US2968661A - 1-amino-2-bromo-4-arylaminoanthraquinone compounds - Google Patents

1-amino-2-bromo-4-arylaminoanthraquinone compounds Download PDF

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US2968661A
US2968661A US757680A US75768058A US2968661A US 2968661 A US2968661 A US 2968661A US 757680 A US757680 A US 757680A US 75768058 A US75768058 A US 75768058A US 2968661 A US2968661 A US 2968661A
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James M Straley
Ralph R Giles
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Eastman Kodak Co
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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
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/16—Amino-anthraquinones
    • C09B1/20—Preparation from starting materials already containing the anthracene nucleus
    • C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
    • C09B1/32—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups

Definitions

  • polyacrylonitrile fibers are ditiicult to dye in deep, fast shades without the use of special dyeing techniques, such as, for example, the use of pressure, carriers or the so-called cuprous ion technique involving the use of acid wool dyes.
  • special dyeing techniques such as, for example, the use of pressure, carriers or the so-called cuprous ion technique involving the use of acid wool dyes.
  • pressure involves the use of pressure equipment which is more expensive than the equipment used where no pressure is involved.
  • the use of carriers involves the expense of providing the carriers. Also, when carriers are employed operations for the recovery of the carrier for reuse are involved and these recovery operations add to the expense of the dyeing operation.
  • R and R each represent an alkyl group having 1 to 4 carbon atoms, a hydroxy alkyl group having 1 to 4 carbon atoms, a l3-methoxyethyl group or a fi-ethoxyethyl group, n represents 2, 3 or 4 and wherein taken together also represent a morpholinyl group or a piperidyl group.
  • anthraquinone compounds of our invention can be prepared by more than one method We prefer to prepare them by condensing the acid chloride of the appropriate 1 amino 2 bromo-4-carboxyanilinoanthraquinone with a primary amine having the formula:
  • Example 1 One gram of 1-amino-2-bromo-4-o-carboxyanilinoanthraquinone was suspended in 20 cc. of dry chlorobenzene. Two cc. of thionyl chloride were added and the reaction mixture obtained was heated on a steam bath, with stirring, until a clear solution was obtained and no further color change toward the red occurred. The solution thus obtained was cooled to C., diluted with an equal volume of n-hexane and cooled to 20 C. The acid chloride thus prepared was recovered by filtration, washed with n-hexane and sucked dry.
  • Example 2 Ten grams of 1-arnino-2-bromo-4-o-carboxyanilinoanthraquinone were suspended in cc. of dry o -dichlorobenzene. 3.4 cc. .of'thionyl chloride were added and the temperature, ofthe reaction mixture. was-gradually raised to 80 C. over a period of about 1.5 hours and held at this temperature for one hour While stirring. Excess thionyl chloride was :removed by passing a stream of dry air through the reaction mixture at 65 70 C.
  • Example 3 Example 1 was repeated using 4 grams of Z-dirnethyl- 'aminoethylamine in place of 3-dimethylaminopropylamine. 'l-am'ino -'2 bromo-- 4-o-[N-(2-dimethy'laminoethyl) carboxamido] anilinoanthraquinone was obtained as a blue solid. It dyes polyacrylonitrile textile materials blue shades which have excellent fastness to light and wet processing.
  • Example '5 Example 1 was .repeated using 1 gram of l-amino-2- bromo-4-p-carboxyanilinoanthraquinone and 3.5 grams of '3-dimethylaminopropy1amine.
  • 1-amino-2-brorno-4-p-[N- (3 dimethylaminoprqpyl) carboxamido] anilinoanthraquinone was obtainedas a blue solid. It dyes polyacrylonitrile textile materials blue shades which have excellent fastness to .light and wet processing.
  • Example '6 Example 1 was repeated using 4.5 grams of 3-diethylaminopropylamine in place of 3-dimethylaminopropylamine. l-amino-2-bromo-4-o-['N-(3-diethylaminopropyl) H l-amino-Z-bromo--o- C ONCHQCHzCHIN carboxamido]anilinoanthraquinone was obtained as a blue solid. It dyes polyacrylonitrile textile materials blue shades which have excellent "fastness to light and wet processing.
  • Example7 Example 7 was repeated using 1 gram of 1-amino-2- bromo-4sm-carboxyanilinoanthraquinone and 3 grams of Z-diethylanfinoethylamine. l-amino-Z-bromol-m-[N-.(2- diethylaminoethyl)car.boxarnido] anilinoanthraquinone was obtained as a blue solid. .It dyes polyacrylonitrile textile materials blue shades which have excellent fastness to light and wet processing.
