JP4483476B2 - Disperse dye composition - Google Patents

Description

  The present invention relates to a yellow disperse dye composition for three primary colors and a method for dyeing a hydrophobic fiber material using the same.

The quinoline derivative represented by the following formula (1) is a compound known as the color index generic name Disperse Yellow 79. The 1,3-indandione derivative represented by the following formula (2) is a compound known as the color index generic name Disperse Yellow 54. Furthermore, the monobrominated product of the 1,3-indandione derivative represented by the following formula (3) is a compound known as the color index generic name Disperse Yellow 64. The dibrominated product of the 1,3-indandione derivative represented by the following formula (4) and the dibrominated product of the 1,3-indandione derivative represented by the following formula (5) are composed of an indigo dye. It is a known compound used for dyeing cotton yarn for denim as a product (see Patent Document 1 below).
On the other hand, it is also known to use a quinoline derivative represented by the formula (1) and a monobrominated product of a 1,3-indandione derivative represented by the formula (3) having good light fastness (described below). (See Patent Document 2).

Japanese Patent Laid-Open No. 2-170861 [Refer to Example 1 and Example 3] JP 11-269402 A [Refer to Example 1 and Example 2]

  However, the dibrominated product (4) of the 1,3-indandione derivative and the dibrominated product (5) of the 1,3-indandione derivative described in Patent Document 1 are both indigo dyes. It is used for dyeing cotton yarn for denim as a composition.

The above-described quinoline derivative (1) has a relatively good dyeing property when dyeing a hydrophobic fiber material as a disperse dye, and can be obtained at a low cost. Therefore, if it can be used as a yellow disperse dye for three primary colors, it is economical. From a general point of view.
However, if the quinoline derivative (1) is used in combination with a red disperse dye and / or a blue disperse dye to obtain a dyed product having various hues, the above-described red disperse dye and / or blue disperse dye are used together. Compared to the speed, the dyeing speed of the quinoline derivative (1) was extremely slow (that is, the compatibility was poor), and it was difficult to uniformly dye the hydrophobic fiber material.

  Further, a method for dyeing a hydrophobic fiber material using a quinoline derivative (1) and a monobrominated product (3) of a 1,3-indandione derivative as described in Patent Document 2 is also used. There was a problem that it was difficult to use as a yellow disperse dye for the three primary colors because of its slow wearing speed.

  Furthermore, in recent years, due to rationalization such as speeding up of the spinning speed of polyester and omission of the drawing process, fibers using yarns with inconsistent molecular structure orientation are often used, and conventional polyester fibers are used. The occurrence rate of the occurrence of stained spots, poor reproducibility of dyeing, and the like is higher than that of the case. Also, in the case of new synthetic fibers composed of ultrafine fibers, irregular cross-section yarns, different shrinkage mixed yarns, etc. alone, in combination or in combination, it is generally difficult to dye homogeneously, unlike conventional hydrophobic fiber materials. It is.

Based on the above circumstances, there is a demand for a method for dyeing hydrophobic fiber materials economically and with good reproducibility by using the quinoline derivative (1) in combination with an existing red disperse dye / or blue disperse dye. .
An object of the present invention is to provide a yellow disperse dye composition for three primary colors when a hydrophobic fiber material is dyed in light to medium dark colors.
Another object of the present invention is to provide a method for dyeing a hydrophobic fiber material in light to medium dark colors.

That is, the present invention provides the following (i) to (iii).
(I) Three primary colors comprising a quinoline derivative represented by the following formula (1), a 1,3-indandione derivative represented by the following formula (2), and a bromide of the 1,3-indandione derivative: Yellow disperse dye composition.

（ｉｉ）上記（ｉ）の三原色用黄色分散染料組成物を用いることを特徴とする疎水性繊維材料の染色方法。
（ｉｉｉ）上記（ｉ）の三原色用黄色分散染料組成物に加えて、さらに赤色分散染料及び／又は青色分散染料を用いることを特徴とする疎水性繊維材料の染色方法。

(Ii) A method for dyeing a hydrophobic fiber material, wherein the yellow disperse dye composition for three primary colors (i) is used.
(Iii) A method for dyeing a hydrophobic fiber material, wherein a red disperse dye and / or a blue disperse dye is further used in addition to the yellow disperse dye composition for three primary colors of (i) above.

