DE221620C - - Google Patents
Info
- Publication number
- DE221620C DE221620C DENDAT221620D DE221620DA DE221620C DE 221620 C DE221620 C DE 221620C DE NDAT221620 D DENDAT221620 D DE NDAT221620D DE 221620D A DE221620D A DE 221620DA DE 221620 C DE221620 C DE 221620C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- dyes
- red
- cresotinic
- water
- 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 8
- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 6
- WHSXTWFYRGOBGO-UHFFFAOYSA-N 3-methylsalicylic acid Chemical compound CC1=CC=CC(C(O)=O)=C1O WHSXTWFYRGOBGO-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 229960004889 salicylic acid Drugs 0.000 claims description 3
- -1 aminocresol ethers Chemical class 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- LVSGHVJKKSBAJQ-UHFFFAOYSA-N 5-diazocyclohexa-1,3-diene-1-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC(=[N+]=[N-])C1 LVSGHVJKKSBAJQ-UHFFFAOYSA-N 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000008049 diazo compounds Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 2
- NJESAXZANHETJV-UHFFFAOYSA-N 4-Methylsalicylic acid Chemical compound CC1=CC=C(C(O)=O)C(O)=C1 NJESAXZANHETJV-UHFFFAOYSA-N 0.000 description 1
- PPVRMPPLECDING-UHFFFAOYSA-N 4-[(4-aminophenyl)diazenyl]benzenesulfonic acid Chemical compound C1=CC(N)=CC=C1N=NC1=CC=C(S(O)(=O)=O)C=C1 PPVRMPPLECDING-UHFFFAOYSA-N 0.000 description 1
- 241000947840 Alteromonadales Species 0.000 description 1
- QPQKUYVSJWQSDY-CCEZHUSRSA-N Aniline Yellow Chemical compound C1=CC(N)=CC=C1\N=N\C1=CC=CC=C1 QPQKUYVSJWQSDY-CCEZHUSRSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- HVBSAKJJOYLTQU-UHFFFAOYSA-N Sulfanilic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 1
- 210000002268 Wool Anatomy 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004532 chromating Methods 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- QGCCEFRDKCNAJA-UHFFFAOYSA-N hydrazinylidenesulfamic acid Chemical compound N\N=N\S(O)(=O)=O QGCCEFRDKCNAJA-UHFFFAOYSA-N 0.000 description 1
- 125000005429 oxyalkyl group Chemical group 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
- 239000000843 powder Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- KSVSZLXDULFGDQ-UHFFFAOYSA-M sodium;4-aminobenzenesulfonate Chemical compound [Na+].NC1=CC=C(S([O-])(=O)=O)C=C1 KSVSZLXDULFGDQ-UHFFFAOYSA-M 0.000 description 1
- 229950000244 sulfanilic acid Drugs 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)
- Paper (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- M 221620 —' KLASSE 22 a. GRUPPE- M 221620 - 'CLASS 22 a. GROUP
Verfahren zur Darstellung roter chromierbarer Farbstoffe.Process for the preparation of red chromable dyes.
Patentiert im Deutschen Reiche vom 17. April 1908 abPatented in the German Empire on April 17, 1908
Durch Einwirkung der Diazoverbindungen von Aminoazobenzolsulfosäure und ihren Homologen auf Salicylsäure erhält man orange färbende Chromierungsfarbstoffe. Es wurde nun gefunden, daß durch Einführung der Oxyalkylgruppe in den die Aminogruppe tragenden Kern der Aminoazobenzol- und -toluolsulfosäuren Nuance und Eigenschaften der Farbstoffe erheblich verändert und wertvolle rote ίο Farbstoffe erhalten werden. Die Färbungen zeichnen sich durch sehr gute Säure-, Walk-, Dekatur- und Lichtechtheit aus.By the action of the diazo compounds of aminoazobenzenesulfonic acid and its homologues on salicylic acid, chromating dyes that turn orange are obtained. It was now found that by introducing the oxyalkyl group into those bearing the amino group Core of the aminoazobenzene and toluene sulfonic acids Nuance and properties of the dyes significantly changed and valuable red ίο dyes are preserved. The colorations are characterized by very good acid, milled, decatur and light fastness.
