Patent GB-911501-A (GB)
IPC: C07D213/30
Filed: 1958-11-27
Abstract: 911,501. Photographic silver halide emulsions; developers. KODAK Ltd. Nov. 27, 1958 [Nov. 27, 1957 (3)], No. 38308/58. Class 98 (2). [Also in Group IV (b)] The speed of a photographic silver halide emulsion is increased by incorporating therein or in the developer solution a bis-quaternary ammonium compound in which the two quaternary nitrogen atoms are linked by a chain member of 14 to 32 carbon atoms which chain member has one of the formulae: wherein R and R 1  each represent a hydrocarbon chain composed of -CH 2 - or -CH= groups with no olefinically unsaturated linkages, R<SP>2</SP> is (CH 2 ) m  (m being 1 to 10), R<SP>3</SP> is H or an alkyl group of 1 to 4 carbon atoms, n is 0 or, when R and R<SP>1</SP> are the same, 1, n<SP>1</SP> is 0 or 1, n<SP>11</SP> is 1 to 4, A<SP>1</SP> is an alkylene group of 2 to 10 carbon atoms, A<SP>2</SP> is an alkylene group of 1 to 10 carbon atoms and A is an alkylene group of 2 to 10 carbon atoms, a biphenylene radical, a naphthylene radical, -R<SP>2</SP>SR<SP>2</SP>-, -R<SP>2</SP>OR<SP>2</SP>-, -R<SP>2</SP>-phenylene-R<SP>2</SP>- or -CH 2 CONHR<SP>2</SP>NHCOCH 2 -. The quaternary groups may be pyridine, quinoline, isoquinoline or trimethylamine. When the quaternary nitrogen atom is part of a heterocyclic ring, the groups R or R<SP>1</SP> may consist of or include one or more of the -CH = groups of that ring. In the compounds specified, the chain member is of the formula I wherein R and R<SP>1</SP> are (CH 2 ) 10 ; of formula II wherein R and R<SP>1</SP> are CH 2 , (CH 2 ) 2 , (CH 2 ) 5 , (CH 2 ) 8 , (CH 2 ) 10  or CH 2  CONH(CH 2 ) 6 NHCOCH 2 , and A is (CH 2 ) 2 , (CH 2 ) 4 , (CR 2 ) 6 , (CH 2 ) 10 , (CH 2 ) 2 -S-(CH 2 ) 2  or CH 2 -C 6 H 4 -CH 2 ; of formula III wherein R is (CH 2 ) 2  and R<SP>1</SP> is (CH 2 ) 10 ; of formula IV wherein n is 0, R and R<SP>1</SP> are (CH 2 ) 2 , (CH 2 ) 3  plus part of a pyridine ring, (CH 2 ) 5 , (CH 2 ) 6  or (CH 2 ) 10  and A<SP>1</SP> is (CH 2 ) 6  and wherein n is I, R, R<SP>1</SP> and R<SP>2</SP> are (CH 2 ) 2  and A<SP>1</SP> is (CH 2 ) 6 ; of formula V wherein n<SP>1</SP> is 0, R is (CH 2 ) 2  and R<SP>1</SP> is (CH 2 ) 10  and wherein n<SP>1</SP> is 1, R and R<SP>1</SP> are (CH 2 ) 2  and A<SP>1</SP> is (CH 2 ) 10 ; of formula VI wherein R and R<SP>1</SP> are (CH 2 ) 2  and/or part of a pyridine ring, R<SP>3</SP> is H or CH 3  and A<SP>1</SP> is (CH 2 ) 6  or (CH 2 ) 10 ; of formula VII wherein R and R<SP>1</SP> are (CH 2 ) 10 ; of formula VIII wherein R and R<SP>1</SP> are (CH 2 ) 4 , (CH 2 ) 5 , (CH 2 ) 6  or (CH 2 ) 10  and A<SP>2</SP> is (CH 2 ) 4  or (CH 2 ) 8 ; of formula IX wherein R and R<SP>1</SP> are (CH 2 ) 5 and A<SP>1</SP> is (CH 2 ) 10 ; and of formula X wherein Rand R<SP>11</SP> are (CH 2 ) 5  and n<SP>11</SP> is 4. The quaternary groups are present as perchlorates, p-toluene sulphonates, iodides and tetraphenyl boron salts. The photographic emulsions also may contain polyoxyethylene compounds and 4- hydroxy - 6 - methyl - 1; 3; 3a ; 7 - tetrazaindene as stabilizer. Sulphur and gold sensitizers also may be added and the invention is particularly useful for emulsions containing colour couplers. Specifications 524,154,524,554,524,555,541,589, 557,178, 558,710, 566,314, 874,077 and 874,082 are referred to.