Antistatic treatment agent for fibers, antistatically treated fiber, and method for producing antistatically treated fiber

Abstract

To provide an antistatic treatment agent for fibers exhibiting excellent water absorbency and excellent antistatic performance after washing, a fiber exhibiting excellent water absorbency and antistatic performance after washing, and a method for producing the same.SOLUTION: An antistatic treatment agent for fibers, wherein, with respect to nonvolatile components, a content of at least one selected from the following compound (A) and an acid salt of the compound (A) is 6 to 100 mass%. Compound (A): an imidazoline compound having an unsaturated hydrocarbon group with 15 to 21 carbon atoms.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to an antistatic agent for fibers, antistatically treated fibers, and a method for producing antistatically treated fibers. [Background technology]

[0002] In general, synthetic fibers are non-conductive and hydrophobic, and are easily charged with static electricity due to friction, etc. When synthetic fibers are used in clothing, the generation of static electricity not only reduces workability and comfort, but also makes the fabric more susceptible to the adhesion of soiling substances. Therefore, clothing made of synthetic fibers requires the use of antistatic finishing agents.

[0003] Conventionally, amine compounds such as those described in Patent Document 1 have been used as antistatic finishing agents, but they fall off during home laundering, making it impossible to obtain a sustained antistatic effect. In an attempt to improve washing durability, a method has been proposed in which a diacrylate copolymer having a cationic functional group, such as that described in Patent Document 2, is used as an antistatic finishing agent. However, while washing durability is good, the antistatic properties before washing are insufficient and the texture of the treated fabric is impaired. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Japanese Patent Application Publication No. 7-82669 [Patent Document 2] Patent Publication No. 2021-107599 Summary of the Invention [Problem to be solved by the invention]

[0005] Furthermore, conventional antistatic finishing agents have had the water absorbency of treated fabrics but poor antistatic properties after washing, or have had good antistatic properties after washing but poor water absorbency; there have been no agents that have both water absorbency and antistatic properties after washing. In other words, the object of the present invention is to provide an antistatic agent having excellent water absorbency and antistatic properties after washing, antistatically treated fibers to which an antistatic agent having excellent water absorbency and antistatic properties after washing is attached, and a method for producing antistatically treated fibers having excellent water absorbency and antistatic properties after washing. [Means for solving the problem]

[0006] As a result of intensive research aimed at solving the above-mentioned problems, the present inventors have found that these problems can be solved by including a specific amount of at least one selected from a specific compound (A) and an acid salt thereof, and have arrived at the present invention. That is, the present invention includes the following aspects. <1> An antistatic finishing agent for fibers, wherein the proportion of at least one selected from the following compound (A) and an acid salt of the following compound (A) is 6 to 100% by weight relative to the nonvolatile content: Compound (A): an imidazoline compound having an unsaturated hydrocarbon group having 15 to 21 carbon atoms <2> The compound (A) is at least one selected from the group consisting of a compound represented by the following general formula (1) and a compound represented by the following general formula (2): <1> The antistatic finishing agent for fibers according to claim 1. [ka] (In formula (1), R 1 represents an unsaturated hydrocarbon group having 15 to 21 carbon atoms, and X represents an amino group or a hydroxy group. [ka] (In formula (2), R 2 represents an unsaturated hydrocarbon group having 15 to 21 carbon atoms, Y represents -O- or -NH-, and R 3 represents an alkyl group having 1 to 21 carbon atoms or an unsaturated hydrocarbon group having 15 to 21 carbon atoms. <3> R in the general formula (2) 3 is an alkyl group having 1 to 15 carbon atoms; <2> The antistatic finishing agent for fibers according to claim 1. <4> The compound (A) and the acid salt of the compound (A) include at least one selected from the compound represented by the general formula (1) and an acid salt thereof. <2> or <3> The antistatic finishing agent for fibers according to claim 1. <5> the proportion of at least one compound selected from the group consisting of the compound represented by the general formula (2) and an acid salt thereof in the nonvolatile content is less than 35% by weight; <2> ~ <4> The antistatic finishing agent for fibers according to any one of the preceding claims. <6> the proportion of at least one selected from the compound (A) and an acid salt of the compound (A) in the nonvolatile content is 50 to 100% by weight; <1> ~ <5> The antistatic finishing agent for fibers according to claim 1. <7> The iodine value of the compound (A) is 35 to 150 g I / 100 g. <1> ~ <6> The antistatic finishing agent for fibers according to any one of the preceding claims. <8> The acid value of the non-volatile matter is 0.2 to 260 mg KOH / g. <1> ~ <7> The antistatic finishing agent for fibers according to any one of the preceding claims. <9> For textile materials, <1> ~ <8> 10. A method for producing antistatic treated fibers, comprising a step of applying the antistatic agent for fibers according to any one of claims 1 to 9. <10> For textile materials, <1> ~ <8> 1. An antistatic treated fiber to which the antistatic treating agent for fibers according to any one of claims 1 to 9 is adhered. [Effects of the Invention]

[0007] The antistatic agent for fibers of the present invention can impart excellent water absorbency and antistatic properties after washing. The antistatic treated fiber of the present invention is excellent in water absorbency and antistatic properties after washing. DETAILED DESCRIPTION OF THE INVENTION

[0008] The antistatic agent for fibers of the present invention contains a specific amount of at least one selected from a specific compound (A) and an acid salt of compound (A), which will be explained in detail below.

[0009] [Compound (A)] The antistatic finishing agent for fibers of the present invention contains at least one compound selected from compound (A), which is an imidazoline compound having an unsaturated hydrocarbon group having 15 to 21 carbon atoms, and its acid salt. The imidazoline compound having an unsaturated hydrocarbon group having 15 to 21 carbon atoms is not particularly limited as long as it is a compound having an imidazoline ring and an unsaturated hydrocarbon group having 15 to 21 carbon atoms in the molecule.

[0010] The iodine value of compound (A) is not particularly limited, but is preferably 35 to 150 gI2 / 100 g from the viewpoint of static stability. The upper limit of the iodine value is more preferably 145 gI2 / 100 g, even more preferably 140 gI2 / 100 g, and particularly preferably 135 gI2 / 100 g. On the other hand, the lower limit of the iodine value is more preferably 40 gI2 / 100 g, even more preferably 45 gI2 / 100 g, and particularly preferably 50 gI2 / 100 g. Also, for example, 40 to 140 gI2 / 100 g is more preferable, and 50 to 135 gI2 / 100 g is more preferable. The iodine value in the present invention is determined by the method described in the Examples.

[0011] There are no particular limitations on the compound (A) and the acid salt of compound (A) as long as they are imidazoline compounds having an unsaturated hydrocarbon group having 15 to 21 carbon atoms and acid salts thereof. However, from the viewpoint of increasing the number of adsorption points with fibers, they are preferably at least one selected from the compound represented by the general formula (1) and acid salts thereof, and the compound represented by the general formula (2) and acid salts thereof, and more preferably at least one selected from the compound represented by the general formula (1) and acid salts thereof.

