JP5336203B2 - Textile treatment composition - Google Patents

Description

  The present invention relates to a textile product treating agent composition and a textile product treating method.

  In recent years, with the increasing awareness of the fragrance of textile products, various textile composition treatment compositions such as detergents and finishes for clothing using persistent fragrances and sustainability-imparting ingredients, and treatment methods thereof have been studied. Yes. However, since these fiber treatment agent compositions are processed into a fiber product through water or an organic solvent, the fragrance imparted to the fiber product volatilizes with the solvent during drying, or the fragrance is spread over the cloth over time after drying. By evaporating from the scent, the scent emitted from the cloth becomes weaker. Usually, textile products are stored and stored in a chiffon after washing if they become dirty. And the period until the next time you use or wear it is generally less than 4 days, at most less than a week. Even after such a period, for example, it is strongly demanded that the smell of the storage location is not applied to the textile product, and that the scent continues throughout the storage even if it is worn and used after storage.

  In order to meet these demands, for example, Patent Document 1 discloses a fiber fragrance imparting agent containing an organosiliconate and water, and a fiber fragrance method. Patent Document 2 discloses a fabric softening composition that contains a specific long-lasting perfume composition and improves the life of the perfume on the fabric. Patent Document 3 discloses a fabric softener composition that contains a specific long-lasting perfume composition and exhibits improved perfume durability on the laundry. On the other hand, a technique for imparting scent sustainability and a technique for improving the texture of clothing using a specific silicon compound are disclosed. Patent Document 4 discloses a knitted fabric conditioner composition containing a specific silicon compound and a fatty alkyl quaternary ammonium compound and imparts a long-lasting fragrance to the knitted fabric. Patent Document 5 discloses a specific silicon compound. And a cleaning composition containing a fragrance imparting component that imparts a long-lasting fragrance to the knitted fabric. Patent Document 6 discloses a silicate ester mixture containing a specific silicate ester excellent in hydrolysis resistance, and a composition containing them. Furthermore, Patent Document 7 discloses a silane derivative having an alkenyloxy group that imparts durability to fragrance diffusion and is useful as a long-life fragrance material.

JP 2008-223156 A Japanese National Patent Publication No. 11-504994 JP 10-507793 A JP-A-54-59498 Japanese Patent Laid-Open No. 54-93006 Special table 2003-526644 JP 58-90593 A

  The techniques disclosed in Patent Documents 1 to 3 improve the fragrance life on the fabric, and the intensity of the fragrance does not change with time from immediately after the treatment. Patent Documents 4 to 7 disclose a silicon compound having a structure similar to that of the present invention and a composition containing the silicon compound. There is no suggestion of positively maintaining the intensity of the scent throughout use.

  The object of the present invention is to maintain the optimal fragrance strength for a textile product even after a period (approximately 4 days or less, within 1 week for a long one) after washing and storing or storing the textile product until it is used or worn. It is another object of the present invention to provide a fiber product treating agent composition that can exhibit the best scent strength when worn.

The present invention includes a fiber product treating agent composition containing the following component (a) and component (b) at a mass ratio of (a) component / (b) component = 1/10 to 10/1, and the fiber product. A textile product processing method for treating a textile composition with a treating agent composition is provided.
(A) Component: Compound represented by the general formula (1)

[Wherein, X is —OH, —R ¹ (R ¹ is an aliphatic hydrocarbon group having 1 to 22 carbon atoms in total which may have a phenyl group, a hydroxyl group or an alkoxy group as a substituent) or —OR ^{2. (R 2} is a hydrocarbon group having 6 to 22 carbon atoms), Y represents X or -OSi _(X) 3, n is a number of 0 to 15 showing an average value. The plurality of X and Y may be the same or different, but have at least one —OR ^{2 in} one molecule. ]
Component (b): a tertiary amine having at least one hydrocarbon group having 12 to 28 carbon atoms which may be separated by an ester group or an amide group in the molecule, an acid salt thereof or a quaternized product thereof At least one cationic surfactant.

  According to the present invention, it is possible to maintain the optimal fragrance strength for a textile product even after a period of washing the textile product and using or wearing it after storage / storage (generally within 4 days, even within a week even if it is long). Furthermore, it is possible to provide a fiber product treating agent composition that can exhibit the best scent strength when worn.

[(A) component]
The component (a) of the present invention is a compound represented by the above general formula (1).

In the general formula (1), X is —OH, —R ¹ or —OR ² , Y is X or —OSi (X) ₃ , n is a number of 0 to 15 indicating an average value, and a plurality of X and Y may be the same or different, but has at least one —OR ^{2 in} one molecule.

R ¹ represents an aliphatic hydrocarbon group having 1 to 22 carbon atoms which may have a phenyl group, a hydroxyl group or an alkoxy group as a substituent, but has a phenyl group, a hydroxyl group or an alkoxy group as a substituent. A linear or branched alkyl group or alkenyl group having 1 to 22 total carbon atoms may be preferable, and when n is 0, a linear or branched alkyl group having 6 to 18 carbon atoms is more preferable, Straight chain alkyl groups having 6 to 18 carbon atoms such as n-hexyl group, n-octyl group, n-decyl group, n-dodecyl group, n-hexadecyl group and n-octadecyl group are more preferable, and the number of carbon atoms is 10 to 18 Are even more preferred.

R ² represents a hydrocarbon group having 6 to 22 carbon atoms, preferably 6 to 15 carbon atoms, more preferably 8 to 15 carbon atoms, and the hydrocarbon group is preferably an alkyl group, an alkenyl group, an alkylaryl group or an arylalkyl group, In particular, a group selected from an alkyl group and an alkenyl group having a branched structure is preferable from the viewpoint of developing a good scent.

In the general formula (1), when n is 0, a compound in which 2 to 4 of 4 X, preferably 3 or 4 is —OR ² and the rest is —R ¹ is suitable. is there.

  A preferable compound in the case of n = 0 includes a compound represented by the following formula (1-1) or (1-2).

[Wherein, R ¹ and R ² have the same meaning as described above. ]
In the general formula (1), when n is 1 to 15, n represents an average value, and for all X and Y, 1/10 or more, preferably 1/8 or more is -OR ² A compound in which the remainder is —R ¹ is preferred, and a compound in which all X and Y are —OR ² is particularly preferred. As n, 1-10 are preferable and 1-5 are more preferable.

  Preferred compounds when n is 1 to 15 include compounds represented by the following formula (1-3) or (1-4).

[Wherein, R ¹ and R ² have the same meaning as described above. m represents a number of 1 to 15, T represents the -OR ² or -R ^1. ]
The compound represented by the general formula (1) can be obtained by the methods described in Patent Document 4, Patent Document 6, and the like.

[Component (b)]
In order to further enhance the effect of the present invention, particularly for the purpose of further enhancing the effect when treated in a treatment bath containing a large amount of detergent components, the textile product treating agent composition of the present invention is a molecule as a component (b). Cationic surface activity selected from tertiary amines having at least one hydrocarbon group having a total carbon number of 12 to 28 which may be separated by an ester group or an amide group, their acid salts or quaternized products thereof It is preferable to contain an agent.

  (B) As a component, at least 1 sort (s) chosen from the tertiary amine represented by General formula (2), its acid salt, or its quaternization thing is preferable.

[Wherein, the R ^a1 group is a hydrocarbon group having 12 to 28 carbon atoms which may be separated by an ester group or an amide group, and the R ^a2 group and the R ^a3 group are each independently an R ^a1 group, It is a group selected from an alkyl group having 1 to 3 carbon atoms and a hydroxyalkyl group having 1 to 3 carbon atoms. ]
In the general formula (2), examples of the R ^a1 group include the groups shown in the following (i) to (iii), and the R ^a2 group and the R ^a3 group are each independently the following (i) to (v): The group shown in these is mentioned.
(I) a total carbon number of 12 to 28 divided by an ester group or an amide group, preferably a saturated hydrocarbon group of 14 to 26 (ii) a total number of carbon atoms of 12 to 28 divided by an ester group or an amide group, Preferably, an unsaturated hydrocarbon group having one or more double bonds of 14 to 26 (iii) a mixture of the groups (i) and (ii) (iv) a hydroxyalkyl group having 1 to 3 carbon atoms (v ) Alkyl group having 1 to 3 carbon atoms (b) The component is obtained by subjecting a fatty acid or a fatty acid lower alkyl ester and an amine such as an alkanolamine or aminoalkylamine to an esterification reaction, an amidation reaction, or an ester exchange reaction. be able to. In order to obtain a fatty acid or fatty acid lower alkyl ester having the above-mentioned preferred hydrocarbon composition, if it cannot be achieved simply by using a fatty acid as commonly known in oil and fat manuals, etc., hydrogenation reaction to unsaturated bond, It can be obtained by isomerization reaction of saturated bonds, distillation operation, bottom cut, adjustment of alkyl chain length by top cut, or mixing of a plurality of fatty acids.
The aminoalkylamine is preferably an amine having at least two amino groups selected from a primary amino group, a secondary amino group, and a tertiary amino group in the molecule. The alkanolamine is preferably an amine having a hydroxyl group in the molecule and having a primary to tertiary amino group. More specific examples include dialkylmonoalkanolamines (preferably dimethylmonoethanolamine or dimethylmonopropanolamine), monoalkyldialkanolamines (preferably methyldiethanolamine or methyldipropanolamine), or trialkanolamines (preferably trialkanolamines). Ethanolamine or tripropanolamine), or di (aminoalkyl) alkylamine (eg, N-methyl-N, N-di (3-aminopropyl) amine), dialkylaminoalkylamine ((eg, N, N-dimethyl). -N- (3-aminopropyl) amine), alkylaminopropylmonoalkylalkanolamine (preferably N-methyl-N- (2-hydroxyethyl) -N- (3-aminopropyl) amine In particular, N-methyldiethanolamine, triethanolamine, N-methyl-N- (2-hydroxyethyl) -N- (3-aminopropyl) amine, N, N -Dimethyl-N- (3-aminopropyl) amine, N, N-dimethyl-N- (2-hydroxyethyl) amine.