The yellow disperse dye composition for the three primary colors of the present invention (i) can be used in combination with an existing red disperse dye and / or a blue disperse dye, and the yellow disperse dye composition for the three primary colors is improved in dyeing speed and compatibility. Excellent.
Moreover, according to the dyeing method of the present invention (ii), dyeing reproducibility is excellent, so that a dyed product having no dyeing spots can be obtained.
Furthermore, according to the dyeing method of the present invention (iii), the hydrophobic fiber material can be dyed in a desired color tone.

Hereinafter, the present invention will be described in detail.
In the above (i) and (ii) of the present invention, the brominated product of the 1,3-indandione derivative (2) is any one of the following dibrominated product (4) and dibrominated product (5) and a monobrominated product. It is preferable that it is a mixture with (3).

  The ratio of the total weight of the 1,3-indandione derivative (2), monobromide (3) and dibromide (4) and / or dibromide (5) to the weight of the quinoline derivative (1) is , (30-80): More preferably in the range of (70-20).

In the present invention, the brominated product of the 1,3-indandione derivative (2) is preferably the above-mentioned monobrominated product (3) and any one of the above-described dibrominated product (4) and dibrominated product (5). It is a mixture.
In the present invention, the weight ratio of the monobrominated product (3) and the total of the dibrominated product (4) and / or dibrominated product (5) to the 1,3-indandione derivative (2) is (80 to 20). ): The range of (20-80) is preferable.
In the present invention, the ratio of the total weight of the dibrominated product (4) and / or the dibrominated product (5) to the weight of the monobrominated product (3) is (30 to 0.5): (70 to 99.5). The range of is particularly preferable.

The composition of the present invention (i) is prepared by mixing the quinoline derivative (1), the 1,3-indandione derivative (2), and the brominated product of the 1,3-indandione derivative in a desired ratio. Preferably, it is obtained by treating with a dispersant described later.
Further, the composition of the present invention (i) is prepared by individually treating the quinoline derivative (1), the 1,3-indandione derivative (2), and the brominated product of the 1,3-indandione derivative with a dispersant described later. After the dispersion treatment, it is obtained by mixing the dispersed dye in a predetermined ratio.
Furthermore, the composition of the present invention (i) may be prepared by mixing the disperse dye obtained by the dispersion method in a predetermined ratio in a dyeing bath.

More preferably, the treatment with the dispersant described above is to treat the quinoline derivative (1), 1,3-indandione derivative (2), monobromide (3), dibromide (4) or dibromide (5). For example, in an aqueous medium, using a sand mill or the like in the presence of a dispersant [eg, an anionic surfactant such as a formalin condensate of naphthalene sulfonic acid, a lignin sulfonic acid or a cresol-Shafer acid formalin condensate] be able to. In the dispersion treatment, if necessary, nonionic surfactants such as polyoxyethylene alkyl ethers and polyoxyethylene alkylphenyl ethers may be used in combination.
The dispersion obtained by the dispersion treatment may be used as it is, or the above dispersion may be dried by spray drying or the like and used as powder or granules.

Further, the yellow disperse dye composition for the three primary colors of the present invention (i) comprises a quinoline derivative (1), a 1,3-indandione derivative (2), a monobromide (3), a dibromide (4), and dibromine. The hue may be adjusted by mixing with a disperse dye other than the compound (5), for example, an azobenzene disperse dye or an anthraquinone disperse dye.
Further, the yellow disperse dye composition for the three primary colors of the present invention (i) includes, in addition to the disperse dye for hue adjustment, a dispersant such as the nonionic surfactant, an extender, a pH adjuster, a disperse leveling agent, and a builder. , Dyeing aids, organic solvents having a boiling point of 100 ° C. or higher, resin binders, and the like.

The yellow disperse dye composition for the three primary colors of the present invention (i) can dye (or print) hydrophobic fiber materials such as polyester, triacetate, diacetate and polyamide.
In dyeing the hydrophobic fiber material, a pH adjusting agent, a dispersion leveling agent, or the like was added to the dye bath in which the composition of the present invention (i) was dispersed in an aqueous medium, as necessary. Thereafter, the hydrophobic fiber material is immersed in this dye bath, and in the case of polyester fiber, for example, it is dyed at 100 ° C. or higher (preferably 105 to 140 ° C.) for 15 to 60 minutes under pressure. This dyeing time can be shortened or extended depending on the state of dyeing.

  Further, in dyeing the hydrophobic fiber material using the composition of the present invention (i), for example, dyeing in the state of boiling water in the presence of a carrier such as o-phenylphenol or methylnaphthalene. You can also Furthermore, when padding dyeing a hydrophobic fiber material using the composition of the present invention (i), the dye dispersion prepared by the above-described method is padded on a cloth and then steamed or dried at a temperature of 100 ° C. or higher. Heat treatment can be performed.

