JPH0921068A - Liquid softening finish composition - Google Patents

Abstract

PURPOSE: To obtain a liquid softening finish composition capable of imparting excellent softness and elasticity to various fibers, having the biodegradability and gentle to the natural environment by blending specific quaternary ammonium salts as bases therein. CONSTITUTION: This liquid softening finish composition uses a quaternary ammonium salt represented by formula I [R<1> , R<2> and R<3> are each H or a 1-4C alkyl or alkenyl or a hydroxyalkyl; R<4> and R<5> are each a straight-chain or branched chain 8-36C alkyl or alkenyl which maybe substituted with OH; X<-> is an anion; (n) is a number of 1-6], preferably a compound represented by formula III [R<1> to R<3> , X<-> and (n) are same as described above] as a component (A) and a quaternary ammonium salt represented by formula II [R<1> to R<5> , X<-> and (n) are same as described above), preferably a compound represented by formula IV [R<1> to R<3> , X<-> and (n) are same as described above] as a component (B). Both the components (A) and (B) are blended so as to provide (99.999/0.001) to (80/20) weight ratio (A)/(B) expressed in terms of weight ratio and 3-40wt.% total content of both the components (A) and (B) in the composition.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION The present invention provides a liquid that imparts excellent flexibility and elasticity (puffiness) to various fibers, has excellent storage stability, is excellent in biodegradability, and is friendly to the natural environment. It relates to a softener composition.

[0002]

2. Description of the Related Art
Commercially available products as household softening agents generally have a composition containing di (cured tallow alkyl) dimethylammonium chloride as a main component. The reason for this is that this quaternary ammonium salt exerts a good softening effect on various fibers even in a small amount. However, although the quaternary ammonium salt has a high softening effect, it has a problem that it is hardly biodegraded when the residual substance after the treatment is released to the natural world such as a river, and adversely affects the organism.
As means for solving this, dimethyldi (alkanoyloxyethyl) ammonium chloride, methyldi (alkanoyloxyethyl) 2-hydroxyethylammonium methylsulfate and the like are marketed, but these are compared with the above quaternary ammonium salt. Thus, the biodegradability is improved, but the flexibility is still insufficient.

Therefore, an object of the present invention is to provide a liquid softener finishing composition which exhibits satisfactory performance in terms of softness and storage stability, is excellent in biodegradability, and is friendly to the natural environment. That is.

[0004]

DISCLOSURE OF THE INVENTION As a result of intensive studies, the present inventors have found that the above-mentioned problems can be solved by a liquid softener finishing composition containing a quaternary ammonium salt having a very specific structure. The present invention has been completed. That is, the present invention contains the following (A) component and (B) component, and the weight ratio of the (A) component and the (B) component is [(A) component] /
[(B) component] = 99.999 / 0.001 to 80/20, and
The present invention provides a liquid softener composition, wherein the total content of the component (A) and the component (B) in the composition is 3 to 40% by weight. Component (A): quaternary ammonium salt represented by general formula (I)

[0005]

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[Wherein R ¹ , R ² and R ^{3 are the} same or different and each is a hydrogen atom or a carbon number 1
4 shows an alkyl group, an alkenyl group or a hydroxyalkyl group. R ⁴ and R ^{5 are the} same or different and each represents a linear or branched alkyl group or alkenyl group having 8 to 36 carbon atoms, which may be substituted with a hydroxyl group. X ^-: represents an anion group. n: shows the number of 1-6. ] (B) component: quaternary ammonium salt represented by general formula (II)

[0007]

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[0008] ^{wherein, R 1, R 2, R} 3, R 4, R 5, X -, n: The meanings of the. Hereinafter, the present invention will be described in detail.

