CH617448A5 - Process for preparing basic oxazine dyes - Google Patents
Process for preparing basic oxazine dyes Download PDFInfo
- Publication number
- CH617448A5 CH617448A5 CH909875A CH909875A CH617448A5 CH 617448 A5 CH617448 A5 CH 617448A5 CH 909875 A CH909875 A CH 909875A CH 909875 A CH909875 A CH 909875A CH 617448 A5 CH617448 A5 CH 617448A5
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- oxazine dyes
- water
- mixture
- ether
- Prior art date
Links
- 239000000975 dye Substances 0.000 title description 16
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 title description 11
- 238000004519 manufacturing process Methods 0.000 title description 2
- 238000000034 method Methods 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 239000000203 mixture Substances 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 9
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
- 150000004292 cyclic ethers Chemical class 0.000 description 7
- 150000002832 nitroso derivatives Chemical class 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 238000009833 condensation Methods 0.000 description 6
- 230000005494 condensation Effects 0.000 description 6
- 230000009935 nitrosation Effects 0.000 description 6
- 238000007034 nitrosation reaction Methods 0.000 description 6
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 2
- WAVOOWVINKGEHS-UHFFFAOYSA-N 3-(diethylamino)phenol Chemical compound CCN(CC)C1=CC=CC(O)=C1 WAVOOWVINKGEHS-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- -1 cyclic sulfone Chemical class 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- KHSTZMGCKHBFJX-UHFFFAOYSA-N 3-(dibutylamino)phenol Chemical compound CCCCN(CCCC)C1=CC=CC(O)=C1 KHSTZMGCKHBFJX-UHFFFAOYSA-N 0.000 description 1
- MESJRHHDBDCQTH-UHFFFAOYSA-N 3-(dimethylamino)phenol Chemical compound CN(C)C1=CC=CC(O)=C1 MESJRHHDBDCQTH-UHFFFAOYSA-N 0.000 description 1
- ODQSBWZDOSNPAH-UHFFFAOYSA-N 3-ethoxy-n,n-diethylaniline Chemical compound CCOC1=CC=CC(N(CC)CC)=C1 ODQSBWZDOSNPAH-UHFFFAOYSA-N 0.000 description 1
- RHFQRLVXCZQRLQ-UHFFFAOYSA-N 3-ethyl-2-(methylamino)phenol Chemical compound CCC1=CC=CC(O)=C1NC RHFQRLVXCZQRLQ-UHFFFAOYSA-N 0.000 description 1
- RGOFZIBJUMVVOL-UHFFFAOYSA-N 5-ethyl-5-(1-ethylcyclohexa-2,4-dien-1-yl)oxycyclohexa-1,3-diene Chemical compound C(C)C1(CC=CC=C1)OC1(CC=CC=C1)CC RGOFZIBJUMVVOL-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 101100387923 Caenorhabditis elegans dos-1 gene Proteins 0.000 description 1
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 150000004893 oxazines Chemical class 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000131 polyvinylidene Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000037380 skin damage Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride 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
- C09B19/00—Oxazine dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Coloring (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH909875A CH617448A5 (en) | 1975-07-11 | 1975-07-11 | Process for preparing basic oxazine dyes |
| GB2847376A GB1550868A (en) | 1975-07-11 | 1976-07-08 | Process for the manufacture of basic oxazine dyestuffs |
| JP8046376A JPS5210328A (en) | 1975-07-11 | 1976-07-08 | Process for producing basic oxazine dyes |
| BR7604498A BR7604498A (pt) | 1975-07-11 | 1976-07-09 | Processo para a preparacao de corantes oxazinicos basicos |
| FR7621179A FR2317336A1 (fr) | 1975-07-11 | 1976-07-09 | Procede de preparation de colorants oxaziniques basiques |
| DE19762631040 DE2631040A1 (de) | 1975-07-11 | 1976-07-09 | Verfahren zur herstellung basischer oxazinfarbstoffe |
| ES449746A ES449746A1 (es) | 1975-07-11 | 1976-07-10 | Procedimiento para la preparacion de colorantes de oxacina basicos. |
| US05/862,881 US4196286A (en) | 1975-07-11 | 1977-12-21 | Process for the manufacture of basic oxazine dyestuffs |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH909875A CH617448A5 (en) | 1975-07-11 | 1975-07-11 | Process for preparing basic oxazine dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH617448A5 true CH617448A5 (en) | 1980-05-30 |
Family
ID=4348294
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH909875A CH617448A5 (en) | 1975-07-11 | 1975-07-11 | Process for preparing basic oxazine dyes |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS5210328A (en:Method) |
| BR (1) | BR7604498A (en:Method) |
| CH (1) | CH617448A5 (en:Method) |
| DE (1) | DE2631040A1 (en:Method) |
| ES (1) | ES449746A1 (en:Method) |
| FR (1) | FR2317336A1 (en:Method) |
| GB (1) | GB1550868A (en:Method) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2480767A1 (fr) * | 1980-04-18 | 1981-10-23 | Ugine Kuhlmann | Procede de preparation de colorants oxaziniques basiques |
| DE3033439A1 (de) * | 1980-09-05 | 1982-04-22 | Basf Ag, 6700 Ludwigshafen | Basische farbstoffe der oxazinreihe |
| FR2693468A1 (fr) * | 1992-07-10 | 1994-01-14 | Ciba Geigy Ag | Procédé de préparation de colorants de type oxazine. |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2036034A5 (en) * | 1969-03-03 | 1970-12-24 | Hoechst Ag | Basic oxazine dyestuffs |
| NL7200948A (en:Method) * | 1971-02-03 | 1972-08-07 | ||
| DE2353987C3 (de) * | 1973-10-27 | 1978-08-24 | Bayer Ag, 5090 Leverkusen | Verfahren zur Isolierung leichtlöslicher basischer Oxazin- und Phenazinfarbstoffe |
| CH593321A5 (en:Method) * | 1974-04-29 | 1977-11-30 | Ciba Geigy Ag |
-
1975
- 1975-07-11 CH CH909875A patent/CH617448A5/de not_active IP Right Cessation
-
1976
- 1976-07-08 GB GB2847376A patent/GB1550868A/en not_active Expired
- 1976-07-08 JP JP8046376A patent/JPS5210328A/ja active Pending
- 1976-07-09 FR FR7621179A patent/FR2317336A1/fr active Granted
- 1976-07-09 BR BR7604498A patent/BR7604498A/pt unknown
- 1976-07-09 DE DE19762631040 patent/DE2631040A1/de active Pending
- 1976-07-10 ES ES449746A patent/ES449746A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2317336A1 (fr) | 1977-02-04 |
| BR7604498A (pt) | 1977-08-02 |
| ES449746A1 (es) | 1977-08-16 |
| GB1550868A (en) | 1979-08-22 |
| JPS5210328A (en) | 1977-01-26 |
| FR2317336B1 (en:Method) | 1978-05-19 |
| DE2631040A1 (de) | 1977-01-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |