PL161926B2 - Method of obtaining novel arylohydrazone cationic dyes - Google Patents
Method of obtaining novel arylohydrazone cationic dyesInfo
- Publication number
- PL161926B2 PL161926B2 PL28773590A PL28773590A PL161926B2 PL 161926 B2 PL161926 B2 PL 161926B2 PL 28773590 A PL28773590 A PL 28773590A PL 28773590 A PL28773590 A PL 28773590A PL 161926 B2 PL161926 B2 PL 161926B2
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- Poland
- Prior art keywords
- general formula
- tetrahydro
- methyl
- mol
- hydrochloric acid
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- 239000000975 dye Substances 0.000 title claims abstract description 11
- 238000000034 method Methods 0.000 title claims abstract description 9
- 125000002091 cationic group Chemical group 0.000 title claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 15
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims abstract description 12
- -1 azo compound Chemical class 0.000 claims abstract description 11
- 229910000029 sodium carbonate Inorganic materials 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 5
- 239000007864 aqueous solution Substances 0.000 claims abstract description 4
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- WIPUJMZJYAXTDA-UHFFFAOYSA-N 10-methyl-2,3,4,4a-tetrahydro-1H-acridine methyl hydrogen sulfate Chemical compound COS(=O)(=O)O.CN1C2CCCCC2=CC2=CC=CC=C12 WIPUJMZJYAXTDA-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- 239000000047 product Substances 0.000 description 10
- 238000000354 decomposition reaction Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 229920002239 polyacrylonitrile Polymers 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 3
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- 150000007857 hydrazones Chemical class 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 210000002268 wool Anatomy 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- GXYLXFITCXXCQV-UHFFFAOYSA-N 10-methylacridin-10-ium Chemical compound C1=CC=C2[N+](C)=C(C=CC=C3)C3=CC2=C1 GXYLXFITCXXCQV-UHFFFAOYSA-N 0.000 description 1
- WVGMYVWWJSIIFJ-UHFFFAOYSA-N 2-methoxybenzenediazonium Chemical compound COC1=CC=CC=C1[N+]#N WVGMYVWWJSIIFJ-UHFFFAOYSA-N 0.000 description 1
- LJDRAKFYYGCAQC-UHFFFAOYSA-N 3-phenyl-1h-pyrrole Chemical compound N1C=CC(C=2C=CC=CC=2)=C1 LJDRAKFYYGCAQC-UHFFFAOYSA-N 0.000 description 1
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
- HDSKJRZKLHXPNF-UHFFFAOYSA-M 4-chlorobenzenediazonium;chloride Chemical compound [Cl-].ClC1=CC=C([N+]#N)C=C1 HDSKJRZKLHXPNF-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- XUESTGHCVFYOLL-UHFFFAOYSA-N acridin-10-ium;chloride Chemical compound [Cl-].C1=CC=CC2=CC3=CC=CC=C3[NH+]=C21 XUESTGHCVFYOLL-UHFFFAOYSA-N 0.000 description 1
- CLRSZXHOSMKUIB-UHFFFAOYSA-M benzenediazonium chloride Chemical compound [Cl-].N#[N+]C1=CC=CC=C1 CLRSZXHOSMKUIB-UHFFFAOYSA-M 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
Landscapes
- Pyridine Compounds (AREA)
Abstract
Description
Przedmiotem wynalazku jest sposób otrzymywania nowych akrylohydrazonowych barwników kationowych o ogólym wzorze 1, w którym R oznacza atom wodoru lub chloru albo grupę metylową lub metyloksylową. Barwniki te barwią poliakrylonitryl ewentualnie jedwab naturalny i wełnę na kolory oranżowy i czerwony.The subject of the invention is a process for the preparation of new cationic acrylohydrazone dyes of the general formula I, in which R represents a hydrogen or chlorine atom or a methyl or methyloxy group. These dyes dye polyacrylonitrile or natural silk and wool in the colors orange and red.
Sposobem według wynalazku na metylosiarczan l,2,3,4-tetrahydro-10-metyloakrydyniowy działa się w roztworze wodnym w obecności nadmiaru węglanu sodu związkiem o ogólnym wzorze 2, w którym R ma wyżej podane znaczenie, po czym na uzyskany związek azowy o ogólnym wzorze 3, w którym R ma wyżej podane znaczenie, działa się rozcieńczonym kwasem solnym.In the process according to the invention, 1,2,3,4-tetrahydro-10-methylacridinium methyl sulfate is treated in an aqueous solution in the presence of an excess of sodium carbonate with a compound of the general formula II, in which R is as defined above, and then the resulting azo compound of general formula Formula 3, wherein R is as defined above, is treated with dilute hydrochloric acid.
