JPS5951950A - Blended dye composition having ultrahigh light fastness - Google Patents

Abstract

PURPOSE:To provide a dye blend compsn. having excellent fastness to light and sublimation, by blending an anthraquinone disperse dye with a quinophthalone disperse dye. CONSTITUTION:An ultra-light-resisting dye blend compsn. is obtd. by blending at least one anthraquinone disperse dye selected from among dyes of formulas III(wherein R<1> is H, phenyl, arylsulfonyl; R<2> is OH, NH2; R<3>, R<4> are each H, halogen, phenoxysulfonyl, etc.), IV or V [wherein R<6>, R<7> are each NO2, NH2, lower alkylamino, (substd.) phenylamino; R<8> is halogen, (substd.) phenyl; m is 0-2] or VI [wherein Z is O, imino; R<9> is (substd.) alkyl] with a quinophthalone disperse dye of formula I (wherein the group of formula II is phenylene or naphthylene which may be substituted with halogen, lower alkoxy, phenyl or benzo-thiazolyl; X is halogen; n is 0-4).

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a blended dye composition having extremely good light fastness.

In recent years, as automobiles have become more sophisticated, the material for automobile interior materials, particularly for passenger seats, has been changing from polyvinyl chloride, which had been widely used in the past, to polyester fibers. Typical dyes for polyester fibers include ordinary clothing dirt.
In addition to requiring better light fastness than conventional dyes, it also needs to have a high level of sublimation fastness because it is heat set to match the shape of the seat after dyeing.

Currently, in order to dye automatic heavy-duty polyester fiber sheets, dyes that are appropriately blended with the three primary colors of berinone-based or anthraquinone-based yellow dyes, anthraquinone-based red dyes, and anthraquinone-based back color dyes are used. Red dyes have the disadvantage of poor sublimation fastness, and red dyes have poor light fastness and turn blue.
When used with mixed colors, the light fastness is insufficient, i6
It is not always satisfying, such as getting tired or having a lot of love at the time of heat setting.

The inventors of the present invention were keenly aware of these circumstances and conducted various studies in order to obtain a blended dye with minimal deterioration in dyeing quality even under harsh conditions. The present invention was achieved by discovering that a blended dye obtained by blending a specific anthraquinone disperse dye has excellent light fastness and sublimation fastness.

It is generally known that when disperse dyes are used in combination, the light fastness exhibited by each component is worse than the light fastness exhibited when each component is used alone. This phenomenon is called catalytic fade, and is particularly noticeable in azo dyes. On the other hand, according to the studies of the present inventors, when a specific anthraquinone disperse dye is used in combination with a specific quinophthalone disperse dye, the light fastness of the anthraquinone disperse dye itself is The light fastness of the quinophthalone disperse dye itself was significantly improved compared to when used alone, which is the complete opposite of the catalytic fade phenomenon. be.

The quinophthalone disperse dye used as an essential component in the blended dye composition of the present invention is represented by the following general formula [I].

(In the formula, halogen, lower alkoxy group.

low R flukoxycarbonyl group, lower alkoxy lower alkoxycarbonyl group, lower alkoxy lower alkoxy lower alkoxy carbonyl group, lower alkyl carbamoyl thread, phenylene group optionally substituted with phenyl group, benzoxacylyl group or benzothiazolyl group, or a naphthylene group, X represents glogen, and n is an integer of op. ,
Or indicated by [bar].

(In the formula, R1 represents hydrogen, a phenyl group, or an allylsulfonyl group, R2 represents a hydroxyl group, and R2 represents an amino group, and R3 and R4 represent hydrogen, a halogen, a phenoxysulfonyl group, or Y-R'' (where, Y is oxygen or sulfur, and R5 represents a substituted or unsubstituted lower alkyl group, cyclohexyl group or phenyl group.

) is displayed. ) ... (1) (In the formula, R6 and R7 represent a nitro group, an amino group, a lower alkylamino group, a phenylamino group, or a substituted phenylamino group, and R8 represents a halogen or a substituted or non-1' substituted Represents a phenyl group, and m is an O-λ symmetry.) (In the formula, 2 represents oxygen or imino group, and R9 represents a substituted or unsubstituted alkyl group.) General formula [I]
~ In [■], the lower alkyl group or lower alkoxy group means a linear or branched alkyl group or alkoxy group with m number of atoms/-1, and examples of the halogen include chlorine, bromine or iodine. It will be done.

