JP4368785B2 - Liquid softener composition - Google Patents

Description

  The present invention relates to a liquid softener composition.

A softener composition containing a dilong chain hydrocarbon-type quaternary ammonium compound having an unsaturated bond in the molecule is already known (Patent Document 1). Moreover, the softening agent composition containing a monoalkyl type | mold tertiary amine, its acid salt, or its quaternization thing is also known (patent document 2). Further, these publications describe that malodor is reduced by using two kinds of ammonium compounds in combination. Furthermore, the softening agent composition containing 2 types of ammonium salts is described in patent document 3 and patent document 4.
Special table 2004-522010 gazette JP 2002-339249 A JP 2001-164466 A JP 2000-328454 A

  The softener composition is generally used for the purpose of improving the texture of clothing and the like, but recently, interest in odor has increased, and a technique for imparting a deodorizing effect to the softener composition has been studied.

  Patent Document 1 discloses a technique in which a quaternary ammonium compound having a specific iodine value and an antibacterial quaternary ammonium salt are used in combination. These techniques are techniques for deodorizing odors derived from microorganisms such as raw dry odors, but there is an important problem that odors that are thought to be derived from unsaturated bonds are generated in clothing.

  Patent Document 2 discloses a technique in which a monoalkyl type tertiary amine or quaternary salt and a dialkyl type quaternary ammonium compound are used in combination. According to this publication, it is possible to provide an excellent technique for deodorizing odors derived from bacteria, and there is no problem with the generation of off-flavors that are thought to be derived from unsaturated bonds. However, in the compositions described in the examples of the publication, for example, the effect of deodorizing odors attached to clothing (hereinafter referred to as “external environmental odor”) such as tobacco odor and grilled meat odor is small, and the improvement thereof is It is strongly demanded.

  On the other hand, Patent Document 3 and Patent Document 4 have a monoalkyl quaternary ammonium compound having one alkyl group separated by an ester group and / or an amide group and one or more alkyl groups separated by an ester group. A technique using a dialkyl quaternary ammonium compound in combination is described.

  However, these are technologies for making the softener composition transparent, and by using a dialkyl quaternary ammonium compound having a specific alkenyl group and a specific monoalkyl quaternary ammonium compound in combination, the generation of off-flavors can be eliminated. There is no mention of deodorizing external environmental odors.

  Therefore, the subject of this invention is providing the liquid softening agent composition which does not have the problem of generation | occurrence | production of a strange odor when processing clothing, and has the deodorizing effect of a high external environmental odor.

  As a means for solving the problems, the present invention contains (a) a compound of the following general formulas (1-1) to (1-3), (b) a compound of the following general formula (2), and (c) water, A liquid softener composition in which (a) component is 3 to 30% by mass, (b) component is 0.3 to 15% by mass, and (a) component / (b) component mass ratio is 0.5 to 80. provide.

[Where,
R ¹¹ is an alkyl group or alkenyl group having 15 to 20 carbon atoms,
R ¹² is an alkylene group having 1 to 6 carbon atoms,
R ¹³ is an alkyl group having 1 to 3 carbon atoms or a hydroxyalkyl group,
R ¹⁴ represents an alkyl group having 1 to 3 carbon atoms or a hydroxyalkyl group,
R ¹⁵ is a hydrogen atom, an alkyl group having 1 to 3 carbon atoms or a hydroxyalkyl group,
R ¹⁶ is an alkyl group or alkenyl group having 16 to 20 carbon atoms,
R ¹⁷ is an alkylene group having 1 to 6 carbon atoms,
R ¹⁸ is an alkyl group or alkenyl group having 16 to 20 carbon atoms,
R ¹⁹ is an alkylene group having 1 to 6 carbon atoms,
The alkenyl group is 50 to 100 mol% based on the total number of moles of R ¹¹ , R ¹⁶ and R ¹⁸ ;
A and B are groups selected from —COO—, —OCO—, —CONH— and —NHCO—, a and b are each a number of 0 or 1, and X ⁻ is an anionic group. Of each R in the general formulas (1-1) to (1-3), those having the same meaning may be the same or different. ]