[Component (A)] In the present invention, a quaternary ammonium salt represented by the above general formula (I) (hereinafter abbreviated as quaternary ammonium salt (I)) is used as the component (A). It In the general formula (I), examples of the R ¹ , R ² and R ³ groups specifically include a hydrogen atom, methyl, ethyl, propyl, butyl and hydroxyethyl groups, with a methyl group being particularly preferred. . Specific examples of R ⁴ group and R ⁵ group include groups such as decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, hydroxyoctadecyl, and docosyl, preferably a straight or branched chain having 12 to 24 carbon atoms. Examples thereof include alkyl groups, more preferably octadecyl groups, hexadecyl groups, and mixed groups thereof, with octadecyl groups being particularly preferable. n represents a number of 1 to 6, preferably 1 to 3, and more preferably 1.

Further, X ^- as an example of a group, a halogen anion radical (Cl ^-, Br ^-, etc.), sulfates, hydroxyl which may be the number of 1 to 4 carbons substituted with carboxylate or 1 to 4 carbon atoms alkyl sulfates ^{_{(CH 3 SO 4 -, C}} 2 H 5 SO 4 -
Etc.) and the like, and Cl ⁻ and CH ₃ SO ₄ ^— are particularly preferable. Examples of the quaternary ammonium salt (I) are as follows.

[0011]

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[0012]

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Of these, the quaternary ammonium salts represented by the following general formula (I-1) are preferred, and the general formula (I-2)
The quaternary ammonium salt represented by is particularly preferable.

[0014]

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[0015] ^{wherein, R 1, R 2, R} 3, X -, n: The meanings of the. The quaternary ammonium salt (I) is produced, for example, by the following production methods 1 and 2. <Production Method 1> First, a glycerol derivative represented by the general formula (V) is reacted with a compound represented by the general formula (VI) to effect esterification, and a halo represented by the general formula (VII) is obtained. Obtain the ester. Then, this haloester is reacted with a tertiary amine represented by the general formula (VIII), and further salt exchange is carried out as necessary to obtain a quaternary ammonium salt (I).

[0016]

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[Wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ and n are as defined above. Y: Indicates a halogen atom. R ⁷ : represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. Examples of the compound represented by the general formula (VI) include monochloroacetic acid, monochlorobutyric acid, monochlorohexanoic acid, and their methyl esters and ethyl esters. Examples of the catalyst used for esterification include acid catalysts such as p-toluenesulfonic acid and sulfuric acid.

The tertiary amine represented by the general formula (VIII) includes trimethylamine, triethylamine,
Tripropylamine, N-methyldiethanolamine,
N, N-dimethylethanolamine, triethanolamine, N, N-dimethyl-2-hydroxypropylamine, N, N-dimethylbutylamine, N, N-diethylmethylamine, N, N-dimethylisopropylamine,
Examples thereof include N-methyldibutylamine, and examples of the solvent in the quaternization reaction include methanol, ethanol, isopropanol, and acetone.

<Production Method 2> The general formula (VI
The haloester represented by I) is reacted with the secondary amine represented by the general formula (IX) to obtain an aminoester represented by the general formula (X), and further represented by the general formula (XI). The resulting quaternizing agent is reacted, and if necessary, salt exchange is performed.
A primary ammonium salt (I) is obtained.

[0020]

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[Wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ , X, Y, and n are as defined above. In this case, the secondary amine represented by the general formula (IX) used is dimethylamine, N-ethylmethylamine, diethylamine, N-methylisopropylamine, N-ethylisopropylamine, N-methyl. Butylamine, diisopropylamine, dipropylamine,
N-ethylbutylamine, N-methylethanolamine, diethanolamine, N-methyl-2-hydroxypropylamine, di (2-hydroxypropyl) amine and the like can be mentioned, and as a quaternizing agent represented by the general formula (XI) Examples thereof include lower alkyl halides such as methyl chloride and di-lower alkyl sulfates such as dimethyl sulfate. Examples of the solvent for the quaternization reaction include water, methanol, ethanol, isopropanol, acetone and the like.

