JPH0762260A - Coloring composition for hydrophobic material and coloring of hydrophobic material using the composition - Google Patents

Abstract

PURPOSE:To provide a coloring composition useful for the coloring with three primary colors and having excellent level-dyeing property, reproducibility and color fastness of the dyed product by using a specific benzodifuranone compound as the red component and compounding the component with a yellow disperse dye and a blue disperse dye. CONSTITUTION:This coloring composition contains (A) a benzodifuranone compound of the formula I (R is H, OH, etc.) and (B) a compound selected from a monoazo compound of the formula II (X1 and X2 are H or halogen; R2 is H or 1-4C alkyl; R3 and R4 are H, nitrophenyl, etc.), an azo compound of the formula III (X3 is halogen, nitro, etc.; R5 is H or 1-4C alkoxy; R5 is 1-4C alkyl, halogen, etc.; R7 and R8 are 1-8C alkyl, 1-4C hydroxyalkyl, etc.) and an anthraquinone compound of the formula IV (X4 is O or imino; R9 is 1-4C alkyl or 1-4C alkoxy-1-4C alkyl). This composition can be prepared e.g. by dispersing the components A and B in an aqueous medium using a condensation product of naphthalenesulfonic acid and formaldehyde as a dispersing agent.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a hydrophobic material coloring composition and a method for coloring a hydrophobic material, particularly a polyester material, using the composition. More particularly, the present invention relates to a composition containing a benzodifuranone dye compound as a red component, which is useful for the three primary colors, and an application to the coloring of hydrophobic materials.

[0002]

2. Description of the Related Art For example, Japanese Patent Laid-Open Nos. 60-152567 and 52
-109526 publication, 56-122869 publication, JP-A-3-14876
Various benzodifuranone compounds useful for dyeing or printing hydrophobic fibers are described in JP-A No. 3-72571 and the like.

[0003]

However, when such a benzodifuranone dye is mixed with a general-purpose yellow dye and / or a blue dye and dyed in the three primary colors, problems such as uneven dyeing often occur. It was Especially when the dyeing density between the three primary colors is greatly different,
There is a problem in that the dyeing speeds are greatly different, and a hue difference occurs between dyeing batches, or dyeing unevenness occurs. The present inventors have completed the present invention as a result of earnest studies for solving these problems.

[0004]

The present invention has the general formula (I)

[0005]

[Chemical 5]

[Wherein R represents a hydrogen atom, a hydroxyl group, C₁~_Four
Alkoxy group, C₁~_FourAlkoxy C₁~_FourAlkoxy
Base, C₁~_FourAlkylcarbonyloxy group, C₁~_FourA
Lucoxycarbonyloxy C₁~_FourAlkoxy group,
Nil C₁~_FourAlkylcarbonyloxy group, pyridine
Rubonyloxy group, phenylcarbonyloxy group, C ₁
~_FourAlkoxy C₁~_FourAlkoxycarbonyl C₁~_Four
Alkoxy group or OR₁Q (here R₁Is methyl
Group, or hydroxyl group, C₁~_FourAn alkoxy group, or
C₁~_FourSubstituted with an alkylcarbonyloxy group
May be straight chain or branched C₂~₆Show alkylene group
And Q is an optionally substituted 5 or 6 saturation or
Represents an unsaturated heterocyclic residue. ) Represents. ] Indicated by
At least one selected from the group of nzodifuranone compounds
And the general formula (II)

[0007]

[Chemical 6]

[0008] [wherein X _1, X ₂ are independently a hydrogen atom or a halogen atom together, R ₂ is a hydrogen atom, a halogen atom or C ₁ ~ ₄ alkyl groups, R _3, R ₄ are each independently hydrogen atom, C ₁ ~ ₄ alkyl group, a cyano C ₁ ~ ₄ alkyl group, C ₁ ~ ₄ alkylcarbonyloxy C ₁ ~ ₄
Alkyl group, C ₁ ~ ₄ alkoxycarbonyloxy C _1
1-4 alkyl group, phenyl carbonyloxy C ₁ - ₄ alkyl group, a benzyl group, a nitrophenyl group, or a phenoxy C ₁ - ₄ alkyl group. ] A monoazo compound represented by the general formula (III)

