JP5303866B2 - Fragrance composition - Google Patents

Description

  The present invention relates to a fragrance composition having excellent mint-like fragrance sustainability and residual fragrance properties.

  The refreshing and refreshing fragrance is favored by consumers as the scent of consumer products such as cosmetics such as milky lotion and shampoo, household detergents such as detergents for clothes and softeners. One of these refreshing and refreshing scents is a mint-like scent. Some of these consumer goods products are applied to human skin and hair from the perspective of application, and other are applied to non-human objects such as fibers and hard surfaces. After application, it is divided into those that are washed away with water and those that are not washed away. In any case, it is required that a refreshing mint-like scent is maintained not only in the initial scent but also in the remaining scent.

  By the way, a fragrance composition for imparting a mint-like scent to cosmetics and household products is prepared by blending a large amount of mint-based fragrance materials such as menthol, menton, peppermint oil, peppermint oil, spearmint oil and the like. However, these materials are relatively easy to volatilize, and the sustainability of the fragrance and the remaining fragrance are not sufficient.

  Therefore, in order to impart good sustainability and residual fragrance to a mint-like fragrance composition, it is generally practiced to use a mint-based fragrance material in combination with a fragrance material having good residual fragrance properties such as woody, musky and amber. It has been broken. Further, in order to improve the residual fragrance property of the fragrance composition used for the fabric softener, a fragrance composition having a boiling point of 250 ° C. or higher and a ClogP value (octanol / water partition coefficient) of about 3 or higher is used. A technique of blending into the above has been proposed (Patent Document 1).

Japanese National Patent Publication No. 11-504994

  However, when a mint-based fragrance material is used in combination with a fragrance material having a relatively good fragrance such as woody, musky, or amber, the fragrance is improved, but a sweet and soft cosmetic fragrance is obtained. The refreshing aftercense was not obtained. Further, even with the technique of Patent Document 1, a specific fragrance composition exhibiting a good mint-like residual fragrance property has not yet been obtained. Therefore, after applying cosmetics and household products perfumed with a mint-like fragrance composition to subjects such as human skin, hair, fibers, hard surfaces, etc., a mint-like refreshing scent can be imparted. There is no current situation.

  An object of the present invention is to solve the above-described problems of the prior art and to maintain a refreshing mint-like scent or to impart a good residual scent.

  Under the hypothesis that if the mint-like fragrance can be created without using the conventional mint-based fragrance material, the researchers will be able to eliminate the disadvantages associated with the use of the conventional mint-based fragrance material. As a result of examining the combination of fragrance materials, conventional mint can be obtained by combining specific fragrance materials showing three different fragrances (ie, citrus green fragrance, spicy herbal fragrance, floral fruity fragrance). The present inventors have found that a fragrance composition having a mint-like scent superior in sustainability and residual fragrance compared to a fragrance composition can be obtained.

  That is, the present invention is selected from the following fragrances having at least one citrus green tone fragrance selected from the following fragrance groups A, at least one fragrance having spicy herbal tone fragrances selected from the fragrance group B, and fragrance groups C. Provided is a fragrance composition containing a fragrance having at least one floral fruity fragrance.

    Fragrance group A: 6-isopropyl-2 (1H) -octahydronaphthalenone, 2-methyl-4-phenyl-1-pentanol, 3,4,4a, 5,8,8a-hexahydro-3 ', 6 ( 7) -Dimethyl-spiro [1,4-methanonaphthalene-2 (1H), 2'-oxirane], 6-ethylideneoctahydro-5,8-methano-2H-1-benzopyran, 4-phenyl-4-methyl 2-pentanone, 3 (4)-(5-ethylbicyclo [2,2,1] heptyl-2) -cyclohexanol, 2-methyl-4-propyl-1.3-oxathiane, 2,4,4 7-tetramethyl-6,8-nonadien-3-one-oxime, 1,5-dimethyl-bicyclo [3,2,1] octane-8-one oxime.

    Fragrance group B: thymol, estragole, anisylacetone, heliotropylacetone.

    Fragrance Group C: Phenoxyethanol, phenylhexanol, 1- (2-methyl-2-propenyloxy) -2,2,4-trimethylpentan-3-ol, farnesol, benzyl cinnamate, 2-methyl 2-methylpentanoate Pentyl, 5-methyl-5-propyl-2- (1-methylbutyl) -1,3-dioxane.

  Moreover, this invention provides the cosmetics or household product containing the above-mentioned fragrance | flavor composition.

  Since the fragrance composition of the present invention combines a specific fragrance material exhibiting three different fragrances other than the mint fragrance, which is excellent in sustainability and residual fragrance as compared to the conventional mint fragrance composition, After the fragrance composition itself having a mint-like fragrance is applied to an object such as human skin, hair or the like, fiber, hard surface or the like, a mint-like refreshing fragrance can be maintained or a good residual scent can be imparted.

  The mint-like fragrance composition of the present invention comprises at least one fragrance material selected from fragrance group A described below, at least one fragrance material selected from fragrance group B, and at least one fragrance material selected from fragrance group C. Containing.