[0012] In formula (1), R 1 represents an unsaturated hydrocarbon group having 15 to 21 carbon atoms, and from the viewpoint of antistatic properties after washing, the upper limit of the number of carbon atoms is preferably 19, more preferably 17. On the other hand, the lower limit of the number of carbon atoms is preferably 17. R 1 Specifically, the alkyl group preferably has 15 to 19 carbon atoms, and more preferably has 15 to 17 carbon atoms. In formula (1), X represents an amino group or a hydroxy group, with an amino group being preferred in terms of the adsorptive power to fibers, and a hydroxy group being preferred in terms of suppressing coloration of the antistatic agent for fibers.

[0013] The acid constituting the acid salt of the compound represented by general formula (1) is not particularly limited, but may be an organic acid or an inorganic acid, and is preferably an organic acid in terms of water absorbency and antistatic properties after washing. The organic acid is not particularly limited, but examples thereof include formic acid, acetic acid, lactic acid, succinic acid, fumaric acid, malic acid, adipic acid, tartaric acid, benzoic acid, citric acid, pyrrolidonecarboxylic acid, and salicylic acid. From the viewpoints of emulsifying properties and ease of handling, formic acid, acetic acid, and lactic acid are preferred, and acetic acid is most preferred. The inorganic acid is not particularly limited, but examples thereof include sulfuric acid, nitric acid, hydrochloric acid, carbonic acid, phosphoric acid, boric acid, metasilicic acid, and silicic anhydride.

[0014] The compound represented by the general formula (1) and its acid salt are not particularly limited, but for example, R 1 is an alkenyl group having 15 carbon atoms and containing one unsaturated bond, and X is an amino group; 1 is a C19 alkenyl group containing one unsaturated bond and X is a hydroxy group, 1 is an alkenyl group having 17 carbon atoms and containing one unsaturated bond, and X is an amino group; and 1 is a 17-carbon alkadienyl group containing two unsaturated bonds, and X is an amino group. 1 is a C17 alkadienyl group containing two unsaturated bonds and X is an amino group, and 1 is a C17 alkenyl group containing one unsaturated bond, and X is an amino group; 1 More preferred are compounds in which X is an alkenyl group having 17 carbon atoms and one unsaturated bond, and X is an amino group.

[0015] In formula (2), R 2represents an unsaturated hydrocarbon group having 15 to 21 carbon atoms, and from the viewpoint of antistatic properties after washing, the upper limit of the number of carbon atoms is preferably 19, more preferably 17. On the other hand, the lower limit of the number of carbon atoms is preferably 17. R 2 Specifically, the alkyl group preferably has 15 to 19 carbon atoms, and more preferably has 15 to 17 carbon atoms. In formula (2), Y represents -O- or -NH-, and -NH- is preferred from the viewpoint of hydrolysis resistance, and -O- is preferred from the viewpoint of suppressing coloration of the antistatic agent for fibers.

[0016] In formula (2), R 3 represents an alkyl group having 1 to 21 carbon atoms or an unsaturated hydrocarbon group having 15 to 21 carbon atoms, and from the viewpoint of emulsifiability, an alkyl group having 1 to 15 carbon atoms or an unsaturated hydrocarbon group having 15 to 21 carbon atoms is preferred, an alkyl group having 1 to 15 carbon atoms is more preferred, an alkyl group having 1 to 13 carbon atoms is even more preferred, and an alkyl group having 1 to 11 carbon atoms is particularly preferred.

[0017] The acid constituting the acid salt of the compound represented by general formula (2) is not particularly limited, but may be an organic acid or an inorganic acid, and from the viewpoint of water absorbency and antistatic properties after washing, an organic acid is preferred. The organic acid is not particularly limited, but examples thereof include formic acid, acetic acid, lactic acid, succinic acid, fumaric acid, malic acid, adipic acid, tartaric acid, benzoic acid, citric acid, pyrrolidonecarboxylic acid, and salicylic acid. From the viewpoints of emulsifying properties and ease of handling, formic acid, acetic acid, and lactic acid are preferred, and acetic acid is most preferred. The inorganic acid is not particularly limited, but examples thereof include sulfuric acid, nitric acid, hydrochloric acid, carbonic acid, phosphoric acid, boric acid, metasilicic acid, and silicic anhydride.

[0018] The compound represented by the general formula (2) and its acid salt are not particularly limited, but R 2 is a hydrocarbon group with 17 carbon atoms containing one unsaturated bond, and R 3 is a hydrocarbon group having 11 carbon atoms and no unsaturated bond, and Y is -NH-; 2 is a hydrocarbon group with 17 carbon atoms containing two unsaturated bonds, and R 3is a hydrocarbon group having 11 carbon atoms and not containing an unsaturated bond, and X is -NH-.

[0019] Compounds (A) other than the compounds represented by general formula (1) and general formula (2) are not particularly limited, but include compounds represented by the following general formula (3) and 2-(9-heptadecenyl)-1,3-imidazoline. [ka] (In formula (3), R 4 represents an unsaturated hydrocarbon group having 15 to 21 carbon atoms.

[0020] [Other ingredients] The antistatic agent for fibers of the present invention may contain other components in addition to the compound (A) and the acid salt of the compound (A) as long as the effects of the present invention are not impaired. Other components include water, solvents, nonionic surfactants, anionic surfactants, cationic surfactants, amphoteric surfactants, inorganic substances, preservatives, pH adjusters, and antifoaming agents.

[0021] The solvents include methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-butanol, 2-methylpropanol, 1,1-dimethylethanol, 1-pentanol, 2-pentanol, 3-pentanol, 2-methyl-1-butanol, 3-methyl-1-butanol, 1,1-dimethylpropanol, 3-methyl-2-butanol, 1,2-dimethylpropanol, 1-hexanol, 2-methyl-1-pentanol, 4-methyl-2-pentanol, 2-ethyl-1-butanol, 1-heptanol, 2-heptanol, 3-heptanol, ethylene glycol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, diethylene glycol monobutyl ether, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, and ethylene glycol monobutyl ether acetate. ester, propylene glycol, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol dimethyl ether, dipropylene glycol, dipropylene glycol monomethyl ether, dipropylene glycol dimethyl ether, dipropylene glycol monoethyl ether, tripropylene glycol, tripropylene glycol monomethyl ether, polypropylene glycol, hexylene glycol, benzyl alcohol, sorbite, polyalkylene glycol, acetone, methyl ethyl ketone, 2-pentanone, 3-pentanone, 2-hexanone, methyl isobutyl ketone, methyl acetate, ethyl acetate, butyl acetate, methyl propionate, methyl lactate, ethyl lactate, pentyl lactate, diisopropyl ether, dioxane, tetrahydrofuran, pyridine, N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

