JPS58142938A - Bisazo compound and dyeing of fiber using the same - Google Patents

Abstract

NEW MATERIAL:The compound of formulaI[R<1> and R<2> are H, methyl or methoxy; Q is -SO2CH=CH2 or -SO2CH2CH2R (R is a group eliminable with alkali)] as free acid. EXAMPLE:The compound of formula II. USE:Dye for dyeing cellulosic fiber in navy color with excellent percentage of exhaustion and build up property. PROCESS:2-Naphthylamine-1-sulfonic acid is diazotized and coupled with equimolar amount of 1-amino-8-hydroxynaphthalene-3,6-disulfonic acid (salt) in an acidic medium at -5-+80 deg.C optionally in the presence of a reaction accelerator. The product is mixed with a compound obtained by diazotizing equimolar amount of the aromatic diamine of formula III and coupled at -5-+40 deg.C under weakly acidic-weakly alkaline conditions.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel bisazo compound and a method for dyeing cellulose fiber F7 using the same.

More specifically, the present invention relates to a novel fiber-reactive bisazo compound and a method for dyeing cellulose fibers navy color using the same.

C, I, Reactive Black 5 is known as a reactive dye that dyes cellulose fibers blue or black.However, although it has two vinyl sulfone-type fiber-reactive groups in its molecule, it does not dye cellulose fibers. However, there is a problem that the dyeing rate is insufficient.

In order to solve this problem, Examples 18 and 14 of Japanese Patent Publication No. 48-15299 describe dyes represented by the following formula and (B).

Example 17 of aSζ Japanese Patent Publication No. 45-4887 describes the dye (C) shown by the following formula, and the dyeing rate is
) is about 60% of that, dye (machi is about 6096 and dye (C
) is only about 60%, however, the present inventors conducted a thorough study to solve this problem, and found that a specific bisazo compound in which a specific number of sulfonic acids are present at a specific position in the structure. It has been found that these problems can be solved and a navy color dyed product having excellent dyeing rate and build-up property can be obtained in one go, and the present invention has been completed.

That is, the present invention provides a compound of the following general formula (I) in the form of a free acid [wherein s'1 m'l each independently represents hydrogen;
CkL-Mouse or -SO Snowfake MouseK is shown. Here, k is a group that leaves with an alkali. ] A bisazo compound shown in the following is provided.

The present invention also provides a method for dyeing cellulose fibers, which is characterized by using a bisazo compound represented by the general formula <Il.

The general formula (Q in Il is -50, CI(,C)l
, R, the alkali-removable group 1 includes, for example, halogen atoms such as chlorine and bromine atoms, ester groups of organic carboxylic acids and sulfonic acids, lower alkanoyloxy residues such as acetyloxy residues, benzoyloxy residues, etc. Examples include an oxy group, an S- group represented by the formula -0-8 or -050,H in the form of free acetic acid, or an acidic ester group of sulfuric acid.

Although the bisazo compounds of the invention can be present both in the free acid form and in the form of their salts, they are preferably in the form of the salts, especially the alkali and alkaline earth gold-1, especially the sodium, potassium and calcium salts. More preferred forms are alkali metal salts.

The bisazo compound represented by the general formula (i) of the present invention has excellent hospitality properties as a fiber-reactive dye, such as dyeing rate, alkali stability, dry-up properties, wash-off properties, etc., and has excellent gift fastness. is also a useful compound giving excellent navy dyeings.

The novel bisazo compound represented by the general formula (Il) can be produced as follows: 2-na7thylamine-1
- diazotizing sulfonic acid by a known method, adding equimolar amounts of 1-amino-8-hydroxynaphthalene-8,6-disulfonic acid or a salt thereof in an acidic medium, optionally with the addition of a reaction accelerator; -6 to B (11), and then the general formula ((I) [wherein, R1*IL1 and q have the above-mentioned meanings].

] Add equimole of the aromatic amine represented by diazotized by a known method, and add -6 under weak acidity to weak alkalinity.
It can be produced by coupling at ~40°C.

Depending on the reaction conditions, the starting compounds are present or used in the form of salts and/or salts, in particular alkali metal salts.

The bisazo compounds produced according to the invention can be separated by generally known methods, such as salting with electrolytes such as sodium chloride or potassium chloride, or evaporation of the reaction solution, e.g. by spray drying, optionally with the addition of auxiliaries such as stabilizers. and can be done.

