Dispersing and uniforming agent for dyeing polyester fibers and method for manufacturing polyester fiber dyed products using the same

Abstract

This invention provides a dispersing dyeing agent that enables good removal of oil from fabrics, even when dyeing polyester fibers at high temperature and pressure using dispersing dyes, and prevents dye aggregation, resulting in uniform and even dyeing without unevenness, even when dyeing fabrics that have not been sufficiently scoured and have residual oil. It also provides a method for manufacturing polyester fiber dyed products using the same. [Solution] A dispersing and uniforming agent for dyeing polyester fibers, comprising: component (A), which is a glycerol monofatty acid ester; component (B-1), which is an ester compound with a specific structure having a polyoxyalkylene moiety and / or a glyceryl moiety; and component (B-2), which is a hydroxy compound with a specific structure having a polyoxyalkylene moiety and / or a glyceryl moiety.

Description

[Technical Field]

[0001] The present invention relates to a dispersing and leveling agent for dyeing polyester fibers and a method for producing dyed polyester fiber products using the same. In particular, the present invention relates to a dispersing and leveling agent that prevents dye aggregation and enables uniform dyeing even when dyeing polyester fibers that have not been sufficiently scoured and have residual oil, and a method for producing dyed polyester fiber products using the same. [Background technology]

[0002] In recent years, the increasing use of differentiated materials such as irregularly shaped cross-section yarns, composite yarns, and yarns with varying shrinkage rates, along with the increased surface area due to the use of ultrafine yarns, the increased density of fabrics, and the increased amount of oils and sizing agents adhering to fabrics, has made it easier for problems such as uneven dyeing, color variations between dyeing batches, staining of dyed products, and staining of dyeing machines to occur in clothing and textile materials.

[0003] Furthermore, in recent dyeing processes, there is a trend towards high-mix, low-volume production to meet diverse demands, which has led to rising processing costs. To reduce these costs, processing methods are being shortened or simplified. In particular, methods to simplify the scouring and washing processes have become mainstream, taking into consideration the improvement of productivity and energy conservation. However, weaving oils, sizing agents, etc., that should be removed in the scouring and washing processes remain on the material to be dyed and enter the dyeing process, which causes uneven dyeing, color variations, and staining.

[0004] To solve these problems, Patent Document 1 describes a method for producing polyester dyed fibers, which involves scouring and dyeing in a single bath containing a specific nonionic surfactant, a specific anionic surfactant, and a disperse dye. Patent Document 2 describes a method for dyeing polyester fibers using a disperse and uniform dyeing agent that contains at least one selected from the group consisting of an alkylene oxide adduct of a specific alkenylphenol, an esterified alkenylphenol alkylene oxide adduct, and an anionic alkenylphenol alkylene oxide adduct. Patent Document 3 describes that dirt components such as fiber oils and oligomers can be easily removed by using a compound that is a reaction product of an organic compound having a hydroxyl group and an acid anhydride. [Prior art documents] [Patent Documents]

[0005] [Patent Document 1] International Publication No. 2011 / 007696 [Patent Document 2] Japanese Patent Publication No. 2014-47438 [Patent Document 3] Japanese Patent Publication No. 2018-9124 [Overview of the Initiative] [Problems that the invention aims to solve]

[0006] However, even after implementing these steps, problems still occurred during the dyeing process, and the effectiveness could not be said to have improved sufficiently. The present invention aims to provide a dispersing dyeing agent that enables good removal of oil from fabric, prevents dye aggregation, and allows for uniform dyeing of polyester fibers without unevenness, even when dyeing fabrics that have not been sufficiently scoured and have residual oil, in high-temperature, high-pressure dyeing using dispersing dyes, and a method for producing dyed polyester fiber products using the same. [Means for solving the problem]

[0007] As a result of intensive studies to solve the above problems, the inventors of the present invention have found that when polyester fibers are dyed under high temperature and high pressure using disperse dyes, by using a specific disperse leveling agent, even when dyeing a fabric with insufficient scouring and residual oil agent, the oil agent can be removed well from the fabric, there is no aggregation of dyes, and a polyester fiber dyed product that is uniformly dyed without spots can be obtained, thus completing the present invention.

[0008] That is, the present invention includes the following items. [1] A disperse leveling agent for dyeing polyester fibers, containing component (A), component (B-1) and component (B-2), where the component (A) is glycerin monofatty acid ester, the component (B-1) is represented by the following general formulas (B-1-1), (B-1-2) and (B-1-3), R-O-(AO)n 1 -CO-R’ ···(B-1-1) R’-COO-(AO)n 2 -CO-R’ ···(B-1-2)

Chemical formula

[0009] By using the dispersing and leveling agent for polyester fiber dyeing of the present invention, when dyeing polyester fibers at high temperature and pressure using disperse dyes, even when dyeing fabrics that have not been sufficiently scoured and have residual oil, the oil can be removed from the fabric well, and a polyester fiber dyed product can be obtained that is dyed uniformly without dye aggregation and without unevenness. [Brief explanation of the drawing]

[0010] [Figure 1] This figure shows the grades 5 to 1 in the evaluation of dye dispersibility 1. [Figure 2] This diagram shows the grades from 5 to 1 in the evaluation of scouring properties. [Modes for carrying out the invention]

[0011] The following describes specific exemplary embodiments of the present invention, but the present invention is not limited to these embodiments.

[0012] Dispersing and uniforming agent for dyeing polyester fibers One aspect of the present invention provides a dispersion and uniform dyeing agent for polyester fibers. The dispersion and uniform dyeing agent for polyester fibers according to one aspect is: (A) Components: Glycerin mono fatty acid ester, and (B) Components: At least one selected from compounds having hydroxyl groups and polyoxyalkylene groups and their esters (especially fatty acid esters), and glycerin and its di- or tri-esters (especially fatty acid esters), It contains. Compounds having hydroxyl groups and polyoxyalkylene groups can be nonionic surfactants. A dispersion dyeing agent for polyester fibers according to one embodiment is: (A) Ingredients: Glycerin mono fatty acid ester, (B-1) Component: At least one compound selected from the compounds represented by any of the general formulas (B-1-1), (B-1-2), and (B-1-3) described below, (B-2) Component: At least one compound selected from those represented by any of the general formulas (B-2-1), (B-2-2), and (B-2-3) described below. It contains.