[0022] The nonionic surfactant is not particularly limited, and examples thereof include polyalkylene glycols such as oxyethylene-oxypropylene block or random copolymers, terminal alkyl ether compounds of polyalkylene glycols such as oxyethylene-oxypropylene block or random copolymers, polyoxyalkylene alkyl ethers, polyoxyalkylene alkylaryl ethers (polyoxyalkylene nonylphenyl ether, etc.), polyoxyalkylene polycyclic aryl ethers (polyoxyalkylene tristyrylphenyl ether, polyoxyalkylene distyrylphenyl ether, polyoxyalkylene styrylphenyl ether, polyoxyalkylene tristyrylmethylphenyl ether, polyoxyalkylene distyrylmethylphenyl ether, polyoxyalkylene benzyl ether, polyoxyalkylene tristyrylmethylphenyl ether, polyoxyalkylene methyl ... benzyl phenyl ether, polyoxyalkylene cumyl phenyl ether, polyoxyalkylene dicumyl phenyl ether, polyoxyalkylene naphthyl ether, etc.), polyoxyalkylene alkylamine, polyoxyalkylene alkylamide, polyoxyalkylene fatty acid ester, polyoxyalkylene fatty acid diester, polyoxyalkylene alkyl ether fatty acid ester, polyoxyalkylene alkyl aryl ether fatty acid ester, polyoxyalkylene polycyclic aryl ether fatty acid ester, polyoxyalkylene castor oil ether, polyoxyalkylene hydrogenated castor oil ether, polyoxyalkylene polyhydric alcohol ether, and a product obtained by adding ethylene oxide to polypropylene glycol (the so-called Pluronic (registered trademark) type surfactant).

[0023] Examples of alkyl groups constituting nonionic surfactants include methyl, ethyl, propyl, butyl, hexyl, 2-ethylhexyl, decyl, lauryl, isodecyl, tridecyl, cetyl, stearyl, oleyl, and behenyl groups, and may have an unsaturated bond and may be primary, secondary, or tertiary, and may have a linear or branched structure.

[0024] Examples of alkylaryl groups constituting nonionic surfactants include tolyl, xylyl, cumyl, octylphenyl, 2-ethylhexylphenyl, nonylphenyl, decylphenyl, and methylnaphthyl groups, and there are no limitations on the position or number of the alkyl groups.

[0025] Examples of polycyclic aryl groups constituting the nonionic surfactant include a styrylphenyl group, a styrylmethylphenyl group, a styrylnonylphenyl group, an alkylstyrylphenyl group, a tristyrylphenyl group, a distyrylphenyl group, a distyrylmethylphenyl group, a tristyrylphenyl group, a benzylphenyl group, a dibenzylphenyl group, an alkyldiphenyl group, a diphenyl group, a cumylphenyl group, and a naphthyl group, and there are no limitations on the position or number of the substituent.

[0026] Examples of polyhydric alcohols constituting nonionic surfactants include sorbitol, sorbide, sorbitan, pentaerythritol, trimethylolpropane, glycerin, neopentyl glycol, xylitol, erythritol, alkanolamines, and sugars.

[0027] Examples of polyoxyalkylene groups constituting the nonionic surfactant include polyoxyethylene groups, polyoxypropylene groups, polyoxybutylene groups, etc., with polyoxyethylene groups and polyoxypropylene groups being preferred. When two or more types are used, they may form any of block adducts, alternating adducts, and random adducts. Furthermore, it is preferred that the polyoxyalkylene group contains a polyoxyethylene group. The proportion of polyoxyethylene groups in the polyoxyalkylene groups is preferably 40 mol% or more, more preferably 50 mol%, even more preferably 60 mol% or more, and particularly preferably 80 mol% or more. The number of moles of oxyalkylene groups added is preferably 1 to 300 mol, more preferably 3 to 200 mol, and even more preferably 5 to 100 mol.

[0028] The anionic surfactant is not particularly limited, and examples thereof include fatty acids (salts) such as oleic acid, palmitic acid, sodium oleate, potassium palmitate, and triethanolamine oleate; hydroxyl group-containing carboxylic acids (salts) such as hydroxyacetic acid, potassium hydroxyacetate, lactic acid, and potassium lactate; polyoxyalkylene alkyl ether acetic acids (salts) such as polyoxyethylene tridecyl ether acetic acid (sodium salt); salts of carboxyl group-polysubstituted aromatic compounds such as potassium trimellitate and potassium pyromellitate; alkylbenzenesulfonic acids (salts) such as dodecylbenzenesulfonic acid (sodium salt); polyoxyalkylene alkyl ether sulfonic acids (salts) such as polyoxyethylene 2-ethylhexyl ether sulfonic acid (potassium salt); higher fatty acid amide sulfonic acids (salts) such as stearoyl methyl taurine (sodium), lauroyl methyl taurine (sodium), myristoyl methyl taurine N (sodium), and palmitoyl methyl taurine (sodium); lauroyl sarcosinic acid ( N-acyl sarcosinic acid (salts) such as sodium sulphate; alkyl phosphonic acids (salts) such as octyl phosphonate (potassium salt); aromatic phosphonic acids (salts) such as phenyl phosphonate (potassium salt); alkyl phosphonic acid alkyl phosphate esters (salts) such as 2-ethylhexyl phosphonate mono 2-ethylhexyl ester (potassium salt); nitrogen-containing alkyl phosphonic acids (salts) such as aminoethyl phosphonic acid (diethanolamine salt); alkyl sulphate esters (salts) such as 2-ethylhexyl sulphate (sodium salt); polyoxyalkylene sulphate esters (salts) such as polyoxyethylene 2-ethylhexyl ether sulphate (sodium salt); alkyl phosphate esters (salts) such as lauryl phosphate (potassium salt), cetyl phosphate (potassium salt), stearyl phosphate (diethanolamine salt); polyoxyethylene lauryl ether phosphate (potassium salt), polyoxyethylene oleyl ether phosphate (triethanolamine salt) and other polyoxyalkylene alkyl (alkenyl) ether phosphate esters (salts);Examples include polyoxyalkylene alkylphenyl ether phosphate esters (salts) such as polyoxyethylene nonylphenyl ether phosphate (potassium salt) and polyoxyethylene dodecylphenyl ether phosphate (potassium salt); long-chain sulfosuccinates such as sodium di-2-ethylhexyl sulfosuccinate and sodium dioctyl sulfosuccinate; and long-chain N-acyl glutamates such as sodium monosodium N-lauroyl glutamate and disodium N-stearoyl-L-glutamate.

