DE42227C - Process for the preparation of azo dyes from tetrazodibenzolazodiphenyl and the like and resorcinol, orcinol and naphthoic acid. ' - Google Patents
Process for the preparation of azo dyes from tetrazodibenzolazodiphenyl and the like and resorcinol, orcinol and naphthoic acid. 'Info
- Publication number
- DE42227C DE42227C DENDAT42227D DE42227DA DE42227C DE 42227 C DE42227 C DE 42227C DE NDAT42227 D DENDAT42227 D DE NDAT42227D DE 42227D A DE42227D A DE 42227DA DE 42227 C DE42227 C DE 42227C
- Authority
- DE
- Germany
- Prior art keywords
- resorcinol
- tetrazodibenzolazodiphenyl
- orcinol
- preparation
- naphthoic 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.)
- Expired - Lifetime
Links
- GHMLBKRAJCXXBS-UHFFFAOYSA-N Resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 title claims description 18
- OIPPWFOQEKKFEE-UHFFFAOYSA-N Orcinol Chemical compound CC1=CC(O)=CC(O)=C1 OIPPWFOQEKKFEE-UHFFFAOYSA-N 0.000 title claims description 11
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 title description 3
- 239000000987 azo dye Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 4
- NRZRRZAVMCAKEP-UHFFFAOYSA-N Naphthionic acid Chemical compound C1=CC=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 NRZRRZAVMCAKEP-UHFFFAOYSA-N 0.000 claims 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 150000004992 toluidines Chemical class 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 2
- LRTFPLFDLJYEKT-UHFFFAOYSA-N para-isopropylaniline Chemical compound CC(C)C1=CC=C(N)C=C1 LRTFPLFDLJYEKT-UHFFFAOYSA-N 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 235000015450 Tilia cordata Nutrition 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- ZOXJIQNURSAHRV-UHFFFAOYSA-N [4-(4-azaniumylphenyl)phenyl]azanium;sulfate Chemical compound [O-]S([O-])(=O)=O.C1=CC([NH3+])=CC=C1C1=CC=C([NH3+])C=C1 ZOXJIQNURSAHRV-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000001816 cooling 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
- 230000001809 detectable Effects 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000001264 neutralization Effects 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- 239000001272 nitrous oxide Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- JWSRMCCRAJUMLX-UHFFFAOYSA-M sodium;4-aminonaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(N)=CC=C(S([O-])(=O)=O)C2=C1 JWSRMCCRAJUMLX-UHFFFAOYSA-M 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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/36—Trisazo dyes of the type
- C09B35/366—D is diphenyl
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMTPATENT OFFICE
EDUARD KEGEL in LEIPZIG.EDUARD KEGEL in LEIPZIG.
Durch Einwirkung von überschüssigem Anilin und salzsaurem Anilin auf Tetrazodiphenyl erhält
man (analog der Bildung des Amidoazobenzols) das Diamidodibenzolazodiphenyl:
C6 H±N = NC6H, NH2 The action of excess aniline and hydrochloric aniline on tetrazodiphenyl gives diamidodibenzolazodiphenyl (analogous to the formation of amidoazobenzene):
C 6 H ± N = NC 6 H, NH 2
C H1N= N C6H4 NH2,
dessen salzsaures Salz stahlblaue Nädelchen bildet. CH 1 N = NC 6 H 4 NH 2 ,
whose hydrochloric acid salt forms steel-blue needles.
Nimmt man statt Anilin dessen Homologen : Toluidin, Xylidine und Cumidine, so erhält man in gleicher Weise die Homologen des Diamidobenzolazodiphenyls.If, instead of aniline, one takes its homologues: toluidine, xylidine and cumidine, one obtains one in the same way the homologues of diamidobenzolazodiphenyls.
Durch Anwendung eines Gemisches obiger Basen, z.B. Anilin und Toluidin etc., erhält man auch gemischte Verbindungen. Diese so erhaltenen Diamidoazobasen lassen sich durch Einwirkung von salpetriger Säure in ihre Tetrazo verbindungen überführen, welche, mit Resorcin in alkalischer oder neutraler Lösung combinirt, scharlachrothe Farbstoffe von um so blauerer Nuance geben, je höher der Kohlenstoffgehalt der Basen ist.By using a mixture of the above bases, e.g. aniline and toluidine, etc. you also get mixed connections. These diamidoazo bases obtained in this way can be passed through Conversion of nitrous acid into their tetrazo compounds, which, with Resorcinol combined in an alkaline or neutral solution, scarlet coloring matter from around The higher the carbon content of the bases, the bluer the shade.
