JP6661758B2 - Dyeing aid and method for producing dyed fiber products - Google Patents

Description

  The present invention relates to a dyeing assistant used for dyeing fibers and the like including polyester fibers, and a method for producing a dyed fiber product obtained by dyeing using the dyeing assistant.

  Generally, fiber dyeing is performed over time under high temperature and high pressure conditions. For example, dyeing on polyester fiber is performed as follows. First, the treatment bath is heated to about 40 to 60 ° C., and usually gradually heated for about 50 to 80 minutes, and when it is desired to complete the dyeing quickly, about 30 to 50 minutes, and gradually heated to 120 to 135 ° C. (usually , About 130 ° C.) for about 30 to 90 minutes (usually about 60 minutes).

  In order to reduce energy and work time, it has been conventionally desired to shorten the dyeing time, that is, to increase the heating rate. However, when the heating rate is increased, dye spots are easily generated or sufficient dyeing properties are obtained. There was a problem that it was difficult to be. In particular, when a dye having low dispersibility or a plurality of dyes is used, when a dyeing object contains a blended fiber or an ultrafine fiber, dyeing spots are easily generated.

  By the way, in the fiber dyeing, there is a case where the fiber is heat-treated with dry heat of about 180 to 200 ° C. as a pretreatment before the fiber is put into the dyeing treatment liquid. This is performed in order to improve the dimensional stability of the fibers or prevent wrinkles, or prevent the fibers including elastic fibers such as polyurethane from being cuffed. Further, a leveling agent for preventing dye aggregation and uniformly dyeing without unevenness, and a carrier agent for deeply dyeing, if necessary, are added to the dyeing solution.

  It is considered that such a pretreatment or a leveling agent or a carrier agent solves the above-mentioned problems associated with an increase in the rate of temperature rise. As the pretreatment or leveling agent and carrier agent, the following techniques have been disclosed.

  Examples of the leveling agent include one or two or more selected from benzoic acid esters and dibenzyl ethers, polyalkylene glycol fatty acid diesters, and styrenated phenols or α-methylstyrenated phenols having 2 to 4 carbon atoms. A leveling agent for polyester fibers containing a predetermined amount of a sulfate ester salt or a phosphate ester salt of an alkylene oxide adduct (Patent Document 1) is disclosed. As a carrier agent, one containing a benzoate and a nonionic activator (Patent Document 2) is disclosed. As a pretreatment method, a treatment liquid containing 0.1 to 10.0% by weight of a sulfonate having a molecular weight of 1,000 or less is applied to a cloth containing cellulosic fibers, and then dry heat setting (Patent Document 3) Is disclosed.

JP 2010-090498 A JP 2007-100284 A JP 2007-039842 A

  However, the above-mentioned conventional leveling agent and carrier agent have a problem that the agent emits a peculiar odor, and the working environment is deteriorated and the odor remains in the dyed fiber product. In addition, in the above-mentioned conventional pretreatment method, leveling properties were insufficient when the heating rate was high.

  Therefore, a leveling property that is insufficient for conventional leveling agents or carrier agents is improved, and a dyed fiber product having excellent leveling properties can be obtained even at a higher heating rate than usual, and dyeing with less odor. Drug was desired.

  The present invention has been made in view of the above-mentioned problems of the related art, and by using it for conventional fiber dyeing, a dyed fiber product having excellent leveling properties and dyeing properties can be obtained, and the dyeing rate is higher than usual. A dyed fiber product having excellent leveling properties and dyeing properties can be obtained even at a high temperature rate, and a dyeing aid with less odor and a method for producing a dyed fiber product using the dyeing aid are provided. The purpose is to:

  The present inventors have conducted intensive studies to solve the above problems, and as a result, have found that the above problems can be solved by using a predetermined diester of an aromatic carboxylic acid, and have completed the present invention.

（式（１）中、Ｒ^１及びＲ⁴はそれぞれ独立に炭素数１〜４のアルキル基又はアルコキシ基を表し、ａ及びｃはそれぞれ独立に０〜３の整数を表し、Ｒ^２及びＲ^３はそれぞれ独立に単結合又は炭素数１〜３のアルキレン基を表し、Ａ^１Ｏは炭素数２〜６のアルキレンオキシ基を表し、ｂは１〜１０の整数を表す。） That is, one embodiment of the present invention provides a dyeing aid characterized by containing a component (A): a compound represented by the following general formula (1).

(In the formula (1), R ¹ and R ⁴ each independently represent an alkyl group or an alkoxy group having 1 to 4 carbon atoms, a and c each independently represent an integer of 0 to 3, R ² and R ³ Each independently represents a single bond or an alkylene group having 1 to 3 carbon atoms, A ¹ O represents an alkyleneoxy group having 2 to 6 carbon atoms, and b represents an integer of 1 to 10.)

