US3111407A - Methods for making record materials - Google Patents

Methods for making record materials Download PDF

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Publication number
US3111407A
US3111407A US11287A US1128760A US3111407A US 3111407 A US3111407 A US 3111407A US 11287 A US11287 A US 11287A US 1128760 A US1128760 A US 1128760A US 3111407 A US3111407 A US 3111407A
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United States
Prior art keywords
microcapsules
dye
substrate
solution
ingredients
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Expired - Lifetime
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US11287A
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English (en)
Inventor
Robert M Lindquist
Reyes Zoila
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International Business Machines Corp
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International Business Machines Corp
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Publication date
Priority to IT631615D priority Critical patent/IT631615A/it
Application filed by International Business Machines Corp filed Critical International Business Machines Corp
Priority claimed from US11286A external-priority patent/US3173878A/en
Priority to US11287A priority patent/US3111407A/en
Priority to FR853523A priority patent/FR1286949A/fr
Priority to DEJ19475A priority patent/DE1209999B/de
Priority to AT147561A priority patent/AT250405B/de
Priority to AT605363A priority patent/AT251612B/de
Priority to GB7051/61A priority patent/GB898668A/en
Priority to GB19443/61A priority patent/GB984632A/en
Priority to DEJ20137A priority patent/DE1243643B/de
Publication of US3111407A publication Critical patent/US3111407A/en
Application granted granted Critical
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C3/00—Treatment in general of inorganic materials, other than fibrous fillers, to enhance their pigmenting or filling properties
    • C09C3/08—Treatment with low-molecular-weight non-polymer organic compounds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
    • B01J13/02—Making microcapsules or microballoons
    • B01J13/06—Making microcapsules or microballoons by phase separation
    • B01J13/08—Simple coacervation, i.e. addition of highly hydrophilic material
    • 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
    • G03C1/002—Photosensitive materials containing microcapsules
    • 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
    • G03C5/00—Photographic processes or agents therefor; Regeneration of such processing agents
    • G03C5/18—Diazo-type processes, e.g. thermal development, or agents therefor
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01F—MAGNETS; INDUCTANCES; TRANSFORMERS; SELECTION OF MATERIALS FOR THEIR MAGNETIC PROPERTIES
    • H01F1/00—Magnets or magnetic bodies characterised by the magnetic materials therefor; Selection of materials for their magnetic properties
    • H01F1/44—Magnets or magnetic bodies characterised by the magnetic materials therefor; Selection of materials for their magnetic properties of magnetic liquids, e.g. ferrofluids
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01F—MAGNETS; INDUCTANCES; TRANSFORMERS; SELECTION OF MATERIALS FOR THEIR MAGNETIC PROPERTIES
    • H01F41/00—Apparatus or processes specially adapted for manufacturing or assembling magnets, inductances or transformers; Apparatus or processes specially adapted for manufacturing materials characterised by their magnetic properties
    • H01F41/14—Apparatus or processes specially adapted for manufacturing or assembling magnets, inductances or transformers; Apparatus or processes specially adapted for manufacturing materials characterised by their magnetic properties for applying magnetic films to substrates
    • H01F41/16—Apparatus or processes specially adapted for manufacturing or assembling magnets, inductances or transformers; Apparatus or processes specially adapted for manufacturing materials characterised by their magnetic properties for applying magnetic films to substrates the magnetic material being applied in the form of particles, e.g. by serigraphy, to form thick magnetic films or precursors therefor
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S101/00—Printing
    • Y10S101/29—Printing involving a color-forming phenomenon

Definitions

  • This invention relates generally to record materials, and more particularly to such materials responsive to application of light and pressure.
  • Another object of the invention is to provide a record material of this character adapted to record either an riginal li ht or pressure image, a copy image, or both.
  • Another object is to provide a material of this charac ter which is extremely stable; and in Which reactive ingredients are protected from the environment.
  • a further object is to provide methods for making the improved record materials, and for their use.
  • FiG RE 1 is a cross sectional detail illustrating a record material embodying the invention
  • FIGURES 2 to 4 are like views showing various modifications of the invention.
  • FlGURE 5 is a like view, illustrating a particular application of the invention.
  • the present invention is predicated upon our discovery that particular types of liquid containing microcapsules olier a convenient means of preparing dry, light-andpressure sensitive coatings of dissolved dyes, inks or reactive chemical solutions so that the solutions are isolated and protectcdfrom the surrounding environment. More specifically, it is predicated upon discovery that microcapsules formed of polymerized material, by virtue of their ability to successfully retain aqueous and other polar solutions, make it possible to provide a record or copy material of this type employing the diazo process.
  • this process requires (1) a diazonium compound, (2) a coupler, and (3) a material to adjust the pH so that the coupling or reaction of the first two components to form an azo dye can occur in an alkaline medium.
