US3847612A - Light-sensitive heat-developable sheet material - Google Patents

Light-sensitive heat-developable sheet material Download PDF

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Publication number
US3847612A
US3847612A US00329107A US32910773A US3847612A US 3847612 A US3847612 A US 3847612A US 00329107 A US00329107 A US 00329107A US 32910773 A US32910773 A US 32910773A US 3847612 A US3847612 A US 3847612A
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sheet material
silver
imidazole
phthalic acid
mole
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US00329107A
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J Winslow
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3M Co
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Minnesota Mining and Manufacturing Co
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Application filed by Minnesota Mining and Manufacturing Co filed Critical Minnesota Mining and Manufacturing Co
Priority to US00329107A priority Critical patent/US3847612A/en
Priority to AR252176A priority patent/AR207001A1/en
Priority to CA190,312A priority patent/CA1009888A/en
Priority to NLAANVRAGE7400911,A priority patent/NL175857C/en
Priority to ES422553A priority patent/ES422553A1/en
Priority to SE7400848A priority patent/SE385741B/en
Priority to BR716/74A priority patent/BR7400716D0/en
Priority to IT48105/74A priority patent/IT1008189B/en
Priority to PH15469A priority patent/PH10823A/en
Priority to DE2405431A priority patent/DE2405431C3/en
Priority to BE140479A priority patent/BE810522A/en
Priority to CH143274A priority patent/CH607094A5/xx
Priority to FR7403389A priority patent/FR2216602B1/fr
Priority to GB488774A priority patent/GB1441477A/en
Priority to JP49013571A priority patent/JPS525845B2/ja
Application granted granted Critical
Publication of US3847612A publication Critical patent/US3847612A/en
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    • 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
    • G03C1/494—Silver salt compositions other than silver halide emulsions; Photothermographic systems ; Thermographic systems using noble metal compounds
    • G03C1/498—Photothermographic systems, e.g. dry silver
    • G03C1/49836—Additives
    • G03C1/49845—Active additives, e.g. toners, stabilisers, sensitisers

