US2040796A - Process of dyeing animal fibers with metal complex compounds of organic acid dyestuffs - Google Patents

Process of dyeing animal fibers with metal complex compounds of organic acid dyestuffs Download PDF

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US2040796A
US2040796A US644914A US64491432A US2040796A US 2040796 A US2040796 A US 2040796A US 644914 A US644914 A US 644914A US 64491432 A US64491432 A US 64491432A US 2040796 A US2040796 A US 2040796A
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acid
per cent
dyeing
metal complex
dyestuffs
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Rittinghausen Carl Maria
Haynn Richard
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General Aniline Works Inc
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General Aniline Works Inc
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    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/02Material containing basic nitrogen
    • D06P3/04Material containing basic nitrogen containing amide groups
    • D06P3/14Wool
    • D06P3/20Wool using mordant dyes using metallisable dyes

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  • Our present invention relates to an improvement in the dyeing of animal fibers with metal complex compounds of organic acid dyestuffs, such as copper or chromium complex compounds of acid ortho-hydroxy-azo dyestuffs or other acid dyestuffs capable of forming metal complex compounds; more particularly it relates to a process which comprises carrying out the dyeing process in an acid bath containing only such a 10 quantity of acid as is usual for dyeing with ordinary acid dyestuffs and in the presence of a water-soluble protective colloid of the group consisting of protective colloids of natural and synthetic origin.
  • organic acid dyestuffs such as copper or chromium complex compounds of acid ortho-hydroxy-azo dyestuffs or other acid dyestuffs capable of forming metal complex compounds
  • metal complex compounds of acid dyestuffs if the dyeing operation is carried out in the presence of a water-soluble protective colloid of the group consisting of protective colloids of natural and synthetic origin.
  • a water-soluble protective colloid of the group consisting of protective colloids of natural and synthetic origin In the new process about 3 to at most per cent, generally about 4 percent, of sulfuric acid are sufficient.
  • protective colloid and the class of materials identified thereby and their properties are well known to those skilled in the art.
  • protective colloids i. e. natural products, or products made from natural materials, or protective colloids made by synthesis.
  • process of the present invention is notlimited to any particular class of metal complex compounds of acid dyestuffs; the effect obtained is evident in the case of all dyes included in the general meaning of the term metal complex com-- pounds of acid organic dyestuffs.
  • water-soluble naturalpr'otective colloids or as protective colloids made from natural products there may be mentioned glue, starch, dextrin, derivatives of sugar, sulfite pulp Waste liquors, water-soluble albuminous substances or decomposition products thereof, for instance, compounds of the kind of the so-called protalbinicand lysalbinic acids, such as the mixture of the sodium salts of caseoprotalbinicand caseolysalbinic acid obtainable by causing caustic soda to act upon casein.
  • protalbinicand lysalbinic acids such as the mixture of the sodium salts of caseoprotalbinicand caseolysalbinic acid obtainable by causing caustic soda to act upon casein.
  • protalbinicand lysalbinic acids such as the mixture of the sodium salts of caseoprotalbinicand caseolysalbinic acid obtainable by causing caustic soda to act upon casein.
  • Synthetic compounds which have the properties of protective colloids are, for instance, the compounds obtainable by introducing into organic compounds containing one or more hydroxy, carboxy or amino groups a radical of a polyglycol ether containing 4 or more--CzH4 groups, such as the radicaland further combining, if desired, the thus obtained condensation products which 'still contain free hydroxyl groups, with reactive compounds.
  • a radical of a polyglycol ether containing 4 or more--CzH4 groups such as the radicaland further combining, if desired, the thus obtained condensation products which 'still contain free hydroxyl groups, with reactive compounds.
  • a further increase of the qualities of the dyeings may be attained if, in addition to the protective colloid, Watersoluble salts of hydrohalic acids or similarly acting acids, such as chlorides, bromides, fluorides or thiocyanates, are added to the dye baths.
  • the dyeing operation in the presence of a water-soluble protective colloid may be carried out while using as an acid sulfuric acid, or sulfuric acid together with an organic acid, such as formic acid, or even an organic acid alone.