  The fragrance group A is a group composed of a fragrance material having a citrus green tone fragrance, and the fragrance material is a fragrance material that imparts a refreshing feeling and a transparent feeling of the menthol fragrance to the fragrance composition, and the present invention. Then, two or more kinds from the perfume group A can be used at the same time. The fragrance materials belonging to the fragrance group A are as follows.

  6-Isopropyl-2 (1H) -octahydronaphthalenone (Givaudan product name; Decatone Decatone), 2-methyl-4-phenyl-1-pentanol (IFF product name; Pamplefleur Pulefleur), 3, 4, 4a , 5,8,8a-Hexahydro-3 ', 6 (7) -dimethyl-spiro [1,4-methanonaphthalene-2 (1H), 2'-oxirane] (Productname of Firmenich; Lubofix Rhubfix), 6 -Ethylideneoctahydro-5,8-methano-2H-1-benzopyran (Firmenich product name; Florex Florex), 4-phenyl-4-methyl-2-pentanone (Symrise product name; Veticon Veticone), 3 ( 4)-(5-Ethylbicyclo [2 , 2,1] heptyl-2) -cyclohexanol as a main component (Kao Corporation product name: Magnol), 2-methyl-4-propyl-1.3-oxathiane, 2,4,4,7-tetra Methyl-6,8-nonadien-3-one-oxime (Givaudan product name: Rabienoxime), 1,5-dimethyl-bicyclo [3,2,1] octane-8-one oxime (Symrise product name; Buccoxime Buccoxime) .

  In addition, the following fragrance materials may be added to the fragrance composition of the present invention as the fragrance group A on the premise that at least one kind of fragrance material selected from the above-described fragrance group A is used. .

  7-methyl-3,5-dihydro-2H-benzodioxepin-3-one (Danisco product name; Carone), 2-methyl-3- (3,4-methylenedioxyphenyl) -propanal (IFF Product name; Helional), 2-methyl-3- (p-methoxyphenyl) -propylaldehyde (IFF product name; Canthoxal), p-ethyl-2,2-dimethylhydrocinnamaldehyde (IFF product name; Florazone), acetic acid 4-methyl-4-phenyl-2-pentyl (Symrise product name; Veticol acetate), nootkatone.

  Fragrance group B is a group composed of a fragrance material having a spicy herbal-like fragrance, and the fragrance material is a fragrance material that imparts a herbal feeling of menthol fragrance to the fragrance composition. In the present invention, the fragrance group Two or more of B can be used simultaneously. The fragrance materials belonging to the fragrance group B are as follows.

  Thymol, estragole, anisylacetone, heliotropylacetone.

  In addition, the fragrance material shown below may be additionally blended in the fragrance composition of the present invention as the fragrance group B on the assumption that at least one fragrance material selected from the above-described fragrance group B is used. .

  Creosole, 4- (4-hydroxyphenyl) -2-butanone (product name of Takasago International Corporation; Raspberry ketone)

  Fragrance group C is a group composed of a fragrance material having a floral-fruity fragrance, and the fragrance material is a fragrance material that imparts a gentle fruity floral nuance and volume feeling of menthol fragrance to the fragrance composition. In the present invention, two or more of the perfume group C can be used at the same time. The fragrance materials belonging to the fragrance group C are as follows.

  Phenoxyethanol, phenylhexanol, 1- (2-methyl-2-propenyloxy) -2,2,4-trimethylpentane-3-ol (product name of Takasago Fragrance Co., Ltd .; Polymeflor Polymefluor), farnesol, benzyl cinnamate, 2 2-methylpentyl methylpentanoate (product name of Kao Corporation; Peranat Peranat), 5-methyl-5-propyl-2- (1-methylbutyl) -1,3-dioxane (product name of Kao Corporation; Troenan Troenan).

  In addition, the fragrance material shown below may be additionally blended in the fragrance composition of the present invention as the fragrance group C on the assumption that at least one fragrance material selected from the fragrance group C described above is used. .

  Phenylethyl phenylacetate, 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol (product name of Firmenich; Florol), laral, nerolidol, cinnamyl cinnamate, benzyl benzoate, 1-methyl-4- (4-Methyl-3-pentenyl) -3-cyclohexene-1-carboxaldehyde (IFF product name; Precyclemon B).

  In the fragrance composition of the present invention, the mass ratio [A / B] of the fragrance material belonging to the fragrance group A to the fragrance material belonging to the fragrance group B is preferably 0.15 to 5, more preferably 0.2 to 3. is there.

  The mass ratio [A / C] of the fragrance material belonging to the fragrance group A to the fragrance material belonging to the fragrance group C is preferably 0.01 to 5, more preferably 0.05 to 2.

  In the fragrance composition of the present invention, the total content of the fragrance material selected from the fragrance group A, the fragrance material selected from the fragrance group B, and the fragrance material selected from the fragrance group C is preferably an amount excluding the diluent and the solvent. Is 40 to 100% by mass, more preferably 60 to 100% by mass. If this total content is in this range, it has a mint-like fragrance and a refreshing scent is preferred.