[0013] A dispersing and leveling agent for dyeing polyester fibers containing components (A), (B-1), and (B-2) may be useful in providing polyester fiber dyed products that are uniformly dyed without dye aggregation, even when dyeing fabrics that have not been sufficiently scoured and have residual oil, as it has good oil removal properties from the fabric. The following provides a more detailed explanation of each component.

[0014] <(A) Ingredient: Glycerin monofatty acid ester> In this embodiment, component (A), glycerin monofatty acid ester, refers to a fatty acid monoester of glycerin. Glycerol monofatty acid esters are produced, for example, in the esterification reaction of glycerol with fatty acids, or in the transesterification reaction of oils and fats with nonionic surfactants having hydroxyl groups.

[0015] In the esterification reaction between glycerol and fatty acids, the hydrocarbon group of the fatty acid used may be linear or branched, and may be saturated or unsaturated. The number of carbon atoms in the fatty acid is not particularly limited, but 12 to 24 is preferred, and 16 to 20 is more preferred. Furthermore, it is preferable that the fatty acid includes an unsaturated fatty acid.

[0016] Examples of such fatty acids include saturated fatty acids such as caprylic acid, lauric acid, myristic acid, palmitic acid, stearic acid, isostearic acid, eicosanoic acid, and behenic acid; unsaturated fatty acids containing one unsaturated bond, such as palmitoleic acid, oleic acid, elaidic acid, vaccenic acid, gadoleic acid, eicosenoic acid, erucic acid, and ricinoleic acid; unsaturated fatty acids containing two unsaturated bonds, such as linoleic acid, eicosadienoic acid, and docosadienoic acid; and unsaturated fatty acids containing three unsaturated bonds, such as linolenic acid, pinolenic acid, eleostearic acid, meadic acid, and eicosatrienoic acid.

[0017] Furthermore, fatty acids can also be produced from oils and fats (e.g., natural fatty acids). In addition, in light of the growing environmental awareness in recent years, it is also possible to use regenerated fatty acids produced from oils and fats used in the processing of food products, such as TFA-140F (Tsukuno Foods Industry, acid value 195-202, iodine value 124-134). When using fatty acids produced from oils and fats and / or regenerated fatty acids, for example, the number of carbon atoms can be 12-24, and preferably 16-20. Fatty acids containing unsaturated bonds are also preferred, and those that are liquid at room temperature are preferred. In this disclosure, "liquid at room temperature" means that when the substance to be tested is placed in a flat-bottomed cylindrical glass test tube with an inner diameter of 30 mm to a height of 55 mm at 25°C, and the test tube is held horizontally, the tip of the liquid surface passes through a point 85 mm from the bottom of the test tube within 30 seconds. The iodine value of the fatty acid is preferably 80 to 200, and more preferably 100 to 150. In this disclosure, the iodine value is the value measured according to JIS K 0070 (1992). A higher content of unsaturated fatty acids tends to result in better dispersibility of the dye. The fatty acids and regenerated fatty acids mentioned above may be used individually or in combination of two or more types.

[0018] In the transesterification reaction between oils and fats and nonionic surfactants containing hydroxyl groups, the oils and fats used are not particularly limited, but examples include vegetable oils and animal oils. Examples of vegetable oils include linseed oil, rapeseed oil, soybean oil, grape oil, sunflower oil, corn oil, palm oil, rice oil, peanut oil, sesame oil, and cottonseed oil. Examples of animal oils include beef tallow, lard, and fish oil. Furthermore, oils and fats recovered after being used in the processing of food products can also be used. The iodine value of the oil is preferably between 80 and 200, and more preferably between 100 and 150. The oil is preferably in liquid form at room temperature.

[0019] The fatty acids that make up the oils and fats are not particularly limited, and may be, for example, the fatty acids mentioned above. It is preferable that one or more of the fatty acids that make up the oils and fats are unsaturated fatty acids. A higher content of unsaturated fatty acids tends to result in better dispersibility of the dye.

[0020] The nonionic surfactant having a hydroxyl group used in the transesterification reaction between oils and fats and nonionic surfactants having a hydroxyl group is preferably a compound represented by any of the following general formulas (1) to (3). RO-(AO)n 1 -H ···(1) [In the formula, R is an m-styrene-phenyl group (where m is 0 to 5), an m'-styrene-alkylphenyl group (where m' is 0 to 5 and the alkyl group has 1 to 12 carbon atoms), or an alkyl group with 1 to 22 carbon atoms. AO is an alkylene oxy group having 2 to 4 carbon atoms, and multiple AOs may be identical or different from one another. n 1 This represents the average number of moles of AO added, and is between 5 and 50. HO-(AO)n 2 -H ···(2) [In the formula, AO is an alkylene oxy group having 2 to 4 carbon atoms, and multiple AOs may be identical or different from one another. n2 This represents the average number of moles of AO added, and is between 5 and 50. [ka] [In the formula, AO is an alkylene oxy group having 2 to 4 carbon atoms, and multiple AOs may be identical or different from one another. p is the average number of moles of AO added, ranging from 0 to 30, and multiple p values ​​may be the same or different from one another.

[0021] In the above general formula (1), R is preferably an m-styrene-phenyl group (m is 0 to 5) or an m'-styrene-alkylphenyl group (m' is 0 to 5, the alkyl group has 1 to 12 carbon atoms), and m and m' are each preferably 2 to 5. 1 The ratio of the compound is preferably 10 to 50, and more preferably 15 to 25. The compound preferably contains an ethylene oxy group (EO), and the EO / AO ratio is preferably 50% by weight or more, more preferably 80% by weight or more, and most preferably 100% by weight. In one embodiment, the compound represented by the general formula (1) above may be an ethylene oxide adduct of di- or tri-styrene-modified phenol.

[0022] In the above general formula (2), n 2 The ratio is preferably 5 to 50, and more preferably 10 to 25. AO preferably contains an ethylene oxy group (EO), and the EO / AO ratio is preferably 50% by weight or more, and more preferably 80% by weight or more. The compound represented by the above general formula (2) may be polyethylene glycol in one embodiment.

