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Photographic supports and elements utilizing photobleachable omicron-nitroarylidene dyes

Assignee: Eastman Kodak Co
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Filing: 1975-02-03
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Granted: 1976-10-26
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Expires: 1995-02-03
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Abstract

Abstract Novel o-nitro-substituted arylidene dyes are provided in which the o-nitro aryl group of the arylidene dye is joined through a methine chain linkage to a basic heterocyclic radical containing an electron donating atom. These dyes are photobleachable. The photobleachable properties are useful to provide light-sensitive elements in which images can be formed in or on a support by exposure to light to which the dye is sensitive and to provide photobleachable halation protection in photographic elements having coated thereon a photographic imaging layer. The o-nitro-substituted arylidene dyes can be used for antihalation purposes in photothermographic elements. The dyes can be incorporated within silver halide emulsions to reduce internal light scattering (i.e., internal halation) or to desensitize the emulsion. The dyes are also useful in filter layers.

Inventors

  • 👤 David M. Sturmer

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-25 12:06
CPC Classifications
C; C09; C09B; C09B23/00; C09B23/02; G; G03; G03C; G03C1/00; G03C1/005; G03C1/06; G03C1/36; G03C1/76; G03C1/825; G03C1/83; G03C1/832

Claims Analysis

Total Claims: 27
Claim 1
Independent Claim 174 words
A process for preparing a photographic image which comprises imagewise exposing to electromagnetic radiation a light-sensitive photographic element comprising an otherwise transparent support containing therein a photobleachable o-nitro-substituted arylidene dye wherein said photobleachable dye has the following formula: ##SPC9## wherein a. k represents 0 or 1; b. m represents 0 or 1; c. each L represents a methine group; d. A represents oxygen, sulfur or N--R 1 ; e. R 1 represents an alkyl group, an aralkyl group, a sulfoalkyl group, a sulfoatoalkyl group, an alkoxy carbonylalkyl group, an alkoxyalkyl group, an acyloxyalkyl group, a dialkylaminoalkylene group, a cycloaminoalkylene group, an alkenyl group or an aryl group; f. Z 1 represents the nonmetallic atoms completing a cyanine dye type heterocyclic nucleus comprising a 5- or 6-membered heterocyclic ring whose skeletal atoms consist of the oxygen, sulfur or nitrogen atom of A, carbon atoms and one other atom chosen from the group consisting of carbon, oxygen, nitrogen, selenium and sulfur atoms; and g. Y represents the atoms necessary to complete a phenyl or naphthyl group.
Claim 2
Dependent Claim 174 words
A process for preparing a photographic image which comprises imagewise exposing to electromagnetic radiation a light-sensitive photographic element comprising an otherwise transparent support containing therein a photobleachable o-nitro-substituted arylidene dye wherein said photobleachable dye has the following formula: ##SPC9## wherein a. k represents 0 or 1; b. m represents 0 or 1; c. each L represents a methine group; d. A represents oxygen, sulfur or N--R 1 ; e. R 1 represents an alkyl group, an aralkyl group, a sulfoalkyl group, a sulfoatoalkyl group, an alkoxy carbonylalkyl group, an alkoxyalkyl group, an acyloxyalkyl group, a dialkylaminoalkylene group, a cycloaminoalkylene group, an alkenyl group or an aryl group; f. Z 1 represents the nonmetallic atoms completing a cyanine dye type heterocyclic nucleus comprising a 5- or 6-membered heterocyclic ring whose skeletal atoms consist of the oxygen, sulfur or nitrogen atom of A, carbon atoms and one other atom chosen from the group consisting of carbon, oxygen, nitrogen, selenium and sulfur atoms; and g. Y represents the atoms necessary to complete a phenyl or naphthyl group.
Claim 3
Dependent Claim 56 words
