DE1144678B - Dyeing of polyamide, cellulose ester and polyterephthalic acid ester fibers from aqueous suspension - Google Patents

Description

INTERNAT. KL. D 06 P

GERMAN

PATENT OFFICE

S 62204 IVc / 8m

REGISTRATION DATE: MARCH 18, 1959

NOTICE THE REGISTRATION AND ISSUE OF EDITORIAL: MARCH 7, 1963

It has been found that anthraquinone dyes of the formula

OH O NH ₂

-R

NH ₁

OH

where R is optionally, with the exception of by nitro or amino groups or to the O - X group para halogen atoms, substituted aryl radical, which is in the anthraquinone radical bonded core carries at least one - O - X group, where X is a hydrogen atom or a optionally further substituted alkyl, cycloalkyl or aryl radical, alone or in admixture with one another excellent for dyeing polyamide fibers, cellulose ester fibers and polyterephthalic acid ester fibers from aqueous suspension are suitable.

In some cases, dye mixtures have a better draw power than the individual components on.

The dyeings on acetate artificial silk obtained are distinguished by excellent lightfastness and good quality Wash, sweat and smoke gas fastness. The dyeings on triacetate artificial silk and on polyester fibers have very good fastness to light, heat-setting and pleating as well as good fastness to washing and perspiration. The dye reserves wool, cotton, and viscose well.

The dyeings on polyamide fibers are light, perspiration and washfast.

In the formula given, R preferably denotes a mono-, di- or trihydroxyphenyl radical, a Monohydroxy, monomethoxy or monoethoxynaphthyl radical, a mono- or dialkoxyaryl radical, e.g. B. a mono- or dimethoxy or ethoxyphenyl radical or a monohydroxymonoalkoxyaryl radical, e.g. B. a monohydroxymonomethoxy or monoethoxyphenyl radical.

Of the anthraquinone dyes to be used, those are known which correspond to the formula given, in which R is a hydroxyphenyl, hydroxynaphthyl, methoxyphenyl or dihydroxyphenyl radical.
They are obtained by z. B.
1. phenol is added to the boric acid ester of l, 5-dihydroxy-4,8-diaminoanthraquinone-2,6-disulfonic acid dissolved in concentrated sulfuric acid (German patent 445 269),

Dyeing of polyamide, cellulose ester

and polyterephthalic acid ester fibers

from aqueous suspension

Applicant:
Sandoz AG, Basel (Switzerland)

Representative: Dr. W. Schalk, Dipl.-Ing. P. Wirth,

Dipl.-Ing. G. E. M. Dannenberg

and Dr. V. Schmied-Kowarzik, patent attorneys,

Frankfurt / M., Große Eschenheimer Str. 39

Claimed priority:

Switzerland from March 19, 1958 and March 9, 1959
(No. 57 206 and No. 70 513)

Dr. Paul Bücheier, Reinach (Switzerland),
has been named as the inventor

2. the addition product boils in acidic aqueous solution or in alkaline solution Heated 20 to 60 ° C, with a sulfonic acid group is split off (German Patent 446 563), and

3. reductively splits off the sulfonic acid group that is still present from the latter (German patent 456 235).

The other anthraquinone dyes to be used according to the invention can be used in a corresponding manner getting produced.

Dyeings with the proposed dyes on polyterephthalic acid ester fibers are not pleated than those with the closest comparable dyes of the German patent specification 864 425 and the USA patent 2,773,071 dyeings produced. Colorations obtained with the proposed dyes Polyamide fibers are more heat-set than dyeings with the closest comparable known dyes.

example 1

A dye bath is prepared from 1 part of the dye 1,5-dihydroxy dispersed with HiHe from Turkish red oil - 4,8 - diamino - 2 - (4 '- hydroxy) - phenylanthraquinone, 6 parts of a fatty alcohol sulfonate and

309,538 / 530

3000 parts of water. One enters the bath at room temperature with 100 parts of triacet silk, heats this up to 100 ° C within one hour and keeps it at 100 ° C for one hour this time the dyeing process is finished. The dyed material is taken out of the bath, rinsed and dried it. A blue dyeing of good fastness to washing, flue gas, heat setting and pleating is obtained and very good lightfastness. The dye reserves the wool well. To improve dispersion The dye can be used prior to the dyeing process with suitable wetting agents, dispersants or Wreden wreden emulsifiers. It can also be intimately mixed with a dispersant as an aqueous paste and converted into a dye powder by drying.

