US4419440A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Process for the introduction of hydrophobic photographic additives
Assignee: Filmfabrik Wolfen VEB
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Filing: 1981-11-09
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Granted: 1983-12-06
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Expires: 2001-11-09
Abstract
Abstract The present invention relates to a process for the introduction of water-insoluble photographic additives, especially dye couplers, in aqueous media with the application of high-boiling organic solvents. The purpose of the invention is to develop an improved process for the introduction of hydrophobic photographic additives, especially dye couplers, in gelatin or other hydrophilic bonding agents in order to produce stable dispersions suitable for storage. This invention has the object of creating a new, high-boiling solvent for the dispersion of hydrophobic photographic additives. According to the invention, this aim is achieved by employing phosphonic acid diamides, methane bisphosphonic acid diamides, phosphonic acid esters, methane bisphosphonic acid esters or mixed phosphonic acid esters or methane bisphosphonic acid ester amides as high-boiling solvents.
Inventors
- 👤 Lothar Kuhnert
- 👤 Burkhard Costisella
- 👤 Christoph Roth
- 👤 Walter Kroha
- 👤 Wolfgang Baumbach
- 👤 Renate Hoppe
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 11:34
CPC Classifications
G; G03; G03C; G03C7/00; G03C7/30; G03C7/388; G03C7/3885
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
185 words
Process for the introduction of an hydrophobic photographic additive into a hydrophilic colloidal layer, wherein these additives are dissolved in an organic solvent that is not completely miscible with water and are subsequently dispersed in an aqueous medium, characterized in that at least one phosphonic acid diamide or methane bisphosphonic acid diamide of the general formulae ##STR6## and/or phosphonic acid esters or methane bisphosphonic acid esters of the general formulae ##STR7## and/or mixed phosphonic acid esters amides or methane bisphosphonic acid esters of the general formulae ##STR8## wherein R 1 represents aryl, methyl-substituted aryl, halogen-substituted aryl, alkyl with 1 to 14 carbon atoms or substituted alkyl; R 2 and R 3 represent hydrogen, alkyl, aryl, --N(R 4 ) 2 , --S--R 4 , --OR 4 , or R 2 may represent hydrogen and R 3 represents alkyl, aryl, --N(R 4 ) 2 , --S--R 4 , OR 4 , and R 4 and R 5 represents alkyl with 1 to 14 carbon atoms and R 6 alkyl with 1 to 14 carbon atoms, aryl, methyl-substituted aryl or halogen-substituted aryl, is used as a high-boiling solvent.
Claim 2
Dependent Claim
185 words
Process for the introduction of an hydrophobic photographic additive into a hydrophilic colloidal layer, wherein these additives are dissolved in an organic solvent that is not completely miscible with water and are subsequently dispersed in an aqueous medium, characterized in that at least one phosphonic acid diamide or methane bisphosphonic acid diamide of the general formulae ##STR6## and/or phosphonic acid esters or methane bisphosphonic acid esters of the general formulae ##STR7## and/or mixed phosphonic acid esters amides or methane bisphosphonic acid esters of the general formulae ##STR8## wherein R 1 represents aryl, methyl-substituted aryl, halogen-substituted aryl, alkyl with 1 to 14 carbon atoms or substituted alkyl; R 2 and R 3 represent hydrogen, alkyl, aryl, --N(R 4 ) 2 , --S--R 4 , --OR 4 , or R 2 may represent hydrogen and R 3 represents alkyl, aryl, --N(R 4 ) 2 , --S--R 4 , OR 4 , and R 4 and R 5 represents alkyl with 1 to 14 carbon atoms and R 6 alkyl with 1 to 14 carbon atoms, aryl, methyl-substituted aryl or halogen-substituted aryl, is used as a high-boiling solvent.
Claim 3
Dependent Claim
28 words
Process according to claim 1, characterized in that the high-boiling solvent is used in a proportionate amount of from 25 to 200%, to the additive to be dispersed.
Claim 4
Dependent Claim
16 words
The process of claim 1 comprising a mixture of at least a plurality of compounds I-VII.
Claim 5
Dependent Claim
18 words
The process of claim 3 comprising an additional solvent mixed with at least a plurality of compounds I-VII.
Claim 6
Dependent Claim
172 words
A dispersion comprising a surface active agent, a high-boiling solvent for the introduction of a water-insoluble photographic additive into an aqueous medium, said solvent comprising at least one phosphonic acid derivative of the following formulas I-VII: ##STR9## wherein R 1 ═aryl, methyl, halogen-substituted aryl, alkyl or substituted alkyl of 1 to 14 carbon atoms in length, R 2 ═R 3 ═hydrogen, alkyl, aryl, --N(R 4 ) 2 , --SR 4 , --OR 4 , R 2 and R 3 being the same or different, R 4 ═R 5 ═alkyl of 1 to 14 carbon atoms in length, R 4 and R 5 being the same or different, and R 6 ═alkyl of 1 to 14 carbon atoms in length, aryl, methyl, or halogen-substituted aryl, said surface active agent, comprising at least one of alkyl sulfates, alkyl sulfonates, alkyl aryl sulfonates, dialkyl sulfosuccinates, polyoxyethylene alkylethers and/or sulfate esters thereof, polyoxyethylene alkylarylethers and/or sulfate esters thereof, and polyoxyethylene alkyl esters and/or sulfate esters thereof, and a hydrophilic substance, wherein said hydrophilic substance is gelatin.
Claim 7
Dependent Claim
172 words
A dispersion comprising a surface active agent, a high-boiling solvent for the introduction of a water-insoluble photographic additive into an aqueous medium, said solvent comprising at least one phosphonic acid derivative of the following formulas I-VII: ##STR9## wherein R 1 ═aryl, methyl, halogen-substituted aryl, alkyl or substituted alkyl of 1 to 14 carbon atoms in length, R 2 ═R 3 ═hydrogen, alkyl, aryl, --N(R 4 ) 2 , --SR 4 , --OR 4 , R 2 and R 3 being the same or different, R 4 ═R 5 ═alkyl of 1 to 14 carbon atoms in length, R 4 and R 5 being the same or different, and R 6 ═alkyl of 1 to 14 carbon atoms in length, aryl, methyl, or halogen-substituted aryl, said surface active agent, comprising at least one of alkyl sulfates, alkyl sulfonates, alkyl aryl sulfonates, dialkyl sulfosuccinates, polyoxyethylene alkylethers and/or sulfate esters thereof, polyoxyethylene alkylarylethers and/or sulfate esters thereof, and polyoxyethylene alkyl esters and/or sulfate esters thereof, and a hydrophilic substance, wherein said hydrophilic substance is gelatin.
Claim 8
Dependent Claim
23 words
The dispersion of claim 5 wherein said gelatin is mixed with at least one of polyvinyl alcohol, polyvinyl pyrrolidine, polyacrylamide, and cellulose derivatives.
Claim 9
Dependent Claim
15 words
The dispersion of claim 5 wherein said water insoluble photographic additive is a dye coupler.
Claim 10
Dependent Claim
31 words
The dispersion of claim 7 wherein (A) said dye coupler is ##STR10## (B) said solvent is phenyl phosphonic acid diethyl ester, and (C) said surface active agent is sodium dodecyl sulfate.
Claim 11
Dependent Claim
30 words
The dispersion of claim 7 wherein (A) said dye coupler is ##STR11## (B) said solvent is methane bisphosphonic acid tetra-n-butylester, and (C) said surface active agent is sodium dihexyl sulfosuccinate.
Claim 12
Dependent Claim
35 words
The dispersion of claim 7 wherein (A) said dye coupler is ##STR12## (B) said solvent comprises a mixture of phenylphosphonic acid-dioctylester and phenyl phosphonic acid-n-butylamide, and (C) said surface active agent is sodium dodecyl sulfate.
Claim 13
Dependent Claim
30 words
The dispersion of claim 7 wherein (A) said dye coupler is ##STR13## (B) said solvent is phenylphosphonic acid ethyl ester-di-n-butylamide, and (C) said surface active agent is sodium decylbenzene sulfonate.
Claim 14
Dependent Claim
29 words
The dispersion of claim 7 wherein (A) said dye coupler is ##STR14## (B) said solvent is diethoxymethane-phosphonic acid-(1-n-octyl-ethylene) ester, and (C) said surface active agent is sodium dodecyl sulfate.
Claim 15
Dependent Claim
28 words
The dispersion of claims 8, 9, 10, 11, or 12, wherein ethyl acetate is initially added to said solvent (B), and subsequently removed after said dispersion is formed.
Claim 16
Dependent Claim
21 words
The process of claim 4 wherein said additional solvent is removed after dispersing said hydrophobic photograph additive in an aqueous medium.
Claim 17
Dependent Claim
18 words
The process of claim 14 additionally comprising mixing said solvent with an anionic and/or nonionic surface active agent.
Claim 18
Dependent Claim
14 words
The process of claim 15 wherein said hydrophobic photographic additive is a dye coupler.
Claim 19
Dependent Claim
11 words
The process of claim 16 wherein said hydrophilic colloid is gelatin.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1986-12-05 | 1987-06-06 | 1987-12-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-12-05 | 1991-06-06 | 1991-12-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-12-05 | 1995-06-06 | 1995-12-06 | $7700.00 | Window Closed / Lapsed |