Cyanine compounds

Details Cyanine compounds Cyanine compounds

1990-05-04

1992-02-11

Lee, Mary C.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548430, 548405, C07D20956, C07D491044, C07D491056

Patent

active

050877046

DESCRIPTION:

BRIEF SUMMARY
FIELD OF THE INVENTION

The present invention relates to novel cyanine compounds.


PRIOR ART

Prevalently used among inorganic recording media for semiconductor laser recording are those containing a predominant amount of tellurium for forming a recording layer. However, tellurium-type materials have the drawbacks of being toxic, low in corrosion resistance, expensive and unfit to densify. Research is under way to develop an organic dye which can replace the inorganic tellurium-type materials.
Given below are important characteristics required of organic dyes used as recording media: 700 to 900 nm and undergoing fusion, sublimation, decomposition and like changes by the action of resulting heat energy; detection of signals in reproduction; wet coating method; and an excellent retentivity (assuring a retention for 10 years or more) and unlikely to deteriorate in properties on exposure to light in reproduction.
While organic dyes are advantageous in being low in toxicity, high in corrosion resistance, inexpensive and fit to densify as compared with the foregoing inorganic materials, an organic dye remains to be developed which has the characteristics described above in items (2) and (3) among those in items (1) to (4).


DISCLOSURE OF THE INVENTION

An object of the present invention is to provide a cyanine compound suitable for use as an organic near infrared light-absorbing dye for an optical disc recording medium adapted for semiconductor laser recording.
Another object of the present invention is to provide a cyanine compound having the foregoing characteristics (1) to (4) required of an organic near infrared light-absorbing dye which is useful as an optical disc recording medium adapted for semiconductor laser recording.
A further object of the invention is to provide a cyanine compound having a high reflectivity comparable to that of inorganic tellurium-type materials.
A still further object of the invention is to provide a cyanine compound excellent in solubility in a solvent.
The cyanine compounds of the present invention are novel compounds undisclosed in literature and represented by the following formula (1) ##STR2## wherein R.sup.1 is a hydrogen atom or a lower alkyl group, R.sup.2 is an optionally substituted lower alkyl group, X and Y are the same or different and each represent a methylene group or an oxygen atom, Z is an acidic residue, and n is 2 or 3.
Shown below are specific examples of the groups represented by R.sup.1, R.sup.2 and Z in the formula (1).
Examples of the lower alkyl group are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-hexyl, n-heptyl, n-octyl and like C.sub.1 -C.sub.8 alkyl groups.
Illustrative of the substituents for the lower alkyl group are C.sub.1 -C.sub.8 alkoxy, hydroxyl, sulfonic acid group, carboxy, (C.sub.1 -C.sub.8 alkyl)amino, phenylsulfonyl amino, p-methylphenylsulfonyl amino, acetoxy, (C.sub.1 -C.sub.3 alkoxy)carbonyl, (C.sub.1 -C.sub.3 alkoxy)(C.sub.1 -C.sub.3 alkoxy)carbonyl and the like. Specific examples of the lower alkyl group having such substituents are methoxymethyl, ethoxymethyl, 2-methoxyethyl, 2-ethoxyethyl, 2-(n-butoxy)ethyl, n-butoxymethyl, 2-hydroxyethyl, a group --(CH.sub.2).sub.m --SO.sub.3 Na (wherein m is an integer of 1 to 8), methylaminomethyl, dimethylaminomethyl, 2-(p-methylphenylsufonylamino)ethyl, acetoxymethyl, 2-acetoxyethyl, methoxycarbonylmethyl, methoxymethoxymethyl, 2-ethoxyethoxyethyl and the like.
Examples of the group Z are halogen, alkyl sulfate residue, arylsulfonate residue, perchlorate residue, tetrafluoroborate residue, arylcarboxylic acid residue and the like. When Z is a halogen atom, examples of Z.sup.- are Cl.sup.-, Br.sup.-, I.sup.-, F.sup.- and the like. When Z is an alkyl sulfate residue, examples of Z.sup.- are CH.sub.3 SO.sub.4.sup.-, C.sub.2 H.sub.5 SO.sub.4.sup.-, n-C.sub.3 H.sub.7 SO.sub.4.sup.-, n-C.sub.4 H.sub.9 SO.sub.4.sup.- and the like. When Z is an arylsufonate residue, examples of Z.sup.- are ##STR3## and the like. When Z is a perchlorate residue, examples of Z.sup.- are ClO.s

REFERENCES:
patent: 3592653 (1971-07-01), Fumia et al.
patent: 3916069 (1975-10-01), Tiers et al.
patent: 3974147 (1976-08-01), Tiers et al.
patent: 4025347 (1977-05-01), Beretta et al.
patent: 4600625 (1986-07-01), Abet et al.
patent: 4735839 (1988-04-01), Sato et al.
patent: 4847385 (1989-07-01), Kusakata et al.

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