JP2017214677A - Flavoring agent composition for fiber product - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a flavoring agent composition for fiber product which enhances an adsorption rate of a perfume adsorbed to a fiber product and can strongly feel aroma from the fiber product.SOLUTION: A flavoring agent composition for fiber product contains the following (A) component, (B) component and (C) component, where (content of (B) component)/(content of (A) component) being a mass ratio of a content of the (B) component to a content of the (A) component in the composition is 0 or more and 2.5 or less. The (A) component is internal olefin sulfonate having 14 to 16 carbon atoms. The (B) component is internal olefin sulfonate having 17 to 24 carbon atoms. The (C) component is a perfume compound having a molecular weight of 200 or more and 500 or less.SELECTED DRAWING: None

Description

  The present invention relates to a flavorant composition for textile products.

  Conventionally, anionic surfactants, especially alkylbenzene sulfonates, nonionic surfactants containing oxyalkylene groups having 2 to 3 carbon atoms, olefin sulfonates, especially having double bonds inside the olefin chain instead of at the ends Internal olefin sulfonates obtained from internal olefins as raw materials are widely used as household and industrial cleaning ingredients and perfume emulsifiers.

  Patent Document 1 contains an internal olefin sulfonate having 16 carbon atoms and an internal olefin sulfonate having 18 carbon atoms in a specific ratio, and has a specific ratio of hydroxy body / olefin body, excellent foaming properties, etc. An internal olefin sulfonate composition is disclosed.

  Patent Document 2 discloses a detergent composition excellent in detergency, which contains an internal olefin sulfonate containing 25% or more of a β-hydroxy form. Patent Document 2 describes a cleaning composition containing an internal olefin sulfonate and a nonionic surfactant as a specific example.

  Patent Document 3 describes a detergent composition containing an internal olefin sulfonate derived from an internal olefin having 12 to 18 carbon atoms and a nonionic surfactant having an HLB value of 10.5 or less in a specific ratio. ing.

  Moreover, the fragrance | flavor is used for the washing | cleaning agent for clothing, and the softening agent for clothing as a component which gives a fragrance to textiles.

JP2015-28123A European Patent Publication No. 377261 JP-A-3-126793

  The present invention provides a fragrance composition for a textile product that can increase the adsorption rate of the fragrance adsorbed to the textile product and make the scent feel strongly from the textile product.

The present invention contains the following component (A), component (B) and component (C), and is a mass ratio of the content of component (B) and the content of component (A) in the composition. (B) The flavorant composition for textiles whose content of component] / [content of (A) component] is 0 or more and 2.5 or less.
(A) Component: Internal olefin sulfonate having 14 to 16 carbon atoms (B) Component: Internal olefin sulfonate (C) having 17 to 24 carbon atoms: Fragrance compound having a molecular weight of 200 to 500

  ADVANTAGE OF THE INVENTION According to this invention, the fragrance | flavor composition for fiber products which the adsorption rate of the fragrance | flavor adsorb | sucked to a fiber product can be made to feel strongly from fiber products is provided.

  The present inventors have found that an internal olefin sulfonate having a specific carbon number among anionic surfactants increases the adsorption rate of a perfume compound having a molecular weight of 200 or more and 500 or less to a fiber product.

<(A) component and (B) component>
The component (A) of the present invention is an internal olefin sulfonate having 14 to 16 carbon atoms.
The component (B) of the present invention is an internal olefin sulfonate having 17 to 24 carbon atoms.
The number of carbon atoms of the component (A) and the component (B) represents the number of carbon atoms of the internal olefin to which the sulfonate is covalently bonded.

(A) component of this invention has the effect | action which emulsifies, solubilizes, or disperse | distributes a fragrance | flavor in the flavor composition for textiles with (B) component. However, among the known internal olefin sulfonates having various carbon numbers, the adsorption rate of the perfume compound having a molecular weight of 200 or more and 500 or less to the fiber product is increased by using the component (A). I found.
The number of carbon atoms in the component (A) is preferably 16 in that the adsorption rate of the fragrance compound having a molecular weight of 200 or more and 500 or less to the fiber product is further increased. Moreover, as for carbon number of (B) component, 18 is preferable. In the present invention, it is preferable that an internal olefin sulfonate having 16 carbon atoms is included as the component (A). When the component (B) is used, an internal olefin sulfonate having 18 carbon atoms is preferable, and in that case, a combination in which the component (A) is an internal olefin sulfonate having 16 carbon atoms is more preferable.

