PL146205B2 - Method of obtaining novel azo dyes - Google Patents
Method of obtaining novel azo dyes Download PDFInfo
- Publication number
- PL146205B2 PL146205B2 PL26195986A PL26195986A PL146205B2 PL 146205 B2 PL146205 B2 PL 146205B2 PL 26195986 A PL26195986 A PL 26195986A PL 26195986 A PL26195986 A PL 26195986A PL 146205 B2 PL146205 B2 PL 146205B2
- Authority
- PL
- Poland
- Prior art keywords
- azo dyes
- pyrido
- hydroxy
- methyl
- methoxy
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 239000000987 azo dye Substances 0.000 title claims description 4
- 239000000460 chlorine Chemical group 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- -1 methoxy, ethoxy Chemical group 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- CIZVQWNPBGYCGK-UHFFFAOYSA-N benzenediazonium Chemical class N#[N+]C1=CC=CC=C1 CIZVQWNPBGYCGK-UHFFFAOYSA-N 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
Przedmiotem wynalazkujest sposób otrzymywania nowych barwników azowych pochodnych kwasu 4-hydroksy-2-metylo-l-pirydo[l,2-a]perimidynokarboksylowego o ogólnym wzorze 1, w którym R oznacza atom wodoru, chloru lub bromu albo grupe metoksylowa, etoksylowa lub nitrowa. Barwniki te barwia welne i poliamid na kolor brunatny.Sposobem wedlug wynalazku sprzega sie kwas 4-hydroksy-2-metylo-l-pirydo[l,2-a]perimi- dynokarboksylowy o wzorze 2 z sola benzenodiazoniowa lub jej pochodna podstawiona w poloze¬ niu 4 pierscienia fenylowego atomem chloru lub bromu albo grupa metoksylowa, etoksylowa lub nitrowa. Reakcje prowadzi sie w srodowisku dimetylosulfotlenku.Stosowany jako skladnik binarny reakcji sprzegania kwas 4-hydroksy-2-metylo-l-pirydo[l,2- a]perimidynokarboksylowy jest zwiazkiem nowym.Wynalazek ilustruja nastepujace przyklady, w których procenty oznaczaja procesnty wagowe, a stopnie temperatury podano w stopniach Celsjusza: Przyklad I. W zlewce o pojemnosci 500cm3 rozpuszczono 0,3g (okolo 0,001 mola) kwasu 4-hydroksy-2-metylo-l-pirydo [1,2-a] perimidynokarboksylowego w 25 cm3 dimetylosulfotlenku, a nastepnie dodano przy mieszaniu 25 cm3 wody i 2 cm3 2 M roztworu wodorotlenkusodowego. Po oziebieniu w lazni lodowej do temperatury okolo 5°C dodawano stopniowo, przy mieszaniu, oziebiony roztwór 0,2 g (0,001 mola) fluoroboranu benzenodiazoniowego w 50 cm3 wody. Po dodaniu roztworu soli diazoniowej mieszano calosc przy chlodzeniu w ciagu 1 godziny, a nastepnie dodano 200 cm3 wody i zobojetniono kwasem octowym. Wytracony osad odsaczono, przemyto woda i wysuszono w temperaturze 80-90°. Z wydajnoscia 74% uzyskano barwnik, barwiacy welne i poliamid na kolor brunatny. Temperatura topnienia otrzymanego zwiazku wynosi 235° (z rozkladem).UV-vis (CH3OH) ^max (nm) (£max220 (50000), 231 (59000), 316 (44000),451 (6200)2 146 205 Dalsze przyklady wykonania wynalazku sposobem opisanym w przykladzie I ilustruje naste¬ pujaca tabela: Przyklad nr Temperatura topnienia Wydajnosc (%) UV-vis (CH3OH) Amax(nm) (£max) 3 III IV Cl Br VI OCH3 OC2H5 N02 210° (z rozkladem) 190° (z rozkladem) 245° (z rozkladem) 300° (z rozkladem) 190° (z rozkladem) 76 67 91 63 84 212(20000) 230 (26400) 320 (95600) 420(1360) 214(28000), 230 (38400), 320 (49200), 440(1100) 212(29500), 230 (54000), 317(34280), 455 (1800) 212(13600), 225 (12400), 320 (8800), 425 (2400) 215 (26000), 230 (40250), 317(26000), 385(3100), 490 (800) Zastrzezenie patentowe Sposób otrzymywania nowych barwników azowych pochodnych kwasu 4-hydroksy-2- metylo-l-pirydo[l,2-a]perimidynokarboksylowego o ogólnym wzorze 1, w którym R oznacza atom wodoru, chloru lub bromu albo grupe metoksylowa, etoksylowa lub nitrowa, znamienny tym, ze kwas 4-hydroksy-2-metylo-l-pirydo[l,2-a]perimidynokarboksylowy o wzorze 2 sprzega sie z sola benzenodiazoniowa lub jej pochodne podstawiona w polozeniu 4 pierscienia fenylowego atomem chloru lub bromu albo grupa metoksylowa, etoksylowa lub nitrowa.146205 HOC N^N WZGflU ,» iCH3 WZCfR 2 PLThe subject of the invention is a process for the preparation of new azo dyes of 4-hydroxy-2-methyl-1-pyrido [1,2-a] perimidine carboxylic acid of the general formula I, in which R represents a hydrogen, chlorine or bromine atom or a methoxy, ethoxy or nitro group . These dyes dyes wool and polyamide a brown color. According to the invention, 4-hydroxy-2-methyl-1-pyrido [1,2-a] perimidinecarboxylic acid of the formula II is combined with a benzenediazonium salt or its derivative substituted in a position the phenyl ring with a chlorine or bromine atom, or a methoxy, ethoxy or nitro group. The reactions are carried out in the environment of dimethylsulfoxide. The 4-hydroxy-2-methyl-1-pyrido [1,2-a] perimidine carboxylic acid used as a binary component of the coupling reaction is a novel