DE2847916A1 - REACTIVE DYES - Google Patents
REACTIVE DYESInfo
- Publication number
- DE2847916A1 DE2847916A1 DE19782847916 DE2847916A DE2847916A1 DE 2847916 A1 DE2847916 A1 DE 2847916A1 DE 19782847916 DE19782847916 DE 19782847916 DE 2847916 A DE2847916 A DE 2847916A DE 2847916 A1 DE2847916 A1 DE 2847916A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- amino
- sulfonic acid
- sul
- component
- 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.)
- Granted
Links
- 239000000985 reactive dye Substances 0.000 title description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 238000004043 dyeing Methods 0.000 claims description 3
- -1 hydroxysulfonyl phenyl Chemical group 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical group COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 239000004952 Polyamide Substances 0.000 claims 1
- NSHIYIMHYBAIEY-UHFFFAOYSA-N ethyl hypochlorite Chemical compound CCOCl NSHIYIMHYBAIEY-UHFFFAOYSA-N 0.000 claims 1
- 239000010985 leather Substances 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 229920002647 polyamide Polymers 0.000 claims 1
- 239000004753 textile Substances 0.000 claims 1
- 230000008878 coupling Effects 0.000 description 18
- 238000010168 coupling process Methods 0.000 description 18
- 238000005859 coupling reaction Methods 0.000 description 18
- 239000002253 acid Substances 0.000 description 16
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 15
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 15
- 150000001412 amines Chemical class 0.000 description 12
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 11
- 239000000975 dye Substances 0.000 description 11
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- VOWZNBNDMFLQGM-UHFFFAOYSA-N 2,5-dimethylaniline Chemical compound CC1=CC=C(C)C(N)=C1 VOWZNBNDMFLQGM-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- GFPQSWFFPRQEHH-UHFFFAOYSA-N 7-aminonaphthalene-1,3,6-trisulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C(N)=CC2=C1S(O)(=O)=O GFPQSWFFPRQEHH-UHFFFAOYSA-N 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 150000003918 triazines Chemical class 0.000 description 3
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 2
- VAMXMNNIEUEQDV-UHFFFAOYSA-N Methyl anthranilate Natural products COC(=O)C1=CC=CC=C1N VAMXMNNIEUEQDV-UHFFFAOYSA-N 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ULHFFAFDSSHFDA-UHFFFAOYSA-N 1-amino-2-ethoxybenzene Chemical compound CCOC1=CC=CC=C1N ULHFFAFDSSHFDA-UHFFFAOYSA-N 0.000 description 1
- KQCMTOWTPBNWDB-UHFFFAOYSA-N 2,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C=C1Cl KQCMTOWTPBNWDB-UHFFFAOYSA-N 0.000 description 1
- GEQNZVKIDIPGCO-UHFFFAOYSA-N 2,4-dimethoxyaniline Chemical compound COC1=CC=C(N)C(OC)=C1 GEQNZVKIDIPGCO-UHFFFAOYSA-N 0.000 description 1
- ZCGVPUAAMCMLTM-UHFFFAOYSA-N 2-amino-5-chlorobenzenesulfonic acid Chemical compound NC1=CC=C(Cl)C=C1S(O)(=O)=O ZCGVPUAAMCMLTM-UHFFFAOYSA-N 0.000 description 1
- KZKGEEGADAWJFS-UHFFFAOYSA-N 2-amino-5-methoxybenzenesulfonic acid Chemical compound COC1=CC=C(N)C(S(O)(=O)=O)=C1 KZKGEEGADAWJFS-UHFFFAOYSA-N 0.000 description 1
- ZMCHBSMFKQYNKA-UHFFFAOYSA-N 2-aminobenzenesulfonic acid Chemical compound NC1=CC=CC=C1S(O)(=O)=O ZMCHBSMFKQYNKA-UHFFFAOYSA-N 0.000 description 1
- ZZKWWRXVSXCBIU-UHFFFAOYSA-N 2-chloro-5-methylbenzenesulfonic acid Chemical compound CC1=CC=C(Cl)C(S(O)(=O)=O)=C1 ZZKWWRXVSXCBIU-UHFFFAOYSA-N 0.000 description 1
- MNURPFVONZPVLA-UHFFFAOYSA-N 2-chlorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1Cl MNURPFVONZPVLA-UHFFFAOYSA-N 0.000 description 1
- AJHPGXZOIAYYDW-UHFFFAOYSA-N 3-(2-cyanophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound CC(C)(C)OC(=O)NC(C(O)=O)CC1=CC=CC=C1C#N AJHPGXZOIAYYDW-UHFFFAOYSA-N 0.000 description 1
