JP3466582B2 - Antistatic agent for fiber - Google Patents

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to an antistatic agent for fibers. More specifically, it relates to an antistatic agent for fibers, which can impart antistatic properties to the fibers by post-processing.

[0002]

2. Description of the Related Art Conventionally, as an antistatic agent for fibers, for example, a combination of a cation polymer and a guanidine salt and / or an inorganic salt (JP-A-61-69884), an aminophosphate type phosphoric acid ester and a guanidine salt are used. It is known to use a combination of the above and Japanese Patent Publication No. 61-58592.

[0003]

However, JP-A-61-161
The antistatic agent described in Japanese Patent Publication No. 69884 has a problem that rust is generated depending on the material of the processing apparatus and a problem of scum caused by a complex with an anionic agent remaining in the cloth in the previous step. Also, Japanese Patent Publication Sho 61-5
In the antistatic agent described in Japanese Patent No. 8592, the antistatic ability is not sufficient for the presently required performance, and in addition to water spots (water droplets are attached to the fabric and the fabric is dried and dried) It is a ring-shaped stain that develops, and it tends to occur when the affinity between the fiber and the drug is small.). In addition, the conventional antistatic agent has a problem that the antistatic treatment becomes extremely difficult depending on the processing apparatus and the processing conditions, because foaming is severe in the processing apparatus. That is, an object of the present invention is to provide an antistatic agent that imparts excellent antistatic ability to fibers, and is excellent in rust prevention, suppression of water spot development, and low foaming property.

[0004]

Means for Solving the Problems As a result of intensive studies to achieve the above object, the present inventors have found that a compound having a specific water vapor pressure (saturated aqueous solution), a specific surfactant, and a specific phosphate ester. The inventors have found that the above problems can be solved by combining and and have reached the present invention. That is, the features of the antistatic agent for fibers of the present invention are that the saturated aqueous solution at 20 ° C. has a water vapor pressure of 2.0 to 16.7 mmHg (A) and a quaternary ammonium salt type cationic surfactant (B). And an aminophosphate type phosphoric acid ester (C) are contained as essential components. The present invention is also a fiber treated with the above antistatic agent.

[0005]

BEST MODE FOR CARRYING OUT THE INVENTION The compound (A) of the present invention may be an inorganic compound or an organic compound. As the inorganic compound, an alkali metal salt of nitric acid or hydrochloric acid, an alkaline earth metal salt of nitric acid or hydrochloric acid, an alkali metal salt of sulfuric acid, and the like can be used. Examples of the alkali metal salt of nitric acid include lithium nitrate, sodium nitrate, potassium nitrate and the like.
Examples of the alkaline earth metal salt of nitric acid include magnesium nitrate, calcium nitrate, barium nitrate and the like. Examples of the alkali metal salt of hydrochloric acid include lithium chloride, sodium chloride, potassium chloride and the like. Examples of the alkaline earth metal salt of hydrochloric acid include magnesium chloride, calcium chloride, barium chloride and the like. Examples of the alkali metal salt of sulfuric acid include lithium sulfate, sodium sulfate, potassium sulfate and the like. Among these, preferred are alkali metal salts of nitric acid or hydrochloric acid and alkaline earth metal salts of nitric acid or hydrochloric acid, and particularly preferred are lithium nitrate, calcium chloride and magnesium chloride.

As the organic compound, guanidine salt, carboxylic acid metal salt, saccharide and the like can be used. As the guanidine salt, guanidine hydrochloride, guanidine sulfamate,
Guanidine sulfate, guanidine methyl sulfate, guanidine ethyl sulfate and the like can be mentioned. As the carboxylic acid metal salt,
Examples thereof include alkali metal salts of carboxylic acids having 1 to 5 carbon atoms (including oxycarboxylic acid) such as acetate, formate and lactate. Examples of the acetate include lithium acetate, sodium acetate, potassium acetate and the like, examples of the formate include lithium formate and sodium formate, and examples of the lactate include lithium lactate and the like. Examples of the saccharide include sucrose, fructose, erythritol, sorbitol and the like. Of these, preferred are guanidine salts and carboxylic acid metal salts, more preferably guanidine salts and acetates, particularly preferably guanidine hydrochloride, guanidine sulfamate, guanidine sulfate, and guanidine methylsulfate.
Guanidine ethylsulfate, lithium acetate, sodium acetate, potassium acetate. These compounds (A) are 1
It can be used in one kind or a mixture of two or more kinds.

The water vapor pressure of the saturated aqueous solution of (A) at 20 ° C. is usually 2.0 to 16.7 mmHg, preferably 2.2 to 16.6 mmHg, and more preferably 2.5 to 1 mmHg.
It is 6.5 mmHg. Compounds less than 2.0 mmHg are not preferable because many of them have significant skin irritation such as sodium hydroxide (0.61 mmHg). 16.7m
If it exceeds mHg, the antistatic performance, especially the antistatic performance under low humidity tends to deteriorate. The water vapor pressure of the saturated aqueous solution of (A) at 20 ° C. is a literature value (for example,
Chemical manual basics [Maruzen], physics and chemistry textbooks [Zokabo] and the like) are used). If there is no literature value of the substance, it can be easily calculated from the humidity at 20 ° C. of the gas phase portion in the closed container containing the saturated aqueous solution of (A).

As the quaternary ammonium salt type cationic surfactant (B), aromatic and / or aliphatic compounds can be used,
Other than this, a polymer having a quaternary ammonium cation group can be used. As the aromatic and / or aliphatic compound,
Examples thereof include compounds represented by the general formula (1).

In the formula, R ^{1 to} R ⁴ each represent an aliphatic hydrocarbon group, an alicyclic hydrocarbon group or an aromatic hydrocarbon group,
The number of carbon atoms of these hydrocarbon groups is usually 1 to 20, preferably 1 to 18, and more preferably 1 to 16.

Examples of the aliphatic hydrocarbon group include methyl group, ethyl group, propyl group, butyl group, 2-ethylhexyl group, decyl group and undecyl group. Examples of the alicyclic hydrocarbon group include a cyclopentyl group,
Examples thereof include a cyclohexyl group and a 2-methylcyclohexyl group. Examples of the aromatic hydrocarbon group include a phenyl group, a tolyl group, a benzyl group, a xylyl group, a naphthyl group, a methylnaphthyl group, an ethylnaphthyl group and the like. Of these groups, an aliphatic hydrocarbon group is preferred.

