DE129494C - - Google Patents
Info
- Publication number
- DE129494C DE129494C DE1900129494D DE129494DA DE129494C DE 129494 C DE129494 C DE 129494C DE 1900129494 D DE1900129494 D DE 1900129494D DE 129494D A DE129494D A DE 129494DA DE 129494 C DE129494 C DE 129494C
- Authority
- DE
- Germany
- Prior art keywords
- sulfonic acid
- naphthylamine
- naphthol
- dye
- 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.)
- Expired - Lifetime
Links
- 239000000975 dye Substances 0.000 claims description 27
- LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 10
- 229920000742 Cotton Polymers 0.000 claims description 8
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- 150000008049 diazo compounds Chemical class 0.000 claims description 6
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-Naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 235000010288 sodium nitrite Nutrition 0.000 claims description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 4
- 239000000982 direct dye Substances 0.000 claims description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 238000010168 coupling process Methods 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 2
- 230000001808 coupling Effects 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- IMPPGHMHELILKG-UHFFFAOYSA-N 4-ethoxyaniline Chemical compound CCOC1=CC=C(N)C=C1 IMPPGHMHELILKG-UHFFFAOYSA-N 0.000 claims 4
- 240000000358 Viola adunca Species 0.000 claims 2
- 239000000987 azo dye Substances 0.000 claims 2
- 239000000835 fiber Substances 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 159000000000 sodium salts Chemical class 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 claims 1
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-Naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 claims 1
- VVPHSMHEYVOVLH-UHFFFAOYSA-N 6-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=CC2=CC(O)=CC=C21 VVPHSMHEYVOVLH-UHFFFAOYSA-N 0.000 claims 1
- 235000005811 Viola adunca Nutrition 0.000 claims 1
- 235000013487 Viola odorata Nutrition 0.000 claims 1
- 235000002254 Viola papilionacea Nutrition 0.000 claims 1
- BDKZHNJTLHOSDW-UHFFFAOYSA-N [Na].CC(O)=O Chemical compound [Na].CC(O)=O BDKZHNJTLHOSDW-UHFFFAOYSA-N 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 230000000875 corresponding Effects 0.000 claims 1
- 238000006193 diazotization reaction Methods 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 238000005755 formation reaction Methods 0.000 claims 1
- 239000005457 ice water Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 230000002035 prolonged Effects 0.000 claims 1
- VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims 1
- 239000001632 sodium acetate Substances 0.000 claims 1
- 235000017281 sodium acetate Nutrition 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 2
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 238000002955 isolation 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
- 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
- C09B31/025—Disazo dyes containing acid groups, e.g. -COOH, -SO3H, -PO3H2, -OSO3H, -OPO2H2; Salts thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
In den Patentschriften 88846 und 92708 ist die Darstellung gewisser sekundärer Thiodisazofarbstoffe beschrieben, welche als Mittelcomponente die 2 · 5 - Amidonaphtol-7-monosulfosäure enthalten. Dafs diese Farbstoffe Baumwolle direkt anzufärben vermögen, ist mit Rücksicht auf das darin enthaltene Thioderivat nicht zu verwundern.Patents 88846 and 92708 depict certain secondary thiodisazo dyes described, which as a middle component the 2 · 5 - amidonaphtol-7-monosulfonic acid contain. The fact that these dyes are able to dye cotton directly is not surprising considering the thio derivative it contains.
Es wurde nun gefunden, dafs auch andere, bisher nicht beschriebene sekundäre Disazofarbstoffe, welche die genannte Amidonaphtolsulfosäure in Mittelstellung enthalten, an erster Stelle dagegen statt jener Thioderivate solche Amine, welche wie Anilin, a-Naphtylamin etc. an sich nicht zur Darstellung substantiver Farbstoffe geeignet sind, unerwarteter Weise eine grofse Affinität zur Baumwollfaser aufweisen. Diese Thatsache ist um so überraschender, als in diesen Farbstoffen im Gegensatz zu den sonstigen bisher bekannt gewordenen, Baumwolle färbenden sekundären Disazofarbstoffen die beiden Azogruppen nicht in ρ-Stellung, sondern in 2-6-StelIung zu einander stehen. '..·■■It has now been found that other secondary disazo dyes not previously described which contain the said amidonaphthol sulfonic acid in the middle position, first Instead of those thio derivatives, substitute amines such as aniline, a-naphthylamine, etc. are not per se suitable for the representation of substantive dyes, unexpectedly have a great affinity for cotton fibers. This fact is all the more surprising, than in these dyes in contrast to the other previously known, Secondary disazo dyes that dye cotton do not have the two azo groups in ρ-position, but in 2-6-position to each other stand. '.. · ■■
Man erhält diese neuen Farbstoffe,, indem •man entweder die Diazoverbindung eines sonst nicht zur Darstellung von Substantiven Farbstoffen geeigneten Amins auf 2-A,mido-5-naphtol-7-sulfosäure in alkalischer Lösung einwirken läfst, die entstehende Amidoazoverbindung weiter diazotirt und nun mit einer beliebigen Endcomponente in bekannter Weise vereinigt, oder indem man durch Diazotirung der 2 - Amido - 5 - naphtol - 7 - sulfosäure und Kuppelung mit einer beliebigen kuppelungsfähigen Verbindung einen Monoazofarbstoffe darstellt, auf welchen man dann die Diazoverbindung eines der genannten Amine einwirken läfst.These new dyes are obtained by using either the diazo compound of an otherwise Amine on 2-A, mido-5-naphthol-7-sulfonic acid, not suitable for the representation of substantive dyes in an alkaline solution, the resulting amidoazo compound can act further diazotized and now with any end component in a known manner combined, or by diazotizing the 2 - amido - 5 - naphthol - 7 - sulfonic acid and Coupling with any couplingable compound a monoazo dye represents, on which one then act the diazo compound of one of the amines mentioned running.
