CH640253A5 - AZO DYES. - Google Patents
AZO DYES. Download PDFInfo
- Publication number
- CH640253A5 CH640253A5 CH131279A CH131279A CH640253A5 CH 640253 A5 CH640253 A5 CH 640253A5 CH 131279 A CH131279 A CH 131279A CH 131279 A CH131279 A CH 131279A CH 640253 A5 CH640253 A5 CH 640253A5
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- Switzerland
- Prior art keywords
- dyes
- formula
- dye
- solution
- mixture
- Prior art date
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- 239000000975 dye Substances 0.000 claims description 46
- 239000000203 mixture Substances 0.000 claims description 20
- 238000004040 coloring Methods 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 7
- 239000002480 mineral oil Substances 0.000 claims description 7
- 235000010446 mineral oil Nutrition 0.000 claims description 7
- 239000003921 oil Substances 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 1
- 238000004043 dyeing Methods 0.000 claims 1
- 239000000243 solution Substances 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 238000002372 labelling Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- QNLZIZAQLLYXTC-UHFFFAOYSA-N 1,2-dimethylnaphthalene Chemical compound C1=CC=CC2=C(C)C(C)=CC=C21 QNLZIZAQLLYXTC-UHFFFAOYSA-N 0.000 description 2
- IVUQHXKKRQEFBU-UHFFFAOYSA-N 3-methyl-4-[(3-methylphenyl)diazenyl]aniline Chemical compound CC1=CC=CC(N=NC=2C(=CC(N)=CC=2)C)=C1 IVUQHXKKRQEFBU-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 238000006193 diazotization reaction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical class C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 1
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
- PMPBFICDXLLSRM-UHFFFAOYSA-N 1-propan-2-ylnaphthalene Chemical class C1=CC=C2C(C(C)C)=CC=CC2=C1 PMPBFICDXLLSRM-UHFFFAOYSA-N 0.000 description 1
- PRSBHXQGUJNHKA-UHFFFAOYSA-N 2-ethyl-3-methylnaphthalen-1-amine Chemical compound C(C)C1=C(C2=CC=CC=C2C=C1C)N PRSBHXQGUJNHKA-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 235000015243 ice cream Nutrition 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/003—Marking, e.g. coloration by addition of pigments
-
- 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
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/02—Disazo dyes
- C09B31/04—Disazo dyes from a coupling component "C" containing a directive amino group
- C09B31/053—Amino naphthalenes
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Lubricants (AREA)
- Optical Filters (AREA)
Description
Die Erfindung betrifft Azofarbstoffe der Formel (I) 60 The invention relates to azo dyes of the formula (I) 60
nur in verdünnter Mineralsäure mit Natriumnitrit diazotiert und anschliessend mit 2-Äthyl(Methyl)-aminonaphthalin kuppelt. Die Kupplung wird im allgemeinen im Temperaturbereich von 0 bis 40° C, vorzugsweise bei 5 bis 25° C, durchgeführt und liefert die Farbstoffe in nahezu quantiativer Ausbeute. diazotized only in dilute mineral acid with sodium nitrite and then coupled with 2-ethyl (methyl) -aminonaphthalene. The coupling is generally carried out in the temperature range from 0 to 40 ° C., preferably at 5 to 25 ° C., and provides the dyes in almost quantitative yield.
Die neuen, roten Farbstoffe sind in gegebenenfalls chlorierten Kohlenwasserstoffen, Alkoholen und Estern löslich und eignen sich zum Färben von Kunststoffen, Lacken, Wachsen, Fetten und insbesondere zum Färben und Kennzeichnen von Mineralölprodukten, wobei unter Mineralölprodukten vor allem Vergasertreibstoffe und Heizöle verstanden werden. The new, red dyes are soluble in optionally chlorinated hydrocarbons, alcohols and esters and are suitable for coloring plastics, paints, waxes, fats and in particular for coloring and labeling mineral oil products, whereby mineral oil products are understood to mean primarily gasoline fuels and heating oils.
