohols, glycerin,
Examples thereof include sorbitol, pentaerythritol and trimethylolpropane.

The present invention requires that all or part of at least one of the perfume components in the prepared perfume, or all or part of the two or more perfume components be incorporated in the form of the precursor substance. The above-mentioned fragrance component to be blended as a precursor substance can be appropriately selected depending on the combination with other fragrance components to be prepared, and a plurality of precursor substances can be combined and blended as necessary. Particularly preferably, the precursor substance is blended for the purpose of compensating for the shortage of the top note component, which is often volatilized and reduced in the early stage of use in the conventional blended fragrance.

The above-mentioned precursor substances can be used as various perfume ingredients in various formulations, which are the same as the conventional formulations of prepared perfumes.

On the other hand, the acid compounded in the present invention for decomposing the precursor substance is not particularly limited as long as it can act on the compounded precursor substance to generate a fragrance component. , Used in combination with precursor materials. Typical acids in the present invention, hydrochloric acid, sulfuric acid, nitric acid, pyrosulfuric acid, phosphoric acid, chloric acid, silicic acid, thiocyanic acid, inorganic acids such as iodic acid, adipic acid, salicylic acid, benzoic acid, malic acid, Acetic acid, formic acid, p-toluenesulfonic acid, isovaleric acid, citric acid, oxalic acid, trichloroacetic acid, fluoroacetic acid, trifluoroacetic acid, fumaric acid,
Examples thereof include organic acids such as bromoacetic acid, tribromoacetic acid, benzenesulfonic acid, maleic acid, iodoacetic acid, phenylacetic acid, p-nitrobenzoic acid, p-aminobenzoic acid and p-methoxybenzoic acid.

The amount of the above acid to be used is not particularly limited as long as it is an amount that causes a reaction with the acid, but is usually about 0.1 to 200% by weight, more preferably 1 to 100% by weight relative to the precursor substance. It is preferable to set it to about wt%.

In the present invention, depending on the combination of the precursor substance and the acid or the amount of the acid with respect to the precursor substance, the reaction proceeds slowly and the perfume component can be gradually released.

The fragrance compounded according to the present invention may be formulated as a two-pack type in which the precursor substance and the acid are separated and brought into contact with each other at the time of use, or both may be blended as a one-pack type.

The present invention also relates to an aromatic composition containing the above-mentioned mixed fragrance of the present invention. The fragrance composition of the present invention includes various compositions containing the fragrance of the present invention blended therein to emit an aroma based on the fragrance.

Specifically, for example, perfume, cologne,
Cosmetics such as shampoo, conditioner, soap, hairdressing, mouthwash, antiperspirant, soft drink, confectionery, frozen dessert, dairy products, alcohol, meat,
Examples thereof include foods such as toothpaste and tobacco, fragrances for clothes, kitchens, homes, baths, bath agents, detergents and the like.

More specifically, the following application examples can be exemplified.

A main agent which is a liquid agent, a powder agent, a gel agent or a tablet containing a fragrance and a precursor substance constituting the fragrance prepared according to the present invention;
Fragrances, bath agents, detergents, etc. in combination with acid-containing liquids, powders, gels or side agents that are tablets.

A perfume which volatilizes a liquid agent containing a fragrance and a precursor substance constituting the fragrance prepared according to the present invention through a core material having an acid fixed thereto or a volatile paper having an acid fixed thereto.

In the aromatic composition of the present invention, the additive to be added to the fragrance composition of the present invention is not particularly limited as long as it is usually added to the aromatic composition of this type.

[0066]

EXAMPLES Examples and comparative examples will be shown below to further clarify the features of the present invention.

In the following, "%" means "% by weight".

In the following description, the compounded fragrance is a mixture of fragrance components belonging to the top note, middle note and base note, respectively, as described above.

Example 1 Shipley-based compounded fragrance 3.00% bornyl glucoside 0.15% polyoxyethylene nonylphenyl ether 3.00% ethanol 5.00% water 88.85% 100.00% It was prepared as follows.

The above raw materials except water were stirred and mixed at room temperature for 10 minutes, and then water was added and mixed and dissolved for another 10 minutes.

100 ml of the obtained liquid agent was placed in a bottle,
The scent when volatilized through volatilized paper to which 0.1 g of hydrochloric acid was added in advance through the core material was subjected to a sensory evaluation based on the following criteria. The results are shown in Table 1.

Comparative Example 1 A general liquid fragrance was prepared in the same manner as in Example 1 except that borneol was used in place of bornyl glucoside and hydrochloric acid was not added.

100 ml of this fragrance was put into a bottle, and the scent when the volatile paper was volatilized through the core material was subjected to a sensory evaluation based on the following criteria. The results are shown in Table 1.

Example 2 Rose-based compounded fragrance 0.500% β-phenethylglucoside 0.025% polyethylene glycol 8.000% malic acid 20.000% soda ash 71.475% 100.000% It was prepared as follows.

After polyethylene glycol, malic acid and soda ash were mixed by stirring with a Henschel mixer for 10 minutes, the rose-based compounded flavor and β-phenethyl glucoside were sprayed and perfume.

50 g of the obtained bath agent and 0.01 g of hydrochloric acid were separately put in hot water (about 40 ° C.) in a bath and stirred for 1 minute,
The scent was sensory evaluated according to the following criteria. The results are shown in Table 1.

Comparative Example 2 A general bath agent was prepared in the same manner as in Example 2 except that β-phenylethyl alcohol was used instead of β-phenethyl glucoside.

