JP2001192455A - Polysiloxane containing quaternary ammonium salt, its production process and fiber-treating agent composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a polysiloxane containing a quaternary ammonium salt and widely usable as a fiber-treating agent composition capable of imparting various fibers and textile products with excellent antibacterial property, softness and washing resistance. SOLUTION: The objective polysiloxane containing a quaternary ammonium salt contains at least one unit expressed by the following general formula (1) (R1 is a 1-20C substituted or non-substituted univalent organic group; R2 is a univalent organic group containing at least one quaternary ammonium salt; R3 is an organoxy group expressed by OR1; and (p) is a positive number satisfying the formula 2<=p<=2,000).

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a quaternary ammonium salt which is effective as a main component of a fiber treatment composition having antibacterial properties and imparting excellent flexibility and washing resistance to various fibers or textile products. The present invention relates to a polysiloxane, a method for producing the same, and a fiber treatment composition.

[0002]

2. Description of the Related Art
Quaternary ammonium salt-containing silanes represented by 3- (trimethoxysilyl) propyldimethyloctadecyl ammonium chloride are widely used as treatment agents for imparting antibacterial properties to various fibers or fiber products. This product is characterized by low toxicity, little irritation and hypersensitivity to the skin, and excellent washing resistance to natural fibers such as cotton, but polyester and nylon. There is a disadvantage that the washing resistance is not sufficient for synthetic fibers. In addition, since the quaternary ammonium salt-containing silane is a solid, it must be supplied as an alcohol solution such as methanol, which poses a cost problem on the transportation surface. However, there is a problem that there is a risk of environmental pollution, a danger of ignition or the like, and a lack of safety.

In order to compensate for these disadvantages, Japanese Patent Application Laid-Open No.
JP-A-01174 proposes a polysiloxane having a quaternary ammonium salt in the side chain, and JP-A-6-298775 proposes a compound having a quaternary ammonium salt at both ends. However, all of the intermediates for producing these siloxanes have complicated manufacturing processes and are expensive, and the obtained siloxanes have poor washing resistance because they rely only on quaternary ammonium bases for adsorption to fibers. Has the disadvantage that

[0004] The present invention has been made in view of the above circumstances,
A novel quaternary ammonium salt-containing polysiloxane that is excellent in antibacterial properties and can impart good flexibility to fibers or textiles even after washing when blended as a main component of a fiber treatment composition, and is inexpensive. It is an object of the present invention to provide a novel production method and a fiber treatment composition containing this polysiloxane as a main component.

[0005]

Means for Solving the Problems and Embodiments of the Invention The present inventors have made intensive studies to achieve the above object, and as a result, have reached the present invention. In other words, the present inventors have found that a novel polysiloxane having a siloxane skeleton with a quaternary ammonium salt obtained by subjecting α, ω-dihydroxydimethylsiloxane and a quaternary ammonium salt-containing trialkoxysilane to a dealcoholation reaction is relatively It is easy to manufacture and can be synthesized from inexpensive materials.Since it has both a siloxane skeleton and an alkoxy group, it has excellent adsorption to fibers, excellent washing resistance, and contains alcohol. It is excellent in safety because it is not used. In addition, aminopropylamino trialkoxysilane, N-aminoethyl-3-
By using an aminosilane such as aminopropyl trialkoxysilane in combination, a siloxane containing both an amino group and a quaternary ammonium salt-containing group in the skeleton can be obtained, and by using this compound, the softening treatment and the antibacterial treatment can be performed simultaneously. It has been found that such an advantage can be provided.

A siloxane having a quaternary ammonium salt having a siloxane skeleton is exemplified in Japanese Patent Publication No. 49-11760, which is used as a foam stabilizer, and furthermore, some of the polymers have anti-resistance. It does not contain an alkoxy group necessary for imparting washability, and its synthesis method is completely different from that of using a dealcoholation reaction.

Accordingly, the present invention firstly provides a quaternary ammonium salt-containing polysiloxane containing at least one unit represented by the following general formula (1).

