DE61707C - Process for the preparation of blue-violet, blue-green to black secondary disazo dyes from 1. 8 Dioxynaphthalene-α-monosulfonic acid - Google Patents
Process for the preparation of blue-violet, blue-green to black secondary disazo dyes from 1. 8 Dioxynaphthalene-α-monosulfonic acidInfo
- Publication number
- DE61707C DE61707C DENDAT61707D DE61707DA DE61707C DE 61707 C DE61707 C DE 61707C DE NDAT61707 D DENDAT61707 D DE NDAT61707D DE 61707D A DE61707D A DE 61707DA DE 61707 C DE61707 C DE 61707C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- blue
- dioxynaphthalene
- monosulfonic
- naphtylamine
- 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 47
- 239000000975 dye Substances 0.000 title claims description 12
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims description 4
- 235000005811 Viola adunca Nutrition 0.000 title claims description 3
- 235000013487 Viola odorata Nutrition 0.000 title claims description 3
- 235000002254 Viola papilionacea Nutrition 0.000 title claims description 3
- 238000000034 method Methods 0.000 title claims description 3
- 240000000358 Viola adunca Species 0.000 title claims 2
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-Naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 claims description 10
- 150000004992 toluidines Chemical class 0.000 claims description 5
- HVBSAKJJOYLTQU-UHFFFAOYSA-N Sulfanilic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 4
- 150000008049 diazo compounds Chemical class 0.000 claims description 4
- 229950000244 sulfanilic acid Drugs 0.000 claims description 4
- 238000004040 coloring Methods 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 3
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-Naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 210000002268 Wool Anatomy 0.000 description 2
- -1 naphthol sulfonic acids Chemical class 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- PGLRGMMNMUPZTG-UHFFFAOYSA-N (4-methylphenyl)sulfamic acid Chemical compound CC1=CC=C(NS(O)(=O)=O)C=C1 PGLRGMMNMUPZTG-UHFFFAOYSA-N 0.000 description 1
- COHYTHOBJLSHDF-UHFFFAOYSA-N Indigo Blue Chemical compound N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 description 1
- 240000009038 Viola odorata Species 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000002572 peristaltic Effects 0.000 description 1
- UPKAWFACSJWKND-ZXFFUEEESA-J tetrasodium;(6E)-4-amino-6-[[4-[4-[(2Z)-2-(8-amino-1-oxo-5,7-disulfonatonaphthalen-2-ylidene)hydrazinyl]-3-methoxyphenyl]-2-methoxyphenyl]hydrazinylidene]-5-oxonaphthalene-1,3-disulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].C\1=CC2=C(S([O-])(=O)=O)C=C(S([O-])(=O)=O)C(N)=C2C(=O)C/1=N/NC(C(OC)=C1)=CC=C1C1=CC=C(N\N=C\2C(C3=C(N)C(=CC(=C3C=C/2)S([O-])(=O)=O)S([O-])(=O)=O)=O)C(OC)=C1 UPKAWFACSJWKND-ZXFFUEEESA-J 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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)
- Coloring (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Durch Einwirkung der Diazoverbindungen jener Amidoazokörper, deren einfachste Repräsentanten aus diazotirter Sulfanilsäure bezw. p-Toluidinsulfosäure -f- α - Naphtylamin durch Combination mit Naptholsulfosäuren, die unter den Namen »echtviolett röthlich und bläulich« bekannten Farbstoffe liefern, auf die Dioxynaphtalinmonosulfosäure S (i-8-Dioxynap'htalina-monosulfosäure), welche aus der a-Naphtoldisulfosäure S des Patentes No. 40571 durch Verschmelzen mit Alkalien entsteht, erhält man ä'ufserst werthvolle, blauviolette, rein blaue und grünblaue bis blauschwarze Disazofarbstoffe, welche sich, gegenüber den mit Dioxynaphtalinen, Naphtolsulfosäuren und den anderen bekannten Dioxynaphtalinmonosulfosäuren hergestellten Farbstoffen der Patente No. 39029, 40977 und 50907 durch ihre bedeutend blaueren bezw. grüneren, zum Theil prachtvoll indigoblauen Nuancen auszeichnen.By the action of the diazo compounds of those amidoazo bodies, their simplest representatives from diazotized sulfanilic acid respectively. p-toluidine sulfonic acid -f- α - naphthylamine Combination with naphthol sulfonic acids, which are known as "real violet reddish and bluish" supply known dyes, on the Dioxynaphtalinmonosulfosäure S (i-8-Dioxynap'htalina-monosulfosäure), which is obtained from the a-naphthol disulfonic acid S of patent no. 40571 by Melting with alkalis results in extremely valuable, blue-violet, pure blue and green-blue to blue-black disazo dyes, which, compared to those with dioxynaphthalene, Naphthol sulfonic acids and the other known dioxynaphthalene monosulfonic acids Colorants of the patents no. 39029, 40977 and 50907 by their significantly bluer respectively. greener, partly splendid distinguish indigo blue nuances.
