JPS58142939A - Bisazo compound and dyeing of fiber using the same - Google Patents

Abstract

NEW MATERIAL:The compound of formulaI[R1 and R2 are H, methyl or methoxy provided that they are not H at the same time; Q is -SO2CH=CH2 or -SO2CH2CH2R (R is group eliminable with alkali); n is 0 or 1; one of the sulfonic acid groups is adjacent to the azo group bonded to the naphthalene ring] as a free acid. EXAMPLE:The compound of formula II. USE:A dye dyeing a cellulosic fiber in navy color with excellent degree of exhaustion and build up property. PROCESS:The aromatic amine of formula III is diazotized and coupled with equimolar amount of 1-amino-3-hydroxynaphthalene-3,6-disulfonic acid (salt) in an acidic medium at -5-+30 deg.C optionally in the presence of a reaction accelerator. The product is mixed with a compound obtained by diazotizing equimolar amount of the naphthylaminesulfonic acid derivative of formula IV, 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 fibers using the same. More specifically, the present invention relates to a novel fiber-reactive bis-1zo compound and a method for dyeing cellulose fibers navy color using the same.

Reactive dyes for dyeing cellulose fibers blue or black, Toshite C, ■, and Reaettve BlaCk 5, are known, but despite having two vinyl sulfone fibers in the molecule and reactive groups, cellulose System fiber number ζ
However, there is a problem that the dyeing rate is insufficient.

For the purpose of solving this problem, Examples 18 and 14 of the Public Separation Bond No. 16299/1977 are given to dyes represented by the following formulas).
and (b) are stated.

(To) Example 17 of Sara-ζ Nutrient No. 1145-48117 describes dye 0 represented by the following formula.

Shikashi, 0.1. R@aotive Black 5
Compared to that, the dyeing rate (to dye) is about 60-1 to dye)
ρE is about 11, and dye 0 is only about φ60, and the build-up property is also poor, and the above problems have not yet been solved.

The present inventors conducted intensive studies to solve these problems, and found that a specific bisazo compound in which a specific number of sulfonic acid groups are present at specific positions in the structure solves these problems, It was discovered that a dyed product with a high density of navy color having an excellent dyeing rate and build-up property can be obtained.
The present invention has now been completed.

In other words, the present invention provides the following formula (1) in the form of a free acid: [wherein] L1 and sulfur each independently represent a hydrogen atom, a methyl group, or a methoxy group, provided that either tortoise or sulfur is hydrogen and the other is a methyl group or a methoxy group. Q is a group -80g0B=(shi or -80zOH20
Indicates HzB. Here, L is a group that is eliminated with an alkali. n represents 0 or l, and one of the sulfonic acid groups is located adjacent to the azo group bonded to the naphthalene amount. 〕 □
Provided is a bisazo compound represented by

The present invention provides a method for dyeing cellulose fibers, which is characterized by using a bisazo compound represented by the general formula (I).

If Q in the above general formula 〇) is 1802CH2CH2B, it will be cloudy, and groups that can be removed with alkali, such as halogen atoms, such as chlorine and bromine atoms, ester groups of organic carboxylic acids and sulfonic acids, such as acetyloxy residues, etc. In the form of a lower alkanoyloxy residue, a benzoyloxy residue or a benzenesulfonyloxy group, or a free acid, the formula % is an acidic ester group of sulfuric acid.

The real bisazo compounds can exist either in the free acid form or in the form of their salts, or are preferably in the form of salts, especially alkali and alkaline earth metal, especially sodium, potassium and calcium salts. A more preferred shade is alkali metal salt ink.

The bisazo compound represented by the above general formula of the present invention has excellent dyeing properties as a reactive dye for embroidery, such as dyeing rate, alkali stability, build-up properties, and wash-off properties, as well as excellent fixing properties. It is a useful compound that gives navy-colored dyeings.

The novel bisazo compounds of general formula (I) are manufactured in the following manner. That is, the general formula (to) R 鵞 [wherein ILI, R1 and Q have the above-mentioned meanings.

] The aromatic amine represented by is diazotized by a known method to obtain l-amino-8-hydroxynaphthalene-8,6? Coupling is carried out with an equal amount of disulfonic acid or a salt thereof in an acidic medium at -6 to 80°C, optionally with the addition of a reaction promoter, and then the reaction mixture of general formula (1) [wherein, The positional relationship between n and the substituent has the above meaning. ] Diazotized L-diamine was added to a mol of the naphthylamine sulfonic acid derivative shown by a known method to give a weakly acidic to
It can be produced by coupling at -5 to 40''C under weak alkalinity.