  The fragrance composition of the present invention can further contain one or more fragrance materials selected from the following fragrance group D. The fragrance group D is a group composed of fragrance materials having woody, amber, and musk-like fragrances. The fragrance material is a material that reinforces the effect of the fragrance material belonging to the fragrance group C, and is a fragrance material that imparts a transparent volume to the fragrance composition of the present invention. Two or more can be used simultaneously. The fragrance materials belonging to the fragrance group D are as follows.

  1- (2-t-butylcyclohexyloxy) -2-butanol (Kao product name; Ambercore Amber core), 3- (2-bornyloxy) -2-methyl-1-propanol (IFF product name; Bornafix Bornafix) ), Ethoxymethylcyclododecyl ether (product name of Kao Corporation; Boisambrene forte), 3α, 6,6,9α-tetramethyldodecahydronaphtho [2,1-b] furan (product name of Kao Corporation; ambroxan) Ambroxan), 4-cyclopentadecene-1-one (IFF product name; Musk Musk Z-4), 3-methylcyclopentadecenone (Product name of Firmenich; Musenone Muscenone), Copayba balsam.

  In addition, the fragrance materials shown below may be additionally blended in the fragrance composition of the present invention as the fragrance group D on the assumption that the fragrance materials included in the fragrance group D described above are used.

  Cedrol, acetyl cedrene, 2,6,10-trimethyl-2,5,9-cyclododecatrien-1-ylmethylketone (IFF product name; Trimofix “O”), 1- (2,2,6-trimethyl) Cyclohexyl) -3-hexanol (Symrise product name; Timbelol), Ethylene brushate, Oxacycloheptadeca-10-en-2-one (IFF product name; Ambrettolide), Cyclohexadecenone (Iwata perfume product name; Musk ™) -II), Opoponax oil, Oliveranum oil.

  In the fragrance composition of the present invention, the mass ratio [A / D] of the fragrance material belonging to the fragrance group A to the fragrance material belonging to the fragrance group D is preferably 0.01 to 5, more preferably 0.05 to 3. It is. If this mass ratio is within this range, it is preferable because it has a clean, clean scent and a more mint-like refreshing scent.

  When the fragrance material belonging to the fragrance group D is used in the fragrance composition of the present invention, the fragrance material selected from the fragrance group A, the fragrance material selected from the fragrance group B, the fragrance material selected from the fragrance group C, and the fragrance group D. The total content of the selected fragrance materials is preferably 60 to 100% by mass, more preferably 80 to 100% by mass of the amount excluding the diluent and solvent. If this total content is in this range, it has a mint-like fragrance and a refreshing scent is preferred.

  In the fragrance composition of the present invention, other fragrance materials can be blended to such an extent that the mint-like fragrance is not impaired. Conventional mint-based fragrance materials such as menthol, mentone, peppermint oil, peppermint oil, spearmint oil and the like can be used in combination.

  The perfume composition of the present invention can contain a diluent such as diethyl phthalate, dipropylene glycol, propylene glycol, triethyl citrate, butyl diglycol or a solvent such as ethanol, if necessary. The amount can be appropriately determined according to the intended use, purpose of use, etc. of the fragrance composition of the present invention.

  The fragrance composition of the present invention includes at least one fragrance material selected from the fragrance group A described above, at least one fragrance material selected from the fragrance group B, and at least one fragrance material selected from the fragrance group C. Accordingly, it can be prepared by uniformly mixing at least one perfume material selected from the perfume group D or other perfume materials, and further a solvent and a diluent.

  The fragrance composition of the present invention can be used alone by blending into consumer products such as cosmetics or household products, but the fragrance composition for blending into conventional cosmetics or household products. It can also be added to the product as a mint-like material. Here, as fragrance materials that can be used in conventional fragrance compositions blended in consumer goods products, the fragrances described in "Fundamental knowledge of fragrances and fragrances" (by Nakajima Motoki, industrial books), etc. Materials.

  Specific examples of perfume materials that can be used in conventional perfume compositions include limonene, citral, linalool, linalyl acetate, phenylethyl alcohol, geraniol, citronellol, nerol, hexylcinnamic aldehyde, methyl dihydrojasmonate, benzyl Acetate, Liliaal, Terpineol, Ionone, Methylionone, Acetic acid p-tert-Butylcyclohexyl, Iso-Esuper (IFF product name; Iso-E-super), Cyclopentadecanolide (Iwata perfume product name; Pentalide), Oxacyclohexadecene 2-one (Firmenich product name; Habanolide), hexamethylhexahydrocyclopentabenzopyran (IFF product name; Galaxolide), γ-un Examples include decalactone, coumarin, heliotropin, vanillin, eugenol.

  The blending amount of the fragrance composition of the present invention in the fragrance composition for consumer goods products for consumers is preferably 0.5 to 20% by mass, more preferably 2 to 10% by mass. If the blending amount is within this range, a refreshing mint-like after-scent can be realized after use of the consumer goods product, which is preferable.