Further, at least one hydrocarbon group among R ^{1 to} R ⁴ usually has 3 or more carbon atoms, preferably 4 to 18 carbon atoms.
And the total carbon number of R ^{1 to} R ⁴ is usually 8 to 23, preferably 9 to 21, and in some cases, more preferably 9 to 16, and particularly preferably 10 to 15.
Examples of Q include halogen such as chlorine and bromine, methosulfate, ethosulfate, hydroxide and carbonate. Of these, preferably halogen,
Methosulfate and ethosulfate.

As the compound represented by the general formula (1),
For example, cetyl trimethyl ammonium chloride, lauryl trimethyl ammonium methosulfate, benzyl trimethyl ammonium bromide, cetyl ethyl dimethyl ammonium carbonate, lauryl triethyl ammonium hydroxide, lauryl trimethyl ammonium ethosulfate, dibutyl dimethyl ammonium bromide, 2-ethylhexyl trimethyl ammonium methosulfate and dihexyl. Dimethyl ammonium bromide and the like can be mentioned.

The compound represented by the general formula (1) can be obtained by a known method, and usually a tertiary amine is converted into a quaternizing agent with a quaternizing agent.
It is obtained by grading. For example, dimethylsulfuric acid was added dropwise to an aqueous suspension of a tertiary amine compound while stirring at a reaction temperature of 5 to 50 ° C., followed by aging at the same temperature for 1 hour to obtain an aqueous solution, which was heated to 50 to 150 ° C. Dimethylsulfuric acid was added dropwise to the tertiary amine compound with stirring and the mixture was stirred at the same temperature for 1
The method of obtaining by aging for time can be illustrated.

There are various quaternizing agents for synthesizing the compound represented by the general formula (1). For example, the number of carbon atoms is 1.
~ 12 alkyl halides, dialkyl carbonates,
Dimethylsulfate, diethylsulfate and the like can be mentioned. Examples of the alkyl halide include methyl chloride, methyl bromide, ethyl bromide, butyl chloride, 2-ethylhexyl bromide, decyl chloride and the like. Examples of the dialkyl carbonate include dimethyl carbonate, diethyl carbonate and dibutyl carbonate.

Examples of the polymer having a quaternary ammonium cation group include quaternary ammonium cation group-containing vinyl (co) polymer, quaternary ammonium cation group-containing polyurethane, quaternary ammonium cation group-containing polyester, and mixtures thereof. To be Among these, preferred are quaternary ammonium cation group-containing vinyl (co) polymers.

As the monomer constituting the quaternary ammonium cation group-containing vinyl (co) polymer, a quaternary ammonium cation group-containing vinyl monomer can be used. For example, (meth) acryloxytrialkylammonium salt, (meth) ) Acryloxyalkylene trialkyl ammonium salts and the like can be mentioned.

Examples of the (meth) acryloxytrialkylammonium salt include (meth) acryloxytrimethylammonium chloride, (meth) acryloxydimethylethylammonium methosulfate, (meth) acryloxytrimethylammonium bromide, and (meth) acryloxydimethyl. Examples thereof include ethylammonium ethosulfate, (meth) acryloxytriethylammonium chloride, (meth) acryloxydimethylbutylammonium methosulfate, (meth) acryloxydimethylhexylammonium bromide and (meth) acryloxydimethyldecylammonium ethosulfate.

Examples of the (meth) acryloxyalkylene trialkylammonium salt include dialkylamino such as (meth) acryloxyethylenetrimethylammonium chloride, (meth) acryloxyethylenetrimethylammonium methosulfate and (meth) acryloxyethylenetrimethylammonium bromide. Examples thereof include quaternary products of alkyl (meth) acrylate. As the quaternizing agent used in the production of these quaternary ammonium cation group-containing monomers, the same ones as described above can be used.

Other quaternary ammonium cation group-containing vinyl monomers include quaternized compounds such as N, N-dialkylaminoacrylamide and diallylamine. For example, dimethylaminoethyl (meth) acrylamide, diethylaminoethyl (meth) acrylamide, alkyl halide, dimethylsulfate, diethylsulfate,
Examples thereof include those quaternized with dialkyl carbonate and the like.

(B) may be a quaternized product obtained by synthesizing a tertiary nitrogen-containing vinyl (co) polymer. From the viewpoint of quaternization efficiency, it is preferable to obtain a (co) polymer from a quaternary ammonium cation group-containing vinyl monomer. Further, (B) may be a copolymer of a vinyl monomer containing a quaternary ammonium cation group and another vinyl monomer, and a copolymer of a vinyl monomer containing a tertiary nitrogen and another vinyl monomer was synthesized. It may be quaternized later. From the viewpoint of quaternization efficiency, a copolymer of a vinyl monomer containing a quaternary ammonium cation group and another vinyl monomer is preferable.

The vinyl monomers that can be used in the copolymerization include the following (a) to (i). In the case of a copolymer, the molar ratio of (quaternary ammonium cation group-containing vinyl monomer) / (other vinyl monomer) is usually 1/100 to 100 / 0.1, preferably 50/100.
~ 100/1. The weight average molecular weight of the quaternary ammonium cation group-containing (co) polymer is usually 1,000 to 1.
From the viewpoint of easy solubility, it is preferably 2,000 to 30,000, more preferably 3,000.
It is 0 to 10,000.

(A) Vinyl hydrocarbon (a1) Aliphatic vinyl hydrocarbon: ethylene, propylene, butene, isobutylene, pentene, heptene, diisobutylene, octene, dodecene, octadecene, butadiene, isoprene, 1,4-pentadiene, 1 , 6-
Hexadiene, 1,7-octadiene, other α-
Olefin, etc. (A2) alicyclic vinyl hydrocarbon: cyclohexene,
(Di) cyclopentadiene, pinene, limonene, indene, vinylcyclohexene, ethylidene bicycloheptene and the like. (A3) Aromatic vinyl hydrocarbon: styrene, α-methylstyrene, vinyltoluene, 2,4-dimethylstyrene, ethylstyrene, isopropylstyrene, butylstyrene, phenylstyrene, cyclohexylstyrene,
Benzylstyrene, crotylbenzene, vinylnaphthalene, divinylbenzene, divinyltoluene, divinylxylene, divinylketone, trivinylbenzene, etc.

(B) Hydroxyl group-containing vinyl monomer hydroxystyrene, N-methylol (meth) acrylamide, hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, polyethylene glycol mono (meth) acrylate, (meth) allyl alcohol, Crotyl alcohol, isocrotyl alcohol, 1-buten-3-ol, 2-buten-1-ol, 2-butene-1,4-diol, propargyl alcohol, 2-hydroxyethylpropenyl ether, sucrose allyl ether and the like.