[Component (B)] In the present invention, a quaternary ammonium salt represented by the above general formula (II) (hereinafter abbreviated as quaternary ammonium salt (II)) is used as the component (B). It In the general formula (II), R ¹ , R ² , R ³ and R groups
Examples of the group ⁴ , R ^{5, the} group n, and the group X ⁻ include those specifically exemplified in the above general formula (I).
Further, preferred examples of the respective groups include those exemplified in the above general formula (I). Examples of the quaternary ammonium salt (II) are as follows.

[0023]

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[0024]

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Of these, the quaternary ammonium salts represented by the following general formula (II-1) are preferred, and the general formula (II-2)
The quaternary ammonium salt represented by is particularly preferable.

[0026]

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[In the formula, R ¹ , R ² , R ³ , X ⁻ , and n are as defined above. The quaternary ammonium salt (II) is produced, for example, by the following production methods 3 and 4. <Production Method 3> In the production method 1 of the quaternary ammonium salt (I), the glycerol derivative represented by the general formula (XII) is used in place of the glycerol derivative represented by the general formula (V),
The same esterification reaction is carried out to obtain a haloester represented by the general formula (XIII), and a third haloester represented by the general formula (VIII) is also obtained.
A quaternary ammonium salt (II) is obtained by reacting with a primary amine and further salt exchange if necessary.

[0028]

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[Wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁷ , Y, and n are as defined above. <Production Method 4> The same as in Production Method 2 for quaternary ammonium salt (I), except that a haloester represented by the general formula (XIII) is used instead of the haloester represented by the general formula (VII). Is reacted with a secondary amine represented by the general formula (IX) to give an amino ester represented by the general formula (XIV).
The quaternary agent represented by (XI) is reacted and, if necessary, salt exchange is carried out to obtain a quaternary ammonium salt (II).

[0030]

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[Wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ , X, Y, and n are as defined above. ] [Softening agent composition] The softening agent composition of the present invention is
The composition contains the component (A) and the component (B), and the total content of the component (A) and the component (B) is 3 to 40% by weight, preferably 4 to 30% by weight, more preferably 4 to 25% by weight. In weight percent, the balance is water and optional ingredients. In addition, the weight ratio of component (A) and component (B) is
[(A) component] / [(B) component] = 99.999 / 0.001 to 80/2
It is 0, preferably 99.999 / 0.001 to 90/10, and more preferably 99.995 / 0.005 to 94/6.

When the total content of the component (A) and the component (B) is less than 3% by weight, the softening effect desired by the present invention cannot be obtained,
When it exceeds 40% by weight, the viscosity of the composition is increased, resulting in poor handling property. Further, when the weight ratio of the component (A) and the component (B) exceeds 99.999 / 0.001, the long-term stabilizing effect decreases, and when it is less than 80/20, the composition tends to thicken with time. Become.

For the purpose of improving the softening performance of the composition of the present invention, the compounds represented by the general formulas (III-1) to (III-7) as the component (C) and the compound (D The compounds represented by the general formulas (IV-1) to (IV-9) can be blended as the component).

[0034]

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[Wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ , X ⁻ , and n are as defined above. M: represents a hydrogen atom or a cation group. ]

[0036]

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[In the formula, R ⁴ , R ⁵ , n, and M are as defined above. R ⁶ : represents an alkyl group or an alkenyl group having 1 to 22 carbon atoms. Z: Indicates a halogen atom. As the component (C), compounds represented by the general formulas (III-1) to (III-7) are used.
The compounds represented by formulas (-1) to (III-3) are preferable, and the compounds represented by formulas (III-1) to (III-2) are particularly preferable. Examples of R ¹ , R ² and R ³ in these formulas are (R ¹ , R ² and R ³ ) = (methyl group, methyl group, methyl group), (ethyl group, ethyl group, ethyl group), (Methyl group, methyl group, hydroxyethyl group), (methyl group, methyl group, ethyl group), (hydroxyethyl group, hydroxyethyl group, hydroxyethyl group) and the like, preferably (methyl group, methyl group, (Methyl group), (ethyl group, ethyl group, ethyl group) and the like. Examples of R ⁴ and R ⁵ include a decyl group, a dodecyl group, a tetradecyl group, a hexadecyl group, an octadecyl group and the like, and a hexadecyl group and an octadecyl group are preferable. Further, n represents a number of 1 to 6, preferably 1 to 3, and more preferably 1. Further, X ^- as preferred ^{examples, Cl -, Br -, HCO} 3 -, C
H ₃ SO ₄ ^{− and the} like can be mentioned, and Cl ⁻ is more preferable. Preferred examples of M include H and Na.

