JP5960349B2 - Dyeing aid for polyester fiber, polyester fiber dyeing method using the same, and dyed product manufacturing method - Google Patents

Description

  TECHNICAL FIELD The present invention relates to a dyeing aid for polyester fibers, a method for dyeing polyester fibers using the same, and a method for producing a dyed product, and in particular, a dyeing aid used when dyeing polyester fibers with a disperse dye, and The present invention relates to a method for dyeing a used polyester fiber and a method for producing a dyed product.

  In general, dyeing of polyester fibers is carried out by carrying out a sufficient scouring process to remove oils and glues attached at the stage of spinning, etc., and then dispersed in the presence of a dyeing aid under a high temperature and high pressure of 110 to 140 ° C. Dye is used.

  However, in recent years, the scouring process has been simplified in order to reduce the processing cost and shorten the process, and scouring and dyeing have been frequently performed in the same bath treatment. In this case, an oil agent or the like often remains in the fiber, which causes various problems such as stains due to dye aggregates, color spots on the dyed product, and contamination of the can of the dyeing machine.

  On the other hand, the processing of high-density materials is increasing due to market demands, and such materials tend to be insufficiently scouring in the first place, leaving oils and pastes, and penetrating dyeing aids such as leveling agents. However, the problem is that a uniform dyed product cannot be obtained.

  Japanese Patent Application Laid-Open No. 2003-227077 (Patent Document 1) discloses dispersive leveling including an anionic surfactant with a limited addition form and addition amount of alkylene oxide and a specific ester-type nonionic surfactant. Have been proposed.

  JP 2010-90498 A (Patent Document 2) discloses a high-density, containing one or more selected from benzoic acid esters and dibenzyl ether and a specific polyalkylene glycol fatty acid diester. A leveling agent can be obtained for fabrics and composite fiber materials in a short time, and a leveling agent suitable for continuous processing by rapid dyeing has been proposed.

JP 2003-227077 A JP 2010-90498 A

  However, although the low-foaming dyeing aid described in Patent Document 1 has a certain effect on the dye dispersibility and foam-suppressing property, it is still not suitable for a material having a high woven / knitted density such as a high-density polyester fiber. There is a problem that dyed spots occur. In addition, the leveling agent described in Patent Document 2 is still insufficient in leveling property, and the leveling agent remains on the dyed product, resulting in a problem that light fastness and friction fastness are reduced. There is a point.

  In view of such problems of the prior art, the present invention suitably uses dye fibers using disperse dyes at high temperatures, particularly unrefined or poorly scoured polyester fibers for dyeing using disperse dyes at high temperatures. It is an object of the present invention to provide a dyeing assistant that can obtain a dyed product that is excellent in light fastness and uniformly dyed. Another object of the present invention is to provide a method for dyeing polyester fibers and a method for producing a dyed polyester fiber using this dyeing assistant.

  As a result of intensive studies in order to solve the above problems, the present inventors have determined that a specific ester-type nonionic surfactant, dibenzyl ether and / or benzyl benzoate, a specific ether-type nonionic surfactant, and a specific By adding a combination of anionic surfactants at a specific ratio, we found a dyeing assistant that can be used suitably when dyeing unscoured or poorly scoured polyester fibers with disperse dyes at high temperatures. Based on this finding, the present invention has been completed.

  That is, the present invention is represented by a compound (A) represented by the following general formula (I), at least one compound (B) selected from dibenzyl ether and benzyl benzoate, and represented by the following general formula (II). The compound (C) and the compound (D) represented by the following general formula (III) are included, and the compound (A), (B), (C) and (D) are combined with respect to 100 parts by mass of the compound ( 40) to 80 parts by mass of A), 5 to 30 parts by mass of compound (B), 5 to 25 parts by mass of compound (C), and 1 to 25 parts by mass of compound (D). A dyeing aid for polyester fibers is provided.

(In the formula, R ¹ represents a divalent group represented by the following formula (i). A and b are each independently an integer of 1 to 5, and when b is 2 or more, a plurality of a are the same. However, the total number of R ¹ in the compound (A) represented by the general formula (I) is an integer of 1 to 5. EO represents an ethyleneoxy group, and c is EO. The average added mole number is 8 to 22. R ² is a hydrocarbon group having 7 to 21 carbon atoms.

(Wherein, R ¹ is the general formula (.k and l are the same as R ¹ in I) are each independently an integer of 1 to 5, and when l is 2 or more, a plurality of k are the same However, the total number of R ¹ in the compound (C) represented by the general formula (II) is an integer of 1 to 5. EO represents an ethyleneoxy group, and n is an average addition of EO. The number of moles is 8 to 20.)

(Wherein, R ¹ is the same as R ¹ in the general formula (I) .w and x are each independently an integer of 1 to 5, when x is 2 or more, a plurality of w is the same However, the total number of R ¹ in the compound (D) represented by the general formula (III) is an integer of 1 to 5. PO represents a propyleneoxy group, and y represents an average addition of PO. The number of moles is 0 to 15. EO represents an ethyleneoxy group, z represents the average number of moles of EO added, and is 2 to 14. The addition form of PO and EO in [] is a block addition or (R is random addition. M represents a monovalent cation.)

  The dyeing assistant of the present invention can be suitably used for dyeing with disperse dyes at high temperatures, particularly dyeing unscoured or insufficiently refined polyester fibers. The dyeing assistant of the present invention has foam suppression and decoloring resistance, is excellent in dye dispersibility, scouring property and leveling property, and can improve the light fastness of the dyed product obtained.

  The present invention also provides a method for dyeing polyester fibers, comprising the step of dyeing polyester fibers in the presence of the dyeing aid for polyester fibers.

  The dyeing method of the present invention is suitable for dyeing using a disperse dye at a high temperature, particularly for dyeing unscoured or insufficiently refined polyester fibers. According to the dyeing | staining method of this invention, it is excellent in light fastness and can obtain the dyed material dye | stained uniformly.

  The present invention further provides a method for producing a dyed product comprising the steps of preparing polyester fibers and dyeing the polyester fibers in the presence of the dyeing aid for polyester fibers.

  According to the method for producing a dyed product of the present invention, even if a polyester fiber to be dyed is unscoured or insufficiently scoured, it is excellent in light fastness and uniformly by a dyeing method using a normal disperse dye. A dyed dyeing can be produced.

  According to the dyeing assistant and dyeing method for polyester fibers of the present invention, suitable for dyeing with disperse dyes at high temperatures, particularly dyeing unscoured or poorly scoured polyester fibers with disperse dyes at high temperatures. Accordingly, a dyed product excellent in light fastness and uniformly dyed can be obtained. According to the method for producing a dyed product of the present invention, even if a polyester fiber to be dyed is unscoured or insufficiently scoured, it is excellent in light fastness and uniformly by a dyeing method using a normal disperse dye. A dyed dyeing can be produced.