Definitions

  • This invention relates to photosensitive heatdevelopable dry silver sheet materials and has particular reference to improved means for obtaining images of desirable density and color.
  • Photosensitive heat-developable dry silver sheet materials contain a photosensitive silver halide catalyst-forming means in catalytic proximity with a heatsensitive combination of organic silver salt and reducing agent.
  • the reducing agent is a hindered phenol, it is found. desirable to include an image intensifier or toner material, of which phthalazinone has been an outstanding example.
  • Phthalazinone and various other materials have previously been employed as toners in light-stable heatsensitive copy-sheets based on organic silver salts and reducing agents.
  • Phthalazinone is a preferred material in compositions shown in U.S. Pat. No. 3,080,254; other materials therein disclosed, such for example as imidazole, must be employed in much larger amounts and are generally less effective.
  • Both phthalic acid and phthalazinone areshown in U.S. Pat. No. 3,218,166 to be effective toners for heat-sensitive compositions'containing organic silver salts and hindered phenolic reducing agents.
  • Phthalic acid may effectively be replaced in whole or in part by corresponding molar amounts of naphthalene-2,3-dicarboxylic acid or of o-phthalamic acid. Each of these compounds will be seen to be capable of condensation to form a five-membered heterocyclic ring structure.
  • substituted imidazoles having the S-membered heterocyclic imidazole ring strucparts by weight of phthalic acid and about 15 parts by.
  • the coating made with the half soap, containing 14.5 percent silver may be shown by calculation to contain 0.44 mole of phthalic acid and 0.73 mole of imidazole per mole of silver.
  • the transparent coating containing the full soap may be shown to contain 0.18 mole of phthalic acid and 0.057 mole. of benzimidazole per mole of silver. More broadly, it has been foundipossible to obtain distinct improvement in imageappearance with dry silver coatings based onv organic. silver. salts and hindered phenolic reducingagents by incorporating as toner materials animidazoleand;phthalic acid orequivalent in amounts within the.
  • silver half-soaps For use on paper or other non-transparent backings it is found convenient to use silver half-soaps, of which an equimolar. blend of silver behenate and behenic acid, prepared by precipitation from aqueous solution of the sodium salt of commercial behenic acid andanalyzing about 14.5 percent silver, represents a preferred example.
  • Other components suchfor example as colorings, opacifiers, extenders, spectral sensitizing-dyesetc. may be incorporated as required for various specific purposes.
  • a second composition is prepared by first mixing together acetone 339.9 grams methanol 1 18.5 cellulose acetate 25.0 colloidal silica 3.5
  • the mixture is applied over the previous layer and dried.
  • the dry coating weight is 2.7 grams/sq.m.
  • the spectral sensitizer is l-methyl-3-allyl-5[ (3-ethyl-2- benzoxazolinylidene) ethylidine]-2-thiohydantoin.
  • the molar ratios of phthalic acid and imidazole to total silver are 0.37 and 0.71 respectively.
  • EXAMPLE 2 A homogenate is prepared of silver behenate full soap gm. methyl isobutyl ketone 54 I toluene methyl ethyl ketone To 72 grams of the homogenate is added acetone acetone mercuric bromide (as .5% soln. in methanol) .0045
  • the vinyl resin is a copolymer, of vinyl acetate and vinyl chloride, containing hydroxyl radicals.
  • the Sudan yellow dye is optional
  • the mixture is prepared under darkroom conditions.
  • a second composition is prepared using toluene 34 gm. methyl ethyl ketone 32 methanol 22 vinyl chloride-vinyl acetate copolymer 6 tetrachlorophthalic anhydride .43 phthalic acid 2.2 benzimidazole .43 phenolic reducing agent of Example 1 3.42 antistatic agent (optional) ("Catanac SN") .43
  • the molar ratios of phthalic acid and benzimidazole to total silver are 0.167 and 0.046 respectively.
  • the film is exposed through a 0-4 continuous wedge to illumination from a carbon arc and developed by holding for 30 seconds in a bath of inert fluorocarbon liquid maintained at 260F.
  • the sensitometric values attained are:.
  • a photosensitive heat-developable sheet material having an image-forming stratum comprising (1) photo-sensitive silver halide catalyst-forming means and (2) heat-sensitive reactant image-forming means including an organic silver salt oxidizing agent and a hindered phenolic reducing agent for silver ion, the oxidation-reduction reaction of which to produce a visible change is accelerated by said catalyst, and (3) as sifier material consists of phthalic acid and imidazole.
  • Sheet material of claim 3 wherein said image intensifier material consists of phthalic acid and benzimidazole.

Abstract

Dust formation is avoided and dense black images are obtained during heat development of exposed dry silver sheet materials by employing a synergistic combination of individually ineffective toner materials.

