PL415663A1 - 4-[(E)-phenyloazo]-N-(2-pyridyl)benzenesulfonamide dyes and method for producing them - Google Patents
4-[(E)-phenyloazo]-N-(2-pyridyl)benzenesulfonamide dyes and method for producing themInfo
- Publication number
- PL415663A1 PL415663A1 PL415663A PL41566315A PL415663A1 PL 415663 A1 PL415663 A1 PL 415663A1 PL 415663 A PL415663 A PL 415663A PL 41566315 A PL41566315 A PL 41566315A PL 415663 A1 PL415663 A1 PL 415663A1
- Authority
- PL
- Poland
- Prior art keywords
- hydroxyethyl
- benzenesulfonamide
- pyridyl
- amino
- dyes
- Prior art date
Links
- 239000000975 dye Substances 0.000 title abstract 3
- 238000004519 manufacturing process Methods 0.000 title 1
- -1 2-hydroxyethyl (methyl) amino, ethyl (2-hydroxyethylamino) Chemical group 0.000 abstract 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 abstract 2
- HYVGFUIWHXLVNV-UHFFFAOYSA-N 2-(n-ethylanilino)ethanol Chemical compound OCCN(CC)C1=CC=CC=C1 HYVGFUIWHXLVNV-UHFFFAOYSA-N 0.000 abstract 1
- VIIZJXNVVJKISZ-UHFFFAOYSA-N 2-(n-methylanilino)ethanol Chemical compound OCCN(C)C1=CC=CC=C1 VIIZJXNVVJKISZ-UHFFFAOYSA-N 0.000 abstract 1
- RGNDWNXPMRAFCA-UHFFFAOYSA-M 4-(pyridin-2-ylsulfamoyl)benzenediazonium;chloride Chemical compound [Cl-].C=1C=C([N+]#N)C=CC=1S(=O)(=O)NC1=CC=CC=N1 RGNDWNXPMRAFCA-UHFFFAOYSA-M 0.000 abstract 1
- 229960000583 acetic acid Drugs 0.000 abstract 1
- PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000012954 diazonium Substances 0.000 abstract 1
- 150000001989 diazonium salts Chemical class 0.000 abstract 1
- 238000006193 diazotization reaction Methods 0.000 abstract 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical group OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 239000012362 glacial acetic acid Substances 0.000 abstract 1
- 238000001093 holography Methods 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 238000006386 neutralization reaction Methods 0.000 abstract 1
- 230000003287 optical effect Effects 0.000 abstract 1
- 230000005693 optoelectronics Effects 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 239000004317 sodium nitrate Substances 0.000 abstract 1
- 235000010344 sodium nitrate Nutrition 0.000 abstract 1
- GECHUMIMRBOMGK-UHFFFAOYSA-N sulfapyridine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=CC=CC=N1 GECHUMIMRBOMGK-UHFFFAOYSA-N 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Landscapes
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Zgłoszenie dotyczy barwników 4-[(E)-fenyloazo]-N-(2-pirydylo)benzenosulfonamidowych o wzorze ogólnym 1, w którym R oznacza grupę 2-hydroksyetylo(metylo)aminową, etylo(2-hydroksyetyloaminową) lub bis(2-hydroksyetylo)aminową znajdujących zastosowanie w syntezie materiałów użytecznych w optoelektronice, holografii, optycznym magazynowaniu informacji oraz optyce nieliniowej. Zgłoszenie ujawnia również sposób otrzymywania barwników 4-[(E)-fenyloazo]-N-(2-pirydylo)benzenosulfonamidowych o wzorze ogólnym 1, w którym R oznacza grupę 2-hydroksyetylo(metylo)aminową, etylo(2-hydroksyetyloaminową) lub bis(2-hydroksyetylo)aminową polegający tym, że 4-amino-N-(2-pirydylo)benzenosulfonamid poddaje się reakcji diazowania azotanem (III) sodu w mieszaninie stężonego kwasu solnego, wody i lodowatego kwasu octowego w temperaturze z zakresu od -2 do 10°C, po czym powstałą sól diazoniową w postaci chlorku 4-(2-pirydylosulfamoilo)benzenodiazoniowego sprzęga się z aniliną, wybraną spośród 2-(N-metyloanilino)etanolu, 2-(N-etyloanilino)etanolu lub 2-[N-(2-hydroksyetylo)anilino)]etanolu w temperaturze poniżej 10°C, a następnie otrzymany produkt wydziela się z mieszaniny reakcyjnej poprzez zobojętnienie i sączenie.The application relates to 4 - [(E) -phenylazo] -N- (2-pyridyl) benzenesulfonamide dyes of the general formula 1 in which R is 2-hydroxyethyl (methyl) amino, ethyl (2-hydroxyethylamino) or bis (2- hydroxyethyl) amine used in the synthesis of materials useful in optoelectronics, holography, optical information storage and nonlinear optics. The application also discloses a method for preparing 4 - [(E) -phenylazo] -N- (2-pyridyl) benzenesulfonamide dyes of general formula 1, wherein R is 2-hydroxyethyl (methyl) amino, ethyl (2-hydroxyethylamino) or bis (2-hydroxyethyl) amino consisting in that 4-amino-N- (2-pyridyl) benzenesulfonamide is subjected to a sodium nitrate diazotization reaction in a mixture of concentrated hydrochloric acid, water and glacial acetic acid at a temperature in the range from -2 to 10 ° C, after which the resulting diazonium salt in the form of 4- (2-pyridylsulfamoyl) benzenediazonium chloride is coupled to aniline, selected from 2- (N-methylanilino) ethanol, 2- (N-ethylanilino) ethanol or 2- [N- (2-hydroxyethyl) anilino)] ethanol at a temperature below 10 ° C, and then the product obtained is separated from the reaction mixture by neutralization and filtration.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL415663A PL229885B1 (en) | 2015-12-30 | 2015-12-30 | 4-[(E)-phenyloazo]-N-(2-pyridyl)benzenesulfonamide dyes and method for producing them |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL415663A PL229885B1 (en) | 2015-12-30 | 2015-12-30 | 4-[(E)-phenyloazo]-N-(2-pyridyl)benzenesulfonamide dyes and method for producing them |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL415663A1 true PL415663A1 (en) | 2016-07-18 |
| PL229885B1 PL229885B1 (en) | 2018-09-28 |
Family
ID=56370095
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL415663A PL229885B1 (en) | 2015-12-30 | 2015-12-30 | 4-[(E)-phenyloazo]-N-(2-pyridyl)benzenesulfonamide dyes and method for producing them |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL229885B1 (en) |
-
2015
- 2015-12-30 PL PL415663A patent/PL229885B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL229885B1 (en) | 2018-09-28 |
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