US3218166A - Heat sensitive copy sheet - Google Patents

Heat sensitive copy sheet Download PDF

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Publication number
US3218166A
US3218166A US239807A US23980762A US3218166A US 3218166 A US3218166 A US 3218166A US 239807 A US239807 A US 239807A US 23980762 A US23980762 A US 23980762A US 3218166 A US3218166 A US 3218166A
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United States
Prior art keywords
silver
image
reducing agent
sheet
soap
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Expired - Lifetime
Application number
US239807A
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English (en)
Inventor
John L Reitter
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3M Co
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Minnesota Mining and Manufacturing Co
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Filing date
Publication date
Priority to DENDAT1250842D priority Critical patent/DE1250842B/de
Priority to NL300853D priority patent/NL300853A/xx
Application filed by Minnesota Mining and Manufacturing Co filed Critical Minnesota Mining and Manufacturing Co
Priority to US239807A priority patent/US3218166A/en
Priority to GB44452/63A priority patent/GB1071021A/en
Priority to ES0293547A priority patent/ES293547A1/es
Priority to BE640183A priority patent/BE640183A/xx
Priority to SE12849/63A priority patent/SE328472B/xx
Priority to NL63300853A priority patent/NL139485B/xx
Priority to AT940263A priority patent/AT268875B/de
Priority to CH1433663A priority patent/CH454188A/de
Priority to FR954747A priority patent/FR1383197A/fr
Priority to DK549463AA priority patent/DK121305B/da
Application granted granted Critical
Publication of US3218166A publication Critical patent/US3218166A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • G03C1/4989—Photothermographic systems, e.g. dry silver characterised by a thermal imaging step, with or without exposure to light, e.g. with a thermal head, using a laser