[Where,
R ²¹ is an alkyl group or alkenyl group having 15 to 22 carbon atoms,
D is a group selected from -CONH- and -NHCO-,
R ²² is an alkylene group having 1 to 6 carbon atoms,
R ²³ and R ²⁴ are an alkyl group having 1 to 3 carbon atoms or a hydroxyalkyl group,
R ²⁵ is a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, or a hydroxyalkyl group. ]

  The liquid softener composition of the present invention can give an excellent softening effect when treating textile products such as clothing (especially textile products used at home), and has an off-flavor caused by the components contained in the composition. There is no problem of generation, and it has a high deodorizing effect on the external environmental odor.

<(A) component>
The component (a) of the present invention comprises (a1) a compound of the general formula (1-1), (a2) a compound of the general formula (1-2), and (a3) a mixture of the compounds of the general formula (1-3). It is.

[Where,
R ¹¹ is an alkyl group having 15 to 20 carbon atoms or an alkenyl group having 15 to 20 carbon atoms,
R ¹² is an alkylene group having 1 to 6 carbon atoms,
R ¹³ is an alkyl group having 1 to 3 carbon atoms or a hydroxyalkyl group having 1 to 3 carbon atoms,
R ¹⁴ is an alkyl group having 1 to 3 carbon atoms or a hydroxyalkyl group having 1 to 3 carbon atoms,
R ¹⁵ is a hydrogen atom, an alkyl group having 1 to 3 carbon atoms or a hydroxyalkyl group having 1 to 3 carbon atoms, and R ¹⁶ is an alkyl group having 16 to 20 carbon atoms or an alkenyl group having 16 to 20 carbon atoms,
R ¹⁷ is an alkylene group having 1 to 6 carbon atoms, R ¹⁸ is an alkyl group having 16 to 20 carbon atoms or an alkenyl group having 16 to 20 carbon atoms, and R ¹⁹ is an alkylene group having 1 to 6 carbon atoms,
The alkenyl group is 50 to 100 mol% based on the total number of moles of R ¹¹ , R ¹⁶ and R ¹⁸ ;
A and B are groups selected from —COO—, —OCO—, —CONH— and —NHCO—, a and b are each a number of 0 or 1, and X ⁻ is an anionic group. Of each R in the general formulas (1-1) to (1-3), those having the same meaning may be the same or different. For example, although R ¹³ and R ¹⁴ have the same meaning, It may be different.

In the general formula (1-1), R ¹³ is preferably a hydroxyethyl group. A and B are preferably —COO—, and a and b are preferably the number of 1. R ¹¹ , R ¹⁶ and R ¹⁸ are preferably alkyl groups or alkenyl groups having 15 to 17 carbon atoms.

Moreover, with respect to the total number of moles of R ¹¹ , R ¹⁶ and R ¹⁸ (when only R ¹¹ is included, when two of R ¹¹ and R ¹⁶ are included, or three of R ¹¹ , R ¹⁶ and R ¹⁸ are Each having a alkenyl group of 50 to 100 mol%, preferably 85 to 99 mol%, more preferably 87 to 99 mol%, still more preferably 90 to 99 mol%, and particularly preferably 95 to 99 mol%. Mol%. In addition, since an alkenyl group having two or more carbon-carbon unsaturated bonds tends to promote the generation of a strange odor, it has the same meaning as described above with respect to the total number of moles of R ¹¹ , R ¹⁶ and R ¹⁸ . ), Preferably 10 mol% or less, more preferably 8 mol% or less, still more preferably 5 mol% or less, particularly preferably 3 mol% or less.

  In the general formula (1), a compound in which A and B are —COO— is a monoalkyl dialkanolamine (preferably methyldiethanolamine) corresponding to a fatty acid having the above preferred alkyl and alkenyl composition, or a trialkanolamine (preferably trialkanolamine). Dehydration esterification reaction with ethanolamine) or fatty acid lower alkyl (C1-3) ester having a preferred alkyl composition and monoalkyl dialkanolamine (preferably methyldiethanolamine), or trialkanolamine (preferably triethanolamine) ) Produced by performing a quaternization reaction using an alkylating agent selected from dialkyl sulfuric acid (1 to 3 carbon atoms) and halogenated alkyl (1 to 3 carbon atoms). can do.

