JP2009249501A - Perfume composition - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a perfume composition excellent in perfume sustaining properties and a fiber finishing agent using the same. <P>SOLUTION: The perfume composition contains (a) a specific silicone compound represented by general formula (I) and (b) a perfume. The fiber finishing agent contains the composition. <P>COPYRIGHT: (C)2010,JPO&INPIT

Description

  The present invention relates to a perfume composition and a fiber finish containing the same.

  Conventionally, fragrances are generally used in toiletry products and home care products, and various techniques for improving the sustainability of a given fragrance have been known.

For example, the technique using the fragrance | flavor component with a low vapor pressure is disclosed (patent document 1). Further, a therapeutic composition or cosmetic composition in which a silica capsule containing an active ingredient such as a fragrance is applied topically is disclosed (Patent Document 2). Furthermore, a composition for controlled release of an active substance in which an active substance such as a fragrance is mixed with a waxy cyclopolysiloxane is disclosed (Patent Document 3).
Japanese Patent Laid-Open No. 2004-210959 Special table 2003-534249 gazette JP-T-2006-524200

  However, in the technique disclosed in Patent Document 1, although low vapor pressure fragrance can be left scented, middle or high vapor pressure fragrance cannot be left scented. Moreover, although it is possible to leave a fragrance in the technique disclosed by patent document 2, since a fragrance | flavor volatilizes over time after that, there exists a fault that fragrance sustainability is inadequate. Furthermore, with the technique disclosed in Patent Document 3, although some improvement in fragrance persistence is recognized, further improvement in fragrance persistence has been desired.

  The subject of this invention is providing the fragrance | flavor composition excellent in fragrance sustainability, and the fiber finishing agent using the same.

  The present invention relates to a fragrance composition containing (a) a compound represented by general formula (I) [hereinafter referred to as component (a)] and (b) a fragrance [hereinafter referred to as component (b)].

[Wherein, R ¹ and R ² are alkyl groups having 1 to 6 carbon atoms, or aromatic hydrocarbon groups having 6 to 10 carbon atoms that may be substituted with alkyl groups, and R ³ is an average carbon number of 16 to 600 saturated hydrocarbon groups, n is an average value of 0 to 3000. ]

  The present invention also relates to a fiber finish containing the fragrance composition of the present invention.

  ADVANTAGE OF THE INVENTION According to this invention, the fiber finish which can perform the fragrance | flavor process excellent in sustainability with respect to the fragrance | flavor composition excellent in the fragrance sustainability, and the textiles is provided.

<(A) component>
The fragrance composition of the present invention contains the compound represented by the general formula (I) as the component (a).

In the general formula ^{(I), R 1, R} 2 is an aromatic hydrocarbon group of the alkyl group or alkyl atoms in total may be carbon optionally substituted with a group 6-10, having 1 to 6 carbon atoms, R ^1, Among those represented by R ² , examples of the alkyl group having 1 to 6 carbon atoms include methyl group, ethyl group, propyl group, isopropyl group, butyl group, sec-butyl group, tert-butyl group, pentyl group, hexyl group and the like. Can be mentioned. In addition, examples of the aromatic hydrocarbon group having 6 to 10 carbon atoms that may be substituted with an alkyl group include a phenyl group, a methylphenyl group, and a naphthyl group. R ¹ and R ² are particularly preferably a methyl group or a phenyl group. These R ¹ and R ² may be the same or different for each repeating unit.

R ³ in the general formula (I) is a saturated hydrocarbon group having an average carbon number of 16 to 600, and the average carbon number is preferably 30 to 300, more preferably 30 to 100.

  Moreover, n in general formula (I) is a number whose average value is 0-3000, the number whose average value is 0-1000 is preferable, the number whose average value is 0-100 is more preferable, and the average value is 0- A number of 10 is particularly preferred.