  • a dyebath is prepared from 6 per cent of the chromium complex compound of the diphenylnaphthylmethane dyestufi from 1 mo of 2-hydroxy-1-naphthaldehyde-3.6-disu1fonic' acid and 2 mols of ortho-cresotinic acid (obtainable by heating in an autoclave at 120 C. for 1 hour 100 parts of the dyestuif with 400 parts of a chromium formiate solution containing per cent of CrzOz), 4 per cent of sulfuric acid and 5 to per cent of glue, the material is introduced into the dyebath, the whole is heated to boiling within half an hour and boiling is continued for 1 to 1 hours.
  • the dyebath is prepared from 6 per cent of the dyestuif used in Example (1), 4 per cent of sulfuric acid, 5 to 10 per cent of glue and 2 /2 per cent of ammonium fluoride or ammonium chloride and the material is treated as indicated in Example (1).
  • W001 is dyed in a dyebath containing 6 per cent of the dyestuif used in Example 1), 4 per cent of formic acid of 85 per cent strength and 5 to 10 per cent of glue.
  • the material is entered into the dyebath, the whole is heated to boiling temperature and the material is dyed at this temperature for 1 to 1 hours.
  • glue there may be used the corresponding quantity of an albuminous decomposition product which is obtainable from casein by the action of caustic soda in the heat.
  • the dyebath is prepared from 6 per cent of the chromium complex compound of the azo dyestuff from diazotized 1-amino-2-naphthol-4- sulfonic acid and fi-naphthol (obtainable by heating in an autoclave at 105 C for 2 hours 100 parts of the azo dyestuif with 60 parts of a chromium salt and 1000 parts of water), 4 per cent of formic acid of 85 per cent strength and 5 to 10 per cent of glue or the same quantity of a water-soluble albuminous decomposition product.
  • the material to be dyed is introduced into the dyebath, the whole is heated to boiling within hour, the material is dyed at this temperature for hour, 4 per cent of sulfuric acid of 96 per cent strength are added and boiling is continued for 1 hour.
  • W001 is dyed as follows:
  • a dyebath containingfi per cent of the dyestufi used in Example (1), 4 per cent of sulfuric acid of 96 per cent strength and 2 to 3 per cent of a reaction product from ethylene oxide and dodecylalcohol obtainable, for instance, by heating 200 parts of dodecylalcohol to about 180 C. in an autoclave with about 400 parts of ethylene oxide which is introduced a little at a time. The material is introduced into the dyebath, the whole is heated to' boiling within hour and boiling is continued for 1 to 1 hours.
  • the dyebath is prepared from 6 per cent of the dyestuff used in Example (1); 4 per cent of sulfuric acid of 96 per cent strength, 2 to 3 per cent of a condensation product obtainable according to one of the examples of the British Specifications Nos. 380,431 and 380,851 or of the French Patent No. 727,202, for instance, a condensation product of mols of ethylene oxide with 1 mol. leading about 880 parts of ethylene oxide, while stirring at a temperature between 130 C. and 140 C. into 270parts of octodecylalcohol containing 2.7 parts of an aqueous caustic soda solution of 40 B., and 2.5 per cent of ammonium fluoride or ammonium chloride.
  • the material is dyed as indicated in Example 5.
  • a dyebath is prepared from 6 per cent of the chromium complex compound of the dyestuif from diazotized 4-nitro-2-aminophenyl. and phenyl-2-amino-8-naphthol-6-sulfonac acid, 4 per cent of formic acid of 85 per cent strength and 2 to 3 per cent of the reaction product from ethylene oxide with dodecylalcohol mentioned in Example (5).
  • W001 is dyed in. this bath with or without addition of ammonium fluoride or ammonium chloride.
  • W001 is dyed in a bath which is prepared from 6 per cent of the dyestuif used in Example 1, 4 per cent of formic acid of 85 per cent strength, 2 to 3 per cent of the reaction product from ethylene oxyde and dodecylalcohol. The whole is heated to boiling within hour, the material is dyed at boiling temperature for A hour, 4 per cent of sulfuric acid of 96 per cent strength are added and boiling is continued for 1 hour.
  • a dyebath is prepared containing 4 per cent of a chromium complex compound of the azo dyestuff from diazotized nitro-l-amino-Z- hydroxynaphthalene-4-sulfonic acid and B-naphtho], 4 per cent of sulfuric acid of 96 per cent strength and about 2 per cent of a poly-oxyethylether of sorbit-tetra-palm oil fatty acid ester, obtainable by introducing ethylene oxyde at about 140 C. to about 160 C. and in the presence of 0.5 per cent of caustic soda solution of 40 B.
