DE293429C - - Google Patents
Info
- Publication number
- DE293429C DE293429C DENDAT293429D DE293429DA DE293429C DE 293429 C DE293429 C DE 293429C DE NDAT293429 D DENDAT293429 D DE NDAT293429D DE 293429D A DE293429D A DE 293429DA DE 293429 C DE293429 C DE 293429C
- Authority
- DE
- Germany
- Prior art keywords
- dye
- acid
- parts
- azo dyes
- acetoacetic
- 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
- 239000002253 acid Substances 0.000 claims description 6
- 239000000987 azo dye Substances 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- AXWKFRWLYPZEFQ-UHFFFAOYSA-N 3-oxobutanoyl chloride Chemical compound CC(=O)CC(Cl)=O AXWKFRWLYPZEFQ-UHFFFAOYSA-N 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 150000004982 aromatic amines Chemical class 0.000 claims 1
- 239000000975 dye Substances 0.000 description 16
- MVPPADPHJFYWMZ-UHFFFAOYSA-N Chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N Thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Chemical compound CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 230000000875 corresponding Effects 0.000 description 3
- WGQKYBSKWIADBV-UHFFFAOYSA-N Benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-Naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-Naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 1
- DRGIDRZFKRLQTE-UHFFFAOYSA-N 2-chloroaniline;hydron;chloride Chemical compound Cl.NC1=CC=CC=C1Cl DRGIDRZFKRLQTE-UHFFFAOYSA-N 0.000 description 1
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4,4'-Oxydianiline Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 1
- 241000947840 Alteromonadales Species 0.000 description 1
- QPQKUYVSJWQSDY-CCEZHUSRSA-N Aniline Yellow Chemical compound C1=CC(N)=CC=C1\N=N\C1=CC=CC=C1 QPQKUYVSJWQSDY-CCEZHUSRSA-N 0.000 description 1
- JPYQFYIEOUVJDU-UHFFFAOYSA-N Beclamide Chemical compound ClCCC(=O)NCC1=CC=CC=C1 JPYQFYIEOUVJDU-UHFFFAOYSA-N 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N Benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- JBCSOBKDUKAJHR-UHFFFAOYSA-N ClO.NC1=CC=CC=C1 Chemical compound ClO.NC1=CC=CC=C1 JBCSOBKDUKAJHR-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N M-Phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- BFVHBHKMLIBQNN-UHFFFAOYSA-N N-(2-chlorophenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1Cl BFVHBHKMLIBQNN-UHFFFAOYSA-N 0.000 description 1
- KOHNUEXAOQRRPI-UHFFFAOYSA-N N-benzyl-3-oxobutanamide Chemical compound CC(=O)CC(=O)NCC1=CC=CC=C1 KOHNUEXAOQRRPI-UHFFFAOYSA-N 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N P-Anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N P-Phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- WXWCDTXEKCVRRO-UHFFFAOYSA-N Para-Cresidine Chemical compound COC1=CC=C(C)C=C1N WXWCDTXEKCVRRO-UHFFFAOYSA-N 0.000 description 1
- -1 Use aminonaphtol Chemical compound 0.000 description 1
- GCPWJFKTWGFEHH-UHFFFAOYSA-N acetoacetamide Chemical class CC(=O)CC(N)=O GCPWJFKTWGFEHH-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- XKXHCNPAFAXVRZ-UHFFFAOYSA-N benzylazanium;chloride Chemical compound [Cl-].[NH3+]CC1=CC=CC=C1 XKXHCNPAFAXVRZ-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 150000004992 toluidines Chemical class 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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/32—Preparation of azo dyes from other azo compounds by reacting carboxylic or sulfonic groups, or derivatives thereof, with amines; by reacting keto-groups with amines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
-JVl 293429-KLASSE 22 a. GRUPPE-JVl 293429-CLASS 22 a. GROUP
FARBENFABRIKEN vorm. FRIEDR. BAYER & CO. in LEVERKUSEN b. CÖLN a. Rh.FARBENFABRIKEN vorm. FRIEDR. BAYER & CO. in LEVERKUSEN b. CÖLN a. Rh.