  • Light and pressure modulation of the record material can therefore be obtained in several Ways, for example, by exposure to light followed by a uniform pressure to develop the image; or the use of selected pressure to print the image followed by a light exposure to destroy the residual diazo compound and thus iix the image.
  • a uniform pressure to develop the image or the use of selected pressure to print the image followed by a light exposure to destroy the residual diazo compound and thus iix the image.
  • the record materials of the present invention are made by the deposit of the pressure-rupturable polymeric microcapsules on a suitable substrate or base sheet material such as paper, plastic, cloth, glass, etc, along with a coating reactive with the es psulated solution to form the azo dye.
  • the microcapsules are applied to the substrate in the form of a coating containing the microcapsules.
  • the microcapsul s are applied as a thin film-like layer separately from the coating, which may lie above or beneath the microcapsules on the surface of the substrate.
  • a manifold may be prepared by assembling a number of coated substrates in such fashion that the encapsulated component is brought into contact with the remaining components carried by an adjoining substrate.
  • FIGURE 1 represents a substrate it? on Which a coating 12 containing uniformly dispersed microcapsules 14 has been deposited.
  • the microcapsules contain an aqueous or other polar solution of one or more dye forming compoents, Whereas the coating contains the remaining components necessary to form an azo dye.
  • the coating 12 may comprise intermixed coupler and material to adjust pH, and the microcapsules 1d diazonium salt.
  • the microcapsules 14 may contain a solution to adjust pH (or such solution intermixed with the coupler) whereas the coating 12 may contain the additional dye forming ingredients. It Will be understood that the coating 12 and microcapsules 14 are most conveniently deposited on the substrate 19 in a single operation, for example, by flooding of the surface, although such processing is not essential.
  • FIGURE 2 illustrates a modified record material in Which the microcapsules 24 are first deposited on the substrate 20, as an underlayer following which the coating 22 is deposited as a surface layer.
  • the dye forming components can be separated as before, that is, the microcapsules 2-4 may contain either a diazonium salt, a coupler, or a mixture of coupler and solution to adjust pH, and the surface coating 22 addit onal dye ingredients as necessary to react with the isolated content of the microcapsules.
  • FIGURE '3 The record material of FIGURE '3 is similar to that of FIGURE 2 except that the coating layer 32 is deposited first with the microcapsules 34 being adhered to this coating as the surface layer.
  • various techniques have been developed to deposit the microcapsules in successive cooperative layers upon a substrate, for example, by a series of successive spray drying operations.
  • FIGURE 4 illustrates a further modification in which a number of separate coated substrates are assembled into a manifold record material.
  • the microcapsules 44 are deposited on one side of a base sheet it), and a coating containing the remaining dye-forming components deposited on the reverse side of the sheet, as at 42.
  • Upper and lower sheets 45 and 48 are similarly prepared except that exterior surfaces need not be coated.
  • a manifold can be prepared by assembling the sheets 45 and 48 so that the encapsulated component (in the microcapsules 44) is brought into contact with the remaining components dispersed in the containing layers 42.
  • Marking of the record materials just described is accomplished by crushing or breaking the microcapsules to release the isolated dye forming component.
  • marl;- ing may result from localized pressure or impact, for example, the scratch of a stylus or the stroke of a typewriter key.
  • marking may be in response to uniform pressure applied over the entire surface of the record material, as in calendering operation.
  • the color reaction in either case, is of the well known coupling type to form an azo dye, the fundamental reaction being expressed as follows:
  • RN X represents a diazonium salt (X- an acid radical)
  • coupling is believed to occur through the agency of the diazonium ion. Coupling is obtained in an a kaline medium with aromatic amines and with phenols, occurring in the para position of the ring. thro derivatives may also result if the para position is occupied. If a very active d-iazon-ium compound is used, coupling may be obtained by modified couplers (e.g., phenolic ether and compounds containing activated methylene groups). Coupling occurs quite rapidly upon application of pressure to the record material to release the isolated component, and produces a mark of distinctive color.
  • modified couplers e.g., phenolic ether and compounds containing activated methylene groups
  • microcapsules employed in the record materials of the present invention consist of an aqueous or other polar solvent solution of one or more of the components for dye formation as a core, and a polymerized material, encapsulating such solution and forming an outer protective shell.
  • Any suitable hydrophobic polymer having desired characteristics for encapsulation purposes may be employed.
  • Preferred polymers are those which possess excellent chemical and water resistance and dimensional stability, which are heat stable, and which retain suitable flexibility and toughness upon variation in temperature. Examples of suitable polymers include those ba ed on cellulose, such as ethyl cellulose, cellulose nitrate, cellulose acetate-butyrate and other mixed and higher esters of cellulose.