compound. degrees of temperature are given in degrees Celsius: Example I. In a 500 cm3 beaker 0.3 g (about 0.001 mol) of 4-hydroxy-2-methyl-1-pyrido [1,2-a] perimidine carboxylic acid was dissolved in 25 cm3 of dimethyl sulfoxide, and 25 cm <3> of water and 2 cm <3> of a 2M sodium hydroxide solution were then added with stirring. After cooling in an ice bath to a temperature of about 5 ° C, a cooled solution of 0.2 g (0.001 mol) of benzenediazonium fluoroborate in 50 cm 3 of water was gradually added with stirring. After the addition of the diazonium salt solution, the mixture was stirred under cooling for 1 hour, then 200 cm 3 of water were added and neutralized with acetic acid. The resulting precipitate was filtered off, washed with water and dried at 80-90 °. With the efficiency of 74%, the dye, wool dyes and brown polyamide were obtained. The melting point of the compound obtained is 235 ° (with decomposition) .UV-vis (CH3OH) ^ max (nm) (£ max220 (50,000), 231 (59,000), 316 (44,000), 451 (6,200) 2 146 205 Further examples of implementation The invention is illustrated in the following table by the method described in Example 1: Example No. Melting point Efficiency (%) UV-vis (CH3OH) Amax (nm) (≤max) 3 III IV Cl Br VI OCH3 OC2H5 NO2 210 ° (with decomposition) 190 ° (with distribution) 245 ° (with distribution) 300 ° (with distribution) 190 ° (with distribution) 76 67 91 63 84 212 (20,000) 230 (26,400) 320 (95,600) 420 (1,360) 214 (28,000), 230 (38400), 320 (49200), 440 (1100) 212 (29500), 230 (54000), 317 (34280), 455 (1800) 212 (13600), 225 (12400), 320 (8800), 425 (2400) ) 215 (26000), 230 (40250), 317 (26000), 385 (3100), 490 (800) Patent claim The method of obtaining new azo dyes derived from 4-hydroxy-2-methyl-1-pyrido [1,2 a] perimidinecarboxylic acid of the general formula I, in which R represents a hydrogen, chlorine or bromine atom or a methoxy, ethoxy or nitro group, characterized by that 4-hydroxy-2-methyl-1-pyrido [1,2-a] perimidinecarboxylic acid of formula II is contacted with a benzenediazonium salt or its derivatives substituted in position 4 of the phenyl ring with chlorine or bromine or a methoxy, ethoxy group or nitro. 146205 HOC N ^ N WZGflU, »iCH3 WZCfR 2 PL
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL26195986A PL146205B2 (en) | 1986-10-20 | 1986-10-20 | Method of obtaining novel azo dyes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL26195986A PL146205B2 (en) | 1986-10-20 | 1986-10-20 | Method of obtaining novel azo dyes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL261959A2 PL261959A2 (en) | 1987-12-14 |
| PL146205B2 true PL146205B2 (en) | 1989-01-31 |
Family
ID=20033127
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL26195986A PL146205B2 (en) | 1986-10-20 | 1986-10-20 | Method of obtaining novel azo dyes |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL146205B2 (en) |
-
1986
- 1986-10-20 PL PL26195986A patent/PL146205B2/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL261959A2 (en) | 1987-12-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| PL146205B2 (en) | Method of obtaining novel azo dyes | |
| JPS58157863A (en) | Production of monoazo dye | |
| US4083846A (en) | Process for the preparation of azo dyestuffs | |
| KR900004223B1 (en) | Process for the preparation of reactive disazo dyes | |
| JPS645069B2 (en) | ||
| KR100406648B1 (en) | Monoazo pigments | |
| JPS5839182B2 (en) | Diazotization method of aromatic amines | |
| PL88919B1 (en) | ||
| US4187218A (en) | Water-soluble acid azo dye | |
| JPS59187061A (en) | Production of disazo dye | |
| US5811529A (en) | Bis-pyridone compounds | |
| JPH01141953A (en) | Azo dye | |
| US5696241A (en) | Sulfonated quinolone compound and method of preparation | |
| KR102282524B1 (en) | Azo based reactive-disperse dyes for supercritical fluid dyeing and supercritical fluid dyeing using the same | |
| JPH0156102B2 (en) | ||
| JPH0693197A (en) | Production of fiber-reactive formazane dye, and aminophenol | |
| JP4482671B2 (en) | Pyridone azo dye | |
| KR20000048244A (en) | Thermomigrationfast Azo Dyes | |
| US4005067A (en) | Process for the synthesis of nitrite ion-containing 1:1 complexes of cobalt and metallizable monoazo or azomethine compounds and such complexes | |
| JPS58136656A (en) | Monoazo dye for polyester fibers | |
| JPH02302471A (en) | Azo compound and its production | |
| PL163595B1 (en) | The method of producing carbazole dyes | |
| GB1562991A (en) | Water-soluble monoazo dyes based on alkoxyaniline sulphonic acid and phenols | |
| PL146477B2 (en) | Method of obtaining novel monoazo dyes | |
| GB2080287A (en) | 2-Alkoxy-5-aminobenzene Sulfonates and 5-Diazo Derivatives thereof |