Definitions

  • the film may contain a photosensitive aromatic hydroxy reducing agent, the image sheet then containing a water-insolublev silver 3,2'l8,166 Patented Nov. 16, 1965 ICC 2 z image sheet.
  • the visible change occurring on uniformly heating the exposed intermediate film, with its remaining small amounts of photosensitive reducing agent at image areas, in contact with the image sheet containing the small amount of uniformly distributed non-photosensitive reducing agent, is of much greater intensity than could be ing comprising silver soap and a small amount of a light stable reducing agent.
  • FIGURE 2 represents another embodiment in which both of -the reducing-agent cornponents are incorporated with the silver coating.
  • the reducing agent is reactive with the silver soap at moderately elevated temperatures with liberation of free silver, accompanied by a visible change.
  • Exposure to actinic radiation desensitizes the reducing agent, i.e. renders it nonreactive with the silver ion, and thus prevents occurrence of the image forming reaction at the I exposed areas when the two sheets are subsequentlyl heated in contacting face-to-face relationship.
  • the reducing agents employed in the intermediate films are photosensitive, being rendered incapable of causing reduction of the silver ion when sut'- ciently 'exposed to actinic radiation.
  • Other known reducing agents for silver ions-do not possess this property of photosen'sitivity, or are so slightly photosensitive as to be essentially, permanently stable under long continued exposure u'der ordi-nary storage and use conditions.v
  • the incorporation of such materials into the silver soap coating of the image sheet causes pronounced darkening of the -sheet when heated.
  • Excellent heat-sensitive copy sheets havey been made containing these light stable reducing agents inlintimate juxtaposition Withy the particles of v tion in the image or receptor sheet coating of certain essentially light-stable reducing agents for silver ion, and in significantly lesser amounts than normally required to produce desired image density on momentary heating-is effective-in providing fully defined, high density images while avoiding any darkening of background areas of the film, Mylar polyester film being thermographic copying procedure.
  • y Paper is a preferrred substrate for the image sheet. Itmay be of any desired weight.
  • the reactive coating may also be applied to other heat-resisting substrates, e.g. wood, glass, and fabric.
  • the transparent carrier of the intermediate sheet will ordinarily be a thin plastic a preferred example. Thin unfilled paper is also useful.
  • the reactive components will ordinarily be retained in place on the carrier or substrate by means of minimal amounts of film-forming binder materials. Suitable subcoats or prime coats may be used to insure proper bonding of the active coating, particularly on the transparent films.
  • the reactants may alternatively be introduced into fibrous paper-like webs during the formation thereof -and in the substantial absence of any nlm-forming binder components.
  • n Silver soaps of long-chain fatty acids e.g. silver behenate and silver stearate, are colorless, visibly stable ⁇ toward light, insoluble in many volatile liquid vehicles,
  • Photosensitive reducing agents which have been found effective include l-hydroxy-rl-methoxy naphthalene, 1- hydroxy-2-methyl-4-methoxy naphthalene, l-hydroxy-4- ethoxy naphthalene, 4,4'dimethoxyl,1dihydroxy2,2' binaphthyl, l,l'-dihydroxy-LZ'-binaphthyl, 1,4-dihydroxy napthtalene, 1,3-dihydroxy naphthalene, 1-hydroxy-4- amino naphthalene, the bis-dihydroxynaphthalene-dimethylmethane condensation product of 1,5-dihydroxy naphthalene and acetone, 1-hydroxy-2-phenyl-4-methoxy naphthalene, the condensation product of two mols of 1,5-dihydroxynaphthalene and one mol of adipoyl chloride.
  • the photosensitive reducing agent may be an alpha-naphthol having attached directly to the hydroxy. substituted aromatic ring a preponderance of electron donor groups which may be alkyl, aryl, alkoxy, aryloxy, hydroxy or amino.
  • Readily volatile photosensitive reducing agents are employed in the intermediate sheet of the two-sheet composite; materials lof lesser volatility are Ti useful in unitary copy-sheets in which all of the reactants are contained in a single layer.
  • a particularly effective light stable silver ion reducing agent which has given excellent results in the practice of the invention is 2,6-ditertiarybutyl-p-cresol, also known as Ionol or CAO-3.
  • Ionol also known as Ionol or CAO-3.
  • this material reduces the silver ionand produces a visible change when the sheet is heated for a somewhat longer time and at somewhat higher temperature than is normally the case in thermographic copying processes.
  • the sheet fails to provide the required density of image when so heated, and remains virtually unchanged when heated for a time and at a temperature such as are ordinarily encountered in thermographic copying processes.
  • the test is run as follows: a blend of 0.25 g. of silver behenate, 0.25 g. of the reducing agent, 0.05 g. of phthalazinone, and 3 ml. of methylethyl ketone is prepared by thorough mixing, yand a single drop of the mixture is placed on a small thin cover glass and allowed to dry. The glass is placed on the iiat surface of a metal plate heated to 100 C. and the time required to cause rapid darkening of the dry ilm is noted. It is assumed that the sample reaches the plate temperature within the first second, and accordingly no correction is applied for this period.
  • a convenient means for obtaining the desired thorough mixing is an ordinary electrically driven high speed dental mixer. A few small glass beads may be added to assist in the mixing if desired. In any event the reactants must be thoroughly mixed so that the color change occurs uniformly throughout the entire ⁇ lm on the glass slide.
  • test with p,pmethy1enebis(N,Ndimethyl aniline) requires some 70 seconds to develop full color change. With these materials the test mixture does not undergo the required rapid darkening, in which the full color change takes place within not more than one or two seconds, and usually even more rapidly.
  • Ionol requiring six to eight seconds for the color change in the described test, provides intense blacliimage and clean white background areas when similarly employed.
  • Other useful light stable reducing agents having analogous image amplifying properties, and the time required for them to produce rapid blackening in the test described, include: 2,6-ditertiarybutyl-li-methoxymethyl phenol, 8-9 seconds; 2,6-ditertiarybutyl-li-etbyl penol, 13-14 seconds; 2,6-ditertiarybutyl-4-octyl phenol, 17-20 seconds; p-cresol, 10 seconds; 2,4,6-tritertiaryamyl phenol, 25 seconds; and 4,4'methylenebis(2,6-ditertiarybutylphenol), l2 seconds.
