DE1047965B - Process for the production of water-insoluble azo dyes - Google Patents
Process for the production of water-insoluble azo dyesInfo
- Publication number
- DE1047965B DE1047965B DEF20583A DEF0020583A DE1047965B DE 1047965 B DE1047965 B DE 1047965B DE F20583 A DEF20583 A DE F20583A DE F0020583 A DEF0020583 A DE F0020583A DE 1047965 B DE1047965 B DE 1047965B
- Authority
- DE
- Germany
- Prior art keywords
- water
- azo dyes
- production
- insoluble azo
- amino
- 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 9
- 239000000987 azo dye Substances 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 239000000835 fiber Substances 0.000 claims description 5
- PUDDYSBKCDKATP-UHFFFAOYSA-N methyl 2-amino-5-fluorobenzoate Chemical compound COC(=O)C1=CC(F)=CC=C1N PUDDYSBKCDKATP-UHFFFAOYSA-N 0.000 claims description 5
- 238000004040 coloring Methods 0.000 claims description 3
- OCISOSJGBCQHHN-UHFFFAOYSA-N 3-hydroxynaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC(O)=CC2=C1 OCISOSJGBCQHHN-UHFFFAOYSA-N 0.000 claims description 2
- 230000008878 coupling Effects 0.000 claims description 2
- 238000010168 coupling process Methods 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- 150000001989 diazonium salts Chemical class 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 5
- -1 aryl amides Chemical class 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 238000004043 dyeing Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KHJWSKNOMFJTDN-UHFFFAOYSA-N 2-[2-[bis(carboxymethyl)amino]ethyl-(carboxymethyl)amino]acetic acid;sodium Chemical compound [Na].OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KHJWSKNOMFJTDN-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 239000011928 denatured alcohol Substances 0.000 description 2
- 150000008049 diazo compounds Chemical class 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002964 rayon Substances 0.000 description 2
- 239000004627 regenerated cellulose Substances 0.000 description 2
- 239000001488 sodium phosphate Substances 0.000 description 2
- JRTYPYSADXRJBQ-UHFFFAOYSA-N 1-fluoro-3-(trichloromethyl)benzene Chemical compound FC1=CC=CC(C(Cl)(Cl)Cl)=C1 JRTYPYSADXRJBQ-UHFFFAOYSA-N 0.000 description 1
- SYVNVEGIRVXRQH-UHFFFAOYSA-N 3-fluorobenzoyl chloride Chemical compound FC1=CC=CC(C(Cl)=O)=C1 SYVNVEGIRVXRQH-UHFFFAOYSA-N 0.000 description 1
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- 240000002129 Malva sylvestris Species 0.000 description 1
- 235000006770 Malva sylvestris Nutrition 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- SMEGJBVQLJJKKX-HOTMZDKISA-N [(2R,3S,4S,5R,6R)-5-acetyloxy-3,4,6-trihydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC(=O)C)O)O SMEGJBVQLJJKKX-HOTMZDKISA-N 0.000 description 1
- 229940081735 acetylcellulose Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- 235000013351 cheese Nutrition 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 235000019800 disodium phosphate Nutrition 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- XWWBMLMEVRIPSX-UHFFFAOYSA-N ethyl 2-amino-5-chlorobenzoate Chemical compound CCOC(=O)C1=CC(Cl)=CC=C1N XWWBMLMEVRIPSX-UHFFFAOYSA-N 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- YXZNVLYXBIIIOB-UHFFFAOYSA-N methyl 3-fluorobenzoate Chemical compound COC(=O)C1=CC=CC(F)=C1 YXZNVLYXBIIIOB-UHFFFAOYSA-N 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000017854 proteolysis Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 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
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D17/00—Pigment pastes, e.g. for mixing in paints
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
- C09B29/18—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides
- C09B29/20—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides of the naphthalene series
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/02—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using azo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Textile Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung von wasserunlöslichen Azofarbstoffen Es wurde gefunden, daß man zu wertvollen wasserunlöslichen Azofarbstoffen gelangt, wenn man die Diazoniumverbindung aus 1-Amino-4-fluorbenzol-2-carbonsäuremethylester mit Arylamiden der 2,3-Oxynaphthoesäure in Substanz, auf der Faser oder auf einer anderen Grundlage kuppelt.Process for the production of water-insoluble azo dyes Es it was found that valuable water-insoluble azo dyes can be obtained, when you get the diazonium compound from 1-amino-4-fluorobenzene-2-carboxylic acid methyl ester with aryl amides of 2,3-oxynaphthoic acid in substance, on the fiber or on a other basis couples.
