JPS5843515B2 - Senshiyokuhouhou - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for dyeing synthetic fibers using novel dyes.

The present inventors have conducted repeated research on the dyeing of synthetic fibers, particularly polyester fibers, cellulose ester fibers, and blended products or mixed fiber products containing these fibers. The present invention has been achieved based on the discovery that it can be dyed in a scarlet to purple tone with excellent fastness properties such as heat resistance, light resistance, sublimation resistance, and washing fastness after resin processing.

That is, the purpose of the present invention is to dye synthetic fibers in a scarlet to purple tone with excellent fastness.
For this purpose, the general formula [wherein X represents a hydrogen atom, a halogen atom or a lower alkyl group, and Y represents a hydrogen atom or a halogen atom,
Z represents a halogen atom, a nitro group or a cyano group, W
represents a hydrogen atom, a lower alkyl group or a lower alkoxy group, R1 is a hydrogen atom, a lower alkyl group or -C2H4
COOR2 represents a lower alkyl group, a lower alkoxyalkyl group, an allyl group, an aryl group, an aralkyl group which may have a substituent, a furfuryl group, a tetrahydrofurfuryl group, a cyclohexyl group, and R3 represents a lower alkyl group. represents a group.

] This is achieved by using a dispersed monoazo dye represented by:

To explain the present invention in more detail, the dye represented by the general formula CI) is, for example, a dye represented by the general formula (wherein X, Y and 2 have the same meanings as in the general formula (I)).

] A 2-aminobenzothiazole derivative represented by the general formula [wherein W, R1, R2 and R3 are general formula CI]
has the same meaning as in .

It is produced by coupling with an aniline represented by ].

Specific examples of the 2-aminobenzothiazole derivatives represented by the general formula [■] include 2-amino-6-nitrobenzothiazole, 2-amino-4-7'rom-6-nitrobenzothiazole, 2-amino- 4,6-dichlorobenzothiazole, 2-amino-4,6-dichlorobenzothiazole, 2-amino-5,6-dichlorobenzothiazole, 2-amino-5,6-dichlorobenzothiazole 2-amino -6-Chlorhensothiazole 2-
Amino-6-bromobenzothiazole, 2-amino-6
-diatubenzothiazole, 2-amino-4-methyl-
Examples include 6-nitrobenzothiazole.

Further, as specific examples of anilines represented by the general formula (II[), 3-acetylamino-N-β-(methoxycarbonyl)ethylaniline 3-acetylamino-N-N-bis-β-(ethoxycarbonyl) carbonyl)ethylaniline 3-propionylamino-N-ethyl-N-β
-(methoxycarbonyl)ethylaniline 2-ethoxy-5-acetylamino-N-β-(furfuryloxycarbonyl)ethylaniline, 2-methoxy-5-acetylamino-N-ethyl-N-β-(cyclohexanoxycarbonyl ) Ethylaniline, 3-acetylamino-N
-Methyl-N-β-(ethoxyethoxycarbonyl)ethylaniline, 3-acetylamino-N-butyl-N-
β-(tetrahydrofurfuryloxycarbonyl)ethylaniline, 2-methyl-5-acetylamino-N-propyl-N-β-(-r-)*dicarbonyl)ethylaniline 3-acetylamino-N-N-bis- β-(benzyloxycarbonyl)ethylaniline, 3-acetylamino-N-ethyl-N-β-(phenethyloxycarbonyl)ethylaniline, 3-acetylamino-N-N-
bis-β-(phenoxycarbonyl)ethylaniline,
2-ethoxy-5-acetylamino-N-7''ropyru-N-β-(,a/-methylphenyloxycarbonyl)ethylaniline 3-acetylamino-N-N-bis-β-(furophokidicarbonyl)ethyl Aniline, 3-
Examples include acetylamino-N-butyl-N-β-(butoxycarbonyl)ethylaniline.

In order to dye synthetic fibers, such as polyester fibers, cellulose ester fibers, or blended fabrics or blended fabrics containing these, according to the present invention, the dye represented by the general formula CI) may be used in combination with two or more types of dyes. Using a dyeing bath or printing paste prepared by dispersing the mixture in an aqueous medium by a conventional method,
Dipping or printing is carried out by a known method.

To prepare this dyeing bath or printing paste, for example, a condensate of naphthalene sulfonic acid and formaldehyde, a higher alcohol sulfuric acid ester, or a higher alkylbenzene sulfonate is used as a dispersing agent.

Furthermore, when dyeing is carried out using the above-mentioned dyeing bath or printing paste, phenylphenols, chlorobenzenes, hydroxybenzoic acid esters, benzenedicarboxylic acid esters, phenylmethyl carbinols, or alkyl Naphthalenes and the like can also be used.