[0023] In the above general formula (3), p is between 0 and 30. AO preferably contains an ethylene oxy group (EO), and the EO / AO ratio is preferably 50% by weight or more, and more preferably 80% by weight or more. The compound represented by the above general formula (3) may be glycerin in one embodiment.

[0024] <(B) Components: Compounds having hydroxyl groups and polyoxyalkylene groups and their esters, as well as glycerin and its di- or tri-esters> A dispersing and leveling agent for dyeing polyester fibers according to one embodiment contains component (B), which is at least one selected from compounds having a hydroxyl group and a polyoxyalkylene group and their esters (particularly fatty acid esters), and glycerin and its di- or tri-esters (particularly fatty acid esters). Component (B) according to one embodiment contains components (B-1) and (B-2) described below, and may further contain components (B-3) and / or (B-4) described below as optional components.

[0025] Compounds having a hydroxyl group and a polyoxyalkylene group may be nonionic surfactants. Examples of such compounds include the hydroxyl group-containing nonionic surfactants exemplified with respect to component (A). Examples of fatty acid esters of hydroxyl group-containing nonionic surfactants include those produced in the esterification reaction between the hydroxyl group-containing nonionic surfactant exemplified with respect to component (A) and the fatty acid exemplified with respect to component (A), or those produced in the transesterification reaction between the hydroxyl group-containing nonionic surfactant exemplified with respect to component (A) and the oil or fat exemplified with respect to component (A). The compound having a hydroxyl group and a polyoxyalkylene group may, in one embodiment, be a polyalkylene oxide adduct of styrene-modified phenol; in one embodiment, be a polyalkylene oxide adduct of styrene-modified alkylphenol; in one embodiment, be a polyalkylene oxide or alkylated polyalkylene oxide; and in one embodiment, be a polyalkylene oxide adduct of glycerin.

[0026] Components (B-1) to (B-4) are classified as follows according to the number of hydroxyl groups remaining in one molecule.

[0027] ((B-1) component: No residual hydroxyl groups) Component (B-1) is at least one compound selected from those represented by any of the following general formulas (B-1-1), (B-1-2), and (B-1-3). Therefore, component (B-1) is an ester compound with a specific structure having a polyoxyalkylene moiety and / or a glyceryl moiety. RO-(AO)n 1 -CO-R' ···(B-1-1) R'-COO-(AO)n 2 -CO-R' ···(B-1-2) [ka] [In the formula, R is an m-styrene-phenyl group (where m is 0 to 5), an m'-styrene-alkylphenyl group (where m' is 0 to 5 and the alkyl group has 1 to 12 carbon atoms), or an alkyl group with 1 to 22 carbon atoms. R' is a monovalent hydrocarbon group, and if there are multiple R' groups, they may be the same or different from each other. AO is an alkylene oxy group having 2 to 4 carbon atoms, and multiple AOs may be identical or different from one another. n 1 This is the average number of moles of AO added, and is between 5 and 50. n 2 This is the average number of moles of AO added, and is between 5 and 50. p is the average number of moles of AO added, ranging from 0 to 30, and multiple p values ​​may be the same or different from one another.

[0028] (Component B-2: Contains one residual hydroxyl group) Component (B-2) is at least one compound selected from those represented by any of the following general formulas (B-2-1), (B-2-2), and (B-2-3). Therefore, component (B-2) is a hydroxy compound of a specific structure having a polyoxyalkylene moiety and / or a glyceryl moiety. RO-(AO)n 1 -H ···(B-2-1) R'-COO-(AO)n 2-H ···(B-2-2)

[0029] [ka] [In the formula, R is an m-styrene-phenyl group (where m is 0 to 5), an m'-styrene-alkylphenyl group (where m' is 0 to 5 and the alkyl group has 1 to 12 carbon atoms), or an alkyl group with 1 to 22 carbon atoms. R' is a monovalent hydrocarbon group, and if there are multiple R' groups, they may be the same or different from each other. X 1 and X 2 One side is H, and the other side is CO-R', AO is an alkylene oxy group having 2 to 4 carbon atoms, and multiple AOs may be identical or different from one another. n 1 This is the average number of moles of AO added, and is between 5 and 50. n 2 This is the average number of moles of AO added, and is between 5 and 50. p is the average number of moles of AO added, ranging from 0 to 30, and multiple p values ​​may be the same or different from one another.

[0030] (Component B-3: Contains two residual hydroxyl groups) Component (B-3) is at least one compound selected from those represented by either of the following general formulas (B-3-2) and (B-3-3). HO-(AO)n 2 -H ···(B-3-2) [In the formula, AO is an alkylene oxy group having 2 to 4 carbon atoms, and multiple AOs may be identical or different from one another. n 2 This represents the average number of moles of AO added, and is between 5 and 50. [ka] [In the formula, AO is an alkylene oxy group having 2 to 4 carbon atoms, and multiple AOs may be identical or different from one another. R' is a monovalent hydrocarbon group, q is the average number of moles added to AO, and is between 0 and 30. Multiple qs may be the same or different from each other, but at least one of the qs must be 1 or greater.

[0031] In this embodiment, component (A) is a glycerol monofatty acid ester, and in one embodiment, it may be a compound in which all q values ​​in the above general formula (B-3-3) are 0.

[0032] (Component B-4: Contains three residual hydroxyl groups) Component (B-4) is a compound represented by the following general formula (B-4-3). [ka]

[0033] [In the formula, AO is an alkylene oxy group having 2 to 4 carbon atoms, and multiple AOs may be identical or different from one another. p is the average number of moles of AO added, ranging from 0 to 30, and multiple p values ​​may be the same or different from one another.

[0034] In one embodiment, R' may be an aliphatic hydrocarbon group. R' is derived, for example, from the fatty acids exemplified with respect to component (A), or the oils and fats exemplified with respect to component (A), and preferably contains an unsaturated hydrocarbon. If there are multiple R' groups in one molecule, it is preferable that one or more contain an unsaturated hydrocarbon. The number of carbon atoms is preferably 12 to 24, and more preferably 16 to 20.