- XRDCAKRYIFMDMC-UHFFFAOYSA-N 3-(methylamino)benzenesulfonic acid Chemical compound CNC1=CC=CC(S(O)(=O)=O)=C1 XRDCAKRYIFMDMC-UHFFFAOYSA-N 0.000 description 1
- XJQRCFRVWZHIPN-UHFFFAOYSA-N 3-amino-4-chlorobenzenesulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC=C1Cl XJQRCFRVWZHIPN-UHFFFAOYSA-N 0.000 description 1
- JPVKCHIPRSQDKL-UHFFFAOYSA-N 3-aminobenzenesulfonamide Chemical compound NC1=CC=CC(S(N)(=O)=O)=C1 JPVKCHIPRSQDKL-UHFFFAOYSA-N 0.000 description 1
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 description 1
- WFGYSQDPURFIFL-UHFFFAOYSA-N 3-chloro-n-methylaniline Chemical compound CNC1=CC=CC(Cl)=C1 WFGYSQDPURFIFL-UHFFFAOYSA-N 0.000 description 1
- PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 description 1
- ZDIRCGKEOWZBIM-UHFFFAOYSA-N 4-amino-2-methylbenzenesulfonic acid Chemical compound CC1=CC(N)=CC=C1S(O)(=O)=O ZDIRCGKEOWZBIM-UHFFFAOYSA-N 0.000 description 1
- YBAZINRZQSAIAY-UHFFFAOYSA-N 4-aminobenzonitrile Chemical compound NC1=CC=C(C#N)C=C1 YBAZINRZQSAIAY-UHFFFAOYSA-N 0.000 description 1
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 1
- VPXCXBHLKDPWQV-UHFFFAOYSA-N 5-amino-2-chlorobenzenesulfonic acid Chemical compound NC1=CC=C(Cl)C(S(O)(=O)=O)=C1 VPXCXBHLKDPWQV-UHFFFAOYSA-N 0.000 description 1
- JXZGTFLJFKLVAX-UHFFFAOYSA-N 5-amino-2-methoxybenzenesulfonic acid Chemical compound COC1=CC=C(N)C=C1S(O)(=O)=O JXZGTFLJFKLVAX-UHFFFAOYSA-N 0.000 description 1
- UWPJYQYRSWYIGZ-UHFFFAOYSA-N 5-aminonaphthalene-2-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2C(N)=CC=CC2=C1 UWPJYQYRSWYIGZ-UHFFFAOYSA-N 0.000 description 1
- WBSMIPLNPSCJFS-UHFFFAOYSA-N 5-chloro-2-methoxyaniline Chemical compound COC1=CC=C(Cl)C=C1N WBSMIPLNPSCJFS-UHFFFAOYSA-N 0.000 description 1
- RJSYPKWVIJGNLO-UHFFFAOYSA-N CCOClOC Chemical compound CCOClOC RJSYPKWVIJGNLO-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- BZORFPDSXLZWJF-UHFFFAOYSA-N N,N-dimethyl-1,4-phenylenediamine Chemical compound CN(C)C1=CC=C(N)C=C1 BZORFPDSXLZWJF-UHFFFAOYSA-N 0.000 description 1
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-ethyl-N-phenylamine Natural products CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 1
- 108010013381 Porins Proteins 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000005521 carbonamide group Chemical group 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 238000010016 exhaust dyeing Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- BAVYZALUXZFZLV-UHFFFAOYSA-N mono-methylamine Natural products NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 1
- GUAWMXYQZKVRCW-UHFFFAOYSA-N n,2-dimethylaniline Chemical compound CNC1=CC=CC=C1C GUAWMXYQZKVRCW-UHFFFAOYSA-N 0.000 description 1
- DADSZOFTIIETSV-UHFFFAOYSA-N n,n-dichloroaniline Chemical compound ClN(Cl)C1=CC=CC=C1 DADSZOFTIIETSV-UHFFFAOYSA-N 0.000 description 1
- PEMGGJDINLGTON-UHFFFAOYSA-N n-(3-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(N)=C1 PEMGGJDINLGTON-UHFFFAOYSA-N 0.000 description 1
- NSTOKAMMRZTATB-UHFFFAOYSA-N n-butyl-2-methylaniline Chemical compound CCCCNC1=CC=CC=C1C NSTOKAMMRZTATB-UHFFFAOYSA-N 0.000 description 1
- VSHTWPWTCXQLQN-UHFFFAOYSA-N n-butylaniline Chemical compound CCCCNC1=CC=CC=C1 VSHTWPWTCXQLQN-UHFFFAOYSA-N 0.000 description 1
- MWOUGPLLVVEUMM-UHFFFAOYSA-N n-ethyl-2-methylaniline Chemical compound CCNC1=CC=CC=C1C MWOUGPLLVVEUMM-UHFFFAOYSA-N 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- WXWCDTXEKCVRRO-UHFFFAOYSA-N para-Cresidine Chemical compound COC1=CC=C(C)C=C1N WXWCDTXEKCVRRO-UHFFFAOYSA-N 0.000 description 1
- 102000007739 porin activity proteins Human genes 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- RCTGMCJBQGBLKT-PAMTUDGESA-N scarlet red Chemical compound CC1=CC=CC=C1\N=N\C(C=C1C)=CC=C1\N=N\C1=C(O)C=CC2=CC=CC=C12 RCTGMCJBQGBLKT-PAMTUDGESA-N 0.000 description 1
