DE2847916C2 - Reactive dyes and their use - Google Patents
Reactive dyes and their useInfo
- Publication number
- DE2847916C2 DE2847916C2 DE2847916A DE2847916A DE2847916C2 DE 2847916 C2 DE2847916 C2 DE 2847916C2 DE 2847916 A DE2847916 A DE 2847916A DE 2847916 A DE2847916 A DE 2847916A DE 2847916 C2 DE2847916 C2 DE 2847916C2
- Authority
- DE
- Germany
- Prior art keywords
- same
- scarlet
- methyl
- formula
- reactive 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.)
- Expired
Links
- 239000000985 reactive dye Substances 0.000 title claims 2
- 239000002253 acid Substances 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 2
- 239000000975 dye Substances 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- -1 sulfonaphthyl Chemical group 0.000 description 3
- RJSYPKWVIJGNLO-UHFFFAOYSA-N CCOClOC Chemical compound CCOClOC RJSYPKWVIJGNLO-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical group COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- VUUHXRVVDUAGOL-UHFFFAOYSA-N 3-(3-methylanilino)propanenitrile Chemical compound CC1=CC=CC(NCCC#N)=C1 VUUHXRVVDUAGOL-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
- FENJKTQEFUPECW-UHFFFAOYSA-N 3-anilinopropanenitrile Chemical compound N#CCCNC1=CC=CC=C1 FENJKTQEFUPECW-UHFFFAOYSA-N 0.000 description 1
- YYYARFHFWYKNLF-UHFFFAOYSA-N 4-[(2,4-dimethylphenyl)diazenyl]-3-hydroxynaphthalene-2,7-disulfonic acid Chemical compound CC1=CC(C)=CC=C1N=NC1=C(O)C(S(O)(=O)=O)=CC2=CC(S(O)(=O)=O)=CC=C12 YYYARFHFWYKNLF-UHFFFAOYSA-N 0.000 description 1
- 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 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- WVMBPWMAQDVZCM-UHFFFAOYSA-N N-methyl anthranilic acid Natural products CNC1=CC=CC=C1C(O)=O WVMBPWMAQDVZCM-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- GUAWMXYQZKVRCW-UHFFFAOYSA-N n,2-dimethylaniline Chemical compound CNC1=CC=CC=C1C GUAWMXYQZKVRCW-UHFFFAOYSA-N 0.000 description 1
- GTWJETSWSUWSEJ-UHFFFAOYSA-N n-benzylaniline Chemical compound C=1C=CC=CC=1CNC1=CC=CC=C1 GTWJETSWSUWSEJ-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
- UUSGZWZUYJHBJS-UHFFFAOYSA-N n-butyl-3-methylaniline Chemical compound CCCCNC1=CC=CC(C)=C1 UUSGZWZUYJHBJS-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
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-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
- 230000007935 neutral effect Effects 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000004753 textile Substances 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)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Cosmetics (AREA)
Description
SO3H HO3SSO 3 H HO 3 S
entsprechen, in dercorrespond in the
X Chlor oder Brom und
R1 Wasserstoff oder C,- bis C4-Alkyl,
R2 C1- bis Cj-Alkyl undX chlorine or bromine and
R 1 is hydrogen or C, - to C 4 -alkyl,
R 2 C 1 - to Cj-alkyl and
R3 ggf. durch Methyl, Äthyl, Methoxy, Äthoxy, Chlor, Brom, Carboxyl, Cyan, C1- bis C4-AIk-R 3 if necessary by methyl, ethyl, methoxy, ethoxy, chlorine, bromine, carboxyl, cyano, C 1 - to C 4 -AIk-
2. Farbstoffe gemäß Anspruch 1 der Formel2. Dyestuffs according to Claim 1 of the formula
HO3S OHHO 3 S OH
HO,SHO, S
N = NN = N
SO3H HO3SSO 3 H HO 3 S
oxycarbonyl, Carbamoyl, Sulfamoyl, N-monooderN,N-disubstituiertes Cr bis C4-Alkylcarbamoyl oder -sulfamoyl oder Hydroxysulfonyl ein- oder mehrfach substituiertes Phenyl oder ggf. durch Hydroxysulfonyl ein- oder mehrfach substituiertes Naphthyl bedeuten.oxycarbonyl, carbamoyl, sulfamoyl, N-mono or N, N-disubstituted C r to C 4 -alkylcarbamoyl or -sulfamoyl or hydroxysulfonyl monosubstituted or polysubstituted phenyl or optionally naphthyl monosubstituted or polysubstituted by hydroxysulfonyl.