  • Sorbittetra-palm oil fatty acid ester is obtainable by heating sorbit with a quantity of palm oil fatty acid necessary for forming the tetra-ester at about 200 C. to about 215 C. until free fatty acid is no longer detectable.
  • the dyeing operation is commenced at 40 C. the material to be dyed is heated to boiling within hour and boiling is continued for about 1 hour.
  • a modification of the process as claimed in claim 1 which comprises adding to the dye bath a small quantity of a salt of the group consisting of water-soluble salts or hydrohalic acids and thiocyanic acid.
  • a dye bath for dyeing animal fibers with metal complex compounds of organic acid dyestufls comprising a metal complex compound of an organic acid dyestufi, about 3 to 5 per cent of acid as is usual for dyeing with ordinary acid dyestuffs and a water soluble protective colloid.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)

Description

Patented May 12, 1936 UNITED STATES PROCESS or DY'EING ANIMAL FIBERS WITH METAL COMPLEX COMPOUNDS OF OR- GANIC ACID DYESTUFFS Carl Maria Rittinghausen,
faunus, and Richard Haynn,
Bad Soden-on-the- Frankfort-onthe-Main, Germany, assignors to General Aniline Works, 1:10., New York, N. Y.,
of Delaware No Drawing. Applicati Serial No. 644,914. 1931 9 Claims.
Our present invention relates to an improvement in the dyeing of animal fibers with metal complex compounds of organic acid dyestuffs, such as copper or chromium complex compounds of acid ortho-hydroxy-azo dyestuffs or other acid dyestuffs capable of forming metal complex compounds; more particularly it relates to a process which comprises carrying out the dyeing process in an acid bath containing only such a 10 quantity of acid as is usual for dyeing with ordinary acid dyestuffs and in the presence of a water-soluble protective colloid of the group consisting of protective colloids of natural and synthetic origin.
It is known that in the dyeing process by means of metal complex compounds of acid organic dyestufis, sulfuric acid or an organic acid together with sulfuric acid is added to the dye bath. In order to obtain a satisfactory evenness of the 20 dyeings and a normal development of the fastness properties of the dyestuffs, the hitherto known process of dyeing with this classof dyestuffs requires a considerably high quantity of acid, for instance, about 8 to 10 per cent of sul- 25 furic acid calculated on the weight of the material to be dyed, and prolonged boiling is required to finish the dyeing operation.
This method has the disadvantage that the dye baths are only insufficiently utilized, even when a high percentage of dyestuif is used, that the dye tubs or vessels are soon corroded and that the vegetable ,efiect threads contained in the woolen or other animal materials are injured. The use of formic acid or of formic acid together with 35 sulfuric acid, as suggested in the French Patent No. 702,387 yields, in the case of most of the metal complex compounds of acid dyestuffs, mixture (uneven and spotted) dyeings which, with the exception of a few cases, do not possess the nor- 40 mal and characteristic fastness properties of the dyestuffs proper. Furthermore, this latter method is not suited for the production of fancy (light) shades.
We have now found that the dyeing with metal 45 complex compounds of organic acid dyestuffs,
such as copper or chromium or other metal complex compounds of acid ortho-hydroxy azo dyestuffs or other acid dyestuffs capable of forming metal complex compounds, may be carried out in 50 normal acid dye baths containing only the normal quantities of acid as are usual for dyeing with ordinary acid dyestuffs which do not contain metal in a complex binding, that is to say, with smaller quantities of sulfuric acid than those Y 55 hitherto used. for dyeing with the said class of a corporation on November 29, 1932, Germany December '1,
metal complex compounds of acid dyestuffs, if the dyeing operation is carried out in the presence of a water-soluble protective colloid of the group consisting of protective colloids of natural and synthetic origin. In the new process about 3 to at most per cent, generally about 4 percent, of sulfuric acid are sufficient.
The term protective colloid and the class of materials identified thereby and their properties are well known to those skilled in the art. There may be used in our present process all kinds of protective colloids, i. e. natural products, or products made from natural materials, or protective colloids made by synthesis. Furthermore, the process of the present invention is notlimited to any particular class of metal complex compounds of acid dyestuffs; the effect obtained is evident in the case of all dyes included in the general meaning of the term metal complex com-- pounds of acid organic dyestuffs.
