Patent GB-1112034-A (GB)
Title: Merocyanine dyes,photographic silver halide emulsions containing them and multilayer photographic elements
IPC: C09B23/04
Filed: 1965-05-03
Abstract: The invention comprises merocyanine dyes of the formulae <FORM:1112034/C4-C5/1> <FORM:1112034/C4-C5/2> wherein R is a substituted or unsubstituted alkyl or aryl group, Z completes a 5- or 6-membered heterocyclic nucleus, L is a methine group and one L may be substituted, j is 0 or 1, n is 0, 1, 2, or 3, Q is a <FORM:1112034/C4-C5/3> or <FORM:1112034/C4-C5/4> group, R1 is hydrogen, alkyl, aryl which may substituted, amino or substituted amino, carbonamido, sulphonamido, sulphamyl or carbamyl, W is oxygen or sulphur, at least one of Y and Y1 is a -(CH2)q-N(R2)R3, <FORM:1112034/C4-C5/5> or <FORM:1112034/C4-C5/6> group and, where only one of Y and Y1 is such a group, the other is hydrogen, alkyl or aryl, q is 2, 3 or 4, R2, R3 and R4 are each alkyl, R5, R6 and R7 are each hydrogen, alkyl or aryl, m is 0 or 1 and p is 0, 1 or 2.  The dyes of Formula I above are made by condensing a compound of the formula <FORM:1112034/C4-C5/7> either with a compound of the formula <FORM:1112034/C4-C5/8> to give dyes of Formula I where n is 0, or with a compound of the formula <FORM:1112034/C4-C5/9> to give dyes of Formula I where n is 1 to 3, X being an acid anion, R8 being alkyl or aryl either of which may be substituted, J being -N(R9) R10, -SR11 or halogen, R9 being hydrogen, alkyl or carboxylic acyl and R10 being aryl or R9 and R10 together forming a heterocyclic ring, and R11 being alkyl.  The dyes of Formula II are made by condensing a compound of the formula <FORM:1112034/C4-C5/100> with a compound of the formula <FORM:1112034/C4-C5/111> R12 being hydrogen or acetyl. The dyes are sensitizing dyes for silver halide emulsions (see Division G2).ALSO:In preparations, (1), 3 - (2 - diethylaminoethyl) - rhodanine, (2), 3 - (2 - morpholinoethyl) rhodanine, (7), 3 - (3 - dimethylaminopropyl) rhodanine, (9) 3 - [3 - (4 - methyl - 1 - piperazinyl)propyl] - rhodanine and 3 - (3 - diethylaminopropyl)rhodanine are made by reacting bis-(carboxymethyl) - trithiocarbonate with, respectively, N : N-diethyl-ethylenediamine, N - (2 - aminoethyl) - morpholine, N,N-dimethyl - 1,3 - propanediamine, 1 - (3 - aminopropyl) - 4 - methylpiperazine and N,N - diethyl - 1,3 - propanediamine and acidifying with HCl to obtain probably an impure hydrochloride; in (1) and (2) this is eluted through alumina to obtain the free bases and in (7), (9) and (10) it is reacted with sodium perchlorate to form the hydroperchlorate.  In further preparations, (3), 3-(2-diethylaminoethyl) - 2 - thio - 2,4 - oxazolidenedione and, (4), 3 - (3 - dimethylaminopropyl) - 2 - thio - 2,4 - oxazolidenedione are made by reacting carbamoylmethylthiothiocarbonyl glycolic acid with N : N-diethylethylene diamine and N : N-dimethylpropylene diamine respectively: ethylisocyanate is reacted with N : N - diethyl - ethylene diamine and N - (2 - aminoethyl) morpholine respectively to form, (5), 1 - (2 - diethylaminoethyl) - 3 - ethylurea and, (6), 1 - ethyl - 3 - (2 - morpholinoethyl) urea, which products are then condensed with malonic acid or diethyl malonate to give, (5), 1-(2-diethylaminoethyl) - 3 - ethylbarbituric acid and, (6), 1 - ethyl - 3 - (2 - morpholinoethyl) - bar - bituric acid; (8), potassium N - [(3 - dimethylamino)propyl] thiocarbamyl glycolate is made by reacting carbamoylmethylthiothiocarbonyl glycolic acid with N : N-dimethyl-1,3-propylene diamine.