US3232763A - Gelatin compositions containing a bisisomaleimide hardener - Google Patents
Gelatin compositions containing a bisisomaleimide hardener Download PDFInfo
- Publication number
- US3232763A US3232763A US265043A US26504363A US3232763A US 3232763 A US3232763 A US 3232763A US 265043 A US265043 A US 265043A US 26504363 A US26504363 A US 26504363A US 3232763 A US3232763 A US 3232763A
- Authority
- US
- United States
- Prior art keywords
- gelatin
- bisisomaleimide
- hardener
- compositions containing
- gelatin compositions
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 108010010803 Gelatin Proteins 0.000 title description 13
- 239000008273 gelatin Substances 0.000 title description 13
- 229920000159 gelatin Polymers 0.000 title description 13
- 235000019322 gelatine Nutrition 0.000 title description 13
- 235000011852 gelatine desserts Nutrition 0.000 title description 13
- 239000004848 polyfunctional curative Substances 0.000 title description 8
- 239000000203 mixture Substances 0.000 title description 4
- 239000000839 emulsion Substances 0.000 claims description 8
- 229910052709 silver Inorganic materials 0.000 claims description 5
- 239000004332 silver Substances 0.000 claims description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 229920002301 cellulose acetate Polymers 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 2
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 description 1
- SLJJEYCPTRKHFI-UHFFFAOYSA-N 3-[6-(2,5-dioxopyrrol-3-yl)hexyl]pyrrole-2,5-dione Chemical compound O=C1NC(=O)C(CCCCCCC=2C(NC(=O)C=2)=O)=C1 SLJJEYCPTRKHFI-UHFFFAOYSA-N 0.000 description 1
- OMIHGPLIXGGMJB-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]hepta-1,3,5-triene Chemical compound C1=CC=C2OC2=C1 OMIHGPLIXGGMJB-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical group C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 239000007888 film coating Substances 0.000 description 1
- 238000009501 film coating Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 229920003192 poly(bis maleimide) Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- ZUNKMNLKJXRCDM-UHFFFAOYSA-N silver bromoiodide Chemical compound [Ag].IBr ZUNKMNLKJXRCDM-UHFFFAOYSA-N 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
- G03C1/06—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
- G03C1/30—Hardeners
Definitions
- hexamethylene bisisomaleimide were added to separate portions of a high speed gelatin-silver bromoiodide emul- Thls lnvemlon relates to gelatm coatmg compqsltlons 10 sion, which had been panchromatical-ly sensitized with a d layers prepared therefrom composed of ge af and cyanine dye, in the proportions indicated inthe table.
- n is an integer of 4 to 10.
- Example 2 A slurry of 51.2 grams of N,N-tetramethylene-bismaleamic acid in 500 ml. of dichloromethane was stirred vigorously while a solution of 82.5 grams of commercial dicyclohexylcarbodiimide in ml. of dichloromethane Was added dropwise over a period of 50 minutes. The mixture was stirred for 24 hours, then cooled and the solids were removed by filtration. The crude residue was extracted with hot benzene, filtered and evaporated to dryness. The residue was slurried with cold ether and filtered. The crude, colorless crystalline solid was recrystallized With benzene-ether to give N,N'-tetramethylenebisisomaleimide having a melting point of 146.5 to 148.5 C.
- Example 2 The tetramethylene bisisomaleimide prepared in Example 2 was added to separate portions of high-speed silver bromoiodide emulsion which had been panchromatically sensitized with a cyanine dye, in the proportions indicated in the table. A sample of the emulsion without hardener was also taken. Each emulsion sample was coated onto a cellulose acetate film support at a coverage of 459 mg. of silver and 1040 mg. of gelatin per square foot. A sample of each film coating was exposed on an Eastman 1B sensitometer, processed for five mine; utes in Kodak DK-SO developer, fixed, Washed and dried with the following results:
- composition comprising gelatin containing therein hexamethylene bisisomaleimide.
- HC-O o n being an integer of 4 to 10.
- composition comprising gelatin containing therein tetrarnethylene bisisomaleimide.
Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- General Physics & Mathematics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1054123D GB1054123A (enrdf_load_stackoverflow) | 1963-03-14 | ||
| US265043A US3232763A (en) | 1963-03-14 | 1963-03-14 | Gelatin compositions containing a bisisomaleimide hardener |
| FR966014A FR1383643A (fr) | 1963-03-14 | 1964-03-04 | Nouvelle composition à base de gélatine utilisable en photographie |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US265043A US3232763A (en) | 1963-03-14 | 1963-03-14 | Gelatin compositions containing a bisisomaleimide hardener |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3232763A true US3232763A (en) | 1966-02-01 |
Family
ID=23008712
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US265043A Expired - Lifetime US3232763A (en) | 1963-03-14 | 1963-03-14 | Gelatin compositions containing a bisisomaleimide hardener |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US3232763A (enrdf_load_stackoverflow) |
| FR (1) | FR1383643A (enrdf_load_stackoverflow) |
| GB (1) | GB1054123A (enrdf_load_stackoverflow) |
Cited By (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3462273A (en) * | 1965-10-08 | 1969-08-19 | Agfa Gevaert Nv | 2-dioxolanones (carboxylic acid esters) protein hardeners |
| EP0124795A2 (en) | 1983-04-11 | 1984-11-14 | Fuji Photo Film Co., Ltd. | Silver halide photographic emulsion |
| US5744574A (en) * | 1995-12-05 | 1998-04-28 | Minnesota Mining And Manufacturing Company | Isomaleimides and polymers derived therefrom |
| US6020398A (en) * | 1998-05-22 | 2000-02-01 | Eastman Kodak Company | Pigmented ink jet inks for poly (vinylalcohol) receivers |
| US6045219A (en) * | 1998-05-22 | 2000-04-04 | Eastman Kodak Company | Pigmented ink jet prints on gelatin overcoated with hardeners |
| US6074057A (en) * | 1998-05-22 | 2000-06-13 | Eastman Kodak Company | Pigmented ink jet inks and recording elements containing hardening agents |
| US6082853A (en) * | 1998-05-22 | 2000-07-04 | Eastman Kodak Company | Printing apparatus with processing tank |
| US6161929A (en) * | 1998-05-22 | 2000-12-19 | Eastman Kodak Company | Inkjet images on PVA overcoated with hardener solution |
| US6176574B1 (en) | 1998-05-22 | 2001-01-23 | Eastman Kodak Company | Printing apparatus with spray bar for improved durability |
| US6254230B1 (en) | 1998-05-22 | 2001-07-03 | Eastman Kodak Company | Ink jet printing apparatus with print head for improved image durability |
| US6435678B1 (en) | 1998-05-22 | 2002-08-20 | Eastman Kodak Company | Waterfast ink jet images treated with hardeners |
| US20060181658A1 (en) * | 2005-02-16 | 2006-08-17 | Eastman Kodak Company | Conductive absorption layer for flexible displays |
| US20060215077A1 (en) * | 2005-03-22 | 2006-09-28 | Eastman Kodak Company | High performance flexible display with improved mechanical properties |
| WO2008038764A1 (fr) | 2006-09-28 | 2008-04-03 | Fujifilm Corporation | Écran à émission spontanée, procédé de fabrication d'un écran à émission spontanée, film conducteur transparent, dispositif électroluminescent, électrode transparente de cellule solaire et électrode transparente de papier électronique |
| US7507449B2 (en) | 2006-05-30 | 2009-03-24 | Industrial Technology Research Institute | Displays with low driving voltage and anisotropic particles |
| DE112007001129T5 (de) | 2006-06-29 | 2009-07-09 | Industrial Technology Research Institute | Gast-Wirt-Polymer-Flüssigkristallanzeigen auf einem einzigen Substrat |
| EP2385425A1 (en) | 2010-05-07 | 2011-11-09 | Fujifilm Corporation | Silver halide photographic light-sensitive material for movie |
| WO2012035314A1 (en) | 2010-09-17 | 2012-03-22 | Fujifilm Manufacturing Europe Bv | Photographic paper |
| WO2021213762A1 (en) | 2020-04-24 | 2021-10-28 | Fujifilm Manufacturing Europe Bv | Photographic paper |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2726162A (en) * | 1951-12-01 | 1955-12-06 | Eastman Kodak Co | Hardening of gelatin |
| US2899327A (en) * | 1959-08-11 | Glue setting accelerators | ||