  • Polystyrene and polystryene copolymers can also be satisfactorily employed, likewise vinyl acetate-vinyl chloride copolymers, polyvinyl chloride, polyvinylidene chloride, polyethylene, polypropylene, polybutene, polyisobutylene, and natural and synthetic rubbers, polyvinyl fluoride, polyesters such as styrenated polyesters, resins such as alkyd resins and blends of these polymers and resins.
  • Ethyl cellulose is particularly satisfactory because of its extensive compatibility, its stability to light, and its resistance to heat and chemical action by acids and bases.
  • the formation of the solution filled rnicrocapsules, and the depositing of a profusion of such microcapsules on a sheet of base material, can be accomplished in a number or": different ways.
  • One suitable procedure is disclosed in the copending Reyes application Serial No. 11,341, filed February 25, 1969. This procedure involves the dispersing of a polar solution of a component for dye formation in a continuous phase solution of a polymer followed by the addition of a nonsolvent for the polymer to cause its precipitation about colloidal droplets of this solution to produce microcapsules. Also disclosed is the step of coating with the microcapsules by spray drying onto a substrate.
  • Another suitable procedure is disclosed in copending Hull and Marshall application, Serial No. 39,150, filed lune 27, 1960.
  • the procedure of this application involves a freeze hardening technique by which the solution filled polymeric microcapsules can be readily insolubilized and separated from the continuous phase liquid for deposit on the substrate.
  • the last two procedures produce a profusion of isolated microcapsules in the form of a fine powder, which is dry to the touch, although the powder may actually comprise as much as of aqueous or other dye-containing solution.
  • This powder may be applied to the substrate separately, or as part of a diazo coating, by any one of a number of well known techniques.
  • Example 1 The following solution is prepared, in parts by weight:
  • borax 1.4 of trisodium phosphate 25.0 of polyethylene glycol 460 72.6 of water
  • the solution is emulsified in 400 parts of 5% ethyl cellulose in xylene-carbon tetrachloride (1:1 by weight).
  • a finely divided solidified castor oil derivative (Thixcin R,) is used as emulsifying agent in the proportion of 1% on the weight of the aqueous solution.
  • the emulsion is diluted with carbon tetrachloride to 2 /2 with respect to ethyl cellulose.
  • petroleum ether 65- C.
  • microcapsule suspension obtained is cooled to 15 C. with simultaneous agitation, and allowed to settle.
  • the equilibrium liquid is decanted and the wet capsules suspended in a -1:2 mixture (-by volume) of carbon tetrachloride and petroleum ether (65-110 C.).
  • the resulting suspension is sprayed on paper or film along with a current of Warm air (3080 C.) to form a coating.
  • a De Vil'bis fog-type spray gun with No. 30 nozzle, and operated at 40 to 50 p.s.i., can be used for these coatings.
  • the coatings When the coatings are deposited on plain paper, they can be used to print by pressure on (e.g., develop) diazo papers which contain both components of the azo dye, the diazonium salt and the coupler in one layer. Such use would be similar to that described in connection with FIGURE 4.
  • the coatings are made by spraying the capsule suspension directly on a diazo paper, which contains the diazonium salt and the coupler in one layer, a self-developing diazo paper results, as in FIGURE 3.
  • Example 2 Powder-like capsules are also obtained by spray drying Inicrocapsule suspensions, obtained as in Example 1, in a Nerco-Niro Spray Dryer (portable model). The resulting powder-like microcapsules can be dispersed in -a coating medium, containing the other two components of the diazo process, and coated in a single operation to give a self-developing diazo paper of the type illustrated in FIG- URE 1.
  • a dispersion of the microcapsules in 4% polyisobutylene is mixed with an emulsion of a solution of the other two components (the diazonium salt and the coupler) in the same polymer, and coated on plain paper to give the self-developing diazo paper containing all components in one layer, as in FIGURE 1.
  • Example 3 A solution is prepared having the following composition in parts by Weight:
  • the solution is emulsified in :1 16 /370 solution of polystyrene in xylene, employing 1.0% of weight of sorbitan sesquioleate (eg. Arlacel C), as an emulsifying agent.
  • the weight ratio of polar solution to polystyrene is 4:1.
  • the emulsion is treated with a petroleum solvent (e.g. solvent A) to precipitate the polymer around the internal phase. The solvent is added very slowly, with agitation, to achieve a gradual precipitation.
  • the microcapsules can also be isolated as a dry powder by spray drying. A dispersion of these powder-like microcapsules in a coating medium, when coated on a diazonium' paper which contains only the diazonium compound, gives a self-developing diazo paper as in FIGURE 3.
  • coatings of microcapsu-les, prepared by spraying the capsule suspension on a substrate are subsequently sprayed with a solution of a diazom'um salt, a self-developing diazo paper of the type illustrated in FIGURE 2 is produced.
