DE1106442B - Verfahren zur Herstellung von Farbstoffen - Google Patents
Verfahren zur Herstellung von FarbstoffenInfo
- Publication number
- DE1106442B DE1106442B DEF23379A DEF0023379A DE1106442B DE 1106442 B DE1106442 B DE 1106442B DE F23379 A DEF23379 A DE F23379A DE F0023379 A DEF0023379 A DE F0023379A DE 1106442 B DE1106442 B DE 1106442B
- Authority
- DE
- Germany
- Prior art keywords
- parts
- weight
- imino
- amino
- dithia
- 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
- 239000000975 dye Substances 0.000 title claims description 29
- 238000000034 method Methods 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title description 3
- 229910001385 heavy metal Inorganic materials 0.000 claims description 9
- 150000002736 metal compounds Chemical class 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 3
- 239000000758 substrate Substances 0.000 claims description 3
- 238000004040 coloring Methods 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- FBSVHCGELQWERO-UHFFFAOYSA-N 2,3-dihydro-1,4-dithiine-5,6-dicarbonitrile Chemical compound N#CC1=C(C#N)SCCS1 FBSVHCGELQWERO-UHFFFAOYSA-N 0.000 description 6
- 229920000742 Cotton Polymers 0.000 description 6
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 229910021529 ammonia Inorganic materials 0.000 description 6
- 239000000835 fiber Substances 0.000 description 6
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 6
- 229950006389 thiodiglycol Drugs 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- -1 1,2-dicyano-4,6-dithiacyclohexene Chemical class 0.000 description 5
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 4
- 241000416162 Astragalus gummifer Species 0.000 description 4
- 229920001615 Tragacanth Polymers 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 150000003335 secondary amines Chemical class 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 230000008719 thickening Effects 0.000 description 4
- 239000000196 tragacanth Substances 0.000 description 4
- 229940116362 tragacanth Drugs 0.000 description 4
- 235000010487 tragacanth Nutrition 0.000 description 4
- RZVCEPSDYHAHLX-UHFFFAOYSA-N 3-iminoisoindol-1-amine Chemical compound C1=CC=C2C(N)=NC(=N)C2=C1 RZVCEPSDYHAHLX-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- MQRWBMAEBQOWAF-UHFFFAOYSA-N acetic acid;nickel Chemical compound [Ni].CC(O)=O.CC(O)=O MQRWBMAEBQOWAF-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 229940078494 nickel acetate Drugs 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- QCYJCZJMOAWVPC-UHFFFAOYSA-N 1-phenyl-1,2,4-triazole-3,5-diamine Chemical compound N1=C(N)N=C(N)N1C1=CC=CC=C1 QCYJCZJMOAWVPC-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- 239000012433 hydrogen halide Substances 0.000 description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine group Chemical group N1=CCC2=CC=CC=C12 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 2
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 2
- 239000002964 rayon Substances 0.000 description 2
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000010025 steaming Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 229960004418 trolamine Drugs 0.000 description 2
- XTFKKPTYHWLGMD-UHFFFAOYSA-N 5-imino-2,3-dihydro-[1,4]dithiino[2,3-c]pyrrol-7-amine Chemical compound S1CCSC2=C1C(N)=NC2=N XTFKKPTYHWLGMD-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 108010077895 Sarcosine Proteins 0.000 description 1
- 241000872198 Serjania polyphylla Species 0.000 description 1
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001049 brown dye Substances 0.000 description 1
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- JIKUXBYRTXDNIY-UHFFFAOYSA-N n-methyl-n-phenylformamide Chemical compound O=CN(C)C1=CC=CC=C1 JIKUXBYRTXDNIY-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229940043230 sarcosine Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure Methods 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