  In addition, when blending the fragrance composition of the present invention, when it is desired to strongly express the mint-like fragrance from the beginning of use, such as cosmetics or household products with improved mint-like fragrance persistence and residual fragrance properties. The mint flavor, mint oil, peppermint oil and other common mint-based fragrance materials may be added in a relatively large amount to the fragrance composition to be added. In this case, the compounding quantity of the total menthol in a fragrance | flavor composition becomes like this. Preferably it is 2-50 mass%, More preferably, it is 5-20 mass%. The mass ratio of the fragrance composition of the present invention to the total menthol [mint-like fragrance composition of the present invention / total menthol] is preferably 0.01 to 5, more preferably 0.2 to 1. If this mass ratio is in this range, it is preferable because it enhances the refreshing feeling of menthol at the beginning of use and gives a more refreshing fragrance. Here, the total menthol amount means the total menthol amount obtained by adding the menthol and the menthol amount in peppermint oil or peppermint oil.

  In addition, at the beginning of use of consumer products such as cosmetics or household products, a fresh floral fragrance, green herbal fragrance or citrus fragrance is expressed, leaving a refreshing mint-like fragrance after aging or washing. If it is desired, a small amount of mint-based fragrance materials such as menthol, mint, peppermint and the like may be used without adding them.

  The perfume composition for consumer goods products may contain a diluent such as diethyl phthalate, dipropylene glycol, propylene glycol, triethyl citrate, butyl diglycol, and a solvent such as ethanol. In the calculation of the mass ratio of each fragrance material constituting the fragrance composition of the present invention in the fragrance composition for consumer goods products, the calculation of the mass ratio of the fragrance composition of the present invention relative to the total menthol, these dilutions Calculations shall be made excluding agents and solvents.

  Cosmetics to which the fragrance composition of the present invention can be preferably applied include fragrance products (perfume, eau de parfum, body colon, etc.), skin care cosmetics (basic cosmetics such as skin lotions, emulsions, creams, makeup cosmetics such as lipsticks, foundations, Facial cleansers, soaps, body shampoos and other body cleaners, body care agents, bathing agents, antiperspirant deodorants, etc., hair care cosmetics (shampoos, rinses, conditioners, hair treatments, hair tonics, hair restorers, hair colors Ring agents, hair styling agents, permanent agents and the like).

  Household products to which the fragrance composition of the present invention is preferably applied include detergents for clothes, softeners for clothes, finishing agents for clothes, various cleaning agents (for textiles, leather, hard surfaces, residential use, and household use) , Toilet, bath etc.), fragrance deodorant, scented toilet pepper, wax agent and the like.

  The consumer goods products such as cosmetics and household products to be blended with the fragrance composition of the present invention described above are interfaces such as an anionic surfactant, a cationic surfactant or a nonionic surfactant in addition to the fragrance composition. Activators, fatty acids or salts thereof, inorganic salts, sequestering agents, antioxidants, silicones and the like can be contained. The blending amount of the fragrance composition of the present invention in these consumer goods products is preferably 0.01 to 10% by mass, more preferably 0.05 to 5% by mass, although it depends on the purpose of use.

  As anionic surfactants, alkylbenzene sulfonate, alkyl (or alkenyl) sulfate, polyoxyethylene alkyl (or alkenyl) ether sulfate, olefin sulfonic acid, alkane sulfonic acid, α-sulfo fatty acid, α-sulfo fatty acid ester And salts thereof. Specific examples of these salts include glycolic acid N-alkyl (or alkenyl) amide sulfate esters, alkyl (or alkenyl) ether sulfates, alkyl (or alkenyl) sulfates, and olefins having an average carbon number of 10 to 20. Sulfonate, alkane sulfonate having an average carbon number of 10 to 20, saturated or unsaturated fatty acid salt having an average carbon number of 10 to 24, alkyl (or alkenyl) ether carboxylate, α- having an alkyl group or an alkenyl group Examples include sulfo fatty acid salts or esters, N-acyl amino acid type surfactants, phosphoric acid mono- or diester type surfactants, sulfosuccinic acid esters, and sulfosuccinic acid esters derived from higher fatty acid amides.

  Examples of the cationic surfactant include mono long-chain alkyl quaternary ammonium salts. Specific examples include cetyltrimethylammonium chloride, stearyltrimethylammonium chloride, aralkyltrimethylammonium chloride, and behenyltrimethylammonium chloride. Among these, behenyltrimethylammonium chloride can be preferably used. Further, a tertiary amine and an organic acid described later can be blended in a softener composition, and those salted in the softener composition can be used as a cationic surfactant.

  Nonionic surfactants include polyoxyalkylene sorbitan fatty acid esters, polyoxyalkylene sorbite fatty acid esters, polyoxyalkylene glycerin fatty acid esters, polyoxyalkylene fatty acid esters, polyoxyalkylene alkyl ethers (for example, polyoxyalkylene alkyl ethers). Ethylene alkyl (or alkenyl) ether, polyoxypropylene alkyl (or alkenyl) ether, polyoxybutylene alkyl (or alkenyl) ether, polyoxyalkylene alkyl (or alkenyl) ether), polyoxyalkylene alkyl phenyl ethers (eg, poly Oxyethylene alkylphenyl ether), polyoxyalkylene (hardened) castor oil, sucrose fatty acid esters, polyglycerin alkyl Ethers, polyglycerol fatty acid esters, (higher) fatty acid alkanolamides or alkylene oxide adducts thereof, alkyl glycosides, glycerol fatty acid monoester, polyoxyethylene alkyl amide, polyoxyethylene alkylamine, and the like.

