JPS58213049A - Method for coloring organic material - Google Patents

Abstract

PURPOSE:To dye org. materials, particularly hydrophobic synthetic resin fibers in clear color tone with good fastness to light and sublimation by using a specified anthraquinone dye. CONSTITUTION:An org. material such as polyester fiber is dyed by using a dye compd. of formula I (wherein R1, R2 are each H, amino, hydroxyl, halogen, nitro, methyl, methoxy, cyano; m is 1,2,3; n is 1,2) which exhibits excellent dyeability by any of high-temperature dyeing method or carrier dyeing method. Said dye compd. can be produced by reacting an anthraquinone derivative of formula IIsuch as 1,5-dihydroxy-8-nitroanthraquinone with tetrachlorophthalic acid (derivative) in an approximately equimolar ratio in an inert solvent at 50-250 deg.C for 0.5-10hr.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates generally to a method for coloring organic materials, and more specifically to a method for dyeing organic materials, particularly hydrophobic synthetic fibers and synthetic resins such as polyester fibers, using a novel dye. Regarding.

Conventionally, various dyes for dyeing hydrophobic fibers such as polyester fibers have been developed and widely used.
Since such dyes dye hydrophobic fibers, their molecular weights are relatively low and their crystallinity is low. Therefore, sublimation resistance is inevitably low, and various problems occur during various heat treatments of dyed fabrics. Further, for the same reason, the dye tends to migrate to the surface of the fiber after dyeing, and the dry and wet rubbing fastness and light resistance are insufficient. One way to solve these drawbacks is to use a dye that has a high molecular weight and good crystallinity, that is, is stable against heat. A new problem arises: the speed is drastically reduced.

As a result of intensive research to solve the above-mentioned drawbacks of the conventional technology, the present inventor has found that by incorporating a certain structure into the chemical structure of the dye, even dyes with relatively high molecular weight and good crystallinity can be used. The present invention was completed based on the finding that the dye has excellent dyeing properties.

That is, the present invention provides an organic material 0 characterized in that it uses a dye represented by the following general formula (I).
0 (However, R3 in the formula & is a hydrogen atom, an amino group, a hydroxyl group, a halogen atom, a methyl group,
It is a methoxy group, a cyano group, or a nitro group, and m is 1.
2 or 3, n is 1- or 2. ) To explain the present invention in detail, the dye represented by the above general formula Approximately 50 ~ in an inert solvent
React at a temperature of 250°C for about 0.5 to 10 hours.
Therefore, it can be easily obtained.

Island, Fb and m s n (in the above formula) have the same meanings as above.

Alternatively, the above general formula (
The dye 1) can be obtained.

ct R2 and n in the above formula have the same meanings as above.

The anthraquinone derivative represented by the above general formula (It) is a known compound, and representative examples include U, 1,5-
dihydroxy-8-nitroanthraquinone, 1,5-dihydroxy-8-aminoanthraquinone, 1,8-dihydroxy-5-nitroanthraquinone, 1,5.8-)
Lihydroxyanthraquinone, 1,8-dihydroxy-
As a substituent at position 4 of 5-aminoanthraquinone, 4-amino or 3-aminophenylamino group, 3
-chloro-5-akinophenylamino group, 3-chloro-
4-aminophenylamino group, 2-methyl-5-chloro-4-aminophenylamino group, 2-methyl-5-methoxy-4-aminophenylamino group, 2.5-dimethyl-4-aminophenyl group, 2 , 5-dichloro-4-aminophenylamino group, 2-methyl-3-aminophenylamino group% 2-methoxy-4-aminophenylamino group, 2-cyano-4-aminophenylamino group, etc. .

Synthetic fibers to which the method of the present invention is applied include:

Examples include polyester fibers, polyester ether fibers, cellulose ester fibers such as acetate fibers and triacetate fibers, and polyamide fibers, but these fibers or blends of these fibers with other types of fibers may be used. The method of the present invention can also be applied to woven fiber products.

According to the method of the present invention, the synthetic fibers described above can be dyed in vivid colors with excellent light fastness, sublimation resistance, and other fastness properties. A dyed product with good sublimability can be obtained. Furthermore, the dye of the present invention exhibits excellent dyeing properties both in high-temperature dyeing and carrier dyeing, and is therefore extremely advantageous industrially.

It is surprising that the dye used in the present invention has such excellent dyeing properties even though it has a relatively high molecular weight and crystalline sleeve.

The dye used in the method of the present invention is particularly useful for coloring not only the above-mentioned hydrophobic fibers but also various other organic materials, such as synthetic resins, synthetic paints, printing inks, etc., according to the conventional methods in each field. By coloring organic materials, colored products with excellent clarity, transparency, and light resistance can be obtained.

