DE46203C - Process for the preparation of yellow and brown dyes by the action of nitrated diazo compounds on oxycarboxylic acid - Google Patents
Process for the preparation of yellow and brown dyes by the action of nitrated diazo compounds on oxycarboxylic acidInfo
- Publication number
- DE46203C DE46203C DENDAT46203D DE46203DA DE46203C DE 46203 C DE46203 C DE 46203C DE NDAT46203 D DENDAT46203 D DE NDAT46203D DE 46203D A DE46203D A DE 46203DA DE 46203 C DE46203 C DE 46203C
- Authority
- DE
- Germany
- Prior art keywords
- action
- dyes
- yellow
- preparation
- acid
- 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 9
- 239000001049 brown dye Substances 0.000 title description 2
- 150000008049 diazo compounds Chemical class 0.000 title description 2
- 239000001043 yellow dye Substances 0.000 title 1
- 239000000975 dye Substances 0.000 claims description 16
- 150000007513 acids Chemical class 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 2
- 150000001896 cresols Chemical class 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 2
- SSQQBRZUIXIPIP-UHFFFAOYSA-N 5-diazo-2-nitrocyclohexa-1,3-diene Chemical compound [O-][N+](=O)C1=CCC(=[N+]=[N-])C=C1 SSQQBRZUIXIPIP-UHFFFAOYSA-N 0.000 claims 1
- RLSSMJSEOOYNOY-UHFFFAOYSA-N M-Cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 claims 1
- QWVGKYWNOKOFNN-UHFFFAOYSA-N O-Cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 claims 1
- IWDCLRJOBJJRNH-UHFFFAOYSA-N P-Cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 239000003245 coal Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 238000006193 diazotization reaction Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- XJCVRTZCHMZPBD-UHFFFAOYSA-N 3-Nitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1 XJCVRTZCHMZPBD-UHFFFAOYSA-N 0.000 description 3
- WHSXTWFYRGOBGO-UHFFFAOYSA-N 3-methylsalicylic acid Chemical compound CC1=CC=CC(C(O)=O)=C1O WHSXTWFYRGOBGO-UHFFFAOYSA-N 0.000 description 3
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-Nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 235000002639 sodium chloride Nutrition 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- RGCKGOZRHPZPFP-UHFFFAOYSA-N Alizarin Chemical compound C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 description 2
- 239000000987 azo dye Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 229960004889 salicylic acid Drugs 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- DLGBEGBHXSAQOC-UHFFFAOYSA-N 2-hydroxy-5-methylbenzoic acid Chemical compound CC1=CC=C(O)C(C(O)=O)=C1 DLGBEGBHXSAQOC-UHFFFAOYSA-N 0.000 description 1
- GDIIPKWHAQGCJF-UHFFFAOYSA-N 4-Amino-2-nitrotoluene Chemical compound CC1=CC=C(N)C=C1[N+]([O-])=O GDIIPKWHAQGCJF-UHFFFAOYSA-N 0.000 description 1
- NJESAXZANHETJV-UHFFFAOYSA-N 4-Methylsalicylic acid Chemical compound CC1=CC=C(C(O)=O)C(O)=C1 NJESAXZANHETJV-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000000875 corresponding Effects 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
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000002966 varnish Substances 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
- C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
- C09B29/12—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group of the benzene series
- C09B29/14—Hydroxy carboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
KAASSE 22: Farbstoffe, Firnisse, Lacke.KAASSE 22: dyes, varnishes, lacquers.
Dr. R. NIETZKI in BASEL.Dr. R. NIETZKI in BASEL.
Zusatz zum Patent No. 44170 vom 16. November 1887.Addition to patent no. 44170 of November 16, 1887.
Patentirt im Deutschen Reiche vom 25. Februar 1888 ab. Längste Dauer: 15. November 1902.Patented in the German Empire on February 25, 1888. Longest duration: November 15, 1902.
Die im Haupt - Patent benutzte Salicylsäure kann mit ähnlichem Erfolg durch die aus den drei isomeren Kresolen durch Einwirkung von Kohlensäure erhaltenen Kresotinsäuren ersetzt werden.The salicylic acid used in the main patent can be used with similar success by the three isomeric cresols replaced by the action of carbonic acid obtained cresotinic acids will.