[0035] The general formulas (1) to (3) mentioned above for component (A) are defined in the same way as the general formulas (B-2-1), (B-3-2), and (B-4-3), respectively. For example, when a compound represented by general formula (1) is used as a raw material for the production of component (A), a portion of the compound may remain as unreacted material. This unreacted material is represented by general formula (B-2-1) and contains R, AO, and n in the dispersing and uniforming dye for polyester fibers. 1 It may be contained as a compound having the same general formula (1) as the raw material. The same applies to general formulas (2) and (3).

[0036] Components (B-1) and (B-2) may be produced simultaneously or separately using the method described above. Commercially available products may also be used.

[0037] It is also possible to produce component (A) and component (B-1) and / or component (B-2) simultaneously.

[0038] The mixing ratio (by weight) of component (A) and components (B-1) and (B-2) (A):{(B-1)+(B-2)} is not particularly limited, but is preferably 3:97 to 20:80, and more preferably 5:95 to 15:85, in terms of the balance between dyeability and scouring properties. When the blending ratio of component (A) to the total of component (A), component (B-1), and component (B-2) is 3% by weight or more, the scouring properties of the dyed fabric tend to be superior during dyeing, and when it is 20% by weight or less, the dispersibility of the dye during dyeing is superior, and the dyeing properties tend to be superior.

[0039] The mixing ratio (by weight) of component (B-1):(B-2) is not particularly limited, but is preferably 25:75 to 90:10, and more preferably 35:65 to 85:15. When the proportion of component (B-1) to the total of component (B-1) and component (B-2) is 25% by weight or more, the dispersibility of the dye during dyeing tends to be superior.

[0040] <(C) Ingredients: Anionic surfactant> A dispersing and leveling agent for dyeing polyester fibers according to one embodiment may further contain component (C), which is an anionic surfactant. The use of an anionic surfactant in combination tends to improve the dispersibility of dyes and oils that have been removed from the fabric. The anionic surfactant may be at least one selected from, for example, sulfate esters, phosphate esters, or salts thereof of alkylene oxide adducts of aliphatic alcohols having 1 to 22 carbon atoms; sulfate esters, phosphate esters, or salts thereof of polyalkylene glycols obtained from alkylene oxides having 2 to 4 carbon atoms; sulfate esters, phosphate esters, or salts thereof of alkylene oxide adducts of mono or polystyrene-modified phenols; sulfate esters, phosphate esters, or salts thereof of alkylene oxide adducts of mono or polystyrene-modified alkyl(alkyl group having 1 to 10 carbon atoms) phenols; alkyl(alkyl group having 8 to 22 carbon atoms) benzenesulfonic acid or a salt thereof; alkyl(alkyl group having 8 to 22 carbon atoms) sulfonic acid or a salt thereof; α-olefin sulfonic acid having 8 to 22 carbon atoms or a salt thereof; and α-sulfo fatty acid alkyl esters (α-sulfo fatty acid having 8 to 22 carbon atoms, alkyl group having 1 to 12 carbon atoms), or a salt thereof. The salt may be at least one selected from, for example, alkali metal salts, alkaline earth metal salts, ammonium salts, and alkanolamine salts. The anionic surfactant is preferably a sulfate ester from the viewpoint of excellent dye dispersibility during dyeing.

[0041] The mixing ratio (by weight) {(A)+(B-1)+(B-2)}:(C) of the sum of components (A), (B-1), and (B-2) to component (C) is not particularly limited, but 60:40 to 95:5 is preferred. When the mixing ratio of component (C) is 40% by weight or less relative to 100% by weight of the sum of components (A), (B-1), (B-2), and (C), the scouring performance tends to be excellent, and when it is 5% by weight or more, the dye dispersibility performance tends to be excellent.

[0042] The dispersing and leveling agent for dyeing polyester fibers of this embodiment may further contain additional components other than those exemplified above, as long as the effects of the present invention are not impaired. Additional components that can be used in combination include cationic surfactants, amphoteric surfactants, organic solvents, pH adjusters, chelating agents (EDTA, NTA, polycarboxylic acids or their salts, organic phosphonic acids or their salts, etc.), fatty acids or their salts (sodium coconut fatty acid salt, etc.), defoaming agents (silicone oil, higher alcohols, mineral oil, etc.), carrier components (benzyl benzoate, dibenzyl ether, N-butylphthalimide, etc.), antioxidants, viscosity modifiers, preservatives, and the like.

[0043] ≪Method for manufacturing dyed polyester fiber products≫ One aspect of the present invention provides a method for producing a polyester fiber dyed product. The method for producing a polyester fiber dyed product according to one aspect includes dyeing a polyester fiber product with a dyeing bath containing component (A), component (B-1), and component (B-2), and optionally component (C).

[0044] The polyester fiber products that can be treated with the dispersing and uniforming agent for dyeing polyester fibers of this embodiment are not particularly limited, but examples include regular polyester fibers, cationic dyeable polyester fibers, recycled polyester fibers, polylactic acid (PLA) fibers, polytrimethylene terephthalate (PTT) fibers, polybutylene terephthalate (PCT) fibers, or polyester fibers consisting of two or more of these, and composite or blended fibers made of these polyester fibers with natural fibers such as cotton, linen, silk, and wool; semi-synthetic fibers such as rayon and acetate; synthetic fibers such as polyamide (nylon), acrylic, polyurethane, polyethylene, and polypropylene; and inorganic fibers such as carbon, glass, ceramics, asbestos, and metal. The polyester fiber preferably contains 30% by mass or more of the above-mentioned polyester fibers, more preferably 50% by mass or more, and even more preferably 65% ​​by mass or more.

[0045] Furthermore, there are no particular restrictions on the form of the textile product, and examples include short fibers, long fibers, yarn, woven fabrics, knitted fabrics, cotton, sliver, top, and nonwoven fabrics.

[0046] When dyeing polyester fiber products, dyed polyester fiber products can be obtained by using commonly used dyeing machines, such as winches, jet dyers, jickers, cheese dyers, and hank dyers, and dyeing them for 10 to 100 minutes at a predetermined temperature, pH, and bath ratio, followed by drying. In addition, commonly used inorganic or organic chemicals and dyes can be used in the dyeing bath without any problems. After the dyeing process, washing with hot water, cold water, or reductive washing can be performed to wash away any unfixed disperse dyes.

