Fiber treatment aid and treatment agent for polyester fibers

Abstract

To provide a fiber treatment auxiliary agent capable of preventing dye aggregation and aggregation of the dye and functional medicine, in dyeing of polyester fiber or the like at a high temperature and high pressure, and in combination of the dye and the functional medicine such as a flame retardant, and providing uniform matters which are dyed.SOLUTION: A fiber treatment auxiliary agent comprises: (A) 40-90 pts.mass of a compound expressed by a specific general formula (1), as the compound expressed by the general formula (1), for example, an ammonium saltpand a metal salt of polyoxyethylene polyoxypropylene glycol monosulphate; (B) 5-25 pts.mass of a compound expressed by a specific general formula (2), as the compound expressed by the general formula (2), for example, an ammonium salt and a metal salt of polyoxyethylene tristyrenated phenyl ether sulphate; and (C) 5-35 pts.mass of polyoxy alkylene polyhydric alcohol fatty acid ester.SELECTED DRAWING: None

Description

Technical Field

[0001] The present invention relates to a fiber treatment aid and a treatment agent for polyester fibers. More specifically, when dyeing polyester fibers at high temperatures, it stabilizes the dispersion state of dyes, and further provides a treatment agent for polyester fibers that gives a uniform dyed product without aggregating dyes and flame retardants when a flame retardant is used in combination.

Background Art

[0002] Generally, the dyeing of polyester-based fibers is generally carried out using disperse dyes in a weakly acidic pH range under high temperature and high pressure in an aqueous solution system at 110 to 140°C. At this time, it is common for the disperse dye itself to contain a naphthalenesulfonic acid-based dispersant. However, under high temperature and high pressure, the dispersibility of the dye decreases, causing poor dyeing and aggregation of the dye, resulting in contamination of the dyed product and contamination of the dyeing machine. Therefore, a method of obtaining a uniform dyed product by using a surfactant composition called a dispersion leveling agent has been adopted.

[0003] Furthermore, in order to impart functionality to the dyed product in the dyeing process, it is generally common to carry out dyeing in combination with functional agents such as flame retardants and lightfast agents. At this time, the hydrophobic structures in the functional agents cause aggregation with the dyes, resulting in problems such as contamination of the dyed product and contamination of the dyeing machine.

[0004] The occurrence of poor dyeing and contamination of the dyeing machine requires redyeing of the dyed product and frequent cleaning of the dyeing machine, leading to a decrease in energy efficiency and an increase in running costs due to an increase in drainage. Therefore, countermeasures to eliminate poor dyeing and the contamination situation of the dyeing machine are required.

[0005] To solve such problems, the development of dispersion leveling agents such as the methods described in Patent Document 1 and Patent Document 2, and the development of flame retardants having a uniform dispersion state such as Patent Document 3, Patent Document 4, and Patent Document 5 have been carried out.

Prior Art Documents

Patent Documents

[0006] [Patent Document 1] Japanese Patent Publication No. 2015-522721 [Patent Document 2] Japanese Unexamined Patent Application Publication No. 2014-047438 [Patent Document 3] Japanese Unexamined Patent Application Publication No. 2019-6992 [Patent Document 4] Patent No. 6039326 [Patent Document 5] Japanese Unexamined Patent Application Publication No. 2014-189914 [Summary of the Invention] [Problems to be Solved by the Invention]

[0007] When dyeing fibers such as polyester under high temperature and high pressure, or when using functional chemicals such as dyes and flame retardants in combination, it is an object of the present invention to provide a fiber treatment aid that can prevent dye aggregation and aggregation of dyes and functional chemicals, and can provide a uniform dyed product. [Means for Solving the Problems]

[0008] As a result of intensive studies to solve the above problems, the present inventors have found that when dyeing fibers such as polyester under high temperature and high pressure, or when using functional chemicals such as dyes and flame retardants in combination, by using a fiber treatment aid containing a combination of a specific anionic surfactant and a polyoxyalkylene polyhydric alcohol fatty acid ester, dye aggregation can be suppressed, and aggregation of dyes and functional chemicals can be prevented, and a uniform dyed product can be provided. More specifically, the present invention has found that a treatment agent for polyester fibers characterized by containing (A) an anionic surfactant represented by the following general formula (1), (B) an anionic surfactant represented by the following general formula (2), and (C) a polyoxyalkylene polyhydric alcohol fatty acid ester can solve the above problems, and thus the present invention has been completed.

[0009] That is, the present invention is (A) 40 to 90 parts by mass of a compound represented by the following general formula (1) X 1 -O-(A 1 O) n1 (A 2 O) n2 -X 2 (1) (In the formula, A 1 is an ethylene group, A 2 is an alkylene group having 3 or 4 carbon atoms, n 1 is a number from 3 to 30, n 2 is a number from 5 to 60, A 1 O and A 2 The mutual arrangement of O is not limited, and they may form a block unit or be randomly bonded. X 1 is a hydrogen atom, an alkyl group or alkenyl group having 8 to 22 carbon atoms, -SO3M, or -PO3M, and X 2 is -SO3M, or -PO3M, and M is a hydrogen atom, an ammonium ion, an organic ammonium ion, or a monovalent metal ion), (B) 5 to 25 parts by mass of a compound represented by the following general formula (2)

Chemical formula

Advantages of the Invention

[0010] The fiber treatment aid of the present invention can suppress the generation of aggregates of dyes and flame retardants and provide a dyed product with good and uniform dyeing in the dyeing process of fibers such as polyester at high temperatures.