In the case of printing, the dye dispersion is kneaded together with an appropriate paste, printed on a cloth, dried, and then subjected to steaming or dry heat treatment. Moreover, it can also be printed by an inkjet system.
Typical examples of the hydrophobic fiber material applied to the dyeing method of the present invention (ii) include polyester fibers obtained by polycondensation of ethylene glycol and terephthalic acid. Moreover, as a polyester fiber applied to the dyeing | staining method of this invention (ii), the polyester fiber obtained by polycondensation of polyols other than ethylene glycol and terephthalic acid is also mentioned. Further, examples of the hydrophobic fiber material applied to the dyeing method of the present invention (ii) include triacetate fiber, diacetate fiber, and polyamide fiber.
Examples of the hydrophobic fiber material applied to the dyeing method of the present invention (ii) also include the above-exemplified blended fibers or unwoven products. Examples of the blended product or union product include the above-exemplified blends or union products of fibers, cellulose fibers other than the above examples, blends with wool or silk, union products, and the like. As the hydrophobic fiber material applied to the dyeing method (including the printing method) of the present invention (ii), a polyester fiber material is particularly preferable.
Moreover, a new synthetic fiber material is also mentioned as a hydrophobic fiber material applied to the dyeing | staining method of this invention (ii). Examples of the new synthetic fiber material include polyester fibers such as polyethylene terephthalate, polybutylene terephthalate, or a polycondensate of terephthalic acid and 1,4-bis- (hydroxymethyl) cyclohexane; polyamide fibers such as nylon And blended products of the above-mentioned polyester fibers and blended products; blended products and blended products of natural fibers such as cotton, silk and wool and the above-mentioned polyester fibers.
Examples of the material exemplified above include yarn, woven fabric, and knitted fabric.

  For example, when the above-mentioned new synthetic fiber is in the form of a yarn, it is a fine denier fiber yarn of 0.3 denier or less, an ultra microfiber yarn of 0.3 denier or less, a modified cross-section yarn, or a different shrinkage. Examples thereof include blended yarn. These yarns may be in the form of filaments, or may be yarns that have been subjected to various processing and modifications such as matte processing yarns containing titanium dioxide and the like.

Examples of red and / or blue disperse dyes used in combination in the dyeing method of the present invention (ii) include monoazo disperse dyes, disazo disperse dyes, benzeneazo series including naphthaleneazo, thiazole azo, benzothiazole azo, pyridine azo, and imidazole azo. Or a dye group such as a heterocyclic azo group such as thiophenazo or anthraquinone group.
In the present invention using the yellow disperse dye composition (i) above, preferred red disperse dyes and blue disperse dyes used in combination include, for example, dyes represented by the following formulas (6) to (14). .

［式中、Ｒ_１はニトロ基を表す。Ｒ_２及びＲ_３は、それぞれ独立に水素原子、ハロゲン原子、ニトロ基、シアノ基、炭素数１〜３のアルコキシ基又は炭素数１〜３のアルキルスルホニル基を表す。Ｒ_４は水素原子、ハロゲン原子、炭素数１〜３のアルキル基、炭素数２〜４のアルキルアミド基又はベンズアミド基を表す。Ｒ_５は水素原子、ハロゲン原子、炭素数１〜３のアルコキシ基又は炭素数２〜４のアルコキシアルコキシ基を表す。
Ｒ_６及びＲ_７は、それぞれ独立に水素原子、炭素数１〜５のアルキル基、炭素数２〜５のアルケニル基、炭素数１〜４のヒドロキシアルキル基、炭素数２〜６のアルコキシアルキル基、炭素数３〜８のアルキルカルボニルオキシアルキル基、炭素数３〜８のアルコキシカルボニルアルキル基、炭素数４〜８のアルコキシアルコキシカルボニルアルキル基、炭素数２〜８のシアノアルキル基、炭素数３〜８のアルコキシカルボニルオキシアルキル基、炭素数８〜１２のフェニルカルボニルオキシアルキル基、フェニル基、炭素数７〜９のフェニルアルキル基又は炭素数７〜９のフェノキシアルキル基等を表す。］