| US2992109A (en) * | 1960-06-17 | 1961-07-11 | Eastman Kodak Co | Hardening of photographic emulsions |
| US2994611A (en) * | 1958-03-19 | 1961-08-01 | Hoechst Ag | Hardening of protein |
-
0
- GB GB1054123D patent/GB1054123A/en active Active
-
1963
- 1963-03-14 US US265043A patent/US3232763A/en not_active Expired - Lifetime
-
1964
- 1964-03-04 FR FR966014A patent/FR1383643A/fr not_active Expired
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2899327A (en) * | 1959-08-11 | Glue setting accelerators | ||
| US2726162A (en) * | 1951-12-01 | 1955-12-06 | Eastman Kodak Co | Hardening of gelatin |
| US2994611A (en) * | 1958-03-19 | 1961-08-01 | Hoechst Ag | Hardening of protein |
| US2992109A (en) * | 1960-06-17 | 1961-07-11 | Eastman Kodak Co | Hardening of photographic emulsions |
Cited By (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3462273A (en) * | 1965-10-08 | 1969-08-19 | Agfa Gevaert Nv | 2-dioxolanones (carboxylic acid esters) protein hardeners |
| EP0124795A2 (en) | 1983-04-11 | 1984-11-14 | Fuji Photo Film Co., Ltd. | Silver halide photographic emulsion |
| US5744574A (en) * | 1995-12-05 | 1998-04-28 | Minnesota Mining And Manufacturing Company | Isomaleimides and polymers derived therefrom |
| US6435678B1 (en) | 1998-05-22 | 2002-08-20 | Eastman Kodak Company | Waterfast ink jet images treated with hardeners |
| US6074057A (en) * | 1998-05-22 | 2000-06-13 | Eastman Kodak Company | Pigmented ink jet inks and recording elements containing hardening agents |
| US6082853A (en) * | 1998-05-22 | 2000-07-04 | Eastman Kodak Company | Printing apparatus with processing tank |
| US6161929A (en) * | 1998-05-22 | 2000-12-19 | Eastman Kodak Company | Inkjet images on PVA overcoated with hardener solution |
| US6176574B1 (en) | 1998-05-22 | 2001-01-23 | Eastman Kodak Company | Printing apparatus with spray bar for improved durability |
| US6254230B1 (en) | 1998-05-22 | 2001-07-03 | Eastman Kodak Company | Ink jet printing apparatus with print head for improved image durability |
| US6020398A (en) * | 1998-05-22 | 2000-02-01 | Eastman Kodak Company | Pigmented ink jet inks for poly (vinylalcohol) receivers |
| US6045219A (en) * | 1998-05-22 | 2000-04-04 | Eastman Kodak Company | Pigmented ink jet prints on gelatin overcoated with hardeners |
| US7630029B2 (en) | 2005-02-16 | 2009-12-08 | Industrial Technology Research Institute | Conductive absorption layer for flexible displays |
| US20060181658A1 (en) * | 2005-02-16 | 2006-08-17 | Eastman Kodak Company | Conductive absorption layer for flexible displays |
| US20060215077A1 (en) * | 2005-03-22 | 2006-09-28 | Eastman Kodak Company | High performance flexible display with improved mechanical properties |
| US7557875B2 (en) | 2005-03-22 | 2009-07-07 | Industrial Technology Research Institute | High performance flexible display with improved mechanical properties having electrically modulated material mixed with binder material in a ratio between 6:1 and 0.5:1 |
| US7507449B2 (en) | 2006-05-30 | 2009-03-24 | Industrial Technology Research Institute | Displays with low driving voltage and anisotropic particles |
| DE112007001129T5 (de) | 2006-06-29 | 2009-07-09 | Industrial Technology Research Institute | Gast-Wirt-Polymer-Flüssigkristallanzeigen auf einem einzigen Substrat |
| WO2008038764A1 (fr) | 2006-09-28 | 2008-04-03 | Fujifilm Corporation | Écran à émission spontanée, procédé de fabrication d'un écran à émission spontanée, film conducteur transparent, dispositif électroluminescent, électrode transparente de cellule solaire et électrode transparente de papier électronique |
| EP2385425A1 (en) | 2010-05-07 | 2011-11-09 | Fujifilm Corporation | Silver halide photographic light-sensitive material for movie |
| WO2012035314A1 (en) | 2010-09-17 | 2012-03-22 | Fujifilm Manufacturing Europe Bv | Photographic paper |
| WO2021213762A1 (en) | 2020-04-24 | 2021-10-28 | Fujifilm Manufacturing Europe Bv | Photographic paper |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1054123A (enrdf_load_stackoverflow) | |
| FR1383643A (fr) | 1964-12-24 |
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