DE1203895B - Process for the production of anthraquinone dyes - Google Patents
Process for the production of anthraquinone dyesInfo
- Publication number
- DE1203895B DE1203895B DEC19339A DEC0019339A DE1203895B DE 1203895 B DE1203895 B DE 1203895B DE C19339 A DEC19339 A DE C19339A DE C0019339 A DEC0019339 A DE C0019339A DE 1203895 B DE1203895 B DE 1203895B
- Authority
- DE
- Germany
- Prior art keywords
- oxy
- phenylaminoanthraquinone
- parts
- sulfuric acid
- dyes
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 14
- 239000001000 anthraquinone dye Substances 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 20
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 16
- 239000000975 dye Substances 0.000 claims description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 7
- 239000007858 starting material Substances 0.000 claims description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 4
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 3
- 229920002866 paraformaldehyde Polymers 0.000 claims description 3
- XRIGHGYEGNDPEU-UHFFFAOYSA-N 1-anilinoanthracene-9,10-dione Chemical class C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1NC1=CC=CC=C1 XRIGHGYEGNDPEU-UHFFFAOYSA-N 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000002270 dispersing agent Substances 0.000 claims description 2
- 238000004043 dyeing Methods 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 claims 1
- 238000004040 coloring Methods 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 5
- -1 benzene radical Chemical class 0.000 description 4
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 235000005811 Viola adunca Nutrition 0.000 description 2
- 240000009038 Viola odorata Species 0.000 description 2
- 235000013487 Viola odorata Nutrition 0.000 description 2
- 235000002254 Viola papilionacea Nutrition 0.000 description 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 2
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- 229920004934 Dacron® Polymers 0.000 description 1
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 150000001555 benzenes Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000001351 cycling effect Effects 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 239000004312 hexamethylene tetramine Substances 0.000 description 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 101150032584 oxy-4 gene Proteins 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- 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
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/51—N-substituted amino-hydroxy anthraquinone
- C09B1/514—N-aryl derivatives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
BUNDESREPUBLIK DEUTSCHLANDFEDERAL REPUBLIC OF GERMANY
DEUTSCHESGERMAN
PATENTAMTPATENT OFFICE
AUSLEGESCHRIFTEDITORIAL
Int. CL:Int. CL:
Nummer:
Aktenzeichen:
Anmeldetag:
Auslegetag:Number:
File number:
Registration date:
Display day:
C09bC09b
Deutsche Kl.: 22 b-3/02 German class: 22 b -3/02
1 203 895
C19339IVc/22b
3. Juli 1959
28. Oktober 19651 203 895
C19339IVc / 22b
3rd July 1959
October 28, 1965
Es wurde gefunden, daß man zu wertvollen neuen Anthrachinonfarbstoffen gelangt, wenn man von Nitrogruppen freie l-Oxy-4-arylaminoanthrachinone der FormelIt has been found that valuable new anthraquinone dyes can be obtained from L-oxy-4-arylaminoanthraquinones free of nitro groups the formula
OHOH
Verfahren zur Herstellung von Anthrachinonfarbstoffen Process for the preparation of anthraquinone dyes
O NH-ArylO NH-aryl
worin Aryl einen gegebenenfalls substituierten Benzolrest bedeutet, mit Formaldehyd in 75- bis 9O°/oiger Schwefelsäure bei Temperaturen zwischen 10 und 400C behandelt.wherein aryl means an optionally substituted benzene residue, treated with formaldehyde in 75 to 9O ° / cent sulfuric acid at temperatures between 10 and 40 0 C.