Description

United States Patent 1 Winslow Nov. 12, 1974 1 LIGHT-SENSITIVE HEAT-DEVELOPABLE SHEET MATERIAL [75] Inventor: John M. Winslow, St. Paul, Minn.
[73] Assignee: Minnesota Mining and Manufacturing Company, St. Paul, Minn.
[22] Filed: Feb. 2, 1973 [21] Appl. No.: 329,107
[52] US. Cl 96/67, 96/114.1, 96/1 14.6 [51] Int. Cl G036 1/02 [58] Field of Search..... 96/67, 52, 58, 114.1, 114.6;
[56] References Cited UNITED STATES PATENTS 3,080,254 3/1963 Grant, Jr 117/36.8
Ritter 96/67 Birkeland 96/67 Primary Examine rDavid Klein Assistant Examiner-A1fonso T. Suro Pico Attorney, Agent, or FirmAlexander, Sell, Steldt & DeLaHunt [5 7 1 ABSTRACT 6 Claims, No Drawings LIGHT-SENSITIVE HEAT-DEVELOPABLE SHEET MATERIAL I This invention relates to photosensitive heatdevelopable dry silver sheet materials and has particular reference to improved means for obtaining images of desirable density and color.
Photosensitive heat-developable dry silver sheet materials, as described for example in U.S. Pat. No. 3,457,075, contain a photosensitive silver halide catalyst-forming means in catalytic proximity with a heatsensitive combination of organic silver salt and reducing agent. Particularly where the reducing agent is a hindered phenol, it is found. desirable to include an image intensifier or toner material, of which phthalazinone has been an outstanding example.
Phthalazinone and various other materials have previously been employed as toners in light-stable heatsensitive copy-sheets based on organic silver salts and reducing agents. Phthalazinone is a preferred material in compositions shown in U.S. Pat. No. 3,080,254; other materials therein disclosed, such for example as imidazole, must be employed in much larger amounts and are generally less effective. Both phthalic acid and phthalazinone areshown in U.S. Pat. No. 3,218,166 to be effective toners for heat-sensitive compositions'containing organic silver salts and hindered phenolic reducing agents. However in dry silver sheet materials employing the hindered phenolic reducing agents and containing also a catalytic quantity of photosensitive silver halide, neither phthalic acid nor imidazole has been found effective in causing useful darkening of the image. Phthalazinone is fully effective in dry silver sheets both as an image toner and for other purposes, as noted for example in U.S. Pat. No. 3,589,903; but this compound has been found to cause slight dusting, which becomes noticeable during heat development of large numbers of the exposed sheets. The dust factor apparently is a result of sublimation of the toner material, the vapor then condensing on cooler portions of the developing apparatus. It has also been observed that dry silver sheets containing phthalazinone have a tendency to lose photosensitivity and to provide less desirable images when first subjected to prolonged storage at elevated temperature and humidity.
It has now been found possible to provide photosensitive heat-developable dry silver imaging sheets which given dense black images, retain full effectiveness dur ing prolonged storage, and do not emit dust-forming vapors during development, by incorporating with the combination of silver halide, organic silver salt and bindered phenolic reducing agent significant small amounts of each phthalic acidand imidazole.
As'previously indicated, neither of these materials is at all effective by itself as an image toner for these dry silver sheet materials; yet the two together are found to be fully as effective as phthalazinone in providing image areas of desirable cold tone and this ability is maintained during prolonged storage.
Phthalic acid may effectively be replaced in whole or in part by corresponding molar amounts of naphthalene-2,3-dicarboxylic acid or of o-phthalamic acid. Each of these compounds will be seen to be capable of condensation to form a five-membered heterocyclic ring structure.
Somewhat analogously, substituted imidazoles having the S-membered heterocyclic imidazole ring strucparts by weight of phthalic acid and about 15 parts by.
weight of imidazole in a coating prepared with about 225 parts of silver behenate half soap, 155 parts of hindered phenolic reducing agent, and 4 par-ts of resinous binders, applied at a dry coating weight, after. removal of volatile liquid vehicle, of about ten grarnsper.
square meter. In another example, 50 parts by weight of phthalic acid and 10 parts of benzimidazole. are foundto be effective in atransparent coating prepared with approximately 715 parts of silver behenate full soap, 1,000 parts of resinous binders, and 770. parts of hindered phenolic reducing agent, applied at 19 grams per sq. meter.
The coating made with the half soap, containing 14.5 percent silver, may be shown by calculation to contain 0.44 mole of phthalic acid and 0.73 mole of imidazole per mole of silver. Similarly, the transparent coating containing the full soap may be shown to contain 0.18 mole of phthalic acid and 0.057 mole. of benzimidazole per mole of silver. More broadly, it has been foundipossible to obtain distinct improvement in imageappearance with dry silver coatings based onv organic. silver. salts and hindered phenolic reducingagents by incorporating as toner materials animidazoleand;phthalic acid orequivalent in amounts within the. approximate range of 0.04 to 0.8 mole of the acid and 0.02 to 1.4 moles of the imidazole per mole of total silver. Apreferred range is about 0.15 to 0.5 mole of acid and 0.1 to 0.7 mole of imidazole per mole of silver. In these coatings it willbe recognized that-some minor amount, not more than about ten percent, of the total silvenwill be present as photosensitive silver halide, the remainder being light-stable organic silver salt.