  • Example 8 Example 1 was repeated using 1 gram of l-amino-Z- bromo-4-p-carboxyanilinoanthraquinone and 4 grams of N-(Z-aminoethyllpiperidine. "l-amino-z-bromol-p-[N- (2-piperidylethyl) carboxamido] anilinoanthraquinone having'th'e formula:
  • Example 10 Example 1 was repeated using 6 grams of 3-(di-fl-hydroxyethylamino)propylamine in place of 3-dimethylaminopropylarnine. l-amino-2-bromo-4-o-[N-3-di-phhydroxyethylaminopropyl) carboxamido] anilinoanthraquinone was obtained as a blue solid. It dyes polyacrylonitrile textile materials blue shades which have excellent fastness to light and wet processing.
  • Example 11 Example 2 'was repeated using 3.3 grams of 3-'('4-1norpholino) propylamine .H2 )H2 0-o in place of 3-dimethylaminopropylamine.
  • H2 H2 C-O O anilinoanthraquinone was obtained as a blue solid. It dyes polyacrylonitrile textile materials blue shades which have excellent fastness to light and wet processing.
  • Example 1 2 Example 4 was repeated using 4.1 grams of 4-diethylamino-n-butylarrn'ne in place of S-dimethylaminopropylamine. 1-amino-2-bromo-4-m-[N (4 diethylamino-nbutyl)carboxamido] anilino-anthraquinone was obtained as a blue solid. It dyes polyacrylonitrile textile materials blue shades which have excellent fastness to light and wet processing.
  • Example 13 was obtained as a blue solid. It dyes polyacrylonitrile textile materials blue shades which have excellent fastness to light and wet processing.
  • Example 14 Example 2 was repeated using 3.4 grams of 3-(di- 8- methoxyethylamino)propylamine in place of 3-dimethy1- aminopropylamine.
  • Example Example 2 was repeated using 4.6 grams of 3-(di-18- Example 16 16.7 milligrams of the dye compound prepared in Example 1 was dissolved by warming in 5 cos. of ethylene glycol monomethyl ether. 20 ccs. of a 1% aqueous solution of Igepon T (3113 (Or- H 0 ONCH CHzSOaNa) were added and the volume brought to 200 ccs. by the addition of water at 50 C. Five cos. of a aqueous solution of formic acid were added, followed by 5 grams of Verel fabric. The temperature was brought to the boil and held there for 1 hour. The cloth was then rinsed in hot water and allowed to dry. It was dyed an attractive blue shade having excellent wash and light fastness. Similar results are obtained when Orlon 42 fabric is used instead of Verel fabric.
  • the primary amine compounds having the Formula I used in preparing the new anthraquinone compounds of the invention appear to include new as well as old comjlanilinoanthraquinone pounds. Many of these amines are specifically disclosed in the prior art. Those not specifically disclosed can be prepared by the methods used to prepare the known compounds.
  • the preferred amine 3-dimethylaminopropylamine is an article of commerce.
  • primary amines that can be used to prepare compounds of our invention include, for example Z-di-n-propylaminoethylamine, Z-diisopropylaminoethylaming 2-di-n butylaminoethylamine,
  • the new anthraquinone compounds of our invention can be applied to polyacrylonitrile textile materials from an aqueous dyebath in the same manner that water-insoluble cellulose acetate dyestulfs are commonly applied to cellulose acetate textile materials.
  • they may be directly applied to the polyacrylonitrile textile material undergoing coloration in the form of an aqueous suspension which can be prepared by grinding them to a paste in the presence of a sulfonated oil, soap, sodium lignin sulfonate, or other suitable dispersing agent and dispersing the resulting paste in water.
  • the dyes should be in finely divided condition.
  • the following example illustrates how the anthraquinone compounds of our invention can be applied to polyacrylonitrile textile materials.
  • the anthraquinone compounds are particularly useful in connection with the dyeing of modified polyacrylonitrile textile materials, such as Verel.
  • R1 II is condensed with a chloroalkylnitrile having the formula: Cl(CH CN, and the product obtained is reduced by sodium-alcohol or with hydrogen over Raney nickel to give the desired product:
  • a secondary amine is added to an unsaturated nitrile, e.g. methacrylonitrile, and the product hydrogenated to the primary amine: NH,
  • R1 CH 8. The anthraquinone compound having the formula:
  • R and R each represents a member selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, a hydroxyalkyl group having 1 to 4 carbon atoms, a fi-methoxyethyl group and a fl-ethoxyethyl group, n represents a whole number selected from 2, 3 and 4 and wherein taken together also represent a member selected from the group conslstmg of a morpholinyl group and a References Cited in the file of this patent peridyl group.
  • R UNITED ATES PATENTS and R each represents an alkyl group having 1 to 4 car- 7 5 5 Boyd Aug 30, 1955 bon atoms.