The component (a) is preferably a compound in which the weight ratio of the sum of two saturated hydrocarbon groups represented by R ³ in the general formula (I) and the remaining polysiloxane moiety is 99: 1 to 30:70. 99: 1 to 50:50 is more preferable, and 99: 1 to 70:30 is particularly preferable.

  The compound represented by the general formula (I) can be synthesized, for example, according to a method for synthesizing a long-chain alkyl-modified polysiloxane described in JP-A-7-278310. That is, the living polyethylene obtained after the polymerization of ethylene is reacted with a cyclic siloxane, and further polymerized with a cyclic siloxane, a chain polysiloxane having a silanol group at the end, or a mixture thereof in the presence of a catalyst, so that both ends are long. Polysiloxanes having chain saturated hydrocarbon groups can be synthesized with good reproducibility.

  Moreover, 40-140 degreeC is preferable, as for melting | fusing point of (a) component, 50-120 degreeC is more preferable, and 60-100 degreeC is especially preferable.

  It is preferable that the fragrance | flavor composition of this invention contains (a) component 10-90 mass%, and also 20-80 mass%.

<(B) component>
There is no restriction | limiting in particular as a fragrance | flavor of (b) component, According to the objective, it can select suitably. The fragrance | flavor which can be used is illustrated below, and may be used independently, and in order to expand the variation of fragrance | flavor, you may use it combining several fragrance | flavors.

(1) Hydrocarbons α-pinene, β-pinene, limonene, terpinolene, p-cymene and the like.
(2) Alcohols Linalol, geraniol, nerol, citronellol, dihydromyrcenol, terpineol, menthol, borneol, cedrol, benzyl alcohol, phenylethyl alcohol, cinnamic alcohol, phenylpropyl alcohol, eugenol, synthetic sandals and the like.
(3) Ethers 8-cineole, rose oxide, acetoxyamyl tetrahydropyran, cedolyl methyl ether, ethoxymethylcyclododecyl ether, rubofix, ambroxane, anethole, diphenyl oxide, β-naphthylmethyl ether, β-naphthylethyl ether etc.
(4) Aldehydes Nonyl aldehyde, decyl aldehyde, undecyl aldehyde, dodecyl aldehyde, 2,6-nonadienal aldehyde, undecylene aldehyde, citral, citronellal, miracaldehyde, rilal, perunaldehyde, benzaldehyde, phenylacetaldehyde, cinnamic aldehyde, Anisaldehyde, p-ethyl-2,2-dimethylhydrocinnamaldehyde, heliotropin, helional, vanillin, ethyl vanillin and the like.
(5) Acetals Fluoropearl, herboxane, magnolan, caranal, etc.
(6) Ketones Ethyl amyl ketone, camphor, carvone, menthone, geranyl acetone, cedol methyl ketone, ionone, methyl ionone, damascon, damascenone, dynascon, maltol, ethyl maltol, cis jasmon, iso-e super, benzylacetone, Calone, raspberry ketone, anisylacetone, methyl naphthyl ketone, benzophenone, etc.
(7) Esters Ethyl acetate, butyl acetate, isoamyl acetate, isononyl acetate, tapinyl acetate, nopylacetate, bornyl acetate, pt-butylcyclohexyl acetate, ot-butylhexyl acetate, tricyclodece Nyl acetate, benzyl acetate, styryl acetate, benzyl benzoate, methyl cinnamate, cinnamyl cinnamate, methyl salicylate, hexyl salicylate, cis-3-hexenyl salicylate, benzyl salicylate, methyl anthranilate, methyl jasmonate and the like.
(8) Lactone γ-decalactone, γ-undecalactone, γ-nonalactone, coumarin, jasmolactone and the like.
(9) Synthetic musk muscone, cyclopentadecanolide, ethylene brushate, musk ketone, musk xylol, musk ambrette, musk tibutene, 4-acetyldimethyl-t-butylindane, 6-acetyl-1,1,2,4 4,7-hexamethyltetralin, hexamethylhexahydrocyclopentazopyran and the like.
(10) Nitrogen / sulfur compounds Indole, geranyl nitrile and the like.

