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US4201589A
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Silver halide photo-sensitive material prepared with solvent and solvent soluble polymer
Assignee: Fujifilm Holdings Corp
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Filing: 1979-04-20
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Granted: 1980-05-06
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Expires: 1999-04-20
Abstract
Abstract A silver halide photo-sensitive material is provided having a hydrophilic colloid layer containing dispersed therein finely divided particles of a substantially water-immiscible mixture containing a hydrophobic photographic substance. The aforesaid mixture contains a polymer having recurring units represented by the following general formula (I) ##STR1## where, in the above formula, R 1 represents a hydrogen atom or methyl group, R 2 represents a hydrogen atom or substituted or unsubstituted aliphatic hydrocarbon radical containing 1 to 12 carbon atoms, X represents a bivalent substituted or unsubstituted aliphatic hydrocarbon radical containing 2 to 8 carbon atoms, and n is an integer of 1 to 50.
Inventors
- 👤 Shinji Sakaguchi
- 👤 Seiiti Kubodera
- 👤 Jun Arakawa
- 👤 Keisuke Shiba
- 👤 Nobuo Tsuji
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 23:30
CPC Classifications
G; G03; G03C; G03C1/00; G03C1/005; G03C1/04; G03C1/053; G03C7/00; G03C7/30; G03C7/388; G03C7/3882
Claims Analysis
Total Claims: 23
Claim 1
Independent Claim
197 words
A method of incorporating a hydrophobic photographic substance which is a hydrophobic photographic coupler, an antioxidant, an antifogging agent or a fluorescent whitening agent into a hydrophilic colloid of a silver halide photo-sensitive material which comprising mixing said hydrophobic photographic substance with a solution in an organic solvent of an organic solvent soluble polymer containing 5 to 100 mol % of recurring units represented by the following general formula (I) ##STR18## where, in the formula R 1 represents a hydrogen atom or methyl group; R 2 represents a hydrogen atom or an alkyl group containing 1 to 12 carbon atoms, X is a bivalent hydrocarbon radical containing 2 to 8 carbon atoms selected from the group consisting of a alkylene group, a haloalkylene group and a hydroxy alkylene group, and n is an integer of 1 to 50, the remaining part of the polymer being made of recurring units of an addition polymerizable unsaturated compound, the organic solvent soluble polymer being present in a weight ratio to said hydrophobic photographic substance of from 20 to 0.01:1 to form a substantially water-immiscible mixture, and finely dispersing said substantially water-immiscible mixture in an aqueous solution of said hydrophilic colloid.
Claim 2
Independent Claim
197 words
A method of incorporating a hydrophobic photographic substance which is a hydrophobic photographic coupler, an antioxidant, an antifogging agent or a fluorescent whitening agent into a hydrophilic colloid of a silver halide photo-sensitive material which comprising mixing said hydrophobic photographic substance with a solution in an organic solvent of an organic solvent soluble polymer containing 5 to 100 mol % of recurring units represented by the following general formula (I) ##STR18## where, in the formula R 1 represents a hydrogen atom or methyl group; R 2 represents a hydrogen atom or an alkyl group containing 1 to 12 carbon atoms, X is a bivalent hydrocarbon radical containing 2 to 8 carbon atoms selected from the group consisting of a alkylene group, a haloalkylene group and a hydroxy alkylene group, and n is an integer of 1 to 50, the remaining part of the polymer being made of recurring units of an addition polymerizable unsaturated compound, the organic solvent soluble polymer being present in a weight ratio to said hydrophobic photographic substance of from 20 to 0.01:1 to form a substantially water-immiscible mixture, and finely dispersing said substantially water-immiscible mixture in an aqueous solution of said hydrophilic colloid.
Claim 3
Dependent Claim
15 words
A method according to claim 1 wherein said hydrophobic photographic substance is a hydrophobic coupler.
Claim 4
Dependent Claim
163 words
A method according to claim 1 wherein the polymer is a homopolymer or copolymer with at least one copolymerizable unsaturated monomer represented by the following general formula (II) ##STR19## wherein the formula, R 1 represents a hydrogen atom or methyl group; R 2 represents a hydrogen atom or alkyl containing 1 to 12 carbon atoms; X represents an alkylene, haloalkylene or hydroxyalkylene group containing 2 to 8 carbon atoms; and n is an integer of 1 to 50, said copolymerizable monomer being selected from the group consisting of acrylic acid, ethacrylic acid, methacrylic acid, an acrylamide, a methacrylamide, methyl sorbate, an allyl compound, a vinyl ether, a vinyl ester, a vinyl heterocyclic compound, styrene, alkyl styrene, chloroacrylic acid, mesaconic acid, halostyrene, maleic acid, fumaric acid, itaconic acid, citraconic acid, crotonic acid, an acrylate, a methacrylate, a vinyl ketone, an olefin, itaconic anhydride, an alkyl itaconate, sorbic acid, cinnamic acid, maleic anhydride, an alkyl maleate, halogenated olefin, an alkyl fumarate and an unsaturated nitrile.
Claim 5
Dependent Claim
16 words
A method according to claim 1 wherein said organic solvent is a lower boiling organic solvent.
Claim 6
Dependent Claim
35 words
A method according to claim 4 wherein the organic solvent is a member selected from the group consisting of methyl acetate, ethyl acetate, methyl isobutyl ketone, beta-ethoxyethyl acetate, methyl carbitol, dioxane, cyclohexanone and dipropylene glycol.
Claim 7
Dependent Claim
10 words
A photo-sensitive material prepared by the process of claim 1.
