DE1619347C - Anthraquinone dyes and their use - Google Patents

Description

2. Use before dyes according to claim 1 for dyeing or printing of structures Polyesters.

The invention relates to new anthraquinone dyes and their use for dyeing or printing of structures made of polyesters.

The new dyes have the general formula

O HN

CH = CH-R ₁

in which R _{1 is} an optionally substituted phenyl radical, the naphthyl (1) radical or the thienyl (2) radical and R _{2 is} a hydrogen, chlorine or bromine atom.

Substituents on the phenyl radical R ₁ are chlorine or bromine atoms, hydroxyl groups, amino groups, methyl, ethyl, propyl, isopropyl, butyl groups, tertiary butyl groups, methoxy, ethoxy groups, mercapto groups, methyl mercapto groups or nitro groups. The rest can e.g. B. have the following meanings: phenyl, 4-, 3- or 2-methylphenyl, 4-isopropylphenyl-, 4-, 3- or 2-methoxyphenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 2-methoxy-4-methylphenyl , 2-methoxy-5-methylphenyl, 4-aminophenyl, 4-nitrophenyl, 2-hydroxyphenyl, 4-methylmercaptophenyl, naphthyl- (1) and thienyl- (2). Dyes with an aromatic R ₁ radical are preferred.

The dyes of formula 1 can, for. B. obtained by using 1,2-diaminoanthraquinone, 1,2-diamino - 3 - chloranthraquinone or 1,2 - diamino-3-bromoanthraquinone with acids of general formula

R ₁ - CH = CH - COOH

or the corresponding acid halides. Aldehydes. Orthoesters or Acctalen converts. Example

Br

by adding 1,2-diamino-3-bromoanthraquinone with 4-methylcinnamic acid chloride at elevated temperature in Nitrobenzene converts.

The new dyes can be used to dye structures made of polyesters.

Structures made from polyester are, for example, films. Films or textiles, such as fibers, threads, flakes, Woven and knitted fabrics made from these materials. As polyester selenium z. B. those from terephthalic acid and ethylene glycol or α-dimethylolcyclohexane called.

Dye liquors which advantageously contain the dyes in finely divided form are used for dyeing. These liquors can be used to produce textile goods made of polyesters

z. B. at temperatures between 95 to 100 ⁰ C under normal pressure or at temperatures above 100 ° C by the so-called HT process or the thermosol process. If strong dyeings are to be obtained at temperatures around 100 ° C., it is advisable to add dye accelerators, so-called "carriers", to the dye liquor.

Printing pastes, in addition to the usual thickeners, are used to print polyester fabrics and printing auxiliaries contain the dyes mentioned in finely divided form. Appropriate dye accelerators are also added to the printing pastes. After printing, the item becomes steamed and finished as usual.

With the dyes according to the invention, one obtains Dyeings and prints that can be easily washed. Light, friction and thermal fastness properties distinguish and such colorations on polyester significantly exceed in color strength that with those in the published documents of the Belgian patent 661 414 and those in the German patents 238 981 and 238 982 dyes described can be obtained. The hue ranges from the greenish Yellow to orange.

The parts and percentages given in the examples are weight units. The parts of the room behave to parts by weight as the liter to the kilo

gram.

example 1

15.9 parts 1.2 - diamino - 3 - bromo - anthraquinone, 16.6 parts of cinnamic acid chloride and 160 parts by volume of nitrobenzene are heated to 150 ° C. for 4 hours. One lets cool and add acetone. The residue is filtered off with suction and washed with acetone. The dried one The crude product of the dye (22.5 parts) is dissolved in the pyridine. This solution becomes the dye precipitated with methanol. 19 parts are obtained (88% of the

Theory) of the dye of the formula

CH = CH

OHN-

₌ ΓΗ_ / \

with a melting point of 240 ^° C., which dyes polyester fabric in yellow tones.

Is used in Example 1 instead of cinnamic acid chloride the corresponding amount of an acid chloride of the formula

Cl - ■ OC - CH = CH - R ₁

and instead of 1,2-diamino-3-bromoanthraquinone a 1,2-diaminoanthraquinone which contains the radical R ₂ in the 3-position, dyes of the formula I in which R and R _{2 are obtained are} those in the table for Example 2 denoted substituents.

