Patent GB-1458471-A (GB)
Title: Compounds having a diffusible dye moiety and photosensitive  silver halide elements containing said compounds
IPC: G03C8/18
Filed: 1974-02-12
Abstract: 1458471 Compounds having a diffusible dye moiety EASTMAN KODAK CO 12 Feb 1974 [12 Feb 1973] 06247/74 Heading C4P [Also in Division G2] Novel compounds having a dye moiety and a carrier moiety have the formulµ and wherein Car is the carrier moiety; X is where each R<SP>2</SP> is individually C 1-8  alkylene or is is optionally substituted C 6-10  phenylene; L is O, CO, CONH, NHCO, SO 2 NH, NHSO 2 , SO 2  or SO; n is zero or 1; p is 1 when n is 1 and is 1 or zero when n is zero and when p is 1 the carbon content of both R<SP>2</SP> groups does not exceed 14; R is H or C 1-6  alkyl optionally substituted by CN, OH or OCH 3 ; J is SO 2  or CO; m and q are each zero or 1; Q is H, OH, NHCOR<SP>3</SP> or R<SP>3</SP> is optionally substituted C 1-6  alkyl, benzyl or optionally substituted C 6-9  phenyl; G is OH, salified OH, O.CO.R<SP>4</SP> or O.CO.OR<SP>4</SP>; R<SP>4</SP> is C 1-18  alkyl or optionally substituted C 6-18  phenyl; D is halogen, CN, NO 2 , CF 3 , C 1-6  alkyl or alkoxy, optionally salified CO 2 H, CO 2 R<SP>4</SP>, SO 2 F, optionally substituted C 6-9  phenylsulphonyloxy, optionally salified SO 3 H, SONR<SP>2</SP>R<SP>6</SP>, CON(R<SP>2</SP>) 2 , optionally substituted C 1-8  alkylsulphonyl, optionally substituted C 6-9  phenylsulphonyl, Car-[X-(NR-J) q ] m - or Car-X-J- provided that the Car-[X-(NR-J) q ] m - substituent on the naphthalene nucleus of (I) is replaced by an M group or the Car-X-J-NR- substituent on the naphthalene nucleus of (II) is replaced by a Q group; R<SP>5</SP> is H or C 1-6  alkyl ; R<SP>6</SP> is H, optionally substituted C 1-6  alkyl, optionally substituted C 6-9  phenyl, C 2-8  alkylcarbonyl, phenylcarbonyl, phenylmethylcarbonyl or B methylphenylcarbonyl, but the total number of C atoms in R<SP>5</SP> and R<SP>6</SP> is at most 14; E is H, halogen, SO 2 NH 2 , NO 2 , CN or CF 3 ; and M is H, optionally salified CO 2 H or SO 3 H, COOR<SP>4</SP>, SO 2 NR<SP>5</SP>R<SP>6</SP>, CON(R<SP>5</SP>) 2 , optionally substituted C 1-8  alkylsulphonyl or optionally substituted C 6-9  phenylsulphonyl; but there is no more than one SO 3 H and no more than one CO 2 H group present. The carrier moiety comprises a ballast group of a molecular size and configuration such that the compound is non- diffusible in the presence of an alkaline aqueous photographic processing composition in a photo sensitive element comprising a support having thereon at least one photosensitive silver halide emulsion layer having associated therewith a compound of the Formula (I) or (II). In representative preparations 2-amino-5-nitrophenylmethylsulphone is diazotized and coupled with 5-hydroxy-2-naphthalenesulphonic acid and the product is converted to the acid chloride and condensed with 4-amino-N-X-1-hydroxy-2- napthamide (X herein is 4-(2,4-di-t.-pentylphenoxy)-butyl) to give a compound of the formula Use of 5-hydroxy-1-naphthenesulphonic acid, 4 - acetamido - 5 - hydroxy - 1 - and 2 - naphthalenesulphonic acids and 4-propionamido-5- hydroxy - 1 - naphthalene - sulphonic acid in place of 5-hydroxy-2-naphthalenesulphonic acid gives a corresponding product. Use of 2-chloro- 4,6 - dinitro - aniline and 4 - nitro - 2 - trifluoromethylaniline in place of 2-amino-5-nitrophenylmethylsulphone gives corresponding products. Other similar products are also described. By a similar condensation method is prepared as are other similar compounds of the invention. Other starting material preparations include Alternatively the final product can be obtained by a diazotization and coupling process as in where Group is 4-hydroxy-3-(CONHX)-naphth- 1-yl. Products wherein G is O acyl may be prepared by acylation of products wherein G is OH.