As water-soluble naturalpr'otective colloids or as protective colloids made from natural products there may be mentioned glue, starch, dextrin, derivatives of sugar, sulfite pulp Waste liquors, water-soluble albuminous substances or decomposition products thereof, for instance, compounds of the kind of the so-called protalbinicand lysalbinic acids, such as the mixture of the sodium salts of caseoprotalbinicand caseolysalbinic acid obtainable by causing caustic soda to act upon casein. Compounds of this class are, for instance, disclosed by Paal in Berlchte der deutschen Chemischen Ges'ellschaft, volume 35, page 2195 and following.
Synthetic compounds which have the properties of protective colloids are, for instance, the compounds obtainable by introducing into organic compounds containing one or more hydroxy, carboxy or amino groups a radical of a polyglycol ether containing 4 or more--CzH4 groups, such as the radicaland further combining, if desired, the thus obtained condensation products which 'still contain free hydroxyl groups, with reactive compounds. Compounds of this kind are more fully disclosed in French Patent No. 727,202 and British Patents Nos, 380,431 and 380,851.
By these additions the efficiency of the dye baths is increased and very even dyeings are 'ob tained; simultaneously the other disadvantages which appear if the old process with the high percentage of acid is used, are avoided. Itis surprising that the addition of'only a small quantity of a water-soluble protective colloid allows the dyeing of animal fibers by means of metal complex compounds of acid dyestuffs in the presence of much less'sulfuric acid and yet with better results than by the old method.
A further increase of the qualities of the dyeings may be attained if, in addition to the protective colloid, Watersoluble salts of hydrohalic acids or similarly acting acids, such as chlorides, bromides, fluorides or thiocyanates, are added to the dye baths.
Accordance to our new process the dyeing operation in the presence of a water-soluble protective colloid may be carried out while using as an acid sulfuric acid, or sulfuric acid together with an organic acid, such as formic acid, or even an organic acid alone.
The following examples serve to illustrate the invention, but they are not intended to limit it thereto, the parts being by weight, unless stated otherwise: The percentage quantities are calculated on the weight of the material to be dyedz.
( 1) W001 is dyed as follows;
A dyebath is prepared from 6 per cent of the chromium complex compound of the diphenylnaphthylmethane dyestufi from 1 mo of 2-hydroxy-1-naphthaldehyde-3.6-disu1fonic' acid and 2 mols of ortho-cresotinic acid (obtainable by heating in an autoclave at 120 C. for 1 hour 100 parts of the dyestuif with 400 parts of a chromium formiate solution containing per cent of CrzOz), 4 per cent of sulfuric acid and 5 to per cent of glue, the material is introduced into the dyebath, the whole is heated to boiling within half an hour and boiling is continued for 1 to 1 hours.
(2) The dyebath is prepared from 6 per cent of the dyestuif used in Example (1), 4 per cent of sulfuric acid, 5 to 10 per cent of glue and 2 /2 per cent of ammonium fluoride or ammonium chloride and the material is treated as indicated in Example (1).
(3) W001 is dyed in a dyebath containing 6 per cent of the dyestuif used in Example 1), 4 per cent of formic acid of 85 per cent strength and 5 to 10 per cent of glue. The material is entered into the dyebath, the whole is heated to boiling temperature and the material is dyed at this temperature for 1 to 1 hours.
Instead of glue there may be used the corresponding quantity of an albuminous decomposition product which is obtainable from casein by the action of caustic soda in the heat.
(4) The dyebath is prepared from 6 per cent of the chromium complex compound of the azo dyestuff from diazotized 1-amino-2-naphthol-4- sulfonic acid and fi-naphthol (obtainable by heating in an autoclave at 105 C for 2 hours 100 parts of the azo dyestuif with 60 parts of a chromium salt and 1000 parts of water), 4 per cent of formic acid of 85 per cent strength and 5 to 10 per cent of glue or the same quantity of a water-soluble albuminous decomposition product. The material to be dyed is introduced into the dyebath, the whole is heated to boiling within hour, the material is dyed at this temperature for hour, 4 per cent of sulfuric acid of 96 per cent strength are added and boiling is continued for 1 hour.
(5) W001 is dyed as follows:
There is prepared a dyebath containingfi per cent of the dyestufi used in Example (1), 4 per cent of sulfuric acid of 96 per cent strength and 2 to 3 per cent of a reaction product from ethylene oxide and dodecylalcohol, obtainable, for instance, by heating 200 parts of dodecylalcohol to about 180 C. in an autoclave with about 400 parts of ethylene oxide which is introduced a little at a time. The material is introduced into the dyebath, the whole is heated to' boiling within hour and boiling is continued for 1 to 1 hours.