Description

, United States Patent l-AMINO-Z-BROMO-4-ARYLAMINOANTHRA- QUIN ONE COMPOUNDS James M. Straley and Ralph R. Giles, Kingsport, Tenu., assignors to Eastman Kodak Company, Rochester, N.Y., a corporation of New Jersey No Drawing. Filed Aug. 28, 1958, Ser. No. 757,680
8 Claims. (Cl. 260-377) This invention relates to new anthraquinone compounds and their application to the art of dyeing or coloring.
It is well known that polyacrylonitrile fibers are ditiicult to dye in deep, fast shades without the use of special dyeing techniques, such as, for example, the use of pressure, carriers or the so-called cuprous ion technique involving the use of acid wool dyes. Each of these methods involves one or more disadvantages. The use of pressure involves the use of pressure equipment which is more expensive than the equipment used where no pressure is involved. The use of carriers involves the expense of providing the carriers. Also, when carriers are employed operations for the recovery of the carrier for reuse are involved and these recovery operations add to the expense of the dyeing operation.
While many variations in the cuprous ion technique have been proposed all sufi'er some disadvantage. One of the chief disadvantages of this method is the fact that it is almost impossible to restrict the amount of copper absorbed to such a low degree that serious browning of the dyed fabric upon exposure to light does not occur.
It is an object of our invention to provide dyes which can be readily applied to the polyacrylonitrile fibers, especially modified polyacrylonitrile fibers, from ordinary dyebaths. That is, the dyes in finely divided condition are intimately dispersed in water and applied directly to the fiber. Another object of our invention is to provide dyes which yield dyeings on polyacrylonitrile textile materials which have excellent fastness to light and washing. A further object of our invention is to provide dies which are capable of dyeing polyacrylonitrile textile materials in deep shades.
The new anthraquinone compounds of our invention by means of which the objects of our invention can be accomplished have the formula:
C\ Br 2 o ooiionnnn l e-@ Rx wherein R and R each represent an alkyl group having 1 to 4 carbon atoms, a hydroxy alkyl group having 1 to 4 carbon atoms, a l3-methoxyethyl group or a fi-ethoxyethyl group, n represents 2, 3 or 4 and wherein taken together also represent a morpholinyl group or a piperidyl group.
Ethylene, trimethylene, propylene, tetramethylene and Z-methyl trimethylene:
2,968,661 Patented Jan. 17, 1961 for example, are illustrative of the alkylene radicals rep resented by C H The new anthraquinone compounds of our invention readily dye polyacrylonitrile textile materials and yield blue dyeings thereon which have excellent fastness to light and washing. They are conveniently applied directly to the polyacrylonitrile textile material from an aqueous dispersion. Deep blue shades can be obtained on polyacrylonitrile textile materials with the new anthraquinone compounds of the invention. Verel and Orlon are illustrative of the polyacrylonitrile materials that can be dyed.
While the anthraquinone compounds of our invention can be prepared by more than one method We prefer to prepare them by condensing the acid chloride of the appropriate 1 amino 2 bromo-4-carboxyanilinoanthraquinone with a primary amine having the formula:
R H:NCnH2nN i I wherein n, R, R and have the meaning previously assigned to them. The acid chloride of the 1-amino-2-bromo-4-carboxyanilinoanthraquinone compound is prepared by known methods.
The following examples illustrate the compounds of our invention and their manner of preparation.
Example 1 One gram of 1-amino-2-bromo-4-o-carboxyanilinoanthraquinone was suspended in 20 cc. of dry chlorobenzene. Two cc. of thionyl chloride were added and the reaction mixture obtained was heated on a steam bath, with stirring, until a clear solution was obtained and no further color change toward the red occurred. The solution thus obtained was cooled to C., diluted with an equal volume of n-hexane and cooled to 20 C. The acid chloride thus prepared was recovered by filtration, washed with n-hexane and sucked dry. The acid chloride product thus obtained was added to 3.5 grams of 3- dimethylaminopropylamine and the resulting mixture was warmed on a steam bath to complete solution. The reaction mixture was then poured into five times its volume of water and the reaction product which precipitated was recovered by filtration and dried at 110 C. 0.95 gram of 1-arnino-2-bromo-4-o-[N-(3-dimethy1aminopropyl)car- 'was obtained as a blue solid which dissolved readily warm dilute HCl. It dyes polyacrylonitrile fibers blue shades having excellent fastness to light and wet processing. I