Aus technischen Gründen werden die Farbstoffe zur Kennzeichnung von Mineralölprodukten bevorzugt in Form von Lösungen in aromatischen Kohlenwasserstoffen eingesetzt. Solche Lösungen enthalten ungefähr 5 bis 30 % Farbstoff und 95 bis 70 % Lösungsmittel. Als aromatische Kohlenwasserstoffe eignen sich insbesondere Alkylbenzole, Naphthalin und Alkylnaphthaline mit Ci-C4-Alkylgruppen. Im einzelnen seien beispielsweise To-luol, Xylole, Äthylbenzol, Isopropylbenzol, Mesitylen, Diphe-nyl, Naphthalin, Methylnaphthaline und Isopropylnaphthaline und insbesondere Mischungen dieser Aromaten genannt. For technical reasons, the dyes are preferably used to identify mineral oil products in the form of solutions in aromatic hydrocarbons. Such solutions contain approximately 5 to 30% dye and 95 to 70% solvent. Particularly suitable aromatic hydrocarbons are alkylbenzenes, naphthalene and alkylnaphthalenes with C 1 -C 4 -alkyl groups. Examples include to-toluene, xylenes, ethylbenzene, isopropylbenzene, mesitylene, diphenyl, naphthalene, methylnaphthalenes and isopropylnaphthalenes and in particular mixtures of these aromatics.
Die erfindungsgemässen Farbstoffe der Formel (I) haben den Vorteil, dass sie Farbstoffen der Formel (II), die an sich bekannt sind, in den genannten aromatischen Kohlenwasserstoffen, insbesondere in Mischung mit Furfurol, eine ausreichende Kältestabilitätverleihen, ohne dass weitere Lösungsmittel wie Cyclohex-anon erforderlich sind. The dyes of the formula (I) according to the invention have the advantage that they impart sufficient cold stability to dyes of the formula (II), which are known per se, in the aromatic hydrocarbons mentioned, in particular in a mixture with furfural, without further solvents such as cyclohexane. anon are required.
Die erfindungsgemässen Farbstoffe sind insbesondere im Gemisch mit den folgenden Farbstoffen zur Färbung und Kennzeichnung von Mineralölprodukten geeignet, wobei das Verhältnis I:IV:V vorzugsweise 20 bis 40:30 bis 60:20 bis 40 beträgt. The dyes according to the invention are particularly suitable in a mixture with the following dyes for coloring and labeling mineral oil products, the ratio I: IV: V preferably being from 20 to 40:30 to 60:20 to 40.
II II
/ V / V
f f
CH. CH.
-n=n -n = n
-// \ - // \
-N=N -N = N
CH. CH.
nh-c2h5 nh-c2h5
(I) (I)
65 65
7 a\-n=n-</ n)-n=n-// 7 a \ -n = n - </ n) -n = n - //
(IV) (IV)
3 640 253 3,640,253
Beispiel 3 Example 3
10 g eines Farbstoffgemisches, bestehend aus 50 Gew.-% des Farbstoffs der Formel (IV), 25 Gew.-% des Farbstoffs der (V) Formel (I) (R = Äthyl) und 25 Gew.-% des Farbstoffs der 10 g of a dye mixture consisting of 50% by weight of the dye of formula (IV), 25% by weight of the dye of (V) formula (I) (R = ethyl) and 25% by weight of the dye of
5 Formel (V) werden bei etwa 20° C in 70 g eines handelsüblichen Aromatengemisches (technisches Dimethylnaphthalin) mit einem Siedebereich von oberhalb 200° C und 20 g Furfurol gelöst. Die Lösung wird gegebenenfalls von geringen Mengen unlöslicher Verunreinigungen durch Filtration befreit. Die Lösung 10 bleibt bei —15° C unverändert. 5 Formula (V) are dissolved at about 20 ° C in 70 g of a commercially available aromatic mixture (technical dimethylnaphthalene) with a boiling range above 200 ° C and 20 g furfural. If necessary, the solution is freed from small amounts of insoluble impurities by filtration. Solution 10 remains unchanged at -15 ° C.