(6) The dyebath is prepared from 6 per cent of the dyestuff used in Example (1); 4 per cent of sulfuric acid of 96 per cent strength, 2 to 3 per cent of a condensation product obtainable according to one of the examples of the British Specifications Nos. 380,431 and 380,851 or of the French Patent No. 727,202, for instance, a condensation product of mols of ethylene oxide with 1 mol. leading about 880 parts of ethylene oxide, while stirring at a temperature between 130 C. and 140 C. into 270parts of octodecylalcohol containing 2.7 parts of an aqueous caustic soda solution of 40 B., and 2.5 per cent of ammonium fluoride or ammonium chloride. The material is dyed as indicated in Example 5.
(7) A dyebath is prepared from 6 per cent of the chromium complex compound of the dyestuif from diazotized 4-nitro-2-aminophenyl. and phenyl-2-amino-8-naphthol-6-sulfonac acid, 4 per cent of formic acid of 85 per cent strength and 2 to 3 per cent of the reaction product from ethylene oxide with dodecylalcohol mentioned in Example (5). W001 is dyed in. this bath with or without addition of ammonium fluoride or ammonium chloride.
(8) W001 is dyed in a bath which is prepared from 6 per cent of the dyestuif used in Example 1, 4 per cent of formic acid of 85 per cent strength, 2 to 3 per cent of the reaction product from ethylene oxyde and dodecylalcohol. The whole is heated to boiling within hour, the material is dyed at boiling temperature for A hour, 4 per cent of sulfuric acid of 96 per cent strength are added and boiling is continued for 1 hour.
(9) A dyebath is prepared containing 4 per cent of a chromium complex compound of the azo dyestuff from diazotized nitro-l-amino-Z- hydroxynaphthalene-4-sulfonic acid and B-naphtho], 4 per cent of sulfuric acid of 96 per cent strength and about 2 per cent of a poly-oxyethylether of sorbit-tetra-palm oil fatty acid ester, obtainable by introducing ethylene oxyde at about 140 C. to about 160 C. and in the presence of 0.5 per cent of caustic soda solution of 40 B. into a melt of the sorbit-tetra-palm oil fatty acid ester, until about 70 mols of ehylene oxyde per mol. of the ester have been absorbed. Sorbittetra-palm oil fatty acid ester is obtainable by heating sorbit with a quantity of palm oil fatty acid necessary for forming the tetra-ester at about 200 C. to about 215 C. until free fatty acid is no longer detectable.
The dyeing operation is commenced at 40 C. the material to be dyed is heated to boiling within hour and boiling is continued for about 1 hour.
Instead of the protective colloids, used in the foregoing examples, the following compounds may be used:
(a) 2 to 3 per cent. wool fat alcohols;
(b) 2 to 3 per cent. of a product obtainable by condensation. of oleylalcohol with 20 mols of ethylene oxide and subsequent ethylation;
, (c) 2 to 3 per cent. of a polyglycolester of ricinoleic acid (obtainable as described in Example 2 of British Patent No. 380,431)
(d) 2 to 3 per cent. of a product consisting of of a polyglycolether of of octodecylalcohol, obtainable by 95 parts of a condensation product, obtainable from oleic acid and 6 mole of ethylene oxide and subsequent ethylation, and parts of product b) We claim:
1. The process of dyeing animal fibers with metal complex compounds of organic acid dyestuffs which comprises carrying out the -dye ing in normal acid dye baths, containing about 3 to 5 per cent of acid as is usual for dyeing with ordinary acid dyestufis, and in the presence of a water-soluble protective colloid.
2. A modification of the process as claimed in claim 1 which comprises adding to the dye bath a small quantity of a salt of the group consisting of water-soluble salts or hydrohalic acids and thiocyanic acid.
3. The process of dyeing animal fibers with a metal complex compound of an organic acid dyestuif which comprises carrying out the dyeing in a normal acid dye bath containing about 4 per cent of sulfuric acid and about 2 to per cent of a water-soluble protective colloid, calculated on the weight of the material to be dyed.
