CS225528B1 - Mono-azo dye made based om 2,6-diaminomesythylene-4-sulphoacid and its preparation - Google Patents
Mono-azo dye made based om 2,6-diaminomesythylene-4-sulphoacid and its preparation Download PDFInfo
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- CS225528B1 CS225528B1 CS624982A CS624982A CS225528B1 CS 225528 B1 CS225528 B1 CS 225528B1 CS 624982 A CS624982 A CS 624982A CS 624982 A CS624982 A CS 624982A CS 225528 B1 CS225528 B1 CS 225528B1
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- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 5
- 239000000987 azo dye Substances 0.000 title description 2
- PKKGGWLTUCMSSD-UHFFFAOYSA-N 3,5-diamino-2,4,6-trimethylbenzenesulfonic acid Chemical compound CC1=C(N)C(C)=C(S(O)(=O)=O)C(C)=C1N PKKGGWLTUCMSSD-UHFFFAOYSA-N 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000001768 cations Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 230000003213 activating effect Effects 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- 239000000975 dye Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000012954 diazonium Substances 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 150000001989 diazonium salts Chemical class 0.000 description 6
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- -1 1-aryl-5-pyrazolones Chemical class 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- 150000002790 naphthalenes Chemical class 0.000 description 2
- 150000004780 naphthols Chemical class 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000001043 yellow dye Substances 0.000 description 2
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- YVFMPXVMGPZCRS-UHFFFAOYSA-N 1-(2,5-dichloro-4-sulfophenyl)-5-oxo-4h-pyrazole-3-carboxylic acid Chemical compound O=C1CC(C(=O)O)=NN1C1=CC(Cl)=C(S(O)(=O)=O)C=C1Cl YVFMPXVMGPZCRS-UHFFFAOYSA-N 0.000 description 1
- GLDQAMYCGOIJDV-UHFFFAOYSA-N 2,3-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC(O)=C1O GLDQAMYCGOIJDV-UHFFFAOYSA-N 0.000 description 1
- QPKNFEVLZVJGBM-UHFFFAOYSA-N 2-aminonaphthalen-1-ol Chemical class C1=CC=CC2=C(O)C(N)=CC=C21 QPKNFEVLZVJGBM-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- WHSXTWFYRGOBGO-UHFFFAOYSA-N 3-methylsalicylic acid Chemical compound CC1=CC=CC(C(O)=O)=C1O WHSXTWFYRGOBGO-UHFFFAOYSA-N 0.000 description 1
- UWPJYQYRSWYIGZ-UHFFFAOYSA-N 5-aminonaphthalene-2-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2C(N)=CC=CC2=C1 UWPJYQYRSWYIGZ-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 125000002339 acetoacetyl group Chemical group O=C([*])C([H])([H])C(=O)C([H])([H])[H] 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 description 1
- UIAFKZKHHVMJGS-UHFFFAOYSA-N beta-resorcylic acid Natural products OC(=O)C1=CC=C(O)C=C1O UIAFKZKHHVMJGS-UHFFFAOYSA-N 0.000 description 1
- 229950011260 betanaphthol Drugs 0.000 description 1
- 239000001049 brown dye Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- FNXKBSAUKFCXIK-UHFFFAOYSA-M sodium;hydrogen carbonate;8-hydroxy-7-iodoquinoline-5-sulfonic acid Chemical class [Na+].OC([O-])=O.C1=CN=C2C(O)=C(I)C=C(S(O)(=O)=O)C2=C1 FNXKBSAUKFCXIK-UHFFFAOYSA-M 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
Description
Vynález se týká nových monoazobarviv na bázi 2,6-diaminomesitylen-4-sulfonové kyseliny a způsobu jejich přípravy kopulací diazoniových solí diaininomesitylensulfokyseliny s pasivními azokomponentami.The present invention relates to novel monoazo dyes based on 2,6-diaminomesitylene-4-sulfonic acid and to a process for their preparation by coupling diazonium salts of diaininomesitylene sulfonic acid with passive azo components.