[0009]

[Chemical 7]

[Wherein X ₃ is a halogen atom, a nitro group,
Or C ₁ ~ ₄ alkylsulfonyl group, a R ₅ is a hydrogen atom or C ₁ ~ ₄ alkoxy group, R ₆ is, C ₁ ~ ₄ alkyl group, a halogen atom, C ₁ ~ ₄ alkyl carbonyl amino group or a phenyl carbonylamino R _7, R
₈ independently of one another represent C ₁ - ₄ alkoxy optionally substituted C ₁ to ₈ alkyl group with a group, hydroxy C ₁ - ₄ alkyl or C ₁ - ₄ alkylcarbonyloxy C _1,
~ ₄ represents an alkyl group. ] And an azo compound represented by the general formula (IV)

[0011]

[Chemical 8]

[0012] [wherein X ₄ is an oxygen atom or an imino group, R ₉ is C ₁ ~ ₄ alkyl group, C ₁ ~ ₄ alkoxy C ₁ ~ ₄ alkyl or C ₁ ~ ₄ alkoxy C ₁ ~ ₄
Alkoxy C ₁ ~ ₄ alkyl group. ] The hydrophobic material coloring composition containing at least 1 sort (s) selected from the group which consists of the anthraquinone type compound shown by these, and the coloring method of the hydrophobic material characterized by using the same are provided.

The compound represented by the general formula (I) is a compound selected from the known compound group described in, for example, JP-A-3-72571. Examples of the saturated heterocyclic residue represented by Q in the general formula (I) include tetrahydrofuryl, tetrahydrothienyl, tetrahydropyranyl, pyrrolidyl, piperidyl, piperazyl and morpholinyl. These heterocyclic residue is a halogen atom, a hydroxyl group, C ₁ ~ ₄ alkyl group, C ₁ ~ ₄ alkoxy group, C ₁ ~ ₄ alkyl group, C ₁ ~ ₄ alkoxycarbonyl group, a cyano group, an amino group, a keto group It may be replaced by During these heterocyclic residue, such as C ₁ ~ ₄ alkyl which may tetrahydrofuryl or tetrahydropyranyl be the Le or morpholinyl substituted by group. Table 1 shows specific examples of compounds that are particularly preferably used in the present invention.

[0014]

[Table 1]

General formulas (II) and (III) in the present invention
Each of the compounds represented by and (IV) is a known compound, and specific examples of the compounds that are particularly preferably used are shown in Tables 2, 3 and 4, respectively.

[0016]

[Table 2]

[0017]

[Table 3]

[0018]

[Table 4]

The benzidifuranone compound of the general formula (I) which is the red component of the present invention, and the general formula (II) which is the yellow component
The monoazo compound of the formula (1), the azo compound of the general formula (III) and the anthraquinone compound of the general formula (IV), which are blue components, are used as a dispersion obtained by dispersing, or in the form of dried powder or granules. To be

General formulas (I), (II), (III) and (I
Dispersion of each compound represented by V) is carried out, for example, in a sand mill by using an anionic dispersant such as naphthalenesulfonic acid formalin condensate, ligninsulfonic acid, cresol-shepha acid formalin condensate or polyoxyethylene alkyl. It can be carried out in an appropriate amount of an aqueous medium using a dispersant selected from various dispersants such as ethers, polyoxyethylene alkylphenyl ethers and other nonionic dispersants. The obtained dispersion liquid can be used as a liquid or as a powder or granules by drying.

The composition of the present invention comprises a benzodifuranone compound represented by the general formula (I) alone or in a mixture thereof.
A monoazo compound represented by the general formula (II) or a mixture thereof, an azo compound represented by the general formula (III) or a mixture thereof, and an anthraquinone compound represented by the general formula (IV), or a mixture thereof. It can be obtained by blending at least one selected from a monoazo compound, an azo compound and an anthraquinone compound with at least one benzodifuranone compound, and the blending ratio can be appropriately determined depending on a desired hue.