  Amphoteric surfactants include amide amino acid surfactants, carbobetaine surfactants, sulfobetaine surfactants, amide sulfobetaine surfactants, imidazolinium betaine surfactants, and amino acid betaine surfactants. Agents, phosphobetaine surfactants, and the like.

  Examples of fatty acids or salts thereof include fatty acids having 12 to 21 carbon atoms or salts thereof. Specific examples include lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, or a mixture thereof. Particularly preferred fatty acids or salts thereof include lauric acid, stearic acid, oleic acid and the like. Moreover, the fatty acid which has the alkyl composition induced | guided | derived from palm oil, palm oil, palm kernel oil, and beef tallow, or those salts are also mentioned preferably. In addition, when using as a salt, it uses as a sodium salt, potassium salt, magnesium salt, and alkanolamine salt.

  Examples of inorganic salts include sodium chloride, sodium sulfate, magnesium chloride, calcium chloride and the like.

  Examples of the metal sequestering agent include ethylenediaminetetraacetate, aminocarboxylate represented by diethylenetriaminepentaacetate, tripolyphosphate, inorganic phosphorus compound represented by pyrophosphate, 1-hydroxyethane-1,1-diphosphonic acid Examples thereof include organic phosphorus compounds represented by salts, polyphosphonates, and phytic acid.

  Examples of the antioxidant include 1,6-di-tert-butyl-4-methylphenol, 2,6-di-tert-butyl-4-methylphenol, and 2 (3) -butyl-4-oxyanisole. It is done.

  Examples of silicones include dimethylpolysiloxane, amino-modified silicone, polyether-modified silicone, methylphenylpolysiloxane, fatty acid-modified silicone, alcohol-modified silicone, alkoxy-modified silicone, epoxy-modified silicone, fluorine-modified silicone, cyclic silicone, and alkyl-modified silicone. Is mentioned.

  The consumer goods product may further contain a fatty acid ester of a polyhydric alcohol as required. Preferred fatty acid esters of polyhydric alcohols include sugar esters, ethylene glycol esters, pentaerythritol esters, glycerin esters and the like. Examples of the fatty acid constituting the fatty acid ester include hardened beef tallow fatty acid, palm stearic acid, oleic acid, beef tallow fatty acid, uncured palm oil-derived fatty acid, stearic acid, lauric acid, fatty acid derived from soybean fatty acid, and the like. Among these, mono-, di-, and triglycerides, sorbitan mono-, di-, and triesters of saturated and unsaturated fatty acids having 12 to 22 carbon atoms can be preferably used. Further, an ethylene oxide (5 to 50 mol) adduct of polyglyceride or sorbitan ester can also be used.

  Moreover, you may mix | blend solvents, such as ethanol, isopropyl alcohol, glycerol, ethylene glycol, and propylene glycol, with consumer goods products as needed.

  In addition, consumer goods products for consumers such as cosmetics or household products in which the fragrance composition of the present invention is blended, as additives generally blended, in addition to the components described above, organic acids, oils , Conditioning agents, moisturizers, thickeners, viscosity modifiers, stabilizers, preservatives, emulsions, colorants, UV absorbers, pH adjusters, flame retardants, bactericides and anti-dandruff agents, antifoaming agents In addition, fluorescent brighteners, antioxidants, nutritional components, animal and plant extracts and the like can be appropriately selected and used as necessary.

  Examples of the organic acid include carboxylic acids such as monocarboxylic acids, dicarboxylic acids, hydroxycarboxylic acids, and polycarboxylic acids, and alkyl phosphoric acids. Among these, carboxylic acids, particularly dicarboxylic acids and hydroxycarboxylic acids are preferable. Examples of the dicarboxylic acid include malonic acid, succinic acid, glutaric acid, adipic acid, maleic acid, fumaric acid, and phthalic acid. Examples of the hydroxycarboxylic acid include glycolic acid, lactic acid, hydroxyacrylic acid, oxybutyric acid, and glyceric acid. , Malic acid, tartaric acid, citric acid and the like.

  Specific examples of the oil include higher alcohols having 12 to 24 carbon atoms such as cetanol, stearyl alcohol and myristyl alcohol, hydrocarbons such as liquid paraffin, squalane, squalene and petrolatum, vegetable oils such as jojoba oil and camellia oil, silicone or silicone Derivatives, lanolin, protein derivatives, fatty acid esters of polyethylene glycol, and the like.

  The consumer goods product for consumers such as cosmetics or household products in which the fragrance composition of the present invention is blended is selected according to its use, form, etc., and mixed uniformly. The fragrance composition can be added and mixed.

  Hereinafter, the present invention will be described in more detail with reference to examples.

Examples 1-12
Each fragrance | flavor composition was prepared by mixing and stirring the component of Table 1 uniformly according to a conventional method. About the obtained mint-like fragrance | flavor composition of Examples 1-12, test evaluation was carried out so that the intensity | strength of a fragrance, mintness, and a clean feeling may be demonstrated below.