Předmětem tohoto vynálezu jsou monoazobarviva na bázi 2,6-diaminomesitylen-4-sulfonové kyseliny obecného vzorce IThe present invention provides monoazo dyes based on 2,6-diaminomesitylene-4-sulfonic acid of formula I
kde X značí vodík nebo kationt, Z je zbytek pasivní azokomponenty alifatických, aromatických iuí>o heterocyklických derivátů, A zna čí aktivující auxochromní skupinu např. OH, NH2, OR, NHR, NR2, NHAr, NH-SO^H, NH-SOgAr, NH-N02, kde R značí alkyl s jedním nebo dvěma uhlíky a Ar aryl s 6 až 10 atomy uhlíku a způsob jejich přípravy spočívající v tom, že se vzájemně působí diazoniovými solemi 2,6-diaminomesitylen-4-sulfonové kyseliny, charakterizovanými obecnými vzorci Ila resp. libwherein X is hydrogen or a cation, Z is a passive azo moiety of aliphatic, aromatic or heterocyclic derivatives, A denotes an activochromic moiety such as OH, NH 2 , OR, NHR, NR 2 , NHAr, NH-SO 4 H, NH -SOgAr, NH-NO 2 , wherein R represents a alkyl of one or two carbons and Ar aryl of 6 to 10 carbon atoms and a process for their preparation by interacting with diazonium salts of 2,6-diaminomesitylene-4-sulfonic acid , characterized by the general formulas IIIa, resp. lib
značí aniont silné kyseliny, kde Ydenotes a strong acid anion where Y
X má výše uvedený význam, a pasivními azokomponentami obecného vzorce H-Z-A, kde Z a A majíX is as defined above, and the passive azo components of the formula H-Z-A, wherein Z and A are each
- 2 225 528 výše uvedený význam, při teplotě 0 až 40 °C v prostředí, kde je pH 3 až 13.- 2,225,528 as defined above, at a temperature of 0 to 40 ° C in an environment where the pH is 3 to 13.
Z pasivních azokomponent jsou vhodné sloučeniny alifatické např. s acetoacetylovým zbytkem v molekule, sloučeniny heterocyklické např. l-aryl-5-pyrazolony, hydroxychinoliny a komponenty aromatického charakteru např. fenoly, aminofenoly, aminy, naftoly, aminonaftoly a podobně.Among the passive azo components, aliphatic compounds with, for example, an acetoacetyl moiety in the molecule, heterocyclic compounds such as 1-aryl-5-pyrazolones, hydroxyquinolines and aromatic components such as phenols, aminophenols, amines, naphthols, aminonaphthols and the like are suitable.
Diazoniové soli obecného vzorce Ha resp. lib lze připravit z 2,6-diaminomesitylen-4-sulfonové kyseliny a jejích solí podle A.O. 225037.The diazonium salts of the formula IIa and IIa, respectively. IIb can be prepared from 2,6-diaminomesitylene-4-sulfonic acid and its salts according to A.O. 225037.
Kopulaci diazoniových solí se zvolenými pasivními azokomponentami lze provést některým ze známých způsobů běžných v azochemii. V technické praxi je výhodný postup, kdy se reakční směs po diazotaci 2,6-diaminomesitylen-4-sulfonové kyseliny směšuje s roztokem pasivní azokomponenty a pH reakční směsi se - podle požadavku upraví přídavkem alkálie nebo kyseliny. Tak lze kopulovat fenoly a naftoly v alkalickém prostředí, kopulace s aminy provádět v neutrálním nebo slabě kyselém prostředí. Vysoké výtěžky azobarviv se dosáhnou při práci za snížených teplot, při intenzivním míchání, případně s mírným nadbytkem pasivních azokomponent.Coupling of diazonium salts with selected passive azo components can be accomplished by any of the known methods of azochemistry. In technical practice, the reaction mixture is preferably mixed with a passive azo component solution after diazotization of 2,6-diaminomesitylene-4-sulfonic acid and the pH of the reaction mixture is adjusted by adding alkali or acid as desired. Thus, the phenols and naphthols can be coupled in an alkaline medium, the amines coupled in a neutral or weakly acidic medium. High yields of azo dyes are achieved when working at reduced temperatures, with intensive stirring, possibly with a slight excess of passive azo components.