  In the esterification reaction, amidation reaction or transesterification reaction, the molar ratio of the fatty acid or fatty acid lower alkyl ester to the total number of moles of the hydroxyl group and primary to secondary amino group of the amine is 0.5: 1. ~ 2: 1 is preferred, 0.6: 1 to 2: 1 is more preferred, 0.7: 1 to 0.98: 1 is particularly preferred, and most preferably 0.8: 1 to 0.98: 1. It is.

  Examples of the tertiary amine acid salt represented by the general formula (2) include acid salts neutralized with inorganic acids and organic acids. Preferred inorganic acids are hydrochloric acid, sulfuric acid, and phosphoric acid, and preferred organic acids are monovalent or polyvalent carboxylic acids having 1 to 10 carbon atoms, or monovalent or polyvalent sulfonic acids having 1 to 20 carbon atoms, or It is an alkyl sulfate ester having 6 to 36 carbon atoms or a polyoxyalkylene alkyl (alkyl group having 6 to 36 carbon atoms) sulfate ester. More preferably, methyl sulfuric acid, ethyl sulfuric acid, p-toluenesulfonic acid, (o-, m-, p-) xylenesulfonic acid, benzenesulfonic acid, dodecylbenzenesulfonic acid, glycolic acid, citric acid, benzoic acid, salicylic acid, carbon It is an alkyl sulfate ester having 12 to 36 or a polyoxyalkylene alkyl (alkyl group having 12 to 36 carbon atoms) sulfate ester. As the quaternized product of the tertiary amine represented by the general formula (2), the tertiary amine represented by the general formula (2) is converted to 4 with an alkylating agent such as alkyl halide, dialkyl sulfuric acid, alkylene oxide or the like. Examples include graded compounds. The alkyl halide is preferably methyl chloride, the dialkyl sulfuric acid is preferably dimethyl sulfuric acid or diethyl sulfuric acid, and the alkylene oxide is preferably ethylene oxide. In addition, the quaternization reaction using an alkylating agent can be performed in the presence of a solvent (for example, ethanol), but the viewpoint of maintaining the odor and storage stability of the synthesized product and / or suppressing the generation of impurities. From the above, it can be carried out in the absence of a solvent.

[Fiber product treatment composition]
The content of the component (a) in the textile product treating agent composition of the present invention is preferably 0.01 to 90% by mass, and 0.05 to 50% by mass from the viewpoint of obtaining the effects of the present invention and an economic viewpoint. Is more preferable, 0.1-20 mass% is still more preferable, and 0.1-10 mass% is especially preferable. Further, the content of the component (b) in the fiber product treating agent composition of the present invention is preferably 0.1 to 10% by mass, more preferably 0. 0% from the viewpoint of maintaining the optimum fragrance strength for the fiber product. 1-8 mass%, More preferably, it is 0.5-5 mass%.

  The fiber treatment agent composition of the present invention has a viscosity ratio of the treatment agent composition and a uniform dispersibility that realizes uniform adsorption on the fiber product during use, and the mass ratio of the component (a) / (b) is: 1/10 to 10/1, preferably 1/8 to 8/1, more preferably 1/5 to 5/1.

  In addition to the components (a) and (b), the fiber treatment agent composition of the present invention has the effects of the present invention for the purpose of improving the solubility and dispersion of each component in the composition and the emulsified state. It is preferable to contain a nonionic surfactant [hereinafter referred to as component (c)] in an amount that does not impair the amount.

