JPH0525402A - Azo dye composition showing good dyeing reproducibility - Google Patents

Abstract

PURPOSE:To provide an azo dye composition showing good dyeing reproducibility. CONSTITUTION:The objective composition comprises 5-70wt.% powdery starting material of a water-insoluble azo dye, 5-95wt.% product of the condensation of formalin with an alkylnaphthalenesulfonic acid and/or product of the condensation of formalin with creosote oil sulfonic acid, and 0-90wt.% water. This composition shows improved dyeing reproducibility even in dyeing in a dye bath which is acidic or is neutral to weakly alkaline.

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to an azo disperse dye composition used for dyeing synthetic fibers such as polyester fibers and triacetate fibers.

[0002]

2. Description of the Related Art Synthetic fibers such as polyester fibers and triacetate fibers are usually dyed with a disperse dye under high temperature and high pressure. Generally, a disperse dye contains a water-insoluble chromogen and a dispersant, which are finely pulverized to about 1 μm, as main components, and there are various kinds of dispersants used at this time. For example, as a commonly used dispersant, polyoxyethylene, alkyl ether, polyoxyethylene alkylphenyl ether, polyoxyethylene, distyrenated phenyl ether, polyoxyethylene, polyoxypropylene cocondensate, higher grade Nonionic surfactants such as aliphatic alcohol ethylene oxide adducts, higher fatty acid ethylene oxide condensates, polyoxyethylene alkylamines, higher fatty acid glycerin esters, and higher fatty acid sorbitan esters, and higher alcohol sulfuric acid. There are anionic surfactants such as ester, sulfuric acid ester of higher fatty acid, alkylbenzene sulfonic acid, phosphoric acid ester of higher alcohol, and copolymer of styrene and maleic acid. Commonly used anionic dispersants are formalin condensates of naphthalene sulfonic acid and alkylbenzene sulfonic acid, lignin sulfonic acid (hereinafter abbreviated as LS), formalin condensate of cresol sulfonic acid (hereinafter abbreviated as CrSF), and cresol. And 2-naphthol-6-
Formalin condensate of sulfonic acid (hereinafter abbreviated as CrNSF), formalin condensate of naphthalene sulfonic acid (hereinafter abbreviated as NSF), formalin condensate of alkylnaphthalene sulfonic acid (hereinafter abbreviated as ANSF), formalin of creosate oil sulfonic acid Examples thereof include condensates (hereinafter abbreviated as CrOSF).

However, each of these dispersants is a dispersion speed at the time of producing a disperse dye, stability of the dispersion over time, cohesiveness at spray drying, or deterioration of dispersibility at high temperature and high pressure dyeing, and color in printing. There are merits and demerits in terms of paste stability cost and the like, and it is extremely common in the art to produce a disperse dye by combining a plurality of dispersants. For example, NSF alone causes significant deterioration in high temperature dispersibility, so LS and Cr
Frequently, SF is mixed, NSF and LS are used in combination at a specific ratio in order to adjust the permeability of the cloth for printing. Further, NSF lowers the viscosity when making the dye base fine particles into dispersed particles and facilitates the operation of dispersion, but on the other hand, the dispersion speed is remarkably inferior and the dispersibility deteriorates with time. Are used together. or,
NSF is used together with LS and CrOSF because it tends to cause aggregation of the dye during spray drying of the dye, and conversely, because LS is highly contaminated with the fibers during dyeing, NSF and ANSF are used together in appropriate amounts.

[0004]

Disperse dyes are roughly classified into three types of anthraquinone dyes, azo dyes, and condensation dyes according to their structural skeletons.
It has been pointed out that the reproducibility of dyeing is inferior to the types of dyes. That is, in general, azo dyes are liable to cause color blur density blur due to hydrolysis of azo groups and terminal groups during dyeing under high temperature and high pressure, and are affected by dye bath pH, bath ratio, type of dyeing object, etc. It is pointed out that it is an easy genus. In particular, further improvement in dyeing reproducibility of azo dyes in neutral to alkaline dyeing baths, which has been remarkably popularized in recent years, is required.

