JPS62172062A - Triazine compound - Google Patents

Abstract

NEW MATERIAL:A compound shown by formula I [D is dyestuff residue of monoazo type, polyazo type, metallic complex type, anthraquinone type, phthalocyanine type or formazan type; R<1> is H or (substituted) alkyl; X is halogen; Y is H, halogen or (substituted) alkyl; X is halogen; Y is H, halogen or (substituted) alkyl; Z is -CH=CH2 or -CH2CHOSO3H]. EXAMPLE:A compound shown by formula II. USE:Dye for dyeing cellulosic fiber under pH and dyeing conditions wherein polyester fibers are dyed with disperse dye. PREPARATION:For example, 2mols compound shown by formula III is condensed with 1mol diamine compound shown by formula IV.

Description

DETAILED DESCRIPTION OF THE INVENTION Field of Industrial Application The present invention relates to a novel triazine compound useful as a dye for cellulose fibers, for example.

Conventional technology Traditionally, when dyeing cellulose fibers, reactive dyes are used, and pH is adjusted in the presence of acid binders such as sodium carbonate, potassium carbonate, and sodium hydroxide, and electrolytes such as sodium chloride and sodium sulfate. / Above 0, the temperature /
A method is adopted in which the process is carried out under conditions of p 0°C or lower.

However, in recent years, the demand for blended fabrics of cellulose fibers and other fibers, especially polyester fibers, etc. has increased, and in order to dye such cellulose/polyester mixed fibers (hereinafter sometimes simply referred to as 0/P fibers). To do this, it was necessary to apply dyes and dyeing conditions to cellulose fibers and dyes and dyeing conditions to polyester fibers, respectively. That is, the dye and dyeing conditions for dyeing polyester fiber are the same as those for cellulose fiber.
This was because there was a big difference. That is, to dye polyester fibers, disperse dyes are used and the temperature is about 73℃.
This is because it was necessary to dye at 0°C.

For example, if the C/P fibers mentioned above were to be dyed in the same process, two different dyes would be used in combination, a reactive dye and a disperse dye, which would pose several problems. Ta.

In other words, in order to dye the reactive dye sufficiently on the cellulose fiber side, it is necessary to use an acid binder to raise the pH to 10 or more. Dyeing is insufficient. On the other hand, in order to dye disperse dyes on the polyester fiber side, high-temperature conditions (normally 3oC) are required, but at high temperatures under the above-mentioned high-pitched conditions, the hydrolysis of reactive dyes is promoted, and cellulose fibers are The dyeing will be significantly inhibited. Therefore, when dyeing this straight ayp fiber, a two-bath method is generally used in which one fiber, cellulose or polyester, is dyed and then the other fiber is dyed in a separate bath. .

Problems to be Solved by the Invention The present invention seeks to provide a polyester fiber compound using a disperse dye.

Means for Solving the Problems The above problems could be solved by the triazine compound of the present invention having a specific structural formula.

That is, the triazine compound of the present invention has the general formula (1
) [In the formula, D represents a monoazo-based, polyazo-based, metal complex azo-based, anthraquinone-based, phthalocyanine-based or formazan-based dye residue, and R1 represents a hydrogen atom or an alkyl group which may have a substituent. where X represents a halogen atom, Y represents a hydrogen atom, a halogen atom, or an alkyl group which may have a substituent, and 2 represents -ca
=CH=CH2 or -or -(!H2CH,08
0, H) is a triazine-based compound.

In the triazine compound represented by the general formula CI) of the present invention, the dye residue represented by is exemplified by the following.

(1) Monoazo dye residue (2) Polyazo dye residue (3) Metal complex azo dye residue (4) Anthraquinone dye residue (5) 7-thalocyanine dye residue (6) Formazan dye residue In addition to the hydrogen atom, the group R1 includes a methyl group, an ethyl group,
Examples of the alkyl group which may have a substituent such as a methyl group, a β-hydroxyethyl group, and a .beta.-hydroxyethyl group, and examples of the halogen atom represented by X include a chlorine atom, a fluorine atom, and a bromine atom.

The halogen atom and alkyl group represented by Y include those mentioned above, with chlorine atom and methyl group being preferred, respectively.

The triazine compound represented by the general formula [I] can be produced as follows.