  As the component (c), a nonionic surfactant having an alkyl group or alkenyl group having 8 to 20 carbon atoms and an oxyalkylene group is preferable, and a nonionic surfactant represented by the following general formula (3) is more preferable. .

R ^2a -A-[(R ^2b O) _p -R ^2c ] _q (3)
[Wherein R ^2a is an alkyl group or alkenyl group having 8 to 18 carbon atoms, preferably 10 to 16 carbon atoms, R ^2b is an alkylene group having 2 or 3 carbon atoms, preferably an ethylene group, R ^2c is an alkyl group having 1 to 3 carbon atoms or a hydrogen atom, p is 2 to 100, preferably 5 to 80, more preferably 5 to 60, still more preferably 10 to 60, and A is -O-, -COO-, -CON- or -N-, q is 1 when A is -O- or -COO-, and q is 1 or when A is -CON- or -N-. 2. ]
Specific examples of the compound of the general formula (3) include compounds represented by the following formulas (3-1) to (3-3).

R ^2a —O— (C ₂ H ₄ O) _r —H (3-1)
[Wherein R ^2a has the above-mentioned meaning. r is a number of 8 to 100, preferably 10 to 60. ]
_{^{R 2a -O- (C 2 H 4}} O) s - (C 3 H 6 O) t -H (3-2)
[Wherein R ^2a has the above-mentioned meaning. s and t are each independently a number of 2 to 40, preferably 5 to 40, and (C ₂ H ₄ O) and (C ₃ H ₆ O) may be random or block adducts. ]

[Wherein R ^2a has the above-mentioned meaning. B is -N <or -CON <, u and v are each independently a number from 0 to 40, and u + v is a number from 5 to 60, preferably from 5 to 40. R ^2d and R ^2e are each independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. ]
From the viewpoint of maintaining the optimum fragrance strength for the fiber product within one week after the fiber product is treated with the fiber treatment composition of the present invention, the mass ratio of component (b) / component (c) is 20 / 1 to 1/10, preferably 15/1 to 1/5, more preferably 10/1 to 1/3.

  The textile product treating agent composition of the present invention can contain a fatty acid (hereinafter referred to as the component (d)) from the viewpoint of improving the dispersibility of the component (a) and the component (b), specifically, lauric acid. Saturated or unsaturated fatty acids having 12 to 22 carbon atoms such as myristic acid, palmitic acid, palmitoleic acid, stearic acid, oleic acid, linoleic acid, erucic acid, behenic acid, etc. are preferred, especially palmitic acid, stearic acid, oleic acid, Linoleic acid is preferred.

  The composition of the present invention can contain an inorganic salt as the component (e) as necessary for the purpose of improving storage stability. As the inorganic salt, sodium chloride, calcium chloride, and magnesium chloride are preferable from the viewpoint of storage stability.

  The composition of the present invention may contain an ester compound of a saturated or unsaturated fatty acid having 8 to 22 carbon atoms and a polyhydric alcohol as the component (f) for the purpose of improving storage stability. Examples of the component (f) that can be blended include triglycerides, diglycerides, monoglycerides, mono-, di-, tri-fatty acid esters, and sorbitan fatty acid esters of pentaerythritol.

  The composition of this invention may contain a solvent as (g) component as needed from a viewpoint of the dispersibility improvement of (a) component and (b) component. As the solvent, a solvent selected from ethanol, isopropanol, glycerin, ethylene glycol, and propylene glycol is preferable, and ethanol is particularly preferable from the point of smell.

[Treatment method for textile products]
Examples of the method for treating a textile product using the textile product treating agent composition of the present invention include the following methods (i) and (ii).
(I) A method of adding the treatment composition to rinsing water at the rinsing stage in the washing process of the textile product (ii) A method of spraying the treatment composition onto the textile product using a sprayer such as a trigger container ( When using the method of i), 3-20 are preferable and, as for bath ratio (mass ratio of water / textile product), 4-17 are more preferable. In the use of a drum-type washing machine, these bath ratios are usually set automatically according to the weight of the laundry. In consideration of these bath ratios and the like, it is preferable to select a rinsing condition so that the component (a) and the component (b) adhere to the textile product efficiently. In this method, the treating agent composition of the present invention is used so that the component (a) per kg of the textile product is 0.005 to 10.0 g, preferably 0.05 to 5.0 g. When using a washing dryer, a drying function may be used. The heat treatment temperature at that time is preferably 40 to 120 ° C., more preferably 50 to 100 ° C., and the heat treatment time is about 5 to 400 minutes, although it depends largely on the function of the washing and drying machine.