  The dyeing aid for polyester fibers of the present invention comprises at least one compound (B) selected from the compound (A) represented by the following general formula (I), dibenzyl ether and benzyl benzoate, the following general formula (II) ) And the compound (D) represented by the following general formula (III), and a total of 100 parts by mass of the compounds (A), (B), (C) and (D) On the other hand, 40-80 mass parts of compound (A), 5-30 mass parts of compound (B), 5-25 mass parts of compound (C), and 1-25 mass parts of compound (D) are contained. It is characterized by this.

(In the formula, R ¹ represents a divalent group represented by the following formula (i). A and b are each independently an integer of 1 to 5, and when b is 2 or more, a plurality of a are the same. However, the total number of R ¹ in the compound (A) represented by the general formula (I) is an integer of 1 to 5. EO represents an ethyleneoxy group, and c is EO. The average added mole number is 8 to 22. R ² is a hydrocarbon group having 7 to 21 carbon atoms.

(Wherein, R ¹ is the general formula (.k and l are the same as R ¹ in I) are each independently an integer of 1 to 5, and when l is 2 or more, a plurality of k are the same However, the total number of R ¹ in the compound (C) represented by the general formula (II) is an integer of 1 to 5. EO represents an ethyleneoxy group, and n is an average addition of EO. The number of moles is 8 to 20.)

(Wherein, R ¹ is the same as R ¹ in the general formula (I) .w and x are each independently an integer of 1 to 5, when x is 2 or more, a plurality of w is the same However, the total number of R ¹ in the compound (D) represented by the general formula (III) is an integer of 1 to 5. PO represents a propyleneoxy group, and y represents an average addition of PO. The number of moles is 0 to 15. EO represents an ethyleneoxy group, z represents the average number of moles of EO added, and is 2 to 14. The addition form of PO and EO in [] is a block addition or (R is random addition. M represents a monovalent cation.)

In the general formula (I), a and b are each independently an integer of 1 to 5, and when b is 2 or more, a plurality of a may be the same or different. However, the total number of R ¹ in the compound (A) represented by the general formula (I) is an integer of 1 to 5. For example, when b is 1, a may be an integer of 1 to 5, and in this case, the total number of R ¹ in the compound (A) represented by the general formula (I) is an integer of 1 to 5, respectively. . When b is 2 and two a's are the same, a can be 1 or 2, in which case the total number of R ¹ in the compound (A) represented by the general formula (I) is 2 or 4. When b is 2 and two a's are different, when one a of the two is 1, the other a may be an integer of 2 to 4, in this case, represented by the general formula (I) In the compound (A), the total number of R ¹ is an integer of 3 to 5, respectively. When b is 2 and two a are different, when one of the two is 2, the other a may be 1 or 3, in which case the compound represented by the general formula (I) The total number of R ¹ in (A) is 3 or 5, respectively. If b is 3 or more, it is analogized.

In the general formula (I), R ¹ is a styrene group (phenylethylene group). The styrenated phenol that is a raw material of the compound (A) represented by the general formula (I) may be a mixture of compounds having different styrene addition moles per mole of phenol. Such mixtures are expressed by the average added moles of styrene per mole of phenol. For example, when the average added mole number of styrene per mole of phenol in the mixture is 3, it is expressed as tristyrenated phenol. In the present invention, as the compound (A) represented by the general formula (I), a mixture of compounds (A) having different addition mole numbers may be used. In this case, the average value of the total number of individual R ¹ in the compound (A) represented by the general formula (I) contained in the mixture (that is, the average added mole number of styrene with respect to 1 mole of phenol in the mixture) is 1 to 5. Any integer of. In this case, if the average value of the total number of R ¹ in the compound (A) represented by the general formula (I) contained in this mixture is an integer of 1 to 5, it is represented by the individual general formula (I). The total number of R ¹ in the compound (A) may be 6 or more. Moreover, the mixture as a compound (A) represented by general formula (I) is described by the average addition mole number of the styrene. For example, an ethylene oxide 16-mol adduct oleic acid ester of styrenated phenol having an average value of the total number of R ¹ in the compound (A) represented by the general formula (I) (that is, an average addition mole number of styrene) of 3 If so, it is expressed as tristyrenated phenol ethylene oxide 16-mol adduct oleate.

  In the general formula (I), EO represents an ethyleneoxy group. c shows the average addition mole number of EO, and is 8-22. If c is less than 8, the solubility in water decreases, and the components may be separated. On the other hand, if c exceeds 22, the leveling property may decrease, and the leveling effect on the fibers may be decreased. From the viewpoint of the stability and levelness of the dyeing assistant, c is preferably 10-20.

  In the general formula (I), R represents a hydrocarbon group having 7 to 21 carbon atoms. In the present specification, —COR combined with R and the —CO group bonded thereto may be referred to as “fatty acid residue”. If the number of carbon atoms is less than 7 or exceeds 21, the leveling property may be reduced, and the leveling effect on the fiber may be reduced. From the viewpoint of levelness, R is preferably a hydrocarbon group having 11 to 19 carbon atoms. This hydrocarbon group may be saturated or unsaturated, and may have a substituent. Examples of the hydrocarbon group include a heptadecenyl group, an isoheptadecenyl group, a heptadecene group, and a heptadecadiene group.

  It is estimated that the compound (A) represented by the general formula (I) mainly has an action of emulsifying and dispersing the compound (B), and also has an improvement in leveling property of the disperse dye to the fiber. The action by the compound (A) is not limited to these.

  The synthesis of compound (A) can be obtained by a conventionally known method. For example, after adding a predetermined amount of ethylene oxide to tristyrenated phenol at 120 to 170 ° C. under pressure using an alkali catalyst such as sodium hydroxide or potassium hydroxide, a fatty acid having 8 to 22 carbon atoms is added. In addition, the compound (A) can be obtained by esterification at 160 to 200 ° C. In this case, -COR in the general formula (I) is a fatty acid residue derived from a fatty acid having 8 to 22 carbon atoms. The fatty acid having 8 to 22 carbon atoms may be either a saturated fatty acid or an unsaturated fatty acid, and stearic acid, isostearic acid, oleic acid, linoleic acid, tall oil fatty acid and the like are preferably used.