'4. A modification of the process as claimed in claim 3 which comprises replacing the sulfuric acid by a corresponding quantity of formic acid. 5. The process of dyeing wool with a chromium complex compound oi an organic acid dyestufi' which comprises carrying out the dyeing in a normal acid dye bath containing about 4 per cent ofsulfuric acid, about 5 to 10 per cent of glue and about 2 per cent of ammonium fluoride, calculated von the weight of the material to be dyed,
6. The process of r'yeing wool with a chromium complex compound of an organic acid dyestui! which comprises carrying out the dyeing in a normal acid dye bath containing about 4 per cent of sulfuric acid, about 2 to 3 per cent of the condensation product from 20 mols ethylenoxyde and 1 mol. octodecylalcohol and about 2 per decylalcohol, calculated on the weight of the material to be dyed.
8. The process of dyeing animal fibers with a metal complex compound of an organic acid dyestun which comprises carrying out the dyeing in a normal acid dye bath containing about 3 to 5 per cent of sulfuric acid and about 2 to 10 per cent, calculated on the .weight of the material to be dyed, of the condensation product from an 'alkyle'ne oxide and a high molecular weight aliphatic alcohol.
9. A dye bath for dyeing animal fibers with metal complex compounds of organic acid dyestufls comprising a metal complex compound of an organic acid dyestufi, about 3 to 5 per cent of acid as is usual for dyeing with ordinary acid dyestuffs and a water soluble protective colloid.
CARL MARIA RI'ITINGHAUSEN. RICHARD HAYNN.
US644914A 1931-12-07 1932-11-29 Process of dyeing animal fibers with metal complex compounds of organic acid dyestuffs Expired - Lifetime US2040796A (en)

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Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2434178A (en) * 1948-01-06 Metachkome dyeing with a colloid
US2443166A (en) * 1945-01-13 1948-06-08 American Cyanamid Co Metachrome dyeing with cationic and non-ionic agents
US2470080A (en) * 1946-06-18 1949-05-10 American Cyanamid Co Method of dyeing with metallized dyes
US2524041A (en) * 1946-07-11 1950-10-03 Arkansas Company Inc Tippy wool dyeing assistants
US2638404A (en) * 1951-02-10 1953-05-12 American Cyanamid Co Method of dyeing nitrogenous fibers with metallized azo dyes
US2643211A (en) * 1949-11-30 1953-06-23 Rayette Inc Hair color-rinse concentrate
US2723178A (en) * 1951-02-10 1955-11-08 American Cyanamid Co Method of controlling the migration of metallized dyes between dye bath and fabric
US2763530A (en) * 1951-01-11 1956-09-18 Ciba Ltd Process for dyeing loose wool
US2869968A (en) * 1952-03-28 1959-01-20 Saul & Co Method of dyeing mixtures of animal fibers and synthetic polyamide fibers with reservation of the latter
US3043648A (en) * 1955-12-09 1962-07-10 Sandoz Ltd Process for the fast dyeing of natural and artificial polyamide fibers with water-soluble metal-containing azo dyestuffs
US3444157A (en) * 1964-03-16 1969-05-13 Dainichiseika Color Chem Process for the manufacture of aqueous azo and basic lake pigments

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2434178A (en) * 1948-01-06 Metachkome dyeing with a colloid
US2443166A (en) * 1945-01-13 1948-06-08 American Cyanamid Co Metachrome dyeing with cationic and non-ionic agents
US2470080A (en) * 1946-06-18 1949-05-10 American Cyanamid Co Method of dyeing with metallized dyes
US2524041A (en) * 1946-07-11 1950-10-03 Arkansas Company Inc Tippy wool dyeing assistants
US2643211A (en) * 1949-11-30 1953-06-23 Rayette Inc Hair color-rinse concentrate
US2763530A (en) * 1951-01-11 1956-09-18 Ciba Ltd Process for dyeing loose wool
US2638404A (en) * 1951-02-10 1953-05-12 American Cyanamid Co Method of dyeing nitrogenous fibers with metallized azo dyes
US2723178A (en) * 1951-02-10 1955-11-08 American Cyanamid Co Method of controlling the migration of metallized dyes between dye bath and fabric
US2869968A (en) * 1952-03-28 1959-01-20 Saul & Co Method of dyeing mixtures of animal fibers and synthetic polyamide fibers with reservation of the latter
US3043648A (en) * 1955-12-09 1962-07-10 Sandoz Ltd Process for the fast dyeing of natural and artificial polyamide fibers with water-soluble metal-containing azo dyestuffs
US3444157A (en) * 1964-03-16 1969-05-13 Dainichiseika Color Chem Process for the manufacture of aqueous azo and basic lake pigments

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