DE211966C - - Google Patents
Info
- Publication number
- DE211966C DE211966C DENDAT211966D DE211966DA DE211966C DE 211966 C DE211966 C DE 211966C DE NDAT211966 D DENDAT211966 D DE NDAT211966D DE 211966D A DE211966D A DE 211966DA DE 211966 C DE211966 C DE 211966C
- Authority
- DE
- Germany
- Prior art keywords
- phenylenediamine
- acidyl
- dyes
- parts
- dye
- 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 9
- -1 aminonaphthol sulfonic acids Chemical class 0.000 claims description 4
- 150000008049 diazo compounds Chemical class 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- ZTQDYDIRBKMMQB-UHFFFAOYSA-N N-(4-aminophenyl)nitramide Chemical class NC1=CC=C(N[N+]([O-])=O)C=C1 ZTQDYDIRBKMMQB-UHFFFAOYSA-N 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 230000004048 modification Effects 0.000 claims 1
- 238000006011 modification reaction Methods 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 210000002268 Wool Anatomy 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 230000001808 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 229910014033 C-OH Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 229910014570 C—OH Inorganic materials 0.000 description 1
- FYTRVVJHEWUARG-UHFFFAOYSA-N N-(2-aminophenyl)nitramide Chemical class NC1=CC=CC=C1N[N+]([O-])=O FYTRVVJHEWUARG-UHFFFAOYSA-N 0.000 description 1
- 239000000980 acid dye Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 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 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 230000000802 nitrating Effects 0.000 description 1
- 125000003431 oxalo group Chemical group 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000003756 stirring 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- JVe 211966 KLASSE 22a. GRUPPE- JVe 211966 CLASS 22a. GROUP
Zusatz zum Patente 172168 vom 8. Mai 1904.*)Addendum to patent 172168 of May 8, 1904. *)
Patentiert im Deutschen Reiche vom 3. November 1904 ab. Längste Dauer: 7. Mai 1919.Patented in the German Empire on November 3rd, 1904. Longest duration: May 7, 1919.
Im Hauptpatent 172168 und dem Zusatzpatent 199080 wurde ein Verfahren zur Darstellung von Monoazofarbstoffen beschrieben, welches darin besteht, daß man die Diazoverbindungen des Mononitroacet-p-phenylendiamins der Formel:In the main patent 172168 and the additional patent 199080 a process for the preparation of monoazo dyes was described, which consists in the fact that the diazo compounds of mononitroacet-p-phenylenediamine the formula:
CH,-CO-NH-CH, -CO-NH-
-NH,-NH,
NO0 NO 0
mit Dioxynaphtalin bzw. Aminonaphtolsulfosäuren oder Substitutionsprodukten dieser Säuren kuppelt und die so erhaltenen Farbstoffe verseift.with dioxynaphthalene or aminonaphthol sulfonic acids or substitution products of these Acids are coupled and the dyes obtained in this way are saponified.
Es wurde nun gefunden, daß man in diesen Verfahren das oben erwähnte Mononitroacetp-phenylendiamin durch die anderen bisher nicht bekannten Acidylderivate des Mononitrop-phenylendiamins It has now been found that the above-mentioned mononitroacetop-phenylenediamine can be used in this process by the other previously unknown acidyl derivatives of mononitrophenylenediamine
(NH2 : NO2: NH — Acidyl = 1:2:4; (NH 2 : NO 2 : NH - acidyl = 1: 2: 4;
wie z. B. das Formyl-, das Benzoyl-, das Oxalylderivat usw. ersetzen kann. Die genannten Acidylverbindungen werden am besten durch Nitrieren der Mono- oder Diacidylverbindungen und teilweiser Verseifung der Diacidylderivate des Nitro-p-phenylendiamins erhalten. Behandelt man die aus den Nitroacidylverbindungen und den genannten Naphtalinderivaten erhältlichen Farbstoffe mit verseifenden Agenzien, so erhält man die in dem Hauptpatent und dem ersten Zusatzpatent beschriebenen Produkte, und zwar verläuft das Verfahren dabei zum Teil noch leichter und glatter.such as B. the formyl, the benzoyl, the oxalyl derivative, etc. can replace. The mentioned Acidyl compounds are best made by nitrating the mono- or diacidyl compounds and partial saponification of the diacidyl derivatives of nitro-p-phenylenediamine. If you treat those from the nitroacidyl compounds and the naphthalene derivatives mentioned available dyes with saponifying agents, one obtains those in the main patent and the first additional patent the products described, and the process is even easier in some cases and smoother.