The process of claim 1 wherein Z 1 represents the nonmetallic atoms completing a thiazole nucleus, an oxazole nucleus, a selenazole nucleus, a thiazoline nucleus, a pyridine nucleus, an imidazole nucleus, a quinoline nucleus, an indolenine nucleus, an imidazo[4,5-b]quinoxaline nucleus, a 3H-pyrrolo[2,3-b]pyridine nucleus, a thiazolo[4,5-b]quinoline nucleus, a 2H-pyran nucleus, a 4H-pyran nucleus or a dithiolane nucleus.
Claim 4
Dependent Claim 37 words
A process for preapring a photographic image which comprises imagewise exposing a light-sensitive photographic element comprising on otherwise transparent support containing therein the dye 6-chloro-2-(2,4-dinitrobenzylidene)-1,3-diethyl-2,3-dihydro-1H-imidazo-[4,5-b]quinoxaline, said exposure being to electromagnetic radiation to which said dye is sensitive.
Claim 5
Dependent Claim 37 words
A process for preapring a photographic image which comprises imagewise exposing a light-sensitive photographic element comprising on otherwise transparent support containing therein the dye 6-chloro-2-(2,4-dinitrobenzylidene)-1,3-diethyl-2,3-dihydro-1H-imidazo-[4,5-b]quinoxaline, said exposure being to electromagnetic radiation to which said dye is sensitive.
Claim 6
Dependent Claim 42 words
A process for preparing a photographic image which comprises imagewise exposing to electromagnetic radiation a light-sensitive photographic element comprising an otherwise transparent support containing therein a dye selected from: a. 2-(2,4-dinitrobenzylidene)-1,3-diethyl-2,3-dihydro-1H-imidazo[4,5-b]quinoxaline; b. 2-(2,4-dinitrobenzylidene)-3-ethyl-2,3-dihydrothiazolo[4,5-b]quinoline; c. 2-(2,4-dinitrobenzylidene)-3-ethyl-6-nitrobenzothiazoline; d. 2-(2,4-dinitrobenzylidene)-1,3,3-trimethylindolenine; e. 4-(2,4-dinitrobenzylidene)-1-ethylquinoline; and f. 4-(2,4-dinitrobenzylidene)-2,6-diphenyl-4H-pyran.
Claim 7
Dependent Claim 42 words
A process for preparing a photographic image which comprises imagewise exposing to electromagnetic radiation a light-sensitive photographic element comprising an otherwise transparent support containing therein a dye selected from: a. 2-(2,4-dinitrobenzylidene)-1,3-diethyl-2,3-dihydro-1H-imidazo[4,5-b]quinoxaline; b. 2-(2,4-dinitrobenzylidene)-3-ethyl-2,3-dihydrothiazolo[4,5-b]quinoline; c. 2-(2,4-dinitrobenzylidene)-3-ethyl-6-nitrobenzothiazoline; d. 2-(2,4-dinitrobenzylidene)-1,3,3-trimethylindolenine; e. 4-(2,4-dinitrobenzylidene)-1-ethylquinoline; and f. 4-(2,4-dinitrobenzylidene)-2,6-diphenyl-4H-pyran.
Claim 8
Dependent Claim 24 words
A process of preparing a photographic image according to claim 1 in which a photobleachable image is formed by the dye upon imagewise exposure.
Claim 9
Dependent Claim 33 words
A process of preparing a photographic image according to claim 1 in which the dye is present in an amount sufficient to impart to the support an optical density of at least 0.2.
Claim 10
Dependent Claim 23 words
A process of preparing a photographic image according to claim 6 in which the dye is photobleached by exposure subsequent to imagewise exposure.
Claim 11
Dependent Claim 212 words
A process for preparing a photothermographic image employing a photothermographic element comprising an otherwise transparent support and, as a coating on the support, an image-recording layer comprising: a. an oxidation-reduction image-forming combination comprising i. a reducing agent and ii. a heavy metal salt oxidizing agent, b. a catalyst for the oxidation-reduction image-reduction image-forming combination, and c. a binder, the process comprising: A. choosing the support to include in an amount sufficient to impart antihalation protection a photobleachable dye having the following formula: ##SPC10## wherein: a. k represents 0 or 1; b. m represents 0 or 1; c. each L represents a methine group; d. A represents oxygen, sulfur or N--R 1 ; e. R 1 represents an alkyl group, an alkenyl group or an aryl group; f. Z 1 represents the nonmetallic atoms completing a cyanine dye type heterocyclic nucleus comprising a 5- or 6-membered heterocyclic ring whose skeletal atoms consist of the oxygen, sulfur or nitrogen atom of A, carbon atoms and one other atom chosen from the group consisting of carbon, oxygen, nitrogen, selenium and sulfur atoms, and g. Y represents the atoms necessary to complete a phenyl or naphthyl group, B. imagewise exposing to electromagnetic radiation the image-recording layer and C. heating the photothermographic element to form an image.