These compounds may be compounded at the stage of dispersing each compound, or after dispersing each compound, and when they are used as disperse dyes, they may be blended in a dye bath at the stage of dyeing. Good. Further, the composition of the present invention, for the purpose of adjusting the hue and the like, compounds other than the compounds represented by the above general formulas, further, dispersants, extenders, pH adjusters, dispersion leveling agents, dyeing aids, It may contain a solvent, a resin binder and the like.

The composition of the present invention is useful as a disperse dye, a dye for sublimation transfer type heat-sensitive recording, and the like for coloring hydrophobic materials such as polyester, triacetate, diacetate, polyamide and polycarbonate. is there. In particular, the composition of the present invention is useful as a disperse dye for dyeing or printing a hydrophobic fiber material. In dyeing a hydrophobic fiber material, a dye bath in which the composition of the present invention is dispersed in an aqueous medium is added with a pH adjuster, a dispersion leveling agent, etc., if necessary, and then the hydrophobic fiber is dipped. For example, in the case of polyester fiber, the pressure is 105 ° C or higher, preferably 100-140 ° C
-Stain for 60 minutes. This dyeing time can be shortened or extended depending on the dyeing condition.

It is also possible to dye in the presence of a carrier such as o-phenylphenol or methylnaphthalene at a relatively high temperature, for example, in the boiling state of water. Furthermore, when the dye dispersion is padded on the cloth,
A dyeing method such as minging or dry heat treatment is also possible.

In the case of printing, the dye dispersion is kneaded together with an appropriate sizing agent, and the cloth is printed and dried, and then steaming or dry heat treatment is performed. Further, it is also possible to print by an inkjet method. As a hydrophobic fiber,
Examples thereof include polyester fibers, triacetate fibers, diacetate fibers, and polyamide fiber materials. As the blended or mixed woven products thereof, there are mixed spun woven products of the above fibers and / or those and cellulosic fibers, wool, and silk. Examples include mixed-spun mixed woven products with natural fibers such as. The composition of the present invention is particularly useful for dyeing or printing polyester fiber materials.

According to the present invention, in coloring a hydrophobic fiber material, it is possible to obtain colored products of various hues such as brown, gray or beige, which have good dyeing reproducibility and excellent leveling property. In particular, when the dyeing densities of the three primary colors are greatly different, the dyeing speeds of the three primary colors are close to each other, and even if the dyeing speeds of the three primary colors are greatly different, the dyeing speeds of the three primary colors are close to each other, and excellent leveling properties are obtained. The feature is that it has reproducibility. Furthermore, the obtained dyed product has extremely excellent fastness.

Hereinafter, the present invention will be described in more detail with reference to examples. In the text, parts represent parts by weight.

[0028]

【Example】

Example 1 A compound represented by the specific example a-12 of the general formula (I) 8.7
Part, a compound represented by the specific example b-4 of the general formula (II) 1
A disperse dye composition was obtained by commercializing a mixture of 1.8 parts and 4.5 parts of the compound represented by the specific example c-9 of the general formula (III) with 75 parts of a formalin condensate dispersant of naphthalenesulfonic acid. 1.7 parts of this disperse dye composition and Sumipon TF
1,500 parts of a brown dye bath containing 1.5 parts (a dyeing aid manufactured by Sumitomo Chemical Co., Ltd.) were prepared. This dispersion was used to dye a polyester fiber woven fabric as described below. The obtained dyed product was uniform without spots, and the compatibility of each compound was excellent. The obtained dyed product had excellent fastness.