3535
18 Teile Mononitroformyl-p-phenylendiamin (NH2:NO2:NH —C-OH = 1:2:4) 18 parts of mononitroformyl-p-phenylenediamine (NH 2 : NO 2 : NH —C-OH = 1: 2: 4)
4040
werden in der bekannten Weise diazotiert und die so erhaltene Diazoverbindung in eine wässerige Lösung von 32 Teilen 1 · 8-Dioxynaphtalin-3 · 6-disulfosäure eingegossen. Nach kurzem Rühren wird etwas essigsaures Natron oder Soda zugesetzt, die Kupplung zu Ende geführt und der so entstandene Azofarbstoff ausgesalzen, abfiltriert und getrocknet. Derselbe färbt Wolle rotviolett. Zur Abspaltung der Formylgruppe wird der Farbstoff mit 3 Teilen 10 prozentiger Schwefelsäure gekocht, wobei sich das verseifte Produkt kristallinisch ausscheidet. Der so entstandene . Farbstoff färbt Wolle in lebhaften blauschwarzen Nuancen an. Er ist identisch mit dem in dem Beispiele des Hauptpatents beschriebenen Produkt. are diazotized in the known manner and the diazo compound thus obtained in a aqueous solution of 32 parts of 1x8-dioxynaphthalene-3 · Poured 6-disulfonic acid. After stirring briefly, it will turn out to be a little bit of baking soda or soda was added, the coupling completed and the azo dye thus formed salted out, filtered off and dried. The same dyes wool red-violet. To the spin-off the formyl group, the dye is boiled with 3 parts of 10 percent sulfuric acid, the saponified product separating out in crystalline form. The resulting. dye colors wool in lively blue-black shades. It is identical to the one in that Examples of the main patent product described.
*) Frühere Zusatzpatente: 186988, 199080.*) Earlier additional patents: 186988, 199080.
Die im Beispiel beschriebene Isolierung des formylierten Farbstoffes kann auch unterbleiben. Nachdem die Kupplung beendet ist, kann man die Lösung desselben direkt mit verdünnter Schwefelsäure verkochen.The isolation of the formylated dye described in the example can also be omitted. After the coupling has ended, the solution of the same can be boiled off directly with dilute sulfuric acid.
18 Teile Mononitroformyl-p-phenylendiamin werden diazotiert und in alkalischer Lösung mit 36 Teilen i-Äthylamino-8-naphtol-3 · 6-disulfosäure gekuppelt. Nach beendeter Reaktion wird durch Kochen mit Schwefelsäure die Formylgruppe abgespalten. Der so erhaltene Farbstoff der i-Äthylamino-8-naphtol-3 · 6-disulfosäure färbt Wolle schwarz. Er ist identisch mit dem in Beispiel 2 des Zusatzpatents 199080 beschriebenen Produkt.18 parts of mononitroformyl-p-phenylenediamine are diazotized and in alkaline solution with 36 parts of i-ethylamino-8-naphthol-3 · 6-disulfonic acid coupled. After the reaction has ended, the formyl group is split off by boiling with sulfuric acid. The thus obtained The i-ethylamino-8-naphthol-3 · 6-disulfonic acid dye dyes wool black. He is identical with the product described in Example 2 of the additional patent 199080.
Claims (1)
Abänderung des Verfahrens des Hauptpatents 172168 und des Zusatzpatents 199080, darin bestehend, daß man statt der Diazoverbindungen des Mononitroacet - ρ - phenylendiamine Patent claim:
Modification of the process of the main patent 172168 and the additional patent 199080, in that instead of the diazo compounds of mononitroacet - ρ - phenylenediamine
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE211966C true DE211966C (en) |
Family
ID=473729
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT211966D Active DE211966C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE211966C (en) |
-
0
- DE DENDAT211966D patent/DE211966C/de active Active
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