For example, a 2 molar proportion of a compound represented by the general formula Cn) (in which D , R' and/or all have the same meanings as the above definitions) and the following general 02z (in the formula, Y and 2 have the same meanings as the above definitions). By condensing with 1 molar proportion of the diamine compound shown, a triazine compound of the general formula [■] can be produced.

Incidentally, the diamine compound represented by the above general formula [■] can be produced as follows.

For example, a compound represented by the following general formula [■] (wherein Y represents the same meaning as defined above) is reacted in chlorosulfonic acid, and the compound represented by the following general formula [v] (wherein Y represents the same meaning as defined above) is reacted in chlorosulfonic acid. After forming a compound represented by the general formula (VD (wherein, Y represents the above definition and IiJ definition), it is reduced with sulfite to form a sulfinic acid, and then ethylene oxide is added to this compound. It is a compound that

/' Furthermore, the diamine compound represented by the general formula [■] can be produced by further treating the esterified product with a dilute alkali.

The triazine compound of the present invention is excellent as a dye, especially as a dye for cellulose fibers.

That is, examples of fibers that can be dyed with the triazine compound of the present invention include cellulose fibers such as cotton, viscose rayon, cufurammonium rayon, and hemp. However, cellulose fibers in mixed fibers such as polyester, triacetate, polyacrylonitrile, polyamide, wool, silk, etc. containing cellulose fibers can of course be dyed well.

In the fiber dyeing method using the disazo compound of the present invention, dyes necessary for dyeing non-cellulose fibers, such as disperse dyes described in Co1our Index (3rd edition), are added to the dye bath at the same time. In addition, it can be dyed.

When dyeing cellulose fibers using the disazo compound of the present invention, for example, the disazo compound represented by the above general formula [■] and the dye bath during dyeing may be
Buffers necessary to maintain the temperature at 0 (e.g. carbonic acid, phosphoric acid,
Acids such as acetic acid, citric acid, and sodium salts or potassium salts of these acids, singly or in mixtures, usually 0.5~! ,0
-9/), and if necessary electrolytes (sodium chloride or sodium sulfate, etc.)
Prepare a dye bath to which 700-j.
Good dyeing can be achieved by heating for 0 minutes.

In addition, in order to dye blended fabrics, blended knitted fabrics, etc. that are produced by adding other fibers such as polyester fibers to cellulose fibers, a disazo compound represented by the above general formula [1] of the present invention, By adding the disperse dye listed in the 0o1our Index to the dye bath, cellulose fibers and polyester fibers can be dyed simultaneously by a one-bath, one-stage method.

In addition, when dyeing blended fabrics, blended knitted fabrics, etc., as described above, the conventional one-bath two-step method of dyeing one fiber and then dyeing the other fiber in the same bath is used. Furthermore, a two-bath method in which cellulose fibers and other fibers are dyed from separate baths by combining the dyeing method using the triazine compound of the present invention and the dyeing method for fibers other than cellulose fibers may be used. It is also possible to adopt the law.

EXAMPLES Hereinafter, the method of the present invention will be specifically explained by examples, but the present invention is not limited to the following examples.

Example/ Potassium salt of 3.5-dinitrobenzenesulfonic acid 30
9 is chlorsulfoni/acid? ! Add to r- and heat to 0°C.
After stirring for 2 hours, the mixture was cooled and discharged into ice water to give 31j-dinitrobenzenesulfonyl chloride, followed by sulfite).
The mixture was stirred at 50 to 60° C. for 3 hours in an aqueous solution of IJum while maintaining the pH at ~10 to reduce it to sulfinic acid. Adding an alkali to this at the same temperature and blowing in ethylene oxide while maintaining the pH at 7 to 7 g. After the pH had lost its ability to change, the mixture was stirred at the same temperature for an additional 5 hours to obtain the following structural formula. The compound was reduced with an iron powder/hydrochloric acid system and then esterified in concentrated sulfuric acid to produce a diamine compound represented by the following structural formula.

Next, a molar proportion of a monoazo dye represented by the following structural formula and a 1 molar proportion of a diamine compound represented by the above structural formula were mixed in an aqueous medium with 3 molar proportions.
After condensation at 0 to aO<0>C, salting out with sodium chloride was carried out to produce a triazine compound of the present invention represented by the following structural formula and having the following visible light absorption analysis values.

