USRE30303E
Expired / Lapsed
US
⏱️ 0.0 years remaining
Novel (UV absorbing compounds and) photographic elements containing UV absorbing compounds
Assignee: Eastman Kodak Co
•
Filing: 1978-04-14
•
Granted: 1980-06-10
•
Expires: 1998-04-14
Abstract
Abstract 1-Amino-4-cyano-1,3-butadiene compounds of the formula ##STR1## wherein n is 1 or 2, when n is 1 R 1 and R 2 can be the same or different and represent hydrogen, alkyl including substituted alkyl, aryl including substituted aryl or cyclic alkyl groups, except that both R 1 and R 2 cannot be hydrogen, or taken together R 1 and R 2 represent the elements necessary to complete a cyclic amino group and when n is 2 at least one of R 1 and R 2 is alkylene or arylene; G represents an electron withdrawing group. The compounds are especially useful in photographic elements as UV absorbers.
Inventors
- 👤 II Wayne W. Weber
- 👤 Donald W. Heseltine
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 10:07
CPC Classifications
C; C07; C07D; C07D295/00; C07D295/04; C07D295/14; C07D295/145; C07C; C07C255/00; G; G03; G03C; G03C1/00; G03C1/76; G03C1/815; G03C1/8155
Claims Analysis
Total Claims: 32
Claim 1
Independent Claim
151 words
In a photographic element comprising a support, at least one radiation sensitive silver halide emulsion layer and an ultraviolet absorbing compound, the improvement comprising the use of a 1-amino-4-cyano-1,3-butadiene ultraviolet absorbing compound..]. .[.2. The element according to claim 1 wherein said 1-amino-4-cyano-1,3-butadiene compound is of the formula: ##STR26## wherein n is 1 or 2, when n is 1, R 1 and R 2 are independently chosen to represent hydrogen, an alkyl group of 1 to 10 carbon atoms, an aryl group of 6 to 20 carbon atoms, or a cyclic alkyl group of 5 or 6 carbon atoms provided that R 1 and R 2 cannot both be hydrogen, or R 1 and R 2 taken together represent the atoms necessary to complete a cyclic amino group and when n is 2 at least one of R 1 and R 2 is alkylene or arylene, and G represents an electron withdrawing
Claim 2
Dependent Claim
139 words
group..]. 3. A photographic element comprising a support having thereon at least one radiation sensitive silver halide emulsion layer and an ultraviolet filter layer comprising a binder and at least one compound having the formula: ##STR27## wherein n is 1 or 2, when n is 1, R 1 and R 2 are independently chosen to represent hydrogen, an alkyl group of 1 to 10 carbon atoms, an aryl group of 6 to 10 carbon atoms, or a cyclic alkyl group of 5 to 6 carbon atoms provided that R 1 and R 2 cannot both be hydrogen, or R 1 and R 2 taken together represent the atoms necessary to complete a cyclic amino group and when n is 2 at least one of R 1 and R 2 is alkylene or arylene, and G represents an electron withdrawing
Claim 3
Dependent Claim
139 words
group..]. 3. A photographic element comprising a support having thereon at least one radiation sensitive silver halide emulsion layer and an ultraviolet filter layer comprising a binder and at least one compound having the formula: ##STR27## wherein n is 1 or 2, when n is 1, R 1 and R 2 are independently chosen to represent hydrogen, an alkyl group of 1 to 10 carbon atoms, an aryl group of 6 to 10 carbon atoms, or a cyclic alkyl group of 5 to 6 carbon atoms provided that R 1 and R 2 cannot both be hydrogen, or R 1 and R 2 taken together represent the atoms necessary to complete a cyclic amino group and when n is 2 at least one of R 1 and R 2 is alkylene or arylene, and G represents an electron withdrawing
Claim 4
Dependent Claim
12 words
group. 4. A photographic element according to claim 3 wherein the binder
Claim 5
Dependent Claim
41 words
is a hydrophillic colloid. 5. A photographic element according to claim 3 wherein the electron withdrawing group is selected from the group consisting of ##STR28## where R represents an alkyl group of 1 to 10 carbon atoms or aryl group of
Claim 6
Dependent Claim
30 words
6 to 10 carbon atoms. 6. A photographic element according to claim 3 wherein G is the group CN and R 1 and R 2 are both alkyl groups of
Claim 7
Dependent Claim
29 words
1 to 10 carbon atoms. 7. A photographic element according to claim 3 wherein G is the group CN, R 1 is hydrogen and R 2 is an alkyl
Claim 8
Dependent Claim
58 words