  • a photosensitive volatilizable reducing agent in the intermediate sheet permits the 'preparation of reproductions of graphie originals capable of providing differential light images and is ordinarily preferred.
  • Other reducing agents may be substituted where heat images are to be employed, as in direct thermographic copying or in printing with heated metal typeor stylus.
  • the coating on the intermediate film may contain pyrogallol or catechol in place of l-hydroxy-4-methoxy naphthalene, and images may be produced on animage sheet containing silver soap and small amounts of Ionol by locally heating the intermediate lm at image areas in contact with the image sheet.
  • reducing agents with Ionol or i the like and withthe silver soap in a one-sheet heat-sensitive copy-paper which may at the same time be photosensitive if desired.
  • a combination of silvery behenate, phthalazinone, Ionol and 1-hydroxy-4-methoxy naphthalene provides a coating which converts rapidly to an intense black on brief heating ybut which after exposure to actinic light does not darken beyond a Weak brownish black even on prolonged heating.
  • Example 1 A mixture of equal mol percent of silver behenate and behenic acid is prepared by reacting together one m01V of silver nitrate and two mols of sodium behenate, made from commercial behenic acid, in acidic aqueous medium.
  • the Washed and dried precipitate is in the form of a fine powder fusing at about C. and melting to a liquid at about 175 C.
  • a coating mixture is prepared by mixi the coating assuming a dull brownish black appearance when the sheet is heated, for example for 2 minutes at C.
  • a light-sensitive film product is prepared by applying to one mil (.001 inch) Mylar transparent polyester film a thin uniform coating of a blend of 50 parts by weight of ethyl cellulose, 1.4 parts of 1-hydroxy-4-methoxynaphthalene, and 0.3 part of erythrosin B. The mixture is applied from solution in acetone. The weight of the dried coating is 0.2 gram per square foot.
  • the film is placed with its coated surface in contact with a printed original having light-absorptive inked image areas on a reliective white paper background and which is then uniformly exposed through the film, i.e. in the reflex position, to intense illumination from a bank of tungsten filament lamps for a time just suliicient to desensitize the coating completely at the background areas.
  • a typical exposure time may be 12-15 seconds.
  • the image areas are also affected but to a significantly lesser extent due to absorption in the image areas of the graphic original of that portion of the actinic radiation not previously absorbed in the sensitive coating.
  • the exposed film is next placed with its coated surface against the coated sheet surface and the composite is heated, for example between rolls or platens, for 4-5 seconds at 12S-140 C.
  • a copy of the graphic original is produced on the coated sheet.
  • the image areas are a dense black; the background areas remain visibly unchanged.
  • Heating a similary exposed film in contact with a coated sheet from which the 2,6-di-t-butyl-4-methy1- phenol has been omitted produces a faint and incomplete copy of the original, with brownish image areas ⁇
  • Films coated with much larger amounts of the 1-hydroxy-4- methoxynaphthalene and exposed to complete desensitization at background areas produce darker but still incomplete image areas when heated in contact with such silvercoated sheets, and require excessive exposure for desensitization.
  • Example 2 Essentially the same results are obtained when the phthalazinone of the foregoing example is replaced with phthalic anhydride as the toner for the silver image. More specifically, the silver soap mixture differs from that of Example 1 in substituting 2.6 parts of phthalic acid for the 5.2 parts of phthalazinone, and by increasing the amount of 2,6-di-tertiary-butyl-Lt-methylpheibl from 2.2 parts to 8 parts. On heating the reflex-exposed lightsensitive film in Contact with the coated image paper, there is developed on the latter a blue-brown image.
  • Example 3 An image sheet prepared as in Examples 1 and 2 with a silver soap coating on a paper-like carrier may be converted into a unitary copy-sheet by the application of a further coating over the silver soap layer.
  • a mixture of 0.1 part by weight of 4-methoxy-l-naphthol, 5 parts of ethyl cellulose, and 95 parts of methanol is coated at a 3-mil orifice over the silver soap coating of an image sheet prepared as described in Example 1, and the sheet is dried, forming a unitary heat-sensitive copy sheet with which copies of graphic originals may be prepared by thermographic back-print copying procedures.
  • Such copies may be desensitized against further heat-induced visible change in the unprinted areas by exposure to ultraviolet radiation.
  • the sheet may first be exposed to an ultraviolet radiation image. as by exposure through a negative transparency or a stencil, and the unexposed areas then developed by heating to produce a visible pattern.
  • a heat-sensitive copy sheet product capable o'f providing high contrast dense black images on a white background when briefly heated at image areas to conversion temperature within the approximate range of 90-150" C., said product containing, uniformly applied over a paperlike carrier and in position for heat-induced inter-reaction, reactants comprising a silver soap of an organic acid, a toner for the silver image, a di-tertiaryalkyl substituted phenol first reducing agent for the silver ion in an amount of at least about 0.01 mol per mol of silver soap and in- (i vsufiicient to form with said silver soap a dense image when briefly heated therewith, and a photosensitve different active-hydrogen aromatic organic second reducing agent for said silver ion in an amount no greater than that of said first reducing agent, said first reducing agent being further characterized as forming with an equal weight of silver behenate and one-fifth said weight of phthalazinone a uniformly blended trace deposit requiring at least six seconds preheat at
  • a heat-sensitive copy sheet product capable of providing high contrast dense black images on a white background when briefly heated at image areas to conversion temperature Within the approximate range of -150 C., said product containing, uniformly applied over a paperlike carrier and in position for heat-induced inter-reaction, reactants comprising a silver soap of an Iorganic acid, phthalazinone toner for the silver image, a di-tertiaryalkyl substituted phenol first reducing agent for the silver ion in an amount within the range of approximately 0.01 to 0.4 mol per mol of silver soap and insufficient to form with said silver soap a dense image
  • said first reducing agent being further characterized as forming with an equal weight of silver behenate and one-fifth said weight of phthalazinone a uniformly blended trace deposit requiring at least six seconds preheat at C. before rapidly dark
