JPS5934825B2 - Dyeing method for synthetic fibers - Google Patents

Description

[Detailed description of the invention] The present invention relates to a method for dyeing synthetic fibers,
More specifically, the present invention relates to a method for dyeing polyester fibers, cellulose ester fibers, or blends or mixed fibers thereof into a red tone with excellent light resistance, sublimation resistance, and washability after resin processing.

That is, the present invention is based on the following general formula Tani, Nimi]--1-e-<1 (wherein, R1 is an unsubstituted alkyl group; a hydroxyl group;
Alkyl group substituted with a cyano group or carbamoyl group; represents an aralkyl group or an allyl group, R2 is a hydrogen atom; unsubstituted alkyl group; hydroxyl group, alkoxy group, alkoxyalkoxy group, furfuryloxy group, tetrahydrofurofuryl Oxy group, acyloxy group, alkoxycarbonyl group, alkoxycarbonyloxy group, cyano group, halogen atom, alkoxyalkoxycarbonyl group, furfuryloxycarbonyl group, tetrahydrofurfuryloxycarbonyl group, furyl group, tetrahydrofuryl group, morpholino group, carbamoyl R3 represents a hydrogen atom or a methyl group; an aralkyl group or an allyl group; R3 represents a hydrogen atom or a methyl group;

) is a method for dyeing synthetic fibers using a water-solubilizable dispersed monoazo dye that does not contain sulfonic acid groups or carboxyl groups.

The present invention will be explained in detail.

In the monoazo dye represented by the general formula (1) in the method of the present invention, specific examples of R1 are as follows:
Unsubstituted alkyl groups such as methyl group, ethyl group or propyl group, β-hydroxyethyl group, β-hydroxypropyl group, β,γ-dihydroxypropyl group, β-cyanoethyl group, β-methoxycarbonylethyl group, β- Examples include substituted alkyl groups such as ethoxycarbonylethyl group or carbamoylethyl group, aralkyl group such as benzyl group, and β-phenylethyl group, or allyl group.

Next, examples of R2 include a hydrogen atom, an allyl group, an unsubstituted alkyl group such as a methyl group, an ethyl group, a propyl group, or a butyl group, a benzyl group, or a β-
Aralkyl groups such as phenylethyl groups, hydroxy groups,
A substituted alkyl group having a substituent such as an alkoxy group, a cyano group, a halogen atom, an alkoxycarbonyl group, an acyloxy group, an alkoxycarbonyloxy group, a furyl group, a tetrahydrofuryl group, a morpholino group, a carbamoyl group or an N-alkyl substituted carbamoyl group can give.

As specific examples of alkyl groups having these substituents, those having a hydroxy group include a β-hydroxyethyl group, a β-hydroxypropyl group, a β-γ-dihydroxypropyl group, and an α-hydroxymethyl-β-hydroxyethyl group. group, γ-hydroxybutyl group or β-(!-hydroxyethoxy)ethyl group. As the lower alkyl group having an alkoxy group, an acyloxy group, an alkoxycarbonyloxy group, a furyl group, or a tetrahydrofuryl group, the hydroxy group of the lower alkyl group having a hydroxy group mentioned above can be replaced with a methoxy group, an ethoxy group,
propoxy group, butoxy group, β-methoxyethoxy group,
β-ethoxyethoxy group, β-butoxyethoxy group, furfuryloxy group, tetrahydrofurfuryloxy group,
Examples include those converted to an acetoxy group, a propionyloxy group, a benzoyloxy group, a methoxycarbonyloxy group, an ethoxycarbonyloxy group, or a butoxycarbonyloxy group.

The lower alkyl group having a cyano group, halogen atom, alkoxycarbonyl group, furyl group, tetrahydrofuryl group, morpholino group, carbamoyl group or N-alkyl substituted carbamoyl group includes β-cyanoethyl group, β-
Chloroethyl group, β-bromoethyl group, methoxycarbonylmethyl group, ethoxycarbonylmethyl group, butoxycarbonylmethyl group, β-methoxycarbonylethyl group, β-ethoxycarbonylethyl group, β-propoxycarbonylethyl group, β-butoxycarbonylethyl group ,
β-(β5-methoxyethoxycarbonino(c)ethyl group, β-(methoxyethoxycarbonyl)ethyl group, β-furfuryloxycarbonylethyl group, β-tetrahydrofurfuryloxycarbonylethyl group, furfuryl group, tetrahydrofuryl group) Furyl group, morpholinoethyl group, β-carbamoylethyl group, β-(N-methylcarbamoino(ha)ethyl group, β-(N-ethylcarbamoinole)ethyl group, β-(N,N-dimethylcarbamoyl) Examples include a monoethyl group, and a β-(N,N-diethylcarbamoyl)ethyl group.

Further, R6 represents a hydrogen atom or a methyl group.

