DE268792C - - Google Patents
Info
- Publication number
- DE268792C DE268792C DENDAT268792D DE268792DA DE268792C DE 268792 C DE268792 C DE 268792C DE NDAT268792 D DENDAT268792 D DE NDAT268792D DE 268792D A DE268792D A DE 268792DA DE 268792 C DE268792 C DE 268792C
- Authority
- DE
- Germany
- Prior art keywords
- sulfonic acid
- aminonaphthol
- amino
- derivatives
- 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.)
- Active
Links
- 239000000975 dye Substances 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 230000001808 coupling Effects 0.000 claims description 3
- 238000010168 coupling process Methods 0.000 claims description 3
- 238000005859 coupling reaction Methods 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 150000008049 diazo compounds Chemical class 0.000 claims description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- YUNBHHWDQDGWHC-UHFFFAOYSA-N 6-aminonaphthalene-1-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC2=CC(N)=CC=C21 YUNBHHWDQDGWHC-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- QELUYTUMUWHWMC-UHFFFAOYSA-N Edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- -1 aminophenyl Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- BHKWXQBWGLKDKU-UHFFFAOYSA-N 3-(aminodiazenyl)benzene-1,2-disulfonic acid Chemical compound NN=NC1=CC=CC(S(O)(=O)=O)=C1S(O)(=O)=O BHKWXQBWGLKDKU-UHFFFAOYSA-N 0.000 description 1
- KYUJRVJIBJQDFR-UHFFFAOYSA-N 4-amino-2-chloro-3-methylbenzenesulfonic acid Chemical compound CC1=C(N)C=CC(S(O)(=O)=O)=C1Cl KYUJRVJIBJQDFR-UHFFFAOYSA-N 0.000 description 1
- DYRDKSSFIWVSNM-UHFFFAOYSA-N Acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 229950009041 edaravone Drugs 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 235000021384 green leafy vegetables Nutrition 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 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
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- KLASSE-22«. GRUPPE- CLASS-22 «. GROUP
FARBENFABRIKEN vorm. FRIEDR. BAYER & CO ^LEVERKUSEN b. CÖLN.FARBENFABRIKEN vorm. FRIEDR. BAYER & CO ^ LEVERKUSEN b. COLOGNE.
Verfahren zur Darstellung von Entwicklerfarbstoffen. Patentiert im Deutschen Reiche vom 28. Dezember 1912 ab.Process for the preparation of developer dyes. Patented in the German Empire on December 28, 1912.
Es wurde gefunden, daß man zu wertvollen Entwicklerfarbstoffen gelangt, wenn man die Farbstoffe, welche durch Kupplung von beliebigen Diazo- oder Diazoazoverbindungen auf ι · 5-Aminonaphtol und seine Sulfosäuren nach der Aminoseite erhältlich sind, weiter diazotiert und mit solchen Derivaten der 2-5-Aminonaphtol-7-sulfosäure oder ihren in i-Stellung substituierten Derivaten vereinigt, die in heteronuklearen Seitenketten diazotierbare Aminogruppen erhalten.It has been found that valuable developer dyes can be obtained by using the Dyes obtained by coupling any diazo or diazoazo compounds ι · 5-Aminonaphtol and its sulfonic acids are obtainable on the amino side, further diazotized and with such derivatives of 2-5-aminonaphthol-7-sulfonic acid or their derivatives substituted in i-position combined, which in heteronuclear side chains obtained diazotizable amino groups.
Solche Derivate der 2 · 5-Aminonaphtol-7-sulfosäure sind z. B. die Aminobenzoyl-2 · 5-aminonaphtol-7-sulfosäure (Patentschrift 170045), Aminophenyl -1 · 2-naphtimidazol-5-oxy-7-sulfosäure (Patentschrift 172319), Aminophenyl-i · 2-naphtothiazol-5-oxy-7-sulfosäure (Patentschrift 165126), Amino-y-5-oxy-7-sulfo-2-naphtylbenzimidazol (Patentschrift 252575).Such derivatives of 2 x 5-aminonaphthol-7-sulfonic acid are e.g. B. the aminobenzoyl-2 · 5-aminonaphthol-7-sulfonic acid (Patent 170045), aminophenyl -1 x 2-naphtimidazole-5-oxy-7-sulfonic acid (Patent 172319), aminophenyl-i.2-naphtothiazole-5-oxy-7-sulfonic acid (Patent 165126), Amino-y-5-oxy-7-sulfo-2-naphthylbenzimidazole (Patent 252575).