Claim 8
Dependent Claim
165 words
A photo-sensitive material according to claim 6 in which the polymer is a homopolymer or copolymer with at least one copolymerizable unsaturated monomer represented by the following general formula (II) ##STR20## wherein the formula, R 1 represents a hydrogen atom or methyl group; R 2 represents a hydrogen atom or alkyl containing 1 to 12 carbon atoms; X represents an alkylene, haloalkylene or hydroxyalkylene group containing 2 to 8 carbon atoms; and n is a integer of 1 to 50, said copolymerizable monomer being selected from the group consisting of acrylic acid, ethacrylic acid, methacrylic acid, an acrylamide, a methacrylamide, methyl sorbate, a allyl compound, a vinyl ether, a vinyl ester, a vinyl heterocyclic compound, styrene alkyl styrene, chloroacrylic acid, mesaconic acid, halostyrene, maleic acid, fumaric acid, itaconic acid, citraconic acid, crotonic acid, an acrylate, a methacrylate, a vinyl ketone, an olefin, itaconic anhydridem, an alkyl itaconate, sorbic acid, cinnamic acid, maleic anhydride, a alkyl maleate, halogenated olefin, an alkyl fumarate and an unsaturated nitrile.
Claim 9
Dependent Claim
49 words
A silver halide photo-sensitive material according to claim 7 suitable for color photography and wherein the hydrophilic colloid containing layer comprises a silver halide photo emulsion containing dispersed therein a mixture of said polymer and a hydrophobic coupler, said mixture having an average particle size not exceeding 5 microns.
Claim 10
Dependent Claim
72 words
A silver halide photo-sensitive material according to claim 8 wherein said emulsion also has dispersed therein a high boiling oil former, said mixture of polymer and hydrophobic coupler has an average particle size not exceeding 0.2 microns, the weight ratio of polymer to coupler being from 1.0 to 0.05:1, said polymer being a polymer of 20 to 70% of said monomer having furmula II, with 80 to 30% of said copolymerizable monomer.
Claim 11
Dependent Claim
12 words
The silver halide photo-sensitive material prepared by the method of claim 3.
Claim 12
Dependent Claim
14 words
A silver halide photo-sensitive material according to claim 20 wherein R 2 is hydrogen.
Claim 13
Dependent Claim
23 words
A photo-sensitive material according to claim 6 in which the n in the general formula (I) is an integer of 1 to 10.
Claim 14
Dependent Claim
30 words
A photo-sensitive material according to claim 6 in which the R 2 in the general formula (I) is a hydrogen atom or alkyl group containing 1 to 5 carbon atoms.
Claim 15
Dependent Claim
26 words
A photo-sensitive material according to claim 7 in which the n in the general formula (II) of the monomer is an integer of 1 to 10.
Claim 16
Dependent Claim
33 words
A photo-sensitive material according to claim 7 in which the R 2 in the general formula (II) of the monomer is a hydrogen atom or alkyl group containing 1 to 5 carbon atoms.
Claim 17
Dependent Claim
29 words
A photo-sensitive material according to claim 7 in which the polymer contains as its integral units 20 to 70 mol% of the monomer represented by the general formula (II).
Claim 18
Dependent Claim
28 words
A photo-sensitive material according to claim 6 in which the organic solvent-soluble polymer is used in a weight ratio to hydrophilic photographic material of from 1.0 to 0.05.
Claim 19
Dependent Claim
17 words
A photo-sensitive material according to claim 6 in which the hydrophobic photographic substance is a hydrophobic coupler.
Claim 20
Dependent Claim
248 words
A photo-sensitive material according to claim 18 in which the hydrophobic coupler is a member selected from the class consisting of the compounds represented by one of the following general formulae (III), (IV), (V), and (VI) ##STR21## where, in the formula, R 11 represents a primary, secondary or tertiary alkyl group or substituted alkyl group, aryl group, heterocyclic radical, amino group, carbonamido group, ureido group or alkoxy group; R 12 represents a hydrogen atom, aryl group or substituted aryl group, heterocyclic radical or alkyl group; and Z 1 represents a hydrogen atom or radical capable of being liberated during development, ##STR22## where, in the formula, R 13 represents a primary, secondary or tertiary alkyl group or substituted alkyl group containing 1 to 18 carbon atoms, aryl group, substituted aryl group or amino group; R 14 represents an aryl group or substituted aryl group; and Z 2 represents a hydrogen atom or radical capable of being liberated during development, ##STR23## where, in the formula, R 15 represents a substituent that is conventional in cyan couplers; and Z 3 represents a hydrogen atom or radical capable of being liberated during development, and ##STR24## where, in the formula, R 16 represents an alkyl group, aryl group, heterocyclic radical, amino group, carbonamido group, sulfamyl group or carbamyl group; R 17 , R 18 , and R 19 are as defined for R 16 or halogen or alkoxy; and Z 4 represents a hydrogen atom or radical capable of being liberated during development.
Claim 21
Dependent Claim
20 words
A photo-sensitive material according to claim 6 in which the hydrophilic colloid layer is a silver halide photo emulsion layer.
Claim 22
Dependent Claim
20 words
A photo-sensitive material according to claim 8 in which the hydrophilic colloid contains in addition a high boiling oil former.
Claim 23
Dependent Claim
17 words
A photo-sensitive material according to claim 8 in which the hydrophobic photographic substance is a hydrophobic coupler.
References Cited (Backward Citations)
US3607290A
Cited
US3655389A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-05-06 | 1983-11-05 | 1984-05-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-05-06 | 1987-11-05 | 1988-05-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-05-06 | 1991-11-05 | 1992-05-06 | $7700.00 | Window Closed / Lapsed |