US1843670A - Manufacture of coloring matters and dyeings therewith - Google Patents
Manufacture of coloring matters and dyeings therewith Download PDFInfo
- Publication number
- US1843670A US1843670A US31666A US3166625A US1843670A US 1843670 A US1843670 A US 1843670A US 31666 A US31666 A US 31666A US 3166625 A US3166625 A US 3166625A US 1843670 A US1843670 A US 1843670A
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- United States
- Prior art keywords
- chromium
- parts
- dyeing
- dyeings
- manufacture
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/38—Preparation from compounds with —OH and —COOH adjacent in the same ring or in peri position
- C09B45/40—Chromium compounds
Definitions
- Azo dyestuffs containing chromium and capable of dyeing wool are already known.
- chromium derivatives can also be prepared in a water-soluble a form from direct coloring matters which contain groups enabling them to be chromed and that such chromium derivatives will still have the property of directly dyeing cotton or other cellulose fibres whether natural or arti- Ilu ficial. They produce dyeings of excellent fastness.
- Water-soluble chromium derivatives of the aforesaid character can especially be obtained from azo dyestufl's containing two radicles of an ortho-hydroxy-carboxylic 1 acid in their molecule. In some cases even chromium compounds of wool dyestuffs have the character of direct dyestufis and may be employed like the chromated direct coloring matters.
- the dyestuffs may be simply mixed with a soluble chromium salt.
- the mixture can serve for dyeing without further treatment and produces dyein s usually of greater fastness than those 0 tained with the coloring matters alone on chrome mordanted cotton or with afterchroming.
- the dyeing baths may be directly prepared from the dyestufl's and the chromi um saltsseparately.
- fluoride, acetate, oxalate, formate and other salts of chromium may be used or mixtures of such and similar salts.
- azo dyestufi's containing, as aforesaid, two radicles of an ortho-hydroxy carboxylic acid in their molecule, and which are particularly adapted to give water-soluble chromium derivatives are especially suitable.
- Chromium salts of a complex character which contain chromium both in an anion and in a cation state may also particularly be mentioned.
- Dyeing with the said chromium compounds of dyestuds or with dyestuds and chromium salts or mixtures made therefrom may be effected either in a hot bath or in the cold and it may oiten be advisable, in particular when working with cold baths, to employ an after- 1 treatment with an alkaline agent.
- Example 1 10 parts of the direct azo dyestufl' made from 4.4;-diamino-stilbene-2.2'-disulphonic acid and two molecular proportions of salicylic acid corresponding to the formula:
- chromium salt solution may be prepared from 6 molecular proportions of chromium formate, 4 molecular proportions of chromium fluoride and 1 molecular proportion of chromium sulphate. After boiling the dyestufl' with the chromium salt solution for about 3 hours, the solution is filtered, if necessary, and the new compound salted out. It should be dried with caution. The quantity of chromium salts can be considerably reduced.
- Example 2 3 parts of the direct azo dyestufi' representing the urea of the azo combination paraphenylene-diamine sulfonic acid salicylic acid, as expressed by the formula:
- chro mium salts composed of 6 molecular praportions of chromium formate, 4 molecular proportions of chromium fluoride and 1 molecular proportion of chromium sulfate
- Such mixture may be used for dyeing cotton in a hot bath, while gradually adding a solution of common salt.
- Example 3 Instead of first making the chromated dyestufl as described in Example 1, 10 parts of cotton maybe dyed with 0.3 part of the azo dyestuff mentioned in said example, 0.3 part of crystallized sodium acetate, 3 parts of the chromium salt solution mentioned in Example 1 and 200 parts of water, while gradually adding 12 parts of saturated common salt solution.
- the following dyestufis may also be mixed With soluble chromium salts and the mixtures used for dyeing, or the dye-hath may be prepared with the coloring matters and an addition of a chromium salt:
- som nopmr 7 NH on 003 PQ 00H 1 i H our soul H prepared from 1 molecular proportion of 1 molecular proportion of p.p-diamino-di- 65 tetrazotized benzidine-o-o-disulfonic acid phenyl urea 2 molecular proportions of salicylic acid corresponding to the formula: of a direct azo dyestufi containing in its mole- Ewample formate-d i b y d r ox o tri-ch romium-formate and pota'ssium-tri-oxalate-chromate.
- Example 5 30parts of one of the dyestuffs mentioned in Example 3 are-mixed wlth 9 parts of dried sodium acetate and 43 parts of dried chromium-acetate-oxalate (see Example 4) containing 35 per cent of chromium. For dyeing 100 parts of cotton, 8 parts of such mixture are used with 10 parts of common salt, and dyed in ahot bath for an hour.
- chromium derivatives capable of dyeing cellulose fibers, of dyestuffs which consists in combining a direct azo dyestufi' containing groups enabling it to be chromed, and free from any heavy metal, with a soluble chromium salt.