[0008]

Embedded image (Wherein, R ¹ is a substituted or unsubstituted monovalent organic group having 1 to 20 carbon atoms, R ² is a monovalent organic group containing at least one quaternary ammonium salt, and R ³ is represented by —OR ¹ . And p represents a positive number satisfying 2 ≦ p ≦ 2,000.)

Secondly, there is provided a quaternary ammonium salt-containing polysiloxane having at least one terminal group represented by the following general formula (2).

Embedded image (In the formula, R ¹ , R ² , R ³ , and p have the same meaning as described above. A is 0 or 1.)

Third, (A) the following general formula (5)

Embedded image (Wherein R ¹ and p have the same meanings as described above), and (B) the following general formula (6)

Embedded image (Wherein, R ¹ , R ² and R ³ have the same meanings as above. A
Is 0 or 1. A) providing a method for producing the above quaternary ammonium salt-containing polysiloxane, which comprises subjecting the organosilane represented by the above) to a dealcoholation reaction, and thirdly, containing the quaternary ammonium salt-containing polysiloxane as a main component. A fiber treatment composition is provided.

Hereinafter, the present invention will be described in more detail.
The quaternary ammonium salt-containing polysiloxane of the present invention contains at least one unit represented by the following general formula (1) and / or a terminal group represented by the following general formula (2).

[0012]

Embedded image (Wherein, R ¹ is a substituted or unsubstituted monovalent organic group having 1 to 20 carbon atoms, R ² is a monovalent organic group containing at least one quaternary ammonium salt, and R ³ is represented by —OR ¹ . And p represents a positive number satisfying 2 ≦ p ≦ 2,000.)

[0013]

Embedded image (In the formula, R ¹ , R ² , R ³ , and p have the same meaning as described above. A is 0 or 1.)

Examples of the organic group represented by R ¹ include an unsubstituted or substituted monovalent hydrocarbon group.
~ 3. Specific examples of R ¹ in the organopolysiloxane of the present invention include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group,
Octyl, decyl, dodecyl, tetradecyl,
Alkyl groups such as octadecyl group and eicosyl group, alkenyl groups such as vinyl group, allyl group, propenyl group, butenyl group and hexenyl group, aryl groups such as phenyl group and tolyl group, benzyl group, phenylethyl group and phenylpropyl group Aralkyl group, cyclopentyl group, cycloalkyl group such as cyclohexyl group, or halogen such as chloromethyl group, trifluoropropyl group, chlorophenyl group or the like in which part or all of the hydrogen atoms bonded to these carbon atoms are substituted with halogen atoms And a halogenated aryl group such as a halogenated alkyl group and a halogenated phenyl group. Among them, it is particularly preferable that 90 mol% or more is a methyl group, a phenyl group, or a trifluoropropyl group.

Further, the monovalent hydrocarbon group such as an alkyl group represented by R ¹ may be one obtained by partially substituting a hydrogen atom with a nitrogen-containing monovalent organic group such as an amino group or an alkylamino group. Further, a nitrogen-containing divalent organic group such as an NH group, an NCH ₃ group, or an NC ₂ H ₅ group may be used.

R ² is a monovalent organic group having at least one quaternary ammonium salt and represented by the following general formula (3): —CH ₂ CH ₂ CH ₂ N ⁺ R ⁴ R ⁵ R ⁶ Cl ⁻ (3) ( In the formula, R ⁴ and R ⁵ are the same or different from each other and have 1 to 3 carbon atoms.
Is a monovalent hydrocarbon group, and R ⁶ is a monovalent hydrocarbon group having 1 to 30 carbon atoms. ) In which those are exemplary shown, in particular the following general formula _{(4) -CH 2 CH 2 CH} 2 N + (CH 3) 2 C n H 2n + 1 Cl - (4) ( wherein, n 12-24 Is preferable.) Is preferable.

