DE1906382A1 - Disazo dyes of the pyrazolone category containing sulfonic acid groups - Google Patents

Description

Our reference: OZ 2β 017 Bg /

6? 00 Ludwigshafen, February 7, 1969 SuIfons acid group-containing disazofaiibst-o ££ e-dBir ~ i ⁾ yi ¹ & zalon series

The refinement relates to disazof a-rJastof-f-a containing sulfonic acid groups. the general formula ....___.- · ■ ■ -— ^ 7 "" "^ -—- -

, S- / \ - N = N

in which R stands for a methyl, phenyl, carboxyl, carboalkoxy or carbonamide radical. X is a hydrogen, chlorine or bromine atom, or a methyl, ethyl, acetylamino, propionylamino, benzoylamino or a nitro group and Y denotes a hydrogen or chlorine atom.

Carboalkoxy groups for R are, in particular, carbomethoxy and To call carboethoxy.

The new dyes, which are also available in the form of their alkali salts can, are yellow to orange and are particularly suitable for dyeing of textile material made of synthetic polyamides such as nylon-6, nylon-β, β or similarly structured condensation products, as well as of Wool. It can be used to produce colors on synthetic polyamides with excellent fastness properties.

Of particular industrial importance are general dyes formula

^m r \ / ^^ \ t ^m ^ TT ^R i

-2- 0.Z -. "- 26 01?

in which R _{1 is} a methyl group and Z is a hydrogen or CnXoratom or a methyl or ethyl group. ;

The new dyes can be prepared in the usual way by coupling diazotized 4 · -amlnoazob «nzol-3,4" ^{: l} '-d ± s.ulfanic acid / with coupling components of the general formula

Y-I-4-X

obtained where R and X have the meanings given above. Ads coupling components come into consideration, for example:

1- (2 ^f -methylphenyl) -3-methylpyrazolone- (5) 1- (2'-ethylphenyl) -3-methylpyrazolone-C5) ^; l- (3 ^t -Acetyiaminophenyl) -3-methylpyrazolon- (5) 1 - (3'-Benzoylaminophenyl) -3-methylpyrazOlön- (5) 1 - (4 ¹ -Acetylaminophenyl) -3-methyiiiyrszOiLon- (5)

1-Phenylpyrazoloh- (5) -earbons'äureäthyleste.r- !, ^ - Diphenylpyrazolon-CS.) ... ■

in the following examples the specifications relate: and percentages on the weights ν

Warm to 40 ^ö C: Eosung "of 401 iei-len so; I am ^ ^ tAumsal Zes ^ ¹ ^ tdiei

O.Z. 26 017

Add concentrated sodium nitrite solution and allow this mixture to flow into the mixture of 800 parts by volume of 5 normal hydrochloric acid and 1 part of ice over the course ^{of 30 minutes with vigorous stirring at 5 to 10 ° C.} . "...

After two hours of stirring at 5 to 10 ⁰ C, excess nitrous acid is destroyed with sulfamic acid as usual.

In the thus obtained thick Diazogemisch "is then allowed to at 5 to 10 ⁰ C allmählich_die, i © sung-of" 192 "parts of l-phenyl-3-methylpyrazolon- (5) in 2000 parts Wassej? J and 60 parts by volume of 50- percent sodium hydroxide solution. Thereafter, 1,250 parts by volume of 50 percent sodium acetate solution are added in one hour, after which the coupling is completed in a short time. The precipitated dye is filtered off with suction and dried at 100 ⁰ C. After grinding, an orange powder is obtained which dissolves in water with a golden yellow color. ■

If the coupling component is used instead of l-phenyl-3-methylpyrazolone- (5) equimolecular amounts of those listed in the table Compounds, dyes are obtained with similar ones coloristic properties. .

Example of a coupling component

5 6

Color shade of the coloring on nylon-6

l- (2'-methylphenyl) -3-methyl- golden yellow pyrazolone- (5)

1- (2'-ethylphenyl) -3-methyl-golden yellow pyrazolone- (5)

l- (2'-chlorophenyl) -3-methyl- golden yellow pyrazolone- (5) '-

1 - (2 ', 5' -Dichlorophenyl) -jj-methyl- golden yellow pyrazolone- (5)

1- (4'-acetylaminophenyl) -3-methyl-orange

pyrazolone- (5) ■,

1- (3 ^! -Benzoylaminopheny1) -3-methyl- orange pyrazolone- (5)

8 ^:% * ". ■ 1 -. ("5 '-Nitrophenyl) -3-methylpyra, zolon. Orange

1098 19/1936

-4-

Example of a coupling component

Color shade of the coloring on nylon-6

9 10

1-phenylpyrazolone- (5) -carboxylic acid- (3)

1-Phenylpyrazolon- (5) -carboxylic acid ethyl ester- (3)

1-Phenylpyrazolon- (5) -carbon acid arid

1,3-diphenylpyrazolone- (5)

orange

- '■ \ . Orange c ¹

orange ■

. orange

Example I3

10 parts of a fabric made of polycaprolactam thread are in 400 Parts of the volume of a dyebath introduced containing 0.2 parts of the, dye from Example 1, 0.3 part of 30 percent acetic acid and 0.2 part of a commercially available leveling agent. One starts dyeing at 40 ° C, the dyebath heats up within 30 minutes to the boil and cook for 60 to 90 minutes. Then will the dyed fabric is rinsed and dried. A yellow-orange shade is obtained which is distinguished by very good fastness properties excels.

Example 14

10 parts of polyhexamethylenediamine adipate flake in a liquor ratio of 1:40 in a bath containing 0.2 part of the dye from Example 3 »0.2 part of a commercial leveling agent and 2.% 85 percent formic acid (based on the weight of the goods to be dyed) , colored at the boil for an hour. After rinsing, Mari takes on a golden yellow color with excellent fastness properties.

Example 15.

In 400 parts by volume of a dyebath containing 0.2 parts of the dye from Example 12, 1 part of anhydrous sodium sulfate and 0.3 part Contains 30 percent acetic acid, 10 g of woolen yarn are added, The dyeing begins at 40 ° C., the dyebath is brought to the boil within 30 minutes and boiled for 45 minutes. Then more are added Add 0.3 parts of 30 percent acetic acid and cook more.

109819/1936 ~ ⁵ "

■■ # - OZ 26 017

30 minutes. The then orange-colored wool is taken out of the Liquor, rinses them with water and dries them. The dyeing obtained in this way is distinguished by very good fastness properties.

-6-

1098 197 19 36

Claims (1)

OZ 2β 017 β! ί / Claims 1. Disazo dyes containing sulfonic acid groups of the pyrazolone series of the general formula - ^; ; ". - Yn = N- / in which R stands for a methyl, phenyl, carboxyl, Garboälkoxy- or carbonamide radical, X is a hydrogen, chlorine or bromine atom or a methyl, ethyl, acetylamino, propionyiamino, Benzoylamino or nitro group and Y denotes a hydrogen or chlorine atom. 2. Dyestuffs according to Claim 1 of the general formula in which R is a methyl group and Z is a hydrogen or chlorine atom or a methyl or ethyl group. ' A process for the preparation of dyes according to Claim 1, characterized in that "the diazo compound of aminoazobenzene-3,4'-disulfonic acid is mixed with compounds of the" general formula:. . -T- 1098 19/1936 -Τ ο. ζ. 26 017 HO .R clutch. 4.The use of the dyes according to claim 1 for dyeing Wool or synthetic polyamides. - Badische Anilin- & Soda-Fabrik AG 10 9819/1936