When performing dip dyeing, prepare a dyeing bath according to the desired dyeing concentration as described above, and for high-temperature dyeing of polyester fibers, dye at 120 to 130°C for 60 to 120 minutes, then soap using a conventional method. However, in order to carry out carrier dyeing, an appropriate amount of the carrier is added to the dye bath, dyeing is carried out at 80 to 100 DEG C., and then soaping is carried out in a conventional manner.

In addition, in the case of dyeing cellulose ester fibers, prepare the dyeing bath as described above and dye the dye at 80 to 120℃ at 80 to 120℃.
After staining for a minute, soap the area.

When using the method of the present invention, synthetic fibers can be dyed in scarlet to purple tones with excellent fastness properties, particularly heat resistance, light resistance, sublimation resistance, and washing fastness after resin processing.

Examples are shown below, but the present invention is not limited to the following examples unless it exceeds the gist thereof.

Note that the various fastnesses described in the examples were measured according to the following standards.

Heat fastness (abbreviated as HF) JISL 0879 (1968) 180°C x 30 seconds Iron tester Light fastness (abbreviated as LF) JISL 0842 (1971) Fade meter sublimation fastness (abbreviated as SF) JISL 0879 (1968) 180 ℃×30 seconds Iron tester Washing fastness after resin processing (abbreviated as WF) ASAL14.
81 (1963) TestAnA Nylon Contamination In the examples, "parts" indicate "parts by weight."

Example 1 Dye of the formula (λmaX533 in acetone)
mμ) was finely kneaded with 2 parts of a condensate of naphthalene sulfonic acid and formaldehyde, and then mixed with 3000 g of water.
100 parts of polyester fibers were immersed in this dye bath and dyed at 130° C. for 60 minutes.

The dyed product was dyed deep red by immersing it in 3,000 parts of water containing 6 parts of IJum, 6 parts of hydrosulfide and 6 parts of monogen and soaping at 80°C for 10 minutes. Obtained.

The LF of the dyed product was grade 5-6, the SF was grade 5, the WF was grade 4-5, and the HF was grade 5.

The dye used in this example was produced by diazotizing 2-amino-4,6-difuromebenzothiazole in a conventional manner and coupling it with 3-acetylamino-N-N-bis-β-(ethoxycarbonyl)ethylaniline. did.

A dyebath was prepared in the same manner as in Example 1 using 1 part of the dye represented by Example 2 (λmax 565 mμ) and further 5 parts of methylnaphthalene were added.

100 parts of polyester fibers were immersed in this dye bath at 100°C.
After washing with water, the dyed product was immersed in 3,000 parts of water containing 5 parts of Marcel soap and soaped at 90° C. for 10 minutes to obtain a deep purple dyed product.

LF of dyeing is grade 56, SF is grade 4-5, WF is grade 4-5.
The grade and HF were **5 grade.

The dye used in this example was prepared by diazotizing 2-amino-6-nitrobenzothiazole and coupling it with 3-acetylamino-N-ethyl-N-β-(tetrahydrofurfuryloxycarbonyl)ethylaniline.

Example 3 Polyester fibers were dyed in the same manner as in Example 1 using the dye represented by the formula (λmax 588 mμ) to obtain a deep reddish-blue dyed product.

The LF of the dyed product was grade 5-6, the SF was grade 4-5, the WF was grade 4, and the HF was grade 5.

The dye used in this example was produced by diazotizing 2-amino-4from*6-nitrobenzothiazole and coupling it with 2-ethoxy-5-acetylamino-N-β-(ethoxycarbonyl)ethylaniline.

Examples 4 to 21 Polyester fibers (tetron) and cellulose ester fibers (acetate) were dyed in the same manner as in Example 1 using dyes represented by the general formulas having substituents shown in the table below, and the results are shown in the table below. I got it.

Note that LF, SF, WF, and HF were measured with respect to Tetron.

Claims (1)

[Claims] 1 General formula CI) [wherein, X represents a hydrogen atom, a halogen atom or a lower alkyl group, and Y represents a hydrogen atom or a halogen atom,
Z represents a halogen atom, a nitro group or a cyano group, W
represents a hydrogen atom, a lower alkyl group or a lower alkoxy group, R1 is a hydrogen atom, a lower alkyl group or -C2H4
COOR2 represents a lower alkyl group, a lower alkoxyalkyl group, an allyl group, an aryl group, an aralkyl group which may have a substituent, a furfuryl group, a tetrahydrofurfuryl group, a cyclohexyl group, and R3 represents a lower alkyl group. represents a group. A method for dyeing synthetic fibers characterized by using a dispersed monoazo dye represented by (excluding methods).