(Evaluation method of mint-like fragrance composition)
The prepared mint-like fragrance compositions of Examples 1 to 12 were immersed in the lower end 1 cm of filter paper odor test paper (length 12 cm × width 5 mm) and evaluated for fragrance immediately after being left and left indoors. .

Evaluation of “scent intensity” The scent intensity of the fragrance composition was subjected to sensory evaluation by 10 expert panelists according to the following evaluation criteria, the average value of the obtained evaluation values was obtained, and the average value was expressed. It is shown in 1. Practically, it is desirable that the average value is 2.5 immediately after that and 2.0 or more after one day.

“Scent intensity” criteria 5: Smells fairly strongly 4: Smells strongly 3: Smells clearly 2: Slightly smells 1: Slightly smells 0: Does not smell

Evaluation of “Mint-likeness” and “Cleanliness” The “Mintness-likeness” and “Cleanliness” of the fragrance composition were subjected to sensory evaluation by 10 expert panelists according to the following evaluation criteria, respectively, “A” or “B”. Table 1 shows the number of people evaluated. Practically, it can be evaluated that the desired scent quality is satisfied when the number is 6 or more and 8 or less, and it can be evaluated that the desired quality is satisfied when the number is 9 or more.

[Mint-likeness] Criteria A: Has an excellent mint-like fragrance B: Has a mint-like fragrance C: Has a slight mint-like fragrance D: Does not have a mint-like fragrance

[Cleanliness] Criteria A: Excellent cleanliness B: Cleanliness C: Slightly clean D: No cleanliness

  From Table 1, it can be seen that all of the fragrance compositions of Examples 1 to 12 gave good results with respect to fragrance strength, mintiness and cleanliness. Among them, in the case of the fragrance composition of Example 12 containing the fragrance material selected from the fragrance group D in addition to the fragrance material selected from the fragrance group A, the fragrance group B, and the fragrance group C, the mint quality and the cleanliness are 1 It was confirmed that the evaluation after the day was improved.

Examples 13 to 16 and Comparative Examples 1 and 2
A perfume composition for consumer products was prepared by uniformly mixing and stirring the ingredients in Table 2. The fragrance compositions of Examples 13 to 16 are examples containing the mint-like fragrance composition of the present invention of Example 11 or 12, while the fragrance compositions of Comparative Examples 1 and 2 are of the present invention. It is an example which does not contain a mint-like fragrance composition.

  For these consumer fragrance compositions for consumer goods products, fabric softeners (Example 17, Comparative Example 3), shampoo (Example 18, Comparative Example 4), body shampoo (Example 19) or “Scent intensity”, “scent quality (mintness), and (cleanliness)” when blended with lotion (Example 20) were evaluated as described below.

Example 17 and Comparative Example 3
(1) Synthesis of Cationic Surfactant to be Blended in Fabric Softener A fatty acid mixture in which stearic acid and palmitic acid are mixed at a molar ratio of 6: 4, and N- (3-alkanoylaminopropyl) -N- (2- Hydroxyethyl) -N-methylamine was mixed at a molar ratio of 1.8: 1, and both were subjected to a dehydration condensation reaction according to a conventional method. When the acid value reached 9, the reaction was stopped to obtain a condensate. The total amine number of this condensate was measured.

  The obtained condensate was heated to 70 ° C. and melted, and 9 times the amount of ion-exchanged water (65 ° C.) was added to the condensate, and 35% hydrochloric acid aqueous solution was added dropwise with stirring. After neutralizing in water and stirring for 10 minutes, the mixture was cooled to 30 ° C. to obtain a precipitate. The amount of 35% aqueous hydrochloric acid solution required for neutralization was calculated based on the total amine value measured previously. Next, the precipitate is freeze-dried, and the amine salt compound [N- (3-alkanoylaminopropyl) -N- (2-alkanoyloxyethyl) -N-methylamine hydrochloride] which is the target cationic surfactant is obtained. Obtained.

(2) Preparation of fabric softener A fabric softener was prepared by uniformly mixing the components shown in Table 3. Specifically, first, ion-exchange water corresponding to 90% of the amount necessary for the finished mass of the fabric softener to be 200 g was put into a 300 mL beaker, and the temperature was raised to 60 ° C. in a water bath. While stirring with a stirring blade having three blades each having a length of 2 cm and a width of 0.8 cm (200 rpm / min), a nonionic surfactant (into a linear primary alcohol having 12 carbon atoms). An average of 25 mol of ethylene oxide was added, and then a cationic surfactant dissolved by heating was added. After stirring for 5 minutes, 10% hydrochloric acid aqueous solution and 10% sodium hydroxide aqueous solution were added to adjust the pH to 2.5. Further, after stirring for 5 minutes, a predetermined amount of calcium chloride was added, and after stirring for 5 minutes, a fragrance composition was added, and then an amount of 60 ° C. ion-exchanged water necessary to make the finished mass was added. Thereafter, the beaker was transferred to a water bath containing 5 ° C. water, and cooled to 30 ° C. with stirring (80 r / min). Thereby, the fabric softener of Example 17 and Comparative Example 3 was obtained.