  In the method (i), when the treating agent composition of the present invention is added during the rinsing treatment, the amount of addition is preferably such that the proportion of the component (a) is 0.001 to 1000 ppm relative to water. A ratio of ˜100 ppm is more preferable. After the treatment agent composition of the present invention is added to rinsing water, it is preferable to dehydrate and air dry.

When the method (ii) is used, the sprayer is not particularly limited, and a commercially available spray vial, a trigger sprayer, or the like can be used. The amount of spray from the sprayer is 0.01-2.0 g, preferably 0.05-1.5 g, more preferably 0.1-1.0 g of the treatment agent composition of the present invention in one stroke. Is preferred. As the spray vial used in the present invention, for example, a Marem spray vial can be mentioned. As the trigger type sprayer, a pressure accumulation type trigger as disclosed in Japanese Utility Model Publication No. 4-37554 is particularly suitable from the viewpoint of spray uniformity. The spray characteristics, consuming liquid area 10～800Cm ² when sprayed from a distance 15cm to the object placed perpendicularly to the ground, the trigger preferably as a 100～800Cm ^2, more preferably 150～600Cm ² A sprayer is preferred. In the present invention, when the method (ii) is used, the content of the component (a) in the treatment agent composition of the present invention filled in the sprayer is 0.001 to 5.0 from the viewpoint of spray characteristics. % By mass is preferable, 0.005 to 3.0% by mass is more preferable, and 0.01 to 1.0% by mass is still more preferable. The trigger type sprayer is used so that the component (a) is preferably 0.005 to 10.0 g, more preferably 0.05 to 5.0 g per 1 kg of the textile product. It is preferable to air dry after the spray treatment.

  In the textile product treating agent composition of the present invention, hydrolysis proceeds at a certain rate on the textile product, and an appropriate amount of the scent component can be released. As a result, the fiber product treated with the fiber product treating agent composition of the present invention is stored and stored in a chiffon etc., and is used for the next time it is used or worn, that is, within 4 days, or within 1 week. Even after passing through, the optimum scent intensity can be maintained. In order to obtain a satisfactory scent over the period as described above, it is preferable that the retention rate of the scent component of the fiber product treating agent composition is in the range of 10% to 90% after the lapse of the period. The retention rate of the scent component means a relative value when the amount of the scent component present on the fiber product immediately after being treated with the textile product treating agent composition of the present invention is 100%. In addition, the scent component in this case means both the scent component released in the component (a) and the hydrolysis of the component (a).

  Each component used in the examples and comparative examples is summarized below.

<(A) component>
(A-1): Silicon compound obtained in Synthesis Example 1 below (a-2): Silicon compound obtained in Synthesis Example 2 below <Component (a ′) (Comparative product of Component (a))>
(A′-1): 3,7-dimethyl-trans-2,6-octadien-1-ol
(A′-2): Phenylethyl alcohol <(b) component>
(B-1): Quaternary ammonium salt obtained in Synthesis Example 3 below (b-2): Quaternary ammonium salt obtained in Synthesis Example 4 below (b-3): Quaternary ammonium obtained in Synthesis Example 5 below Salt (b-4): Quaternary ammonium salt obtained in Synthesis Example 6 (b-5): Dimethyldioctadecylammonium chloride (manufactured by Wako Pure Chemical Industries, Ltd., distributor code 043-22091)
<(C) component>
(C-1): An average of 12 moles of EO added to a primary alcohol having 12 carbon atoms
<(D) component>
(D-1): Stearic acid <(e) component>
(E-1): Calcium chloride <(f) component>
(F-1): Cured beef tallow fatty acid monoglyceride <(g) component>
(G-1): Ethanol <Other components>
LAS: C10-14 linear alkylbenzene sulfonic acid
Synthesis Example 1: Synthesis of silicon compound (a-1) In a 200 mL four-necked flask, 27.08 g (0.13 mol) of tetraethoxysilane, 3,7-dimethyl-trans-2,6-octadien-1-ol 72 0.5 g (0.47 mol), 0.485 mL of a 2.8% sodium methoxide methanol solution was added, and the mixture was stirred at 110 to 120 ° C. for 2 hours while distilling ethanol under a nitrogen stream. After 2 hours, the pressure in the tank was gradually lowered to 8 kPa, and the mixture was further stirred at 117 to 120 ° C. for 4 hours while distilling ethanol. After 4 hours, cooling and depressurization were canceled, followed by filtration to obtain a silicon compound (a-1). The ratio of 3,7-dimethyl-trans-2,6-octadien-1-yloxy group in all substituents of the obtained silicon compound was analyzed by ¹ H-NMR measurement. The results are shown in Table 1.