Example 2 Ten grams of 1-arnino-2-bromo-4-o-carboxyanilinoanthraquinone were suspended in cc. of dry o -dichlorobenzene. 3.4 cc. .of'thionyl chloride were added and the temperature, ofthe reaction mixture. was-gradually raised to 80 C. over a period of about 1.5 hours and held at this temperature for one hour While stirring. Excess thionyl chloride was :removed by passing a stream of dry air through the reaction mixture at 65 70 C. After cooling the reaction mixture to room temperature 2.8 grams of 3edimethylaminopropylarriine and 2.26 grams of anhydroussodium acetate .were added and the reaction mixture was stirred at 70" C.'7S C. for one hour. The reaction mixture was cooled and the product which precipitated was recovered by filtration, washed with n-hexane and then with hot water and dried at 110 C. 11.3 grams of product identical with that prepared in Example 1 were obtained.
Example 3 Example 1 was repeated using 4 grams of Z-dirnethyl- 'aminoethylamine in place of 3-dimethylaminopropylamine. 'l-am'ino -'2 bromo-- 4-o-[N-(2-dimethy'laminoethyl) carboxamido] anilinoanthraquinone was obtained as a blue solid. It dyes polyacrylonitrile textile materials blue shades which have excellent fastness to light and wet processing.
H l-amlno-Z-bromoA-p-(C ONCHqCHz CHiN Exam p [a 4 Example 1 was repeated using 1 gram of l-amino-Z- bromo-4-m-carboxyanilinoanthraquinone and 3.5 grams of 3-dimethyl-aminopropylamine. l-amino-2-bromo-4- m [N (3 dimethylaminopropyl)carboxamido]anilinoanthraquinone was obtained as a blue solid. It dyes polyacrylonitrile textile materials blue shades which have excellent fastness to light and wet processing.
Example '5 Example 1 was .repeated using 1 gram of l-amino-2- bromo-4-p-carboxyanilinoanthraquinone and 3.5 grams of '3-dimethylaminopropy1amine. 1-amino-2-brorno-4-p-[N- (3 dimethylaminoprqpyl) carboxamido] anilinoanthraquinone was obtainedas a blue solid. It dyes polyacrylonitrile textile materials blue shades which have excellent fastness to .light and wet processing.
Example '6 Example 1 was repeated using 4.5 grams of 3-diethylaminopropylamine in place of 3-dimethylaminopropylamine. l-amino-2-bromo-4-o-['N-(3-diethylaminopropyl) H l-amino-Z-bromo--o- C ONCHQCHzCHIN carboxamido]anilinoanthraquinone was obtained as a blue solid. It dyes polyacrylonitrile textile materials blue shades which have excellent "fastness to light and wet processing.
Example7 Example 1 was repeated using 1 gram of 1-amino-2- bromo-4sm-carboxyanilinoanthraquinone and 3 grams of Z-diethylanfinoethylamine. l-amino-Z-bromol-m-[N-.(2- diethylaminoethyl)car.boxarnido] anilinoanthraquinone was obtained as a blue solid. .It dyes polyacrylonitrile textile materials blue shades which have excellent fastness to light and wet processing.
Example 8 Example 1 was repeated using 1 gram of l-amino-Z- bromo-4-p-carboxyanilinoanthraquinone and 4 grams of N-(Z-aminoethyllpiperidine. "l-amino-z-bromol-p-[N- (2-piperidylethyl) carboxamido] anilinoanthraquinone having'th'e formula:
(I? NH2 Example 1 was repeated using 1 gram of 1-amino-2- bromo-4-p-carboxyanilinoanthraquinone and 5 grams of 3-(N-methyl-N-n-butyl)propylamine /CHa (HzNCHzCH2CH2N\ (34H!) )anllinoanthraquinone 4 11 was obtained as a blue solid. It dyes polyacrylonitrile textile materials blue shades which have excellent fastness to light and wet processing.
Example 10 Example 1 was repeated using 6 grams of 3-(di-fl-hydroxyethylamino)propylamine in place of 3-dimethylaminopropylarnine. l-amino-2-bromo-4-o-[N-3-di-phhydroxyethylaminopropyl) carboxamido] anilinoanthraquinone was obtained as a blue solid. It dyes polyacrylonitrile textile materials blue shades which have excellent fastness to light and wet processing.
Example 11 Example 2 'was repeated using 3.3 grams of 3-'('4-1norpholino) propylamine .H2 )H2 0-o in place of 3-dimethylaminopropylamine.
"H2 H2 C-O O anilinoanthraquinone was obtained as a blue solid. It dyes polyacrylonitrile textile materials blue shades which have excellent fastness to light and wet processing.
Example 1 2 Example 4 was repeated using 4.1 grams of 4-diethylamino-n-butylarrn'ne in place of S-dimethylaminopropylamine. 1-amino-2-bromo-4-m-[N (4 diethylamino-nbutyl)carboxamido] anilino-anthraquinone was obtained as a blue solid. It dyes polyacrylonitrile textile materials blue shades which have excellent fastness to light and wet processing.
By the use of an equivalent amount of 4-dimethylamino-n-butylamine in place of 4-diethylamino-n-butylamine, 1-amin0-2-bromo-4-m [N- .(-4-.'dimethylamino-nbutyl)carboxamidoLanilinoanthraquinone is obtained as a blue solid. It dyes polyacrylonitrile textile materials blue shades which have excellent fastness to light and wet processing.
Example 13 was obtained as a blue solid. It dyes polyacrylonitrile textile materials blue shades which have excellent fastness to light and wet processing.
Example 14 Example 2 was repeated using 3.4 grams of 3-(di- 8- methoxyethylamino)propylamine in place of 3-dimethy1- aminopropylamine.
CHzCHlOCHZ H l-amino-2-bromo4-o- O ONCHnCHgCHzN C H: Hz 0 G H;
was obtained as a blue solid. It dyes polyacrylonitrile textile materials blue shades which have excellent fastness 30 to light and wet processing.