  The compounding quantity of the compound (A) in the dyeing assistant of this invention is 40-80 mass parts with respect to a total of 100 mass parts of compounds (A), (B), (C), and (D). If the compounding amount of the compound (A) is less than 40 parts by mass, the leveling property may be lowered, and the leveling effect on the fibers may not be obtained. On the other hand, when the compounding amount of the compound (A) exceeds 80 parts by mass, the dye dispersibility in the dyeing bath is lowered, which may lead to dyeing troubles such as taring stains due to aggregation. From the viewpoint of leveling and dye dispersibility, the compounding amount of the compound (A) is preferably 50 to 70 parts by mass.

  Compound (B) is at least one selected from dibenzyl ether and benzyl benzoate. The compound (B) is presumed to have a role of mainly causing leveling by swelling the polyester fiber and allowing the disperse dye to penetrate into the fiber in the dyeing step. The action by the compound (B) is not limited to these. From the viewpoint of leveling properties, the compound (B) is preferably dibenzyl ether.

  The compounding quantity of the compound (B) in the dyeing assistant of this invention is 5-30 mass parts with respect to a total of 100 mass parts of compounds (A), (B), (C), and (D). If the compounding amount of the compound (B) is less than 5 parts by mass, the leveling property may be lowered and uniform dyeing may not be obtained. On the other hand, when the compounding amount of the compound (B) exceeds 30 parts by mass, the residue on the dyed product increases, which may reduce the light fastness of the dyed product. From the viewpoint of leveling and light fastness of the dyed product obtained, the compounding amount of the compound (B) is more preferably 10 to 25 parts by mass.

In the general formula (II), k and l are each independently an integer of 1 to 5, and when l is 2 or more, a plurality of k may be the same or different. However, the total number of R ¹ in the compound (C) represented by the general formula (II) is an integer of 1 to 5. For example, when l is 1, k may be an integer of 1 to 5, and in this case, the total number of R ¹ in the compound (A) represented by the general formula (I) is an integer of 1 to 5, respectively. . When l is 2 and two k are the same, k may be 1 or 2, in which case the total number of R ¹ in the compound (A) represented by the general formula (I) is 2 or 2 respectively. 4. When l is 2 and two k are different, when one of the two k is 1, the other k may be an integer of 2 to 4, in this case represented by the general formula (I) In the compound (A), the total number of R ¹ is an integer of 3 to 5, respectively. When l is 2 and two k are different, when one k of two is 2, the other k may be 1 or 3, in which case the compound represented by the general formula (I) The total number of R ¹ in (A) is 3 or 5, respectively. If l is 3 or more, it is analogized.

In the general formula (II), R ¹ is a styrene group (phenylethylene group). The styrenated phenol that is a raw material of the compound (C) represented by the general formula (II) may be a mixture of compounds having different styrene addition moles per mole of phenol. Such mixtures are expressed by the average added moles of styrene per mole of phenol. For example, when the average added mole number of styrene per mole of phenol in the mixture is 3, it is expressed as tristyrenated phenol. In the present invention, as the compound (C) represented by the general formula (II), a mixture of compounds (C) having different addition mole numbers may be used. In this case, the average value of the total number of individual R ¹ in the compound (C) represented by the general formula (II) contained in the mixture (that is, the average number of added moles of styrene with respect to 1 mole of phenol in the mixture) is 1 to 5 Any integer of. In this case, if the average value of the total number of R ¹ in the compound (C) represented by the general formula (II) contained in this mixture is an integer of 1 to 5, it is represented by the individual general formula (II). The total number of R ¹ in the compound (C) may be 6 or more. Moreover, the mixture as the compound (C) represented by the general formula (II) is represented by the average added mole number of styrene. For example, if the average value of the total number of R ¹ in the compound (C) represented by the general formula (II) (that is, the average addition mole number of styrene) is 3, the ethylene oxide 16 mol addition product of styrenated phenol , Expressed as a tristyrenated phenol ethylene oxide 16 mole adduct.

  In the general formula (II), EO represents an ethyleneoxy group. n shows the average addition mole number of EO, and is 8-20. If n is less than 8, the solubility in water decreases, and the components may be separated. On the other hand, if n exceeds 20, the leveling property is lowered and the leveling effect on the fibers may not be obtained. From the viewpoint of the stability and levelness of the dyeing assistant, n is preferably 10-18.

  The compound (C) represented by the general formula (II) mainly has an action of emulsifying and dispersing the compound (B), and improves the scourability of unscoured or insufficiently scoured fibers and disperse dye fibers. It is presumed that it also has an improvement in leveling. The effect | action by a compound (C) is not limited to these.

  The synthesis of compound (C) can be obtained by a conventionally known method. For example, compound (C) can be obtained by adding a predetermined amount of ethylene oxide to tristyrenated phenol at 120 to 170 ° C. under pressure using an alkali catalyst such as sodium hydroxide or potassium hydroxide. it can.

  The compounding amount of the compound (C) in the dyeing assistant of the present invention is 5 to 25 parts by mass with respect to 100 parts by mass in total of the compounds (A), (B), (C) and (D). If the compounding amount of the compound (C) is less than 5 parts by mass, it may not be possible to cope with unscoured or insufficiently refined fibers. On the other hand, when the compounding amount of the compound (C) exceeds 25 parts by mass, the foam-suppressing property in the dyeing process is lowered, which may hinder the operation. From the viewpoint of scourability and foam suppression in the dyeing step, the compound (C) content is preferably 10 to 20 parts by mass.

In general formula (III), w and x are each independently an integer of 1 to 5, and when x is 2 or more, a plurality of ws may be the same or different. However, the total number of R ¹ in the compound (D) represented by the general formula (III) is an integer of 1 to 5. For example, when x is 1, w may be an integer of 1 to 5. In this case, the total number of R ¹ in the compound (A) represented by the general formula (I) is an integer of 1 to 5, respectively. . When x is 2 and two w are the same, w may be 1 or 2, and in this case, the total number of R ¹ in the compound (A) represented by the general formula (I) is 2 or 2 respectively. 4. When x is 2 and two w are different, when one of the two is 1, the other w may be an integer of 2 to 4, in this case, represented by the general formula (I) In the compound (A), the total number of R ¹ is an integer of 3 to 5, respectively. When x is 2 and two w are different, when one of the two is 2, the other w may be 1 or 3, in which case the compound represented by the general formula (I) The total number of R ¹ in (A) is 3 or 5, respectively. When x is 3 or more, it is analogized.

