JPS61166857A - Quinophthalone compound - Google Patents

Abstract

NEW MATERIAL:A compound of formula I [W is halogen; Q is formulas II, III (R<1> is H, alkyl; R<2> is alkylene; R<3> is alkyl; A is anion)]. EXAMPLE:The compound of formula IV. USE:A dye dyeing OH-containing fibers such as cotton, amino group-containing fibers such as wool and anion-bearing fibers such as acrylic fibers yellow fast to moisture. PREPARATION:The reaction of a compound of formula V with an s-triazine of formula VI gives a compound of formula IX. Then, the product is allowed to react with an alkylating agent of formula R<3>-A in an organic solvent at room temperature - 90 deg.C for 0.5-5hr.

Description

[Detailed description of the invention] Industrial applications The present invention relates to quinophthalone compounds.

Specifically, the present invention relates to quinophthalone compounds capable of dyeing fibers containing human myxyl groups, amino groups or anionic groups.

Conventional technology Conventionally, anionic water-soluble dyes having a -soma group have been used to dye syl group-containing fibers and amino group-containing fibers. In this case, a cationic water-soluble dye having a q-classified nitrogen atom is conveniently used.

When dyeing mixed fibers of hydroxyl group-containing fibers, amino group-containing fibers, and anionic group-containing fibers, two types of dyes, the above-mentioned anionic water-soluble dyes and cationic water-soluble dyes, are used. Therefore, the dyeing conditions are different for each, and it is impossible to dye hydroxyl group-containing fibers, amino group-containing fibers, and anionic group-containing fibers at the same time. There were problems such as the formation of complexes and poor dyeing.

Problems to be Solved by the Invention The present invention is directed to a hydroxyl group-containing fiber and an amino base 1i.
When dyeing mixed fibers of r fibers and anionic group-containing fibers, use /fi dyes to simultaneously dye dorosyl group-containing fibers, amino group-containing fibers, and anionic group-containing fibers. The object of the present invention is to provide a quinophthalone compound that can be dyed.

Means for Solving the Problems The present invention is based on the following general formula CI] In the formula, -W represents a halogen atom, -Q represents a group, R1 represents a hydrogen atom or an alkyl group, and R3
represents an alkyl group, R3 represents an alkyl group,
Ae is a quinophthalone compound represented by the symbol ``0'' representing an anion.

In the quinophthalone compound of the present invention represented by the general formula [1], the halogen atom represented by -W includes a fluorine atom, a chlorine atom, or a bromine atom, and particularly preferably a fluorine atom. Examples of the alkyl group represented by R3 include methyl group and ethyl group, and examples of the alkyl group represented by Rz include ethylene group,
Examples of the anion represented by M include halogen anions; alkyl sulfate anions such as methyl sulfate anions and ethyl sulfate anions; and aryl sulfate anions such as methylphenyl sulfate anions.

The compound represented by the above general formula [1] is represented by the compound represented by the following structural formula [n), the following general formula 1] and -R3 are the same as defined above. −
A compound represented by the following general formula (in the formula, -W and -Q' are the same as defined above) obtained by reacting a 6-triazine compound with a general formula [■ Ra -A...・・・・・・・・・・・・・・・
... an algylating agent represented by [■] (-R3 and -A are the same as 1 above definition) in an organic solvent at room temperature to 9.
It can be easily produced by reacting at 0°C for 0.3 to 5 hours.

Specific examples of the alkylating agent represented by the above general formula (1) include dimethyl R[, diethyl (IIIE powder, methyl bromide, ethyl bromide, methyl iodide, ethyl iodide, p-toluenesulfonic acid methyl ester, Examples include phosphoric acid triethyl ester, etc., and the fecal dosage of the alkylating agent is /, 0-, - / with respect to the compound represented by the above general formula layer.
, 1 mole times the range.

Examples of the organic solvent include acetone, methyl ethyl ketone, dioxane, tetrahydrofuran, toluene, chlorobenzene, dichlorobenzene, and nitrobenzene.

Examples of the hydroxyl group-containing fibers that can be dyed with the Hinophthalone compound of the present invention represented by the above general formula CI) include natural fibers such as cotton and linen, semi-synthetic wtm fibers such as hiscose rayon, and copper ammonia V-yon. Examples of amino group-containing fibers include woven and knitted fabrics such as wool, silk, synthetic polyamide and polyurethane fibers, and examples of anionic group-containing rutted fibers include acrylic fam.
and woven or knitted fabrics of cationically dyeable polyester fibers, particularly blended products, mixed fiber products, and mixed knitted products of the above-mentioned human cuxyl group-containing fibers and amine 7 group-containing fibers with anionic base fibers.

When carrying out dyeing, the aqueous solution of the general formula [■] can be used as it is as a dye bath in the dipping dyeing method, as a padding bath in the padding dyeing method, or as a color paste in the textile printing method when used in combination with a paste. 〇When padding dyeing or printing mixed fibers of acrylic fibers, human cuxyl group-containing fibers, and amino group-containing fibers, use urea or polyethylene glycol, polypropylene gelcol, etc. with an average molecular weight of about 0 to 300 at both ends. It is desirable to use polyhydric alcohols that do not react with dyes whose hydroxyl groups are dimethylated or diacetylated, and furthermore to use acid binders for the purpose of promoting the reaction with dye hydroxyl groups or amino groups. As the a1B mixture, an alkali precursor compound that generates an alkali when heated in the presence of water, such as sodium trichloroacetate, is desirable.

