JPH0662873B2 - Triazine compounds - Google Patents

Description

TECHNICAL FIELD The present invention relates to a novel triazine-based compound useful as a dye for cellulose fibers, for example.

2. Description of the Related Art Conventionally, when dyeing cellulose fibers, a reactive dye has been used, and a pH of 10 has been used in the presence of an acid binder such as sodium carbonate, potassium carbonate and sodium hydroxide and an electrolyte such as sodium chloride and sodium sulfate. Above, temperature 100
The method employed is performed under the condition of ℃ or below.

However, in recent years, there has been an increase in demand for blended fabrics of cellulose fibers and other fibers, especially polyester fibers, and for dyeing such cellulose / polyester mixed fibers (hereinafter sometimes simply referred to as C / P fibers). It was necessary to apply the dye and dyeing conditions for cellulose fibers and the dye and dyeing conditions for polyester fibers, respectively. This is because the dyes and dyeing conditions for dyeing polyester fibers are very different from those for cellulose fibers. That is, in order to dye polyester fibers, disperse dyes are used and the temperature is about 130.
This is because it was necessary to stain at ° C.

For example, if the above C / P fiber is dyed in the same process, two different dyes are used in combination with a reactive dye and a disperse dye, which causes some problems. It was That is, in order to sufficiently dye the reactive dye on the cellulose fiber side, the pH is adjusted to 1 with an acid binder.
It is necessary to make the value 0 or more, and the presence of the acid binder accelerates the decomposition of the disperse dye, resulting in insufficient dyeing of the disperse dye to the polyester fiber. On the other hand, in order to dye the disperse dye on the polyester fiber side, a high temperature condition (usually 130 ° C.) is required, but at the high temperature under the above high pH, hydrolysis of the reactive dye is promoted to form a cellulose fiber. Dyeing will be significantly hindered. Therefore, when such C / P fibers are dyed, a two-bath method in which one fiber of cellulose or polyester is dyed and the other fiber is dyed in another bath is generally performed. It becomes.

DISCLOSURE OF THE INVENTION Problems to be Solved by the Invention The present invention is intended to provide a triazine-based compound capable of dyeing cellulose fibers under pH and dyeing conditions when dyeing polyester fibers with a disperse dye.

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

That is, the triazine-based compound of the present invention has the general formula [I] (In the formula, D represents a monoazo type, polyazo type, metal complex azo type, anthraquinone type, phthalocyanine type or formazan type dye residue, and R ¹ represents a hydrogen atom or an alkyl group which may have a substituent. X represents a halogen atom, Y represents a hydrogen atom, a halogen atom or an alkyl group which may have a substituent, and Z represents —CH.
= CH ₂ or -CH ₂ CH ₂ OSO ₃ H)).

In the triazine compound represented by the general formula [I] of the present invention, examples of the dye residue represented by D include the following.

(1) Monoazo dye residue (2) Polyazo dye residue (3) Metal complex azo dye residue (4) Anthraquinone dye residue (5) Phthalocyanine dye residue (6) Formazan dye residue Further, as R ¹ , a methyl group, an ethyl group,
Examples thereof include an alkyl group which may have a substituent such as a butyl group and β-hydroxyethyl group, and examples of the halogen atom represented by X include a chlorine atom, a fluorine atom and a bromine atom. Examples of the halogen atom and the alkyl group represented by Y include the same ones as described above, and a chlorine atom and a methyl group are preferable, respectively.

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

For example, the general formula [II] (Wherein D, R ¹ and X have the same meanings as defined above) and 2 mole ratio of the compound represented by the following general formula [III] The triazine compound of the general formula [I] shown above can be produced by condensing 1 mol ratio of the diamine compound represented by the formula (Y and Z have the same meanings as defined above).

The diamine compound represented by the above general formula [III] can be produced as follows.