Synthesis Example 2: Synthesis of silicon compound (a-2) In a 200 mL four-necked flask, 41.68 g (0.20 mol) of tetraethoxysilane, 87.98 g (0.72 mol) of 2-phenylethanol, 2.8% sodium 1.85 mL of a methoxide methanol solution was added, and the mixture was stirred at 112 ° C. to 118 ° C. for about 2 hours while distilling ethanol under a nitrogen stream. After 2 hours, the pressure in the tank was gradually lowered to 8 kPa, and the mixture was further stirred for 3 hours while distilling ethanol. After 3 hours, cooling and depressurization were canceled, followed by filtration to obtain a silicon compound (a-2). The ratio of 2-phenylethoxy group in all the substituents of the obtained silicon compound was analyzed by ¹ H-NMR measurement. The results are shown in Table 1.

Synthesis Example 3 Synthesis of Cationic Surfactant (b-1) Myristic acid and N- (3-aminopropyl) -N- (2-hydroxyethyl) -N-methylamine were mixed to give 1.9 / 1. The mixture was mixed at a molar ratio, and dehydration condensation was performed according to a conventional method. The acid value of the reaction product was measured over time, and when the acid value reached 9, the reaction was stopped to obtain a condensate. The total amine value of this condensate was measured. Next, 8% by mass of ethanol was added to the condensate, and 0.98 equivalents of methyl chloride was used with respect to the amine equivalents determined from the total amine value of the condensate. After that, the mixture was diluted with ethanol so that the solid content was 90% by mass to obtain a quaternary ammonium salt mixture containing the target compound. The content of N- (3-alkanoylaminopropyl) -N- (2-alkanoyloxyethyl) -N, N-dimethylammonium chloride in the solid content excluding ethanol in this composition was determined by high performance liquid chromatography. As a result, it was 86 mass%. The alkanoyl group is a residue obtained by removing a hydroxyl group from a fatty acid used as a raw material.

Synthesis Example 4: Synthesis of Cationic Surfactant (b-2) Palmitic acid was used as a raw material fatty acid, and (b-2) was synthesized in the same manner as in Synthesis Example 3. The content of N- (3-alkanoylaminopropyl) -N- (2-alkanoyloxyethyl) -N, N-dimethylammonium chloride as component (b-2) in the reaction-terminated composition was 86% by mass. Met.

Synthesis Example 5: Synthesis of Cationic Surfactant (b-3) (b-3) was synthesized in the same manner as in Synthesis Example 3 using stearic acid as a raw material fatty acid. The content of N- (3-alkanoylaminopropyl) -N- (2-alkanoyloxyethyl) -N, N-dimethylammonium chloride as component (b-3) in the reaction-terminated composition was 86% by mass. Met.

Synthesis Example 6 Synthesis of Cationic Surfactant (b-4) (b-4) was synthesized in the same manner as in Synthesis Example 3 using behenic acid as a raw material fatty acid. The content of N- (3-alkanoylaminopropyl) -N- (2-alkanoyloxyethyl) -N, N-dimethylammonium chloride as component (b-4) in the reaction-terminated composition was 86% by mass. Met.

Examples 1-12 and Comparative Examples 1-6
Using the components shown in Table 2, a fiber product treating agent composition having the composition shown in Table 2 was prepared by the following method. In addition, (b-1)-(b-4) in Table 2 composition table | surface shows the compounding rate of each component itself calculated by the purity of each component. The obtained fiber product treating agent composition was processed into a fiber product by the following treatment method 1, the fragrance strength was evaluated by the following method, and the retention rate of the fragrance component was determined. Moreover, the following method evaluated the external appearance of the obtained textile product processing agent composition. The results are shown in Table 2.

<Method for preparing textile product treating agent composition>
50 mL screw tube No. 7 (manufactured by Maruemu Co., Ltd.) is charged with 90% of the amount of ion-exchanged water and a stirrer piece of φ8 mm × 30 mm necessary for the finished mass of the fiber product treating agent composition to be 20 g. The temperature was raised to 65 ° C. to 70 ° C. in a bath (300 rpm). Next, (b) component was mix | blended and it heat-dissolved in the state which closed the cap. After the temperature was lowered to 50 ° C., the component (a) was blended and stirred at 50 ° C. for 5 minutes with the cap closed again. The fiber product treating agent composition was obtained by cooling this with stirring to 25 ° C. In addition, when blending component (c), the necessary amount is blended in advance with ion-exchanged water, and when blending component (e), blending is performed after blending component (b) and heating and dissolving. .