  The dyeing assistant of the present embodiment preferably further contains at least one surfactant selected from the group consisting of the component (B): an anionic surfactant and a nonionic surfactant.

（式（２）中、Ｒ^５、Ｒ^６及びＲ^７はそれぞれ独立に水素原子又はメチル基を表し、ｄは１〜３、ｅは０〜２、ｆは０〜５の整数を表し、［（ｄｅ＋ｅ）＋ｆ］は１〜５であり、Ａ^２Ｏは炭素数２〜４のアルキレンオキシ基を表し、ｇは１〜１００の整数を表し、Ｘは水素原子或いは下記一般式（２−１）、（２−２）、（２−３）又は（２−４）で表される基を表す。）

（式（２−１）中、Ｒ^８は炭素数７〜２３の脂肪族炭化水素基を表す。）

（式（２−２）、式（２−３）及び式（２−４）中、Ｍ^１、Ｍ^２、Ｍ^３及びＭ^４はそれぞれ独立に水素原子、アルカリ金属原子又はアンモニウムを表す。）

（式（３）中、Ｒ^９及びＲ^１０はそれぞれ独立に炭素数７〜２３の脂肪族炭化水素基を表し、Ａ^３Ｏは炭素数２〜４のアルキレンオキシ基を表し、ｈは１〜１００の整数を表す。） In the dyeing assistant of the present embodiment, the component (B) is a group consisting of a compound (B1) represented by the following general formula (2) and a compound (B2) represented by the following general formula (3). Preferably, the compound is at least one compound selected from the group consisting of:

(In the formula (2), R ⁵ , R ⁶ and R ⁷ each independently represent a hydrogen atom or a methyl group, d represents 1 to 3, e represents 0 to 2, f represents an integer of 0 to 5, (De + e) + f] is 1 to 5, A ² O represents an alkyleneoxy group having 2 to 4 carbon atoms, g represents an integer of 1 to 100, X represents a hydrogen atom or the following general formula (2-1) ), (2-2), (2-3) or (2-4).)

(In the formula (2-1), R ⁸ represents an aliphatic hydrocarbon group having 7 to 23 carbon atoms.)

(In the formulas (2-2), (2-3) and (2-4), M ¹ , M ² , M ³ and M ⁴ each independently represent a hydrogen atom, an alkali metal atom or ammonium.)

(In the formula (3), R ⁹ and R ¹⁰ each independently represent an aliphatic hydrocarbon group having 7 to 23 carbon atoms; A ³ O represents an alkyleneoxy group having 2 to 4 carbon atoms; Represents an integer of 100.)

  In the dyeing aid of the present embodiment, the mass ratio between the component (A) and the component (B) is preferably from 20:80 to 98: 2.

  Another embodiment of the present invention provides a method for producing a dyed fiber product, comprising a step of dyeing the fiber after adhering the dyeing assistant to the fiber.

  Still another embodiment of the present invention provides a method for producing a dyed fiber product, comprising a step of dyeing a fiber using a dyeing treatment solution containing the dyeing aid.

  In the method for producing a dyed fiber product, it is preferable that the fibers include polyester fibers.

  By using the dyeing assistant of one embodiment of the present invention for conventional fiber dyeing, a dyed fiber product having excellent levelness and dyeing properties can be obtained. Therefore, it is possible to uniformly dye even a blended fiber, a conjugate fiber, or a fiber containing an ultrafine fiber, which is difficult to dye uniformly.

  Further, by using the dyeing assistant of one embodiment of the present invention, it is possible to obtain a dyed fiber product having excellent leveling properties and dyeing properties even at a temperature rising rate higher than usual. Therefore, it is possible to contribute to saving of energy and shortening of working time, and also to cost reduction. Furthermore, since the dyeing assistant of one embodiment of the present invention has little odor, there is little possibility that the odor derived from the agent will adhere to the fiber or deteriorate the working environment.

The dyeing assistant of one embodiment of the present invention contains a compound represented by the following general formula (1) as the component (A). The component (A) functions as a carrier that expands the crystal region of the fiber and facilitates the dye to enter the fiber, particularly in dyeing a synthetic fiber such as a polyester fiber or a blended fiber or a composite fiber containing the same.

In the formula (1), R ¹ and R ⁴ each independently represent an alkyl group or an alkoxy group having 1 to 4 carbon atoms, and a and c each independently represent an integer of 0 to 3. When there are a plurality of R ¹ or R ⁴ , they may be the same or different. From the viewpoint of more excellent leveling properties and dyeing properties, R ¹ and R ⁴ are preferably alkyl groups having 1 to 3 carbon atoms. From the same viewpoint, a and c are each preferably 0 or 1, and more preferably 0.

R ² and R ³ each independently represent a single bond or an alkylene group having 1 to 3 carbon atoms. A single bond is preferable as R ² and R ³ from the viewpoint of more excellent leveling properties and dyeing properties.