Example 2

100 parts of polyethylene glycol terephthalate fabric are in a dyebath consisting of 5000 parts of water, 5 parts of a duich reaction of 1 mole of sperm oil with 80 moles of Ethy'enoxu 'and subsequent sulfonation and 1 part of the finely divided dye of the form * "I, in the R ₁ denotes a phenyl radical and R ₂ denotes a chlorine atom, is treated for 90 minutes at 135 ° C. A very strong yellow dyeing with good to very good fastness properties is obtained.

Similar greenish yellow to orange colorations are obtained if, instead of the dye mentioned, those dyes of the formula I are used in which R ₁ and R ₂ contain the substituents indicated in the table below.

R ₁ CHj CHj CH
\ 3 R ₂ \
CH ₃ Br CHj C (CHj) ₃ OCH Cl Br H -ο- Cl OCH
I.
ι Cl

R, R, 5 CH ₃ "C> Br to OCH ₃ H '5 OH -C [^ - NO ₂ Br 20th H Cl
I. 25th H - <]>. Cl 30th 35 S.
-O Br
H

Example 3

100 parts of polyethylene glycol terephthalate fabric are in a dyebath consisting of 5000 parts of water, 10 parts of finely divided o-phenylphenol, 2 parts of a finely divided dye given in Example 2, 5 parts of a compound obtainable by reacting 1 mol of sperm oil alcohol with 80 mol of ethylene oxide and subsequent sulfonation, and 1 Part consists of glacial acetic acid, ^{treated at 95 to 10O 0} C for 90 minutes.

The dyed fabric is washed with water and then in a bath that consists of 5000 parts Water, 5 parts of sodium dithionite, 20 parts of 38 ° Be sodium hydroxide solution and 5 parts of a reaction of 1 mole of oleylamine with 12 moles of ethylene oxide is available, treated at 85 ° C for 15 minutes. Then it is treated again with water. The dyeings obtained are analogous to those of Example 2.

Example 4

A polyethylene glycol terephthalate fabric is printed with a printing paste consisting of 20 parts Diisobutyl phosphate, 5 parts of a mixture of the sodium salts of the disulfonimides of such hydrocarbons, which in the molecule average ! Enstoffatome contain 650 parts of crystal rubber, 275 parts of water and 40 parts of the first in the example 2 mentioned dye. After drying, the fabric is placed under a pressure of 30 minutes

1.5 atmospheres damped. A strongly colored yellow print with good fastness properties is obtained.

Example 5

0.6 parts of the first of the dyes mentioned in Example 2 are in a mixture of 60 parts of water, 0.3 parts of the sodium salt of the reaction product of / I-naphthalenesulfonic acid and formaldehyde, 6 parts of 38 ° Be sodium hydroxide and 2.5 parts of sodium dithionite, 10 minutes at 60 ⁰ C küpt. 4 parts of glacial acetic acid and 30 parts of water are then added. The vat acid precipitates in finely divided form.

This dye suspension 10Ö g of a Polyäthylenterephthalatgewebes at 50 ° C padded (70% liquor pick-up pad) and thermosol without intermediate drying for 1 minute at 220 ⁰ C "".

The dyed fabric is then in a bath consisting of 5000 parts of water and 20 parts of sodium hydroxide solution 38 ° Be, 15 parts of sodium dithionite, rinsed hot. Then a solution of 5000 parts of water, 10 parts of a coconut fatty alcohol sulfonate and 5 parts of sodium carbonate for 15 minutes

ίο Soaped at the boil and then rinsed with hot water and dried. A strong yellow dyeing with good fastness properties is obtained.

If the dye is in finely divided form, so the linking described in the first section of this example can be omitted.

Claims (1)

wisely one obtains the dye of the formula Patent claims:
1. Anthraquinone dyes of the formula CH = CH-R ₁ OHN- in which R _{1 is} an optionally substituted phenyl radical, the naphthyl (1) radical or the thieny ί (2) radical and R _{2 is} a hydrogen, chlorine or bromine atom.