PL146209B2 - Method of obtaining novel monoazo suspension dyes - Google Patents

Method of obtaining novel monoazo suspension dyes Download PDF

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PL146209B2
PL146209B2 PL26297786A PL26297786A PL146209B2 PL 146209 B2 PL146209 B2 PL 146209B2 PL 26297786 A PL26297786 A PL 26297786A PL 26297786 A PL26297786 A PL 26297786A PL 146209 B2 PL146209 B2 PL 146209B2
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amino
methyl
hydroxyethyl
tetramethylpiperidyl
cyano
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PL26297786A
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Polish (pl)
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PL262977A2 (en
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Przedmiotem wynalazku jest sposób otrzymywania nowych zawiesinowych barwników mo¬ noazowych o ogólnym wzorze podstawionym na rysunku, w którym R oznacza grupe 2- hydroksyetylowa, 2-hydroksypropylowa lub 2,2,6,6-tetrametylopiperydylowa, a R' oznacza atom wodoru lub grupe 2-hydroksyetylowa albo 2,2,6,6-tetrametylopiperydylowa. Barwniki te barwia wlókna poliakrylonitrylowe i poliamidowe oraz welne na kolor zólty.Sposobem wedlug wynalazku diazuje sie 2-amino-5-chlorobenzhydrol i sprzega otrzymany zwiazek diazoniowy w srodowisku kwasnym z 2-amino-3-cyjano-4-metylo-6-/2-hydroksyetylo/- aminopirydyna, 2-amino-3-cyjano-4-metylo-6-/2-hydroksypropylo/aminopirydyna, 2-[4'-/2',2\ 6,,6'-tetrametylopiperydylo/]-amino-3-cyjno-4-metylo-6-/2-hydroksyetylo/-aminopirydyna,2-[4/- /2',2',6',6'-tetrametylopiperydylo/]-amino-3-cyjano-4-metylo-6-/2-hydroksypropylo/-aminopiry- dyna albo z 2-/hydroksyetylo/-amino-3-cyjano-4-metylo-6-[4V2',2,,6',6'-tetrametylopiperydy- lo/]-aminopirydyna.Sposób wedlug wynalazku ilustruja nastepujace przyklady, w których procenty oznaczaja procenty wagowe, a stopnie temperatury podano w stopniach Celsjusza: Przyklad I. 2,34 g (0,01 mola) 2-amino-5-chlorobenzhydrolu rozpuszcza sie w 3 cm3 lodo¬ watego kwasu octowego i 3 cm3 stezonego kwasu solnego. Uzyskany roztwór chlodzi sie w lazni lodowej do temperatury 10-12° i wkrapla, energicznie mieszajac, roztwór 0,8 g (0,012 mola) azotynu sodowego w 2,5 cm3 wody, utrzymujac temperature ponizej 15°. Po 20 minutach usuwa sie nadmiar kwasu azotawego, dodajac mocznika, po czym wprowadza sie 8 cm3 wody z lodem i saczy. Roztwór soli diazoniowej moze byc przechowywany w temperaturze do 10° bez obawy rozkladu w ciagu kilkunastu godzin.Oddzielnie rozpuszcza sie 3,28 g (0,011 mola) 6-chloro-3-cyjano-4-metylo-2-[4'/2',2',6',6'- tetrametylopiperydylo/-amino]pirydyny w 5 cm3 N-metylo-2-pirolidonu i do uzyskanego roz¬ tworu dodaje 2,47 g (0,033 mola) 2-hydroksypropyloaminy. Calosc ogrzewa sie w ciagu 5 godzin pod chlodnica zwrotna w temperaturze 140°C.Do ochlodzonej mieszaniny reakcyjnej dodaje sie nastepnie 5 ml lodowatego kwasu octowego.Do przygotowanego w ten sposób roztworu skladnika biernego wprowadza sie roztwór otrzymanej opisanym wyzej sposobem soli diazoniowej. W trakcie dodawania roztworu soli dia-2 146 209 zoniowej wypada barwnik, który wydziela sie calkowicie z roztworu, dodajac staly octan sodowy.Osad odsaczacza sie, przymwa woda i suszy. Otrzymuje sie 5,5 g (80% wydajnosci) barwnika, barwiacego wlókna poliakrylonitrylowe i poliamidowe oraz welne na kolor zólty.Dalsze przyklady wykonania wynalazku sposobem opisanym w przykladzie I ilustruje naste¬ pujaca tabela: Przyklad nr II III IV V Podstawniki we wzorze przedstawionym na R 2-hydroksyetyl 2,2,6,6-tetra metylopiperydyl 2-hydroksy¬ etyl 2-hydroksy- propyl rysunku R' 2,2,6,6-tetra- metylopiperydyl 2-hydroksyetyl atom wodoru atom wodoru Zastrzezenie Uzyskany barwnik zólcien zólcien zólcien zólcien patentowe Sposób otrzymywania nowych zawiesinowych barwników monoazowych o ogólnym wzorze przedstawionym na rysunku, w którym R oznacza grupe 2-hydroksyetylowa, 2-hydroksypro- pylowa lub 2,2,6,6-tetrametylopiperydylowa, a R' oznacza atom wodoru lub grupe 2-hydroksy¬ etylowa albo 2,2,6,6-tetrametylopiperydylowa, znamienny tym, ze 2-amino-5-chlorobenzhydrol diazuje sie i sprzega otrzymany zwiazek diazoniowy w srodowisku kwasnym z 2-amino-3-cyjano-4- metylo-6-/2-hydroksyetylo/-aminopirydyna,2-amino-3-cyjano-4-metylo-6-/2-hydroksypropylo/- aminopirydyna,2-[4V2',2',6',6/-tetrametylopiperydylo/]-amino-3-cyjano-4-metylo-6-/2-hydroksy- etyloAaminopirydyna, 2-[4/-/2,,2,,6',6'-tetrametylopiperydylo/]-amino-3-cyjano-4-metylo-6-/2- hydroksypropyloAaminopirydyna albo z 2-/hydroksyetylo/-amino-3-cyjano-4-metylo-6-[4'-/2', 2',6',6'-tetrametylopiperydylo/]-amino-pirydyna.R'HN N NHR Pracownia Poligraficzna UP PRL. Naklad 100 egz.Cena 400 zl PLThe subject of the invention is a process for the preparation of new suspension monoazo dyes of the general formula shown in the figure, where R is 2-hydroxyethyl, 2-hydroxypropyl or 2,2,6,6-tetramethylpiperidyl, and R 'represents a hydrogen atom or the group 2. -hydroxyethyl or 2,2,6,6-tetramethylpiperidyl. These dyes dyes polyacrylonitrile and polyamide fibers and wool fibers yellow. According to the invention, 2-amino-5-chlorobenzhydrol is diazotized and the obtained diazonium compound is combined in an acidic environment with 2-amino-3-cyano-4-methyl-6- / 2 -hydroxyethyl) - aminopyridine, 2-amino-3-cyano-4-methyl-6- (2-hydroxypropyl) aminopyridine, 2- [4 '- (2', 2] 6,6, 6'-tetramethylpiperidyl)] amino -3-cyno-4-methyl-6- (2-hydroxyethyl) -aminopyridine, 2- [4- (2 ', 2', 6 ', 6'-tetramethylpiperidyl)] amino-3-cyano-4- methyl-6- (2-hydroxypropyl) -aminopyridine or with 2- (hydroxyethyl) -amino-3-cyano-4-methyl-6- [4V2 ', 2, 6', 6'-tetramethylpiperidyl) ] -aminopyridine. The method of the invention is illustrated by the following examples, in which the percentages are percentages by weight and the degrees of temperatures are in degrees Celsius: Example I. 2.34 g (0.01 mol) of 2-amino-5-chlorobenzhydrol is dissolved in 3 cm 3 of glacial acetic acid and 3 cm 3 of concentrated hydrochloric acid. The resulting solution is cooled in an ice bath to 10-12 ° and a solution of 0.8 g (0.012 mol) of sodium nitrite in 2.5 cm 3 of water is added dropwise with vigorous stirring, keeping the temperature below 15 °. After 20 minutes, the excess nitrous acid is removed by adding urea, then 8 cm3 of ice water are added and filtered. The diazonium salt solution can be stored at a temperature of up to 10 ° without the risk of decomposition within several hours. 3.28 g (0.011 mol) of 6-chloro-3-cyano-4-methyl-2- [4 '/ 2' are dissolved separately , 2 ', 6', 6'-tetramethylpiperidylamino] pyridine in 5 cm 3 of N-methyl-2-pyrrolidone and 2.47 g (0.033 mol) of 2-hydroxypropylamine are added to the resulting solution. The whole is heated for 5 hours under a reflux condenser at 140 ° C. 5 ml of glacial acetic acid are then added to the cooled reaction mixture. The solution of the diazonium salt obtained as described above is added to the inert solution prepared in this way. During the addition of the dia-2 ion salt solution, a dye falls out, which separates completely from the solution by adding solid sodium acetate. The precipitate is drained, washed with water and dried. 5.5 g (80% yield) of the dye is obtained, which dyes polyacrylonitrile, polyamide and wool fibers yellow. Further embodiments of the invention according to the method described in example I are illustrated in the following table: Example No. II III IV V Substituents in the formula shown in R 2-hydroxyethyl 2,2,6,6-tetramethylpiperidyl 2-hydroxyethyl 2-hydroxypropyl Figure R '2,2,6,6-tetramethylpiperidyl 2-hydroxyethyl hydrogen atom Hydrogen yellows yellows Patent A method for the preparation of new suspension monoazo dyes with the general formula shown in the figure, where R is a 2-hydroxyethyl, 2-hydroxypropyl or 2,2,6,6-tetramethylpiperidyl group, and R 'is a hydrogen atom or a group 2 -hydroxy-ethyl or 2,2,6,6-tetramethylpiperidyl, characterized in that 2-amino-5-chlorobenzhydrol is diazotized and the obtained diazonium compound is coupled in an acidic environment with 2-amino-3-cyano-4-methyl-6 - (2-hydroxyethyl) nopyridine, 2-amino-3-cyano-4-methyl-6- (2-hydroxypropyl) -aminopyridine, 2- [4V2 ', 2', 6 ', 6) -tetramethylpiperidyl] - amino-3-cyano-4 -methyl-6- (2-hydroxy-ethyl) aminopyridine, 2- [4 (- (2, 2, 6 ', 6'-tetramethylpiperidyl)] amino-3-cyano-4-methyl-6- (2-) hydroxypropylAaminopyridine or with 2- (Hydroxyethyl) amino-3-cyano-4-methyl-6- [4 '- (2', 2 ', 6', 6'-tetramethylpiperidyl)] amino-pyridine. R'HN N NHR Printing House of the UP PRL. Mintage 100 copies Price PLN 400 PL

