DE2339030A1 - DISPERSION DYES - Google Patents

Description

Folder 23270 - Dr.K./H, Case Dd. 25352

IMPERIAL CHEMICAL INDUSTRIES LIMITED

London, UK

Disperse dyes

Priority: 8/11/72 - Great Britain

The invention relates to disperse dyes of the quinophthalone series, which are used for dyeing synthetic textile materials, in particular aromatic polyester textile materials. According to the invention, disperse dyes of the formula

COOH

409808/1071

12 T

proposed where one of the symbols ϊ, Y and Y for a

1 p

Chlorine or bromine atom and the other of the symbols Y, Y and Y ⁵ each independently represent a hydrogen, chlorine or bromine atom ..

According to the invention, a method for producing the dyes according to the invention is also proposed, which thereby is carried out that one is a compound of the formula

OH

Formula I.

with an anhydride of the formula

or the corresponding free acid, where X is a Hydrogen, chlorine or bromine atom or a carboxylic acid group

2 3

and Y and Y each independently represent a hydrogen, Chlorine or bromine atoms, the two reactants together having 1 to 3 chlorine and / or bromine atoms contain.

The method according to the invention is expediently carried out by that the reactants are heated together, preferably to a temperature between 150 ° and 250 ° C and; preferably also in the presence of an inert organic liquid such as trichlorobenzene or o-dichlorobenzene. The dye obtained can then be isolated in a customary manner, for example by using the inert organic Liquid removed by distillation in the presence of steam and the insoluble dye from the resulting aqueous The liquid is filtered off.

Specific examples of compounds of the formula I are 2-methyl-3-hydroxyquinoline and 4- (chloro- or bromo-) - 2-methyl-3-hydro-

409808/1071

xychinolin. ,

Examples of the anhydrides mentioned or the corresponding free acid are trimillitic acid, triillitic anhydride, Hemimellitic acid and 1- (chloro- or bromo-) ~ benzene-2,4,5-tricarboxylic acid.

According to the invention there is also a method of manufacture proposed the dyes according to the invention in which Y stands for a chlorine or bromine atom, which is thereby carried out is that the corresponding quinophthalone, in which Y is a hydrogen atom, chlorinated or brominated. The process according to the invention can expediently be carried out by a stream of chlorine gas or bromine gas passed through the molten quinophthalone compound. Alternatively, the chlorine or the bromine can be made into a solution being added to the quinophthalone compound in an inert organic liquid such as trichlorobenzene or acetic acid The reaction mixture can optionally also contain a halogenation catalyst such as iodine.

The quinophthalone compounds mentioned, in which Y stands for a hydrogen atom, can themselves be obtained by that a compound of the formula i, wherein X is a hydrogen atom or a carboxylic acid group, with an anhydride condensed according to the above definition or with the corresponding acid, the condensation preferably in an inert Solvent such as trichlorobenzene is carried out. The quinophthalone compound obtained can then be used in the usual manner can be isolated, but optionally the bromination or chlorination can be carried out without the quinophthalone compound is isolated in between.

The dyes according to the invention are yellow and can be used for dyeing synthetic textile materials in the form of dispersions using methods which are known per se in the art. Synthetic textile materials, which can be colored are, for example, aromatic polyesters such as polyethylene terephthalate, cellulose esters such as cellulose acetate and cellulose triacetate, polyamides, v / ie'z.3. liylon-66 and Nylon-6, polyacrylonitrile and polyurethanes, as well as mixtures of

409808/1071

BATH ORIGINAL

same with each other or with natural fibers, such as wool and cellulose fibers,

The dyes according to the invention are particularly suitable for dyeing of aromatic polyester textile materials by a process in which one or more of the said dyes are dissolved in an aqueous solution of an alkali, the the solution obtained is acidified in an aqueous dye bath, in a padding liquid or a printing paste, the dyebath obtained, the padding liquid obtained or the printing paste obtained on the aromatic polyester textile material is applied using methods known per se and finally the dyed textile material is diluted in a hot aqueous alkali solution is rinsed.

The dyeings obtained have excellent fastness to Light, wet treatments, dry heat treatments and rubbing.

The invention is illustrated by the following examples, in which the parts and percentages are expressed by weight. example 1

20.3 parts of 2-methyl _T ; / - hydroxyquinoline-4-carboxylic acid are gradually introduced into a mixture of 22 parts of trimellitic anhydride and 90 parts of trichlorobenzene at 170 ° C., and the mixture obtained is then at 190 ° to 205 ° for 2 hours C stirred. The mixture is then cooled to 60 ° C., then a solution of 17.16 parts of bromine in 90 parts of trichlorobenzene is added, and the mixture is then stirred at 68 ° to 73 ° C. for 18 hours. Nitrogen is then bubbled through the mixture to remove any residual bromine or hydrogen bromide, 100 parts of an 8% aqueous sodium hydroxide solution are added, and the trichlorobenzene is removed by distillation in the presence of steam. The aqueous liquid obtained is filtered, the piltrate is acidified, and the precipitated dye is filtered off, washed with water and dried.
It is 3'-hydroxy-4'-bromoquinophthalone-5-carboxylic acid of the formula