- the process of dyeing cellulosic fiber which consists in applying a bath containing a dissolved direct azo dyestufi with two residues of an ortho-hydroxy-carboxylic acid inits molecule and a soluble chromium salt I:[a)'ndhaftertreating the dyeings in an alkaline 8.
- the process of dyeing cellulosic fiber which comprises applying thereto a bath containing a dissolved direct azo coloring matter having groups enabling it to be.
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- Organic Chemistry (AREA)
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Description
Patented Feb. 2, 1932 UNITED STATES PATENT OFFICE FRITZ G'lINTHER FRITZ' LANG-E, AND WILHELM SCHNEIDER, OF LUD'WIGSHAFEN-ON- GERMANY, ASSIGNORS, BY MESNE ASSIGNMENTS, TO GENERAL ANILINE WORKS, INC., OF NEW YORK, N. Y., A CORPORATION OF DELAWARE MANUFACTURE OF COLORING MATTERS AND DYEINGS THEREWITE flll'o Drawing. Application filed May 20, 1925, Serial No. 31,666, and in Germany June 30, 1924.
Azo dyestuffs containing chromium and capable of dyeing wool are already known.
We have now found that chromium derivatives can also be prepared in a water-soluble a form from direct coloring matters which contain groups enabling them to be chromed and that such chromium derivatives will still have the property of directly dyeing cotton or other cellulose fibres whether natural or arti- Ilu ficial. They produce dyeings of excellent fastness. Water-soluble chromium derivatives of the aforesaid character can especially be obtained from azo dyestufl's containing two radicles of an ortho-hydroxy-carboxylic 1 acid in their molecule. In some cases even chromium compounds of wool dyestuffs have the character of direct dyestufis and may be employed like the chromated direct coloring matters.
We have further found that it is not necessary to first prepare the chromium compounds of the dyestuffs, but the dyestuffs may be simply mixed with a soluble chromium salt. The mixture can serve for dyeing without further treatment and produces dyein s usually of greater fastness than those 0 tained with the coloring matters alone on chrome mordanted cotton or with afterchroming. Or the dyeing baths may be directly prepared from the dyestufl's and the chromi um saltsseparately. For example fluoride, acetate, oxalate, formate and other salts of chromium may be used or mixtures of such and similar salts. For such mixtures direct azo dyestufi's containing, as aforesaid, two radicles of an ortho-hydroxy carboxylic acid in their molecule, and which are particularly adapted to give water-soluble chromium derivatives are especially suitable. Chromium salts of a complex character which contain chromium both in an anion and in a cation state may also particularly be mentioned.
Dyeing with the said chromium compounds of dyestuds or with dyestuds and chromium salts or mixtures made therefrom may be effected either in a hot bath or in the cold and it may oiten be advisable, in particular when working with cold baths, to employ an after- 1 treatment with an alkaline agent.
The following examples illustrate more fully how the invention maybe carried into practice but the invention is not restricted to these examples. The parts are by weight.
Example 1 10 parts of the direct azo dyestufl' made from 4.4;-diamino-stilbene-2.2'-disulphonic acid and two molecular proportions of salicylic acid corresponding to the formula:
are dissolved in 400 parts of water, and boiled, after an addition of 5 parts of crystallized sodium acetate has been made, with 100 parts of a solution of a chromium salt, containing about 10 parts of chromium oxide Cr O;. Such chromium salt solution may be prepared from 6 molecular proportions of chromium formate, 4 molecular proportions of chromium fluoride and 1 molecular proportion of chromium sulphate. After boiling the dyestufl' with the chromium salt solution for about 3 hours, the solution is filtered, if necessary, and the new compound salted out. It should be dried with caution. The quantity of chromium salts can be considerably reduced.
For dyeing, 100 partsof cotton are treated in a hot bathcontaining say 3 parts of the new chromium compound and a little Glau bers or common salt, for about an hour, or manipulated for several hours at ordinary temperature, then rinsed for a short time and put into lime water for a while. Fast orange shades are so obtained.
Example 2 3 parts of the direct azo dyestufi' representing the urea of the azo combination paraphenylene-diamine sulfonic acid salicylic acid, as expressed by the formula:
are mixed with so much of a mixture of chro mium salts (composed of 6 molecular praportions of chromium formate, 4 molecular proportions of chromium fluoride and 1 molecular proportion of chromium sulfate) as corresponds to 8 parts of chromium oxide, and with 3 parts of dehydrated sodium acetate. Such mixture may be used for dyeing cotton in a hot bath, while gradually adding a solution of common salt.
Example 3 Instead of first making the chromated dyestufl as described in Example 1, 10 parts of cotton maybe dyed with 0.3 part of the azo dyestuff mentioned in said example, 0.3 part of crystallized sodium acetate, 3 parts of the chromium salt solution mentioned in Example 1 and 200 parts of water, while gradually adding 12 parts of saturated common salt solution.