Since the component (A) and the component (B) have a common structure except for the number of carbon atoms, the common items will be described below. The component (A) and the component (B) may be collectively referred to as the internal olefin sulfonate of the present invention.
The internal olefin sulfonate of the present invention is obtained by sulfonating, neutralizing and hydrolyzing an internal olefin having 14 to 16 carbon atoms or 17 to 24 carbon atoms (olefin having a double bond inside the olefin chain) as a raw material. It is a sulfonate obtained by decomposing.
Such internal olefins include those containing trace amounts of so-called alpha olefins (hereinafter also referred to as α-olefins) in which the position of the double bond is located at the 1st position of the carbon chain.
In addition, when the internal olefin is sulfonated, β-sultone is quantitatively generated, and a part of β-sultone is changed to γ-sultone and olefin sulfonic acid, and these are further converted to hydroxy in the neutralization / hydrolysis step. Conversion to alkane sulfonate and olefin sulfonate (eg, J. Am. Oil Chem. Soc. 69, 39 (1992)). Here, the hydroxy group of the resulting hydroxyalkane sulfonate is inside the alkane chain, and the double bond of the olefin sulfonate is inside the olefin chain. In addition, the product obtained is mainly a mixture of these, part of which is a hydroxyalkane sulfonate having a hydroxy group at the end of the carbon chain, or an olefin having a double bond at the end of the carbon chain. A sulfonate may be contained in a trace amount.
In the present specification, each of these products and a mixture thereof are collectively referred to as an internal olefin sulfonate (component (A) or component (B)). Further, the hydroxyalkane sulfonate is referred to as a hydroxy form of internal olefin sulfonate (hereinafter also referred to as HAS), and the olefin sulfonate is referred to as an olefin form of internal olefin sulfonate (hereinafter also referred to as IOS).

In addition, the mass ratio of HAS and IOS of the compound in the component (A) or the component (B) can be measured by a high performance liquid chromatography mass spectrometer (hereinafter abbreviated as HPLC-MS). Specifically, the mass ratio can be determined from the HPLC-MS peak area of the component (A) or the component (B).
Moreover, also when an internal olefin sulfonate is obtained as a mixture containing (A) component and (B) component, if the ratio of the compound in this mixture is calculated | required similarly and the conditions of this invention are satisfy | filled, , (A) component and (B) component.

  Examples of the salt of the internal olefin sulfonate of the present invention include alkali metal salts, alkaline earth metal (1/2 atom) salts, ammonium salts, and organic ammonium salts. Examples of the organic ammonium salt include alkanol ammonium salts having 2 to 6 carbon atoms. Examples of the alkali metal salt include Na salt and K salt.

  In the present invention, when the mass of the component (A) is used, a value obtained by converting the counter ion of the component (A) into a sodium salt is used.

The sulfonic acid group of the internal olefin sulfonate of the present invention is present in the carbon chain of the internal olefin sulfonate, that is, the olefin chain or alkane chain, as is clear from the above-mentioned production method, and a carbon chain is partly included in the carbon chain. Some of which have a sulfonic acid group at the end thereof may be contained in a trace amount.
In the component (A) or the component (B), the content of the internal olefin sulfonate having a sulfonic acid group at the 2-position of the olefin chain or alkane chain is preferably 10% by mass or more and 60% by mass or less.
In addition, in the component (A) or the component (B), the content of the internal olefin sulfonate in which the sulfonic acid group is present at the 5-position or higher of the olefin chain or alkane chain is a fragrance compound having a molecular weight of 200 or more and 500 or less. From the viewpoint of increasing the adsorption rate to the fiber product, it is preferably 10% by mass or more, more preferably 20% by mass or more, and preferably 60% by mass or less.
In addition, in the component (A) or the component (B), the content of the olefin sulfonate having a sulfonic acid group at the 1-position of the olefin chain or alkane chain is a fiber product of a fragrance compound having a molecular weight of 200 to 500. From the viewpoint of increasing the adsorption rate to the water, it is preferably 10% by mass or less, more preferably 7% by mass or less, still more preferably 5% by mass or less, and still more preferably 3% by mass or less. And from a viewpoint of reduction of production cost and productivity improvement, Preferably it is 0.01 mass% or more.
The position of the sulfonic acid group of these compounds is the position in the olefin chain or alkane chain.

