DE1260426B - Process for dyeing and / or printing textile fibers made of metal-containing polypropylene - Google Patents

Description

FEDERAL REPUBLIC OF GERMANY

GERMAN

PATENT OFFICE

EDITORIAL

Int. α .:

Number: File number: Registration date: Display day:

D 06p

German class: 8m-1/01

1260426
B79106IVc / 8m
October 28, 1964
February 8, 1968

It has been found that water-insoluble azo dyes of the general formula I

HO

NR ²

in which R ¹ denotes an optionally substituted alkyl or aryl group, R ² denotes an optionally substituted aryl group and ring A can also carry nonionic substituents such as halogen atoms, alkyl, alkoxy, dialkylamino or aroylamino groups, excellent for dyeing textile fibers made of metal Polypropylene are suitable.

With dyes of the formula I, which are prepared in the customary manner by grinding together with a dispersant have been brought into finely divided form, is obtained on hydrophobic, synthetic fibers, in particular textile materials made of polypropylene, which contains small amounts of metal compounds such as oxides, Very real salts or chelate complexes of Zn, Al, Cr, Co, Fe or, in particular, nickel Colorations.

The polypropylene containing the metal compounds of the type mentioned can be the metal compounds contained as catalyst residues from the manufacture of the polymer. The metal compounds can also to stabilize the polymer against exposure, against temperature stress or Oxydationseinfiüsse or be added to the polypropylene to improve the dyeability. The polypropylene to be colored should, however, expediently be more than 0.01 percent by weight, e.g. B. 0.1 percent by weight, of the metal.

The polypropylene fibers are dyed with the dyes which can be used according to the invention according to the for dyeing with disperse dyes customary methods. The water-insoluble dyes are used in the form of aqueous dispersions which are obtained in a conventional manner. A high level of fine distribution of the dye is very desirable in terms of a good color yield.

The dyestuffs of the formula I can be used for dyeing from a “long liquor” or by impregnating with a “short liquor” on a padder. From a long liquor dyeing advantageously at 70 to 130 ^c C, preferably at 90 to 130 ⁰ C. When the dyed material is impregnated on a padder means working z. B. at room temperature or slightly elevated temperature process for dyeing and / or printing textile fibers made of metal-containing polypropylene

Applicant:

Aniline & Soda Factory in Baden

Aktiengesellschaft, 6700 Ludwigshafen

Named as inventor:

Dr. Dieter Lauchs,

Reinhold Krallmann, 6700 Ludwigshafen

and heats the impregnated material after drying at 70 to 100 ⁰ C for a short time to about 130 ⁰ C.

It is advisable to dye in neutral or weakly acidic areas; an adjustment of the pH value of the Dye liquor to 4 to 5 by adding acetic acid increases the color yield in many cases.

In some cases it is advantageous to use the dyebath in addition to those already in the dye preparation contained dispersants to add further dispersants or emulsifiers, z. B. Naphthalenesulfonic acid-formaldehyde condensation products, fatty acid oxyethylation products, oxyethylation products aliphatic amines or alcohols or polyglycol ethers, also in sulfated form.

With the dyes which can be used according to the invention, the textile material made of polypropylene can also be printed. The usual thickeners are used to produce the printing pastes, such as methyl cellulose, locust bean gum, industrial gum, alginates or tragacanth. The printing pastes can also contain conventional additives, such as urea or thiourea, and substances that Make it easier to apply insoluble dyes to textile fibers, such as thiodiglycol or sulfonated oils.

The printing ink is applied to the textile in a known manner, e.g. B. by film, screen or roller printing applied. The textile material is then dried and treated either with steam under normal pressure or increased pressure, or the printed textile material is treated with hot air at 110 to 130 ^° C.

The dyed or printed textile material made of metal-containing polypropylene can then be used as usual post-treatment, such as washing, finishing, decating or heat setting.

809 507/593

However, all thermal treatments must be below the softening point of the polypropylene are executed.

The dyes of the general formula I which can be used according to the invention are obtained if Diazo compounds of amines of the formula II ßend the diazo solution slowly turns into a solution of 175 parts of l-phenyl-ß-imino-S-oxopyrazolidine in 1500 parts of water, 40 parts of sodium hydroxide and 50 parts of sodium acetate are stirred in. After finished Coupling, the precipitated dye is filtered off, washed with water and dried. Man receives 290 parts of the dye of the formula

OR ¹

OCB

HO

NH ₂

II

with compounds of the formula III

HO

N -R ²

III

H, N

couples, where R ¹ , R ² and A have the meanings given above.