Example 2

1 part l, 5-dihydroxy-4,8-diamino-2- (4'-methoxy) -phenylanthraquinone, 1 part of sodium salt of Dinaph- ao thyhnethandisulfonsäure and 8 parts of water grind until a fine dispersion is achieved. This mixture is poured into one of 3000 parts Dye bath consisting of water and 6 parts of Marseilles soap. After introducing 100 parts of a Acetate rayon fabric is heated to 80 ° C in half an hour and during kept at this temperature for one hour. The fabric is then taken out of the liquor, rinsed with water and dried. A clear blue dyeing of excellent lightfastness is obtained and good fastness to washing, sweat and smoke gas.

Example 3

35

100 parts of polyethylene terephthalate fibers are placed in a dyebath at 60 ° C., which consists of 3,000 parts Water, 2 parts of the dye used in Example 1 and 1.5 parts of 2-hydroxy-l, l'-diphenyl consists. The dyebath is heated to boiling temperature within 20 minutes. The dyed material is Dyed for 60 minutes at 100 ° C, removed from the dyebath, rinsed with water and dried. The polyester fiber is in a beautiful blue, washable and very light, heat-setting colored and pleated clay. Treated cotton is well reserved.

Example 4

A fine dye dispersion is prepared from 1 part 1,5 - dihydroxy - 4,8 - diamino - 2 - (4'-ethoxy> phenylanthraquinone, 1 part sulphite cellulose liquor powder and 8 parts water. This paste is poured into one of 3,000 parts of water and 3 parts of one Dispersing agent existing dye liquor, which is located in a high-temperature dyeing machine, adds 100 parts of polyethylene terephthalate fiber added, closes the dyeing machine and heated it until the Internal temperature is 102 ° C. After one hour at 120 ° C., the dyeing has ended. You take that dyed goods out of the apparatus, rinses it and dries it. The blue color obtained is good wash- and sweat-proof as well as very good light, heat-setting and pleating fast. If you carry out the staining in Presence of wool, the latter remains undyed.

Example 5

1 part l, 5-dihydroxy-4,8-diamino-2- (4'-methoxy) -phenylanthraquinone, 1 part of the sodium salt of DinaphthyhnethandisuÜOnsäure and 8 parts of water ground until a fine dispersion is achieved. This mixture is poured into a dyebath that is made from 4000 parts of water and 4 parts of a highly sulfonated castor oil. One leads into this bathroom 100 parts of polyamide fabric and the temperature is increased to 100 ° C. in the course of 45 minutes dyes for one hour at 95 to 100 ° C. The fabric is then rinsed cold and cold and then dried. A clear blue dyeing of very good wash and perspiration fastness and good fastness is obtained Lightfastness.

The following table contains other dyes of the formula given which are used for dyeing of acetate rayon, triacetate rayon and polyester fibers are very suitable. They are in the table by the hydrocarbon RH on which the radical R is based, the material to be colored and the Hue of the coloring marked.

at
game R-H Phenoxybenzene Textile material hue blue 6th l-hydroxy-2-chlorobenzene Polyethylene terephthalate fiber Reddish blue 7th 1-hydroxy-2-methylbenzene the same Pure blue 8th 1-hydroxy-3-methylbenzene Acetate rayon blue 9 1-hydroxy-4-methylbenzene Polyethylene terephthalate fiber blue 10 l-hydroxy-4-ethylbenzene the same blue 11 1-hydroxynaphthalene Acetate rayon blue 12th 2-hydroxynaphthalene the same blue 13th 1-hydroxy-2-amylbenzene Polyethylene terephthalate fiber Pure blue 14th 1-hydroxy-4-amylbenzene Acetate rayon Pure blue 15th 1-hydroxy-4-octylbenzene Triacetate rayon Pure blue 16 1-hydroxy-4-cyclohexylbenzene the same Reddish blue 17th 1-hydroxy-2-phenylbenzene the same Reddish blue 18th 1-hydroxy-4-phenylbenzene Acetate rayon blue 19th 1-hydroxy-2,6rdiisopropylbenzene Polyethylene terephthalate fiber blue 20th 1-Hydroxy ^ -tert-butyi-S-methylbenzene the same blue 21 1-hydroxy-2,6-dimethylbenzene the same blue 22nd 1,2-dimethoxybenzene the same blue 23 1,4-dimethoxybenzene the same blue 24 Acetate rayon