  • said image sheet including a layer consisting essentially of a silver soap of an organic acid, a toner for the silver image, and a di-tertiaryalkyl substituted first reducing agent in an amount of at least about 0.01 mol per mol of said silver soap and insufficient to form with said silver soap a dense image on briey heating said image sheet at 150 C. and characterized as forming with an equal weight of silver behenate and onefifth said weight of phthalazinone a uniformly blended trace deposit requiring at least six seconds preheat at 100 C. before rapidly darkening at that temperature; said intermediate sheet having image and background areas, said image areas including a volatilizable activehydrogen aromatic organic second reducing agent for the silver ion.
  • a two-sheet heat-sensitive copy sheet composite capable of providing high contrast dense black images on a White background when briey heated in face-to-face contact at image areas to conversion temperature Within the approximate range of 90-150 C. and comprising: an image sheet including a layer comprising a silver soap of an organic acid, a toner for the silver image, and a ditertiaryalkyl substituted phenol first reducing agent for the silver ion in an amount of at least about 0.01 mol per mol of silver soap and insufiicient to form with said silver soap a dense image when said sheet is briefly heated, said first reducing agent being further characterized as forming with an equal weight of silver behenate and onefifth said weight of phthalazinone a uniformly blended trace deposit requiring at least six seconds preheat at 100 C.
  • an intermediate sheet including a photosensitve volatilizable active-hydrogen aromatic organic second reducing agent for said silver ion in a concentration no greater than that of said first reducing agent and which on exposure to actinic radiation is rendered incapable of reducing silver ion on briey heating with silver soap at 150 C.
  • a two-sheet heat-sensitive copy sheet composite capable of providing high contrast dense black images on a white background when briefly heated in face-tofacc contact at image areas to conversion temperature within the approximate .range of 90-150 C. and comprising; an image sheet including a layer comprising a silver soap of an organic acid, phthalazinone toner for the silver image, and a di-tertiaryalkyl substituted phenol tirst reducing agent for the silver ion in an amount within the approximate rangcof 0.01 to 0.4 mol per mol of silver soap and insuliicient to lor-m ywith said silver soap a dense image when said sheet is bricliy heated, said iirst reducing agent being further characterized as forming with an equal weight of silver behenate and one-fifth said weight ot ⁇ phthalazinone a uniformly blended trace deposit requiring at least six seconds prehcat at 100 C.
  • an intermediate sheet including a photosensitive volatilizable substituted alpha-naphthol second reducing agent for said silver ion in a concentration no greater than that of said rst reducing agent and which on exposure to actiaic radiation is rendered incapable of reducing silver ion on briefly heating with silver soap at 150 C.
  • the transparent intermediate sheet includes a transparent carrier film having a coating comprising the photosensitive second reducing agent and a photoreducible dye.
  • a visible change consistingessentially of a silver soap of an organic acid, a toner for the silver image, and a di-tertiaryalkyl substituted phenol iirst reducing agent in an amount of at least about 0.01 mol per mol of said silver soap and insulicient to form with said silver soap a dense image on briefly heating said image sheet at 150 C.
  • said first reducing agent being further characterized as forming with an equal weight of silver behenate and one-fifth said Weight of phthalazinone a uniformly blended trace deposit requiring at least six seconds preheat at 100 C. before rapidly darkening at that temperature.
  • a visible change consisting essentially of a silver soap of an organic acid, phthalazinone toner for the silver image, and a di-tertiarya liyl substituted phenol rst reducing agent in an amount within the approximate range of 0.01 to 0.4 mol per mol of said silver soap and insuicient to form with said silver soap a dense image on briefly heating said image sheet at 150 C., said lirst reducing agent being further characterized as forming with an equal weight of silver behcnate and one-fifth said? weight of phthalazinone a uniformly blended trace deposit requiring at least six seconds prcheat at 100 C. bcl lore rapidly darkening at that temperature.
  • An image sheet comprising a paper-like backing and a coating thereon comprising a silver soap, phthalazinonc. and 2,6-ditertiarybutyl-p-ciesol, the amount of 2,6- ditertiarybutyl-p-cresol being within the approxiate range of 0.0i to 0.4 -mol per mol of silver soap and insuiiicient to form with said soap a dense image on briefly heating said image sheet at 150 C.
  • a heat-sensitive copy sheet product capable of providing high contrast dense black images on a white background when hrictly heated at image areas to conversion temperature within the approximate range of -150 C., said product containing, in position for image-forming heat-induced interreaction, reactants comprising a silver soap ot an organic acid, a toner for the silver image, a ditertiarybutyl alkyl phenol reducing agent for silver ion in an amount of at least about 0.01 mol per mol of silver soap and insufficient to form with said silver soap a dense image when briefly heated therewith and further characterized as forming with an equal Weight of silver behenate and onc-fth said weight of phthalazinone a uniformly blended trace deposit requiring at least six seconds preheat at C.
  • a photosensitive alpha-naphthol reducing agent for silver ion which reducing agent on exposure to actinic radiation is rendered incapable of reducing silver ion in a test procedure involving briefly heating with silver soap at C.
  • a heat-sensitive copy sheet product including an image sheet and a transparent intermediate sheet in faceto-face contact; said image sheet including a surface ⁇ layer comprising a silver soap of an organic acid, a toner for the silver image, and a 2,-ditertiaryalkyl-4-alkyl phenol reducing agent for silver ion in an amount of at least about 0.01 mol per mol of silver soap and insulticient to form with said silver soap a dense image on brieliy heating an image area of said image sheet, said phenol being further characterized as forming with an equal Weight of silver behenate and one-litth said Weight of phthalazinone a uniformly blended trace deposit requiring at least six seconds preheat at 100 C.
  • said intermediate sheet including a surface layer comprising a photosensitive alpha-naphthol reducing agent for silverfion, said alpha-naphthol being further characterized as being rendered incapable oi' reducing silver ion, in a test procedure involving brieily heating with silver soap at 150 C., by exposure to actinic radiation.