(C) Nitrogen-containing vinyl monomer (c1) Amino group-containing vinyl monomer: aminoethyl (meth) acrylate, dimethylaminoethyl (meth)
Acrylate, diethylaminoethyl (meth) acrylate, t-butylaminoethylmethacrylate, N-aminoethyl (meth) acrylamide, (meth) allylamine, morpholinoethyl (meth) acrylate, 4-vinylpyridine, 2-vinylpyridine, crotylamine,
N, N-dimethylaminostyrene, methyl α-acetaminoacrylate, vinylimidazole, N-vinylpyrrole, N-vinylthiopyrrolidone, N-arylphenylenediamine, aminocarbazole, aminothiazole, aminoindole, aminopyrrole, aminoimidazole, Aminomercaptothiazole, salts thereof and the like.

(C2) Amide group-containing vinyl monomer:
(Meth) acrylamide, N-methyl (meth) acrylamide, N-butyl acrylamide, diacetone acrylamide, N-methylol (meth) acrylamide,
N, N'-methylene-bis (meth) acrylamide, cinnamic acid amide, N, N-dimethylacrylamide, N, N
-Dibenzylacrylamide, methacrylformamide, N-methyl N-vinylacetamide, N-vinylpyrrolidone and the like. (C3) Nitrile group-containing vinyl monomer: (meth) acrylonitrile, cyanostyrene and the like. (D) Epoxy group-containing vinyl monomer glycidyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, p-vinylphenylphenyl oxide and the like.

(E) vinyl ester, vinyl ether,
Vinyl ketone vinyl acetate, vinyl butyrate, vinyl propionate,
Vinyl butyrate, diallyl phthalate, diallyl adipate, isopropenyl acetate, vinyl methacrylate, methyl 4-vinylbenzoate, cyclohexyl methacrylate, benzyl methacrylate, phenyl (meth) acrylate, vinyl methoxyacetate, vinyl benzoate, vinyl methyl ether, vinyl ethyl ether, vinyl Propyl ether, vinyl butyl ether, vinyl 2-ethylhexyl ether, vinyl phenyl ether, vinyl 2-methoxyethyl ether, methoxybutadiene, vinyl 2-butoxyethyl ether,
3,4-dihydro-1,2-pyran, 2-butoxy-2 '
-Vinyloxydiethyl ether, vinyl 2-ethylmercaptoethyl ether, vinyl methyl ketone, vinyl ethyl ketone, vinyl phenyl ketone, divinyl sulfide, p-vinyl diphenyl sulfide, vinyl ethyl sulfide, vinyl ethyl sulfone, divinyl sulfone, divinyl sulfoxide Side, dialkyl fumarate (two alkyl groups have 2 to 8 carbon atoms, straight chain,
Branched-chain or alicyclic group), dialkyl maleate (two alkyl groups are straight-chain, branched-chain or alicyclic group having 2 to 8 carbon atoms), poly (meth) ) Allyloxyalkanes [diaryloxyethane, triaryloxyethane, tetraallyloxyethane, tetraallyloxypropane, tetraallyloxybutane, tetrametaaryloxyethane, etc.] and the like.

(F) Alkyl (meth) acrylate Alkyl (meth) having an alkyl group having 1 to 50 carbon atoms
Acrylates, such as methyl (meth) acrylate,
Ethyl (meth) acrylate, propyl (meth) acrylate, butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, dodecyl (meth) acrylate, hexadecyl (meth) acrylate, heptadecyl (meth) acrylate, eicosyl (meth) acrylate, etc. . (G) Vinyl monomer having a polyalkylene glycol chain Polyethylene glycol (molecular weight 300) Mono (meth)
Acrylate, polypropylene glycol (molecular weight 50
0) Monoacrylate, methyl alcohol ethylene oxide 10 mol adduct (meth) acrylate, lauryl alcohol ethylene oxide 30 mol adduct (meth)
Acrylate etc. (H) Polyhydric alcohol poly (meth) acrylate ethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, trimethylolpropane tri (meth) acrylate, polyethylene glycol di ( (Meth) acrylate and the like.

(I) Other vinyl monomers acetoxystyrene, phenoxystyrene, ethyl α-
Ethoxy acrylate, isocyanatoethyl (meth) acrylate, cyanoacrylate, m-isopropenyl-α, α-dimethylmethylbenzyl isocyanate and the like.

In the present invention, (B) HLB (hydrophilicity-
The hydrophobic balance) value is usually 9 to 24, preferably 10
~ 23. In some cases, more preferably 12
-23, particularly preferably 13-22. When the HLB value is in this range, generation of water spots on the treated fiber can be suppressed, and a low foaming antistatic agent can be more easily obtained.

The HLB value means a value calculated by the Oda formula based on the organic conceptual diagram, and this calculation method is described, for example, in "Emulsification / solubilization technology" (Engineering book [shares], 1976). Has been done. Further, regarding the calculation of the organic value and the inorganic value for deriving the HLB value, the inorganic value table (1974, 1993, Sankyo Publishing Co., Ltd.) described in "Organic Conceptual Diagram -Basics and Applications-" , Reported by Fujita et al.). However, the inorganic value of the quaternary nitrogen portion is set to 400, and the organic and inorganic values of the counter ion (chlorine ion, bromine ion, methosulfate ion, etc.) of the surfactant are excluded and HLB is excluded.
Calculate the value. Preferred among these (B) are the compounds represented by the general formula (1).

Aminophosphate type phosphoric acid ester (C)
Examples of the amino acid phosphoric acid (mono, di) ester represented by the following general formula (2) and the amino alcohol phosphoric acid (mono, diester represented by the following general formula (3)
Di) esters can be used.

R ⁵ —NH—R ⁶ — (AO) m—OH (2)

In the general formula (2), R ⁵ and R ⁶ are, respectively, R ⁵ is monovalent, R ⁶ is divalent, an aliphatic hydrocarbon group or aromatic hydrocarbon group having 1 to 18 carbon atoms. Is. The total carbon number of R ⁵ and R ⁶ is usually 2 to 19, preferably 2 to
12, more preferably 2-8. When the total number of carbon atoms of R ⁵ and R ⁶ is within this range, the compatibility between the obtained antistatic agent and other agents (softening agent, etc.) will be further improved. m is usually 0 or 1 to 10, preferably 0 or 1
6, and more preferably 0 or 1-4. When m is in this range, reduction in the friction fastness of the dyeing dye is further reduced particularly when the dyed polyester fiber is treated.

