JPH02228366A - Disazo disperse dye - Google Patents

Abstract

NEW MATERIAL: A compd. represented by formula I (wherein R₁ and R₁' are H, chloro, bromo, 1-3C alkyl or 1-2C alkoxy and R₃ and R₄ are 2-3C alkylene).

EXAMPLE: A compd. represented by formula II.

USE: A dis-azo disperse dye dyeing a hydrophobic fiber material yellow-orange.

PROCESS: 1 mol of a diazotized aminobenzene compd. represented by formula III and 1 mol of a compd. represented by formula IV are coupled.

COPYRIGHT: (C)1990,JPO

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to disazopyridone disperse dyes and mixtures thereof and their suitability as disperse dyes for dyeing, pad dyeing or printing hydrophobic fiber materials.

According to the invention, the following formula I, wherein R1, p+ and R2 are each independently hydrogen, chloro, bromo, Cl-2alkyl or CI-
selected from Z alkoxy, Ryu and R4 are each independently C! -, representing alkylene] or mixtures thereof are provided.

Furthermore, according to the invention there is provided a mixture comprising from 10 to 90% by weight of one or more dyes of formula I and from 90 to 10% by weight of one or more yellow disperse dyes (
(based on the weight of dye in the composition).

Preferably R1 is hydrogen or chlorine, R"1 is hydrogen and R2 is hydrogen, chlorine, methyl or methoxy. More preferably R'1, R"1 and R2 are hydrogen.

Preferably, R1 and R4 each have the formula -CH2-C
H.

- is a group of

Preferably, in the mixture defined above, the amount of compound 2 is from 50 to 90% by weight and the amount of one or more other yellow disperse dyes is from 10 to 50% by weight.

Preferred other yellow disperse dyes are selected from the disperse dyes of formulas 1 to 1 below.

NyloxyC2-, alkoxycarbonyl, Cl-3alkoxyC2-, alkoxyCZ-1alkoxycarbonyl, phenoxyC2-ff alkoxycarbonyl, phenylCl-3alkoxycarbonyl, benzylcarbonyloxy, C5-, alkylaminocarbonyl, C1
-, alkylaminosulfonyl, Cl-3 alkylbenzoyl, phenylsulfonyloxy, benzyloxycarbonyl, tetrahydrofuryl Cl-3 alkoxycarbonyl, cyano, trifluoromethyl or Cl-7 alkoxy, and R6 is hydrogen, nitro, CI- I+
represents alkoxycarbonyl or chloro, R7 represents hydrogen or chloro, R11 represents hydrogen, Cl-4 alkyl, Cl-4 alkoxyCZ-4 alkyl or Cl-4
Represents alkoxycarbonyl C1-2 alkyl.

In the above formula, R2 is at the 3 or 4 position and is hydrogen, chloro, bromo, Cl-1 alkoxy carbonyl % CI-: l alkoxy C2-3 alkoxycarbonyl, C2-3 fluorine, and R1 is C1-6 Alkyl, C1-4 alkoxy C2 alkyl, Cl-4 alkylcarbonyloxy C
t-Z alkyl, C2-yualkenyloxyC2-3 alkoxyC! -, alkyl, cl-4furkylcarbonyloxyC2-coalkoxyC2-, alkyl, Cl-
2alkoxycarbonyloxyC1-3alkyl or a group of the formula -CtbCtli-0-CI(, CH!OH).

In the above formula, both Ro represent chloro or bromo, and Rl
g represents hydrogen or acetoxy.

6IL5 1 mol of the aminobenzene compound represented by the following formula x■
, Other most preferred yellow dyes are dyes of formulas ■ and ■.

Dyes of formula I can be prepared by known methods from known compounds.
For example, 1 mole of diazotized compound of the following formula [[In the above formula, R1, R1, and R2 represent the same thing as defined above] [In the above formula, R1 and R4 represent the same thing as defined above] ] It can be produced by coupling with the compound shown below.