The following dyestufis may also be mixed With soluble chromium salts and the mixtures used for dyeing, or the dye-hath may be prepared with the coloring matters and an addition of a chromium salt:
A dyestuif from 2 molecular proportions SOaH no-Qrmdyes red.
A similar dyestufi', but with 1 molecular proportion of 5.5,-dihydroxy-2.2'-dinaphthylamine-7.7-disulfonic acid instead of the urea named which corresponds to the formula S0311 H038 Boas NH sous N=NQ-0 E E0 N=N ooon dyes violet. The same dyeings are obtained with a dyestufi' derived from ortho-aminopara-sulfo-salicylic acid.
A dyestuif corresponding to the formula:
HOaS
E 03S EN 0 H Q Q W 2 1 C O OH 5 0311 5H also dyes violet.
The same amino-naphthol-sulfonic acid derivative with 1 molecular proportion of 4.4-diamino stilbene 2.2 disulfonic acid which gives a dyestulf corresponding to the formula:
NHQOH OOH OaH H dyes blue,
As further examples may be cited the sulfonation products of the following disazodyestuffs, dyeing from golden yellow to orange yellow:
1 molecular proportion of benzidine 2 molecular proportions of salicylic acid corresponding to the formula:
HOQN=N COOH COOH 80:5:
1 molecular proportion of o.o-dianisidine 2 molecular proportions of salicylic acid corresponding to the formula:
p 0011 (film E OOH H OCH: 8 a
1 molecular proportion of benzidine 2 molecular proportions of meta-cresotinic acid corresponding to the formula:
som nopmr 7 NH on 003 PQ 00H 1 i H our soul H prepared from 1 molecular proportion of 1 molecular proportion of p.p-diamino-di- 65 tetrazotized benzidine-o-o-disulfonic acid phenyl urea 2 molecular proportions of salicylic acid corresponding to the formula: of a direct azo dyestufi containing in its mole- Ewample formate-d i b y d r ox o tri-ch romium-formate and pota'ssium-tri-oxalate-chromate.
Example 5 30parts of one of the dyestuffs mentioned in Example 3 are-mixed wlth 9 parts of dried sodium acetate and 43 parts of dried chromium-acetate-oxalate (see Example 4) containing 35 per cent of chromium. For dyeing 100 parts of cotton, 8 parts of such mixture are used with 10 parts of common salt, and dyed in ahot bath for an hour.
We claim:
1. The process of manufacturing chromium derivatives, capable of dyeing cellulose fibers, of dyestuffs which consists in combining a direct azo dyestufi' containing groups enabling it to be chromed, and free from any heavy metal, with a soluble chromium salt.
2. The process of manufacturing chr0mi-' um derivatives, capable of dyein cellulose fibers, of dyestuifs which consists 1n combining a direct azo dyestuif, containing in its molecule two residues of an ortho-hydroxycarboxylic acid and free from any heavy metal, with a water-soluble chromium salt.
3. AS1111 article of manufacture a directly dyeing water-soluble product containingchromium. but no other heavymetal and a direct azo dye-stufi having groups enabling it to be chromed.
4. As an article of manufacture a directly dyeing water soluble product containing chromium but no' other heavy metal-and a direct azo dyestufi containin in its molecule twpi residues of an ortho-hyd roxy-carboxylic aci 5. As a com osition of matter, a mixture of a direct azo yestufi containing in itsmolecule two residues of an ortho-hydroxy-carboxylic acid and free from any heavy metal and a water-soluble chromium salt.
'6, Asa composition of matter, a a:
cule two residues of an ortho-hydroxy-carboxylic acid and free from any heavy metal and a water-soluble complex chromium salt which composition is soluble in water and has the property of directly dyeing cellulosic er. a
7. The process of dyeing cellulosic fiber which consists in applying a bath containing a dissolved direct azo dyestufi with two residues of an ortho-hydroxy-carboxylic acid inits molecule and a soluble chromium salt I:[a)'ndhaftertreating the dyeings in an alkaline 8. The process of dyeing cellulosic fiber, which comprises applying thereto a bath containing a dissolved direct azo coloring matter having groups enabling it to be.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE1843670X | 1924-06-30 |
Publications (1)
Publication Number | Publication Date |
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US1843670A true US1843670A (en) | 1932-02-02 |
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Application Number | Title | Priority Date | Filing Date |
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US31666A Expired - Lifetime US1843670A (en) | 1924-06-30 | 1925-05-20 | Manufacture of coloring matters and dyeings therewith |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2777840A (en) * | 1951-05-25 | 1957-01-15 | Ciba Ltd | Asymmetrical urea derivatives of monoazo-dyestuffs |
-
1925
- 1925-05-20 US US31666A patent/US1843670A/en not_active Expired - Lifetime
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2777840A (en) * | 1951-05-25 | 1957-01-15 | Ciba Ltd | Asymmetrical urea derivatives of monoazo-dyestuffs |
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