[Wherein R ₁ represents a nitro group. R ₂ and R ₃ each independently represent a hydrogen atom, a halogen atom, a nitro group, a cyano group, an alkoxy group having 1 to 3 carbon atoms, or an alkylsulfonyl group having 1 to 3 carbon atoms. R ₄ represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 3 carbon atoms, an alkylamide group having 2 to 4 carbon atoms, or a benzamide group. R ₅ represents a hydrogen atom, a halogen atom, an alkoxy group having 1 to 3 carbon atoms or an alkoxyalkoxy group having 2 to 4 carbon atoms.
R ₆ and R ₇ are each independently a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, a hydroxyalkyl group having 1 to 4 carbon atoms, or an alkoxyalkyl group having 2 to 6 carbon atoms. C3-C8 alkylcarbonyloxyalkyl group, C3-C8 alkoxycarbonylalkyl group, C4-C8 alkoxyalkoxycarbonylalkyl group, C2-C8 cyanoalkyl group, C3-C3 An alkoxycarbonyloxyalkyl group having 8 carbon atoms, a phenylcarbonyloxyalkyl group having 8 to 12 carbon atoms, a phenyl group, a phenylalkyl group having 7 to 9 carbon atoms, or a phenoxyalkyl group having 7 to 9 carbon atoms. ]

［式中、Ｒ_８は水素原子、ハロゲン原子、ニトロ基又は炭素数１〜３のアルキルスルホニル基を表す。Ｒ_９、Ｒ_１０及びＲ_１１は、それぞれ独立に水素原子又はハロゲン原子を表す。Ｒ_１２は水素原子、炭素数１〜３のアルキル基、炭素数２〜４のアルキルカルボニルアミノ基又はフェニルカルボニルアミノ基を表し、該フェニルカルボニルアミノ基におけるフェニルの水素原子は炭素数１〜５のアルキル基、炭素数１〜５のアルコキシ基及びハロゲン原子からなる群より選ばれる置換基で置換されていてもよい。Ｒ_１３は水素原子又は炭素数１〜３のアルキル基を表す。
Ｒ_１４及びＲ_１５は、それぞれ独立に炭素数１〜５のアルキル基、炭素数２〜５のアルケニル基、炭素数１〜４のヒドロキシアルキル基、炭素数２〜６のアルコキシアルキル基、炭素数３〜７のアルキルカルボニルオキシアルキル基、炭素数４〜８のアルコキシアルコキシカルボニルアルキル基、炭素数３〜８のアルコキシカルボニルアルキル基、炭素数２〜８のシアノアルキル基、炭素数３〜８のアルコキシカルボニルオキシアルキル基、フェニル基、炭素数７〜９のフェニルアルキル基又は炭素数７〜９のフェノキシアルキル基を表す。］

[Wherein R ₈ represents a hydrogen atom, a halogen atom, a nitro group or an alkylsulfonyl group having 1 to 3 carbon atoms. R ₉ , R ₁₀ and R ₁₁ each independently represent a hydrogen atom or a halogen atom. R ₁₂ represents a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, an alkylcarbonylamino group having 2 to 4 carbon atoms or a phenylcarbonylamino group, and the hydrogen atom of phenyl in the phenylcarbonylamino group has 1 to 5 carbon atoms. It may be substituted with a substituent selected from the group consisting of an alkyl group, an alkoxy group having 1 to 5 carbon atoms and a halogen atom. R ₁₃ represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.
R ₁₄ and R ₁₅ are each independently an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, a hydroxyalkyl group having 1 to 4 carbon atoms, an alkoxyalkyl group having 2 to 6 carbon atoms, or a carbon number. An alkylcarbonyloxyalkyl group having 3 to 7 carbon atoms, an alkoxyalkoxycarbonylalkyl group having 4 to 8 carbon atoms, an alkoxycarbonylalkyl group having 3 to 8 carbon atoms, a cyanoalkyl group having 2 to 8 carbon atoms, and an alkoxy having 3 to 8 carbon atoms A carbonyloxyalkyl group, a phenyl group, a phenylalkyl group having 7 to 9 carbon atoms or a phenoxyalkyl group having 7 to 9 carbon atoms is represented. ]