Mit den neuen Farbstoffen erhält man auf der pflanzlichen Faser, einschließlich solcher aus regenerierter Cellulose, nach den bekannten Färbeverfahren orangefarbige bis scharlachrote Färbungen, die sich bei sehr guten Lichtechtheiten vielfach durch gute Chlor- und Superoxydechtheiten auszeichnen. Auf synthetischen Fasern, wie Acetylcellulose-, Polyamid- oder Polyäthylenterephthalatfasern, erhält man ebenfalls Färbungen von wertvollen Echtheitseigenschaften.With the new dyes one gets on the vegetable fiber, including those made from regenerated cellulose, orange-colored according to the known dyeing processes to scarlet colorings, which show very good lightfastness in many cases have good chlorine and superoxide fastness properties. On synthetic fibers, such as acetyl cellulose, Polyamide or polyethylene terephthalate fibers are also obtained by dyeing valuable authenticity properties.
Die Farbstoffe lassen sich auch in Substanz oder auf einem Substrat herstellen und können zum Färben von hochmolekularen plastischen Massen oder für die Zubereitung von Farblacken verwendet werden. Sie können außerdem zur Herstellung gefärbter Filme in Massen aus Celluloseestern oder -äthern eingebracht oder im Pigmentdruckverfahren auf Textilien aufgebracht werden. Die Diazokomponente kann bei dem erfindungsgemäßen Verfahren gegebenenfalls als stabilisierte Diazoverbindung, beispielsweise als Diazoniumchlorid-Chlorzinkdoppelsalz, Diazoaminoverbindung oder als Antidiazotat nach einem der üblichen Färbe- oder Druckverfahren verwendet werden.The dyes can also be used in bulk or on a substrate manufacture and can be used for coloring high molecular weight plastic masses or for the preparation of colored lakes can be used. You can also use it to manufacture colored films introduced in bulk from cellulose esters or ethers or in the pigment printing process can be applied to textiles. The diazo component can be used in the inventive Process optionally as a stabilized diazo compound, for example as a diazonium chloride-chlorozinc double salt, Diazoamino compound or as an antidiazotate by one of the customary dyeing or printing processes be used.
Die Herstellung des als Diazokomponente verwendeten 1-Amino-4-fluorbenzol-2-carbonsäuremethylesters kann nach bekannten Verfahren erfolgen, beispielsweise durch Veresterung des aus 3-Fluorbenzotrichlorid erhaltenen 3-Fluorbenzoylchlorids mit Methylalkohol, Nitrierung des 3-Fluorbenzoesäuremethylesters und Reduktion zur Aminoverbindung.The preparation of the 1-amino-4-fluorobenzene-2-carboxylic acid methyl ester used as the diazo component can be carried out by known methods, for example by esterification of the from 3-fluorobenzotrichloride obtained 3-fluorobenzoyl chloride with methyl alcohol, nitration of 3-fluorobenzoic acid methyl ester and reduction to the amino compound.