Auch läfst sich noch ein weiterer Effect durch Verwendung dieser Dioxynaphtalinmonosulfosäure S erreichen. Da sich in derselben nämlich die Hydroxylgruppen in der Peristellung zu einander befinden,· haben die mit ihrer Hülfe hergestellten Farbstoffe den Charakter von beizenfärbenden Farbstoffen, während eine solche beizenfärbende Eigenschaft den Farbstoffen der oben citirten Patente nicht zukommt. Another effect can also be achieved by using this dioxynaphthalene monosulfonic acid Reach S. Since in it the hydroxyl groups are in the peristaltic position are to one another, · the dyes produced with their help have the character of stain-coloring dyes, while such a stain-coloring property denotes Dyes of the patents cited above are not included.
Das Verfahren zur Herstellung dieser neuen Disazofarbstoffe besteht im Allgemeinen darin, dafs man die Diazoverbindungen der Amidoazokörper in eine mit Soda alkalisch gehaltene oder essigsaure Lösung der Dioxynaphtalinmonosulfosäure einfliefsen läfst.The process of making these new disazo dyes generally consists of that the diazo compounds of the amidoazo bodies are poured into a solution kept alkaline with soda or acetic acid solution of dioxynaphthalene monosulfonic acid.
Beispiel: Farbstoff aus a-Diazonaphtalinazobenzoldisulfosäure und Dioxynaphtalinmonosulfosäure S.Example: Dye from a-diazonaphthalenezobenzene disulfonic acid and dioxynaphthalene monosulfonic acid S.
25,3 kg p-Amidobenzoldisulfosäure in Lösung werden auf bekannte Weise mit 7 kg Natriumnitrit diazotirt und die Lösung der Diazoverbindung mit der salzsauren Lösung von 1 5 kg a-Naphtylamin vereinigt. Der Amidoazokörper ist nach kurzem Stehen gebildet. Zur.Weiterdiazotirung läfst man eine Lösung von 8 kg Natriumnitrit in 40 1 Wasser zufliefsen und mehrere Stunden stehen. Der Diazoazokörper scheidet sich dabei in glänzenden Kryställchen ab. Derselbe wird abfiltrirt und in eine, essigsaures Natron enthaltende, eiskalte Lösung von 28kgdioxynaphtalinmonosulfosaurem Natron (S) eingetragen. Die Bildung des Farbstoffes geht sofort vor sich und wird durch gelindes Erwärmen auf 50 ° vollendet.25.3 kg of p-amidobenzenesulfonic acid in solution are diazotized in a known manner with 7 kg of sodium nitrite and the solution of the diazo compound combined with the hydrochloric acid solution of 15 kg of a-naphthylamine. The amidoazo body is formed after standing for a short time. A solution of 8 kg is used for further diazotization Add sodium nitrite in 40 l of water and stand for several hours. The diazoazo body is deposited in shiny crystals. It is filtered off and converted into an acetic acid Soda-containing, ice-cold solution of 28kg dioxynaphthalene monosulfonic acid soda (S) registered. The formation of the dye goes on immediately and is made possible by gentle warming completed to 50 °.
Der so erhaltene Farbstoff färbt Wolle in saurem Bade sehr schön blauschwarz.The dye thus obtained dyes wool very beautifully blue-black in an acid bath.
An Stelle der p-A'midobenzoldisulfosäure im vorstehenden Beispiel können auch Sulfanilsäure, Toluidinmono - und disulfosäuren, sowie die Mono- und Disulfosäuren des α- und ß-Naphtylamins verwendet werden.Instead of the p-amidobenzene disulfonic acid im The above example can also include sulfanilic acid, toluidine mono- and disulfonic acids, as well as the mono- and disulfonic acids of α- and ß-naphthylamine are used.