Příklad 1Example 1
Do 100 ml vody se přidá 1,2 g hydroxidu sodného a 0,03 molTo 100 ml of water was added 1.2 g of sodium hydroxide and 0.03 mol
2,6-diaminomesitylen-4--sulfonové kyseliny a k získanému roztoku se přilije 18 ml kyseliny chlorovodíkové o koncentraci £ (HC1) β 5mol/l (0,09 mol). Vzniklá suspenze se ochladí na Uplotu 5 °C vhozením 72 g ledu, načež se během 30 minut přikape 12 ml vodného roztoku dusitanu sodného o koncetraci £ (NaNOg) =2,5 mol/1 (0,03 mol) při teplotě 5 °C za intenzivního míchání. Získaná reakční směs se přidá k roztoku připravenému z 80 ml vody, 5,42 g 100% acetoaceanilidu (0,0306 mol) a 17 ml roztoku hydroxidu sodného o konc^raci £ (NaOH) =2,5 mol/1, ochlazenému na 10 °C. Vzniklá žlutá suspenze se zalkalizuje přídavkem 10 ml hydroxidu sodného o koncentraci £ (NaOH) =2,5 mol/1 a míchá se po dobu 30 minut. Potom se reakční směs zahřeje na 80 °C a z roztoku se barvivo vysolí přídavkem 29 g NaCl. Suspenze se ze|, tnicharií ochladí na 20 °0, pevný podíl se odfiltruje a filtrační koláč usušíOf 2,6-diaminomesitylene-4-sulfonic acid and 18 ml of δ (HCl) β 5mol / l (0.09 mol) are added to the solution obtained. The resulting suspension is cooled to 5 ° C by introducing 72 g of ice, then 12 ml of an aqueous solution of sodium nitrite having a concentration of δ (NaNO 3) = 2.5 mol / l (0.03 mol) at 5 ° C is added dropwise over 30 minutes. with vigorous stirring. The reaction mixture obtained is added to a solution prepared from 80 ml of water, 5.42 g of 100% acetoaceanilide (0.0306 mol) and 17 ml of sodium hydroxide solution with a concentration of (NaOH) = 2.5 mol / l, cooled to Low: 14 ° C. The resulting yellow suspension was basified by the addition of 10 ml of NaOH (NaOH) = 2.5 mol / l and stirred for 30 minutes. Then the reaction mixture is heated to 80 ° C and the dye is salted out of solution by adding 29 g of NaCl. The suspension is cooled to 20 DEG C., the solid is filtered off and the filter cake is dried.
- 3 225 528 při 105 °C do konstantní hmotnosti získá se 92 % teorie žlutého barviva konstituce- 3 225 528 at 105 ° C to constant weight gives 92% of the theory of yellow dye of constitution
Příklad 2Example 2
Postupem popsaným u př. 1 se připraví suspenze diazoniové soli z 0,03 mol 2,6-diaminomesitylen-4-sulfonové kyseliny; tato suspenze se vlije do zneutralisovaného vodného roztoku připraveného z 11,74 g 92% 1-(2^5-díchlor-4-sulfofenyl)-3-karboxy-5-pyrazolunu (0,0306 mol), 100 ml vody a 10% NaOH, načež se reakční směs zalkalizuje 20 ml vodného roztoku hydroxidu sodného o koncentraci c (NaOH) =2,5 mol/l. Oranžově žlutý roztok se zahřeje na 70 °C a při této teplotě se barvivo vysolí přídavkem 75 g NaCl. Vzniklá suspenze se 30 minut míchá,načež se pevný podíl odfiltruje a koláč usuší. Získá se 89 % teorie oranžově žlutého barviva konstitucePreparation of a suspension of diazonium salt from 0.03 mol of 2,6-diaminomesitylene-4-sulfonic acid as described in Example 1; this suspension is poured into a neutralized aqueous solution prepared from 11.74 g of 92% 1- (2,5-dichloro-4-sulfophenyl) -3-carboxy-5-pyrazolone (0.0306 mol), 100 ml of water and 10% NaOH, whereupon the reaction mixture is basified with 20 ml of an aqueous solution of sodium hydroxide c (NaOH) = 2.5 mol / l. The orange-yellow solution is heated to 70 ° C and at this temperature the dye is salted out by adding 75 g of NaCl. The resulting suspension was stirred for 30 minutes, then the solid was filtered off and dried. 89% of theory of an orange-yellow dye of constitution are obtained
- 4 Příklad 3- 4 Example 3
* 225 528 se připraví z 0,03 mol 2,6-diaminomesitylen-4-sulfonové kyseliny a 0,0306 mol 2-naftolu analogickým způsobem jako u příkladu 1 a 2 ve výtěžku 93,5 % teorie.225 528 was prepared from 0.03 mol of 2,6-diaminomesitylene-4-sulfonic acid and 0.0306 mol of 2-naphthol in an analogous manner to Examples 1 and 2 in a yield of 93.5% of theory.