[Wherein R ₁₆ and R ₁₇ represent a cyano group. R ₁₈ represents an alkyl group having 1 to 3 carbon atoms, a cyanoalkyl group having 2 to 5 carbon atoms, an alkylphenyl group having 7 to 10 carbon atoms, or an alkoxyphenyl group having 7 to 10 carbon atoms. R ₁₉ represents a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, or an alkylcarbonylamino group having 2 to 5 carbon atoms. R ₂₀ represents a hydrogen atom. R ₂₁ and R ₂₂ are each independently an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, a hydroxyalkyl group having 1 to 4 carbon atoms, an alkoxyalkyl group having 2 to 6 carbon atoms, carbon An alkylcarbonyloxyalkyl group having 3 to 6 carbon atoms, an alkoxycarbonylalkyl group having 3 to 6 carbon atoms, an alkoxycarbonyloxyalkyl group having 3 to 6 carbon atoms, an alkoxyalkoxycarbonylalkyl group having 4 to 8 carbon atoms, an alkoxyalkoxy (carbon A 2 to 5) alkyl (2 to 4 carbon) group, a cyanoalkyl group having 2 to 5 carbon atoms, a phenylalkyl group having 7 to 9 carbon atoms, a phenyl group, or a phenoxyalkyl group having 7 to 9 carbon atoms. ]

［式中、Ｒ_２３は水素原子又は炭素数２〜５のアルキルカルボニルアミノ基を表す。Ｒ_２４は水素原子を表す。Ｒ_２５及びＲ_２６は、それぞれ独立に炭素数１〜５のアルキル基、炭素数２〜５のアルケニル基、炭素数１〜４のヒドロキシアルキル基、炭素数２〜６のアルコキシアルキル基、炭素数３〜７のアルキルカルボニルオキシアルキル基、炭素数３〜８のアルコキシカルボニルアルキル基、炭素数３〜８のアルコキシカルボニルオキシアルキル基、炭素数２〜５のシアノアルキル基又は炭素数９〜１２のフェニルアルコキシカルボニルアルキル基を表す。］

[Wherein, R ₂₃ represents a hydrogen atom or an alkylcarbonylamino group having 2 to 5 carbon atoms. R ₂₄ represents a hydrogen atom. R ₂₅ and R ₂₆ are each independently an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, a hydroxyalkyl group having 1 to 4 carbon atoms, an alkoxyalkyl group having 2 to 6 carbon atoms, or a carbon number. An alkylcarbonyloxyalkyl group having 3 to 7 carbon atoms, an alkoxycarbonylalkyl group having 3 to 8 carbon atoms, an alkoxycarbonyloxyalkyl group having 3 to 8 carbon atoms, a cyanoalkyl group having 2 to 5 carbon atoms, or phenyl having 9 to 12 carbon atoms Represents an alkoxycarbonylalkyl group. ]

［式中、Ｙ_１及びＹ_２の一方は水酸基を表し、他方は−ＮＨ（Ｒ_２７）を表す。Ｒ_２７はハロゲン原子、炭素数１〜３のヒドロキシアルキル基、炭素数１〜３のアルキルスルホニル基、炭素数２〜４のアルキルカルボニルオキシ基、フェニル基又はフェニルカルボニルオキシフェニル基を表す。］

[Wherein, one of Y ₁ and Y ₂ represents a hydroxyl group, and the other represents —NH (R ₂₇ ). R ₂₇ represents a halogen atom, a hydroxyalkyl group having 1 to 3 carbon atoms, an alkylsulfonyl group having 1 to 3 carbon atoms, an alkylcarbonyloxy group having 2 to 4 carbon atoms, phenyl or phenyl carbonyloxy phenyl group. ]

［式中、Ｙ_３及びＹ_４の一方は水酸基を表し、他方はアミノ基を表す。ｎは０、１又は２を表す。Ｒ_２８は水素原子、炭素数１〜３のアルコキシ基又はフェニル基を表す。該フェニル基における水素原子は、ヒドロキシ基、炭素数１〜３のアルコキシ基、炭素数２〜４のアルキルカルボニルオキシ基、炭素数２〜４のアルコキシカルボニルオキシ基及びフェニルカルボニルオキシ基からなる群より選ばれる置換基で置換されていてもよい。］

[Wherein, one of Y ₃ and Y ₄ represents a hydroxyl group, and the other represents an amino group. n represents 0, 1 or 2. R ₂₈ represents a hydrogen atom, an alkoxy group having 1 to 3 carbon atoms, or a phenyl group. The hydrogen atom in the phenyl group is selected from the group consisting of a hydroxy group, an alkoxy group having 1 to 3 carbon atoms, an alkylcarbonyloxy group having 2 to 4 carbon atoms, an alkoxycarbonyloxy group having 2 to 4 carbon atoms, and a phenylcarbonyloxy group. It may be substituted with a selected substituent. ]

［式中、Ｒ_２９は炭素数１〜５のアルキル基、炭素数２〜８のアルコキシアルキル基又は炭素数２〜８のアルコキシアルコキシアルキル基を表す。］

[Wherein R ₂₉ represents an alkyl group having 1 to 5 carbon atoms, an alkoxyalkyl group having 2 to 8 carbon atoms, or an alkoxyalkoxyalkyl group having 2 to 8 carbon atoms. ]