Examples of the monovalent hydrocarbon group of R ⁴ , R ⁵ and R ⁶ include those having 1 to 30 carbon atoms and 1 to 30 carbon atoms among those exemplified for R ¹ described above. Can be

Particularly preferred as R ² are the following. ^{_{-CH 2 CH 2 CH 2 N +}} (CH 3) 2 C 18 H 37 Cl - -CH 2 CH 2 CH 2 N + (CH 3) 2 CH 2 C 6 H 5 Cl -

R ³ is an organooxy group represented by —OR ¹ , particularly preferably an alkoxy group having 1 to 6 carbon atoms. Specific examples of R ³ include a methoxy group,
Examples thereof include an ethoxy group and a propoxy group, and a methoxy group is most preferable.

P represents a positive number satisfying 2 ≦ p ≦ 2,000.
Preferably, p is 2 or more, particularly 10 or more, and 2,000 or less, preferably 1,000 or less, more preferably 100 or less. If p is too large, the content of the quaternary ammonium salt decreases, and therefore, the antibacterial property decreases.

The terminal group of the quaternary ammonium salt-containing polysiloxane containing at least one unit represented by the general formula (1) is arbitrary, and may be a dialkylhydroxysilyl group, a trialkylsilyl group, an alkyldialkoxysilyl group, A dialkylalkoxy group and the like are exemplified, and from the viewpoint of stability, a dialkylhydroxysilyl group, a trialkylsilyl group, and an alkyldialkoxysilyl group are preferable, and a group represented by the general formula (2) is particularly preferable.

Examples of the polysiloxane of the present invention include those represented by the following general formula (I).

[0023]

Embedded image(However, R 'is -SiR¹ _TwoOH, -SiR¹ _TwoR^Three, -S
iR¹R^Three _Two, -SiR¹ _aR ^TwoR^Three _2-aAnd the like.
R's may be the same or different. q is 0-3
0, preferably 1 to 30, especially 1, 2 or 3,
At least one R in one molecule^TwoAnd R^ThreeHaving. What
Contact, R¹, R^Two, R^Three, P have the same meaning as described above. )

Examples of the quaternary ammonium salt-containing polysiloxane containing at least one unit represented by the general formula (1) include the following.

[0025]

Embedded image

[0026]

Embedded image

The quaternary ammonium salt-containing polysiloxane of the present invention comprises (A) an organopolysiloxane having hydroxyl groups at both ends and represented by the following general formula (5), and (B) a quaternary organopolysiloxane represented by the following general formula (6). It can be obtained by subjecting an ammonium silane-containing organosilane to a dealcoholation reaction.

[0028]

Embedded image (In the formula, R ¹ , R ² , R ³ , p, and a have the same meaning as described above.)

In the general formula (5), p is 2 as described above.
≤ p ≤ 2,000. If p is less than 2, the silanol is unstable, and a condensation reaction occurs in parallel with the reaction with the component (B). As a result, cyclics are by-produced. R ¹ is as described above, particularly 90 mol%
The above is preferably a methyl group, a phenyl group, and a trifluoropropyl group. Specifically, those represented by the following formulas are exemplified.

[0030]

Embedded image

In the general formula (6), R ² and R ³ represent the general formula (1)
Wherein R ² is excellent in reactivity with the component (A), has high antibacterial properties, and is easy to synthesize, as represented by the above general formula (3) —CH ₂ CH ₂ CH ₂ N ⁺ R ⁴ R ⁵ R ⁶ Cl ⁻ (3) is preferable, and —CH ₂ CH ₂ CH ₂ N ⁺ (CH ₃ ) ₂ C ₁₈ H ₃₇ Cl ⁻ is particularly preferable.