Example Example 2 was repeated using 4.6 grams of 3-(di-18- Example 16 16.7 milligrams of the dye compound prepared in Example 1 was dissolved by warming in 5 cos. of ethylene glycol monomethyl ether. 20 ccs. of a 1% aqueous solution of Igepon T (3113 (Or- H 0 ONCH CHzSOaNa) were added and the volume brought to 200 ccs. by the addition of water at 50 C. Five cos. of a aqueous solution of formic acid were added, followed by 5 grams of Verel fabric. The temperature was brought to the boil and held there for 1 hour. The cloth was then rinsed in hot water and allowed to dry. It was dyed an attractive blue shade having excellent wash and light fastness. Similar results are obtained when Orlon 42 fabric is used instead of Verel fabric.
The primary amine compounds having the Formula I used in preparing the new anthraquinone compounds of the invention appear to include new as well as old comjlanilinoanthraquinone pounds. Many of these amines are specifically disclosed in the prior art. Those not specifically disclosed can be prepared by the methods used to prepare the known compounds. The preferred amine 3-dimethylaminopropylamine is an article of commerce.
Three general processes by which primary amines havethoxyethylamino)propylamine in place of S-dimethyling the formula I can be prepared are set forth hereinornomo cm,
was obtained as a blue solid. It dyes polyacrylonitrile textile materials blue shades which have excellent fastmess to light and wet processing.
Other primary amines that can be used to prepare compounds of our invention include, for example Z-di-n-propylaminoethylamine, Z-diisopropylaminoethylaming 2-di-n butylaminoethylamine,
2-( di-fl-hydroxyethylamino) ethylamine, Z-(di-fi-ethoxyethylamino etllylamine,
3-( di-fl-hydroxypropylamino propylamine, 3-(di-fi-hydroxybutylamino) propylamine, 4-(di-5-hydroxyethylamino) butylamine and 4-(4'-morpholino) propylamine. i
The new anthraquinone compounds of our invention can be applied to polyacrylonitrile textile materials from an aqueous dyebath in the same manner that water-insoluble cellulose acetate dyestulfs are commonly applied to cellulose acetate textile materials. Thus they may be directly applied to the polyacrylonitrile textile material undergoing coloration in the form of an aqueous suspension which can be prepared by grinding them to a paste in the presence of a sulfonated oil, soap, sodium lignin sulfonate, or other suitable dispersing agent and dispersing the resulting paste in water. As previously indicated the dyes should be in finely divided condition.
The following example illustrates how the anthraquinone compounds of our invention can be applied to polyacrylonitrile textile materials. As noted hereinbefore the anthraquinone compounds are particularly useful in connection with the dyeing of modified polyacrylonitrile textile materials, such as Verel.
after:
:lanilinoantlnaquinone (1) an amine having the formula:
R1 II is condensed with a chloroalkylnitrile having the formula: Cl(CH CN, and the product obtained is reduced by sodium-alcohol or with hydrogen over Raney nickel to give the desired product:
(2) Potassium phthalimide is condensed with a dibromoalkyl compound having the formula: Br(CH Br to obtain C H (CO) N(CH Br which is treated with II to give which is hydrolyzed with dilute mineral acid to give HzN(CH2) IN the desired product. Method 2 is the well-known Gabriel synthesis.
(3) A secondary amine is added to an unsaturated nitrile, e.g. methacrylonitrile, and the product hydrogenated to the primary amine: NH,
II I R R\ Br NOHzCHCN--- NCHzOHOH NHg 6 R1 CH3 R1 CH3 0113 on; N I H HgNCHgCHCHzN CH3 L H CH3 ONOHzCHaCHzN and CH3 OH; 02115 5. The anthraquinone compound having the formula:
I HzNCHzOHOHgN NH;
for example, can be readily prepared by method 3 by reacting dimethylamine and diethylamine, respectively,
with methacrylonitrile and then hydrogenating the products obtained to their primary amine form. 0
0Hv R J7 H t ONCHZGHZN R, R1 and N \R CH3 i 6. The anthraquinone compound having the formula:
as used herein have the meaning previously assigned to 0 NH:
CHa H ?ONCH2CH2CHEN\ O N H 7. The anthraquinone compound having the formula:
R1 CH: 8. The anthraquinone compound having the formula:
wherein R and R each represents a member selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, a hydroxyalkyl group having 1 to 4 carbon atoms, a fi-methoxyethyl group and a fl-ethoxyethyl group, n represents a whole number selected from 2, 3 and 4 and wherein taken together also represent a member selected from the group conslstmg of a morpholinyl group and a References Cited in the file of this patent peridyl group.
2. The anthraquinone compounds of claim 1 wherein R UNITED ATES PATENTS and R each represents an alkyl group having 1 to 4 car- 7 5 5 Boyd Aug 30, 1955 bon atoms.
3. The anthraquinone compounds of claim 2 wherein FOREIGN PATENTS C H is -CH CH CH 855,541 Germany Nov. 13, 1952 4. The anthraquinone compound having the formula:

Claims (1)

1. THE ANTHRAQUINONE COMPOUNDS HAVING THE FORMULA:
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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3079375A (en) * 1960-09-29 1963-02-26 Eastman Kodak Co Metallizable and metallized azo dyestuffs for acrylonitrile polymers
US3253877A (en) * 1963-05-24 1966-05-31 Eastman Kodak Co Acrylonitrile-vinyl chloride copolymer textile materials dyed with black cationic dyestuffs
US3274198A (en) * 1963-06-14 1966-09-20 Gen Aniline & Film Corp Quaternary anthraquinone dyestuffs
US3501259A (en) * 1958-10-28 1970-03-17 American Cyanamid Co Process for simultaneous coloration and finishing of cellulose fibers and reactive dyes therefor

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE855541C (en) * 1944-08-03 1952-11-13 Bayer Ag Coloring of linear polyamides and polyurethanes
US2716655A (en) * 1954-01-12 1955-08-30 Du Pont Dyes and dye intermediates of the anthraquinone series

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE855541C (en) * 1944-08-03 1952-11-13 Bayer Ag Coloring of linear polyamides and polyurethanes
US2716655A (en) * 1954-01-12 1955-08-30 Du Pont Dyes and dye intermediates of the anthraquinone series

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3501259A (en) * 1958-10-28 1970-03-17 American Cyanamid Co Process for simultaneous coloration and finishing of cellulose fibers and reactive dyes therefor
US3079375A (en) * 1960-09-29 1963-02-26 Eastman Kodak Co Metallizable and metallized azo dyestuffs for acrylonitrile polymers
US3253877A (en) * 1963-05-24 1966-05-31 Eastman Kodak Co Acrylonitrile-vinyl chloride copolymer textile materials dyed with black cationic dyestuffs
US3274198A (en) * 1963-06-14 1966-09-20 Gen Aniline & Film Corp Quaternary anthraquinone dyestuffs

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