Embodiments for Carrying Out the Invention

[0011] Hereinafter, each component will be described in more detail. The component (A) is a compound represented by the following general formula (1). The component (A) is important in that it exhibits the effect of preventing dye aggregation and aggregation of functional agents such as dyes and flame retardants in the dyeing of polyester fibers under high temperature and high pressure. X 1 -O-(A 1 O) n1 (A 2 O) n2 -X 2 (1) In the formula, A 1 is an ethylene group. A 2 is an alkylene group having 3 or 4 carbon atoms, preferably a propylene group having 3 carbon atoms. n 1 is a number from 3 to 30, n 2 is a number from 5 to 60, and the mutual arrangement of A 1 O and A 2 O is not limited, and they may form a block unit or may be randomly bonded. X 1 is a hydrogen atom, an alkyl group or alkenyl group having 8 to 22 carbon atoms, -SO3M, or -PO3M, and X 2 is -SO3M, or -PO3M. M is a monovalent cation selected from a hydrogen atom, an ammonium ion, an organic ammonium ion, and a monovalent metal ion.

[0012] More specifically, the component (A) is a polyoxyalkylene glycol sulfonate or polyoxyalkylene glycol phosphate, a polyoxyalkylene aliphatic alcohol sulfonate, and a polyoxyalkylene aliphatic alcohol phosphate.

[0013] A 1 O is an oxyethylene group, and A 2 O is an oxyalkylene group having 3 or 4 carbon atoms. n 1 Or n 2 represents the average number of moles of oxyalkylene added, represented by (A 1 O) and (A 2 O), and it does not have to be an integer. n 1 is from 3 to 30, preferably from 5 to 25. n 1 If it is less than 3, the hydrophobicity of the (A) component increases, and aggregation of dyes and functional agents is likely to occur, and the dispersibility may deteriorate. n 1 If it is greater than 30, the hydrophilicity of the (A) component increases, and sufficient dispersibility cannot be exhibited. n 2 is from 5 to 60, preferably from 10 to 50. n 2 If it is less than 5, the proportion of hydrophobic groups in the structure of the (A) component becomes small, and sufficient surface activity and dispersing performance cannot be exhibited. Also, n 2 If it is greater than 60, the proportion of hydrophobic groups in the structure of the (A) component becomes too high, and aggregation of dyes and functional agents is likely to occur, and the dispersibility may deteriorate. (A 1 O) and (A 2 O) The mutual arrangement (the addition order of oxyalkylene groups) is not limited. The addition method when adding alkylene oxide may be either block addition or random addition.

[0014] X 1 is a hydrogen atom, an alkyl group or alkenyl group having 8 to 22 carbon atoms, preferably 7 to 21 carbon atoms, -SO3M, or -PO3M, and X 2It is -SO3M or -PO3M. M is a hydrogen atom, an ammonium ion, an organic ammonium ion, or a monovalent metal ion. The monovalent metal ion is preferably a sodium ion or a potassium ion. The alkyl group or alkenyl group having 8 to 22 carbon atoms, preferably 7 to 21 carbon atoms, includes, for example, heptyl group, octyl group, nonyl group, decyl group, decenyl group, undecyl group, dodecyl group, tridecyl group, tridecenyl group, tetradecyl group, tetradecenyl group, pentadecyl group, hexadecyl group, heptadecyl group, heptadecenyl group, octadecyl group, isooctadecyl group, nonadecyl group, nonadecenyl group, icosyl group, and henicosyl group. Among them, octyl group, decyl group, dodecyl group, and tridecyl group are preferable.

[0015] In -SO3M, M is a hydrogen atom, an ammonium ion, an organic ammonium ion, or a monovalent metal ion. The monovalent metal ion is preferably a sodium ion or a potassium ion. Preferably, M is an ammonium ion, an organic ammonium ion, a sodium ion, or a potassium ion. This functional group can be introduced into polyoxyalkylene glycol by a general sulfonation or sulfuric acidification method. For example, it can be introduced by reacting polyoxyalkylene glycol with chlorosulfonic acid, sulfuric anhydride, sulfamic acid, or sulfuric acid. More specifically, in the case of chlorosulfonic acid or sulfuric anhydride, the reaction temperature is 0 to 70°C, and in the case of sulfamic acid or sulfuric acid, the reaction temperature is 50 to 150°C. The reaction state can be determined by measuring the amount of bound sulfuric acid, and the degree of anionization is usually 80% or more, preferably 85% or more.

[0016] In -PO3M, M is a hydrogen atom, an ammonium ion, an organic ammonium ion, or a monovalent metal ion. The organic ammonium ion is an ammonium ion (NH4 +) Among the four hydrogens, one or more are substituted with organic groups such as alkyl groups or hydroxyalkyl groups. Examples include monoethanolammonium ions, diethanolammonium ions, triethanolammonium ions, etc. The monovalent metal ion is preferably a sodium ion or a potassium ion. Preferably, M is an ammonium ion, an organic ammonium ion, a sodium ion, or a potassium ion. The introduction of the functional group can be introduced into the polyoxyalkylene glycol by a general phosphorylation method. For example, it can be introduced by reacting a phosphorylating agent such as phosphoric acid, polyphosphoric acid, phosphoric anhydride, phosphorus oxychloride, etc. with the polyoxyalkylene glycol. More specifically, the reaction with phosphoric anhydride can be carried out at a reaction temperature of 30 to 150 °C in a nitrogen atmosphere. The reaction is determined by measuring the acid value, and the degree of anionization is usually 90 mol% or more, preferably 95 mol% or more.