- 229960005369 scarlet red Drugs 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- 150000004992 toluidines Chemical class 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
- C09B62/08—Azo dyes
- C09B62/085—Monoazo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Cosmetics (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Description
Die Erfindung betrifft Verbindungen, die in Porin der freien Säuren der allgemeinen Formel IThe invention relates to compounds in the porin of the free Acids of the general formula I
HO_S
5 HO_S
5
entsprechen, in dercorrespond in the
X ;Chlor oder Brom undX; chlorine or bromine and
R Wasserstoff oder C-- bis C^-Alkyl, R Wasserstoff oder C.- bis C^-Alkyl undR is hydrogen or C-- to C ^ -alkyl, R is hydrogen or C.- to C ^ -alkyl and
R ggf. durch Methyl, Äthyl, Methoxy, Äthoxy, Chlor, Brom, Carboxyl, Cyan, C.- bis C^-Alkoxycarbonyl, Carbamoyl, Sulfamoyl, N-mono- oder N,N-disubstituiertes C1- bis C2,- -Alkylcarbamoyl oder -sulfamoyl oder Hydroxysulfonyl ein- oder mehrfach substituiertes Phenyl oder ggf. durch Hydroxysulfonyl ein- oder mehrfach substituiertes Naphthyl bedeuten.R optionally by methyl, ethyl, methoxy, ethoxy, chlorine, bromine, carboxyl, cyano, C.- to C ^ -alkoxycarbonyl, carbamoyl, sulfamoyl, N-mono- or N, N-disubstituted C 1 - to C 2 , - -Alkylcarbamoyl or -sulphamoyl or hydroxysulphonyl denotes phenyl which is mono- or polysubstituted or, if appropriate, naphthyl which is monosubstituted or polysubstituted by hydroxysulphonyl.
Zur Herstellung der Verbindungen der Formel I kann man eine Diazonlurnverbindung des Amins der FormelFor the preparation of the compounds of the formula I can be a Diazonium compound of the amine of the formula
030021/0098030021/0098
O.Z. 0050/033510O.Z. 0050/033510
mit einer Kupplungskomponente der Formelwith a coupling component of the formula
HOHO
N-R-NO-
umsetzen.realize.
Man kann die Einzelkomponenten der Farbstoffe der Formel I auch in anderer Reihenfolge miteinander kombinieren.The individual components of the dyes of the formula I can be used also combine with each other in a different order.
Die Reaktionen sind im Prinzip bekannt, Einzelheiten der Umsetzungen können den Beispielen entnommen werden, in denen sich Angaben über Teile und Prozente, sofern nicht anders vermerkt, auf das Gewicht beziehen.The reactions are known in principle, details of the conversions can be found in the examples, which contain information on parts and percentages, unless otherwise noted, refer to weight.
Die Farbstoffe der Formel I sind scharlachfarben und ergeben auf cellulosehaltigen Fasern brillante Färbungen, die sich durch gute Echtheiten, wie durch Licht- und Naßechtheiten auszeichnen. Sie sind vorwiegend für die Ausziehfärberei bei erhöhter Temperatur (60 bis 8O0C) sowie teilweise für den Druck geeignet.The dyes of the formula I are scarlet in color and produce brilliant dyeings on cellulose-containing fibers which are distinguished by good fastness properties such as light and wet fastness properties. They are primarily suitable for the exhaust dyeing at an elevated temperature (60 to 8O 0 C) and partially for printing.
Von besonderer Bedeutung sind Verbindungen der Formel IaCompounds of the formula Ia are of particular importance
030 0 21/0 098030 0 21/0 098
O. Z. 0050/033510O. Z. 0050/033510
H03§H0 3 §
HOHO
in derin the
B "ggf. durch Methyl, Methoxy, Chlor, Carboxy oder Hydroxysulfonyl substituiertes Phenyl oder Suflonaphthyl undB "optionally by methyl, methoxy, chlorine, carboxy or hydroxysulfonyl substituted phenyl or suflonaphthyl and
ti . 2 ti . 2
R Wasserstoff oder Methyl bedeuten und R die angegebene Bedeutung hat.R is hydrogen or methyl and R has the meaning given.