The dye represented by the general formula (1) shown above is, for example, the dye represented by the formula ()
A diazo compound obtained by diazotizing 2-amino-4,5-dicyanoimidazole represented by λT is expressed by the general formula (1) (
In the formula, R2 and R3 have the same meanings as in the general formula (1) above.

) (where R2, R
3 has the same meaning as in the general formula (1) above.

) is produced by alkylating one of the nitrogen atoms in the imidazole ring.

In order to dye synthetic fibers such as polyester fibers, cellulose ester fibers, or blends or mixed fibers thereof according to the method of the present invention, dyes represented by the general formula (1) above may be used alone or in combination. Using a dyeing bath or printing paste prepared by dispersing the above mixture in an aqueous medium by a conventional method, dyeing or printing is carried out by a known method. To prepare this dyeing bath or printing paste, for example, a condensate of naphthalenesulfonic acid and formaldehyde, a higher alcohol sulfate, or a higher alkylbenzene sulfonate is used as a dispersant.

In addition, when dyeing is carried out using the above dyeing bath or printing paste, phenylphenols, chlorobenzenes, hydroxybenzoic acid esters, phenylmethyl carbinols, or alkylnaphthalenes may be used as carriers, if necessary. You can also use When performing dip dyeing, prepare a dyeing bath according to the desired dyeing concentration as described above, and perform high-temperature dyeing of polyester fibers.
After dyeing at 120 to 130°C for 60 to 120 minutes, soaping is carried out according to a conventional method.To carry out carrier dyeing, add an appropriate amount of the carrier to the dyeing bath,
After dyeing at 100°C, soaping is carried out in a conventional manner.

In addition, when dyeing cellulose ester fibers, prepare a dyeing bath as described above at 80-100℃ and 60-120℃.
After staining for 0 minutes, soaping is performed. When synthetic fibers are dyed according to the method of the present invention, it is possible to obtain a red-toned dyed product with excellent light fastness, sublimation resistance, and washing resistance after resin processing. 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 dye bath was prepared by dispersing 0.59 of a dye represented by the following structural formula in water 32 containing 19 of a naphthalene sulfonic acid formaldehyde condensate and 29 of a higher alcohol sulfate ester.

Polyester fiber 1009 was immersed in this dye bath, and 130
After dyeing at ℃ for 60 minutes, soaping, washing with water, and drying were performed to obtain a bluish-red polyester fiber dyed material BS with good light fastness and sublimation fastness.

The dye used in this example was prepared by diazotizing 2-amino-4,5-dicyanoimidazole in a conventional manner and coupling it to 8-γ-methoxypropylaminoquinoline. It was manufactured by

In addition, the maximum absorption wavelength λMax of the dye (acetone) is
It was 530 nm. Example 2 0.5 g of a dye represented by the following structural formula was dispersed in water 31 containing 1.59 of a naphthalene sulfonic acid formaldehyde condensate and 19 of a higher alcohol sulfate ester, and a methylnaphthalene carrier 159 was added thereto to prepare a dye bath. was prepared.

Polyester fiber 1009 was immersed in this dye bath,
After dyeing at 0.degree. C. for 90 minutes, soaping, washing with water, and drying were performed, a bluish-red polyester fiber dyed material BS with good light fastness and sublimation fastness was obtained. The dye used in this example was prepared by diazotizing 2-amino-4,5-dicyanoimidazole in a conventional manner, coupling it to 8-β-hydroxyethylaminoquinaldine, and adding the resulting compound to diethyl sulfate. Produced by ethylation.

Moreover, the maximum absorption wavelength (acetone) of this dye is 530n
It was m. Example 3 Polyester fibers were dyed in the same manner as in Example 1 using the dyes shown in the table below to obtain dyed products with excellent color fastness in the colors shown in the table below.

Claims (1)

[Claims] 1 The following general formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) (In the formula, R
_1 is an unsubstituted lower alkyl group; a lower alkyl group substituted with a hydroxyl group, a cyano group, or a carbamoyl group; a benzyl group; a β-phenylethyl group; a P-chlorobenzyl group; an allyl group; R_2 is a hydrogen atom; Unsubstituted lower alkyl group; hydroxyl group, lower alkoxy group, lower alkoxy lower alkoxy group, furfuryloxy group, tetrahydrofurfuryloxy group, acyloxy group, lower alkoxycarbonyl group, lower alkoxycarbonyloxy group, cyano group, halogen atom , lower alkoxy substituted with lower alkoxycarbonyl group, furfuryloxycarbonyl group, tetrahydrofurfuryloxycarbonyl group, furyl group, tetrahydrofuryl group, monophorino group, carbamoyl group, N-lower alkylcarbamoyl group, or acyloxy lower alkoxy group Lower alkyl group; benzyl group; β-phenylethyl group; allyl group; R_3 represents a hydrogen atom or a methyl group. ) A dyeing method for synthetic fibers, characterized by using a water-solubilizable dispersed monoazo dye that does not contain sulfonic acid groups or carboxyl groups.