[0017] Examples of the compound represented by the general formula (1) include Polyoxyethylene polyoxypropylene glycol monosulfate ammonium salt and metal (Na, K) salts Polyoxyethylene polyoxypropylene glycol disulfate ammonium salt and metal (Na, K) salts Polyoxyethylene polyoxypropylene glycol monophosphate ammonium salt and metal (Na, K) salts Polyoxyethylene polyoxypropylene glycol diphosphate ammonium salt and metal (Na, K) salts Polyoxyethylene polyoxypropylene octyl alcohol sulfate ammonium salt and metal (Na, K) salts Polyoxyethylene polyoxypropylene octyl alcohol phosphate ammonium salt and metal (Na, K) salts Polyoxyethylene polyoxypropylene lauryl alcohol sulfate ammonium salt and metal (Na, K) salts Polyoxyethylene polyoxypropylene lauryl alcohol phosphate ammonium salt and metal (Na, K) salts Ammonium polyoxyethylene polyoxypropylene tridecanol sulfate and metal (Na, K) salts Ammonium polyoxyethylene polyoxypropylene tridecanol phosphate and metal (Na, K) salts Ammonium polyoxyethylene polyoxypropylene oleyl alcohol sulfate and metal (Na, K) salts Ammonium polyoxyethylene polyoxypropylene oleyl alcohol phosphate and metal (Na, K) salts etc. can be mentioned.

[0018] More preferably Ammonium polyoxyethylene polyoxypropylene glycol monosulfate and metal (Na, K) salts Ammonium polyoxyethylene polyoxypropylene glycol disulfate and metal (Na, K) salts Ammonium polyoxyethylene polyoxypropylene tridecanol sulfate and metal (Na, K) salts Ammonium polyoxyethylene polyoxypropylene lauryl alcohol phosphate and metal (Na, K) salts Ammonium polyoxyethylene polyoxypropylene tridecanol phosphate and metal (Na, K) salts etc. can be mentioned.

[0019] (A) component can be prepared according to a conventionally well-known method. For example, (A) ammonium polyoxyalkylene glycol sulfonate and metal (Na, K) salts, or ammonium polyoxyalkylene glycol phosphate and metal (Na, K) salts can be produced by adding alkylene oxide to ethylene glycol and then by the aforementioned sulfonation method or phosphorylation method. Furthermore, the polyoxyalkylene aliphatic alcohol sulfonic acid ester ammonium salt and metal (Na, K) salts, or the polyoxyalkylene aliphatic alcohol phosphate ester ammonium salt and metal (Na, K) salts can be produced, for example, by adding an alkylene oxide to an aliphatic alcohol under normal conditions, then adding a functional group by the above-described sulfonation method or phosphorylation method, and then performing neutralization as necessary.

[0020] The amount of component (A) contained in the fiber treatment aid of the present invention is 40 to 90% by mass, preferably 50 to 90% by mass, more preferably 60 to 85% by mass based on the total mass of the fiber treatment aid.

[0021] Component (B) is a compound represented by the following general formula (2).

Chemical formula

[0022] In the above formula (2), m represents the average number of moles of addition of the styryl group, and it is not necessary for it to be an integer. m is from 1 to 3, more preferably from 2 to 3.

[0023] A 3 is an alkylene group having 2 to 4 carbon atoms, preferably an alkylene group having 2 or 3 carbon atoms, and more preferably an ethylene group having 2 carbon atoms. n 3 is the average number of moles of addition of the oxyalkylene group, which is from 5 to 60, more preferably from 8 to 50, and still more preferably a number from 10 to 40.

[0024] As the component (B) above, preferably, an ammonium salt and metal (Na, K) salts of polyoxyethylene tristyrenated phenyl ether sulfate are mentioned.

[0025] The preparation of the component (B) may be carried out according to a conventionally known method. For example, ammonium salts and metal (Na, K) salts of polyoxyethylene styrenated phenyl ether sulfate can be produced, for example, by reacting a styrene monomer with phenol under normal conditions, then adding ethylene oxide, sulfonating by the above method, and performing neutralization as necessary.

[0026] The amount of the component (B) contained in the fiber treatment aid of the present invention is 5 to 25% by mass, preferably 5 to 20% by mass, and more preferably 8 to 18% by mass with respect to the total mass of the fiber treatment aid.

[0027] The (C) component is a polyoxyalkylene polyhydric alcohol fatty acid ester, preferably a compound represented by the following general formula (3). This compound is a component necessary for eliminating uneven dyeing during dyeing and obtaining a uniformly dyed object. [H-(OA 4 ) n4 -O-] r R 1 [-O-(A 5 O) n5 -C(=O)-R 2 s (3) In the above formula (3), R 1 is a residue obtained by removing two or more hydroxy groups from a polyhydric alcohol having 2 to 30 carbon atoms, preferably 2 to 10 carbon atoms, more preferably 2 to 6 carbon atoms, and having 2 to 8 valences, preferably 2 to 6 valences, more preferably 2 to 4 valences. A 4 is a divalent alkylene group having 2 to 4 carbon atoms, preferably ethylene having 2 carbon atoms. n 4 is a number obtained by dividing the average number of moles of oxyalkylene added by (r + s), and is a number from 1 to 80, preferably 1 to 40, more preferably 2 to 30, still more preferably 3 to 25. R 2 is an alkyl group having 1 to 30 carbon atoms or an alkenyl group having 2 to 30 carbon atoms, preferably an octyl group, a dodecyl group, a hexadecyl group, an octadecyl group, an octadecenyl group, an isooctadecyl group. A 5 is a divalent alkylene group having 2 to 4 carbon atoms, preferably ethylene having 2 carbon atoms. n 5 is a number obtained by dividing the average number of moles of alkylene oxide added by (r + s), and is a number from 1 to 80, preferably 1 to 40, more preferably 2 to 30, still more preferably 3 to 25. r and s are integers satisfying 0 ≦ r ≦ 7, 1 ≦ s ≦ 8, and 2 ≦ r + s ≦ 8. Preferably, r is an integer from 0 to 1, and s is an integer from 2 to 6.