Further, as the component (D), one of the general formulas (IV-1) to (IV-
The compound represented by 9) is used, and among these, the compounds represented by the general formulas (IV-1) to (IV-4) are preferable, and particularly, the compounds represented by the general formulas (IV-1) to (IV- The compound represented by 2) is preferable. Examples of R ⁴ and R ⁵ in these formulas include decyl group, dodecyl group, tetradecyl group, hexadecyl group, octadecyl group and the like, preferably hexadecyl group and octadecyl group. Further, n represents a number of 1 to 6,
It is preferably 1 to 3, more preferably 1. Preferable examples of Z include Cl and Br. Further, preferred examples of the compound represented by the general formula (IV-8) used as the component (D) include methyl chloroacetate, ethyl chloroacetate, n-butyl chloroacetate, isopropyl chloroacetate,
T-butyl chloroacetate, methyl bromoacetate, ethyl bromoacetate and the like can be mentioned, with preference given to methyl chloroacetate and ethyl chloroacetate.

Further, the general formula (I) used as the component (D)
As a preferable example of the compound represented by V-9), ClCH ₂ COO
M, ClC ₂ H ₄ COOM, ClC ₃ H ₆ COOM, ClC ₄ H ₈ COOM, ClC ₅ H ₁₀ COO
M, BrCH ₂ COOM, BrC ₂ H ₄ COOM and the like, and preferably
ClCH ₂ COOM can be mentioned. Here, as a preferred example of M, a cationic group selected from the group consisting of alkali metals, alkaline earth metals, and alkaline earth metals and transition elements in the periodic table of elements, or an amine salt having 1 to 10 carbon atoms Or a quaternary ammonium salt is exemplified. Preferably, an alkali metal salt, an alkaline earth metal salt, and a carbon number of 1 to 6
Amine salts (eg, monoethanolamine salts, diethanolamine salts, triethanolamine salts, etc.) or the fourth
Examples include primary ammonium salts and the like.

In the composition of the present invention, when the component (C) is contained, the component (C) is in a weight ratio of [(C) component] /
[(A) component + (B) component + (C) component] can be blended in a ratio of 20/80 or less, and the blending amount of the (C) component in the composition is (A) component, ( The total content of the component (B) and the component (C) is 3 to 40% by weight. Further, in the composition of the present invention, when the component (D) is contained, the component (D) is in a weight ratio,
[(D) component] / [(A) component + (B) component + (C) component + (D)
Ingredient] can be blended in a ratio of 20/80 or less,
The amount of component (D) in the composition is (A) component, (B) component,
3-40% by weight as the total content of component (C) and component (D)
It is.

In the composition of the present invention, a known cationic compound (quaternary ammonium salt, imidazolinium salt, etc.), ester or amide, or a mixture of two or more thereof is added as a softening agent base. can do. As an example of these, the fourth represented by the following general formula (XV)
Examples thereof include secondary ammonium salts and compounds represented by the following general formulas (XVI-1) to (XVI-8).