Some improvement in image appearance may be achieved in accordance with the principles of the invention when using other hindered phenolic reducing agents, such for example as those listed in the afore mentioned U.S. Pat. No. 3,218,166; but the best image appearance has been realized when using as the reducing agent the compound 2,6-methy1ene?bis(2-hydroxy- 3-tertiarybuty1-5-methy1phenyl)-4-methylphenol, a commercial form of which is also known as Plastanox 80 antioxidant; and this substance is presently greatly preferred in the sheet materials of this invention.
For use on paper or other non-transparent backings it is found convenient to use silver half-soaps, of which an equimolar. blend of silver behenate and behenic acid, prepared by precipitation from aqueous solution of the sodium salt of commercial behenic acid andanalyzing about 14.5 percent silver, represents a preferred example. Transparentsheet materials .rnade ontransparent film backings require atransparentcoatingand for this purpose the silver behenate full soap, containing not more than about fouror five percent of free behenic acid and analyzing about 25 .2=percent silver, may be used. Other components, suchfor example as colorings, opacifiers, extenders, spectral sensitizing-dyesetc. may be incorporated as required for various specific purposes.
The following examples are offered for further illustration, but not as limitation, of the principles of the invention'. Proportions are in parts by weight unless otherwise noted.
EXAMPLE 1 Silver behenate half soap is homogenized in acetone and then diluted with further acetone and toluene to the formula half soap 10.83 parts acetone 58.94 toluene 30.23 v
' To 80.85 grams of the homogenate is added, under darkroom conditions,
acetone 6.37 grams polyvinyl butyral (B-76 resin) 10.40 gm. 3% solution of mercuric acetate in methanol 1 ml. 5% solution of calcium bromide in methanol 1 ml.
6 grams hindered phenolic reducing agent (Plastanox 80) i and the mixture is coated on paper pre-treated with polyvinyl alcohol. The coating weight after drying is seven grams per square meter.
A second composition is prepared by first mixing together acetone 339.9 grams methanol 1 18.5 cellulose acetate 25.0 colloidal silica 3.5
To 100 grams of the mixture is then added 0.25% Victoria Blue dye in methanol 0 1 ml. 0.05% spectral sensitizer in methanol 1.5 ml. phthalic acid 0.6 gm. imidazole 0 4 gm.
The mixture is applied over the previous layer and dried. The dry coating weight is 2.7 grams/sq.m. The spectral sensitizer is l-methyl-3-allyl-5[ (3-ethyl-2- benzoxazolinylidene) ethylidine]-2-thiohydantoin. The molar ratios of phthalic acid and imidazole to total silver are 0.37 and 0.71 respectively.
A sample is exposed sensitometrically and is developed by heating for three seconds at 260F. with results as follows:
D D,,,,, gamma speed image .19 1.28 1.35 1.0 black 1),, D g, gamma speed image color .13 1.30 1.20 1.20 blaclt The test conditions, which are sufficiently severe to cause significant deterioration of properties in sheets prepared with phthalazinone, are seen to have very little if any adverse effect on the .productof the present example.
EXAMPLE 2 A homogenate is prepared of silver behenate full soap gm. methyl isobutyl ketone 54 I toluene methyl ethyl ketone To 72 grams of the homogenate is added acetone acetone mercuric bromide (as .5% soln. in methanol) .0045
mercuric acetate (as 2.5% soln. in methanol) .216. polyvinyl butyral 92 vinyl resin (VAGHU 1.8
Sudan yellow (as .05% soln. in methanol .015.
The vinyl resin is a copolymer, of vinyl acetate and vinyl chloride, containing hydroxyl radicals.
The Sudan yellow dye is optional The mixture is prepared under darkroom conditions.
It is coated on transparent polyester film to a coating weight, after drying, of 16.2 gm/sq.m. Y
A second composition is prepared using toluene 34 gm. methyl ethyl ketone 32 methanol 22 vinyl chloride-vinyl acetate copolymer 6 tetrachlorophthalic anhydride .43 phthalic acid 2.2 benzimidazole .43 phenolic reducing agent of Example 1 3.42 antistatic agent (optional) ("Catanac SN") .43
and is applied over the first coat at a coating weight, after drying, of 2.7 grams/sqm. The molar ratios of phthalic acid and benzimidazole to total silver are 0.167 and 0.046 respectively.
The film is exposed through a 0-4 continuous wedge to illumination from a carbon arc and developed by holding for 30 seconds in a bath of inert fluorocarbon liquid maintained at 260F. The sensitometric values attained are:.
D, D gamma image color .08 2.60 2.0 blue-black What is claimed is as follows:
1. A photosensitive heat-developable sheet material having an image-forming stratum comprising (1) photo-sensitive silver halide catalyst-forming means and (2) heat-sensitive reactant image-forming means including an organic silver salt oxidizing agent and a hindered phenolic reducing agent for silver ion, the oxidation-reduction reaction of which to produce a visible change is accelerated by said catalyst, and (3) as sifier material consists of phthalic acid and imidazole.
5. Sheet material of claim 3 wherein said image intensifier material consists of phthalic acid and benzimidazole. Y
6. Sheet material of claim 1 wherein said hindered phenolic reducing agent is 2,6-methylene-bis(2- hydroxy-3-tertiarybutyl-5-methylphenyl)-4- methylphenol and said image intensifier material consists of 0. l 5 to 0.5 mole of phthalic acid and 0.04 to 0.7 mole of imidazole or benzimidazole per mole of total silver.