Examples of the allylsulfonyl group represented by R1 include a phenylsulfonyl group and a tolylsulfonyl group.

Substituents for the f& substituted lower alkyl group represented by R'' include halogen, cyano group, hydroxyl group, lower alkoxy group, lower alkoxy lower alkoxy group, cyano lower alkoxy group, lower alkoxycarbonyl group, lower alkoxycarbonyloxy aryloxy groups, such as allyloxycarbonyl groups, carbamoyl or phenoxy groups, and hydroxyethoxyphenyloxy groups;
Aralkyloxy groups such as benzyloxy groups and chlorobenzyloxy groups, aryl groups such as phenyl groups and chlorophenyl groups, acetyloxy groups, chloroacetyloxy groups,
Examples include acyloxy groups such as chloropropionyloxy, benzoyloxy, aralkyloxycarbonyl groups such as benzyloxycarbonyl, and substituents for the cyclohexyl group placed 1q include halogen, hydroxyl, etc. Substituents for the phenyl group include haloken, lower alkyl group, lower alkoxy group, lower alkylthio group, phenoxy lower alkoxy group, cyano lower alkyl group, low M alkoxycarbonyl lower alkyl group, lower alkyl sulfonyloxy group,
Examples include phenoxysulfonyl group, lower alkylsulfamoyl group, and lower alkoxy lower argylsulfamoyl group.

The substituted phenylamino group represented by R6 and R7 includes halogenophenylaminonor such as N-(chlorophenyl)ami/group, N'-(bromophenyl)amino group, N-)lylamino group, N-(ethylphenyl) Examples include lower alkylphenylamine groups such as ami/group, lower acid alkyl phenylamine groups such as N-(ethoxyphenyl)amine, hydroxy lower alkylphenylamine groups such as N-(hydroxyethylphenyl)amine/group, etc. I get kicked.

Examples of the crystals of the phenyl group represented by R8 include a hydroxyl group, a lower alkyl group, and a lower alkoxy group.

Examples of the alkyl group represented by R9 include linear or branched alkyl groups having l-carbon atoms, and examples of substituents for the alkyl group include the same direct substituents for the lower alkyl group in R5 above. One head substitution is honored.

The dyes represented by the general formulas [1] to [1v] contain various colors such as yellow, red, purple, tone color, and turquoise blue, so by appropriately blending these dyes, Compound dyes of almost any shade can be borrowed.Of course,
The blending of each dye can also be carried out at the time of preparing the dye bath or printing paste.

Among the 0゛.4 names that can be dyed with the blended dye composition of the present invention, polyester fibers made of polyethylene terephthalate, polycondensates with terephthalate, lI-bis-(hydroxymethyl)cyclohexane, etc. Blend products and mixed fiber products of natural fibers such as cotton, silk, and wool and the above-mentioned polyester fibers are added.

When dyeing Polynysterte 14 fibers using the blended dye composition of the present invention, a dispersing agent such as a condensate of naphthalene sulfonyl 7 and formaldehyde, a higher alcohol phosphoric acid ester, or a higher alkylbenzene sulfonate is used. The blended dye composition of the present invention may be dispersed in an aqueous medium to prepare a printing paste, and then dyeing or printing can be carried out.For example, when carrying out dyeing,
By applying ordinary dyeing methods such as high-temperature dyeing, gearier dyeing, and thermosol dyeing, it is possible to dye polyester reduced fibers, their blends, and mixed fiber products with excellent fastness and beauty. However, in some cases, even better results may be obtained by adding an acidic substance such as formic acid, acetic acid, i3"Ge, or ammonium sulfate to the dyeing bath.

