DE291963C - - Google Patents
Info
- Publication number
- DE291963C DE291963C DENDAT291963D DE291963DA DE291963C DE 291963 C DE291963 C DE 291963C DE NDAT291963 D DENDAT291963 D DE NDAT291963D DE 291963D A DE291963D A DE 291963DA DE 291963 C DE291963 C DE 291963C
- Authority
- DE
- Germany
- Prior art keywords
- sulfonic acid
- amino
- oxynaphthalene
- dye
- acetylamino
- 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 5
- 239000000243 solution Substances 0.000 claims description 4
- 239000003929 acidic solution Substances 0.000 claims description 2
- 239000000987 azo dye Substances 0.000 claims description 2
- 230000001808 coupling Effects 0.000 claims description 2
- 238000010168 coupling process Methods 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- 150000008049 diazo compounds Chemical class 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- 230000001264 neutralization Effects 0.000 claims 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 125000000542 sulfonic acid group Chemical group 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 210000002268 Wool Anatomy 0.000 description 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BDCJBCKISOZMBR-UHFFFAOYSA-N 2-amino-4-methoxybenzenesulfonic acid Chemical compound COC1=CC=C(S(O)(=O)=O)C(N)=C1 BDCJBCKISOZMBR-UHFFFAOYSA-N 0.000 description 1
- -1 4-acetylamino-i-diazo-3-methoxybenzene-6-sulfonic acid Chemical compound 0.000 description 1
- AMFHFNIIWXMMEG-UHFFFAOYSA-N 5-acetamido-2-amino-4-methoxybenzenesulfonic acid Chemical compound COC1=CC(N)=C(S(O)(=O)=O)C=C1NC(C)=O AMFHFNIIWXMMEG-UHFFFAOYSA-N 0.000 description 1
- HBZVNWNSRNTWPS-UHFFFAOYSA-N 6-amino-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(O)C2=CC(N)=CC=C21 HBZVNWNSRNTWPS-UHFFFAOYSA-N 0.000 description 1
- WDFSYFIRFAWWGG-UHFFFAOYSA-N C(C)(=O)NC1=CCC(C=C1)=[N+]=[N-] Chemical compound C(C)(=O)NC1=CCC(C=C1)=[N+]=[N-] WDFSYFIRFAWWGG-UHFFFAOYSA-N 0.000 description 1
- OKCJAKISDDNNHL-UHFFFAOYSA-N NC=1C(=C(C(=CC=1)OC)S(=O)(=O)O)N Chemical compound NC=1C(=C(C(=CC=1)OC)S(=O)(=O)O)N OKCJAKISDDNNHL-UHFFFAOYSA-N 0.000 description 1
- VMPITZXILSNTON-UHFFFAOYSA-N O-Anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N P-Anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- 241000588733 Pseudescherichia vulneris Species 0.000 description 1
- NVBFHJWHLNUMCV-UHFFFAOYSA-N Sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 1
- 240000000358 Viola adunca Species 0.000 description 1
- 235000005811 Viola adunca Nutrition 0.000 description 1
- 235000013487 Viola odorata Nutrition 0.000 description 1
- 235000002254 Viola papilionacea Nutrition 0.000 description 1
- LQBVQRPQACQWSC-UHFFFAOYSA-N [N+](=O)([O-])C1=CC(C(C=C1)=[N+]=[N-])S(=O)(=O)O Chemical compound [N+](=O)([O-])C1=CC(C(C=C1)=[N+]=[N-])S(=O)(=O)O LQBVQRPQACQWSC-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 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
- 238000000034 method Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 230000002085 persistent Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000001180 sulfating Effects 0.000 description 1
- BBDNZMUIQBRBJH-UHFFFAOYSA-N sulfurochloridic acid;toluene Chemical compound OS(Cl)(=O)=O.CC1=CC=CC=C1 BBDNZMUIQBRBJH-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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/24—Monoazo dyes prepared by diazotising and coupling from coupling components containing both hydroxyl and amino directing groups
- C09B29/28—Amino naphthols
- C09B29/30—Amino naphtholsulfonic acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
.■-JV* 291963
KLASSE 22 a. GRUPPE 1.. ■ -JV * 291963
CLASS 22 a. GROUP 1.