R ³ is most preferably a methoxy group in which the dealcoholation reaction can easily proceed. Specific examples of the quaternary ammonium salt-containing organosilane represented by the formula (6) include:
The following are exemplified. (CH ₃ O) ₃ SiCH ₂ CH ₂ CH ₂ N ⁺ (CH ₃ ) ₂ C ₁₈ H
_{^{37 Cl - (CH 3 O)}} 3 SiCH 2 CH 2 CH 2 N + (CH 3) 2 CH 2
C ₆ H ₅ Cl ^-

In addition to the silane represented by the general formula (6),
It is also optional to use aminosilanes as shown below as the component (C), and examples of the aminosilanes are shown below. _{(CH 3 O) 3 SiCH 2} CH 2 CH 2 NH 2 (CH 3 O) 3 SiCH 2 CH 2 CH 2 NHCH 2 CH 2 NH 2 (CH 3 O) 3 SiCH 2 CH 2 CH 2 NHCH 2 CH 2 NH
CH ₂ CH ₂ NH ₂

Embedded image

The reaction conditions of the component (A) and the component (B) are as follows:
Although it depends on the reactivity of the silanol of the component (A) and the reactivity of the organooxy group, particularly the alkoxy group of the component (B), the reaction is generally preferably performed at a reaction temperature of 50 to 180 ° C. for 3 to 20 hours. By this reaction, a quaternary ammonium salt-containing polysiloxane represented by the general formula (1) can be easily obtained.

Since the quaternary ammonium salt of the component (B) is usually in the form of an alcohol solution such as methanol, it is necessary to react in an alcohol solution or to remove the alcohol before the reaction. . In order for the reaction to proceed efficiently, it is preferable to carry out the reaction while removing the alcohol from the system.

In addition to the components (A) and (B), it is also possible to use the above-mentioned aminosilane of the component (C) in combination, whereby the dealcoholization reaction can be promoted.
A solvent is not particularly necessary, but when the viscosity of the component (A) is high,
Alternatively, when the viscosity of the product is high, the reaction may be performed using a solvent such as toluene or xylene.

The components (A) and (B) are (A) /
When (B) is larger than 2, it is not preferable because a large amount of polysiloxane containing no quaternary ammonium salt remains, and when it is smaller than 0.5, it is preferable because quaternary ammonium silane remains. Is 0.5 ≦
(A) / (B) ≦ 2.0.

Further, if the quaternary nitrogen atom content of the obtained polysiloxane is less than 0.05% by weight, a sufficient antibacterial effect cannot be exhibited, so that it is preferably 0.05% by weight or more.

The amino group-containing polysiloxane is usually modified by reacting it with an organic acid, an inorganic acid, or an epoxy compound, and the quaternary ammonium salt-containing polysiloxane obtained in the present invention is also modified.
When the aminosilane described above is used in addition to the components (A) and (B), modification with an organic acid, an inorganic acid, or an epoxy compound is optional. For example, one or _two of the hydrogen atoms of NH or NH ₂ are substituted with COR (R is an alkyl group having 1 to 10 carbon atoms), or CH ₂ CH
(OH) CH ₂ O (C ₂ H ₄ O) _n R ⁷ (R ⁷ is a hydrogen atom or a monovalent hydrocarbon group such as an alkyl group having 1 to 8 carbon atoms, and n is 0
To be modified with an organic acid, an inorganic acid, or an epoxy compound.
As the organic acid, formic acid, acetic acid, acetic anhydride, propanoic acid and the like are exemplified, and acetic acid and acetic anhydride are preferable. Examples of inorganic acids include hydrochloric acid, phosphoric acid, and the like.

Examples of the epoxy compound include those represented by the following general formula (8).

[0041]

Embedded image (In the formula, R ⁸ is a hydrogen atom or a monovalent hydrocarbon group such as an alkyl group having 1 to 8 carbon atoms, and m is a positive number of 0 to 10.) Note that R ⁸ is a hydrogen atom or a butyl group. It is preferred that

