DE70031C - Process for converting the azo dyes derived from α! «4-diamido / 5a /? 5-disulphonic acid into the corresponding dyes from« i a + -amidonaphthol - /? 233-disulphonic acid - Google Patents
Process for converting the azo dyes derived from α! «4-diamido / 5a /? 5-disulphonic acid into the corresponding dyes from« i a + -amidonaphthol - /? 233-disulphonic acidInfo
- Publication number
- DE70031C DE70031C DENDAT70031D DE70031DA DE70031C DE 70031 C DE70031 C DE 70031C DE NDAT70031 D DENDAT70031 D DE NDAT70031D DE 70031D A DE70031D A DE 70031DA DE 70031 C DE70031 C DE 70031C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- disulphonic acid
- dyes
- amidonaphthol
- diamido
- 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
- 239000002253 acid Substances 0.000 title claims description 22
- 238000000034 method Methods 0.000 title claims description 4
- 230000000875 corresponding Effects 0.000 title claims description 3
- 239000000987 azo dye Substances 0.000 title claims 2
- 239000000975 dye Substances 0.000 title description 12
- 150000007513 acids Chemical class 0.000 claims description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
- 239000011707 mineral Substances 0.000 claims description 4
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-Naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 claims description 3
- 239000003518 caustics Substances 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims 2
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-Naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 claims 1
- 239000005711 Benzoic acid Substances 0.000 claims 1
- HVBSAKJJOYLTQU-UHFFFAOYSA-N Sulfanilic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 claims 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 1
- 229950000244 sulfanilic acid Drugs 0.000 claims 1
- 150000004992 toluidines Chemical class 0.000 claims 1
- -1 xylidine Chemical compound 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KVUMAMKEDVSBSO-UHFFFAOYSA-N [N+](=[N-])=C1C(C=CC=C1)N=NC1=CC=CC=C1 Chemical compound [N+](=[N-])=C1C(C=CC=C1)N=NC1=CC=CC=C1 KVUMAMKEDVSBSO-UHFFFAOYSA-N 0.000 description 2
- 150000008049 diazo compounds Chemical class 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- SATZKZRGXNAHHL-UHFFFAOYSA-N 1-(diazomethyl)-2-methylbenzene Chemical compound CC1=CC=CC=C1C=[N+]=[N-] SATZKZRGXNAHHL-UHFFFAOYSA-N 0.000 description 1
- MBENGEYDAUUYCZ-UHFFFAOYSA-N 1-diazo-2H-naphthalene Chemical compound C1=CC=C2C(=[N+]=[N-])CC=CC2=C1 MBENGEYDAUUYCZ-UHFFFAOYSA-N 0.000 description 1
- NPAYBXSLOLNULX-UHFFFAOYSA-N 2-diazo-1H-naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)C(=[N+]=[N-])C=CC2=C1 NPAYBXSLOLNULX-UHFFFAOYSA-N 0.000 description 1
- MFCDHQNPTNBIGC-UHFFFAOYSA-N 6-diazocyclohexa-2,4-diene-1-carboxylic acid Chemical compound OC(=O)C1C=CC=CC1=[N+]=[N-] MFCDHQNPTNBIGC-UHFFFAOYSA-N 0.000 description 1
- 210000002268 Wool Anatomy 0.000 description 1
- 239000000980 acid dye Substances 0.000 description 1
- 230000002378 acidificating Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001049 brown dye Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- QDHHCQZDFGDHMP-UHFFFAOYSA-O chloroamine;hydron Chemical compound Cl[NH3+] QDHHCQZDFGDHMP-UHFFFAOYSA-O 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- CRGRWBQSZSQVIE-UHFFFAOYSA-N diazomethylbenzene Chemical compound [N-]=[N+]=CC1=CC=CC=C1 CRGRWBQSZSQVIE-UHFFFAOYSA-N 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000003472 neutralizing Effects 0.000 description 1
- NIXKBAZVOQAHGC-UHFFFAOYSA-N phenylmethanesulfonic acid Chemical class OS(=O)(=O)CC1=CC=CC=C1 NIXKBAZVOQAHGC-UHFFFAOYSA-N 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/44—Preparation of azo dyes from other azo compounds by substituting amine groups for hydroxyl groups or hydroxyl groups for amine groups; Desacylation of amino-acyl groups; Deaminating
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Aus den durch Combination von Diazoverbindungen mit der Diamidonaphtalin-α-disulfosäure erhaltenen Farbstoffen gelingt es, unter gewissen Bedingungen eine Amidogruppe abzuspalten und durch die Hydroxylgruppe zu ersetzen. Bei dieser Umwandlung erhält man Farbstoffe, welche identisch sind mit den aus Diazoverbindungen und der Amidonaphtoldisulfosäure H in alkalischer Lösung gebildeten Farbstoffen. Die Amidonaphtoldisulfosäure H, welche aus Diamidonaphtalin-α-disulfosäure durch Erhitzen mit Mineralsäuren entsteht, ist identisch mit der Säure, die aus der Koctischen Naphtylamintfisulfosäure in der Alkalischmelze gebildet wird. Daher sind die Farbstoffe, welche nach dem vorliegenden Verfahren erhalten werden, identisch mit den Farbstoffen des Patentes Nr. 62368. Als geeignete Mittel zur Ueberführung kommen verdünnte Mineralsäuren und wässerige kaustische Alkalien zur Verwendung.From the dyes obtained by combining diazo compounds with diamidonaphthalene-α-disulfonic acid, it is possible, under certain conditions, to split off an amido group and replace it with the hydroxyl group. In this conversion, dyes are obtained which are identical to the dyes formed from diazo compounds and amidonaphthol disulfonic acid H in an alkaline solution. The amidonaphthol disulfonic acid H, which is formed from diamidonaphthalene-α-disulfonic acid by heating with mineral acids, is identical to the acid which is formed from the octal naphthylamine disulfonic acid in the alkali melt. Therefore, the dyes obtained by the present process are identical to the dyes of Patent No. 62368. Dilute mineral acids and aqueous caustic alkalis are used as suitable conversion agents.
