JP2913254B2 - Water-insoluble disperse dye composition and method for dyeing polyester fiber using the same - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a water-insoluble disperse dye composition (dark blue or black) and a method for dyeing polyester fibers using the dye composition.

[0002]

2. Description of the Related Art Conventionally, dyeing of polyester fiber using a disperse dye has been carried out in an acidic (pH = 4 to
5) It is usually carried out in a bath, and the dyeing of cotton / polyester blended fibers is also performed by a dyeing method using a dye for dyeing cotton and a dyeing method using a dye for dyeing polyester. Due to the difference, the two-bath dyeing method or the one-bath two-step dyeing method was performed. However, in recent years, in order to carry out weight reduction processing using an alkali agent for the purpose of improving the texture of the dyed cloth, an alkali agent is mixed into the dyeing process, or dyed in an alkaline bath in a single bath dyeing process of a mixed fiber of cotton and polyester. In addition, an alkaline bath dyeing method has been implemented for the purpose of preventing oligomers and simplifying the process. As a result, those having small pH dependence, that is, acidic (p
When dyeing in the range of H = 4) to alkalinity (pH = 9), a disperse dye having a small change in hue of a material to be dyed has been required.

[0003] Further, the dye compositions which have been generally used in the past and have a low pH dependency are, as represented by JP-B-62-6592 and JP-B-1-210465, excellent in light fastness, washing fastness, and the like. It is strongly desired to develop a disperse dye composition having water fastness, rub fastness, but poor sublimation fastness, which has a small pH dependency and good various fastnesses including sublimation fastness. I have.

[0004]

DISCLOSURE OF THE INVENTION The present invention has been made to solve the problem of the prior art having a low pH dependence and poor sublimation fastness as described above. It is an object of the present invention to provide a navy blue or black disperse dye composition having low fastness and good fastness including sublimation fastness. Another object of the present invention is to provide a method for dyeing polyester fibers using these disperse dye compositions which has solved the problems of the prior art.

[0005]

The above objects can be achieved by the following disperse dye composition of the present invention and a dyeing method using the same.

That is, the present invention provides a dye represented by the following structural formula (I):

Embedded image [In the formula (I), X represents a chlorine or bromine atom, Y represents an acetyl group or a benzoyl group] A dye represented by the following structural formula (II),

Embedded image [In the formula (II), X represents a chlorine or bromine atom] and a dye represented by the following structural formula (III):

Embedded image [In the formula (III), X represents a chlorine or bromine atom, Y represents a nitro group or a cyano group, Z represents an acetyl group or a benzoyl group, a combination of Y is a cyano group and Z is a benzoyl group. Is excluded.] Is a water-insoluble navy blue disperse dye composition.

The inventor of the present invention prepared a navy blue disperse dye composed of the formulas (I) and (III) in order to obtain a navy blue disperse dye composition having a small pH dependency and various fastnesses including sublimation fastness. The use of a dye of formula (II) in a specific proportion in the composition was considered. Those dyed with the navy blue dispersing compositions composed of the formulas (I) and (III) have low pH dependency and good various fastnesses except for sublimation fastness.
By using a specific ratio of a dye having a high pH dependency represented by the formula (II) but having various fastnesses including sublimation at a specific ratio, the pH dependence of the dark blue disperse dye composition as a whole is small and the sublimation fastness is low. In addition, various fastnesses including those are good.

The navy blue disperse dye composition of the present invention is based on the total amount of the dye base powder to be used, and the amount of the dye represented by the above formula (I) is 40 to 55.
% By weight, 20 to 35% by weight of the dye represented by the formula (II),
The dye of the formula (II) may be blended in an amount of 15 to 30% by weight. In order to obtain a particularly desirable dark blue dyed product, the dye of the formula (I) is 45 to 50% by weight and the dye of the formula (II) 20 to 30% by weight of the dye and 20 of the dye represented by the formula (III)
A blending ratio of ３０30% by weight is good. Formula used in the present invention
The dyes represented by (I) to (III) are described in JP-B-41-546.
8, JP-B-45-12035, JP-A-55-7544
8. Dyes known in JP-B-47-43495. Alternatively, it is an azo dye similar thereto, and can be easily obtained or produced according to a conventional method.

