US4045229A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Novel UV absorbing compounds and photographic elements containing UV absorbing compounds
Assignee: Eastman Kodak Co
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Filing: 1975-12-18
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Granted: 1977-08-30
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Expires: 1995-12-18
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 Woodrow Weber
- 👤 Donald Warren Heseltine
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 09:31
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: 30
Claim 1
Independent Claim
32 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.
Claim 2
Dependent Claim
32 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.
Claim 3
Dependent Claim
119 words
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 group.
Claim 4
Dependent Claim
138 words
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 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 group.
Claim 5
Dependent Claim
138 words
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 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 group.
Claim 6
Dependent Claim
14 words
A photographic element according to claim 3 wherein the binder is a hydrophillic colloid.
Claim 7
Dependent Claim
41 words
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 6 to 10 carbon atoms.
Claim 8
Dependent Claim
29 words
A photographic element according to claim 3 wherein G is the group CN and R 1 and R 2 are both alkyl groups of 1 to 10 carbon atoms.
Claim 9
Dependent Claim
30 words
A photographic element according to claim 3 wherein G is the group CN, R 1 is hydrogen and R 2 is an alkyl group of 1 to 10 carbon atoms.
Claim 10
Dependent Claim
51 words
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 3[N,N-bis(2-cyanoethyl)amino]allylidenemalononitrile.
Claim 11
Dependent Claim
51 words
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 3[N,N-bis(2-cyanoethyl)amino]allylidenemalononitrile.
Claim 12
Dependent Claim
45 words
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 4-tert-butylphenylsulfonylacetonitrile.
Claim 13
Dependent Claim
45 words
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 4-tert-butylphenylsulfonylacetonitrile.
Claim 14
Dependent Claim
147 words
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 group.
Claim 15
Dependent Claim
147 words
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 group.
Claim 16
Dependent Claim
41 words
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 6 to 10 carbon atoms.
Claim 17
Dependent Claim
28 words
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 10 carbon atoms.
Claim 18
Dependent Claim
30 words
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 to 10 carbon atoms.
Claim 19
Dependent Claim
60 words
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-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-dicyanobutadienyl)-1,6-diaminohexane and 3-[N,N-bis(2-cyanoethyl)amino]allylidenemalononitrile.
Claim 20
Dependent Claim
60 words
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-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-dicyanobutadienyl)-1,6-diaminohexane and 3-[N,N-bis(2-cyanoethyl)amino]allylidenemalononitrile.
Claim 21
Dependent Claim
54 words
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-morpholinoallylidene methylsulfonylacetonitrile, 3-morpholinoallylidene 4-tert-butylphenylsulfonylacetonitrile, 3-piperazinoallylidene 4-tert-butylphenylsulfonylacetonitrile and 3-N-methylpiperazinoallylidene 4-tert-butylphenylsulfonylacetonitrile.
Claim 22
Dependent Claim
54 words
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-morpholinoallylidene methylsulfonylacetonitrile, 3-morpholinoallylidene 4-tert-butylphenylsulfonylacetonitrile, 3-piperazinoallylidene 4-tert-butylphenylsulfonylacetonitrile and 3-N-methylpiperazinoallylidene 4-tert-butylphenylsulfonylacetonitrile.
Claim 23
Dependent Claim
27 words
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 3-dibutylaminoallylidenemalononitrile.
Claim 24
Dependent Claim
27 words
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 3-dibutylaminoallylidenemalononitrile.
Claim 25
Dependent Claim
27 words
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 3-dihexylaminoallylidenemalononitrile.
Claim 26
Dependent Claim
27 words
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 3-dihexylaminoallylidenemalononitrile.
Claim 27
Dependent Claim
36 words
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 compound 3-dibutylaminoallylidenemalononitrile.
Claim 28
Dependent Claim
36 words
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 compound 3-dibutylaminoallylidenemalononitrile.
Claim 29
Dependent Claim
36 words
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 compound 3-dihexylaminoallylidenemalononitrile.
Claim 30
Dependent Claim
36 words
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 compound 3-dihexylaminoallylidenemalononitrile.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-08-29 | 1981-02-28 | 1981-08-30 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-08-29 | 1985-02-28 | 1985-08-30 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-08-29 | 1989-02-28 | 1989-08-30 | $7700.00 | Window Closed / Lapsed |