JPS58136656A - Monoazo dye for polyester fiber - Google Patents

Abstract

NEW MATERIAL:Compounds of formulaIwherein R<1> is hexyl, 2-ethylhexyl, benzyl, phenethyl, cyclohexyl, R<2> is a C1-C4 alkyl, a C1-C4 alkoxycarbonyl- C1-C4 alkyl, a C1-C4 alkoxy-C1-C4 alkyl; n is 1, 2. USE:Monoazo dyes which dye polyester fibers clear greenish yellow with excellent fastness to sunlight, sublimation and water and exhibit good temperature stability and pH stability during dyeing. PREPARATION:A compd. of formula II is reacted with a compd. of formula III (wherein X is halogen), IV (wherein D is phenyl, tolyl) or formula V. Alternatively, an aniline of formula VI is diazotized by a conventional method, and then coupled with a pyridone of formula VII.

Description

[Detailed Description of the Invention] This invention relates to a monoazo dye for polyester fibers, and more specifically, it dyes polyester fibers in a vivid greenish-yellow color and improves various fastnesses, particularly sunlight fastness, sublimation fastness, and This invention relates to a monoazo dye that has excellent water fastness, temperature stability during dyeing, and PMI stability.

The present invention will be explained in detail below.

The monoazo dye of the present invention has the following general formula CI) (wherein I'
ll represents a hexyl group, a coethylhexyl group, a 7-ethyl group, a benzyl group, a phenethyl group, or a cyclohexyl group. Hz represents a C&-4 alkyl group, a 01-4 alkoxycarbonyl group, a 01-1 alkyl group, or a 01-4 alkoxy carbonyl group. It represents an alkyl group, and n is /fi or co. ) is a monoazo dye for polyester fibers.

The monoazo dye represented by the above general formula CI) is.

For example, a compound represented by the general formula ([1 (in the formula, R1 and n are the same as defined above)] can be expressed as a compound represented by the general formula (9). ...l〕(
In the formula, X represents a halogen atom and Rm is the same as the above definition) or a compound represented by the general formula] D-80 Hatake 1s ・・・・・・・・・・・・ QV
) (In the formula, D represents a phenyl group or a tolyl group, and the cluster is the same as the above definition.) Compounds represented by the following or general formula [■ (RIO), 1! O,・・・・・・・・・・・・(G)
(In the formula, W is the same as defined above) By reacting with a compound represented by (B
) Anilines represented by the general formula (8) (wherein R1 and n are the same as defined above) are diazotized by a conventional method.

From K, coupling with a pyridone represented by the general formula [■] 1m (in the formula, R1 is the same as the above definition),
Manufactured.

According to the method (m) for producing dyes of the present invention, anilines represented by the general formula (1) are diazotized by a conventional method, and then J-cyano-4-hydroxy-monomethylpyrido, coon or an alkali metal salt thereof is added to the diazotized compound by a conventional method. Coupling is carried out to obtain an azo compound represented by the general formula [■].Then, the resulting azo compound is clebenzene. Dichlorobenzene.

Aromatic compounds such as nitrobenzene and O-nitrotoluene, N-alkylformamides such as dimeterformide, alkylpyrrolidones such as N-methylpyrrolidone, ketones such as acetone and methyl ethyl ketone, alcohols such as methanol and ethanol. In the presence of an organic base such as pyridine, piperidine, trietheraion, etc. or an inorganic base such as potassium carbonate, magnesium oxide, sodium hydroxide, etc., in an inert organic solvent such as
By reacting with a sulfonic acid ester represented by the general formula (g), a halogen atom represented by the general formula (■), or a sulfuric acid ester represented by the general formula ] Pyridone azo
The family is Nil (obtained in high yield).

The anilines represented by the general formula [1] used as the diazo component in the method (B) for producing the dye of the present invention include, for example, 0+, 0-*+p-hexyloxyethoxycarbonylanili/.

o-, m-, or p-2-ethylhexyloxyethoxycarbonylaniline.

O-+1- or p-2-ethylhexyloxyethoxyethoxycarbonylaniline.

o-, m-, or p-(phenoxy7ethoxycarbonyl)aniline.

o-sm +, or p-(phenoxyethoxy7ethoxycarbonyl)aniline.

o+, 11-, or 'P-(benzyloxyethoxycarbonyl)aniline.

o-lm-, or p-(benzyloxyethoxyethoxycarbonyl)aniline.