In the general formula (III), R ¹ is a styrene group (phenylethylene group). The styrenated phenol that is a raw material of the compound (D) represented by the general formula (III) may be a mixture of compounds having different styrene addition moles per mole of phenol. Such mixtures are expressed by the average added moles of styrene per mole of phenol. For example, when the average added mole number of styrene per mole of phenol in the mixture is 3, it is expressed as tristyrenated phenol. In the present invention, as the compound (D) represented by the general formula (III), a mixture of compounds (D) having different addition mole numbers may be used. In this case, the average value of the total number of individual R ¹ in the compound (D) represented by the general formula (III) contained in the mixture (that is, the average number of added moles of styrene with respect to 1 mole of phenol in the mixture) is 1 to 5 Any integer of. In this case, if the average value of the total number of R ¹ in the compound (D) represented by the general formula (III) contained in this mixture is an integer of 1 to 5, it is represented by each general formula (III) The total number of R ¹ in the compound (D) may be 6 or more. Moreover, the mixture as the compound (D) represented by the general formula (III) is represented by the average added mole number of styrene. For example, propylene oxide 12 mol ethylene oxide 4 mol addition of styrenated phenol whose average value of the total number of R ¹ in the compound (D) represented by the general formula (III) (that is, the average addition mol number of styrene) is 3. If it is a product sulfate ammonium salt, it is expressed as tristyrenated phenol propylene oxide 12 mol ethylene oxide 4 mol adduct sulfate ammonium salt.

  In the general formula (III), PO represents a propyleneoxy group. y shows the average addition mole number of PO, and is 0-15. If y increases, foam suppression tends to be improved in the dyeing process. However, if y exceeds 15, the dispersibility of the dye in the dyeing bath may be reduced, which may lead to dyeing troubles such as tarling stains due to aggregation. is there. From the viewpoint of dye dispersibility and foam suppression in the dyeing step, y is preferably 6 to 13.

  In the general formula (III), EO represents an ethyleneoxy group. z shows the average addition mole number of EO, and is 2-14. When z is less than 2, the dispersibility of the dye in the dyeing bath is lowered, and there is a possibility that it may lead to dyeing troubles such as taring dirt due to aggregation. On the other hand, if z exceeds 14, foam suppression in the dyeing process is lowered, and there is a risk of hindering operation. From the viewpoint of dye dispersibility and foam suppression in the dyeing step, z is preferably 3 to 11.

  In general formula (III), the addition form of PO and EO in [] is block addition or random addition. From the viewpoint of dye dispersibility and ease of production, the addition form is preferably a block addition, and particularly preferably an addition form in the order of PO block-EO block. Such a compound can be obtained, for example, by block addition of PO to styrenated phenol, followed by block addition of EO and sulfation.

In the general formula (III), M represents a monovalent cation. Examples of M include H ⁺ , alkali metal cation, ammonium ion (NH ₄ ⁺ ), monovalent cation of organic amine, and quaternary ammonium cation. Examples of the alkali metal cation include K ⁺ , Na ⁺ and Li ⁺ , and examples of the organic amine cation include primary, secondary and tertiary alkyl groups having 1 to 12 carbon atoms and / or hydroxy having 2 to 4 carbon atoms. Examples include monovalent cations of organic amines having substituents such as alkyl groups (for example, diethylamine, triethylamine, monoethanolamine, diethanolamine, and triethanolamine). Examples of quaternary ammonium cations include, for example, 1 to 12 carbon atoms. And tetraalkylammonium having an alkyl group. Further, M includes, for example, alkaline earth metal cations such as Ca ^{1/2 +} and Mg ^{1/2 +} . From the viewpoint of the stability of the dyeing aid, M is preferably K ⁺ , Na ⁺ or NH ₄ ⁺ , and more preferably NH ₄ ⁺ .

  The compound (D) represented by the general formula (III) has an action of emulsifying and dispersing the compound (B), and mainly has an action of imparting foam suppression in the dyeing process, and into the dyeing bath of the disperse dye. It is presumed that it also has a dispersing action. The action by the compound (D) is not limited to these.

  The synthesis of compound (D) can be obtained by a conventionally known method. For example, an alkali catalyst such as sodium hydroxide or potassium hydroxide is added to tristyrenated phenol, a predetermined amount of propylene oxide is added at 120 to 170 ° C. under pressure, then ethylene oxide is added, sulfuric acid, The compound (D) is obtained by sulfating with a sulfating agent such as sulfuric anhydride, chlorosulfonic acid or sulfamic acid, and neutralizing with an alkaline agent such as aqueous ammonia, sodium hydroxide or potassium hydroxide as necessary. be able to.

  The compounding amount of the compound (D) in the dyeing assistant of the present invention is 1 to 25 parts by mass with respect to 100 parts by mass in total of the compounds (A), (B), (C) and (D). If the compounding amount of the compound (D) is less than 1 part by mass, the foam-suppressing property in the dyeing process is lowered, and the operation may be hindered. On the other hand, when the compounding amount of the compound (D) exceeds 25 parts by mass, the leveling property is lowered and the leveling effect on the fibers may not be obtained. From the viewpoint of foam suppression and leveling in the dyeing step, the compounding amount of the compound (D) is preferably 2 to 20 parts by mass.

  The dyeing aid of the present invention has foam suppression and decoloring resistance compared to conventional dyeing aids, and is excellent in dye dispersibility, scouring and leveling properties, thereby being excellent in light fastness, A uniformly dyed product can be obtained. This is presumed to be a result of using a combination of predetermined compounds (A), (B), (C) and (D) contained in the dyeing aid of the present invention in a predetermined blending amount. In particular, regarding the light fastness, the present inventors infer as follows. The conventional dyeing aid for polyester fibers in which the compound (B) is blended needs to blend the compound (B) in a large amount (with a high blending amount) in order to obtain sufficient leveling. For this reason, the compound (B) tends to remain in the dyed product, thereby causing a problem that the light fastness of the dyed product is greatly reduced. However, by using a predetermined compounding amount of a combination of the predetermined compounds (A), (B), (C) and (D) in the dyeing assistant of the present invention, the compound is maintained while maintaining sufficient leveling. It is presumed that the blending amount of (B) can be reduced, and as a result, the residue of the compound (B) in the dyed product is reduced and the light fastness of the dyed product can be improved.

  In the dyeing aid for polyester fibers of the present invention, the compounds (A) to (D) may be contained in one agent, or may be contained in a plurality of agents. From the viewpoint of convenience during use, one agent is preferable.

  The polyester fiber dyeing assistant of the present invention may be a compound or a mixture containing no solvent, or may be a solvent dispersion dispersed in a solvent such as water. The dyeing aid of the present invention is particularly preferably an aqueous dispersion dispersed in water. In this case, water can lower the viscosity of the dyeing assistant and improve the handling property and the developability in the dyeing bath. In the aqueous dispersion, when the total mass of the dyeing aid of the present invention is 100% by mass, the total amount of the compounds (A), (B), (C) and (D) is the stability and handling of the dyeing aid. From the viewpoint of properties and the like, the content is preferably 5% by mass to 80% by mass.

