DE2158121A1 - Blue-blue/green oxazine dyes contg arylamine gps - - for faast dyeing polyacrylonitrile,anionically-modified polyesters, - Google Patents
Blue-blue/green oxazine dyes contg arylamine gps - - for faast dyeing polyacrylonitrile,anionically-modified polyesters,Info
- Publication number
- DE2158121A1 DE2158121A1 DE19712158121 DE2158121A DE2158121A1 DE 2158121 A1 DE2158121 A1 DE 2158121A1 DE 19712158121 DE19712158121 DE 19712158121 DE 2158121 A DE2158121 A DE 2158121A DE 2158121 A1 DE2158121 A1 DE 2158121A1
- Authority
- DE
- Germany
- Prior art keywords
- blue
- alkyl
- formula
- anionically
- faast
- 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
- 239000000975 dye Substances 0.000 title claims abstract description 16
- 238000004043 dyeing Methods 0.000 title claims description 6
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 title claims description 3
- 229920002239 polyacrylonitrile Polymers 0.000 title description 3
- 229920000728 polyester Polymers 0.000 title description 2
- 150000004982 aromatic amines Chemical class 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
- 150000001450 anions Chemical class 0.000 claims abstract description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 5
- -1 carbalkoxyethyl Chemical group 0.000 claims description 4
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- 239000000835 fiber Substances 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000000463 material Substances 0.000 claims 1
- 239000004753 textile Substances 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 239000002798 polar solvent Substances 0.000 abstract 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 10
- 235000005074 zinc chloride Nutrition 0.000 description 5
- 239000011592 zinc chloride Substances 0.000 description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- XVTSEZVYBJFEED-UHFFFAOYSA-N [Cl-].COC=1C=C(C=CC1N=O)[NH2+]C1=C(C=CC=C1)C Chemical compound [Cl-].COC=1C=C(C=CC1N=O)[NH2+]C1=C(C=CC=C1)C XVTSEZVYBJFEED-UHFFFAOYSA-N 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 description 1
- ZPFAVCIQZKRBGF-UHFFFAOYSA-N 1,3,2-dioxathiolane 2,2-dioxide Chemical compound O=S1(=O)OCCO1 ZPFAVCIQZKRBGF-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- APLCRWNVGMWDNL-UHFFFAOYSA-N 3-(5-hydroxy-2-methylanilino)propanenitrile Chemical compound C(#N)CCNC=1C=C(C=CC1C)O APLCRWNVGMWDNL-UHFFFAOYSA-N 0.000 description 1
- CTGSQPRDMHCIMM-UHFFFAOYSA-N 3-(ethylamino)-4-methylphenol Chemical compound CCNC1=CC(O)=CC=C1C CTGSQPRDMHCIMM-UHFFFAOYSA-N 0.000 description 1
- NUNAWQZKZVVELQ-UHFFFAOYSA-N 3-amino-4-methylphenol Chemical compound CC1=CC=C(O)C=C1N NUNAWQZKZVVELQ-UHFFFAOYSA-N 0.000 description 1
- SGHZXLIDFTYFHQ-UHFFFAOYSA-L Brilliant Blue Chemical compound [Na+].[Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=2C(=CC=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 SGHZXLIDFTYFHQ-UHFFFAOYSA-L 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- 125000006226 butoxyethyl group Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001424 substituent group Chemical group 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
- C09B19/00—Oxazine dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
Abstract
Description
Basische Oxazinfarbstoffe Die Erfindung betrifft Farbstoffe der Formel I in der R Wasserstoff, Alkyl mit 1 bis 4 C-Atomen, CyanEthyl, Chloräthyl, Carbalkoxyäthyl oder Hydroxyalkyl, R1 Wasserstoff, Methyl oder Äthyl, R2 Wasserstoff, Alkyl mit 1 bis 4 C-Atomen, Mydroxyalkyl, Carbalkoxyäthyl, Cyanäthyl oder Chloräthyl, R3 Alkyl mit 1 bis 4 C-Atomen und ein Anion bedeuten.Basic Oxazine Dyes The invention relates to dyes of the formula I in which R is hydrogen, alkyl with 1 to 4 carbon atoms, cyanoethyl, chloroethyl, carbalkoxyethyl or hydroxyalkyl, R1 is hydrogen, methyl or ethyl, R2 is hydrogen, alkyl with 1 to 4 carbon atoms, hydroxyalkyl, carbalkoxyethyl, cyanoethyl or chloroethyl, R3 Mean alkyl having 1 to 4 carbon atoms and an anion.
