US4207109A
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Element for photographic use containing crosslinkable polymers having acrylamidophenol units
Assignee: Eastman Kodak Co
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Filing: 1978-04-05
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Granted: 1980-06-10
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Expires: 1998-04-05
Abstract
Abstract Copolymers containing an acrylamidophenol as a crosslinking site and the corresponding crosslinked polymers are disclosed. The acrylamidophenol unit can be copolymerized with a wide variety of other monomers to provide crosslinkable and crosslinked polymers with useful properties. The acrylamidophenol unit provides for crosslinking at low pH with conventional crosslinking agents. The acrylamidophenol monomer unit is present in the copolymer from about 0.5 to 50 percent by weight and has the formula: ##STR1## wherein: x is 1 or 0, L is a linking group, R represents hydrogen or methyl, and R 1 through R 5 are independently selected from the group consisting of hydrogen, hydroxy, alkyl from 1 to 6 carbon atoms and aryl from 6 to 10 carbon atoms; with the proviso that at least one of R 1 through R 5 is hydroxy and at least one of the positions ortho or para to said hydroxy has a hydrogen atom attached thereto. The remainder of the polymer can comprise from 50 to 99.5 percent by weight of at least one additional polymerized ethylenically unsaturated monomer. Elements, particularly photographic elements, comprising a support having coated thereon either the crosslinked or uncrosslinked polymer are also disclosed.
Inventors
- 👤 Gerald A. Campbell
- 👤 Kenneth R. Hollister
- 👤 Richard C. Sutton
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 10:49
CPC Classifications
G; G03; G03C; G03C1/00; G03C1/005; G03C1/04; G03C1/053; C; C08; C08F; C08F246/00; C08F220/00; C08F220/02; C08F220/52; C08F220/54; C08F220/60; C08F220/603; Y; Y10; Y10S; Y10S430/00; Y10S430/142
Claims Analysis
Total Claims: 30
Claim 1
Independent Claim
137 words
An element comprising a support having coated thereon a layer comprising an addition copolymer; said copolymer consisting essentially of: A. from about 0.5 to 50 percent by weight of a unit having the formula: ##STR3## wherein: x is 1 or 0, R represents hydrogen or methyl, L is a linking group, and R 1 through R 5 are independently selected from the group consisting of hydrogen, hydroxy, alkyl from 1 to 6 carbon atoms and aryl from 6 to 10 carbon atoms; with the proviso that at least one of R 1 through R 5 is hydroxy and at least one of the positions ortho or para to said hydroxy has a hydrogen atom attached thereto; and B. from about 50 to 99.5 percent by weight of units of at least one additional polymerized ethylenically unsaturated monomer.
Claim 2
Dependent Claim
137 words
An element comprising a support having coated thereon a layer comprising an addition copolymer; said copolymer consisting essentially of: A. from about 0.5 to 50 percent by weight of a unit having the formula: ##STR3## wherein: x is 1 or 0, R represents hydrogen or methyl, L is a linking group, and R 1 through R 5 are independently selected from the group consisting of hydrogen, hydroxy, alkyl from 1 to 6 carbon atoms and aryl from 6 to 10 carbon atoms; with the proviso that at least one of R 1 through R 5 is hydroxy and at least one of the positions ortho or para to said hydroxy has a hydrogen atom attached thereto; and B. from about 50 to 99.5 percent by weight of units of at least one additional polymerized ethylenically unsaturated monomer.
Claim 3
Dependent Claim
161 words
An element comprising a support having coated thereon a layer comprising a crosslinked addition copolymer formed by crosslinking a copolymer consisting essentially of: A. from about 0.5 to 50 percent by weight of a unit having the formula: ##STR4## wherein: x is 1 or 0, R represents hydrogen or methyl, L is a linking group, and R 1 through R 5 are independently selected from the group consisting of hydrogen, hydroxy, alkyl from 1 to 6 carbon atoms and aryl from 6 to 10 carbon atoms; with the proviso that at least one of R 1 through R 5 is hydroxy and at least one of the positions ortho or para to said hydroxy has a hydrogen atom attached thereto; and B. from about 50 to 99.5 percent by weight of units of at least one additional polymerized ethylenically unsaturated monomer, with 0.1 to 25 percent by weight based on the total weight of the uncrosslinked polymer of a crosslinking agent.
Claim 4
Dependent Claim
161 words
An element comprising a support having coated thereon a layer comprising a crosslinked addition copolymer formed by crosslinking a copolymer consisting essentially of: A. from about 0.5 to 50 percent by weight of a unit having the formula: ##STR4## wherein: x is 1 or 0, R represents hydrogen or methyl, L is a linking group, and R 1 through R 5 are independently selected from the group consisting of hydrogen, hydroxy, alkyl from 1 to 6 carbon atoms and aryl from 6 to 10 carbon atoms; with the proviso that at least one of R 1 through R 5 is hydroxy and at least one of the positions ortho or para to said hydroxy has a hydrogen atom attached thereto; and B. from about 50 to 99.5 percent by weight of units of at least one additional polymerized ethylenically unsaturated monomer, with 0.1 to 25 percent by weight based on the total weight of the uncrosslinked polymer of a crosslinking agent.
Claim 5
Dependent Claim
23 words
The element of claim 2 wherein said cross-linking agent is an aldehyde or an organic compound having at least two activated double bonds.
Claim 6
Dependent Claim
20 words
The element of claim 2 wherein said cross-linking agent is selected from the group consisting of formaldehyde and bis(vinylsulfonylmethyl) ether.
Claim 7
Dependent Claim
31 words
The element of claim 2 wherein said cross-linking copolymer is crosslinked with 0.1 to 10 percent by weight of said crosslinking agent based on the total weight of the uncrosslinked polymer.
Claim 8
Dependent Claim
16 words
The element of claim 2 wherein B is a polymerized monomer which hydrolyzes at high pH.
Claim 9
Dependent Claim
18 words
The element of claim 2 wherein R 2 or R 4 is hydroxy and R 3 is hydrogen.
Claim 10
Dependent Claim
18 words
The element of claim 2 wherein A is from about 0.1 to 20 weight percent of the copolymer.
Claim 11
Dependent Claim
10 words
The element of claim 2 wherein A is polymerized m-acrylamidophenol.
Claim 12
Dependent Claim
15 words
The element of claim 2 wherein B is polymerized acrylic acid or polymerized methacrylic acid.
Claim 13
Dependent Claim
145 words
A photographic element comprising a support having coated thereon at least one radiation-sensitive layer and a layer comprising an addition copolymer, said copolymer consisting essentially of: A. from about 0.5 to 50 percent by weight of a unit having the formula: ##STR5## wherein: x is 1 or 0, R represents hydrogen or methyl, L is a linking group, and R 1 through R 5 are independently selected from the group consisting of hydrogen, hydroxy, and alkyl from 1 to 6 carbon atoms and aryl from 6 to 10 carbon atoms; with the proviso that at least one of R 1 through R 5 is hydroxy and at least one of the positions ortho or para to said hydroxy has a hydrogen atom attached thereto; and B. from about 50 to 99.5 percent by weight of units of at least one additional polymerized ethylenically unsaturated monomer.
Claim 14
Dependent Claim
145 words
A photographic element comprising a support having coated thereon at least one radiation-sensitive layer and a layer comprising an addition copolymer, said copolymer consisting essentially of: A. from about 0.5 to 50 percent by weight of a unit having the formula: ##STR5## wherein: x is 1 or 0, R represents hydrogen or methyl, L is a linking group, and R 1 through R 5 are independently selected from the group consisting of hydrogen, hydroxy, and alkyl from 1 to 6 carbon atoms and aryl from 6 to 10 carbon atoms; with the proviso that at least one of R 1 through R 5 is hydroxy and at least one of the positions ortho or para to said hydroxy has a hydrogen atom attached thereto; and B. from about 50 to 99.5 percent by weight of units of at least one additional polymerized ethylenically unsaturated monomer.
Claim 15
Dependent Claim
167 words
A photographic element comprising a support having coated thereon at least one radiation-sensitive layer and a layer comprising a crosslinked addition copolymer formed by crosslinking a copolymer consisting essentially of: A. from about 0.5 to 50 percent by weight of a unit having the formula: ##STR6## wherein: x is 1 or 0, R represents hydrogen or methyl, L is a linking group, and R 1 through R 5 are independently selected from the group consisting of hydrogen, hydroxy, alkyl from 1 to 6 carbon atoms and aryl from 6 to 10 carbon atoms; with the proviso that at least one of R 1 through R 5 is hydroxy and at least one of the positions ortho or para to said hydroxy has a hydrogen atom attached thereto; and B. from about 50 to 99.5 percent by weight of units of at least one additional polymerized ethylenically unsaturated monomer, with 0.1 to 25 percent by weight based on the total weight of the uncrosslinked polymer of crosslinking agent.
Claim 16
Dependent Claim
167 words
A photographic element comprising a support having coated thereon at least one radiation-sensitive layer and a layer comprising a crosslinked addition copolymer formed by crosslinking a copolymer consisting essentially of: A. from about 0.5 to 50 percent by weight of a unit having the formula: ##STR6## wherein: x is 1 or 0, R represents hydrogen or methyl, L is a linking group, and R 1 through R 5 are independently selected from the group consisting of hydrogen, hydroxy, alkyl from 1 to 6 carbon atoms and aryl from 6 to 10 carbon atoms; with the proviso that at least one of R 1 through R 5 is hydroxy and at least one of the positions ortho or para to said hydroxy has a hydrogen atom attached thereto; and B. from about 50 to 99.5 percent by weight of units of at least one additional polymerized ethylenically unsaturated monomer, with 0.1 to 25 percent by weight based on the total weight of the uncrosslinked polymer of crosslinking agent.
