JP2018070806A - Flavor precursor composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a flavor precursor composition capable of continuously providing flavor with efficient rising from skin when applied to the skin.SOLUTION: There is provided a flavor precursor composition containing Components (A) to (C) and satisfying Conditions 1 to 3. (A):one or more kind of flavor precursor selected from ester of unsaturated alcohol flavor having 6 to 10 carbon atoms and saturated monocarboxylic acid having 12 to 18 carbon atoms or saturated dicarboxylic acid having 4 to 10 carbon atoms. (B):one or more kind of polyoxyethylene sorbitan fatty acid ester having HLB of 8 to 15. (C):one or more kind selected from aliphatic acid having 16 to 22 carbon atoms and monoglyceride of the aliphatic acid. Condition 1:mass ratio (B)/(A) is 0.0001 to 0.8. Condition 2: mass ratio (C)/(A) is 0.02 to 4. Condition 3: mass ratio [(B)+(C)]/(A) is 0.55 to 2.SELECTED DRAWING: None

Description

  The present invention relates to a fragrance precursor composition.

  In recent years, consumer interest in fragrances such as clothing and cosmetics has increased, and various techniques relating to sustained-release fragrances have been studied.

  For example, in Patent Document 1, when a composition containing a polyvalent carboxylic acid derivative composed of an alcohol-based fragrance and a polyvalent carboxylic acid is used for the human body, it is gradually decomposed by fungi including skin resident bacteria, and the fragrance is long. It is disclosed that it is released stably over time. Patent Document 2 discloses that a fabric is treated with a laundry or detergent composition containing a nonionic ester or anionic ester of an allylic alcohol fragrance to release a fragrance over a long period of time by hydrolysis of an ester compound. ing.

Japanese Patent Laid-Open No. 08-218089 Japanese National Patent Publication No. 10-502959

  On the other hand, body odors such as scalp odor and foot odor are generated from human skin by metabolizing sebum and sweat into resident bacteria. Therefore, a fragrance with sufficient strength cannot be obtained only by applying the ester compound of the fragrance to the skin.

  Therefore, this invention relates to the fragrance | flavor precursor composition from which sufficient intensity | strength fragrance is continuously obtained from the skin when it applies to skin.

  As a result of earnest research, the inventor of the present invention uses a specific nonionic surfactant and a fatty acid or a monoglyceride thereof in a specific ratio in an ester compound of an alcohol-based fragrance and a mono- or dicarboxylic acid. I found that the requirements were met.

The present invention provides a fragrance precursor composition containing the following components (A) to (C) and satisfying the following conditions 1 to 3.
(A): selected from esters of linear or branched unsaturated alcohol fragrances having 6 to 10 carbon atoms and saturated monocarboxylic acids having 12 to 18 carbon atoms or saturated dicarboxylic acids having 4 to 10 carbon atoms One or more perfume precursors
(B): One or more polyoxyethylene sorbitan fatty acid esters of HLB 8 to 15
(C): one or more selected from saturated or unsaturated linear or branched fatty acids having 16 to 22 carbon atoms and monoglycerides of the fatty acids Condition 1: Component (B) for Component (A) Content ratio (B) / (A) of 0.0001 or more and 0.8 or less Condition 2: Component mass ratio of component (C) to component (A) (C) / (A) is 0.02 or more and 4 or less Condition 3: Component (A ) The total mass ratio [(B) + (C)] / (A) of component (B) and component (C) to 0.55 or more and 2 or less

  Moreover, this invention provides the method of making sustained release of a fragrance | flavor by making the product containing the said fragrance | flavor precursor composition contact the human skin resident bacteria or a living environment resident bacteria.

  When applied to the skin, the fragrance precursor composition of the present invention continuously provides a sufficient fragrance from the skin.

[Component (A): Fragrance precursor]
The fragrance precursor of component (A) is a straight chain or branched chain unsaturated alcohol fragrance having 6 to 10 carbon atoms, saturated monocarboxylic acid having 12 to 18 carbon atoms, or saturated dicarboxylic acid having 4 to 10 carbon atoms. It is 1 type, or 2 or more types chosen from ester with an acid.