[0029] The cationic surfactant is not particularly limited, and examples thereof include alkyl quaternary ammonium salts such as lauryl trimethyl ammonium chloride, myristyl trimethyl ammonium chloride, palmityl trimethyl ammonium chloride, stearyl trimethyl ammonium chloride, oleyl trimethyl ammonium chloride, cetyl trimethyl ammonium chloride, behenyl trimethyl ammonium chloride, coconut oil alkyl trimethyl ammonium chloride, beef tallow alkyl trimethyl ammonium chloride, stearyl trimethyl ammonium bromide, coconut oil alkyl trimethyl ammonium bromide, cetyl trimethyl ammonium methosulfate, oleyl dimethyl ethyl ammonium ethosulfate, dioctyl dimethyl ammonium chloride, dilauryl dimethyl ammonium chloride, distearyl dimethyl ammonium chloride, and octadecyl diethyl methyl ammonium sulfate; (polyoxyethylene) lauryl amino ether lactate, stearyl amino ether lactate, and di(polyoxyethylene) lauryl methyl ammonium chloride. (Polyoxyalkylene) alkylamino ether salts such as alkylaminoether dimethyl phosphate, di(polyoxyethylene) laurylethylammonium ethosulfate, di(polyoxyethylene) hardened beef tallow alkylethylamine ethosulfate, di(polyoxyethylene) laurylmethylammonium dimethyl phosphate, and di(polyoxyethylene) stearylamine lactate; acylamidoalkyl quaternary ammonium salts such as N-(2-hydroxyethyl)-N,N-dimethyl-N-stearoylamidopropylammonium nitrate, lanolin fatty acid amidopropylethyldimethylammonium ethosulfate, and lauroylamidoethylmethyldiethylammonium methosulfate; alkylethenoxy quaternary ammonium salts such as dipalmityl polyethenoxyethyl ammonium chloride and distearyl polyethenoxymethyl ammonium chloride; alkylisoquinolinium salts such as laurylisoquinolinium chloride; benzalkonium salts such as lauryldimethylbenzylammonium chloride and stearyldimethylbenzylammonium chloride;Benzethonium salts such as benzyldimethyl{2-[2-(p-1,1,3,3-tetramethylbutylphenoxy)ethoxy]ethyl}ammonium chloride; pyridinium salts such as cetylpyridinium chloride; acyl basic amino acid alkyl ester salts such as N-cocoyl arginine ethyl ester pyrrolidone carboxylate and N-lauroyl lysine ethyl ester chloride; Examples of the amine salts include primary amine salts such as laurylamine chloride, stearylamine bromide, hardened beef tallow alkylamine chloride, and rosinamine acetate; secondary amine salts such as cetylmethylamine sulfate, laurylmethylamine chloride, dilaurylamine acetate, stearylethylamine bromide, laurylpropylamine acetate, dioctylamine chloride, and octadecylethylamine hydroxide; tertiary amine salts such as dilaurylmethylamine sulfate, lauryldiethylamine chloride, laurylethylmethylamine bromide, diethanolstearylamidoethylamine trihydroxyethylphosphate salt, and stearylamidoethylethanolamine urea polycondensate acetate salt; fatty acid amide guanidinium salts; and alkyltrialkylene glycol ammonium salts such as lauryltriethyleneglycolammonium hydroxide.

[0030] The amphoteric surfactant is not particularly limited, and examples thereof include betaine-based amphoteric surfactants such as 2-heptadecyl-N-carboxymethyl-N-hydroxyethylimidazolium betaine, lauryl dimethylaminoacetic acid betaine, alkyl betaine, amido betaine, and sulfobetaine; and amino acid-based amphoteric surfactants such as N-lauryl glycine, N-lauryl β-alanine, and N-stearyl β-alanine.

[0031] When the present invention includes water, the water may be any of pure water, distilled water, purified water, soft water, ion-exchanged water, and tap water.

[0032] The antistatic finishing agent for fibers of the present invention may contain finishing chemicals that can be used simultaneously with the antistatic finishing for fibers, as long as the effects of the present invention are not impaired. Examples of finishing chemicals that can be used simultaneously include discoloration inhibitors, discoloration inhibitors, insect repellents, mildewproofing agents, anti-mite agents, deodorizers, water and oil repellents, UV absorbers, flame retardants, stain resistant agents, deep color deepening agents, smoothing agents, softeners, water absorbents, pigments, fluorescent brighteners, matting agents, penetrating agents, wetting agents, emulsifiers, defoamers, hydrophilic agents, antibacterial agents, deodorizers, antiviral agents, antiallergens, heat-shielding finishing agents, hard finishing agents, synthetic resins, sewability improvers, crosslinking agents, solvents, or water absorbents. A plurality of these chemicals may be used. Known chemicals can be used for each chemical.

[0033] [Antistatic finishing agent for textiles] In the antistatic finishing agent for fibers of the present invention, the proportion of at least one selected from the compound (A) and an acid salt of the compound (A) in the nonvolatile matter is 6 to 100% by weight. The reason why the antistatic finishing agent for fibers of the present invention can impart excellent water absorbency is not particularly limited, but it is believed that the imidazoline compound and its acid salt have unsaturated bonds in the hydrocarbon chain, which causes steric hindrance and makes it easier for them to adsorb evenly to the fiber surface, and that the presence of unsaturated bonds further improves hydrophilicity, making it easier for them to attract water molecules.

[0034] The proportion of at least one selected from compound (A) and an acid salt of compound (A) in the nonvolatile content of the antistatic agent for fibers of the present invention is 6 to 100% by weight. From the viewpoint of antistatic properties, the upper limit of this weight proportion is preferably 99% by weight, more preferably 98% by weight. Meanwhile, the lower limit of this weight proportion is preferably 10% by weight, even more preferably 30% by weight, and particularly preferably 50% by weight. For example, 10 to 100% by weight is preferred, 30 to 100% by weight is more preferred, and 50 to 100% by weight is particularly preferred. The non-volatile content in the present invention refers to the bone-dry components when the processing agent is heat-treated at 105°C to remove the solvent and the like, and reaches a constant weight.

[0035] The proportion of at least one compound selected from the group consisting of compounds represented by general formula (1) and acid salts thereof in the nonvolatile content of the antistatic agent for fibers of the present invention is not particularly limited, but from the viewpoint of water absorbency, it is preferably 65 to 100% by weight. The upper limit of this weight proportion is preferably 100% by weight, more preferably 99% by weight, and even more preferably 98% by weight. Meanwhile, the lower limit of this weight proportion is preferably 65% ​​by weight, even more preferably 80% by weight, and particularly preferably 90% by weight. Furthermore, for example, 65 to 100% by weight is preferred, 80 to 100% by weight is more preferred, and 90 to 100% by weight is particularly preferred.

[0036] The proportion of the compound represented by general formula (2) in the nonvolatile content of the antistatic agent for fibers of the present invention is not particularly limited, but from the viewpoint of water absorbency, it is preferably less than 35% by weight. The upper limit of this weight proportion is preferably 15% by weight, more preferably 5% by weight. Meanwhile, the lower limit of this weight proportion is preferably 0% by weight, even more preferably 1% by weight, and particularly preferably 2% by weight. Furthermore, for example, it is preferably 0 to less than 35% by weight, more preferably 0 to 15% by weight, and particularly preferably 0 to 5% by weight.