  The garment treated with the obtained fabric softener was subjected to a test evaluation as described below for the strength of the scent and the quality of the scent (like mint and cleanliness).

(Evaluation of the remaining scent of clothes after treatment with softener and dehydrated or after drying)
Three new blouse (60% acrylic, 20% polyester, 20% nylon), 2 bath towels (100% cotton) and 2 T-shirts (100% cotton) are commercially available weak alkaline detergents (Kao Corporation) It was washed in a washing machine using an attack (Toshiba Corporation, 2-tank washing machine VH-360S1; detergent concentration 0.0667% by mass, 30 L of tap water, water temperature 20 ° C., 10 minutes). Thereafter, the washing liquid was drained, and after dehydration for 3 minutes, 30 L of tap water was poured and rinsed for 5 minutes, and dewatering was performed for 3 minutes after drainage. Thereafter, 30 L of tap water was injected again, and rinsing and dehydration were performed in the same manner. After repeating this operation once more, each of the fabric softeners (Example 17, Comparative Example 3) having the composition shown in Table 3 was added and stirred for 5 minutes. The amount of fabric softener added was 10 mL.

“Scent intensity” evaluation The intensity of the scent of wet clothes after dehydration, and the intensity of the scent left on the clothes after 1 day and 3 days after natural drying, and in the case of Examples 1-12 According to the same evaluation criteria, 10 expert panelists performed sensory evaluations, respectively, and obtained average values of the obtained evaluation numerical values. Table 3 shows the average values. Practically, if the average value is 3 or more, it can be evaluated that the desired fragrance strength is satisfied, and if it is 4 or more, it can be evaluated that the strength is more desirable.

“Mint-likeness” and “cleanliness” evaluation The mintiness and cleanliness of wet and dried clothes after dehydration were sensory-evaluated by 10 expert panelists according to the same evaluation criteria as in Examples 1-12. Table 3 shows the number of people who were evaluated as “A” or “B”. Practically, it can be evaluated that the desired fragrance quality is satisfied when the number is 6 or more and 8 or less, and it can be evaluated that the desired quality is satisfied when the number is 9 or more.

  From Table 3, the fabric softener of Example 17 containing the fragrance composition of the present invention is greatly improved in terms of mintiness and cleanliness compared to the fabric softener of Comparative Example 3 not containing. I understand that.

Example 18 and Comparative Example 4
A shampoo was prepared by uniformly mixing the components shown in Table 4. The hair treated with the obtained shampoo was subjected to test evaluation as described below for the strength of scent, the mintiness and the cleanliness.

(Residual odor evaluation of hair immediately after washing or after drying in shampoo treatment)
Ten professional panelists were allowed to shampoo their hair with the obtained shampoo composition, and tested and evaluated the aroma immediately after washing (after towel drying) and after natural drying (after drying) as described below.

“Strength of fragrance” evaluation The strength of the scent during hair washing and the strength of the scent left by natural drying of the scent by 10 professional panelists according to the same evaluation criteria as in Examples 1 to 12, respectively. Sensory evaluation was performed, the average value of the obtained evaluation numerical values was determined, and the average value is shown in Table 4. Practically, if the average value is 3 or more, it can be evaluated that the desired fragrance strength is satisfied, and if it is 4 or more, it can be evaluated that the strength is more desirable.

“Mint-likeness” and “cleanliness” evaluation With respect to the mintiness and cleanliness of wet and dry hair, according to the same evaluation criteria as in Examples 1 to 12, each of 10 expert panelists had a sensory evaluation, Table 4 shows the number of persons evaluated as “A” or “B”, respectively. Practically, it can be evaluated that the desired fragrance quality is satisfied when the number is 6 or more and 8 or less, and it can be evaluated that the desired quality is satisfied when the number is 9 or more.

  From Table 4, it can be seen that the shampoo of Example 18 containing the mint-like fragrance composition of the present invention is greatly improved in any evaluation item as compared with the shampoo of Comparative Example 4 not containing. .

Example 19
A body shampoo was prepared by uniformly mixing the components shown in Table 5. The body washed with the obtained body shampoo was subjected to test evaluation as described below for the intensity of fragrance, the mintiness and the clean feeling.

(Remaining scent evaluation immediately after use in body shampoo treatment or after 1 hour of use)
Have 10 professional panelists wash their bodies with the obtained body shampoo, and show the strength of the scent immediately after use (after towel drying) and after 1 hour of use, the quality of the scent (feels like mint and cleanliness) Test evaluation was performed as described below.

"Scent intensity" evaluation The strength of the scent immediately after the use of the body shampoo and the strength of the scent after 1 hour of use are evaluated by 10 professional panelists according to the same evaluation criteria as in Examples 1 to 12, Each of them was subjected to sensory evaluation, and the average value of the obtained evaluation values was determined. The average value is shown in Table 5. Practically, if the average value is 3 or more, it can be evaluated that the desired fragrance strength is satisfied, and if it is 4 or more, it can be evaluated that the strength is more desirable.