Die entstehenden Farbstoffe sind unlöslich in Wasser, Säuren und kohlensauren Alkalien, lösen sich aber in freiem Alkali leicht auf und färben Baumwolle im alkalischen Bade wasch- und seifenecht roth.The resulting dyes are insoluble in water, acids and carbonic acid alkalis, but dissolve easily in free alkali and dye cotton in an alkaline bath. and soapy red.
Statt Resorcin kann auch Orcin verwendet werden.Orcin can also be used instead of resorcinol.
Wenn man die aus der Kuppelung von Tetrazodiphenyl mit Anilin, Toluidin, Xylidin und Cumidin erhaltenen Diamidoazokörper von neuem diazotirt und zuerst mit 1 Molecül Naphtionsäure zu einer intermediären Verbindung combinirt und diese dann mit 1 Molecül Resorcin oder Orcin weiter verbindet, so gelangt man zu gemischten Verbindungen.If you think of the coupling of tetrazodiphenyl with aniline, toluidine, xylidine and cumidine obtained diamidoazo bodies again diazotized and first with 1 molecule Naphthoic acid is combined to form an intermediate compound, and this is then combined with 1 molecule Resorcinol or orcin further connects, so one arrives at mixed connections.
Beispiel: Das aus 28 kg schwefelsaurem Benzidin als Paste erhaltene Diamidodibenzolazodiphenyl wird mit 3001 Wasser und 50 kg concentrirter Salzsäure unter Eiskühlung verrührt und allmälig mit so viel gelöstem Natriumnitrit versetzt, bis eine Spur freier salpetriger Säure nachweisbar ist.Example: Diamidodibenzolazodiphenyl obtained as a paste from 28 kg of sulfuric acid benzidine is stirred with 300 liters of water and 50 kg of concentrated hydrochloric acid while cooling with ice and gradually so much dissolved sodium nitrite is added until a trace of more free nitrous oxide Acid is detectable.
Hat man zur völligen Diazotirung 14 kg Natriumnitrit verbraucht, so läfst man die Lösung der Tetrazoverbindung in eine kalte Lösung von 22 kg Resorcin oder 28 kg Orcin in : 00 1 Wasser und 25 kg Soda einlaufen. Der Farbstoff scheidet sich als rothbrauner, feiner Niederschlag aus, welcher abfiltrirt, ausgewaschen und direct als Paste verwendet oder ungelöst mit Kalk gereinigt und behutsam getrocknet werden kann.If 14 kg of sodium nitrite have been used for complete diazotization, the solution is dissolved the tetrazo compound run into a cold solution of 22 kg of resorcinol or 28 kg of orcine in: 00 1 water and 25 kg soda. The dye separates out as a red-brown, fine precipitate, which is filtered off and washed out and used directly as a paste or undissolved cleaned with lime and carefully dried can be.
Die gemischten Farbstoffe stellt man in folgender Weise dar: z. B. das Tetrazodibenzolazodiphenyl, wie oben erhalten, läfst man in eine Lösung von 31,8 kg krystallisirtem Natriumnaphtionat und 46 kg Natriumacetat in 150 1 Wasser einlaufen; dann fügt man eine Lösung von 11 kg Resorcin oder 14 kg Orcin in 100 1 Wasser zu, läfst 1 Tag stehen oder erwärmt einige Stunden auf 30 bis 500 C, oder neutralism mit Soda. Der gebildete Farbstoff wird dann abfiltrirt, gewaschen und eventuell gereinigt und getrocknet.The mixed dyes are represented in the following way: e.g. B. the tetrazodibenzolazodiphenyl, obtained as above, is run into a solution of 31.8 kg of crystallized sodium naphthionate and 46 kg of sodium acetate in 150 l of water; then added a solution of 11 kg of resorcinol or orcinol in 14 kg of water to 1 100, läfst stand for 1 day or a few hours heated to 30 to 50 0 C, or neutralism with soda. The dye formed is then filtered off, washed and, if necessary, cleaned and dried.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE42227C true DE42227C (en) |
Family
ID=317645
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT42227D Expired - Lifetime DE42227C (en) | Process for the preparation of azo dyes from tetrazodibenzolazodiphenyl and the like and resorcinol, orcinol and naphthoic acid. ' |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE42227C (en) |
-
0
- DE DENDAT42227D patent/DE42227C/en not_active Expired - Lifetime
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