Verfahren zur Darstellung von Azofarbstoffen. Patentiert im Deutschen Reiche vom 21. Februar 1914 ab. Process for the preparation of azo dyes. Patented in the German Empire on February 21, 1914.
Es wurde gefunden, daß man Acetessigsäure-It has been found that acetoacetic acid
chloridazofarbstoffe, die durch Einwirkung von Thionylchlorid auf Acetessigsäureazofarbstoffe erhältlich sind, in glatter Weise mit Aminen in die entsprechenden Säureamidfarbstoffe über-. führen kann.Chloride azo dyes produced by the action of thionyl chloride on acetoacetic acid azo dyes are available, in a smooth manner with amines in the corresponding acid amide dyes. can lead.
Derartige Farbstoffe sind bisher durch Kup-,· pein der entsprechenden Amide der Acetessigsäure mit Diazoverbindungen erhalten worden. ίο Das vorliegende Verfahren hat den Vorteil, daß es die Herstellung einer großen Zahl von Farbstoffen ermöglicht, die nach dem bekannten Verfahren technisch nicht herstellbar sind, weil die entsprechenden Acetessigsäureamide gar nicht oder nur in technisch unzureichender Ausbeute zugänglich sind.Such dyes have hitherto been obtained by cup-, pein of the corresponding amides of acetoacetic acid with diazo compounds. ίο The present procedure has the advantage that it allows the production of a large number of dyes according to the known Processes cannot be produced industrially because the corresponding acetoacetamides even are not accessible or only in technically inadequate yield.
In eine Chlorbenzollösung von 285,5 Gewichtsteilen des Acetessigsäurechloridfarbstoffes, der aus 4-Chlor-2-nitrobenzol-l-azoacetessigsäure durch Umsetzung mit Thionylchlorid erhältlich ist, läßt man bei 20 ° 214 Gewichtsteile Benzylamin einlaufen. Es scheidet sich der Benzylamidfarbstoff vermischt mit dem Chlorhydrat des Benzylamins ab. Nach Auswaschen des salzsauren Benzylamins mit heißem Wasser bleibt der Acetessigbenzylamidfarbstoff zurück. Schmelzpunkt 192°. Ein zweiter Anteil des Farbstoffes kristallisiert beim Einengen der abgesaugten Chlorbenzollösung aus. Die Gesamtausbeute ist nahezu quantitativ.In a chlorobenzene solution of 285.5 parts by weight of the acetoacetic acid chloride dye, obtainable from 4-chloro-2-nitrobenzene-1-azoacetoacetic acid by reaction with thionyl chloride is, is allowed to run in at 20 ° 214 parts by weight of benzylamine. It separates Benzylamide dye mixed with the chlorohydrate of benzylamine. After washing out of the hydrochloric acid benzylamine with hot water, the acetoacetic benzylamide dye remains. Melting point 192 °. A second portion of the dye crystallizes when the extracted chlorobenzene solution. The overall yield is almost quantitative.
283,5 Teile des Farbstoffsäurechlorides, das aus dem Farbstoff 2-Nitro-4-toluol-i-azoacetessigsäure durch Umsetzung mit Thionylchlorid erhältlich ist, werden in Solventnaphta gelöst. Zu der auf 20° abgekühlten Lösung läßt man 186 Gewichtsteile Anilin unter Kühlung zulaufen. Es scheidet sich der größte Teil des Acetessiganilidfarbstoffes vermischt mit Anilinchlorhydrat ab. Das Gemisch wird abgesaugt und aus ihm das salzsaure Salz des Anilins mit heißem Wasser herausgewaschen. ' .283.5 parts of the dye acid chloride obtained from the dye 2-nitro-4-toluene-i-azoacetoacetic acid obtainable by reaction with thionyl chloride are dissolved in solvent naphtha. 186 parts by weight of aniline are allowed to run into the solution, which has been cooled to 20 °, with cooling. Most of the acetoacetanolide dye separates out mixed with aniline chlorohydrate away. The mixture is suctioned off and from it the hydrochloric acid salt of aniline washed out of hot water. '.
