DE76118C - Process for the preparation of primary disazo dyes with m-phenylenediamine disulfonic acid - Google Patents
Process for the preparation of primary disazo dyes with m-phenylenediamine disulfonic acidInfo
- Publication number
- DE76118C DE76118C DENDAT76118D DE76118DA DE76118C DE 76118 C DE76118 C DE 76118C DE NDAT76118 D DENDAT76118 D DE NDAT76118D DE 76118D A DE76118D A DE 76118DA DE 76118 C DE76118 C DE 76118C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- molecule
- naphthylamine
- preparation
- disulfonic 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
- 239000002253 acid Substances 0.000 title claims description 15
- 229940018564 M-PHENYLENEDIAMINE Drugs 0.000 title claims description 9
- WZCQRUWWHSTZEM-UHFFFAOYSA-N M-Phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 title claims description 9
- 239000000975 dye Substances 0.000 title description 6
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title description 2
- 150000008049 diazo compounds Chemical class 0.000 claims description 10
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-Naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 claims description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 5
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 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
- 150000001412 amines Chemical class 0.000 claims description 4
- 229950000244 sulfanilic acid Drugs 0.000 claims description 4
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 claims description 3
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 claims description 3
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 claims description 3
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-Naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 claims description 2
- CZZZABOKJQXEBO-UHFFFAOYSA-N 2,4-Xylidine Chemical group CC1=CC=C(N)C(C)=C1 CZZZABOKJQXEBO-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 239000000987 azo dye Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- PXUQTDZNOHRWLI-QOPOCTTISA-O Primulin Natural products O(C)c1c(O)c(OC)cc(-c2c(O[C@H]3[C@H](O)[C@@H](O)[C@@H](O)[C@H](CO)O3)cc3c(O)cc(O)cc3[o+]2)c1 PXUQTDZNOHRWLI-QOPOCTTISA-O 0.000 description 12
- LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 235000010288 sodium nitrite Nutrition 0.000 description 6
- 239000000047 product Substances 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- -1 m- xylidine Chemical compound 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000001264 neutralization Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- YUNBHHWDQDGWHC-UHFFFAOYSA-N 6-aminonaphthalene-1-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC2=CC(N)=CC=C21 YUNBHHWDQDGWHC-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N Sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 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
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
- C09B33/00—Disazo and polyazo dyes of the types A->K<-B, A->B->K<-C, or the like, prepared by diazotising and coupling
- C09B33/02—Disazo dyes
- C09B33/06—Disazo dyes in which the coupling component is a diamine or polyamine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Paper (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMTS^PATENT OFFICE ^
In der Patentschrift Nr. 73369 ist die Gewinnung von Farbstoffen durch Combination von einem Molecül einer Diazoverbindung mit einem Molecül der durch Sulfuriren von m-Phenylendiamin zu erhaltenden m-Phenylendiamindisulfosäure beschrieben. Weitere Untersuchungen erwiesen nun die Möglichkeit, ein Molecül dieser Disulfosäure auch mit zwei Molecülen Diazoverbindung, die unter sich gleich oder verschieden sein können, zu combiniren. Während aber die Vereinigung der Disulfosäure mit nur einem Molecül Diazoverbindung ziemlich leicht und sowohl in alkalischer wie in neutraler oder essigsaurer Lösung erfolgt, vollzieht sich der Eintritt eines zweiten Molecules Diazoverbindung schwieriger, die Reaction bedarf zu ihrer Vollendung längerer Zeit und verläuft in den meisten Fällen am besten in neutraler oder essigsaurer Lösung.In the patent specification No. 73369 is the production of dyes by combination of a molecule of a diazo compound with a molecule obtained by sulfurizing m-phenylenediamine m-phenylenediaminedisulfonic acid to be obtained is described. Further investigations have now proven the possibility of a Molecül of this disulfonic acid also with two Moleculen diazo compound, which among themselves can be the same or different, to combine. But while the union of Disulfonic acid with only one molecule of diazo compound fairly easily and both in alkaline as occurs in a neutral or acetic acid solution, one takes place The second molecular diazo compound is more difficult, the reaction takes longer to complete Time and in most cases passes best in a neutral or acetic acid solution.
