Bipyridyls and their use as inks

Details Bipyridyls and their use as inks Bipyridyls and their use as inks

1991-12-31

1993-11-30

Cintins, Marianne M.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

546141, 546153, 546257, C07D21716, C07D21520, C07D21330

Patent

active

052667006

DESCRIPTION:

BRIEF SUMMARY
The invention relates to bipyridyls of the general formula I ##STR2## in which
R, R', independently of one another, are hydrogen, alkyl or alkylcarbonyl, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, independently of one another, are hydrogen, aromatic radicals and/or heterocyclic radicals and/or other non-water-solubilizing radicals and also R.sup.1 and R.sup.2 or R.sup.2 and R.sup.3, and/or R.sup.4 and R.sup.5 or R.sup.5 and R.sup.6 together with the pyridine ring to which they are bound can be a fused-on phenyl ring, which can also be substituted, under the condition that R.sup.1, R.sup.2, R.sup.4, R.sup.5 are not hydrogen if R.sup.3 and R.sup.6 are hydrogen or methyl, and to processes for their preparation and to their use.
In the bipyridyls of the formula I, one to six, preferably one to four, aromatic radicals and/or heterocyclic radical [sic] and/or other non-water-solubilizing radicals can be present as R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6.
R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and/or R.sup.6 as aromatic radicals are in particular mono- to tetracyclic and preferably mono- or bicyclic. Examples of radicals of this type are: phenyl, naphthyl, diphenyl, phenanthryl, fluorenyl, acenaphthyl, pyrenyl, chrysenyl, naphthacenyl.
R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and/or R.sup.6 as heterocyclic aromatic radicals are preferably mono- to tricyclic and can be purely heterocyclic or contain a heterocyclic ring and one or more fused-on benzene rings.
R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and/or R.sup.6 as heterocyclic radicals can be saturated or unsaturated and contain one or more keto, hydroxyl, sulfonyl or sulfone groups. They can contain one or more hetero atoms, in particular from the series comprising O, S and N. Examples of suitable heterocyclic radicals are imides, lactams, sulfoimides.
Examples of heterocyclic aromatic and heterocyclic radicals are: pyridyl, pyrimidinyl, pyrazinyl, triazinyl, furanyl, pyrrolyl, thiophenyl, quinolyl, isoquinolyl, coumarinyl, benzobenzimidazolyl, benzoxazolyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, indolyl, carbazolyl, pyrazolyl, pyrazinyl, imidazolyl, oxazolyl, isooxazolyl, thiazolyl, indazolyl, benzothiazolyl, pyridazinyl, cinnolinyl, quinazolyl, quinoxalyl, phthalazinyl, phthalazinedionyl, phthalimidyl, chromonyl, naphtholactamyl, benzopyridonyl, ortho-sulfobenzimidyl, maleimidyl, naphtharidinyl, benzimidazolonyl, benzoxazolinyl, benzothiazolonyl, benzothiazolinyl, quinazolonyl, quinoxazolinyl, phthalazonyl, dioxapyrimidinyl, pyridonyl, isoquinolonyl, isothiazolyl, benzisoxazolyl, benzisothiazolyl, indazolonyl, acridinyl, acridonyl, quinazolinedionyl, benzoxazinedionyl, benzoxazinonyl and naphthalimidyl.
R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and/or R.sup.6 as aromatic or heterocyclic aromatic or heterocyclic radicals can also contain one or more, in particular one to three, non-water-solubilizing substituents, in particular, for example, those listed below under a to r:
a) Halogen atoms, for example chlorine, bromine, iodine or fluorine.
b) Branched or unbranched alkyl groups preferably having 1 to 18, in particular 1 to 12, in particular 1 to 8, and particularly preferably 1 to 4, C atoms. These alkyl groups can have one or more, preferably one, non-water-solubilizing substituent, such as, for example, fluorine, hydroxyl, cyano, --OCO.sup.7, --OR.sup.8, --OCOOR.sup.7 --CON(R.sup.8)(R.sup.9) or --OCONHR.sup.7, in which R.sup.7 is alkyl, aryl, such as phenyl or naphthyl, or unsubstituted or halogen-, alkyl- or --O-alkyl-substituted benzyl or a heterocyclic radical, R.sup.8 and R.sup.9 are hydrogen, unsubstituted or cyano- or hydroxyl-substituted alkyl, C.sub.3 - to C.sub.24 -cycloalkyl, preferably C.sub.5 -, C.sub.6 -, C.sub.12 -, C.sub.15 -, C.sub.16 -, C.sub.20 - and C.sub.24 -cycloalkyl, aryl or heteroaryl, in particular unsubstituted or halogen-, alkyl- or --O-alkyl-substituted phenyl, or in which R.sup.8 and R.sup.9 together with, in each case, one of the other radicals R.sup.2 to R.sup.4 form a 5- or 6

REFERENCES:
patent: 3751419 (1973-08-01), Ziegler
patent: 4656278 (1987-04-01), Rossey et al.

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