[0037] The proportion of nonionic surfactant in the nonvolatile content of the antistatic finishing agent for fibers of the present invention is not particularly limited, but from the viewpoint of improving dispersibility in water, it is preferably 0 to 94% by weight. The upper limit of this proportion is more preferably 90% by weight, even more preferably 50% by weight, and particularly preferably 20% by weight. Meanwhile, the lower limit of this proportion is more preferably 1% by weight, even more preferably 2% by weight. Also, for example, it is more preferably 0 to 90% by weight, and even more preferably 1 to 50% by weight.

[0038] The proportion of anionic surfactant in the nonvolatile content of the antistatic agent for fibers of the present invention is not particularly limited, but from the viewpoint of improving antistatic properties after washing, it is preferably 0 to 10.0 wt%. The upper limit of this proportion is more preferably 9.0 wt%, even more preferably 8.0 wt%, and particularly preferably 7.0 wt%. Meanwhile, the lower limit of this proportion is more preferably 0.5 wt%, even more preferably 1.0 wt%. Also, for example, it is more preferably 0 to 9.0 wt%, and even more preferably 0.5 to 8.0 wt%.

[0039] The proportion of cationic surfactant in the nonvolatile content of the antistatic agent for fibers of the present invention is not particularly limited, but from the viewpoint of improving the softness of the treated fabric, it is preferably 0 to 94% by weight. The upper limit of this proportion is more preferably 90% by weight, even more preferably 50% by weight, and particularly preferably 20% by weight. Meanwhile, the lower limit of this proportion is more preferably 1% by weight, even more preferably 2% by weight. Also, for example, it is more preferably 0 to 90% by weight, and even more preferably 1 to 50% by weight.

[0040] The proportion of amphoteric surfactant in the nonvolatile content of the antistatic finishing agent for fibers of the present invention is not particularly limited, but from the viewpoint of improving dispersibility in water, it is preferably 0 to 94% by weight. The upper limit of this proportion is more preferably 90% by weight, even more preferably 50% by weight, and particularly preferably 20% by weight. Meanwhile, the lower limit of this proportion is more preferably 1% by weight, even more preferably 2% by weight. Also, for example, it is more preferably 0 to 90% by weight, and even more preferably 1 to 50% by weight.

[0041] The weight ratio of the nonionic surfactant to the total of 100 of compound (A) and its acid salt is not particularly limited, but from the viewpoint of improving dispersibility in water, it is preferably 0 to 1500. The upper limit of this weight ratio is more preferably 1000, even more preferably 500, and particularly preferably 100. On the other hand, the lower limit of this weight ratio is more preferably 0, even more preferably 1, and particularly preferably 2. Also, for example, it is more preferably 0 to 500, and even more preferably 1 to 100.

[0042] The weight ratio of the anionic surfactant to the total weight of compound (A) and its acid salt (100) is not particularly limited, but from the viewpoint of improving antistatic properties after washing, it is preferably 0 to 10.0. The upper limit of this weight ratio is more preferably 9.0, even more preferably 8.0, and particularly preferably 7.0. Meanwhile, the lower limit of this ratio is more preferably 0, even more preferably 0.5, and particularly preferably 1.0. Also, for example, it is more preferably 0 to 9.0, and even more preferably 0.5 to 8.0.

[0043] The weight ratio of the cationic surfactant to the total of compound (A) and its acid salt (100) is not particularly limited, but from the viewpoint of improving the softness of the processed fabric, it is preferably 0 to 1500. The upper limit of this weight ratio is more preferably 1000, even more preferably 500, and particularly preferably 100. On the other hand, the lower limit of this weight ratio is more preferably 0, even more preferably 1, and particularly preferably 2. Also, for example, it is more preferably 0 to 500, and even more preferably 1 to 100.

[0044] The weight ratio of the amphoteric surfactant to the total of 100 of compound (A) and its acid salt is not particularly limited, but from the viewpoint of improving dispersibility in water, it is preferably 0 to 1500. The upper limit of this weight ratio is more preferably 1000, even more preferably 500, and particularly preferably 100. On the other hand, the lower limit of this weight ratio is more preferably 0, even more preferably 1, and particularly preferably 2. Also, for example, it is more preferably 0 to 500, and even more preferably 1 to 100.

[0045] The acid value of the nonvolatile content of the antistatic finishing agent for fibers of the present invention is not particularly limited, but is preferably 0.2 to 260 mgKOH / g from the viewpoint of agent stability. The upper limit of the acid value is more preferably 250 mgKOH / g, even more preferably 180 mgKOH / g, and particularly preferably 100 mgKOH / g. Meanwhile, the lower limit of the acid value is more preferably 0.3 mgKOH / g, even more preferably 0.4 mgKOH / g, and particularly preferably 0.5 mgKOH / g. For example, the acid value of the nonvolatile content of the antistatic finishing agent for fibers can be controlled by adjusting the content of acid components such as unreacted fatty acids during the production of compound (A), acids used in the production of the acid salt of compound (A), and anionic surfactants. The acid value in this case is determined by the method described in the Examples.

[0046] The pH of the antistatic finishing agent for fibers of the present invention is not particularly limited, but is preferably 4 to 12, more preferably 5 to 12, from the viewpoint of storage stability of the finishing agent.

[0047] The viscosity (20°C) of an aqueous dispersion of the antistatic finishing agent for fibers of the present invention, which has a nonvolatile content of 5% by weight, is not particularly limited, but is preferably 0.1 to 100 mPa·s. The upper limit of the viscosity is more preferably 50 mPa·s, even more preferably 10 mPa·s, and particularly preferably 5 mPa·s. On the other hand, the lower limit of the viscosity is more preferably 0.2 mPa·s, even more preferably 0.5 mPa·s, and particularly preferably 1 mPa·s. Note that when the antistatic finishing agent for fibers is composed of two or more liquids, the viscosity refers to the viscosity when all the liquids are mixed to form an aqueous dispersion with a nonvolatile content of 5% by weight.

[0048] The antistatic finishing agent for fibers of the present invention may be diluted with a solvent such as water, alcohol, etc. When the finishing agent of the present invention is diluted with a solvent, the weight ratio of the nonvolatile content in the finishing agent is preferably 0.01 to 10% by weight, more preferably 0.1 to 7% by weight, and even more preferably 0.5 to 5% by weight.

[0049] The method for preparing the antistatic finishing agent for fibers of the present invention is not particularly limited, and known methods can be used. For example, all of the constituent components may be mixed at once, or some of the constituent components may be mixed and then the remaining components may be mixed. Furthermore, concentration adjustment or dilution with water may be carried out at any timing and as many times as necessary.