In der Patentschrift 220532 ist ein Monoazofarbstoff aus 4-Nitro-i-diazobenzol-2-sulfosäure und^-Amino-S-oxynaphtalin-o-sulfosäure, sauer gekuppelt, beschrieben worden, der Wolle blauviolett färbt. Ein bräunlich-roter Farbstoff wird nach dem Verfahren der Pa-In patent specification 220532 there is a monoazo dye from 4-nitro-i-diazobenzene-2-sulfonic acid and ^ -amino-S-oxynaphthalene-o-sulfonic acid, acid-coupled, has been described, which dyes wool blue-violet. A brownish-red one Dye is produced according to the method of pa-
CH3O tentschrift 96496 erhalten, wenn man 4-Acetylamino-i-diazobenzol sauer mit 2-Amino-8-oxynaphtalin-6-sulfosäure kuppelt.CH 3 O tentschrift 96496 obtained when 4-acetylamino-i-diazobenzene is acidically coupled with 2-amino-8-oxynaphthalene-6-sulfonic acid.
Es wurde nun gefunden, daß der Farbstoff von der Konstitution:It has now been found that the dye has the constitution:
CHoCO. Η-Ν-<4CHoCO. Η-Ν- <4
.15 ■ :.15 ■:
der durch Kuppelung von 4-Acetylamino-i-diazo-3-methoxybenzol-6-sulfosäure mit 2-Amino-8-naphtol-6-sulfosäure in schwach saurer Lösung entsteht, die wertvollen Eigenschaften klarer blauroter Farbtöne, hervorragender Lichtechtheit seiner Färbungen auf Wolle und ausgezeichneten Egalisierungsvermögens in einem so hohen Grade vereinigt, wie man es bisher bei keinem für Egalisierungszwecke dienenden Azofarbstoff von einem ähnlichen Farbton angetroffen hat.that by coupling 4-acetylamino-i-diazo-3-methoxybenzene-6-sulfonic acid with 2-amino-8-naphthol-6-sulfonic acid in a weakly acidic solution, the valuable properties become clearer blue-red shades, excellent lightfastness of its dyeings on wool and excellent Ability to equalize in as high a degree as one has hitherto Not found in any azo dye of a similar shade used for leveling purposes Has.
Die als Ausgangsstoff des Verfahrens dienende 4-Acetylamino -i-amino -3 - methoxybenzol-6-sulfosäure läßt sich gewinnen, indem man o-Anisidin sulfiert, die AnisidinsulfosäureThe 4-acetylamino-i-amino -3-methoxybenzene-6-sulfonic acid used as the starting material for the process can be obtained by sulfating o-anisidine, the anisidine sulfonic acid
(NH2: OCH3: SO3H = 1:2: 5)(NH 2 : OCH 3 : SO 3 H = 1: 2: 5)
mit Toluolsulfochlorid kondensiert, das SuIfamid mit Salpeterschwefelsäure nitriert, diecondensed with toluene sulfochloride, the sulfamide nitrated with nitric sulfuric acid, the
SO3H,SO 3 H,
Toluolsulfogruppe abspaltet, die Nitrogruppe reduziert und die DiaminoanisolsulfosäureEliminates toluenesulfo group, reduces the nitro group and the diaminoanisolesulfonic acid
(NH2: NH2 : OCH3: SO3H = 1:4: 3: 6)(NH 2 : NH 2 : OCH 3 : SO 3 H = 1: 4: 3: 6)
in wäßriger Lösung mit Essigsäureanhydrid monoacetyliert. Aus der Lösung wird durch Salzsäure die Säure kristallinisch ausgeschieden. Sie bildet trocken ein farbloses Pulver, das sich in heißem Wasser löst und beim Erkalten in perlmutterglänzenden Blättchen auskristallisiert. Ihr Natriumsalz ist in kaltem Wasser sehr leicht löslich. Ihre ziemlich beständige Diazoverbindung scheidet sich aus konzentrierten Lösungen aus.monoacetylated in aqueous solution with acetic anhydride. The solution becomes through Hydrochloric acid precipitated the acid in crystalline form. When dry it forms a colorless powder, which dissolves in hot water and crystallizes in pearlescent leaves when it cools. Its sodium salt is very easily soluble in cold water. Your pretty persistent Diazo compound separates out from concentrated solutions.
Die in üblicherweise aus 26Teilen 4-Acetylamino -i- amino- 3 - methoxybenzol -6- sulf osäure, 30 Teilen Salzsäure 12 ° Be und 7 Teilen Na-The usually made up of 26 parts of 4-acetylamino -i amino- 3 - methoxybenzene -6- sulfonic acid, 30 parts of hydrochloric acid 12 ° Be and 7 parts of Na-
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE291963C true DE291963C (en) |
Family
ID=546789
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT291963D Active DE291963C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE291963C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3142669A (en) * | 1960-12-12 | 1964-07-28 | Crompton & Knowles Corp | Monoazo dyes |
-
0
- DE DENDAT291963D patent/DE291963C/de active Active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3142669A (en) * | 1960-12-12 | 1964-07-28 | Crompton & Knowles Corp | Monoazo dyes |
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