JPS585368A - Disazo dye - Google Patents

Abstract

NEW MATERIAL:To provide a new disazo compd. for dye shown by formulaI (where X is cyano, alkoxycarbonyl or alkylsulfonyl; Y is H, Cl, methyl or acylamino; Z is H, Cl, methyl, methoxy or ethoxy; R<1> and R<2> are H, (un)substituted alkyl, cyclohexyl, alkenyl or aryl). USE:The disazo compd. dyes polyester, cellulose and nitrogen-contg. fibres in blue color with excellent fastness to light, sublimation, water and washing. PREPARATION:An amine of formula II is diazotized and coupled with an aminothiophene of formula III. The resultant monoazo compd. of formula IV is diazotized and coupled with an aniline of formula V.

Description

[Detailed Description of the Invention] The present invention relates to a disazo dye, which specifically dyes polynisdel fibers blue, and improves various fastnesses, particularly light fastness, sublimation fastness, water fastness, and color fastness during dyeing. It is a disazo dye that has excellent temperature stability and pH stability, and is a reactive dye that dyes natural fibers such as cotton, wool, and silk blue, and has excellent color fastness, especially light fastness and washing fastness. be.

The following general formula (1) (in the formula, xF
i represents a cyano group, an alkoxycarbonyl group, or an alkylsulfonyl group; Y represents a hydrogen atom, a chlorine atom, a methyl group, or an acylamino group; 2 represents a hydrogen atom, a chlorine atom, a methyl group, a methoxy group; In the formula, R' and R8 represent a hydrogen atom, a substituted or unsubstituted alkyl group, a cyclohexyl group, an alkenyl group, or an aryl group. ) is a disazo dye shown by

In the general formula (1) shown above, ! Examples of the alkoxycarbonyl group represented by include methoxycarbonyl group, ethoxycarbonyl group, butoxycarbonyl group, and alkylsulfonyl group, C/1ilsulfonyl group, ethylsulfonyl group, butylsulfonyl group, etc. Examples of the acylamino group represented by Y include an acetelaino group, a chloroacetylamino group, a benzoylamino group, a methylsulfonylamino group, a chloroprobionylamino group, an ethoxycarbonylamino group, an ethylaminocarbonylamino group, and in R1 and R3, Examples of unsubstituted alkyl groups include methyl group, ethyl group,
Examples include linear or branched glopyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, etc. Substituted alkyl groups include lower alkoxy groups such as methoxyethyl group, ethoxyethyl group, butoxyethyl group, etc. Alkyl group: phenoxyalkyl group such as methoxyethyl group;
Benzyloxy ether group, optionally substituted aralkyloxy lower alkyl group of chlorobenzyloxy ether JHj; hydroxyethyl group, bitroxypropyl group, hydroxybutyl group, hydroxyhexyl group, λ-hydroxy-3-methoxypropyl group, etc. Optionally substituted hydroxyalkyl group, dianomethyl group, cyanolower alkyl group such as cyanoethyl group; substituted hydroxyalkyl group such as acetyloxyethyl group, chloroacetyloxyethyl group, chloropropionyloxyethyl group, benzoyloxyethyl group, etc. Good acyloxy lower alkyl groups: Alkoxycarbonyloxy lower alkyl groups such as methoxycarbonyloxyethyl group and methoxyethoxycarbonyloxyethyl group; Carbamoyl lower alkyl groups such as carbamoylmethyl group and carbamoylether group: methoxycarbonylmethyl group, ethoxycarbonyl group Methyl group:
Optionally substituted alkoxycarbonyl lower alkyl groups such as methoxyethoxycarbonylmethyl group and penzyloxycarmenylmethel group; optionally substituted aralkyl groups such as benzyl group, phenethyl group, and chlorobenzyl group: allyloxycarboxylic group; Allyloxycarbonyl lower alkyl groups such as Nyl ether group and allyloxycarbonylmethyl group; Tetrahydro-furfuryl group; Succinimide lower alkyl group such as Conodate imide ether group; Heptathalimide lower alkyl group such as phthalimidoethyl group A cyanoalkoxy lower alkyl group having a cyanoethoxyethyl group or a cyanomethoxyethyl group; a 10-geno lower alkyl group having a chloroethyl group; a methanesulfonic acid group; examples of the aryl group include a phenyl group, a chlorophenyl group, and a methyl group; The disazo dye represented by the general formula (11) has a phenyl group.
) The amines represented by the formula % are diazotized to form the following formula [sulfur] (in the formula,
I is the same as defined above. ), and the obtained monoazo compound represented by the following formula (IV) (wherein, X is 0 as defined above) is diazotized to form a monoazo compound represented by the following general formula (V) Among them, Y, Z, R'' and R3 can be produced by coupling with the anilines shown in 1) in the above definition.

The fibers that can be dyed with the disazo dye of the present invention include:
Polyethylene terephthalate, terephthalic acid door, 4'
- Polyester fibers made from polycondensates of -bis-(human-oxymethyl) sulfate, etc., cellulose fibers such as cotton and hemp, nitrogen-containing fibers such as silk and wool, or polyesters with the above natural fibers. Examples include blended products with fibers and mixed fiber products.