For example, the following general formula [IV] (Wherein Y has the same meaning as defined above) is reacted in chlorosulfonic acid to give a compound of the following general formula [V] (Wherein Y has the same meaning as defined above), then reduced with sulfite to give sulfinic acid, and then ethylene oxide is added to this compound to give a compound represented by the general formula [VI] (In the formula, Y represents the same meaning as defined above).

Then, after reducing the compound represented by the general formula [VI], esterification in concentrated sulfuric acid, and further if necessary by treating the esterified product with a dilute alkali diamine compound represented by the general formula [III] Can be manufactured.

The triazine-based compound of the present invention is excellent as a dye, particularly as a dye for cellulosic fibers. That is, examples of fibers that can be dyed with the triazine-based compound of the present invention include cellulosic fibers such as cotton, viscose rayon, kupla ammonium rayon, and hemp. Also,
Of course, the cellulosic fibers in the mixed fibers containing the cellulosic fibers such as polyester, triacetate, polyacrylonitrile, polyamide, wool and silk can be dyed well.

In the method for dyeing fibers using the disazo compound of the present invention, dyes necessary for dyeing fibers other than cellulosics, for example, disperse dyes described in Color Index (3rd edition) are simultaneously added to the dye bath. In addition, it can be dyed.

When a cellulosic fiber is dyed using the disazo compound of the present invention, for example, the disazo compound represented by the above general formula [I] and a dyeing bath having a pH of 5 to 10 during dyeing are used.
Buffers required to maintain the concentration of the acid (eg, carbonic acid, phosphoric acid, acetic acid, citric acid, etc. and the sodium or potassium salts of these acids, usually 0.5-5.0 g / about), and optionally Accordingly, a dyeing bath to which an electrolyte (usually 1 to 150 g / sodium chloride or sodium sulfate etc.) is added is prepared, and cellulosic fibers are added to this dyeing bath and heated at 100 to 150 ° C. for 30 to 50 minutes. As a result, good dyeing can be performed.

In order to dye a blended fabric, a blended knitted fabric or the like produced by adding other fibers such as polyester fibers to cellulosic fibers, a disazo compound represented by the above general formula [I] of the present invention, By adding the disperse dye described in the Color Index to the dye bath, it is possible to dye the cellulose fiber and the polyester fiber at the same time by the one-bath one-step method.

Further, in the case of dyeing the above-described mixed-spun fabric, mixed-woven knitted fabric, etc., a one-bath two-step method in which one fiber is dyed and then the other fiber is dyed in the same bath as conventionally used It may be applied, and further, a two-bath in which the cellulosic fiber and the other fiber are dyed from separate baths by combining the method for dyeing with the triazine compound of the present invention and the method for dyeing a fiber other than the cellulosic fiber. It is also possible to adopt the law.

Examples Hereinafter, the method of the present invention will be specifically described with reference to examples, but the present invention is not limited to the following examples.

Example 1 50 g of potassium salt of 3,5-dinitrobenzenesulfonic acid
Was added to 75 ml of chlorosulfonic acid, and the mixture was stirred at 80 ° C. for 2 hours, cooled, discharged into ice water to give 3,5-dinitrobenzenesulfonyl chloride, and then adjusted to pH = 8-10 in a sodium sulfite aqueous solution. While maintaining, the mixture was stirred at 50 to 60 ° C. for 3 hours to reduce to sulfinic acid. While adding alkali at the same temperature and keeping the pH at 7-8, ethylene oxide was blown in to eliminate the pH change, and then the following structural formula was obtained by stirring at the same temperature for 5 hours. The compound represented by is reduced with iron powder / hydrochloric acid system and then esterified in concentrated sulfuric acid to obtain the following structural formula. A diamine compound represented by

Then, the following structural formula 2 mole ratio of the monoazo dye represented by and 1 mole ratio of the diamine compound represented by the above structural formula in an aqueous medium
After condensing at 0 to 40 ° C., salting out with sodium chloride was carried out to prepare a triazine-based compound of the present invention having the following structural formula and having the following analytical value by visible light absorption.

