DE229242C - - Google Patents
Info
- Publication number
- DE229242C DE229242C DENDAT229242D DE229242DA DE229242C DE 229242 C DE229242 C DE 229242C DE NDAT229242 D DENDAT229242 D DE NDAT229242D DE 229242D A DE229242D A DE 229242DA DE 229242 C DE229242 C DE 229242C
- Authority
- DE
- Germany
- Prior art keywords
- dye
- wool
- sulfonic acid
- phenylmethylpyrazolone
- chloroaniline
- 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
- 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 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 241000947840 Alteromonadales Species 0.000 claims 1
- 239000000975 dye Substances 0.000 description 6
- 210000002268 Wool Anatomy 0.000 description 4
- QELUYTUMUWHWMC-UHFFFAOYSA-N Edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 description 3
- 150000008049 diazo compounds Chemical class 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- VPXCXBHLKDPWQV-UHFFFAOYSA-N 5-amino-2-chlorobenzenesulfonic acid Chemical compound NC1=CC=C(Cl)C(S(O)(=O)=O)=C1 VPXCXBHLKDPWQV-UHFFFAOYSA-N 0.000 description 2
- 239000000987 azo dye Substances 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- DTNODBHGOLWROS-UHFFFAOYSA-N 3-amino-4-methylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1N DTNODBHGOLWROS-UHFFFAOYSA-N 0.000 description 1
- VNOYHZYNOWVUFB-UHFFFAOYSA-N 4-benzylpyrazol-3-one Chemical compound O=C1N=NC=C1CC1=CC=CC=C1 VNOYHZYNOWVUFB-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- AJDUTMFFZHIJEM-UHFFFAOYSA-N N-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 1
- 241000490025 Schefflera digitata Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- BEHLMOQXOSLGHN-UHFFFAOYSA-N benzenamine sulfate Chemical compound OS(=O)(=O)NC1=CC=CC=C1 BEHLMOQXOSLGHN-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000006243 chemical reaction Methods 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
- 238000005755 formation reaction Methods 0.000 description 1
- 235000015250 liver sausages Nutrition 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 239000001043 yellow dye 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
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
- C09B29/3647—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms
- C09B29/3652—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles
- C09B29/366—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles containing hydroxy-1,2-diazoles, e.g. pyrazolone
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Es hat sich gezeigt, daß durch Kombination von ρ - Chloranilin-m-sulfosäure mit Phenylmethylpyrazolon ein gelber Farbstoff gebildet wird, der Wolle in saurem Bade klar in gelben Tönen anfärbt und sich durch sehr gute Echtheit auszeichnet.It has been shown that by combining ρ - chloroaniline-m-sulfonic acid with phenylmethylpyrazolone a yellow dye is formed which clears in wool in an acid bath dyes yellow tones and is characterized by very good fastness.
Dieses Ergebnis ist durchaus überraschend,This result is quite surprising,
' da man insbesondere mit Rücksicht auf die Angaben der Patentschrift 152862 erwarten mußte, daß ein Azofarbstoff, der durch Kuppelung eines Derivats einer Anilinmonosulfosäure mit Phenylmethylpyrazolon erhalten wird, sich infolge seiner Schwerlöslichkeit zum Färben von Wolle nicht verwenden lassen würde. Im übrigen ist der neue Farbstoff auf Wolle merklich seifen- und ammoniakechter als der bekannte Pyrazolonfarbstoff aus der Diazoverbindung von 2-Toluidin-5-sulfosäure. Ebenso ließ sich das Ergebnis des vorliegenden Verfahrens auch mit Rücksicht auf die Patentschrift 193142 und die französische Patentschrift 388279 nicht voraussehen. Denn die in diesen Patentschriften beschriebenen und unter anderem zum Färben von Wolle bestimmten Azofarbstoffe enthalten sämtlich im Pyrazolonkern eine Carboxylgruppe zum Teil neben einer Sulfogruppe.'as one would expect especially with regard to the information in patent specification 152862 had to find that an azo dye produced by coupling a derivative of an aniline monosulfonic acid is obtained with Phenylmethylpyrazolon, due to its poor solubility to Dyeing wool would not let use. Otherwise is the new dye Noticeably more resistant to soap and ammonia on wool than the well-known pyrazolone dye from the diazo compound of 2-toluidine-5-sulfonic acid. The result of the present procedure also with regard to the patent 193142 and the French Patent 388279 does not foresee. Because those described in these patents and, among other things, for dyeing Azo dyes determined by wool all contain a carboxyl group in the pyrazolone nucleus partly next to a sulfo group.
20,7 kg p-Chl'oranilin-m-sulfosäure werden in der üblichen Weise durch Einwirkung von Nitrit in saurer Lösung diazotiert; die Diazoverbindung läßt man alsdann einlaufen in eine wäßrige Lösung von 18 kg Phenylmethylpyrazolon und der erforderlichen Menge Natronlauge, der so viel Soda zugesetzt war, um die Reaktionsmasse bis zum Schlüsse alkalisch zu halten. Nach beendeter Farbstoffbildung wird der Farbstoff durch Kochsalzzusatz völlig ausgeschieden, abfiltriert und abgepreßt.20.7 kg of p-chloroaniline-m-sulfonic acid are in the usual way by the action of Nitrite diazotized in acidic solution; the diazo compound is then allowed to run into a aqueous solution of 18 kg of phenylmethylpyrazolone and the required amount Caustic soda, to which so much soda was added, to keep the reaction mass up to the end keep alkaline. After the formation of the dye is complete, the dye is added by adding sodium chloride completely excreted, filtered off and squeezed out.
Pate ν t-An s PRU c η :Pate ν t-An s PRU c η:
Verfahren zur Darstellung eines gelben Monoazofarbstoffs, darin bestehend, daß man die Diazoverbindung der p-Chloranilin-m-sulfosäure mit Phenylmethylpyrazolon kombiniert.A method for preparing a yellow monoazo dye, consisting in that the diazo compound of p-chloroaniline-m-sulfonic acid combined with phenylmethylpyrazolone.
BERLIN. GEDRUCKT IN PER RE'CHSDRUCKEREI,BERLIN. PRINTED IN PRINTING,
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE229242C true DE229242C (en) |
Family
ID=489572
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT229242D Active DE229242C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE229242C (en) |
-
0
- DE DENDAT229242D patent/DE229242C/de active Active
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