“Mint-likeness” and “cleanliness” evaluation Immediately after using the body shampoo, the mintiness and cleanliness after 1 hour of use were evaluated by 10 expert panelists according to the same evaluation criteria as in Examples 1-12. Table 5 shows the numbers of people who were evaluated as “A” or “B”. Practically, it can be evaluated that the desired fragrance quality is satisfied when the number is 6 or more and 8 or less, and it can be evaluated that the desired quality is satisfied when the number is 9 or more.

  From Table 5, it can be seen that the body shampoo containing the fragrance composition of the present invention has obtained good results for any of the evaluation items.

Example 20
A lotion was prepared by uniformly mixing the components shown in Table 6. The skin to which the obtained cosmetic lotion was applied (upper arm inner side) was tested and evaluated as described below for the intensity of fragrance, the mintiness and the cleanliness.

(Remaining scent evaluation immediately after use of skin lotion or after 1 hour of use)
10 expert panelists will explain the strength of the scent and the quality of the scent (feeling of mint and cleanliness) immediately after using the obtained lotion (after being applied to the skin) and after 1 hour of use. The test was evaluated as follows.

"Scent strength" evaluation The strength of the scent immediately after the use of the skin lotion, and the strength of the scent after 1 hour of use, according to the same evaluation criteria as in Examples 1 to 12, by 10 professional panelists, Each of them was subjected to sensory evaluation, and the average value of the obtained evaluation values was determined. The average value is shown in Table 5. Practically, when the average value is 3 or more, it can be evaluated that the desired fragrance strength is satisfied, and when it is 4 or more, it can be evaluated that the strength is more desirable.

Evaluation of “Mintness” and “Cleanliness” Immediately after using lotion, the mintliness and cleanliness after 1 hour of use were evaluated by 10 expert panelists according to the same evaluation criteria as in Examples 1-12. Table 5 shows the numbers of people who were evaluated as “A” or “B”. Practically, it can be evaluated that the desired fragrance quality is satisfied when the number is 6 or more and 8 or less, and it can be evaluated that the desired quality is satisfied when the number is 9 or more.

  From Table 6, it can be seen that the lotion formulated with the fragrance composition of the present invention obtained good results for any of the evaluation items.

  The fragrance composition of the present invention is excellent in sustaining a refreshing mint-like fragrance and can impart a good residual fragrance to subjects such as human skin, so that it imparts a mint-like fragrance to cosmetics or household products. Useful.

Claims (5)

At least one kind of fragrance material having at least one citrus green tone fragrance selected from the following fragrance group A, at least one kind of fragrance material having spicy herbal tone fragrance selected from fragrance group B, and fragrance group C The mass ratio [A / B] of the fragrance material belonging to the fragrance group A to the fragrance material belonging to the fragrance group B containing the fragrance material having a floral fruity tone fragrance is 0.15 to 5, and the fragrance group C The mint-like fragrance | flavor composition whose mass ratio [A / C] of the fragrance | flavor raw material which belongs to the fragrance | flavor group A with respect to the fragrance | flavor material which belongs is 0.01-5 .
Fragrance group A: 6-isopropyl-2 (1H) -octahydronaphthalenone, 2-methyl-4-phenyl-1-pentanol , 6 -ethylideneoctahydro-5,8-methano-2H-1-benzopyran, 4 -Phenyl-4-methyl-2-pentanone, 3 (4)-(5-ethylbicyclo [2,2,1] heptyl-2) -cyclohexanol, 2-methyl-4-propyl-1.3-oxathiane, 2,4,4,7-Tetramethyl-6,8-nonadien-3-one-oxime, 1,5-dimethyl-bicyclo [3,2,1] octane-8-one oxime Fragrance Group B: Thymol, Estragole , Anisylacetone, heliotropylacetone Fragrance group C: Phenoxyethanol, phenylhexanol, 1- (2-methyl-2-propenyloxy) -2, , 4-trimethylpentane-3-ol, farnesol, benzyl cinnamate, 2-methylpentanoic acid 2-methylpentyl, 5-methyl-5-propyl-2- (1-methylbutyl) -1,3-dioxane The mint-like fragrance composition according to claim 1, comprising a total of 40 to 100% by mass of a fragrance material selected from the fragrance group A, a fragrance material selected from the fragrance group B, and a fragrance material selected from the fragrance group C. Furthermore, the mass ratio [A / D] of the fragrance material belonging to the fragrance group A to the fragrance material belonging to the fragrance group D containing at least one fragrance material selected from the following fragrance group (D) is 0.01 to 5 is a claim 1 or 2 SL placing mint-like fragrance composition.
Fragrance group D: 1- (2-t-butylcyclohexyloxy) -2-butanol, 3- (2-bornyloxy) -2-methyl-1-propanol, ethoxymethylcyclododecyl ether, 3α, 6,6,9α- Tetramethyldodecahydronaphtho [2,1-b] furan, 4-cyclopentadecene-1-one, 3-methylcyclopentadecenone, copaiba balsam The fragrance material selected from the fragrance group A, the fragrance material selected from the fragrance group B, the fragrance material selected from the fragrance group C, and the fragrance material selected from the fragrance group D are contained in a total amount of 60 to 100% by mass. Mint-like fragrance composition. Cosmetics or household products containing the mint-like fragrance composition according to any one of claims 1 to 4.