  In order to lower the viscosity of the dyeing assistant and further improve the handling properties, a solvent such as an organic solvent may be added to the aqueous dispersion. In this case, an organic solvent having an antifreezing effect particularly during low-temperature storage is preferable. Although it does not specifically limit as an organic solvent, Diethylene glycol mono n-butyl ether, isopropyl alcohol, methanol, butyl cellosolve, benzyl alcohol, etc. are mentioned, Diethylene glycol mono n-butyl ether is preferable. The addition amount of the organic solvent is preferably 20% by mass or less when the total mass of the dyeing assistant of the present invention is 100% by mass.

  When the dyeing assistant is not a solvent dispersion, it is preferably dispersed in a solvent such as water in advance when it is added to the dyeing bath in order to improve developability in the dyeing bath.

  The dyeing aid for polyester fibers of the present invention is a nonionic surfactant other than compounds (A) and (C), or other than compound (D) for the purpose of improving long-term stability and dye dispersibility in a dyeing bath. The anionic surfactant may be included. In addition, as necessary, antioxidants such as phenolic compounds and benzotriazole compounds, solubilizers such as aromatic sulfonic acid compounds, antifoaming agents, ultraviolet absorbers, chelating dispersants, pH adjusters, etc. May be added.

  The method for dyeing polyester fibers of the present invention includes a step of dyeing polyester fibers in the presence of a dyeing aid for polyester fibers. The polyester fiber to be dyed is not particularly limited as long as it contains polyester fiber, but is composed of a single polymer such as ethylene terephthalate, propylene terephthalate, trimethylene terephthalate, and butylene terephthalate, or a copolymer thereof. Examples thereof include polyester fibers, and those obtained by combining these polyester fibers with other synthetic fibers or natural fibers, such as mixed spinning, knitting, knitting, etc. Examples of the form include yarn, knitting, woven fabric, and non-woven fabric. It is preferable that the polyester fiber imparted to the dyeing process is scoured.

  The dyeing process of the present invention is particularly preferably a dyeing method using a disperse dye at a high temperature. Such a dyeing method is not particularly limited, and examples include immersion methods such as liquid dyeing, cheese dyeing, beam dyeing, overmeier dyeing, and high-pressure jet dyeing.

  As the dyeing bath used in the dyeing method of the present invention, in the case of the dipping method, in addition to the dye and the dyeing aid of the present invention, a chelating agent, a pH adjuster, Components such as a foaming agent, an oligomer removing agent, and an anti-wrinkle agent may be included. Further, if necessary, it may contain a function-imparting agent such as a flame retardant, a softening agent, an antistatic agent, a light resistance improver, and a water-absorbing quick-drying agent.

  The dye is not particularly limited as long as it is a dye that can be used as a disperse dye, and examples thereof include benzeneazo dyes, heterocyclic azo dyes, disazo dyes, anthraquinone dyes, quinoline dyes, nitro dyes, coumarin dyes, methine dyes, and aminoketone dyes.

  The addition amount in the dyeing bath can be adjusted in a timely manner according to the purpose such as the color to be dyed and the dyeing concentration in the case of the dipping method. It is preferably 001 g / L to 20 g / L, and the dyeing aid for polyester fibers of the present invention is preferably 0.01 to 5.0 g / L. The dyeing temperature is preferably 90 to 150 ° C., and the dyeing bath ratio is preferably 1: 1 to 1:50. With these dyeing conditions, the effects of the present invention can be obtained.

  The dyeing assistant of the present invention is usually used in the dyeing treatment, but can also be used in the same bath treatment of scouring and dyeing.

  The manufacturing method of the dyeing | staining thing of this invention includes the process of preparing a polyester fiber, and the process of dye | staining a polyester fiber in presence of the dyeing aid for polyester fibers of this invention. The polyester fiber and the dyeing process are as described above. In the present specification, the “dyed product” refers to a dyed product such as a dyed polyester fiber.

  In the method for producing a dyed product of the present invention, a scouring step is preferably performed before the dyeing step. There are no particular restrictions on the scouring process, for example, nonionic surfactants such as polyoxyalkylene alkyl ethers and polyoxyalkylene alkyl allyl ethers, or nonionic surfactants and alkylbenzene sulfonates, aliphatic alcohol sulfates, etc. Using a scouring agent such as a blend with an anionic surfactant, a refining method such as a batch system using a winch or a liquid dyeing machine or a continuous system using a continuous scouring apparatus can be used. Further, the scouring step and the dyeing step can be performed by the same bath treatment.

  EXAMPLES The present invention will be further described below with reference to examples, but the present invention is not limited to these examples.

Synthesis Example 1 Synthesis of Compound (A) Represented by General Formula (I) A four-necked flask equipped with a thermometer, a condenser tube, and a stirrer was charged with 47 g of phenol and 0.5 g of concentrated sulfuric acid having a purity of 98%, Heating with stirring under a nitrogen gas stream, adding 156 g of styrene dropwise over about 30 minutes at 120-130 ° C. and adding for about 3 hours, then pressurizing the resulting tristyrenated phenol It moved to the reaction apparatus, 0.5 g of sodium hydroxide was added, 352 g of ethylene oxide was dripped over about 3 hours at 160-170 degreeC, and it was made to add by ageing | curing | ripening for about 1 hour, and the fine brown oily substance was obtained. Further, 500 g of the obtained adduct was transferred to a four-necked flask equipped with a thermometer, a condenser, and a stirrer, charged with 127 g of oleic acid, heated with stirring in a nitrogen gas stream, and about 4 at 190 to 200 ° C. By reacting for a period of time, 619 g of tristyrenated phenol ethylene oxide 16 mol adduct oleate was obtained.

  In addition, only the addition amount of ethylene oxide was changed, and tristyrenated phenol ethylene oxide 12 mol adduct oleic acid ester, tristyrenated phenol ethylene oxide 18 mol adduct oleic acid ester, tristyrenated phenol ethylene oxide 14 mol adduct Oleic acid ester and tristyrenated phenol ethylene oxide 24 mol adduct oleic acid ester were also obtained.

Synthesis Example 2 Synthesis of Compound (C) Represented by General Formula (II) A four-necked flask equipped with a thermometer, a condenser tube, and a stirrer was charged with 0.5 g of concentrated sulfuric acid having a purity of 47 g of phenol and nitrogen. Heat with stirring in a gas stream, add 156 g of styrene dropwise at about 120-130 ° C. over about 30 minutes and react for about 3 hours, then pressurize the resulting tristyrenated phenol Transfer to apparatus, 0.5 g of sodium hydroxide is added, 352 g of ethylene oxide is added dropwise at 160-170 ° C. over about 3 hours and aged for about 1 hour to add 556 g of tristyrenated phenol ethylene oxide 16 A molar adduct was obtained.