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

In addition, in the following 9 cases, staining was performed using the following procedure.

l) Test fiber; Polyester tropical cloth 0f 2) Dyeing method; Colorpet dyeing method (high temperature dyeing method using Japanese dyeing machine (Hikiki) (147θ'c, x Ao minute) 3) Kaze bath; Disperse dye iN leveling agent
θS Vt (日-!1゛(Chemistry 7 Earthenware-Linrunlt~700θ)p
lI regulator! r me (Vinegar sorter 3θVt, aqueous solution of acetic acid/07/l)
Remaining water: 30 θm) Post-processing: After cooling, washing with water, cleaning and Example light resistance test: 37) Conducted by carbon arc lamp at 3°C for 200 hours p', t')'t. death,
The light fastness is determined by the gray scale, and the fading rate is determined by measuring the reflectance at the λmax value of each dye using a reflection tester 70 KO2-ig (manufactured by Kollmorgen) and using the Kubelkamunk formula /S = (/-Rλ )2/, 2Rλ1!
K: absorption coefficient, S: scattering coefficient, Rλ: spectral reflectance)
/S was calculated using the following formula.

That's sweet, yl 5f test is a dyed fabric made by Pintenter Thermosol Test (manufactured by Tsujii Senko Kogyo (114→)).
Heat treated with ioc for 60 seconds, and the degree of discoloration of the dyed fabric was measured at NB.
I was saved by S unit.

That is, Y means yellowing, R means reddening, B means bluening, and D means darkening, and the larger the value, the greater the degree of discoloration.

Example 1 The following (A-/) was added to the quinophthalone dye listed in Table-/
Saitake (A-, 2) (A-/) (A-, 2) A mixture (C, 1, A B / 9 g) of anthraquinone disperse dye was blended in /:/ (weight ratio) to make polyester fiber. was dyed, and the fading rate of the yellow component exhibited by the chimephthalone disperse dye was measured by a light fastness test. Table 7 of the results
Shown below.

Table-/ Example.

The quinophthalone disperse dye (Q
-A) to (A, -1,), (A-, 2) and the following pj
-2~SK anthraquinone disperse dye i:t
(weight: 1% ratio) and dye the polyester fiber.1.
The fading rate of the yellow component exhibited by the quinophthalone disperse dye and the red, purple, blue color, or turquoise blue component exhibited by the anthraquinone disperse dye was measured by a light fastness test.

The results are shown in Table-6.

Table-1 Example 3, Comparative Example 1 Yellow component (Q-2), (Q-1') and lower 3
Self (Y-/), (Y-2) and (y-3) (Y-/) (Y-1) ” (A-2), (A-9), (A-wo Hiroshi), (A -25)
, (A-ko9), (A-, rt) and the following (R-/
), (R-co), (R-3), (B-l), (11-2
) and (B-j) (几-l) 11 (R-co) NHCOCH.

(R-,?) CB-/) (B-2) (v3'-,?) was distributed at a ratio of 1:/(superimposition) to dye the polyester fiber. The fading rate of the obtained dyed fabric was measured for each component by a light fastness test, and the results are shown in Table 7.

EXAMPLE DA, COMPARATIVE EXAMPLE For dyeing copolyester fibers dark gray
Dyeing was carried out by blending a predetermined amount of the dye described in g. The results of the 171f light test and thermal change test of the obtained dyed fabric are shown in 11-g.

Human-g Example J, Comparative Example 3 In order to dye polyester fibers silver gray, a predetermined amount of the dye listed in the table was blended and dyed.

The results of the light resistance test (h/k) and thermal change test of the obtained dyed fabric are shown in Table-9.Table-9

Claims (1)

[Claims] (1) General formula Even if substituted by a lower alkoxycarbonyl group, a lower alkoxy lower alkoxycarbonyl group, a lower alkoxy lower alkoxy lower alkoxycarbonyl group, a lower alkylcarbamoyl group, a phenyl group, a benzoxacylyl group or a benzothiazolyl group It represents a good phenylene group or a naphthylene group, X represents a halogen, and n is an integer from o to g. ), a quinophthalone-based disperse dye represented by the general formula (wherein R1 represents hydrogen, a phenyl group or an allylsulfonyl group, R2 represents a hydroxyl group or an amino group, and R3 and R4 represent hydrogen halogen or a phenoxysulfonyl group) is used. or Y-R5 (Y represents oxygen or sulfur, and R5 represents a substituted or unsubstituted lower alkyl group, cyclohexyl group, or phenyl group.)
It shows the horns. ) General formula (wherein R6 and R7 represent a nitro group, an amino group, a lower alkylamino group, a phenylamino group, or a substituted phenylamino group; L/, n'lj represents a halogen or a substituted or unsubstituted phenyl group; , m is an integer from θ to co. A super light-fast compounded dye composition comprising at least one dye.