Das Kondensationsprodukt aus 23,9 Teilen 2-Amino-5-hydroxynaphthalin-7-sulfonsäure und 18,8 Teilen Cyanurchlorid wird mit einer Lösung von 21,8 Teilen l-Naphthylamin-6-sulfonsäure in 3OO Teilen Wasser versetzt. Man erwärmt auf 40 bis 50°C und führt die Acylierung mit 6,8 Teilen Natriumbicarbonat bei pH 5 zu Ende. Das Reaktionsgemisch wird mit Eis auf 100C gekühlt, danach wird die durch Diazotierung von 37,5 Teilen 2-Aminonaphthalin-3,6,8-trisulfonsäure entstandene Diazosuspension eingetragen. Man kuppelt bei erhöhter Temperatur, vorzugsweise bei 10 bis 200C, und hält dabei den Kupplungs-pH-Wert mit 16,8 Teilen Natriumbicarbonat bei 6. Aus neutraler Lösung wird der Farbstoff durch Zugabe von Kochsalz ausgefällt und getrocknet. Man erhält ein rötlichbraunes Pulver, das Baumwolle in klaren scharlachroten Tönen echt färbt.A solution of 21.8 parts of 1-naphthylamine-6-sulfonic acid in 300 parts of water is added to the condensation product of 23.9 parts of 2-amino-5-hydroxynaphthalene-7-sulfonic acid and 18.8 parts of cyanuric chloride. The mixture is heated to 40 to 50 ° C. and the acylation is completed with 6.8 parts of sodium bicarbonate at pH 5. The reaction mixture is cooled with ice to 10 0 C, after which the 2-aminonaphthalene-3,6,8-trisulphonic acid by diazotization of 37.5 parts resulting diazo suspension is added. Coupling is carried out at an elevated temperature, preferably at 10 to 20 ° C., and the coupling pH is kept at 6 with 16.8 parts of sodium bicarbonate. The dye is precipitated from neutral solution by adding sodium chloride and dried. A reddish-brown powder is obtained which really dyes cotton in clear, scarlet shades.
18.8 Teile Cyanurchlorid werden in wäßriger Lösung mit18.8 parts of cyanuric chloride are added in aqueous solution
23.9 Teilen 2-Amino-5-hydroxynaphtalin-7-sulfonsäure bei 00C kondensiert, dabei wird der Acylierungs-pH-Wert mit 50 Tei-23.9 parts of 2-amino-5-hydroxynaphthalene-7-sulfonic acid condensed at 0 0 C, the acylation pH is 50 parts
030021/0098030021/0098
-β - Ο.Ζ. ΟΟ5Ο/Ο5351Ο-β - Ο.Ζ. ΟΟ5Ο / Ο5351Ο
1 m Natriumcarbonatlösung bei 5 gehalten. Zum Reaktionsgemisch werden dann 200 Teile einer Lösung von 13,4 Teilen 2-Aminobenzoesäure in Wasser gegeben, die Temperatur wird auf 40 C erhöht und der pH bei der Zweitkondensatlon mit 6,8 Teilen Natriumbicarbonat bei 5 gehalten. 37,-5 Teile 2-Naphthylamin-3,6,8-trisulfonsäure werden wie üblich diazoliert und in die mit Eis auf 100C abgekühlte Kupplungskomponentenlösung eingetragen. Man kuppelt bei erhöhter Temperatur, vorzugsweise bei 10 bis 200C und hält dabei den pH-Wert mit 16,8 Teilen Natriumbicarbonat bei 6. Durch Zugabe von Kochsalz wird der Farbstoff aus neutraler Lösung ausgefällt und getrocknet.1 M sodium carbonate solution held at 5. 200 parts of a solution of 13.4 parts of 2-aminobenzoic acid in water are then added to the reaction mixture, the temperature is increased to 40 ° C. and the pH is maintained at 5 during the second condensation with 6.8 parts of sodium bicarbonate. 37 -5 parts of 2-naphthylamine-3,6,8-trisulfonic acid are as diazoliert usual and added to the cooled with ice to 10 0 C coupling component solution. Coupling is carried out at an elevated temperature, preferably at 10 to 20 ° C., while keeping the pH at 6 with 16.8 parts of sodium bicarbonate. The dye is precipitated from neutral solution and dried by adding sodium chloride.
Eine andere Methode zur Isolierung des Farbstoffs ist die Zerstäubungstrocknung des Reaktionsgemisches.Another method of isolating the dye is to spray dry the reaction mixture.
Auf Baumwolle erhält man echte Färbungen in klaren, scharlachroten Tönen.Real dyeings in clear, scarlet red are obtained on cotton Tones.