Dagegen ist eine Lösung aus 10 g des Farbstoffs der Formel (IV) in 70 g des o.g. Aromatengemisches und 20 g Furfurol nicht kältestabil. In contrast, a solution of 10 g of the dye of formula (IV) in 70 g of the above. Aromatic mixture and 20 g furfurol not stable to cold.
22,5 g 4-Amino-2,3'-dimethylazobenzol werden in einer Lö- Die o.g. Lösung der Farbstoffmischung eignet sich zur Kenn- 22.5 g of 4-amino-2,3'-dimethylazobenzene are dissolved in a solvent. Solution of the dye mixture is suitable for
sung aus 6,9 g Natriumnitrit in 200 g Wasser ca. 3 h bei is Zeichnung von leichtem Heizöl. Dazu werden 50 g der Kenn- solution of 6.9 g sodium nitrite in 200 g water for approx. 3 h with the drawing of light heating oil. 50 g of the identification
Raumtemperatur verrührt. Diese Suspension wird unter Rühren Zeichnungslösung pro 1000 kg Heizöl verwendet. Stirred room temperature. This suspension is used with stirring drawing solution per 1000 kg of heating oil.
in eine Vorlage aus 30 g Wasser, 45 g Salzsäure (19,5° Bé) und 30 Statt 10 g eines Farbstoffgemisches, bestehen aus 50 Gew.-% g Eis gegeben. Die Diazotierung ist im Verlauf von ca. 3 h bei des Farbstoffs der Formel (IV), 25 Gew.-% des Farbstoffs I (R = placed in a template of 30 g of water, 45 g of hydrochloric acid (19.5 ° Bé) and 30 instead of 10 g of a dye mixture consist of 50 wt .-% g of ice. The diazotization is in the course of about 3 hours for the dye of the formula (IV), 25% by weight of the dye I (R =
etwa 20° C beendet. Man lässt die Lösung zur Trennung von Äthyl) und 25 Gew. -% des Farbstoffs V kann man auch 5 g des geringen Verunreinigungen durch ein Filter laufen und zersetzt 20 nach Beispiel 2 erhaltenen Farbstoffgemischs und 5 g des Farb-den Nitritüberschuss mit Amidosulfonsäure. In die mit 30 g Eis stoffs IV verwenden. about 20 ° C ended. The solution for separating ethyl) and 25% by weight of the dye V is also allowed to pass 5 g of the minor impurities through a filter and decomposes 20 dye mixture obtained according to Example 2 and 5 g of the dye-the nitrite excess with amidosulfonic acid. Use in with 30 g of ice cream IV.
versetzte Diazoniumsalzlösung gibt man unter Rühren bei 15 bis added diazonium salt solution is added with stirring at 15 to
20° C eine Suspension aus 18 g 2-N-Äthylnaphthylamin in 160 g Beispiel 4 20 ° C a suspension of 18 g of 2-N-ethylnaphthylamine in 160 g of Example 4
Wasser und 25 g Salzsäure (19,5° Bé). Nach der Kupplung wird 12,5 g eines Farbstoffgemisches, bestehend aus 40 Gew.-% des der Farbstoff abfiltriert, mit Wasser neutral gewaschen und 25 Farbstoffs IV, 30 Gew.-% des Farbstoffes I (R = Äthyl) und 30 getrocknet. Man erhält 35,7 g. Gew.-% des Farbstoffs V werden bei 20° C in 87,5 g des in Water and 25 g hydrochloric acid (19.5 ° Bé). After coupling, 12.5 g of a dye mixture consisting of 40% by weight of the dye is filtered off, washed neutral with water and 25 dye IV, 30% by weight of dye I (R = ethyl) and 30 dried. 35.7 g are obtained. % By weight of the dye V are at 20 ° C. in 87.5 g of the in
Beispiel 3 genannten Aromatengemisches gelöst. Die Lösung wird gegebenenfalls von geringen Mengen unlöslicher Verunreinigungen durch Filtration befreit. Die Lösung bleibt bei — 15°C Beispiel 2 30 unverändert stabil. Example 3 aromatic mixture dissolved. If necessary, the solution is freed from small amounts of insoluble impurities by filtration. The solution remains stable at −15 ° C. Example 2 30 unchanged.
