Treatment agents for synthetic fibers and synthetic fibers

Abstract

The objective of this invention is to provide a synthetic fiber treatment agent that can reduce burrs on fibers treated with the synthetic fiber treatment agent and improve the durability of the fibers. The synthetic fiber treatment agent of this invention is characterized by containing a smoothing agent, a nonionic surfactant, and an ionic surfactant, wherein the nonionic surfactant comprises an ester compound (A) formed from a polyol and a hydroxycarboxylic acid condensate.

Description

Technical Field

[0001] The present invention relates to a synthetic fiber treatment agent capable of reducing burrs on fibers treated with the synthetic fiber treatment agent and improving the durability of the fibers, as well as synthetic fibers treated with the synthetic fiber treatment agent. Background Technology

[0002] In processes such as the spinning and stretching of synthetic fibers, treatments are sometimes performed to attach a treatment agent to the surface of the synthetic fibers, for example, to improve smoothness and antistatic properties.

[0003] Previously known treatment agents for synthetic fibers were disclosed in Patent Documents 1 and 2. Patent Document 1 discloses a treatment agent for synthetic fibers comprising a substance obtained by further esterifying an alkylene oxide adduct of a polyol and a hydroxy monocarboxylic acid using a dicarboxylic acid. Patent Document 2 discloses a treatment agent for synthetic fibers comprising an alkylene oxide adduct of polymerized castor oil and an ester of a carboxylic acid.

[0004] Existing technical documents

[0005] Patent documents

[0006] Patent Document 1: Japanese Patent Application Publication No. 56-159364

[0007] Patent Document 2: Japanese Patent Application Publication No. 03-873 Summary of the Invention

[0008] The problem that the invention aims to solve

[0009] However, existing synthetic fiber treatment agents have the problem that the burr reduction effect and durability improvement effect on the fibers treated with the agent are insufficient.

[0010] Methods for solving problems

[0011] In order to solve the above-mentioned problems, the inventors conducted research and found that it is particularly suitable to mix an ester compound formed by the condensation of polyols and hydroxycarboxylic acids in the treatment agent for synthetic fibers.

[0012] The various methods used to solve the above problems are recorded.

[0013] The synthetic fiber treatment agent of Method 1 is characterized in that it contains a smoothing agent, a nonionic surfactant and an ionic surfactant, wherein the nonionic surfactant comprises an ester compound (A) formed by a polyol and a hydroxycarboxylic acid condensate.

[0014] Regarding Method 2, in the synthetic fiber treatment agent described in Method 1, the aforementioned polyol has a (poly)oxyalkylene group in its molecule.

[0015] Regarding method 3, in the synthetic fiber treatment agent described in method 1 or 2, the above-mentioned ester compound (A) comprises a compound in which the ratio of the number of hydroxyl groups (X) to the number of ester bonds (Y) in the molecule satisfies X:Y = 1:0.5 to 1:2.5.

[0016] Regarding Method 4, the synthetic fiber treatment agent described in any of Methods 1 to 3 contains the above-mentioned ester compound (A) in a proportion of 5% by mass or more and 30% by mass or less relative to the total mass of the synthetic fiber treatment agent.

[0017] Regarding Method 5, the synthetic fiber treatment agent described in any of Methods 1 to 4 contains a hydroxycarboxylic acid condensate in a proportion of 10,000 ppm or less relative to the total mass of the synthetic fiber treatment agent.

[0018] The synthetic fiber of method 6 is characterized in that it is coated with a synthetic fiber treatment agent as described in any of methods 1 to 5.

[0019] Invention Effects

[0020] According to the present invention, burrs on fibers treated with synthetic fibers can be reduced, and the durability of the fibers can be improved. Detailed Implementation

[0021] <First Implementation>

[0022] The following describes a first embodiment of the synthetic fiber treatment agent (hereinafter referred to as the treatment agent) of the present invention. The treatment agent of this embodiment contains a smoothing agent, a nonionic surfactant, and an ionic surfactant.

[0023] (Smoothing agent)

[0024] Examples of smoothing agents used in the processing agents provided in this embodiment include ester oils, mineral oils, and polyolefins.

[0025] There are no particular limitations on ester oils; examples include ester oils made from fatty acids and alcohols. For instance, ester oils can be made from fatty acids and alcohols having an odd or even number of hydrocarbon groups, as described later.

[0026] There are no particular restrictions on the number of carbon atoms, branching, or valence of fatty acids used as raw materials for ester oils. For example, they can be higher fatty acids, cyclic fatty acids, or aromatic fatty acids. Similarly, there are no particular restrictions on the number of carbon atoms, branching, or valence of alcohols used as raw materials for ester oils. For example, they can be higher alcohols, cyclic alcohols, or aromatic alcohols.

[0027] Specific examples of ester oils include: (1) ester compounds of aliphatic monohydric alcohols and aliphatic monocarboxylic acids, such as octyl palmitate, laurate, oleate, isotriadecyl stearate, and isotetracosyl oleate; (2) complete ester compounds of aliphatic polyhydric alcohols and aliphatic monocarboxylic acids, such as 1,6-hexanediol didecanoate, glyceryl trioleate, trimethylolpropane trilaurate, trimethylolpropane trioleate, trimethylolpropane trioleate, trimethylolpropane and coconut oil fatty acid triesters, and pentaerythritol tetraoctanoate; (3) diisostearate adipate, dioleanoate azelaate, diisostearate thiodipropionate, and diisostearate thiodipropionate. (3) Complete ester compounds of aliphatic monohydric alcohols and aliphatic polycarboxylic acids, such as oleate esters and diisoceryl thiopropionate; (4) Ester compounds of aromatic monohydric alcohols and aliphatic monocarboxylic acids, such as benzyl oleate and benzyl laurate; (5) Complete ester compounds of aromatic polyhydric alcohols and aliphatic monocarboxylic acids, such as bisphenol A dilaurate; (6) Complete ester compounds of aliphatic monohydric alcohols and aromatic polycarboxylic acids, such as di(2-ethylhexyl) phthalate, diisostearate isophthalate, and trioctyl trimellitate; (7) Natural oils such as coconut oil, rapeseed oil, sunflower oil, soybean oil, castor oil, sesame oil, fish oil, and tallow; etc.

[0028] Mineral oil, for example, with a kinematic viscosity of 5 mm at 40°C. 2 Substances with a concentration of / s or higher. Examples of mineral oils include, for example, aromatic hydrocarbons, alkane hydrocarbons, and cycloalkanes. More specifically, examples include, for example, spindle oil and liquid paraffin. These mineral oils may be commercially available products.

[0029] Polyolefins can be used as smoothing agents, such as poly-α-olefins. Specific examples of polyolefins include poly-α-olefins obtained by polymerizing 1-butene, 1-hexene, 1-decene, etc. Commercially available poly-α-olefins are suitable.

[0030] These smoothing agents can be used alone or in combination of two or more.

[0031] In the treatment agent, the lower limit of the content of the smoothing agent is preferably 20% by mass or more, more preferably 25% by mass or more. When the content is 20% by mass or more, the smoothness of the fibers treated with the treatment agent can be further improved. The upper limit of the content of the smoothing agent is preferably 70% by mass or less, more preferably 60% by mass or less. When the content is 70% by mass or less, the stability of the treatment agent can be further improved. It should be noted that any combination of the above upper and lower limits is also conceivable.

[0032] (Nonionic surfactant)

[0033] The nonionic surfactant supplied in the treatment agent of this embodiment comprises an ester compound (A) formed from a polyol and a hydroxycarboxylic acid condensate.

[0034] The hydroxycarboxylic acid condensate of the raw material constituting the ester compound (A) is obtained, for example, by subjecting a mixture of one or more hydroxycarboxylic acids as raw materials to a dehydration condensation reaction under an inert gas stream such as nitrogen or under reduced pressure, at a temperature of 60°C or higher and 200°C or lower, for 30 minutes or higher and 12 hours or lower. The reaction can be catalytic or non-catalytic. Examples of hydroxycarboxylic acids include fatty acids having hydroxyl groups. There are no particular limitations on the number of carbon atoms, branching, or valence of the fatty acid, and it can be, for example, a higher fatty acid or a cyclic fatty acid. Furthermore, it can be a saturated fatty acid or an unsaturated fatty acid. Specific examples of hydroxycarboxylic acids include 12-hydroxystearic acid, 12-hydroxyoleic acid (ricinoleic acid), 16-hydroxyhexadecanoic acid (juniper acid), 18-hydroxyoctadecanoic acid, 9-hydroxystearic acid, 10-hydroxystearic acid, 12-hydroxydodecanoic acid (hinoki acid), and 9,10-dihydroxyoctadecanoic acid. Alternatively, naturally derived fatty acids can be used as the hydroxycarboxylic acid. In the case where fatty acids other than hydroxycarboxylic acids are also present, the hydroxycarboxylic acid must constitute at least 80% by mass of the total fatty acids. The degree of condensation of the hydroxycarboxylic acid condensate can be suitably set, preferably between a dimer and an octamer.

[0035] Among these, from the perspective of further reducing burrs on fibers treated with the treatment agent, condensates of saturated fatty acids having hydroxyl groups are preferred, and condensates of 12-hydroxystearic acid are more preferred.

[0036] Specific examples of polyols used as raw materials for ester compound (A) include ethylene glycol, propylene glycol, 1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, 2-methyl-1,2-propanediol, 1,5-pentanediol, 1,6-hexanediol, 2,5-hexanediol, 2-methyl-2,4-pentanediol, 2,3-dimethyl-2,3-butanediol, glycerol, diglycerol, 2-methyl-2-hydroxymethyl-1,3-propanediol, trimethylolpropane, sorbitan, pentaerythritol, sorbitol, etc.

[0037] Polyols can be added to form (poly)oxyalkylene oxides. Regarding the epoxides used as raw materials for forming (poly)oxyalkylene oxides, epoxides with 2 or more and 4 or fewer carbon atoms are preferred. Specific examples of epoxides include ethylene oxide, propylene oxide, and butane oxide. The number of moles of epoxide added can be suitably set, preferably 0.1 moles or more and 250 moles or less, more preferably 1 mole or more and 200 moles or less, further preferably 2 moles or more and 150 moles or less, and particularly preferably 3 moles or more and 40 moles or less. Ranges formed by any combination of the above upper and lower limits are also conceivable. It should be noted that the number of moles of epoxide added represents the number of moles of epoxide relative to 1 mole of the target compound added to the raw material. An epoxide can be used alone, or two or more epoxides can be suitably combined. When two or more epoxides are used, their addition can be any of the following: block addition, random addition, or a combination of block addition and random addition, without particular restriction.

[0038] Specific examples of ester compounds (A) include ester compounds of pentaerythritol or its alkylene oxide adduct and 12-hydroxystearic acid condensate, ester compounds of trimethylolpropane or its alkylene oxide adduct and 12-hydroxystearic acid condensate, ester compounds of glycerol or its alkylene oxide adduct and 12-hydroxystearic acid condensate, ester compounds of diglycerol or its alkylene oxide adduct and 12-hydroxystearic acid condensate, and ester compounds of trimethylolpropane or its alkylene oxide adduct and 12-hydroxyoleic acid condensate.

[0039] These ester compounds (A) can be used alone or in combination of two or more.

[0040] The ester compound (A) preferably comprises a compound in which the ratio of the number of hydroxyl groups (X) to the number of ester bonds (Y) in the molecule satisfies X:Y = 1:0.5 to 1:2.5, and more preferably comprises a compound in which the ratio satisfies X:Y = 1:1.5 to 1:2.5. By limiting the ratio of X to Y within this numerical range, the effects of the present invention can be further improved. In one embodiment of this invention, the value of X / Y obtained by dividing the number of hydroxyl groups in the molecule of the ester compound (A) by the number of ester bonds is, for example, 0.25 (= 1 / 4) or more, 0.4 (= 1 / 2.5) or more, 0.5 (= 1 / 2) or more, 0.6 (≒ 1 / 1.67) or more, 0.67 (≒ 1 / 1.5) or more, or 0.75 (≒ 1 / 1.33) or more. Similarly, the value of X / Y is, for example, 3 (≒1 / 0.33) or less, 0.75 (≒1 / 1.33) or less, 0.67 (≒1 / 1.5) or less, 0.6 (≒1 / 1.67) or less, 0.5 (=1 / 2) or less, or 0.4 (=1 / 2.5) or less.

[0041] X:Y is calculated by counting the number of hydroxyl groups (X) and the number of ester bonds (Y) in the structural formula of the mixed ester compound (A).

[0042] Ester compound (A) is obtained, for example, by reacting a polyol and a hydroxycarboxylic acid condensate, which are used as raw materials, under conditions of 60°C or higher and 200°C or lower, for 30 minutes or more and 12 hours or less. The reaction can be carried out simultaneously with the condensation reaction of the hydroxycarboxylic acid, or it can be an transesterification reaction of the polyol and the hydroxycarboxylic acid condensate derivative. The reaction can be a catalytic reaction or a non-catalytic reaction. Examples of catalysts include: (1) inorganic acids such as hydrochloric acid, sulfuric acid, and phosphoric acid; (2) alkyl sulfonic acids such as p-toluenesulfonic acid, methanesulfonic acid, and alkylbenzenesulfonic acid; (3) organometallic compounds such as tetraisopropyl titanate, tetrabutyl titanate, tetraoctyl titanate, tetrazirconate, and tetrabutyl zirconate; (4) enzymes such as lipases; and (5) bases such as potassium hydroxide, sodium hydroxide, and sodium methoxide. These can be removed from the ester compound by adsorption using inorganic adsorbents and / or ion exchange resins based on known methods, or by purification using neutralization and washing with water.

[0043] In the treatment agent, the lower limit of the content of ester compound (A) is preferably 3% by mass or more, more preferably 5% by mass or more. The upper limit of the content of ester compound (A) is preferably 35% by mass or less, more preferably 30% by mass or less. By limiting the content to this range, the effect of the present invention can be further improved. It should be noted that any combination of the above-mentioned upper and lower limits is also conceivable. In one embodiment of this invention, the content of ester compound (A) in the treatment agent is 5% by mass or more, 10% by mass or more, 15% by mass or more, 20% by mass or more, or 25% by mass or more. Similarly, the content of ester compound (A) in the treatment agent is 35% by mass or less, 25% by mass or less, 20% by mass or less, 15% by mass or less, or 10% by mass or less.

[0044] The treatment agent may further contain other nonionic surfactants besides the aforementioned ester compound (A).

[0045] Other nonionic surfactants include, for example, compounds with a (poly)oxyalkylene structure formed by adding an epoxide to an alcohol or carboxylic acid; ether / ester compounds with a (poly)oxyalkylene structure formed by adding an epoxide to an ester compound of a carboxylic acid and a polyol; compounds with a (poly)oxyalkylene structure formed by adding an epoxide to an amine compound, such as an organic primary amine; partial ester compounds of a carboxylic acid and a polyol; amide compounds formed by condensing an amine compound with a carboxylic acid; compounds with a (poly)oxyalkylene structure formed by adding an epoxide to a fatty amide; and derivatives of the above-mentioned ester compound (A).