Beispiel: 46,5 kg des aus 1 Aequivalent Diazobenzol und 1 Aequivalent Diamidonaphtalin-a-disulfosäure erhaltenen braunen Farbstoffes werden in 1000 1 Wasser gelöst und 100 kg Salzsäure (210B.) hinzugegeben. Man erwärmt zunächst auf 6o° C. Bei dieser Temperatur beginnt die violette Farbe der Flüssigkeit allmälig in roth überzugehen. Zum Schlufs erwärmt man kurze Zeit zum Kochen. Nach dem Erkalten wird der ausgeschiedene Farbstoff abfiltrirt. In der Lösung findet sich ι Aequivalent Chlorammonium; oderExample: 46.5 kg of the 1 equivalent of diazobenzene and 1 equivalent Diamidonaphtalin-a-disulfonic acid resulting brown dye are dissolved in 1000 1 of water and add 100 kg of hydrochloric acid (21 0 B.). It is first heated to 60 ° C. At this temperature the violet color of the liquid begins to gradually turn red. At the end, warm up to boil for a short time. After cooling, the precipitated dye is filtered off. In the solution there is an equivalent of chlorammonium; or
62 kg des aus 1 Aequivalent ß-Naphtylaminß-sulfosäure (Brönner) und 1. Aequivalent Diamidonaphtalin - α - disulfosäure erhaltenen Farbstoffes werden mit 300 1 Wasser und 120 kg Natronhydrat so lange zum Kochen erhitzt, bis die Entwickelung von Ammoniak aufgehört hat. Durch Neutralisiren wird der Farbstoff abgeschieden.62 kg of 1 equivalent of ß-naphthylamineß-sulfonic acid (Brönner) and the 1st equivalent of diamidonaphthalene - α - disulfonic acid The dye is boiled with 300 l of water and 120 kg of sodium hydrate heated until the development of ammonia has ceased. By neutralizing the Dye deposited.
In analoger Weise werden die Combinationen behandelt, welche aus Diazotoluol, Diazoxylol, Diazoazobenzol- und Toluolsulfosäuren, Diazobenzoesäure, Diazonaphtalin, Diazoazobenzol, Diazonaphtalinsulfosäure u. s. f. erhalten werden.The combinations which consist of diazotoluene, diazoxylol, Diazoazobenzene and toluene sulfonic acids, diazobenzoic acid, diazonaphthalene, diazoazobenzene, Diazonaphthalene sulfonic acid and the like.
Die sämmtlichen Farbstoffe färben Wolle in saurem Bade roth bis blauroth. Sie besitzen ein gutes Egalisirungsvermögen; sie zeigen die für alkalisch combinirte Amidonaphtolsulfosäurefarbstoffe charakteristische Eigenschaft der Diazotirbarkeit. Hieraus, sowie aus den Nuancen und den Reductionsproducten hat sich die Identität der Farbstoffe mit den entsprechenden Azoderivaten der Amidonaphtoldisulfosäure H ergeben.All the dyes dye wool in an acidic bath red to bluish-red. You own good leveling power; they show the amidonaphthol sulfonic acid dyes combined for alkaline characteristic property of diazotization. From this, as well as from the nuances and the reduction products have the identity of the dyes with the corresponding Azo derivatives of amidonaphthol disulfonic acid H give.
Claims (2)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE70031C true DE70031C (en) |
Family
ID=343447
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT70031D Expired - Lifetime DE70031C (en) | Process for converting the azo dyes derived from α! «4-diamido / 5a /? 5-disulphonic acid into the corresponding dyes from« i a + -amidonaphthol - /? 233-disulphonic acid |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE70031C (en) |
-
0
- DE DENDAT70031D patent/DE70031C/en not_active Expired - Lifetime
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