[0028] ​The above component (C) is an ester of a 2- to 8-valent, preferably 2- to 6-valent polyhydric alcohol and a fatty acid. Examples of the polyhydric alcohol include ethylene glycol, diethylene glycol, trimethylolpropane, glycerin, pentaerythritol, sorbitol, etc. Examples of the fatty acid include caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, oleic acid, linoleic acid, stearic acid, and behenic acid, etc. The above component (C) is preferably a fatty acid ester of a polyoxyethylene polyhydric alcohol, and more preferably polyoxyethylene glycol dioleate, polyoxyethylene glycerol trioleate, etc.

[0029] In the above component (C), the average number of moles of ethylene oxide added is preferably 3 to 40, more preferably 6 to 30, and still more preferably 8 to 25 moles. When the number of moles of ethylene oxide added is less than 3, the hydrophobicity increases, which may cause aggregation of the dye and contaminate the dyed object. When it is 40 moles or more, the hydrophilicity increases, and there is a possibility that the level dyeing property of the dyed object is insufficient.

[0030] (C) The preparation of the polyoxyethylene polyhydric alcohol fatty acid ester may follow a conventionally known method. For example, it can be produced by adding ethylene oxide to a polyhydric alcohol and then reacting with a fatty acid, or by reacting a polyhydric alcohol and a fatty acid to synthesize an ester and then adding ethylene oxide.

[0031] The amount of component (C) contained in the fiber treatment aid of the present invention is 5 to 35% by mass, preferably 8 to 30% by mass, and more preferably 10 to 25% by mass based on the total mass of the fiber treatment aid.

[0032] The mass ratio [(A) / (B) / (C)] of the component (A), component (B), and component (C) is 40 to 90 / 5 to 25 / 5 to 35. Preferably, the mass ratio [(A) / (B) / (C)] is 50 to 80 / 5 to 20 / 10 to 30. However, the total of component (A), component (B), and component (C) is 100. Thereby, the fiber treatment auxiliary agent of the present invention can prevent the aggregation of dyes and the aggregation of dyes and functional agents in dyeing under high temperature and high pressure, and can maintain a uniform dispersion state. When the mass ratio of component (A) to components (B) and (C) is less than the above lower limit value, sufficient dispersion performance cannot be obtained under the dyeing conditions under high temperature and high pressure. Further, when the mass ratio of component (A) is greater than the above upper limit, the level dyeing property required for dyeing is insufficient and the dyeing performance deteriorates.

[0033] The production method of the fiber treatment auxiliary agent of the present invention is not particularly limited, and may follow a conventionally known method. For example, for the mixing of component (A), component (B), and component (C), after charging each component into a container, it is uniformly mixed at a temperature of 40 to 60°C. The fiber treatment auxiliary agent may contain water and / or a solvent for the purpose of improving the appearance stability of the chemical agent and the solubility when added to the dyeing solution.

[0034] The fiber treatment auxiliary agent of the present invention is used in the dyeing of fibers such as polyester and the treatment process with functional agents. Examples of the polyester fiber include polyester fiber, cation-dyeable polyester fiber, recycled polyester fiber, and polyester fiber composed of two or more of these. Further, as other fibers, fiber products composed of blended fibers of the polyester fiber and natural fibers (such as cotton, hemp, silk, wool, etc.), semi-synthetic fibers (such as rayon, acetates, etc.), and other synthetic fibers (such as nylon, acrylic, polyamide, polyurethane, polyethylene, polypropylene, etc.) are also included. The fiber treatment auxiliary agent of the present invention is preferably a fiber treatment auxiliary agent for polyester fiber.

[0035] The form of the fiber product is not particularly limited, and may be short fiber, long fiber, yarn, woven fabric, knitted fabric, non-woven fabric, etc.

[0036] For the dyeing using the fiber treatment aid of the present invention, within a range that does not inhibit the effects of the present invention as necessary, flame retardants such as brominated flame retardants or phosphorus-based flame retardants, deodorants, antibacterial agents, softeners, water absorbents, water and oil repellents, smoothing agents, penetrants, antistatic agents, chelating agents, antioxidants, defoaming agents, carrier agents, fixing agents, light stabilizers, ultraviolet absorbers, thickeners, and additives such as yellowing inhibitors can be used. These additives can be used simultaneously with the dyeing process of polyester fibers using the fiber treatment aid of the present invention and / or in the pretreatment process and / or the post-treatment process. Further, the present invention can provide a fiber treatment agent containing the fiber treatment aid composed of the above components (A) to (C) and optionally other additives described above, preferably a treatment agent for polyester fibers. The blending amount may be appropriately adjusted according to conventionally known fiber treatment agents.

[0037] Method for producing a fiber dyed product The present invention provides a method for producing a fiber dyed product, which includes a step of adding the fiber treatment aid to a dyeing bath and a step of dyeing the fiber in the dyeing bath to obtain a dyed product. The dyeing method of fibers such as polyester may follow a conventionally known method. For example, a dyed cloth, a dye, other additives for imparting the above functions, and the fiber treatment aid of the present invention can be added to a dyeing bath solution adjusted to pH 4.5 to 6.0, and using a dyeing machine, dyeing can be performed at an arbitrary dyeing temperature. The dyeing temperature is 80°C to 150°C, preferably 100°C to 140°C, and the pressure may be 0.00 MPa to 0.80 MPa, preferably 0.05 MPa to 0.60 MPa. Also, each of the above components (A), (B), and (C) may be separately added to the dyeing bath at the above-described mass ratio. That is, the present invention also provides a method for producing a fiber dyed product, which includes a step of adding each of the components (A), (B), and (C) to the dyeing bath and a step of dyeing the fiber in the dyeing bath to obtain a dyed product. The blending mass ratio [(A) / (B) / (C)] of the component (A), the component (B), and the component (C) is 40 to 90 / 5 to 25 / 5 to 35 as described above, and preferably the mass ratio [(A) / (B) / (C)] is 50 to 80 / 5 to 20 / 10 to 30. However, the total of the components (A), (B), and (C) is 100.