Gegenüber den aus der deutschen Patentschrift 942325 bekannten wasserunlöslichen Azofarbstoffen aus diazotiertem 1-Amino-4-chlorbenzol-2-carbonsäureäthylester und 2,3-Oxynaphthoesäurearylamiden zeichnen sich die neuen Farbstoffe durch eine bessere Licht-, Chlor-, Superoxyd- und Bügelechtheit aus.Compared to the water-insoluble ones known from German patent 942325 Azo dyes from diazotized 1-amino-4-chlorobenzene-2-carboxylic acid ethyl ester and 2,3-Oxynaphthoesäurearylamiden the new dyes are characterized by better Fastness to light, chlorine, superoxide and iron.
Beispiel 1 100 kg Baumwollgarn auf Kreuzspulen, das gut vorgereinigt, gespült und entwässert ist, werden 30 Minuten bei 35 bis 40° C in dem nachstehenden Bad behandelt: 2 kg 1-(2',3'-Oxynaphthoylamino)-2-methoxy-4-chlor-5-methylbenzol weiden mit 31 denaturiertem Alkohol angeteigt und unter Rühren in 11 Natronlauge von 38'B6 und 41 Wasser von 40°C gelöst. Nach Zugabe von 1 1 Formaldehydlösung (33°,`g) wird die so erhaltene Lösung nach etwa lO Minuten in ein Bad eingerührt, das in 10001 Wasser 51 eines Kondensationsproduktes aus höhermolekularen Fettsäuren und Eiweißabbauprodukten sowie 101 Natronlauge von 38° B6 enthält.Example 1 100 kg of cotton yarn on cheeses, which has been thoroughly pre-cleaned, rinsed and drained, are treated for 30 minutes at 35 to 40 ° C in the following bath: 2 kg of 1- (2 ', 3'-oxynaphthoylamino) -2-methoxy- 4-chloro-5-methylbenzene is made into a paste with 31 denatured alcohol and dissolved in 11 sodium hydroxide solution at 38 ° C and 41 ° C water at 40 ° C. while stirring. After adding 1 liter of formaldehyde solution (33 °, `g), the resulting solution is stirred, after about 10 minutes, into a bath which contains, in 10001 of water, 51 of a condensation product of higher molecular weight fatty acids and protein degradation products, as well as 101 sodium hydroxide solution of 38 ° B6.
Dann wird auf einen Flottengehalt von etwa 100 0/0 abgesaugt, mit einer Lösung von 30 kg Natriumchlorid und 21 Natronlauge von 38° B6 in 10001 kaltem Wasser zwischengespült, wieder abgesaugt und 30 Minuten bei 10 bis 15° C mit einer Diazolösung entwickelt, die in 10001 Wasser die Diazoverbindung aus 1,69 kg 1-Amino-4-fluorbenzol-2-carbonsäuremethylester, 10,5 kg Mononatriumphosphat, 112 kg Dinatriumphosphat und 0,51 eines Einwirkungsproduktes von etwa 20 12o1 Äthylenoxyd auf 1 DZol eines Fettalkohols enthält.Then it is sucked off to a liquor content of about 100 0/0, rinsed with a solution of 30 kg sodium chloride and 21 sodium hydroxide solution of 38 ° B6 in 10001 cold water, sucked off again and developed for 30 minutes at 10 to 15 ° C with a diazo solution, which in 10001 of water contains the diazo compound of 1.69 kg of 1-amino-4-fluorobenzene-2-carboxylic acid methyl ester, 10.5 kg of monosodium phosphate, 112 kg of disodium phosphate and 0.51 of an action product of about 20121 ethylene oxide to 1 double of a fatty alcohol.
