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Dichroic Photoconductors

IP.com Disclosure Number: IPCOM000074062D
Original Publication Date: 1971-Mar-01
Included in the Prior Art Database: 2005-Feb-23
Document File: 2 page(s) / 21K

Publishing Venue

IBM

Related People

Cox, RJ: AUTHOR [+2]

Abstract

Conjugated nitro amines having the formula: wherein x is N=N, N=CH, CH=CH-CH=H or CH=CH, y is CH=CH, CH=H, N=CH-CH=CH or NH, and n is 0,1 or 2. have been prepared and found useful as dichroic photoconductors in a process of contact reflex reproduction. They differ from prior art dichroic photoconductors in that they are unsymmetrically substituted, which proves that symmetrical substitution is not necessary for dichroic activity. Compounds having the given formula are: N,N-dimethyl-4-(4-p-nitrostyrylphenylazo)aniline; N,N-dimethyl-4-(p-nitrocinnamilydeneamino)aniline; N,N-dimethyl-4-(4-p-nitrophenyl-2,4-butadienyl)aniline; p-N,N-dimethylaminocinnamylidene-p-nitrophenylhydrazone 4-(p-dimethylaminobenzylideneamino)4'- (p-nitrocinnamylideneamino)biphenylazo) aniline N,N-dimethylaniline is coupled with 4-formylbenzene.

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Dichroic Photoconductors

Conjugated nitro amines having the formula: wherein x is N=N, N=CH, CH=CH-CH=H or CH=CH, y is CH=CH, CH=H, N=CH-CH=CH or NH, and n is 0,1 or 2. have been prepared and found useful as dichroic photoconductors in a process of contact reflex reproduction. They differ from prior art dichroic photoconductors in that they are unsymmetrically substituted, which proves that symmetrical substitution is not necessary for dichroic activity. Compounds having the given formula are: N,N-dimethyl-4-(4-p-nitrostyrylphenylazo)aniline; N,N- dimethyl-4-(p-nitrocinnamilydeneamino)aniline; N,N-dimethyl-4-(4-p-nitrophenyl- 2,4-butadienyl)aniline; p-N,N-dimethylaminocinnamylidene-p- nitrophenylhydrazone 4-(p-dimethylaminobenzylideneamino)4'- (p- nitrocinnamylideneamino)biphenylazo) aniline N,N-dimethylaniline is coupled with 4-formylbenzene. diazoniumchloride to an aldehyde as described in J. Chem. Soc. 1173 (1926). A solution of 0.07g., 0.01 mole, of lithium in 25 ml. of absolute ethanol is added dropwise with stirring to a slurry of 2.9g., 0.079 mole, of the aldehyde and 5.0g., 0.01 mole of p-nitrobenzyltriphenylphosphonium bromide in 75 ml. of absolute ethanol. The reaction is kept under nitrogen during the addition and for a further two hours. Fifty ml. of water is added to the reaction mixture. The resultant precipitate is filtered and washed with 60% aqueous ethanol, dried and recrystallized from dimethylformamide. Analysis of the red solid is as follows:...