Process of preparing thiopyrylium sensitizing dyes

Details Process of preparing thiopyrylium sensitizing dyes Process of preparing thiopyrylium sensitizing dyes

1981-09-14

1983-01-11

Raymond, Richard

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

544145, 546 94, 546165, C07D33502

Patent

active

043683290

DESCRIPTION:

BRIEF SUMMARY
FIELD OF THE INVENTION

This invention relates to thiopyrylium compounds, to their preparation and to their use as photoconductors or sensitizers in photosensitive elements for image recording. In particular the invention relates to 2-(4-aminophenyl)thiopyrylium compounds.


BACKGROUND OF THE INVENTION

Photoconductive elements have achieved a broadly based acceptance in commercial technology. Almost all of these systems utilize the phenomenon exhibited by certain materials to change their conductivity when struck by radiation to which they are sensitive and thus are able to selectively discharge accumulated electrical charges. One important area of research in this technical area has been an effort to sensitize these photoconductive materials to different and more useful portions of the electromagnetic spectrum and to increase the efficiency of the photoconductive effect.
Electrophotographic imaging systems are well known in the art, as shown, for example, in U.S. Pat. Nos. 2,221,776; 2,277,013; 2,825,814; 3,220,831; 3,615,414, and others.
One generally accepted type of unitary photoconductive construction comprises a substrate having a conductive layer on at least one surface and a photoconductive composition over said conductive layer. The inclusion of photosensitizing materials or adjuvants to the photoconductive material is conveniently used to change the sensitivity and/or speed of the construction, as shown in U.S. Pat. Nos. 2,987,395 and 3,250,615.
U.S. Pat. No. 3,615,414 discloses the use of particulate discontinuous phases of pyrylium dyes in electrically insulating polymeric materials containing photoconductors to sensitize the photoconductive layer. Difficult and complex processing to effect the dispersion and agglomeration of the particule phases are disclosed therein to achieve some expansion of the range of spectral response for the photoconductors.


SUMMARY OF THE INVENTION

According to the present invention there is provided a method of preparing a compound of the general formula: ##STR4## in which: R.sup.1 and R.sup.2 independently represent a hydrogen atom, an alkyl or substituted alkyl group (preferably of up to 20 carbon atoms, more preferably of 1 to 8 carbon atoms), an aryl or substituted aryl group (preferably of up to 20 carbon atoms, more preferably phenyl), an aralkyl or substituted aralkyl group (preferably of up to 20 carbon atoms, preferably up to 10 carbon atoms), a cycloaliphatic or substituted cycloaliphatic group (preferably of 3 to 6 ring atoms) or a heterocyclic or substituted heterocyclic group (preferably of C, S, N and O atoms in 5, 6 or 7 membered rings) providing R.sup.1 and R.sup.2 do not both represent cyclic groups of aromatic nature, or R.sup.1 and R.sup.2 together may represent the necessary atoms to complete a non-aromatic heterocyclic ring comprised of C, S, N and O ring atoms, preferably of 5, 6 or 7 ring atoms, e.g. morpholine ring, atom or any substituent providing the sum of their .sigma..sub.p constants (Hammet sigma, para) has a value of less than .+-.0.5, preferably +0.4, or R.sup.3 and R.sup.4 and/or R.sup.5 and R.sup.6 may represent the necessary atoms to complete an alicyclic or aromatic ring (preferably of 5, 6 or 7 ring atoms, preferably selected from C, S, N and O, preferably of up to 20 carbon atoms on the group), R.sup.3 and R.sup.2 and/or R.sup.1 and R.sup.6 may represent the necessary atoms to complete a non-aromatic heterocyclic ring (preferably comprised of C, S, N and O ring atoms, preferably with 5, 6 or 7 ring atoms, preferably with up to 20 carbon atoms in the group), linked substituent containing up to 16 carbon atoms, preferably hydrocarbons such as alkyl and phenyl groups (preferably up to 4 carbons in the former and up to 10 carbons in the latter), group having 1 to 4 carbon atoms, a phenyl group, or any two adjacent substituents R.sup.7, R.sup.8, R.sup.9 and R.sup.10 together may complete an alicyclic or aromatic ring (preferably hydrocarbon aromatic rings, most preferably benzene groups, substituted or not), and ##STR5## in whic

REFERENCES:
patent: 4315983 (1982-02-01), Kawamura et al.

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