A ¹ O represents an alkyleneoxy group having 2 to 6 carbon atoms, and b is 1 to 10. When there are a plurality of A ¹ Os, they may be the same or different. A ¹ O is preferably an alkyleneoxy group having 2 to 4 carbon atoms from the viewpoint of more excellent leveling properties and dyeing properties. Further, b is preferably 1 to 5 from the viewpoint of more excellent leveling properties and dyeing properties.

  As a method for producing the compound represented by the formula (1), for example, a polymer of an aromatic carboxylic acid which may have an alkyl group or an alkoxy group and an alkylene oxide having 2 to 4 carbon atoms or 2 carbon atoms To 6 alkanediols.

  The aromatic carboxylic acid has an alkyl group having 1 to 4 carbon atoms such as benzoic acid, 2-methylbenzoic acid, 4-ethylbenzoic acid, 4-n-propylbenzoic acid, and 4-t-butylbenzoic acid. Benzoic acid and benzoic acid having an alkoxy group having 1 to 4 carbon atoms, such as 2-methoxybenzoic acid and 4-t-butoxybenzoic acid, may be mentioned. As the aromatic carboxylic acid, benzoic acid or a benzoic acid having an alkyl group having 1 to 4 carbon atoms is more preferable from the viewpoint of more excellent leveling properties and dyeing properties.

  Examples of the alkanediol having 2 to 6 carbon atoms include ethane-1,2-diol, 1,3-propanediol, and 1,4-butanediol.

  The content of the component (A) in the dyeing aid may be 0.1 to 100% by mass. Examples of the component other than the component (A) that can be included in the dyeing assistant include water, an organic solvent, and a surfactant other than the component (A).

  The organic solvent is added, for example, for adjusting the viscosity of the dyeing aid or for stabilizing the agent. Examples thereof include alcohols having 1 to 10 carbon atoms such as methanol, ethanol, isopropyl alcohol, ethylene glycol monobutyl ether, and diethylene glycol monobutyl ether. Among them, diethylene glycol monobutyl ether is preferred. The content of the organic solvent in the dyeing assistant is preferably 0.5 to 15% by mass based on the total amount of the dyeing assistant.

  As the surfactant other than the component (A), a known surfactant can be used without particular limitation. For example, an anionic surfactant, a nonionic surfactant, a cationic surfactant and the like can be mentioned.

  Examples of the anionic surfactant include a sulfuric acid ester or a phosphoric acid ester of an alkylene oxide adduct of an aliphatic alcohol (having an aliphatic alcohol having 1 to 22 carbon atoms) or a salt thereof, and an alkylene oxide having 2 to 4 carbon atoms. Sulfuric acid ester or phosphoric acid ester of polyalkylene glycol or a salt thereof, sulfuric acid ester or phosphoric acid ester of an alkylene oxide adduct of mono- or polystyrene-modified phenol or a salt thereof, mono- or polystyrene-modified alkyl (alkyl group having 1 to 1 carbon atoms) 10) Sulfuric acid ester or phosphoric acid ester of alkylene oxide adduct of phenol or a salt thereof, alkyl (alkyl having 8 to 22 carbon atoms) benzenesulfonic acid or a salt thereof, alkyl (alkyl having 8 to 22 carbon atoms) sulfone Acid or , Α-olefinsulfonic acid (α-olefinsulfonic acid having 8 to 22 carbon atoms) or a salt thereof, α-sulfofatty acid alkyl ester (α-sulfofatty acid having 8 to 22 carbon atoms, alkyl group having 1 to 1 carbon atom) 12) or a salt thereof.

  Salts include alkali metal salts, alkaline earth metal salts, ammonium salts, alkanolamine salts and the like.

  Examples of the nonionic surfactant include, for example, an alkylene oxide adduct of an aliphatic alcohol (having 1 to 22 carbon atoms in an aliphatic alcohol) or a fatty acid thereof (having 8 to 24 carbon atoms in a fatty acid) and a fatty acid having 2 to 4 carbon atoms. Polyalkylene glycol or its fatty acid (fatty acid having 8 to 24 carbon atoms) ester obtained from alkylene oxide, mono- or polystyrene-modified alkylene oxide adduct of phenol or its fatty acid (fatty acid having 8 to 24 carbon atoms) ester, mono- or polystyrene-modified Fatty acids (fatty acids having 8 to 24 carbon atoms) esters of alkylene oxide adducts of alkyl (alkyl groups having 1 to 10 carbon atoms) phenols and the like can be mentioned.

