Photographic materials comprising azo sensitizing dyes

Claim 2

In a photothermographic composition comprising: a. an oxidation-reduction image-forming combination comprising: i. a silver salt oxidizing agent with ii. a reducing agent; and b. a photosensitive component consisting essentially of photosensitive silver halide spectrally sensitized with c. at least one spectral sensitizing dye, the improvement wherein said dye comprises at least one azo spectral sensitizing dye represented by the formula: A--N═N--B wherein A comprises at least one 5 to 12 membered heterocyclic ring having a -NH- moiety as part of the ring which enables the dye to form a substantially water-insoluble silver salt, which heterocyclic ring is linked directly or through a second diazo group; and B is either a 6 to 14 membered aryl or a 5 to 12 membered heterocyclic ring.

Claim 3

The photothermographic composition of claim 1 wherein the spectral sensitizing dye is present in a concentration of from about 10 to about 2000 mg per mole of photographic silver halide.

Claim 4

The photothermographic composition of claim 1 wherein the azo spectral sensitizing dye is represented by the formula: R--N═N--R.sup.1).sub.m (L).sub.n R.sup.2 wherein m is 0 or 1; n is 0 when m is 0, and is 0 or 1 when m is 1; R is aryl having 6 to 14 carbon atoms or R 2 ; R 1 is arylene having 6 to 14 carbon atoms; R 2 is selected from the group consisting of benzotriazole, benzimidazole, indazole, triazole, hydroxytetraazaindene, tetrazole, and pyrazolotriazole heterocyclic moieties and a 6 to 14 membered aryl having one of these moieties as a substituent; and L is a linking group selected from the group consisting of --CONR 3 --, --NR 3 CO--, --SO 2 NR 3 --, --NR 3 CONR 3 --, --NR 3 SO 2 --, --CONR 3 CH 2 -- and --CONR 3 R 1 -- wherein R 3 is hydrogen, alkyl having 1 to 10 carbon atoms or aryl having 6 to 14 carbon atoms; said dye containing an acidic nitrogen in said heterocyclic moieties.

Claim 5

In a photothermographic composition comprising: a. an oxidation-reduction image-forming combination comprising: i. a fatty acid silver salt oxidizing agent with ii. a reducing agent; an b. a photosensitive component consisting essentially of photosensitive silver halide spectrally sensitized with c. at least one spectral sensitizing dye, the improvement wherein said dye comprises at least one azo spectral sensitizing dye represented by the formula: R--N═N--R.sup.1).sub.m (L).sub.n R.sup.2 wherein m is 0 or 1; n is 0 when m is 0, and is 0 or 1 when m is 1; R is aryl having 6 to 14 carbon atoms; R 2 is selected from the group consisting of benzotriazole, benzimidazole, indazole, triazole, hydroxytetraazaindene, tetrazole, and pyrazolotriazole heterocyclic moieties, and a 6 to 14 membered aryl having one of the moieties as a substituent; and L is a linking group selected from the group consisting of --CONR 3 --, --NR 3 CO--, --SO 2 NR 3 --, --NR 3 CONR 3 --, --NR 3 SO 2 --, --CONR 3 CH 2 -- and --CONR 3 R 1 -- wherein R 3 is hydrogen, alkyl having 1 to 10 carbon atoms or aryl having 6 to 14 carbon atoms; said dye containing an acidic nitrogen in said heterocyclic moiety.

Claim 6

In a photothermographic composition comprising: a. an oxidation-reduction image-forming combination comprising: i. a fatty acid silver salt oxidizing agent with ii. a reducing agent; an b. a photosensitive component consisting essentially of photosensitive silver halide spectrally sensitized with c. at least one spectral sensitizing dye, the improvement wherein said dye comprises at least one azo spectral sensitizing dye represented by the formula: R--N═N--R.sup.1).sub.m (L).sub.n R.sup.2 wherein m is 0 or 1; n is 0 when m is 0, and is 0 or 1 when m is 1; R is aryl having 6 to 14 carbon atoms; R 2 is selected from the group consisting of benzotriazole, benzimidazole, indazole, triazole, hydroxytetraazaindene, tetrazole, and pyrazolotriazole heterocyclic moieties, and a 6 to 14 membered aryl having one of the moieties as a substituent; and L is a linking group selected from the group consisting of --CONR 3 --, --NR 3 CO--, --SO 2 NR 3 --, --NR 3 CONR 3 --, --NR 3 SO 2 --, --CONR 3 CH 2 -- and --CONR 3 R 1 -- wherein R 3 is hydrogen, alkyl having 1 to 10 carbon atoms or aryl having 6 to 14 carbon atoms; said dye containing an acidic nitrogen in said heterocyclic moiety.