[0047] When dyeing polyester fiber products, the temperature is preferably 80 to 180°C, more preferably 90 to 150°C, even more preferably 100 to 150°C, and even more preferably 110 to 140°C.

[0048] When dyeing polyester fiber products, the pH is preferably 3 to 6, and more preferably 4 to 6, at 25°C. Suitable pH adjusters include acetic acid, sodium acetate, phosphoric acid, sodium dihydrogen phosphate, disodium hydrogen phosphate, trisodium phosphate, lactic acid, sodium lactate, and ammonium sulfate.

[0049] When dyeing polyester fiber products, the bath ratio is preferably 1:2 to 1:50, more preferably 1:5 to 1:30, and even more preferably 1:5 to 1:20. A ratio less than 1:2 tends to result in poor dye dispersibility, uniform dyeing, and scouring. Furthermore, a ratio exceeding 1:50 is not economical.

[0050] There are no particular restrictions on the drying conditions; for example, drying at 0-200°C for 10 seconds to several days is sufficient. If necessary, after drying, the material may be heat-treated (cured) at a temperature of 100°C or higher, preferably around 110-180°C, for 10 seconds to 10 minutes, preferably 30 seconds to 3 minutes.

[0051] The total concentration of components (A), (B-1), (B-2), and (C) in the staining bath is preferably in the range of 0.01 to 10 g / L, more preferably in the range of 0.01 to 5 g / L, and even more preferably in the range of 0.05 to 3 g / L. When the concentration is 0.01 g / L or higher, dye dispersibility, scouring properties, and uniform dyeing properties tend to be superior. When the concentration is 10 g / L or lower, dye dispersibility, scouring properties, and uniform dyeing properties improve, and the colorfastness of dyed polyester fiber products tends to be superior.

[0052] In the method for manufacturing polyester fiber dyed products of this embodiment, flame retardants, lightfastness enhancers, water absorption and quick-drying agents, etc., can be added to the dyeing bath, and these functional agents can be imparted to the polyester fiber dyed product in a single bath simultaneously with the dyeing treatment.

[0053] As for the flame retardant, there are no particular limitations as long as it is a flame-retardant substance that can be treated simultaneously with the dyeing process; known substances can be used. Examples of such flame retardants include phosphate esters, condensed phosphate esters, hypophosphate esters, phosphine oxides, phosphate ester amides, phosphazenes, and halogens. As for the lightfastness enhancer, there are no particular limitations as long as it is a substance that improves lightfastness and can be treated simultaneously with the dyeing process; known substances can be used. Examples of such lightfastness enhancers include benzotriazoles, benzophenones, triazines, benzoxazinones, cyanoacrylates, and salicylates (ultraviolet absorbers). As for the water-absorbing and quick-drying agent, there are no particular limitations as long as it is a substance that absorbs and dries quickly and can be treated simultaneously with the dyeing process; known substances can be used. Examples of such water-absorbing and quick-drying agents include polyester resins and acrylic resins.

[0054] The dyeing bath may contain cationic surfactants, amphoteric surfactants, organic solvents, pH adjusters, chelating agents (EDTA, NTA, polycarboxylic acids or their salts, organic phosphonic acids or their salts, etc.), fatty acids or their salts (such as sodium coconut fatty acid salt), defoaming agents (silicone oil, higher alcohols, mineral oil, etc.), carrier components (benzyl benzoate, dibenzyl ether, N-butylphthalimide, etc.), antioxidants, viscosity modifiers, preservatives, etc., to the extent that they do not impair the effects of the present invention. [Examples]

[0055] The present invention will be described in more detail below with reference to examples of the present invention, but the present invention is not limited to these examples.

[0056] The ratio of each component is calculated as follows: The reaction products obtained in the following synthesis examples may include glycerin and fatty acids. The residual amount of glycerin was measured using gas chromatography (GC-16A [Shimadzu Corporation]). The measurement conditions are as follows. Column: GL Science TC-1 (15m x 0.25mm, ID 0.25μm) Column temperature: 180~300℃ (heating rate: 15℃ / min) Injection temperature: 320℃ Detector temperature: 320℃ Split ratio: 1:25 Sample injection volume: 1 μL

[0057] For fatty acids, the acid value of the reaction product was measured, and the residual amount was calculated using the following formula. The acid value was measured according to the neutralization titration method in JIS K 0070 (1992), section 3.1. 10 g of the sample was accurately weighed, dissolved in 60 ml of ethanol, and measured. Fatty acid residue = Molecular weight of fatty acid × Acid value / 56100 The component ratios of component (A) and component (B) were measured using a gel permeation chromatography (GPC) instrument (Tosoh Corporation GPC "HLC-8020") with tetrahydrofuran as the eluent, and calculated from the area ratio of each peak on a polystyrene calibration curve. The column used was a combination of three columns from Tosoh Corporation, product names TSK-GELG5000HHR, G4000HHR, and G3000HHR.

[0058] The compounds used are as follows:

[0059] <Fatty acid> TFA-140F (Regenerated fatty acid: Tsukuno Foods Industry, Acid value 197, Iodine value 128) KORTACID1811 (oleic acid: Pacific Oleo, acid value 199, iodine value 95) Hartol FA-1 (Harima Chemicals, Acid value 196, Iodine value 130)

[0060] <Nonionic surfactants containing hydroxyl groups> (Compounds represented by general formula (1)) 3SP-10EO: Tristyrenated phenol 10-ethylene oxide adduct 3SP-18.5EO: 18.5-ethylene oxide adduct of tristylenized phenol 3SP-30EO: Tristyrenated phenol 30-ethylene oxide adduct 2SP-13.5EO: 13.5-ethylene oxide adduct of distyrenated phenol

[0061] (Compound represented by general formula (2)) PEG-400: Polyethylene glycol (molecular weight 400) (in general formula (2), n 2 =9.1) PEG-600: Polyethylene glycol (molecular weight 600) (in general formula (2), n 2 =13.6) PEG-1000: Polyethylene glycol (molecular weight 1000) (in general formula (2), n 2 =22.7) PEG-2000: Polyethylene glycol (molecular weight 2000) (in general formula (2), n 2 =45.4)