[0050] [Method of manufacturing antistatic processed fibers] The method for producing antistatically treated fibers of the present invention includes a step of applying the antistatic agent for fibers of the present invention to a fiber material. In addition, a finishing agent other than the antistatic agent for fibers of the present invention may be applied simultaneously or separately. According to this production method, antistatic treated fibers with excellent water absorbency can be obtained.

[0051] The fiber material may be either natural or chemical. Examples of natural fibers include plant fibers such as cotton, hemp, flax, palm, and rush; animal fibers such as wool, goat hair, mohair, cashmere, camel hair, and silk; and mineral fibers such as asbestos. Examples of chemical fibers include inorganic fibers such as rock fiber, metal fibers, graphite, silica, and titanates; regenerated cellulose fibers such as rayon, cupra, viscose, polynosic, and purified cellulose fibers; melt-spun cellulose fibers; protein fibers such as milk protein and soy protein; regenerated and semi-synthetic fibers such as regenerated silk and alginate fiber; and synthetic fibers such as polyamide fibers, polyester fibers, cationic dyeable polyester fibers, polyvinyl fibers, polyacrylic alcohol fibers, polyurethane fibers, acrylic fibers, polyethylene fibers, polyvinylidene fibers, and polystyrene fibers. Furthermore, two or more of these fibers may be combined (by blending, interweaving, interknitting, etc.). As the fiber material, chemical fibers and animal fibers are preferred, with chemical fibers being more preferred and synthetic fibers being even more preferred, in terms of achieving better antistatic properties. Furthermore, when two or more fiber materials are combined, a composite fiber of a fiber material containing at least two or more selected from animal fibers, semi-synthetic fibers and synthetic fibers is preferred, a composite fiber of a fiber material containing at least two or more selected from polyamide fibers, polyester fibers, cationic dyeable polyester fibers, polyvinyl fibers, polyurethane fibers, acrylic fibers, polyethylene fibers and polyvinylidene fibers is more preferred, and a composite fiber of a fiber material containing at least two or more selected from polyamide fibers, polyester fibers, cationic dyeable polyester fibers, polyurethane fibers and acrylic fibers is even more preferred. In addition, from the viewpoint of achieving better water absorption, chemical fibers and plant fibers are preferred, semi-synthetic fibers and plant fibers are more preferred, and plant fibers are even more preferred. Furthermore, when two or more types of fiber materials are combined, composite fibers of fiber materials containing at least two or more types selected from plant fibers, semi-synthetic fibers, and synthetic fibers are preferred, more preferred are composite fibers of fiber materials containing at least two or more types selected from cotton, rayon, cupro, viscose, polynosic, polyamide fibers, polyester fibers, cationic dyeable polyester fibers, polyurethane fibers, and acrylic fibers, and even more preferred are composite fibers of fiber materials containing at least two or more types selected from cotton, rayon, polyamide fibers, polyester fibers, cationic dyeable polyester fibers, and polyurethane fibers.

[0052] Examples of the form of the fiber material include woven fabric, knitted fabric, fabric, thread, nonwoven fabric, etc. Examples of uses of the fiber material include objects to which antistatic properties, quick-drying properties, and wash resistance are to be imparted, such as underwear, work clothes, sportswear, bedding, covers, etc.

[0053] The method for applying the antistatic agent for fibers to a textile material is not particularly limited, and any known method can be used. Among these, at least one method selected from the exhaust method, pad-drying method, spraying method, and coating method is preferred, with the pad-drying method being more preferred, in order to ensure that the antistatic agent for fibers can be reliably fixed to the textile material.

[0054] Known methods can be used for the exhaustion method, pad-drying method, spraying method, and coating method. The exhaustion method uses a dilute solution of the processing agent and selectively absorbs the agent onto the fiber by adjusting conditions such as temperature, immersion time, and number of liquid circulations. This is then typically followed by water washing, centrifugal dehydration, and drying. The pad-drying method involves immersing the fiber in the processing agent solution for a short period of time and immediately squeezing it with a dehydration mangle or similar to adhere the agent to the fiber. This is followed by drying and, if necessary, curing. The spraying method involves placing the fiber on a conveyor moving at a constant speed and spraying a fixed amount of the processing agent solution onto the fiber to adhere the agent. This is followed by drying and, if necessary, curing. The coating method typically involves applying the processing agent solution to one side of the fiber using a mangle. The excess processing agent is then scraped off with a doctor blade, dried, and, if necessary, cured.

[0055] The temperature at which the antistatic agent for fibers of the present invention is applied to a textile material is preferably 5 to 40° C. If the application temperature is lower than 5° C., it may be difficult to maintain a constant temperature, making it impossible to apply the agent to the textile material at a constant temperature. On the other hand, if the application temperature is higher than 40° C., the elution of dyes and other substances contained in the textile material may increase.

[0056] [Antistatic processed fiber] The antistatically treated fiber of the present invention is a fiber in which the antistatic agent for fibers of the present invention is adhered to a fiber material. The antistatically treated fiber of the present invention is preferably an antistatically treated fiber obtained by the above-mentioned method for producing an antistatically treated fiber.

[0057] The amount of nonvolatile matter attached to the antistatic fiber of the antistatic agent for fibers can be selected as appropriate and may be the amount required to provide the desired functionality of the antistatic fiber. The amount attached is preferably 0.01 to 10% by weight, more preferably 0.03 to 7% by weight, and even more preferably 0.05 to 5% by weight, based on the fiber material.

[0058] The antistatically treated fiber of the present invention may contain an agent that can be used simultaneously with the antistatic treatment, provided that the effects of the present invention are not impaired. Examples of agents that can be used simultaneously include discoloration inhibitors, discoloration inhibitors, insect repellents, mildewproofing agents, anti-mite agents, deodorizers, water and oil repellents, UV absorbers, flame retardants, stain resistant agents, deep color deepening agents, smoothing agents, softeners, pigments, fluorescent brighteners, matting agents, penetrating agents, wetting agents, emulsifiers, defoamers, hydrophilic agents, antibacterial agents, deodorizing agents, antiviral agents, antiallergens, heat-shielding agents, hard finishing agents, synthetic resins, sewability improvers, crosslinking agents, solvents, and water-absorbing agents. Known agents can be used for each agent. [Example]

[0059] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples. In the examples, "parts" and "%" refer to "parts by weight" and "% by weight" unless otherwise specified.