Claim 7

The photothermographic composition of claim 4 wherein the spectral sensitizing dye consists essentially of 2-benzotriazol-5-ylazo-4-methoxynaphth-1-ol.

Claim 8

The photothermographic composition of claim 4 wherein the spectral sensitizing dye is present in a concentration of from about 10 to about 2000 mg per mole of photographic silver halide.

Claim 9

The photothermographic composition of claim 4 wherein the reducing agent is a sulfonamidophenol.

Claim 10

The photothermographic composition of claim 4 wherein the silver halide is silver bromide.

Claim 11

A photothermographic composition comprising: a. an oxidation-reduction image-forming combination comprising: i. a silver salt of a long-chain fatty acid with ii. a sulfonamidophenol reducing agent; and b. a photosensitive component consisting essentially of photosensitive silver bromide spectrally sensitized with c. a spectral sensitizing dye consisting essentially of 2-benzotriazol-5-ylazo-4-methoxynaphth-1-ol.

Claim 12

A photothermographic composition comprising: a. an oxidation-reduction image-forming combination comprising: i. a silver salt of a long-chain fatty acid with ii. a sulfonamidophenol reducing agent; and b. a photosensitive component consisting essentially of photosensitive silver bromide spectrally sensitized with c. a spectral sensitizing dye consisting essentially of 2-benzotriazol-5-ylazo-4-methoxynaphth-1-ol.

Claim 13

In a photothermographic element comprising a support having thereon in reactive association: a. an oxidation-reduction image-forming combination comprising: i. a silver salt oxidizing agent with ii. a reducing agent; and b. a photosensitive component consisting essentially of photosensitive silver halide spectrally sensitized with c. at least one spectral sensitizing dye, the improvement wherein said dye comprises at least one azo spectral sensitizing dye represented by the formula: A--N═N--B wherein A comprises at least one 5 to 12 membered heterocyclic ring having a --NH-- moiety as part of the ring which enables the dye to form a substantially water-insoluble silver salt, which heterocyclic ring is linked directly or through a second diazo group; and B is either a 6 to 14 membered aryl or a 5 to 12 membered heterocyclic ring.

Claim 14

In a photothermographic element comprising a support having thereon in reactive association: a. an oxidation-reduction image-forming combination comprising: i. a silver salt oxidizing agent with ii. a reducing agent; and b. a photosensitive component consisting essentially of photosensitive silver halide spectrally sensitized with c. at least one spectral sensitizing dye, the improvement wherein said dye comprises at least one azo spectral sensitizing dye represented by the formula: A--N═N--B wherein A comprises at least one 5 to 12 membered heterocyclic ring having a --NH-- moiety as part of the ring which enables the dye to form a substantially water-insoluble silver salt, which heterocyclic ring is linked directly or through a second diazo group; and B is either a 6 to 14 membered aryl or a 5 to 12 membered heterocyclic ring.

Claim 15

The photothermographic element of claim 10 wherein the spectral sensitizing dye is present in a concentration of from about 10 to about 2000 mg per mole of photographic silver halide.

Claim 16

The photothermographic element of claim 10 wherein the azo spectral sensitizing dye is represented by the formula: R--N═N--R.sup.1).sub.m (L).sub.n R.sup.2 wherein m is 0 or 1; n is 0 when m is 0, and is 0 or 1 when m is 1; R is aryl having 6 to 14 carbon atoms or R 2 ; R 1 is arylene having 6 to 14 carbon atoms; R 2 is selected from the group consisting of benzotriazole, benzimidazole, indazole, triazole, hydroxytetraazaindene, tetrazole, and pyrazolotriazole moieties, and a 6 to 14 membered aryl having one of these moieties as a substituent; and L is a linking group selected from the group consisting of --CONR 3 --, --NR 3 CO--, --SO 2 NR 3 --, --NR 3 CONR 3 --, --NR 3 SO 2 --, --CONR 3 CH 2 -- and --CONR 3 R 1 -- wherein R 3 is hydrogen, alkyl having 1 to 10 carbon atoms or aryl having 6 to 14 carbon atoms; said dye containing an acidic nitrogen in said heterocyclic moiety.