  Further, only the addition amount of ethylene oxide was changed, and a tristyrenated phenol ethylene oxide 12 mol adduct, a tristyrenated phenol ethylene oxide 14 mol adduct, a tristyrenated phenol ethylene oxide 20 mol adduct, and a tristyrenated product. A phenol ethylene oxide 24 mole adduct was also obtained.

Synthesis Example 3 Synthesis of Compound (D) Represented by General Formula (III) A four-necked flask equipped with a thermometer, a condenser tube, and a stirring device was charged with 47 g of phenol and 0.5 g of concentrated sulfuric acid having a purity of 98%, Heating with stirring under a nitrogen gas stream, adding 156 g of styrene dropwise over about 30 minutes at 120-130 ° C. and adding for about 3 hours, then pressurizing the resulting tristyrenated phenol Transfer to a reactor, add 0.5 g of sodium hydroxide, add 261 g of propylene oxide at 120-130 ° C. over about 5 hours, and then add 66 g of ethylene oxide at 160-170 ° C. over about 3 hours. It was added dropwise by aging for about 1 hour to obtain a light brown oily substance. This fine brown oily substance is neutralized, dehydrated and filtered, transferred to another four-necked flask and transferred to 500 g, gradually added dropwise 55 g of chlorosulfonic acid over about 4 hours at 40 ° C. or lower, and then introduced with nitrogen gas. Then, dehydrochlorination was carried out for about 4 hours, and the obtained sulfate was neutralized with 25% aqueous ammonia to obtain 581 g of tristyrenated phenol propylene oxide 9 mol ethylene oxide 3 mol adduct sulfate ammonium salt.

  Also, only the addition amount of propylene oxide and ethylene oxide was changed, tristyrenated phenol ethylene oxide 8 mol adduct sulfate ammonium salt, tristyrenated phenol propylene oxide 12 mol ethylene oxide 4 mol adduct sulfate ammonium salt, and Further, an 18 mol adduct adduct sulfate ammonium salt of tristyrenated phenol propylene oxide was also obtained. Furthermore, using sodium hydroxide instead of 25% aqueous ammonia as a neutralizing agent, tristyrenated phenol propylene oxide 9 mol ethylene oxide 3 mol adduct sulfate sodium salt was also obtained.

Example 1
60 parts by mass of tristyrenated phenol ethylene oxide 16-mol adduct obtained in Synthesis Example 1 and 16 parts by mass of dibenzyl ether, and 16 mol of tristyrenated phenol ethylene oxide obtained in Synthesis Example 2 14 parts by mass, 9 parts by mass of tristyrenated phenolpropylene oxide 9 mol ethylene oxide 3 mol adduct sulfate ester ammonium salt obtained in Synthesis Example 3, 10 parts by mass of diethylene glycol mono n-butyl ether, and 20 parts by mass of water Thus, the dyeing assistant of Example 1 was obtained.

Example 2
66 parts by mass of tristyrenated phenol ethylene oxide 16 mol adduct obtained in Synthesis Example 1 and 16 parts by mass of dibenzyl ether, 16 mol adduct of tristyrenated phenol ethylene oxide obtained in Synthesis Example 2 14 parts by mass, 4 parts by mass of tristyrenated phenolpropylene oxide 9 mol ethylene oxide 3 mol adduct sulfate ammonium salt obtained in Synthesis Example 3, 10 parts by mass of diethylene glycol mono n-butyl ether, and 20 parts by mass of water Thus, the dyeing assistant of Example 2 was obtained.

Example 3
Tristyrene obtained by changing the addition amount of ethylene oxide in Synthesis Example 1 and 52 parts by mass of oleic acid ester of 18 mol adduct of tristyrenated phenol ethylene oxide, 24 parts by mass of dibenzyl ether, and tristyrene obtained in Synthesis Example 2 14 parts by mass of a 16 mol of phenolic ethylene oxide adduct, and a tristyrenated phenol propylene oxide 12 mol ethylene oxide 4 mol adduct sulfate ammonium salt obtained by changing the addition amount of propylene oxide and ethylene oxide in Synthesis Example 3 10 parts by weight, 10 parts by weight of butycellosolve, and 20 parts by weight of water were mixed to obtain a dyeing assistant of Example 3.

Example 4
60 parts by mass of tristyrenated phenol ethylene oxide 16-mol adduct oleic acid ester obtained in Synthesis Example 1 and 8 parts by mass of dibenzyl ether, and tristyrene obtained by changing only the addition amount of ethylene oxide in Synthesis Example 2 14 parts by mass of adduct of 14 mol of phenolic ethylene oxide, 9 mol of tristyrenated phenolpropylene oxide obtained by using sodium hydroxide instead of 25% aqueous ammonia as a neutralizing agent in Synthesis Example 3 3 mol of ethylene oxide 18 parts by mass of adduct sulfate sodium salt, 10 parts by mass of diethylene glycol mono n-butyl ether, and 20 parts by mass of water were mixed to obtain a dyeing assistant of Example 4.

Example 5
60 parts by mass of tristyrenated phenol ethylene oxide 16 mol adduct obtained in Synthesis Example 1 and 24 parts by mass of dibenzyl ether, 16 mol adduct of tristyrenated phenol ethylene oxide obtained in Synthesis Example 2 6 parts by mass, 9 parts by mass of tristyrenated phenol propylene oxide 9 mol ethylene oxide 3 mol adduct sulfate ester ammonium salt obtained in Synthesis Example 3, 10 parts by mass of diethylene glycol mono n-butyl ether, and 20 parts by mass of water Thus, the dyeing assistant of Example 5 was obtained.

Example 6
60 parts by mass of oleic acid ester of tristyrenated phenol ethylene oxide 14 mol adduct obtained by changing only the addition amount of ethylene oxide in Synthesis Example 1, 16 parts by mass of benzyl benzoate, and addition amount of ethylene oxide in Synthesis Example 2 14 parts by weight of a tristyrenated phenol ethylene oxide 20 mol adduct obtained by changing only 10 parts by mass of a tristyrenated phenol propylene oxide 9 mol ethylene oxide 3 mol adduct sulfate ammonium salt obtained in Synthesis Example 3. Then, 10 parts by mass of diethylene glycol mono n-butyl ether and 20 parts by mass of water were mixed to obtain a dyeing assistant of Example 6.