  C6-C10 linear or branched unsaturated alcohol fragrances used in the fragrance precursor include trans-2-hexenol, 9-decenol, cis-3-hexenol, geraniol, nerol, citronellol, 2 -Isopropenyl-5-methyl-4-hexen-1-ol (Labandulol), symmetric alcohol and the like. Of these, geraniol, citronellol, and cis-3-hexenol are preferable in terms of extending the variation of fragrance.

  Examples of the saturated monocarboxylic acid having 12 to 18 carbon atoms used for the perfume precursor include lauric acid, myristic acid, palmitic acid, and stearic acid. Examples of the saturated dicarboxylic acid having 4 to 10 carbon atoms include succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, and sebacic acid. Of these, palmitic acid, stearic acid, succinic acid, and adipic acid are preferred.

  Specific examples of the fragrance precursor of component (A) include digeranyl succinate, digeranyl adipate, digeranyl sebacate, citronellyl palmitate, cis-3-hexenyl stearate, geranyl stearate, and the like. These fragrance | flavor precursors can be used individually or in combination of 2 or more types.

  The content of the component (A) in the fragrance precursor composition of the present invention is preferably 0.001% by mass or more, more preferably 0.01% by mass or more, and still more preferably 0.1% by mass from the viewpoint of easily perceiving a fragrance during decomposition. Further, it is preferably 10% by mass or less, more preferably 5% by mass or less, and still more preferably 1% by mass or less.

[Component (B): Polyoxyethylene sorbitan fatty acid ester]
Component (B) is one or more polyoxyethylene sorbitan fatty acid esters having an HLB of 8 to 15. Here, the HLB value is an index representing the ratio of relative affinity of the surfactant to both liquids in an oil-water system, and means the HLB value at 25 ° C. according to the definition of Griffin. The HLB value by Griffin is defined in J. Soc. Cosm. Chem., 1954, 5: 249-256. These can be used alone or in combination of two or more.

Examples of the polyoxyethylene sorbitan fatty acid ester include polyoxyethylene sorbitan monooleate, polyoxyethylene sorbitan monostearate, polyoxyethylene sorbitan trioleate, and polyoxyethylene sorbitan tristearate. More specifically, polyoxyethylene (20) sorbitan monostearate (HLB: 14.9), polyoxyethylene (6) sorbitan monostearate (HLB: 9.6), polyoxyethylene (20) sorbitan tristearate (HLB) : 10.5), polyoxyethylene (20) sorbitan monooleate (HLB: 15.0), polyoxyethylene (6) sorbitan monooleate (HLB: 10.0), polyoxyethylene (20) sorbitan trioleate (HLB: 11.0) Is mentioned.
Of these, polyoxyethylene sorbitan monooleate and polyoxyethylene sorbitan monostearate are preferred.

  The content of the component (B) in the fragrance precursor composition of the present invention is preferably 0.0001% by mass or more, more preferably 0.001% by mass or more, and still more preferably, from the viewpoint of promoting decomposition by contact with resident bacteria. Is 0.01% by mass or more, preferably 4% by mass or less, more preferably 0.2% by mass or less, and still more preferably 0.1% by mass or less.

[Component (C): Fatty acid or fatty acid monoglyceride]
Component (C) is one or more selected from saturated or unsaturated linear or branched fatty acids having 16 to 22 carbon atoms and monoglycerides of the fatty acids.

  Among the component (C), examples of the saturated or unsaturated linear or branched fatty acid having 16 to 22 carbon atoms include palmitic acid, stearic acid, arachidic acid, behenic acid, isostearic acid, oleic acid and the like. Examples of monoglycerides of these fatty acids include palmitic acid monoglyceride, stearic acid monoglyceride, and oleic acid monoglyceride. The number of carbon atoms of the fatty acid or the number of carbon atoms of the fatty acid in the monoglyceride is preferably 16 or more and 20 or less, more preferably 16 or more and 18 or less, from the viewpoint of promoting decomposition by contact with resident bacteria.