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  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • General Physics & Mathematics (AREA)
  • Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
  • Heat Sensitive Colour Forming Recording (AREA)
US239807A 1962-11-23 1962-11-23 Heat sensitive copy sheet Expired - Lifetime US3218166A (en)

Priority Applications (12)

Application Number Priority Date Filing Date Title
DENDAT1250842D DE1250842B (de) 1962-11-23 Wärmeempfindliches Kopiermaterial
NL300853D NL300853A (is") 1962-11-23
US239807A US3218166A (en) 1962-11-23 1962-11-23 Heat sensitive copy sheet
GB44452/63A GB1071021A (en) 1962-11-23 1963-11-11 Copy-sheet product
ES0293547A ES293547A1 (es) 1962-11-23 1963-11-15 Mejoras introducidas en la fabricaciën de hojas copiadoras sensibles al calor
BE640183A BE640183A (is") 1962-11-23 1963-11-20
SE12849/63A SE328472B (is") 1962-11-23 1963-11-21
NL63300853A NL139485B (nl) 1962-11-23 1963-11-22 Warmtegevoelig kopieermateriaal.
AT940263A AT268875B (de) 1962-11-23 1963-11-22 Wärmeempfindliches Kopiermaterial
CH1433663A CH454188A (de) 1962-11-23 1963-11-22 Wärmeempfindliches flächenförmiges Kopiermaterial
FR954747A FR1383197A (fr) 1962-11-23 1963-11-22 Feuille de copie thermo-sensible
DK549463AA DK121305B (da) 1962-11-23 1963-11-22 Varmefølsomt kopieringsmateriale.