[0060] In Tables 1 and 2, the following components were used. Polyoxyethylene polyoxypropylene glycol: polyethylene glycol / polypropylene glycol = 20 / 80 (weight ratio), polyethylene glycol-polypropylene glycol-polyethylene glycol type block copolymer with a molecular weight of 10,000 POE(15)C12 ether: Lauryl ether with an average of 15 moles of oxyethylene groups added POE(9) isoC13 ether: isotridecyl ether with an average of 9 moles of oxyethylene groups

[0061] [Preparation of imidazoline compound (a1)] Oleic acid and diethylenetriamine were charged in a molar ratio of 1.0:1.5 into a 1-liter reaction vessel equipped with a thermometer, a condenser, and a stirrer, and the mixture was reacted at 240°C for 15 hours to form the compound represented by the general formula (1) R 1 An imidazoline compound (a1) was obtained in which X was a heptadecenyl group and X was an amino group and had an iodine value of 72.6 g I2 / 100 g.

[0062] [Preparation of imidazoline compound acetate (a1-1)] Acetic acid was added to the imidazoline compound (a1) so that the molar ratio was 1:0.5, and the mixture was stirred for 1 hour to obtain an imidazoline compound acetate (a1-1).

[0063] [Preparation of imidazoline compound (a2)] Linoleic acid and diethylenetriamine were charged in a molar ratio of 1.0:1.4 into a 1-liter reaction vessel equipped with a thermometer, a condenser, and a stirrer, and the mixture was reacted at 240°C for 15 hours to obtain the compound represented by the general formula (1) R 1 An imidazoline compound (a2) was obtained in which X was a heptadecadienyl group and X was an amino group and had an iodine value of 146.0 g I2 / 100 g.

[0064] [Preparation of imidazoline compound (a3)] Oleic acid and 2-(2-aminoethylamino)ethanol were charged in a molar ratio of 1.0:1.3 into a 1-liter reaction vessel equipped with a thermometer, a condenser, and a stirrer, and the mixture was heated to 200°C under a reduced pressure of 400 mmHg and reacted for 3 hours. After that, the vacuum was reduced to 100 mmHg while maintaining the temperature at 200°C, and the reaction was continued for 6 hours, thereby obtaining the product of R 1 An imidazoline compound (a3) ​​was obtained in which X was a heptadecenyl group and X was a hydroxy group and had an iodine value of 72.4 g I2 / 100 g.

[0065] [Preparation of imidazoline compound (b1)] The imidazoline compound (a1) can be produced by the same reaction method as above except that oleic acid used in the production of the imidazoline compound (a1) is replaced with stearic acid, thereby obtaining a compound represented by the general formula (1) R 1 An imidazoline compound (b1) was obtained in which X is a heptadecyl group and X is an amino group.

[0066] [Preparation of imidazoline compound (b2)] The imidazoline compound (a1) can be produced by the same reaction method as above except that the oleic acid used in the production method of the imidazoline compound (a1) is replaced with palmitic acid, thereby obtaining the compound represented by the general formula (1) R 1An imidazoline compound (b1) was obtained in which X is a pentadecyl group and X is an amino group.

[0067] [Preparation of imidazoline compound (b3)] The imidazoline compound (a3) ​​can be produced by the same reaction method as above except that the oleic acid used in the production method of the imidazoline compound (a3) ​​is replaced with palmitic acid, thereby obtaining the compound represented by the general formula (1) R 1 An imidazoline compound (b3) was obtained in which X is a pentadecyl group and X is a hydroxy group.

[0068] [Preparation of imidazoline amide compound (a4)] Lauric acid was added to the imidazoline compound (a1) obtained by the above production method in a molar ratio of 1:1, and the mixture was reacted at 200°C for 6 hours to form the compound R 2 is a heptadecenyl group, Y is -NH-, and R 3 An imidazoline amide compound (a4) having an iodine value of 47.7 g I2 / 100 g, in which the group is an undecyl group, was obtained.

[0069] [Preparation of imidazoline amide compound (b4)] Oleic acid and diethylenetriamine were charged in a molar ratio of 2.05:1 into a 1-liter reaction vessel equipped with a thermometer, a condenser, and a stirrer, and the mixture was reacted at 240°C for 15 hours to form the compound represented by the general formula (2) R 2 is a heptadecenyl group, Y is -NH-, and R 3 The imidazoline amide compound (b4) was obtained, in which the substituent is a heptadecenyl group.

[0070] [Preparation of imidazoline ester compound (a5)] Capric acid was added to the imidazoline compound (a3) ​​obtained by the above production method in a molar ratio of 1:1, and the mixture was reacted at 250°C for 6 hours to form the compound R 2 is a heptadecenyl group, Y is -O-, R 3 An imidazoline ester compound (a5) having an iodine value of 50.3 g I2 / 100 g in which the group is a nonyl group was obtained.

[0071] [Preparation of acid salts of imidazoline compounds (a2-1) to (a5-1)] The imidazoline compound (a1) in the preparation of the imidazoline compound acetate salt (a1-1) was changed to the following (a2) to (a5), respectively, and acids were added in the following molar ratios and stirred for 1 hour, thereby obtaining imidazoline compound acid salts (a2-1) to (a5-1).

[0072] a2-1: Imidazoline compound lactate obtained by adding lactic acid to the imidazoline compound (a2) in a molar ratio of 1:1 and stirring for 1 hour a3-1: an imidazoline compound acetate obtained by adding acetic acid to the imidazoline compound (a3) ​​in a molar ratio of 1:0.3 and stirring for 1 hour a4-1: imidazoline compound formate obtained by adding formic acid to the imidazoline amide compound (a4) in a molar ratio of 1:1 and stirring for 1 hour a5-1: an imidazoline compound acetate salt obtained by adding acetic acid to the imidazoline ester compound (a5) in a molar ratio of 1:1 and stirring for 1 hour

[0073] [Preparation of Acid Salts (b1-1) and (b3-1) of Imidazoline Compounds] In the preparation of the imidazoline compound acetate salt (a1-1), the imidazoline compound (a1) was changed to the following (b1) and (b3), respectively, and acids were added in the following molar ratios and stirred for 1 hour, thereby obtaining imidazoline compound acid salts (b1-1) and (b3-1).

[0074] b1-1: an imidazoline compound acetate obtained by adding acetic acid to the imidazoline compound (b1) in a molar ratio of 1:1 and stirring for 1 hour b3-1: Imidazoline compound acetate obtained by adding acetic acid to the imidazoline compound (b3) in a molar ratio of 1:0.5 and stirring for 1 hour

[0075] [Preparation of Quaternary Cations of Imidazoline (Amide) Compounds (b1-2 and b2-2)] To the imidazoline compound (a3) ​​or imidazoline amide compound (b4) obtained by the above method, an equimolar amount of dimethyl sulfate was gradually added at 80°C over 2 hours, and the mixture was aged at the same temperature for 2 hours to obtain imidazoline compound quaternary cation (b1-2), which is a quaternary product of imidazoline compound (a3), and imidazoline amide compound quaternary cation (b2-2), which is a quaternary product of imidazoline amide compound (b4).