Als Ausgangsstoffe für das vorliegende Verfahren kommen in Betracht insbesondere solche 1-Oxy-4-arylaminoanthrachinone, die als Arylrest einen gegebenenfalls substituierten Benzolrest enthalten. Als allfällige Substituenten kommen beispielsweise Methylgruppen oder vorteilhaft Acylaminogruppen in Betracht, also vorzugsweise Farbstoffe der FormelThe starting materials for the present process are in particular those 1-oxy-4-arylaminoanthraquinones, which contain an optionally substituted benzene radical as the aryl radical. Possible substituents include, for example Methyl groups or, advantageously, acylamino groups are suitable, that is to say preferably dyes of the formula
OHOH
Anmelder:Applicant:
CIBA Aktiengesellschaft, Basel (Schweiz)CIBA Aktiengesellschaft, Basel (Switzerland)
Vertreter:Representative:
Dr.-Ing. Dr. jur. F. Redies,
Dr. rer. nat. B. Redies, Dr. rer. nat. D. Türk
und Dipl.-Ing. Ch. Gille, Patentanwälte,
Opladen, Rennbaumstr. 27Dr.-Ing. Dr. jur. F. Redies,
Dr. rer. nat. B. Redies, Dr. rer. nat. D. Turk
and Dipl.-Ing. Ch. Gille, patent attorneys,
Opladen, Rennbaumstr. 27
Als Erfinder benannt:Named as inventor:
Dr. Paul Grossmann, Binningen (Schweiz)Dr. Paul Grossmann, Binningen (Switzerland)
Beanspruchte Priorität:
Schweiz vom 4. Juli 1958Claimed priority:
Switzerland from July 4, 1958
IIII
O NHO NH
NHCOR2 NHCOR 2
worin R2 für ein Η-Atom oder einen Alkylrest, enthaltend höchstens 11 C-Atome, beispielsweise eine Methyl-, Äthyl-, Propyl-, Oktyl-, Undecyl- oder Isopropylgruppe, steht.where R2 stands for a Η atom or an alkyl radical, containing at most 11 carbon atoms, for example a methyl, ethyl, propyl, octyl, undecyl or Isopropyl group.
Bei der Durchführung des erfindungsgemäßen Verfahrens erhält man im allgemeinen schon mit 1 Mol Formaldehyd pro Mol l.-Oxy-4-arylaminoanthrachinon sehr gute Resultate. In gewissen Fällen kann jedoch die Verwendung eines Überschusses an Formaldehyd, beispielsweise 10 Mol und 1 Mol der Anthrachinonverbindung, von Vorteil sein. Der Formaldehyd kann als konzentrierte wäßrige Lösung oder in polymerer Form, beispielsweise als Paraformaldehyd, zugegeben werden. An Stelle von Formaldehyd kann man auch formaldehydabgebende Mittel, beispielsweise Hexamethylentetramin, verwenden. When carrying out the process according to the invention, one generally already obtains with 1 mole of formaldehyde per mole of l.-oxy-4-arylaminoanthraquinone very good results. In certain cases, however, you can use an excess of formaldehyde, for example 10 mol and 1 mol of the anthraquinone compound, of advantage be. The formaldehyde can be used as a concentrated aqueous solution or in polymeric form, for example as Paraformaldehyde, can be added. Instead of formaldehyde, formaldehyde-releasing agents can also be used Use agents such as hexamethylenetetramine.
Die Umsetzung wird bei 10 bis 400C, Vorzugsweise bei 10 bis 300C, in 75- bis 90°/oiger, vorzugsweise in 80- bis 85%iger Schwefelsäure durchgeführt.The reaction is o acetic, preferably performed at 10 to 40 0 C, preferably at 10 to 30 0 C, in 75 to 90 ° / in 80 to 85% sulfuric acid.
Die Umsetzungsdauer hängt von der Konzentration der Schwefelsäure und der Temperatur ab.The reaction time depends on the concentration of sulfuric acid and the temperature.
Die Aufarbeitung erfolgt zweckmäßig durch Aus-1 gießen des Umsetzungsgemisches auf ein Wasser-Eis-Gemisch, wobei das Verfahrensprodukt ausfallt und durch Filtration abgetrennt werden kann. Zweckmäßig wird der Farbstoff mit Wasser so lange gewaschen, bis er frei von Schwefelsäure ist.The work-up is advantageously carried out by cycling 1 Pour the reaction mixture on a water-ice mixture, wherein the process product precipitates and can be separated by filtration. The dye is expediently washed with water until it is free from sulfuric acid.