  Among the above compounds, stearic acid, oleic acid, palmitic acid, stearic acid monoglyceride, oleic acid monoglyceride, and palmitic acid monoglyceride are preferable. One of these fatty acids and fatty acid monoglycerides can be used alone or in combination of two or more thereof, and one or more fatty acids and one or more fatty acid monoglycerides are used in combination. You can also.

  From the same viewpoint, the content of the component (C) in the fragrance precursor composition of the present invention is preferably 0.001% by mass or more, more preferably 0.01% by mass or more, and preferably 1% by mass or less. More preferably, it is 0.2 mass% or less.

[Ratio of each component]
The fragrance precursor composition of the present invention must contain the above components (A) to (C) and satisfy the following conditions 1 to 3.

・ Condition 1: The mass ratio (B) / (A) of component (B) to component (A) is 0.0001 or more and 0.8 or less. The mass ratio (B) / (A) of component (B) to component (A) is From the viewpoint of promoting the decomposition of the component (A), it is 0.001 or more, preferably 0.05 or more, more preferably 0.3 or more, and 0.8 or less, preferably 0.6 or less, more preferably 0.5 or less. It is.

・ Condition 2: The mass ratio (C) / (A) of component (C) to component (A) is 0.02 or more and 4 or less The mass ratio (C) / (A) of component (C) to component (A) is From the viewpoint of promoting the decomposition of the component (A), it is 0.02 or more, preferably 0.03 or more, more preferably 0.05 or more, and 4 or less, preferably 3 or less, more preferably 2 or less. It is.

・ Condition 3: Total mass ratio of component (B) and component (C) to component (A) [(B) + (C)] / (A) is 0.55 or more and 2 or less Component (B) for component (A) (B ) And the total content ratio of component (C) [(B) + (C)] / (A) is 0.55 or more from the viewpoint of promoting the decomposition of component (A) and the stability of the formulation. Preferably, it is 0.8 or more, more preferably 1 or more, and 2 or less, preferably 1.8 or less, more preferably 1.6 or less.

[Optional ingredients]
In addition to the above components (A) to (C), the fragrance precursor composition of the present invention contains natural essential oils generally used, fragrance compounds, or blended fragrances obtained by appropriately mixing them. Can be made. Specifically, natural essential oils such as peppermint oil, spearmint oil, rose oil, patchouli oil, orange oil, neroli oil and lemon oil; terpene hydrocarbons such as α-pinene, β-pinene, terpinolene and p-cymene; Aliphatic alcohols such as cis-3-hexenol, n-undecylene alcohol, n-octyl alcohol; terpene alcohols such as linalool, geraniol, citronellol, l-menthol, nerolidol, santalol; phenylethyl alcohol, cinnamic alcohol, methyl Aromatic alcohols such as phenyl carbinol and t-butylcyclohexanol or derivatives thereof; phenol derivatives such as anisole, anethole, eugenol; aliphatic aldehydes such as n-heptylaldehyde, undecylene aldehyde, 2,6-nonadienal; citral, Terpene aldehydes such as citronellal, hydroxycitronellal, and perilaldehyde; aromatic aldehydes such as benzaldehyde, phenylacetaldehyde, cinnamic aldehyde, anisaldehyde, cuminaldehyde, heliotropin, cyclamenaldehyde, and vanillin; methyl n-amyl ketone, methyl heptenone Aliphatic ketones such as diacetyl, terpene cyclic ketones such as l-carvone, menthone, piperiton, camphor, etc .; Cyclic ketones such as benzophenone, ionone, methylionone, Iron, maltol, jasmon; Muscon, cyclopentadecanone, ethylene brush rate Musk fragrance compounds such as macrocyclic musk, nitromusk, indane musk, etc .; oxides such as rose oxide, linalool oxide; aliphatic Examples include esters of acids or aromatic acids with terpene alcohols, aliphatic alcohols, aromatic alcohols, phenols, etc .; nitrogen-containing fragrance compounds; sulfur-containing fragrance compounds. In addition to these, "Fundamentals of perfumes and fragrances" (edited by Motoki Nakajima, Sangyo Tosho Co., Ltd., first edition on June 21, 1995), "Synthetic perfumes-Chemistry and product knowledge" (Genji Into, Chemical Industry The fragrance materials described in Nikkansha, March 25, 2005 supplement revised edition) can be used as appropriate.