[0042]

[Chemical 21]

[In the formula, R ¹¹ represents an alkyl or hydroxyalkyl group having 1 to 4 carbon atoms. A ¹ , A ² and A ³ : the same or different from each other, a hydrogen atom or R ¹² C
A group represented by O- (wherein R ¹² represents a straight chain or branched chain alkyl or alkenyl group having 7 to 35 carbon atoms). However, at least one of A ¹ , A ² and A ³ is a group represented by R ¹² CO— (wherein R ¹² is as defined above). Q ^-: represents an anion group. Examples of Q ⁻ are halogen ions such as Cl ⁻ and Br ⁻ , and alkylsulfate groups having 1 to 5 carbon atoms. In the composition of the present invention, Q ⁻ in the quaternary ammonium salt represented by the general formula (XV) may be the same as X ⁻ in the quaternary ammonium salts (I) and (II) used at the same time. , May be different.

[0044]

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[Wherein R ¹⁵ and R ¹⁶ are the same or different from each other and represent a linear or branched alkyl, alkenyl or 2-hydroxyalkyl group having 10 to 24 carbon atoms. R ^17: alkyl or hydroxyalkyl group having 1 to 3 carbon atoms, a benzyl group, or the formula _{- (C 2 H 4 O)} p H ( wherein p is 1-3
Represents the number of). R ¹⁸ : a hydrogen atom, an alkyl or hydroxyalkyl group having 1 to 3 carbon atoms, a benzyl group or a group represented by the formula — (C ₂ H ₄ O) _pH (where p is as defined above); Show. Q ^-: is as defined above. ]

[0046]

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[Wherein R ¹⁷ , R ¹⁸ and Q ⁻ are as defined above]. R ¹⁹ and R ²⁰ are the same or different from each other and are straight-chain or branched-chain C 9-23 alkyl, alkenyl or 2-
A hydroxyalkyl group is shown. ]

[0048]

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[Wherein R ¹⁷ , R ¹⁸ , R ¹⁹ , and Q ⁻ are as defined above. ]

[0050]

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[Wherein R ¹⁸ , R ¹⁹ , R ²⁰ , and Q ⁻ are as defined above. B: represents a group represented by the formula -OCO- or -NHCO-. ]

[0052]

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[In the formula, R ¹⁸ , R ¹⁹ , R ²⁰ , B, and Q ⁻ are as defined above. ]

[0054]

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[Wherein R ¹⁹ is as defined above]. ]

[0056]

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[Wherein R ¹⁹ and R ²⁰ are as defined above]. ]

[0058]

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[Wherein R ¹⁹ and R ²⁰ are as defined above]. R ^21: a straight chain or branched chain alkyl having a carbon number of 9 to 23, alkenyl or 2-hydroxyalkyl group. When the concentration of the component (A) and the component (B) in the softening agent composition of the present invention is high, the composition tends to thicken during storage. To suppress this tendency of thickening, 3 active hydrogen was added.
Ethylene oxide and, if necessary, propylene oxide and / or trimethylene oxide are added to a compound having at least one of them, and the weight average molecular weight is 5,000 to 2,000,000, and the proportion of the oxyethylene group portion in the molecular weight is 55.
Polyether compound or derivative thereof in an amount of not less than wt%
It is preferable to add ((E) component).

Examples of the compound having three or more active hydrogens as a starting material for obtaining the component (E) include the following. As polyhydric alcohols, trimethylolpropane, diethanolamine, triethanolamine, glycerin, pentaerythritol, sorbitol, sucrose,
Examples thereof include partially saponified products of polyglycerin, polyvinyl alcohol and polyvinyl acetate. Examples of the polyphenols include phenol resins and formalin condensates of alkylphenols. Examples of the polyamine compound include polyethylenedimine such as ethylenediamine and diethylenetriamine, triethylenetetramine, tetraethylenepentamine, and pentaethylenehexamine. Further, partial amidated products and N-alkylated products which are derivatives of these polyamine compounds can also be used as the starting materials for obtaining the component (E) as long as three or more active hydrogens remain. Particularly preferred among these (E) components are glycerin, sorbitol, tetraethylenepentamine and polyethyleneimine.