Die neuen Produkte färben die Baumwolle in stumpfen, blau- bis grünschwarzen Nuancen an und lassen sich überraschenderweise durch Diazotierung auf der Faser und Nachbehandlung mit geeigneten Entwicklern, wie Phenylmethylpyrazolon, Acetessiganilid u. a. zu licht- und waschechten Grüns entwickeln, wie sie von ähnlicher Klarheit und Lichtechtheit bisher nicht erreichbar waren.The new products dye the cotton in dull, blue to green-black nuances and surprisingly, by diazotization on the fiber and aftertreatment with suitable developers such as phenylmethylpyrazolone, aceto-aceticanilide and others. to light and Real greens develop as they have so far been of similar clarity and lightfastness were not available.
Die Diazoverbindung aus 223 Teilen 2-Naphtylamin-5-sulfosäure wird mit 303 Teilen des Natriumsalzes der in der Hydroxylgruppe acetylierten 1 · 5 - Aminonaphtol- 7 - sulfosäure zum Zwischenprodukt vereinigt, mit 69 Teilen Natriumnitrit und Salzsäure weiter diazotiert und alsdann zu einer überschüssige Soda enthaltenden Lösung von 380 Teilen 4'-aminobenzoyl-2 · 5-aminonaphtol-7-sulfosauren Natriums gegeben; nach eventuell weiterem Zusatz von Soda wird die Acetylgruppe durch Aufkochen abgespalten und der Farbstoff durch Aussalzen isoliert. Er färbt auf Baumwolle ein grünstichiges Blauschwarz, das mit Methylphenylpyrazolon entwickelt ein schönes gelbstichiges Grün liefert.The diazo compound from 223 parts of 2-naphthylamine-5-sulfonic acid is with 303 parts of the sodium salt of the 1 · 5 - aminonaphthol- 7 - sulfonic acid acetylated in the hydroxyl group Combined intermediate product, further diazotized with 69 parts of sodium nitrite and hydrochloric acid and then to a solution of 380 parts of 4'-aminobenzoyl-2 containing excess soda · Given 5-aminonaphthol-7-sulphonic acid sodium; after any further addition of soda, the acetyl group is boiled up split off and the dye isolated by salting out. It dyes a greenish blue-black on cotton with methylphenylpyrazolone develops a beautiful yellowish green.
Statt der 2-Naphtylamin-5-sulfosäure können andere diazotierbare aromatische Aminoverbindungen und Aminoazoverbindungen verwendet werden, wie z. B. 2-Naphtylamin-4 · 8-disulfosäure, i-Naphtylamin-4-sulfosäure, 3-Chlor-2-toluidin-4-sulfosäure, p-Nitranilin-o-sulfosäure, Aminoazobenzoldisulfosäure usw. An Stelle der in der Hydroxylgruppe acidylierten 1-5-Aminonaphtol-7-sulfosäure kann diese selbst oder das 1 · 5-Aminonaphtol oder die 1 · 5-Aminonaphtol-6-suHosäure verwendet werden, wobei die Kupplung nach der Aminoseite erfolgen muß. An Stelle der Amino benzoyl-2 · 5-aminonaphtol-7-sulfosäure kann man ganz allgemein solche heteronukleare Derivate der 2 · 5-Aminonaphtol-7-sulfosäure und ihrer in i-Stellung substituierten Derivate verwenden, die eine diazotierbare Aminogruppe enthalten, wie z. B. Aminophenyl-i · 2-naphtimidazol-5-oxy-7-sulfosäure (Patentschrift 172319), Aminoy-5-oxy-7-sulfo-2-naphtylbenzimidazol (Patentschrift 252575).Instead of 2-naphthylamine-5-sulfonic acid, other diazotizable aromatic amino compounds can be used and aminoazo compounds can be used, e.g. B. 2-naphthylamine-4 · 8-disulfonic acid, i-naphthylamine-4-sulfonic acid, 3-chloro-2-toluidine-4-sulfonic acid, p-Nitraniline-o-sulfonic acid, aminoazobenzene disulfonic acid, etc. in place 1-5-aminonaphthol-7-sulfonic acid acidylated in the hydroxyl group can this itself or the 1x5-aminonaphtol or the 1x5-aminonaphthol-6-suHosäure can be used, the coupling must take place after the amino side. Instead of the amino benzoyl-2 · 5-aminonaphthol-7-sulfonic acid can be used quite generally such heteronuclear derivatives of Use 2 5-aminonaphthol-7-sulfonic acid and its derivatives substituted in i-position, which contain a diazotizable amino group, such as. B. Aminophenyl-i.2-naphthimidazole-5-oxy-7-sulfonic acid (Patent 172319), Aminoy-5-oxy-7-sulfo-2-naphthylbenzimidazole (Patent 252575).
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE268792C true DE268792C (en) |
Family
ID=525722
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT268792D Active DE268792C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE268792C (en) |
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- DE DENDAT268792D patent/DE268792C/de active Active
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