  It is preferable that the fragrance | flavor composition of this invention contains (b) component 10-50 mass%, and also 20-40 mass%.

  In the fragrance composition of the present invention, the mass ratio of the component (a) and the component (b) is (b) / (a) = 1/1 to 1/9, and further 2/3 to 1/9. It is preferable.

<(C) component>
The perfume composition of the present invention preferably contains (c) a waxy hydrophobic material [component (c)] having a melting point of 40 ° C. or higher and 100 ° C. or lower. The component (c) is preferably paraffin wax. The melting point of the component (c) is preferably 40 to 90 ° C, more preferably 40 to 80 ° C.

  As used herein, the wax of the hydrophobic hydrophobic material refers to an oily substance having a melting point higher than room temperature, which is interpreted broadly, and includes, for example, hydrocarbons, fatty acids and esters thereof.

  The hydrophobicity of the waxy hydrophobic material means that the water / octanol partition coefficient (log P) is 0 or more. Here, log P is a coefficient indicating the affinity of an organic compound for water and 1-octanol. 1-octanol / water partition coefficient P is a distribution equilibrium when a trace amount of compound is dissolved as a solute in a two-liquid solvent of 1-octanol and water, and is a ratio of the equilibrium concentration of the compound in each solvent. It is common to show them in the form of their logarithm logP for the base 10.

  Log P values of many compounds are reported, and many values are listed in a database available from Daylight Chemical Information Systems, Inc. (Daylight CIS), and can be referred to. When there is no measured log P value, it is most convenient to calculate with the program “CLOGP” available from Daylight CIS. This program outputs the value of “calculated logP (ClogP)” calculated by the Hansch, Leo fragment approach together with the measured logP value, if any.

  The mass ratio of the component (c) to the component (a) is preferably (c) component / (a) component = 2/8 to 8/2, more preferably 2/8 to 7/3, and 2/8. ~ 6/4 is more preferred. Moreover, the mass ratio of the sum of (a) component, (b) component, (c) component, and (b) component is (b) component / {(a) component + (b) component + (c) component}. = 1/2 to 1/10 is preferable, and 2/5 to 1/10 is more preferable. After satisfying these mass ratios, the fragrance composition of the present invention preferably contains 10 to 80% by mass, more preferably 10 to 60% by mass of the component (c).

  It is considered that the remaining fragrance can be improved by delaying or adjusting the volatilization of the fragrance by confining and solidifying the fragrance component using a normal temperature solid component on the surface of the fiber product such as clothing. If the melting point of the room temperature solid component is too high, the confined fragrance component is unlikely to move and the fragrance strength will decrease, so it is necessary to adjust it to a specific melting point range. is there. As for the crystals produced by the solid component, the finer the crystals, the easier it is for the fragrance to be confined between the fine crystals, and the fragrance is not firmly confined between the crystals of the room temperature solid component. It is considered that a good sustained-release effect of the fragrance component can be obtained due to the fact that it easily moves to the target and easily volatilizes in the air. In the perfume sustained-release technology using a room temperature solid component, it is considered important to control the movement speed of these perfume components. From this point of view, (a) represented by the general formula (1) selected in the present invention. It is considered that the component takes a good crystal state and exhibits a good sustained release effect of the fragrance component. Furthermore, it has been found that when a waxy hydrophobic material having a melting point of 40 ° C. or more and 100 ° C. or less is used in combination with the component (a) as the component (c), the fragrance sustainability is excellent. When the component (c) and the component (a) are used in combination, it is considered that each of them takes a crystalline state different from that of the component alone, and since the crystal structure becomes finer than that of the component (a) alone, the fragrance sustainability is improved. Estimated.

  The method for producing the fragrance composition of the present invention is not particularly limited, and can be used in any form, for example, a solid form, a fine particulate form, or an emulsion form.

