Synthetic fiber treatment agent and synthetic fiber

Abstract

The present invention provides a synthetic fiber treatment agent characterized by containing an amino-modified silicone (A) and a glycerol derivative (B), the glycerol derivative (B) contains at least one ester compound selected from the group consisting of a first ester compound (B1) that is a polyoxyalkylene castor oil ether derivative, a second ester compound (B2) that is a polyoxyalkylene hydrogenated castor oil ether derivative, and a third ester compound (B3) that is a polyoxyalkylene glycerol ether derivative. The strength and the antistatic property of the synthetic fiber can be improved.

Description

Technical Field

[0001] The present invention relates to a treating agent for synthetic fibers and synthetic fibers. Background Art

[0002] The common method for producing carbon fibers involves spinning a fibrous material and then firing it. This fibrous material is called a carbon fiber precursor. Carbon fiber precursors are sometimes made from polymeric or other fiber materials with a carbon fiber precursor treatment agent attached to their surface. This treatment agent is used to improve the handling of the carbon fiber precursor during the various steps of carbon fiber production. As shown in this example, various synthetic fiber treatment agents are sometimes used in the processing of synthetic fibers to improve their handling.

[0003] For example, Japanese Patent No. 7098210 (Patent Document 1) discloses a carbon fiber precursor treatment agent containing a smoothing agent comprising an ester compound that is a glycerol derivative. The invention described in Patent Document 1 can reduce fuzz in flame-resistant fibers after flame-resistant treatment of a carbon fiber precursor.

[0004] Prior art literature

[0005] Patent Document 1: Japanese Patent No. 7098210 Summary of the Invention

[0006] Problems to be solved by the invention

[0007] The invention described in Patent Document 1 still has room for improvement in the strength and antistatic properties of synthetic fibers treated with a treating agent.

[0008] Therefore, there is a demand for a synthetic fiber treatment agent that can improve the strength and antistatic properties of synthetic fibers compared to conventional technologies, and a synthetic fiber provided with the synthetic fiber treatment agent.

[0009] Means of solving the problem

[0010] The processing agent for synthetic fibers of the present invention is characterized in that it contains an amino-modified silicone (A) and a glycerol derivative (B); the glycerol derivative (B) contains at least one ester compound selected from a first ester compound (B1), a second ester compound (B2) and a third ester compound (B3); the first ester compound (B1) is an ester compound of a polyoxyalkylene castor oil ether and at least one compound selected from a carboxylic acid, a hydroxy acid, an alkylene oxide adduct of a hydroxy acid and a polymer of a hydroxy acid; the second ester compound (B2) is an ester compound of a polyoxyalkylene hydrogenated castor oil ether and at least one compound selected from a carboxylic acid, a hydroxy acid, an alkylene oxide adduct of a hydroxy acid and a polymer of a hydroxy acid; the third ester compound (B3) is an ester compound of a polyoxyalkylene glycerol ether and at least one hydroxy acid derivative selected from a carboxylic acid-hydroxy acid ester and a polymer of a hydroxy acid; the carboxylic acid-hydroxy acid ester is an ester compound of a carboxylic acid and at least one compound selected from a hydroxy acid, an alkylene oxide adduct of a hydroxy acid and a polymer of a hydroxy acid.

[0011] With this configuration, a synthetic fiber treating agent capable of improving the strength and antistatic properties of synthetic fibers compared to conventional technologies can be obtained.

[0012] In one embodiment, in the synthetic fiber processing agent of the present invention, it is preferred that the proportion of polyoxyethylene groups in the polyoxyalkylene groups in the glycerol derivative (B) is 99% by mass or more.

[0013] This configuration can easily reduce friction between the synthetic fiber to which the synthetic fiber treatment agent has been applied and the metal, thereby facilitating smooth winding of the synthetic fiber.

[0014] As one embodiment, the synthetic fiber processing agent of the present invention preferably comprises the glycerol derivative (B) containing at least one ester compound selected from the group consisting of the first ester compound (B1), the second ester compound (B2) and a specific third ester compound (B3a); the specific third ester compound (B3a) is a third ester compound (B3) having a content of hydroxy acid derivative residues of 2.5 mol or more and 3.0 mol or less per 1 mol of the polyoxyalkylene glycerol ether residue.

[0015] This configuration can improve the bundling properties of the synthetic fibers to which the synthetic fiber treatment agent has been applied, and thus the winding of the synthetic fibers can be easily and smoothly performed.

[0016] In one embodiment, in the synthetic fiber processing agent of the present invention, the glycerol derivative (B) preferably contains a carboxylic acid residue, and the proportion of the monocarboxylic acid-derived residue in the carboxylic acid residue is 99% by mass or more.

[0017] With this configuration, the synthetic fibers to which the synthetic fiber treating agent has been applied are less likely to be fused, and unwinding of the synthetic fibers wound around a roll or the like can be easily and smoothly performed.

[0018] In one embodiment, the synthetic fiber processing agent of the present invention preferably comprises the amino-modified silicone (A) in an amount of 5% by mass to 98% by mass based on the total mass of the amino-modified silicone (A) and the glycerol derivative (B).

[0019] With this configuration, the synthetic fiber to which the synthetic fiber treatment agent is applied has better strength and antistatic properties.

[0020] As one embodiment, the synthetic fiber treating agent of the present invention preferably further contains at least one cationic compound (C) selected from phosphonium salts and ammonium salts.

[0021] With this configuration, the antistatic properties of the synthetic fiber to which the synthetic fiber treatment agent is applied are further improved.

[0022] As one embodiment, the synthetic fiber processing agent of the present invention preferably has a proportion of the amino-modified silicone (A) of 8.0 mass% to 94.5 mass% or less, a proportion of the glycerol derivative (B) of 5.0 mass% to 90 mass% or less, and a proportion of the cationic compound (C) of 0.5 mass% to 5.0 mass% or less, relative to the total mass of the amino-modified silicone (A), the glycerol derivative (B) and the cationic compound (C).

[0023] With this configuration, the antistatic properties of the synthetic fiber to which the synthetic fiber treatment agent is applied are further improved.

[0024] The synthetic fiber of the present invention is characterized in that the above-mentioned synthetic fiber treating agent is attached to a fiber material.

[0025] This configuration can provide a synthetic fiber having improved strength and antistatic properties compared to conventional fibers.

[0026] As an embodiment, in the synthetic fiber of the present invention, preferably, the fiber material is a carbon fiber precursor.

[0027] With this configuration, a carbon fiber precursor having improved strength and antistatic properties compared to conventional technologies can be obtained.

[0028] Further features and advantages of the present invention will become clearer from the following description of exemplary and non-limiting embodiments. DETAILED DESCRIPTION

[0029] Embodiments of the synthetic fiber treatment agent and synthetic fiber of the present invention will be described. Hereinafter, an example in which the synthetic fiber treatment agent of the present invention is applied to the treatment of a carbon fiber precursor will be described.