Claim 12
Dependent Claim 212 words
A process for preparing a photothermographic image employing a photothermographic element comprising an otherwise transparent support and, as a coating on the support, an image-recording layer comprising: a. an oxidation-reduction image-forming combination comprising i. a reducing agent and ii. a heavy metal salt oxidizing agent, b. a catalyst for the oxidation-reduction image-reduction image-forming combination, and c. a binder, the process comprising: A. choosing the support to include in an amount sufficient to impart antihalation protection a photobleachable dye having the following formula: ##SPC10## wherein: a. k represents 0 or 1; b. m represents 0 or 1; c. each L represents a methine group; d. A represents oxygen, sulfur or N--R 1 ; e. R 1 represents an alkyl group, an alkenyl group or an aryl group; f. Z 1 represents the nonmetallic atoms completing a cyanine dye type heterocyclic nucleus comprising a 5- or 6-membered heterocyclic ring whose skeletal atoms consist of the oxygen, sulfur or nitrogen atom of A, carbon atoms and one other atom chosen from the group consisting of carbon, oxygen, nitrogen, selenium and sulfur atoms, and g. Y represents the atoms necessary to complete a phenyl or naphthyl group, B. imagewise exposing to electromagnetic radiation the image-recording layer and C. heating the photothermographic element to form an image.
Claim 13
Dependent Claim 153 words
The process for preparing a photographic image which comprises imagewise exposing to electromagnetic radiation a light-sensitive photographic element comprising a support having coated thereon a transparent polymeric binder containing a photobleachable o-nitro-substituted arylidene dye wherein said photobleachable dye has the following formula: ##SPC11## wherein: a. k represents 0 or 1; b. m represents 0 or 1; c. each L represents a methine group; d. A represents oxygen, sulfur or N--R 1 ; e. R 1 represents an alkyl group, an alkenyl group or an aryl group; f. Z 1 represents the nonmetallic atoms completing a cyanine dye type heterocyclic nucleus comprising a 5- or 6-membered heterocyclic ring whose skeletal atoms consist of the oxygen, sulfur or nitrogen atom of A, carbon atoms and one other atom chosen from the group consisting of carbon, oxygen, nitrogen, selenium and sulfur atoms; and g. Y represents the atoms necessary to complete a phenyl or naphthyl group.
Claim 14
Dependent Claim 153 words
The process for preparing a photographic image which comprises imagewise exposing to electromagnetic radiation a light-sensitive photographic element comprising a support having coated thereon a transparent polymeric binder containing a photobleachable o-nitro-substituted arylidene dye wherein said photobleachable dye has the following formula: ##SPC11## wherein: a. k represents 0 or 1; b. m represents 0 or 1; c. each L represents a methine group; d. A represents oxygen, sulfur or N--R 1 ; e. R 1 represents an alkyl group, an alkenyl group or an aryl group; f. Z 1 represents the nonmetallic atoms completing a cyanine dye type heterocyclic nucleus comprising a 5- or 6-membered heterocyclic ring whose skeletal atoms consist of the oxygen, sulfur or nitrogen atom of A, carbon atoms and one other atom chosen from the group consisting of carbon, oxygen, nitrogen, selenium and sulfur atoms; and g. Y represents the atoms necessary to complete a phenyl or naphthyl group.
Claim 15
Dependent Claim 53 words
The process of claim 9 wherein Z 1 represents the nonmetallic atoms completing a thiazole nucleus, an oxazole nucleus, a selenazole nucleus, a thiazoline nucleus, a pyridine nucleus, an imidazole nucleus, a quinoline nucleus, an indolenine nucleus, an imidazo[4,5-b]quinoxaline nucleus, a 3H-pyrrolo[2,3-b]pyridine nucleus, a thiazolo[4,5-b]quinoline nucleus, a 2H-pyran nucleus, or a 4H-pyran nucleus.
Claim 16
Dependent Claim 41 words
A process for preparing a photographic image which comprises imagewise exposing a light-sensitive photographic element comprising a support having coated thereon a transparent polymeric binder containing the dye 6-chloro-2-(2,4-dinitrobenzylidene)-1,3-diethyl-2,3-dihydro-1H-imidazo[4,5-b]quinoxaline, said exposure being to electromagnetic radiation to which said dye is sensitive.