Es bleibt der reine Anilidfarbstoff zurück. Durch Einengen der abgesaugten Solventnaphta wird noch eine zweite schmelzpunktreine Färb st off menge gewonnen. Die Gesamtausbeute ist nahezu quantitativ. Schmelzpunkt 256 °.The pure anilide dye remains. By concentrating the sucked off solvent naphtha a second amount of dye with a pure melting point is obtained. The total yield is almost quantitative. Melting point 256 °.
304 Gewichtsteile des Farbstoffsäurechlorides, das aus dem Farbstoff 4-Chlor-2-nitrobenzol-iazoacetessigsäure durch Umsetzung mit Thionylchlorid erhältlich ist, werden in Chlorbenzol gelöst. Zu dieser Lösung läßt man bei 20° 255 Gewichtsteile o-Chloranilin (2 Mol.) zulaufen. Es scheidet sich ein dicker gelber Brei ab, der ab-304 parts by weight of the dye acid chloride obtained from the dye 4-chloro-2-nitrobenzene-iazoacetoacetic acid obtainable by reaction with thionyl chloride are dissolved in chlorobenzene. 255 parts by weight of o-chloroaniline (2 mol.) Are allowed to run into this solution at 20.degree. It a thick yellow pulp is deposited, which
gesaugt wird. Nach dem Herauswaschen des salzsauren o-Chloranilins verbleibt der reine Acetessig-o-chloranilidfarbstofi zurück. Ein zweiter Anteil des Farbstoffes ist durch Einengen der abgesaugten Chlorbenzollösung zu gewinnen. Die Gesamtausbeute ist nahezu quantitativ. Schmelzpunkt 249 bis 250 °.is sucked. After washing out the hydrochloric acid o-chloroaniline, the pure remains Acetoacetic acid-o-chloroanilide dye back. A The second part of the dye is closed by concentrating the extracted chlorobenzene solution to win. The overall yield is almost quantitative. Melting point 249 to 250 °.
Statt der in den Beispielen zur Umsetzungverwandten Aminoverbindungen kann man beliebige andere, wie die Toluidine, Anisidin, Kresidin, Nitranilin, m- und p-Phenylendiamin, Benzidin,Diaminodiphenyläther, α-und ß-Naphtylamin, Aminonaphtol, Aminoazobenzol und andere, verwenden.Instead of the amino compounds used for the reaction in the examples, any desired others, such as the toluidines, anisidine, cresidine, nitraniline, m- and p-phenylenediamine, Benzidine, diaminodiphenyl ether, α- and ß-naphthylamine, Use aminonaphtol, aminoazobenzene, and others.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE293429C true DE293429C (en) |
Family
ID=548088
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT293429D Active DE293429C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE293429C (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE921223C (en) * | 1951-03-02 | 1954-12-13 | Ciba Geigy | Process for the preparation of acid amide derivatives of azo compounds |
| DE943901C (en) * | 1952-12-24 | 1956-06-01 | Ciba Geigy | Process for the preparation of new carboxamide derivatives of azo dyes |
| DE1013018B (en) * | 1952-03-27 | 1957-08-01 | Ciba Geigy | Process for the preparation of o-oxyazo dye sulfonic acid amides or esters |
| US5664521A (en) * | 1992-10-09 | 1997-09-09 | Tickleford Limited | Apparatus for and method of milking an animal |
-
0
- DE DENDAT293429D patent/DE293429C/de active Active
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE921223C (en) * | 1951-03-02 | 1954-12-13 | Ciba Geigy | Process for the preparation of acid amide derivatives of azo compounds |
| DE1013018B (en) * | 1952-03-27 | 1957-08-01 | Ciba Geigy | Process for the preparation of o-oxyazo dye sulfonic acid amides or esters |
| DE943901C (en) * | 1952-12-24 | 1956-06-01 | Ciba Geigy | Process for the preparation of new carboxamide derivatives of azo dyes |
| US5664521A (en) * | 1992-10-09 | 1997-09-09 | Tickleford Limited | Apparatus for and method of milking an animal |
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