Claims (6)

1. A PHOTOSENSITIVE HEAT-DEVELOPABLE SHEET MATERIAL HAVING AN IMAGE-FORMING STRATUM COMPRISING (1) PHOTO-SENSITIVE SILVER HALIDE CATALYST-FORMING MEANS AND (2) HEAT-SENSITIVE REACTING IMAGE-FORMING MEANS INCLUDING AN ORGANIC SILVER SALT OXIDIZING AGENT AND A HINDERED PHENOLIC REDUCING AGENT FOR SILVER ION, THE OXIDATION-REDUCTION REACTION OF WHICH TO PRODUCE A VISIBLE CHANGE IS ACCELERATED BY SAID CATALYST, AND (3) AS IMAGE INTENSIFIER MATERIAL, A MIXTURE OF (A) ONE OR MORE OF THE COMPOUNDS PHTHALIC ACID, MAPHTHALENE -2,3-DICARBOXYLIC ACID, OR PHTHALAMIC ACIE, AND (B) AN IMIDAZOLE.
2. Sheet material of claim 1 wherein said hindered phenolic reducing agent is 2,6-methylene-bis(2-hydroxy-3-tertiary-butyl-5-methylphenyl)-4-methylphenol.
3. Sheet material of claim 1 wherein said intensifier material is constituted of 0.04 to 0.8 mole of said acid and 0.02 to 1.4 moles of said imidazole per mole of total silver.
4. Sheet material of claim 3 wherein said image intensifier material consists of phthalic acid and imidazole.
5. Sheet material of claim 3 wherein said image intensifier material consists of phthalic acid and benzimidazole.
6. Sheet material of claim 1 wherein said hindered phenolic reducing agent is 2,6-methylene-bis(2-hydroxy-3-tertiarybutyl-5-methylphenyl)-4-methylphenol and said image intensifier material consists of 0.15 to 0.5 mole of phthalic acid and 0.04 to 0.7 mole of imidazole or benzimidazole per mole of total silver.
US00329107A 1973-02-02 1973-02-02 Light-sensitive heat-developable sheet material Expired - Lifetime US3847612A (en)

Priority Applications (15)

Application Number Priority Date Filing Date Title
US00329107A US3847612A (en) 1973-02-02 1973-02-02 Light-sensitive heat-developable sheet material
AR252176A AR207001A1 (en) 1973-02-02 1974-01-01 HEAT REVELABLE PHOTOSENSITIVE LAMINAR MATERIAL
CA190,312A CA1009888A (en) 1973-02-02 1974-01-16 Light-sensitive heat-developable sheet material
NLAANVRAGE7400911,A NL175857C (en) 1973-02-02 1974-01-23 PHOTO SENSITIVE, SHEET MATERIAL.
ES422553A ES422553A1 (en) 1973-02-02 1974-01-23 Light-sensitive heat-developable sheet material
SE7400848A SE385741B (en) 1973-02-02 1974-01-23 PHOTOSENSITIVE, HEAT-PRODUCING SHEET MATERIAL
BR716/74A BR7400716D0 (en) 1973-02-02 1974-01-31 SHEET MATERIAL, PHOTOSENSITIVE, REVELABLE BY HEAT
PH15469A PH10823A (en) 1973-02-02 1974-02-01 Light-sensitive heat-developable sheet material
IT48105/74A IT1008189B (en) 1973-02-02 1974-02-01 IMPROVEMENT IN MATERIALS IN PHOTOSENSITIVE SHEETS DEVELOPABLE BY THERMAL ACTION
DE2405431A DE2405431C3 (en) 1973-02-02 1974-02-01 Thermophotographic recording material
BE140479A BE810522A (en) 1973-02-02 1974-02-01 HOT-DEVELOPABLE PHOTOSENSITIVE SHEET
CH143274A CH607094A5 (en) 1973-02-02 1974-02-01
FR7403389A FR2216602B1 (en) 1973-02-02 1974-02-01
GB488774A GB1441477A (en) 1973-02-02 1974-02-01 Light-sensitive heat developable sheet material
JP49013571A JPS525845B2 (en) 1973-02-02 1974-02-01

