DE221214C - - Google Patents
Info
- Publication number
- DE221214C DE221214C DENDAT221214D DE221214DA DE221214C DE 221214 C DE221214 C DE 221214C DE NDAT221214 D DENDAT221214 D DE NDAT221214D DE 221214D A DE221214D A DE 221214DA DE 221214 C DE221214 C DE 221214C
- Authority
- DE
- Germany
- Prior art keywords
- nitro
- sulfonic acid
- derivatives
- parts
- amino
- 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
- 150000008049 diazo compounds Chemical class 0.000 claims description 4
- 238000006467 substitution reaction Methods 0.000 claims description 4
- 210000002268 Wool Anatomy 0.000 claims description 3
- HBZVNWNSRNTWPS-UHFFFAOYSA-N 6-amino-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(O)C2=CC(N)=CC=C21 HBZVNWNSRNTWPS-UHFFFAOYSA-N 0.000 claims description 2
- 239000003929 acidic solution Substances 0.000 claims description 2
- 150000005215 alkyl ethers Chemical group 0.000 claims description 2
- 150000008378 aryl ethers Chemical class 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 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 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- 239000003086 colorant Substances 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 150000002989 phenols Chemical class 0.000 claims 1
- 239000000975 dye Substances 0.000 description 5
- 230000002378 acidificating Effects 0.000 description 3
- DOPJTDJKZNWLRB-UHFFFAOYSA-N 2-Amino-5-nitrophenol Chemical compound NC1=CC=C([N+]([O-])=O)C=C1O DOPJTDJKZNWLRB-UHFFFAOYSA-N 0.000 description 2
- GVBHRNIWBGTNQA-UHFFFAOYSA-N 2-methoxy-4-nitroaniline Chemical compound COC1=CC([N+]([O-])=O)=CC=C1N GVBHRNIWBGTNQA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- OWRHDQKCCXTFFE-UHFFFAOYSA-N 2-ethoxy-4-nitroaniline Chemical compound CCOC1=CC([N+]([O-])=O)=CC=C1N OWRHDQKCCXTFFE-UHFFFAOYSA-N 0.000 description 1
- VXUMJWGCPAUKTB-UHFFFAOYSA-N 2-methoxy-5-methyl-4-nitroaniline Chemical compound COC1=CC([N+]([O-])=O)=C(C)C=C1N VXUMJWGCPAUKTB-UHFFFAOYSA-N 0.000 description 1
- POKAEVPBUOLQIY-UHFFFAOYSA-N 5-chloro-2-methoxy-4-nitroaniline Chemical compound COC1=CC([N+]([O-])=O)=C(Cl)C=C1N POKAEVPBUOLQIY-UHFFFAOYSA-N 0.000 description 1
- QYFYIOWLBSPSDM-UHFFFAOYSA-N 6-aminonaphthalen-1-ol Chemical compound OC1=CC=CC2=CC(N)=CC=C21 QYFYIOWLBSPSDM-UHFFFAOYSA-N 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N Diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- SMQCFBREXKRRGJ-UHFFFAOYSA-N N-(3-hydroxyphenyl)nitramide Chemical compound OC1=CC=CC(N[N+]([O-])=O)=C1 SMQCFBREXKRRGJ-UHFFFAOYSA-N 0.000 description 1
- UORDUEVECRBKJF-UHFFFAOYSA-N OC1=C2C=C(NC3=CC=CC=C3)C=CC2=CC=C1 Chemical compound OC1=C2C=C(NC3=CC=CC=C3)C=CC2=CC=C1 UORDUEVECRBKJF-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000001808 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000009963 fulling Methods 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- -1 p-tolyl- Chemical group 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 125000005023 xylyl group Chemical group 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/24—Monoazo dyes prepared by diazotising and coupling from coupling components containing both hydroxyl and amino directing groups
- C09B29/28—Amino naphthols
- C09B29/30—Amino naphtholsulfonic acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- M 221214 -KLASSE 22«. GRUPPE - M 221214 - CLASS 22 «. GROUP
Patentiert im Deutschen Reiche vom 6. Oktober 1908 ab.Patented in the German Empire on October 6, 1908.