The fiber treatment composition using the quaternary ammonium salt-containing polysiloxane of the present invention includes toluene,
It may be dissolved in an organic solvent such as xylene, n-hexane, n-heptane, methyl ethyl ketone, methyl isobutyl ketone, ethyl acetate, butyl acetate, mineral turbene, or nonionic, anionic, cationic, or amphoteric. An emulsion is prepared using a surfactant or the like. Although there is no particular limitation on these emulsifiers, examples of nonionic surfactants include ethoxylated higher alcohols, ethoxylated alkylphenols, polyhydric alcohol fatty acid esters, ethoxylated polyhydric alcohol fatty acid esters, ethoxylated fatty acids, and ethoxylated fatty acids. Examples thereof include amide, sorbitol, sorbitan fatty acid ester, ethoxylated sorbitan fatty acid ester, and sucrose fatty acid ester, and their HLB is preferably in the range of 5 to 20, particularly preferably in the range of 10 to 16. . Examples of anionic emulsifiers include higher alcohol sulfates, alkyl phenyl ether sulfates, alkyl benzene sulfonates, higher alcohol phosphates, ethoxylated higher alcohol sulfates, and ethoxylated alkyl phenyl ether sulfates. Examples thereof include salts, ethoxylated higher alcohol phosphates, and examples of the cationic emulsifier include alkyltrimethylammonium chloride, alkylamine hydrochloride, coconutamine acetate, alkylamine acetate, and alkylbenzenedimethylammonium chloride. Examples of the amphoteric surfactant include N-acylamidopropyl-N, N-dimethylammoniobetaines, N-acylamidopropyl-N,
N'-dimethyl-N'-β-hydroxypropylammoniobetaines are exemplified. In addition, the amount used
The amount is preferably 5 to 50 parts by weight, more preferably 10 to 50 parts by weight, per 100 parts by weight of the quaternary ammonium salt-containing polysiloxane.
-30 parts by weight. The amount of water used for emulsification is 4
Grade ammonium salt-containing polysiloxane concentration of 10 to 10
The content may be 80% by weight, preferably 20 to
The amount is 60% by weight.

The above-mentioned emulsion can be obtained by a conventionally known method. The organopolysiloxane of the present invention is mixed with a surfactant, and the mixture is mixed with a homomixer, a homogenizer, a colloid mill, a line mixer, a universal mixer (commercially available). ), An ultra mixer (trade name), a planetary mixer (trade name), a combimix (trade name), and a three-roll mixer.

The fiber treating agent composition of the present invention may further contain other additives as long as its properties are not impaired, such as a wrinkle inhibitor, a flame retardant, an antistatic agent, an antioxidant, an antiseptic, and a rust preventive. There is no problem even if an agent is added.

When treating various fibers or fiber products using the fiber treating agent composition of the present invention, the emulsion of this composition is adjusted to a predetermined concentration, and immersed, sprayed, roll-coated or the like to give the fiber. Attach. The amount of adhesion varies depending on the type of fiber and is not particularly limited, but is generally in the range of 0.01 to 10% by weight as the amount of quaternary ammonium salt-containing polysiloxane. Then, it may be dried by hot air blowing, a heating furnace or the like. Drying may be performed at 100 to 150 ° C. for 2 to 5 minutes, although it depends on the type of fiber.

There are no particular restrictions on the fibers or fiber products that can be treated with the fiber treatment composition of the present invention.
It is also effective for natural fibers such as silk, hemp, wool, angora and mohair, and synthetic fibers such as polyester, nylon, acrylic and spandex. Also, there is no limitation on the form and shape, staples, filaments, tows,
Not only raw materials such as yarn, but also various processed forms such as woven fabric, knitted fabric, wadding, and non-woven fabric can be treated with the fiber treating agent composition of the present invention.

[0047]

Industrial Applicability The quaternary ammonium salt-containing polysiloxane of the present invention is widely used as a fiber treatment composition for imparting excellent antibacterial properties, flexibility and washing resistance to various fibers or textile products. .

[0048]

EXAMPLES The present invention will be described below in detail with reference to Examples and Comparative Examples, but the present invention is not limited to the following Examples. In the following examples, the viscosities were all 25.
It is a value at ° C. <Structural analysis by ²⁹ Si-NMR> Sample 1.65
g, toluene 1.50 g, benzene-d ⁶ 0.20 g,
0.04 g of tris- (2,4-pentanedionate) chromium as a relaxation reagent was uniformly dissolved, and the diameter was 10 m.
m sample tube, Lambda 300
Using WB (JEOL), the peak of ²⁹ Si-NMR was observed by integrating 600 to 3,000 times.