The amount of urea or polyhydric alcohol is about J to C weight % based on the padding bath or printing dyeing paste, and the amount of sodium trichloroacetate used is - in general formula [I].
Since W has high in-situ reactivity with fluorine atoms, 0-3~o, r
weight]t%, 1 for chlorine or bromine atoms. Q~
/, j% by weight is desirable.

Although it is a dye solidification method, in the dip dyeing method, the temperature is 93℃~
/ JO ~ 60 minutes at 30°C, for padding dyeing or textile printing, after drying lθ 0° ~ 130°C saturated steam for 3 minutes ~ IQ minutes, / 40'~2 0°C hot air or superheated steam for 30 seconds ~ Heat treatment may be performed for 0 minutes.

Subsequently, by washing with hot water containing a common surfactant, a vivid and uniformly dyed product with good wet fastness can be obtained.

Hereinafter, the BA of the present invention will be explained in more detail with reference to examples, but the present invention is not limited to the following examples.

Example 1 Compounds r and og represented by the following structural formula and dimethyl sulfate 1. With Jfi, in the Geo competition Sun 100-! The reaction was carried out at rθ°C for 3 hours, and the precipitated crystals were filtered after cooling to obtain 6.1 g of the 1,000-7 tano compound of the present invention represented by the following structural formula. 0% methanol water) is 4c40
It was nm.

[The above structural compound of the bile base of printing dyeing paste Illμ la carbomethoxy cellulose water Hg z s i tetraethylene glycol dimethyl ether! rI
Sodium trichloride vinegar o,
r g water
3g3g Prepare the above crude printing dyeing paste, print on acrylic/cotton (mix ratio: so7 to O) blended fabric using a screen printing machine, dry for 3 minutes at 10°C, and then print using superheated steam. , and treated at 170°C for 7 minutes. After washing this product with water, fill it with nonionic surfactant (
Using a cleaning solution containing Kao Soap Co., Ltd. Urazo (trademark) Nucoaroll + Hiro 00no, the bath ratio was 2θ at 90°C at a bath ratio of /:30.
I did noping for a minute.

In this way, a uniform yellow dyeing with excellent wet fastness was obtained.

EXAMPLES According to the method described in Example 1, a quinophthalone compound of the present invention represented by the following structural formula was produced.

This product's λ, 1nax (K O% methanol water) is
It was Ionm.

Composition of Pub Ink Bath The above structural compound -g Diethylene glycol 1,000-onythyl 4g Sodium trichloroacetate 0. j jj Prepare a padding bath with the above composition and add acrylic/6-nylon (
A blended fabric (mixing ratio: 0700) was impregnated and fixed by steaming for 7 minutes at GIOO°C with a squeezing rate of 30%. When this product was treated according to the procedure described in Examples, a yellow dyed product was obtained which was uniform, clear, and had excellent wet fastness.

Example 3 According to the method described in Example 1, a quinophthalone compound of the present invention represented by the following structural formula was produced.

The λmax (g 0% methanol water) of this product is 4 (39
It was nm.

/71% of the quinophthalone compound represented by the above structural formula
Aqueous solution (pEi7.3) and acrylic/wool (& combination!
rO7!0) The mixed fiber product was treated at qt° C. for 1 hour and then washed with hot water to obtain a uniform yellow dyed product with no irritation.

Example j The same is true except that the fiber used in Example 1 was changed to acrylic/wool (mixing ratio!; 0/OJ blend fabric)
(Thus, upon dyeing, a yellow dyed product with uniform wet fastness was obtained.

Example! Dyeing was carried out according to the method described in Example 1, except that the fiber used in Example 1 was replaced with cotton cloth, and a yellow dyed product with excellent wet fastness was obtained.

Example 6 The fiber used in Example 3 was dyed according to the method described in Example 3, except that it was changed to a cationically dyeable polyester/wool (mixing ratio: 0/! OJ blend fabric), and uniform wet fastness was obtained. An excellent yellow dyeing was obtained.

Example 7 In Table 7 below, 3 were prepared according to the method described in Example 1.
Padding staining was carried out using a self-contained quinophthalone compound according to the method described in Examples. The color tone of the obtained dyed product and the λm of the quinophthalone (L)
ax (K O% methanol water) is shown in the first column.

Example g When dyed according to the method described in Example 3 except that the fibers used in Example 3 were changed to a cotton/nylon/acrylic (mixing ratio: rO/30/YUO) mixed woven fabric, uniform wet fastness was obtained. A yellow dyed product with excellent strength was obtained.

Claims (1)

[Claims] (1) General formula [I] ▲There are mathematical formulas, chemical formulas, tables, etc.▼[I] (In the formula, -W represents a halogen atom, -Q is ▲mathematical formula,
There are chemical formulas, tables, etc. ▼ groups or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ Represents a group, -R^1 represents a hydrogen atom or an alkyl group, R^2 represents an alkylene group, and R^3 represents an alkyl group. A quinophthalone compound represented by the following formula (A^■ represents an anion).