<Treatment method 1 with a textile product treating agent composition>
(1) Preparation method of pre-treated cotton knitted fabric In advance, using a commercially available weak alkaline detergent (attack manufactured by Kao Corporation), cotton knitted fabric (made by Tanigami Shoten Co., Ltd., without syltech processing, 50 cm × 10 sheets were cut 5 times with Hitachi fully automatic washing machine NW-6CY and dried indoors to remove excess chemicals (detergent concentration 0.0667 mass%, tap water 47L used, water temperature 20 C, wash 10 minutes, rinse twice).
Further, it was cut into a 3 cm square and used as a test cloth.

(2) Treatment of composition on cotton knitted fabric 4 g of ion-exchanged water and 1 g of a textile product treating agent composition were placed in a Marem spray vial (No. 6). A stirrer piece (φ4 mm × 10 mm) was placed therein, and stirred at 200 rpm for 5 minutes using a magnetic stirrer. This was sprayed with 0.15 g per one test cloth using a Marem spray vial (No. 6) and dried at room temperature for 1 hour. 7 (made by TOP), No. The product was stored at 25 ° C. and 60% RH with a cover for 7 (made by TOP) covered.

<Evaluation of fragrance strength>
The same panelists evaluated the scent intensity of each cotton knitted fabric treated by the above-mentioned treatment method 1 immediately after spraying, after 1 day and after 4 days according to the following criteria. The average score of 10 panelists (5 women in their 20s and 5 men in their 20s) was determined.

Evaluation criteria:
0 ... No scent is felt 1 ... Slight scent is felt 2 ... Slightly strong 3 ... Slightly strong scent is felt <Retention rate of scent components>
20 mL of a stoppered test tube (manufactured by ASONE, centrifuge tube S-20), 5 mL of methanol (manufactured by Wako Pure Chemical Industries), 3 mL of distilled water (manufactured by Wako Pure Chemical Industries) and 5 mol / L sodium hydroxide aqueous solution (manufactured by Wako Pure Chemical Industries) 1 ml was added and stirred well. A cotton knitted fabric treated by the above treatment method 1 was put into this, and after stirring well, a high vacuum grease (Dow Grease manufactured by Toray Dow Corning Co., Ltd.) was applied to the sliding part of the stopper to improve airtightness. The plug was closed with a silicone tape. This was allowed to stand in an 80 ° C. hot water bath for 1 hour, cooled to room temperature (25 ° C.), and then an aqueous hydrochloric acid solution (made by Kishida Chemical) diluted to 5 mol / L with ion-exchanged water was added. It adjusted so that it might become 4-8. In addition, when insoluble matter was produced, it filtered using a disposable filter (Advantech Toyo Co., Ltd. DISMIC 25CS080AN). Subsequently, the scent component was quantified using the following high performance liquid chromatography apparatus and a calibration curve, and the retention rate of the scent component after 1 day and 4 days after the spray treatment, with the amount immediately after spraying as 100, as shown in the following formula: (%) Was calculated.

High performance liquid chromatography equipment: HITACH ELITE LaChrom
UV detector L-2400
Column Even L-2300
Pump L-2130
Autosampler L-2200
Column: L-Column ODS Waters (manufactured by Chemicals Research Institute, 4.6 × 150 mm)
Column temperature: 40 ° C
Eluent: Distilled water (Wako Pure Chemical Industries) / acetonitrile (Wako Pure Chemical Industries) = 60/40 (volume ratio)
Flow rate: 1 mL / min Detector: UV (220 nm)
Calibration curve: A solution obtained by diluting (a′-1) and (a′-2) with acetonitrile to a concentration of 0.5 to 500 mg / L was prepared by quantifying with the above-mentioned high performance liquid chromatography apparatus. thing.

<Appearance evaluation>
Whether the (a) component and the (b) component in the treating agent composition for textile products are uniformly dispersed was evaluated visually according to the following criteria.

Evaluation criteria:
○: After blending, component (a) and component (b) are uniformly dispersed Δ: After blending, component (a) and component (b) are dispersed almost evenly ×: Immediately after blending (A) component and (b) component are separated <Scent intensity and appearance evaluation>
The fragrance strength of each cotton knitted fabric treated by the treatment method 1 was evaluated by the method described above. As a result, the scores of Comparative Examples 3, 5, and 6 were 1.5 or less, whereas in Examples 1 to 12, the score was 2 or more, and sufficient fragrance strength was maintained.