  The internal olefin sulfonate of the present invention can be a mixture of hydroxy and olefin. The mass ratio (olefin body / hydroxy body) of the content of the olefin body of the internal olefin sulfonate and the content of the hydroxy body of the internal olefin sulfonate in the component (A) is 0/100 or more, and further 5 / It can be 95 or more and 50/50 or less, further 40/60 or less, further 30/70 or less, and further 25/75 or less.

The mass ratio of the content of the hydroxy form of the internal olefin sulfonate and the content of the olefin form of the internal olefin sulfonate in the component (A) or the component (B) is from the component (A) or the component (B). After separating the hydroxy form and the olefin form by HPLC, it can be measured by the following method.
<Method of measuring mass ratio of hydroxy body / olefin body>
The mass ratio of hydroxy body / olefin body is measured by HPLC-MS. Specifically, it is identified by separating the hydroxy form and the olefin form from the internal olefin sulfonate to be measured by HPLC and applying each to MS. Each ratio is calculated | required from the HPLC-MS peak area.
In addition, the apparatus and conditions used for a measurement are as follows.
HPLC apparatus (trade name: Agilent Technology 1100, manufactured by Agilent Technologies),
Column (trade name: L-column ODS 4.6 × 150 mm, manufactured by the Chemical Substance Evaluation Research Organization),
Sample preparation (1000-fold dilution with methanol),
Eluent A (10 mM ammonium acetate added water),
Eluent B (methanol with 10 mM ammonium acetate),
Gradient (0 min. (A / B = 30/70%) → 10 min. (30/70%) → 55 min. (0/100%) → 65 min. (0/100%) → 66 min. (30/70%) ) → 75 min. (30/70%)),
MS device (trade name: Agilent Technologies 1100MS SL (G1946D)),
MS detection (anion detection m / z 60-1600, UV 240 nm)

The component (A) and the component (B) can be produced, for example, by sulfonating, neutralizing, and hydrolyzing an internal olefin having a predetermined carbon number as a raw material.
Sulfonation can be performed, for example, by reacting 1.0 to 1.2 mol of sulfur trioxide gas with respect to 1 mol of internal olefin. The reaction temperature can be 20 to 40 ° C.
Neutralization is carried out, for example, by reacting an alkaline aqueous solution such as sodium hydroxide, ammonia, 2-aminoethanol, etc. in an amount of 1.0 to 1.5 mole times the theoretical value of the sulfonic acid group.
For the hydrolysis, for example, the reaction may be performed at 90 to 200 ° C. for 30 minutes to 3 hours in the presence of water.
These reactions can be performed continuously. Moreover, after completion | finish of reaction, it can refine | purify by extraction, washing | cleaning, etc.

  In the production of the internal olefin sulfonate of the present invention, the raw material internal olefin having a distribution of 14 to 16 carbon atoms in the case of the component (A) and 17 to 24 carbon atoms in the case of the component (B). May be used for sulfonation, neutralization, and hydrolysis treatments, and raw material internal olefins having a single carbon number may be used for sulfonation, neutralization, and hydrolysis treatments. Accordingly, a plurality of types of internal olefin sulfonates having different carbon numbers produced in advance may be mixed.

  In the present invention, the internal olefin refers to an olefin having a double bond inside the olefin chain as described above. (A) Carbon number of the internal olefin which is a raw material of a component is 14-16. (B) Carbon number of the internal olefin which is a raw material of a component is 17-24. The internal olefin used for the component (A) or the component (B) may be used alone or in combination of two or more.