In Tabelle 1 sind weitere nach den in Beispiel 1 und 2 angegebenen Verfahren erhältliche Farbstoffe zusammengefaßt:In Table 1, more are given according to those in Examples 1 and 2 Process available dyes summarized:
03 0 0 21/009803 0 0 21/0098
O O NJO O NJ
thalin-3,6,8-
trisulfonsäure2-aminonaphtha-
thalin-3,6,8-
trisulfonic acid
naphthalin-7-sul-
fonsäure2 ~ Amlno-5-hyd roxy-
naphthalene-7-sul-
fonic acid
chlorldCyanur-
chlorld
säure3-aminobenzoic
acid
säure4-aminobenzoene
acid
sulfonsäure2-aminobenzene
sulfonic acid
sulfonsäure3-aminobenzene
sulfonic acid
sulfonsäure4-Aminobeηzol-
sulfonic acid
amlno)-benzoe
säure2- (N-methyl-
amlno) -benzoe
acid
amino)-benzol-
sulfonsäure3- (N-methyl-
amino) -benzene-
sulfonic acid
fobenzoesäure2-Ainino-i | -sul-
fobenzoic acid
O O UlO O Ul
VjJ Ul μ-· OVjJ Ul µ- · O
K3 CX) K3 CX)
O CD ro O CD ro
ο ο co 00 ο ο co 00
lin-3,6,8-tri-
sulfonsäure2-aminonaphtha-
lin-3,6,8-tri-
sulfonic acid
naphthalin-7-sul-
fonsäure2 - amine o-5-h yd ro χ y-
naphthalene-7-sul-
fonic acid
chloridCyanur
chloride
fobenzoesäure2-Arnino-5-sul-
fobenzoic acid
2,5-dlsulfon
säure1-aminobenzene
2,5-dlsulfone
acid
2,4-dlsulfon
säure1-aminobenzene
2,4-dlsulfone
acid
chlorbenzol-
sulfonsäure3-amino-6-
chlorobenzene
sulfonic acid
chlorbenzol-
sulfonsäure3-amino-4-
chlorobenzene
sulfonic acid
chlorbenzol-
sulfonsäure2-amino-4-
chlorobenzene
sulfonic acid
chlorbenzol-
sulfonsäure2-amino-5-
chlorobenzene
sulfonic acid
oo Ioo I
cncn
lin-^,6,8-tri-
sulfonsäure2-aminonaphtha
lin - ^, 6,8-tri-
sulfonic acid
naphthalin-7-sul-
fonsäure2-amino-5-hydroxy
naphthalene-7-sul-
fonic acid
.chloridCyanuric
.chloride
methylbenzol-
sulfonsäure2-Amlno-5-
methylbenzene
sulfonic acid
methylbenzol-
sulfonsäureij -amino- 5-
methylbenzene
sulfonic acid
methylbenzol-
sulfonsäure4-amino-6-
methylbenzene
sulfonic acid
methoxybenzol-
sulfonsäure2-amino-5-
methoxybenzene
sulfonic acid
rnethoxybenzol-
sulfonsäure3-amino-6-
methoxybenzene
sulfonic acid
2-Amino-J|- methyl-5-chlorbenzolsulfonsäure 2-Amino-I | - methyl-5-chlorobenzenesulfonic acid
chlor-5-methylbenzolsulfonsäure chloro-5-methylbenzenesulfonic acid
O O UiO O Ui
I—'I— '
toto O CD KJO CD KJ
CD OUCD OU
.11π-3,6,8-ϊγ1-
sulfonsäure2-aminonaphtha-
.11π-3,6,8-ϊγ1-
sulfonic acid
naphthalin-7-sul-
fonsäure2-AmIn o-5-Hydro xy-
naphthalene-7-sul-
fonic acid
chloridCyanur
chloride
hydroxybenzol-
sulfonsäure3-amino- J i-
hydroxybenzene
sulfonic acid
chlorbenzoe-
säure2-amino-5-
chlorobenzoe
acid
chlorbenzoe-
säure3-amino-6-
chlorobenzoe
acid
benzolsulfon-
säure2, 'i-diamino-
benzenesulfone
acid
benzolsulfon-
säure2.5 diamonds
benzenesulfone
acid
tylaminoben-
zolsulfonsäure3-amino-6-ace-
tylaminoben-
zolsulfonic acid
tylaminoben-
zolsulfonsäure4-amino-6-ace-
tylaminoben-
zolsulfonic acid
I OI. O
O [SI O [SI
O O VJIO O VJI
VjJPrevious year
VJIVJI
H-1 H- 1
coco
CDCD
cncn
line, 6,8- tri-
sulfonsäure2-aminonaphtha
line, 6.8- tri-
sulfonic acid
naphthalin-7-sul-
fonsäure2-amino-5-hydroxy
naphthalene-7-sul-
fonic acid
chloridCyanur
chloride
ij^-disulfo-
säure2-aminotoluo1-
ij ^ -disulfo-
acid
h yd roxynaphthaiin-
7-sulfonsäure2-N-methylamino-5-
h yd roxynaphthaiin-
7-sulfonic acid
zolsulfon-
säure.3-amino-ben-
zolsulfone
acid.