Example 7
60 parts by mass of oleic acid ester obtained by changing the addition amount of ethylene oxide in Synthesis Example 1 and 12 moles of adduct of tristyrenated phenol ethylene oxide, 16 parts by mass of dibenzyl ether, and addition amount of ethylene oxide in Synthesis Example 2 14 parts by mass of a 12 mol adduct of tristyrenated phenol ethylene oxide obtained by changing only 10 parts by mass of an ammonium sulfate ester 9 mol of tristyrenated phenol propylene oxide obtained in Synthesis Example 3 Then, 10 parts by mass of diethylene glycol mono n-butyl ether and 20 parts by mass of water were mixed to obtain a dyeing assistant of Example 7.

Example 8
60 parts by mass of tristyrenated phenol ethylene oxide 16-mol adduct obtained in Synthesis Example 1 and 16 parts by mass of dibenzyl ether, and 16 mol of tristyrenated phenol ethylene oxide obtained in Synthesis Example 2 14 parts by mass, 10 parts by mass of tristyrenated phenol ethylene oxide 8 mol adduct sulfate ammonium salt obtained by changing only the addition amount of propylene oxide and ethylene oxide in Synthesis Example 3, and 10 parts by mass of diethylene glycol mono n-butyl ether 20 parts by mass of water were mixed to obtain the dyeing aid of Example 8.

Comparative Example 1
24 parts by mass of tristyrenated phenol ethylene oxide 16-mol adduct obtained in Synthesis Example 1 and 48 parts by mass of dibenzyl ether, and 16 mol of tristyrenated phenol ethylene oxide obtained in Synthesis Example 2 14 parts by mass, tristyrenated phenol propylene oxide 9 mol ethylene oxide 3 mol adduct sulfate ester ammonium salt obtained in Synthesis Example 3 14 parts by mass, diethylene glycol mono n-butyl ether 10 parts by mass, water 20 parts by mass Thus, the dyeing assistant of Comparative Example 1 was obtained.

Comparative Example 2
66 parts by mass of tristyrenated phenol ethylene oxide 16-mol adduct oleate obtained in Synthesis Example 1 and 24 mol of tristyrenated phenol ethylene oxide obtained by changing only the addition amount of ethylene oxide in Synthesis Example 2 20 parts by mass, tristyrenated phenol propylene oxide 9 mol ethylene oxide 3 mol adduct sulfate ammonium salt obtained in Synthesis Example 3 14 parts by mass, diethylene glycol mono n-butyl ether 10 parts by mass, water 20 parts by mass Thus, the dyeing assistant of Comparative Example 2 was obtained.

Comparative Example 3
66 parts by mass of tristyrenated phenol ethylene oxide 24 mol adduct oleic acid ester obtained by changing only the addition amount of ethylene oxide in Synthesis Example 1, 18 parts by mass of dibenzyl ether, tristyrene obtained in Synthesis Example 2 16 parts by mass of adduct of 16 mol of phenol ethylene oxide, 10 parts by mass of diethylene glycol mono-n-butyl ether, and 20 parts by mass of water were mixed to obtain a dyeing aid of Comparative Example 3.

Comparative Example 4
66 parts by mass of the tristyrenated phenol ethylene oxide 16-mol adduct oleate obtained in Synthesis Example 1 and 18 parts by mass of dibenzyl ether, and in Synthesis Example 3 only by changing the addition amount of propylene oxide and ethylene oxide 16 parts by weight of the obtained tristyrenated phenolpropylene oxide 18 mol adduct sulfate ammonium salt was mixed with 10 parts by weight of diethylene glycol mono n-butyl ether and 20 parts by weight of water to obtain a dyeing assistant of Comparative Example 4.

Comparative Example 5
60 parts by mass of polyethylene glycol dioleate esterified with oleic acid and 16 parts of dibenzyl ether by using commercially available polyethylene glycol having a molecular weight of 600 instead of the tristyrenated phenol ethylene oxide adduct in Synthesis Example 1. 14 parts by mass of tristyrenated phenol ethylene oxide 16 mol adduct obtained in Synthesis Example 2 and 14 parts by mass of tristyrenated phenol propylene oxide 9 mol ethylene oxide 3 mol adduct sulfate ammonium salt obtained in Synthesis Example 3 10 parts by mass, 10 parts by mass of diethylene glycol mono n-butyl ether and 20 parts by mass of water were mixed to obtain a dyeing assistant of Comparative Example 5.

  The performance evaluation of the dyeing assistants prepared in Examples 1 to 8 and Comparative Examples 1 to 5 was performed by the following method. The evaluation results are shown in Table 1.

<Dye dispersibility>
The following dyeing solution is charged into a pot of a color pet (manufactured by Nippon Dyeing Machinery Co., Ltd.), heated to 130 ° C. at 3 ° C./min without putting cloth, held at that temperature for 30 minutes, and then cooled to 80 ° C. The dye liquor was filtered, and the amount of dye aggregate remaining on the filter paper was visually determined in the following four stages.

Dye solution composition Disperse dye: C.I. I. Disperse Red 167 1g / L
Dyeing assistant: 0.5g / L
80% acetic acid: 0.3 g / L

Criteria A: Dye aggregates are not seen at all, very good B: Dye aggregates are hardly seen, good C: Dye aggregates are seen a little, slightly inferior D: Dye aggregates are seen a lot, Inferior

<Scourability>
About 0.3 ml of mineral oil [Diana Fresia S-32] (manufactured by Idemitsu Kosan Co., Ltd.) is dropped on a polyester knit cloth that has been subjected to scouring in advance, and then dried at 120 ° C. for 1 minute. Then, dyeing was performed under the following dyeing conditions with a mini-color dyeing machine (manufactured by Teksam Giken), and the state of oil dripping marks on the obtained cloth to be dyed was visually determined in the following four stages.

Dyeing conditions Disperse dye: C.I. I. Disperse Blue 79 0.05g / L
Dyeing assistant: 0.5g / L
80% acetic acid: 0.3 g / L
Dyeing temperature: 130 ° C. × 30 minutes Temperature increase rate: 2 ° C./minute Bath ratio: 1:20

Criteria A: No trace of oil dripping observed, very good B: Almost no trace of oil dripping observed, good C: Some trace of oil dripping observed, slightly inferior D: Clear trace of oil dripping observed Inferior

<Uniformity>
Using a mini-color dyeing machine (manufactured by Teksam Giken), dyeing was performed under the following dyeing conditions, and the leveling state of the obtained fabric to be dyed was visually determined in the following four stages.

