US4368247A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Photographic materials and processes comprising oxoindolizine and oxoindolizinium compounds
Assignee: Eastman Kodak Co
•
Filing: 1981-06-29
•
Granted: 1983-01-11
•
Expires: 2001-06-29
Abstract
Abstract Oxoindolizine and oxoindolizinium dyes are useful in photographic materials and processes as image dyes. These dyes are formed in unexposed areas of photographic materials, especially photothermographic materials, by the reaction of a photosensitive cyclopropenone with a pyridine compound. Oxoindolizine and oxoindolizinium dyes are alternatively formed by (1) reaction of a photosensitive cyclopropenone with a pyridine compound and (2) reaction of the resulting product with a color forming coupler. The photographic material is imagewise exposed and then heated to a processing temperature to form a dye image. Alternatively, the oxoindolizine and oxoindolizinium dyes are produced by imbibing at least one of the reactants into the photographic material comprising a photosensitive cyclopropenone.
Inventors
- 👤 George L. Fletcher, Jr.
- 👤 Steven L. Bender
- 👤 Donald H. Wadsworth
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 06:11
CPC Classifications
C; C07; C07D; C07D471/00; C07D471/02; C07D471/04; G; G03; G03C; G03C1/00; G03C1/72; G03C1/73
Claims Analysis
Total Claims: 38
Claim 1
Independent Claim
38 words
In a photographic element comprising a support having thereon a photosensitive cyclopropenone in binder, the improvement comprising: in reactive association with said cyclopropenone, a pyridine compound that reacts with said cyclopropenone to form an oxoindolizine or oxoindolizinium dye.
Claim 2
Dependent Claim
38 words
In a photographic element comprising a support having thereon a photosensitive cyclopropenone in binder, the improvement comprising: in reactive association with said cyclopropenone, a pyridine compound that reacts with said cyclopropenone to form an oxoindolizine or oxoindolizinium dye.
Claim 3
Dependent Claim
59 words
In a photographic element comprising a support having thereon a photosensitive cyclopropenone in binder, the improvement comprising: in reactive association with said cyclopropenone, (i) a pyridine compound that reacts with said cyclopropenone to form an oxoindolizine or oxoindolizinium compound, and (ii) a color-forming compound that reacts with said oxoindolizine or oxoindolizinium compound to form an oxoindolizine or oxoindolizinium dye.
Claim 4
Dependent Claim
59 words
In a photographic element comprising a support having thereon a photosensitive cyclopropenone in binder, the improvement comprising: in reactive association with said cyclopropenone, (i) a pyridine compound that reacts with said cyclopropenone to form an oxoindolizine or oxoindolizinium compound, and (ii) a color-forming compound that reacts with said oxoindolizine or oxoindolizinium compound to form an oxoindolizine or oxoindolizinium dye.
Claim 5
Dependent Claim
90 words
A photographic element as in claim 1 or 2 wherein said pyridine compound is represented by the formula: ##STR35## wherein: R 1 is hydrogen, alkyl containing 1 to 18 carbon atoms, acyl containing 2 to 18 carbon atoms, carboalkoxy containing 2 to 18 carbon atoms, aminocarbonyl, and acyloxy containing 2 to 18 carbon atoms; R 2 is hydrogen, alkyl containing 1 to 18 carbon atoms, acyl containing 2 to 18 carbon atoms, benzyl or pyridyl; and R 3 is hydrogen, chlorine, bromine or alkyl containing 1 to 18 carbon atoms.
Claim 6
Dependent Claim
17 words
A photographic element as in claim 1 or 2 wherein said pyridine compound consists essentially of pyridine.
Claim 7
Dependent Claim
17 words
A photographic element as in claim 1 or 2 wherein said pyridine compound consists essentially of 4-picoline.
Claim 8
Dependent Claim
46 words
A photographic element as in claim 1 or 2 wherein said photosensitive cyclopropenone consists essentially of a compound represented by the formula: ##STR36## wherein R 4 and R 5 are individually alkyl containing 1 to 20 carbon atoms or aryl containing 6 to 20 carbon atoms.
Claim 9
Dependent Claim
17 words
A photographic element as in claim 1 or 2 wherein said photosensitive cyclopropenone consists essentially of 1-phenyl-2-(paramethoxyphenyl)cyclopropenone.