［式中、Ｒ_３０は水素原子、炭素数１〜３のアルキル基、炭素数１〜３のアルコキシ基、炭素数１〜３のヒドロキシアルキル基、炭素数１〜４のアルキルスルホニル基、炭素数２〜５のアルキルカルボニルオキシ基、フェニルカルボニルオキシ基又は炭素数７〜９のアルキルフェニルスルフォニル基を表す。］

[Wherein R ₃₀ is a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, a hydroxyalkyl group having 1 to 3 carbon atoms, an alkylsulfonyl group having 1 to 4 carbon atoms, or a carbon number. A 2-5 alkylcarbonyloxy group, a phenylcarbonyloxy group, or a C7-9 alkylphenylsulfonyl group is represented. ]

［式中、Ｒ_３１は炭素数１〜６のアルキル基又はフェニル基を表す。該アルキル基における水素原子は、水酸基、ハロゲン原子、炭素数１〜７のヒドロキシアルキル基、炭素数８〜１２のフェノキシカルボニルオキシアルキル基及び炭素数７〜９のフェノキシアルキル基、炭素数７〜９のフェニルアルキル基、炭素数３〜７のアルコキシカルボニルオキシアルキル基からなる群より選ばれる置換基で置換されていてもよい。
また、上記フェニル基における水素原子は、炭素数１〜３のアルキル基、炭素数１〜３のアルコキシ基、ハロゲン原子、水酸基、炭素数２〜４のアルキルカルボニルオキシ基、炭素数３〜７のアルコキシカルボニルアルコキシ基及び炭素数２〜６のアルコキシアルキルアミノスルホニル基、炭素数３〜６のアルコキシカルボニルアルキル基、炭素数３〜６のアルキルカルボニルアルコキシ基、炭素数７〜９のフェニルアルコキシ基、炭素数３〜６のアルコキシカルボニルアルコキシ基及び炭素数１〜３のヒドロキシアルキルチオエーテル基からなる群より選ばれる置換基で置換されていてもよい。］
上式(６)〜(１４)で示される分散染料は、いずれも公知の化合物である。

[Wherein R ₃₁ represents an alkyl group having 1 to 6 carbon atoms or a phenyl group. The hydrogen atom in the alkyl group is a hydroxyl group, a halogen atom, a hydroxyalkyl group having 1 to 7 carbon atoms, a phenoxycarbonyloxyalkyl group having 8 to 12 carbon atoms, a phenoxyalkyl group having 7 to 9 carbon atoms, or 7 to 9 carbon atoms. And a substituent selected from the group consisting of an alkoxycarbonyloxyalkyl group having 3 to 7 carbon atoms.
Moreover, the hydrogen atom in the said phenyl group is a C1-C3 alkyl group, a C1-C3 alkoxy group, a halogen atom, a hydroxyl group, a C2-C4 alkylcarbonyloxy group, a C3-C7 An alkoxycarbonylalkoxy group and an alkoxyalkylaminosulfonyl group having 2 to 6 carbon atoms, an alkoxycarbonylalkyl group having 3 to 6 carbon atoms, an alkylcarbonylalkoxy group having 3 to 6 carbon atoms, a phenylalkoxy group having 7 to 9 carbon atoms, carbon It may be substituted with a substituent selected from the group consisting of an alkoxycarbonylalkoxy group having 3 to 6 carbon atoms and a hydroxyalkylthioether group having 1 to 3 carbon atoms. ]
The disperse dyes represented by the above formulas (6) to (14) are all known compounds.

  EXAMPLES Hereinafter, although an Example etc. demonstrate this invention further in detail, this invention is not limited by these examples. In addition, the part and% in an example are a weight part and weight%, respectively.

1) Preparation of yellow disperse dye composition Quinoline derivative (1), 1,3-indandione derivative (2), monobromide (3), dibromide (4) and dibromide of the 1,3-indandione derivative Each 1 part of brominated product (5) was individually microparticulated in 6 parts of water together with 3 parts of a condensate of sodium naphthalenesulfonate and formalin to obtain aqueous compositions. These aqueous compositions were used to adjust the blending ratios shown in Table 1, and then diluted 10 times with water to prepare a mother liquor of the composition. The mother liquor of this composition was appropriately diluted and used for dyeing hydrophobic fiber materials.