Es scheinen überhaupt zur Herstellung der beizenfärbenden Azofarbstoffe alle Oxycarbonsäuren geeignet zu sein, welche die Carboxylgruppe zum Hydroxyl in der Orthostellung enthalten. So giebt die a. - Oxynaphtoesäure gerade wie die Salicylsäure und ihre Homologen mit allen nitrirten Diazoverbindungen brauchbare Farbstoffe.In general, all oxycarboxylic acids which contain the carboxyl group in relation to the hydroxyl in the ortho position appear to be suitable for the production of the azo dyes for the staining. So gives the a. - oxynaphthoic acid just like salicylic acid and its homologs with all nitrirten diazo dyes useful.
Die wesentliche Eigenschaft dieser Azofarbstoffe ist die, dafs sie analog den Alizarinfarbstoffen auf metallische Beizen anfärben.The essential property of these azo dyes is that they are analogous to the alizarin dyes stain on metallic stains.
An folgenden Beispielen sollen die Darstellungsmethoden der verschiedenen Gruppen von Farbstoffen, die hier in Betracht kommen, erläutert werden.The following examples are intended to illustrate the various groups of Dyes that come into consideration here are explained.
i. Farbstoff aus p-Nitranilin und
o-Kresotinsäure.i. Dye made from p-nitroaniline and
o-cresotinic acid.
1,38 Theile p-Nitranilin werden in salzsaurer Lösung unter Kühlung mit 0,7 Theilen Natriumnitrit diazotirt. Nach vollendeter Diazotirung läfst man diese Flüssigkeit in eine Lösung von 1,56 Theilen o-Kresotinsäure und 4 Theilen calcinirter Soda oder der entsprechenden Menge Aetznatron in 20 Theilen Wasser einlaufen. Der Farbstoff wird mit Kochsalz ausgesalzen und durch geeignete Behandlung in Form einer Paste gebracht. Der Farbstoff bildet in trockenem Zustande ein hellbraunes Pulver.1.38 parts of p-nitroaniline are dissolved in a hydrochloric acid solution while cooling with 0.7 parts of sodium nitrite diazotized. When the diazotization is complete, this liquid is poured into a Solution of 1.56 parts of o-cresotinic acid and 4 parts of calcined soda or the equivalent Pour a quantity of caustic soda into 20 parts of water. The dye is salted out with table salt and treated appropriately brought in the form of a paste. The dye forms in the dry state light brown powder.
2. Farbstoff aus p-Nitranilin und2. Dye made from p-nitroaniline and
a-Oxynaphtoe säure.a-Oxynaphtoe acid.
Die Diazotirung des ρ - Nitranilins geschieht in oben angegebener Weise. Die Lösung des Diazokörpers läfst man in eine Lösung von 1,9 Theilen a-Oxynaphtoesäure und 4 Theilen calcinirter Soda oder der entsprechenden Menge Aetznatron in 20 Theilen Wasser einlaufen. Der ebenfalls mit Kochsalz ausgeschiedene braune Farbstoff wird in Form einer Paste gebracht.The diazotization of ρ-nitroaniline takes place in the manner indicated above. The solution to the The diazo body is dissolved in a solution of 1.9 parts of α-oxynaphthoic acid and 4 parts Pour calcined soda or the corresponding amount of caustic soda into 20 parts of water. The brown dye, which is also excreted with table salt, is in the form of a paste brought.
3. Farbstoff aus m-Nitranilin und3. M-nitroaniline and dye
p-Kresotinsäure.p-cresotinic acid.