[0030] [Composition of synthetic fiber treatment agent]

[0031] The synthetic fiber processing agent of this embodiment contains amino-modified silicone (A) and glycerin derivative (B). In addition, it is preferable that the synthetic fiber processing agent of this embodiment further contains a cationic compound (C).

[0032] When the synthetic fiber treatment agent of this embodiment is used as a treatment agent for spinning synthetic fibers, it is found that the bundling properties of the synthetic fibers are improved, the antistatic properties during winding are improved, and the friction with metal during winding is reduced, thereby improving the efficiency of spinning the synthetic fibers. In addition, when the synthetic fiber treatment agent of this embodiment is used to produce carbon fiber precursors, carbon fibers having high strength and being difficult to weld can be obtained.

[0033] (Amino-modified silicone)

[0034] Amino-modified silicone (A) is a compound in which amino groups are introduced at the ends of the silicone backbone, at the side chains, or at both ends. When amino groups are introduced at the ends of the silicone backbone, they can be introduced at both ends or at only one end. The introduced amino groups are arbitrary and can be monoamines, diamines, amino polyethers, etc. It should be noted that when the end groups are not modified, they can be alkyl groups (such as methyl), alkoxy groups (such as methoxy), hydroxyl groups, etc.

[0035] The amino-modified silicone (A) preferably has a kinematic viscosity of 50 mm at 25°C. 2 / s and above and 5000mm 2 / s or less. The kinematic viscosity of the amino-modified silicone (A) can be measured using a Cannon-Fenske viscometer.

[0036] The amino equivalent weight (g / mol) of amino-modified silicone can be determined based on the total amine value (KOH-mg / g). This total amine value is determined by accurately weighing 1 g of a mixed solution of 60 mL acetone and 20 mL n-hexane and titrating it with a perchloric acid solution of known concentration. The amino equivalent weight of amino-modified silicone can be between 1000 g / mol and 15000 g / mol.

[0037] (Glycerol derivatives)

[0038] The glycerol derivative (B) contains at least one ester compound selected from the following first ester compound (B1), second ester compound (B2), and third ester compound (B3).

[0039] The first ester compound (B1) is an ester compound of polyoxyalkylene castor oil ether and at least one compound (hereinafter referred to as an acid compound) selected from carboxylic acids, hydroxy acids, alkylene oxide adducts of hydroxy acids, and polymers of hydroxy acids.

[0040] The polyoxyalkylene group in the first ester compound (B1) is not limited and can be polyoxyethylene, polyoxypropylene, etc. In addition, the polyoxyalkylene group can be one type or multiple types. When there are multiple types of polyoxyalkylene groups, the multiple types of polyoxyalkylene groups can exist randomly (random adducts) or exist in blocks (block adducts). The polyoxyalkylene group preferably includes polyoxyethylene. It is particularly preferred that in the polyoxyalkylene group in the first ester compound (B1), the proportion of polyoxyethylene is 99% by mass or more, because in this case, the friction between the synthetic fiber and the metal can be suppressed. It should be noted that in the first ester compound (B1), the polyoxyalkylene group can exist as a polyoxyalkylene group in a polyoxyalkylene castor oil ether residue and a polyoxyalkylene group in the residue when the acid compound residue contains an alkylene oxide adduct residue of a hydroxy acid.

[0041] The number of polyoxyalkylene groups added to the first ester compound (B1) is not particularly limited. For example, the number of polyoxyalkylene groups added may be 5 or more and 60 or less per 1 mol of the first ester compound (B1). It should be noted that when the first ester compound (B1) contains multiple types of polyoxyalkylene groups, the total number of all polyoxyalkylene groups may be within the above range.

[0042] The acid compound preferably contains a carboxylic acid, more preferably a monocarboxylic acid. That is, the first ester compound (B1) preferably contains a carboxylic acid residue. From the perspective of preventing carbon fiber welding, it is particularly preferred that the monocarboxylic acid residue accounts for 99% by mass or more of the carboxylic acid residue.

[0043] When the acid compound includes a carboxylic acid, the carboxylic acid may be isostearic acid (monobasic), lauric acid (monobasic), oleic acid (monobasic), 2-ethylhexanoic acid (monobasic), adipic acid (dibasic), maleic acid (dibasic), succinic acid (dibasic), terephthalic acid (dibasic), sebacic acid (dibasic), etc., but are not limited thereto. When the acid compound includes a hydroxy acid, the hydroxy acid may be lactic acid, 3-hydroxyhexanoic acid, 2-hydroxydecanoic acid, 12-hydroxystearic acid, ricinoleic acid, etc., but are not limited thereto. When the acid compound includes an alkylene oxide adduct of a hydroxy acid, it may be the alkylene oxide adduct of the hydroxy acid exemplified above, but are not limited thereto. The amount of alkylene oxide added to the adduct is not limited, for example, it may be 5 moles or more and 10 moles or less per 1 mole of the adduct. When the acid compound includes a polymer of a hydroxy acid, it may be the polymer of the hydroxy acid exemplified above, but are not limited thereto. The degree of polymerization of the polymer is not particularly limited, for example, it may be a trimer or more and a hexamer or less.

[0044] As an example of the first ester compound (B1), an ester compound of polyoxyethylene castor oil ether (an example of polyoxyalkylene castor oil ether) and lauric acid (an example of carboxylic acid) is shown in Formula 1. However, the structure of the ester compound of polyoxyethylene castor oil ether and lauric acid is not limited to that of Formula 1.

[0045]

[0046] Formula 1 shows an ester compound obtained by reacting polyoxyethylene castor oil ether with lauric acid at a molar ratio of 1:3. In other words, in the example of Formula 1, all the hydroxyl groups of the polyoxyethylene castor oil ether are converted into ester bonds. However, in this embodiment, the first ester compound (B1) may also have a hydroxyl group derived from the hydroxyl group of the polyoxyalkylene castor oil ether. That is, the ratio of the polyoxyalkylene castor oil ether residue to the acid compound residue in the first ester compound (B1) is not limited.

[0047] The second ester compound (B2) is an ester compound of polyoxyalkylene hydrogenated castor oil ether and at least one compound (hereinafter referred to as an acid compound) selected from carboxylic acids, hydroxy acids, alkylene oxide adducts of hydroxy acids, and polymers of hydroxy acids.

[0048] The polyoxyalkylene group in the second ester compound (B2) is not limited and can be polyoxyethylene, polyoxypropylene, etc. In addition, the polyoxyalkylene group can be one type or multiple types. When there are multiple types of polyoxyalkylene groups, the multiple types of polyoxyalkylene groups can exist randomly (random adducts) or exist in blocks (block adducts). The polyoxyalkylene group preferably includes polyoxyethylene. It is particularly preferred that in the polyoxyalkylene group in the second ester compound (B2), the proportion of polyoxyethylene is 99% by mass or more, because at this time, the friction between the synthetic fiber and the metal can be suppressed. It should be noted that in the second ester compound (B2), the polyoxyalkylene group can exist as a polyoxyalkylene group in a polyoxyalkylene hydrogenated castor oil ether residue and a polyoxyalkylene group in the residue when the acid compound residue contains an alkylene oxide adduct residue of a hydroxy acid.