5 R-H 6th Textile material the same hue blue at
game 1-hydroxy-2-methoxybenzene Acetate rayon Pure blue 25th 1-hydroxy-4-methoxybenzene Triacetate rayon Pure blue 26th (2'-hydroxy) ethoxybenzene Polyethylene terephthalate fiber Blue violet 27 1,2-dihydroxybenzene Acetate rayon blue 28 1,3-dihydroxybenzene Polyethylene terephthalate fiber blue 29 1,4-dihydroxybenzene Acetate rayon Reddish blue 30th 1-methoxy-4-methylbenzene the same blue 31 4'-aminophenoxybenzene the same blue 32 1-methoxy-4-propenylbenzene Polyethylene terephthalate fiber blue 33 1-Hydroxy-2-methoxy-4-allylbenzene the same Pure blue 34 [2 '- (2 "-Hydroxy) ethoxy] ethoxybenzene the same Reddish blue 35 1,3,5-trihydroxybenzene Acetate rayon blue 36 1-hydroxy-2-benzoyl-5-methoxybenzene Polyethylene terephthalate fiber Pure blue 37 2,2-bis (4'-hydroxyphenyl) propane the same blue 38 2'-bromoethoxybenzene 39

Example 40

100 parts Polyäthylenterephthalatfaser be brought at 60 ⁰ C in a dye bath consisting of 3000 parts of water, 1 part of the dye used in Example 1, 1 part of the dye as used in Example 2 and 1.5 parts of 2-hydroxy-l, l ' -diphenyl. The dyebath is heated to boiling temperature within 20 minutes. The material to be ^{dyed is dyed at 100 °} C. for 60 minutes, taken out of the dyebath, rinsed with water and dried. The polyester fiber is colored in a beautiful blue, washable and very light, heat-setting and pleating-fast shade. Co-treated wool and cotton are well reserved.

Other blends well suited for dyeing acetate and triacetate rayon and polyester fibers are z. B. 1,5-dihydroxy-4,8-diamino-2- (4'-methoxy) -phenylanthraquinone and 1,5-dihydroxy-4,8-diamino - 2 - (2 '- hydroxy - 5' - amyl) - phenylanthraquinone, 1,5 - dihydroxy - 4,8 - diamino - 2 - (4'-methoxy) phenylanthraquinone and 1,5-dihydroxy-4,8-diamino-2- (4'-ethoxy) phenylanthraquinone as well as 1,5-dihydroxy-diamino-2- (4'-hydroxy) -phenylanthraquinone and 1,5-dihydroxy-4,8-diamino-2- (4'-ethoxy) -phenylanthraquinone. Used in the same concentration, these mixtures give stronger colors than the dye, 5-dihydroxy-4,8-diamino-2- (4'-methoxy) -phenylanthraquinone alone. The stripes remain white in light colors.

Claims (1)

PATENT CLAIM: Use of the anthraquinone dyes of the formula OH O NH ₈ NH ₂ O OH wherein R for an optionally, with the exception of by nitro or amino groups or for O-X group para halogen atoms, substituted Aryl radical which is in the nucleus bound to the anthraquinone radical at least carries an —O — X group, where X is a hydrogen atom or denotes an optionally further substituted alkyl, cycloalkyl or aryl radical, alone or in a mixture with one another for dyeing polyamide fibers, cellulose ester fibers and polyterephthalic acid ester fibers from aqueous suspension. Considered publications:
German Patent No. 864425;
U.S. Patent No. 2,773,071. When the registration was announced, 7 color tables with explanations were laid out. © 30? 538/330 2.63