JPS63213565A - Monoazo compound and method for dyeing hydrophobic fiber using said compound - Google Patents

Abstract

NEW MATERIAL:A compound expressed by formula I (R1 is 2-8C alkyl; R2 is 1-4C alkyl). EXAMPLE:A compound formula II. USE:A dye for dyeing a synthetic fiber such as polyamide fiber, polyester fiber, etc., semisynthetic fiber or mixed fiber material of the above-mentioned fiber with a natural fiber, especially polyester fiber or mixed fiber of the polyester fiber and cellulose fiber in fresh blue. PREPARATION:A compound expressed by formula III (X is halogen; Y is halo gen or cyano) [e.g. 2-(2-bromo-6-cyanol-4-nitrohenylazo)-5-(N,N-bis-2-ethoxy- carbonyloxyethyl)aminoacetoanilide, etc.] is reacted with a metal cyanide [e.g. copper ( I ) cyanide] in a polar solvent (e.g. DMF) to provide the compound expressed by formula I.

Description

DETAILED DESCRIPTION OF THE INVENTION <Industrial Application Field> The present invention relates to monoazo compounds and their application to hydrophobic fibers.

<Prior Art> In recent years, as consumer needs have become more sophisticated, ALF6 materials have been increasingly used in automobile interiors. In particular, polyester fiber materials have been increasingly used as automobile interior materials due to their excellent heat resistance and light resistance. Along with this, the disperse dyes used as coloring agents are also required to have excellent fastness, particularly light fastness at high temperatures.

Light fastness is normally determined by exposure for 40 to 80 hours under the conditions specified in JIS-LO842 (63±8'C), but for automotive interior applications, it is exposed to light for 40 to 80 hours at a high temperature of 838°C. Fastness that can withstand 600 hours of exposure is required.

Particularly in applications for automatic seats, where a polyester material is pasted onto a urethane foam that has heat storage properties, there is a need for dyes that can withstand even harsher conditions.

Even if the L light fastness under normal JIS-LO842 conditions is good, the light fastness under the above harsh conditions is often questionable and low, and it is difficult to predict from the JIS method results. situation.

<Problems to be solved by the invention> As blue dyes with excellent light resistance, the following formulas (A) and (
B) The compounds shown in (b) have been put into practical use, but all of them have the drawbacks of poor build-up properties and lack of concentration, as well as the problem of high cost because they are anthraquinone-based.

On the other hand, compounds represented by the following formula (/U) have been put into practical use as azo-based blue dyes that are cost-effective and have excellent build-up properties. Although there is no problem, the light fastness is significantly reduced in the above-mentioned light fastness test for automobile interior applications, and it cannot be used at all practically.

Compounds represented by the following formula are also known, but these have poor dye properties, including dyeability and build-up properties, and are problematic in practice.

The present inventors conducted extensive research to find a dye that has good build-up properties, light fastness, especially light fastness for automotive interior applications, and is also advantageous in terms of cost. It was discovered that it has the desired performance.

Means for Solving Problems> The present invention is based on the following general formula (1) (wherein R1 is a straight chain or branched alkyl group having 2 to 8 carbon atoms, and R2 is a straight chain or branched alkyl group having 1 to 4 carbon atoms. The present invention provides a monoazo compound represented by the following formula, and a method for dyeing hydrophobic fibers using the same.

The alkyl group represented by % R1 in the general formula (1) includes ethyl group, n-propyl group, 1so-propyl group, n-butyl group, 1so-butyl group, 5ee-butyl group, tert-butyl group, n-pentyl group, 1so-pentyl group, n-hexyl group, 1SO-hexyl group, n-
hebutyl group, n-octyl a, 1so-octyl group, 2
Examples of the alkyl group represented by R2 include methyl group, ethyl group, n-propyl group, 1so-propyl group, n-butyl group, and is.

-butyl group, etc.

Among these, R1 is preferably an ethyl group, n-propyl group, 1so-propyl group, n-butyl group, 1so-butyl group, etc., and R2 is preferably a methyl group, ethyl group, etc.

The monoazo compound represented by the general formula (1) is represented by the following general formula (I) (wherein, X is a halogen atom, Y is a halogen atom or a cyano group, and R+ and R2 each have the above meanings.) The compound represented by
It can be easily obtained by reacting with metal cyanide in a polar solvent by the method described in Japanese Patent No. 785.

In addition, the amine represented by the following formula
-26875, by diazotization and coupling with a compound represented by the following general formula A monoazo compound represented by (■) can be obtained.

When the compound thus obtained is used as a dye, it is dispersed according to a conventional method.

Dispersion can be carried out, for example, in a sand mill by dispersing naphthalene sulfonic acid formalin condensate, lignin sulfonic acid, cresol.
Anionic dispersants such as Scheffer's acid formalin condensate, polyoxyethylene alkyl ethers, polyoxyethylene alkyl phenyl ethers, and other nonionic dispersants are used, and the appropriate dispersant is used. can be carried out in an aqueous medium. The obtained disperse dye liquid can be used as it is in liquid form or after being dried and used as powder or granules.

The compound (1) of the present invention is suitable for use in synthetic fibers such as polyamide fibers and polyester fibers, semi-synthetic fibers such as di- or triacetate fibers, or mixed fiber materials thereof with natural fibers, especially polyester fibers and natural or regenerated cellulose. The fibers mixed with the fibers can be dyed in a vivid blue color by a conventional dyeing method, continuous dyeing method, or printing method.