[0038] The composition of the dyeing bath may follow a conventionally known dyeing method. The addition amount of the fiber treatment aid to the dyeing bath may be adjusted as appropriate, but it is 0.01 to 2 g, preferably 0.05 to 1.5 g, per 1 L of the dyeing bath. When the components (A), (B), and (C) are added separately, the total of the components (A), (B), and (C) is 0.01 to 2 g, preferably 0.05 to 1.5 g, per 1 L of the dyeing bath.

Examples

[0039] Hereinafter, examples and comparative examples will be shown to explain the present invention in more detail, but the present invention is not limited to the following examples.

[0040] Preparation of component (A) [Synthesis Example 1] Component (A1): 150 g of diethylene glycol and 3.5 g of potassium hydroxide were charged into a 5 L autoclave. After sufficiently replacing the nitrogen in the kettle, the temperature was raised to 140°C, and 622 g of ethylene oxide was gradually added. After the reaction of ethylene oxide was completed, the temperature was cooled to 120°C, and then 1640 g of propylene oxide was gradually added and reacted sufficiently, and then cooled to obtain polyoxyethylene (10 moles) polyoxypropylene (20 moles) glycol. Subsequently, 480 g of the obtained polyoxyethylene (10 moles) polyoxypropylene (20 moles) glycol, 29.1 g of sulfamic acid, and 18.0 g of urea were charged into a 1 L glass flask, and the temperature was gradually raised and reacted at 120°C to obtain polyoxyethylene (10 moles) polyoxypropylene (20 moles) glycol monosulfate ammonium salt. The anion purity of the synthesized product by combined sulfuric acid was 87.6%.

[0041] [Synthesis Example 2] Component (A2): 150 g of diethylene glycol and 4.6 g of potassium hydroxide were charged into a 5 L autoclave. After sufficient nitrogen replacement in the autoclave, the temperature was raised to 140 °C, and 622 g of ethylene oxide was gradually added. After the reaction of ethylene oxide was completed, the temperature was cooled to 120 °C, and then 2460 g of propylene oxide was gradually added and reacted sufficiently, and then cooled to obtain polyoxyethylene (10 mol) polyoxypropylene (30 mol) glycol. Subsequently, 687 g of the above polyoxyethylene (10 mol) polyoxypropylene (30 mol) glycol, 29.1 g of sulfamic acid, and 18.0 g of urea were charged into a 1 L glass flask, and the temperature was gradually raised and reacted at 120 °C to obtain polyoxyethylene (10 mol) polyoxypropylene (30 mol) glycol monosulfate ammonium salt. The anion purity of the synthesized product by bound sulfuric acid was 88.1%.

[0042] [Synthesis Example 3] Component (A3): 687 g of the polyoxyethylene (10 mol) polyoxypropylene (30 mol) glycol obtained in the above Synthesis Example 2, 43.6 g of sulfamic acid, and 18.0 g of urea were charged, the temperature was gradually raised, and the reaction was carried out at 120 °C to obtain a mixture of polyoxyethylene (10 mol) polyoxypropylene (30 mol) glycol monosulfate ammonium salt and polyoxyethylene (10 mol) polyoxypropylene (30 mol) glycol disulfate ammonium salt. The anion purity of the synthesized product by bound sulfuric acid was 131.2%.

[0043] [Synthesis Example 4] Component (A4): 687 g of polyoxyethylene (10 mol) polyoxypropylene (30 mol) glycol obtained in Synthesis Example 2 above, 58.1 g of sulfamic acid, and 24.0 g of urea were charged, the temperature was gradually raised, and the reaction was carried out at 120°C to obtain a mixture of polyoxyethylene (10 mol) polyoxypropylene (30 mol) glycol monosulfate·ammonium salt and polyoxyethylene (10 mol) polyoxypropylene (30 mol) glycol disulfate·ammonium salt. The anion purity of the synthesized product based on bound sulfuric acid was 175.8%.

[0044] [Synthesis Example 5] Component (A5): 150 g of diethylene glycol and 5.4 g of potassium hydroxide were charged into a 5 L autoclave. After sufficiently replacing the nitrogen in the kettle, the temperature was raised to 140°C, and 1245 g of ethylene oxide was gradually added. After the reaction of ethylene oxide was completed, the temperature was cooled to 120°C, and then 2460 g of propylene oxide was gradually added and reacted sufficiently, and then cooled to obtain polyoxyethylene (20 mol) polyoxypropylene (30 mol) glycol. Subsequently, 819 g of the obtained polyoxyethylene (20 mol) polyoxypropylene (30 mol) glycol, 29.1 g of sulfamic acid, and 18.0 g of urea were charged into a 1 L glass flask, the temperature was gradually raised, and the reaction was carried out at 120°C to obtain polyoxyethylene (20 mol) polyoxypropylene (30 mol) glycol monosulfate·ammonium salt. The anion purity of the synthesized product based on bound sulfuric acid was 87.9%.