Depending on the reaction conditions, the primary starting compounds are present in the form of acids and/or salts, *iC alkali metal salts, or are used in this form.

The separation of the bisazo compounds produced according to the invention can be carried out using general I.
This known method can be carried out by salting out with an electrolyte, for example sodium chloride or potassium chloride, or by evaporation of the reaction phase solution, for example by spray drying, optionally with the addition of auxiliaries such as stabilizers.

Examples of the bookworm group amine represented by the general formula (to) include the following.

l-Amino-2- or 4-methoxybenzene-6-β
-Sulfur 1-toethylsulfone, l-amino-2-methoxy-6-methylbenzene-4-β-sulfatoethylsulfone, l-amino-2,6-cymethoxybenzene-4-β-sulfate ethyl sulfone, 1-amino-2,4-dimethylbenzene-6-β-sulfatoethyl sulfone, 1-amino-2,4-dimethoxybenzene-6-β-sulfatoethyl sulfone and sulfuric acid esters in the above compounds. Examples of the group include a phosphate ester group, an acetyloxy group, a propionyloxy group, an n- or 10-butyryloxy group, a benzoyloxy group, or a benzenesulfonyloxy group.

The following compounds can be exemplified as naphthylamine sulfonic acid derivatives of general formula (1) that can be used in the present invention.

2-naphthylamine-1-sulfonic acid, 2-naphthylamine-1,5-disulfonic acid, g-naphthylamine-8
, 6-disulfonic acid, 2-naphthylamine-1,6-disulfonic acid 1-naphthylamine-2-sulfonic acid, l-
Naphthylamine-2,7-disulfonic acid.

The bisazo compounds of the present invention can be used to dye cellulosic delicate materials, such as natural or regenerated cellulose, such as wood wire or viscose ash materials, according to conventional methods carried out using water-soluble reactive dyes.

For example, in the case of cellulosic fibers, dyeing is carried out using the bisazo compound of the present invention and an acid binder such as caustic soda, sodium carbonate, phosphate or baking soda.The dyeing method is selected depending on the nature and physical properties of the fiber. For example, exhaustion method,
Textile dyeing methods including textile printing methods or cold butt batch up methods can be employed.

When the bisazo compound of the present invention is used to dye cellulose fiber materials, the resulting dyed product has good binding properties, such as good machinability, good sunlight retention properties, and good moisture retention properties. For example, it has excellent washability, water resistance, acid and alkali resistance, and resistance to peroxide-containing shoes.

Among these, bisazo compounds in which the azo group bonded to the naphthalene ring in the general formula α) is at the β position are preferred, and furthermore, bisazo compounds of the following formula [wherein R1, R2 and Q have the meanings defined in the preceding V] are preferred. ] The bisazo compound represented by the above is extremely excellent in color value and build-up property (1), and is also excellent in perspiration/sunlight ratio and chlorine ratio.

These compounds of the present invention are described in Japanese Patent Publication No. 184 Hatake-152.
No. 99 and Nutrients [No. 14B-4887] not only overcome the problem of soft dyes A cost, but also surprisingly have only one fiber-reactive group in one molecule, even though they do not fold too much. , 0, I, Reaot with two of them
It has characteristics that are superior to ive Bl@ak % and build-up performance.

Next, the present invention will be explained in more detail using actual examples. Part 1 in the text represents parts by weight.

Example 1

Claims (2)

[Claims] (1) In the form of a free acid, the following general formula (I) (17 [In the formula, R1 and Ba each independently represent a hydrogen atom, a methyl group, or a methoxy group. However, either it or ms has a water volume. The other number represents a methyl group or a methoxy group.Q Ha group-80!
Cfi-011t or It-80x01bOH*1 is shown. Kn is a group that is eliminated with alkali. n is O
or 1, and one of the sulfonic acid groups is adjacent to the azo group bonded to the naphthalene ring. ] A bisazo compound represented by (2) General formula α) (I) [In the formula, R1%IL! each independently represents a hydrogen atom, a methyl group or a methoxy group. However, when either R1 or IL2 is hydrogen, the other represents a methyl group or a methoxy group. Q group-80zOH1=OHg i Tal! -Bo
lICklgOlltlL &show. The ζ ni ni 凰 is a group that can be eliminated with an alkali. , n represents Ol or l, and one of the sulfonic acid groups is located next to the azo group bonded to the naphthalene ring. ] Reulose type delicate dyeing power method characterized by the use of a bisazo compound that is exclusively used in