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/06—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide
- C09B47/073—Preparation from isoindolenines, e.g. pyrrolenines
-
- 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
- C09B47/00—Porphines; Azaporphines
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F15—FLUID-PRESSURE ACTUATORS; HYDRAULICS OR PNEUMATICS IN GENERAL
- F15B—SYSTEMS ACTING BY MEANS OF FLUIDS IN GENERAL; FLUID-PRESSURE ACTUATORS, e.g. SERVOMOTORS; DETAILS OF FLUID-PRESSURE SYSTEMS, NOT OTHERWISE PROVIDED FOR
- F15B21/00—Common features of fluid actuator systems; Fluid-pressure actuator systems or details thereof, not covered by any other group of this subclass
- F15B21/10—Delay devices or arrangements
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Analytical Chemistry (AREA)
- Physics & Mathematics (AREA)
- Fluid Mechanics (AREA)
- Mechanical Engineering (AREA)
- General Engineering & Computer Science (AREA)
- Coloring (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF23379A DE1106442B (de) | 1957-07-02 | 1957-07-02 | Verfahren zur Herstellung von Farbstoffen |
| CH5673958A CH407377A (de) | 1957-07-02 | 1958-03-07 | Verfahren zur Herstellung von Farbstoffen |
| NL225931A NL108882C (en, 2012) | 1957-07-02 | 1958-03-17 | |
| FR1205880D FR1205880A (fr) | 1957-07-02 | 1958-03-17 | Procédé de préparation de colorants |
| BE565805D BE565805A (en, 2012) | 1957-07-02 | 1958-03-18 | |
| GB873658A GB881410A (en) | 1957-07-02 | 1958-03-18 | Process for the manufacture of dyestuffs of the tetrazaporphin series |
| FR44314A FR1379959A (fr) | 1957-07-02 | 1963-12-27 | Dispositif de freinage pour le réglage de la vitesse de la course aller du piston de vérins pneumatiques |
| CH102964A CH411587A (de) | 1957-07-02 | 1964-01-29 | Bremsvorrichtung zur Regulierung der Vorlaufgeschwindigkeit des Kolbens von pneumatischen Arbeitszylindern |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF23379A DE1106442B (de) | 1957-07-02 | 1957-07-02 | Verfahren zur Herstellung von Farbstoffen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1106442B true DE1106442B (de) | 1961-05-10 |
Family
ID=7090814
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF23379A Pending DE1106442B (de) | 1957-07-02 | 1957-07-02 | Verfahren zur Herstellung von Farbstoffen |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE565805A (en, 2012) |
| CH (2) | CH407377A (en, 2012) |
| DE (1) | DE1106442B (en, 2012) |
| FR (2) | FR1205880A (en, 2012) |
| GB (1) | GB881410A (en, 2012) |
| NL (1) | NL108882C (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2625967A1 (de) * | 1975-06-19 | 1977-04-07 | Ciba Geigy Ag | Neue lichtschutzmittel |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1001785B (de) | 1954-01-07 | 1957-01-31 | Bayer Ag | Verfahren zur Herstellung von Tetrazaporphinen |
-
1957
- 1957-07-02 DE DEF23379A patent/DE1106442B/de active Pending
-
1958
- 1958-03-07 CH CH5673958A patent/CH407377A/de unknown
- 1958-03-17 FR FR1205880D patent/FR1205880A/fr not_active Expired
- 1958-03-17 NL NL225931A patent/NL108882C/xx active
- 1958-03-18 GB GB873658A patent/GB881410A/en not_active Expired
- 1958-03-18 BE BE565805D patent/BE565805A/xx unknown
-
1963
- 1963-12-27 FR FR44314A patent/FR1379959A/fr not_active Expired
-
1964
- 1964-01-29 CH CH102964A patent/CH411587A/de unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1001785B (de) | 1954-01-07 | 1957-01-31 | Bayer Ag | Verfahren zur Herstellung von Tetrazaporphinen |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2625967A1 (de) * | 1975-06-19 | 1977-04-07 | Ciba Geigy Ag | Neue lichtschutzmittel |
Also Published As
| Publication number | Publication date |
|---|---|
| CH407377A (de) | 1966-02-15 |
| GB881410A (en) | 1961-11-01 |
| FR1205880A (fr) | 1960-02-05 |
| BE565805A (en, 2012) | 1960-07-29 |
| FR1379959A (fr) | 1964-11-27 |
| CH411587A (de) | 1966-04-15 |
| NL108882C (en, 2012) | 1964-07-15 |
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