In the general formula (3), R ⁷ , R ⁸ and R ⁹
Are respectively R ⁷ and R ⁸ are monovalent, R ⁹ is divalent,
It is an aliphatic hydrocarbon group or an aromatic hydrocarbon group having 1 to 18 carbon atoms. The total carbon number of R ^{7 to} R ⁹ is usually 3 to 20, preferably 3 to 12, and more preferably 3 to 9. R ⁷
When the total carbon number of R ⁹ to R ⁹ is in this range, the compatibility between the obtained antistatic agent and other agents (softening agent, etc.) is further improved. n is usually 0 or 1 to 10, preferably 0 or 1 to 6, and more preferably 0 or 1 to 4.
When n is in this range, the reduction in the friction fastness of the dyeing dye is further reduced particularly when the dyed polyester fiber is treated. AO in general formulas (2) and (3)
Represents an oxyalkylene group. The carbon number of AO is usually 2, 3 and / or 4, preferably 2 and / or 3. AO is usually formed by the addition of an alkylene oxide. As the alkylene oxide, ethylene oxide, propylene oxide, 1,2-, 1,4-, 1,3
-And 2,3-butylene oxide and the like.

Specific examples of R ^{5 to} R ⁹ include, as the aliphatic hydrocarbon group, for example, linear, branched or alicyclic hydrocarbon groups, which may be saturated or unsaturated. Good. Further, it may be a mixture of two or more kinds of groups such as linear and branched. As R ⁵ , R ⁷ and R ⁸ , linear saturated aliphatic hydrocarbon groups include methyl group, ethyl group, n-
Examples thereof include alkyl groups having 1 to 18 carbon atoms such as propyl group, n-butyl group, n-hexyl group, capryl group, octyl group, decyl group, lauryl group, tridecyl group, myristyl group, cetyl group and stearyl group. Examples of the branched saturated aliphatic hydrocarbon group include alkyl groups having 3 to 18 carbon atoms such as isopropyl group, isobutyl group, sec- or t-butyl group, neopentyl group and 2-ethylhexyl group.

Examples of the alicyclic saturated hydrocarbon group include alkyl groups having 5 to 10 carbon atoms such as cyclopentyl group, cyclohexyl group and adamantyl group. As the linear unsaturated aliphatic hydrocarbon group, a vinyl group, a propenyl group,
2 carbon atoms such as butenyl group, pentenyl group, hexenyl group, octenyl group, decenyl group, dodecenyl group, tridecenyl group, pentadecenyl group, oleyl group and ethynyl group
~ 18 alkenyl groups. The branched unsaturated aliphatic hydrocarbon group has 3 carbon atoms such as isopropenyl group.
~ 18 alkenyl groups. Examples of the alicyclic unsaturated hydrocarbon group include alkenyl groups having 6 to 10 carbon atoms such as cyclohexenyl group and cyclooctenyl group. Examples of the aromatic hydrocarbon group include groups having 6 to 18 carbon atoms such as phenyl group, benzyl group, tolyl group, xylyl group, naphthyl group and alkylnaphthyl group.

As R ⁶ and R ⁹ , straight-chain saturated aliphatic hydrocarbon groups include methylene group, ethylene group and 1,3-
Propylene group, 1,4-butylene group, 1,6-hexylene group, caprylene group, octylene group, decylene group, laurylene group, tridecylene group, myristyrene group, acetylene group, direct carbon number 1-18 etc. A chain alkylene group is mentioned. Examples of the branched saturated aliphatic hydrocarbon group include 1,2-propylene group, 1,2- and 1,3
-C3 such as butylene group and 2-ethylhexylene group
~ 18 alkylene groups.

Examples of the alicyclic saturated hydrocarbon group include alkylene groups having 5 to 10 carbon atoms such as cyclopentylene group, cyclohexylene group and adamantylene group. Examples of the linear unsaturated aliphatic hydrocarbon group include vinylene group, propenylene group, butenylene group, pentenylene group, hexenylene group, octenylene group, decenylene group, dodecenylene group, tridecenylene group, pentadecenylene group, oleylene group and ethynylene group. A linear alkenylene group having 2 to 18 carbon atoms can be mentioned. The branched unsaturated aliphatic hydrocarbon group has 3 to 18 carbon atoms such as 1-methylvinylene group.
Alkenylene group of is mentioned. Examples of the alicyclic unsaturated hydrocarbon group include alkenylene groups having 6 to 10 carbon atoms such as cyclohexenylene groups and cyclooctenylene groups. Further, as the aromatic hydrocarbon group, a phenylene group,
Examples thereof include groups having 6 to 18 carbon atoms such as a benzylene group, a tolylene group, a xylylene group, a naphthylene group, and an alkylnaphthylene group. Of these R ^{5 to} R ⁹ , preferred are aliphatic hydrocarbon groups, and more preferred are straight-chain saturated aliphatic hydrocarbon groups.

Examples of phosphoric acid (mono, di) esters of aminoalcohol represented by the general formula (2) include, for example, ethylaminoethanol monophosphate, butylaminoethanol monophosphate, benzylaminoethanol monophosphate, ethylaminoethanol diphosphate. Phosphate, butylaminoethanol diphosphate and benzylaminoethanol diphosphate, butylaminopropanol monophosphate, butylaminoethanol ethylene oxide 6 mol adduct monophosphate, benzylaminoethanol ethylene oxide 2 mol adduct diphosphate, ethylaminoethanol propylene oxide 4 Examples thereof include monophosphates of molar adducts.

Examples of the phosphoric acid (mono, di) ester of amino alcohol represented by the general formula (3) include dimethylaminoethanol monophosphate, diethylaminopropanol monophosphate, dibutylaminoethanol monophosphate, dimethylaminoethanol diphosphate and diethylamino. Propanol diphosphate and dibutylaminoethanol diphosphate, diethylaminopropanol ethylene oxide 2 mol Propylene oxide 2 mol Block addition monophosphate, dibutylaminopropanol ethylene oxide 2 mol Propylene oxide 2 mol Random addition monophosphate, dibutylaminoethanol ethylene oxide 10 mol Product monophosphate, diethylaminopropanol ethyleneoxy Monophosphate, such as 2 moles adduct.

As a method for producing (C), a known method is used, and for example, it can be easily obtained by introducing phosphoric anhydride into the alcohol of the general formula (2) or (3) and stirring. The reaction temperature at this time is preferably 0 to 150 ° C.,
More preferably, it is 20 to 90 ° C. Further, the reaction time is preferably 1 to 5 hours, more preferably 2 to 4 hours after the addition of phosphoric anhydride.