amino-benzoe-
säure2-M-methyl-
amino benzene
acid
n aphthalin-7-sul-
fonsäure2-amino-5-hydroxy
naphthalene-7-sul-
fonic acid
thalln-6-sul-
fonsäure1-aminonaph-
thalln-6-sul-
fonic acid
thalin-5-sul-
fonsäure1-aminonaph-
thalin-5-sul-
fonic acid
tIt
t
thalin-'l-sul-
fonsäure1-aminonaph-
thalin-'l-sul-
fonic acid
thalin-3-sul-
fonsäure1-aminonaph-
thalin-3-sul-
fonic acid
O CD CO 00O CD CO 00
lin-3,6,8-tri-
sulfonsäure2-aminonaphtha-
lin-3,6,8-tri-
sulfonic acid
naphthalin-7-sul-
fonsäure2-amino-5-hydroxy
naphthalene-7-sul-
fonic acid
chlorid.Cyanur
chloride
thalin-7-sul-
fonsäure1-amnonaph-
thalin-7-sul-
fonic acid
thalln-3,6-di-
sulfonsäure1-aminonaph-
thalln-3,6-di-
sulfonic acid
thalin-3,7-di-
sulfonsäure1-aminonaph-
thalin-3,7-di-
sulfonic acid
thalin-5-sul-
fonsäure2-aminonaph-
thalin-5-sul-
fonic acid
thalin-6-sul-
fonsäure2-Arninonaph-
thalin-6-sul-
fonic acid
thalin-7-sul-
fonsäure2-aminonaph-
thalin-7-sul-
fonic acid
thalin-5,7-
disul fonsäure2-aminonaph-
thalin-5.7-
disulfonic acid
lln-3,6,8-tri-
sulfonsäure2-aminonaphtha-
lln-3,6,8-tri-
sulfonic acid
hydroxynaphthalin-
7-sulfonsäure2-N-methylamino-5-
hydroxynaphthalene
7-sulfonic acid
chloridCyanur
chloride
thalin-5-sul-
fonsäure1-aminonaph-
thalin-5-sul-
fonic acid
thalin-6-sul-
fonsäure1-aminonaph-
thalin-6-sul-
fonic acid
thalin-6-sul-
fonsäure2-Arninonaph-
thalin-6-sul-
fonic acid
O O VJl OO O VJl O
_ 14 - O.Z. 0050/033510_ 14 - O.Z. 0050/033510
Beispiel 49Example 49 ΊΊ
Die Reaktionslösung des sekundären Kondensationsprodukts aus 23,9 Teilen 2-Amino-5-hydroxynaphthalin-7-sulfonsäure, 18,8 Teilen Cyanurchlorid und 10,4 Teilen N-Methylanilin wird mit Eis auf 100C gekühlt und die Diazosuspension von 37,5 Teilen 2-Naphthylamin-3,6,8-trisulfosäure eingetragen. Man kuppelt bei erhöhter Temperatur, vorzugsweise bei 10 bis 200C und hält dabei den Kupplungs-pH-Wert mit 16,8 Teilen Natriumbicarbonat bei o. Aus neutraler Lösung wird der Farbstoff durch Eintragen von Kochsalz ausgefällt und getrocknet. Der Farbstoff kann auch durch Zerstäubungstrocknung des Reaktionsgemisches isoliert werden. Man erhält ein braunrotes Pulver, das Baumwolle in echten scharlachroten Tönen färbt.The reaction solution of the secondary condensation product of 23.9 parts of 2-amino-5-hydroxynaphthalene-7-sulfonic acid, 18.8 parts of cyanuric chloride and 10.4 parts of N-methylaniline is cooled with ice to 10 0 C and the diazo suspension of 37.5 Parts of 2-naphthylamine-3,6,8-trisulfonic acid entered. Coupling is carried out at an elevated temperature, preferably at 10 to 20 ° C., and the coupling pH is kept at 0 with 16.8 parts of sodium bicarbonate. The dye is precipitated from neutral solution by adding sodium chloride and dried. The dye can also be isolated by spray drying the reaction mixture. A brown-red powder is obtained which dyes cotton in genuine scarlet shades.