409808/1071

BATH

7339030

Br

COOK

obtain. When dispersed in an aqueous medium, it dyes aromatic polyester fabrics into yellow shades with excellent fastness to light, rubbing, wet treatments and dry heat treatments. Example 2

Instead of the trimellitic anhydride used in Example 1, an equivalent amount of hemimellitic acid is used, whereby 3'-hydroxy-4 ^f -bromoquinophthalone-4-carboxylic acid is obtained, which also dyes aromatic polyester textile materials in yellow shades with excellent fastness properties, Example 3

Instead of the solution of the 17.16 parts of bromine in 90 parts of trichlorobenzene, which was used in Examples 1 and 2, a solution of -9 parts of chlorine in 90 parts of trichlorobenzene is used, whereby the corresponding 4'-chlorine compounds are obtained.
Example 4

A mixture of 2.03 parts of 2-methyl-3-hydroxyehinoline-4-carboxylic acid, 2.48 parts of 4-chlorohemimellitic anhydride and 15 parts of trichlorobenzene is stirred at 195 ° C. for 3 hours. The mixture is cooled to 20 ° C. and poured into methyl alcohol, and the precipitated 3'-hydroxy-S-chloroquinophthalone-A-carboxylic acid is filtered off, washed with methyl alcohol and dried. When the dye is dispersed in an aqueous medium, it dyes aromatic polyester textile materials in yellow shades with excellent fastness properties. Example 5

A mixture of 2.03 parts of 2-methyl-3-hydroxyquinophthalone-4-carboxylic acid 2.48 parts of chlorohemimellitic anhydride and 15 parts of trichlorobenzene are stirred at 195 ° C. for 3 hours. The mixture is cooled to 60 ° C, a solution of 1.72 parts of bromine in 9 parts of trichlorobenzene is added, and the mixture is

409808/1071

BATH ORIGINAL

7339030

then stirred at 68 ° to 73 ° C. for 18 st. The product obtained, namely 3 ^f -hydroxy-4 ^l -t »romo-5-chloroquinophthalone-4-carboxylic acid, is then isolated by the method described in Example 1.

When the dye is dispersed in an aqueous medium, it dyes aromatic polyester textile materials in yellow shades with excellent fastness properties. Example 6

A mixture of 20.3 parts of 2-methyl-3-hydroxyquinoline-4-carboxylic acid, 22 parts of trimellitic anhydride and 9 parts of trichlorobenzene is stirred at 19 ° to 195 ° G for 2 hours. The mixture is cooled to 70 ° C. and kept at this temperature for 3 hours, after which a stream of chlorine is then passed through the mixture. The .3'-hydroxy-4 ^f -chioroch-lnophthalone-5-carboxylic acid obtained is then isolated by the method described in Example 1.

This dye also dyes aromatic polyester textile materials in yellow shades with excellent. Authenticity properties. Example 7

Instead of the 2.48 parts of 4-chlorohemiaellitic anhydride, the was used in Example 4, equivalent amounts of the following dyes are used .;

a) 4-Bromohemimellii; h3äiireanhydrid

b) 4,6-Dibromohemime.lliihiiäv.reanhydrid

c) 4,6-dichloroemellin3 acid anhydride or . d) 5-chlorotrimellitic acid aihydride

Similar yellow waxes are obtained. Example 8

Instead of the 2.03 parts of 2-methyl-3-hydroxyquinoline-4-carboxylic acid, which was used in Examples 4 to 7, 1.94 parts of 2-methyl-3-hydroxy-4-chloroquinoline cder are grounded 2.38 parts of 2-methyl-3-hydroxy-4-bromoquinoline are used to give similar dyes containing 2 or 3 chloro and / or broinatorae.
Example 9

Instead of the 2.48 parts of 4-C.alorohe; cir _t &]. Lithic anhydride which was used in Example 5, which uses equivalent amounts of the following substances

409608/10 7 1

BATH ORIGINAL

a) 4-Bromoheniimellitic anhydride

b) 5t 6-dibromohemimelic acid anhydride

c) 4,6-Dichlorohemiinelli thsäureanhydrid and

d) 5-bromotrimellitic anhydride. »

Similar yellow dyes are obtained.

7339030

409808/1071

Claims (4)

Claims Ί. Disperse dyes of the formula OH CO CO y Cf CCOH v >> 1 ^ 3 in which one of the symbols Y, Y and Y stands for a chlorine or a bromine atom and the other of the symbols Y, Y and Y ^v each stand for a hydrogen, chlorine or bromine atom. 2. disperse dyes according to claim 1 are characterized 1 ρ indicates that Y represents a hydrogen atom, Y represents a chlorine atom or is a bromine atom and Y is hydrogen, chlorine or Bromine atom stands. 3. Process for the preparation of the dyes according to claim 1, characterized in that a compound of the formula with an anhydride of the formula OCH or condensed the corresponding free acid, where Ά represents a hydrogen, chlorine or bromine atom or a carboxylic acid 2 3
group and Y and Y each independently represent a hydrogen, chlorine or bromine atom, the reactants mentioned together containing 1 to 3 chlorine and / or bromine atoms. 4. Process for the preparation of the dyestuffs according to Claim 1, in which Y is a chloro or bromine atom, characterized in this 409808/10 ORIGINAL BATHROOM characterized in that the corresponding compound in which Y is a hydrogen atom, chlorinated or brominated. 409808/1071