In this reaction, for example, if the reaction molar ratio of alcohol / phosphoric anhydride is 3/1, the monoester / diester is obtained in a molar ratio of about 1/1. Further, in the case of reacting water in the presence of alcohol in the reaction, most of it can be obtained as a monoester if the reaction molar ratio of alcohol / water / phosphoric anhydride is 2/1/1. . As another method of obtaining a phosphoric acid ester, there is a method of obtaining it from a reaction product of phosphorus oxychloride and an alcohol,
In this method, monoester and diester can be obtained in various ratios by changing the reaction molar ratio of alcohol / phosphorus oxychloride. In the case of the present invention, the monoester / diester molar ratio of (C) is not particularly limited.

Further, an inert solvent (for example, a hydrocarbon such as hexane or cyclohexane, a ketone such as acetone or methyl ethyl ketone, an aromatic hydrocarbon such as toluene or xylene) is used for the purpose of reducing the viscosity of the reaction system during the reaction. May be used. Preferred among (C) are the compounds represented by the general formula (3).

In the antistatic agent for fibers of the present invention,
The usage ratio of (A), (B) and (C) is (A) /
The mass ratio of (B) / (C) is usually 45 to 95 / 0.5 to
25 / 3-45. In some cases, preferably 5
0 to 90/1 to 20/3 to 40, more preferably 60
~ 90/1 to 15/5 to 30, particularly preferably 65 to
90/2 to 15/5 to 25. When the ratio of (A) is in this range, it is under low humidity (for example, 20 ° C., 30% R
In (H), the antistatic performance is further improved, and the occurrence of water spots on the treated fiber is further suppressed. When the ratio of (B) is in this range, the expected antistatic effect is easily obtained, the foaming property is improved, and the rust on the metal is reduced. When the ratio of (C) is in this range,
The anticorrosive property and the compatibility with other ionic agents are further improved.

The antistatic agent for fibers of the present invention may contain a softening agent and a rust preventive agent in addition to (A), (B) and (C), if necessary. Examples of the softening agent include a softening agent (J) using a (modified) silicone and an aliphatic compound. Examples of the softening agent (J) using (modified) silicone include amino-modified silicone,
The preferable range of the amino equivalent is 300 to 50,000.
Is. When the amino equivalent is in this range, the heat resistance (not causing yellowing of white [bleaching]) and flexibility of the treated cloth are further improved. As an aliphatic compound,
Examples include cationic surfactants (K) other than (B), anionic surfactants (L), and nonionic surfactants (N).

Typical examples of the cationic surfactant (K) other than (B) include amine salt type surfactants, quaternary ammonium salt type surfactants, pyridinium salt type surfactants and the like. To be Examples of the amine-type surfactants include Solomin A-type, Arcobel A-type, Sapamine A-type, and imidazoline (salt) type surfactants. Examples of the quaternary ammonium salt type surfactants include those obtained by converting a quaternary ammonium salt with a quaternizing agent from a solomine A type, an Acobel A type, a sapamin A type or an imidazoline type tertiary amine compound. As the quaternizing agent, the above-mentioned ones can be used. Examples of the pyridinium salt include stearamidomethylpyridinium chloride.

Examples of the anionic surfactant (L) include mono (di) alkyl (C8-24) sulfosuccinate, polyhydric alcohol (C2-10, hydroxyl group 2).
-10) Fatty acid (C8-24) ester sulfate ester salt etc. are mentioned. As the counterion of (L), an alkali metal such as sodium or an inorganic alkali substance such as ammonia, and an organic alkali substance such as an amine compound such as (mono-, di-, tri) ethanolamine or (mono, di, tri) alkylamine Is mentioned. As the nonionic surfactant (N), a polyhydric alcohol (C2-10, hydroxyl group 2-10) fatty acid (C8-24) ester or polyvalent alkylamine (C1-10, amino group number) Two
-10) fatty acid (C8-24) amides and the like.

As the rust preventive, inorganic rust preventives (corrosion inhibitors) and organic rust preventives can be used. Examples of the inorganic rust preventives include sodium chromate, sodium nitrite, sodium silicate and sodium polyphosphate. Examples of the organic rust preventive agent include aliphatic and / or
Alternatively, aromatic carboxylic acid (having 10 to 30 carbon atoms), metallic soap (calcium oleate, calcium naphthenate, magnesium lanophosphate, etc.), petroleum sulfonate salt (sodium salt, calcium salt, magnesium salt, etc.), polyhydric alcohol ( Fatty acid (C8-24) ester of C2-10, hydroxyl group C2-10, fatty acid (C8-30) salt of alkylamine (C8-24), phosphate ester salt (2-ethyl) Hexylphosphoric acid [mono, di] sodium salt, lauryl alcohol phosphoric acid [mono, di]
Ester triethanolamine salt, etc.) and the like.
Among these, polyphosphates, metal soaps, salts of petroleum sulfonates, fatty acid esters of polyhydric alcohols, fatty acid salts of alkylamines and phosphoric acid ester salts are preferable, and fatty acid esters of polyhydric alcohols and phosphoric acid are more preferable. It is an ester salt.

In the antistatic agent for fibers of the present invention, if necessary, a solvent, a preservative, a water repellent, an oil repellent, a defoaming agent, a dye discoloration preventing agent, a fluorescent whitening agent, a sequestering agent, a leveling agent, Antibacterial agents, bactericides, antifungal agents, fragrances and the like can be contained. Examples of the solvent include water-soluble organic solvents such as methyl alcohol, ethyl alcohol, isopropyl alcohol and ethylene glycol, water, and mixtures thereof. As the preservative, for example, an isothiazoline compound (2-methyl-4-isothiazoline-3-
On, 5-chloro-2-methyl-4-isothiazoline-
3-on).

Examples of the defoaming agent include mineral oil-based defoaming agents, silicone-based defoaming agents, metal soap-based defoaming agents, and polyether-based defoaming agents (for example, Nopco 8034L manufactured by San Nopco Co., Ltd., Formaster 1407K, SN deformer 170, SN-500E, etc.). Examples of the dye discoloration preventing agent include hypophosphorous acid, hypophosphite (sodium, ammonium, etc.), ammonium dihydrogen phosphate and the like. As the fluorescent whitening agent, for example, Kayaphor AS-150 (Nippon Kayaku Co., Ltd.)
Manufactured) and the like. Examples of the sequestering agent include ethylenediaminetetraacetic acid sodium salt, sodium nitrilotriacetate, and polycarboxylic acid sodium salt having a weight average molecular weight of 20,000 or less.