In the raw material internal olefin, the total content of olefins having a double bond at the 1-position, so-called alpha olefin, is preferable from the viewpoint of increasing the adsorption rate of the fragrance compound having a molecular weight of 200 or more and 500 or less to the fiber product. It is 10 mass% or less, More preferably, it is 7 mass% or less, More preferably, it is 5 mass% or less, More preferably, it is 3 mass% or less. And from a viewpoint of reduction of production cost and productivity improvement, Preferably it is 0.01 mass% or more.
In the raw material internal olefin, the content of the internal olefin having a double bond at the 5-position or higher is preferably 10% by mass from the viewpoint of increasing the adsorption rate of the fragrance compound having a molecular weight of 200 or more and 500 or less to the fiber product. Above, more preferably 20% by mass or more, and preferably 60% by mass or less. In addition, the maximum value of the position of the double bond in a raw material internal olefin changes with carbon number.
The distribution of double bonds in the raw material internal olefin can be measured by a gas chromatograph mass spectrometer (hereinafter abbreviated as GC-MS). Specifically, each component having a different carbon chain length and double bond position is accurately separated by a gas chromatograph analyzer (hereinafter abbreviated as GC), and each is subjected to a mass spectrometer (hereinafter abbreviated as MS). Thus, the position of the double bond can be identified, and each ratio can be obtained from the GC peak area. Below, the measuring method of the double bond position of a raw material internal olefin is shown.
<Measurement method of double bond position of raw material internal olefin>
The double bond position of the internal olefin is measured by gas chromatography (hereinafter abbreviated as GC). Specifically, dimethyl disulfide was reacted with an internal olefin to obtain a dithiolated derivative, and then each component was separated by GC. As a result, the double bond position of the internal olefin is determined from each peak area.
The apparatus and analysis conditions used for the measurement are as follows.
GC device “HP6890” (made by HEWLETT PACKARD),
Column “Ultra-Alloy-1HT capillary column” (30 m × 250 μm × 0.15 μm, manufactured by Frontier Laboratories),
Detector (hydrogen flame ion detector (FID)),
Injection temperature 300 ° C,
Detector temperature 350 ° C,
He flow rate 4.6 mL / min

[Component (C)]
Component (C) is a perfume compound having a molecular weight of 200 or more and 500 or less. Regarding the component (C), the fragrance compound can refer to a compound described as a fragrance component (fragrance material) in publications such as books and documents. In addition, compounds that are known to those skilled in the art can be used as a perfume material empirically. For example, perfume compounds described in patent literature, “Fundamental knowledge of perfume and fragrance” by Nakajima Motoki, published by Sangyo Tosho Co., Ltd., 2nd edition (May 30, 1996), “Actual knowledge of perfume” Indo Mention may be made of compounds described in books such as the original one by Toyo Keizai Shinposha.
The molecular weight of the component (C) is 200 or more, preferably 210 or more, and 500 or less, preferably 450 or less, more preferably in that the adsorption rate of the component (C) to the fiber product becomes higher. Is 300 or less, more preferably 290 or less, and still more preferably 270 or less.

Examples of the fragrance compound of component (C) include the following compounds. The numbers in parentheses are molecular weights.
i) Hydrocarbon fragrance selected from β-caryophyllene (204) and β-farnesene (204)

ii) Alcohol-based fragrance selected from santalol (220), nerolidol (222), β-caryophyllene (204), acetyl eugenol (206), eugenol (206)

iii) an aldehyde selected from amylcinnamic aldehyde (202), α-hexylcinnamic aldehyde (216), lilyal (204), methylionone α (206), methylionone G (206), trimethylundecenal (210), or Ketone perfume

iv) Ester flavors selected from benzyl salicylate (228) and benzyl benzoate (212)

v) An ether-based fragrance selected from cedroxide (220) and ambroxan (236) can be mentioned.

vi) Synthetic musk such as pearl ride (280)

  As component (C), amylcinnamic aldehyde (202), methylionone α (206), methylionone G (206), benzyl salicylate (228), α-hexylcinnamic aldehyde (216), lyial (204), and pearl A perfume compound selected from Ride (280) is preferred because it has a good fragrance and can impart a refreshing fragrance to the textile.