The diazo components II are: l-amino-2-methoxybenzene, 1-amino-2-ethoxybenzene, 1-amino ^ -methoxy-S-methylbenzene, l-amino-2-methoxy-5-chlorobenzene, l-amino-2,4-dimethoxybenzene, 1 - amino - 2,5 - dimethoxybenzene, 1 - amino - 2,5 - diethoxybenzene, 1 - amino - 2 - ethoxy-4 - diethylaminobenzene, 1 - amino - 2,5 - dimethoxy-4 - chlorobenzene, 1 - amino - 2,4 - dimethoxy - 5 - chlorobenzene, 1 - amino - 2 - methoxy - 5 - methyl - 4 - benzoylaminobenzene, 1 - amino - 2,5 - dimethoxy - 4 - benzoylaminobenzene, 2-amino-4-chlorodiphenyl ether or 2-amino-4,4'-dichlorodiphenyl ether.

The following coupling components of the formula III may be mentioned: 1 - phenyl - 3 - imino - 5 - oxopyrazolidine, 1 - ρ - tolyl - 3 - imino - 5 - oxopyrazolidine, 1 - (4 - chlorophenyl) - 3 - imino - 5 - oxopyrazolidine, 1 - (4 - methoxyphenyl) -3-imino-5-oxopyrazolidine. The preparation of these compounds is from Ber. 39, 2282 (1906) and JACS 66, 1851 (1944).

The diazo coupling of the diazotized amino compounds of the formula II with the compounds of Formula III takes place in a manner known per se, preferably in a buffered aqueous solution. The water-insoluble coupling products precipitate.

Compared to the closest comparable dyes known from Belgian patent specification 642 136 The dyes to be used according to the invention are distinguished by the fact that they are based on polypropylene Dyeings with better wash and solvent fastness result.

The parts and percentages given in the examples are weight units.

example 1

a) Preparation of the dye used according to the invention

123 parts of 1-amino-2-methoxyaniline are dissolved cold in 2500 parts of water and 250 parts of 10N hydrochloric acid, 1500 parts of ice are added to the solution and the amine is diazotized with a solution of 69 parts of sodium nitrite in 500 parts of water. The mixture is stirred for a further 2 hours and the excess nitrite is destroyed with sulfamic acid. Then H ₂ N

b) 100 parts of a knitted fabric made of nickel polypropylene are in a bath containing in 3000 parts of water 0.3 parts of the finely divided azo dye of the above formula and 0.5 parts of an order-reduction product of naphthalenesulfonic acid and formaldehyde, 1 hour at 125 ⁰ C treated in a high temperature dyeing machine. A clear, greenish yellow coloration with excellent light sensitivity and very good fastness to washing and solvents is obtained.

Example 2

100 parts of a yarn made of nickel-containing polypropylene are in a bath that is 0.5 parts of the finely divided azo dye in 4000 parts of water formula

OCH ₃ HO

^ X_XT —XT_ ^

OCH,

H ₇ N

1 part of the product obtainable by reacting 1 mole of sperm oil alcohol with 80 moles of ethylene oxide and subsequent sulfation and containing 3 parts of 30% aqueous acetic acid, colored. It brings it the dye bath within 15 minutes from 70 to 100 ⁰ C, dyeing is 90 minutes at the boil, rinsed and dried. A strong yellow color is obtained, which is distinguished by very good fastness to light, washing and solvents.

Example 3

A fabric made of nickel-containing polypropylene is printed with a printing paste of the following composition :

10 parts of the finely divided azo dye of the formula

OCH ₃

f YN = NT

CH,

H, N

50 parts thiodiglycol,
500 parts thickening based on carob seed

..meal (1: 2),
440 parts of water,
1000 parts.

The fabric is dried and the dye is fixed either by heating the fabric for 5 minutes at 130 ^° C. or by steaming for 15 minutes at 1.5 atm overpressure. The yellow print obtained has excellent fastness properties.

In the same manner as indicated in Examples 1 to 3, the following dyes can be used will:

OC ₂ H ₅

HO

N = N

H, N

OC ₂ H

HO

d) (C ₂ H ₅ J ₂ N

H, N

Claims (1)

Claim: Process for dyeing and / or printing textile fibers made of metal-containing polypropylene, characterized in that water-insoluble azo dyes of the general formula OR ¹ HO OC ₂ H ₂ H ₅ H ₇ N H ₇ N in which R ¹ denotes an optionally substituted alkyl or aryl radical, R ² denotes an optionally substituted aryl radical and the ring A can still carry nonionic substituents. Considered publications:
British Patent No. 832 199;
published documents of the Belgian patent No. 642 136. When the application was announced, a coloring table with an explanation was displayed. 809 507/593 1.68 © Bundesdtuckerei Berlin