[0049] The number of polyoxyalkylene groups added to the second ester compound (B2) is not particularly limited. For example, the number may be 5 or more and 60 or less per 1 mol of the second ester compound (B2). It should be noted that when the second ester compound (B2) contains multiple types of polyoxyalkylene groups, the total number of all polyoxyalkylene groups may be within the above range.

[0050] The acid compound preferably contains a carboxylic acid, more preferably a monocarboxylic acid. That is, the second ester compound (B2) preferably contains a carboxylic acid residue. From the perspective of preventing carbon fiber welding, it is particularly preferred that the monocarboxylic acid residue accounts for 99% by mass or more of the carboxylic acid residue.

[0051] When the acid compound includes a carboxylic acid, the carboxylic acid may be isostearic acid (monobasic), lauric acid (monobasic), oleic acid (monobasic), 2-ethylhexanoic acid (monobasic), adipic acid (dibasic), maleic acid (dibasic), succinic acid (dibasic), terephthalic acid (dibasic), sebacic acid (dibasic), etc., but are not limited thereto. When the acid compound includes a hydroxy acid, the hydroxy acid may be lactic acid, 3-hydroxyhexanoic acid, 2-hydroxydecanoic acid, 12-hydroxystearic acid, ricinoleic acid, etc., but are not limited thereto. When the acid compound contains an alkylene oxide adduct of a hydroxy acid, it may be the alkylene oxide adduct of the hydroxy acid exemplified above, but are not limited thereto. The amount of alkylene oxide added to the adduct is not limited, for example, it may be 5 moles or more and 10 moles or less per 1 mole of the adduct. When the acid compound contains a polymer of a hydroxy acid, it may be the polymer of the hydroxy acid exemplified above, but are not limited thereto. The degree of polymerization of the polymer is not particularly limited, for example, it may be a trimer or more and a hexamer or less.

[0052] As an example of the second ester compound (B2), an ester compound of polyoxyethylene hydrogenated castor oil ether (an example of polyoxyalkylene hydrogenated castor oil ether) and oleic acid (an example of carboxylic acid) is shown in Formula 2. However, the structure of the ester compound of polyoxyethylene hydrogenated castor oil ether and oleic acid is not limited to the structure of Formula 2.

[0053]

[0054] In the second ester compound (B2), the ratio of the polyoxyalkylene hydrogenated castor oil ether residue to the acid compound residue is not limited. Therefore, the second ester compound (B2) may have a hydroxyl group derived from the hydroxyl group of the polyoxyalkylene hydrogenated castor oil ether.

[0055] The third ester compound (B3) is an ester compound of a polyoxyalkylene glyceryl ether and at least one hydroxy acid derivative selected from carboxylic acid-hydroxy acid esters and hydroxy acid polymers. Here, the carboxylic acid-hydroxy acid ester is an ester compound of a carboxylic acid and at least one compound selected from hydroxy acids, alkylene oxide adducts of hydroxy acids, and hydroxy acid polymers.

[0056] In the third ester compound (B3), the ratio of the polyoxyalkylene glyceryl ether residue to the hydroxy acid derivative residue is not limited. Therefore, the third ester compound (B3) may have a hydroxyl group derived from the polyoxyalkylene glyceryl ether. However, in the third ester compound (B3), the content of the hydroxy acid derivative residue is preferably 2.5 mol or more and 3.0 mol or less per 1 mol of the polyoxyalkylene glyceryl ether residue, because in this case, the bundling property of the synthetic fiber tends to be improved. Hereinafter, the third ester compound (B3) that meets this requirement will be referred to as a specific third ester compound (B3a) for distinction.

[0057] The polyoxyalkylene group in the third ester compound (B3) is not limited and can be polyoxyethylene, polyoxypropylene, etc. In addition, the polyoxyalkylene group can be one type or multiple types. When there are multiple types of polyoxyalkylene groups, the multiple types of polyoxyalkylene groups can exist randomly (random adducts) or exist in blocks (block adducts). The polyoxyalkylene group preferably includes polyoxyethylene. It is particularly preferred that in the polyoxyalkylene group in the third ester compound (B3), the proportion of polyoxyethylene is 99% by mass or more, because at this time, the friction between synthetic fibers and metals can be suppressed. It should be noted that in the third ester compound (B3), the polyoxyalkylene group can be present as a polyoxyalkylene glyceryl ether residue and a polyoxyalkylene group in the residue when the hydroxy acid derivative residue contains a carboxylic acid-hydroxy acid ester residue and the carboxylic acid-hydroxy acid ester residue contains an alkylene oxide adduct residue of a hydroxy acid.

[0058] The number of polyoxyalkylene groups added to the third ester compound (B3) is not particularly limited. For example, the number of polyoxyalkylene groups added may be 5 or more and 60 or less per 1 mol of the third ester compound (B3). It should be noted that when the third ester compound (B3) contains multiple types of polyoxyalkylene groups, the total number of all polyoxyalkylene groups may be within the above range.

[0059] When the hydroxy acid derivative contains carboxylic acid-hydroxy acid ester, it is preferred that the carboxylic acid constituting the carboxylic acid-hydroxy acid ester contains a monocarboxylic acid. That is, it is preferred that the third ester compound (B3) contains a carboxylic acid-hydroxy acid ester residue, and the carboxylic acid-hydroxy acid ester residue contains a carboxylic acid residue. In order to prevent carbon fiber welding, it is particularly preferred that the proportion of the residue from the monocarboxylic acid in the carboxylic acid residue is 99% by mass or more. The carboxylic acid constituting the carboxylic acid-hydroxy acid ester can be isostearic acid (monobasic), lauric acid (monobasic), oleic acid (monobasic), 2-ethylhexanoic acid (monobasic), adipic acid (dibasic), maleic acid (dibasic), succinic acid (dibasic), terephthalic acid (dibasic), sebacic acid (dibasic), etc., but is not limited thereto.

[0060] When the compound constituting the carboxylic acid-hydroxy acid ester contains a hydroxy acid, the hydroxy acid may be, but is not limited to, lactic acid, 3-hydroxyhexanoic acid, 2-hydroxydecanoic acid, 12-hydroxystearic acid, or ricinoleic acid. When the compound constituting the carboxylic acid-hydroxy acid ester contains an alkylene oxide adduct of a hydroxy acid, it may be, but is not limited to, the alkylene oxide adducts of the hydroxy acids exemplified above. The amount of alkylene oxide added to the adduct is not limited; for example, the amount may be 5 or more and 10 or less per 1 mole of the adduct. When the acid compound contains a hydroxy acid multimer, it may be, but is not limited to, the multimers of the hydroxy acids exemplified above. The degree of polymerization of the multimer is not particularly limited; for example, it may be a trimer or more and a hexamer or less.

[0061] As an example of the third ester compound (B3), an ester compound of polyoxyethylene glycerol ether (an example of polyoxyalkylene glycerol ether) and carboxylic acid-hydroxy acid ester is shown in Formula 3, wherein the carboxylic acid-hydroxy acid ester is an ester compound of oleic acid (an example of carboxylic acid) and 12-hydroxystearic acid (an example of hydroxy acid). However, the structure of the ester compound of polyoxyethylene glycerol ether and the above-mentioned carboxylic acid-hydroxy acid ester is not limited to

[0062] Structure of formula 3.