group of 1 to 10 carbon atoms. 8. A photographic element comprising a support having thereon at least one silver halide emulsion layer and at least one ultraviolet filter layer comprising a binder and at least one compound selected from the group consisting of 3-dibutylaminoallylidenemalononitrile, 3-dihexylaminoallylidenemalononitrile, 3-tert-butylaminoallylidenemalononitrile, 3-diisobutylaminoallylidenemalononitrile, 3-di-sec-butylaminoallylidenemalononitrile, 3-hexahydroazepinoallylidenemalononitrile, 3-N-(n-butyl)-N-cyanomethyl aminoallylidenemalononitrile, 3[N,N-bis-(2,2-diethoxyethyl)amino]allylidenemalononitrile, 3(n-methyl-N-cyanomethyl)aminoallylidenemalononitrile, 1,4-piperazino bis(allylidenemalononitrile), N,N'-diethyl-N,N-di(4,4-dicyenobutadienyl)-1,6-diaminohexane and
Claim 9
Dependent Claim
58 words
group of 1 to 10 carbon atoms. 8. A photographic element comprising a support having thereon at least one silver halide emulsion layer and at least one ultraviolet filter layer comprising a binder and at least one compound selected from the group consisting of 3-dibutylaminoallylidenemalononitrile, 3-dihexylaminoallylidenemalononitrile, 3-tert-butylaminoallylidenemalononitrile, 3-diisobutylaminoallylidenemalononitrile, 3-di-sec-butylaminoallylidenemalononitrile, 3-hexahydroazepinoallylidenemalononitrile, 3-N-(n-butyl)-N-cyanomethyl aminoallylidenemalononitrile, 3[N,N-bis-(2,2-diethoxyethyl)amino]allylidenemalononitrile, 3(n-methyl-N-cyanomethyl)aminoallylidenemalononitrile, 1,4-piperazino bis(allylidenemalononitrile), N,N'-diethyl-N,N-di(4,4-dicyenobutadienyl)-1,6-diaminohexane and
Claim 10
Dependent Claim
46 words
3[N,N-bis(2-cyanoethyl)amino]allylidenemalononitrile. 9. A photographic element comprising a support having thereon at least one silver halide emulsion layer and at least one ultraviolet filter layer comprising a binder and at least one compound selected from the group consisting of 3-morpholinoallylidene methylsulfonylacetonitrile, 3-morpholinoallylidene 4-tert-butylphenylsulfonylacetonitrile, 3-piperazinoallylidene 4-tert-butylphenylsulfonylacetonitrile and 3-N-methylpiperazinoallylidene
Claim 11
Dependent Claim
46 words
3[N,N-bis(2-cyanoethyl)amino]allylidenemalononitrile. 9. A photographic element comprising a support having thereon at least one silver halide emulsion layer and at least one ultraviolet filter layer comprising a binder and at least one compound selected from the group consisting of 3-morpholinoallylidene methylsulfonylacetonitrile, 3-morpholinoallylidene 4-tert-butylphenylsulfonylacetonitrile, 3-piperazinoallylidene 4-tert-butylphenylsulfonylacetonitrile and 3-N-methylpiperazinoallylidene
Claim 12
Dependent Claim
148 words
4-tert-butylphenylsulfonylacetonitrile. 10. A photographic element comprising at least one silver halide emulsion layer coated on a film support, said film support being selected from a solvent cast or melt-formed film support and having incorporated therein at least one ultraviolet filter compound of the formula: ##STR29## wherein n is 1 or 2, when n is 1, R 1 and R 2 are independently chosen to represent hydrogen, an alkyl group of 1 to 10 carbon atoms, an aryl group of 6 to 10 carbon atoms, or a cyclic alkyl group of 5 or 6 carbon atoms provided that R 1 and R 2 cannot both be hydrogen, or R 1 and R 2 taken together represent the atoms necessary to complete a cyclic amino group and when n is 2 at least one of R 1 and R 2 is alkylene or arylene, and G represents an electron withdrawing
Claim 13
Dependent Claim
148 words
4-tert-butylphenylsulfonylacetonitrile. 10. A photographic element comprising at least one silver halide emulsion layer coated on a film support, said film support being selected from a solvent cast or melt-formed film support and having incorporated therein at least one ultraviolet filter compound of the formula: ##STR29## wherein n is 1 or 2, when n is 1, R 1 and R 2 are independently chosen to represent hydrogen, an alkyl group of 1 to 10 carbon atoms, an aryl group of 6 to 10 carbon atoms, or a cyclic alkyl group of 5 or 6 carbon atoms provided that R 1 and R 2 cannot both be hydrogen, or R 1 and R 2 taken together represent the atoms necessary to complete a cyclic amino group and when n is 2 at least one of R 1 and R 2 is alkylene or arylene, and G represents an electron withdrawing
Claim 14
Dependent Claim
38 words
group. 11. A photographic element according to claim 10 wherein the electron withdrawing group is selected from the group consisting of ##STR30## where R represents an alkyl group of 1 to 10 carbon atoms or aryl group of
Claim 15
Dependent Claim
31 words