Über die Art der Umsetzung kann vorläufig noch nichts Bestimmtes ausgesagt werden, man nimmt an, daß Oxymethylgruppen ins Molekül des Ausgangsstoffes eingeführt werden. Die erhaltenen Farbstoffe zeichnen sich gegenüber den Ausgangsstoffen durch ein bedeutend besseres Ziehvermögen für Fasermateräal aus Celluloseestern, beispielsweise Celluloseacetat- oder Cellulosetriacetat, oder durch bessere Sublimierechtheit auf Polyäthylenterephthalatfasern aus. Es werden auf diesen Fasern wertvolle rotblaue bis grünblaue Färbungen erhalten.For the time being, nothing definite can be said about the type of implementation, it is assumed that that oxymethyl groups are introduced into the molecule of the starting material. The dyes obtained are characterized by a significantly better drawability for fiber materials compared to the starting materials from cellulose esters, for example cellulose acetate or cellulose triacetate, or by better ones Sublimation fastness on polyethylene terephthalate fibers. Valuable red-blue ones appear on these fibers to green-blue colorations obtained.
In vielen Fällen werden mit Gemischen von verfahrensgemäß erhaltenen Farbstoffen stärkere Färbungen als mit den Einzelfarbstoffen erhalten, insbesondere mit Gemischen von Farbstoffen, die sich durch den Substituenten im Benzolrest unterscheiden.In many cases, mixtures of dyes obtained according to the process produce stronger colors than obtained with the individual dyes, especially with mixtures of dyes that are differ by the substituent in the benzene residue.
509 719/314509 719/314
Gegenüber dem gemäß Beispiel 3 der USA.-Patentschrift 2 353 108 erhältlichen l-Oxy-4-(m-oxymethylphenyl)-aminoanthrachinon zeigen die erfindungsgemäß erhältlichen Farbstoffe den Vorzug, auf Acetatseide Färbungen von besserer Abgasechtheit zu ergeben.Compared to the 1-oxy-4- (m-oxymethylphenyl) -aminoanthraquinone obtainable according to Example 3 of US Pat. No. 2,353,108 the dyes obtainable according to the invention show the advantage of dyeing on acetate silk with better exhaust gas fastness to surrender.
In den nachfolgenden Beispielen bedeuten die Teile, sofern nichts anderes angegeben wird, Gewichtsteile, die Prozente Gewichtsprozente, und die Temperaturen sind in Celsiusgraden angegeben.In the following examples, unless otherwise stated, the parts mean parts by weight, the percentages by weight and the temperatures are given in degrees Celsius.
6 Teile Paraformaldehyd werden in 85 Teile 85%ige Schwefelsäure bei 203 eingetragen. Nach erfolgter Lösung trägt man 9 Teile l-Oxy-4-phenylamino- '5 anthrachinon ein und verrührt etwa 4 Stunden bei 20 bis 25°. Dann trägt man auf Eis aus, filtriert, wäscht neutral und vermahlt mit einem geeigneten Dispergiermittel.6 parts of paraformaldehyde are introduced into 85 parts of 85% strength sulfuric acid at 20 3 . When the solution is complete, 9 parts of 1-oxy-4-phenylamino- '5 anthraquinone are added and the mixture is stirred for about 4 hours at 20 to 25 °. Then it is poured onto ice, filtered, washed neutral and ground with a suitable dispersant.
Der Farbstoff färbt Polyäthylenglykolterephthalat im Gegensatz zum Ausgangsmaterial in sublimierechten rotblauen Tönen.In contrast to the starting material, the dye colors polyethylene glycol terephthalate in sublimation properties red-blue tones.
Man verfährt nach Beispiel 1, verwendet aber 9 Teile l-Oxy-4-(p-acetylamino)-phenylaminoanthrachinon. Der Farbstoff färbt Acetatseide in blauvioletten und Dacron in rotblauen Tönen. The procedure of Example 1 is followed, but 9 parts of l-oxy-4- (p-acetylamino) phenylaminoanthraquinone are used. The dye dyes acetate silk in blue-violet and dacron in red-blue tones.
Verwendet man statt l-Oxy-4-(p-acetylamino)-phenylaminoanthrachinon das l-Oxy-4-(p-formylamino)-phenylaminoanthrachinon, so erhält man auf Acetatseide ebenfalls kräftige blauviolette Färbungen. Used instead of l-oxy-4- (p-acetylamino) phenylaminoanthraquinone the l-oxy-4- (p-formylamino) phenylaminoanthraquinone is obtained Strong blue-violet colorations on acetate silk as well.