  The fatty acid or fatty acid ester is preferably a fatty acid composition obtained by saponifying fat selected from beef tallow, palm oil, sunflower oil, soybean oil, rapeseed oil, safflower oil, cottonseed oil, corn oil, olive oil, The thing of the fatty acid composition obtained from beef tallow, palm oil, and a sunflower oil from the point of transparency and the deodorizing effect of an external environmental odor is favorable.

  Further, since these contain a large amount of alkenyl groups having two or more carbon-carbon unsaturated bonds, for example, crystallization as described in JP-A-4-306296 or JP-A-6-41578 The ratio of fatty acids containing two or more carbon-carbon unsaturated bonds can be obtained by performing distillation under reduced pressure as described in JP-A-8-99036 or by performing a selective hydrogenation reaction described in JP-A-8-99036. It can be manufactured by a controlling method or the like.

  In addition, when tallow fatty acid or a selective hydrogenation reaction is performed, a mixture of geometric isomers of unsaturated bonds is formed. In the present invention, cis / trans is 25/75 to 100/0, preferably 50 / 50-95 / 5 (molar ratio) is preferable.

  The ratio of fatty acid or fatty acid ester to monomethyl dialkanolamine (preferably methyldiethanolamine) or trialkanolamine (preferably triethanolamine) in the esterification reaction or transesterification reaction is 1.4: 1 to 2.2: 1 is preferable, and 1.6: 1 to 2.0: 1 is more preferable.

In the present invention, when a trialkanolamine (preferably triethanolamine) and a fatty acid or a fatty acid ester are esterified or transesterified and subsequently subjected to a quaternization reaction, (a1) of the general formula (1-1) Compound in which R ¹³ and R ¹⁴ are hydroxyalkyl groups (preferably hydroxyethyl groups) in the compound, (a2) In the compound of general formula (1-2), R ¹⁴ is a hydroxyalkyl group (preferably hydroxyethyl groups) A mixture of the compound and (a3) a compound of the general formula (1-3) in which R ¹⁵ is an alkyl group having 1 to 3 carbon atoms is obtained.

  In the present invention, the component (a1) is preferably 10 to 30% by mass, more preferably 12 to 28% by mass in the component (a) from the viewpoint of the softening effect and storage stability, and the effect of deodorizing the external environmental odor. %, Particularly preferably 15-25% by mass, component (a2) is preferably 35-50% by mass, more preferably 40-50% by mass, particularly preferably 42-48% by mass, and component (a3) is preferably 20%. It is suitable that it is a mixture containing ˜50 mass%, more preferably 20 to 45 mass%, particularly preferably 25 to 40 mass%.

<(B) component>
The component (b) of the present invention is a compound of the following general formula (2).

[Where,
R ²¹ is an alkyl group having 15 to 22 carbon atoms or an alkenyl group having 15 to 22 carbon atoms,
D is a group selected from -CONH- and -NHCO-,
R ²² is an alkylene group having 1 to 6 carbon atoms,
R ²³ and R ²⁴ are an alkyl group having 1 to 3 carbon atoms or a hydroxyalkyl group having 1 to 3 carbon atoms,
R ²⁵ is a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, or a hydroxyalkyl group having 1 to 3 carbon atoms.

In the general formula (2), R ²¹ is preferably an alkyl group having 15 to 22 carbon atoms. R ²¹ may contain an alkenyl group having 16 to 22 carbon atoms, but the content of the alkenyl group is 50 mol% or less, preferably 25 mol% or less, particularly preferably 5 mol, based on the total R ²¹ . % Or less is preferred. D is preferably -CONH-, and R ²² is particularly preferably a propylene group. R ²³ and R ²⁴ are preferably a methyl group or an ethyl group, and R ²⁵ is preferably a hydrogen atom.