In Tabelle 2 sind weitere nach Beispiel 49 erhältliche Farbstoffe zusammengefaßt:Further dyes obtainable according to Example 49 are summarized in Table 2:
030021/0098030021/0098
coco CD OCD O
coco 0000
lin-3,6>8-tri-
sulfonsäure2-aminonaphtha-
lin-3,6> 8-tri-
sulfonic acid
naphthalin-7-sul-
fonsäure2-amino-5-hydroxy
naphthalene-7-sul-
fonic acid
chloridCyanur
chloride
linN-cyanoethylani-
lin
linN-oxethylani-
lin
linN-benzylani-
lin
toluidinN-methyl-o-
toluidine
toluidinN-ethyl-o-
toluidine
toluidinN-butyl-o-
toluidine
toluidinN-butyl-m-
toluidine
O ISlO ISl
O O UlO O Ul
UI t-' OUI t- 'O
lin-3,6,8-tri-
sulfonsäure2-aminonaphtha-
lin-3,6,8-tri-
sulfonic acid
naphthalin-7-sul-
fonsciure2-amino-5-hyd roxy-
naphthalene-7-sul-
fonsciure
chloridCyanur-
chloride
toluidinN-cyanoethyl-m-
toluidine
anilin2,5-dimethyl
aniline
anil in2, 1 I-dimethyl
anil in
lin-3,6,8-tri-
sulfonsäure2-aminonaphtha-
lin-3,6,8-tri-
sulfonic acid
naphthalln-7-sul-
fonsäure2-amino-5-hydroxy
naphthalln-7-sul-
fonic acid
chloridCyanur
chloride
anilin2,3-dimethyl
aniline
anilin2,4-dimethoxy
aniline
anilin2; 5-dimethoxy
aniline
anilin2,4-dichloro
aniline
anllin2.5-DiChIOr-
anllin
anilin3jl dichloro
aniline
anilin3.5 Diehlor
aniline
methylanilin3-chloro-n-
methylaniline
chloranilin2-methyl- J {-
chloraniline
CD CD 00CD CD 00
lin-3,6,8-tri-
sulfonsäure2-aminonaphtha-
lin-3,6,8-tri-
sulfonic acid
, naphthalin-7-sul-
fonsäure2-.amino-5-hyd.roxy-
, naphthalene-7-sul-
fonic acid
chloridCyanur
chloride
chloranilin2-methyl-5-
chloraniline
thylanilin2-chloro-5-me-
thylaniline
ox'yanilin. 3-Chlop-iJ-meth-
ox'yaniline
chlor-anilin2-methoxy-5-
chloro-aniline
chloranilin2-methoxy-'l-
chloraniline
methoxyanilin2-methyl-'l-
methoxyaniline
methylanilin2-methoxy-5-
methylaniline
thylanilln3-methoxy-4-mene-
thylanilln
bonylanilin2-methoxycar-
bonylaniline
bonylanilin2-ethoxycar-
bonylaniline
O toO to
roro
ο ο coο ο co 0000
Iin-3j6,8-tri-
sulfonsäure2-aminonaphtha-
Iin-3j6,8-tri-
sulfonic acid
naphthalin-7-sul-
fonsäure2-amino-5-hydroxy
naphthalene-7-sul-
fonic acid
chloridCyanur
chloride
carbonylanilin2,5-diethoxy
carbonylaniline
bonylanilin^ -Methoxycar-
bonylaniline
bonylanilin4-A'thoxycar-
bonylaniline
noanilin4-dimethylami-
noaniline
noanilin4-diethylamine
noaniline
anilin3-acetylamino
aniline
aniliri^ I-acetylamino-
aniliri
Η· IΗ · I
O ISlO ISl
O O VJIO O VJI
Ul I—' Ul I— '
O coO co O CD K)O CD K)
O O CD COO O CD CO
lin-3,6,8-tri-
sulfonsäure2-aminonaphtha-
lin-3,6,8-tri-
sulfonic acid
naphthalln-7-sul-
fonsäure2-amino-5-hydroxy
naphthalln-7-sul-
fonic acid
chloridCyanur
chloride
sulfonamidp-aminobenzene
sulfonamide
sulfonamidm-aminobenzene
sulfonamide
carbonamido-aminobenzene
carbonamide
carbonamidp-aminobe η zo1-
carbonamide
lin1-aminonaphtha-
lin
lin2-aminonaphtha-
lin
naphthalin1-M-Sthylamino-
naphthalene
hydroxynaphthalin-
7-sulfonsäure2-N-methylamino-5-
hydroxynaphthalene
7-sulfonic acid
sulfonamidp-aminobenzene
sulfonamide
nylanilin2-methoxycarbo-
nylaniline
.111
.
anilin2,5-dimethyl
aniline
ro Oro O
O CSlO CSl
O OO O
V>! V>J uiV>! V> J ui
I—·I— ·
ϋη-3>6Α8-^1-
sulfonsäure2-aminonaphtha-
ϋη-3> 6 Α 8- ^ 1-
sulfonic acid
hydroxynaphthalin-
7-sulfonsäure2-N-methyl amino-5-
hydroxynaphthalene
7-sulfonic acid
chloridCyanur
chloride
O OO O
σ ο co 00 σ ο co 00
roro
O O VJlO O VJl
UlUl
ι—' O- 'O
Claims (2)
Wasserstoff oder C1- bis C,.-Alkyl, Wasserstoff oder C1- bis C,-Alkyl und ggf· durch Methyl, Äthyl, Meshoxy, Äthoxy, Chlor, Brom, Carboxyl, Cyan, C.- bis C^-Alkoxycarbonyl, Carbamoyl, Sulfamoyl, N-mono- oder N,N-disubstituiertes C^- bis C^-Alkylcarbamoyl oder -sulfamoyl oder Hydroxysulfonyl ein- oder mehrfach substituiertes Phenyl oder ggf. durch Hydroxysulfonyl ein- oder mehrfach substituiertes Naphthyl bedeuten.Chlorine or bromine and
Hydrogen or C 1 - to C 1 - alkyl, hydrogen or C 1 - to C 1 - alkyl and optionally by methyl, ethyl, meshoxy, ethoxy, chlorine, bromine, carboxyl, cyano, C 1 - to C 1 - alkoxycarbonyl , Carbamoyl, sulfamoyl, N-mono- or N, N-disubstituted C ^ - to C ^ -alkylcarbamoyl or -sulfamoyl or hydroxysulfonyl phenyl which is mono- or polysubstituted or optionally naphthyl which is mono- or polysubstituted by hydroxysulfonyl.