45 g 4-Amino-2,3'-dimethylazobenzol werden in einer Lösung Dagegen ist eine Lösung des Farbstoffs IV bei entsprechender aus 13,8 g Natriumnitrit in 400 g Wasser ca. 3 h bei Raumtempe- Farbstoffkonzentration in dem o.g. Aromatengemisch nach eini-ratur verrührt. Diese Suspension wird unter Rühren in eine ger Zeit bei —15° C teilweise kristallisiert. 45 g of 4-amino-2,3'-dimethylazobenzene are in a solution. On the other hand, a solution of the dye IV, with the corresponding 13.8 g of sodium nitrite in 400 g of water, is approx. 3 h at room temperature dye concentration in the above. Aromatic mixture stirred after iniature. This suspension is partially crystallized with stirring at -15 ° C for some time.
Vorlage aus 60 g Wasser, 90 g Salzsäure (19,5° Bé) und 60 g Eis Anstelle von 12,5 g eines Farbstoffgemisches aus 40 Gew.-% Preparation from 60 g of water, 90 g of hydrochloric acid (19.5 ° Bé) and 60 g of ice instead of 12.5 g of a dye mixture of 40% by weight
gegeben. Die Diazotierung ist im Verlauf von etwa 3 h bei 20° C 35 des Farbstoffs IV, 30 Gew.-% des Farbstoffs I (R = Äthyl) und beendet. Gegebenenfalls werden anschliessend geringe Mengen 30 Gew.-% des Farbstoffs V kann man auch 5 g Farbstoff IV und Verunreinigungen abfiltriert. Der Nitritüberschuss wird mit 7,5 g des nach Beispiel 2 erhaltenen Farbstoffgemisches ein- given. The diazotization is complete in the course of about 3 hours at 20 ° C. 35 of dye IV, 30% by weight of dye I (R = ethyl). If necessary, small amounts of 30% by weight of dye V can then be filtered off, 5 g of dye IV and impurities. The excess nitrite is mixed with 7.5 g of the dye mixture obtained according to Example 2.
Amidosulfonsäure zerstört. In die mit 60 g Eis versetzte Diazo- setzen. Amidosulfonic acid destroyed. Place in the diazo with 60 g ice.
niumsalzlösung wird bei 15 bis 20° C unter Rühren eine Suspen- Anstelle von 87,5 g des in Beispiel 3 genannten Aromatengesion aus 18 g 2-N-Äthylnaphthylamin und 19,6 g 2-N-Isopropyl- 40 misches kann man auch 75 g dieses Lösungsmittels und 12,5 g naphthylamin in 320 g Wasser und 50 g Salzsäure (19,5°Bé) Furfurol einsetzen. Die so erhaltene Farbstofflösung ist ebenfalls gegeben. Nach beendeter Kupplung wird das Farbstoffgemisch kältestabil und eignet sich zur Kennzeichnung von leichtem abfiltriert, mit Wasser neutral gewaschen und getrocknet. Man Heizöl. Dazu werden 40 g der Kennzeichnungslösung pro 1000 kg erhält 74 g Heizöl verwendet. niumsalzlösung is at 15 to 20 ° C with stirring a Suspen- instead of 87.5 g of the aromatics mentioned in Example 3 from 18 g of 2-N-ethylnaphthylamine and 19.6 g of 2-N-isopropyl 40 one can also mix 75 Use g of this solvent and 12.5 g naphthylamine in 320 g water and 50 g hydrochloric acid (19.5 ° Bé) furfurol. The dye solution thus obtained is also given. After the coupling has ended, the dye mixture becomes stable to cold and is suitable for labeling lightly filtered off, washed neutral with water and dried. Man heating oil. For this purpose, 40 g of the labeling solution per 1000 kg receives 74 g of heating oil.