Examples of the aromatic amine represented by the general formula (1N) include the following.

l-aminobenzene-2-18- or 4-β-sulfur 1-toethylsulpone, l-aminobenzene-2- or 4-methoxybenzene-5-β
-Sulfur 1-toethylsulfone, 1-amino-2-methoxy-6-methylbenzene-4-
β-sulfatoethylsulfone 1-amino-2,5-dimethoxybenzene-4-β-sulfatoethylsulfone 1-amino-2,4-dimethylbenzene-5-β-sulf 1-toethylsulfone 1-amino- 2,4-dimethoxybenzene-6-β-su, 7,-toethylsulfone and the above compounds, in place of the sulfuric acid ester group, a phosphoric acid ester group, acetyloxy group, propionyloxy group, n- or lso
-butyryloxy group, benzoyloxy group, benzenesulfonyloxy group, etc.

The bisazo compounds of the invention can dye cellulose fiber materials, such as natural or biogenic cellulose, such as cotton or viscose rayon materials, according to the customary methods practiced with water-soluble reactive dyes.

For example, in the case of cellulosic fibers, the bisazo compound of the invention is dyed using an acid binder such as caustic soda, carbonate, phosphate or baking soda. The dyeing method can be selected depending on the nature and physical properties of the fibers, such as continuous dyeing methods including exhaustion methods, printing methods or cold pad-batch-up methods.

When dyeing fiber materials with the bisazo compound of the present invention, Japanese Patent Publication No. 4B-1f199 and Japanese Patent Publication No. 45-4887
It is superior in dyeing rate and build-up property as compared to the dye described in the publication.

Furthermore, the compound of the present invention has only one fiber-reactive group in one molecule.
It is surprising that cellulose-based AAK can be dyed darker than C, I, and Reactive Black 6, which have two of them, even though they only have one.

The dyeings obtained have good fastness properties, such as good rub fastness, good sunlight fastness and good wet fastness, such as wash fastness, water resistance, acid and alkali fastness, containing substances in peracids. It is excellent in terms of robustness to chemical treatments.

Next, the present invention will be explained in more detail with reference to Examples. In the text, parts represent parts by weight.

Example 1 After diazotizing 11.15 parts of 2-naphthylamine-1-sulfonic acid by a conventional method, excess nitrous acid was removed with a sulfamine steeper, and 1-amino-8-hydroxynaphthalene-8, A neutral solution of 15.97 parts of 6-disulfonic acid was added to 0
Dropwise over several hours at ~10°C and pHjl ~5,
-Stir overnight. The next morning, 14.05 parts of l-aminobenzene-4-β-sulfatoethyl sulfone was diazotized using a conventional method, and a solution in which excess nitrous acid had been removed with sulfuric acid was added, and the mixture was heated at 0 to 10°C. , pH 6-8. Stir until the diazo compound is no longer detected. The obtained dye solution was adjusted to pH 4.5 to 6.5 and treated with potassium chloride to obtain a bisazo compound represented by the following formula (1) in the form of free acid.

(1m5ix 616 parts ml 1M)) Dissolve 0.6 parts of the above dye in 200 parts of the actual solution, and
1 part, add 10 parts of cotton, and raise the temperature to 60°C. Then, after 80 minutes had elapsed, 4 parts of soda carbonate was added and dyed at the same temperature for 1 hour.

After dyeing, washing and soaping were performed to obtain a solid navy dyed product.

Examples 2 to 9 Corresponding bisazo compounds were obtained in the same manner as in Example 1 using the raw material compounds listed in the table below. Using the obtained bisazo compound, cotton was dyed in the same manner as in Example 1 to obtain a navy colored dyed product having excellent performance similar to that of the compound represented by formula (1).

Claims (1)

[Claims] il+ In the form of free acid, the following general formula (I) [wherein R1
m'' each independently represents a methyl group or a methoxy group;
Indicates ω°C. Here, k is a group that is eliminated with an alkali. ] A bisazo compound represented by (2) General formula (I) [In the formula, R1 and RI each independently represent a hydrogen atom, a methyl group, or a methoxy group, and Q4 is a group -80,6-, Taha-8O, GH, [4(, R A method for dyeing cellulose fibers, characterized in that a bisazo compound shown in the following is used.