Man gelangt dann zu folgenden Resultaten:The following results are then obtained:
Sulfanilsäure + a-Naphtylamin + Dioxynaphtalinmonosulfosäure S = dunkelviolettblau,Sulfanilic acid + a-naphthylamine + dioxynaphthalene monosulfonic acid S = dark purple blue,
Disulfanilsäure -+■ a-Naphtylamin + Dioxynaphtalinmonosulfosäure S = dunkelblau,Disulfanilic acid - + ■ a-naphthylamine + dioxynaphthalene monosulfonic acid S = dark blue,
Toluidinmonosulfosäure + α-Naphtylamin -f- Dioxynaphtalinmonosulfosäure S ==. dunkelblau, Toluidine monosulfonic acid + α-naphthylamine -f- dioxynaphthalene monosulfonic acid S ==. dark blue,
Toluidindisulfosäure -\- a-Naphtylamin -(- Dioxynaphtalinmonosulfosäure S = blauschwarz,Toluidine disulfonic acid - \ - a-naphthylamine - (- Dioxynaphthalene monosulfonic acid S = blue-black,
a-Naphtylamindisulfosäure III (Patentschrift No. 41957 + a-Naphtylamin + Dioxynaphtalinmortosulfosä'ure S == blauschwarz,α-Naphthylamine disulfonic acid III (patent specification No. 41957 + a-naphthylamine + dioxynaphthalene mortosulfonic acid S == blue black,
ß- Naphtylamin-a-monosulfosäure (Patentschrift No. 20760) -f- α-Naphtylamin -f- Dioxynaphtalinmonosulfosäure S = grünschwarz,ß-naphthylamine-a-monosulfonic acid (patent specification No. 20760) -f- α-naphthylamine -f- dioxynaphthalene monosulfonic acid S = green-black,
ß-Naphtylamin-ß-monosulfosäure (Brönner) -f- α-Naphtylamin + Dioxynaphtalinmonosulfosäure S = blauschwarz,ß-naphthylamine-ß-monosulfonic acid (Brönner) -f- α-naphthylamine + dioxynaphthalene monosulfonic acid S = blue black,
ß-Naphtylamin-y-monosulfosäure (Patentschrift No. 29084) + α-Naphtylamin + Dioxynaphtalinmonosulfosäure S = blauschwarz,ß-Naphthylamine-y-monosulfonic acid (patent specification No. 29084) + α-naphthylamine + dioxynaphthalene monosulfonic acid S = blue black,
ß-Naphtylamin-^-monosulfosäure 4- a-Naphtylamin 4" Dioxnaphtalinmonosulfosäure S = grünstichiges Blauschwarz,ß-naphthylamine - ^ - monosulfonic acid 4- a-naphthylamine 4 "Dioxnaphthalene monosulfonic acid S = greenish blue-black,
ß-Naphtylamindisulfosäure R + a-Naphtylamin -j- Dioxynaphtalinmonosulfosäure S = violett- blauschwarz,ß-naphtylamine disulfonic acid R + a-naphtylamine -j- dioxynaphthalene monosulfonic acid S = violet-blue-black,
ß-Naphtylamindisulfosäure G + a-Naphtylamin -j- Dioxynaphtalinmonosulfosäure S = grünschwarz.ß-naphtylamine disulfonic acid G + a-naphtylamine -j- dioxynaphthalene monosulfonic acid S = greenish black.
Chromgebeizte Wolle wird . im Allgemeinen in etwas grüneren Tönen angefärbt, so dafs man auf diese Weise grünschwarze Töne zu erreichen vermag.Chrome-stained wool is made. generally colored in somewhat greener tones, so that one can achieve greenish-black tones in this way.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE61707C true DE61707C (en) |
Family
ID=335752
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT61707D Expired - Lifetime DE61707C (en) | Process for the preparation of blue-violet, blue-green to black secondary disazo dyes from 1. 8 Dioxynaphthalene-α-monosulfonic acid |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE61707C (en) |
-
0
- DE DENDAT61707D patent/DE61707C/en not_active Expired - Lifetime
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE61707C (en) | Process for the preparation of blue-violet, blue-green to black secondary disazo dyes from 1. 8 Dioxynaphthalene-α-monosulfonic acid | |
| DE842975C (en) | Process for the preparation of monoazo dyes | |
| DE79425C (en) | Process for the preparation of azo dyes from amidotriazines | |
| DE230592C (en) | ||
| DE62945C (en) | Process for the preparation of blue-violet, blue-green to black secondary disazo dyes from dioxynaphthalene disulfonic acid S. | |
| DE60494C (en) | Process for the preparation of real azo dyes for dyeing and printing from amidocarboxylic acids | |
| DE97105C (en) | ||
| DE243122C (en) | ||
| DE47068C (en) | Innovations in the process for the preparation of dyes from tetrazodiphenyl or tetrazoditolyl salts, protected by patent nos. 40954, 43493 and 45342. (3 | |
| DE42440C (en) | Process for the preparation of azo dyes from the α-naphthylamine disulfonic acid of Patent No. 41957 | |
| DE432426C (en) | Process for the preparation of azo dyes | |
| DE120048C (en) | ||
| DE241678C (en) | ||
| DE119662C (en) | ||
| DE109424C (en) | ||
| DE117972C (en) | ||
| DE266356C (en) | ||
| DE57331C (en) | Process for the preparation of mixed azo dyes | |
| DE671287C (en) | Process for the production of azo dyes | |
| DE706672C (en) | Process for the preparation of secondary disazo dyes | |
| DE181714C (en) | ||
| DE229002C (en) | ||
| DE416617C (en) | Process for the preparation of azo dyes | |
| DE97106C (en) | ||
| DE548614C (en) | Process for the preparation of trisazo dyes |