[0062] (Compound represented by general formula (3)) DG (Glycerin: NOF Corporation)

[0063] <Oils> Soybean oil (Nisshin Oillio, iodine value 128) C-type vegetable oil (recycled oil: Hamada Chemical, iodine value 102)

[0064] <Glycerin monofatty acid ester> 1-Oleoyl-rac-glycerin (Sigma-Aldrich)

[0065] In synthesis examples (1)-1 to (1)-3, components (A), (B-1), and (B-2) were obtained. Synthesis Example (1)-1 In a reaction vessel, 90.8 g (0.99 mol) of glycerin, 309.2 g (1.08 mol) of TFA-140F, and 1.0 g of p-toluenesulfonic acid were charged. Nitrogen gas was introduced, and the mixture was heated while stirring at 190-200°C for approximately 6 hours to obtain 379 g of reaction product. The proportion of glycerol was quantified from the reaction product by gas chromatography analysis, and the proportion of unreacted fatty acids was quantified by acid value measurement. The remainder after subtracting the glycerol and fatty acid ratios obtained from the above analysis from the reaction product was taken as the ratio of the sum of components (A), (B-1), (B-2), and (B-3). Next, the composition ratio of each component to the sum of components (A), (B-1), (B-2), and (B-3) was analyzed by GPC. The results of the above analysis showed that the sum of components (A), (B-1), (B-2), and (B-3) in the reaction product was 94.1%, and the ratio of glycerol monofatty acid ester (component (A)) to this sum was 52.6% (Table 1).

[0066] Synthesis Example (1)-2 In a reaction vessel, 91.6 g (0.99 mol) of glycerin, 308.4 g (1.1 mol) of oleic acid, and 1.0 g of p-toluenesulfonic acid were charged. Nitrogen gas was introduced, and the mixture was heated with stirring at 190-200°C for approximately 6 hours to obtain 378 g of reaction product. Analysis in the same manner as in Synthesis Example (1)-1 showed that the sum of components (A), (B-1), (B-2), and (B-3) was 94.4%, and the ratio of glycerin monofatty acid ester (component (A)) to this sum was 51.6% (Table 1).

[0067] Synthesis Example (1)-3 In a reaction vessel, 90.3 g (0.98 mol) of glycerin, 309.7 g (1.08 mol) of Hartol FA-1, and 1.0 g of p-toluenesulfonic acid were charged. Nitrogen gas was introduced, and the mixture was heated while stirring at 190-200°C for approximately 6 hours to obtain 378 g of reaction product. Analysis in the same manner as in Synthesis Example (1)-1 showed that the sum of components (A), (B-1), (B-2), and (B-3) was 94.3%, and the ratio of glycerin monofatty acid ester (component (A)) to this sum was 50.7% (Table 1).

[0068] [Table 1]

[0069] In synthesis examples (2)-1 to (2)-13, component (B-1) and / or component (B-2) were obtained. In synthesis examples (3)-1 to (3)-13, component (B-1) and / or component (B-2) and component (A) were obtained.

[0070] Synthesis Example (2)-1 In a reaction vessel, 299.3g (0.35 mol) of 3SP-10EO, 100.7g (0.35 mol) of TFA-140F, and 0.8g of p-toluenesulfonic acid were charged. Nitrogen gas was introduced, and the mixture was heated while stirring at 210-220°C for approximately 6 hours to obtain 394.4g of reaction product. The proportion of unreacted fatty acids was quantified from the reaction product by measuring the acid value. The remainder after subtracting the fatty acid ratio obtained from the above analysis from the reaction product was taken as the ratio of the sum of components (A), (B-1), (B-2), and (B-3). Next, the composition ratio of each component to this sum was analyzed by GPC. The moles of raw materials used and the composition of the resulting reaction product are shown in Table 2.

[0071] Synthesis Examples (2)-2 to (2)-13 As shown in Table 2, reaction products ((2)-2) to ((2)-13) were obtained in the same manner as in synthesis example (2)-1, except that the raw materials and the amount of charge were changed.

[0072] [Table 2]

[0073] Synthesis Example (3)-1 In a reaction vessel, 102.6g (0.12 mol) of refined soybean oil, 97.4g (0.35 mol) of 3SP-10EO, and 0.4g of sodium hydroxide were charged. Nitrogen gas was introduced, and the mixture was heated while stirring at 220-230°C for approximately 4 hours to obtain 400.4g of reaction product. The proportion of glycerin was quantified from the reaction product by gas chromatography analysis, and the proportion of unreacted fatty acids was quantified by acid value measurement. The remainder after subtracting the glycerin and fatty acid ratios obtained from the above analysis from the reaction product was taken as the ratio of the sum of components (A), (B-1), (B-2), and (B-3). Next, the composition ratio of each component to this sum was analyzed by GPC. The moles of raw materials and the composition of the resulting reaction product are shown in Table 3.

[0074] Synthesis Examples (3)-2 to (3)-13 As shown in Table 3, reaction products ((3)-2) to ((3)-13) were obtained in the same manner as in synthesis example (3)-1, except that the raw materials and composition (amount charged) were changed.

[0075] [Table 3]

[0076] (Preparation of a mixture of component (A) and component (B)) Preparation Example (3)-14 Mixture ((3)-14) was obtained by mixing 15 parts by mass of the reaction product from synthesis example (1)-1 with 85 parts by mass of the reaction product from synthesis example (2)-1. Furthermore, mixing was carried out in the ratios shown in Table 4 to obtain mixtures ((3)-15) to ((3)-34).

[0077] [Table 4]

[0078] ((C) Ingredient: Anionic surfactant) C-1: Sulfur oxide of the 10-mol ethylene oxide adduct of tristyrenated phenol (The 10-mol ethylene oxide adduct of tristyrenated phenol was reacted with sulfamic acid according to a standard method to obtain an ammonium sulfate salt (50% solid content by mass).) C-2: Tetronic TR-704 (product name, manufactured by ADEKA Corporation) 4 molar sulfide (ammonium sulfate salt (50% solid content by mass) was used).

