CH244603A - Process for the preparation of an azo dye. - Google Patents
Process for the preparation of an azo dye.Info
- Publication number
- CH244603A CH244603A CH244603DA CH244603A CH 244603 A CH244603 A CH 244603A CH 244603D A CH244603D A CH 244603DA CH 244603 A CH244603 A CH 244603A
- Authority
- CH
- Switzerland
- Prior art keywords
- amino
- azo dye
- preparation
- acid
- sulfonic acid
- Prior art date
Links
- 239000000987 azo dye Substances 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 3
- 239000000975 dye Substances 0.000 claims description 3
- ORFSSYGWXNGVFB-UHFFFAOYSA-N sodium 4-amino-6-[[4-[4-[(8-amino-1-hydroxy-5,7-disulfonaphthalen-2-yl)diazenyl]-3-methoxyphenyl]-2-methoxyphenyl]diazenyl]-5-hydroxynaphthalene-1,3-disulfonic acid Chemical compound COC1=C(C=CC(=C1)C2=CC(=C(C=C2)N=NC3=C(C4=C(C=C3)C(=CC(=C4N)S(=O)(=O)O)S(=O)(=O)O)O)OC)N=NC5=C(C6=C(C=C5)C(=CC(=C6N)S(=O)(=O)O)S(=O)(=O)O)O.[Na+] ORFSSYGWXNGVFB-UHFFFAOYSA-N 0.000 claims description 3
- 210000002268 wool Anatomy 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 150000001989 diazonium salts Chemical class 0.000 description 3
- CYJJLCDCWVZEDZ-UHFFFAOYSA-N 8-aminonaphthalene-1-sulfonic acid Chemical compound C1=CC(S(O)(=O)=O)=C2C(N)=CC=CC2=C1 CYJJLCDCWVZEDZ-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
- 125000003277 amino group Chemical group 0.000 description 1
- 150000001987 diarylethers Chemical class 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Natural products C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000005292 vacuum distillation 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/24—Monoazo dyes prepared by diazotising and coupling from coupling components containing both hydroxyl and amino directing groups
- C09B29/28—Amino naphthols
- C09B29/30—Amino naphtholsulfonic acid
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
- C09B29/3647—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms
- C09B29/3652—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles
- C09B29/366—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles containing hydroxy-1,2-diazoles, e.g. pyrazolone
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
'Verfahren zur Herstellung eines Azofarbstoffes. Es wurde gefunden, dass man zu einem neuen wertvollen Azofarbstoff gelangt, wenn man die Diazoniumverbindung der 1-Amino- 8-oxynaphthalin-3,6-disulfonsäure mit einer solchen 1-Amino -naphthalin - 8 - sulf onsäure vereinigt, die in der Aminogruppe durch einen Diarylätherrest substituiert ist.
Das neue Verfahren ist also dadurch gekennzeich net, dass diazotierte 1-Amino-8-oxynaphtha- lin-3,6-disulfonsäure mit 1-N-Phenyl-(4'- phenoxy)-aminonaphthalin-8-sulfonsäure ge kuppelt wird.
Der neue Farbstoff bildet ein dunkel blaues Pulver, das aus essigsaurem Bade auf Wolle gefärbt ein echtes, reines Blau ergibt. <I>Beispiel:</I> Die wie üblich dargestellte Diazonium- verbindung aus 319 Teilen 1-Amino-8-oxy- naphthalin-3,6-disulfonsäure wird bei 0 C mit der Lösung von 400 Teilen 1-N-Phenyl- (4'-phenoxy) -aminonaphtha.lin-8-sulfonsäure in 4000 Teilen Methylalkohol vermischt.
Man verrührt die tiefblau erscheinende Suspen sion, bis keine Diazoniumverbindung mehr nachgewiesen werden kann, und isoliert den Farbstoff durch Zugabe von wässeriger Na triumchloridlösung. Zur Reinigung wird er in verdünnter Natriumcarbonatlösung gelöst und mit Kochsalzlösung wieder gefällt. Er stellt getrocknet ein dunkelblaues Pulver dar und ergibt aus essigsaurem Bade auf Wolle gefärbt ein echtes, reines Blau.
Die 1- N - Phenyl - (4'- phenoxy) - amino- naphthaa-8-sulfonsäure wird erhalten, in dem man 1-Aminonaphthalin-8-sulfonsäure 20 Stunden bei 180 C mit einem Überschuss an 4 - Amino -1,1' - diphenyläther verrührt. Nach Entfernung des überschüssigen Diaryl- äthers, z. B. durch Vakuumdestillation, lässt sich die neue Säure dank ihrer überraschen den Löslichkeit, z. B. in Benzol, mit Hilfe von organischen Lösungsmitteln reinigen.
Process for the production of an azo dye. It has been found that a new, valuable azo dye is obtained if the diazonium compound of 1-amino-8-oxynaphthalene-3,6-disulfonic acid is combined with such a 1-amino-naphthalene-8-sulfonic acid which is in the amino group is substituted by a diaryl ether radical.
The new process is thus characterized in that diazotized 1-amino-8-oxynaphthalene-3,6-disulfonic acid is coupled with 1-N-phenyl- (4'-phenoxy) -aminonaphthalene-8-sulfonic acid.
The new dye forms a dark blue powder which, when dyed with an acetic acid bath on wool, turns into a real, pure blue. <I> Example: </I> The diazonium compound prepared as usual from 319 parts of 1-amino-8-oxynaphthalene-3,6-disulfonic acid is mixed with a solution of 400 parts of 1-N-phenyl- (4'-phenoxy) -aminonaphtha.lin-8-sulfonic acid mixed in 4000 parts of methyl alcohol.
The suspension, which appears deep blue, is stirred until no more diazonium compound can be detected, and the dye is isolated by adding aqueous sodium chloride solution. To clean it, it is dissolved in dilute sodium carbonate solution and reprecipitated with saline solution. When dried, it represents a dark blue powder and, when dyed on wool in an acetic acid bath, produces a real, pure blue.
The 1-N-phenyl- (4'-phenoxy) -amino-naphthaa-8-sulfonic acid is obtained by adding 1-aminonaphthalene-8-sulfonic acid for 20 hours at 180.degree. C. with an excess of 4-amino-1.1 '- diphenyl ether stirred. After removing the excess diaryl ether, z. B. by vacuum distillation, the new acid can surprise thanks to its solubility, z. B. in benzene, clean with the help of organic solvents.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH244603T | 1946-06-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH244603A true CH244603A (en) | 1946-09-30 |
Family
ID=4464373
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH244603D CH244603A (en) | 1946-06-07 | 1945-07-12 | Process for the preparation of an azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH244603A (en) |
-
1945
- 1945-07-12 CH CH244603D patent/CH244603A/en unknown
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