[0076] Example 1 An antistatic finishing agent for textiles was obtained by mixing 95% by weight of the imidazoline compound (a1) obtained by the above method and 5% by weight of POE(9) isoC13 ether. POE stands for polyoxyethylene, and the number in parentheses indicates the number of moles of oxyalkylene added. POE(9) indicates that 9 moles of polyoxyethylene have been added. The resulting antistatic finishing agent was diluted with water to a nonvolatile concentration of 1% to obtain a treatment solution. A polyester fabric (polyester tropical) was immersed in this treatment solution and treated at a wringing rate of 65% by weight, followed by a heat treatment at 130°C for 2 minutes. The frictional electrification voltage and water absorbency of the resulting treated fabric (test fabric) were evaluated before and after five washes. The results are shown in Table 1. The washing method, static stability evaluation, frictional electrification voltage, and water absorbency tests were performed as follows.

[0077] (Examples 2 to 11 and Comparative Examples 1 to 9) The nonvolatile compositions of the antistatic finishing agents for fibers in Examples 2 to 11 and Comparative Examples 2 to 9 were prepared so as to have the nonvolatile compositions shown in Tables 1 and 2, and were evaluated in the same manner as in Example 1. In Comparative Example 1, a test fabric to which no antistatic finishing agent for fibers had been applied was evaluated.

[0078] [Acid value] The acid value (x mgKOH / g) referred to in the present invention is the acid value of the nonvolatile content of the antistatic agent for fibers, and was measured by the following method. The nonvolatile content of each antistatic finishing agent for textiles was used as a measurement sample, and 1 g of each sample was dissolved in 50 mL of a 1:1 xylene / ethanol solution containing 0.01% phenolphthalein. A 0.1 mol / L potassium hydroxide ethanol solution was added dropwise to the solution, and the volume of liquid (y mL) required to turn a faint pink color was measured and calculated using the following formula. x=y×5.61

[0079] [Iodine value] The iodine value referred to in the present invention was determined by titration. Specifically, it was measured by the following method. 0.1 g to 10 g of sample was dissolved in 20 ml of carbon tetrachloride, and the solution was added to 25 ml of Wyss's reagent and 10% potassium iodide solution. The liberated iodine was titrated with 0.1 mol / L sodium thiosulfate solution using a potentiometric titrator, and the amount of iodine (g) was calculated as the amount of halogen consumed per 100 g of sample.

[0080] [Standing stability] The appearance of the treatment solution prepared in a room at 20°C and 65% humidity was judged according to the following criteria, with ○ and △ being considered acceptable. <Verdict> ○: Uniform △: Slightly uneven ×: Uneven

[0081] [Water absorption] The water absorption rate (seconds) was measured using the test cloth obtained above according to the JIS-L-1907 dropping method. A water absorption rate of less than 0.5 seconds indicates good water absorption.

[0082] [Frictional charging voltage] The test cloth obtained above was conditioned in a thermostatic chamber at 20°C and 45% RH for 2 hours, and then the frictional electrification voltage (V) was measured using a rotary static tester in accordance with JIS L-1094 Method B. A frictional electrification voltage of 3000 V or less indicates good antistatic properties.

[0083] [Washing Instructions] The test cloth was washed according to JIS-L-0217 103 method. The detergent used was Attack (manufactured by Kao Corporation), and the detergent concentration in the washing liquid was 1.0 g / L. Washing was repeated five times under the above conditions.

[0084] [Evaluation of antistatic properties after washing] The washed items were measured for frictional electrification voltage in the same manner as above and evaluated. If the frictional electrification voltage after washing was 3000 V or less, it indicated that the antistatic properties after washing were good.

[0085] [Table 1]

[0086] [Table 2]

[0087] As can be seen from Tables 1 and 2, the antistatic finishing agents for fibers according to Examples 1 to 11 are antistatic finishing agents for fibers in which the proportion of at least one selected from compound (A) and an acid salt of compound (A) in the nonvolatile matter is 6 to 100 wt %, and therefore are able to solve the problem of the present application, namely, excellent water absorbency and antistatic properties after washing. On the other hand, the antistatic agents according to Comparative Examples 2 to 11 do not contain compound (A) and an acid salt of compound (A) (Comparative Examples 2 to 9, 11), the content of compound (A) and an acid salt of compound (A) is not 6 to 100% by weight (Comparative Example 10), or there is no processing agent at all (Comparative Example 1), and therefore, they are unable to solve any of the problems of the present application. [Industrial Applicability]

[0088] The antistatic agent of the present invention, when applied to textile products, etc., has excellent water absorbency and antistatic properties after washing, and can therefore be particularly suitably used for textile products with a wide range of uses.

Claims

1. An antistatic finishing agent for fibers, wherein the proportion of at least one selected from the following compound (A) and an acid salt of the following compound (A) is 6 to 100% by weight based on the nonvolatile content: Compound (A): an imidazoline compound having an unsaturated hydrocarbon group having 15 to 21 carbon atoms

2. 2. The antistatic finishing agent for fibers according to claim 1, wherein the compound (A) is at least one selected from the group consisting of compounds represented by the following general formula (1) and compounds represented by the following general formula (2): 【Chemistry 1】 (In formula (1), R １ represents an unsaturated hydrocarbon group having 15 to 21 carbon atoms, and X represents an amino group or a hydroxy group. 【Chemistry 2】 (In formula (2), R ２ represents an unsaturated hydrocarbon group having 15 to 21 carbon atoms, Y represents —O— or —NH—, and R ３ represents an alkyl group having 1 to 21 carbon atoms or an unsaturated hydrocarbon group having 15 to 21 carbon atoms.

3. R in the general formula (2) ３ The antistatic finishing agent for fibers according to claim 2, wherein is an alkyl group having 1 to 15 carbon atoms.

4. 3. The antistatic finishing agent for fibers according to claim 2, wherein the compound (A) and the acid salt of the compound (A) comprise at least one selected from the group consisting of the compound represented by general formula (1) and an acid salt thereof.

5. 3. The antistatic finishing agent for fibers according to claim 2, wherein the content of at least one compound selected from the group consisting of the compound represented by formula (2) and its acid salt is less than 35% by weight.

6. 3. The antistatic finishing agent for fibers according to claim 1, wherein the proportion of at least one selected from the group consisting of compound (A) and an acid salt of compound (A) in the nonvolatile matter is 50 to 100% by weight.

7. The iodine value of the compound (A) is 35 to 150 gI ２ 3. The antistatic finishing agent for fibers according to claim 1, wherein the amount of the antistatic finishing agent for fibers is 100 g / 100 g.

8. 3. The antistatic finishing agent for fibers according to claim 1, wherein the acid value of the nonvolatile content of the finishing agent is 0.2 to 260 mgKOH / g.

9. A method for producing antistatically treated fibers, comprising a step of applying the antistatic agent for fibers according to claim 1 or 2 to a fiber material.

10. 3. An antistatic treated fiber, comprising a fiber material to which the antistatic agent for fibers according to claim 1 or 2 is adhered.

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