[0046] Specific examples of alcohols used as raw materials for nonionic surfactants include: (1) straight-chain alkyl alcohols such as methanol, ethanol, propanol, butanol, pentanol, hexanol, octanol, nonanol, decanol, undecanol, dodecanol, tridecanol, tetradecanol, pentadecanol, hexadecanol, heptadecanol, octadecanol, nonadecanol, eicosane, dodecanol, dodecanol, tridecanol, tetradecanol, pentadecanol, hexadecanol, heptadecanol, octadecanol, nonadecanol, and triadecanol; and (2) isopropanol, isobutanol, isohexanol, 2-ethylhexanol, isononanol, isodecanol, isodecanol, isodecanol, isodecanol, and isotriadecanol. Branched alkyl alcohols such as isohexadecanol, isohexadecanol, isohexadecanol, isohexadecanol, isohexadecanol, isohexadecanol, isohexadecanol, isohexadecanol, isohexadecanol, isohexadecanol, isohexadecanol, isohexadecanol, isohexadecanol, isohexadecanol, isohexadecanol, isohexadecanol, isohexadecanol, isohexadecanol, and isohexadecanol; (3) Straight-chain alkenyl alcohols such as tetradecenol, hexadecenol, heptadecenol, octadecenol, and nonadecenol; (4) Branched alkenyl alcohols such as isohexadecanol and isohexadecanol; (5) Cyclic alkyl alcohols such as cyclopentanol and cyclohexanol; (6) Aromatic alcohols such as phenol, nonylphenol, benzyl alcohol, monostyrene phenol, stilbene phenol, and tristyrene phenol; etc.

[0047] Specific examples of carboxylic acids used as raw materials for nonionic surfactants include: (1) straight-chain alkyl carboxylic acids such as octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, eicosanoic acid, dodecanoic acid, etc.; (2) branched-chain alkyl carboxylic acids such as 2-ethylhexanoic acid, isododecanoic acid, isotridecanoic acid, isotetradecanoic acid, isohexadecanoic acid, etc.; (3) straight-chain alkenyl carboxylic acids such as octadecenoic acid, octadecadienoic acid, octadectrienoic acid, etc.; (4) aromatic carboxylic acids such as benzoic acid; (5) hydroxycarboxylic acids such as ricinoleic acid; etc.

[0048] Details regarding the epoxides used as raw materials for forming the (poly)oxyalkylene structure of nonionic surfactants are the same as those described above regarding the epoxides used as raw materials for forming the (poly)oxyalkylene structure of polyols that can be added to ester compounds (A), and therefore are omitted.

[0049] Specific examples of polyols used as raw materials for nonionic surfactants include ethylene glycol, propylene glycol, 1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, 2-methyl-1,2-propanediol, 1,5-pentanediol, 1,6-hexanediol, 2,5-hexanediol, 2-methyl-2,4-pentanediol, 2,3-dimethyl-2,3-butanediol, glycerol, 2-methyl-2-hydroxymethyl-1,3-propanediol, trimethylolpropane, sorbitan, pentaerythritol, and sorbitol.

[0050] Specific examples of amine compounds used as raw materials for nonionic surfactants include methylamine, ethylamine, butylamine, octylamine, laurylamine, stearylamine, octadecylamine, and cocoamine.

[0051] Specific examples of fatty amides used as raw materials for nonionic surfactants include octylamide, lauramide, palmitamide, stearamide, oleamide, behenamide, wood wax amide, amides of fatty acids and diethanolamine, and amides of fatty acids and ethyleneamine.

[0052] Examples of derivatives of ester compound (A) include substances formed by esterifying more than 30% of the hydroxyl groups of ester compound (A) with monobasic fatty acids, condensates of ester compound (A) and diacids, and substances formed by esterifying the hydroxyl groups of condensates of ester compound (A) and diacids with monobasic fatty acids.

[0053] Specific examples of other nonionic surfactants include ester compounds of polyalkylene glycols and oleic acid, ester compounds of polyalkylene glycols and palm oil fatty acids, compounds formed by the addition of epoxides to oleyl alcohol, compounds formed by the addition of epoxides to isotriadecyl alcohol, compounds formed by the addition of epoxides to isododecyl alcohol, sorbitan monooleate, sorbitan trioleate, trimethylolpropane dioleate, glyceryl dioleate, oleic acid diethanolamide, compounds formed by the addition of epoxides to stearamine, compounds formed by the esterification of glycerol epoxide adducts and 12-hydroxystearic acid condensates with oleic acid, and compounds formed by crosslinking glycerol epoxide adducts and 12-hydroxystearic acid condensates with adipic acid and terminal esterification with palmitic acid.

[0054] These other nonionic surfactants can be used alone, or two or more can be used in combination as appropriate.

[0055] In the treatment agent, the lower limit of the content of the nonionic surfactant is preferably 30% by mass or more, more preferably 45% by mass or more. The upper limit of the content of the nonionic surfactant is preferably 75% by mass or less, more preferably 70% by mass or less. By limiting the content to this range, the effect of the present invention can be further improved. It should be noted that any combination of the above-mentioned upper and lower limits is also conceivable.

[0056] (Ionic surfactants)

[0057] As the ionic surfactant supplied in the processing agent of this embodiment, a known substance may be suitably used. Examples of ionic surfactants include anionic surfactants, cationic surfactants, and amphoteric surfactants.