Otrzymane sposobem według wynalazku nowe barwniki kationowe wykazują dobre odporności mokre i na światło.The new cationic dyes obtained by the process according to the invention show good wet and lightfastness.
Wynalazek ilustrują następujące przykłady, w których procenty oznaczają procenty wagowe, a stopnie temperatury podano w stopniach Celsjusza: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:
Przykład I. Do roztworu chlorku benzenodiazoniowego, otrzymanego z 1,02 g (0,011 mola) aniliny, 2,9 cm3 stężonego kwasu solnego, 0,81 g (0,0117 mola) azotynu sodu i 20 cm3 wody dodano 3,09 g (0,01 mola) metylosiarczanu l,2,3,4-tetrahydro-10-metyloakrydyniowego i uzyskany roztwór wkroplono w ciągu 15 minut do mieszanego mechanicznie roztworu 15,90 g (0,15 mola) węglanu sodu w 160 cm3 wody. Mieszanie kontynuowano przez 2 godziny, a następnie odsączono osad, przemyto trzykrotnie porcjami po 20 cm3 2% wodnego roztworu amoniaku i wysuszono. Uzyskano 2,92 g (97% wydajności) ciemnego produktu (4-fenyloazol,2,3,10-tetrahydro-10-metyloakrydyny) o temperaturze topnienia około 135°. 1,51 g (0,005 mola) 4-fenyloazo-1,2,3,10-tetrahydro-10-metyloakrydyny ogrzano następnie do wrzenia z 38 cm3 2% wodnego roztworu kwasu solnego, przesączono otrzymany roztwór i pozostawiono do powolnego ochłodzenia. Po kilkunastu godzinach odsączono osad, przemyto trzykrotnie porcjami po 10 cm3 eteru i wysuszono w temperaturze 80°. Uzyskano 1,43 g (85% wydajności) brunatnoczerwonego produktu (chlorku 4-fenylohydrazon-1,2,3,4-tetrahydro-l0-metylo-akrydyniowego) o temperaturze topnienia 151 - 153° ( z rozkładem). Otrzymany produkt barwi poliakrylonitryl na kolor oranżowy.Example I. To a solution of benzenediazonium chloride prepared from 1.02 g (0.011 mol) of aniline, 2.9 cm 3 of concentrated hydrochloric acid, 0.81 g (0.0117 mol) of sodium nitrite and 20 cm 3 of water was added 3.09 g (0.01 mol) 1,2,3,4-tetrahydro-10-methylacridinium methyl sulfate and the resulting solution was added dropwise over 15 minutes to a mechanically stirred solution of 15.90 g (0.15 mol) of sodium carbonate in 160 cm3 of water. Stirring was continued for 2 hours, then the precipitate was filtered off, washed three times with 20 cm3 of 2% aqueous ammonia solution and dried. The yield was 2.92 g (97% yield) of the dark product (4-phenylazole, 2,3,10-tetrahydro-10-methylacridine) with a melting point of about 135 °. 1.51 g (0.005 mol) of 4-phenylazo-1,2,3,10-tetrahydro-10-methylacridine was then boiled with 38 cm 3 of 2% aqueous hydrochloric acid, the solution obtained was filtered and allowed to cool slowly. After several hours, the precipitate was filtered off, washed three times with 10 cm3 of ether three times and dried at 80 °. 1.43 g (85% yield) of a brown red product (4-phenylhydrazone-1,2,3,4-tetrahydro-10-methyl-acridinium chloride) with a melting point of 151-153 ° (decomposition) was obtained. The obtained product dyes polyacrylonitrile in an orange color.
Przykład Π. Postępując w pierwszym etapie sposobem opisanym w pierwszej części przykładu I, przy użyciu zamiast aniliny 1,35 g (0,011 mola) 4-anizydyny, uzyskano 3,31 g (100% wydajności) ciemnego związku l,2,3,10-tetrahydro-4-[(4-metoksyfenylo)azo]-10-metyloakrydyny) o temperaturze topnienia około 55°.Example Π. By following the procedure described in the first part of Example 1, using 1.35 g (0.011 mol) of 4-anisidine instead of the aniline, 3.31 g (100% yield) of the dark compound 1,2,3,10-tetrahydro was obtained. 4 - [(4-methoxyphenyl) azo] -10-methylacridine) having a melting point of about 55 °.