[0063]

[0064] (Cationic compound)

[0065] The synthetic fiber treatment agent of this embodiment preferably further contains at least one cationic compound (C) selected from phosphonium salts and ammonium salts. From the viewpoint of preventing the synthetic fiber from being charged, it is preferable that the synthetic fiber treatment agent contains the cationic compound (C).

[0066] As the phosphonium salt, tributylethylphosphonium diethyl phosphate, tetrabutylphosphonium dodecylbenzenesulfonic acid and the like can be exemplified, but are not limited thereto.

[0067] As the ammonium salt, benzalkonium chloride, benzethonium bromide, stearyltrimethylammonium dimethylphosphate, didecyldimethylammonium chloride and the like can be exemplified, but are not limited thereto.

[0068] (Other ingredients)

[0069] The synthetic fiber treatment agent of this embodiment may contain other components in addition to the amino-modified silicone (A), the glycerin derivative (B), and the optional cationic compound (C). Examples of such other components include, but are not limited to, preservatives, antistatic agents, antioxidants, ultraviolet absorbers, and defoaming agents.

[0070] The synthetic fiber treatment agent of this embodiment may further contain a silicone compound other than the amino-modified silicone (A). Examples of the silicone compound include, but are not limited to, dimethyl silicone and polyether-modified silicone.

[0071] The synthetic fiber treatment agent of this embodiment may contain a polyoxyalkylene derivative other than the glycerol derivative (B). Examples of the polyoxyalkylene derivative include, but are not limited to, alkylene oxide adducts of castor oil, alkylene oxide adducts of hydrogenated castor oil, and alkylene oxide adducts of saturated or unsaturated alcohols.

[0072] (Content of each ingredient)

[0073] In the synthetic fiber treatment agent of this embodiment, the proportion of the amino-modified silicone (A) relative to the total mass of the amino-modified silicone (A) and the glycerol derivative (B) is preferably 5% by mass or more and 98% by mass or less. If the proportion of the amino-modified silicone (A) is within this range, when the synthetic fiber treatment agent is used in the production of carbon fibers, the strength of the resulting carbon fibers is likely to be increased.

[0074] In the synthetic fiber treatment agent of this embodiment, preferably, the proportion of the amino-modified silicone (A) is 8.0% by mass or more and 94.5% by mass or less, the proportion of the glycerol derivative (B) is 5.0% by mass or more and 90% by mass or less, and the proportion of the cationic compound (C) is 0.5% by mass or more and 5.0% by mass or less, relative to the total mass of the amino-modified silicone (A), the glycerol derivative (B), and the cationic compound (C). If the proportions of the amino-modified silicone (A), the glycerol derivative (B), and the cationic compound (C) are within the above ranges, when the synthetic fiber treatment agent is used in the production of carbon fibers, the strength of the resulting carbon fibers is likely to be increased.

[0075] [Other embodiments]

[0076] For other configurations, it should be understood that the embodiments disclosed in this specification are illustrative in all respects, and the scope of the present invention is not limited thereto. It is readily understood by those skilled in the art that appropriate changes can be made without departing from the gist of the present invention. Therefore, other embodiments that are modified without departing from the gist of the present invention are naturally also included within the scope of the present invention.

[0077] Example

[0078] The present invention will be further described below with reference to the following examples. However, the following examples do not limit the present invention.

[0079] [Preparation of treatment agents for synthetic fibers]

[0080] The synthetic fiber treating agents of Examples 1 to 68 and Comparative Examples 1 to 7 shown in Tables 2 to 8 below were obtained by the following method.

[0081] (1) Reagents

[0082] (1-1) Amino-modified silicone

[0083] As amino-modified silicones, amino-modified silicones A-1 to A-8 having the properties shown in Table 1 were used. All amino-modified silicones correspond to amino-modified silicone (A) in the above embodiment. It should be noted that the kinematic viscosity and amino equivalent weight shown in Table 1 are values ​​measured by the methods described in the above embodiment.

[0084] Table 1: Amino-modified silicones

[0085] Table 1

[0086]

[0087] (1-2) Glycerol derivatives

[0088] (1-2-1) First Ester Compound

[0089] The following first ester compounds B1-1 to B1-7 were used as glycerol derivatives corresponding to the first ester compound. All of the first ester compounds correspond to the first ester compound (B1) of the above embodiment. However, the production methods described for each first ester compound are merely examples, and the results of the Examples and Comparative Examples will not change even if the first ester compound is produced using a method different from the methods described below.

[0090] (First ester compound B1-1)

[0091] Castor oil and ethylene oxide were reacted at a molar ratio of 1:5 to obtain polyoxyethylene castor oil ether. Polyoxyethylene castor oil ether and 3-hydroxyhexanoic acid (hydroxy acid) were reacted at a molar ratio of 1:1 to obtain the first ester compound B1-1.

[0092] (First Ester Compound B1-2)

[0093] Castor oil and ethylene oxide were reacted at a molar ratio of 1:10 to obtain polyoxyethylene castor oil ether. 2-Hydroxydecanoic acid and ethylene oxide were reacted at a molar ratio of 1:5 using methanesulfonic acid as an acid catalyst to obtain an ethylene oxide adduct of 2-hydroxydecanoic acid. Polyoxyethylene castor oil ether and the ethylene oxide adduct of 2-hydroxydecanoic acid were reacted at a molar ratio of 1:2 to obtain the first ester compound B1-2.

[0094] (First ester compound B1-3)

[0095] Castor oil and ethylene oxide were reacted at a molar ratio of 1:25 to obtain polyoxyethylene castor oil ether. Polyoxyethylene castor oil ether and isostearic acid (monocarboxylic acid) were reacted at a molar ratio of 1:2 to obtain the first ester compound B1-3.

[0096] (First ester compound B1-4)

[0097] Castor oil and ethylene oxide were reacted at a molar ratio of 1:40 to obtain polyoxyethylene castor oil ether. Polyoxyethylene castor oil ether and adipic acid (dicarboxylic acid) were reacted at a molar ratio of 1:3 to obtain the first ester compound B1-4.

[0098] (First ester compound B1-5)

[0099] Castor oil, ethylene oxide, and propylene oxide are reacted in a molar ratio of 1:10:10 to obtain polyoxyalkylene castor oil ether. The addition of ethylene oxide and propylene oxide to castor oil is performed by random addition. Using methanesulfonic acid as an acid catalyst, 3-hydroxycaproic acid (hydroxy acid), ethylene oxide, and propylene oxide are reacted in a molar ratio of 1:5:5 to obtain an alkylene oxide adduct of 3-hydroxycaproic acid. The addition of ethylene oxide and propylene oxide to 3-hydroxycaproic acid is performed by random addition. Polyoxyalkylene castor oil ether and the alkylene oxide adduct of 3-hydroxycaproic acid are reacted in a molar ratio of 1:2 to obtain the first ester compound B1-5.

[0100] (First Ester Compound B1-6)

[0101] Castor oil and propylene oxide are reacted at a molar ratio of 1:10 to obtain polyoxypropylene castor oil ether. Polyoxypropylene castor oil ether is reacted with lauric acid (monocarboxylic acid) at a molar ratio of 1:2 to obtain a first ester compound B1-6.

[0102] (First ester compound B1-7)

[0103] Castor oil, ethylene oxide, and propylene oxide were reacted at a molar ratio of 1:20:40 to obtain a polyoxyalkylene castor oil ether. Ethylene oxide and propylene oxide were added to castor oil in a random addition pattern. The polyoxyalkylene castor oil ether was reacted with a trimer of lactic acid (a hydroxy acid) at a molar ratio of 1:3 to obtain the first ester compound B1-7.

[0104] (1-2-2) Second Ester Compound

[0105] The following second ester compounds B2-1 to B2-6 were used as the second ester compounds. All of these second ester compounds correspond to the second ester compound (B2) in the above-described embodiment. However, the production methods described for each second ester compound are merely examples, and the results of the Examples and Comparative Examples will not change even if the second ester compound is produced using a method different from the methods described below.

[0106] (Second ester compound B2-1)

[0107] Hydrogenated castor oil and ethylene oxide were reacted at a molar ratio of 1:5 to obtain polyoxyethylene hydrogenated castor oil ether. Polyoxyethylene hydrogenated castor oil ether and 12-hydroxystearic acid (hydroxy acid) were reacted at a molar ratio of 1:3 to obtain a second ester compound B2-1.

[0108] (Second ester compound B2-2)

[0109] Hydrogenated castor oil and ethylene oxide were reacted at a molar ratio of 1:20 to obtain polyoxyethylene hydrogenated castor oil ether. Polyoxyethylene hydrogenated castor oil ether and oleic acid (monocarboxylic acid) were reacted at a molar ratio of 1:2 to obtain a second ester compound B2-2.

[0110] (Second ester compound B2-3)

[0111] Hydrogenated castor oil and ethylene oxide were reacted at a molar ratio of 1:60 to obtain polyoxyethylene hydrogenated castor oil ether. Polyoxyethylene hydrogenated castor oil ether was reacted with a hexamer of 12-hydroxystearic acid (hydroxy acid) at a molar ratio of 1:2 to obtain a second ester compound B2-3.

[0112] (Second ester compound B2-4)

[0113] Hydrogenated castor oil and ethylene oxide were reacted at a molar ratio of 1:25 to obtain polyoxyethylene hydrogenated castor oil ether. Polyoxyethylene hydrogenated castor oil ether and maleic acid (dicarboxylic acid) were reacted at a molar ratio of 1:1 to obtain a second ester compound B2-4.

[0114] (Second ester compound B2-5)

[0115] Hydrogenated castor oil, ethylene oxide, and propylene oxide were reacted in a molar ratio of 1:10:5 to obtain a polyoxyalkylene hydrogenated castor oil ether. Ethylene oxide and propylene oxide were added to the hydrogenated castor oil in a random manner. The polyoxyalkylene hydrogenated castor oil ether was reacted with isostearic acid (monocarboxylic acid) in a molar ratio of 1:1 to obtain a second ester compound B2-5.

[0116] (Second ester compound B2-6)

[0117] Hydrogenated castor oil and propylene oxide were reacted at a molar ratio of 1:50 to obtain polyoxypropylene hydrogenated castor oil ether. Polyoxypropylene hydrogenated castor oil ether and succinic acid (dicarboxylic acid) were reacted at a molar ratio of 1:3 to obtain a second ester compound B2-6.

[0118] (1-2-3) Third Ester Compound

[0119] The following tertiary ester compounds B3a-1 to B3a-8 and B3-9 to B3-20 were used as tertiary ester compounds. All tertiary ester compounds correspond to the tertiary ester compound (B3) in the above-described embodiment, and tertiary ester compounds B3a-1 to B3a-8 correspond to the specific tertiary ester compound (B3a) in the above-described embodiment. However, the production methods described for each tertiary ester compound are merely examples, and the results of the Examples and Comparative Examples will not change even if the tertiary ester compound is produced using a method different from the methods described below.

[0120] (Third ester compound B3a-1)

[0121] Glycerol and ethylene oxide were reacted in a molar ratio of 1:5 to produce polyoxyethylene glycerol ether. 2-ethylhexanoic acid (monocarboxylic acid) and 3-hydroxyhexanoic acid (hydroxy acid) were reacted in a molar ratio of 1:1 to produce a carboxylic acid-hydroxy acid ester. Polyoxyethylene glycerol ether and a carboxylic acid-hydroxy acid ester were reacted in a molar ratio of 1:3 to produce the third ester compound B3a-1.

[0122] The third ester compound B3a-1 has a 3 mol content of 3-hydroxyhexanoic acid residues (hydroxy acid derivative residues) per mol of polyoxyethylene glyceryl ether residues. This value corresponds to the molar ratio when polyoxyethylene glyceryl ether and carboxylic acid-hydroxy acid ester are reacted. It should be noted that in the following examples, the content of hydroxy acid derivative residues per mol of polyoxyethylene glyceryl ether residues in the third ester compound corresponds to the molar ratio when polyoxyethylene glyceryl ether and carboxylic acid-hydroxy acid ester are reacted.

[0123] (Third ester compound B3a-2)

[0124] Glycerol and ethylene oxide were reacted at a molar ratio of 1:20 to produce polyoxyethylene glycerol ether. Oleic acid (monocarboxylic acid) and 12-hydroxystearic acid (hydroxy acid) were reacted at a molar ratio of 1:1 to produce a carboxylic acid-hydroxy acid ester. Polyoxyethylene glycerol ether and a carboxylic acid-hydroxy acid ester were reacted at a molar ratio of 1:3 to produce the third ester compound B3a-2.

[0125] (Third ester compound B3a-3)

[0126] Glycerol is reacted with ethylene oxide at a molar ratio of 1:35 to produce polyoxyethylene glycerol ether. Using methanesulfonic acid as an acid catalyst, 12-hydroxystearic acid (hydroxy acid) is reacted with ethylene oxide at a molar ratio of 1:5 to produce an ethylene oxide adduct of 12-hydroxystearic acid. Isostearic acid (monocarboxylic acid) is reacted with the ethylene oxide adduct of 12-hydroxystearic acid at a molar ratio of 1:1 to produce a carboxylic acid-hydroxy acid ester. Polyoxyethylene glycerol ether is reacted with a carboxylic acid-hydroxy acid ester at a molar ratio of 1:3 to produce the third ester compound B3a-3.

[0127] (Third ester compound B3a-4)

[0128] Glycerol and ethylene oxide were reacted at a molar ratio of 1:50 to obtain polyoxyethylene glycerol ether. Polyoxyethylene glycerol ether was reacted with a hexamer of 12-hydroxystearic acid (hydroxy acid) at a molar ratio of 1:3 to obtain a third ester compound B3a-4.