  Examples of the cationic surfactant include benzalkonium chloride, a reaction product of a trialkylamine having one or two long-chain alkyl groups with a quaternizing agent, an alkylene oxide adduct of a mono- or dialkylamine with a quaternary agent. Examples thereof include a reaction product with an agent, and a quaternary ammonium surfactant such as an alkylpyridinium salt. The long-chain alkyl group of the trialkylamine has 6 to 24 carbon atoms, and the remaining alkyl group has 1 to 5 carbon atoms. The carbon number of the alkyl group of the mono- or dialkylamine is 6 to 24. Examples of the alkylene oxide include alkylene oxides having 2 to 4 carbon atoms, and the number of added moles thereof is 2 to 50. Examples of the quaternizing agent include an alkyl halide having an alkyl group having 1 to 5 carbon atoms and a dialkyl sulfate having an alkyl group having 1 to 5 carbon atoms. The number of carbon atoms in the alkyl group of the alkylpyridinium salt is 3 to 24.

  In the dyeing assistant, at least one surfactant selected from the group consisting of an anionic surfactant and a nonionic surfactant is used as the component (B) from the viewpoint of more excellent leveling properties and dyeing properties. Further, it is preferable that it is contained.

  Furthermore, among these anionic surfactants and nonionic surfactants, the following compound (B1) and / or the following compound (B2) from the viewpoint that the component (B) has more excellent leveling properties and dyeing properties. It is preferred that

Compound (B1) is a compound represented by the following general formula (2).

In the formula (2), R ⁵ , R ⁶ and R ⁷ each independently represent a hydrogen atom or a methyl group, and a hydrogen atom is preferable from the viewpoint of more excellent leveling properties and dyeing properties.

  d represents an integer of 1 to 3, e represents an integer of 0 to 2, f represents an integer of 0 to 5, and [(de + e) + f] represents 1 to 5. [(De + e) + f] is preferably 1 to 4, and more preferably 2 or 3, from the viewpoint of more excellent leveling properties and dyeing properties.

A ² O represents an alkyleneoxy group having 2 to 4 carbon atoms, and g is an integer of 1 to 100. When there are a plurality of A ² O, they may be the same or different. From the viewpoint of more excellent leveling properties and dyeing properties, A ² O is preferably an ethyleneoxy group or a propyleneoxy group, and more preferably an ethyleneoxy group. In addition, g is preferably 2 to 50, and more preferably 4 to 20, from the viewpoint of more excellent leveling properties and dyeing properties.

  X represents a hydrogen atom or a group represented by the following general formula (2-1), (2-2), (2-3) or (2-4).

As a method for producing the compound represented by the formula (2) in which X is a hydrogen atom, for example, a base catalyst (potassium hydroxide, sodium hydroxide, etc.) is added to mono- or polystyrene-modified phenol, and sufficiently added at high temperature and reduced pressure. After the dehydration, an alkylene oxide having 2 to 4 carbon atoms is subjected to an addition reaction at 80 to 200 ° C.

In the formula (2-1), R ⁸ represents an aliphatic hydrocarbon group having 7 to 23 carbon atoms, which may be saturated or unsaturated, linear or branched. You may. From the viewpoint of more excellent leveling properties and dyeing properties, the carbon number is preferably 11 to 21, and more preferably 13 to 19.

  As a method for producing a compound of the formula (2) wherein X is a group represented by the formula (2-1), for example, an alkylene oxide adduct of 2 to 4 carbon atoms of mono- or polystyrene-modified phenol and 8 to 24 carbon atoms By reacting with a fatty acid.

Examples of the fatty acid having 8 to 24 carbon atoms include octanoic acid, nonanoic acid, decanoic acid, dodecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, 9-hexadecenoic acid, heptadecanoic acid, 2-heptylundecanoic acid, and cis-9- Octadecenoic acid, 11-octadecenoic acid, cis, cis-9,12-octadecadienoic acid and the like can be mentioned. In addition, as the fatty acid having 8 to 24 carbon atoms, those derived from natural products may be used, and examples thereof include tall fatty acids purified from tall oil and coconut oil fatty acids obtained by hydrolyzing coconut oil. Among these, cis-9-octadecenoic acid, tall fatty acid, cis, cis-9,12-octadecadienoic acid are preferable, and cis-9, from the viewpoint that dye dispersibility, leveling property, and dyeing property are more excellent. -Octadecenoic acid is more preferred.

In the formulas (2-2), (2-3) and (2-4), M ¹ , M ² , M ³ and M ⁴ represent a hydrogen atom, an alkali metal atom or ammonium. As M ¹ , M ² , M ³ and M ⁴ , ammonium is preferred from the viewpoint of more excellent leveling properties and dyeing properties.

  X is preferably a hydrogen atom or a group represented by the formula (2-1), and more preferably a hydrogen atom, from the viewpoint of more excellent leveling properties and dyeing properties.

Next, (B2) will be described. (B2) is a compound represented by the following general formula (3).

In the formula (3), R ⁹ and R ¹⁰ each independently represent an aliphatic hydrocarbon group having 7 to 23 carbon atoms, may be saturated or unsaturated, and may be linear or branched. It may be chain-like. From the viewpoint of more excellent leveling properties and dyeing properties, the carbon number is preferably 11 to 21, and more preferably 13 to 19.