The dye of the formula (I) is disclosed in JP-A-55-75448.
And the method described in JP-B-41-5468, the following formula
It can be produced by a method of diazotizing an amine of (I) -1 and coupling with a coupling component of the following formula (I) -2.

[0010]

Embedded image [In the formula (I) -1, X represents a chlorine or bromine atom]

[0011]

Embedded image [In the formula (I) -2, Y represents an acetyl group or a benzoyl group.]

The dyes represented by the formula (I) used in the present invention include, for example, the following (formulas (I-1) to (I-
4)).

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According to the method described in JP-B-45-12035, the dye of the formula (II) is prepared by diazotizing an amine of the following formula (I) -1 and coupling with a coupling component of the following formula (II) -2. Can be manufactured.

[0014]

Embedded image [In the formula (I) -1, X represents a chlorine or bromine atom]

[0015]

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The dyes represented by the formula (II) used in the present invention include, for example, the following (formulas (II-1) and (II-
2)).

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According to the method described in JP-B-41-5468, the dye of the formula (III) is prepared by diazotizing an amine of the following formula (III) -1 and coupling with a coupling component of the following formula (III) -2. Can be manufactured.

[0018]

Embedded image [In formula (III) -1, X represents a chlorine or bromine atom, and Y represents a nitro group or a cyano group.]

[0019]

Embedded image [In the formula (III) -2, Z represents an acetyl group or a benzoyl group.]

The dyes represented by the formula (III) used in the present invention include, for example, the following (formulas (III-1) to (III-6)).

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Further, some of the navy blue disperse dye compositions of the present invention can be produced by the following method.

Embedded image [In the formula (V), Y represents an acetyl group or a benzoyl group.]
40 to 55% by weight of a coupling component represented by

Embedded image 20 to 35% by weight of a coupling component represented by

Embedded image Wherein, in the formula (VII), Z represents an acetyl group or a benzoyl group, a mixture of 15 to 30% by weight of a coupling component represented by the following formula:

Embedded image [In the formula (VIII), X represents a chlorine or bromine atom], and a diazotized amine is obtained to obtain a navy blue disperse dye composition. Further, similarly, an appropriate two components can be synthesized according to the above, and the other one component synthesized separately can be added for production.

In carrying out the present invention, a press cake of each dye to be blended is finely dispersed in an aqueous medium together with a suitable dispersing agent, and is then converted into a liquid state or a powdery state by a spray drying method or the like, and then subjected to a predetermined process. A method of preparing a navy blue disperse dye composition by blending in a proportion or a navy blue disperse dye composition by finely dispersing a press cake of the navy blue disperse dye composition described above with an appropriate dispersant in an aqueous medium. There is. In the above, the micronization treatment is performed by a known method, and for example, a dye (primary powder)
And a formalin condensate of naphthalenesulfonate, ligninsulfonate, alkylbenzenesulfonate, and the like, are subjected to fine-particle dispersion treatment in a wet state with a fine-particle facility such as a sand mill to obtain a disperse dye. The disperse dye which has been subjected to the fine particle dispersion treatment for carrying out the method of the present invention may be either a dry product or a liquid product.

The water-insoluble navy blue disperse dye composition of the present invention is useful as a base for obtaining a black disperse dye composition having a small pH dependency and good fastnesses including various fastnesses including sublimation fastness.

That is, the water-insoluble black disperse dye composition is a dye (raw powder) represented by the following formula (IV):

Embedded image [In the formula (IV), X represents a chlorine, bromine or hydrogen atom, and Y represents a cyano group, a phenoxy group or an oxybenzoyl group], and subjected to the same treatment as the above-described method for producing a dark blue disperse dye. Yellow brown to orange disperse dye,
This was used to prepare the water-insoluble dark blue disperse dye composition 40 of the present invention.
It can be achieved by blending 30 to 60% by weight with respect to 70% by weight.

The dye of the formula (IV) used in the present invention is a known dye described in JP-B-43-15310, JP-B-59-43594, Industrial Chemistry Magazine 59, 619 (1956). It can be manufactured by the manufacturing method described.

That is, it can be produced by a method of diazotizing an amine of the following formula (IV) -1 and coupling with a coupling component of the following formula (IV) -2.

[0027]

Embedded image [In the formula (IV) -1, X represents a chlorine, bromine or hydrogen atom]

[0028]

Embedded image [In Formula (IV) -2, Y represents a cyano group, a phenoxy group, or an oxybenzoyl group.]

The dyes represented by the formula (IV) used in the present invention include, for example, the following (formulas (IV-1) to (IV-
9)).

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In order to dye polyester fibers using the navy blue disperse dye composition and the black disperse dye composition thus obtained, the polyester fiber is pressurized at 105 ° C. or higher, preferably 11 ° C. or higher.
A method of dyeing at 0 to 140 ° C., a method of dyeing at a relatively high temperature in the presence of a carrier such as o-phenylphenol or trichlorobenzene, for example, in a boiling state of water, or a method of padding a dye dispersion onto a cloth, 150-230 ° C
And a so-called thermosol method of performing a drying treatment for 30 to 60 seconds. On the other hand, in the case of printing, the disperse dye composition is kneaded with an appropriate sizing agent such as guar gum or locust bean gum, printed on a cloth and treated by a steaming or thermosol method to achieve the purpose. can do. Further, the disperse dye composition of the present invention is a so-called alkali bath dyeing method in which the dye bath is adjusted to pH = 9 to 9.5 using a pH adjuster corresponding to an alkali bath, and then dyed at 110 to 140 ° C. under pressure. But it can be used.

[0031]

According to the present invention, a polyester fiber is dyed in dark blue having good light fastness, fastness to sublimation, fastness to washing, fastness to water and fastness to rubbing, and has a small pH dependency. The present invention provides a dye composition. formula
Those dyed with the dark blue dispersion composition composed of (I) and (III) have a small pH dependency but poor sublimation fastness. On the other hand, as a result of dyeing using a dye having a large pH dependency represented by the formula (II) but a good sublimation fastness at a specific ratio, the pH dependency as a whole as a dark blue disperse dye composition was small and the dye was sublimated. Good in various fastnesses including fastness can be obtained. Furthermore, this dark blue dye composition is useful as a base for obtaining a black dye having good pH dependency and various fastnesses including sublimation, and has low pH dependency and various fastnesses including sublimation. Good degree yellow brown ~
By using the orange component, it is possible to obtain a black disperse dye composition having low pH dependency and excellent fastness including sublimation fastness.

[0032]

EXAMPLES The present invention will be described more specifically with reference to examples, but the present invention is not limited to the following examples (in the description, "parts" means "parts by weight").

Example 1 In the above formula (I), 25 parts of a dye precursor in which X is a chlorine atom and Y is a benzoyl group were prepared by combining 12.5 parts of a formaldehyde condensate of naphthalene sulfonate with 12.5 parts of lignin sulfonate.
2.5 parts and 50 parts of water were finely dispersed together to prepare a component (A). Similarly, in the above formula (II), 13 parts of the dye precursor in which X is a bromine atom is dispersed in fine particles together with 6.5 parts of a formaldehyde condensate of naphthalenesulfonate, 6.5 parts of a ligninsulfonate and 26 parts of water. Then, the blending component (B) was adjusted. Further, in the above formula (III), 12 parts of a dye precursor in which X is a bromine atom, Y is a nitro group, and Z is an acetyl group is obtained by combining 6 parts of a formaldehyde condensate of naphthalene sulfonate and 6 parts of lignin sulfonate with The mixture was dispersed into fine particles together with 24 parts of water to adjust the compounding component (C), and these compounding components (A), (B) and (C) were mixed to obtain 200 parts of a dark blue dye composition.