The mixtures according to the invention can be prepared from known compounds by known methods, for example by mixing the component dyes before or after formulation as a dye preparation, or by adding a coupling component of formula XIV to a diazo component of formula XIII. Coupling with other coupling moieties, or coupling two different diazo moieties with one coupling moiety, or coupling a dye of formula I with a dye of formula
in which R9 is C1-4 alkylcarbonyloxyC2
If it is desired to prepare mixtures with similar dyes which are -1-flucoxy C2-, alkyl, they can be further prepared by acylating a portion of the disperse dye of formula 1.

Diazotization, coupling and acylation are generally carried out by known methods. The compounds of formulas XIII and XTV are known or obtainable analogously to methods known for the preparation of analogous compounds.

The processing of the novel compounds of formula (1) and disperse dye mixtures containing them into dyeing preparations is known, for example by comminution in the presence of dispersants and/or fillers. After addition of a controlled amount of water, dyeing, pad dyeing or printing can be carried out in long or short baths with these preparations, optionally vacuum-dried or spray-dried.

From the aqueous suspension, dyes and dye mixtures are fully absorbed onto textile materials consisting of fully synthetic or semi-synthetic, hydrophobic, high molecular weight organic materials. They are particularly suitable for dyeing or printing fiber materials consisting of linear aromatic polyesters and of cellulose 21/2 acetate and cellulose triacetate.

Dyeing or printing is described, for example, in British Patent No. 1,114,43.
This is carried out according to known methods such as those described in 3.

The dyeings obtained have good to very good all-round fastnesses, in particular fastnesses to sunlight, heat setting, sublimation and pleating, good fixing ability, high exhaustion or fixation rates and good bath exhaustion. .

The invention is further illustrated by the following examples. In the examples, unless otherwise specified, parts and % are expressed in t amounts, and temperatures are in degrees Celsius. When 0 parts represent parts by volume, 1 part by volume corresponds to the volume of 1 part by weight of water.

Preparation of Compound 2'' 32 parts of 4-aminobenzene were stirred in 150 parts of 15% hydrochloric acid overnight and then mixed with 350 parts of ice/water.

The partially crystallized mixture is then heated at 5-10° for about 30°C.
Diazotization was carried out with 34 parts by volume of 5N aqueous sodium nitrite solution for 1 minute. The crystalline solid was dissolved. After 2 hours, the slightly excess nitrous acid was decomposed with amidosulfonic acid,
The dark reddish-brown diazonium salt solution was filtered until clear.

(49
, 5%) aqueous solution was diluted with 600 parts of ice water and mixed with the diazonium salt solution obtained above for about 1 hour while maintaining the temperature below 10°. The pH was maintained at 3-6 by adding sodium acetate. Stirring was continued for several hours without cooling, and the insoluble dye was filtered off and washed with water until salt-free. The obtained dye has a λwax of 461 parts m
(OMF÷1χ in glacial acetic acid) The melting point of the dye after recrystallization from lube in acid on ice was 200°.

Amendment L1 Preparation of a dye mixture containing 60% of a dye of formula ■ and 40% of a dye of formula ■ in which R9 is β″-acetoxyethoxy-β-ethyl 10 parts of a dye of formula ■° prepared according to Example 1 50 parts of glacial acetic acid and 1
Heat in a mixture of 0 parts acetic anhydride. The crystalline material was dissolved. After cooling, the acetylated dye precipitated and was filtered off, washed first with dilute acetic acid and then with water and dried in vacuo. The dye obtained had a λmax of 462 parts m. The melting point was 145-147.

±38.9 parts of main (49.5%) aqueous solution containing 19.25 parts of the coupling component of Example 1 and 19.1 parts of r-ethoxy-〇-propyl-3-cyano-6-hydroxy-4 - Methylpyridone-2 (23,6%) in an aqueous solution containing 50%
A mixture of the dye of Example 1 and 50% of the dye of formula 1 in which R is T-ethoxy-n-propyl was prepared.

Grasping soil 2■ In the same manner as in the above example, other disperse dye mixtures according to the present invention as shown in the table below could be prepared using a disperse dye of formula 0 and a dispersion in which R7 is hydrogen. The mixtures with dyes are shown in Table i below.