Reste R und R2 sind außer den schon einzeln genannten z. B.: Propyl, Butyl, Carbomethoxy-,- -äthoxy- oder -butoxyäthyl, ß-Hydroxyäthyl, 8-Hydroxypropyl und vorzugsweise Methyl oder Äthyl.R and R2 are apart from those already mentioned individually, for. E.g .: propyl, Butyl, carbomethoxy, ethoxy or butoxyethyl, β-hydroxyethyl, 8-hydroxypropyl and preferably methyl or ethyl.
Reste R3 sind z. B. Butyl, Äthyl und insbesondere Methyl.R3 radicals are e.g. B. butyl, ethyl and especially methyl.
Anionen X@ sind beispielsweise Chlorid, Bromid, Nitrat, Sulfat, Methosulfat, Äthosulfat, Formiat, Acetat, Toluolsulfonat oder Tetrachlorozinkat.Anions X @ are, for example, chloride, bromide, nitrate, sulfate, methosulfate, Ethosulfate, formate, acetate, toluenesulfonate or tetrachlorozincate.
Von besonderer technischer Bedeutung sind Farbstoffe der Formel Ia Bevorzugte Reste R für Formel Ia sind Wasserstoff, Methyl, Äthyl oder Cyanat-hyl.Dyes of the formula Ia are of particular industrial importance Preferred radicals R for formula Ia are hydrogen, methyl, ethyl or cyanate-hyl.
Die neuen Farbstoffe sind blau und eignen sich zum Färben von anionisch modifizierten Fasern, insbesondere Acrylnitrilpolymerisaten und Polyestern. Man erhält damit brillante blaue bis grünstichig blaue Färbungen mit vorzüglichen Echtheiten.The new dyes are blue and are suitable for dyeing anionic modified fibers, especially acrylonitrile polymers and polyesters. Man thus obtains brilliant blue to greenish blue dyeings with excellent fastness properties.
Außerdem haben die Farbstoffe eine gute bis sehr gute Wasserlöslichkeit Zur Herstellung der Farbstoffe der Formel I kann man Verbindungen der Formel II in der B Alkyl, vorzugsweise Methyl oder Äthyl, bedeutet, mit Verbindungen der Formel III 2 umsetzen. R, R1, R und R3 haben dabei die angegebenen Bedeutungen.In addition, the dyes have good to very good solubility in water. For the preparation of the dyes of the formula I, compounds of the formula II can be used in which B is alkyl, preferably methyl or ethyl, with compounds of the formula III 2 implement. R, R1, R and R3 have the meanings given.
Einzelheiten der Umsetzungen sind denfolgenden Beispielen zu entnehmen.Details of the conversions can be found in the following examples.
Beispiel 1 27 g 3-Methoxy-4-nitrosophenyl-o-tolylammoniumchlorid werden in zwei Stunden in eine 60 °C warme Lösung von 18 g 3-Cyanäthylamino-4-methylphenol und 13 g Zinkchlorid in 100 ml Äthanol eingetragen. Nach einer weiteren Stunde bei 60 °C wird die Lösung mit 300 ml Wasser versetzt und die Fällung durch Zugabe von gesättigter Kochsalzlösung vervollständigt. Example 1 27 g of 3-methoxy-4-nitrosophenyl-o-tolylammonium chloride are in two hours in a 60 ° C solution of 18 g of 3-cyanoethylamino-4-methylphenol and added 13 g of zinc chloride in 100 ml of ethanol. After another hour at 60 ° C, the solution is mixed with 300 ml of water and the precipitation by adding saturated saline solution.