[Drug type]
The dosage form of the fragrance precursor composition of the present invention is not particularly limited, and for example, it can be a dosage form such as liquid, cream, gel, spray and the like. Further, the perfume precursor composition of the present invention is applied to fine fragrance products such as perfume, eau de toilette, and colon; skin care products such as body creams, emulsions, body lotions, and antiperspirant deodorants; hair treatments, hair creams, hair lotions, hairs. Hair care products such as sprays; surface finishes (for fibers and hard surfaces), household products such as wiping-type residential detergents, etc. If these products are used, fragrance precursors are resident in human skin The fragrance can be released slowly by being decomposed by contact with bacteria or living environment resident bacteria.

Test Examples 1-14
Table 1 shows component (B) and component (C) (or only component (B ')) in a liquid medium for staphylococci (medium containing 0.1% by weight of meat extract, 1% by weight of peptone, 7.5% by weight of NaCl). The amount shown in .about.3 (all numerical values are concentrations after addition) was added and mixed by heating. Then, after adding the amount of component (A) shown in Tables 1 to 3 to the medium cooled to room temperature, St. capitis which is a skin resident bacterium was added so as to be 10 ⁷ CFU / mL at 37 ° C. Cultured with shaking for 48 hours. After completion of the culture, the amount of geraniol produced by the degradation of digeranyl succinate was analyzed by SPME HS-GC / MS.
As a control, the detected amount of geraniol when St.capitis was 10 ⁷ CFU / mL, digeranyl succinate 0.2% by mass, and polyoxyethylene lauryl ether (HLB = 10.5) 0.1% by mass was cultured in the same manner. The relative ratios are shown in each table.
SPME HS-GC / MS
Injection conditions: Splitless
Inlet temperature: 250 ° C
Oven temp ： 40 ℃ (4 min hold) −6 ℃ / min−70 ℃ −2 ℃ / min−240 ℃
Column: DB-WAX (60 m × 0.25 mm × 0.25 μm)

Examples 1-1 to 1-3, Comparative Examples 1-1 to 1-4
To the same liquid medium for staphylococci as in the test examples, 10 ⁷ CFU / mL of St. capitis, which is a skin resident bacterium, and the components shown in Table 4 were added so as to have the concentrations shown in the table. Cultured with shaking for 1 day. The amount of geraniol produced by the decomposition of digeranyl succinate was analyzed by SPME HS-GC / MS in the same manner as in the test example, and the relative ratio based on Comparative Example 1-4 is shown in Table 4.
Moreover, it was evaluated whether or not the scent of geraniol could be recognized with respect to a sample obtained by adding 0.5 g of sodium chloride to 1 mL of the sample after 3-day culture diluted 10 times. The evaluation is performed by three panelists according to the following criteria, and the first decimal place of the average value of the evaluation is rounded off and shown in Table 4.
(Evaluation criteria)
3: Clearly understand 2: Weak but understand 1: Faintly understood 0: Unable to perceive fragrance