The compound of the present invention has Q-adhesive pill door 1. It is possible to provide a dyed product which has excellent dyeing properties such as dyeing properties, and also has excellent wet fastness, sublimation fastness, post-processing fastness, and light fastness, especially when used in a motor vehicle.

Hereinafter, the present invention will be explained in more detail with reference to Examples. In the examples, "part" refers to the crawling part, and "color tone" refers to the color on the polyester fiber.

Example 1 6.85 parts of 2-(2-bromo-6-dia-4-nitrophenylazo)-5-(N,N-bis-2-ethoxycarbonyloxyethyl)aminoacetanilide was quenched with dimethylforma. After 1×1; e; 4, the residue was removed by filtration, and then the mixture was discharged into water to precipitate crystals. The precipitated crystals were separated in a furnace, washed with water, and dried to obtain a compound of the following formula (1).

λmax 600 nrrN DMF) Color tone: Blue Note that 2-(2-bromo-6-dia-4-nitrophenylazo)-5-(N,N-bis-2-ethoxycarbonyloxyethyl)aminoacetanilide is 2- Bromo-6-cyano-4-nitroaniline is diazotized to form 8-
Obtained by cambling with (N,N-bis-2-ethoxycarbonyloxyethyl)aminoacetanilide.

Example 2 78 parts of 921.9 parts of 2.6-dicyano-4-nitroani
% sulfuric acid at 0-5°C.

After adding 3.1 parts of 48% nitrosyl sulfuric acid at 0 to 5°C, the mixture is stirred at the same temperature for 5 hours to effect diazotization. On the other hand, 8
-4.1 parts of (N,N-bis-2-n-propoxycarbonyloxyethyl)aminoacetanilide and 10 parts of glacial acetic acid
The diazotide is added at θ˜5′ O while cooling with ice. The coupling reaction is completed by stirring at the same temperature for 1 hour. The precipitated crystals were washed with water and dried to obtain a compound of the following formula (2).

λmax 601 parts m (DMF) Color tone: Blue Example 8 Dyeing was carried out using the compound (1) obtained in Practical Example 1 and the compound (2) obtained in Example 2 by the following procedure.

a) Preparation of dispersion Compound (1) or (2) 20 parts Anionic dispersant (Note 1) 20 parts Water
60 copies □

- Total 100 parts (Note 1) Natsuta 1-rulsulfonic acid formalin condensate The above mixture was processed in a sand mill for 10 hours to obtain a dispersion.

b) Staining 3 parts of the dispersion obtained in a) are placed in a dyeing pot together with aooo parts of water and adjusted to pH 5 using acetic acid. Next, 100 parts of polyester fabric was added and coloring was carried out at 180°C for 60 minutes. After dyeing is completed, reduction washing and rinsing are performed by a conventional method, followed by drying. It has excellent light fastness and other fastness properties, and produces a vivid, deep blue dyed product.

Examples 4 to 47 Compounds shown in the table below were obtained in the same manner as in Example 1 or 2,
Example 48 In each case, dyeing was carried out in the same manner as in Example 8 using the compound (1) obtained in Example 1 by the following operations.

a) Preparation of dispersion Compound (1) 20 parts Anionic dispersant (Note 1) 200 parts Total 100 parts (Note 1) See Example 8 The mixture was treated in an Andmill for 10 hours to obtain a dispersion. b) Color 0 Put 6 parts of the dispersion obtained in a) into a dyeing pot together with 1500 parts of water, add 0.6 parts of acetic acid, 2.4 parts of sodium acetate and Sumipon TF (Sumitomo Chemical Co., Ltd. Dyeing Assistant). agent) 1
．． Add 6 parts. Next, polyester fiber raised fabric 1
00 copies were added, and coloring was carried out at 180°C for 60 minutes. After dyeing is completed, reduction washing and rinsing are performed by a conventional method, followed by drying. It has excellent light fastness and other fastness properties, and produces dyed products with a bright, deep reddish color. This dyed product showed particularly good results in the light resistance test as shown below (Note 2) as a material for automobile interiors.

(Note 2) Light fastness test method for automobile interior materials A dyed material lined with urethane foam is irradiated for 800 hours with a fade meter (black panel temperature 88 ``O''), and the discoloration and fading of the irradiated area is determined by JIS L. Judgment was made by comparing with the gray scale for discoloration and fading of -0804.

Example 49 Using the dispersion obtained in Example 8 a), a printing paste having the following composition is prepared.

(Printing paste composition) Above dispersion 8 parts Half emulsion Nikgen paste (e2) 60 parts Tartaric acid 0.8 parts Sodium chlorate 1 part 0.2B water
Remainder - total 10
0 parts (Note 2) Half-emulgitane base glue composition Kerosene
70 parts water
25 part Viscon KM-B
(Note 8) Total of 5 parts 100 parts (Note 3 Shin Nakamura Chemical Co., Ltd. product: Emulsifier 8) Mix the above in a high-tl Z mixer.
0 parts of Tomeibrogum NP 12% paste (product of Grinara) and 70 parts of it are mixed to prepare a half emulsion paste.

Claims (2)

[Claims] (1) The following general formula (I) ▲Mathematical formulas, chemical formulas, tables, etc.▼(I) A monoazo compound represented by (representing a chain or branched alkyl group). (2) The following general formula (I) ▲Mathematical formulas, chemical formulas, tables, etc.▼(I) A method for dyeing hydrophobic fibers, characterized by using a monoazo compound represented by the following (representing a chain or branched alkyl group).