Claim 10
Dependent Claim
28 words
A photographic element as in claim 2 wherein said color-forming compound is selected from (i) phenolic, (ii) active methylene and (iii) aniline color forming couplers and combinations thereof.
Claim 11
Dependent Claim
14 words
A photographic element as in claim 1 or 2 which is a photothermographic element.
Claim 12
Dependent Claim
17 words
A photographic element comprising a support having thereon, in reactive association, phenylanisyl cyclopropenone and 1-methyl-4-(4-pyridyl)-pyridinium-p-toluenesulfonate in binder.
Claim 13
Dependent Claim
17 words
A photographic element comprising a support having thereon, in reactive association, phenylanisyl cyclopropenone and 1-methyl-4-(4-pyridyl)-pyridinium-p-toluenesulfonate in binder.
Claim 14
Dependent Claim
17 words
A photographic element comprising a support having thereon, in reactive association, phenylanisyl cyclopropenone and 4-azastyryl-1-methyl-pyridinium-p-toluenesulfonate in binder.
Claim 15
Dependent Claim
17 words
A photographic element comprising a support having thereon, in reactive association, phenylanisyl cyclopropenone and 4-azastyryl-1-methyl-pyridinium-p-toluenesulfonate in binder.
Claim 16
Dependent Claim
60 words
A photographic composition comprising (i) a photosensitive cyclopropenone, (ii) a pyridine compound that reacts with cyclopropenone to form an oxoindolizine or oxoindolizinium compound and (iii) a color-forming compound that reacts with said oxoindolizine or oxoindolizinium compound to form a dye wherein the color-forming compound is selected from (i) phenolic (ii) active methylene and (iii) aniline color-forming couplers and combinations thereof.
Claim 17
Dependent Claim
60 words
A photographic composition comprising (i) a photosensitive cyclopropenone, (ii) a pyridine compound that reacts with cyclopropenone to form an oxoindolizine or oxoindolizinium compound and (iii) a color-forming compound that reacts with said oxoindolizine or oxoindolizinium compound to form a dye wherein the color-forming compound is selected from (i) phenolic (ii) active methylene and (iii) aniline color-forming couplers and combinations thereof.
Claim 18
Dependent Claim
88 words
A photographic composition as in claim 12 wherein said pyridine compound is represented by the formula: ##STR37## wherein: R 1 is hydrogen, alkyl containing 1 to 18 carbon atoms, acyl containing 2 to 18 carbon atoms, carboalkoxy containing 2 to 18 carbon atoms, aminocarbonyl, and acyloxy containing 2 to 18 carbon atoms; R 2 is hydrogen, alkyl containing 1 to 18 carbon atoms, acyl containing 2 to 18 carbon atoms, benzyl or pyridyl; and R 3 is hydrogen, chlorine, bromine or alkyl containing 1 to 18 carbon atoms.
Claim 19
Dependent Claim
15 words
A photographic composition as in claim 12 wherein said pyridine compound consists essentially of pyridine.
Claim 20
Dependent Claim
15 words
A photographic composition as in claim 12 wherein said pyridine compound consists essentially of 4-picoline.
Claim 21
Dependent Claim
44 words
A photographic composition as in claim 12 wherein said photosensitive cyclopropenone consists essentially of a compound represented by the formula: ##STR38## wherein R 4 and R 5 are individually alkyl containing 1 to 20 carbon atoms or aryl containing 6 to 20 carbon atoms.
Claim 22
Dependent Claim
12 words
A photographic composition as in claim 12 which is a photothermographic composition.
Claim 23
Dependent Claim
16 words
A photographic composition as in claim 12 wherein said photosensitive cyclopropenone consists essentially of phenylanisyl cyclopropenone.
Claim 24
Dependent Claim
14 words
A photographic composition as in claim 12 wherein said photosensitive cyclopropenone consists of 1-ortho-methoxyphenyl-2-(para-methoxyphenyl)cyclopropenone.
Claim 25
Dependent Claim
39 words
A method of producing a dye image in an exposed photographic element as described in claim 1 comprising heating said element to a temperature within the range of 80° C. to 150° C. until a dye image is formed.