Claims (4)

1. Zastrzezenie Uzyskany barwnik zólcien zólcien zólcien zólcien patentowe Sposób otrzymywania nowych zawiesinowych barwników monoazowych o ogólnym wzorze przedstawionym na rysunku, w którym R oznacza grupe 2-hydroksyetylowa, 2-hydroksypro- pylowa lub 2,2,6,6-tetrametylopiperydylowa, a R' oznacza atom wodoru lub grupe 2-hydroksy¬ etylowa albo 2,2,6,6-tetrametylopiperydylowa, znamienny tym, ze 2-amino-5-chlorobenzhydrol diazuje sie i sprzega otrzymany zwiazek diazoniowy w srodowisku kwasnym z 2-amino-3-cyjano-4- metylo-6-/2-hydroksyetylo/-aminopirydyna,2-amino-3-cyjano-4-metylo-6-/2-hydroksypropylo/- aminopirydyna,2-[4V2',2',6',6/-tetrametylopiperydylo/]-amino-3-cyjano-4-metylo-6-/2-hydroksy- etyloAaminopirydyna, 2-[4/-/2,,2,,6',6'-tetrametylopiperydylo/]-amino-3-cyjano-4-metylo-6-/2- hydroksypropyloAaminopirydyna albo z1. Claim The obtained yellows yellows dye yellows yellows patent A method for the preparation of new suspension monoazo dyes with the general formula shown in the figure, in which R is a 2-hydroxyethyl, 2-hydroxypropyl or 2,2,6,6-tetramethylpiperidyl group, and R is a hydrogen atom or a 2-hydroxyethyl or 2,2,6,6-tetramethylpiperidyl group, characterized in that 2-amino-5-chlorobenzhydrol is diazotized and the resulting diazonium compound is coupled in an acidic environment with 2-amino-3- cyano-4-methyl-6- (2-hydroxyethyl) -aminopyridine, 2-amino-3-cyano-4-methyl-6- (2-hydroxypropyl) -aminopyridine, 2- [4V2 ', 2', 6 ', 6 (-tetramethylpiperidyl)] - amino-3-cyano-4-methyl-6- (2-hydroxyethyl) aminopyridine, 2- [4H-/ 2, 2, 6 ', 6'-tetramethylpiperidyl)] amino -3-cyano-4-methyl-6- (2-hydroxypropylAaminopyridine or z 2. -/hydroksyetylo/-amino-2.- / Hydroxyethyl / -amino- 3. -cyjano-3.-cyano- 4. -metylo-6-[4'-/2', 2',6',6'-tetrametylopiperydylo/]-amino-pirydyna. R'HN N NHR Pracownia Poligraficzna UP PRL. Naklad 100 egz. Cena 400 zl PL4.-methyl-6- [4 '- (2', 2 ', 6', 6'-tetramethylpiperidyl)] -amino-pyridine. R'HN N NHR Printing studio of the UP PRL. Mintage 100 copies. Price PLN 400 PL
PL26297786A 1986-12-12 1986-12-12 Method of obtaining novel monoazo suspension dyes PL146209B2 (en)

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PL146209B2 true PL146209B2 (en) 1989-01-31

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