Man diazotiert in der üblichen Weise 39 kg Natriumsulfanilat mit 58 kg Salzsäure 21 ° Be. und 14 kg Nitrit in 500 1 Wasser bei einer Temperatur von 50C. Nach Verlauf einer Stunde wird die Lösung von 29 kg m-Aminop-kresoläther in 25 kg Salzsäure und 1000 1 Wasser hinzugefügt. Nach 6 Stunden ist bei einer Temperatur von etwa 10 ° C. die Aminoazosulfosäure gebildet. Man fügt 46 kg Salzsäure und 17 kg Nitrit hinzu und rührt, bis die Diazotierung vollendet ist, was 5 bis 10 Stunden in Anspruch nimmt. Man filtriert die kristallisierte Diazoverbindung ab und trägt sie nach und nach während einer Dauer von etwa 3 Stunden in eine Lösung von 34 kg o-Kresotinsäure und 35 kg Natronlauge 350 Be. und 40 kg Soda in 1000 1 Wasser bei einer Temperatur von 15 ° C. ein. Sobald die Bildung des Farbstoffs vollendet ist, erwärmt man auf 75 ° C, fällt mittels Kochsalz, filtriert und trocknet.39 kg of sodium sulfanilate are diazotized in the customary manner with 58 kg of hydrochloric acid at 21 ° Be. and 14 kg of added nitrite in 500 1 water at a temperature of 0 5 C. After the lapse of one hour is added to the solution of 29 kg m-Aminop-kresoläther in 25 kg of hydrochloric acid and 1000 1 of water. After 6 hours at a temperature of about 10 ° C., the aminoazosulfonic acid is formed. 46 kg of hydrochloric acid and 17 kg of nitrite are added and the mixture is stirred until the diazotization is complete, which takes 5 to 10 hours. Is filtered off the crystallized diazo compound and transmits it gradually over a period of about 3 hours in a solution of 34 kg of o-cresotinic acid and 35 kg of sodium hydroxide 35 0 Be. and 40 kg of soda in 1000 l of water at a temperature of 15 ° C. As soon as the formation of the dye is complete, the mixture is heated to 75 ° C., precipitated using common salt, filtered and dried.
In trocknen} Zustand stellt der Farbstoff ein rotes Pulver dar, das in Wasser sehr löslich ist. Er färbt die Wolle direkt dunkelgelb. Durch Behandlung mit Chromkali schlägt die Farbe in dunkelrot um. An Stelle der Sulfanilsäure können die Isomeren, Analogen und Homologen dieser Säure verwendet werden, an Stelle der o-Kresotinsäure die Salicylsäure oder m-Kresotinsäure, ohne daß das Resultat wesentlich beeinflußt wird.In the dry} state, the dye represents is a red powder that is very soluble in water. It directly dyes the wool dark yellow. By treatment with chromium potassium beats the color to dark red. Instead of sulfanilic acid, the isomers, analogs and homologues of this acid can be used, instead of o-cresotinic acid, salicylic acid or m-cresotinic acid without significantly affecting the result.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE221620C true DE221620C (en) |
Family
ID=482580
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT221620D Active DE221620C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE221620C (en) |
-
0
- DE DENDAT221620D patent/DE221620C/de active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE221620C (en) | ||
| DE579840C (en) | Process for the production of azo dyes | |
| DE636358C (en) | Process for the production of copper-containing azo dyes | |
| DE955082C (en) | Process for the preparation of disazo dye salts | |
| DE868034C (en) | Process for the preparation of new trisazo dyes | |
| DE222930C (en) | ||
| DE226348C (en) | ||
| DE695400C (en) | Process for the preparation of disazo dyes | |
| DE402643C (en) | Process for the preparation of related dyes | |
| DE407564C (en) | Process for the preparation of tetrakisazo dyes | |
| DE632444C (en) | Process for the preparation of disazo dyes | |
| DE659840C (en) | Process for the production of azo dyes | |
| DE221621C (en) | ||
| DE629743C (en) | Process for the preparation of trisazo dyes | |
| DE741291C (en) | Process for the preparation of disazo dyes | |
| DE538668C (en) | Process for the preparation of chromium-containing azo dyes | |
| DE431264C (en) | Process for the preparation of related disazo dyes | |
| DE682344C (en) | Process for the preparation of ethylene azo dyes | |
| DE732303C (en) | Process for the preparation of water-soluble monoazo dyes | |
| DE498586C (en) | Process for the preparation of polyazo dyes | |
| DE234805C (en) | ||
| DE924524C (en) | Process for the preparation of symmetrical disazo dyes | |
| DE339183C (en) | Process for the preparation of substantive trisazo dyes for cotton | |
| DE504331C (en) | Process for the preparation of alkaline acid dyes of the phenonaphthosafranine series | |
| DE409564C (en) | Process for the production of azo dyes |