DE1278393B - Dyeing of aromatic polyester materials - Google Patents

Description

FEDERAL REPUBLIC OF GERMANY

Int. CL:

D06p

GERMAN

PATENT OFFICE

EDITORIAL

German class: 8m-l / 01

Number: 1278 393

File number: P 12 78 393.6-43 (F 44811)

Filing date: December 24, 1964

Opening day: September 26, 1968

It has been found that dyes of the formula

NO ₂ O OH

HO

O NH - / \

wherein the ring A is substituted by one or two chlorine atoms, very good for coloring materials made of aromatic polyesters are suitable.

The dyes may be obtained by reacting lS ^ S-dihydroxy-dinitro-anthraquinone with mono- or dichloroaniline in inert organic solvents or preferably in an excess of mono- or dichloroaniline at temperatures between 100 and 200 ⁰ C..

Before the use according to the invention, the dyes are advantageously according to the known ones Methods brought into fine distribution, e.g. B. by pasting, kneading or grinding in the presence common dispersant.

The aromatic polyesters, e.g. B. fibers, woven or knitted fabrics made of polyethylene terephthalate or polyester made of terephthalic acid and dimethylolcyclohexane are dyed with the dyes used according to the invention according to the customary methods. One dyes z. B. at 120 to 130 ° C under pressure or at boiling temperature in the presence of dye accelerators, so-called carriers, such as chlorobenzene, 2- or 4-hydroxydiphenyl, salicylic acid or cresotinic acid ester. Because of their very good heat-setting fastness, the dyes are particularly suitable for use according to the so-called thermosol process, where they are fixed ^{to temperatures around 200 ° C. by brief heating.}

The clear blue dyeings obtained have very good light and wet fastness properties and excellent properties Thermosetting fastness.

It is already known from German Auslegeschrift 1 042 160 that by implementing Dihydroxy-dinitro-anthraquinone mixtures with aniline available dye mixtures for dyeing Polyester materials are suitable. It is also known that in the series of disperse dyes from Dye mixtures consisting of isomer mixtures have particularly good drawability on polyester. In contrast, it was completely surprising that the definitions to be used according to the invention were also defined

Coloring materials from aromatic
Polyesters

Applicant:

Paint factories Bayer Aktiengesellschaft,

5090 Leverkusen

Named as inventor:

Dr. Günter Gehrke, 5000 Cologne-Flittard

Individual dyes have good drawability on polyester fibers.

The following examples are parts and percentages by weight.

example 1

100 parts of 1,5-dihydroxy-4,8-dinitro-anthraquinone are heated in 500 parts of 3-chloroaniline at 150 ° C. for about 4 hours until starting material can no longer be detected. In 6oC is then diluted with 1,000 parts of methanol, the precipitated shares at 20 ⁰ C is filtered off, washed with 500 parts of methanol and dried. 110 parts of 1,5-dihydroxy-4- (3'-chloroanilino) -8-nitro-anthraquinone are obtained.

With a portion of this dye which has previously brought in the presence of dispersants in fine distribution, are dyed in 100 parts PoIyäthylenterephthalatfasern 3000 parts of water for 1 hour at 13O ⁰ C under pressure. A clear blue dyeing of very good fastness to light and sublimation is obtained.

Example 2

100 parts of 1,5-dihydroxy-4,8-dinitro-anthraquinone are in 500 parts of 3,4-dichloroaniline for about 4 hours heated to 180 C until no more starting material can be detected. At 75 C you dilute with 1000 parts of ethanol, filtered off with suction at 20 C, washed with 500 parts of ethanol and dried. You get 130 parts of 1,5-dihydroxy-4- (3'.4'-dichloroanilino) -8-nitro-anthraquinone.

A fabric made of polyethylene terephthalate is impregnated on a padder with a liquor which contains 2 ⁰ / ₍₎ contains the finely divided dye. Then it is squeezed off to a weight increase of about 70 "and dried at 10OC. Then the fabric is ^{treated with hot air for 60 seconds at 190 to 210:} C to fix the dye. A strong blue dyeing of excellent lightfastness and sublimation fastness is obtained.

809 618 528

In an analogous manner, the dyes compiled in the table below are obtained, which are also deliver blue dyeings with very good lightfastness and sublimation fastness.

example

dye

1,5-dihydroxy-4- (2'-chloroanilino) -8-nitroanthraquinone

1,5-dihydroxy-4- (4'-chloroanilino) -8-nitroanthraquinone

1,5-dihydroxy-4- (2 ', 3'-dichloroanilino) -8-nitro-anthraquinone

1,5-dihydroxy-4- (2 ', 4'-dichloroanilino) -8-nitro-anthraquinone

1,5-dihydroxy-4- (2 ', 5'-dichloroanilino) -8-nitro-anthraquinone

1,5-dihydroxy-4- (3 ^/ , 5 ^/ -dichloroanilino) -8-nitro-anthraquinone

Claims (1)

Claim: Use of dyes of the formula OH HO O wherein the ring A is substituted by one or two chlorine atoms, for coloring materials made of aromatic polyesters. Documents considered: German Auslegeschrift No. 1042160; British Patent No. 894,388. When the application was announced, a coloring table provided with explanations was displayed. 809 618/521 J. 6 * β Bundle »printer» l IwUn