Claim 17
Dependent Claim 41 words
A process for preparing a photographic image which comprises imagewise exposing a light-sensitive photographic element comprising a support having coated thereon a transparent polymeric binder containing the dye 6-chloro-2-(2,4-dinitrobenzylidene)-1,3-diethyl-2,3-dihydro-1H-imidazo[4,5-b]quinoxaline, said exposure being to electromagnetic radiation to which said dye is sensitive.
Claim 18
Dependent Claim 46 words
A process for preparing a photographic image which comprises imagewise exposing to electromagnetic radiation a light-sensitive photographic element comprising a support having coated thereon a transparent polymeric binder containing a dye selected from: a. 2-(2,4-dinitrobenzylidene)-1,3-diethyl-2,3-dihydro-1H-imidazo[4,5-b]quinoxaline; b. 2-(2,4-dinitrobenzylidene)-3-ethyl-2,3-dihydrothiazolo[4,5-b]quinoline; c. 2-(2,4-dinitrobenzylidene)-3-ethyl-6-nitrobenzothiazoline; d. 2-(2,4-dinitrobenzylidene)-1,3,3-trimethylindolenine; e. 4-(2,4-dinitrobenzylidene)-1-ethylquinoline; and f. 4-(2,4-dinitrobenzylidene-2,6-diphenyl-4H-pyran.
Claim 19
Dependent Claim 46 words
A process for preparing a photographic image which comprises imagewise exposing to electromagnetic radiation a light-sensitive photographic element comprising a support having coated thereon a transparent polymeric binder containing a dye selected from: a. 2-(2,4-dinitrobenzylidene)-1,3-diethyl-2,3-dihydro-1H-imidazo[4,5-b]quinoxaline; b. 2-(2,4-dinitrobenzylidene)-3-ethyl-2,3-dihydrothiazolo[4,5-b]quinoline; c. 2-(2,4-dinitrobenzylidene)-3-ethyl-6-nitrobenzothiazoline; d. 2-(2,4-dinitrobenzylidene)-1,3,3-trimethylindolenine; e. 4-(2,4-dinitrobenzylidene)-1-ethylquinoline; and f. 4-(2,4-dinitrobenzylidene-2,6-diphenyl-4H-pyran.
Claim 20
Dependent Claim 24 words
A process of preparing a photographic image according to claim 9 in which a photobleachable image is formed by the dye upon imagewise exposure.
Claim 21
Dependent Claim 34 words
A process of preparing a photographic image according to claim 9 in which the dye is present in an amount sufficient to impart an optical density of at least 0.2 to the binder coating.
Claim 22
Dependent Claim 23 words
A process of preparing a photographic image according to calim 14 in which the dye is photobleached by exposure subsequent to imagewise exposure.
Claim 23
Dependent Claim 23 words
A process of preparing a photographic image according to calim 14 in which the dye is photobleached by exposure subsequent to imagewise exposure.
Claim 24
Dependent Claim 29 words
The process according to claim 9 wherein the photobleachable dye is present in an amount sufficient to impart an optical density of at least 0.5 to the binder coating.
Claim 25
Dependent Claim 54 words
A process according to claim 16 in which a photothermographic layer forms a separate coating overlying the binder coating and is comprised of a. an oxidation-reduction image-forming combination comprising i. a reducing agent and ii. a heavy metal salt oxidizing agent, b. a catalyst for the oxidation-reduction image-reduction image-forming combination, and c. a binder.
Claim 26
Dependent Claim 32 words
A process of preparing a photographic image according to claim 6 wherein the dye is present in an amount sufficient to impart to the support an optical density of at least 0.5.
Claim 27
Dependent Claim 20 words
The process according to claim 27 wherein a silver halide emulsion coating forms a separate coating overlying the binder coating.

References Cited (Backward Citations)

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US2669515A Cited
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US3023102A Cited
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USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1979-10-26 1980-04-26 1980-10-26 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1983-10-26 1984-04-26 1984-10-26 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1987-10-26 1988-04-26 1988-10-26 $7700.00 Window Closed / Lapsed

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