Meng-U 50 Same as above R 204-C1fl, -CR(C)Rs)CIhNdayso
, -1253-B, C, -50, -0-I1 Same as above 3-11. C, -CIIl-COJ- -C1 day 4-(p-1-11,C3-C,i,-Co)-4+c
1+(-(9)- 〇4-CIIm-CM-C1iO(Cflx)1-0-c
,4-TI,c,-oca,ca,o-co-x-u,
c, -ocIllcamo-c.

4-H, CICII(C,1ls)-C1h-c,
4-H, c, -CB, C11,0CB3CIl, 0-C
O--C8°-CI, CH, CH, OCR.

-C, II.

-CIH@ -C, I+.

-C[I,c,0C,H.

-CM.

Same as above - C-IIS formula! A mixture of the disperse dyes No. 1 and No. 2 is shown in Table 2 below.

, Table-1”-Equation! Disperse dye in which R1, is H and R9 in formula (2) is -C1 (tcll zcJl 1OcHicH3
Mixtures with disperse dyes are shown in Table 3 below.

Table 1-1 Item-C1-CI Mixtures of the disperse dyes of formula I° and the disperse dyes ② to ② are shown in Table 4 below.

Theft---Upper 30 (IV) 15 (V) 25 (VXX F20 (IX) 15 (X) 20 (V engineering) 15 (X engineering) 15 (XI engineering) 15 (V engineering) R11 Gen C1, R12 =O-COCFisall, C
1, R12 "Day Layer 1 Using the method of Additional Example 1, 38.5 parts of 3-cyano-6-hydroxy-1-β"-hydroxy-β-ethoxyethyl-4-methylpyridone-2 was added to 22. 3 parts of diazotized 4-amino-1,1"-azobenzene and 7.86
Coupling with a mixture of diazotized 3,4-dichloroaniline to give a yellow-orange azo dye mixture.

250 parts of a 16% aqueous paste of the dye of Example 1 were milled in a glass bar mill with 60 parts of a commercially available genin sulfonate dispersant until the particles had an average diameter of up to 1 micron. The pH was brought to 7-8 (by filtration through a glass bar) and the formulation was dried in a hot air atomizer. The resulting fine powder contained 40% pure dye. A portion of the dye preparation thus obtained was
' and stirred with 4,000 parts of water buffered to pH 5. Using this dye liquor, 100 parts of polyester fabric was bundled in a closed dyeing machine at 130' for 1 hour. After cooling, rinsing, soaping, rinsing again and drying, a uniform yellow-orange dyeing with very good all-round fastness properties was obtained. Examples 2-4
Dye No. 9 could be used in a manner similar to the example above.

The above application example could be repeated using the dye of Example 2 or 3 or the mixture of Examples 4 to 50 instead of the dye of Example 1. The dyeing hue on the polyester fiber material was yellow-orange in all cases.

Claims (1)