[0058] As anionic surfactants, known substances can be suitably used. Specific examples of anionic surfactants include, for example: (1) phosphate salts of aliphatic alcohols such as lauryl phosphate, cetyl phosphate, octyl phosphate, oleyl phosphate, stearyl phosphate, and isostearyl phosphate; and (2) phosphate salts of substances formed by adding at least one epoxide selected from ethylene oxide and propylene oxide to an aliphatic alcohol, such as polyoxyethylene lauryl ether phosphate, polyoxyethylene oleyl ether phosphate, and polyoxyethylene stearyl ether phosphate. (3) aliphatic or aromatic sulfonates such as lauryl sulfonate, myristyl sulfonate, cetyl sulfonate, stearyl sulfonate, tetradecane sulfonate, dodecylbenzene sulfonate, secondary alkyl sulfonate (13 or more and 15 carbon atoms) salts, secondary alkyl sulfonate (11 or more and 14 carbon atoms) salts, and α-olefin sulfonates; (4) sulfate salts of aliphatic alcohols such as lauryl sulfate, oleyl sulfate, and stearyl sulfate; (5) poly(lactic acid) sulfates; Sulfate salts of substances formed by the addition of at least one epoxide selected from ethylene oxide and propylene oxide to an aliphatic alcohol; (6) Sulfate salts of natural fatty acids such as castor oil, sesame oil, tall oil, soybean oil, rapeseed oil, and palm oil. Sulfated esters of fatty acids from various sources; (7) sulfated esters of castor oil, sesame oil, tall oil, soybean oil, rapeseed oil, palm oil, and other natural oils; (8) fatty acid salts such as 2-ethylhexanoate, laurate, oleate, and stearate; (9) sulfonated succinate salts of aliphatic alcohols such as dioctyl sulfonated succinate; (10) N-acyl sarcosine salts such as oleoyl sarcosine salts; etc. Counterions for anionic surfactants include, for example, alkali metal salts such as potassium salts and sodium salts, ammonium salts, triethanolamine salts, (poly)oxyalkylene alkylamine salts, dibutylethanolamine salts, and other alkanolamine salts.

[0059] Specific examples of cationic surfactants include lauryltrimethylammonium chloride, cetyltrimethylammonium chloride, stearyltrimethylammonium chloride, docosyltrimethylammonium chloride, and dialcyldimethylammonium chloride.

[0060] Specific examples of amphoteric surfactants include betaine-type amphoteric surfactants. These ionic surfactants can be used alone, or two or more can be used in combination as appropriate.

[0061] In the treatment agent, the lower limit of the content of the ionic surfactant is preferably 0.1% by mass or more, more preferably 1% by mass or more. The upper limit of the content of the ionic surfactant is preferably 10% by mass or less, more preferably 6% by mass or less. By limiting the content to this range, the effect of the present invention can be further improved. It should be noted that any combination of the above-mentioned upper and lower limits is also conceivable.

[0062] (other)

[0063] The hydroxycarboxylic acid condensate can be contained in a proportion of less than 10,000 ppm relative to the total mass of the treatment agent. By limiting this range, it is possible to reduce smoke generation during the spinning or stretching process of the fibers treated with the treatment agent.

[0064] <Second Implementation Method>

[0065] Next, a second embodiment embodying the synthetic fiber based on the present invention will be described. The synthetic fiber of this embodiment is coated with the treatment agent of the first embodiment. The form of the treatment agent used to coat the synthetic fiber can be a diluted solution obtained by diluting with a diluent, such as an organic solvent solution, an aqueous solution, etc. From the perspective of the adhesion of the treatment agent to the fiber and economy, hydrocarbons with 10 or more but less than 15 carbon atoms and / or water are preferably used in the diluent. The mixing ratio of the treatment agent to the diluent is preferably 99:1 to 10:90 (mass of treatment agent:mass of diluent). The diluted solution, such as an aqueous solution, is coated onto the synthetic fiber, for example, in a spinning or stretching process. The diluted solution coated onto the synthetic fiber can be evaporated by a stretching process or a drying process. There are no particular limitations on the process in which the diluted solution is coated, as long as it is a spinning process. The effects of the invention can be further expected by using manufacturing equipment that includes a process in which rollers at 150°C or higher pass through during the stretching or heat treatment process. High pressure is applied at high temperatures when the fibers come into contact with the equipment or with each other, thus enhancing the effectiveness of the invention.

[0066] Specific examples of synthetic fibers to which the treatment agent of this embodiment is applied are not particularly limited, and examples include: (1) polyester fibers such as polyethylene terephthalate (PET), polyethylene terephthalate, polyethylene terephthalate, polyethylene naphthalate, polylactic acid, and composite fibers containing these polyester resins; (2) polyamide fibers such as nylon 6 and nylon 66; (3) polyacrylic acid fibers such as polyacrylic acid and modified acrylic acid; (4) polyolefin fibers such as polyethylene and polypropylene; and so on. Among these, polyester fibers and polyamide fibers are preferred. The fineness of the manufactured synthetic fiber is not particularly limited, but is preferably 150 dtex or more, more preferably 500 dtex or more, and even more preferably 1000 dtex or more. In addition, the strength of the manufactured synthetic fiber is not particularly limited, but is preferably 5.0 cN / dtex or more, more preferably 6.0 cN / dtex or more, and even more preferably 7.0 cN / dtex or more.

[0067] There are no particular limitations on the proportion of the treatment agent adhering to the synthetic fiber, but it is preferable that the treatment agent is adhering at a proportion of 0.1% to 3% by mass relative to the synthetic fiber (excluding the proportion of solvents such as water). This configuration further enhances the effectiveness of the present invention. Furthermore, there are no particular limitations on the method of adhering the treatment agent; for example, known methods such as roller oiling, guided oiling using a metering pump, impregnation oiling, and spray oiling can be employed.