50 g of the obtained bath agent was added to the bath water (about 40
(° C) and stirred for 1 minute, the scent was sensory-evaluated according to the following criteria. The results are shown in Table 1.

[0079] Example 3 floral blended fragrance 3.0% phenethyl 0.15% glucoside 1.5% agar Glycerin 1.0% sulfuric acid 0.1% polyoxyethylene nonyl phenyl ether 1.0% Water qs 100% The fragrance | flavor of the said composition was prepared as follows.

Water, agar and glycerin were mixed and dissolved by stirring at 97 ° C. for 30 minutes. After dissolution, the mixture was cooled to 60 ° C., a floral mixed fragrance, phenethyl glucoside and polyoxyethylene nonylphenyl ether were added, and sulfuric acid was further added. Then, water was added in an appropriate amount to 100 g, and the mixture was mixed for 10 minutes. After mixing, the mixture was filled in a gel-like aromatic agent container, cooled and solidified, and the fragrance when volatilized was sensory-evaluated according to the following criteria. The results are shown in Table 1.

Comparative Example 3 In the same manner as in Example 3 except that phenylethyl alcohol was used instead of phenethyl glucoside and sulfuric acid was not used, a gel-like aromatic agent was prepared and volatilized. The scent was sensory evaluated according to the following criteria.
The results are shown in Table 1.

Example 4 Floral compounded fragrance 50% Phenethyl glucoside 10% Sulfuric acid 0.5% Isoparaffin 39.5% 100.0% The above raw materials were prepared by stirring and mixing at room temperature for 10 minutes.

10 g of the mixed liquid agent was prepared to have a diameter of about 10 cm,
A fragrance was prepared by impregnating a non-woven fabric having a thickness of about 0.5 cm.

The scent when volatilized from this fragrance was sensory-evaluated according to the following criteria. The results are shown in Table 1.

Comparative Example 4 An impregnated fragrance was prepared in the same manner as in Example 4 except that phenylethyl alcohol was used instead of phenethyl glucoside and sulfuric acid was not used.
The fragrance when volatilized was sensory-evaluated according to the following criteria. The results are shown in Table 1.

[0086]

[Table 1]

Example 5 Woody type perfume 3.00% cinnamic acid monoglyceride 0.15% polyoxyethylene nonylphenyl ether 3.00% ethanol 5.00% water 88.85% 100.00% Prepared as in Example 1.

That is, the above raw materials except water were stirred and mixed at room temperature for 10 minutes, and then water was added and mixed and dissolved for another 10 minutes.

100 ml of the liquid agent was put into a bottle in which the above liquid agent was volatilized through a volatilizing paper to which 0.1 g of citric acid had been added in advance through the core material to prepare an aromatic agent.

Example 6 Floral compounded fragrance 3.00% 1,2,5,6-di-O-methylhexylidene-d-glucofuranose 0.15% polyoxyethylene nonylphenyl ether 3.00% ethanol 5.00% Water 88.85% 100.00% A liquid agent having the above composition was prepared in the same manner as in Example 1.

That is, the above raw materials except water were stirred and mixed at room temperature for 10 minutes, and then water was added and mixed and dissolved for another 10 minutes.

An aromatic agent was prepared by placing 100 ml of the liquid agent in a bottle in which the liquid agent was volatilized through a volatilizing paper to which 0.1 g of benzoic acid had been added in advance through the core material.

Sensory evaluation [Method] The obtained fragrance was placed in an odorless box of about 2 m ³ at room temperature of 25 ° C., and the fragrance and aroma potency were measured by the panel 6
It was evaluated by name. However, in Example 2 and Comparative Example 2, the scent quality and aroma titer of the bath agent in the bathroom were evaluated. still,
In Table 1 above, the average value of the above 6 persons is shown.

[Evaluation Criteria] Standard fragrance quality Aroma titer 5 Good Strong 4 Somewhat good Somewhat strong 3 Neither 2 Somewhat bad Somewhat weak 1 Poor Weak

[0095]

EFFECTS OF THE INVENTION With the fragrance compounded according to the present invention, each fragrance component can be volatilized while maintaining a predetermined mixing balance, and a certain fragrance quality and aroma potency can be maintained for a long time.

Claims (4)

[Claims] 1. A compounded fragrance comprising one or more fragrance ingredients belonging to each of top note, middle note and base note, wherein at least one fragrance ingredient in the fragrance ingredient is all or part of In addition to being compounded in the form of a precursor substance that decomposes by the action to become the perfume ingredient,
A compounded fragrance comprising an acid that decomposes the precursor substance. 2. A compounded fragrance comprising one or more kinds of fragrance ingredients belonging to each of top note, middle note and base note, wherein at least one fragrance ingredient belonging to top note in the fragrance ingredient is wholly or partially. Is added in the form of a precursor substance which is decomposed by the action of an acid to be the perfume component, and an acid which decomposes the precursor substance is also added. 3. A compounded fragrance containing one or more fragrance components belonging to each of top note, middle note and base note, wherein at least one fragrance component in the fragrance component is partially or entirely acidified. In addition to being compounded in the form of a precursor substance that decomposes by the action to become the perfume ingredient,
An aromatic composition containing a prepared perfume, characterized in that an acid that decomposes the precursor substance is added. 4. A compounded fragrance in which one or more fragrance ingredients belonging to each of top note, middle note, and base note are mixed, and at least one fragrance ingredient belonging to the top note in the fragrance ingredients is wholly or partially. Is added in the form of a precursor substance that is decomposed by the action of an acid to be the perfume component, and an acid that decomposes the precursor substance is also added, and an aromatic composition containing a prepared perfume.