DE2721187B1 - Color-stable monoazo dye - Google Patents

Description

Θ 4.3 5.75 6.4 6.7 6.95 7.6 7.75 d values 10.28 7.69 6.92 6.71 6.37 5.83 5.72 relative intensities 57
B. 26th 44 35 42 46 57 Θ 9.0 9.1 10.75 11.1 11.8 12.45 12.75 d values 4.93 4.87 4.13 4.00 3.77 3.58 3.49 relative intensity 42 29 50 50 68 39 81 Θ 13.4 d values 3.33 relative intensity 100

2. A method for producing the ^ modification according to claim 1, characterized in that the «modification of the dye mentioned, characterized by the X-ray diffraction spectrum of the Fig. 2,

a) heated in aqueous suspension to temperatures between 60 and 150 ⁰ C or

b) heated in an organic solvent to temperatures between 40 and 120 ° C or

c) in aqueous suspension with addition of water-soluble organic solvents at temperatures between 40 and 120 ⁰ C.

heated or

d) intensively mixed in aqueous suspension or with water-insoluble organic solvents at 10 to 120 ⁰ C.

e) grinding the mixture in the presence of a dispersing agent at temperatures of about 80 to 90 ⁰ C.

3. Use of the / ^ - modification according to claim 1 for dyeing textile materials made of cellulose esters or synthetic linear polyesters.

4. Use of the ^ modification according to claim 1 for coloring polyurethane plastics.

The present invention relates to a new color-stable crystallographic modification ("j3 modification") of the dye of the formula

Cl

Cl

n N- ^ Vn (C ₂ H ₄ OH) ₂

NHCOCH.,

the X-ray diffraction diagram shown in Fig. 1 with the characteristic reflections in the following Glance angles θ (CuK -x radiation) and the specified intensities.

ORIGINAL INSPECTEG

3 4.3 B. 9.0 27 21 187 6.7 4th B. 7.6 7.75 10.28 4.93 6.71 5.83 5.72 57 42 35 6.95 46 57 θ 13.4 5.75 6.4 6.37 d values 3.33 7.69 6.92 11.1 42 12.45 12.75 relative intensity 100 26th 44 4.00 3.58 3.49 50 11.8 39 81 θ 9.1 10.75 3.77 d values 4.87 4.13 68 relative intensity 29 50 θ d values relative intensity

The dye of the above formula can be prepared by known methods, where he in the α-modification is obtained under the conditions occurring in the practice of dyeing, in particular when coloring polyurethane plastics according to the method claimed in DE-OS 24 26 171, does not have sufficient stability. The α-modification has the X-ray diffraction diagram shown in Fig with the characteristic reflections at the following glancing angles θ (Cuk α radiation) with the specified intensities to:

θ 3.4 3.6 6.1 6.55 6.85 7.25 7.95 8.45 d values 13.00 12.28 7.25 6.76 6.46 6.11 5.57 5.25 relative intensity 41 29 37 37 41 45 29 40 θ 8.7 9.45 9.9 10.2 10.8 11.4 11.9 12.1 d values 5.10 4.70 4.48 4.40 4.11 3.90 3.74 3.68 relative intensity 38 27 45 49 38 47 50 48 θ 12.6 12.9 13.1 13.5 13.95 14.4 d values 3.60 3.45 3.40 3.30 3.20 3.10 relative intensity 100 71 72 64 59 38

Under dyeing conditions, such as high temperature and in the presence of dyeing auxiliaries, the changes / ^ - modification in terms of crystal size and shape practically no longer, so that the coloring properties and the stability of the dispersion in the In contrast to the α-modification, this is not impaired.

When coloring polyurethane plastics with the formation of covalent bonds between the dye and the isocyanate component of the plastic are in the case of using the α-modification of the The technical properties of the plastic (elasticity, rise time, setting time, etc.) a non-colored plastic clearly changed, if the »j9 modification« is used such a change does not occur.