[0129] (Third ester compound B3a-5)

[0130] Glycerol and ethylene oxide are reacted in a molar ratio of 1:10 to produce polyoxyethylene glyceryl ether. Terephthalic acid (dicarboxylic acid) and 12-hydroxystearic acid (hydroxy acid) are reacted in a molar ratio of 1:1 to produce a carboxylic acid-hydroxy acid ester. Polyoxyethylene glyceryl ether and a carboxylic acid-hydroxy acid ester are reacted in a molar ratio of 1:3 to produce the third ester compound B3a-5.

[0131] (Third ester compound B3a-6)

[0132] Glycerol and ethylene oxide were reacted in a molar ratio of 1:20 to produce polyoxyethylene glycerol ether. Sebacic acid (dicarboxylic acid) and 12-hydroxystearic acid (hydroxy acid) were reacted in a molar ratio of 1:1 to produce a carboxylic acid-hydroxy acid ester. Polyoxyethylene glycerol ether and a carboxylic acid-hydroxy acid ester were reacted in a molar ratio of 1:3 to produce the third ester compound B3a-6.

[0133] (Third ester compound B3a-7)

[0134] Glycerol and ethylene oxide were reacted in a molar ratio of 1:25 to produce polyoxyethylene glycerol ether. Maleic acid (a dicarboxylic acid) and ricinoleic acid (a hydroxy acid) were reacted in a molar ratio of 1:1 to produce a carboxylic acid-hydroxy acid ester. Polyoxyethylene glycerol ether and a carboxylic acid-hydroxy acid ester were reacted in a molar ratio of 1:3 to produce the third ester compound B3a-7.

[0135] (Third ester compound B3a-8)

[0136] Glycerol and ethylene oxide are reacted at a molar ratio of 1:40 to produce polyoxyethylene glyceryl ether. Adipic acid (dicarboxylic acid) and 3-hydroxycaproic acid (hydroxy acid) are reacted at a molar ratio of 1:1 to produce a carboxylic acid-hydroxy acid ester. Polyoxyethylene glyceryl ether and a carboxylic acid-hydroxy acid ester are reacted at a molar ratio of 1:3 to produce the third ester compound B3a-8.

[0137] (Third ester compound B3-9)

[0138] Glycerol and ethylene oxide were reacted in a molar ratio of 1:15 to obtain polyoxyethylene glycerol ether. Oleic acid (monocarboxylic acid) and 12-hydroxystearic acid (hydroxy acid) were reacted in a molar ratio of 1:1 to obtain a carboxylic acid-hydroxy acid ester. Polyoxyethylene glycerol ether and a carboxylic acid-hydroxy acid ester were reacted in a molar ratio of 1:2 to obtain a third ester compound B3-9.

[0139] (Third ester compound B3-10)

[0140] Glycerol is reacted with ethylene oxide in a molar ratio of 1:45 to obtain polyoxyethylene glycerol ether. Using methanesulfonic acid as an acid catalyst, 12-hydroxystearic acid (hydroxy acid) is reacted with ethylene oxide in a molar ratio of 1:5 to obtain an ethylene oxide adduct of 12-hydroxystearic acid. Isostearic acid (monocarboxylic acid) is reacted with an ethylene oxide adduct of 12-hydroxystearic acid in a molar ratio of 1:1 to obtain a carboxylic acid-hydroxy acid ester. Polyoxyethylene glycerol ether is reacted with a carboxylic acid-hydroxy acid ester in a molar ratio of 1:2 to obtain a third ester compound B3-10.

[0141] (Third ester compound B3-11)

[0142] Glycerol and ethylene oxide were reacted at a molar ratio of 1:5 to obtain polyoxyethylene glycerol ether. Polyoxyethylene glycerol ether was reacted with a hexamer of 12-hydroxystearic acid (hydroxy acid) at a molar ratio of 1:2 to obtain a third ester compound B3-11.

[0143] (Third ester compound B3-12)

[0144] Glycerol and ethylene oxide are reacted at a molar ratio of 1:20 to produce polyoxyethylene glycerol ether. Oleic acid (monocarboxylic acid) and 12-hydroxystearic acid (hydroxy acid) are reacted at a molar ratio of 1:1 to produce a carboxylic acid-hydroxy acid ester. Polyoxyethylene glycerol ether and a carboxylic acid-hydroxy acid ester are reacted at a molar ratio of 1:1 to produce a third ester compound B3-12.

[0145] (Third ester compound B3-13)

[0146] Glycerol and ethylene oxide were reacted in a molar ratio of 1:25 to obtain polyoxyethylene glyceryl ether. Adipic acid (dicarboxylic acid) and 3-hydroxycaproic acid (hydroxy acid) were reacted in a molar ratio of 1:1 to obtain a carboxylic acid-hydroxy acid ester. Polyoxyethylene glyceryl ether and a carboxylic acid-hydroxy acid ester were reacted in a molar ratio of 1:2 to obtain the third ester compound B3-13.

[0147] (Third ester compound B3-14)

[0148] Glycerol and ethylene oxide were reacted in a molar ratio of 1:30 to obtain polyoxyethylene glyceryl ether. Maleic acid (dicarboxylic acid) and ricinoleic acid (hydroxy acid) were reacted in a molar ratio of 1:1 to obtain a carboxylic acid-hydroxy acid ester. Polyoxyethylene glyceryl ether and a carboxylic acid-hydroxy acid ester were reacted in a molar ratio of 1:2 to obtain the third ester compound B3-14.

[0149] (Third ester compound B3-15)

[0150] Glycerol, ethylene oxide, and propylene oxide were reacted in a molar ratio of 1:10:10 to obtain a polyoxyalkylene glyceryl ether. Ethylene oxide and propylene oxide were added to glycerol in a random manner. Oleic acid (monocarboxylic acid) and 12-hydroxystearic acid (hydroxy acid) were reacted in a molar ratio of 1:1 to obtain a carboxylic acid-hydroxy acid ester. A polyoxyalkylene glyceryl ether and a carboxylic acid-hydroxy acid ester were reacted in a molar ratio of 1:2 to obtain a third ester compound B3-15.

[0151] (Third ester compound B3-16)

[0152] Glycerol, ethylene oxide, and propylene oxide were reacted in a molar ratio of 1:35:5 to obtain a polyoxyalkylene glycerol ether. Ethylene oxide and propylene oxide were added to glycerol in a random manner. 2-ethylhexanoic acid (monocarboxylic acid) and 3-hydroxyhexanoic acid (hydroxy acid) were reacted in a molar ratio of 1:1 to obtain a carboxylic acid-hydroxy acid ester. The polyoxyalkylene glycerol ether and the carboxylic acid-hydroxy acid ester were reacted in a molar ratio of 1:2 to obtain a third ester compound, B3-16.