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JP (1) JPS525845B2 (en)
AR (1) AR207001A1 (en)
BE (1) BE810522A (en)
BR (1) BR7400716D0 (en)
CA (1) CA1009888A (en)
CH (1) CH607094A5 (en)
DE (1) DE2405431C3 (en)
ES (1) ES422553A1 (en)
FR (1) FR2216602B1 (en)
GB (1) GB1441477A (en)
IT (1) IT1008189B (en)
NL (1) NL175857C (en)
PH (1) PH10823A (en)
SE (1) SE385741B (en)

Cited By (31)

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US3994732A (en) * 1975-09-08 1976-11-30 Minnesota Mining & Mfg Dry silver toners
FR2412870A1 (en) * 1977-12-23 1979-07-20 Asahi Chemical Ind HOT-DEVELOPABLE PHOTOSENSITIVE MATERIALS
US4260677A (en) * 1976-03-12 1981-04-07 Minnesota Mining And Manufacturing Company Thermographic and photothermographic materials having silver salt complexes therein
US4585734A (en) * 1985-02-01 1986-04-29 Minnesota Mining And Manufacturing Company Photothermographic toners
US4675277A (en) * 1984-09-25 1987-06-23 Fuji Photo Film Co., Ltd. Heat developable light-sensitive material
US5275932A (en) * 1992-03-16 1994-01-04 Minnesota Mining And Manufacturing Company Thermal development accelerators for thermographic materials
US5464737A (en) * 1993-04-29 1995-11-07 Minnesota Mining And Manufacturing Company Post-processing stabilizers for photothermographic articles
US5492803A (en) * 1995-01-06 1996-02-20 Minnesota Mining And Manufacturing Company Hydrazide redox-dye-releasing compounds for photothermographic elements
US5492804A (en) * 1994-06-30 1996-02-20 Minnesota Mining And Manufacturing Company Chromogenic leuco redox-dye-releasing compounds for photothermographic elements
US5492805A (en) * 1994-06-30 1996-02-20 Minnesota Mining And Manufacturing Company Blocked leuco dyes for photothermographic elements
US5891615A (en) * 1997-04-08 1999-04-06 Imation Corp. Chemical sensitization of photothermographic silver halide emulsions
US5928857A (en) * 1994-11-16 1999-07-27 Minnesota Mining And Manufacturing Company Photothermographic element with improved adherence between layers
US5939249A (en) * 1997-06-24 1999-08-17 Imation Corp. Photothermographic element with iridium and copper doped silver halide grains
US6117624A (en) * 1993-06-04 2000-09-12 Eastman Kodak Company Infrared sensitized, photothermographic article
US6171707B1 (en) 1994-01-18 2001-01-09 3M Innovative Properties Company Polymeric film base having a coating layer of organic solvent based polymer with a fluorinated antistatic agent
US6340985B1 (en) 1997-12-10 2002-01-22 Fuji Photo Film Co. Ltd. Thermal recording apparatus
US6630291B1 (en) 2002-08-21 2003-10-07 Eastman Kodak Company Thermally sensitive imaging materials containing phthalazine precursor
US20050186520A1 (en) * 2004-02-25 2005-08-25 Eastman Kodak Company Silver-free black-and-white thermographic materials
US20050186518A1 (en) * 2004-02-25 2005-08-25 Eastman Kodak Company Silver-free black-and-white thermographic materials containing a benzoquinone and methods of imaging
US20050186521A1 (en) * 2004-02-25 2005-08-25 Eastman Kodak Company Black-and-white thermographic materials with improved image tone
US7468241B1 (en) 2007-09-21 2008-12-23 Carestream Health, Inc. Processing latitude stabilizers for photothermographic materials
US7524621B2 (en) 2007-09-21 2009-04-28 Carestream Health, Inc. Method of preparing silver carboxylate soaps
US7622247B2 (en) 2008-01-14 2009-11-24 Carestream Health, Inc. Protective overcoats for thermally developable materials
US20100022744A1 (en) * 2006-12-21 2010-01-28 Nippon Soda Co., Ltd. Clathrate compound, curing catalyst, composition for forming cured resin, and cured resin
US20100179250A1 (en) * 2007-09-21 2010-07-15 Nippon Soda Co., Ltd. Inclusion complex containing epoxy resin composition for semiconductor encapsulation
US8623942B2 (en) 2009-03-11 2014-01-07 Nippon Soda Co., Ltd. Epoxy resin composition, curing agent, and curing accelerator
US8735529B2 (en) 2006-12-21 2014-05-27 Nippon Soda Co., Ltd. Clathrate compound, curing catalyst, composition for forming cured resin, and cured resin
WO2015148028A1 (en) 2014-03-24 2015-10-01 Carestream Health, Inc. Thermally developable imaging materials
WO2016073086A1 (en) 2014-11-04 2016-05-12 Carestream Health, Inc. Image forming materials, preparations, and compositions
WO2016195950A1 (en) 2015-06-02 2016-12-08 Carestream Health, Inc. Thermally developable imaging materials and methods
WO2017123444A1 (en) 2016-01-15 2017-07-20 Carestream Health, Inc. Method of preparing silver carboxylate soaps

