JPS5911363A - Monoazo dye for polyester fiber - Google Patents

Abstract

NEW MATERIAL:Monoazo compds. of formula I , wherein X, Y are H, halogen, nitro, cyano; R<1> is H, Cl, methyl, acylamino; R<2> is H, methyl, Cl, methoxy, ethoxy; R<3>, R<4> are H, (un)satd. alkyl, cyclohexyl, alkenyl, aryl; R<5> is cyano, alkoxycarbonyl, benzyloxycarbonyl, phenoxyethyloxycarbonyl. USE:Monoazo dyes coloring polyester fiber orange to green. PREPARATION:Amines of formula II are diazotized and then coupled with amines of formula III to yield monoazo compds. of formula IV, which are subjected to reaction with active methylene compds. of formula V in the presence of an org. or inorg. base in inert solvents (e.g., dimethylformamide) to yield methinated monoazo compds. of formula VI. Said methinated monoazo compds. are reacted with hydrocyanic acids, and the reaction product is treated with oxides.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a monoazo dye for polyester fibers, and more specifically, it dyes polyester fibers from orange to green and has excellent color fastness, particularly light fastness, sublimation fastness, and water fastness. This invention relates to monoazo dyes for polyester fibers.

The monoazo dye for polyester fibers of the present invention has the general formula [D (wherein, where R2 represents a hydrogen atom, a methyl group, a chlorine atom, a methoxy group or an ethoxy group, Ha and R4 represent a hydrogen atom, a substituted or unsubstituted alkyl group, a cyclohexyl group, an alkenyl group or an aryl group, and R11 represents a cyanide group. This is a novel water-insoluble monoazo dye represented by the following formula: a phenoxyethyloxycarbonyl group, an alkoxycarbonyl group, a benzyloxycarbonyl group, or a phenoxyethyloxycarbonyl group. In the forefoot general formula [I], examples of the halogen atom represented by Examples include amino group, methylsulfonylamino group, chloropropionylamine group, ethoxycarbonylamino group, ethylaminocarbonylamino group, and Ra and R
The unsubstituted alkyl group represented by 4 is a methyl group,
Examples of substituted alkyl groups include ethyl group, linear or branched propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, etc. Substituted alkyl groups include methoxyethyl group, ethoxyether group, butoxyether group, etc. Lower alkoxyalkyl groups; lower alkoxyalkoxyalkyl groups such as methoxyethoxyethoxyether and ethoxyethoxyethyl groups; phenoxyalkyl groups such as phenoxyethyl; optionally substituted aralkyl such as benzyloxyethyl and chlorobenzyloxyethyl groups; Oxy lower alkyl group; optionally substituted hydroxyalkyl group such as hydroxyethyl group, hydroxypropyl group, hydroxybutyl group, hydroxyhexyl group, -monohydroxy-3-methoxypropyl group; cyano lower such as cyanomethyl group, cyanoethyl group Alkyl group; optionally substituted acyloxy lower alkyl group such as acetyloxyethyl group, chloroacetyloxyethyl group, chloropropionyloxyethyl group, benzoyloxyethyl group; methoxycarbonyloxyethyl group, methoxyethoxycarbonyloxyethyl group, etc. alkoxycarbonyloxy lower alkyl group; carbamoyl-3= lower alkyl group such as carbamoylmethyl group, carbamoylethyl group; substituted alkoxycarbonylmethyl group, ethoxycarbonylmethyl group, methoxyethoxycarbonylmethyl group, benzyloxycarbonylmethyl group, etc. an optionally alkoxycarbonyl lower alkyl group;
Optionally substituted aralkyl groups such as benzyl group, phenethyl group, and chlorobenzyl group; allyloxycarbonyl lower alkyl groups such as allyloxycarbonylethyl group and allyloxycarbonylmethyl group; tetrahydrofurfuryl group; Cono-1 phosphoric acid imide lower alkyl groups such as groups; phthalic acid imide lower alkyl groups such as doethyl group; cyanoalkoxy lower alkyl groups such as cyanoethoxy ether group and cyano methoxy ether group; Examples of the aryl group include phenyl group, chlorophenyl group, methylphenyl group, etc.; examples of the alkenyl group include allyl group, cometerallyl group, cochloroallyl group, crotyl group, etc.; A1 - Chain-like alkoxycarbonyl groups, etc. are mentioned.