[0079] (Example 1) 51.0 parts by mass of Synthesis Example (3)-1, 18.0 parts by mass of anionic surfactant C-1, and 31.0 parts by mass of water were added and mixed to prepare a dispersing and uniforming agent for dyeing polyester fibers with a total component content of 60% by mass other than water.

[0080] Furthermore, dispersing and uniform dyeing agents for polyester fibers were obtained using the mixing ratios shown in Table 5 for Examples 2-16, the mixing ratios shown in Table 6 for Examples 17-30, and the mixing ratios shown in Table 7 for Examples 31-39.

[0081] (Comparative Example 1) A dispersion and uniform dyeing agent for polyester fibers was prepared by adding and mixing 51 parts by mass of 1-oleoyl-rac-glycerin (manufactured by Sigma-Aldrich), 18 parts by mass of anionic surfactant C-1, and 31 parts by mass of water. Furthermore, comparative dispersion and uniform dyeing agents for polyester fibers related to Comparative Examples 2 to 7 were obtained using the mixing ratios shown in Table 8.

[0082] Dye dispersibility evaluation 1 A 300 ml dyeing bath was prepared by mixing water, 1 g / L of the above-mentioned dispersing and uniforming agent for polyester fiber dyeing, 0.3 g / L of 80% acetic acid, and 1 g / L of the following disperse dye in a Colorpet pot (manufactured by Nippon Dyeing Machinery Co., Ltd.) until uniform. Without adding any fabric, the dyeing bath was heated from 60°C to 130°C at a rate of 3°C / min, held at the same temperature for 30 minutes, then cooled to 80°C. The dyeing bath was filtered through 5A filter paper (manufactured by ADVANTEC) and evaluated according to the following criteria. Figure 1 shows the grades 5 to 1 in the dye dispersibility evaluation 1. Grade 5 indicates better uniformity, and grade 1 indicates poor uniformity. Disperse dye: Foron Rubine S-2GFL 5: No dye aggregates were observed, and the dispersibility was very good (no clogging of the filter paper). 4: Almost no dye aggregates were observed, and the dispersibility was good (slight clogging of the filter paper). 3: Some dye aggregates were observed, but the dispersibility was sufficient for use (there was some clogging of the filter paper). 2: Some dye aggregates were observed, and dispersibility was slightly poor (the filter paper was slightly more prone to clogging). 1: Many dye aggregates remain, resulting in poor dispersibility (frequent clogging of filter paper).

[0083] Dye dispersibility evaluation 2 A 300 ml dye bath was prepared by adding water, 1 g / L of the above-mentioned dispersing and uniforming agent for polyester fiber dyeing, 0.3 g / L of 80% acetic acid, and 1 g / L of the following disperse dye to a Colorpet pot (manufactured by Nippon Dyeing Machinery Co., Ltd.), mixing until uniform, and then adding 0.1 ml of knitting oil (product name Sun Oil 410-B) and mixing. Without adding any fabric, the dye bath was heated from 60°C to 130°C at a rate of 3°C / min, held at the same temperature for 30 minutes, then cooled to 80°C, and the dye bath was filtered using 5A filter paper (manufactured by ADVANTEC) and evaluated according to the following criteria. Grade 5 indicates better uniformity, and Grade 1 indicates poor uniformity. Disperse dye: Foron Rubine S-2GFL 5: No dye aggregates were observed, and the dispersibility was very good (no clogging of the filter paper). 4: Almost no dye aggregates were observed, and the dispersibility was good (slight clogging of the filter paper). 3: Some dye aggregates were observed, but the dispersibility was sufficient for use (there was some clogging of the filter paper). 2: Some dye aggregates were observed, and dispersibility was slightly poor (the filter paper was slightly more prone to clogging). 1: Many dye aggregates remain, resulting in poor dispersibility (frequent clogging of filter paper).

[0084] Evaluation of uniformity Water, 1 g / L of the above-mentioned dispersing and uniforming agent for polyester fiber dyeing, 0.3 g / L of 80% acetic acid, CIDisperse Red 167 (0.3% owf), CIDisperse Orange 30 (0.3% owf), and CIDisperse Blue 79 (0.3% owf) were added to the pot of a mini color dyeing machine (manufactured by Techsam Giken), and the mixture was heated until uniform to prepare the dyeing bath. Next, polyester knit scouring cloth (manufactured by Sakai Obex Co., Ltd.) was added to the dyeing bath in a bath ratio of 1:15. The dyeing bath was heated from 60°C to 130°C at a rate of 2°C / min and held at this temperature for 30 minutes. After cooling, it was removed at 80°C, washed, dehydrated, and dried to obtain dyed polyester fiber products. The uniformity of the dyed polyester fiber products was evaluated according to the following criteria. 5: No staining streaks were observed, and the staining uniformity was excellent. 4: Almost no staining streaks were observed, and the staining was uniform. 3: Some staining inconsistencies are observed, and the uniformity of staining is slightly poor. 2: Some staining inconsistencies are observed, and the uniformity of staining is somewhat poor. 1: Many staining spots are observed, and uniform staining is poor.

[0085] Evaluation of refining properties Pre-scouring polyester knit fabric (manufactured by Sakai Obex Co., Ltd.) was subjected to 0.3 ml each of knitting oil (product name Sun Oil 410-B, manufactured by Meisei Chemical Industry Co., Ltd.) and esterification oil (product name Yukanol OL, manufactured by Tetsuno Oil & Chemical Co., Ltd.) being dropped into separate locations. The fabric was then dried at 180°C for 1 minute to produce an oil-adhered polyester fiber product. Next, water, 1 g / L of the above-mentioned dispersing and uniforming agent for polyester fiber dyeing, 0.3 g / L of 80% acetic acid, and CIDisperse Blue 79 (0.1% owf) were added to the pot of the mini color dyeing machine (manufactured by Techsam Giken), and the dyeing bath was prepared by mixing until uniform. Next, the oil-contaminated polyester fiber products described above were placed in a dyeing bath at a bath ratio of 1:20. The dyeing bath was heated from 60°C to 130°C at a rate of 2°C / min and held at that temperature for 30 minutes. After cooling, the products were removed at 80°C, washed, dehydrated, and dried to obtain dyed polyester fiber products. The scouring properties of the obtained dyed polyester fiber products were evaluated according to the following criteria. Figure 2 shows the grades 5 to 1 in the evaluation of scouring properties. 5: No oil droplet marks were observed at all, indicating excellent scouring properties. 4: Almost no oil droplet marks are visible, indicating good scouring properties. 3: Slight oil droplet marks are visible. 2: Some oil droplet marks are visible, and the scouring ability is slightly inferior. 1: Clear oil droplet marks are visible, indicating poor scouring ability.