[Dyeing conditions] 1.2 parts of acetic acid and 4.8 parts of soda acetate are added to the dyeing bath. 100 parts of Tetron tropical (Toray polyester fiber woven fabric) cloth is put into this dyeing bath, and the temperature is raised from 60 ° C to 130 ° C at a rate of 1 ° C / minute.
Stain for 60 minutes. After dyeing, the dyed product in the dye bath is taken out by cooling to 90 ° C. or lower, washed with water, reduced, washed with water and dried to obtain a dyed product.

Example 2 Compound 8.0 represented by the specific example a-12 of the general formula (I)
Parts, 2.1 parts of the compound represented by the specific example b-1, and 12.7 parts of the compound represented by the specific example c-3 of the general formula (III) are commercialized with 77.2 parts of the ligninsulfonic acid-based dispersant to prepare a disperse dye. A composition was obtained. 1500 parts of a gray color dyeing bath containing 0.4 parts of the same, 1.5 parts of Sumipon TF (a dyeing aid manufactured by Sumitomo Chemical Co., Ltd.), 0.6 part of acetic acid and 2.4 parts of soda acetate were prepared, and the same as in Example 1. When the dyeing was carried out, the obtained dyed product was uniform without spots, and the compatibility of each compound was excellent. The obtained dyed product had excellent fastness.

Examples 3 to 6 Instead of the compound represented by the specific example c-9 shown in Example 1, the compounds represented by the specific examples c-3, c-6, d-1, d-5 are used. The following dyeing was carried out in the same manner as in Example 1, and the dyed product obtained was uniform without spots and showed excellent compatibility. The obtained dyed product had excellent fastness.

Examples 7 to 8 The compounds shown in Concrete examples c-9 and d-1 were used in place of the compounds shown in concrete example c-3 shown in Example 2, and dyeing was carried out in the same manner as in Example 2 below. The dyed product thus obtained was uniform without spots and showed excellent compatibility. The obtained dyed product had excellent fastness.

Example 9 0.07 part of a disperse dye obtained by commercializing 30 parts of the compound represented by the specific example a-5 of the general formula (I) with 70 parts of a ligninsulfonic acid-based dispersant, and a compound of the general formula (II) Compound shown in Example b-10
Commercialized 30 parts of disperse dye with 30 parts of ligninsulfonic acid-based dispersant as 70 parts and 30 parts of compound represented by the specific example c-9 of the general formula (III) as ligninsulfonic acid-based dispersant as 70 parts. 0.03 part of the above disperse dye, 0.6 part of acetic acid and sodium acetate
Six 1500 parts of beige dye bath containing 2.4 parts of Da and 1.5 parts of Sumipon TF (Sumitomo Chemical Co., Ltd. dyeing auxiliary agent) were prepared, and Tetoron Tropical (Toray polyester fiber fabric) was prepared for each of them. 100 copies were put in. And 2 for each 3
Dyeing was performed for 20 minutes at 130 ° C. using a single color pet dyeing machine (manufactured by Nippon Dyeing Machine Co., Ltd.), reduction washing, washing with water and drying to obtain 6 beige colored dyeings. Each of the obtained dyed products had no dyeing spots, had the same density and hue, had no difference between dyeing machines, and had excellent dyeing reproducibility.

Examples 10 to 11 The compounds shown in Concrete Examples a-3 and a-13 are used in place of the compounds shown in Concrete Example a-5 shown in Example 9, and dyeing is carried out in the same manner as in Example 9 below. As a result, each of the obtained dyed products has no stain spots, and has the same density and hue,
There was no difference between the dyeing machines and the dyeing reproducibility was excellent.

Example 12 The compound shown in Concrete Example b-16 was used in place of the compound shown in Concrete Example b-10 shown in Example 9, and the compound shown in Concrete Example c-9 was used instead of the compound shown in Concrete Example b-9. Using the compound represented by d-1, the following dyeing was carried out in the same manner as in Example 9, and all the obtained dyed products had no uneven stain and had the same density and hue, There was no difference and the dyeing reproducibility was excellent.