[0068] In this invention, the use of synthetic fibers is not particularly limited, but synthetic fibers used in industrial materials are preferred. For example, synthetic fibers used in the automotive, construction, commerce, agriculture and fisheries, and civil engineering fields, such as airbag fibers, seat belt fibers, tire cord fibers, carpet fibers, tent fibers, advertising fabric fibers, fishing net fibers, conveyor belt fibers, and rope fibers, are more preferred.

[0069] The effects of the treatment agent and synthetic fiber in the above embodiments will be explained.

[0070] (1) The treatment agent of the above embodiment contains a smoothing agent, a nonionic surfactant, and an ionic surfactant. The nonionic surfactant is configured to include an ester compound (A) formed from a polyol and a hydroxycarboxylic acid condensate. Therefore, burrs on the fibers treated with the treatment agent can be reduced. In particular, burrs generated by friction between the fiber and a metal rubbing body can be reduced. Furthermore, the strength of the coating formed on the fiber surface based on the treatment agent is improved, resulting in increased fiber durability.

[0071] It should be noted that the above implementation methods can be modified as follows. The above implementation methods and the following modifications can be combined with each other to implement them within the scope of technical inconsistency.

[0072] • In the treatment agent of the above embodiments, without hindering the effect of the present invention, during or after the manufacturing of the treatment agent, other than the above-mentioned stabilizers, charge control agents, binders, antioxidants, ultraviolet absorbers, defoamers, preservatives, rust inhibitors and other components commonly used in treatment agents may be further mixed in to maintain the quality of the treatment agent.

[0073] • To improve the appearance stability during storage, the treatment agent can be premixed with water. In this case, the preferred mixing ratio of treatment agent to water is treatment agent mass: water mass = 85:15 to 99.9:0.1.

[0074] Example

[0075] Hereinafter, embodiments are given to illustrate the structure and effects of the present invention in more detail, but the present invention is not limited to these embodiments. It should be noted that, unless otherwise stated, in the following descriptions of embodiments and comparative examples, parts refer to parts by mass, and % refers to percentages by mass.

[0076] Experimental Group 1 (Preparation of the Treatment Agent)

[0077] (Example 1)

[0078] As shown in Table 1, the treatment agent of Example 1 was prepared, comprising: 20 parts (%) of trimethylolpropane trioleate (ES-1) as a smoothing agent, 10 parts (%) of rapeseed oil (ES-3), 5 parts (%) of diisostearic acid thiodipropionate (ES-5), 25 parts (%) of an ester compound (A-1) as a nonionic surfactant, 15 parts (%) of a substance (A3-1) obtained by esterifying 2 moles of oleic acid with 1 mole of polyethylene glycol (weight average molecular weight 600), and 10 moles of ethylene oxide (hereinafter referred to as E) added to 1 mole of oleic alcohol. 5 parts (%) of the substance formed by adding 10 moles of EO to 1 mole of isotriadecyl alcohol (N-1), 10 parts (%) of the substance formed by adding 10 moles of EO to 1 mole of isotriadecyl alcohol (N-2), 5 parts (%) of sorbitan monooleate (N-5), 3 parts (%) of the substance formed by adding 5 moles of EO to 1 mole of stearylamine (N-10), 1.5 parts (%) of sodium secondary alkyl sulfonate (carbon number 11-14) as an ionic surfactant (I-1), and 0.5 parts (%) of the phosphate ester-laurhodium EO 10 mole adduct salt of oleyl alcohol EO 5 moles adduct (I-5).

[0079] (Examples 2-16, Comparative Examples 1-4)

[0080] The treatment agents of Examples 2-16 and Comparative Examples 1-4 were prepared in the same manner as the treatment agent of Example 1, comprising a smoothing agent, a nonionic surfactant, and an ionic surfactant in the proportions shown in Tables 1 and 2.

[0081] The types and contents of smoothing agents, nonionic surfactants, and ionic surfactants are shown in the "Smoothing Agents", "Nonionic Surfactants", and "Ionic Surfactants" columns of Tables 1 and 2, respectively.

[0082] It should be noted that the proportion of hydroxycarboxylic acid condensates in the treatment agent is calculated based on the content of ester compound (A) and the content of hydroxycarboxylic acid condensates contained in ester compound (A). The proportion of hydroxycarboxylic acid condensates in ester compound (A) is determined by the method shown below. The calculation results are shown in the "Proportion of Hydroxycarboxylic Acid Condensates in Treatment Agent" column of Tables 1 and 2.

[0083] (Quantitative methods for hydroxycarboxylic acid condensates)

[0084] The hydroxycarboxylic acid condensate was separated from the ester compound (A) by column chromatography. The column chromatography conditions are described below.

[0085] Stationary phase: silica gel

[0086] Mobile phase: a mixed solvent of n-hexane / chloroform = 60 / 40 (vol%)

[0087] After the extract was recovered, it was dried and concentrated using a heater, and the amount of hydroxycarboxylic acid condensate contained in the ester compound (A) was quantified based on the mass of the obtained product.

[0088] [Table 1]

[0089]

[0090] [Table 2]

[0091]

[0092] The details of the smoothing agents, nonionic surfactants, and ionic surfactants listed in Tables 1 and 2 are as follows.