Example 2-1, Comparative examples 2-1 to 2-3
To a liquid medium for staphylococci similar to the test example, St. capitis, which is a resident skin bacterium, was added at 10 ⁷ CFU / mL and the components shown in Table 5 so as to have the concentrations shown in the table. Cultured with shaking for 1 day. The amount of geraniol produced by the decomposition of digeranyl adipate was analyzed by SPME HS-GC / MS in the same manner as in the test example, and the relative ratio based on Comparative Example 2-3 is shown in Table 5.
Moreover, it was evaluated whether or not the scent of geraniol could be recognized with respect to a sample obtained by adding 0.5 g of sodium chloride to 1 mL of the sample after 3-day culture diluted 10 times. Evaluation is carried out by three panelists according to the following criteria, and the average value of the evaluation is rounded to the first decimal place and shown in Table 5.
(Evaluation criteria)
3: Clearly understand 2: Weak but understand 1: Faintly understood 0: Unable to perceive fragrance

Example 3-1, Comparative examples 3-1 to 3-3
To the same liquid medium for staphylococci as in the test examples, 10 ⁷ CFU / mL of St. capitis, which is a skin resident bacterium, and the components shown in Table 6 were added so as to have the concentrations shown in the table. Cultured with shaking for 1 day. The amount of geraniol produced by the decomposition of digeranyl sebacate was analyzed by SPME HS-GC / MS in the same manner as in the test example, and the relative ratio based on Comparative Example 3-3 is shown in Table 6.
Moreover, it was evaluated whether or not the scent of geraniol could be recognized with respect to a sample obtained by adding 0.5 g of sodium chloride to 1 mL of the sample after 3-day culture diluted 10 times. The evaluation is carried out by three panelists according to the following criteria, and the average value of the evaluation is rounded to the first decimal place and shown in Table 6.
(Evaluation criteria)
3: Clearly understand 2: Weak but understand 1: Faintly understood 0: Unable to perceive fragrance

Example 4-1, Comparative examples 4-1 to 4-3
To a liquid medium for staphylococci similar to the test example, 10 ⁷ CFU / mL of St. capitis, which is a skin resident bacterium, and the components shown in Table 7 were added so as to have the concentrations shown in the table. Cultured with shaking for 1 day. The amount of cis-3-hexenol produced by the decomposition of cis-3-hexenyl stearate was analyzed by SPME HS-GC / MS in the same manner as in the test example, and the relative ratio based on Comparative Example 4-3 is shown in Table 7. Show.
In addition, it was evaluated whether or not the scent of cis-3-hexenol could be recognized in a sample obtained by adding 0.5 g of sodium chloride to 1 mL of a sample that had been diluted 10 times and cultured for 3 days. The evaluation is performed by three panelists according to the following criteria, and the first decimal place of the average value of the evaluation is rounded off and shown in Table 7.
(Evaluation criteria)
3: Clearly understand 2: Weak but understand 1: Faintly understood 0: Unable to perceive fragrance

Example 5-1, Comparative examples 5-1 to 5-3
To the same staphylococcal liquid medium as in the test example, 10 ⁷ CFU / mL of St. capitis, a skin resident bacterium, and the components shown in Table 8 were added so as to have the concentrations shown in the table. Cultured with shaking for 1 day. The amount of citronellol produced by the decomposition of citronellyl palmitate was analyzed by SPME HS-GC / MS in the same manner as in the test examples, and the relative ratio based on Comparative Example 5-3 is shown in Table 8.
Moreover, it evaluated whether the scent of citronellol could be recognized about what added 0.5g of sodium chloride to the sample 1mL after 3 days culture | cultivation diluted 10 times. The evaluation is performed by three panelists according to the following criteria, and the first evaluation is rounded off to the first decimal place.
(Evaluation criteria)
3: Clearly understand 2: Weak but understand 1: Faintly understood 0: Unable to perceive fragrance

Formulation Example 1 Emulsion The following ingredients were mixed uniformly to prepare an emulsion containing the fragrance precursor.
(mass%)
Digeranyl succinate 1
Polyoxyethylene sorbitan monooleate 0.5
Stearic acid 0.8
Cetyl alcohol 1
Vaseline 4
Liquid paraffin 8
Polyoxyethylene monooleate (20E.O.) 2
Perfume Appropriate amount Ion-exchange water Remaining amount

