Effects of anthrone products

Disclosed is a process for the preparation of anthraquinodimethane derivatives and anthrone derivatives useful as electron transporting molecules which comprises the condensation reaction of anthraquinones with active methylene compounds in the presence of a Lewis acid and a base.A process for the preparation of anthraquinodimethane derivative and anthrone derivatives which consists essentially of the reaction of an anthraquinone with an active methylene compound selected from the group consisting of malononitrile, malonate, dinitromethane, and betadiketone in the presence of an organic solvent, a base, and a Lewis acid, which reaction is affected at a temperature of from about 0° C. to about 30° C.

This invention is generally directed to processes for the preparation of electron transporting compounds, and more specifically the present invention is directed to specific processes for obtaining anthraquinodimethane derivatives and related anthrone derivatives. Therefore, in one embodiment of the present invention there are prepared anthraquinone and anthrone Pharmaceutical Intermediates  derivatives by the reaction of an anthraquinodimethane with active methylene compounds, inclusive of malononitrile, in a suitable organic solvent, which reaction is accomplished in the presence of a base and a Lewis acid. The resulting anthraquinodimethane derivatives and related anthrone derivatives are useful as electron transporting compounds in imaging members containing therein a photogenerating layer. These imaging members are the claimed subject matter of a copending application U.S. Ser. No. 709,867 entitled Photoresponsive Imaging Members With Electron Transporting Layers, the disclosure of this copending application being totally incorporated herein by reference.

There is also disclosed in U.S. Pat. No. 4,474,865 imaging members with electron transporting layers of fluorenylidene derivatives. These electron transporting compounds differ from those of the present invention in that they are based on the fluorenone structure with a 5-member central ring; while the transporting compounds of the present invention are based on anthrone manufacturer and anthraquinone structures which contain a 6-member central ring. In addition, while the fluorenylidene derivatives are relatively planar in structure, the anthrone and anthraquinone derivatives of the present invention are buckled and assume a butterfly-like conformation.

While the above-described photoresponsive imaging members are suitable for their intended purposes there continues to be a need for improved imaging members, particularly layered imaging members, which not only generate acceptable images but which can be repeatedly used in a number of imaging cycles without deterioration thereof from the machine environment or surrounding conditions. Additionally, there continues to be a need for improved layered photoconductive imaging members wherein the materials selected are substantially inert to users of these members. Also, there continues to be a need for positively charged imaging members with electron transporting compounds. Additionally, there continues to be a need for improved photoresponsive imaging members which can be prepared with a minimum number of processing steps, and wherein the layers are sufficiently adhered to one another to allow the continuous use of these members in imaging and printing processes.

Also, there is a need for electron transport compounds which are compatible with common matrix polymers, inclusive of polycarbonates, and polyesters enabling the dispersion of these compounds to be maintained for the useful life of the layered imaging members. Moreover, there continues to be a need for a simple synthetic process for the preparation of anthrone products , and anthraquinodimethane electron transporting compounds.

A further specific object of the present invention is the provision of an improved photoresponsive imaging member containing a photogenerating layer, and in contact therewith an electron transporting layer of anthrone derivatives prepared by the processes illustrated herein.

Another specific object of the present invention is the provision of an improved photoresponsive imaging member containing a photogenerating layer, and in contact therewith an electron transporting layer of anthraquinodimethane derivatives prepared by the processes illustrated herein.

The primary object of the present invention and other related objects are accomplished by the provision of processes for the preparation of anthraquinodimethane derivatives and anthrone supplier derivatives useful as electron transporting molecules which comprises the condensation reaction of anthraquinones with active methylene compounds in the presence of a Lewis acid and a base. The aforementioned electron transporting compounds prepared in accordance with the process of the present invention are useful for incorporation into the layered photoresponsive imaging members are disclosed in the referenced copending application entitled Photoresponsive Imaging Members With Electron Transporting Layers. source:townhall|anthrone