The monoazo dye represented by the forepaw general formula [I] is represented by the following formula [1].
1) % formula % (in the formula, X, Y, R1, R2, Ra, R4
Oj and R'5 are the same as defined above. ), N-alkylformamides such as dimethylformaldehyde, N-methylpyrrolidone, etc.
Good yields can be obtained by dissolving alkylpyrrolidones in an inert solvent such as an ether solvent such as dioxanetetrahydro7rane, reacting with cyanogenic acids such as sodium cyanide, and then treating with an oxide such as bromine or hydrogen peroxide. It can be obtained with The compound represented by the general formula (II) is the following formula (1)
A monoazo compound represented by R2 (wherein X, Y, R1, R2, RB and R' are the same as defined above) is represented by the following formula % (wherein R5 is the same as defined above). An active methylene compound and an ether solvent such as dioxane/tetrahydrofuran, an N-alkylformamide such as dimethylformamide, an N-alkylpyrrolidone such as N-methylpyrrolidone, or in an inert solvent such as water/N-methylpyrrolidone, water/ The coexistence of organic bases such as piperidine and morpholine or inorganic bases such as sodium carbonate and sodium hydroxide in water/organic solvents,
-obtained in good yield by heating to s o C.

An amine represented by the general formula [lf] (wherein X and Y are the same as defined above) is diazotized by a conventional method,
It is obtained by coupling with an amine represented by the general formula (wherein R1, R2, R8 and R4 are the same as defined above).

Fibers that can be dyed with the monoazo dye of the present invention include polyethylene terephthalate and terephthalate. L! :/
, polyester fibers made of polycondensates with 4'-bis-(hydroxymethyl)cyclohexane, or cotton, silk, wool, etc. 71 To dye polyester fibers using the monoazo dye of the present invention, a conventional method is used. A dyeing bath or printing paste is prepared by dispersing in an aqueous medium using a condensate of naphthalene sulfonic acid and formaldehyde, higher alcohol sulfuric ester, higher alkylbenzene sulfonate, etc. as a dispersant, and dyeing or printing is carried out. Bye. For example, in the case of dip dyeing, if ordinary dyeing methods such as high-temperature dyeing, carrier dyeing, and thermosol dyeing are applied, it is possible to dye polyester fibers and blends with excellent fastness. . 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 forelimb structural formula [I] used in the method of the present invention may be used in combination with dyes of the same type or dyes of other systems. Good results, such as improved 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 1 A dyeing bath was prepared by dispersing dyes O and S t represented by the following structural formulas in 3 t of water containing a naphthalene sulfonic acid-formaldehyde condensate/l and higher alcohol sulfate Jr. 100% polyester fiber in this dye bath? Soak %
After dyeing at /30C for 60 minutes, washing with water and drying, a purple dyed fabric was obtained. The light fastness, sublimation fastness and water fastness of the obtained dyed fabric, as well as the temperature stability during dyeing of the above dye, were good.

The dye used in this example was produced as follows.

P-formylaniline u and lIr were diazotized according to a conventional method to obtain N-ethyl-N-cyanoethylaniline3. Ri1
Intermediate left obtained by coupling with, Of is dissolved in dioxane Sθ-, malonitrile H31 is added,
The mixture was stirred at room temperature for 7 hours. Collect the precipitated crystals, dissolve the obtained crystals in 5θcc of dimethylformamide, and add an aqueous solution of prussic acid of dichloromethane dissolved in water. Then bromine 3. , l F are added at 20"Q to 30c. Stir for 1 hour at the same temperature and discharge into water. The resulting precipitate is filtered, washed with water and dried. The λmax (acetone) of the crystal is !r 'I It was !r nm.

Example λ Dye θ, tr'6 naphthalenesulfonic acid represented by the following structural formula % Formula %
A dyeing bath was prepared by dispersing formaldehyde condensate/l and higher alcohol sulfate 22 in water 31.
I did J. Polyester fiber 7002 was immersed in this dyeing bath, dyed with i,:ioc for 6θ minutes, and then dyed with so pink,
After washing with water and drying, a green dyed fabric was obtained. The color fastness to light, sublimation fastness and water fastness of the dyed cloth as well as the temperature stability during dyeing of the dye described in "1" were good.

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

The λmax (acetone) of the crystal was Alonm.

Example 3 0.51 of the dye represented by the following structural formula was mixed with naphthalenesulfonic acid = 11
- A dyeing bath was prepared by dispersing the monoformaldehyde condensate/f and higher alcohol sulfate ester, 2f, in 3 t of water. Polyester fiber 1002 was immersed in this dyeing bath and dyed at /307 for 6θ minutes, followed by soaping, washing with water, and drying to obtain a blue dyed fabric. The light fastness, sublimation fastness and water fastness of the obtained dyed fabric as well as the temperature stability during dyeing of the above dye were good.

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

The λmax (acetone) of the crystal was tater nm.

