DE742662C - Process for the preparation of acidic disazo dyes - Google Patents
Process for the preparation of acidic disazo dyesInfo
- Publication number
- DE742662C DE742662C DEG103956D DEG0103956D DE742662C DE 742662 C DE742662 C DE 742662C DE G103956 D DEG103956 D DE G103956D DE G0103956 D DEG0103956 D DE G0103956D DE 742662 C DE742662 C DE 742662C
- Authority
- DE
- Germany
- Prior art keywords
- acidic
- preparation
- disazo dyes
- dyes
- sulfonic
- 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
Links
- 239000000975 dye Substances 0.000 title claims description 12
- 238000000034 method Methods 0.000 title claims description 6
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims description 5
- 230000002378 acidificating effect Effects 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical group OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- 239000003929 acidic solution Substances 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims 1
- 150000004985 diamines Chemical class 0.000 claims 1
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000003457 sulfones Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 125000003545 alkoxy group Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229910052736 halogen Chemical class 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- WPPDXAHGCGPUPK-UHFFFAOYSA-N red 2 Chemical compound C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=2C=3C4=CC=C5C6=CC=C7C8=C(C=9C=CC=CC=9)C9=CC=CC=C9C(C=9C=CC=CC=9)=C8C8=CC=C(C6=C87)C(C=35)=CC=2)C4=C1C1=CC=CC=C1 WPPDXAHGCGPUPK-UHFFFAOYSA-N 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 210000002268 wool Anatomy 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
- C09B35/02—Disazo dyes
- C09B35/039—Disazo dyes characterised by the tetrazo component
- C09B35/28—Disazo dyes characterised by the tetrazo component the tetrazo component containing two aryl nuclei linked by at least one of the groups —CON<, —SO2N<, —SO2—, or —SO2—O—
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung von 'sauren Disazofarbstoffen Es wurde ,gefunden, daß man wertvolle rote Disazofarbstofte erhält, wenn man sulfon- und carbonsäuregruppen:freie Diaminodiphenylsulfone oder Diarninod'iphenylsulfoxyde und deren Abkömmlinge, wie die Alkyl-, Alkoxy- oder Halogenderivate, tetrazotiert und die Tetrazoverbindungen mit 2 Molekülen 2-Ami.no-8-oxynaphthalin-6-sulfonsäure in saurer Lösung vereinigt.Process for the preparation of 'acidic disazo dyes It has been found that valuable red disazo dyes are obtained if sulfonic and carboxylic acid groups are free Diaminodiphenylsulfone or Diarninod'iphenylsulfoxde and their derivatives, such as the alkyl, alkoxy or halogen derivatives, tetrazotized and the tetrazo compounds combined with 2 molecules of 2-Ami.no-8-oxynaphthalene-6-sulfonic acid in acidic solution.
Die neuen Farbstoffe besitzen eine überraschend gute Lichtechtheit und eine bemerkenswerte Seewasiserechtheit.The new dyes have surprisingly good lightfastness and a remarkable seawater fairness.
Es ist zwar bekannt, @daß man Disazofarbstoffedurch Kuppeln von z Mol 2-A.mino-8-oxynaphthal.in-6-sulfonsäure mit z Mol eines tetrazotierten D@iaminodiphenyls, in dem beide Phenylreste.durch eine aus einem oder mehreren Schwefelatomen -bestehende Brücke miteinander verbunden sind, hergestellt hat. Ebenso" ist bekannt, @daß man nitrogruppenhaltige Tetrazokomponenten obiger Zusammensetzung für die Herstellung ähnlicher Farbstoffe verwendet hat: Verglichen damit, besitzen die nach hem vorliegenden Verfahren erhältlichen Farbstoffe eine überlegene Lichtechtheit.It is known that disazo dyes can be obtained by coupling e.g. Mol of 2-A.mino-8-oxynaphthal.in-6-sulfonic acid with z mol of a tetrazotized D @ iaminodiphenyl, in which both Phenylreste.by one consisting of one or more sulfur atoms Bridge are connected to each other. It is also known @ that one Nitro-group-containing tetrazo components of the above composition for the production has used similar dyes: Compared with this, the ones present after hem Processes obtainable dyes have a superior lightfastness.
Beispiel 27;6 Teile 4, 4'-Dimethyl-3, 3'-diaminod'iphenyIsulfon werden in üblicher Weise tetrazotiert. Die Tetrazoniumverbindung kuppelt man mit 47,8 Teilen 2-Amino-8-oxynaphthalin--6-sulfonsäure, die man in Zoo Teilen Wasser mit der nötigen Sodamenge neutral gelöst und wieder mit Salzsäure durch Ansäuern bis zu kongosaurer Reaktion ausgefällt hat. Die Kupplung erfolgt langsam. Durch Erwärmen und Zusatz von Natriumacetat kann sie jedoch beschleunigt werden. Nach Beendigung der Fa-rbstoffbildung stellt man mit Sodalösung kongoneutral, filtriert und trocknet. .Der -Farbstoff., .ein dunkelrotes Pulver, löst sich in Wasser gelbstichigrot, in konzentriert`er Schwefelsäure violett und färbt `rolle aus saurem Bade in blaustichig roten. lichtechten Tönen.Example 27; 6 parts of 4,4'-dimethyl-3, 3'-diaminod'iphenyIsulfon become tetrazotized in the usual way. The tetrazonium compound is coupled with 47.8 parts 2-Amino-8-oxynaphthalene - 6-sulfonic acid, which one in zoo parts of water with the necessary Soda amount dissolved neutrally and again with hydrochloric acid by acidification up to Congo acid Response has failed. The coupling is slow. By heating and adding of sodium acetate, however, it can be accelerated. After completion the dye formation is made Congo-neutral with soda solution, filtered and dried. .The dye.,. A dark red powder, dissolves in water with a yellowish tinge, in concentrated sulfuric acid violet and colors the roll of acid bath with a bluish tinge redden. lightfast tones.
Nach dem gleichen Verfahren können folgende Farbstoffe hergestellt
werden:
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH742662X | 1941-07-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE742662C true DE742662C (en) | 1943-12-14 |
Family
ID=4533278
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEG103956D Expired DE742662C (en) | 1941-07-29 | 1941-08-20 | Process for the preparation of acidic disazo dyes |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE742662C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0598244A1 (en) * | 1992-11-19 | 1994-05-25 | BASF Aktiengesellschaft | Process for dyeing of leather with a red azo dyestuff |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE161462C (en) * | ||||
| US1821256A (en) * | 1927-04-22 | 1931-09-01 | British Dyestuffs Corp Ltd | New azo dyestuffs and their application |
-
1941
- 1941-08-20 DE DEG103956D patent/DE742662C/en not_active Expired
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE161462C (en) * | ||||
| US1821256A (en) * | 1927-04-22 | 1931-09-01 | British Dyestuffs Corp Ltd | New azo dyestuffs and their application |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0598244A1 (en) * | 1992-11-19 | 1994-05-25 | BASF Aktiengesellschaft | Process for dyeing of leather with a red azo dyestuff |
| US5411556A (en) * | 1992-11-19 | 1995-05-02 | Basf Aktiengesellschaft | Dyeing leather with a red azo dye |
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