6 to 10 carbon atoms. 12. A photographic element according to claim 10 wherein G is the group CN and R 1 and R 2 are alkyl groups of 1 to
Claim 16
Dependent Claim
30 words
10 carbon atoms. 13. A photographic element according to claim 10 wherein G is the group CN, R 1 is hydrogen and R 2 is an alkyl group of 1
Claim 17
Dependent Claim
63 words
to 10 carbon atoms. 14. A photographic element comprising at least one silver halide emulsion layer coated on a film support, said film support being selected from a solvent-cast or melt-formed film support and said support having therein at least one ultraviolet filter compound selected from the group consisting of 3-dibutylaminoallylidenemalononitrile, 3-dihexylaminoallylidenemalononitrile, 3-tert-butylaminoallylidenemalononitrile, 3-diisobutylaminoallylidenemalononitrile, 3-di-sec-butylaminoallylidenemalononitrile, 3-hexahydroazepinoallylidenemalononitrile, 3-N(n-butyl)-N-cyanomethylaminoallylidenemalononitrile, 3(N,N-bis-(2,2-diethoxyethyl)amino]allylidenemalononitrile, 3(n-methyl-N-cyanomethyl)aminoallylidenemalononitrile, 1,4-piperazino bis(allylidenemalononitrile), N,N'-diethyl-N,N-di(4,4-dicyanobutadienyl)-1,6-diaminohexane and
Claim 18
Dependent Claim
63 words
to 10 carbon atoms. 14. A photographic element comprising at least one silver halide emulsion layer coated on a film support, said film support being selected from a solvent-cast or melt-formed film support and said support having therein at least one ultraviolet filter compound selected from the group consisting of 3-dibutylaminoallylidenemalononitrile, 3-dihexylaminoallylidenemalononitrile, 3-tert-butylaminoallylidenemalononitrile, 3-diisobutylaminoallylidenemalononitrile, 3-di-sec-butylaminoallylidenemalononitrile, 3-hexahydroazepinoallylidenemalononitrile, 3-N(n-butyl)-N-cyanomethylaminoallylidenemalononitrile, 3(N,N-bis-(2,2-diethoxyethyl)amino]allylidenemalononitrile, 3(n-methyl-N-cyanomethyl)aminoallylidenemalononitrile, 1,4-piperazino bis(allylidenemalononitrile), N,N'-diethyl-N,N-di(4,4-dicyanobutadienyl)-1,6-diaminohexane and
Claim 19
Dependent Claim
54 words
3-[N,N-bis(2-cyanoethyl)amino]allylidenemalononitrile. 15. A photographic element comprising at least one silver halide emulsion layer coated on a film support, said film support being selected from a solvent-cast or melt-formed film support and said support having therein at least one ultraviolet filter compound selected from the group consisting of 3-morpholinoallylidenemethylsulfonylacetonitrile, 3-morpholinoallylidene 4-tert-butylphenylsulfonylacetonitrile, 3-piperazinoallylidene 4-tert-butylphenylsulfonylacetonitrile and 3-N-methylpiperazinoallylidene
Claim 20
Dependent Claim
54 words
3-[N,N-bis(2-cyanoethyl)amino]allylidenemalononitrile. 15. A photographic element comprising at least one silver halide emulsion layer coated on a film support, said film support being selected from a solvent-cast or melt-formed film support and said support having therein at least one ultraviolet filter compound selected from the group consisting of 3-morpholinoallylidenemethylsulfonylacetonitrile, 3-morpholinoallylidene 4-tert-butylphenylsulfonylacetonitrile, 3-piperazinoallylidene 4-tert-butylphenylsulfonylacetonitrile and 3-N-methylpiperazinoallylidene
Claim 21
Dependent Claim
28 words
4-tert-butylphenylsulfonylacetonitrile. 16. A photographic element comprising a support having thereon at least one silver halide emulsion layer and at least one ultraviolet filter layer comprising a binder and
Claim 22
Dependent Claim
28 words
4-tert-butylphenylsulfonylacetonitrile. 16. A photographic element comprising a support having thereon at least one silver halide emulsion layer and at least one ultraviolet filter layer comprising a binder and
Claim 23
Dependent Claim
28 words
3-dibutylaminoallylidenemalononitrile. 17. A photographic element comprising a support having thereon at least one silver halide emulsion layer and at least one ultraviolet filter layer comprising a binder and
Claim 24
Dependent Claim
28 words
3-dibutylaminoallylidenemalononitrile. 17. A photographic element comprising a support having thereon at least one silver halide emulsion layer and at least one ultraviolet filter layer comprising a binder and
Claim 25
Dependent Claim
36 words
3-dihexylaminoallylidenemalononitrile. 18. A photographic element comprising at least one silver halide emulsion layer coated on a film support, said film support being selected from a solvent-cast or melt-formed film support and having therein the ultraviolet filter