EXAMPLE A dyeing bath was prepared by dispersing the dye θ, S1 represented by the following structural formula in 3 t of water containing 2 vol of naphthalene sulfonic acid-formaldehyde condensate/f and 2 vol of higher alcohol 12-col sulfate. In this dyeing bath, 5 polyester fibers/θo
After soaking and dyeing at 1.30'Q for 60 minutes, soaping, washing with water and drying were performed, a purple dyed fabric was obtained. The light fastness, sublimation fastness and water fastness of the obtained dyed fabric as well as the temperature stability during dyeing of the above dye were good.

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

The λmax (acetone) of the crystal was kAknm.

Example S A dye bath was prepared by dispersing dye O1S represented by the following structural formula % in 3 t of water containing naphthalene sulfonic acid-formaldehyde condensate/f and higher alcohol sulfate ester.

Polyester fiber 10O in the dye bath? Soak /3
After dyeing at 0'Q for 6θ minutes, soaping, washing with water and drying were performed to obtain a blue dyed fabric. The light fastness, sublimation fastness and water fastness of the obtained dyed fabric as well as the temperature stability during dyeing of the above dye were good.

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

The λmax (acetone) of the crystal was 113 nm.

EXAMPLE 1 A dyeing bath was prepared by dispersing 0.51 of a dye represented by the following structural formula in 3 t of water containing 11 of a naphthalene sulfonic acid-formaldehyde condensate and a higher alcohol TAR ester co-V. Polyester fiber /θor is immersed in this dyeing bath, /
After dyeing with 30'l:: for 6θ minutes, soaping, washing with water and drying were performed to obtain a green dyed fabric. The light fastness, sublimation fastness and water fastness of the obtained dyed fabric as well as the temperature stability during dyeing of the above dye were good.

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

The λmaX (acetone) of the crystal was the base core nm.

Example 7 A dyeing bath was prepared by dispersing dyes O and S t represented by the following structural formulas in 3 t of water containing a naphthalene sulfonic acid-formaldehyde condensate/f and 2 t of higher alcohol sulfate ester. Polyester fiber 1009 is immersed in this dyeing bath, /
, 307: for 6θ minutes for 15 minutes, soaping, washing and drying yielded a blue dyed fabric. The light fastness, sublimation fastness and water fastness of the obtained dyed fabric as well as the temperature stability during dyeing of the above dye were good.

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

The λmax (acetone) of the crystal was 6θ3 nm.

EXAMPLES A dyeing bath was prepared by dispersing dyes o and rt represented by the following structural formulas in 3 t of water containing naphthalene sulfonic acid-formaldehyde condensate/f and higher alcohol sulfate ester. Polyester fiber 1009 is immersed in this dyeing bath, /
After dyeing at 30C for 6 minutes, soaping, washing with water and drying for 16 minutes, a red dyed fabric was obtained. The light fastness, sublimation fastness and water fastness of the obtained dyed fabric as well as the temperature stability during dyeing of the above dye were good.

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

Crystal λ111aX (acetone)! It was set at flI/nm.

Example 1 A dyeing bath was prepared by dispersing dyes o and sy represented by the following structural formulas in 3 t of water containing naphthalene sulfonic acid-formaldehyde condensate/f and higher alcohol sulfate ester, 2 f. Polyester fiber/θOf is immersed in this dyeing bath,
After dyeing at /30C for AO minutes, soaping, washing with water and drying were performed to obtain a red dyed fabric. The light fastness, sublimation fastness and water fastness of the obtained dyed fabric as well as the temperature stability during dyeing of the dye were good.

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

The λmax (acetone) of this product was SSlnm.

Example IO Dye represented by the following structural formula θt! A dyeing bath was prepared by dispersing rt in water 31 containing naphthalene sulfonic acid-formaldehyde condensate/f and higher alcohol sulfate co-1. Polyester fiber/θOf is immersed in this dyeing bath,
After dyeing at 30C for 60 minutes, soaping, washing with water and drying were performed, a blue dyed fabric was obtained. The light fastness, sublimation fastness and water fastness of the obtained dyed fabric as well as the temperature stability during dyeing of the above dye were good.

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

The λmax (acetone) of this product is sq.

It was nm.

Example// Polyester fibers were dyed using the dyes shown in the table below in the same manner as in Example// to obtain dyed products having the tones shown in the table.

Claims (1)

[Claims] (1) General formula % formula % (wherein, X and Y represent a hydrogen atom, a halogen atom, a nido tetragroup, or a cyano group, R1 represents a hydrogen atom, a chlorine atom, a methyl group, or an acylamino group, and R2 represents a hydrogen atom) , represents a methyl group, a chlorine atom, a methoxy group or an ethoxy group, R3 and the total represent a hydrogen atom, a substituted or unsubstituted alkyl group, a cyclohexyl group, an alkenyl group or an aryl group, and %R1 represents a cyan group, an alkoxycarbonyl group, Monoazo dye for polyester fibers represented by benzyloxycarbonyl group or phenoxyetheroxycarbonyl group