In the general formula (2), a compound in which D is —CONH— is a corresponding dialkylaminoalkylamine (preferably dimethylaminopropylamine) and R ²¹ -COOR ²⁶ (R ²⁶ is a hydrogen atom or an alkyl having 1 to 3 carbon atoms). It can be obtained by carrying out an amidation reaction with a group. The compound in which R ²⁵ is a hydrogen atom is an inorganic acid selected from hydrochloric acid, sulfuric acid and phosphoric acid, citric acid, malic acid, lactic acid, succinic acid, glycolic acid, a fatty acid having 1 to 12 carbon atoms, carbon after amidation reaction It can obtain by neutralizing with the organic acid chosen from the benzenesulfonic acid which the alkyl group of several 1-3 may substitute 1-3.

When R ²⁵ is an alkyl group having 1 to 3 carbon atoms, it can be obtained by alkylating with an alkylating agent selected from dialkyl sulfuric acid and alkyl halide. Further, when R ²⁵ is a hydroxyalkyl group, it can be obtained by neutralizing with the above inorganic acid or organic acid and then alkylating with ethylene oxide or propylene oxide.

<(C) component>
The component (c) of the present invention is water, and water from which hardness components such as calcium and magnesium and heavy metals such as iron, which are present in trace amounts, are preferably removed, and ion-exchanged water or distilled water can be used. A small amount of chlorine may be contained for the purpose of sterilizing or sterilizing water.

<Other ingredients>
Although it is optional in the present invention, it is preferable to contain an anionic surfactant (hereinafter referred to as component (d)) for the purpose of improving the softening effect and the effect of deodorizing the external environmental odor.

Component (d) is a saturated or unsaturated fatty acid having 14 to 22 carbon atoms, preferably 16 to 18 carbon atoms, or an alkali metal or alkaline earth metal salt thereof (hereinafter referred to as (d1) component), or 10 to 10 carbon atoms. 36, preferably an anionic surfactant having an alkyl group or an alkenyl group having 16 to 28 carbon atoms and having a —SO ₃ M group and / or —OSO ₃ M group [M: counter ion] [hereinafter (d2) Component)] is preferred.

  Specific examples of the component (d1) include fatty acids selected from myristic acid, palmitic acid, stearic acid, oleic acid, and palmitoleic acid, and salts thereof, and stearic acid and oleic acid are particularly preferable.

  As the component (d2), alkylbenzene sulfonic acid having the above carbon number, alkyl (or alkenyl) sulfate, polyoxyalkylene alkyl (or alkenyl) ether sulfate, olefin sulfonic acid, alkane sulfonic acid, α-sulfo fatty acid, α Sulfo fatty acid esters and their salts are preferred.

  Among these, in particular, an alkyl (or alkenyl) sulfate having an alkyl group having 16 to 28 carbon atoms or an alkenyl group having 16 to 28 carbon atoms, an alkyl group having 16 to 28 carbon atoms or an alkenyl group, and an average addition of ethylene oxide. It is preferable to blend one or more selected from polyoxyethylene alkyl (or alkenyl) ether sulfates having 1 to 6 moles, preferably 1 to 4 and particularly preferably 1 to 3 moles and salts thereof. As the salt, sodium salt, potassium salt, and magnesium salt are preferable from the viewpoint of storage stability.

  In the present invention, for the purpose of improving storage stability, it is preferable to contain a nonionic surfactant as the component (e), and it may contain a saturated or unsaturated fatty acid having 8 to 22 carbon atoms and ethylene oxide. One or more selected from ester compounds (e1) with polyhydric alcohols and polyoxyalkylene alkyl ethers (e2) are preferred.

  Examples of the component (e1) include triglyceride, diglyceride, monoglyceride, mono, di or triester of pentaerythritol, and sorbitan ester. As the component (e2), a compound represented by the following general formula (3) is preferable.

R ³¹ —O— (FO) _d —OH (3)
[In the formula, R ³¹ is an alkyl group or alkenyl group having 8 to 18 carbon atoms, F is an ethylene group or propylene group, d is an average addition mole number, and is a number exceeding 21 and less than 40] .

R ³¹ is preferably 12 to 14, and F is preferably an ethylene group. Furthermore, d is preferably 22 to 35, more preferably 22 to 30, and particularly preferably 22 to 28.

