DE161277C - - Google Patents
Info
- Publication number
- DE161277C DE161277C DENDAT161277D DE161277DA DE161277C DE 161277 C DE161277 C DE 161277C DE NDAT161277 D DENDAT161277 D DE NDAT161277D DE 161277D A DE161277D A DE 161277DA DE 161277 C DE161277 C DE 161277C
- Authority
- DE
- Germany
- Prior art keywords
- diazo
- yellow
- acid
- nitro
- sulfonic 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.)
- Active
Links
- UOZQNVWSYKGFFU-UHFFFAOYSA-N N-(3-aminophenyl)nitramide Chemical compound NC1=CC=CC(N[N+]([O-])=O)=C1 UOZQNVWSYKGFFU-UHFFFAOYSA-N 0.000 claims description 4
- RJTNINZVTNAHPE-UHFFFAOYSA-N [N+](=O)([O-])CC1(CC(=CC=C1)N)N Chemical compound [N+](=O)([O-])CC1(CC(=CC=C1)N)N RJTNINZVTNAHPE-UHFFFAOYSA-N 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 3
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 claims description 3
- 230000004048 modification Effects 0.000 claims 1
- 238000006011 modification reaction Methods 0.000 claims 1
- 239000002253 acid Substances 0.000 description 12
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 6
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-Naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 4
- -1 Diazo-p-toluidine sulfonic acid Chemical compound 0.000 description 4
- ZMOZWMXGDWPAMN-VXLYETTFSA-N (E)-1-[4-[bis(carboxymethyl)amino]-2-[2-[2-[bis(carboxymethyl)amino]-5-methylphenoxy]ethoxy]phenyl]-2-diazonioethenolate Chemical compound CC1=CC=C(N(CC(O)=O)CC(O)=O)C(OCCOC=2C(=CC=C(C=2)N(CC(O)=O)CC(O)=O)\C([O-])=C/[N+]#N)=C1 ZMOZWMXGDWPAMN-VXLYETTFSA-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 3
- 239000000460 chlorine Substances 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 239000004922 lacquer Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- GEYOCULIXLDCMW-UHFFFAOYSA-N O-Phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 2
- HVBSAKJJOYLTQU-UHFFFAOYSA-N Sulfanilic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 229950000244 sulfanilic acid Drugs 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- UEUIKXVPXLWUDU-UHFFFAOYSA-N 4-diazoniobenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C([N+]#N)C=C1 UEUIKXVPXLWUDU-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 229940018564 M-PHENYLENEDIAMINE Drugs 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N M-Phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N Sulfamic acid Chemical class NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- UXZBASJUBLVECL-UHFFFAOYSA-N [N+](=[N-])=CC1=C(C=CC=C1)NS(O)(=O)=O Chemical compound [N+](=[N-])=CC1=C(C=CC=C1)NS(O)(=O)=O UXZBASJUBLVECL-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 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
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Im Patent 156352 wurde gezeigt, daß man durch Kombination von Diazosulfosäuren der Benzol- und Naphtalinreihe mit Nitro-m-phenylendiamin bezw. Nitro-m-toluylendiamin zu Farbstoffen gelangt, welche in ausgezeichneter Weise zur Darstellung gelber bis orangegelber Farblacke geeignet sind.In the patent 156352 it was shown that by combining diazosulfonic acids the benzene and naphthalene series with nitro-m-phenylenediamine respectively. Nitro-m-toluenediamine arrives at dyes, which are excellently suited for the representation of yellow to orange-yellow colored lakes are.
Es hat sich nun gezeigt, daß man ebenfalls wertvolle, zur Darstellung von Farblacken geeignete Farbstoffe erhält, wenn man an Stelle von Nitro-m-phenylendiamin bezw. Nitro-m-toluylendiamin die Nitro-m-phenylendiaminsulfosäure anwendet.It has now been shown that one is also valuable for the representation of colored lacquers suitable dyes are obtained if, in place of nitro-m-phenylenediamine, respectively. Nitro-m-toluenediamine the nitro-m-phenylenediamine sulfonic acid applies.
Dieses Verhalten war nicht ohne weiteres vorauszusehen, da nach den bisherigen Erfahrungen durch die Vermehrung der Sulfogruppen im Molekül die betreffenden Kombinationen sehr wohl viel zu löslich und daher zur Lackdarstellung weniger geeignet hätten werden können. Überraschend ist auch, daß die aus den Nitro-m-phenylendiaminsulfosäure-Kombinationen dargestellten Lacke in bezug auf Lichtechtheit diejenigen aus Nitro-This behavior could not be foreseen without further ado, as based on previous experience by increasing the number of sulfo groups in the molecule, the combinations in question very much too soluble and therefore less suitable for representing lacquer could have been. It is also surprising that from the nitro-m-phenylenediaminesulfonic acid combinations lacquers shown in terms of lightfastness those made of nitro
1. Diazo-Sulfanilsäure1. Diazo-sulfanilic acid
2. Diazo - Metanilsäure2. Diazo - metanilic acid
3. Diazo-o-Toluidinsulfosäure3. Diazo-o-toluidine sulfonic acid
(C H3: NH? : S O3 H = 1 : 2 : 4) 4.· Diazo-p-Toluidinsulfosäure(C H 3 : NH ?: SO 3 H = 1: 2: 4) 4. · Diazo-p-toluidine sulfonic acid
(C H3 : NH2 -.SO3H= 1:4:6) m-phenylendiamin bezw. Nitro-m-toluylendiamin noch wesentlich übertreffen.(C H 3 : NH 2 -SO 3 H = 1: 4: 6) m-phenylenediamine or. Nitro-m-toluenediamine still significantly outperform.
25 Teile nitro-m-phenylendiaminsulfosaures Ammonium werden in 1000 Teilen Wasser heiß gelöst; es wird dann auf etwa 300 abgekühlt und die aus 17,3 Teilen Sulfanilsäure erhaltene Diazoverbindung zugefügt.25 parts of nitro-m-phenylenediaminesulfonic acid ammonium are dissolved in 1000 parts of hot water; it is then cooled to about 30 0 and added to the diazo compound from 17.3 parts of sulphanilic acid.
Nach mehrstündigem Rühren ist die Farbstoffbildung beendet. Es wird dann durch Zusatz von 6 Teilen calc. Soda das Natriumsalz dargestellt, welches durch 250 Teile Kochsalz als gelbes Pulver abgeschieden wird.After several hours of stirring, the formation of the dye has ended. It will then go through Addition of 6 parts of calc. Soda the sodium salt shown, which is deposited as a yellow powder by 250 parts of table salt.
Dasselbe ist in Wasser leicht mit gelber Farbe löslich, die Farbe der Lösung wird durch Alkalien oder Säuren kaum verändert.The same is easily soluble in water with yellow color, the color of the solution becomes hardly changed by alkalis or acids.
In analoger Weise verfährt man bei Verwendung anderer Aminosulfosäuren an Stelle von Sulfanilsäure.An analogous procedure is followed when using other aminosulfonic acids instead of sulfanilic acid.
In nachstehender Tabelle sind die Nuancen der Lackaufstriche einer größeren Anzahl der nach vorliegendem Verfahren erhaltenen Kombinationen angeführt.In the table below are the nuances of the varnish spreads of a larger number of combinations obtained by the present process are listed.
-f- Nitro -m--f- nitro -m-
phenylendiamin-phenylenediamine
sulfosäuresulfonic acid
gelb
gelb
gelbyellow
yellow
yellow
gelbyellow
- Xylidinsulf osäure- xylidine sulfonic acid
CH3 :NH2 : SO3H= 1:4:2:5) CH 3 : NH 2 : SO 3 H = 1: 4: 2: 5)
- Chlormetanilsäure- chlorometanilic acid
: Cl: S O3 H = I : 2 : 5): Cl: SO 3 H = I: 2: 5)
- Chlormetanilsäure- chlorometanilic acid
: Cl: SO3H= 1:4:5) : Cl: SO 3 H = 1: 4: 5)
- Chlor - ρ - toluidinsulf osäure -.NH2: Cl: SO3H= 1:4:2:5)- chlorine - ρ - toluidinsulfonic acid -.NH 2 : Cl: SO 3 H = 1: 4: 2: 5)
- Nitranilin - ρ - sulf osäure- Nitraniline - ρ - sulfonic acid
• 4-Naphtylaminsulfosäure• 4-naphthylamine sulfonic acid
• 5-Naphtylaminsulfosäure• 5-naphthylamine sulfonic acid
• 3 · 6-Naphtylamindisulfosäure• 3 x 6-naphthylamine disulfonic acid
• 4 · 6-Naphtylamindisulfosäure• 4x6-naphthylamine disulfonic acid
• 4 · 7-Naphtylamindisulfosäure• 4 x 7-naphthylamine disulfonic acid
• " -Naphtylamindisulfosäure• "-Naphthylamine disulfonic acid
• 8-Naphtylaminsulf osäure• 8-naphthylamine sulfonic acid
• 3 · 6-Naphtylamindisulfosäure• 3 x 6-naphthylamine disulfonic acid
• 6 · 8-Naphtylamindisulfosäure• 6 · 8-naphthylamine disulfonic acid
-f Nitro - m--f nitro - m-
phenylendiamin-phenylenediamine
sulf osäuresulfonic acid
gelb
gelb
gelb
bräunlichgelbyellow
yellow
yellow
brownish yellow
orangegelborange yellow
orangeorange
orangegelborange yellow
orangegelborange yellow
orangegelborange yellow
orangegelborange yellow
orangegelborange yellow
gelb
orange gelb.'yellow
orange yellow. '
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE161277C true DE161277C (en) |
Family
ID=427165
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT161277D Active DE161277C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE161277C (en) |
-
0
- DE DENDAT161277D patent/DE161277C/de active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE161277C (en) | ||
| DE943662C (en) | Process for the preparation of tris and polyazo dyes | |
| DE927041C (en) | Process for the preparation of polyazo dyes | |
| DE971896C (en) | Process for the production of cobalt-containing azo dyes | |
| DE165502C (en) | ||
| DE216685C (en) | ||
| DE436830C (en) | Process for the preparation of acidic triarylmethane dyes | |
| DE271445C (en) | ||
| DE241678C (en) | ||
| DE129388C (en) | ||
| DE125991C (en) | ||
| DE48528C (en) | Process for the preparation of dyes from p-nitrotoluenesulfonic acid | |
| DE89910C (en) | ||
| DE49139C (en) | Innovation in the process for the representation of yellow to brown-red azo dyes from chrysoidine, which color in an alkaline bath. | |
| DE245230C (en) | ||
| DE494445C (en) | Process for the preparation of chromable azo dyes | |
| DE955881C (en) | Process for the production of cobalt-containing azo dyes | |
| DE484968C (en) | Process for the preparation of water-soluble arylazodiarylamines | |
| DE956710C (en) | Process for the production of azo dyes | |
| DE203535C (en) | ||
| DE177296C (en) | ||
| DE235775C (en) | ||
| DE1619594C3 (en) | Reactive dye preparation and its use for dyeing cellulose textile materials | |
| DE508811C (en) | Process for the preparation of yellow monoazo dyes | |
| DE133466C (en) |