4 parts of this navy blue disperse dye composition and 3 parts of higher alcohol sulfate ester were adjusted to pH = 4 (adjusted with acetic acid-sodium acetate), pH = 7 (ion exchange water), pH = 9 (Diaserver PH95 (Mitsubishi) The dyeing bath is prepared by uniformly dispersing each of the three types of water in 3000 parts of water (adjusted by Kasei-Hoechst Co.). 100 parts of a polyester cloth is immersed in the dyeing solution and dyed at 135 ° C. for 40 minutes. The dyed product is placed in a bath composed of 6 parts of caustic soda, 6 parts of hydrosulfite, 6 parts of a nonionic surfactant and 3000 parts of water. 1 at 85 ° C
After performing reduction washing for 5 minutes, washing with water and drying, a dark blue dyed product was obtained. This dyed product dyed in three kinds of dye baths of pH = 4, 7, 9 has excellent fastnesses such as light fastness, sublimation, washing, water and friction after heat setting at 180 ° C. for 60 seconds. P. For dark blue dyed goods dyed in a dye bath of pH = 4
The hue differences of the dark blue dyeings dyed with the dye baths of H = 7 and 9 were slight.

Example 2 In the above formula (I), 24 parts of a dye precursor in which X is a bromine atom and Y is an acetyl group were prepared by mixing 12 parts of a formaldehyde condensate of naphthalenesulfonate, 12 parts of a ligninsulfonate and water Fine particles were dispersed together with 48 parts to prepare a compounding component (A). Similarly, in the above formula (II), 14 parts of the dye precursor in which X is a bromine atom was combined with 7 parts of a formaldehyde condensate of naphthalenesulfonate, 7 parts of a ligninsulfonate, and 28 parts of water.
And the mixture was dispersed in fine particles together with the mixture to prepare the component (B).
Further, in the above formula (III), 12 parts of a dye precursor in which X is a bromine atom, Y is a cyano group, and Z is an acetyl group are combined with 6 parts of a formaldehyde condensate of naphthalenesulfonate and 6 parts of a ligninsulfonate. And 24 parts of water to form fine particles and disperse the mixture, to adjust the compounding component (C), and to mix these compounding components (A), (B) and (C) to prepare a dark blue dye composition 20
0 parts were obtained. 4 parts of this navy blue disperse dye composition was used in Example 1
Dyeing and reduction washing were carried out under the same conditions as described above, washed with water and dried to obtain a dark blue dyed product. This dyed product dyed in three kinds of dye baths of pH = 4, 7, 9 has excellent fastnesses such as light fastness, sublimation, washing, water and friction after heat setting at 180 ° C. for 60 seconds. There was a slight difference in the hue between the dark blue dyed products in the pH = 7 and 9 dye baths compared to the dark blue dye products dyed in the pH = 4 dye bath.

Example 3 25 parts of concentrated sulfuric acid and nitrosyl sulfuric acid 57 at a concentration of 43.6%
50 parts of the compound represented by the formula (VIII) wherein X is bromine was added to the mixed solution of the above formula (VIII), and the mixture was stirred at 50 ± 3 ° C. for 2 hours to obtain the compound of the formula (VIII)
Thus, a diazotized solution of a compound in which X is bromine was obtained. Meanwhile, 1
In 500 parts of 7.5% hydrochloric acid, 26 parts of the compound represented by the formula (V) wherein Y is a benzoyl group, 11 parts of the compound represented by the formula (VI), and Z represented by the formula (VII) Then, 13 parts of the compound (1) was mixed and dissolved, and then 1000 parts of ice was added, and the mixture was cooled to 0 ° C. or lower, and a diazotized solution was added dropwise to perform coupling. After completion of the reaction, the mixture was filtered and washed with water to obtain 90 parts of a blue dye composition (equivalent to drying). 50 parts of the dark blue disperse dye composition was finely dispersed together with 25 parts of a formalin condensate of naphthalenesulfonate, 25 parts of ligninsulfonate and 100 parts of water to obtain a dark blue disperse dye composition. 4 parts of this navy blue disperse dye composition was dyed and reduced under the same conditions as in Example 1, washed with water and dried to obtain a navy blue dyed product. This dyed product dyed in three kinds of dye baths of pH = 4, 7, 9 has excellent fastnesses such as light fastness, sublimation, washing, water and friction after heat setting at 180 ° C. for 60 seconds. Was. Further, the difference in hue between the dark blue dyed product dyed in the pH = 7 and 9 dye baths was slightly different from that of the dark blue dyed product dyed in the pH = 4 dye bath, as in Examples 1 and 2. The same result as that of the dark blue disperse dye composition obtained by blending was obtained.