Claim 17

A photothermographic element comprising a support having thereon in reactive association: a. an oxidation-reduction image-forming combination comprising: i. a fatty acid silver salt oxidizing agent with ii. a reducing agent; and b. a photosensitive component consisting essentially of photosensitive silver halide spectrally sensitized with c. at least one spectral sensitizing dye, the improvement wherein said dye comprises at least one azo spectral sensitizing dye represented by the formula: R--N═N--R.sup.1).sub.m (L).sub.n R.sup.2 wherein m is 0 or 1; n is 0 when m is 0, and is 0 or 1 when m is 1; R is aryl having 6 to 14 carbon atoms or R 2 ; R 1 is arylene having 6 to 14 carbon atoms; R 2 is selected from the group consisting of benzotriazole, benzimidazole, indazole, triazole, hydroxytetraazaindene, tetrazole, and pyrazolotriazole heterocyclic moieties and a 6 to 14 membered aryl having one of these moieties as a substituent; and L is a linking group selected from the group consisting of --CONR 3 --, --NR 3 CO--, --SO 2 NR 3 --, --NR 3 CONR 3 --, --NR 3 SO 2 --, --CONR 3 CH 2 -- and --CONR 3 R 1 -- wherein R 3 is hydrogen, alkyl having 1 to 10 carbon atoms or aryl having 6 to 14 carbon atoms; said dye containing an acidic nitrogen in said heterocyclic moiety.

Claim 18

A photothermographic element comprising a support having thereon in reactive association: a. an oxidation-reduction image-forming combination comprising: i. a fatty acid silver salt oxidizing agent with ii. a reducing agent; and b. a photosensitive component consisting essentially of photosensitive silver halide spectrally sensitized with c. at least one spectral sensitizing dye, the improvement wherein said dye comprises at least one azo spectral sensitizing dye represented by the formula: R--N═N--R.sup.1).sub.m (L).sub.n R.sup.2 wherein m is 0 or 1; n is 0 when m is 0, and is 0 or 1 when m is 1; R is aryl having 6 to 14 carbon atoms or R 2 ; R 1 is arylene having 6 to 14 carbon atoms; R 2 is selected from the group consisting of benzotriazole, benzimidazole, indazole, triazole, hydroxytetraazaindene, tetrazole, and pyrazolotriazole heterocyclic moieties and a 6 to 14 membered aryl having one of these moieties as a substituent; and L is a linking group selected from the group consisting of --CONR 3 --, --NR 3 CO--, --SO 2 NR 3 --, --NR 3 CONR 3 --, --NR 3 SO 2 --, --CONR 3 CH 2 -- and --CONR 3 R 1 -- wherein R 3 is hydrogen, alkyl having 1 to 10 carbon atoms or aryl having 6 to 14 carbon atoms; said dye containing an acidic nitrogen in said heterocyclic moiety.

Claim 19

The photothermographic element of claim 13 wherein the azo spectral sensitizing dye consists essentially of 2-(benzotriazol-5-ylazo)-4-methoxynaphth-1-ol.

Claim 20

The photothermographic element of claim 13 wherein the azo spectral sensitizing dye is present in a concentration of from about 10 to about 2000 mg per mole of photographic silver halide.

Claim 21

The photothermographic element of claim 13 wherein the reducing agent is a sulfonamidophenol.

Claim 22

The photothermographic element of claim 13 wherein the silver halide is silver bromide.

Claim 23

A photothermographic element comprising a support having thereon in reactive association: a. an oxidation-reduction image-forming combination comprising: i. a silver salt of a long-chain fatty acid with ii. a sulfonamidophenol reducing agent; and b. a photosensitive component consisting essentially of silver bromide spectrally sensitized with c. a spectral sensitizing dye consisting essentially of 2-benzotriazol-5-ylazo-4-methoxynaphth-1-ol.

