Oligomeric triarylmethane dyes

Details Oligomeric triarylmethane dyes Oligomeric triarylmethane dyes

1997-02-19

1998-05-12

Raymond, Richard L.

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

Organic compounds

Acyclic carbon bonded directly to three benzene rings or to...

564326, C07C21742

Patent

active

057507422

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/EP95/03111, filed Aug. 4, 1995. The present invention relates to novel triarylmethanes of the formula I ##STR2## where m is from 1 to 100, -alkylene, -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or halogen, substsituted by hydroxyl, C.sub.1 -C.sub.4 -alkoxy, halogen or cyano, -C.sub.4 -alkyl, which may be hydroxyl-, C.sub.1 -C.sub.4 -alkoxy-, halogen- or cyano-substituted, substituted or unsubstituted phenyl or a radical of the formula ##STR3## where L.sup.1, L.sup.2, R.sup.2 and R.sup.3 are each as defined above, Q is a radical of the formula ##STR4## where R.sup.1 is as defined above, radical of the formula --NZ.sup.1 Z.sup.2, and -C.sub.4 -alkyl, which may be hydroxyl-, C.sub.1 -C.sub.4 -alkoxy-, halogen- or cyano-substituted, or substituted or unsubstituted phenyl, and
EP-A-31 070 discloses oligomeric triarylmethane dyes which are linked by alkylene bridges. However, it has been found that the dyes mentioned therein have disadvantages in their application properties.
It is an object of the present invention to provide novel oligomeric triarylmethane dyes. The novel dyes shall be advantageous for dyeing or printing polymeric material, especially paper stock, and shall be readily obtainable.
We have found that this object is achieved by the above-defined triarylmethanes of the formula I.
In the triarylmethanes of the formula I, the positive charge may also be mesomerically shifted.
Any alkyl or alkylene appearing in the abovementioned formula I may be straight-chain or branched.
In any substituted alkyl appearing in the abovementioned formula I the number of substituents is generally from 1 to 3.
Any substituted phenyl appearing in the abovementioned formula I may have as substituents for example C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or halogen. The number of substituents in substituted phenyl is generally from 1 to 3.
Within multiple L.sup.1, as also within multiple L.sup.2, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7 and Q, the individual meanings can be identical or different. (CH.sub.2).sub.3, (CH.sub.2).sub.4, CH(CH.sub.3)CH.sub.2 or CH(CH.sub.3)CH(CH.sub.3). and Z.sup.2 are each for example methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl or tert-butyl. also be for example 2-hydroxyethyl, 2- or 3-hydroxypropyl, 2- or 4-hydroxybutyl, 2-methoxyethyl, 2- or 3-methoxypropyl, 2- or 4-methoxybutyl, 2-ethoxyethyl, 2- or 3-ethoxypropyl, 2- or 4-ethoxybutyl, fluoromethyl, chloromethyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, 2-fluoroethyl, 2-chloroethyl, 2- or 3-fluoropropyl, 2- or 3-chloropropyl, 2- or 4-fluorobutyl, 2- or 4-chlorobutyl, cyanomethyl, 2-cyanoethyl, 2- or 3-cyanopropyl or 2- or 4-cyanobutyl. propoxy, isopropoxy, butoxy, isobutoxy or sec-butoxy. bromine. for example phenyl, 2-, 3- or 4-methylphenyl, 2,4-dimethylphenyl, 2-, 3- or 4-ethylphenyl, 2-, 3- or 4-methoxyphenyl, 2,4-dimethoxyphenyl, 2-, 3- or 4-chlorophenyl or 2,4-dichlorophenyl.
Suitable anions for derivation of An.sup..crclbar. include for example fluoride, chloride, bromide, iodide, perchlorate, hydrogensulfate, sulfate, aminosulfate, nitrate, dihydrogenphosphate, phosphate, hydrogencarbonate, carbonate, methosulfate, ethosulfate, cyanate, thiocyanate, tetrachlorozincate, borate, tetrafluoroborate, acetate, cyanoacetate, hydroxyacetate, aminoacetate, methylaminoacetate, mono-, di- or trichloroacetate, 2-chloropropionate, 2-hydroxypropionate, glycolate, thioglycolate, thioacetate, phenoxyacetate, trimethylacetate, valerate, palmitate, oleate, acrylate, oxalate, malonate, crotonate, succinate, citrate, methylenebisthioglycolate, ethylenebisiminoacetate, nitrilotriacetate, fumarate, maleate, benzoate, methylbenzoate, chlorobenzoate, dichlorobenzoate, hydroxybenzoate, aminobenzoate, phthalate, terephthalate, indolylacetate, chlorobenzenesulfonate, benzenesulfonate, toluenesulfonate, biphenylsulfonate or chlorotoluenesulfonate.
Preference is given to triarylmethanes of the formula I where m is from 2 to 30. Preference is further given to tr

REFERENCES:
patent: 4223144 (1980-09-01), Kast et al.
patent: 4353833 (1982-10-01), Bruder et al.

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