Examples 4 to 56 and Comparative Examples 1, 2, and 3 Examples 4 to 49 and Comparative Examples 1, 2, and 3 are shown in Table 1.
According to the described components of formulas (I) to (III), the amounts used and the fine particle composition, the same as in Examples 1 and 2, and also in Examples 50 to
With respect to No. 56, a navy blue disperse dye composition was obtained in the same manner as in Example 3 according to the components of formulas (V) to (VIII) shown in Table 1, the amounts used, and the fine particle composition. The dyeing method and the measurement of various fastnesses were performed in the same manner as in Examples 1, 2 and 3.

[0038]

[Table 1]

[0039]

[Table 2]

[0040]

[Table 3]

[0041]

[Table 4]

[0042]

[Table 5]

[0043]

[Table 6]

[0044]

[Table 7]

[0045]

[Table 8]

[0046]

[Table 9]

[0047]

[Table 10]

Next, Table 2 shows Examples and Comparative Examples of the navy blue disperse dye composition of the present invention, a disperse dye composition represented by the formulas (I) and (III), a disperse dye of the formula (II), It shows the results of dyeing using a commercially available dye and further measuring various fastnesses.

[0049]

[Table 11]

[0050]

[Table 12]

The methods for measuring the various fastnesses are as follows. Lightfastness: JIS L-0842 (Carbon Fade Meter) JIS Blue Scale Judgment Sublimation Fastness: JIS L-0879 B (Iron Tester, 180 ° C-30 seconds) JIS Contamination Gray Scale Judgment Washing Fastness: JIS L- 0844 A-4 JIS
Gray scale judgment for contamination Water fastness: JIS L-0846 Method A JIS Gray scale judgment for contamination Friction fastness: JIS L-0849 (friction tester II
Type) Gray scale judgment for JIS contamination

The pH dependency was evaluated by the following method. Staining is performed in three stages of pH = 4, 7, and 9, and pH = 4
PH = 7, p for the hue of the dyed product dyed in the dye bath
The hues of the dyed products dyed in a dye bath of H = 9 were compared. JIS gray scale judgment for discoloration and fading pH = 4 (prepared with acetic acid and sodium acetate) pH = 7 (ion exchange water) pH = 9 (Mitsubishi Kasei Hoechst Co. Diaserver PH9)
(Adjust at 5)

As is evident from the measurement results in Table 2, the navy blue disperse dye compositions of the present invention have low pH dependence and good various fastnesses including sublimation fastness as compared with commercially available dyes. I understand.

Further, a black disperse dye composition obtained by using the navy blue disperse dye composition obtained in the present invention as a base and having a small pH dependency and good fastness including sublimation, is also specifically described in the following Examples. It will be described, but the present invention is not limited to these examples (where "parts" means "parts by weight"
Represents).

Example 1 'In the above formula (I), 10 parts of a dye precursor in which X is a chlorine atom and Y is a benzoyl group were combined with 5 parts of a formaldehyde condensate of naphthalenesulfonate and 5 parts of a ligninsulfonate, Fine particles were dispersed together with 20 parts of water to prepare a compounding component (A). Similarly, in the above formula (II), 8 parts of the dye precursor in which X is a bromine atom is finely dispersed together with 4 parts of a formaldehyde condensate of naphthalenesulfonate, 4 parts of a ligninsulfonate, and 16 parts of water. Component (B) was adjusted. Similarly, in the above formula (III), 7 parts of a dye precursor in which X is a bromine atom, Y is a nitro group, and Z is an acetyl group, are mixed with 3.5 parts of a formaldehyde condensate of naphthalene sulfonate and lignin sulfonate. It was finely dispersed together with 3.5 parts and 14 parts of water to prepare a blending component (C). Further, the formula (IV)
25 parts of a dye precursor in which X is a chlorine atom and Y is a cyano group are combined with 12.5 parts of a formaldehyde condensate of a naphthalene sulfonate, 12.5 parts of a lignin sulfonate and 5 parts of water.
0 parts and finely dispersed, to adjust the blending component (D),
These components (A), (B), (C) and (D) were blended to obtain 200 parts of a black disperse dye composition.