The component (E) can be produced by adding ethylene oxide and, if necessary, propylene oxide and / or trimethylene oxide to a compound having 3 or more active hydrogens by a conventional method.
As the component (E), an adduct of ethylene oxide alone, a block adduct of ethylene oxide and propylene oxide, and a partially block adduct of ethylene oxide and propylene oxide are particularly preferable. When two or more kinds of alkylene oxides are added to a compound having three or more active hydrogens, the order of addition may be any,
Propylene oxide (hereinafter abbreviated as PO) is first added, and then ethylene oxide (hereinafter abbreviated as EO) is added to the composition of the present invention in which the concentrations of the component (A) and the component (B) are high. It is preferable for suppressing the tendency of the material to thicken during storage.

The molecular weight of the component (E) is 5,000 to 2,000,000.
And preferably in the range of 10,000 to 100,000. The proportion of the oxyethylene group (EO chain) in the molecule is 55% by weight or more of the total molecular weight, preferably
80% by weight or more. In this case, if the molecular weight of the component (E) is less than 5,000, the effect of suppressing the tendency of thickening during storage of the softening agent composition is low, while 2,000,00
When it exceeds 0, the viscosity of the softening agent composition remarkably increases, and it is difficult to take it out of the bottle. Also,
When the proportion (total weight) of oxyethylene groups in the molecular weight of component (E) is less than 55% by weight, the effect of suppressing the thickening tendency of the softening agent composition during storage is low.

The derivative of the polyether compound, which is the component (E), is a crosslinking reaction product obtained by the reaction of the polyether compound with a compound having an isocyanate group, or sulfuric acid of the terminal hydroxyl group of the polyether compound. Compounds, phosphorus oxides, carboxyalkylated products, fatty acid esterified products, and those obtained by cationizing a part of nitrogen atoms of the above-mentioned polyether compound. Among them, fatty acid esterified products and cationized products are particularly preferable. The fatty acid used in the production of the fatty acid esterified product preferably has 7 to 23 carbon atoms, but the number of double bonds, the presence or absence of branching, etc. do not significantly affect the performance. As the cationized compound, a compound obtained by cationizing a part of nitrogen atoms in the polyether compound with a dialkyl sulfuric acid or an alkyl halide, or after cationization and neutralizing with acetic acid, alkylbenzenesulfonic acid or the like can be obtained. Examples include cationized compounds.

Fatty acids and nonionic surfactants may be added to the composition of the present invention as optional components. Examples of fatty acids that can be blended are fatty acids having 8 to 36 carbon atoms, beef tallow,
Fatty acids derived from natural fats and oils such as lard, palm oil, palm kernel oil, coconut oil and rapeseed oil can be used. Preferred examples include lauric acid, myristic acid, palmitic acid, stearyl acid, oleic acid, eicosanoic acid, docosanoic acid and the like.
As the nonionic surfactant, polyoxyethylene (5 to 100 moles) alkyl or alkenyl (C ₁₂ -C ₂₄₎ ethers or polyoxyethylene (5 to 100 moles) alkyl or alkenyl (C ₁₂ -C ₂₄₎ amine Etc. are illustrated.

Further, a hydrotrope agent such as ethylene glycol, propylene glycol, glycerin, pentaerythritol or urea may be blended. Also,
As needed, isopropyl alcohol, ethanol,
8-Acetylated sucrose, denatured alcohol and the like can be added.

The composition of the present invention contains NaCl, CaCl ₂ , MgCl ₂ , NaNO ₃ , NaNO ₂ , Na ₂ SO ₄ , M in order to adjust the viscosity of the composition.
An inorganic electrolyte such as gSO ₄ or CaSO ₄ can be added. In this case, the content of the inorganic electrolyte in the composition is 0 to 2% by weight, preferably 0 to 1% by weight. In the softener composition of the present invention, further, in order to adjust the pH of the composition,
Acidic or alkaline substances can be added. In this case, it is possible to add an acidic or alkaline substance so that the pH of the composition of the present invention is within the range of 1.5 to 7.5.
It is desirable from the viewpoint of viscosity and storage stability of the composition. Further, the composition of the present invention may contain a pigment or dye for improving its appearance, silicone for defoaming during rinsing, and fragrance for improving taste after use and after finishing. . Further, an antibacterial agent can be added.