W dalszym ciągu postępowano sposobem opisanym w drugiej części przykładu I, przy użyciu 1,66 g (0,005 mola) 1,2,3,10-tetrahydro- 4-[(4-metoksyfenylo)azo]-10-metylo-akrydyny i 42 cm 2% wodnego roztworu kwasu solnego. Uzyskano 1,47 g (80% wydajności) ciemnego związku (chlorku l,2,3,4-tetrahydro-4-[(4-metoksyfenylo)hydrazono]-10-metyloakrydyniowego) o temperaturze topnienia 247 - 248° (z rozkładem).The process described in the second part of Example 1 was continued with 1.66 g (0.005 mol) 1,2,3,10-tetrahydro-4 - [(4-methoxyphenyl) azo] -10-methyl-acridine and 42 cm 2% aqueous solution of hydrochloric acid. 1.47 g (80% yield) of the dark compound (1,2,3,4-tetrahydro-4 - [(4-methoxyphenyl) hydrazone] -10-methylacridinium chloride) was obtained, m.p. 247-248 ° (with decomposition) .
Przykład ΠΙ. Roztwór soli diazoniowej otrzymany z 1,19 g (0,011 mola) 4-toluidyny i 3,09 g (0,01 mola) metylosiarczanu l,2,3,4-terahydro-10-metyloakrydyniowego w 20 cm3 wody dodano w temperaturze 20° przy silnym mieszaniu do 100 g 15% roztworu węglanu sodu. Następnego dnia produkt odsączono, przemyto kilkakrotnie 2% wodnym roztworem amoniaku i wysuszono. Uzyskano 3,15 g (100% wydajności) l,2,3,10-tetrahydro-10-metylo-4-[(4-metylofenylo)azo] akrydyny o temperaturze rozkładu 130 - 131°.Example ΠΙ. A solution of the diazonium salt prepared from 1.19 g (0.011 mol) of 4-toluidine and 3.09 g (0.01 mol) of 1,2,3,4-tetrahydro-10-methylacridinium methylsulfate in 20 cm 3 of water was added at 20 ° with vigorous stirring up to 100 g of 15% sodium carbonate solution. The next day, the product was filtered off, washed several times with 2% aqueous ammonia solution and dried. 3.15 g (100% yield) of 1,2,3,10-tetrahydro-10-methyl-4 - [(4-methylphenyl) azo] acridine with a decomposition temperature of 130-131 ° were obtained.
3,15 g (0,01 mola) l,2,3,10-tetrahydiO-10-mety'lo-4--[(4-metylofenylo)azo]akrydyny zadano następnie 350 cm3 5% kwasu solnego, ogrzano do wrzenia i przesączono. Następnego dnia odsączono wytrącony produkt. Uzyskano 3,5 g (91% wydajności) chlorku 1,2,3,4-tetrahydro10-metylo-4-[(4-metylofenylo)hydrazono]akrydyniowego o temperaturze rozkładu 166 - 167°. Otrzymany produkt barwi poliakrylonitryl na kolor czerwony o odcieniu oranżowym.3.15 g (0.01 mole) of l, 2,3,10-tetrahydiO-10-mety'lo-4 - [(4-methylphenyl) azo] acridine then treated with 350 cm 3 of 5% hydrochloric acid, heated to boiling and filtered. The precipitated product was filtered off the next day. There was obtained 3.5 g (91% yield) of 1,2,3,4-tetrahydro-10-methyl-4 - [(4-methylphenyl) hydrazone] acridinium chloride with a decomposition point of 166-167 °. The obtained product dyes polyacrylonitrile red with an orange shade.
Przykład IV. Roztwór chlorku 4-chlorobenzenodiazoniowego otrzymany z 1,43 g(0,011 mola) 4-chloroaniliny i 3,09 g (0,01 mola) metylosiarczanu 1,2,3,4-tetrahydro-10-metylo-akrydyniowego, rozpuszczonego w 20 cm3 wody dodano, intensywnie mieszając, w temperaturze 20°, do 100 g 15% roztworu węglanu sodu. Następnego dnia produkt odsączono, przemyto kilkakrotnie 2% wodnym roztworem amoniaku i wysuszono. Uzyskano 3,10 (93% wydajności) 4-[(4-chlorofenylo)azo]l-l,2,3,10-metyloakrydyny o temperaturze rozkładu 156 - 158°.Example IV. A solution of 4-chlorobenzenediazonium chloride obtained from 1.43 g (0.011 mol) of 4-chloroaniline and 3.09 g (0.01 mol) of 1,2,3,4-tetrahydro-10-methyl-acridinium methylsulfate, dissolved in 20 cm3 Water was added with vigorous stirring at 20 ° to 100 g of a 15% sodium carbonate solution. The next day, the product was filtered off, washed several times with 2% aqueous ammonia solution and dried. 3.10 (93% yield) of 4 - [(4-chlorophenyl) azo] 1,2,3,10-methylacridine with decomposition temperature 156 - 158 ° was obtained.