Příklad 4Example 4
Do 90 ml vody se přidá 7,65 g 88,8% l-naftylamin-6-sulfonové kyseliny (0,0306 mol) a 4,5 ml roztoku hydroxidu sodného o koncentraci c (NaOH) =2,5 mol/1. K vzniklému roztoku se při teplotě 8 °C přidá 180 ml suspenze diazoniové soli 2,6-diaminomesitylen-4-sulfonové kyseliny (0,03 mol) připravené dle příkladuTo 90 ml of water was added 7.65 g of 88.8% 1-naphthylamine-6-sulfonic acid (0.0306 mol) and 4.5 ml of sodium hydroxide solution with a c (NaOH) concentration of 2.5 mol / l. 180 ml of a suspension of 2,6-diaminomesitylene-4-sulfonic acid diazonium salt (0.03 mol) prepared according to the example was added at 8 ° C.
1. Kyselost reakční směsi se otupí 20 ml roztoku hydroxidu sodného o koncentraci £ (NaOH) - 2,5 mol/1 (pH 5 až 6) a míchá se 30 minut. Potom se při teplotě 70 °0 přidá 75 g chloridu sodného, reakční směs se okyselí koncentrovanou kyselinou chlorovodíkovou na pH 3 a vzniklá suspenze se míchá 1 hodinu při 20 °C, načež se pevný podíl odfiltruje a koláč usuší. Získá se 9G,5 % teorie tmavě hnědého barviva konstituce.1. Acidify the reaction mixture with 20 mL of δ (NaOH) - 2.5 M sodium hydroxide solution (pH 5-6) and stir for 30 minutes. Sodium chloride (75 g) was then added at 70 ° C, the reaction mixture was acidified to pH 3 with concentrated hydrochloric acid, and the suspension was stirred at 20 ° C for 1 hour, then the solid was filtered off and dried. 9G, 5% of a theory of dark brown dye constitution is obtained.
- 5 Příklad 5 225 528- 5 Example 5 225 528
180 ml suspenze diazoniové soli teploty 5 °C, připravené z 0,03 mol 2,6-diarainomesitylen-4-sulfonové kyseliny postupem popsaným v příkladu 1, se za intenzivního míchání vlije do neutrálního roztoku objemu 100 ml, teploty 8 °C, obsahujícího 0,030 6 mol l-naftol-3-amino-6-sulfonové kyseliny. Reakční směs se alkalizuje na pH 8,5, načež se míchá 1 hodinu, potom vyhřeje na 80 °C a z roztoku se barvivo vysolí analogicky jako v příkladu 2. Získá se 88 % teorie barviva následující k&nstituce180 ml of a 5 ° C diazonium salt suspension, prepared from 0.03 mol of 2,6-diarainomesitylene-4-sulfonic acid as described in Example 1, is poured into a 100 ml neutral solution containing 8 ° C containing vigorous stirring. 0.030 6 mol of 1-naphthol-3-amino-6-sulfonic acid. The reaction mixture is basified to pH 8.5, then stirred for 1 hour, then heated to 80 ° C and the dye is salted out analogously to Example 2. 88% of the dye theory is obtained as follows
Další příklady monoazobarviv na bázi 2,6-diaminomesitylen-4-sulfonové kyseliny s pasivními azokomponentami z benzenové řady obsahuje Tabulka X (příklad 6 až 20) a s pasivními komponentami z naftalenové řady Tabulka II (příklad 20 až 30). V uvedených vzorcích je označen pro jednoduchostFurther examples of 2,6-diaminomesitylene-4-sulfonic acid monoazo dyes with passive azo components of the benzene series are shown in Table X (Examples 6 to 20) and with passive naphthalene series components Table II (Examples 20 to 30). In the above formulas, it is marked for simplicity
jako Ar —as Ar -
- 6 Tabulka I- 6 Table I
225 528225 528
Monoazobarviva na bázi 2,6-diaminomesitylen-4-sulfonové kyseliny s pasivními azokomponentami z benzenové řady.Monoazo dyes based on 2,6-diaminomesitylene-4-sulfonic acid with passive azo components from the benzene series.