2) Dyeing speed test i) 20 parts of the mother liquor of the composition described above and 3 parts of Ionette RAP-1170 [manufactured by Sanyo Chemical Co., Ltd.] were uniformly dispersed in water. Subsequently, 1.2 parts of acetic acid and 4.8 parts of sodium acetate were added to this dispersion to prepare a dye bath having a total amount of 3000 parts.
ii) 100 parts of Tetoron Tropical [polyester fiber fabric manufactured by Toray Industries, Inc.] is added to the above dye bath, heated from 60 ° C. to 130 ° C. at a rate of 1 ° C. per minute, and then kept at 130 ° C. for 45 minutes. Then, staining was performed. After completion of the dyeing, the cloth was cooled to 90 ° C. or lower, and the tetron tropical in the dyeing bath was taken out and treated in the order of water washing, reduction washing and drying to obtain dyed fabric A.
iii) 100 parts of tetron tropical is added to the dye bath, the temperature is increased from 60 ° C. at a rate of 1 ° C. per minute, and when the temperature of the dye bath reaches 100 ° C., the tetron tropical in the dye bath is taken out, Dyeing cloth B was obtained by processing in the order of water washing, reduction washing and drying.

3) Evaluation of dyeing speed The color density of the dyed cloth A dyed at 130 ° C. for 30 minutes and the color density of the dyed cloth B taken out at 100 ° C., respectively, were manufactured by Sumika Analysis Center Co., Ltd. A colorimetric device equipped with a photometer or the like), and a dyeing speed index was calculated from the obtained measured value and the following equation (15).

  Dyeing speed index = (measured value of dyed fabric B) / (measured value of dyed fabric A) (15)

The above dyeing speed index has a value of (ii) in the range of 0.25 to 0.55, a good dyed product is obtained, and the above numerical value is (b) 0.20 or more and less than 0.25. There is a risk that a certain range and a range of 0.55 or more and less than 0.60 may cause uneven dyeing, and the above numerical value is (c) less than 0.20 and not more than 0.60. It has been empirically known by the present inventor that a uniform dyeing can be obtained.
Therefore, the dyeing speed was evaluated by ◯ when (i) above, Δ when (b) above, and x when (c) above.

4) Compound dyeing test (confirmation of suitability of three primary colors)
i) 3.0 parts of a commercially available red disperse dye containing a compound represented by the formula (16) (Sumikaron Rubin SE-GL, manufactured by Sumitomo Chemical Co., Ltd.) and a commercially available product comprising a compound represented by the formula (17) 94 parts of water was added to 3.0 parts of a red disperse dye (Sumicaron Brilliant Red SB, manufactured by Sumitomo Chemical Co., Ltd.) to prepare a red mixed mother liquor.

  In addition, 2.0 parts of a commercially available blue disperse dye [Foron Navy S-2GL, manufactured by Sand Co., Ltd.] containing a compound represented by the following formula (18), and a commercially available product comprising a compound represented by the following formula (19) A blue mixed mother liquor was prepared by adding 94 parts of water to 4.0 parts of the blue disperse dye [Sumikaron Blue S-BG, manufactured by Sumitomo Chemical Co., Ltd.].

  The mother liquor obtained by mixing 50 parts of the mixed mother liquor of the red disperse dye and 50 parts of the mixed mother liquor of the blue disperse dye prepared above was subjected to the following test.

ii) 20 parts of the mother liquor of the disperse dye composition obtained in 1) above, 20 parts of the mother liquor obtained by mixing the red disperse dye and the blue disperse dye, and Ionette RAP-1170 [Sanyo Kasei Co., Ltd.] Product] After 2 parts were uniformly dispersed in water, 0.8 part of acetic acid and 3.2 parts of sodium acetate were added to the dispersion to prepare a dyeing bath having a total amount of 2000 parts. This operation was repeated to prepare a total of seven identical dye baths.

iii) After adding 100 parts of Tetron Tropical [polyester fiber fabric manufactured by Toray Industries, Inc.] to each of the above dye baths, the temperature is raised from 60 ° C. to 130 ° C. at a rate of 1 ° C. per minute and then kept at 130 ° C. for 30 minutes. And stained. In the above temperature raising step, when the temperature reached 80 ° C., 90 ° C., 100 ° C., 110 ° C., 120 ° C. and 130 ° C., Tetron tropical was extracted from the six dye baths of the same seven dye baths and washed with water. . In the remaining one dye bath, after reaching 130 ° C., the tetron tropical obtained by further maintaining the temperature at the same temperature for 30 minutes was extracted and washed with water. These seven tetron tropicals were each reduced and washed, and further dried to obtain dyed cloths of Nos. 1 to 7.

