DE37021C - Process for the preparation of yellow basic azo dyes from diazotized metanitraniline etc. and metaphenylenediamine - Google Patents
Process for the preparation of yellow basic azo dyes from diazotized metanitraniline etc. and metaphenylenediamineInfo
- Publication number
- DE37021C DE37021C DENDAT37021D DE37021DA DE37021C DE 37021 C DE37021 C DE 37021C DE NDAT37021 D DENDAT37021 D DE NDAT37021D DE 37021D A DE37021D A DE 37021DA DE 37021 C DE37021 C DE 37021C
- Authority
- DE
- Germany
- Prior art keywords
- metaphenylenediamine
- diazotized
- metanitraniline
- preparation
- azo dyes
- 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
- WZCQRUWWHSTZEM-UHFFFAOYSA-N M-Phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 title claims description 6
- 239000000987 azo dye Substances 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000011780 sodium chloride Substances 0.000 claims description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 2
- HFCFJYRLBAANKN-UHFFFAOYSA-N 2-methyl-3-nitroaniline Chemical compound CC1=C(N)C=CC=C1[N+]([O-])=O HFCFJYRLBAANKN-UHFFFAOYSA-N 0.000 claims 1
- XJCVRTZCHMZPBD-UHFFFAOYSA-N 3-Nitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1 XJCVRTZCHMZPBD-UHFFFAOYSA-N 0.000 claims 1
- GDIIPKWHAQGCJF-UHFFFAOYSA-N 4-Amino-2-nitrotoluene Chemical compound CC1=CC=C(N)C=C1[N+]([O-])=O GDIIPKWHAQGCJF-UHFFFAOYSA-N 0.000 claims 1
- 239000005711 Benzoic acid Substances 0.000 claims 1
- 235000010233 benzoic acid Nutrition 0.000 claims 1
- 239000001043 yellow dye Substances 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 239000000975 dye Substances 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- GEYOCULIXLDCMW-UHFFFAOYSA-N O-Phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- MCTQNEBFZMBRSQ-UHFFFAOYSA-N (3-amino-4-phenyldiazenylphenyl)azanium;chloride Chemical compound Cl.NC1=CC(N)=CC=C1N=NC1=CC=CC=C1 MCTQNEBFZMBRSQ-UHFFFAOYSA-N 0.000 description 1
- VYWYYJYRVSBHJQ-UHFFFAOYSA-N 3,5-Dinitrobenzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 VYWYYJYRVSBHJQ-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K Iron(III) chloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 210000002268 Wool Anatomy 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 description 1
- GNNALEGJVYVIIH-UHFFFAOYSA-N benzene-1,2-diamine;hydrochloride Chemical compound Cl.NC1=CC=CC=C1N GNNALEGJVYVIIH-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003638 reducing agent Substances 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- KEAYESYHFKHZAL-OUBTZVSYSA-N sodium-24 Chemical compound [24Na] KEAYESYHFKHZAL-OUBTZVSYSA-N 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N tolylenediamine group Chemical group CC1=C(C=C(C=C1)N)N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMTPATENT OFFICE
und Metaphenylendiamin.and metaphenylenediamine.
Aus Diazobenzol und Metaphenylendiamin wird bekanntlich der als Chrysoidin bezeichnete Farbstoff gewonnen. Ersetzt man nun den Diazokörper durch nitrirte Substitutionsproducte, so entstehen nitrirte Derivate von basischer Natur, die Seide, Wolle und Bäumwolle gelb bezw. braun färben und welche unter dem Namen »Azophosphine« zusammengefafst werden sollen.It is well known that diazobenzene and metaphenylenediamine are made into what is known as chrysoidin Dye obtained. If the diazo body is now replaced by nitrided substitution products, in this way nitrated derivatives of a basic nature are produced, the silk, wool and cotton wool yellow respectively brown in color and which are grouped under the name "Azophosphine" should.
Speciell sind es die Metanitroverbindungen und unter diesen wieder die des Anilins, des Orthotoluidins, des Paratoluidins und der Amidobenzoesäure, welche, diazotirt und mit Phenylendiamin in Combination gebracht, Farbstoffe von rein gelber, phosphinähnlicher Nuance liefern.Specifically there are the metanitro compounds and among these again those of aniline, des Orthotoluidins, Paratoluidins and Amidobenzoic acid, which, diazotized and with Phenylenediamine brought into combination, colorings with a pure yellow, phosphine-like shade deliver.
An Stelle von Phenylendiamin kann natürlich auch Toluylendiamin treten, und werden damit Farbstoffe von etwas rötherer Nuance erhalten.Instead of phenylenediamine, tolylenediamine can of course also be used so that dyes of a slightly redder shade are obtained.
Die Azophosphine zeigen eine grofse Uebereinstimmung in ihren allgemeinen Eigenschaften und lassen sich am besten durch Ausfärbungen von einander unterscheiden; sie bilden braunrothe bis schwarzbraune Pulver, welche sich in Wasser mit Leichtigkeit lösen. Infolge der Anwesenheit einer VNitrogruppe werden die Salze durch gröfsere Mengen Wassers leicht zersetzt Und müssen aus diesem Grunde der Lösung stets einige Tropfen Säure zugesetzt werden.The azophosphines show great agreement in their general properties and can best be distinguished from one another by coloration; they form brownish-red to black-brown powders, which dissolve easily in water. As a result of In the presence of a V-nitro group, the salts become light with larger amounts of water decomposed And for this reason a few drops of acid must always be added to the solution will.