Claim 26
Dependent Claim
39 words
A method of producing a dye image in an exposed photographic element as described in claim 2 comprising heating said element to a temperature within the range of 80° C. to 150° C. until a dye image is formed.
Claim 27
Dependent Claim
39 words
A method of producing a dye image in an exposed photographic element as described in claim 10 comprising heating said element to a temperature within the range of 80° C. to 150° C. until the dye image is formed.
Claim 28
Dependent Claim
39 words
A method of producing a dye image in an exposed photographic element as described in claim 11 comprising heating said element to a temperature within the range of 80° C. to 150° C. until the dye image is formed.
Claim 29
Dependent Claim
23 words
In an exposed and processed photographic element comprising a dye image, the improvement wherein: said dye image comprises an oxoindolizine or oxoindolizinium dye.
Claim 30
Dependent Claim
23 words
In an exposed and processed photographic element comprising a dye image, the improvement wherein: said dye image comprises an oxoindolizine or oxoindolizinium dye.
Claim 31
Dependent Claim
36 words
An exposed and processed photographic element as in claim 24 wherein said oxoindolizine or oxoindolizinium dye image comprises a dye selected from the group consisting of methyleneoxoindolizine, (4-oxoarylene)oxoindolizine, bis-oxoindolizine, 1,2-bis(oxoindolizinyl)ethylene, (2- and 4-aminoarylene)oxoindolizine and pyridiniumoxoindolizine dyes.
Claim 32
Dependent Claim
113 words
An exposed and processed photographic element as in claim 24 wherein said dye image comprises an oxoindolizine dye represented by the formula: ##STR39## wherein R 6 and R 7 are individually selected from alkyl containing 1 to 20 carbon atoms and aryl containing 6 to 20 carbon atoms; R 8 is a divalent group which with the indolizinone nucleus completes an organic chromophore; R 9 is alkyl containing 1 to 18 carbon atoms, acyl containing 2 to 18 carbon atoms, carboalkoxy containing 1 to 18 carbon atoms, aminocarbonyl, acyloxy containing 2 to 18 carbon atoms, bromine or chlorine; and R 10 is hydrogen, chlorine, bromine or alkyl containing 1 to 18 carbon atoms.
Claim 33
Dependent Claim
118 words
An exposed and processed photographic element as in claim 24 wherein said dye image comprises an oxoindolizinium dye represented by the formula: ##STR40## wherein X is an anion; R 11 and R 12 are individually selected from alkyl containing 1 to 20 carbon atoms and aryl containing 6 to 20 carbon atoms; R 13 is hydrogen, alkyl containing 1 to 18 carbon atoms, acyl containing 2 to 18 carbon atoms, carboalkoxy containing 1 to 18 carbon atoms, aminocarbonyl, acyloxy containing 2 to 18 carbon atoms, bromine or chlorine; R 14 is hydrogen, chlorine, bromine or alkyl containing 1 to 18 carbon atoms; and R 15 is a monovalent group which with the indolizinium nucleus completes an organic chromophore.
Claim 34
Dependent Claim
23 words
An exposed and processed photographic element as in claim 24 wherein said dye image comprises an oxoindolizine dye represented by the formula: ##STR41##
Claim 35
Dependent Claim
7 words
A photographic composition comprising 1-phenyl-2-(p-methoxyphenyl)cyclopropenone and 1-methyl-4-(4-pyridyl)pyridinium-p-toluenesulfonate.
Claim 36
Dependent Claim
7 words
A photographic composition comprising 1-phenyl-2-(p-methoxyphenyl)cyclopropenone and 1-methyl-4-(4-pyridyl)pyridinium-p-toluenesulfonate.
Claim 37
Dependent Claim
8 words
A photographic composition comprising phenylanisyl cyclopropenone and 4-azastyryl-1-methylpyridinium-p-toluenesulfonate.
Claim 38
Dependent Claim
8 words
A photographic composition comprising phenylanisyl cyclopropenone and 4-azastyryl-1-methylpyridinium-p-toluenesulfonate.
References Cited (Backward Citations)
US4128422A
Cited
US4106938A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1986-01-10 | 1986-07-12 | 1987-01-11 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-01-10 | 1990-07-12 | 1991-01-11 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-01-10 | 1994-07-12 | 1995-01-11 | $7700.00 | Window Closed / Lapsed |