[0153] (Third ester compound B3-17)

[0154] Glycerol, ethylene oxide, and propylene oxide were reacted in a molar ratio of 1:10:20 to obtain a polyoxyalkylene glycerol ether. The addition of ethylene oxide and propylene oxide to glycerol was performed by block addition, with propylene oxide then ethylene oxide added in that order. The polyoxyalkylene glycerol ether was reacted with a hexamer of 12-hydroxystearic acid (hydroxy acid) in a molar ratio of 1:1 to obtain a third ester compound, B3-17.

[0155] (Third ester compound B3-18)

[0156] Glycerol, ethylene oxide, and propylene oxide were reacted in a molar ratio of 1:5:35 to obtain a polyoxyalkylene glyceryl ether. Ethylene oxide and propylene oxide were added to glycerol in a random manner. Maleic acid (a dicarboxylic acid) and ricinoleic acid (a hydroxy acid) were reacted in a molar ratio of 1:1 to obtain a carboxylic acid-hydroxy acid ester. The polyoxyalkylene glyceryl ether and the carboxylic acid-hydroxy acid ester were reacted in a molar ratio of 1:2 to obtain a third ester compound, B3-18.

[0157] (Third ester compound B3-19)

[0158] Glycerol and propylene oxide were reacted in a molar ratio of 1:60 to obtain polyoxypropylene glyceryl ether. Adipic acid (dicarboxylic acid) and 3-hydroxycaproic acid (hydroxy acid) were reacted in a molar ratio of 1:1 to obtain a carboxylic acid-hydroxy acid ester. Polyoxypropylene glyceryl ether and a carboxylic acid-hydroxy acid ester were reacted in a molar ratio of 1:2 to obtain a third ester compound B3-19.

[0159] (Third ester compound B3-20)

[0160] Glycerol, ethylene oxide, and propylene oxide are reacted in a molar ratio of 1:20:10 to produce a polyoxyalkylene glycerol ether. The addition of ethylene oxide and propylene oxide to glycerol is a block addition, with ethylene oxide then propylene oxide added in that order. Adipic acid (dicarboxylic acid) and 3-hydroxycaproic acid (hydroxy acid) are reacted in a molar ratio of 1:1 to produce a carboxylic acid-hydroxy acid ester. The polyoxyalkylene glycerol ether and the carboxylic acid-hydroxy acid ester are reacted in a molar ratio of 1:1 to produce a third ester compound, compound B3-20.

[0161] (1-3) Cationic compounds

[0162] The following cationic compounds C-1 to C-6 were used as cationic compounds. All of the cationic compounds correspond to the cationic compound (C) of the above embodiment. In addition, cationic compounds C-1 to C-4 are ammonium salts, and cationic compounds C-5 to C-6 are phosphonium salts.

[0163] C-1: Benzalkonium chloride

[0164] C-2: Benzethonium Bromide

[0165] C-3: Stearyltrimonium dimethyl phosphate

[0166] C-4: Didecyldimethylammonium chloride

[0167] C-5: Tributylethylphosphonium diethyl phosphate

[0168] C-6: Tetrabutylphosphonium dodecylbenzenesulfonic acid

[0169] (1-4) Other ingredients

[0170] The following other components are used. Other components Z-1 and Z-2 are silicone compounds. It should be noted that the kinematic viscosities of other components Z-1 and Z-2 are values ​​measured using a Cannon-Fenske viscometer. Hereinafter, these components will be referred to as silicone compounds Z-1 and Z-2, respectively.

[0171] Z-1: Kinematic viscosity at 25°C is 350 mm 2 / s dimethicone

[0172] Z-2: Kinematic viscosity at 25°C is 1700 mm 2 / s polyether modified silicone

[0173] The mass ratio of silicone to polyether is 20:80, and the molar ratio of polyoxyethylene to polyoxypropylene in the polyether part is 40:60.

[0174] Other components Z-3 to Z-6 are polyoxyalkylene derivatives. Hereinafter, these components will be referred to as polyoxyalkylene derivatives Z-3 to Z-6, respectively, and their production methods will be described. The production methods described here are merely examples. Even if the polyoxyalkylene derivatives are produced using methods different from those described below, the results of the Examples and Comparative Examples will not be altered.

[0175] Z-3: Polyoxyethylene hydrogenated castor oil ether obtained by reacting hydrogenated castor oil with ethylene oxide at a molar ratio of 1:20

[0176] Z-4: Polyoxyethylene isononyl ether obtained by reacting isononyl alcohol and ethylene oxide at a molar ratio of 1:15

[0177] Z-5: Polyoxyethylene lauryl ether obtained by reacting secondary dodecyl alcohol with ethylene oxide at a molar ratio of 1:9

[0178] Z-6: a polyoxyalkylene oleyl ether obtained by reacting oleyl alcohol, ethylene oxide, and propylene oxide in a molar ratio of 1:45:5, wherein ethylene oxide and propylene oxide are added to oleyl alcohol in a block addition process in the order of propylene oxide and ethylene oxide.

[0179] (2) Preparation of treatment agents for synthetic fibers

[0180] (Preparation of Example 1)

[0181] 45% by mass of amino-modified silicone A-5, 35% by mass of first ester compound B1-1, 1% by mass of cationic compound C-6, and 19% by mass of polyoxyalkylene derivative Z-5 were weighed and placed in a beaker. After thoroughly mixing the components, ion-exchanged water was gradually added while stirring to prepare an aqueous solution with a total component concentration of 30% by mass. This aqueous solution was used as the synthetic fiber treatment agent of Example 1.

[0182] (Preparation of Other Examples and Comparative Examples)

[0183] Except for changing the types and ratios of the reagents to be mixed, the synthetic fiber treatment agents of each example were prepared in the same manner as in Example 1. The preparation conditions of all examples including Example 1 are shown in Tables 2 to 8 below.

[0184] [Evaluation of Treatment Agents for Synthetic Fibers]

[0185] (1) Production of carbon fiber

[0186] (1-1) Preparation of fiber materials

[0187] A copolymer composed of 95% by mass of acrylonitrile, 3.5% by mass of methyl acrylate, and 1.5% by mass of methacrylic acid with an intrinsic viscosity of 1.80 was dissolved in dimethylacetamide (DMAC) to prepare a spinning solution with a polymer concentration of 21.0% by mass and a viscosity of 500 poise at 60°C. The spinning solution was ejected from a spinneret with an inner diameter of 0.075 mm and 12,000 holes at a draft ratio of 0.8 into a coagulation bath containing a 70% by mass aqueous solution of DMAC maintained at a spinning bath temperature of 35°C. The coagulated fibers were then stretched 5 times while removing the solvent in a water washing tank to produce a water-swollen acrylic fiber bundle (an example of a fiber material).

[0188] (1-2) Preparation of carbon fiber precursor

[0189] The prepared acrylic fiber bundles were impregnated with a 4% ion-exchange aqueous solution of the synthetic fiber treatment agent of each example and comparative example, resulting in an attached amount of the treatment agent of 1% by mass (excluding the solvent). The acrylic fiber bundles, with the treatment agent attached, were then dried and densified using heated rollers at 150°C. The fibers were then stretched 1.7 times between heated rollers at 170°C and wound onto a fiber tube to produce a carbon fiber precursor.