Der Farbstoff ergibt auf Acrylnitrilpolymerisatfasern blaue Färbungen mit sehr guten Echtheiten.The dye produces blue dyeings on acrylonitrile polymer fibers with very good fastness properties.
Beispiel 2 27 g 3-Methoxy-4-nitrosophenyl-o-tolylammoniumchlorid werden langsam in eine 50 oC warme Lösung von 12 g 3-Amino-4-methylphenol und 26 g Zinkchlorid in 100 ml Methanol eingetragen. Example 2 27 g of 3-methoxy-4-nitrosophenyl-o-tolylammonium chloride are slowly poured into a 50 oC solution of 12 g of 3-amino-4-methylphenol and Entered 26 g of zinc chloride in 100 ml of methanol.
Der Farbstoff fällt rein als schwerlösliches Zinkchlorid-Doppelsalz aus Durch Überführen in das Acetat erhält man einen gut löslichen Farbstoff, der Färbungen mit sehr guten Echtheitseigenschaften ergibt.The dye falls in the form of a sparingly soluble zinc chloride double salt By converting it into the acetate, a readily soluble dye is obtained, the Dyeings with very good fastness properties results.
Beispiel 3 27 g 3-Methoxy-4-nitrosophenyl-o-tolylammoniumchlorid werden langsam in eine 80 °C warme Lösung von 15 g 3-Äthylamino-4-methylphenol und 13 g Zinkchlorid in 100 ml Methylglykol eingetragen. Der Farbstoff fällt rein als Zinkchlorid-Doppelsalz aus. Er kann leicht über die Base in das gut lösliche Farbstoff@hlorid übergeführt werden. Example 3 27 g of 3-methoxy-4-nitrosophenyl-o-tolylammonium chloride are slowly in a 80 ° C solution of 15 g of 3-ethylamino-4-methylphenol and 13 g of zinc chloride added to 100 ml of methyl glycol. The dye falls pure as Zinc chloride double salt. It can easily be converted into the readily soluble dye @chloride via the base be transferred.
Analog der angegebenen Arbeitsweise erhält man auch die in der folgenden Tabelle durch Angabe der Substituenten charakterisierten blauen Farbstoffe: Beisp. R R1 R2 R3 4 C4H9 H H o-CH3 5 C2H4OH CH3 H p-CH3 6 CH2CHOHCH3 CH3 H p-CH3 7 C2H4Cl CH3 H o-CH3 8 C2H4COOCH3 CH3 H p-CH3 9 C2H4COOC4H9 CH3 H p-CH3 10 CH3 C2H5 H o-CH3 11 H CH3 CH3 p-CH3 12 C2H5 CH3 C4H9 p-CH3 13 C2H5 CH3 C2H4OH p-CH3 14 C2H5 CH3 CH2CHOHCH p-CH3 15 C2H5 CH3 C2H4COOC2H5 p-CH3 16 C2H5 CH3 C2H4CN p-CH3 17 C2H5 CH3 C2H4Cl p-CH3 18 H CH3 H p-C2H5 19 H CH3 II p-C4H9The blue dyes characterized in the following table by specifying the substituents are also obtained analogously to the procedure given: Ex. R R1 R2 R3 4 C4H9 HH o-CH3 5 C2H4OH CH3 H p-CH3 6 CH2CHOHCH3 CH3 H p-CH3 7 C2H4Cl CH3 H o-CH3 8 C2H4COOCH3 CH3 H p-CH3 9 C2H4COOC4H9 CH3 H p-CH3 10 CH3 C2H5 H o-CH3 11 H CH3 CH3 p-CH3 12 C2H5 CH3 C4H9 p-CH3 13 C2H5 CH3 C2H4OH p-CH3 14 C2H5 CH3 CH2CHOHCH p-CH3 15 C2H5 CH3 C2H4COOC2H5 p-CH3 16 C2H5 CH3 C2H4CN p-CH3 17 C2H5 CH3 C2H4Cl5 CH3 p-CH3 18 H CH3 H p-C2H5 19 H CH3 II p-C4H9
Claims (4)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712158121 DE2158121C3 (en) | 1971-11-24 | 1971-11-24 | Basic oxazine dyes, their preparation and use |
