CH370856A - Process for the production of water-insoluble azo dyes - Google Patents
Process for the production of water-insoluble azo dyesInfo
- Publication number
- CH370856A CH370856A CH6447058A CH6447058A CH370856A CH 370856 A CH370856 A CH 370856A CH 6447058 A CH6447058 A CH 6447058A CH 6447058 A CH6447058 A CH 6447058A CH 370856 A CH370856 A CH 370856A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- benzene
- water
- azo dyes
- production
- Prior art date
Links
- 239000000987 azo dye Substances 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- 150000001989 diazonium salts Chemical class 0.000 claims description 3
- OCISOSJGBCQHHN-UHFFFAOYSA-N 3-hydroxynaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC(O)=CC2=C1 OCISOSJGBCQHHN-UHFFFAOYSA-N 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- HVZZVTRUVBRVHQ-UHFFFAOYSA-N (4-nitro-6-sulfonylcyclohexa-2,4-dien-1-yl)-phenyldiazene Chemical compound S(=O)(=O)=C1C(C=CC(=C1)[N+](=O)[O-])N=NC1=CC=CC=C1 HVZZVTRUVBRVHQ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000004043 dyeing Methods 0.000 description 3
- IVSZLXZYQVIEFR-UHFFFAOYSA-N 1,3-Dimethylbenzene Natural products CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- OSIGJGFTADMDOB-UHFFFAOYSA-N 1-Methoxy-3-methylbenzene Chemical compound COC1=CC=CC(C)=C1 OSIGJGFTADMDOB-UHFFFAOYSA-N 0.000 description 2
- OACCRGFGCIQFNR-UHFFFAOYSA-N 1-chloro-2,4-dimethoxybenzene Chemical compound COC1=CC=C(Cl)C(OC)=C1 OACCRGFGCIQFNR-UHFFFAOYSA-N 0.000 description 2
- QMXZSRVFIWACJH-UHFFFAOYSA-N 1-chloro-2,5-dimethoxybenzene Natural products COC1=CC=C(OC)C(Cl)=C1 QMXZSRVFIWACJH-UHFFFAOYSA-N 0.000 description 2
- YRGAYAGBVIXNAQ-UHFFFAOYSA-N 1-chloro-4-methoxybenzene Chemical compound COC1=CC=C(Cl)C=C1 YRGAYAGBVIXNAQ-UHFFFAOYSA-N 0.000 description 2
- ZMZVVVASCILFJL-UHFFFAOYSA-N 2-chloro-4-methoxy-1-methylbenzene Chemical compound COC1=CC=C(C)C(Cl)=C1 ZMZVVVASCILFJL-UHFFFAOYSA-N 0.000 description 2
- OHBQPCCCRFSCAX-UHFFFAOYSA-N Hydroquinone dimethyl ether Natural products COC1=CC=C(OC)C=C1 OHBQPCCCRFSCAX-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- DSZOTMKIKJOOPG-UHFFFAOYSA-N (2-nitrophenyl)-phenyldiazene Chemical compound [O-][N+](=O)C1=CC=CC=C1N=NC1=CC=CC=C1 DSZOTMKIKJOOPG-UHFFFAOYSA-N 0.000 description 1
- NPDACUSDTOMAMK-UHFFFAOYSA-N 4-Chlorotoluene Chemical compound CC1=CC=C(Cl)C=C1 NPDACUSDTOMAMK-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000010409 ironing Methods 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- -1 naphthyl radical Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/02—Disazo dyes
- C09B31/06—Disazo dyes from a coupling component "C" containing a directive hydroxyl group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung von wasserunlöslichen Azofarbstoffen Es wurde gefunden, dass man zu neuen, wert vollen wasserunlöslichen Azofarbstoffen gelangt, wenn man die Diazoniumverbindungen aus o-Aminoazover- bindungen von der allgemeinen Formel
EMI0001.0009
mit Arylamid'en der 2,3-Oxy-naphthoes.äure von der allgemeinen Formel
EMI0001.0012
worin R einen durch mindestens ein Halogenatom,
eine Alkyl- oder Alkoxygruppe substituierten Phenyl- rest oder einen Naphthylrest bedeutet, kuppelt.
Mit den neuen Farbstoffen erhält man auf pflanz lichen Fasern, einschliesslich solchen aus regenerier ter Cellulose, nach den bekannten Färbe- und Druck- verfahren vorwiegend grünstichig-braune bis grüne Färbungen und Drucke von guten Echtheitseigen schaften, wie sie bisher in der Eisfarbenreihe unter Verwendung geeigneter Diazokomponenten noch nicht erhalten werden konnten.