[Water and organic solvents]
The flavorant composition for textile products of the present invention preferably contains water and / or an organic solvent. More preferably, the flavor composition for textiles of the present invention contains water. As water, deionized water (sometimes referred to as ion-exchanged water) or sodium hypochlorite added in an amount of 1 mg / kg to 5 mg / kg with respect to the ion-exchanged water can be used. Tap water can also be used. Water is used to bring the composition into a liquid state, for example, a property at 4 ° C to 40 ° C. Water is a component that occupies the rest of the components other than water in the composition, and is usually used in an amount such that the composition of the entire composition is 100% by mass.

  Further, from the viewpoint of dispersibility, an organic solvent, preferably a water-miscible organic solvent may be contained. The water-miscible organic solvent referred to in the present invention refers to a solvent that dissolves 50 g or more in 1 L of ion-exchanged water at 25 ° C., that is, a solvent having a degree of dissolution of 50 g / L or more. The content of the organic solvent, preferably the water-miscible organic solvent, is preferably 1% by mass or more, more preferably 2% by mass or more, and preferably 40% by mass or less, more preferably 35% by mass or less in the composition. It is. Depending on the concentrations of the component (A) and the component (B), it may be less than 10% by mass. As the water-miscible organic solvent, a water-miscible organic solvent having a hydroxyl group and / or an ether group is preferable.

<Composition of a flavoring agent composition for textile products>
The fragrance composition for textiles of the present invention optionally contains a component (B).
The fragrance composition for textiles of the present invention is a mass ratio of the content of the component (B) and the content of the component (A) in the composition, [content of the component (B)] / [ (A) Component content] is 0 or more and 2.5 or less. The mass ratio [content of component (B)] / [content of component (A)] is 2.5 or less from the viewpoint of increasing the adsorption rate of the perfume compound having a molecular weight of 200 or more and 500 or less to the fiber product. Yes, preferably 2.3 or less, more preferably 2.0 or less, still more preferably 1.8 or less, still more preferably 1.6 or less, still more preferably 1.4 or less, and even more preferably 1.3. Or less, more preferably 1.1 or less, still more preferably 1.0 or less, still more preferably 0.8 or less, still more preferably 0.7 or less, still more preferably 0.6 or less, and even more preferably. Is 0.5 or less, more preferably 0.4 or less, even more preferably 0.3 or less, and preferably 0.01 or more, more preferably 0.05 or more. The mass ratio [content of component (B)] / [content of component (A)] may be zero.

  Moreover, the flavorant composition for textiles of this invention is the content of (A) component in a composition, and (B) component from a viewpoint that the adsorption rate of (C) component to textiles becomes higher. The total content is preferably 1% by mass or more, more preferably 3% by mass or more, and preferably 50% by mass or less, more preferably 45% by mass or less.

  Further, in the fragrance composition for textiles of the present invention, the content of the component (C) in the composition is preferably 0.01% by mass or more, more preferably 0.05% by mass or more, and preferably Is 5% by mass or less, more preferably 3% by mass or less.

  The fiber product flavoring composition of the present invention comprises, as an optional component, an alkali agent, a chelating agent, a recontamination inhibitor and a dispersant, a bleaching agent, a softening agent, an enzyme, a fluorescent dye, an antioxidant, a pigment, an antibacterial antiseptic Agents, antifoaming agents, and the like.

  The fiber product flavoring composition of the present invention has a pH at 20 ° C. of preferably 2 or more, more preferably 2.5 or more, and preferably 9 or less, more preferably 8.5 or less.