Example 13 The compound shown in Concrete Example a-3 was used in place of the compound shown in Concrete Example a-5 shown in Example 9, and the compound shown in Concrete Example b-10 was used instead of the concrete example. Specific examples of the compounds represented by b-16 are used instead of the compounds represented by specific example c-9.
Using the compound represented by c-6, the following dyeing was carried out in the same manner as in Example 9, and all of the obtained dyed products had no stain spots and had the same density and hue. There was no difference and the dyeing reproducibility was excellent.

Example 14 The compound of the specific example a-13 was used in place of the compound of the specific example a-5 shown in Example 9, and the specific example of the compound was replaced with the compound of the specific example b-10. Specific examples of the compounds represented by b-16 are used instead of the compounds represented by specific example c-9.
Using the compound represented by c-4, the following dyeing was carried out in the same manner as in Example 9, and all the obtained dyed products had no stain spots and had the same density and hue, There was no difference and the dyeing reproducibility was excellent.

Continuation of front page (51) Int.Cl. ⁶ Identification number Office reference number FI technical display location D06P 3/26 3/54

Claims (2)

[Claims] 1. A compound represented by the general formula (I):[Wherein R is a hydrogen atom, a hydroxyl group, C₁~_FourAlkoxy
Base, C₁~_FourAlkoxy C₁~_FourAlkoxy group, C₁~
_FourAlkylcarbonyloxy group, C₁~_FourAlkoxyca
Lubonyloxy C₁~_FourAlkoxy group, phenyl C₁~
_FourAlkylcarbonyloxy group, pyridinecarbonylo
Xy group, phenylcarbonyloxy group, C ₁~_FourArco
Kishi C₁~_FourAlkoxycarbonyl C₁~_FourAlkoxy
Group or OR₁Q (here R₁Is a methylene group,
Is a hydroxyl group, C₁~_FourAlkoxy group or C₁~_FourA
A straight chain optionally substituted with a rualkylcarbonyloxy group
Or C at the branch₂~₆Represents an alkylene group, Q is substituted
Optionally saturated or unsaturated complex of 5 or 6
Represents a ring residue. ) Represents. ] Benzodifurano
At least one selected from the group of compounds
(II) [Chemical formula 2][X in the formula_1,X₂Are hydrogen atoms or halogens independently of each other.
R atom₂Is a hydrogen atom, a halogen atom or C₁
~_FourAn alkyl group, R_3,R_FourAre hydrogen sources independently of each other
Child, C₁~_FourAlkyl group, cyano C₁~_FourAn alkyl group,
C₁~_FourAlkylcarbonyloxy C₁~_FourAlkyl
Base, C₁~_FourAlkoxycarbonyloxy C₁~_FourAl
Kill group, phenylcarbonyloxy C₁~_FourAlkyl
Group, benzyl group, nitrophenyl group or phenoxy C
₁~_FourRepresents an alkyl group. ] Monoazo compound
A compound of the general formula (III):[X in the formula₃Is a halogen atom, a nitro group, or C₁~
_FourAn alkylsulfonyl group, R_FiveIs a hydrogen atom or C₁
~_FourR is an alkoxy group₆Is C₁~_FourAlkyl group, ha
Rogen atom, C₁~_FourAlkylcarbonylamino group
Is a phenylcarbonylamino group, R_7,R₈Are alone with each other
Vertically C₁~_FourC optionally substituted with an alkoxy group₁
~₈Alkyl group, hydroxy C₁~_FourAlkyl group
Is C₁~_FourAlkylcarbonyloxy C₁~_FourAlkyl
Represents a group. ] An azo compound represented by
(IV) [Chemical 4][X in the formula_FourIs an oxygen atom or imino group, R₉Is C
₁~_FourAlkyl group, C₁~_FourAlkoxy C₁~_FourArchi
Ru radical or C₁~_FourAlkoxy C₁~_FourAlkoxy C₁
~_FourRepresents an alkyl group. ] Anthraquinone series
Contains at least one selected from the group consisting of compounds
And a hydrophobic material coloring composition. 2. A method for coloring a hydrophobic material, which comprises using the composition according to claim 1.