The new color-stable modification ^, by 10 to 60 minutes long heating, optionally under pressure, an aqueous suspension of α-modification at temperatures of 60-150 ° C, preferably 80- 120 ⁰ C ₁ are obtained.

The ^ modification can also be achieved by heating the α-modification in organic solvents, such as Alcohols, for example ethanol or butanol, ethers such as dioxane, or glycols or glycol ethers, to temperatures of 40 ° C to about 120 ° C, if necessary under pressure or aromatic hydrocarbons such as chlorobenzene, dichlorobenzene, Toluene, xylene or benzene. In addition, the ^ -modification can by drying the α-modification obtained at temperatures of 100-120 ° C will.

4> The conversion into the stable β- modification also takes place by heating the α-modification in aqueous suspension with the addition of water-soluble organic solvents such as alcohols such as methanol, ethanol, butanol, glycols or

> () Glycol ethers, acetone or dimethylformamide, whose lower limit is held within a temperature range about 40 ⁰ C and whose upper limit is given by the composition of the mixture of water and organic solvent, 120 ⁰ C, however,

V) should not exceed.

Another possibility for converting the »α-modification« is the color-stable »^ -modification« consists of several hours of intensive mixing of an aqueous suspension of the "α-modification" of the

w) Dyestuff with 1-20% by volume, preferably 5-10% by volume, of an organic solvent that is insoluble in water, such as benzene, chlorobenzene, dichlorobenzene, toluene or xylene at temperatures between 10 and 120 ^° C., preferably between 40 and

h-, 90 ° C.

The ^ modification is also obtained by heating an aqueous suspension of the α modification Addition of anionic, cationic or non-ionic

see surface-active compounds at temperatures from 60 to about 100 ° C. For this purpose, suitable surface-active compounds are, for example Sodium diisobutylnaphthalene sulfonic acid, the adduct of 25 moles of ethylene oxide and 1 mole Stearyl alcohol, a mixture of alkyl dimethylbenzylammonium chlorides, a fatty acid polyglycol ester or tertiary organic phosphoric acid ester of the adduct of 2 moles of ethylene oxide to 1 mole of lauryl alcohol.

Finally, the ^ modification can be obtained through this be that the α-modification with the addition of conventional dispersants, such as alkylated Naphthalene sulfonic acids, polyvinyl sulfonates, condensation products from naphthalene sulfonic acid and formaldehyde or from phenol and formaldehyde, alkali salts of lignosulfonates or sulfite cellulose waste liquor Grinds temperatures of around 80 - 90 ° C.

The ^ modification is made, for example, by filtering separated from the liquid phase and given a known finish with the addition of dispersants, such as, for example, alkylated naphthalene sulfonic acids, polyvinyl sulfonates, condensation products Naphthalenesulfonic acid and formaldehyde or from

Phenol and formaldehyde, alkali salts of lignin sulphonates or sulphite cellulose waste liquor, with the usual ones Subject to temperatures not exceeding 60 ° C. The usual ones are suitable for fine distribution Devices such as ball mills or sand mills.

The liquid or powdery preparations of the stable /! Modifications obtained in this way In contrast to comparable preparations of the «modification, they are unrestrictedly suitable for Dyeing of textile materials made of cellulose esters or synthetic linear polyesters such as polyethylene glycol terephthalate, at temperatures between 100 and 220 ° C. The stable preparations flocculate in water Medium and when exposed to high temperatures, which is particularly important for the coloring of wound bodies, for example cross-wound bobbins, is important and give better test results with different Dyeing tests.

The "/? - modification" of the dye mentioned can be used in particular for coloring polyurethane plastics according to Examples 1 to 8 of DE-OS 24 26 171 can be used.

For this purpose 2 sheets of drawings

Claims (1)

Patent claims: . ^ - modification of the dye of the formula Cl (C ₂ Hs) ₂ NSO ₂ · <
Cl " MV VN (C ₂ H ₄ OH) ₂ / NHCOCH, characterized by the in A b b. 1 shown X-ray diffraction diagram with the characteristic reflections at the glancing angles θ with the specified relative intensities: