Pyridone colorants

Details Pyridone colorants Pyridone colorants

1998-11-18

2000-11-07

Fan, Jane

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

8568, C07D41706

Patent

active

061438987

DESCRIPTION:

BRIEF SUMMARY
DESCRIPTION

The present invention relates to novel pyridone dyes of the formula I ##STR2## where R.sup.1 is C.sub.1 -C.sub.20 -alkyl with or without substitution and with or without interruption by from 1 to 4 oxygen atoms in ether function or is substituted or unsubstituted phenyl, without benzofusion, oxygen atoms in ether function and with or without phenyl or hydroxyl substitution, or is substituted or unsubstituted phenyl, and C.sub.1 -C.sub.4 -alkanoyl, dyeing or printing synthetic materials.
U.S. Pat. No. 5,079,365 discloses pyridone dyes with a methyl group in position 4 of the pyridine ring.
It is an object of the present invention to provide novel pyridone dyes having a different chemical structure and advantageous properties.
We have found that this object is achieved by the pyridone dyes of the formula I defined at the beginning.
R.sup.2 is a 5- or 6-membered carbocyclic or heterocyclic radical with or without substitution and with or without benzofusion.
R.sup.2 can be derived for example from components of the benzene, indole, quinoline, naphthalene, pyrrole, thiazole, benzimidazole, benzothiazole, thiophene or diaminopyridine series.
Important R.sup.2 radicals include for example those of the formulae IIa to IIj ##STR3## where n is 0 or 1, by 1 or 2 oxygen atoms in ether function, hydroxyl, C.sub.1 -C.sub.4 -alkoxy, especially methoxy or ethoxy, formylamino, C.sub.1 -C.sub.4 -alkylsulfonylamino, mono- or di(C.sub.1 -C.sub.4 -alkyl)aminosulfonylamino or the radical --NHCOZ.sup.7 or --NHCO.sub.2 Z.sup.7, where Z.sup.7 is phenyl, benzyl, tolyl or C.sub.1 -C.sub.8 -alkyl with or without interruption by 1 or 2 oxygen atoms in ether function, -C.sub.4 -alkoxy, especially methoxy or ethoxy, -C.sub.8 -alkyl with or without substitution and with or without interruption by 1 or 2 oxygen atoms in ether function, C.sub.3 -C.sub.4 -alkenyl, C.sub.5 -C.sub.7 -cycloalkyl or substituted or unsubstituted phenyl, or are together with the adjacent nitrogen atom a 5- or 6-membered saturated heterocyclic radical with or without further heteroatoms, unsubstituted phenyl, substituted or unsubstituted benzyl, cyclohexyl, thienyl, hydroxyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio or mono(C.sub.1 -C.sub.8 -alkyl)amino.
Any alkyl or alkenyl appearing in the hereinmentioned formulae may be straight-chain or branched.
Any substituted alkyl appearing in the hereinmentioned formulae may contain as substituents for example substituted or unsubstituted phenyl, substituted or unsubstituted phenoxy, carboxyl, C.sub.1 -C.sub.20 -alkoxycarbonyl whose alkyl chain is with or without interruption by from 1 to 4 oxygen atoms in ether function and with or without phenyl or phenoxy substitution, hydroxyl, halogen, cyano, C.sub.1 -C.sub.8 -alkanoyloxy, C.sub.1 -C.sub.8 -alkylaminocarbonyloxy or C.sub.1 -C.sub.8 -alkoxycarbonyloxy, the alkoxy group in the last three cases being with or without phenyl or C.sub.1 -C.sub.4 -alkoxy substitution. The number of substituents in substituted alkyl is generally from 1 to 3.
In any alkyl appearing in the hereinmentioned formulae with interruption by oxygen atoms in ether function, the number of oxygen atoms interrupting in ether function is preferably 1 or 2.
Any substituted phenyl or thienyl appearing in the hereinmentioned formulae may contain as substituents for example C.sub.1 -C.sub.4 -alkyl, trifluoromethyl, C.sub.1 -C.sub.4 -alkoxy, halogen, nitro or carboxyl. The number of substituents in substituted phenyl or thienyl is generally from 1 to 3.
Suitable R.sup.1, R.sup.3, R.sup.4, R.sup.5, Z.sup.1, Z.sup.2, Z.sup.3, Z.sup.4, Z.sup.5, Z.sup.6 and Z.sup.7 are each for example, like the belowmentioned L.sup.2 and L.sup.3, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl or tert-butyl.
R.sup.1, R.sup.5, Z.sup.1, Z.sup.3, Z.sup.4, Z.sup.6 and Z.sup.7 may each also be for example pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, 2-methylpentyl, heptyl, octyl, 2-ethylhexyl or isooctyl.
R.sup.1 may also be for example nonyl, isononyl, decyl, isodecyl, undecyl, dodecyl, tr

REFERENCES:
patent: 5079365 (1992-01-01), Sens et al.
patent: 5132438 (1992-07-01), Bach et al.
patent: 5545235 (1996-08-01), Sens et al.
patent: 5719288 (1998-02-01), Sens et al.

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