  The composition of the present invention preferably contains a metal sequestering agent as the component (f) for the purpose of suppressing the generation of off-flavors.

As a sequestering agent,
i) polycarboxylic acid compounds such as citric acid, malic acid, succinic acid,
ii) aminopolycarboxylic acids such as ethylenediaminetetraacetic acid, diethylenetriaminepentaacetic acid, hydroxyethyliminodiacetic acid,
iii) One or more selected from phosphonic acids such as 1-hydroxyethylidene-1,1-diphosphonic acid and ethylenediaminetetramethylphosphonic acid are preferred.

  The component (f) of the present invention is particularly preferably ethylenediaminetetraacetic acid and / or 1-hydroxyethylidene-1,1-diphosphonic acid.

  The composition of the present invention can contain an inorganic salt as the component (g). As the inorganic salt, sodium sulfate, sodium chloride, calcium chloride, and magnesium chloride are preferable from the viewpoint of storage stability. However, although surfactants such as fatty acid salts include sodium salts and potassium salts, inorganic salts mixed into the composition by using such surfactants are not subject to the above restrictions.

  The composition of the present invention preferably contains a solvent as the component (h). Specifically, it is a solvent selected from ethanol, isopropanol, glycerin, ethylene glycol, propylene glycol, hexylene glycol, phenoxyethanol, diethylene glycol monophenyl ether, triethylene glycol monophenyl ether, particularly ethanol, phenoxyethanol, diethylene glycol monophenyl ether. Triethylene glycol monophenyl ether is preferred from the point of smell.

  The composition of the present invention usually uses a fragrance (particularly preferably a combination of the fragrance components shown in components (c) and (d) described in JP-A-8-113871) incorporated in a softener. Also good. The composition of the present invention may contain a water-soluble dye, preferably a compound shown as component (b) in JP-A No. 11-256474 or component (c) in JP-A No. 2004-60079. The compounds described as are preferred.

<Liquid softener composition>
The component (a) in the composition of the present invention is known as a component that exhibits an excellent softening effect when it is blended with a softening agent to treat clothing, but is a softening agent containing the component (a). When clothing is processed (usually used in combination with a cleaning agent and further dried), it is derived from laundry (a) component [especially when the compound of general formula (1) contains an unsaturated bond] There is a problem that an unpleasant odor occurs, and this bad odor is prominently expressed when the clothes after washing are sun-dried. Therefore, in the composition of the present invention, by combining the components (a) and (b) at a specific ratio, and more preferably by combining the component (d), the excellent softening effect of the component (a) is imparted. Therefore, there is no problem of generation of a strange odor due to the components contained in the composition, and a high deodorizing effect of the external environmental odor is exhibited.

  The composition of the present invention can be obtained by mixing the above-described components so as to have the following contents.

  (A) Content of a component is 3-30 mass%, Preferably it is 4-28 mass%, Most preferably, it is 5-25 mass%.

  (B) Content of a component is 0.3-15 mass%, Preferably it is 1-15 mass%, Most preferably, it is 3-10 mass%.

  Further, the component (a) / component (b) is contained in a mass ratio of 0.5 to 80, preferably 0.5 to 30, more preferably 0.8 to 10, and particularly preferably 1 to 3.

  The component (d) is optional but improves the softening effect and is preferably contained from the point of deodorizing the external environmental odor, and the content in the composition is preferably 0.5 to 20% by mass. More preferably, it is 1-15 mass%, Most preferably, it is 2-10 mass%. Moreover, (a) component / (d1) component is 3-100 by mass ratio, Preferably it is 5-80, More preferably, it is 10-50, Most preferably, it is 15-30, (b) component / (d2) component is mass. The ratio is preferably 0.5 to 100, preferably 1 to 50, more preferably 1 to 30, and particularly preferably 1 to 10 in view of suppressing the external environmental odor.

  The component (e) is an important component from the viewpoint of storage stability, and the content in the composition is preferably 0.5 to 10% by mass, more preferably 0.8 to 8% by mass, and particularly preferably 1 It is -8 mass%. In particular, the component (e2) is important, and the content in the composition is preferably 0.5 to 10% by mass, more preferably 0.8 to 8% by mass, and particularly preferably 1 to 8% by mass.