Man verfährt nach Beispiel 1, verwendet aber 9 Teile 1 - Oxy - 4 - (ρ - butyrylamino) - phenylaminoanthrachinon. Der Farbstoff färbt Acetatseide und Polyäthylenglykolterephthalat in rotstichigblauen Tönen.The procedure of Example 1 is followed, but 9 parts of 1 - oxy - 4 - (ρ - butyrylamino) phenylaminoanthraquinone are used. The dye dyes acetate silk and polyethylene glycol terephthalate in reddish blue Tones.
Ähnliche Farbtöne erhält man mit 1 - Oxy-4-(p-acrylylamino)- und I-Oxy-4-(p-propionylamino)-phenylaminoanthrachinon, während man mit den Caprylyl- und Laurylderivaten etwas weniger rotstichige Farbtöne erhält.Similar shades are obtained with 1 - Oxy-4- (p-acrylylamino) - and I-oxy-4- (p-propionylamino) -phenylaminoanthraquinone, while with the caprylyl and lauryl derivatives, slightly less reddish tones are obtained.
In 17 Teile Schwefelsäure 85% und 34 Teile Schwefelsäure 100% gibt man unter 20° 10 Teile einer 40%igen wäßrigen Formaldehydlösung und trägt dann 6 Teile l-Oxy^-phenylaminoanthrachinon ein. Man verrührt 4 Stunden bei 20 bis 25°, trennt ab und dispergiert den Farbstoff, wie im Beispiel 4 beschrieben. Man erhält gegenüber dem Ausgangsprodukt eine erhebliche Steigerung des Ziehvermögens auf Acetatseide.In 17 parts of 85% sulfuric acid and 34 parts of 100% sulfuric acid, 10 parts are added below 20 ° a 40% aqueous formaldehyde solution and then carries 6 parts of l-oxy ^ -phenylaminoanthraquinone a. The mixture is stirred for 4 hours at 20 to 25 °, and the dye is separated off and dispersed, as in Example 4 described. A considerable increase in the drawability is obtained compared with the starting product on acetate silk.
Claims (6)
Belgische Patentschrift Nr. 552 173;
USA.-Patentschrift Nr. 2 353 108.Considered publications:
Belgian Patent No. 552 173;
U.S. Patent No. 2,353,108.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH6138158A CH374789A (en) | 1958-07-04 | 1958-07-04 | Process for the production of new anthraquinone dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1203895B true DE1203895B (en) | 1965-10-28 |
Family
ID=4523594
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC19339A Pending DE1203895B (en) | 1958-07-04 | 1959-07-03 | Process for the production of anthraquinone dyes |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE580316A (en) |
| CH (1) | CH374789A (en) |
| DE (1) | DE1203895B (en) |
| ES (1) | ES250507A1 (en) |
| FR (1) | FR1228645A (en) |
| GB (1) | GB887876A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1271856B (en) * | 1963-02-21 | 1968-07-04 | Bayer Ag | Process for the production of organic pigment dyes |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE552173A (en) * | 1955-10-28 | |||
| US2353108A (en) * | 1940-10-24 | 1944-07-04 | Du Pont | Anthraquinone dyestuffs |
-
0
- BE BE580316D patent/BE580316A/xx unknown
-
1958
- 1958-07-04 CH CH6138158A patent/CH374789A/en unknown
-
1959
- 1959-06-19 FR FR798034A patent/FR1228645A/en not_active Expired
- 1959-07-02 GB GB2277759A patent/GB887876A/en not_active Expired
- 1959-07-03 ES ES0250507A patent/ES250507A1/en not_active Expired
- 1959-07-03 DE DEC19339A patent/DE1203895B/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2353108A (en) * | 1940-10-24 | 1944-07-04 | Du Pont | Anthraquinone dyestuffs |
| BE552173A (en) * | 1955-10-28 |
Also Published As
| Publication number | Publication date |
|---|---|
| GB887876A (en) | 1962-01-24 |
| FR1228645A (en) | 1960-08-31 |
| ES250507A1 (en) | 1960-01-16 |
| BE580316A (en) | |
| CH374789A (en) | 1964-01-31 |
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