N-BN-B
in derin the
B ggf. durch Methyl, Methoxy, Chlor, Carboxy oder Hydroxysulfonyl substituiertes Phenyl oder Sulfonaphthyl und R4 Wasserstoff oder Methyl bedeuten und R2 die angegebene Bedeutung hat.B is phenyl or sulfonaphthyl optionally substituted by methyl, methoxy, chlorine, carboxy or hydroxysulfonyl and R 4 is hydrogen or methyl and R 2 has the meaning given.
3. Verwendung der Farbstoffe gemäB Anspruch 1 zum Färben von Polyamiden, Leber oder cellulosehaltigen! Textilmaterial.3. Use of the dyes according to claim 1 for dyeing polyamides, liver or cellulose-containing! Textile material.
Die Erfindung betrifft Verbindungen, die in Form der freien Säuren der allgemeinen Formel I HO3S OHThe invention relates to compounds which, in the form of the free acids of the general formula I HO 3 S OH
HO3SHO 3 S
entsprechen, in dercorrespond in the
Chlor oder Brom und
Wasserstoff oder C,- bis C4-Alkyl,
C1- bis C3-Alkyl undChlorine or bromine and
Hydrogen or C, - to C 4 -alkyl,
C 1 - to C 3 -alkyl and
ggf. durch Methyl, Äthyl, Methoxy, Äthoxy, Chlor, Brom, Carboxyl, Cyan. C,- bis C4-Alkoxycarbonyl, Carbamoyl, Sulfamoyl, N-mono- oder N,N-disubstituiertes Cr bis C4-Alkylcarbamoyl oder -sulfamoyl oder Hydroxysulfonyl ein- oder mehrfach substituiertes Phenyl oder ggf. durch Hydroxysulfonyl ein- oder mehrfach substituiertes Naphthvl bedeuten.possibly by methyl, ethyl, methoxy, ethoxy, chlorine, bromine, carboxyl, cyano. C 1 to C 4 alkoxycarbonyl, carbamoyl, sulfamoyl, N-mono- or N, N-disubstituted C r to C 4 -alkylcarbamoyl or -sulfamoyl or hydroxysulfonyl mono- or poly-substituted phenyl or optionally mono- or poly-substituted by hydroxysulphonyl substituted naphthyl.
Zur Herstellung der Verbindungen der Formel I kann man eine Diazoniumverbindung des Amins der FormelA diazonium compound of the amine of the formula I can be used to prepare the compounds of the formula I
HO3SHO 3 S
HOjSHOjS
NH7 NH 7
SO3HSO 3 H
mit einer Kupplungskomponente der Formelwith a coupling component of the formula
HOHO
HO3SHO 3 S
N-R3 NR 3
umsetzen.realize.
Man kann die Einzelkcmponenten der Farbstoffe der Formel I auch in anderer Reihenfolge miteinander kombinieren. The individual components of the dyes of the formula I can also be combined with one another 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 reactions can be found in the examples, in which information on parts and percentages is based on weight, unless otherwise stated relate.
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 Ausziehiarberei bei erhöhter Temperatur (60 bis 800C) sowie teilweise für den Druck geeignetThe dyes of the formula I are scarlet colors 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 Ausziehiarberei at elevated temperature (60 to 80 0 C) and partly for the pressure
Von besonderer Bedeutung sind Verbindungen der Formel IaCompounds of the formula Ia are of particular importance
HO3SHO 3 S
in derin the
B ggf. durch Methyl, Methoxy, Chlor, Carboxy oder Hydroxysulfonyl substituiertes Phenyl oder Suflonaphthyl und R4 Wasserstoff oder Methyl bedeuten und R2 die angegebene Bedeutung hat.B is phenyl or suflonaphthyl optionally substituted by methyl, methoxy, chlorine, carboxy or hydroxysulfonyl and R 4 is hydrogen or methyl and R 2 has the meaning given.
Gegenüber einem nächstvergleichbaren aus der FR-PS 23 58 450 bekannten Farbstoff zeichnen sich die erfindungsgemäßen Verbindungen in unvorhersehbarer Weise durch verbesserte Bleich- und Sodahochechtheit aus.Compared to a next comparable from FR-PS 23 58 450 known dye stand out Compounds according to the invention in an unpredictable manner due to improved bleach and soda high fastness the end.