[0005]

Means for Solving the Problems The inventors of the present invention have completed the present invention as a result of earnest research on a composition that solves the above-mentioned drawbacks and reproducibly brings out a high color value originally possessed by an azo dye. It came to. As a result, it was discovered that the specific dispersant in the disperse dye influences the dyeing reproducibility. According to the present invention, high color value and dyeing reproducibility can be obtained by combining an azo dye and a specific dispersant. That is, the present invention relates to a formalin condensate (ANSF) of 5 to 70% by weight of a water-insoluble azo dye raw material alkylnaphthalenesulfonic acid in a composition and / or a formalin condensation of creosate oil sulfonic acid (CrO).
SF) An azo dye composition containing 5 to 95% by weight of water and 0 to 90% by weight of water, and a dyeing method using the same are provided. It is difficult to obtain good dyeing reproducibility when a dispersant that is usually used other than those described in the present invention is used alone or in combination.

Examples of the water-insoluble azo dye precursor of the present patent include monoazo dyes and disazo dyes.
Further, a method in which a formalin condensate of an alkylnaphthalene sulfonic acid or a formalin condensate of a cleosoate oil sulfonic acid used as a dispersant is respectively sulfonated in a sulfuric acid of an alkylnaphthalene or a creosote oil, and then condensed with formalin ( For example, it can be obtained in the same manner as in “Synthesis of Surfactants and Their Applications” (published by Enoki Shoten, 1957, page 90). The raw material naphthalene may be crude or refined naphthalene, and examples of the alkyl group of the alkylnaphthalene include an alkyl group having 1 to 4 carbon atoms such as methyl, ethyl, propyl, butyl and isobutyl groups. The creosote oil may be any of medium, light and heavy components.

The preferred azo dye composition of the present invention is 10 to 50% by weight of a water-insoluble azo dye,
It is a composition containing 20 to 80% by weight of a formalin condensate of an alkylnaphthalene sulfonic acid and / or a formalin condensate of a cleosate oil sulfonic acid and 0 to 70% by weight of water. In the composition of the present invention, a water-insoluble azo dye, which is usually provided in the form of a press cake, is mixed with water and the specific dispersant of the present invention to prepare a uniform slurry, which is then pulverized by a colloid mill or sand grinder. It is obtained by wet pulverization to about 1 μm.

Further, the liquid disperse dye obtained by forming fine particles can be put in a can as it is and can be marketed, or can be marketed as a powdered product by spray drying or the like. Further, the composition of the present invention contains a small amount of a defoaming agent, an antifungal agent, a wetting agent, an antidust agent, a dispersion stabilizer, and a builder such as mirabilite and dextrin, which do not affect the dyeing. It is also possible to let.

The dye composition of the present invention is dissolved or diluted in water and then synthetic fiber such as polyester fiber, triacetate fiber and the like and other fibers (for example, cotton and ray
Yon, wool, nylon) and mixed fabrics and dyed mixed woven products. The dye composition of the present invention may be used to dye the polyester fiber, the triacetate fiber, or the mixed fiber of the polyester fiber, the triacetate fiber and the other fiber in various manners. The dye composition is dissolved in an acidic or weakly alkaline aqueous medium, and the dye composition is mixed with the dye cloth under high pressure at 100 to
It is also possible to carry out dip dyeing at 130 ° C. or to carry out dyeing by a printing method or a pad method by adjusting a printing paste and a pad bath by a conventional method. In the dyeing, various embodiments, for example, a batch dyeing method using Wins, Jitsuger, a jet dyeing machine, a continuous dyeing method using a pad roll, a pad dry, a pad steam, a screen, or the like. Alternatively, a printing method using a roll or the like can be adopted.

[0010]

EXAMPLES The present invention will be specifically described by way of examples, but the present invention is not limited to these examples. Example 1 Azo dye C.I. I. Disperse Blue 183 Bulk powder 32.6 parts, water 167 parts and sodium salt of formalin condensate of methylnaphthalene sulfonic acid (hereinafter abbreviated as MeNSF) 6
After adding 7.4 parts and stirring well to make a slurry,
The pH was adjusted to 7.0 with acetic acid and finely divided into particles of about 1 μm using a sand grinder by a conventional method to obtain 267 parts of a liquid azo dye composition. This dye composition had stable dispersibility for 3 months and did not generate coarse particles. Further, in order to observe the dyeing reproducibility of this composition, the following standard dyeing and severe dyeing were carried out.