Die so erhaltenen Farbstoffe variiren je nach der Wahl der Componenten von roth bis violett und schwarz und sind durch ihre Echtheit und Intensität ausgezeichnet.The dyes thus obtained vary, depending on the choice of components, from red to purple and black and are distinguished by their authenticity and intensity.
Der aus 9,3 kg diazotirtem Anilin und 23,9 kg 2-Amido-5-naphtol-7-sulfosäure in alkalischer Lösung dargestellte Monoazofarbstoffe wird mit 7 kg Natriumnitrit in bekannter Weise weiter diazotirt und die entstehende Diazoazoverbindung, gleichgültig, ob direkt oder nach vorheriger Isolirung, in eine sodaalkalische Lösung von 23,9 kg 2-Amido-5-naphtol-7-sulfosäure einlaufen lassen. Der so gebildete und dann in üblicher Weise isolirte Farbstoff färbt Baumwolle in Bordeauxtönen von grofser Klarheit und Lichtechtheit an.The from 9.3 kg of diazotized aniline and 23.9 kg of 2-amido-5-naphthol-7-sulfonic acid in alkaline solution represented monoazo dyes with 7 kg of sodium nitrite in a known manner further diazotized and the resulting diazoazo compound, irrespective of whether it is direct or after isolation, in a soda-alkaline solution of 23.9 kg of 2-amido-5-naphthol-7-sulfonic acid let in. The dye thus formed and then isolated in the usual manner dyes cotton in shades of bordeaux of great clarity and lightfastness.
23,9 kg 2 -Amido - 5 - naphtol - 7 - sulfosäure werden mittels 7 kg Natriumnitrit und 25 kg Salzsäure von 30 pCt. in die Diazoverbindung übergeführt und hierauf mit einer Lösung von 23,9 kg 2-Amido-5-naphtol-7-sulfosäure und 18 kg Soda vereinigt. Zu dem so erhaltenen23.9 kg of 2-amido-5-naphthol-7-sulfonic acid are converted into 7 kg of sodium nitrite and 25 kg Hydrochloric acid of 30 pCt. converted into the diazo compound and then with a solution of 23.9 kg of 2-amido-5-naphthol-7-sulfonic acid and 18 kg of soda combined. To the one thus obtained
Claims (1)
p-Toluidin +
Anilin 4"
p-Phenetidin 4~
p-Phenetidin -jp-Xylidin 4-a-Naphtylamin 4"
a-Naphtylamin 4-8-Naphtylamin -ji · 4-Naphtionsäure 4"
p-Phenetidin +
p-Phenetidin 4"
p-Amidosalicylsäure 4"0-toluidine 4-aniline 4 "
p-toluidine +
Aniline 4 "
p-phenetidine 4 ~
p-phenetidine -jp-xylidine 4-a-naphtylamine 4 "
a-naphtylamine 4-8-naphtylamine -ji · 4-naphthoic acid 4 "
p-phenetidine +
p-phenetidine 4 "
p-amidosalicylic acid 4 "
ο al
ο
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AT10509D AT10509B (en) | 1900-01-26 | 1902-02-24 | Process for the preparation of secondary disazo dyes which directly dye cotton. |
Publications (1)
Publication Number | Publication Date |
---|---|
DE129494C true DE129494C (en) |
Family
ID=397952
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE1900129494D Expired - Lifetime DE129494C (en) | 1900-01-26 | 1900-01-26 |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE129494C (en) |
-
1900
- 1900-01-26 DE DE1900129494D patent/DE129494C/de not_active Expired - Lifetime
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