A ³ O represents an alkyleneoxy group having 2 to 4 carbon atoms, and h represents an integer of 1 to 100. When there are a plurality of A ³ Os, they may be the same or different. From the viewpoint of more excellent leveling properties and dyeing properties, A ³ O is preferably an ethyleneoxy group or a propyleneoxy group, and more preferably an ethyleneoxy group. H is preferably 5 to 25 from the viewpoint of more excellent leveling properties and dyeing properties.

  As a method for producing the compound represented by the general formula (3), for example, a fatty acid having 8 to 24 carbon atoms is reacted with a polymer of an alkylene oxide having 2 to 4 carbon atoms or an alkanediol having 2 to 4 carbon atoms. Can be obtained.

  As the fatty acid having 8 to 24 carbon atoms, the same as those described above can be exemplified. Examples of the alkanediol having 2 to 4 carbon atoms include ethane-1,2-diol, 1,3-propanediol, and 1,4-butanediol.

  As the component (B) in the dyeing assistant, among the compounds (B1) and (B2), the compound (B1) is more preferable from the viewpoint of more excellent leveling properties and dyeing properties.

  The mass ratio of the component (A) to the component (B) in the dyeing aid is (A) :( B) = 20: 80 to 98: 2 from the viewpoint that the leveling property and the dyeing property are more excellent. Is preferably 30:70 to 90:10, more preferably 40:60 to 85:15.

  The total content of the component (A) and the component (B) in the dyeing aid is 0.1 to 100% by mass.

  Next, an embodiment of a method for producing a dyed fiber product will be described.

  As a method for producing a dyed fiber product, a method including a step of dyeing after adhering a dyeing aid to a fiber before being put into a dyeing treatment liquid (a method for producing a dyed fiber product including a pretreatment method), and And a method including a step of dyeing a fiber using a dyeing treatment solution containing a dyeing aid.

  In the pretreatment method, as a method of attaching the dyeing assistant to the fiber, for example, a dyeing assistant is used as it is or dispersed in water or the like to prepare a treatment liquid, and a dipping method, a padding method, a spray method, a coating method ( (A coating method, a printing method) and the like, and a method of attaching a dyeing aid to the fiber. After attaching, it may be dried. In the case of the immersion method, a commonly used dyeing machine, for example, a wins dyeing machine, a liquid jet dyeing machine, a zicker, a cheese dyeing machine, a skein dyeing machine and the like can be used. In the case of a coating method, a method such as brush coating, roller coating, flow coater coating and the like can be mentioned.

  The drying conditions are not particularly limited, and may be normal temperature or heating. Further, heat treatment is preferably performed at the same time as or after the drying. Examples of the heat treatment method include a method performed by using a heat setting machine such as a tenter machine. The condition may be wet heat or dry heat, but dry heat is preferable, and the temperature is preferably 120 to 190 ° C, more preferably 150 to 170 ° C.

  The amount of the dyeing aid of the present embodiment attached to the fibers is preferably such that the amount of the component (A) attached is 0.1 to 10% by mass of the fibers, and 0.5 to 5% by mass. % Is more preferable.

  When the fiber is dyed using a dyeing solution containing a dyeing aid, the amount of the dyeing aid to be added to the dyeing solution can be appropriately adjusted depending on the type of the dye. 0.01-15% o. w. f. And an amount of 0.3 to 8% o. w. f. Is more preferred.

  As a method for producing a dyed fiber product, a method including a pretreatment method is preferred from the viewpoint of more excellent levelness.

  A leveling agent is added to the dyeing treatment solution in the method for producing a dyed fiber product, and a conventionally known leveling agent can be used without any particular limitation. The amount of the leveling agent added to the dyeing solution is 0.01 to 15% o. w. f. And an amount of 0.3 to 8% o. w. f. Is more preferred.

  In the method for producing a dyed fiber product, the fiber to be dyed is not particularly limited, and examples thereof include natural fibers, chemical fibers, and blended fibers or composite fibers thereof. Natural fibers include cotton, hemp, wool, and the like. Chemical fibers include regenerated fibers such as rayon and cupra, semi-synthetic fibers such as acetate, and synthetic fibers such as polyester, polyamide, acrylic, and spandex. The form of the fibers is not particularly limited, and examples thereof include yarns, ultrafine fibers, knits, woven fabrics, and nonwoven fabrics.

  The method for producing a dyed fiber product is preferably used in the production of a dyed fiber product containing polyester fibers, from the viewpoint of more excellent leveling properties and dyeing properties.

  The bath ratio between the fiber to be dyed and the dyeing solution varies depending on the desired dyeing properties and the like, but may be in the range of 1: 3 to 1:30, more preferably 1: 5 to 1:25.