100 in total of (A), (B) and (C)
The amount of each of these components added with respect to parts by mass is as follows. The softening agent is preferably 300 parts by mass or less, more preferably 50 to 200 parts by mass. The rust preventive agent is
Preferably 50 parts by mass or less, more preferably 0.1 to
10 parts by mass. The solvent is preferably 2000 parts by mass or less, more preferably 100 to 1000 parts by mass. The water repellent is preferably 200 parts by mass or less, more preferably 50 to 150 parts by mass. The oil repellent is preferably 200 parts by mass or less, more preferably 50 to 150.
Parts by mass. The leveling agent is preferably 300 parts by mass or less, more preferably 50 to 200 parts by mass. Of the above optional components other than these, each is preferably 30
It is not more than 10 parts by mass, more preferably 0.1 to 10 parts by mass. The total addition amount of each of the above optional components excluding the solvent is preferably 0.5 to 1000 parts by mass based on 100 parts by mass of (A), (B) and (C).

The antistatic agent for fibers of the present invention comprises (A),
(B), (C) and optionally a solvent, a water repellent, an oil repellent,
Antibacterial agent, bactericidal agent, antifungal agent, fragrance, rust preventive agent, antiseptic agent, softening agent, defoaming agent, dye discoloration preventing agent, fluorescent whitening agent, sequestering agent, smoothing agent, etc. are mixed by a known method. It is obtained by As the form of the antistatic agent of the present invention, all the components may be mixed in advance as an antistatic agent, and this may be treated into fibers, or each component may be mixed or a part of the components may be mixed. The fiber may be treated (mixing all the components on the fiber) for each of a plurality of component groups.

Examples of fibers to which the antistatic agent for fibers of the present invention can be applied include natural fibers such as cotton, wool, silk and hemp; synthetic fibers such as polyester, nylon, acrylic and spandex, and semi-fibers such as rayon and acetate. Examples include synthetic fibers. Further, it can be applied to a mixed fiber of cotton and polyester, wool and polyester, and the like. Further, the antistatic agent for fibers of the present invention can be applied regardless of the processing form of these fibers such as cotton, yarn and knitted fabric.

As a method for applying the antistatic agent for fibers of the present invention to the fibers, if necessary, after diluting with water and a hydrophilic organic solvent such as isopropyl alcohol, the usual methods such as padding method, dipping method and spray method are used. A treatment method can be applied. The dilution ratio at this time is the solid content concentration (total concentration of each component excluding the solvent), and preferably 0.0
It is 1 to 40 mass%. The amount of use of the antistatic agent of the present invention is preferably 0.01 to, based on the mass of the fiber, in terms of solid content (meaning that when a solvent is used, it is converted into the remaining amount excluding this). 5% by mass, more preferably 0.02 to 3% by mass, particularly preferably 0.03 to
It is 1.5% by mass.

[0055]

EXAMPLES The present invention will be further described below with reference to examples, but the present invention is not limited thereto. In the following, parts and% represent parts by mass and% by mass, respectively.
The HLB value of (B) used is a value calculated by the Oda formula. In addition, regarding the calculation of the organic value and the inorganic value for deriving the HLB value, "organic conceptual diagram-basic and applied-"
(Showa 59, Sankyo Publishing Co., Ltd.) Inorganic value table (Showa 49, Fujita et al. Reported value). However,
The calculation was performed by setting the inorganic value of the quaternary nitrogen portion to 400, and further excluding the organic value and inorganic value of the counter ion (chlorine ion, bromine ion, methosulfate ion, etc.) of the activator.

Production Example 1 A mixture of the following compounds was prepared at room temperature (20 to 25 ° C.) to obtain 1,000 parts of the fiber antistatic agent (D1) of the present invention containing 30% of the active ingredient. A1: Guanidine sulfamate [steam pressure of saturated aqueous solution at 20 ° C .: 16.5 mmHg] 220 parts B1: hexyltrimethylammonium chloride [HLB value: 22.2] 30 parts C1: N, N-dimethylaminoethanol phosphoric acid Ester (monoester: diester molar ratio 1: 1) 50 parts solvent: water 700 parts

Production Example 2 A mixture of the following compounds was prepared at room temperature, and an antistatic agent for fibers (D2) 1,000 of the present invention containing 30% of active ingredient was prepared.
I got a part. A1: Guanidine sulfamate 220 parts B2: Cetyltrimethylammonium methosulfate [HLB value: 10.5] 30 parts C1: N, N-Dimethylaminoethanol phosphate ester (monoester: diester molar ratio 1: 1) 50 parts Solvent: Isopropyl alcohol 40 parts Water 660 parts

Production Example 3 A mixture of the following compounds was prepared at room temperature, and an antistatic agent for fibers (D3) of the present invention having an active ingredient content of 30% (D3) 1,000 was prepared.
I got a part. A2: potassium acetate [steam pressure of saturated aqueous solution at 20 ° C .: 3.7 mmHg] 70 parts A1: guanidine sulfamate 200 parts B3: lauryltrimethylammonium methosulfate [HLB value: 13.3] 12 parts C1: N, N -Phosphate ester of dimethylaminoethanol (monoester: diester molar ratio 1: 1) 18 parts Solvent: isopropyl alcohol 40 parts Water 660 parts

Production Example 4 An antistatic agent for fibers (D4) of the present invention containing 1,000% of an active ingredient was prepared by preparing a mixture of the following compounds at room temperature.
I got a part. A2: potassium acetate 50 parts A1: guanidine sulfamate 100 parts B3: lauryltrimethylammonium methosulfate 45 parts C1: N, N-dimethylaminoethanol phosphate ester (monoester: diester molar ratio 1: 1) 105 parts solvent: Isopropyl alcohol 40 parts Water 660 parts

Production Example 5 An antistatic agent (D5) 1,000 for fibers of the present invention containing 30% of active ingredient was prepared by preparing a mixture of the following compounds at room temperature.
I got a part. A2: Potassium acetate 30 parts A1: Guanidine sulfamate 150 parts B3: Lauryltrimethylammonium methosulfate 60 parts C1: N, N-Dimethylaminoethanol phosphate ester (monoester: diester molar ratio 1: 1) 60 parts Solvent: Isopropyl alcohol 40 parts Water 660 parts

Production Example 6 An antistatic agent for fibers (D6) of the present invention having an active ingredient content of 30% was prepared by preparing a mixture of the following compounds at room temperature.
I got a part. A2: Potassium acetate 47 parts A1: Guanidine sulfamate 160 parts B3: Lauryltrimethylammonium methosulfate 3 parts C1: N, N-Dimethylaminoethanol phosphate ester (monoester: diester molar ratio 1: 1) 90 parts Solvent: Isopropyl alcohol 40 parts Water 660 parts