The black disperse dye composition (6 parts) contained 3 parts of a higher alcohol sulfate ester, pH = 4 (prepared with acetic acid-sodium acetate), pH = 7 (ion-exchanged water), pH = 4
9 (Diaserver PH95 (Mitsubishi Kasei-Hoechst))
), And uniformly dispersed in 3000 parts of three types of water to adjust each dyeing bath. Add a polyester cloth 1
After dyeing at 135 ° C. for 40 minutes, the dyed product was treated in a bath consisting of 6 parts of caustic soda, 6 parts of hydrosulfite, 6 parts of a nonionic surfactant and 3000 parts of water in a bath consisting of 8 parts.
Reduction washing was performed at 5 ° C for 15 minutes, followed by washing with water and drying to obtain a black dyed product. This dyed product dyed in three kinds of dye baths of pH = 4, 7, 9 has excellent fastnesses such as light fastness, sublimation, washing, water and friction after heat setting at 180 ° C. for 60 seconds. There was almost no difference in hue between the black dyed product dyed with the pH = 7 and 9 dye baths with the black dyed product dyed with the pH = 4 dye bath.

Examples 2 'to 15' Examples 2 'to 15' were prepared according to the formulas (I) to (I) shown in Table 3.
A black disperse dye composition was obtained in the same manner as in Example 1 ', based on each component of V), the amount used and the composition of fine particles. The dyeing method and various fastnesses were measured in the same manner as in Example 1 '.

[0058]

[Table 13]

[0059]

[Table 14]

[0060]

[Table 15]

Table 4 shows the results obtained by dyeing a black disperse dye composition based on the navy blue disperse dye composition of the present invention as an example and a comparative example using a commercially available dye and further measuring various fastnesses. It is a thing. In addition, the method of measuring various fastnesses and the method of evaluating pH dependency were performed in the same manner as in Examples and Comparative Examples of the navy blue disperse dye composition.

[0062]

[Table 16]

As is evident from the measurement results in Table 4, the black disperse dye compositions based on the navy blue disperse dye compositions of the present invention all have a lower pH dependency and a lower sublimation fastness than commercially available dyes. It can be seen that the various types of fastness are good.

──────────────────────────────────────────────────続 き Continuation of the front page (56) References JP-A-53-137229 (JP, A) JP-A-1-210465 (JP, A) JP-A-57-167356 (JP, A) JP-A-56-167356 135560 (JP, A) JP-A-61-223039 (JP, A) (58) Fields investigated (Int. Cl. ⁶ , DB name) C09B 67/22 D06P 1/18 D06P 3/54 CA (STN) REGISTRY (STN) WPIDS (STN)

Claims (3)

(57) [Claims] A dye 40 to 5 represented by the following structural formula (I)
5% by weight [In the formula (I), X represents a chlorine or bromine atom, and Y represents an acetyl group or a benzoyl group] 20 to 35% by weight of a dye represented by the following structural formula (II): [In the formula (II), X represents a chlorine or bromine atom] and 15 to 30% by weight of a dye represented by the following structural formula (III): [In the formula (III), X represents a chlorine or bromine atom, Y represents a nitro group or a cyano group, Z represents an acetyl group or a benzoyl group, a combination of Y is a cyano group and Z is a benzoyl group. A water-insoluble dark blue disperse dye composition having low pH dependency and good sublimation fastness. 2. A dye represented by the following structural formula (IV):
0% by weight Wherein in the formula (IV), X represents a chlorine, bromine or hydrogen atom, and Y represents a cyano group, a phenoxy group or an oxybenzoyl group.
A water-insoluble black disperse dye composition characterized by being blended in an amount of from 70 to 70% by weight. 3. A method for dyeing polyester fibers, comprising using the disperse dye composition according to claim 1 or 2.