[0093] Smoothing Agent

[0094] ES-1: Trimethylolpropane trioleate

[0095] ES-2: Triester of trimethylolpropane and coconut oil fatty acids

[0096] ES-3: Rapeseed oil

[0097] ES-4: Diisostearic acid ester

[0098] ES-5: Diisostearyl thiodipropionate

[0099] ES-6: Isotetraalkyl oleate

[0100] <Nonionic surfactants>

[0101] (Ester compound (A))

[0102] Use the ester compounds (A-1) to (A-15) listed in Table 3 below.

[0103] Synthesis of ester compound (A-1)

[0104] In a 2L four-necked flask equipped with a thermometer, nitrogen inlet pipe, stirrer, and cooling trap, pentaerythritol-ethylene oxide 10 molar adduct as the starting polyol and 12-hydroxystearic acid condensate as the hydroxycarboxylic acid condensate were added in the specified molar proportions shown in Table 3. Toluenesulfonic acid monohydrate (0.5% by mass of the mixture) was added as a catalyst to this mixture. The reactor was heated with a heating mantle and the reaction was carried out at 160°C under a nitrogen flow. The reaction was continued until the acid value of the reaction solution reached below 1 mg KOH / g. After cooling the reactor to 80°C, a 10% sodium hydroxide aqueous solution was added to the reaction solution in an amount sufficient to completely neutralize the residual fatty acids and acid catalyst, and the mixture was stirred for 30 minutes. Dehydration was then carried out by stirring at 100°C and 5 kPa for 1 hour. Finally, activated clay (2% by mass relative to the reaction solution) was added, and the mixture was stirred at 80°C and 5 kPa for 1 hour. The mixture was then filtered to remove neutralizing salts and adsorbent, thereby obtaining the desired ester compound (A-1).

[0105] Synthesis of ester compounds (A-2) to (A-15)

[0106] Regarding ester compounds (A-2) to (A-15), the polyol and hydroxycarboxylic acid condensate, as raw materials, were reacted in the same proportions shown in Table 3 as with ester compound (A-1). Furthermore, each ester compound was reacted for a different reaction time. The types of polyols, the types of hydroxycarboxylic acid condensates, and the molar ratios of polyols to hydroxycarboxylic acid condensates are shown in the "Polyols," "Hydroxycarboxylic Acid Condensates," and "Ratios" columns of Table 3, respectively. The numbers in parentheses in the "Hydroxycarboxylic Acid Condensates" column indicate the degree of condensation of the hydroxycarboxylic acid, for example, (2) in the case of a dimer and (4) in the case of a tetramer.

[0107] It should be noted that the X:Y ratio is calculated by counting the number of hydroxyl groups (X) and the number of ester bonds (Y) based on the structural formula of the main component constituting the synthesized ester compound (A). Furthermore, the content of unreacted hydroxycarboxylic acid condensates contained in the synthesized ester compound (A) is determined according to the method described above as a "quantitative method for hydroxycarboxylic acid condensates". The values ​​are shown in the columns "Number of hydroxyl groups (X): Number of ester bonds (Y) in the ester compound (A) molecule" and "Amount of unreacted hydroxycarboxylic acid condensates contained in the ester compound (A)" in Table 3.

[0108] [Table 3]

[0109]

[0110] (Other (1): Ester compounds of epoxides and monocarboxylic acids)

[0111] A3-1: A substance obtained by esterifying 2 moles of oleic acid with 1 mole of polyethylene glycol (weight average molecular weight 600).

[0112] A3-2: A substance obtained by esterifying 1.8 moles of palm oil fatty acids with 1 mole of polyethylene glycol (weight average molecular weight 400).

[0113] A3-3: A substance obtained by esterifying 2 moles of palm oil fatty acids with 1 mole of polyethylene glycol (weight average molecular weight 600).

[0114] A3-4: A substance obtained by esterifying 1.5 moles of oleic acid with 1 mole of polyethylene glycol (weight average molecular weight 400).

[0115] It should be noted that the mass-average molecular weight was determined by using gel permeation chromatography to make the standard substance polyethylene glycol.

[0116] (Other (2): Nonionic surfactants other than those mentioned above)

[0117] N-1: The substance formed by adding 10 moles of EO to 1 mole of oleyl alcohol.

[0118] N-2: A substance formed by adding 10 moles of EO to 1 mole of isotracene alcohol.

[0119] N-3: A substance formed by the random addition of 1 mole of isotracene alcohol to 10 moles of EO and 10 moles of propylene oxide (hereinafter referred to as PO).

[0120] N-4: A substance formed by adding 5 moles of PO to 1 mole of isododecanool, followed by adding 5 moles of EO.

[0121] N-5: Sorbitan monooleate

[0122] N-6: Sorbitan trioleate

[0123] N-7: Trimethylolpropane dioleate

[0124] N-8: Diglyceride

[0125] N-9: Oleic diethanolamide

[0126] N-10: A substance formed by adding 5 moles of EO to 1 mole of stearamine.

[0127] N-11: A substance formed by adding 10 moles of EO to 1 mole of stearamine.

[0128] N-12: A substance obtained by esterifying 3 moles of oleic acid with respect to 1 mole of ester compound (A-6).