[Synthesis Example 1] In a 1,000 ml glass flask equipped with a mechanical stirring blade, a cooling tube and a thermometer,
As the component (A), α represented by the following average structural formula (9),
308.3 g of ω-dihydroxydimethylsiloxane
(0.100 mol) and a 38% solids methanol solution 26 of 3- (trimethoxysilyl) propyldimethyloctadecyl ammonium chloride as the component (B) 26
1.1 g (0.200 mol) was charged and reacted at 70 ° C. for 2 hours under reflux of methanol. Next, an ester adapter was attached, and methanol was distilled off under aeration with nitrogen. Thereafter, the liquid temperature was set to 120 ° C., and the mixture was stirred for 4 hours under nitrogen. After completion of the reaction, a highly viscous colorless and transparent oily substance was obtained (A-1). ²⁹ about the obtained product
When the structure was identified by Si-NMR, the assignments were as shown in Table 1.

[0050]

Embedded image

[0051]

[Table 1]

From the results of the analysis and the reaction route, 95% of 3- (trimethoxysilyl) propyldimethyloctadecyl ammonium chloride reacted with the siloxane polymer, resulting in 60% as a structure represented by the following average structural formula (10).
%, 35 as a structure represented by the following average structural formula (11):
%. Table 3 shows the measurement results of the volatile content and the rotational viscosity.

[0053]

Embedded image

[Synthesis Example 2] (A) was placed in a 500 ml glass flask equipped with an ester adapter, a cooling tube and a thermometer.
Α, ω-dihydroxydimethylsiloxane 30 previously dehydrated and represented by the above average structural formula (9) as a component
8.3 g (0.050 mol) and N as the component (C)
10.3 g (0.050 mol) of -β- (aminoethyl) -γ-aminopropylmethyldimethoxysilane was charged and reacted at 120 ° C for 2 hours. Distillation of methanol by demethanol reaction was observed in the ester adapter. After cooling, 32.7 g (0.3%) of a 38% solids methanol solution of 3- (trimethoxysilyl) propyldimethyloctadecyl ammonium chloride as the component (B).
(025 mol), and reacted at 70 ° C. under reflux of methanol for 4 hours. Then, methanol was distilled off under nitrogen aeration, and then the solution was heated to 120 ° C. and stirred for 2 hours under a nitrogen aeration. After completion of the reaction, a viscous colorless and transparent oily substance was obtained (A-2). About the obtained product,
^{When the} structure was identified by ²⁹ Si-NMR, it was found that the compound was represented by the following average structural formula (12) on average.

[0055]

Embedded image

[Synthesis Example 3] (A) was placed in a 500 ml glass flask equipped with an ester adapter, a condenser, and a thermometer.
Α, ω-dihydroxydimethylsiloxane 30 previously dehydrated and represented by the above average structural formula (9) as a component
8.3 g (0.050 mol) and N as the component (C)
5.56 g (0.025 mol) of -β- (aminoethyl) -γ-aminopropylmethyltrimethoxysilane was charged and reacted at 120 ° C for 2 hours. Distillation of methanol by demethanol reaction was observed in the ester adapter. After cooling, 130.6 g of a 38% solids methanol solution of 3- (trimethoxysilyl) propyldimethyloctadecyl ammonium chloride as the component (B)
(0.100 mol), and methanol was distilled off under nitrogen aeration. Thereafter, the liquid temperature was set to 120 ° C., and the mixture was stirred for 2 hours under nitrogen. After the completion of the reaction, a viscous colorless and transparent oily substance was obtained (A-3). About the obtained product,
^{When the} structure was identified by ²⁹ Si-NMR, the assignments were on average those having the following structures.

[0057]

[Table 2]

From the results of the analysis and the reaction route, 85% of 3- (trimethoxysilyl) propyldimethyloctadecyl ammonium chloride was reacted with the siloxane polymer, and the structure represented by the above average structural formula (10) was 60%.
%, 25 as the structure represented by the average structural formula (11).
%. Table 3 shows the measurement results of the volatile content and the rotational viscosity.