  As the dye, a disperse dye is suitable, and the amount of the dye used can be appropriately selected. For example, 0.001 to 20% o. w. f. Amount.

  Further, an acid or a chelating agent for adjusting pH, a surfactant other than the components (A) and (B), and the like can be added to the treatment liquid as in the past.

  There is no particular limitation on the dyeing machine to be used, and conventional ones can be used, for example, a liquid jet dyeing machine, a Wins dyeing machine, a Jigger dyeing machine, a beam dyeing machine, a cheese dyeing machine, an Overmeyer dyeing machine, and a high-pressure jetting machine. And a dyeing machine.

  Conventional conditions can be applied to the dyeing temperature and dyeing time. For example, the treatment solution is heated to about 40 to 60 ° C., usually about 50 to 80 minutes, and about 30 to 50 minutes to complete the dyeing quickly. The temperature is gradually raised, and a high-temperature treatment is performed at 120 to 135 ° C. for about 30 to 90 minutes. Thereafter, it is preferable to perform a soaping process such as reduction cleaning.

  The pressure during dyeing and the soaping method after dyeing are not particularly limited, and conventional methods and conditions can be employed.

  The dyeing assistant can provide a dyed fiber product having excellent leveling properties and dyeing properties not only at the time of dyeing at a normal heating rate but also at a higher heating rate than usual. . Therefore, it can contribute to reduction of energy and working time. Further, the dyeing aid can suppress odor.

  Hereinafter, the present invention will be described in more detail with reference to Examples, but the present invention is not limited to these Examples.

{1} Production of Dyeing Aid Using the compounds obtained in the following Synthesis Examples and Comparative Synthesis Examples, dyeing aids having the compositions shown in Tables 1 and 2 (Examples 1 to 5, 8 to 15, 18 to 25 and 28-30, Reference Examples 6-7, 16-17 and 26-27 , and Comparative Examples 1-8) were obtained.

（上記式において、ＥＯはエチレンオキシ基を表す。） Synthesis Example 1 Synthesis of Compound (A-1) as Component (A) 150.1 g of triethylene glycol in a 1-L glass reaction vessel equipped with a stirrer, thermometer, reflux condenser with water separator, and nitrogen gas inlet tube. (1.0 mol), 244.2 g (2.0 mol) of benzoic acid, 1.22 g of tin oxide and 36 g of xylene were charged, and the temperature was raised to 180 ° C. while blowing nitrogen into the reaction solution at a flow rate of 30 ml / min. . After reaching 180 ° C., esterification was carried out at the same temperature for 8 to 10 hours. Water generated by the reaction was removed from the reaction system by azeotropy with xylene. The obtained esterification reaction product is neutralized with a 5% by mass aqueous solution of sodium hydroxide, washed with warm water, and then the remaining xylene is distilled off at 120 to 135 ° C. under a reduced pressure of 1.5 kPa. The compound A-1 represented was obtained.

(In the above formula, EO represents an ethyleneoxy group.)

〔上記式において、ＰＯはプロピレンオキシ基を表す。〕 Synthesis Example 2 Synthesis of Compound (A-2) as Component (A) Synthesis Example 1 was repeated except that triethylene glycol 150.1 g (1.0 mol) was changed to dipropylene glycol 134 g (1.0 mol). Similarly, compound A-2 represented by the following formula was obtained.

[In the above formula, PO represents a propyleneoxy group. ]

（上記式において、ＥＯはエチレンオキシ基を表し、ｐは８〜１０を表す。） Synthesis Example 3 Synthesis of Compound (A-3) as Component (A) Except that 150.1 g (1.0 mol) of triethylene glycol was changed to 400 g (1.0 mol) of polyethylene glycol (average molecular weight: 400) A compound represented by the following formula was obtained in the same manner as in Synthesis Example 1.

(In the above formula, EO represents an ethyleneoxy group, and p represents 8 to 10.)

Synthesis Example 4 Synthesis of Compound (A-4) as Component (A) Except that 150.1 g (1.0 mol) of triethylene glycol was changed to 90.1 g (1.0 mol) of 1,4-butanediol In the same manner as in Synthesis Example 1, a compound represented by the following formula was obtained.

Synthesis Example 5 Synthesis of Compound (A-5) as Component (A) Synthesis Example 1 except that 244.2 g (2.0 mol) of benzoic acid was changed to 272.3 g (2.0 mol) of methyl benzoic acid. In the same manner as in the above, a compound represented by the following formula was obtained.

Synthesis Example 6 Synthesis of Compound (B1-1) as Component (B) An ethylene oxide adduct of tristyrenated phenol (average addition mole number: 20) was used as B1-1.

Synthesis Example 7 Synthesis of Compound (B1-2) as Component (B) A cis-9-octadecenoic acid ester of an ethylene oxide adduct of monostyrenated phenol (average addition mole number: 20) was used as B1-2.