45 45
Claims (7)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2805809A DE2805809C2 (en) | 1978-02-11 | 1978-02-11 | Dye mixtures and their use |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH640253A5 true CH640253A5 (en) | 1983-12-30 |
Family
ID=6031703
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH131279A CH640253A5 (en) | 1978-02-11 | 1979-02-09 | AZO DYES. |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE874062A (en) |
| CH (1) | CH640253A5 (en) |
| DE (1) | DE2805809C2 (en) |
| FR (1) | FR2416923A1 (en) |
| GB (1) | GB2014179B (en) |
| IT (1) | IT7920105A0 (en) |
| NL (1) | NL7900745A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20130104447A1 (en) | 2011-10-28 | 2013-05-02 | Exxonmobil Research And Engineering Company | Dye-stable biofuel blend compositions |
| TWD209552S (en) * | 2020-05-08 | 2021-01-21 | 美商阿姆斯國際股份有限公司 | Cup |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US400985A (en) * | 1889-04-09 | willis | ||
| DE1645876A1 (en) * | 1951-01-28 | 1970-12-23 | Bayer Ag | Process for coloring organic solvents |
| DE1185226B (en) * | 1963-07-16 | 1965-01-14 | Standard Elektrik Lorenz Ag | Counting chain made of electronic switching units |
| US4315756A (en) * | 1973-12-12 | 1982-02-16 | Basf Aktiengesellschaft | Oil-soluble azo dye with N-substituted β-naphthylamine as coupling component |
| DE2361758A1 (en) * | 1973-12-12 | 1975-06-26 | Basf Ag | Amino-naphthyl-azo compounds - as colouring agents |
| DE2413369B2 (en) * | 1974-03-20 | 1978-09-21 | Basf Ag, 6700 Ludwigshafen | Water-insoluble disazo dyes, process for their preparation and their use for coloring mineral oil distillation products |
| FR2276355A1 (en) * | 1974-06-28 | 1976-01-23 | Ugine Kuhlmann | NEW LIQUID AZO-NAPHTHALENIC DYES |
| US4000985A (en) * | 1975-08-01 | 1977-01-04 | Morton-Norwich Products, Inc. | Azo dyes having a high solubility in petroleum fuels |
| DE2603918C3 (en) * | 1976-02-03 | 1979-01-18 | Basf Ag, 6700 Ludwigshafen | Color solutions for petroleum products |
-
1978
- 1978-02-11 DE DE2805809A patent/DE2805809C2/en not_active Expired
-
1979
- 1979-01-30 NL NL7900745A patent/NL7900745A/en not_active Application Discontinuation
- 1979-02-05 GB GB7904007A patent/GB2014179B/en not_active Expired
- 1979-02-09 CH CH131279A patent/CH640253A5/en not_active IP Right Cessation
- 1979-02-09 IT IT7920105A patent/IT7920105A0/en unknown
- 1979-02-09 FR FR7903333A patent/FR2416923A1/en not_active Withdrawn
- 1979-02-09 BE BE0/193372A patent/BE874062A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE2805809A1 (en) | 1979-08-23 |
| DE2805809C2 (en) | 1983-05-26 |
| GB2014179A (en) | 1979-08-22 |
| IT7920105A0 (en) | 1979-02-09 |
| GB2014179B (en) | 1982-07-28 |
| NL7900745A (en) | 1979-08-14 |
| BE874062A (en) | 1979-08-09 |
| FR2416923A1 (en) | 1979-09-07 |
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