Production Example 7 A mixture of the following compounds was prepared at room temperature, and the antistatic agent for fibers (D7) 1,000 of the present invention containing 30% of the active ingredient was prepared.
I got a part. A2: potassium acetate 50 parts A1: guanidine sulfamate 100 parts B3: lauryltrimethylammonium methosulfate 30 parts C1: N, N-dimethylaminoethanol phosphate ester (monoester: diester molar ratio 1: 1) 120 parts solvent: Isopropyl alcohol 40 parts Water 660 parts

Production Example 8 A mixture of the following compounds was prepared at room temperature, and the antistatic agent for fibers (D8) 1,000 of the present invention containing 30% of the active ingredient was prepared.
I got a part. A1: Guanidine sulfamate 265 parts B3: Lauryltrimethylammonium methosulfate 20 parts C1: N, N-Dimethylaminoethanol phosphate ester (monoester: diester molar ratio 1: 1) 15 parts Solvent: Isopropyl alcohol 20 parts Water 680 Department

Production Example 9 An antistatic agent for fibers (D9) of the present invention having an active ingredient content of 30% was prepared by preparing a mixture of the following compounds at room temperature.
I got a part. A2: Potassium acetate 160 parts B3: Lauryl trimethyl ammonium methosulfate 45 parts C1: N, N-Dimethylaminoethanol phosphate ester (monoester: diester molar ratio 1: 1) 95 parts Solvent: Isopropyl alcohol 40 parts Water 660 parts

Production Example 10 A mixture of the following compounds was prepared at room temperature, and an antistatic agent for fibers (D10) 100 of the present invention containing 30% of active ingredient was prepared.
I got 0 copies. A1: Guanidine sulfamate 220 parts B3: Lauryltrimethylammonium methosulfate 30 parts C1: N, N-Dimethylaminoethanol phosphate ester (monoester: diester molar ratio 1: 1) 50 parts Solvent: water 700 parts

Production Example 11 A mixture of the following compounds was prepared at room temperature, and an antistatic agent for fibers (D11) 1,00 of the present invention containing 30% of active ingredient was prepared.
I got 0 copies. A1: Guanidine sulfamate 220 parts B4: Stearyltrimethylammonium methosulfate [HLB value: 9.5] 30 parts C1: N, N-Dimethylaminoethanol phosphate ester (monoester: diester molar ratio 1: 1) 50 parts Solvent: Isopropyl alcohol 40 parts Water 660 parts

Production Example 12 An antistatic agent for fibers (D12) of the present invention containing 30% of active ingredient was prepared by preparing a mixture of the following compounds at room temperature.
I got 0 copies. A2: Potassium acetate 80 parts A1: Guanidine sulfamate 200 parts B3: Lauryl trimethyl ammonium methosulfate 5 parts C1: N, N-Dimethylaminoethanol phosphate ester (monoester: diester molar ratio 1: 1) 15 parts Solvent: Isopropyl alcohol 40 parts Water 660 parts

Production Example 13 A mixture of the following compounds was prepared at room temperature, and an antistatic agent for fibers (D13) of the present invention containing 30% of the active ingredient (D13), 100
I got 0 copies. A2: potassium acetate 35 parts A1: guanidine sulfamate 100 parts B3: lauryltrimethylammonium methosulfate 45 parts C1: N, N-dimethylaminoethanol phosphate ester (monoester: diester molar ratio 1: 1) 120 parts solvent: Isopropyl alcohol 40 parts Water 660 parts

Production Example 14 An antistatic agent for fibers (D14) of the present invention containing 30% of active ingredient was prepared by preparing a mixture of the following compounds at room temperature.
I got 0 copies. A2: Potassium acetate 30 parts A1: Guanidine sulfamate 180 parts B3: Lauryltrimethylammonium methosulfate 70 parts C1: N, N-Dimethylaminoethanol phosphate ester (monoester: diester molar ratio 1: 1) 20 parts Solvent: Isopropyl alcohol 40 parts Water 660 parts

Production Example 15 A mixture of the following compounds was prepared at room temperature, and an antistatic agent for fibers (D15) 1,00 of the present invention containing 30% of active ingredient was prepared.
I got 0 copies. A2: Potassium acetate 58 parts A1: Guanidine sulfamate 200 parts B3: Lauryl trimethyl ammonium methosulfate 2 parts C1: N, N-Dimethylaminoethanol phosphate ester (monoester: diester molar ratio 1: 1) 40 parts Solvent: Isopropyl alcohol 40 parts Water 660 parts

Production Example 16 A mixture of the following compounds was prepared at room temperature, and an antistatic agent for fibers (D16) 1,00 of the present invention containing 30% of active ingredient was prepared.
I got 0 copies. A2: Potassium acetate 30 parts A1: Guanidine sulfamate 130 parts B3: Lauryltrimethylammonium methosulfate 10 parts C1: N, N-Dimethylaminoethanol phosphate ester (monoester: diester molar ratio 1: 1) 130 parts Solvent: Isopropyl alcohol 40 parts Water 660 parts

Production Example 17 A mixture of the following compounds was prepared at room temperature, and an antistatic agent for fibers (D17) 1,00 of the present invention containing 30% of active ingredient was prepared.
I got 0 copies. A2: Potassium acetate 40 parts A1: Guanidine sulfamate 200 parts B3: Lauryltrimethylammonium methosulfate 51 parts C1: N, N-Dimethylaminoethanol phosphate ester (monoester: diester molar ratio 1: 1) 9 parts Solvent: Isopropyl alcohol 40 parts Water 660 parts

Comparative Production Example 1 A mixture of the following compounds was prepared at room temperature to obtain 1,000 parts of a comparative antistatic agent (E1) containing 30% of the active ingredient. A'1: guanidine phosphate [vapor pressure in saturated aqueous solution at 20 ° C. 16.9 mmHg] 220 parts B3: lauryltrimethylammonium methosulfate 30 parts C1: N, N-dimethylaminoethanol phosphate ester (monoester: diester Molar ratio 1: 1) 50 parts solvent: isopropyl alcohol 40 parts water 660 parts

Comparative Production Example 2 A mixture of the following compounds was prepared at room temperature to obtain 1,000 parts of a comparative antistatic agent (E2) containing 30% of the active ingredient. A1: Guanidine sulfamate 240 parts B3: Lauryltrimethylammonium methosulfate 60 parts Solvent: Isopropyl alcohol 40 parts Water 660 parts

Comparative Production Example 3 A mixture of the following compounds was prepared at room temperature to obtain 1,000 parts of a comparative antistatic agent (E3) containing 30% of the active ingredient. A1: Guanidine sulfamate 250 parts C1: Phosphoric acid ester of N, N-dimethylaminoethanol (monoester: diester molar ratio 1: 1) 50 parts Solvent: isopropyl alcohol 40 parts Water 660 parts

Comparative Production Example 4 A mixture of the following compounds was prepared at room temperature to obtain 1,000 parts of a comparative antistatic agent (E4) containing 30% of the active ingredient. B3: Lauryl trimethyl ammonium methosulfate 90 parts C1: N, N-Dimethylaminoethanol phosphate ester (monoester: diester molar ratio 1: 1) 210 parts Solvent: Isopropyl alcohol 40 parts Water 660 parts

Evaluation of Foaming Property, Rust Producing Property, and Compatibility with Anionic Surfactant The antistatic agent for fibers (D
1) to (D17) and the comparative antistatic agents for fibers (E1) to (E4) produced in Comparative Production Examples 1 to 4, respectively, are used for foamability, rust prevention, and compatibility with anion activators. Was evaluated. The evaluation results are shown in Tables 1 to 3. In addition, each evaluation method is as follows. (1) 50 ml of a 1% by mass foaming antistatic agent was placed in a 100 ml graduated cylinder equipped with a stopper and shaken 20 times (stroke length: 30
cm, shaking speed: 20 times / 5 seconds), and after 1 minute, measure the amount of foam (ml) from the liquid surface. Measurement temperature is 40 ℃
Is. When the amount of bubbles is 20 mm or less, it is judged as good.

(2) 50 ml of a 1% by weight aqueous solution of an antirust agent was placed in a 100 ml glass beaker and the pin needle No. 50 (manufactured by Lion Office Machinery, material: iron [nickel plated], shape: [length: 2
7 mm, thickness: 0.7 mm], washed with diethyl ether) 5 pieces bundled with cotton sewing thread 2 sets (10 pieces in total) hung from the top of the beaker and immersed to half the liquid surface Leave at 25 ° C for 72 hours. After leaving, take out the pin needles and count the number of pin needles with rust. When the number of pin needles with rust is 0 or 1, it is judged that the rust prevention property is good.

(3) Compatibility with anionic surfactant 50 ml of 1 mass% aqueous solution of antistatic agent and 50 ml of sodium lauryl sulfate (first-grade reagent) aqueous solution (concentration: 0.5 mass%) 20
After stirring and mixing with ml, the mixture is left at 40 ° C. for 5 hours. The appearance of the mixed solution after standing is visually evaluated according to the following criteria. [Judgment] ○: No scum / aggregate was generated ○ △: Very little scum / aggregate was observed △: Slight scum / aggregate was observed △ ×: A little more scum / aggregate was observed × : Many scum and aggregates

[0080]

[Table 1]

[0081]

[Table 2]

[0082]

[Table 3]

Examples and Comparative Examples Antistatic agents for fibers (D
1) to (D17) and the comparative antistatic agents for fibers (E1) to (E4) produced in Comparative Production Examples 1 to 4, respectively, were used to fabricate fibers under the following conditions (Table 4). Table 5 shows the evaluation results of the untreated cloth and the following test methods. The cloth used in the test was dyed (Green
n), polyester taffeta after reduction cleaning.

[0084]

[Table 4]

Test method (4) Friction electrification voltage JIS L 1094 Test method for electrostatic properties of woven and knitted fabrics (1997 edition) 5.2. Follow the friction electrification voltage measurement method. However, the measured temperature and humidity are 20 ° C and 30% RH.
And 20 ° C / 40% RH. And two levels. The lower the measured voltage in Table 5, the better the antistatic effect. (5) Water spot 20 ° C / 40% RH. In the room of (1), one drop of water is dropped on the treated cloth and untreated cloth, and the cloth is naturally dried at room temperature. The state of occurrence of ring-shaped spots (water spots) where water drops spread around the area where water was dropped on the dry cloth was visually determined based on the following criteria. [Judgment] ○: No water spots (ring spots) were generated ○ △: Water spots were observed very slightly △: Water spots were observed slightly △ ×: Water spots were observed slightly ×: Water spots were observed many Is recognized

[0086]

[Table 5]

From Tables 1 to 5, the antistatic agent for fibers of the present invention not only imparted an excellent antistatic effect to the fibers, but also caused little water spots, and further had a low foaming property and an excellent effect. It can be seen that it has antirust property and excellent compatibility with the anionic surfactant.

[0088]

INDUSTRIAL APPLICABILITY The antistatic agent for fibers of the present invention imparts excellent antistatic properties to the fibers, suppresses the development of water spots, has a low foaming property, is rust preventive and has other agents (especially an anionic interface). Excellent compatibility with active agents). Therefore, the antistatic agent for fibers of the present invention is extremely suitable for the antistatic treatment of natural fibers, compound fiber, and mixed spun and knitted fibers thereof.

─────────────────────────────────────────────────── ─── Continued Front Page (51) Int.Cl. ⁷ Identification Code FI C09K 3/16 108 C09K 3/16 108D D06M 11/11 D06M 11/11 11/55 11/55 11/65 11/65 13 / 292 13/292 13/463 13/463 (56) Reference JP 55-50082 (JP, A) JP 58-149376 (JP, A) JP 58-144176 (JP, A) JP Flat 10-183469 (JP, A) JP-B-54-8800 (JP, B1) (58) Fields investigated (Int.Cl. ⁷ , DB name) D06M 13/00-15/72 F term (4L033)

Claims (5)

(57) [Claims] 1. A compound (A) having a saturated aqueous solution having a water vapor pressure of 2.0 to 16.7 mmHg at 20 ° C., a quaternary ammonium salt type cationic surfactant (B), and an aminophosphate type phosphoric acid ester (C). ) And an antistatic agent for fibers, which are contained as essential components. 2. (A) is an alkali metal salt of nitric acid or hydrochloric acid, an alkaline earth metal salt of nitric acid or hydrochloric acid, an alkali metal salt of sulfuric acid, a guanidine salt, a carboxylic acid metal salt,
And at least one compound selected from sugars.
The antistatic agent described. 3. The antistatic agent according to claim 1, wherein the HLB value of (B) is 9 to 24. 4. The mass ratio of (A) / (B) / (C) is 4
5 to 95 / 0.5 to 25/3 to 45.
The antistatic agent according to any one of 1. 5. A fiber treated with the antistatic agent according to claim 1.