| CH102272A CH571045A5 (en) | 1971-02-03 | 1972-01-24 | Blue-blue/green oxazine dyes contg arylamine gps - - for faast dyeing polyacrylonitrile,anionically-modified polyesters, |
| NL7200948A NL7200948A (en) | 1971-02-03 | 1972-01-24 | |
| BE778707A BE778707A (en) | 1971-02-03 | 1972-01-31 | PROCESS FOR PREPARING OXAZINIC COLORANTS CONTAINING ARYLAMINE GROUPS AND NEW OXAZINIC COLORANTS |
| FR7203107A FR2124306B1 (en) | 1971-02-03 | 1972-01-31 | |
| IT48047/72A IT952020B (en) | 1971-02-03 | 1972-01-31 | PROCEDURE FOR THE PRODUCTION OF BONE DYES WITH ARYLAMINE GROUPS AND DYES OBTAINED |
| US00222678A US3828035A (en) | 1971-02-03 | 1972-02-01 | Production of oxazine dyes with arylamino groups |
| DD160637A DD95439A5 (en) | 1971-02-03 | 1972-02-02 | |
| GB480572A GB1379165A (en) | 1971-02-03 | 1972-02-02 | Oxazine dyes with an arylamino group |
| JP1146272A JPS5521072B1 (en) | 1971-02-03 | 1972-02-02 | |
| PL15324572A PL83378B1 (en) | 1971-11-24 | 1972-02-02 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712158121 DE2158121C3 (en) | 1971-11-24 | 1971-11-24 | Basic oxazine dyes, their preparation and use |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2158121A1 true DE2158121A1 (en) | 1973-06-07 |
| DE2158121B2 DE2158121B2 (en) | 1974-02-14 |
| DE2158121C3 DE2158121C3 (en) | 1984-08-30 |
Family
ID=5825930
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712158121 Expired DE2158121C3 (en) | 1971-02-03 | 1971-11-24 | Basic oxazine dyes, their preparation and use |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE2158121C3 (en) |
| PL (1) | PL83378B1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4880769A (en) * | 1986-12-24 | 1989-11-14 | Basf Aktiengesellschaft | Transfer of catinic dyes in their deprotonated, electrically neutral form |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE661783A (en) * | 1961-09-28 |
-
1971
- 1971-11-24 DE DE19712158121 patent/DE2158121C3/en not_active Expired
-
1972
- 1972-02-02 PL PL15324572A patent/PL83378B1/pl unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE661783A (en) * | 1961-09-28 |
Non-Patent Citations (1)
| Title |
|---|
| Bei der Bekanntmachung der Anmeldung sind drei mit Erläuterungen versehene Färbetafeln ausgelegt worden |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4880769A (en) * | 1986-12-24 | 1989-11-14 | Basf Aktiengesellschaft | Transfer of catinic dyes in their deprotonated, electrically neutral form |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2158121B2 (en) | 1974-02-14 |
| DE2158121C3 (en) | 1984-08-30 |
| PL83378B1 (en) | 1975-12-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8281 | Inventor (new situation) |
Free format text: BAUMANN, HANS, DR., 6700 LUDWIGSHAFEN, DE MAYER, UDO, DR., 6710 FRANKENTHAL, DE |
|
| C3 | Grant after two publication steps (3rd publication) |