Es wurde gefunden, daß sich die Alkyl- und Aryläther des 5-Nitro-2-aminophenols, wie z.B. das 5-Nitro-o-aniinoanisol (NO2:NH2: OC Ha = 5 :2 : τ), und ihre Derivate und Substitutionsprodukte in saurer Lösung mit arylierten Derivaten der 2-Amino-8-naphtol-6-sulfosäure γ zu Monoazofarbstoffen vereinigen lassen, die Wolle aus saurem Bade in blumigen schwarzen Tönen anfärben und überraschenderweise die Eigenschaft, vorzüglich zu egalisieren, mit guter Walk- und Lichtechtheit in sich vereinigen.It has been found that the alkyl and aryl ethers of 5-nitro-2-aminophenol, such as 5-nitro-o-aniinoanisole (NO 2 : NH 2 : OC H a = 5: 2: τ), and their Let derivatives and substitution products combine in acidic solution with arylated derivatives of 2-amino-8-naphthol-6-sulfonic acid γ to form monoazo dyes, dye the wool from acidic baths in flowery black tones and, surprisingly, the property of excellent leveling, with good fulling and unite lightfastness.
168 Teile 5-Nitro-2-aminoanisol werden mit 1000 Teilen 20 prozentiger Salzsäure und 700 Teilen Wasser kochend gelöst, durch Zusatz von Eis auf 15 ° abgekühlt und mit 69 Teilen Nitrit versetzt. Die Diazoverbindung wird nach dem Filtrieren mit Natriumacetatlösung abgestumpft, bis nur noch schwach kongosaure Reaktion vorhanden ist. Bei 5° wird die Diazoverbindung darauf zu einer Lösung von 315 Teilen 2-Phenylamino-8-naphtol-6-sulfosäure und 136 Teilen kristallisiertem Natriumacetat in Wasser zugefügt. Nach kurzer Zeit ist die Kuppelung beendet. Der Farbstoff wird in der üblichen Weise isoliert.168 parts of 5-nitro-2-aminoanisole with 1000 parts of 20 percent hydrochloric acid and 700 Parts of water dissolved at the boil, cooled to 15 ° by adding ice and with 69 parts Nitrite added. The diazo compound is after filtering with sodium acetate solution blunted until only a weak Congo acidic reaction is present. At 5 ° becomes then add the diazo compound to a solution of 315 parts of 2-phenylamino-8-naphthol-6-sulfonic acid and 136 parts of crystallized sodium acetate in water were added. After short Time the coupling is over. The dye is isolated in the usual way.
Der Farbstoff erzeugt auf Wolle in saurem Bade ein volles Schwarz.The dye produces a full black on wool in an acidic bath.
Ganz ähnliche Farbstoffe werden erhalten, wenn man die 2 - Phenylamino - 8 - naphtol - 6-sulfosäure durch andere Arylderivate der 2 · 8 · 6- Aminonaphtolsulfosäure ersetzt, wie z. B. p-Tolyl-, Xylyl-, p-Anisidyl-, m-Carboxyphenyl-2 · S-aminonaphtol-ö-sulfosäure. An Stelle von diazotiertem 5-Nitro-2-aminoanisol können auch die Diazoverbindungen von anderen Äthern des 5-Nitro-2-aminophenols oder deren Derivate und Substitutionsprodukte benutzt werden, wie z. B. 5-Nitro-4-chlor-2-aminoanisol, 5-Nitro-4-methyl-2-aminoanisol, 5-Nitro-2-aminophenetol, der Phenyläther des 5-Nitroaminophenols usf.Very similar dyes are obtained if you add 2 - phenylamino - 8 - naphthol - 6-sulfonic acid replaced by other aryl derivatives of 2 · 8 · 6-aminonaphthol sulfonic acid, such as z. B. p-tolyl-, xylyl-, p-anisidyl-, m-carboxyphenyl-2 · S-aminonaphthol-6-sulfonic acid. At Instead of diazotized 5-nitro-2-aminoanisole, the diazo compounds of others can also be used Ethers of 5-nitro-2-aminophenol or their derivatives and substitution products are used become, such as B. 5-nitro-4-chloro-2-aminoanisole, 5-nitro-4-methyl-2-aminoanisole, 5-nitro-2-aminophenetol, the phenyl ether of 5-nitroaminophenol, etc.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE221214C true DE221214C (en) |
Family
ID=482213
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT221214D Active DE221214C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE221214C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE870301C (en) * | 1945-10-04 | 1953-03-12 | Ciba Geigy | Process for the preparation of monoazo dyes |
-
0
- DE DENDAT221214D patent/DE221214C/de active Active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE870301C (en) * | 1945-10-04 | 1953-03-12 | Ciba Geigy | Process for the preparation of monoazo dyes |
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