  (F) It is preferable to contain a component from the point of the generation | occurrence | production suppression effect of a strange odor, and content in a composition becomes like this. Preferably it is 50-2000 ppm (mass basis), More preferably, it is 50-1000 ppm, Most preferably, it is 50-500 ppm. is there. The component (g) and the component (h) are also preferably contained from the viewpoint of storage stability, and the content in the composition is preferably 0.01 to 5% by mass, particularly preferably the component (g). 0.02-3 mass%, (h) component becomes like this. Preferably it is 0.5-25 mass%, Most preferably, it is 2-20 mass%.

  In the present invention, the above component is in the form of an aqueous solution in which the component (c) is dissolved or dispersed in water, and the component (c) is contained in the composition in an amount of 30 to 95% by mass, and further 50 to 85% by mass. Is preferred. Furthermore, it is preferable that the composition of this invention adjusts the pH in 25 degreeC of a composition to 1-7, 3-6.5, especially 4.6-6.5 from the point of storage stability. As the pH adjuster, inorganic acids such as hydrochloric acid, sulfuric acid, phosphoric acid, and component (f) can be used as acid agents, and sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, etc. can be used as alkali agents. it can.

<Compounding ingredients>
The components used in the examples are shown below.

Synthesis Example 1: (a-1) Synthesis sunflower oil iodine value was used as a raw material 90gI ₂ / 100g, with a fatty acid and triethanolamine acid value 201mgKOH / g, these reaction molar ratio 1.95 / 1 (fatty acid / Triethanolamine), followed by a dehydration condensation reaction according to a conventional method. Next, quaternization was performed according to a conventional method using 0.95 equivalent of dimethyl sulfate in the presence of an ethanol solvent with respect to the obtained condensate, and N-oleoyloxyethyl-N, N-dihydroxyethyl-N- 13% methylammonium methylsulfate, 37% N, N-dioleoyloxyethyl-N-hydroxyethyl-N-methylammonium methylsulfate, N, N, N-trioleoyloxyethyl-N-methylammonium methylsulfate A quaternary ammonium salt mixture containing 31% and 10% ethanol was obtained. (Hereinafter referred to as (a-1)). The remainder is a dehydrated condensate (amine) in which the quaternization reaction did not proceed, its acid salt and fatty acid.

Synthesis Example 2: (a-2) an iodine value 92gI ₂ / 100g for the synthesis tallowate as a raw material of, using a beef tallow fatty acid and triethanolamine acid value 199MgKOH / g, these to reaction molar ratio 1.85 / 1 In the same manner as in Synthesis Example 1, 15% N-oleoyloxyethyl-N, N-dihydroxyethyl-N-methylammonium methylsulfate, N, N-dioleoyloxyethyl-N-hydroxyethyl- A quaternary ammonium salt mixture containing 36% N-methylammonium methylsulfate, 27% N, N, N-trioleoyloxyethyl-N-methylammonium methylsulfate and 10% ethanol was obtained. (Hereinafter referred to as (a-2)). The remainder is a dehydrated condensate (amine) in which the quaternization reaction did not proceed, its acid salt and fatty acid.

Synthesis Example 3: (a-3) Synthesis sunflower oil iodine value was used as a raw material 90gI ₂ / 100g, with a fatty acid and triethanolamine acid value 201mgKOH / g, these reaction molar ratio 1.85 / 1 (fatty acid / Triethanolamine), followed by a dehydration condensation reaction according to a conventional method. Next, in the absence of a solvent, 0.95 equivalent of dimethylsulfuric acid was used for this condensate, and quaternization was performed according to a conventional method, followed by dilution with ethanol and N-oleoyloxyethyl-N, N- Dihydroxyethyl-N-methylammonium methylsulfate 17%, N, N-dioleoyloxyethyl-N-hydroxyethyl-N-methylammonium methylsulfate 40%, N, N, N-trioleoyloxyethyl-N -Methylammonium A quaternary ammonium salt mixture containing 28% methylsulfate and 10% ethanol was obtained. (Hereinafter referred to as (a-3)). The remainder is a dehydrated condensate (amine) in which the quaternization reaction did not proceed, its acid salt and fatty acid.