[λmax: ,)9gnrn (water)] The triazine compound of the present invention represented by the above structural formula 0.29. Glauber's salt/A9, NamHPO,/2H,OO,1 as a buffering agent
1fi+ and KH,, PO4θ, 7El in water −〇〇−
In addition, 70 g of unmercerized cotton knitted fabric was placed in a dye bath adjusted to pH = 7, heated to 720°C over 30 minutes, dyed at the same temperature for 10 minutes, washed with water, annealed, washed with water, and dried. A yellow dyeing was obtained. The degree of dyeing of this dye was very good, and the dyed product obtained was extremely rich, and the light fastness, chlorine fastness, and sweat-sunlight fastness were all good.

Example The diamine compound produced in Example 1 above was stirred in an aqueous medium at pH=g, 0 to g, s, sθ to yt'c for 7 hours to obtain a diamine represented by the following structural formula % Formula % A compound was prepared.

Next, a comol ratio of a monoazo dye represented by the following structural formula and a 1 molar ratio of an S diamine compound represented by the above structural formula are mixed in an aqueous medium at a concentration of 30 to 30%.
After condensation at tio<0>C, salting out with potassium chloride was carried out to produce a triazine compound of the present invention represented by the following structural formula and having the following visible light absorption analysis values.

[λmax: 5J+Anrn (water)] Triazine compound o, xy, mirabilite/of the present invention represented by the above structural formula
61, Na, HPO4/2H, Oθ, 5y as buffering agent
Unmercerized cotton stockinette/θ9 was added to a dye bath prepared by adding KW2P0.0.0.2 and r to water θOmt, and the temperature was raised to /JO℃ over 30 minutes, and at the same temperature JO
After dyeing for a minute, washing with water, nibbling, washing with water, and drying were performed to obtain a red dyed product. This dyeing bath has a p
It was Hg. The dyed product obtained was extremely dense and had good light fastness, chlorine fastness, and sweat-sunlight fastness.

Example 3 In the production of the diamine compound of Example/3, s-
dinitrobenzene sulfone fil f, 3. ! ; −
') nitro-+-merbenzenesulfonic acid,
A diamine compound represented by the following structural formula was produced in the same manner as in Example 1, except for the following.

Next, a comol ratio of a dye represented by the following structural formula and a 1 molar ratio of a diamine compound represented by the above structural formula are condensed in an aqueous medium at 30 to 10 °C, and then spray-dried to obtain a product represented by the following structural formula, and Triazine compound of the present invention having the following analytical value by visible light absorption So, C, H, ○EIO, H [λmax: /s00nm (water)] Triazine compound of the present invention represented by the above structural formula 0.29 , Anthraquinone dye 0.2g 1 Glauber's salt/K11
A polyester/cotton-50:50 blended fabric 101i was added to a dye bath prepared by adding Na2HPO, /uH, ○o, u ti and Kl (tPO40, /11) as a buffer to 200 ydl of water, and the mixture was heated for 30 minutes. te/3θ℃
After dyeing at the same temperature for 60 minutes, washing with water, annealing, washing with water, and drying were performed to obtain a blue dyed product with good same color property. The dyeing bath was at pHg before and after dyeing.

Furthermore, the dyeing property was very good, and the dyed product obtained was extremely rich, and the light fastness, chlorine fastness, and sweat-sunlight fastness were all good.

The triazine compounds of the present invention shown in Table 1 below were produced by a method similar to Example 1, and cotton cloth was dyed with the compounds, and the results were shown in Table 1.

Claims (1)

[Claims] (1) General formula [I] ▲There are mathematical formulas, chemical formulas, tables, etc.▼……[I] (In the formula, D is a monoazo-based, polyazo-based, metal complex azo-based, anthraquinone-based, phthalocyanine-based, or formazan-based dye) Represents a residue, R^1 represents a hydrogen atom or an alkyl group that may have a substituent, X represents a halogen atom, and Y represents a hydrogen atom, a halogen atom, or an optional substituent. represents an alkyl group, Z is -C
A triazine compound represented by H=CH_2 or -CH_2CH_2OSO_3H.