[0045] [Synthesis Example 6] Component (A6): 819 g of polyoxyethylene (20 mol) polyoxypropylene (30 mol) glycol obtained in Synthesis Example 5 above, 43.6 g of sulfamic acid, and 18.0 g of urea were charged, the temperature was gradually raised, and the reaction was carried out at 120°C to obtain a mixture of polyoxyethylene (20 mol) polyoxypropylene (30 mol) glycol monosulfate·ammonium salt and polyoxyethylene (20 mol) polyoxypropylene (30 mol) glycol disulfate·ammonium salt. The anion purity of the synthesized product by bound sulfuric acid was 129.8%.

[0046] [Synthesis Example 7] Component (A7): 819 g of polyoxyethylene (20 mol) polyoxypropylene (30 mol) glycol obtained in Synthesis Example 5 above, 58.1 g of sulfamic acid, and 24.0 g of urea were charged, the temperature was gradually raised, and the reaction was carried out at 120°C to obtain a mixture of polyoxyethylene (20 mol) polyoxypropylene (30 mol) glycol monosulfate·ammonium salt and polyoxyethylene (20 mol) polyoxypropylene (30 mol) glycol disulfate·ammonium salt. The anion purity of the synthesized product by bound sulfuric acid was 173.3%.

[0047] [Synthesis Example 8] Component (A8): 600 g of tridecanol and 5.6 g of potassium hydroxide were charged into a 5 L autoclave. After sufficient nitrogen substitution in the kettle, the temperature was raised to 150°C, and 1320 g of ethylene oxide was gradually added. After the reaction of ethylene oxide was completed, the temperature was cooled to 120°C, and then 870 g of propylene oxide was gradually added and reacted sufficiently, and then cooled to obtain polyoxyethylene (10 mol) polyoxypropylene (5 mol) tridecyl ether. Subsequently, 558 g of polyoxyethylene(10 mol) polyoxypropylene(5 mol) tridecanol ether obtained in a 1 L glass flask, 58.2 g of sulfamic acid, and 36.0 g of urea were charged, and the temperature was gradually raised and reacted at 120 °C to obtain polyoxyethylene(10 mol) polyoxypropylene(5 mol) tridecanol ether monosulfate·ammonium salt. The anion purity of the synthesized product by combined sulfuric acid was 92.3%.

[0048] Synthesis of component (B) [Synthesis Example 9] Component (B1): 400 g of styrenated phenol (main component: tristyrenated phenol) and 2.5 g of potassium hydroxide were charged into a 5 L autoclave. After sufficiently replacing the nitrogen in the kettle, the temperature was raised to 150 °C, and 880 g of ethylene oxide was gradually added to obtain polyoxyethylene(20 mol) styrenated phenyl ether. Subsequently, 500 g of the obtained polyoxyethylene(20 mol) styrenated phenyl ether, 37.9 g of sulfamic acid, and 23.4 g of urea were charged into a 1 L glass flask, and the temperature was gradually raised and reacted at 120 °C to obtain polyoxyethylene(20 mol) styrenated phenyl ether sulfate·ammonium salt. The anion purity of the synthesized product by combined sulfuric acid was 85% or more. The average number of moles of added styryl groups was 2.8 moles.

[0049] [Synthesis Example 10] Component (B2): 400 g of styrenated phenol (main component: tristyrenated phenol) and 3.0 g of potassium hydroxide were charged into a 5 L autoclave. After thoroughly purging the inside of the autoclave with nitrogen, the temperature was raised to 150 °C, and 1100 g of ethylene oxide was gradually added to obtain polyoxyethylene (25 mol) styrenated phenyl ether. Subsequently, 500 g of the obtained polyoxyethylene (25 mol) styrenated phenyl ether, 32.3 g of sulfamic acid, and 20.0 g of urea were charged into a 1 L glass flask, and the temperature was gradually raised and reacted at 120 °C to obtain polyoxyethylene (25 mol) styrenated phenyl ether sulfate ammonium salt. The anion purity of the synthesized product by combined sulfuric acid was 85% or more. The average number of moles of added styryl groups was 2.8 mol.

[0050] [Synthesis Example 11] Component (B3): 400 g of styrenated phenol (main component: tristyrenated phenol) and 3.4 g of potassium hydroxide were charged into a 5 L autoclave. After thoroughly purging the inside of the autoclave with nitrogen, the temperature was raised to 150 °C, and 1320 g of ethylene oxide was gradually added to obtain polyoxyethylene (30 mol) styrenated phenyl ether. Subsequently, 500 g of the obtained polyoxyethylene (30 mol) styrenated phenyl ether, 28.2 g of sulfamic acid, and 17.4 g of urea were charged into a 1 L glass flask, and the temperature was gradually raised and reacted at 120 °C to obtain polyoxyethylene (30 mol) styrenated phenyl ether sulfate ammonium salt. The anion purity of the synthesized product by combined sulfuric acid was 85% or more. The average number of moles of added styryl groups was 2.8 mol.

[0051] Synthesis of Component (C) [Synthesis Example 12] Component (C1): Charge 300 g of glycerin and 6.3 g of potassium hydroxide into a 5 L autoclave. After thoroughly purging the nitrogen inside the kettle, heat up to 150 °C and gradually add 2,870 g of ethylene oxide to obtain polyoxyethylene (20 mol) glycerol ether. Subsequently, charge 500 g of the obtained polyoxyethylene (20 mol) glycerol ether, 1.8 g of potassium hydroxide, and 428 g of oleic acid into a 1 L glass flask, gradually heat up, and react at 180 °C to obtain polyoxyethylene (20 mol) glycerol trioleate. The end point was confirmed by the acid value, and the unreacted oleic acid was less than 0.3%.

[0052] [Synthesis Example 13] Component (C2): Charge 400 g of polyethylene glycol with a molecular weight of 600, 1.5 g of potassium hydroxide, and 361 g of oleic acid into a 1 L glass flask, gradually heat up, and react at 180 °C to obtain polyoxyethylene glycol (600) dioleate. The end point was confirmed by the acid value, and the unreacted oleic acid was less than 0.3%. The average number of moles of ethylene oxide added was 13 moles.