ι ,38 Theile m-Nitranilin werden in 5 Theilen Salzsäure von 200 B. und 20 Theilen Wasser gelöst. Unter Kühlung werden 0,7 Theile Natriumnitrit hinzugefügt und nach vollzogener Diazotirung diese Flüssigkeit in eine Lösung von 1,56 Theilen Kresotinsäure und 4 Theilen calcinirter Soda in 20 Theilen Wasser einlaufen gelassen. Bei der Kupplung mufs man sorgfältiger verfahren, da diese Farbstoffe schwieriger darzustellen sind. Der Farbstoff bildet ein braunes Pulver. ι, 38 parts of m-nitroaniline are dissolved in 5 parts of hydrochloric acid 20 0 B. and 20 parts of water. With cooling, 0.7 part of sodium nitrite is added, and when the diazotization is complete, this liquid is allowed to run into a solution of 1.56 parts of cresotinic acid and 4 parts of calcined soda in 20 parts of water. The coupling must be done more carefully as these dyes are more difficult to represent. The dye forms a brown powder.
4· Farbstoff aus m-Nitro-p-toluidin4 x m-nitro-p-toluidine dye
(Schmelzpunkt 77,5) und m-Kresotin-(Melting point 77.5) and m-cresotin
säure.acid.
Die Diazotirung geschieht wie bei m-Nitranilin. Ebenso die Reaction zwischen Diazoverbindung und m-Kresotinsäure. Der mit Kochsalz ausgeschiedene Farbstoff ist etwas heller und löst sich leichter als die vorhin beschriebenen Farbstoffe.The diazotization occurs as with m-nitroaniline. Likewise the reaction between diazo compounds and m-cresotinic acid. The dye excreted with table salt is a little lighter and dissolves more easily than the ones described above Dyes.
Sä'mmtliche Farbstoffe werden in Form einer Paste in den Handel gebracht.All dyes are marketed in the form of a paste.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE46203C true DE46203C (en) |
Family
ID=321326
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT46203D Expired - Lifetime DE46203C (en) | Process for the preparation of yellow and brown dyes by the action of nitrated diazo compounds on oxycarboxylic acid |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE46203C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4337831A (en) * | 1980-03-07 | 1982-07-06 | Thaxton Darrel G | Fire extinguishing apparatus for oil wells |
-
0
- DE DENDAT46203D patent/DE46203C/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4337831A (en) * | 1980-03-07 | 1982-07-06 | Thaxton Darrel G | Fire extinguishing apparatus for oil wells |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE46203C (en) | Process for the preparation of yellow and brown dyes by the action of nitrated diazo compounds on oxycarboxylic acid | |
| DE695400C (en) | Process for the preparation of disazo dyes | |
| DE39096C (en) | Process for the preparation of azo dyes by combining the chemical products obtained from 1 molecule of tetrazodiphenyl salt or tetrazoditolyl salt with 1 molecule of naphthylamine sulfonic acid etc. with amines etc. | |
| DE287072C (en) | ||
| DE639728C (en) | Process for the production of copper-containing azo dyes | |
| DE247308C (en) | ||
| DE404355C (en) | Process for the preparation of tetrakisazo dyes | |
| DE453133C (en) | Process for the preparation of trisazo dyes | |
| DE924523C (en) | Process for the preparation of copperable disazo dyes | |
| DE710502C (en) | Process for the preparation of polyazo dyes | |
| DE745759C (en) | Process for the production of azo dyes | |
| DE108266C (en) | ||
| DE450998C (en) | Process for the preparation of trisazo dyes | |
| DE477061C (en) | Process for the preparation of related trisazo dyes | |
| DE407564C (en) | Process for the preparation of tetrakisazo dyes | |
| DE454177C (en) | Process for the preparation of related azo dyes | |
| DE199175C (en) | ||
| DE652871C (en) | Process for the preparation of disazo dyes | |
| AT54715B (en) | Process for the preparation of trisazo dyes. | |
| AT68096B (en) | Process for the preparation of developer dyes. | |
| AT128318B (en) | Process for the preparation of diazoamino compounds. | |
| DE75743C (en) | Process for the preparation of blue disazo dyes from ai <Z3-naphthylenediamine | |
| DE625850C (en) | Process for the preparation of monoazo dyes | |
| DE522968C (en) | Process for the preparation of tetrakisazo dyes | |
| DE742764C (en) | Process for the preparation of water-soluble monoazo dyes |