Synthesis Example 4: Synthesis of (b-1) By dehydration amidation reaction of mixed fatty acid obtained by mixing synthetic palmitic acid / stearic acid at 40/60 (weight ratio) and N, N-dimethyl-1,3-propanediamine (B-1) was synthesized. That is, 161 g of N, N-dimethyl-1,3-propanediamine and 273.3 g of mixed fatty acid were placed in a four-necked flask equipped with a stirrer, a thermometer, and a dehydrating tube, and the temperature was raised to 180 ° C. Next, the mixture was heated and stirred while distilling off the water generated at that temperature for about 5 hours. Thereafter, the mixture was cooled to 120 ° C., and the unreacted amine was distilled off under reduced pressure to obtain the desired N-alkanoylaminopropyl-N, N-dimethylamine (b-1).

Synthesis Example 5: Synthesis of (b-2) 100 g of the component (b-1) produced in Synthesis Example 4 and 300 g of ethanol were charged into an autoclave, heated to 100 ° C. with stirring after nitrogen substitution. Thereafter, 18 g of methyl chloride was injected with a press-in pump and reacted for 3 hours. After cooling, ethanol was distilled off under reduced pressure to obtain the desired N-alkanoylaminopropyl-N, N, N-trimethylammonium chloride (b-2).
(A-1): Reactant mainly containing N, N-dioleoyloxyethyl-N-hydroxyethyl-N-methylammonium methyl sulfate obtained in Synthesis Example 1 (a-2): In Synthesis Example 2 N, N-dioleoyloxyethyl-N-hydroxyethyl-N-methylammonium methylsulfate as a main component (a-3): N, N-dioleoyloxy obtained in Synthesis Example 3 Reaction product containing ethyl-N-hydroxyethyl-N-methylammonium methyl sulfate as a main component (b-1): Reaction containing N-alkanoylaminopropyl-N, N-dimethylamine as a main component obtained in Synthesis Example 4 Product (b-2): Reaction product containing N-alkanoylaminopropyl-N, N, N-trimethylammonium chloride as the main component obtained in Synthesis Example 5 (d-1): Olein (D-2): 2-decyl-1-tetradecyl sulfate sodium ester (e-1): polyoxyethylene (average condensation degree 20) sorbitan monolaurate (e-2): polyoxyethylene (average condensation degree 23) Lauryl ether (f-1): Ethylenediaminetetraacetic acid (g-1): Sodium sulfate (h-1): Ethanol (h-2): Phenoxyethanol (h-3): Polyoxyethylene (average condensation degree 3) monophenyl ether.

<Method for preparing softener composition>
Liquid softener compositions shown in Table 1 were prepared using the above components. A 300 mL beaker was charged with 95% of the amount of ion-exchanged water necessary for the finished mass of the softening agent composition to be 200 g, and the temperature was raised to 60 ° C. in a water bath. While stirring with a turbine-type stirring blade having three stirring blades each having a length of 2 cm (300 r / min), the required amounts of the components (a) and (e) were dissolved.

  Next, the mixture (40 degreeC) which mixed the required amount (b) component and (d) component previously was added. After stirring for 5 minutes, add component (c) and components (f) to (h) in sequence, and after stirring for another 5 minutes, adjust to the target pH with 35% aqueous hydrochloric acid and 48% aqueous sodium hydroxide. The amount of ion-exchanged water at 60 ° C. necessary to make the finished mass was added. Then, it stirred for 10 minutes, moved the beaker to the water bath containing 5 degreeC water, and cooled to 25 degreeC, stirring.

  The pH shown in Table 1 was measured after cooling (25 ° C.) using a pH meter D-52S and a pH electrode 6367-10D manufactured by Horiba, Ltd. Within the stated range, almost all the component (b-1) is present in the composition in the form of hydrochloride.