[Claims] 1. A disperse dye represented by the following formula I or a mixture thereof. ▲There are mathematical formulas, chemical formulas, tables, etc.▼ I In the above formula, R_1, R_1' and R_2 are each independently selected from hydrogen, chloro, bromo, C_1_-_2 alkyl or C_1_-_2 alkoxy, and R_3 and R_4 are Each independently represents C_2_-_3 alkylene. 2, R_1 is hydrogen or chlorine, R_1' is hydrogen, R_2 is hydrogen, chlorine, methyl or methoxy, and R_3 and R_4 are each of the formula -CH_2-CH
The disperse dye according to claim 1, which is a group of _2. 3. A dye of formula I according to claim 1 or 2 and 90 to 10
Disperse dye mixture containing % by weight of one or more other yellow disperse dyes. 4. One or more other yellow disperse dyes of formula I
Disperse dye mixture according to claim 3, selected from disperse dyes I to XII. ▲There are mathematical formulas, chemical formulas, tables, etc.▼II In the above formula, R_5 is at the 3rd or 4th position and represents hydrogen, chloro,
Bromo, C_1_-_8 alkoxycarbonyl, C_1
_-_3 alkoxy C_2_-_3 alkoxycarbonyl, C_2_-_3 alkenyloxy C_2_-_3 alkoxycarbonyl, C_1_-_3 alkoxy C_2
_-_3 alkoxy C_2_-_3 alkoxycarbonyl, phenoxy C_2_-_4 alkoxycarbonyl,
Phenyl C_1_-_3 alkoxycarbonyl, benzylcarbonyloxy, C_1_-_8 alkylaminocarbonyl, C_1_-_8 alkylaminosulfonyl,
selected from C_1_-_3 alkylbenzoyl, phenylsulfonyloxy, benzyloxycarbonyl, tetrahydrofuryl C_1_-_3 alkoxycarbonyl, cyano, trifluoromethyl or C_1_-_7 alkoxy, R_6 is hydrogen, nitro, C_1_-_8 alkoxycarbonyl or chloro R_7 represents hydrogen or chloro, R_8 is hydrogen, C_1_-_4 alkyl, C_1_-_4 alkoxyC_2_-_4 alkyl or C_1_-_4 alkoxycarbonylC_1_-
_2 Represents alkyl. ▲There are mathematical formulas, chemical formulas, tables, etc.▼III In the above formula, R_9 is C_1_-_8 alkyl, C_1_-
_4 alkoxy C_2_-_3 alkyl, C_1_-_
4 alkylcarbonyloxy C_2_-_3 alkyl,
C_2_-_3 alkenyloxy C_2_-_3 alkoxy C_2_-_3 alkyl, C_1_-_4 alkylcarbonyloxy C_2_-_3 alkoxy C_2_-
_3 alkyl, C_1_-_2 alkoxycarbonyloxyC_2_-_3 alkyl or formula -CH_2CH_
Represents a group of 2-O-CH_2CH_2OH. ▲There are mathematical formulas, chemical formulas, tables, etc.▼IV; ▲There are mathematical formulas, chemical formulas, tables, etc.▼V; ▲There are mathematical formulas, chemical formulas, tables, etc.▼VI In the above formula, R_1_1 both represent chloro or bromo, and R_1_2 represents Represents hydrogen or acetoxy. ▲There are mathematical formulas, chemical formulas, tables, etc.▼VII; ▲There are mathematical formulas, chemical formulas, tables, etc.▼VIII; ▲There are mathematical formulas, chemical formulas, tables, etc.▼IX; ▲There are mathematical formulas, chemical formulas, tables, etc.▼X; ▲Mathematical formulas , chemical formulas, tables, etc.▼X I; ▲There are mathematical formulas, chemical formulas, tables, etc.▼XII. 5. The other yellow disperse dye is of formula II or III according to claim 4.
A disperse dye mixture according to claim 3 or 4, which is a disperse dye of. 6. In producing the disperse dye of formula I according to claim 1 or 2, 1 mole of diazotized formula and R_2 represent the same thing as defined above] 1 mol of the aminobenzene compound represented by the following formula
V, ▲There are mathematical formulas, chemical formulas, tables, etc.▼XIV [In the above formula, R_3 and R_4 represent the same thing as defined above] A method including coupling with a compound represented by: 7. In preparing the mixture of disperse dyes according to any of claims 1 to 5, a. the component dyes are mixed before or after the formulation as a dye formulation, or b. the diazo component of formula XIII is mixed with the diazo component of formula XIV. coupling moieties with other coupling moieties, or coupling two different diazo moieties with one coupling moiety, or c, dyes of formula I and formula III in which R_9 is C_1_-_4 A process further comprising acylating a portion of the disperse dye of formula I if it is desired to prepare a mixture with a similar dye which is alkylcarbonyloxyC_2_-_3alkoxyC_2_-_3alkyl. 8. Disperse dye according to claim 1 or 2 or claims 3-
A method for dyeing or printing a hydrophobic fiber material, comprising applying the disperse dye mixture according to any one of 5 to the hydrophobic fiber material.