  The fragrance | flavor composition of this invention can be used for various uses like a normal fragrance | flavor composition. For example, the present invention provides a fiber finish containing the above-described fragrance composition of the present invention. Examples of the fiber finishing agent include softeners, styling agents, glues, bleaches, and the like, and softeners are preferable. The content of the fragrance composition of the present invention in the fiber finish is appropriately determined in consideration of each use. In the case of a softener, the fragrance composition of the present invention is contained in an amount of 0.2 to 15% by mass. It is preferable to use in such an amount. More specifically, it is preferable to use the component (a) in an amount of 0.1 to 13.5% by mass and the component (b) in an amount of 0.1 to 1.5% by mass.

<Compounding ingredients>
(A) Component (a-1): Compound (a-1) produced in Synthesis Example 1

<Synthesis Example 1> [Synthesis of R ¹ , R ² = CH ₃ , R ³ = alkyl group having an average carbon number of 36 and n = 0 in formula (I)]
A 1 L glass pressure-resistant reaction vessel purged with nitrogen was charged with 400 mL of n-heptane, 2 mL of N, N, N ′, N′-tetramethylethylenediamine, 150 mL of 15% n-butyllithium hexane solution (1.6 mol / L), While maintaining the temperature of the reaction system at 30 to 80 ° C. and the ethylene gas introduction pressure at 5 kg / cm ² , 84.8 L of ethylene gas was introduced for polymerization. After the introduction of ethylene gas, a part of the reaction solution was sampled, reprecipitated with methanol, and the GPC spectrum was measured. The peak top was an n-alkane having 36 carbon atoms (Aldrich reagent was identified as a standard). . The molecular weight distribution was 1.1. 15 mL of decamethylcyclopentasiloxane was dropped into the polymerization mixture and reacted at 90 ° C. for 2 hours. Then, 72 g of an alkali adsorbent (KYOWARD 700SN; manufactured by Kyowa Chemical Industry Co., Ltd.) was added and stirred at 95 ° C. for 2 hours. did. The adsorbent was removed by hot filtration and the solvent was distilled off to obtain a white waxy solid. The yield was 110g. To 80 g of the obtained terminal silanol group-modified polyethylene, 150 g of n-heptane was added and heated on an oil bath at 110 ° C. for dissolution. 10 g of activated clay was added, a dehydrating tube was attached, and heating and stirring were continued for 4 hours. Further, activated carbon was added, and the mixture was continuously heated and stirred on an oil bath at 100 ° C. for 2 hours. Then, the activated clay and activated carbon were removed by hot filtration, and the solvent was distilled off to obtain a white waxy solid. The yield was 67g.

  When the melting point of the obtained disiloxane was measured with a melting point measuring instrument (manufactured by YANACO), it was 76 to 77.5 ° C., which was the same as the value measured with n-alkane having 36 carbon atoms (Aldrich reagent). did.

(B) Component (b-1): Geraniol

(C) Component (c-1): Paraffin, melting point 75 ° C. (manufactured by Nippon Seiki Co., Ltd .; product name Paraffin wax HNP-9, ClogP = 16.8)
(C-2): Paraffin, melting point 68-70 ° C. (Wako Pure Chemical Industries, Ltd., ClogP = 14.9)
(C-3): Paraffin, melting point 58-60 ° C. (manufactured by Wako Pure Chemical Industries, Ltd., ClogP = 13.1)