Die Farbstoffe lassen sich auch auf einem nicht textilen Substrat herstellen und können zum Färben von hochmolekularen plastischen Massen oder für die Zubereitung von Farblacken verwendet werden. Die Herstellung der als Diazokomponenten ver wendeten o-Aminoazoverbindungen kann nach be kannten Methoden erfolgen. Zweckmässig verwendet man für die Herstellung der neuen Farbstoffe die festen haltbaren Diazoniumverbindungen, wie sie ge mäss Patent Nr.366052 erhalten werden.
Gegenüber dem aus der österreichischen Patent schrift Nr. 141854 bekannten wasserunlöslichen Azo- farbstoff aus diazotiertem 2-Amino-4-methoxy-5- methyl-2'-phenylsülfonyl-4'=nitro-1,1'-azobenzol und 2,3-Oxy-naphthoylaminobenzol zeichnen sich die ver fahrensgemäss erhältlichen Azofarbstoffe durch eine bessere Licht-, Chlor- und Bügelechtheit der Baum- wollfärbungen aus.
<I>Beispiel</I> 43,6 g 2-Amino-4-methoxy-5-methyl-2'-phenyl- sulfonyl-4'-nitro-1,1'-azo'benzol in Form des Diazo- niumsulfats werden in 4 Liter Wasser gelöst. Zu dieser Diazolösung lässt man unter gutem Rühren eine Lö sung von 30 g 1-(2',3'-Oxy-naphthoylamino)-2-me- thoxy-benzol in verdünnter Natronlauge zulaufen. Durch allmähliches Erwärmen auf<B>90 </B> wird die Kupp lung beendet.
Der gebildete grünstichig-schwarze Farbstoff wird abfiltriert, gut ausgewaschen und ge trocknet. Man kann die Kupplung auch in Gegenwart eines zur Farblackherstellung geeigneten Trägerstoffes vor nehmen.
Die folgende Tabelle enthält noch eine Anzahl von weiteren erfindungsgemäss verwendbaren Kom ponenten sowie die auf der Fasererhältlichen Farb töne der daraus hergestellten Azofarbstoffe, die eben falls gute Echtheitseigenschaften besitzen:
EMI0002.0001
Diazokomponente <SEP> Azokomponente <SEP> Farbton
<tb> 2-Amino-4-methoxy-5-methyl-2'-phenyl- <SEP> 1-(2',3'-Oxy-naphthoylamino)- <SEP> gedecktes <SEP> Grün
<tb> sulfonyl-4'-nitro-1,1'-azobenzol <SEP> 2,5-dimethoxy-4-chlor-benzol
<tb> ,> <SEP> 2,5-dimethoxy-benzol <SEP>
<tb> <SEP> 2-methoxy-5-chlor-benzol <SEP>
<tb> <SEP> 2,3-dimethyl-benzol <SEP> stumpfes <SEP> Grün
<tb> <SEP> naphthalin <SEP> Graubraun
<tb> ,> <SEP> 4-methoxy-benzol <SEP>
<tb> <SEP> 2-äthoxy-benzol <SEP> grünstichiges <SEP> Braun
<tb> <SEP> 2-methyl-5-chlor-benzol <SEP> grünstichiges <SEP> Dunkelbraun
<tb> <SEP> 4-äthoxy-benzol <SEP> Graubraun
<tb> <SEP> 2,4-dimethyl-benzol <SEP> Braun
<tb> <SEP> 2-methyl-4-methoxy-benzol <SEP> gedecktes <SEP> Grün
<tb> <SEP> 2,
4-dimethoxy-5-chlor-benzol <SEP>
<tb> <SEP> 2-methoxy-4-chlor-5-methyl-benzol
<tb> 2-Amino-4-methoxy-5-äthyl-2'-phenyl- <SEP> 1-(2',3'-Oxy-naphthoylamino)- <SEP>
<tb> sulfonyl-4'-nitro-1,1'-azobenzol <SEP> 2-methyl-4-methoxy-benzol
<tb> <SEP> 2-methoxy-5-chlor-benzol <SEP>
<tb> <SEP> 2,5-dirnethoxy-benzol <SEP>
<tb> 2-Amino-4-äthoxy-5-methyl-2'-phenyl- <SEP> 2-methoxy-4-chlor-5-methyl-benzol <SEP>
<tb> sulfonyl-4'-nitro-1,1'-azobenzol
<tb> <SEP> 2,4-dimethoxy-5-chlor-benzol <SEP> >
<tb> <SEP> 2-methoxy-benzol <SEP> grünstichiges <SEP> Braun
Process for the preparation of water-insoluble azo dyes It has been found that new, valuable water-insoluble azo dyes are obtained if the diazonium compounds are obtained from o-aminoazo compounds of the general formula
EMI0001.0009
with arylamides of 2,3-oxynaphthoic acid of the general formula
EMI0001.0012
wherein R is one by at least one halogen atom,
denotes an alkyl or alkoxy group substituted phenyl radical or a naphthyl radical, couples.