Příklad Pasivní komponenta Struktura barvivaExample Passive component Dye structure
225 528225 528
1,3-fenylendiamin1,3-phenylenediamine
-4-sulfokyselina-4-sulfoacid
1,3 -f eny 1 endi amin-4,6-disulfokyselina o-kresol1,3-phenylenediamine-4,6-disulfoic acid o-cresol
HOHIM
- 8 15 kyselina salicylová- 8 15 salicylic acid
Ar - N = N pyrokatechin kyselina kresotinováAr - N = N pyrocatechin cresotinic acid
225 528225 528
COOHCOOH
OHOH
i kyselina resorcylováand resorcylic acid
3-βηιίηοΓβηο1-4'3-βηιίηοΓβηο1-4 '
-sulfokyselina-sulfoacid
HOHIM
- 9 225 528- 9 225 528
Tabulka IITable II
Monoazobarviva na bázi 2,6-diaminomesitylen-4~sulfonové kyseliny s pasivními azokomponentami z naftalenové řady.Monoazo dyes based on 2,6-diaminomesitylene-4-sulfonic acid with passive azo components from the naphthalene series.
Příklad Pasivní azokomponenta Struktura barvivaExample Passive azo component Dye structure
l-naftylamin-5-sulfokyselina1-naphthylamine-5-sulfoacid
2-naftylamin-6-sulfokyselina2-Naphthylamine-6-sulfoacid
Ar - N =Ar = N =
2-naf tylamin-3,6· -di sulfokys elina2-naphthylamine-3,6'-di-sulfo acid
Ar - N =Ar = N =
l-naftol-5-sulfokys elina1-Naphthol-5-sulfoacid
OHOH
Ar - N = NAr = N = N
l-hydroxy-8-etoxynaftalen-5-sulfokyselina l-amino-8-naftol-4-sulfokyselina (kopulace v alkalickém prostředí) l-amino-8-naftol-4-sulfokyselina (kopulace v kyselém prostředí)1-hydroxy-8-ethoxynaphthalene-5-sulfoacid 1-amino-8-naphthol-4-sulfoacid (alkaline coupling) 1-amino-8-naphthol-4-sulfoacid (acid coupling)
8-chlor-l-naftol-5-aulfokyselina8-chloro-1-naphthol-5-sulfonic acid
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS624982A CS225528B1 (en) | 1982-08-27 | 1982-08-27 | Mono-azo dye made based om 2,6-diaminomesythylene-4-sulphoacid and its preparation |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS624982A CS225528B1 (en) | 1982-08-27 | 1982-08-27 | Mono-azo dye made based om 2,6-diaminomesythylene-4-sulphoacid and its preparation |
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| Publication Number | Publication Date |
|---|---|
| CS225528B1 true CS225528B1 (en) | 1984-02-13 |
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| CS624982A CS225528B1 (en) | 1982-08-27 | 1982-08-27 | Mono-azo dye made based om 2,6-diaminomesythylene-4-sulphoacid and its preparation |
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1982
- 1982-08-27 CS CS624982A patent/CS225528B1/en unknown
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