Unter den auf diese Weise darstellbaren Producten sind die orangegelben bis braunen Substantiven Baumwollfarbstoffe besonders werthvoll, welche man erhält, wenn ein Molecül m-Phenylendiamindisulfosäure einerseits mit einem Molecül der Diazoverbindung eines Amins," wie Anilin, o-Toluidin, p-Toluidin, m-Xylidin, a-Naphtylamin, ß-Naphtylamin, oder einer Sulfosäure dieser Amine, wie Sulfanilsäure, Metanilsäure, Naphtionsäure, ß-Naphtylaminsulfosäure ßj a4 (Patent Nr. 20760), ß-Naphtylaminsulfosäure P1 ß3 (Brönner'sche Säure), ß-Naphtylaminsulfosäure ßj a3 (Dahl'sche Säure), andererseits mit einem Molecül der Diazoverbindung des Primulins combinirt wird. Bei Anwendung der Sulfosäuren obiger Amine ist es von Vortheil, das Verfahren in der Weise auszuführen, dafs das Primulin zuerst und die Aminsulfosäure zuletzt in die m-Phenylendiamindisulfosäure eingeführt wird, die Einführung der nicht sulfurirten Amine geschieht dagegen zweckmäfsiger an erster Stelle.Among the products that can be represented in this way, the orange-yellow to brown nouns cotton dyes are particularly valuable, which are obtained when a molecule of m-phenylenediamine disulfonic acid on the one hand with a molecule of the diazo compound of an amine, "such as aniline, o-toluidine, p-toluidine, m- xylidine, a- naphthylamine, beta-naphthylamine, or a sulfonic acid of these amines such as sulfanilic acid, metanilic acid, Naphtionsäure, ß-Naphtylaminsulfosäure ßj a 4 (patent no. 20760), ß-Naphtylaminsulfosäure P 1 ß 3 (Brönner'sche acid), ß-Naphthylamine sulfonic acid ßj a 3 (Dahl's acid), on the other hand, is combined with a molecule of the diazo compound of primulin is introduced into the m-phenylenediamine disulphonic acid, whereas the introduction of the non-sulphurized amines is more expedient in the first place.
I. m-Phenylendiamindisulfosäure combinirt mit Anilin und Primulin.I. m-Phenylenediamine disulfonic acid combined with aniline and primulin.
12,95 kg salzsaures Anilin werden in bekannter Weise mit 6,95 kg Natriumnitrit und 1 5 kg Salzsäure (30 pCt.) diazotirt. Die etwa 500 1 betragende Diazolösung wird einer eiskalten Lösung von 26,8 kg m-Phenylendiamindisulfosäure und 85 kg krystallisirtem Natriumacetat in 500 1 Wasser zugesetzt.12.95 kg of hydrochloric aniline are known in Way diazotized with 6.95 kg of sodium nitrite and 15 kg of hydrochloric acid (30 pct.). The approximately 500 1 amount Diazo solution is an ice-cold solution of 26.8 kg of m-phenylenediamine disulfonic acid and 85 kg of crystallized sodium acetate in 500 l of water were added.
Nach 5- bis 8tägigem Rühren ist die Umsetzung beendigt; man giebt nun das diazotirte Primulin, hergestellt aus 56 kg Primulin (bezw. einer 6,95 kg Natriumnitrit entsprechenden Menge), 6,95 kg Natriumnitrit, 500 1 Wasser, 49 kg Salzsäure (30 pCt.), hinzu. Die Farbstoffbildung erfordert wieder einige Tage. Schliefslich wird erhitzt und der Farbstoff durch Zusatz von Salzsäure ausgefällt. Das abfiltrirte Product wird mit der zur Bildung' des löslichen Natriumsalzes erforderlichen Menge Soda gemischt, getrocknet und gemahlen. Man erhält ein braunes,After stirring for 5 to 8 days, the reaction is complete; the diazotized is now given Primulin, made from 56 kg primulin (or a 6.95 kg sodium nitrite equivalent Amount), 6.95 kg sodium nitrite, 500 l water, 49 kg hydrochloric acid (30 pCt.). The dye formation again requires a few days. Finally, it is heated and the dye is added precipitated by hydrochloric acid. The filtered product is mixed with that for the formation of the soluble sodium salt required amount of soda mixed, dried and ground. You get a brown,
in Wasser mit orangebrauner Farbe lösliches Pulver, das ungeheizte Baumwolle röthlich orange färbt.Powder soluble in water with an orange-brown color, unheated cotton reddish colors orange.