Die Sulfosäuren der Azophosphine entstehen durch directe Sulfurirung nur schwierig, bequem läfst, sich dagegen ein hierher gehöriger Körper z. B. erhalten durch Diazotirung der von Post und Härtung (Annalen 205, S. 102) beschriebenen m - Nitranilinsulfosäure und Vereinigung des Products mit Phenylendiamin.The sulphonic acids of the azophosphines are difficult and convenient to produce by direct sulphuration läfst, on the other hand, a body belonging here z. B. obtained by diazotization of the von Post and hardening (Annalen 205, p. 102) m - Nitranilinsulfonic acid and the product's association with phenylenediamine.
Wie schon oben erwähnt, sind die Metanitroverbindungen diejenigen, welche die schönsten und charakteristischsten Farbstoffe liefern, und sei in folgendem unser Verfahren beispielsweise beschrieben.As mentioned above, the metanitro compounds are the most beautiful and deliver the most characteristic dyes, and be our method in the following, for example described.
1. 13,8 kg Metanitranilin werden in 24 kg Salzsäure und 200 1 Wasser gelöst und durch Zusatz einer Lösung von 7 kg Natriumnitrit diazotirt. Das Reactionsproduct wird nach einigem Stehen mit einer wässerigen Lösung von 18 kg salzsaurem 'Metaphenylendiamin in 200 1 Wasser vereinigt. Der Farbstoff entsteht sofort und wird 'durch Umlösen und Aussalzen gereinigt. Die Base des so erhaltenen Farbstoffes läfst sich sowohl durch langsames Erkalten der verdünnten wässerigen Lösung, als auch aus Sprit in Krystallen erhalten; wir haben ihren Schmelzpunkt zu 2040 C. gefunden. 1. 13.8 kg of metanitraniline are dissolved in 24 kg of hydrochloric acid and 200 liters of water and diazotized by adding a solution of 7 kg of sodium nitrite. After standing for a while, the reaction product is combined with an aqueous solution of 18 kg of hydrochloric acid metaphenylenediamine in 200 l of water. The dye arises immediately and is purified by dissolving and salting out. The base of the dye thus obtained can be obtained in crystals both by slowly cooling the dilute aqueous solution and from fuel; we have found its melting point to be 204 ° C.
Saure Reductionsmittel entfärben die Farblösung unter Bildung von Polyaminen, welche mit Oxydationsmitteln, z. B. Eisenchlorid, unbeständige röthliche Färbungen annehmen.Acid reducing agents discolor the color solution with the formation of polyamines, which with oxidizing agents, e.g. B. ferric chloride, assume inconsistent reddish tints.
2. 15,2 kg Metanitroorthotoluidin (Schmelzpunkt 1070 C.) bezw. Metanitroparatoluidin (Schmelzp.unkt 780 C.) werden in ganz derselben Weise diazotirt und mit 18 kg salzsaurem Metaphenylendiamin vereinigt.2. 15.2 kg of metanitroorthotoluidine (melting point 107 ° C.) or Metanitroparatoluidin (Schmelzp.unkt 78 0 C.) diazotirt be in exactly the same way and combined with 18 kg of hydrochloric acid metaphenylene.
Die Farbstoffe entstehen hier- w.ie unter ι. angegeben und werden ebenso isolir.t und' gereinigt. Sie unterscheiden sich von dem aus' Metanitranilin erhältlichen durch eine etwas röthere Farbnüance, sind im übrigen in Bezug auf allgemeine Eigenschaften demselben gleich.The dyes arise here- w.ie under ι. and are also isolated and purified. They differ from that from ' Metanitraniline, available through a slightly redder shade, are also related equal to it in general properties.
3. 20,4 kg metanitramidobenzoesaures Natron aus symmetrischer Dinitrobenzoesäure werden in 200 1 Wasser gelöst, mit einer wässerigen Lösung von 7 kg Natriumnitrit und 24 kg Salzsäure diazotirt und mit 18 kg salzsaurem Phenylendiamin in 200 1 Wasser gepaart.3. 20.4 kg of metanitramidobenzoic acid soda can be obtained from symmetrical dinitrobenzoic acid Dissolved in 200 l of water, with an aqueous solution of 7 kg of sodium nitrite and 24 kg Hydrochloric acid diazotized and paired with 18 kg of hydrochloric acid phenylenediamine in 200 liters of water.
Das salzsaure Salz des Farbstoffes scheidet sich direct aus und wird durch Umlösen gereinigt. Es unterscheidet sich von den unter , 1*1 und 2. erwähnten durch eine mehr gelbe 'Nfiance.The hydrochloric acid salt of the dye is deposited directly and is purified by dissolving. It differs from the ones mentioned under, 1 * 1 and 2. by a more yellow one 'Nfiance.
-i- ι In allen drei Fällen kann an Stelle des salzsa'uren Metaphenylendiamins - ■ die äquivalente 'Menge salzsauren Metatoluylendiamins verwendet werden, und sind die hiermit erhältlichen Farbtöne etwas röther wie die bisher erwähnten.-i- ι In all three cases, instead of hydrochloric acid Metaphenylenediamine - ■ the equivalent 'amount of hydrochloric acid metatoluylenediamine used and the colors available with this are a little redder than those mentioned so far.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE37021C true DE37021C (en) |
Family
ID=312803
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT37021D Expired - Lifetime DE37021C (en) | Process for the preparation of yellow basic azo dyes from diazotized metanitraniline etc. and metaphenylenediamine |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE37021C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1024900B (en) * | 1956-09-25 | 1958-02-20 | Bayer Ag | Process for the processing of sugar crystallization processes |
-
0
- DE DENDAT37021D patent/DE37021C/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1024900B (en) * | 1956-09-25 | 1958-02-20 | Bayer Ag | Process for the processing of sugar crystallization processes |
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