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Application Number Priority Date Filing Date Title
US239807A US3218166A (en) 1962-11-23 1962-11-23 Heat sensitive copy sheet

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US3218166A true US3218166A (en) 1965-11-16

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US239807A Expired - Lifetime US3218166A (en) 1962-11-23 1962-11-23 Heat sensitive copy sheet

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US (1) US3218166A (is")
AT (1) AT268875B (is")
BE (1) BE640183A (is")
CH (1) CH454188A (is")
DE (1) DE1250842B (is")
DK (1) DK121305B (is")
ES (1) ES293547A1 (is")
GB (1) GB1071021A (is")
NL (2) NL139485B (is")
SE (1) SE328472B (is")

Cited By (29)

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US3409438A (en) * 1963-08-26 1968-11-05 Minnesota Mining & Mfg Photosensitive heat developable copysheet
US3446648A (en) * 1965-09-27 1969-05-27 Minnesota Mining & Mfg Reactive copying sheet and method of using
US3455687A (en) * 1964-11-28 1969-07-15 Eastman Kodak Co Photothermographic copying process
US3460946A (en) * 1966-02-03 1969-08-12 Minnesota Mining & Mfg Image receptor sheets containing organic silver salts and metal ion image
US3529963A (en) * 1966-08-23 1970-09-22 Du Pont Image-yielding elements and processes
US3547648A (en) * 1968-01-26 1970-12-15 Minnesota Mining & Mfg Copy-sheet
US3847612A (en) * 1973-02-02 1974-11-12 Minnesota Mining & Mfg Light-sensitive heat-developable sheet material
DE2440678A1 (de) * 1974-08-24 1976-03-04 Agfa Gevaert Ag Verbessertes photographisches aufzeichnungsmaterial zur herstellung von kopien im trockenverfahren
US4001026A (en) * 1972-06-13 1977-01-04 Agfa-Gevaert N.V. Method and materials for thermoplastic recording
US4123282A (en) * 1975-09-08 1978-10-31 Minnesota Mining And Manufacturing Company Photothermographic toners
EP0683428A1 (en) * 1994-05-17 1995-11-22 Agfa-Gevaert N.V. Thermal transfer imaging system based on the heat transfer of a reducing agent for reducing a silver source to metallic silver
US5558972A (en) * 1994-06-27 1996-09-24 Agfa-Gevaert Thermal transfer printing of a reducing agent to a silver source contained in an image receiving layer
US5587269A (en) * 1994-03-25 1996-12-24 Afga-Gevaert N.V. Thermal transfer imaging process and donor element for use therein
US5587270A (en) * 1994-03-10 1996-12-24 Agfa-Gevaert N.V. Thermal imaging process and an assemblage of a donor and receiving element for use therein
US5587268A (en) * 1994-03-25 1996-12-24 Agfa-Gevaert N.V. Thermal transfer imaging process
US5589317A (en) * 1994-03-10 1996-12-31 Agfa-Gevaert N.V. Thermal transfer imaging process
US5595854A (en) * 1994-03-25 1997-01-21 Agfa-Gevaert N.V. Method for the formation of heat mode image
US5601962A (en) * 1994-03-25 1997-02-11 Agfa-Gevaert N.V. Thermal transfer process wherein a reducing agent and toning agent are transferred to a receiving element containing a thermoreducible silver source
US5627008A (en) * 1994-03-25 1997-05-06 Agfa-Gevaert N.V. Thermal transfer printing process using a mixture of reducing agents for image-wise reducing a silver source
US5637550A (en) * 1995-03-02 1997-06-10 Agfa-Gevaert N.V. Heat-sensitive recording material having image-stabilization properties
EP0795997A1 (en) * 1996-03-14 1997-09-17 Agfa-Gevaert N.V. Producing a contone image by sequentially exposing a thermo-sensitive imaging material by means of a set of radiation beams
EP0730196A3 (en) * 1995-03-02 1998-01-21 Agfa-Gevaert N.V. Heat-sensitive recording material having image-stabilization properties
US5719005A (en) * 1994-12-27 1998-02-17 Agfa-Gevaert, N.V. Method for the formation of an improved photo mode image
EP1211093A1 (en) * 2000-11-30 2002-06-05 Agfa-Gevaert Thermographic recording material with improved image tone
US6586363B2 (en) 2000-11-30 2003-07-01 Agfa-Gevaert Thermographic recording material with improved image tone
US6664211B2 (en) 2000-11-30 2003-12-16 Agfa-Gevaert Thermographic recording material with improved image tone
US9125829B2 (en) 2012-08-17 2015-09-08 Hallstar Innovations Corp. Method of photostabilizing UV absorbers, particularly dibenzyolmethane derivatives, e.g., Avobenzone, with cyano-containing fused tricyclic compounds
US9145383B2 (en) 2012-08-10 2015-09-29 Hallstar Innovations Corp. Compositions, apparatus, systems, and methods for resolving electronic excited states
US9867800B2 (en) 2012-08-10 2018-01-16 Hallstar Innovations Corp. Method of quenching singlet and triplet excited states of pigments, such as porphyrin compounds, particularly protoporphyrin IX, with conjugated fused tricyclic compounds have electron withdrawing groups, to reduce generation of reactive oxygen species, particularly singlet oxygen