For coloring materials other than fibers, such as thermoplastic resins and thermosetting resins, substantially the same methods as conventional methods using pigments can be employed. For example, for polyolefin resins such as polyethylene, polypropylene, and polystyrene, the dry color method and masterbatch method are suitable, and for other synthetic resins (e.g., rubber% PVC, polyester, polyamide, urea resin, phenolic resin, etc.) A similar method can be used. The advantage of using the dye of the present invention for thermoplastic resins and thermosetting resins is that the colored product obtained is very uniformly colored, a high coloring effect can be obtained even when a small amount is used, and the dye of the present invention is different from conventional colorants. There is no need for special treatment for fine dispersion treatment as in pigments. According to the present invention, the coloring agent is easily and uniformly dissolved or dispersed in the material to be colored, so that problems such as agglomeration and coarsening of the pigment particles and poor dispersion of the particles can be avoided. This is because no problems arise.

Next, the details of the method of the present invention will be explained more specifically with reference to the following examples.

In the examples, parts and parts are based on weight.

Example 1 3000 ml of water containing 1 part of the dye having the following structural formula, 2 parts of a condensate of oxynaphthalene sulfonic acid and cresol formaldehyde, and 2 parts of 1 m of naphthalene sulfonic acid and formaldehyde.
10 polyester fibers are finely dispersed in this bath.
0 part was immersed and treated at 130°C for 60 minutes. After treatment, wash with water and add 3000 g of water containing 4 parts of higher alcohol sulfate ester.
The dyed material was subjected to noping treatment at 90° C. for 20 minutes, washed with water, and dried to obtain a deep, vivid blue dyed product with excellent light resistance, sublimation resistance, and abrasion resistance.

Light fastness (JIS, L, 1044 (1959) Fade meter 8th grade Sublimation fastness (180° C. x 30 seconds, iron tester) 5th grade The above dye was obtained according to the production method below.

〔Production method〕

1.5-dihydroxy-8-nitro-4-(4-aminophenylamino)anthraquinone 3.9 parts and 4.5,6 parts
．． 39 parts of 7-tetrachlorophthalanhydride WN2.9N and f2) rice vinegar rIRK were added, and the mixture was stirred under reflux for 35 hours. The precipitated blue crystals were filtered and washed to obtain 6.5 parts of a red dye (decomposed above 280° C.) represented by the above structural formula.

Example 2 1 part of the dye with the following structure was converted into a condensate of naphthalene sulfonic acid and formaldehyde 3
30 parts of water containing 1 part and 4 parts of higher alcohol sulfate ester
00 parts of polyester fibers and 100 parts of polyester fibers were added to this bath.
The sample was soaked and treated at 100°C for 90 minutes.

After treatment, soaping treatment was carried out in the same manner as in Example 1 to obtain a solid blue dyed product.

Side light fastness: 7th grade Sublimation fastness: 5th grade
1,5-dihydroxy-8 instead of dihydroxy-8-nitro-4-(4-aminophenyl)anthraquinone
-Amino-4-(4-aminophenylamino)anthraquinone was used, and the others were obtained in the same manner (
decomposes at temperatures above 340°C).

Example 3 A mixture of 05 parts of the dye used in Example 1 and 1.0 part of Pansolve ■ was mixed with 50 parts of a polyvinyl chloride resin compound, and the mixture was kneaded with a 6-inch roll at 155 to 160°C for 3 minutes. Form a sheet and heat this sheet to 170℃
The product, which was press-molded at a pressure of 50 k7 to a thickness of 5 cages, was colored transparent pure blue.

Example 4 5 parts of the finely ground dye used in Example 2 were mixed with 1,000 parts of polyethylene and injection molded at 250°C. The molded products were transparent and uniformly colored to blue.

Example 5 10 parts of the dye, 1 part of the dispersant and 89 parts of ethylene glycol used in Example 1 were ground in a ball mill, and 15 parts of this ground product was obtained from 1 mole of dimethyl terephthalate and 2 moles of ethylene glycol. Transesterification product 10
0 parts, heated and polymerized at about 280°C for 4 hours under reduced pressure,
A uniformly and beautifully colored blue polyester was obtained. When this colored polyester was spun according to a conventional method, no clogging of the spinning nozzle occurred.

Examples 6 to 24 Using the compound of general formula (II) shown in Table 1 below, and using various new dyes obtained in the same manner as in Examples 1 to 2, Example 5 and When polyester resin was colored in the same manner, the results shown in Table 1 below were obtained.

Claims (1)

[Claims] (1) A method for coloring an organic material, characterized by using a dye represented by the following general formula (1). (However, in the formula, hydrogen atom, amino group, hydroxyl group, halogen atom, nitro group, methyl group, methoxy group,
It is a cyano group, and m is 1°2 or 3. n is 1 or 2
It is. )