Farbstoffe ,von ähnlicher Nuance entstehen, wenn in diesem Beispiel das Anilin durch die äquivalente Menge o-Toluidin, p-Toluidin, m-Xylidin, ci-Naphtylamin oder ß-Naphtylamin ersetzt wird.Dyes of a similar shade if in this example the aniline is replaced by the equivalent amount of o-toluidine, p-toluidine, m-xylidine, ci-naphthylamine or ß-naphthylamine replaced will.
II. m-Phenylendiamindisulfosäure combirrirt mit Primulin und Sulfanilsäure. 56 kg Primulin (bezw. eine 6,95 kg Natriumnitrit entsprechende Menge) werden in 500 1 Wasser in bekannter Weise mit 6,95 kg Natriumnitrit und 49 kg Salzsäure 30 pCt. diazotirt und dann in eine eiskalte Lösung von 26,8 kg m-Phenylendiamindisulfosäure und 28 kg calcinirter Soda in 400 1 Wasser gegossen. Nach 24StUndigem Rühren wird die Lösung mit 30 kg krystallisirtem Natriumacetat und dann mit der Diazoverbindung aus 19,5 kg sulfanilsaurem Natrium, 6,95 kg Natriumnitrit, 200 1 Wasser und 39 kg Salzsäure (30 pCt.) versetzt. Man rührt 5 bis 8 Tage, erhitzt hierauf die Lösung, säuert mit Salzsäure an und fällt mit Kochsalz. Das wie in Beispiel I weiter behandelte Product ist ein braunes Pulver, in Wasser mit orangerother Farbe löslich und färbt ungeheizte Baumwolle lebhaft orange. Beim Ersatz der Sulfanilsäure durch die äquivalente Menge Metanilsäure, Naphtionsäure oder eine der oben genannten ß-Naphtylaminsulfosäuren erhält man ähnlich färbende Producte.II. M-Phenylenediamine disulfonic acid combined with primulin and sulfanilic acid. 56 kg of primulin (or a 6.95 kg of sodium nitrite corresponding amount) in 500 l of water in a known manner with 6.95 kg of sodium nitrite and 49 kg hydrochloric acid 30 pCt. diazotized and then in an ice-cold solution of 26.8 kg of m-phenylenediamine disulfonic acid and poured 28 kg of calcined soda into 400 liters of water. After 24 hours The solution is stirred with 30 kg of crystallized sodium acetate and then with the Diazo compound from 19.5 kg of sodium sulfanil, 6.95 kg of sodium nitrite, 200 l of water and 39 kg hydrochloric acid (30 pCt.) are added. The mixture is stirred for 5 to 8 days, then the solution is heated and acidified with hydrochloric acid and precipitates with table salt. The Product treated further as in Example I. a brown powder, soluble in water with an orange-red color, and stains unheated cotton vivid orange. When replacing the sulfanilic acid with the equivalent amount of metanilic acid, Naphthionic acid or one of the ß-naphthylamine sulfonic acids mentioned above are obtained in a similar manner coloring products.
Claims (2)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE76118C true DE76118C (en) |
Family
ID=349031
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT76118D Expired - Lifetime DE76118C (en) | Process for the preparation of primary disazo dyes with m-phenylenediamine disulfonic acid |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE76118C (en) |
-
0
- DE DENDAT76118D patent/DE76118C/en not_active Expired - Lifetime
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