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DE2220618C2 (de) * 1972-04-27 1985-01-10 Agfa-Gevaert Ag, 5090 Leverkusen Bildempfangsmaterial

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US2910377A (en) * 1956-06-28 1959-10-27 Minnesota Mining & Mfg Heat-sensitive copying-paper
US3074809A (en) * 1959-10-26 1963-01-22 Minnesota Mining & Mfg Heat-sensitive copying-paper
US3094619A (en) * 1961-01-03 1963-06-18 Minnesota Mining & Mfg Ultra-violet radiation-desensitizable thermographic copy-sheet and method
US3094417A (en) * 1961-01-03 1963-06-18 Minnesota Mining & Mfg Heat sensitive copy sheet, process of making and using

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US2910377A (en) * 1956-06-28 1959-10-27 Minnesota Mining & Mfg Heat-sensitive copying-paper
US3074809A (en) * 1959-10-26 1963-01-22 Minnesota Mining & Mfg Heat-sensitive copying-paper
US3094619A (en) * 1961-01-03 1963-06-18 Minnesota Mining & Mfg Ultra-violet radiation-desensitizable thermographic copy-sheet and method
US3094417A (en) * 1961-01-03 1963-06-18 Minnesota Mining & Mfg Heat sensitive copy sheet, process of making and using