  The fiber constituting the fiber product treated with the flavorant composition for fiber products of the present invention may be either a hydrophobic fiber or a hydrophilic fiber. Examples of hydrophobic fibers include protein fibers (milk protein casein fiber, promix, etc.), polyamide fibers (nylon, etc.), polyester fibers (polyester, etc.), polyacrylonitrile fibers (acrylic, etc.), and polyvinyl alcohols. Fiber (such as vinylon), polyvinyl chloride fiber (such as polyvinyl chloride), polyvinylidene chloride fiber (such as vinylidene), polyolefin fiber (polyethylene, polypropylene, etc.), polyurethane fiber (polyurethane, etc.), polyvinyl chloride / Polyvinyl alcohol copolymer fiber (such as polycleral), polyalkylene paraoxybenzoate fiber (such as benzoate), polyfluoroethylene fiber (such as polytetrafluoroethylene), glass fiber, carbon fiber, aluminum Fibers, silicone carbide fibers, rock fibers (rock fur Iba), slag fibers (slug fiber), metal fiber (gold, silver thread, steel fibers) and the like. Examples of hydrophilic fibers include seed hair fibers (cotton, rice noodles, kapok, etc.), bast fibers (hemp, flax, hemp, cannabis, jute, etc.), leaf vein fibers (manila hemp, sisal hemp, etc.), palm fibers, Igusa, straw, animal hair fibers (wool, mohair, cashmere, camel hair, alpaca, bicuña, Angola, etc.), silk fibers (rabbit silk, wild silk), feathers, cellulosic fibers (rayon, polynosic, cupra, acetate, etc.) Etc. are exemplified.

In the present invention, the textile product refers to fabrics such as woven fabrics, knitted fabrics, and nonwoven fabrics using the above-mentioned hydrophobic fibers and hydrophilic fibers, and undershirts, T-shirts, Y-shirts, blouses, slacks, and hats obtained using the fabrics. , Handkerchiefs, towels, knitwear, socks, underwear, tights, etc.
From the viewpoint of increasing the adsorption rate of the component (C) to the fiber product, the fiber is preferably a fiber product containing cotton fibers. From the same viewpoint, the content of the cotton fiber in the fiber product is preferably 5% by mass or more, preferably 10% by mass or more, preferably 15% by mass or more, preferably 20% by mass or more, and the upper limit is 100% by mass. is there.

  The treatment of the fiber product using the fiber product flavorant composition of the present invention is carried out by bringing the fiber product flavorant composition of the present invention into contact with the fiber product. Examples of the method of bringing the composition of the present invention into contact with a textile product include a method of immersing the textile product in a diluted solution obtained by diluting the composition of the present invention with water. Here, the immersion refers to a state in which the fiber product is completely immersed in a diluted solution obtained by diluting the composition of the present invention with water.

  In the case of treating a textile product by dipping treatment, a method of adding the composition of the present invention to rinsing water at the rinsing stage of the washing process is preferable. In this case, the added amount of the composition of the present invention is preferably 0.01 mL or more, further 0.05 mL or more, and 50 mL or less, and further 40 mL or less per 1 kg of clothing in order to exhibit the effects of the present invention. The temperature of the rinsing water is preferably 3 ° C. or higher, more preferably 5 ° C. or higher, and preferably 40 ° C. or lower, more preferably 35 ° C. or lower. The treatment time is preferably 2 minutes or longer, more preferably 3 minutes or longer, and preferably 90 minutes or shorter, more preferably 60 minutes or shorter. After soaking, it is dehydrated and dried by natural drying or a rotary heat dryer. The dried fiber product is less wrinkled to the extent that it does not need to be ironed, but it can be ironed if the finish is more important.

The present invention is a method for producing a fragrance composition for textiles, comprising mixing the following component (A), component (B), component (C) and water,
(A) component and (B) component are used at a mass ratio of (A) component / (B) component = 0 to 2.5,
A method for producing a flavorant composition for textile products is provided.
(A) Component: Internal olefin sulfonate having 14 to 16 carbon atoms (B) Component: Internal olefin sulfonate (C) having 17 to 24 carbon atoms Component: Perfume compound having a molecular weight of 200 to 500 The preferable aspect of each component of a method is the same as the flavoring agent composition for textiles of this invention. Moreover, the said mass ratio can also apply the preferable value of the mass ratio in the fragrance | flavor composition for textiles.

  The fragrance composition for textiles of the present invention may be used by blending with a generally known detergent composition for textiles, or by blending with a finishing composition for textiles. May be.

[Production Example A1]
(1) Production of internal olefin having 16 carbon atoms In a flask equipped with a stirrer, 1-hexadecanol (product name: Calcoal 6098, manufactured by Kao Corporation) 7000 g (28.9 mol), γ-alumina (STREM) as a solid acid catalyst (Chemicals, Inc.) 700 g (10% by mass with respect to the raw material alcohol) was charged, and the reaction was carried out while changing the reaction time while circulating nitrogen (7000 mL / min.) Through the system at 280 ° C. with stirring. . The obtained crude internal olefin was transferred to a distillation flask and distilled at 136-160 ° C./4.0 mmHg to obtain a 16-carbon internal olefin having an olefin purity of 100%. Table 1 shows the distribution of double bonds of the obtained internal olefin.