Synthesis Example 8 Synthesis of Compound (B1-3) as Component (B) An ammonium salt of a sulfate of an ethylene oxide adduct of tristyrenated phenol (average number of moles added: 10) was used as B1-3.

Synthesis Example 9 Synthesis of Compound (B2-1) as Component (B) A cis-9-octadecenoic acid diester of polyethylene glycol (average molecular weight: 800) was used as B2-1.

（上記式において、ＥＯはエチレンオキシ基を表し、ｑは１３又は１４を表す。） Comparative Synthesis Example 1 Synthesis of Compound (A ') The same as Synthesis Example 1 except that 150.1 g (1.0 mol) of triethylene glycol was changed to 600 g (1.0 mol) of polyethylene glycol (average molecular weight 600). Thus, a compound represented by the following formula was obtained.

(In the above formula, EO represents an ethyleneoxy group, and q represents 13 or 14.)

{2} Evaluation (I) Odor, (II) Dyeability and leveling property were evaluated for the dyeing assistants of Examples and Comparative Examples by the following methods.

(I) Odor A 1% by mass aqueous solution of the dyeing assistants of Examples and Comparative Examples was prepared, placed in a closed container, and allowed to stand at 80 ° C. for 10 minutes. Thereafter, the odor when the sealed container was opened was evaluated according to the following criteria. The results are shown in Tables 1 and 2.
A: No odor is felt.
B: Odor is slightly felt.
C: An odor is felt very much.

(II) Dyeing and leveling properties Dyed fiber products were obtained by the following dyeing method 1 or dyeing method 2. In addition, about Comparative Examples 5 and 8, dyeing was performed without using a dyeing assistant.

(II) -1. Dyeing method 1
In a pot of a mini-color dyeing machine (Rapid), a dyeing treatment solution having the following composition is prepared using water, and a polyester taffeta scoured cloth (30 denier, basis weight: 50 g / m ² ) as a fiber to be dyed is added to the bath. The mixture was charged at a ratio of 1:10 and stained under the following conditions i or ii.

<Dyeing treatment liquid composition>
-Dyeing assistants of Examples and Comparative Examples 1 g / L
・ Leveling agent 0.5g / L
[Leveling agent composition]
45% by mass of cis-9-octadecenoic acid diester of polyethylene glycol (average molecular weight 800)
・ Sulfuric acid ester ammonium salt of ethylene oxide adduct of tristyrenated phenol (average number of moles added: 10) 45% by mass
・ Diethylene glycol monobutyl ether 5% by mass
・ Water 5% by mass
・ PH adjuster 0.3g / L
Glacial acetic acid / dispersed dye 0.3% o. w. f.
・ Dianix Yellow Brown XF (manufactured by Dystar, trade name)
・ Dianix Ruby XFN (manufactured by Dystar, trade name)
・ Dianix Navy XF (manufactured by Dystar, trade name)

<Staining conditions>

  After the dyeing treatment, the treatment liquid was cooled to about 80 ° C., and the fiber to be dyed was taken out. They were put into a reducing cleaning solution having the following composition at a bath ratio of 1:30, and reduced and washed at 80 ° C. for 15 minutes. Thereafter, washing, dehydration and drying were performed to obtain a dyed fiber product.

<Reduction cleaning liquid composition>
・ SUNMORL M-240 (Zhejiang Nichika Chemical, trade name) 1g / L
・ Sodium carbonate 1g / L
・ Sodium hydrosulfite 1g / L

  (II) -2. Dyeing method 2 (pretreatment method)

Water was mixed so that the concentration of the dyeing assistants of Examples and Comparative Examples was 2.5% by mass to prepare treatment solutions. There, a polyester taffeta scoured cloth (30 denier, basis weight: 50 g / m ² ) was immersed, squeezed with a mangle so as to have a squeezing ratio of 40% by mass, dried at 120 ° C. for 2 minutes, and subsequently dried at 150 ° C. Dry heat treatment was performed at 1 ° C. for 1 minute. The amount of the dyeing aid adhering to the scoured polyester taffeta cloth was 1% by mass of the scoured polyester taffeta cloth.

Thereafter, except that the composition of the dyeing treatment liquid was changed as described below, dyeing was performed in the same manner as in “(II) -1. Dyeing method 1” to obtain a dyed fiber product.
<Dyeing treatment liquid composition>
・ Leveling agent 0.5g / L
[Leveling agent composition]
45% by mass of cis-9-octadecenoic acid diester of polyethylene glycol (average molecular weight 800)
・ Sulfuric acid ester ammonium salt of ethylene oxide adduct of tristyrenated phenol (average number of moles added: 10) 45% by mass
・ Diethylene glycol monobutyl ether 5% by mass
・ Water 5% by mass
・ PH adjuster 0.3g / L
Glacial acetic acid / dispersed dye 0.3% o. w. f.
・ Dianix Yellow Brown XF (manufactured by Dystar, trade name)
・ Dianix Ruby XFN (manufactured by Dystar, trade name)
・ Dianix Navy XF (manufactured by Dystar, trade name)

(II) -3. Evaluation of dyeability
With respect to the obtained dyed fiber product, a K / S value for each 10 nm of 400 to 700 nm was obtained using a spectrophotometer (CM-3600d, manufactured by Konica Minolta Sensing Co., Ltd.), and the integrated value was calculated. The K / S value of the dyed fiber product was used.