Anschließend wird mit 3 ccm Salzsäure von 20° Be im Liter Wasser gespült, zunächst 20 Minuten bei 60° C mit 1 g äthylendiamintetraessigsaurem Natrium und 1 g eines Einwirkungsproduktes von etwa 10 Mol Äthylenoxyd auf 1 Mol eines Alkylphenols im Liter Wasser, dann 20 Minuten. bei 100° C mit 1 g äthylendiamintetraessigsaurem Natrium und 1 g eines Kondensationsproduktes aus einer Aminoalkylsulfonsäure und einer höhermolekularen Fettsäure im Liter Wasser nachbehandelt, gespült und getrocknet.Then it is rinsed with 3 ccm hydrochloric acid of 20 ° Be in the liter of water, first 20 minutes at 60 ° C with 1 g of ethylenediaminetetraacetic acid sodium and 1 g of an action product of about 10 moles of ethylene oxide to 1 mole of an alkylphenol in a liter of water, then 20 minutes. at 100 ° C with 1 g of ethylenediaminetetraacetic acid Sodium and 1 g of a condensation product of an aminoalkylsulfonic acid and a higher molecular weight Fatty acid post-treated per liter of water, rinsed and dried.
Man erhält ein volles Scharlach von guten Echtheitseigenschaften. Dieselbe Färbung kann auch auf regenerierten Cellulosefasern, wie beispielsweise Reyon oder Zellwolle, nach den bei diesen Fasern üblichen Verfahren erhalten werden.A full scarlet with good fastness properties is obtained. The same coloration can also be used on regenerated cellulose fibers, such as Rayon or rayon, can be obtained by the methods customary for these fibers.
Beispiel 2 16,9 kg 1-Amino-4-fluorbenzol-2-carbonsäuremethylester werden in der üblichen Weise diazotiert. Die mit Natriumacetat auf Kongoneutralität abgestumpfte Diazolösung wird in eine durch Lösen in denaturiertem Alkohol und verdünnter Natronlauge und Ausfällen mit Essigsäure erhaltene Suspension von 35,7 kg 1-(2',3'-Oxynaphthoylamino)-2,5-dimethoxy-4-chlorbenzol eingerührt. Der nach beendeter Kupplung erhaltene Farbstoff wird abfiltriert, gut ausgewaschen und getrocknet. Er stellt ein orangefarbiges Pulver dar.Example 2 16.9 kg of 1-amino-4-fluorobenzene-2-carboxylic acid methyl ester are diazotized in the usual way. Those with sodium acetate on Congo neutrality Blunted diazo solution is converted into one by dissolving in denatured alcohol and diluting it Sodium hydroxide solution and precipitation with acetic acid obtained suspension of 35.7 kg of 1- (2 ', 3'-oxynaphthoylamino) -2,5-dimethoxy-4-chlorobenzene stirred in. The dye obtained after the coupling has ended is filtered off, good washed out and dried. It is an orange powder.
Die folgende Tabelle enthält noch eine Anzahl von weiteren unter Verwendung
derselben Diazokomponente erhältlichen Azofarbstoffen sowie die Farbtöne der Baumwollfärbungen,
die ebenfalls gute Echtheitseigenschaften besitzen.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF20583A DE1047965B (en) | 1956-06-20 | 1956-06-20 | Process for the production of water-insoluble azo dyes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF20583A DE1047965B (en) | 1956-06-20 | 1956-06-20 | Process for the production of water-insoluble azo dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1047965B true DE1047965B (en) | 1958-12-31 |
Family
ID=7089733
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF20583A Pending DE1047965B (en) | 1956-06-20 | 1956-06-20 | Process for the production of water-insoluble azo dyes |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1047965B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3321458A (en) * | 1961-12-29 | 1967-05-23 | Hoechst Ag | Water-insoluble monoazo-dyestuffs |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE942325C (en) * | 1952-06-27 | 1956-05-03 | Hoechst Ag | Process for the production of dye-fast dyeings on acetyl cellulose and linear polyamides or polyurethanes |
-
1956
- 1956-06-20 DE DEF20583A patent/DE1047965B/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE942325C (en) * | 1952-06-27 | 1956-05-03 | Hoechst Ag | Process for the production of dye-fast dyeings on acetyl cellulose and linear polyamides or polyurethanes |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3321458A (en) * | 1961-12-29 | 1967-05-23 | Hoechst Ag | Water-insoluble monoazo-dyestuffs |
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