The composition of the present invention can be produced, for example, by the following method. Method of mixing components (A) and (B) in advance and adding them to the aqueous phase Adding component (A) to the aqueous phase and then adding component (B) Adding the component (B) to the aqueous phase , Then adding component (A), adding component (A) and component (B) in advance, and adding water to component (A) and component (B) simultaneously adding to the aqueous phase (A ) Add water to component, then add component (B) Add component (B) to water, then add component (A) Add component (C), nonionic surfactant, etc. In the case of adding the optional component of (A), the component (A), the component (B) and water may be mixed in advance and added, or may be added separately. When each component is solid at room temperature or has high viscosity, it can be added by heating or melting in order to improve the handling property.

[0068]

The liquid softening agent composition of the present invention imparts sufficient flexibility and elasticity (puffiness) to various fibers, and storage stability (does not gel or thicken after storage). , That the softening agent does not hydrolyze after storage) is extremely good.

[0069]

EXAMPLES The present invention will now be described in more detail by showing examples of the present invention, but the present invention is not limited to these examples. An example of synthesizing the component (A) is also shown below. The percentages in the examples are on a weight basis unless otherwise specified.

Synthetic Example 1,3 in a four-necked flask equipped with a stirrer, thermometer, and cooling tube.
-Dioctadecanoxy-2-propanol (177.6 g) and monochloroacetic acid (38 g) were added and the temperature was raised to 140 ° C. After the produced water was distilled off and the reaction was carried out at the same temperature for 7 hours, excess monochloroacetic acid was removed by washing with water to obtain 200 g of the corresponding chloroacetic acid ester. Next, add the above chloroacetic acid ester to an autoclave equipped with a stirrer and a thermometer.
50g, trimethylamine 16g, isopropyl alcohol
40 g was put and it was made to react at 60 degreeC for 4 hours. After the reaction, crystallization with acetone was performed, and after drying, 150 g of a quaternary ammonium salt (component (A)) was obtained as a white powder. NMR spectrum, IR
The following structure was confirmed from the spectrum.

[0071]

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[0072]

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IR spectrum (KBr tablet) 1752 cm ^-1 , 1209 cm ^-1 , 1128 cm ^-1 Examples 1 to 20, Comparative Examples 1 to 6 (A) component shown in Table 1 and (B) component shown in Table 2 Shown in Table 3
(C) component, (D) component shown in Table 4, (E) component shown in Table 5,
And other components were used to prepare liquid softening agent compositions having the compositions shown in Tables 6 to 8. With respect to the obtained liquid softening finish composition, the flexibility, elasticity and storage stability were measured by the following methods, and the results are shown in Tables 6-8. In both cases, CaCl ₂ was 0.2% by weight in the composition.
Compounded, the balance except water is water, and the pH in the composition is
It was adjusted to 3.0 with an aqueous HCl solution.

(1) Evaluation of softness and elasticity A commercially available cotton towel, acrylic fiber, and polyester fiber were repeatedly washed 5 times with a commercially available detergent "Attack" (registered trademark, manufactured by Kao Corporation) and attached to the cloth. After removing the detergent, 0.5% of the weight of the cloth prepared by adding the liquid softening agent composition prepared above was treated at 25 ° C. with a bath ratio of 1/30 for 3 minutes under stirring, and then air-dried indoors, and then 20 The sample was left for 24 hours in a constant temperature and constant humidity chamber at 65 ° C. and 65% RH. The softness and elasticity of these cloths were evaluated.