  When the K / S value of the dyed fiber product of Comparative Example 5 was set to 100, the K / S value of the other dyed fiber product was determined, and the result was defined as the dyeing rate. The results are shown in Tables 1 and 2. The higher the dyeing ratio, the deeper the dyeing, that is, the better the dyeing property.

(II) -4. Evaluation of leveling property The obtained dyed fiber product was visually observed, and the leveling property was evaluated according to the following criteria. The results are shown in Tables 1 and 2.
<Evaluation criteria>
A: Almost no staining spots observed, good levelness B: Slightly spotted spots, slightly good leveling property C: Slight spotting slightly observed, leveling property somewhat poor D: Many staining spots are seen, insufficient leveling

  As shown in Tables 1 and 2, it was found that the dyeing assistant of one embodiment of the present invention suppressed the odor derived from the agent. In addition, it was found that by using the dyeing aid of one embodiment of the present invention, a dyed fiber product having excellent leveling properties and dyeing properties can be produced.

  In addition, it was found that a dyed fiber product having excellent leveling properties and dyeing properties can be produced even when the heating rate is higher than usual.

  Since the dyeing assistant of one embodiment of the present invention has a small odor, the odor derived from the agent is less likely to adhere to the fiber to be dyed, and the working environment for dyeing can be improved. Further, by using the dyeing aid of the present invention, a dyed fiber product having excellent levelness and dyeing properties can be produced. For this reason, it is possible to uniformly dye even a fiber product containing a blended fiber, a conjugate fiber, and an ultrafine fiber, which is difficult to dye uniformly.

  Further, in the dyeing assistant of one embodiment of the present invention, a dyed fiber product having excellent leveling properties and dyeing properties can be produced even when the heating rate is higher than usual. Therefore, it is possible to contribute to saving of energy and shortening of working time, and also to cost reduction.

Claims (5)

Component (A): contains a compound represented by the following general formula (1) and component (B): at least one surfactant selected from the group consisting of an anionic surfactant and a nonionic surfactant. And
The component (B) includes at least one compound selected from the group consisting of a compound (B1) represented by the following general formula (2) and a compound (B2) represented by the following general formula (3),
A dyeing assistant, wherein the mass ratio of the component (A) to the component (B) is from 40:60 to 85:15.

(In the formula (1), R ¹ and R ⁴ each independently represent an alkyl group or an alkoxy group having 1 to 4 carbon atoms, a and c each independently represent an integer of 0 to 3, R ² and R ³ Each independently represents a single bond or an alkylene group having 1 to 3 carbon atoms, A ¹ O represents an alkyleneoxy group having 2 to 6 carbon atoms, and b represents an integer of 1 to 10.)

(In the formula (2), R ⁵ , R ⁶ and R ⁷ each independently represent a hydrogen atom or a methyl group, d represents 1 to 3, e represents 0 to 2, f represents an integer of 0 to 5, (De + e) + f] is 1 to 5, A ² O represents an alkyleneoxy group having 2 to 4 carbon atoms, g represents an integer of 1 to 100, X represents a hydrogen atom or the following general formula (2-1) ), (2-2), (2-3) or (2-4).)

(In the formula (2-1), R ⁸ represents an aliphatic hydrocarbon group having 7 to 23 carbon atoms.)

(In the formulas (2-2), (2-3) and (2-4), M ¹ , M ² , M ³ and M ⁴ each independently represent a hydrogen atom, an alkali metal atom or ammonium.)

(In the formula (3), R ⁹ and R ¹⁰ each independently represent an aliphatic hydrocarbon group having 7 to 23 carbon atoms; A ³ O represents an alkyleneoxy group having 2 to 4 carbon atoms; Represents an integer of 100.) Wherein the component (B), in front Symbol compound represented by the general formula (2) (B1) and front Symbol least one compound selected from the group consisting of compounds represented by the general formula (3) (B2) The dyeing assistant according to claim 1 , wherein A method for producing a dyed fiber product, comprising a step of dyeing the fiber after attaching the dyeing aid according to claim 1 or 2 to the fiber. A method for producing a dyed fiber product, comprising a step of dyeing a fiber using a dyeing treatment solution containing the dyeing aid according to claim 1 or 2 . Method for producing a dyed textile product according to claim 3 or 4 wherein the fiber is characterized in that it comprises a polyester fiber.