(2) Production of internal olefin sulfonate having 16 carbon atoms Sulfur trioxide gas and reaction using the thin film type sulfonation reactor having a jacket on the outside using the internal olefin having 16 carbon atoms obtained in (1). The sulfonation reaction was carried out by passing cooling water at 20 ° C. through the outer jacket of the vessel. The molar ratio of SO ₃ / internal olefin during the sulfonation reaction was set to 1.09. The obtained sulfonated product was added to an alkaline aqueous solution prepared with 1.5 mol times the amount of sodium hydroxide with respect to the theoretical acid value, and neutralized at 30 ° C. for 1 hour with stirring. The neutralized product was hydrolyzed by heating in an autoclave at 160 ° C. for 1 hour to obtain a crude product of 16-carbon sodium olefin sulfonate. 300 g of the crude product was transferred to a separatory funnel, 300 mL of ethanol was added, and 300 mL of petroleum ether was added at one time to extract and remove oil-soluble impurities. At this time, the inorganic compound (main component was sodium sulfate) precipitated at the oil / water interface by addition of ethanol was also separated and removed from the water phase by the oil / water separation operation. This extraction and removal operation was performed three times. The aqueous phase side was evaporated to dryness to obtain an internal sodium olefin sulfonate having 16 carbon atoms.

[Production Example B1]
In Production Example A1 (1), 1-octadecanol was used as a raw material, and the production conditions were appropriately changed to obtain an internal olefin having 18 carbon atoms. Table 1 shows the distribution of double bonds of the obtained internal olefin. Using this internal olefin having 18 carbon atoms, sodium internal olefin sulfonate having 18 carbon atoms was obtained in the same manner as in Production Example A1 (2).

<Blending ingredients>
Each compounding component used in Examples and Comparative Examples is shown below.
(A) Component (a-1): Sodium olefin sulfonate having 16 carbon atoms obtained in Production Example A1

Component (A ′): Comparative compound (a′-1) of component (A): Sodium alkylbenzene sulfonate (Neopelex G-65 (manufactured by Kao Corporation)

(B) Component (b-1): Sodium olefin sulfonate having 18 carbon atoms obtained in Production Example B1

(C) Component (c-1): Pearl Ride (Molecular weight: 280)
(C-2): α-hexylcinnamic aldehyde (molecular weight: 216)
(C-3): Lilianal (molecular weight: 204)

Component (C ′): Comparative compound (c′-1) of component (C): Cyclamenaldehyde (molecular weight: 190)
(C′-2: Estragole (molecular weight: 148)
(C′-3): Phenylethyl alcohol (molecular weight: 122)

Examples 1-1 to 1-3-1 and Comparative Examples 1-1 to 4-8
By the method shown below, the fragrance | flavor composition for textiles of the composition shown to Tables 2-5 was prepared. The obtained fiber product flavoring composition was evaluated for the adsorption rate of the fiber product by the following evaluation method. The results are shown in Tables 2-5.

<Method for preparing a flavoring composition for textile products>
Screw tube No. 2, (A) component or (A) component, (B) component, (C) component or (C ′) component and ions necessary for the finished mass of the fiber product flavoring composition to be 2.0 g Exchange water was added and stirred with a vortex mixer. The obtained mixture was allowed to stand at 60 ° C. for 24 hours and then allowed to stand at 25 ° C. for 3 days to obtain a fiber product flavoring composition.

<Measurement method of adsorption rate of perfume compound to textiles>
(1) Pretreatment of cotton towel for evaluation Twenty-four commercially available cotton towels (100% cotton, Takei towel, TW-220) were repeatedly washed five times with Hitachi automatic washing machine NW-6CY. A nonionic surfactant (ethylene oxide adduct of lauryl alcohol (average added mole number 8)) was used as a surfactant for washing. In addition, the washing condition for one washing was 4.5 g of a nonionic surfactant used, a standard course, a water volume of 45 L, a water temperature of 20 ° C., and a washing time of 10 minutes. After the last washing, it was dried for 1 day at 20 ° C. and 43% RH.