Claim 17
Dependent Claim
14 words
A photographic element according to claim 12 wherein said radiation-sensitive layer comprises silver halide.
Claim 18
Dependent Claim
25 words
A photographic element according to claim 12 wherein said crosslinking agent is an aldehyde or an organic compound having at least two activated double bonds.
Claim 19
Dependent Claim
22 words
A photographic element according to claim 12 wherein said crosslinking agent is selected from the group consisting of formaldehyde and bis(vinylsulfonylmethyl) ether.
Claim 20
Dependent Claim
33 words
A photographic element according to claim 12 wherein said crosslinking copolymer is crosslinked with 0.1 to 10 percent by weight of said crosslinking agent based on the total weight of the uncrosslinked polymer.
Claim 21
Dependent Claim
18 words
A photographic element according to claim 12 wherein B is a polymerized monomer which hydrolyzes at high pH.
Claim 22
Dependent Claim
20 words
A photographic element according to claim 12 wherein R 2 or R 4 is hydroxy and R 3 is hydrogen.
Claim 23
Dependent Claim
20 words
A photographic element according to claim 12 wherein A is from about 0.1 to 20 weight percent of the copolymer.
Claim 24
Dependent Claim
12 words
A photographic element according to claim 12 wherein A is polymerized m-acrylamidophenol.
Claim 25
Dependent Claim
17 words
A photographic element according to claim 12 wherein B is polymerized acrylic acid or polymerized methacrylic acid.
Claim 26
Dependent Claim
142 words
A photographic element comprising a support having coated thereon at least one photographic silver halide emulsion layer containing an addition copolymer consisting essentially of: A. from about 0.5 to 50 percent by weight of a unit having the formula: ##STR7## wherein: x is 1 or 0, R represents hydrogen or methyl, L is a linking group, and R 1 through R 5 are independently selected from the group consisting of hydrogen, hydroxy, alkyl from 1 to 6 carbon atoms and aryl from 6 to 10 carbon atoms; with the proviso that at least one of R 1 through R 5 is hydroxy and at least one of the positions ortho or para to said hydroxy has a hydrogen atom attached thereto; and B. from about 50 to 99.5 percent by weight of units of at least one additional polymerized ethylenically unsaturated monomer.
Claim 27
Dependent Claim
142 words
A photographic element comprising a support having coated thereon at least one photographic silver halide emulsion layer containing an addition copolymer consisting essentially of: A. from about 0.5 to 50 percent by weight of a unit having the formula: ##STR7## wherein: x is 1 or 0, R represents hydrogen or methyl, L is a linking group, and R 1 through R 5 are independently selected from the group consisting of hydrogen, hydroxy, alkyl from 1 to 6 carbon atoms and aryl from 6 to 10 carbon atoms; with the proviso that at least one of R 1 through R 5 is hydroxy and at least one of the positions ortho or para to said hydroxy has a hydrogen atom attached thereto; and B. from about 50 to 99.5 percent by weight of units of at least one additional polymerized ethylenically unsaturated monomer.
Claim 28
Dependent Claim
169 words
A photographic element comprising a support having coated thereon at least one photographic silver halide emulsion layer containing a crosslinked addition copolymer formed by crosslinking a copolymer consisting essentially of: A. from about 0.5 to 50 percent by weight of a unit having the formula: ##STR8## wherein: x is 1 or 0, R represents hydrogen or methyl, L is a linking group, and R 1 through R 5 are independently selected from the group consisting of hydrogen, hydroxy, alkyl from 1 to 6 carbon atoms and aryl from 6 to 10 carbon atoms; with the proviso that at least one of R 1 through R 5 is hydroxy and at least one of the positions ortho or para to said hydroxy has a hydrogen atom attached thereto; and B. from about 50 to about 99.5 percent by weight of units of at least one additional polymerized ethylenically unsaturated monomer; with 0.1 to 25 percent by weight based on the total weight of the uncrosslinked polymer of a crosslinking agent.
Claim 29
Dependent Claim
169 words
A photographic element comprising a support having coated thereon at least one photographic silver halide emulsion layer containing a crosslinked addition copolymer formed by crosslinking a copolymer consisting essentially of: A. from about 0.5 to 50 percent by weight of a unit having the formula: ##STR8## wherein: x is 1 or 0, R represents hydrogen or methyl, L is a linking group, and R 1 through R 5 are independently selected from the group consisting of hydrogen, hydroxy, alkyl from 1 to 6 carbon atoms and aryl from 6 to 10 carbon atoms; with the proviso that at least one of R 1 through R 5 is hydroxy and at least one of the positions ortho or para to said hydroxy has a hydrogen atom attached thereto; and B. from about 50 to about 99.5 percent by weight of units of at least one additional polymerized ethylenically unsaturated monomer; with 0.1 to 25 percent by weight based on the total weight of the uncrosslinked polymer of a crosslinking agent.
Claim 30
Dependent Claim
15 words
The photographic element of claim 23 wherein the silver halide emulsion layer additionally comprises gelatin.
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) | 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 |