[0086] [Table 5]

[0087] [Table 6]

[0088] Table 7

[0089] Table 8

Claims

1. A dispersing and leveling agent for dyeing polyester fibers, comprising component (A), component (B-1), and component (B-2), The aforementioned component (A) is a glycerol monofatty acid ester, The aforementioned (B-1) component is the following general formula (B-1-1), (B-1-2) and (B-1-3), R-O-(AO). 1 ----R' ・・・(B-1-1) R'-AO-AO& 2 ----R' ・・・(B-1-2) 【Chemistry 1】 [In the formula, R is an m-styrene-phenyl group (where m is 0 to 5), an m'-styrene-alkylphenyl group (where m' is 0 to 5 and the alkyl group has 1 to 12 carbon atoms), or an alkyl group having 1 to 22 carbon atoms. R' is a monovalent hydrocarbon group, and if there are multiple R' groups, they may be the same or different from each other. AO is an alkylene oxy group having 2 to 4 carbon atoms, and multiple AOs may be identical or different from one another. n 1 This is the average number of moles of AO added, and is between 5 and 50. n 2 This is the average number of moles of AO added, and is between 5 and 50. p is the average number of moles of AO added, and is between 0 and 30. Multiple values ​​of p may be the same or different from each other. At least one compound selected from those represented by any of the following: The aforementioned (B-2) component is the following general formula (B-2-1), (B-2-2) and (B-2-3), R-O-(AO). 1 -H ・・・(B-2-1) R’-COO-(AO)n 2 -H ・・・(B-2-2) 【Chemistry 2】 [In the formula, R is an m-styrene-phenyl group (where m is 0 to 5), an m'-styrene-alkylphenyl group (where m' is 0 to 5 and the alkyl group has 1 to 12 carbon atoms), or an alkyl group having 1 to 22 carbon atoms. R' is a monovalent hydrocarbon group, and if there are multiple R' groups, they may be the same or different from each other. X 1 and X 2 One side is H, and the other side is CO-R', AO is an alkylene oxy group having 2 to 4 carbon atoms, and multiple AOs may be identical or different from one another. n 1 is the average number of moles of AO added, which is from 5 to 50, n 2 This is the average number of moles of AO added, and is between 5 and 50. p is the average number of moles of AO added, and is between 0 and 30. Multiple values ​​of p may be the same or different from each other. At least one compound selected from those represented by any of the following: Dispersing and uniforming agent for dyeing polyester fibers.

2. The mixing ratio of component (A), component (B-1), and component (B-2) is, by weight, (A): {(B-1) + (B-2)} = 3:97 to 20:80, The dispersing and uniforming agent for dyeing polyester fibers according to claim 1.

3. The mixing ratio of component (B-1) and component (B-2) is, by weight, (B-1):(B-2) = 25:75 to 90:

10. The dispersing and uniforming agent for dyeing polyester fibers according to claim 1.

4. A dispersing and leveling agent for dyeing polyester fibers according to any one of claims 1 to 3, further comprising component (C), which is an anionic surfactant.

5. The total ratio of component (A), component (B-1), and component (B-2) to component (C) is, by weight, {(A) + (B-1) + (B-2)} : (C) = 60:40 to 95:

5. The dispersing and uniforming agent for dyeing polyester fibers according to claim 4.

6. A method for producing a polyester fiber dyed product, comprising dyeing a polyester fiber product with a dye bath containing component (A), component (B-1), and component (B-2), and optionally containing component (C), The aforementioned component (A) is a glycerol monofatty acid ester, The aforementioned (B-1) component is the following general formula (B-1-1), (B-1-2) and (B-1-3), R-O-(AO). 1 ----R' ・・・(B-1-1) R'-AO-AO& 2 ----R' ・・・(B-1-2) 【Transformation 3】 [In the formula, R is an m-styrene-phenyl group (where m is 0 to 5), an m'-styrene-alkylphenyl group (where m' is 0 to 5 and the alkyl group has 1 to 12 carbon atoms), or an alkyl group having 1 to 22 carbon atoms. R' is a monovalent hydrocarbon group, and if there are multiple R' groups, they may be the same or different from each other. AO is an alkylene oxy group having 2 to 4 carbon atoms, and multiple AOs may be identical or different from one another. n 1 This is the average number of moles of AO added, and is between 5 and 50. n 2 This is the average number of moles of AO added, and is between 5 and 50. p is the average number of moles of AO added, and is between 0 and 30. Multiple values ​​of p may be the same or different from each other. At least one compound selected from those represented by any of the following: The aforementioned (B-2) component is the following general formula (B-2-1), (B-2-2) and (B-2-3), R-O-(AO). 1 -H ・・・(B-2-1) R’-COO-(AO)n 2 -H ・・・(B-2-2) 【Chemistry 4】 [In the formula, R is an m-styrene-phenyl group (where m is 0 to 5), an m'-styrene-alkylphenyl group (where m' is 0 to 5 and the alkyl group has 1 to 12 carbon atoms), or an alkyl group having 1 to 22 carbon atoms. R' is a monovalent hydrocarbon group, and if there are multiple R' groups, they may be the same or different from each other. X 1 and X 2 One side is H, and the other side is CO-R', AO is an alkylene oxy group having 2 to 4 carbon atoms, and multiple AOs may be identical or different from one another. n 1 This is the average number of moles of AO added, and is between 5 and 50. n 2 This is the average number of moles of AO added, and is between 5 and 50. p is the average number of moles of AO added, and is between 0 and 30. Multiple values ​​of p may be the same or different from each other. At least one compound selected from those represented by any of the following: The aforementioned component (C) is an anionic surfactant. A method for manufacturing dyed polyester fiber products.

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