0-, to- or I)-(phenethyloxyethoxycarbonyl)aniline.

o-, m+, or p-(7enetheroxyethoxyethoxycarbonyl)aniline.

o-, m+, or p-cyclohexyloxyethquine carbonylaniline.

o+, 1m-at or p-cyclohexyloxyethoxyethoxycarbonylaniline.

The pyridones represented by the general formula (8) used as a coupling component can be obtained, for example, by condensing and concentrating acetoacetate, cyanacetate, and an optionally substituted alkylamine.

In the method for producing vkm of the present invention, commonly used methods are used for diazotization and coupling reactions. For example, phenoxyethoxycarbonylanilines are prepared from concentrated sulfuric acid and sodium nitrite using nitrosyl sulfur m! The kettle to be etediazotized is dissolved in aqueous hydrochloric acid solution.
Or, after suspending, nitrous acid is added to an aqueous solution of IJium water, diazotized, and an alkali such as sodium acetate, sodium carbonate, or sodium hydroxide containing 3-cyano-l-methyl-4-hydroxy-pyridones is added. This is done by adding it to an aqueous solution. Although the coupling reaction may be carried out under neutral or alkaline conditions, it is preferably carried out under slightly acidic conditions.

Fibers that can be dyed with the monoazo dye of the present invention include:
Polyethylene terephthalate, terephthalic acid and 79 μm
Polyester fibers made of polycondensates with bis-(hydroxymethyl)cyclohexane, cotton, silk,
A blend of natural fibers such as wool and the above polyester fibers.

Examples include mixed fiber products.

In order to dye polyester fibers using the dye of the present invention, a conventional method is used since the dye represented by the general formula [I] is insoluble or dissolvable in water.

If a dyeing bath or printing paste is prepared by dispersing it in an aqueous medium using a clamp of naphthalene sulfonic acid and formaldehyde, higher alcohol sulfuric acid ester, higher alkylbenzene sulfonate, etc. as a dispersant, and dyeing or printing is performed. good. For example, in the case of dip dyeing, polyester fibers or their blends can be dyed with excellent fastness by applying ordinary dyeing methods such as high temperature dyeing, carrier dyeing, and thermosol dyeing. In this case, even better results can be obtained if an acidic substance such as formic acid, acetic acid, phosphoric acid or ammonium sulfate is added to the dyeing bath.

Furthermore, the dye represented by the forepaw general formula [I] of the present invention may be used in combination with dyes of the same type or dyes of other systems, and among these, the dyes represented by the forepaw general formula CI) may be mixed together to improve dyeability. Good results such as improvement may be obtained.

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 1 The compound Jt, 411 shown in Example 1 was dissolved in a mixed solution of concentrated hydrochloric acid JJIIj and 100111t of water, and this l
l1I[ was cooled with water to 0-1°C, and sodium nitrite 1/,
A solution of 44 g dissolved in 7j- of water was added dropwise.

After stirring at 0 to 3°C for 1 hour, a small amount of sulfamino acid was added to obtain a diazo liquid.

On the other hand, 3-cyano-bu-hydroxy-V-metherpyridoco/co λ, zg, sodium acetate μJ, /l and 6.3 g of sodium hydroxide in 23 wt. water/r00t
It was dissolved in t and used as a coupling solution.

The diazo solution was added to this coupling solution at VCO-j'C over a period of 30 minutes, and the mixture was further stirred for 1 hour. After the precipitated crystals were separated from each other, they were washed with water and dried to obtain yellow crystals zu and ug of an azo compound represented by the following formula. The maximum absorption wave value (hereinafter abbreviated as λmax) of this azo compound in acetone was -coynm.

Next, the above azo compound μi, rti, sodium sulfate t
o, tg and dimethyl sulfate ii, pg in a mixture of chlorobenzene/jOxi, from 0 to! It was added at ℃ and reacted at the same temperature for 3 hours. After reaction.

Chlorobenzene was distilled off by steam distillation, and the precipitated crystals were separated into two, washed with water and dried to obtain yellow crystals of a dye represented by the following formula. This dye containing WaX is da JO
It was nm.