For the evaluation of softness and elasticity, pairwise comparison was carried out by using the cloth treated with the softening agent composition of Comparative Example 1 as a control. The evaluation is expressed as follows. +2: Softer or more elastic than the control +1: Slightly softer or slightly more elastic than the control 0: Softer or softer than the control or equivalent -1: The control is slightly softer or slightly more elastic -2: The control is softer or more elastic (2) Evaluation of storage stability The liquid softening agent composition prepared above is sealed and
It was stored at 40 ° C and 20 ° C for 20 days, and the appearance and fluidity under the sealed condition were visually observed. As a result, those showing no change in appearance and fluidity were regarded as good, and those showing change in state were specified as such.

[0076]

[Table 1]

[0077]

[Table 2]

[0078]

[Table 3]

[0079]

[Table 4]

[0080]

[Table 5]

[0081]

[Table 6]

[0082]

[Table 7]

[0083]

[Table 8]

Note) In Tables 6 to 8, the numbers in parentheses () indicate the blending amount in the composition, and the unit is% by weight. The balance is water.

From the above results, the soft finish composition of the present invention can impart excellent flexibility and elasticity,
It can be seen that the storage stability is also good.

 ──────────────────────────────────────────────────続 き Continued on the front page (72) Inventor Muneo Aoyagi 1334 Minato, Wakayama City, Wakayama Pref.

Claims (5)

[Claims] 1. A composition comprising the following component (A) and component (B):
The weight ratio of the components (A) and (B) is [(A) component] / [(B)
Ingredient] = 99.999 / 0.001 to 80/20, and the total content of the (A) component and the (B) component in the composition is 3 to 40% by weight. Stuff. Component (A): quaternary ammonium salt represented by the general formula (I) [Wherein R ¹ , R ² and R ^{3 are the} same or different and each is a hydrogen atom or a carbon number 1
4 shows an alkyl group, an alkenyl group or a hydroxyalkyl group. R ⁴ and R ^{5 are the} same or different and each represents a linear or branched alkyl group or alkenyl group having 8 to 36 carbon atoms, which may be substituted with a hydroxyl group. X ^-: represents an anion group. n: shows the number of 1-6. Component (B): quaternary ammonium salt represented by the general formula (II) [In the formula, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , X ⁻ , and n are as defined above. ] 2. The component (A) is a quaternary ammonium salt represented by the general formula (I-1), and the component (B) is a general formula (II-1).
The liquid softening agent composition according to claim 1, which is a quaternary ammonium salt represented by: Embedded image [In the formula, R ¹ , R ² , R ³ , X ⁻ , and n are as defined above. ] 3. Further, as the component (C), any one of the general formulas (III-1) to (I
II-7) containing at least one selected from the group consisting of the compounds represented by the formula (II-7), and in a weight ratio, [(C) component] / [(A)
Component + (B) component + (C) component] is 20/80 or less, and the total content of the (A) component, (B) component and (C) component is 3
The liquid softening agent composition according to claim 1 or 2, which is -40% by weight. Embedded image [In the formula, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , X ⁻ , and n are as defined above. M: represents a hydrogen atom or a cation group. ] 4. Further, as the component (D), one of the general formulas (IV-1) to (IV-
At least one selected from the group consisting of the compounds represented by 9) is included in a weight ratio of [(D) component] / [(A) component + (B) component + (C) component + (D Component) is 20/80 or less, and the total content of the component (A), the component (B), the component (C) and the component (D) is 3 to 40% by weight. The liquid softener composition according to the above paragraph. Embedded image [In the formula, R ⁴ , R ⁵ , n, and M are as defined above. R ⁶ : represents an alkyl group or an alkenyl group having 1 to 22 carbon atoms. Z: Indicates a halogen atom. ] 5. The component (A) is a quaternary ammonium salt represented by the general formula (I-2), and the component (B) is a general formula (II-2).
The liquid softening agent composition according to any one of claims 1 to 4, which is a quaternary ammonium salt represented by: [Chemical 6] [In the formula, X ⁻ : represents the above meaning. ]