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JPS5147429A (en) * 1974-10-21 1976-04-23 Fuji Photo Film Co Ltd Netsugenzokiniokeru haikisochi
JPS51101523A (en) * 1975-03-05 1976-09-08 Fuji Photo Film Co Ltd NETSUGENZOKANKOZAIRYO
AR206458A1 (en) * 1975-03-17 1976-07-23 Minnesota Mining & Mfg THERMAL AND PHOTOTHERMOGRAPHIC SHEET MATERIALS
JPS5271238A (en) * 1975-12-11 1977-06-14 Oriental Photo Ind Co Ltd Method of forming picture with heat development photosensitive material
JPS5911093B2 (en) * 1977-11-01 1984-03-13 富士写真フイルム株式会社 Photosensitive composition for heat-developable photosensitive materials
JP5972847B2 (en) 2013-10-21 2016-08-17 三菱日立パワーシステムズ株式会社 Burner tip and combustion burner and boiler

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US3589903A (en) * 1968-02-28 1971-06-29 Minnesota Mining & Mfg Silver halide,heat-developable image sheet containing mercuric ion

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US4260677A (en) * 1976-03-12 1981-04-07 Minnesota Mining And Manufacturing Company Thermographic and photothermographic materials having silver salt complexes therein
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US5275932A (en) * 1992-03-16 1994-01-04 Minnesota Mining And Manufacturing Company Thermal development accelerators for thermographic materials
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US6171707B1 (en) 1994-01-18 2001-01-09 3M Innovative Properties Company Polymeric film base having a coating layer of organic solvent based polymer with a fluorinated antistatic agent
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US8735529B2 (en) 2006-12-21 2014-05-27 Nippon Soda Co., Ltd. Clathrate compound, curing catalyst, composition for forming cured resin, and cured resin
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Publication number Publication date
DE2405431A1 (en) 1974-08-15
NL175857C (en) 1985-01-02
CA1009888A (en) 1977-05-10
SE385741B (en) 1976-07-19
FR2216602A1 (en) 1974-08-30
CH607094A5 (en) 1978-11-30
FR2216602B1 (en) 1978-03-10
DE2405431C3 (en) 1980-02-28
JPS49107727A (en) 1974-10-14
AR207001A1 (en) 1976-09-09
DE2405431B2 (en) 1979-06-21
JPS525845B2 (en) 1977-02-17
BE810522A (en) 1974-08-01
BR7400716D0 (en) 1974-09-10
ES422553A1 (en) 1976-04-16
NL175857B (en) 1984-08-01
IT1008189B (en) 1976-11-10
GB1441477A (en) 1976-06-30
NL7400911A (en) 1974-08-06
PH10823A (en) 1977-09-08

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