[0053] The (A1) - (A8), (B1) - (B3), and (C1) - (C2) obtained in the above synthesis examples were mixed at the mass ratios shown in Table 1 to prepare a fiber treatment aid. Evaluation tests were conducted on this treatment agent by the following method. In each evaluation test, in order to maintain the dilutability in the test solution and the stability of the mixed solution, the fiber treatment aid having the composition shown in Table 1 was diluted with water and used.

[0054] The components for the comparative examples are as follows. (Component D1) Charge 400 g of polyethylene glycol with a molecular weight of 400, 97.1 g of sulfamic acid, and 60.0 g of urea into a 1 L glass flask, gradually heat up, and react at 120 °C to obtain polyethylene glycol (400) monosulfate ammonium salt. (Component D2) 400 g of oleyl alcohol and 3.5 g of potassium hydroxide were charged into a 5 L autoclave. After sufficient nitrogen replacement in the kettle, the temperature was raised to 150 °C, and 1313 g of ethylene oxide was gradually added. After the reaction, polyoxyethylene (20) oleyl ether was obtained.

[0055] In addition, as common surfactant components used in the comparative examples, polyoxyethylene (10) polyoxypropylene (30) glycol, polyoxyethylene (20) polyoxypropylene (30) glycol, dodecylbenzene sulfonic acid, etc. were used.

[0056] [Performance Evaluation Test Method] (1) High-temperature and high-pressure dyeing test with a flame retardant (Preparation of test solution) To 1 L of water as a solvent, 10 g / L of a brominated flame retardant, 1 g / L of a disperse dye (red, C.I. 60), 0.3 g / L of acetic acid, and 0.4 g of the fiber treatment aid described in Table 1 were added and mixed to prepare a test solution. (Dyeing test) Into the pot of the dyeing tester, a test cloth of untreated polyester fabric and the above test solution with a weight 10 times that of the test cloth were put, and dyeing treatment was carried out at 0.30 MPa and 130 °C for 30 minutes. After dyeing, the test cloth was taken out from the pot, washed with water and dried, and it was confirmed whether there was uneven dyeing or stains due to aggregates on the test cloth. Also, the inside of the pot after dyeing was checked to confirm whether there was no adhesion of aggregates. Less occurrence of uneven dyeing and aggregates indicates better dispersion ability. The evaluation of the dispersion performance was carried out according to the following criteria. (Evaluation) ◎ ··· There is no uneven dyeing or dyeing stain, and there is no pot aggregate. 〇 ··· There is no uneven dyeing or dyeing stain, but a slight pot aggregate was confirmed. △ ··· Slight uneven dyeing or dyeing stain, and pot aggregates were confirmed. × ··· A large number of uneven dyeings or dyeing stains, and many pot aggregates were confirmed.

[0057] (2) Confirmation of aggregates during high-temperature heating The test solution prepared in (1) above was heated while being mixed in a glass container, and heated for 10 minutes under the boiling temperature condition of 95°C to 105°C. After heating, filtration was performed using a funnel and a test cloth, and the amount of aggregates generated during boiling and evaporation of the test solution remaining on the filter cloth was confirmed. The smaller the amount of aggregates generated, the better the dispersion ability. The presence and amount of aggregates were visually confirmed and evaluated according to the following criteria. (Evaluation) ◎ ··· No stains are visible on the filter cloth at all. 〇 ··· One or two small aggregates are visible on the filter cloth. △ ··· Many small aggregates are visible on the filter cloth. × ··· Many large aggregates are visible on the filter cloth.

[0058] (3) High-temperature dispersion test of dyes (Preparation of test solution) To 1 L of water as a solvent, 0.7 g / L of a disperse dye (red or blue), 0.3 g / L of acetic acid, and 0.4 g / L of the fiber treatment aid described in Table 1 were added and mixed to prepare test solutions for red and blue respectively. As the above disperse dyes, C.I. 60 was used for red and C.I. 73 was used for blue. The dispersibility of red and blue was confirmed by the following method. (Dyeing test) A polyester jersey test cloth was set in a color pet-type dyeing tester, and a test solution 15 times the weight of the test cloth was added. After raising the temperature of the tester to 125°C, it was quickly cooled, washed with water, and dried. The amount and concentration of spots generated on the test cloth were confirmed and evaluated according to the following criteria. (Evaluation) ◎ ··· For both red and blue, there are no spots generated and they are dyed uniformly. 〇 ··· For at least one of red and blue, faint spots are visible. △ ··· For at least one of red and blue, dark spots are visible. × ··· For both red and blue, dark spots are visible throughout the test cloth.

[0059] (4) Leveling property test Test fabrics of polyester woven fabrics dyed in advance with 1% by weight of disperse dyes (red, blue, and yellow respectively) based on the weight of the test fabric were prepared (original dyed fabrics). White fabrics of the same weight as the dyed test fabrics (untreated test fabrics) were placed in the pots of the dyeing tester, and a test solution 20 times the weight of the test fabric (a mixture prepared by adding 0.3 g / L of acetic acid and 0.4 g / L of the fiber treatment aid described in Table 1 to 1 L of water) was added thereto, and a dyeing treatment was performed at 130 °C for 30 minutes. After the treatment, the test fabrics were taken out, washed with water, dried, and then the dyeing state of the test fabrics was confirmed. For the white fabrics, the higher the migration ability of the dye during the dyeing process and the better the leveling ability are indicated by the degree of dye migration from the pre-dyed fabric. The dye migration properties of each of red, blue, and yellow were confirmed, and the leveling ability was comprehensively evaluated. (Evaluation) ◎···Both the original dyed fabric and the test fabric are dyed uniformly without dyeing unevenness. 〇···The color of the original dyed fabric is slightly darker, but it is dyed evenly without unevenness. △···The color of the original dyed fabric is slightly darker, and dyeing unevenness can be seen. ×···There is a large color difference between the original dyed fabric and the test fabric, and dyeing unevenness has occurred.