[0190] (1-3) Production of carbon fiber

[0191] A filament was unwound from the carbon fiber precursor of each example and comparative example, and subjected to flame retardant treatment in an ignition furnace with a temperature gradient of 230-270°C under an air atmosphere for 1 hour, and then wound onto a filament tube to obtain a flame retardant filament. Furthermore, the flame retardant filament was unwound and fired in a carbonization furnace with a temperature gradient of 300-1300°C under a nitrogen atmosphere to convert it into carbon fiber, which was then wound onto a filament tube to obtain a carbon fiber.

[0192] (2) Evaluation of carbon fiber strength

[0193] The tensile strength of the carbon fibers in each of the Examples and Comparative Examples was measured in accordance with JIS R 7606: 2000. The tensile strength values ​​were classified into the following three levels.

[0194] A: The tensile strength is 4.5 GPa or more.

[0195] B: The tensile strength is 3.5 GPa or more and less than 4.5 GPa.

[0196] C: Tensile strength is less than 3.5 GPa.

[0197] (3) Evaluation of fiber-metal friction

[0198] For each example and comparative example, the presence and frequency of fiber breakage in the winder during the production of carbon fiber precursors were observed, and the results were classified into the following three levels.

[0199] A: No yarn breakage occurred 24 hours after the start of spinning.

[0200] B: Yarn breakage was observed twice or less within 24 hours from the start of spinning, but did not affect the operation.

[0201] C: Yarn breakage occurred three or more times within 24 hours from the start of spinning, affecting the operation.

[0202] (4) Cluster evaluation

[0203] For each of the Examples and Comparative Examples, the state of the acrylic fiber bundles when passing through the heating rollers was visually observed and classified into the following three levels based on the observation results.

[0204] A: The bundling condition is good, and no entanglement with the heating roller is observed.

[0205] B: The thread is slightly untied, but not broken, so it does not affect the operation.

[0206] C: The wire was found to be loose and broken many times, affecting the operation.

[0207] (5) Evaluation of anti-welding properties

[0208] For each of the carbon fibers in the Examples and Comparative Examples, 1 cm specimens were cut from ten randomly selected locations, yielding ten specimens. The fusion state of the fibers in each specimen was visually observed, and the number of fusion locations was counted. The average number of fusion locations in the ten specimens was used to categorize the fibers into the following three levels:

[0209] A: On average, there are less than 2 welding locations per specimen.

[0210] B: The number of weld locations per test piece is 2 or more and less than 7 on average.

[0211] C: The number of weld locations per test piece is 7 or more on average.

[0212] (6) Evaluation of antistatic properties

[0213] In each of the Examples and Comparative Examples, the power generated just in front of the winder during the production of the carbon fiber precursor was measured using a digital electrostatic potential meter KSD-1000 (manufactured by Kasuga Electric Co., Ltd.) The measured values ​​were classified into the following three levels.

[0214] AA: The power generated is less than 3kV.

[0215] A: The generated power is 3 kV or more and less than 5 kV.

[0216] B: The generated power is 5 kV or more and less than 7 kV.

[0217] C: The generated power is 7kV or more.

[0218] [result]

[0219] The compositions and evaluation results of the synthetic fiber treatment agents of Examples and Comparative Examples are shown in Tables 2 to 8.

[0220] Table 2: Examples 1 to 5

[0221] Table 2

[0222]

[0223] Table 3: Examples 16 to 30

[0224] Table 3

[0225]

[0226] Table 4: Examples 31 to 41

[0227] Table 4

[0228]

[0229] Table 5: Examples 42 to 52

[0230] Table 5

[0231]

[0232] Table 6: Examples 53-62

[0233] Table 6

[0234]

[0235] Table 7: Examples 63-68

[0236] Table 7

[0237]

[0238] Table 8: Comparative Examples 1 to 7

[0239] Table 8

[0240]

[0241] INDUSTRIAL APPLICABILITY The present invention can be used, for example, in the production of a carbon fiber precursor.

Claims

1. A treatment agent for synthetic fibers, characterized in that: The synthetic fiber treating agent contains amino-modified silicone (A) and a glycerin derivative (B); The glycerol derivative (B) contains at least one ester compound selected from the group consisting of a first ester compound (B1), a second ester compound (B2), and a third ester compound (B3); The first ester compound (B1) is an ester compound of polyoxyalkylene castor oil ether and at least one compound selected from carboxylic acid, hydroxy acid, alkylene oxide adduct of hydroxy acid and polymer of hydroxy acid; The second ester compound (B2) is an ester compound of polyoxyalkylene hydrogenated castor oil ether and at least one compound selected from carboxylic acid, hydroxy acid, alkylene oxide adduct of hydroxy acid and polymer of hydroxy acid; The third ester compound (B3) is an ester compound of polyoxyalkylene glycerol ether and at least one hydroxy acid derivative selected from a polymer of carboxylic acid-hydroxy acid ester and hydroxy acid; The carboxylic acid-hydroxy acid ester is an ester compound of a carboxylic acid and at least one compound selected from the group consisting of a hydroxy acid, an alkylene oxide adduct of a hydroxy acid, and a polymer of a hydroxy acid.

2. The synthetic fiber processing agent according to claim 1, wherein Among the polyoxyalkylene groups in the glycerol derivative (B), the proportion of polyoxyethylene groups is 99% by mass or more.

3. The synthetic fiber processing agent according to claim 1, wherein The glycerol derivative (B) contains at least one ester compound selected from the group consisting of the first ester compound (B1), the second ester compound (B2), and a specific third ester compound (B3a); The specific third ester compound (B3a) is a third ester compound (B3) having a hydroxy acid derivative residue content of 2.5 mol or more and 3.0 mol or less per 1 mol of the polyoxyalkylene glyceryl ether residue.

4. The synthetic fiber processing agent according to claim 1, wherein The glycerol derivative (B) contains a carboxylic acid residue; The proportion of the monocarboxylic acid-derived residue in the carboxylic acid residue is 99% by mass or more.

5. The synthetic fiber processing agent according to claim 1, wherein The proportion of the amino-modified silicone (A) relative to the total mass of the amino-modified silicone (A) and the glycerin derivative (B) is 5% by mass or more and 98% by mass or less.

6. The synthetic fiber processing agent according to claim 1, wherein The synthetic fiber treating agent further contains at least one cationic compound (C) selected from phosphonium salts and ammonium salts.

7. The synthetic fiber processing agent according to claim 6, wherein Relative to the total mass of the amino-modified silicone (A), the glycerin derivative (B) and the cationic compound (C); The amino-modified silicone (A) accounts for 8.0% by mass or more and 94.5% by mass or less; The proportion of the glycerol derivative (B) is 5.0% by mass or more and 90% by mass or less; The proportion of the cationic compound (C) is 0.5% by mass or more and 5.0% by mass or less.

8. A synthetic fiber, characterized in that The synthetic fiber treating agent according to any one of claims 1 to 7 is attached to a fiber material.

9. The synthetic fiber according to claim 8, wherein The fiber material is a carbon fiber precursor.

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