(1) Standard Dyeing (Pressure Dyeing) First, 100 mg of the azo dye composition obtained in this Example 1 was precisely weighed and dissolved in 180 ml of dyeing water whose pH was adjusted to 4.5 with acetic acid and sodium acetate. A dyebath was prepared by dispersing. 5 g of a plain weave fabric of polyester fiber was immersed in this at 30 ° C., and the high-pressure dyeing machine was air-pressurized with 3 kg / cm ² and then heated to 130 ° C. in 45 minutes, dyed at the same temperature for 60 minutes, and washed with water. ,
It was reduced and washed and dried at 80 ° C. (2) Severe dyeing 1 (self-pressure dyeing) A dyeing bath is prepared by the same method as the standard dyeing method of (1), and then pressurized with 3 kg / cm ² of air described in the standard dyeing method of (1). Instead of performing the above, close the lid of the high-pressure dyeing machine, raise the temperature to 130 ° C. under autogenous pressure, and dye at the same temperature for 60 minutes,
It was washed with water, reduced, and dried at 80 ° C. (3) Severe dyeing 2 (neutral dyeing) 100 mg of the azo dye composition obtained in Example 1 was precisely weighed,
A dyebath was prepared by dissolving and dispersing in 180 ml of distilled water. 5 g of a plain weave cloth of polyester fiber was immersed in this at 30 ° C., heated to 130 ° C. under air-pressurization as in the standard dyeing method (1), dyed at the same temperature for 60 minutes, washed with water, and reduced and washed. It was dried at 80 ° C. (4) Severe dyeing 3 (alkali dyeing) 100 mg of the azo dye composition obtained in Example 1 was precisely weighed,
180 ml of dyed water adjusted to pH 9.0 with aqueous ammonia
To prepare a dyebath. 5 g of a plain weave cloth of polyester fiber was immersed in this at 30 ° C., heated to 130 ° C. under air-pressurization as in the standard dyeing method (1), dyed at the same temperature for 60 minutes, washed with water, and reduced and washed. And dried at 80 ° C.

The pressure-dyed cloth, the self-dyed cloth, the neutral dyed cloth, and the alkali-dyed cloth thus dyed are each measured for reflectance with a Macbeth reflectometer, and self-dyed with respect to the pressure-dyed cloth (standard dyed cloth). The density and color difference (ΔE) of the cloth, the neutral dyed cloth and the alkali dyed cloth were measured. As a result, the pressure-dyed cloth, the self-dyed cloth, the neutral-dyed cloth, and the alkali-dyed cloth showed a decrease in density and a slight change in hue, but the change was only minimal for severe dyeing.

Comparative Example 1 A liquid azo dye composition was obtained in the same manner as in Example 1 except that LS was used instead of NeNSF in Example 1. This azo dye composition was dyed in the same manner as in Example 1, and the density and color difference (ΔE) of the self-pressure dyeing cloth, the neutral dyeing cloth and the alkali dyeing cloth with respect to the pressure dyeing cloth were measured. . As a result, the decrease in density and the change in color difference were remarkable as compared with Example 1, and the difference was clearly recognized even with the naked eye.

Example Comparative Example 2 Instead of 67.4 parts of MeNSF of Example 1, CrOSF was used.
A liquid azo dye composition was obtained by the same operation as in Example 1 using 67.4 parts. By the method described above, pressure dyeing, self-pressure dyeing, neutral dyeing, and alkali dyeing were performed, and the density and color difference with respect to the pressure dyeing cloth were measured. As in the case of Example 1, the density and hue change were kept to a minimum for severe dyeing.

Comparative Example 2 LS 20 was used in place of 67.4 parts of CrOSF of Example 2.
Part, the result of dyeing the composition using a mixture of 47.4 parts of MeNSF was as follows. Compared with Example 2, the decrease in density and the change in hue were remarkable, and the difference was clearly recognized even with the naked eye. The results of other azo dyes tested in the same manner are shown in the table below (Table 1: Preparation of azo dye composition, Table 2: Dyeing result). What is spray drying?
A liquid composition finely divided by a conventional method is spray-dried at an inlet temperature of 120 ° C. and an outlet temperature of 80 ° C. to obtain a powdery composition.

[0016]

[Table 1]

[0017]

[Table 2]

[0018]

The azo dye composition having good dyeing reproducibility was obtained.

Claims (2)

[Claims] 1. Water-insoluble azo dye 5 to 70% by weight Alkylnaphthalene sulfonic acid formalin condensate and / or creosate oil sulfonic acid formalin condensate 5 to 95% by weight Water 0 to 90% by weight An azo dye composition comprising: 2. A method for dyeing polyester fiber, which comprises using the azo dye composition according to claim 1.