(2) Treatment of evaluation cotton towel A plurality of evaluation cloths were prepared by cutting the cotton towel pretreated by the method of (1) above into a size of 8.5 cm × 8.5 cm.
In a 100 ml beaker, a necessary amount of 4 ° dH water and a flavorant composition for textile products shown in Tables 2 to 5 were placed, and the two evaluation cloths were placed.
As water at 4 ° dH, calcium chloride and magnesium chloride were added to ion-exchanged water in a mass ratio of 8: 2, and the hardness was adjusted to 4 ° dH.
The required amount of the flavoring composition for textile products and the required amount of water at 4 ° dH are calculated based on the condition that the total amount of the component (A) and the component (B) is 300 ppm and the treatment liquid is 20 L / kg of fiber. It was done.
The contents of the beaker were stirred for 10 minutes at 500 rpm using a 3 cm stirrer chip and a digital stirrer (AS ONE magnetic stirrer, REXIM series, RS-4DN). The treatment bath in this treatment is a mixture of 4 ° dH water and the flavorant composition for textiles shown in Tables 2-5.
The adsorption rate of the fragrance compound [component (C) or (C ′)] is the difference between the fragrance compound content (x) in the treatment bath before treatment and the fragrance compound content (y) in the treatment bath after treatment. [(X)-(y)] as the amount adsorbed on the evaluation cloth, the ratio (percentage) to the fragrance compound content (x) before treatment, that is, [(x)-(y)] / (x ) × 100.
In addition, content of the fragrance | flavor compound in the processing bath before and behind a process was measured using the following liquid chromatography apparatus.
Liquid chromatography device: HITACHI L-2455
Column: L-column ODS 4.6 × 150 mm, L-C18, 5 μm, 12 nm
Column temperature: 40 ° C
Eluent: A mixed solution of acetonitrile / water = 6/4 (mass ratio) Flow rate: 1.0 mL / min
Detector: UV (220 nm)

  In an olefin having 16 carbon atoms, an internal olefin having a double bond at the 7-position and an internal olefin having a double bond at the 8-position cannot be distinguished from each other in structure. Specifically, the value obtained by dividing the amount of internal olefin having a double bond at the 7-position by 2 is shown in the respective columns for the 7-position and the 8-position. Similarly, for olefins having 18 carbon atoms, the value obtained by dividing the amount of internal olefin having a double bond at the 8th position by 2 is shown in the respective columns for the 8th and 9th positions.

  It can be seen from Table 2 that the amount of the perfume compound having a specific molecular weight adsorbed on the fiber product is increased by using the component (A) of the present invention.

  From Table 3, it can be seen that even when the component (B) of the present invention is used in a specific ratio with respect to the component (A), the amount of the perfume compound having a specific molecular weight adsorbed on the fiber product is increased.

  From Table 4, it can be seen that the amount of the perfume compound having a specific molecular weight adsorbed to the fiber product is increased by using the component (A) of the present invention.

  From Table 5, it can be seen that by using the component (A) of the present invention, the amount of the perfume compound having a molecular weight of 200 or more and 500 or less adsorbed to the fiber product is increased.

Claims (4)

The following (A) component, (B) component, and (C) component, [B] component which is mass ratio of content of (B) component in a composition, and content of (A) component Content] / [content of component (A)] is 0 or more and 2.5 or less.
(A) Component: Internal olefin sulfonate having 14 to 16 carbon atoms (B) Component: Internal olefin sulfonate (C) having 17 to 24 carbon atoms: Fragrance compound having a molecular weight of 200 to 500   The flavorant composition for textiles according to claim 1, wherein [content of component (B)] / [content of component (A)] is 0 or more and 2.0 or less.   (C) The fragrance | flavor composition for textiles of Claim 1 or 2 whose molecular weight of a component is 200-300.   The fragrance composition for textiles according to any one of claims 1 to 3, comprising water and / or an organic solvent.