[0059]

[Table 3] * Rotation viscometer

[Examples 1 to 3] 4 obtained in Synthesis Examples 1 to 3
Grade ammonium salt-containing polysiloxane (A-1), (A
-2), (A-3) 150 g of polyoxyethylene tridecyl ether (addition number of ethylene oxide = 1)
(0, HLB = 13.6), and after mixing, 160 g of deionized water was added and the mixture was stirred at high speed for 15 minutes with a homomixer to perform phase inversion and kneading. Further, 600 g of deionized water is added, and the mixture is 2,000 with a homomixer.
dilution by stirring for 15 minutes at rpm;
A milky emulsion was obtained.

Polyester / cotton blend (65% / 35%)
The broad cloth is immersed in an aqueous solution prepared to a silicone solid content of 2.0% by weight for 1 minute, squeezed using a roll under the condition of a squeezing ratio of 100%, dried at 135 ° C. for 1 minute, and further at 165 ° C. for 2 minutes. Heat treatment was performed to produce a treated cloth. The treated cloth obtained was treated with JIS L-0217103 method for 10 days.
Washing was carried out twice and the reduction rate of Staphylococcus aureus was compared by the shake flask method. In addition, the texture of the treated cloth before and after the washing treatment was examined by touch. Table 4 shows the results.

For comparison, 3- (trimethoxysilyl)
Using a 38% solids methanol solution of propyldimethyloctadecyl ammonium chloride, solids content 3.
A similar experiment was performed by preparing a 5% by weight aqueous solution. This is referred to as Comparative Example 1. Table 4 shows the results.

[0063]

[Table 4]

As can be seen from the above results, the fiber treatment composition of the present invention uses a washing-resistant antibacterial quaternary ammonium salt-containing polysiloxane, thereby making it possible to compare with the conventional silicone-based antibacterial agent. Thus, the fiber treatment and the antibacterial treatment can be performed simultaneously without containing alcohol.

Claims (6)

[Claims] 1. A quaternary ammonium salt-containing polysiloxane comprising at least one unit represented by the following general formula (1). Embedded image (Wherein, R ¹ is a substituted or unsubstituted monovalent organic group having 1 to 20 carbon atoms, R ² is a monovalent organic group containing at least one quaternary ammonium salt, and R ³ is represented by —OR ¹ . And p represents a positive number satisfying 2 ≦ p ≦ 2,000.) 2. A quaternary ammonium salt-containing polysiloxane having at least one terminal group represented by the following general formula (2). Embedded image (In the formula, R ¹ , R ² , R ³ , and p have the same meaning as described above. A is 0 or 1.) 3. A method according to claim 1, wherein R ² is a group represented by the following general formula (3): —CH ₂ CH ₂ CH ₂ N ⁺ R ⁴ R ⁵ R ⁶ Cl ⁻ (3) (wherein R ⁴ and R ⁵ are the same or different carbon atoms). Numbers 1-3
Is a monovalent hydrocarbon group, and R ⁶ is a monovalent hydrocarbon group having 1 to 30 carbon atoms. The quaternary ammonium salt-containing polysiloxane according to claim 1 or 2, which is a monovalent organic group represented by the formula: 4. A method according to claim 1, wherein R ² is represented by the following general formula (4): —CH ₂ CH ₂ CH ₂ N ⁺ (CH ₃ ) ₂ C _n H _{2n + 1} Cl ⁻ (4) (where n is a positive integer of 12 to 24) The quaternary ammonium salt-containing polysiloxane according to claim 3, which is represented by the following formula: (A) The following general formula (5): (Wherein, R ¹ and p have the same meanings as described above), and (B) the following general formula (6): (Wherein R ¹ , R ² , R ³ , and a have the same meanings as described above), and a dealcoholation reaction with an organosilane represented by the following formula: . 6. The method according to claim 1, wherein
A fiber treating agent composition containing a primary ammonium salt-containing polysiloxane as a main component.