Cited By (35)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3409438A (en) * 1963-08-26 1968-11-05 Minnesota Mining & Mfg Photosensitive heat developable copysheet
US3455687A (en) * 1964-11-28 1969-07-15 Eastman Kodak Co Photothermographic copying process
US3446648A (en) * 1965-09-27 1969-05-27 Minnesota Mining & Mfg Reactive copying sheet and method of using
US3460946A (en) * 1966-02-03 1969-08-12 Minnesota Mining & Mfg Image receptor sheets containing organic silver salts and metal ion image
US3529963A (en) * 1966-08-23 1970-09-22 Du Pont Image-yielding elements and processes
US3547648A (en) * 1968-01-26 1970-12-15 Minnesota Mining & Mfg Copy-sheet
US4001026A (en) * 1972-06-13 1977-01-04 Agfa-Gevaert N.V. Method and materials for thermoplastic recording
US3847612A (en) * 1973-02-02 1974-11-12 Minnesota Mining & Mfg Light-sensitive heat-developable sheet material
DE2440678A1 (de) * 1974-08-24 1976-03-04 Agfa Gevaert Ag Verbessertes photographisches aufzeichnungsmaterial zur herstellung von kopien im trockenverfahren
US4013473A (en) * 1974-08-24 1977-03-22 Agfa-Gevaert N.V. Recording materials and image receiving materials for producing copies in a dry way
US4123282A (en) * 1975-09-08 1978-10-31 Minnesota Mining And Manufacturing Company Photothermographic toners
US5589317A (en) * 1994-03-10 1996-12-31 Agfa-Gevaert N.V. Thermal transfer imaging process
US5587270A (en) * 1994-03-10 1996-12-24 Agfa-Gevaert N.V. Thermal imaging process and an assemblage of a donor and receiving element for use therein
US5587268A (en) * 1994-03-25 1996-12-24 Agfa-Gevaert N.V. Thermal transfer imaging process
US5587269A (en) * 1994-03-25 1996-12-24 Afga-Gevaert N.V. Thermal transfer imaging process and donor element for use therein
US5595854A (en) * 1994-03-25 1997-01-21 Agfa-Gevaert N.V. Method for the formation of heat mode image
US5601962A (en) * 1994-03-25 1997-02-11 Agfa-Gevaert N.V. Thermal transfer process wherein a reducing agent and toning agent are transferred to a receiving element containing a thermoreducible silver source
US5627008A (en) * 1994-03-25 1997-05-06 Agfa-Gevaert N.V. Thermal transfer printing process using a mixture of reducing agents for image-wise reducing a silver source
US5547809A (en) * 1994-05-17 1996-08-20 Agfa-Gevaert, N.V. Thermal transfer imaging system based on the heat transfer of a reducing agent for reducing a silver source to metallic silver
EP0683428A1 (en) * 1994-05-17 1995-11-22 Agfa-Gevaert N.V. Thermal transfer imaging system based on the heat transfer of a reducing agent for reducing a silver source to metallic silver
US5558972A (en) * 1994-06-27 1996-09-24 Agfa-Gevaert Thermal transfer printing of a reducing agent to a silver source contained in an image receiving layer
US5719005A (en) * 1994-12-27 1998-02-17 Agfa-Gevaert, N.V. Method for the formation of an improved photo mode image
EP0730196A3 (en) * 1995-03-02 1998-01-21 Agfa-Gevaert N.V. Heat-sensitive recording material having image-stabilization properties
US5637550A (en) * 1995-03-02 1997-06-10 Agfa-Gevaert N.V. Heat-sensitive recording material having image-stabilization properties
EP0795997A1 (en) * 1996-03-14 1997-09-17 Agfa-Gevaert N.V. Producing a contone image by sequentially exposing a thermo-sensitive imaging material by means of a set of radiation beams
EP1211093A1 (en) * 2000-11-30 2002-06-05 Agfa-Gevaert Thermographic recording material with improved image tone
US6586363B2 (en) 2000-11-30 2003-07-01 Agfa-Gevaert Thermographic recording material with improved image tone
US6664211B2 (en) 2000-11-30 2003-12-16 Agfa-Gevaert Thermographic recording material with improved image tone
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US9145383B2 (en) 2012-08-10 2015-09-29 Hallstar Innovations Corp. Compositions, apparatus, systems, and methods for resolving electronic excited states
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US9926289B2 (en) 2012-08-10 2018-03-27 Hallstar Innovations Corp. Compositions, apparatus, systems, and methods for resolving electronic excited states
US10632096B2 (en) 2012-08-10 2020-04-28 HallStar Beauty and Personal Care Innovations Company Method of quenching singlet and triplet excited states of photodegradable pigments, such as porphyrin compounds, particularly protoporphyrin IX, with conjugated fused tricyclic compounds having electron withdrawing groups, to reduce generation of singlet oxygen
US9125829B2 (en) 2012-08-17 2015-09-08 Hallstar Innovations Corp. Method of photostabilizing UV absorbers, particularly dibenzyolmethane derivatives, e.g., Avobenzone, with cyano-containing fused tricyclic compounds

Also Published As

Publication number Publication date
AT268875B (de) 1969-02-25
SE328472B (is") 1970-09-14
ES293547A1 (es) 1964-01-01
CH454188A (de) 1968-04-15
GB1071021A (en) 1967-06-07
DK121305B (da) 1971-10-04
NL139485B (nl) 1973-08-15
DE1250842B (de) 1967-09-28
NL300853A (is")
BE640183A (is") 1964-03-16

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