3,35 g £0,01 mola) 4-[(4-chlorofenylo)azo]-l,2,3,10-tetrahydro- 10-metyloakrydyny zadano 300 cm3 5% kwasu solnego, ogrzano do wrzenia i następnego dnia odsączono. Uzyskano 3,70 g (100% wydajności) chlorku 4-[(4-chlorofenylo)hydrazono]-l,2,3,4-tetrahydro-10-metyloakrydyniowego o temperaturze rozkładu 170 - 171°. Otrzymany produkt barwi poliakrylonitryl, jedwab naturalny i wełnę na kolor oranżowy.3.35 g (0.01 mol) 4 - [(4-chlorophenyl) azo] -1,2,3,10-tetrahydro-10-methylacridine were treated with 300 ml of 5% hydrochloric acid, heated to reflux and filtered the next day. 3.70 g (100% yield) of 4 - [(4-chlorophenyl) hydrazono] -1,2,3,4-tetrahydro-10-methylacridinium chloride with a decomposition temperature of 170-171 ° were obtained. The obtained product dyes polyacrylonitrile, natural silk and wool in an orange color.
Przykład V. Postępując sposobem opisanym w przykładzie IV uzyskano z chlorkuExample 5 Following the procedure described in Example 4, the chloride was obtained
2-metoksybenzenodiazoniowego, otrzymanego z 1,35 g (0,011 mola) 2-anizydyny, 3,15 g (96% wydajności) 1,2,3,10-tetn±ydro-4-[(2-metoksyfenylo)azo]-10-metyloakrydyny o temperaturze rozkładu 160 -161°2-methoxybenzenediazonium, obtained from 1.35 g (0.011 mol) of 2-anisidine, 3.15 g (96% yield) 1,2,3,10-tetra-4 - [(2-methoxyphenyl) azo] - 10-methylacridine with a decomposition temperature of 160-161 °
3,31 g (0,01 mola) l,2,3,10-tetrahydro-4-[(2-metoks>yfenylo)azo]- 10-metyloakrydyny zadano 25 cm3 2% kwasu solnego, ogrzano do wrzenia, przesączono i następnego dnia odsączono wytrącony produkt. Uzyskano 3,30 g (89% wydajności) chlorku l,2,3,4-tetrahydro-4-[(2-metoksyfenylo)hydrazono]-10-metyloakrydyniowego o temperaturze rozkładu 140 -142°. Otrzymany produkt barwi poliakrylonitryl, jedwab naturalny i wełnę na kolor czerwony.3.31 g (0.01 mol) 1,2,3,10-tetrahydro-4 - [(2-methoxyphenyl) azo] -10-methylacridine were treated with 25 cm3 of 2% hydrochloric acid, heated to boiling, filtered and the next day the precipitated product was filtered off. The obtained was 3.30 g (89% yield) of 1,2,3,4-tetrahydro-4 - [(2-methoxyphenyl) hydrazone] -10-methylacridinium chloride with a decomposition temperature of 140-142 °. The obtained product dyes polyacrylonitrile, natural silk and wool red.
Wzór 2Formula 2
Zakład Wydawnictw UP RP. Nakład 90 egz. Cena 10 000 złDepartment of Publishing of the UP RP. Circulation of 90 copies. Price: PLN 10,000
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL28773590A PL161926B2 (en) | 1990-11-12 | 1990-11-12 | Method of obtaining novel arylohydrazone cationic dyes |
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| Application Number | Priority Date | Filing Date | Title |
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| PL28773590A PL161926B2 (en) | 1990-11-12 | 1990-11-12 | Method of obtaining novel arylohydrazone cationic dyes |
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| Publication Number | Publication Date |
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| PL287735A2 PL287735A2 (en) | 1991-08-26 |
| PL161926B2 true PL161926B2 (en) | 1993-08-31 |
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1990
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| PL287735A2 (en) | 1991-08-26 |
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