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2847916A DE2847916C2 (en) | 1978-11-04 | 1978-11-04 | Reactive dyes and their use |
| FR7926630A FR2440385B1 (en) | 1978-11-04 | 1979-10-26 | REACTIVE DYES AND THEIR APPLICATION |
| IT26943/79A IT1124857B (en) | 1978-11-04 | 1979-10-30 | REACTIVE DYES |
| CH977679A CH641486A5 (en) | 1978-11-04 | 1979-10-31 | REACTIVE DYES. |
| JP14143979A JPS5565259A (en) | 1978-11-04 | 1979-11-02 | Reactive dye |
| GB7937989A GB2036778B (en) | 1978-11-04 | 1979-11-02 | Reactive dyes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2847916A DE2847916C2 (en) | 1978-11-04 | 1978-11-04 | Reactive dyes and their use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2847916A1 true DE2847916A1 (en) | 1980-05-22 |
| DE2847916C2 DE2847916C2 (en) | 1984-04-26 |
Family
ID=6053883
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2847916A Expired DE2847916C2 (en) | 1978-11-04 | 1978-11-04 | Reactive dyes and their use |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS5565259A (en) |
| CH (1) | CH641486A5 (en) |
| DE (1) | DE2847916C2 (en) |
| FR (1) | FR2440385B1 (en) |
| GB (1) | GB2036778B (en) |
| IT (1) | IT1124857B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH641197A5 (en) | 1977-12-23 | 1984-02-15 | Sandoz Ag | REACTIVE MONOAZO DYES AND METHOD FOR THE PRODUCTION THEREOF. |
| CH655735A5 (en) * | 1982-09-17 | 1986-05-15 | Sandoz Ag | REACTIVE MONOAZO CONNECTIONS. |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2358450A1 (en) * | 1976-07-12 | 1978-02-10 | Ciba Geigy Ag | REAGENT NITROGEN DYES ON FIBERS, THEIR PREPARATION PROCESS AND THEIR USE |
| FR2384001A1 (en) * | 1977-03-15 | 1978-10-13 | Bayer Ag | PROCESS FOR THE PREPARATION OF AZOIC REACTIVE DYES |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB908194A (en) * | 1960-08-03 | 1962-10-17 | Ici Ltd | New triazine monoazo dyestuffs |
| JPS49104923A (en) * | 1973-02-05 | 1974-10-04 | ||
| LU78485A1 (en) * | 1977-11-10 | 1979-06-13 | Ciba Geigy Ag | REACTIVE COLORS, THEIR PRODUCTION AND USE |
| CH641197A5 (en) * | 1977-12-23 | 1984-02-15 | Sandoz Ag | REACTIVE MONOAZO DYES AND METHOD FOR THE PRODUCTION THEREOF. |
| DE2838271A1 (en) * | 1978-09-01 | 1980-03-13 | Bayer Ag | AZOREACTIVE DYES |
| DE2838608A1 (en) * | 1978-09-05 | 1980-03-20 | Bayer Ag | AZO REACTIVE DYES |
-
1978
- 1978-11-04 DE DE2847916A patent/DE2847916C2/en not_active Expired
-
1979
- 1979-10-26 FR FR7926630A patent/FR2440385B1/en not_active Expired
- 1979-10-30 IT IT26943/79A patent/IT1124857B/en active
- 1979-10-31 CH CH977679A patent/CH641486A5/en not_active IP Right Cessation
- 1979-11-02 JP JP14143979A patent/JPS5565259A/en active Granted
- 1979-11-02 GB GB7937989A patent/GB2036778B/en not_active Expired
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2358450A1 (en) * | 1976-07-12 | 1978-02-10 | Ciba Geigy Ag | REAGENT NITROGEN DYES ON FIBERS, THEIR PREPARATION PROCESS AND THEIR USE |
| FR2384001A1 (en) * | 1977-03-15 | 1978-10-13 | Bayer Ag | PROCESS FOR THE PREPARATION OF AZOIC REACTIVE DYES |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2036778B (en) | 1983-08-17 |
| IT1124857B (en) | 1986-05-14 |
| DE2847916C2 (en) | 1984-04-26 |
| FR2440385B1 (en) | 1985-08-23 |
| JPS5565259A (en) | 1980-05-16 |
| IT7926943A0 (en) | 1979-10-30 |
| GB2036778A (en) | 1980-07-02 |
| CH641486A5 (en) | 1984-02-29 |
| FR2440385A1 (en) | 1980-05-30 |
| JPS6329709B2 (en) | 1988-06-15 |
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