[0060]

Table 1

[0061]

Table 2

[0062] As shown in Table 1 and Table 2 above, the fiber treatment aid of the present invention can suppress the generation of aggregates of dyes and flame retardants and simultaneously exhibit good dyeability in the dyeing treatment step at high temperature including flame retardant addition treatment. The fiber treatment aid of the present invention can suppress the generation of aggregates of dyes and flame retardants and provide a well-dyed product with uniform dyeing, particularly in the dyeing treatment step of polyester fibers at high temperature.

Claims

1. (A) 40 to 90 parts by mass of a compound represented by the following general formula (1) X １ -O-(A １ O) ｎ１ (A ２ O) ｎ２ -X ２ (1) (wherein, A １ is an ethylene group, and A ２ is an alkylene group having 3 or 4 carbon atoms, n １ is a number from 3 to 30, n ２ is a number from 5 to 60, A １ O and A ２ The mutual arrangement with O is not limited and may form a block unit or may be randomly bonded. X １ is a hydrogen atom, an alkyl group or alkenyl group having 8 to 22 carbon atoms, -SO ３ M, or -PO ３ M, and X ２ is -SO ３ M, or -PO ３ M, and M is a hydrogen atom, an ammonium ion, an organic ammonium ion, or a monovalent metal ion), (B) 5 to 25 parts by mass of a compound represented by the following general formula (2) 【Chemical 1】 (wherein m is a number from 1 to 3, and n ３ is a number from 5 to 60, A ３ is an alkylene group having 2 to 4 carbon atoms, and M' is a hydrogen atom, an ammonium ion, an organic ammonium ion, or a monovalent metal ion), and (C) 5 to 35 parts by mass of a polyoxyalkylene polyhydric alcohol fatty acid ester (However, the total of the components (A), (B), and (C) is 100 parts by mass) A processing aid for polyester fibers containing the same

2. The processing aid for polyester fibers according to Claim 1, wherein the component (C) is represented by the following general formula (3): [H-(OA ４ ) ｎ４ -O-] ｒ R １ [-O-(A ５ O) ｎ５ -C(=O)-R ２ ｓ ​ （３） (wherein, R １ is a residue obtained by removing two or more hydroxy groups from a polyhydric alcohol having 2 to 30 carbon atoms and 2 to 8 valences, A ４ is an alkylene group having 2 to 4 carbon atoms, n ４ is a number from 1 to 80, R ２ is an alkyl group having 1 to 30 carbon atoms or an alkenyl group having 2 to 30 carbon atoms, A ５ is an alkylene group having 2 to 4 carbon atoms, n ５ is a number from 1 to 80, and r and s are integers satisfying the relationships 0 ≦ r ≦ 7, 1 ≦ s ≦ 8, and 2 ≦ r + s ≦ 8)

3. The processing aid for polyester fibers according to Claim 1 or 2, wherein the component (C) is a polyoxyethylene polyhydric alcohol fatty acid ester

4. In the above formulas (1) and (2), M and M' are each independently an ammonium ion, an organic ammonium ion, a sodium ion, or a potassium ion. The processing aid for polyester fibers according to any one of Claims 1 to 3

5. A method for producing a fiber dyed product, comprising a step of adding the processing aid for polyester fibers according to any one of Claims 1 to 4 to a dyeing bath, and a step of dyeing polyester fibers in the dyeing bath to obtain a dyed product

6. The production method according to Claim 5, wherein the addition amount of the processing aid for polyester fibers is 0.01 to 2 g with respect to 1 L of the dyeing bath

7. A step of adding the following components (A), (B), and (C) to a dyeing bath (A) A compound represented by the following general formula (1) 40 to 90 parts by mass with respect to 100 parts by mass of the total of components (A), (B), and (C) X １ -O-(A １ O) ｎ１ (A ２ O) ｎ２ -X ２ (1) (wherein A １ is an ethylene group, and A ２ is an alkylene group having 3 or 4 carbon atoms, n １ is a number from 3 to 30, n ２ is a number from 5 to 60, A １ O and A ２ The mutual arrangement with O is not limited and may form a block unit or may be randomly bonded. X １ is a hydrogen atom, an alkyl group or alkenyl group having 8 to 22 carbon atoms, -SO ３ M, or -PO ３ M, and X ２ is -SO ３ M, or -PO ３ M, and M is a hydrogen atom, an ammonium ion, an organic ammonium ion, or a monovalent metal ion), (B) A compound represented by the following general formula (2) 5 to 25 parts by mass with respect to 100 parts by mass of the total of components (A), (B), and (C) 【Chemical 2】 (wherein m is a number from 1 to 3, and n ３ is a number from 5 to 60, A ３ is an alkylene group having 2 to 4 carbon atoms, and M' is a hydrogen atom, an ammonium ion, an organic ammonium ion, or a monovalent metal ion), (C) Polyoxyalkylene polyhydric alcohol fatty acid ester 5 to 35 parts by mass with respect to 100 parts by mass of the total of components (A), (B), and (C) and a step of dyeing polyester fibers in the dyeing bath to obtain a dyed product. A method for producing a fiber dyed product

8. The production method according to Claim 7, wherein the total amount of the components (A), (B), and (C) is 0.01 to 2 g with respect to 1 L of the dyeing bath

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