With the new dyes, vegetable fibers, including those made from regenerated cellulose, are obtained using the known dyeing and printing processes, predominantly greenish-brown to green dyeings and prints with good fastness properties, such as those previously used in the ice color range Diazo components could not yet be obtained.
The dyes can also be produced on a non-textile substrate and can be used for coloring high-molecular plastic masses or for the preparation of colored lacquers. The o-aminoazo compounds used as diazo components can be prepared by known methods. The solid, durable diazonium compounds, such as those obtained according to Patent No. 366052, are expediently used for the production of the new dyes.
Compared to the water-insoluble azo dye known from Austrian Patent No. 141854 from diazotized 2-amino-4-methoxy-5-methyl-2'-phenylsulfonyl-4 '= nitro-1,1'-azobenzene and 2,3- Oxy-naphthoylaminobenzene, the azo dyes obtainable according to the process are distinguished by the better light, chlorine and ironing fastness of the cotton dyeings.
<I> Example </I> 43.6 g of 2-amino-4-methoxy-5-methyl-2'-phenylsulfonyl-4'-nitro-1,1'-azo'benzene in the form of the diazonium sulfate are dissolved in 4 liters of water. A solution of 30 g of 1- (2 ', 3'-oxynaphthoylamino) -2-methoxybenzene in dilute sodium hydroxide solution is allowed to run into this diazo solution with thorough stirring. The coupling is terminated by gradually heating it to <B> 90 </B>.
The greenish black dye formed is filtered off, washed well and dried. The coupling can also be carried out in the presence of a carrier suitable for the production of colored varnishes.
The following table also contains a number of other components that can be used according to the invention and the colors of the azo dyes produced therefrom which can be obtained on the fiber and which also have good fastness properties:
EMI0002.0001
Diazo component <SEP> azo component <SEP> color
<tb> 2-Amino-4-methoxy-5-methyl-2'-phenyl- <SEP> 1- (2 ', 3'-Oxy-naphthoylamino) - <SEP> muted <SEP> green
<tb> sulfonyl-4'-nitro-1,1'-azobenzene <SEP> 2,5-dimethoxy-4-chlorobenzene
<tb>,> <SEP> 2,5-dimethoxy-benzene <SEP>
<tb> <SEP> 2-methoxy-5-chloro-benzene <SEP>
<tb> <SEP> 2,3-dimethyl-benzene <SEP> dull <SEP> green
<tb> <SEP> naphthalene <SEP> gray-brown
<tb>,> <SEP> 4-methoxy-benzene <SEP>
<tb> <SEP> 2-ethoxy-benzene <SEP> greenish <SEP> brown
<tb> <SEP> 2-methyl-5-chlorobenzene <SEP> greenish <SEP> dark brown
<tb> <SEP> 4-ethoxy-benzene <SEP> gray-brown
<tb> <SEP> 2,4-dimethyl-benzene <SEP> brown
<tb> <SEP> 2-methyl-4-methoxy-benzene <SEP> opaque <SEP> green
<tb> <SEP> 2,
4-dimethoxy-5-chlorobenzene <SEP>
<tb> <SEP> 2-methoxy-4-chloro-5-methyl-benzene
<tb> 2-Amino-4-methoxy-5-ethyl-2'-phenyl- <SEP> 1- (2 ', 3'-oxynaphthoylamino) - <SEP>
<tb> sulfonyl-4'-nitro-1,1'-azobenzene <SEP> 2-methyl-4-methoxy-benzene
<tb> <SEP> 2-methoxy-5-chloro-benzene <SEP>
<tb> <SEP> 2,5-dirnethoxy-benzene <SEP>
<tb> 2-Amino-4-ethoxy-5-methyl-2'-phenyl- <SEP> 2-methoxy-4-chloro-5-methyl-benzene <SEP>
<tb> sulfonyl-4'-nitro-1,1'-azobenzene
<tb> <SEP> 2,4-dimethoxy-5-chlorobenzene <SEP>>
<tb> <SEP> 2-methoxy-benzene <SEP> greenish <SEP> brown
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF24079A DE1084402B (en) | 1957-10-01 | 1957-10-01 | Process for the production of water-insoluble azo dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH370856A true CH370856A (en) | 1963-07-31 |
Family
ID=7091094
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH6447058A CH370856A (en) | 1957-10-01 | 1958-09-29 | Process for the production of water-insoluble azo dyes |
Country Status (2)
| Country | Link |
|---|---|
| CH (1) | CH370856A (en) |
| DE (1) | DE1084402B (en) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT141854B (en) * | 1933-02-02 | 1935-05-25 | Ig Farbenindustrie Ag | Process for the preparation of o-disazo dyes. |
-
1957
- 1957-10-01 DE DEF24079A patent/DE1084402B/en active Pending
-
1958
- 1958-09-29 CH CH6447058A patent/CH370856A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE1084402B (en) | 1960-06-30 |
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