Dyeing conditions Test cloth: High density polyester taffeta Disperse dye: C.I. I. Disperse Red 167 0.07g / L
C. I. Disperse Orange 30 0.07g / L
C. I. Disperse Blue 79 0.07g / L

Dyeing assistant: 0.5g / L
80% acetic acid: 0.3 g / L
Dyeing temperature: 130 ° C. × 30 minutes Temperature increase rate: 2 ° C./minute Bath ratio: 1:15

Judgment criteria A: No staining spots are observed, very good B: Almost no staining spots are observed, good C: Some staining spots are observed, and slightly inferior D: Many staining spots are observed, and inferior

<Light fastness>
Using a UV fade meter (manufactured by Suga Test Instruments Co., Ltd.), the fabric to be dyed obtained in the above evaluation of <leveling property> was irradiated with UV rays at 63 ° C. for 20 hours, and then visually observed for fading. Judgment was made in the following four stages.

Criteria A: No fading, very good B: Little fading, good C: Some fading, slightly inferior D: Many fading is seen, inferior

<Decoloration resistance>
In general, dyeing assistants that are inferior in stability over time in a dyeing bath will lose their function as a dyeing aid if they stay in the hot dyeing bath for a long time. Cause a decrease in color density of the dyed product obtained. This phenomenon is called decolorization, and excellent decoloration resistance in the present invention means that the color density of the dyed product is hardly lowered. In the present invention, evaluation was performed as follows.

  Using a mini-color dyeing machine (manufactured by Teksam Giken), perform the operation once without inserting the cloth under the following dyeing conditions, cool the dyeing solution to 80 ° C over 15 minutes, insert the cloth, and repeat the operation. went. The color density reduction of the obtained fabric to be dyed was visually compared with a blank (tested without adding a dyeing aid), and judged in the following four stages.

Dyeing conditions Specimen cloth: Polyester knit cloth that has been scoured beforehand Disperse dye: I. Disperse Blue 79 0.07g / L
Dyeing assistant: 0.5g / L
80% acetic acid: 0.3 g / L
Dyeing temperature: 130 ° C. × 30 minutes Temperature increase rate: 2 ° C./minute Bath ratio: 1:15

Criteria A. No decrease in density, very good decoloring resistance B: Almost no decrease in density, good decoloring resistance C: Slight decrease in density, slightly decoloration resistance D: Degradation in density Many are seen and inferior in decoloration resistance

<Foam suppression test>
Take 300 mL of the following measuring solution into a 1 L graduated cylinder (diameter 75 mm), put a ball filter to the bottom of the graduated cylinder, blow air at 30 ° C. at a rate of 1 L / min from an air pump, and immediately after stopping blowing. The bubble height (unit: mm) after 10 seconds and the time (unit: seconds) until the liquid level started to be observed were measured.

Measuring solution Dyeing assistant: 2g / L
80% acetic acid: 0.3 g / L

  As can be seen from the performance evaluation results shown in Table 1, Examples 1 to 8 show good results in any of the performances of dye dispersibility, scouring properties, leveling resistance, light fastness, decoloration resistance and foam suppression. Indicated. On the other hand, Comparative Examples 1-5 showed an unfavorable result in at least one item.

  In Comparative Example 1, since the compounding amount of the compound (A) is too small, the leveling and antifoaming properties are lowered, and since the compounding amount of the compound (B) is excessive, the light fastness cannot be obtained. It is speculated that there was.

  In Comparative Example 2, the compound (B) was not blended, and the amount of ethylene oxide added to the compound (C) was excessive, so that it was estimated that leveling was not obtained and the scourability was reduced. The Moreover, since there are many compounding quantities of a compound (C), it is estimated that it was the result that foam suppression property fell a little.

  In Comparative Example 3, since the amount of addition of ethylene oxide in the compound (A) is excessive, it is presumed that the leveling property was deteriorated despite the addition. Moreover, since the compound (D) is not blended, it is presumed that the dye dispersibility was not obtained.

  In Comparative Example 4, since compound (C) was not blended, scourability was not obtained, and because the amount of alkylene oxide added to compound (D) was in an unfavorable range, dye dispersibility was not obtained. Guessed.

  In Comparative Example 5, since the compound (A) was changed to a component other than the present invention, the decoloring resistance was not obtained, and it was presumed that other items were also in a decreasing tendency.

According to the refining aid for polyester fibers of the present invention and the method for dyeing polyester fibers using the same, particularly when dyeing unrefined or insufficiently refined polyester fibers using a disperse dye at high temperature, A high-quality dyed product that is excellent in light fastness and uniformly dyed can be stably obtained. Furthermore, simplification of the scouring process in the processing of the high-density material and the same bath treatment for scouring dyeing are possible, and the processing cost can be reduced and the productivity can be improved.

Claims (3)

Compound (A) represented by the following general formula (I),
At least one compound (B) selected from dibenzyl ether and benzyl benzoate;
Compound (C) represented by the following general formula (II), and compound (D) represented by the following general formula (III)
The compound (A) is 40 to 80 parts by mass, the compound (B) is 5 to 30 parts by mass with respect to a total of 100 parts by mass of the compounds (A), (B), (C) and (D). A dyeing aid for polyester fibers, comprising 5 to 25 parts by mass of the compound (C) and 1 to 25 parts by mass of the compound (D).


(In the formula, R ¹ represents a divalent group represented by the following formula (i). A and b are each independently an integer of 1 to 5, and when b is 2 or more, a plurality of a are the same. However, the total number of R ¹ in the compound (A) represented by the general formula (I) is an integer of 1 to 5. EO represents an ethyleneoxy group, and c is EO. The average added mole number is 8 to 22. R ² is a hydrocarbon group having 7 to 21 carbon atoms.




(Wherein, R ¹ is the general formula (.k and l are the same as R ¹ in I) are each independently an integer of 1 to 5, and when l is 2 or more, a plurality of k are the same However, the total number of R ¹ in the compound (C) represented by the general formula (II) is an integer of 1 to 5. EO represents an ethyleneoxy group, and n is an average addition of EO. The number of moles is 8 to 20.)


(Wherein, R ¹ is the same as R ¹ in the general formula (I) .w and x are each independently an integer of 1 to 5, when x is 2 or more, a plurality of w is the same However, the total number of R ¹ in the compound (D) represented by the general formula (III) is an integer of 1 to 5. PO represents a propyleneoxy group, and y represents an average addition of PO. The number of moles is 0 to 15. EO represents an ethyleneoxy group, z represents the average number of moles of EO added, and is 2 to 14. The addition form of PO and EO in [] is a block addition or (R is random addition. M represents a monovalent cation.)   A method for dyeing polyester fibers, comprising a step of dyeing polyester fibers in the presence of the dyeing aid for polyester fibers according to claim 1. Preparing a polyester fiber;
A process for dyeing polyester fibers in the presence of the dyeing aid for polyester fibers according to claim 1.