A dyeing bath was prepared by dispersing the monoazo dyes o and zg obtained in this example in water JlfC containing naphthalene sulfonic acid-formaldehyde condensate/II and higher alcohol sulfate ester co-I.

A full polyester fiber 1009 is immersed in this dyeing bath,
After dyeing at 130° C. for up to minutes, soaping, washing with water, and drying were performed, a bright greenish-yellow dyed fabric with excellent light resistance, sublimation resistance, and water resistance was obtained. Also.

The temperature stability and pH stability of the dye of this example were good.

Example 3 Compound represented by the following formula 4. ! An azo compound J1. I got Jfl.

Next, the above azo compound, 21.3g, carbonic acid) Liu Go!
A mixture of 71 ml of N-methylbiridone, Jl, butylpamide, 49, and N-methylbiridone was reacted for 3 hours at 20°C to 10°C.

Then, after cooling to room temperature, 7jm of water was added.

The precipitated crystals tF were separated, washed, and dried to obtain 1.7 g of yellow crystals of the dye shown below. λWa of this dye
X was $J/nB.

Monoazo dye 0.19 obtained in this example is dispersed in water 3j containing naphthalene sulfonic acid-formaldehyde condensate t, pg and higher alcohol sulfate ester/g, and methylnaphthalene carrier/Ill is added thereto for dyeing. A bath was prepared.

Polyester fiber 1009 was immersed in this dyeing bath, and
After dyeing at 0° C. for 2θ minutes, soaping, washing with water, and drying, a bright greenish-yellow dyed fabric with excellent light resistance, sublimation resistance, and water resistance was obtained. Also.

The temperature stability and pm stability were also good.

Example 3 Azo compound represented by the following formula obtained in the same manner as in Example 1 -1, -1, sodium vertate z, 3i, p-) luenesulfonic acid ether/J, 09 and N, N- A mixture of dimethylformene and acetate J- was reacted at ~60°C for 3 hours. Then, after cooling to room temperature, water 7j@t was added, and the precipitated crystals were separated in a furnace, washed, and dried to obtain yellow crystals of a dye represented by the following formula, λ/, jli.

The λIIILX of this dye was J□nm.

Polyester fibers were dyed at high temperature using the dye obtained in this example.

A vivid greenish-yellow dyed fabric was obtained. The obtained tomo-dyed fabric had good sunlight, sublimation and water fastness.

Furthermore, the temperature stability and pIi stability during dyeing were also good.

Example Compounds io and ig represented by the following formulas were neutralized and dissolved in 3 owJ of concentrated hydrochloric acid and J001IJ of water, and cooled with water to 0-JC.

Dissolving 7.6g of sodium nitrite in water JOd
It was added dropwise at 0-1°C. After stirring at the same temperature for 1 hour,
A small amount of sulfamic acid was added to form a diazo solution. On the other hand, J.
-7 anor/, l-dimethyl-4-hydroxypyridocone it, ag.

Sodium acetate, 7g and sodium hydroxide #,
Jj1 was dissolved in 1 liter of water to prepare a coupling solution. A diazo solution was added to this coupling solution at 0 to j°C, and the mixture was stirred at the same temperature for 1 hour. After the precipitated crystals were separated by F, they were washed with water and dried to obtain yellow crystals of the dye represented by the following formula #2. Ili was obtained.

1mlLX of this dye was -J/nm.

Using the dye obtained in this example, polyester fibers were dyed at high temperature (130°C), and a clear greenish-yellow dyed fabric was obtained. The dyed fabric obtained had good light emission, sublimation, and fastness. Also, temperature fg during dyeing? ? The properties and PIE stability were good.

Example! ~Reference Table-/-JK Polyester fibers were dyed in the same manner as in Example 1 using the dyes described. λma of each dye
x and the color tone of the dyed fabric are shown in Tables 7 to JK.

Table -ノ Table - Ko

Claims (1)

[Claims] (1) General formula 1 below: where Itl is a hexyl group, -monoethylhexyl group,
Represents a phenyl group, benzyl 1.7enethyl group or cyclohexyl group. Rljl O,=, alkyl group, 01-4 alkoxycarmenyl 014 alkyl group or 01-4 alkoxy 0
1-4 alkyl group, n is 1 or -. ) A monoazo dye for polyester fibers.