[0129] N-13: A substance obtained by cross-linking with 0.5 moles of adipic acid and terminal esterification with 2.5 moles of palmitic acid relative to 1 mole of ester compound (A-5).

[0130] <Ionic Surfactants>

[0131] I-1: Sodium salt of secondary alkyl sulfonate (carbon number 11-14)

[0132] I-2: Sodium dioctylsulfonate

[0133] I-3: Potassium 2-ethylhexanoate

[0134] I-4: Sodium α-olefin sulfonate

[0135] I-5: Phosphate ester of oleyl alcohol EO5 molar adduct - laurylamine EO10 molar adduct salt

[0136] I-6: Isostearyl phosphate-dibutylethanolamine salt

[0137] Experimental Group 2 (Evaluation of Burrs)

[0138] The freshly prepared treatment agents were diluted with an organic solvent (a mixture of n-hexane and ethanol) to prepare a 15% dilution. This dilution was then applied to untreated polyethylene terephthalate (PET) fibers of 1000 dtex, 126 filament length, and intrinsic viscosity of 0.93 using a guided oiling method at an application rate of 1.0% based on non-volatile components. The burrs on the treated fibers were then evaluated using a high-tensile friction testing machine (manufactured by Toray Engineering Co., Ltd.). Specifically, under conditions of yarn speed 100 m / min, load 2 kg, and OPU 1%, the burrs produced when the fibers were visually counted as they rubbed against a satin-finished chrome pin at 230°C were evaluated according to the following criteria. The results are shown in the "Moving Yarn Burrs" column of Tables 1 and 2.

[0139] • Evaluation criteria for burrs

[0140] ○○ (Good): 3 or less

[0141] ○ (Qualified): 4 to 7

[0142] × (Failure): 8 or more

[0143] Test Group 3 (Durability Evaluation)

[0144] Similar to test group 2, diluted solutions of each treatment agent were applied to polyethylene terephthalate fibers using a guided oiling method at an application rate of 1.0% based on non-volatile components. The durability of the treated fibers was then evaluated using a yarn cohesion tester (manufactured by Daiei Scientific Instruments Co., Ltd.). Specifically, the two ends of the test yarn were fixed to a section that alternately moved back and forth, and the yarn was passed through a free roller to create a circular yarn channel. Midway through the yarn channel, the yarn was brought into contact with a stainless steel mirror pin at an angle of approximately 90°. The test conditions were: a load of 1.2 kg, a rubbing length of 20 mm against a stainless steel mirror pin at 230°C, and a speed of 100 reciprocating strokes per minute. The number of reciprocating strokes until the yarn broke at the point of contact with the stainless steel mirror pin was counted, and the results were evaluated according to the following criteria. The results are shown in the "Friction Durability" column of Tables 1 and 2.

[0145] Durability evaluation criteria

[0146] ○○ (Good): 1001 times or more

[0147] ○ (Qualified): 501 times or more but less than 1000 times

[0148] × (Unacceptable): Less than 500 times

[0149] Experimental Group 4 (Evaluation of Smoke Generation)

[0150] The following evaluation of the fumes produced by each prepared treatment agent was conducted. Specifically, a stainless steel plate was placed on a heater at a 45° angle, and the surface temperature of the plate was set to 250°C. The presence of fumes from the treatment agent was visually confirmed when the treatment agent was added dropwise from the top of the plate at a rate of 0.5 mL / min under this condition, and the evaluation was performed according to the following criteria. The results are shown in the "Fume" column of Tables 1 and 2.

[0151] • Evaluation criteria for smoke generation

[0152] ○○ (Good): No smoke was emitted.

[0153] ○ (Pass): Slight smoke was observed.

[0154] × (Unacceptable): Obvious smoke emission

[0155] As can be seen from the results in Tables 1 and 2, the evaluations of burrs, durability, and smoke generation for the treatment agents in each embodiment are all qualified or above. According to the present invention, particularly in the spinning process of synthetic fibers, burrs on fibers treated with the treatment agent can be reduced, and the durability of the fibers can be improved. Furthermore, smoke generation during the spinning or drawing process of fibers treated with the treatment agent can be reduced.

Claims

1. A treatment agent for synthetic fibers, characterized by comprising: It contains a smoothing agent, a nonionic surfactant including an ester compound (A) formed from a polyhydric alcohol and a hydroxycarboxylic acid condensate, and an ionic surfactant.

2. The synthetic fiber treatment agent according to claim 1, wherein The polyhydric alcohol has a polyoxyalkylene group in the molecule.

3. The synthetic fiber treatment agent according to claim 1, wherein The ester compound (A) includes a compound in which the ratio of the number of hydroxyl groups (X) to the number of ester bonds (Y) in the molecule satisfies X:Y = 1:0.5 to 1:2.

5.

4. The synthetic fiber treatment agent according to claim 1, wherein The ester compound (A) is contained in a proportion of 5 mass% or more and 30 mass% or less relative to the total mass of the synthetic fiber treatment agent.

5. The synthetic fiber treatment agent according to claim 1, wherein A hydroxycarboxylic acid condensate is contained in a proportion of 10,000 ppm or less relative to the total mass of the synthetic fiber treatment agent.

6. A synthetic fiber, characterized by, A synthetic fiber to which the synthetic fiber treatment agent described in any one of claims 1 to 5 is attached.

Images