Pyrazolone Oranges

Pyrazoles, 13 599 Pyrazolinone couplers, 19 254-255 Pyrazolo-(3,2,-c)-5-triazole couplers, 19 256 Pyrazolobenzimidazole couplers, 19 256 Pyrazolone dyes, 19 285 Pyrazolone Orange, 19 435 pigment for plastics, 7 367t Pyrazolone reds, 19 437 Pyrazolones, 9 283 13 599... 

Pigment Orange 13 [3520-72-7] 21110 disazo pyrazolone (Pyrazolone Orange) coupling of tetrazotized 3,3 -dichloro-benzidine with l-phenyl-3-methyl-pyrazolone... 

Synonyms Cl 21115 Cl pigment orange 34 Dis-azo pigment pyrazolone Fast orange F2G Pyrazolone orange Empirical CsjFIjsCIjNsOj... 

Pyrazolin-5-one, 3-methyl-1-phenyl- 5-Pyrazolone, 3-methyl-1-phenyl-. Seel-Phenyl-3-methyl-5-pyrazolone Pyrazolone orange. See Pigment orange 34 Pyrazolone red. See Pigment red 38 Pyrazon. See Chloridazon Pyrazophos CAS 13457-18-6... 

Orange pigments cadmium orange, pyrazolone orange... 

Ah. the heterocychc coupling components that provide commercially important azo dyes contain only nitrogen as the hetero atom. They are indoles (31), pyrazolones (32), and especially pyridones (33) they provide yeUow to orange dyes for various substrates. 

Pyrazolones. Pyrazolones are used as coupling components since they couple readily at the 4-position under alkaline conditions to give important azo dyes in the yeUow-orange shade area. 

Pyrazolone derivatives have found many applications as cotton azo dyes because, even if they were more expensive intermediates, they improved qualities such as brightness and light fastness. Rosanthrene Orange (727) and Pyrazol Orange (728) are two representative examples. 

There is a large number of heteroaromatic coupling components of very different structural types. l-Aryl-3-methyl-5-pyrazolones have been widely used for yellow and orange monoazo dyes since the end of the 19th century. Other types have become important as a source of new industrially produced dyes in the last two decades. In reviews on industrial aspects (e.g., Schwander, 1982) these coupling components are classified not on the basis of their structures, but from the viewpoint of what is important for tinctorial properties of the dyes obtained with these types of coupling components. Here we will use a structural approach to systematization. 

Aniline derivatives -> Pyrazolone-5 derivatives yellow to orange... 

Yellow dyes are generally monoazo, and most are pyrazolone or pyri-done couplings. Orange dyes are generally monoazo derived from couplings to pyrazolones or of slightly substituted phenyl and naphthyl groups. 

With regard to heterocyclic compounds as coupling components, the importance of the formerly widespread pyrazolone-, aminopyrazole-, and 4-hydroxy -quinolone-based yellow azo dyes has greatly diminished with the advent of the tinctorially superior and therefore more economical pyridone azo dyes. Only a few examples have survived and then only for special applications such as for dyeing of acetate fibers. Examples are C.I. Disperse Orange 56 and C.I. Disperse Yellow5. (for structure, see Section 3.2.5). 

Acetoacetic acid arylides and pyrazolone derivatives are the coupling components mainly used. Naphtbolsulfonic acids are of only minor importance here. Dehydrothio- p-toluidine sulfonic acid (2) and the sulfonated primulin base are also used as diazo components for certain orange disazo direct dyes. 

Reaction of chlorosulfonic acid with mono- [141] or disazo dyes [142] yields sulfonyl chlorides, which can then be transformed into cationically substituted sulfonamides by reaction with dialkylaminoalkylamines. The coupling product of diazotized 2-anisidine with 2-hydroxynaphthoic acid arylide upon such treatment dyes paper red, and the azo dye from tetrazotized dianisidine and l-phenyl-3-methyl-5 -pyrazolone gives yellowish orange shades. 

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