Formulation Example 2 Antiperspirant Deodorant Spray Composition
Ingredients other than LPG were uniformly mixed, and the resulting mixture was packed in a pressure-resistant glass container for aerosol, and then filled with LPG to prepare an antiperspirant deodorant spray composition containing a fragrance precursor.
(mass%)
Digeranyl succinate 0.2
Polyoxyethylene sorbitan monooleate 0.1
Stearic acid 0.1
Isopropylmethylphenol 0.01
Aluminum hydroxychloride 0.5
Cross-linked silicone / reticular silicone block copolymer ^* 3
Isopropyl palmitate 1
Methyl phenyl silicone 0.5
LPG 94.94
*: KSP-105 (Shin-Etsu Chemical Co., Ltd.)

Formulation Example 3 Sheet-shaped hair cosmetic composition The following components were mixed uniformly to prepare a sheet-shaped hair cosmetic composition in which a fragrance precursor was blended.
(mass%)
Digeranyl succinate 0.2
Polyoxyethylene sorbitan monooleate 0.1
Stearic acid 0.1
Ethanol 20.0
Dipropylene glycol 1.0
Polyoxyethylene (60) hydrogenated castor oil 1.0
CETEARETH-7 0.028
Polysilicone-9 (2) 0.3
Amodimethicone 0.14
Methylparaben 0.15
l-Menthol 0.05
Lactic acid 0.09
Phenoxyethanol 0.002
Fragrance 0.1
Water remaining

Formulation Example 4 Scalp Care Tonic The following ingredients were uniformly mixed to prepare a scalp care tonic containing a fragrance precursor.
(mass%)
Digeranyl succinate 0.2
Polyoxyethylene sorbitan monooleate 0.1
Stearic acid 0.1
Stearyl trimethyl ammonium chloride 0.05
Glycerin 2.0
Polyoxyethylene (60) hydrogenated castor oil 0.4
EDTA 0.05
Ethanol 50.0
Fragrance 0.05
Purified water remaining

Claims (6)

A fragrance precursor composition containing the following components (A) to (C) and satisfying the following conditions 1 to 3.
(A): selected from esters of linear or branched unsaturated alcohol fragrances having 6 to 10 carbon atoms and saturated monocarboxylic acids having 12 to 18 carbon atoms or saturated dicarboxylic acids having 4 to 10 carbon atoms One or more perfume precursors
(B): One or more polyoxyethylene sorbitan fatty acid esters of HLB 8 to 15
(C): one or more selected from saturated or unsaturated linear or branched fatty acids having 16 to 22 carbon atoms and monoglycerides of the fatty acids Condition 1: Component (B) for Component (A) Content ratio (B) / (A) of 0.0001 or more and 0.8 or less Condition 2: Component mass ratio of component (C) to component (A) (C) / (A) is 0.02 or more and 4 or less Condition 3: Component (A ) The total mass ratio [(B) + (C)] / (A) of component (B) and component (C) to 0.55 or more and 2 or less   The fragrance precursor composition according to claim 1, wherein the carbon number of the fatty acid of component (C) or the carbon number of the fatty acid in the monoglyceride is 16 or more and 18 or less.   The fragrance precursor according to claim 1 or 2, wherein the component (C) is one or more selected from the group consisting of stearic acid, oleic acid, palmitic acid, stearic acid monoglyceride, oleic acid monoglyceride and palmitic acid monoglyceride. Composition.   The fragrance precursor composition according to any one of claims 1 to 3, wherein the component (B) is one or more selected from polyoxyethylene sorbitan monooleate and polyoxyethylene sorbitan monostearate.   The method to which a fragrance | flavor is sustained-released by making the product containing the fragrance | flavor precursor composition in any one of Claims 1-4 contact with human skin resident bacteria or living environment resident bacteria.   The method according to claim 5, wherein the product containing the fragrance precursor composition according to any one of claims 1 to 4 is a fine fragrance product, a skin care product, a hair care product or a house hold product.