In order to dye polyester fibers using the dye of the present invention, since the dye represented by the general formula (1) is water-soluble, a dye bath or printing paste dissolved in an aqueous medium is prepared, Dip dyeing or printing may be performed. For example, when dyeing polyester fibers, acidic substances such as formic acid, acetic acid, phosphoric acid, or ammonium sulfate are added to the dyeing bath.
When dyeing natural fibers as a reactive dye, use sodium carbonate, If an alkaline substance such as sodium silicate, caustic soda or sodium bicarbonate is added and the dyeing is carried out under conditions of pH 5' to /3 and temperature 30° C. to 10° C., it is possible to obtain a dyeing with excellent fastness.

Furthermore, the dye represented by the general formula [■] used in the method of the present invention may be used in combination with dyes of the same type or dyes of other types, among which the dye represented by the general formula (1) Good results, such as improved paper dyeing properties, may be obtained by combining them with each other.

Next, the present invention will be explained in more detail with reference to examples, but the present invention is not limited to the following examples unless it exceeds the gist thereof.

Example/ A dye bath was prepared by dissolving 0.31 of a dye represented by the following structural formula in water Jt. Polyester fiber 1001 was immersed in this dyeing bath, dyed at 130° C. for 40 minutes, then washed pink, washed with water, and dried to obtain a dyed fabric with a vivid blue color. The light fastness, sublimation fastness and water fastness of the dyed fabric obtained were 1! □ The toughness and the temperature stability and pH stability of the above dye during dyeing were good.

The dye used in this Example was manufactured as follows.

p-(sulfoxyethylsulfonyl)anilinco4.
71 was dissolved in 1 zO- of sea hydrochloric acid, the solution was cooled to 12 ml, and then 2N sodium nitrite was added.

At this time, the temperature was set not to exceed ju. The obtained diazonium salt solution was added to a solution of co-amino-3-cyanothiophene/co,+1 dissolved in methanol l-Hiroshi at ℃ and stirred for 2 hours at the same temperature, and the precipitated monoazo compound was dissolved into P. After taking it, it was washed with saline and dried. This monoazo compound [coanno J-cyano-3-(p-
Sulfoxyethylsulfonylphenylazo)thiophene) / LOI with acetic acid 1zo- and phosphorus aiizo
(prepared by dissolving mixed sulfuric acid λ0IIIC) was gradually added thereto, and the mixture was stirred for 30 minutes at the same 11°C to prepare a diazo solution of a monotono compound. N-(ethyl)-M-(β-acetoxyethyl)aniline/0. j methanol co00-
and added to ice λ001 and water 100°. The diazo solution prepared above was added thereto, stirred at O-ZC for 2 hours, and then adjusted to pH using soda. The precipitated disazo dye was washed with saline and dried. Ice crystal λmaz (I O-a7ton aqueous solution) F
i1!14'Onm.

EXAMPLE A dye θ, j j represented by the following structural formula % formula % (3) was dissolved in 3 tons of water and a dyeing bath of 1111!!
00g was immersed and dyed at 130°C for 60 minutes, followed by soaping, washing with water, and drying, resulting in a vivid blue dyed fabric. The light fastness, sublimation fastness, and water fastness of the obtained tomo-dyed fabric as well as the temperature stability and pH stability during dyeing of the above dye were good.

The dye used in this example was produced according to Example/.

Ice crystal λ (10-acetone aqueous ax liquid) Fij was 47 nm.

Example J Dye represented by the following structural formula 0. ! A staining bath was prepared by dissolving JtK I in water and running. Polyester fiber 1001 was immersed in this dyeing bath and dyed at 130°C for 40 minutes to produce nine bales, so pink,
After washing with water and drying, a vivid blue dyed fabric was obtained. The light fastness, sublimation viscosity and water viscosity of the dyed fabric obtained, as well as the temperature stability during dyeing of the above dye, p
No. 11 stability was good.

The dye used in this example can be manufactured according to Example/.

λ of ice crystals. ax<to-acetone aqueous solution) ij4JOn
m and nine.

Example 1 Dye represented by the following structural formula 0. A dyeing bath was prepared by dispersing r I in 3 tons of water. Cotton broad cloth 1001 was immersed in this dyeing bath, dyed at 0°C for 60 minutes, then washed pink, washed with water, and dried.
Stability was good.

The dye used in this example was produced according to Example 1.

The ice crystal λmax (lrθ%77 tons of water) is A/j
It was nm.

The dyes were used to dye polyester fibers or natural fibers (cotton broadcloth, Example 1) to obtain dyed products having the tones shown in the table.

Table~l general formula

Claims (1)

[Claims] (1) General formula (where x represents a cyano group, alkoxycarbonyl group, or alkylsulfonyl group, Y represents an aqueous atom, chlorine atom, methyl group, or acylamino group, and 2 represents a hydrogen atom, a chlorine atom, or a methyl a methoxy group or a methoxy group, and R1 and R2 are a hydrogen atom, a substituted or unsubstituted alkyl group, a cyclohexyl group, an alkenyl group or an aryl group.