Claim 26
Dependent Claim
36 words
3-dihexylaminoallylidenemalononitrile. 18. A photographic element comprising at least one silver halide emulsion layer coated on a film support, said film support being selected from a solvent-cast or melt-formed film support and having therein the ultraviolet filter
Claim 27
Dependent Claim
37 words
compound 3-dibutylaminoallylidenemalononitrile. 19. A photographic element comprising at least one silver halide emulsion layer coated on a film support, said film support being selected from a solvent-cast or melt-formed film support and having therein the ultraviolet filter
Claim 28
Dependent Claim
37 words
compound 3-dibutylaminoallylidenemalononitrile. 19. A photographic element comprising at least one silver halide emulsion layer coated on a film support, said film support being selected from a solvent-cast or melt-formed film support and having therein the ultraviolet filter
Claim 29
Dependent Claim
127 words
compound 3-dihexylaminoallylidenemalononitrile. .Iadd.20. A photographic element comprising a support having thereon at least one radiation sensitive silver halide emulsion layer and an ultraviolet filter layer comprising a binder and at least one compound having the formula: ##STR31## wherein n is 1 or 2, when n is 1, R 1 and R 2 are independently chosen to represent hydrogen, an alkyl group of 1 to 10 carbon atoms, or a cyclic alkyl group of 5 or 6 carbon atoms provided that R 1 and R 2 cannot both be hydrogen, or R 1 and R 2 taken together represent the atoms necessary to complete a cyclic amino group and when n is 2 at least one of R 1 and R 2 is alkylene and G represents an
Claim 30
Dependent Claim
127 words
compound 3-dihexylaminoallylidenemalononitrile. .Iadd.20. A photographic element comprising a support having thereon at least one radiation sensitive silver halide emulsion layer and an ultraviolet filter layer comprising a binder and at least one compound having the formula: ##STR31## wherein n is 1 or 2, when n is 1, R 1 and R 2 are independently chosen to represent hydrogen, an alkyl group of 1 to 10 carbon atoms, or a cyclic alkyl group of 5 or 6 carbon atoms provided that R 1 and R 2 cannot both be hydrogen, or R 1 and R 2 taken together represent the atoms necessary to complete a cyclic amino group and when n is 2 at least one of R 1 and R 2 is alkylene and G represents an
Claim 31
Dependent Claim
142 words
electron withdrawing group. .Iaddend. .Iadd.21. A photographic element comprising at least one silver halide emulsion layer coated on a film support, said film support being selected from a solvent cast or melt-formed film support and having incorporated therein at least one ultraviolet filter compound of the formula: ##STR32## wherein n is 1 or 2, when n is 1, R 1 and R 2 are independently chosen to represent hydrogen, an alkyl group of 1 to 10 carbon atoms, or a cyclic alkyl group of 5 to 6 carbon atoms provided that R 1 and R 2 cannot both be hydrogen, or R 1 and R 2 taken together represent the atoms necessary to complete a cyclic amino group and when n is 2 at least one of R 1 and R 2 is alkylene and G represents an electron withdrawing group. .Iaddend.
Claim 32
Dependent Claim
142 words
electron withdrawing group. .Iaddend. .Iadd.21. A photographic element comprising at least one silver halide emulsion layer coated on a film support, said film support being selected from a solvent cast or melt-formed film support and having incorporated therein at least one ultraviolet filter compound of the formula: ##STR32## wherein n is 1 or 2, when n is 1, R 1 and R 2 are independently chosen to represent hydrogen, an alkyl group of 1 to 10 carbon atoms, or a cyclic alkyl group of 5 to 6 carbon atoms provided that R 1 and R 2 cannot both be hydrogen, or R 1 and R 2 taken together represent the atoms necessary to complete a cyclic amino group and when n is 2 at least one of R 1 and R 2 is alkylene and G represents an electron withdrawing group. .Iaddend.
References Cited (Backward Citations)
US3125597A
Cited
GB786168A
Cited
DE1087902B
Cited
US3052636A
Cited
US3652289A
Cited
US3702861A
Cited
US3718472A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-06-10 | 1983-12-10 | 1984-06-10 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-06-10 | 1987-12-10 | 1988-06-10 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-06-10 | 1991-12-10 | 1992-06-10 | $7700.00 | Window Closed / Lapsed |