  In Comparative Example 1, the viscosity in the composition was high, and the dispersion stability was impaired. Therefore, a textile product could not be processed using the composition of this comparative example. Furthermore, Comparative Examples 2 and 4 were unable to uniformly disperse the a-1 component or the a-2 component in the composition, and even when vigorously stirred, the dispersion stability was immediately impaired. Therefore, even if the textile product was processed using the composition of this comparative example, a region where the a-1 component or the a-2 component was not attached was generated, and the effect of the present invention was not sufficiently exhibited. .

  The products of the present invention (Examples 1 to 12) developed good fragrance strength on the first and fourth days after the treatment, but were compared products (comparative examples) using a general fragrance component instead of the component (a). In 5 and 6), although a very strong scent was developed immediately after the treatment, almost no scent remained on the first and fourth days after the treatment. Further, in the comparative product (Comparative Example 3) using the component (c) instead of the component (b), the stability of the component (a) on the fiber product can be improved, but it is stabilized on the contrary. Too much fragrance was weak.

Example 13 and Comparative Example 7
The textile product treating agent composition was treated into a textile product by the following treatment method 2, and the fragrance strength was evaluated.

<Treatment method 2 with a textile product treating agent composition>
(1) Preparation method of pretreated cotton towel In advance, a new thin towel (made by Takei towel, 100% cotton, # 220) and a new article using a commercially available weak alkaline detergent (attack made by Kao Corporation) No. 10 thick towel (manufactured by UNIQLO Co., Ltd., 100% cotton) was washed five times with Hitachi fully automatic washing machine NW-6CY and dried indoors to remove excess drug (detergent concentration 0.0667% by mass) , Using 47 L of tap water, water temperature 20 ° C., washing 10 minutes, rinsing twice).
(2) Treatment of composition on cotton towels Two types of these towels and three underwears are prepared, and underwear (100% cotton) is added as a mass-adjustment cloth, and a total of 3.5 kg of clothing is fully automatic. Using a washing machine (NA-F60E manufactured by Matsushita, amount of water 47L), washing was performed under standard use conditions. Compare 33.7g of detergent (attack manufactured by Kao Corporation) to the automatic loading port of a fully automatic washing machine, and in Example 13, compare 7g of the product of the present invention (textile treatment agent composition of Example 6). In Example 7, 7 g of a comparative product (a textile product treating agent composition of Comparative Example 3) was used by being put in an automatic charging port of a washing machine. In addition, since the textile product treating agent composition was put in the softener charging port, the fiber is treated in the rinsing step after washing. After the washing was completed, the evaluation towel was taken out, hung on a clothesline, allowed to dry naturally, and stored for 4 days.

<Evaluation of fragrance strength>
The fragrance intensity of the towel treated by the above treatment method 2 was evaluated by the method described above. As a result, while the score of Comparative Example 7 was 0.4, in Example 13, it was 2.4, and sufficient fragrance intensity was maintained.

Claims (5)

A fiber product treating agent composition comprising the following component (a) and component (b) in a mass ratio of (a) component / (b) component = 1/10 to 10/1.
Component (a): a compound represented by the general formula (1-1) or (1-2)

[In the formula, R ¹ is an aliphatic hydrocarbon group having 1 to 22 carbon atoms which may have a phenyl group, a hydroxyl group or an alkoxy group as a substituent; R ² is a hydrocarbon group having 6 to 22 carbon atoms; m is a number of 1 to 15 indicating an average value. A plurality of R ² may be the same or different. ]
Component (b): a tertiary amine having at least one hydrocarbon group having 12 to 28 carbon atoms which may be separated by an ester group or an amide group in the molecule, an acid salt thereof or a quaternized product thereof At least one cationic surfactant The fiber product treating agent composition according to claim 1, wherein the component (b) is at least one selected from a tertiary amine represented by the general formula (2), an acid salt thereof or a quaternized product thereof.

[In the formula, R ^a1 group is a hydrocarbon group having a total carbon number of 12 to 28 which may be divided by an ester group or an amide group, and R ^a2 group and R ^a3 group are each independently R ^a1 group, carbon It is a group selected from a C 1-3 alkyl group and a C 1-3 hydroxyalkyl group. ]   A textile product processing method comprising treating the textile product treating agent composition according to claim 1 or 2 into a textile product.   The method for treating a textile product according to claim 3, wherein the textile product treating agent composition is added to the rinsing water at the rinsing stage in the textile product washing step.   The method for treating a textile product according to claim 3, wherein the textile product treating agent composition is sprayed onto the washed textile product.