Die Reaktionslösung des sekundären Kondensationsprodukts aus 23,9 Teilen 2-Amino-5-hydroxynaphtha- N-BThe reaction solution of the secondary condensation product from 23.9 parts of 2-amino-5-hydroxynaphtha- N-B
R2 R 2
ji lin-7-sulfonsäure, 18,8 Teilen Cyanurchlorid und 10,4 Teilen N-Methylanilin wird mit Eis auf 1O0C gekühlt und die Diazosuspension von 37,5 Teilen 2-Naphthylamin-3,6,8-trisulfosäure eingetragen. Man kuppelt bei erhöhter Temperatur, vorzugsweise bei 10ji lin-7-sulfonic acid, 18.8 parts of cyanuric chloride and 10.4 parts of N-methyl aniline is cooled with ice to 1O 0 C and added to the diazo suspension of 37.5 parts of 2-naphthylamine-3,6,8-trisulphonic acid. The coupling is carried out at an elevated temperature, preferably at 10
ι» bis 200C und hält dabei den Kupplungs-pH-Wert mit 16,8 Teilen Natriumbicarbonat bei 6. Aus neutraler Lösung wird der Farbstoff durch Eintragen von Kochsalz ausgefällt und getrocknet. Der Farbstoff kann auch durch Zerstäubungstrocknung des Reaktionsgemischesι »to 20 0 C and keeps the coupling pH with 16.8 parts of sodium bicarbonate at 6. The dye is precipitated from neutral solution by adding sodium chloride and dried. The dye can also be obtained by spray drying the reaction mixture
tr> isoliert werden. Man erhält ein braunrotes Pulver, das Baumwolle in echten scharlachroten Tönen färbt. t r > be isolated. A brown-red powder is obtained which dyes cotton in genuine scarlet shades.
In der folgenden Tabelle sind weitere nach Beispiel 1 erhältliche Farbstoffe zusammengefaßt:The following table summarizes further dyes obtainable according to Example 1:
3,6,8-trisulfonsäure2-aminonaphthalene
3,6,8-trisulfonic acid
7-sulfonsäure2-amino-5-hydroxynaphthalene
7-sulfonic acid
chloridCyanur
chloride
benzoe säure2- (N-methylamino) -
benzoic acid
benzol-sulfonsäure3- (N-methylamino) -
benzene sulfonic acid
naphthalin-7-sulfonsäure2-N-methylamino-5-hydroxy
naphthalene-7-sulfonic acid
benzoe säure2-N-methylamino-
benzoic acid
7-sulfonsäure2-amino-5-hydroxynaphthalene
7-sulfonic acid
m-toluidinN-cyanoethyl
m-toluidine
naphthalin1-N-ethylamino-
naphthalene
naDhthalin-7-sulfonsiure2-N-methylamino-5-hydroxy
NaDthalene-7-sulfonic acid
Claims (1)
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. |
| GB7937989A GB2036778B (en) | 1978-11-04 | 1979-11-02 | Reactive dyes |
| JP14143979A JPS5565259A (en) | 1978-11-04 | 1979-11-02 | Reactive dye |
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 DE2847916A1 (en) | 1980-05-22 |
| DE2847916C2 true 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. |
Family Cites Families (8)
| 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 | ||
| IT1116356B (en) * | 1976-07-12 | 1986-02-10 | Ciba Geigy Ag | REACTIVE AZO DYES FOR FIBERS AND PROCEDURE FOR THEIR PRODUCTION AND APPLICATION |
| DE2711150A1 (en) * | 1977-03-15 | 1978-09-28 | Bayer Ag | METHOD OF PREPARING AZOREACTIVE DYES |
| 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 GB GB7937989A patent/GB2036778B/en not_active Expired
- 1979-11-02 JP JP14143979A patent/JPS5565259A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2440385A1 (en) | 1980-05-30 |
| IT7926943A0 (en) | 1979-10-30 |
| JPS6329709B2 (en) | 1988-06-15 |
| GB2036778A (en) | 1980-07-02 |
| GB2036778B (en) | 1983-08-17 |
| CH641486A5 (en) | 1984-02-29 |
| IT1124857B (en) | 1986-05-14 |
| FR2440385B1 (en) | 1985-08-23 |
| DE2847916A1 (en) | 1980-05-22 |
| JPS5565259A (en) | 1980-05-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8125 | Change of the main classification |
Ipc: C09B 62/085 |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8330 | Complete renunciation |