The triazine compound of the present invention represented by the above structural formula 0.2
g, 16 g of Glauber's salt, 0.4 g of Na ₂ HPO ₄ 12H ₂ O and 0.1 g of KH ₂ PO ₄ as a buffer were added to 200 m of water, and 10 g of unsilked cotton knitted fabric was added to a dyeing bath adjusted to pH = 7,
It took 30 minutes to raise the temperature to 120 ° C., dyed at the same temperature for 60 minutes, washed with water, soaped, washed with water and dried to obtain a yellow dyed product. The dyeing degree of this dye was very good, and the dyed product obtained was extremely dense and had good light fastness, chlorine fastness, and sweat-sunlight fastness.

Example 2 The diamine compound produced in Example 1 was stirred in an aqueous medium at pH = 8.0 to 8.5 and 50 to 55 ° C. for 1 hour to obtain the following structural formula. A diamine compound represented by

Then, the following structural formula 2 mol ratio of the monoazo dye represented by and 1 mol ratio of the diamine compound represented by the above structural formula in an aqueous medium of 30 to
After condensing at 40 ° C., salting out with potassium chloride was performed to prepare a triazine compound of the present invention having the following structural formula and having the following analytical value by visible light absorption.

The triazine compound of the present invention represented by the above structural formula 0.2
g, 16 g of Glauber's salt, 0.5 g of Na ₂ HPO ₄ 12H ₂ O and 0.02 g of KH ₂ PO ₄ as a buffer were added to 200 m of water, and 10 g of unsilked cotton knitted fabric was added to the dyeing bath. After heating up to ℃ and dyeing at the same temperature for 30 minutes,
After washing with water, soaping, washing with water and drying, a red dyed product was obtained. The dyeing bath had a pH of 8 before and after dyeing. The obtained dyed product is extremely dense and has light fastness, chlorine fastness,
The sweat-sunlight fastnesses were all good.

Example 3 In the production of the diamine compound of Example 1, the following structural formula was carried out in the same manner as in Example 1 except that 3,5-dinitrobenzenesulfonic acid was replaced with 3,5-dinitro-4-methylbenzenesulfonic acid. A diamine compound represented by

Then, the following structural formula 2 mol ratio of the dye represented by the formula and 1 mol ratio of the diamine compound represented by the above structural formula are condensed in an aqueous medium at 30 to 40 ° C. and then spray dried to have the following structural formula:
A triazine-based compound of the present invention having the following analytical values by absorption of visible light was prepared.

The triazine compound of the present invention represented by the above structural formula 0.2
g, Anthraquinone dye 0.2 g, Glauber's salt 12 g, Na ₂ HPO ₄ 12H ₂ O 0.4 g and KH ₂ PO ₄ 0.1 g as a buffer were added to 200 m of water, and a polyester / cotton = 50: 50 blended spinning was prepared. A cloth (10 g) was put therein, the temperature was raised to 130 ° C. over 30 minutes, and dyeing was carried out at the same temperature for 60 minutes, followed by washing with water, soaping, washing with water and drying to obtain a blue dyed product having good color uniformity. The dyebath had a pH of 8 before and after dyeing. Further, the dyeing property is very good, and the dyed product obtained is extremely dense and has fastness to light, fastness to chlorine and sweat resistance.
The fastness to sunlight was good in all cases.

Example 4 A triazine compound of the present invention shown in Table 1 below was produced by a method according to Example 1, and a cotton cloth was dyed with the compound, and the results are shown in Table 1.

Claims (1)

[Claims] 1. A general formula [I] (In the formula, D represents a monoazo type, polyazo type, metal complex azo type, anthraquinone type, phthalocyanine type or formazan type dye residue, and R ¹ represents a hydrogen atom or an alkyl group which may have a substituent. X represents a halogen atom, Y represents a hydrogen atom, a halogen atom or an alkyl group which may have a substituent, and Z represents —CH.
= CH ₂ or -CH ₂ CH ₂ OSO ₃ H).