Claim 24

A photothermographic element comprising a support having thereon in reactive association: a. an oxidation-reduction image-forming combination comprising: i. a silver salt of a long-chain fatty acid with ii. a sulfonamidophenol reducing agent; and b. a photosensitive component consisting essentially of silver bromide spectrally sensitized with c. a spectral sensitizing dye consisting essentially of 2-benzotriazol-5-ylazo-4-methoxynaphth-1-ol.

Claim 25

A photothermographic element comprising a support having thereon in reactive association per square meter of support: a. an oxidation-reduction image-forming combination comprising: i. from 0.02 to 20 millimoles of a silver salt oxidizing agent with ii. from 0.1 to 50.0 millimoles of a reducing agent; and b. from 0.085 to 10 millimoles of a photosensitive component consisting essentially of silver halide spectrally sensitized with c. a spectral sensitizing dye, the improvement wherein said dye comprises from 0.1 to 50 mg of an azo spectral sensitizing dye represented by the formula: A--N═N--B wherein A comprises at least one 5 to 12 membered heterocyclic ring having a --NH-- moiety as part of the ring which enables the dye to form a substantially water-insoluble silver salt, which heterocyclic ring is linked directly or through a second diazo group; and B is either a 6 to 14 membered aryl or a 5 to 12 membered heterocyclic ring.

Claim 26

A photothermographic element comprising a support having thereon in reactive association per square meter of support: a. an oxidation-reduction image-forming combination comprising: i. from 0.02 to 20 millimoles of a silver salt oxidizing agent with ii. from 0.1 to 50.0 millimoles of a reducing agent; and b. from 0.085 to 10 millimoles of a photosensitive component consisting essentially of silver halide spectrally sensitized with c. a spectral sensitizing dye, the improvement wherein said dye comprises from 0.1 to 50 mg of an azo spectral sensitizing dye represented by the formula: A--N═N--B wherein A comprises at least one 5 to 12 membered heterocyclic ring having a --NH-- moiety as part of the ring which enables the dye to form a substantially water-insoluble silver salt, which heterocyclic ring is linked directly or through a second diazo group; and B is either a 6 to 14 membered aryl or a 5 to 12 membered heterocyclic ring.

Claim 27

The photothermographic element of claim 19 wherein the azo spectral sensitizing dye is represented by the formula: R--N═N--R.sup.1).sub.m (L).sub.n R.sup.2 wherein m is 0 or 1; n is 0 when m is 0, and is 0 or 1 when m is 1; R is aryl having 6 to 14 carbon atoms or R 2 ; R 1 is arylene having 6 to 14 carbon atoms; R 2 is selected from the group consisting of benzotriazole, benzimidazole, indazole, triazole, hydroxytetraazaindene, tetrazole, and pyrazolotriazole heterocyclic moieties and a 6 to 14 membered aryl having one of these moieties as a substituent; and L is a linking group selected from the group consisting of --CONR 2 --, --NR 3 CO--, --SO 2 NR 3 --, --NR 3 CONR 3 --, --NR 3 SO 2 --, --CONR 3 CH 2 -- and --CONR 3 R 1 -- wherein R 3 is hydrogen, alkyl having 1 to 10 carbon atoms or aryl having 6 to 14 carbon atoms; said dye containing an acidic nitrogen in said heterocyclic moiety.

Claim 30

The method of claim 21 wherein the azo spectral sensitizing dye is represented by the formula: R--N═N--R.sup.1).sub.m (L).sub.n R.sup.2 wherein m is 0 or 1; n is 0 when m is 0 and is 0 or 1 when m is 1; R is aryl having 6 to 14 carbon atoms or R 2 ; R 1 is arylene having 6 to 14 carbon atoms; R 2 is selected from the group consisting of benzotriazole, benzimidazole, indazole, triazole, hydroxytetraazaindene, tetrazole, and pyrazolotriazole heterocyclic moieties and a 6 l to 14 membered aryl having one of these moieties as a substituent; and L is a linking group selected from the group consisting of --CONR 3 --, --NR 3 CO--, --SO 2 NR 3 --, --NR 3 CONR 3 --, --NR 3 SO 2 --, --CONR 3 CH 2 -- and --CONR 3 R 1 -- wherein R 3 is hydrogen, alkyl having 1 to 10 carbon atoms or aryl having 6 to 14 carbon atoms; said dye containing an acidic nitrogen in said heterocyclic moiety.