5) Evaluation of compatibility The dyed cloths of Nos. 1 to 7 described above are arranged in order, and the change in the hue of the dyed cloth surface is visually observed (the change in the mixing ratio of yellow dye, red dye and blue dye is observed). No change in color density was observed), and the consistency (compatibility) of the dyeing rates of the yellow dye, red dye and blue dye used was evaluated.
○ ・ ・ The hue is almost the same as the dyed cloth of No. 7 and only the density is changed. △ ・ The hue is slightly different from the dyed cloth of No. 7, but the hue is almost the same. × ・ ・ No. There is an extraction cloth with a hue completely different from the dyeing cloth of No. 7.

The above dyeing speed and compatibility test results are summarized in Table 1.
As shown in the table, in the compositions of the present invention of Examples 1 to 8, practical dyeing speed and compatibility were obtained in any case. On the other hand, in Comparative Examples 1 to 3, results that were predicted to cause practical problems were obtained.

The three primary color yellow disperse dye composition of the present invention (i) is useful when dyeing or printing hydrophobic fiber materials such as polyester.
Further, according to the dyeing method of the present invention (ii), a dyed product having good compatibility can be obtained.
Furthermore, according to the dyeing method of the present invention (iii), the hydrophobic fiber material can be dyed in a desired color tone.

Claims (14)

A yellow dispersion for three primary colors, comprising a quinoline derivative represented by the following formula (1), a 1,3-indandione derivative represented by the following formula (2), and a bromide of the 1,3-indandione derivative: Dye composition.

The brominated product of the 1,3-indandione derivative represented by the formula (2) is a dibrominated product represented by the following formula (4) and a dibrominated product represented by the following formula (5): The yellow disperse dye composition for three primary colors according to claim 1, which is a mixture with a monobromide represented by formula (1).

  The bromide of the 1,3-indandione derivative represented by the formula (2) is a mixture of a monobromide represented by the formula (3) and a dibromide represented by the formula (4). Yellow disperse dye composition for three primary colors.   The bromide of the 1,3-indandione derivative represented by the formula (2) is a mixture of a monobromide represented by the formula (3) and a dibromide represented by the formula (5). Yellow disperse dye composition for three primary colors.   The total weight of the 1,3-indandione derivative represented by the formula (2), the monobrominated product represented by the formula (3) and the dibrominated product represented by the formula (4), and the quinoline derivative represented by the formula (1) 4. The yellow disperse dye composition for three primary colors according to claim 3, wherein a ratio with respect to the weight of (3) is in the range of (30-80) :( 70-20).   The total weight of the 1,3-indandione derivative represented by the formula (2), the monobrominated product represented by the formula (3) and the dibrominated product represented by the formula (5), and the quinoline derivative represented by the formula (1) The yellow disperse composition for three primary colors according to claim 4, wherein the ratio to the weight of is in the range of (30-80) :( 70-20).   The ratio of the total weight of the monobromide represented by formula (3) and the dibromide represented by formula (4) to the weight of the 1,3-indandione derivative represented by formula (2) is (80 to 20): The range of (20-80), The yellow disperse dye composition for three primary colors of Claim 3.   The ratio of the total weight of the monobromide represented by formula (3) and the dibromide represented by formula (5) to the weight of the 1,3-indandione derivative represented by formula (2) is (80 to 20): The range of (20-80), The yellow disperse dye composition for three primary colors of Claim 4.   The weight ratio of the monobromide represented by the formula (3) and the dibromide represented by the formula (4) is in the range of (70 to 99.5) :( 30 to 0.5). The yellow disperse dye composition for three primary colors as described.   The weight ratio of the monobromide represented by the formula (3) to the dibromide represented by the formula (5) is in the range of (70 to 99.5) :( 30 to 0.5). The yellow disperse dye composition for three primary colors as described.   Furthermore, the yellow disperse composition for three primary colors in any one of Claims 1-10 containing a dispersing agent.   The yellow disperse composition for three primary colors according to claim 11, wherein the dispersant is an anionic surfactant.   A method for dyeing a hydrophobic fiber material, wherein the yellow disperse dye composition for three primary colors according to any one of claims 1 to 12 is used. A method for dyeing a hydrophobic fiber material, wherein a red disperse dye and / or a blue disperse dye is further used in addition to the yellow disperse dye composition for primary colors according to any one of claims 1 to 12.