<Flexible processing method>
Five bath towels (100% cotton) were washed with a washing machine using a commercially available weakly alkaline detergent (attack from Kao Corp.) (Toshiba 2-tank washing machine VH-360S1, detergent concentration 0.0667% by mass, 30L tap water, water temperature 20 ° C, 10 minutes). Thereafter, the cleaning liquid was discharged, dehydrated for 3 minutes, poured 30 L of tap water, rinsed for 5 minutes, and dehydrated for 3 minutes after drainage. Thereafter, after 30 L of tap water was poured again, 7 ml of the softener composition shown in Table 1 was added and stirred for 5 minutes. After that, it was dehydrated and naturally dried in a place exposed to sunlight. About the clothing which repeated this operation 5 times, the softness | flexibility evaluation and the odor evaluation were performed by the following method.

(Flexibility evaluation)
The flexibility of the treated bath towel was determined by 10 panelists (10 men in their 30s) according to the following criteria, and the average score was obtained. An average score of 0 or more and less than 1 was judged as ◯, 1 or more and less than 1.5 as Δ, and 1.5 or more as x.
0 ... Finished very softly.
1 ... Finished softly.
2 ... Finished slightly soft.
3 ... Does not finish softly.

(External environmental odor evaluation)
The above-treated bath towel is hung in a sealed box with a hanger, and after the box is sealed, a smoker takes a cigarette (mild seven; manufactured by Nippon Tobacco Inc.) for about 5 minutes to smoke. Then, smoked for about 5 minutes, took out a bath towel from the box, and the intensity of the odor of the cigarettes after 1 hour was determined by 10 panelists (10 men in their 30s) according to the following criteria.

  The above-treated bath towel is hung in a sealed room and the meat is baked. Thereafter, the bath towel was taken out of the box, and the strength of the baked meat odor after being left for 1 hour was determined by 10 panelists (10 men in their 30s) according to the following criteria.

  Evaluation result of tobacco odor and grilled meat odor An average of 20 points was calculated, and the average score was 1 or more, less than 1.5, ○, 1.5 to less than 2, △, 2 or more × The results are shown in Table 1.

1… There is no odor of tobacco odor or yakiniku odor 2… Slight odor of tobacco odor or yakiniku odor 3… There is odor of tobacco odor or yakiniku odor

Claims (1)

(A) a mixture containing all of the compound of the following general formula (1-1) , the compound of the following general formula (1-2), and the compound of the following general formula (1-3);
(B) containing a compound and (c) water the following general formula (2),
The liquid softening agent composition whose (a) component is 3-30 mass%, (b) component is 0.3-15 mass%, and mass ratio of (a) component / (b) component is 0.8-10.

[Where,
R ¹¹ is an alkyl group or alkenyl group having 15 to 20 carbon atoms,
R ¹² is an alkylene group having 1 to 6 carbon atoms,
R ¹³ is hydroxycarboxylic alkyl group having 1 to 3 carbon atoms,
R ¹⁴ is hydroxycarboxylic alkyl group having 1 to 3 carbon atoms,
R ¹⁵ is a hydrogen atom, an alkyl group having 1 to 3 carbon atoms or a hydroxyalkyl group,
R ¹⁶ is an alkyl group or alkenyl group having 16 to 20 carbon atoms,
R ¹⁷ is an alkylene group having 1 to 6 carbon atoms,
R ¹⁸ is an alkyl group or alkenyl group having 16 to 20 carbon atoms,
R ¹⁹ is an alkylene group having 1 to 6 carbon atoms,
The alkenyl group is 50 to 100 mol% based on the total number of moles of R ¹¹ , R ¹⁶ and R ¹⁸ ;
A and B are groups selected from —COO—, —OCO—, —CONH— and —NHCO—, a and b are numbers of 1 , and X ⁻ is an anionic group. Of each R in the general formulas (1-1) to (1-3), those having the same meaning may be the same or different. ]

[Where,
R ²¹ is an alkyl group or alkenyl group having 15 to 22 carbon atoms,
D is a group selected from -CONH- and -NHCO-,
R ²² is an alkylene group having 1 to 6 carbon atoms,
R ²³ and R ²⁴ are an alkyl group having 1 to 3 carbon atoms or a hydroxyalkyl group,
R ²⁵ is a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, or a hydroxyalkyl group. ]