Example 1 and Comparative Example 1
The components (a), (b) and (c) were mixed in a glass container so as to have a total of 6 g with the composition shown in Table 1, sealed, and heated at 85 ° C. until the solid content was melted. Next, it was quenched with ice water at about 0 ° C. and solidified. The obtained solid was pulverized for 1 minute with a coffee mill (manufactured by National, MK-61M) to obtain a particulate perfume composition. Based on the composition of Table 1, this fragrance composition was weighed on a glass petri dish having a diameter of 8 cm so that the effective amount of component (b) was about 0.1 g (this value is the initial fragrance amount). . Thereafter, the sample was left in a constant temperature room at 20 ° C. and 65% RH, the weight was measured after 3 days and after 5 days, and the residual scent rate was determined by the following formula. In addition, the precision measurement which can measure to four digits after a decimal point was used for the weight measurement in a residual scent rate measurement.
[Remaining fragrance rate (%)] = {(A)-(B)} / (A) × 100
(A): Initial fragrance amount (g)
(B): Weight reduction (g)
However, for Comparative Example 4, about 0.1 g of (b-1) was sprayed onto cotton knitted fabric (made by Color Dyeing Co., Ltd., 100% cotton, new product) cut into a 10 cm square, and a glass having a diameter of 8 cm. The sample was placed on a petri dish and then evaluated in the same manner as described above. The results are shown in Table 1.

Example 2 and Comparative Example 2
(1) Preparation of softener composition In the softener composition of Example 1 of Unexamined-Japanese-Patent No. 2006-257565 and Table 1, it replaces with the fragrance | flavor [(h-1) component] in the said composition, and is the above. The prepared perfume compositions of Example 1-2 and Comparative Examples 1-1, 1-2, and 1-4 were each based on the composition of Table 1, and the effective component (b) was 0 in the softener composition. A softener composition was prepared so as to contain 7% by mass. Moreover, in Comparative Example 1-4, it adjusted so that (b) component [(b-1)] might contain 0.7 mass% in a softening agent composition.

(2) Softener treatment method Using a washing machine (MiniMini Washer National NA-35), two commercial cotton towels were softened. In the softener treatment, 15 g of water was used per 1 g of cloth. First, the softener composition prepared above was added to a washing machine filled with water at a ratio of 10.5 ml / 1.5 kg of towel, pre-stirred for 1 minute, and then two towels were added and stirred for 5 minutes. Subsequently, it was dehydrated for 5 minutes using a dewatering tank of a two-tank washing machine (HITACHI PS-H35L). After the treatment, it was dried in a constant temperature room at 20 ° C. and 65% RH. The softness of the towel after the treatment was at a level equivalent to the softening performance of a softener generally marketed. The residual scent intensity of the towel after the treatment was evaluated according to the following evaluation method.

(3) Residual scent strength evaluation method About the towel which processed the said softening agent, five panelists sniffed and evaluated the residual scent property on the following reference | standard. An average value of 10 panelists and a total of 10 evaluations was calculated for 2 towels, and the remaining scent intensity was evaluated as follows. The results are shown in Table 2. In addition, it evaluated about the residual scent intensity | strength 1 day after a process and 3 days after.
(Evaluation criteria)
2 points: feels strong fragrance 1 point: feels weak fragrance 0 points: does not feel fragrance (score of residual scent)
3: 2.0 or less, 1.5 or more, 2: less than 1.5, 1.0 or more, 1: less than 1.0, 0.5 or more, 0: less than 0.5, 0 or more

Claims (6)

(A) A fragrance composition containing a compound represented by the general formula (I) and (b) a fragrance.

[Wherein, R ¹ and R ² are alkyl groups having 1 to 6 carbon atoms, or aromatic hydrocarbon groups having 6 to 10 carbon atoms that may be substituted with alkyl groups, and R ³ is an average carbon number of 16 to 600 saturated hydrocarbon groups, n is an average value of 0 to 3000. ]   The fragrance composition according to claim 1, further comprising (c) a waxy hydrophobic material having a melting point of 40 ° C to 100 ° C.   The fragrance composition according to claim 2, wherein the component (c) is paraffin.   The fragrance composition according to claim 2 or 3, wherein (c) component / (a) component (mass ratio) = 2/8 to 8/2.   The fragrance composition according to claim 2, wherein (b) component / {(a) component + (b) component + (c) component} (mass ratio) = 1/2 to 1/10.   The fiber finishing agent containing the fragrance | flavor composition in any one of Claims 1-5.