  • Example 4 A polar solution is prepared having the following composition in parts by weight:
  • ethyl cellulose can comprise -a 48% ethoxyl polymer (e.g. Hercules N-).
  • the Weight ratio of aqueous solution to polymer in the disper sion is 5:1, 1% by weight of sorbitan sesquioleate (Arlacel C), being used as emulsifying agent.
  • the polymer Upon the slow addition of petroleum ether (65110 C), the polymer is precipitated about the dispersed aqueous solution to form a profusion of the tiny polymeric microcapsules (0.5 to 5 microns).
  • the microcapsules After stirring and cooling to about 15 C., the microcapsules are separated from the equilibrium liquid by decantation and are hardened by gradual and progressive insolubilization of the ethyl cellulose, by washing with petroleum ether containing decreasing amounts of toluene.
  • the hardened microcapsules are separated from the final wash mixture by filtration and dispersed in a coating medium comprising an emulsion of an alkaline solution of a napthol coupler, and the coating medium applied to paper.
  • the resulting dry paper (which is of the type illustrated in FIGURE 1) can be imprinted by application of a pressure image to rupture of the microcapsules, causing release or" the diazoniurn salt at the point of the pressure application.
  • Example 5 A polar solution is prepared in parts by weight as follows:
  • Example 1 The xylene and petroleum ether are gradually removed from the suspension by evaporation under reduced pressure (e.-g., 20 of Hg) in a Rinco evaporator. Polymeric microcapsules remain suspended in the mineral oil as tiny aggregates and isolated units. These aggregates and units oan be employed to produce light and pressure sensitive papers, as in either Example 1 or Example 2.
  • Example 6 A mixture of two parts by weight of 2 /2% sodium silicate in water and 1 part of polyethylene glycol (mol. wt. 400) is emulsified in a 5% solution of ethyl cellulose in a mixture of xylene and carbon tetrachloride (1:1 by weight).
  • a finely divided, solidified castor oil derivative (Thixcin R) is used as emulsifying agent in an amount comprising 1% by weight of the polar solution.
  • the weight ratio of polar solution to polymer is 5:1.
  • the emulsion is diluted with carbon tetrachloride to 2%% with respect to ethyl cellulose.
  • a dry method for forming a smudge-proof relatively permanent image by means of the diazo process the steps of coating a substrate with a combination of ingredients reactive to form a diazo dye in an alkaline medium, said ingredients including a diazonium salt decomposable upon exposure to light to prevent its entering into the dye-forming reaction, a chemical coupler and a material to adjust pH to render said medium alkaline, at least one and no more than two of said ingredients being normally isolated by containment in aqueous solution in a profusion of hydrophobic rupturable microcapsules; applying pressure to a selected portion of said substrate to rupture the microcapsules contained within that portion to cause admixture of all three of said ingredients in aqueous medium to develop an image; and then exposing at least the portion of said substrate to which pressure has not been applied to light to decompose only the residual diazonium salt and fix said image.
  • microcapsules are formed of a hydrophobic polymeric material.
  • a dry method for forming a smudge-proof relatively permanent image by means of the diazo process the steps of coating a substrate with a combination of ingredients reactive to form a diazo dye in an alkaline medium, said ingredients including a diazonium salt decomposable upon exposure to light to prevent its entering into the dye-forming reaction, a chemical coupler and a material to adjust pH to render said medium alkaline, at least one and no more than two of said ingredients being normally isolated by containment in aqueous solution in a pro'fiusion of hydrophobic rupturable microcapsules; exposing a selected portion of said substrate to light to decompose the diazonium salt contained within that portion and render it incapable of reacting with said coupler to form a dye; and then applying pressure to the entire surface of said substrate to rupture the microca-psules and develop a fixed image by reaction of the residual diazonium salt with said coupler in an aqueous alkaline medium.
  • microcapsules are formed of a hydrophobic polymeric material.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Power Engineering (AREA)
  • General Physics & Mathematics (AREA)
  • Physics & Mathematics (AREA)
  • Dispersion Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Materials Engineering (AREA)
  • Manufacturing & Machinery (AREA)
  • Manufacturing Of Micro-Capsules (AREA)
  • Color Printing (AREA)
  • Heat Sensitive Colour Forming Recording (AREA)
US11287A 1960-02-26 1960-02-26 Methods for making record materials Expired - Lifetime US3111407A (en)

Priority Applications (9)

Application Number Priority Date Filing Date Title
IT631615D IT631615A (ro) 1960-02-26
US11287A US3111407A (en) 1960-02-26 1960-02-26 Methods for making record materials
FR853523A FR1286949A (fr) 1960-02-26 1961-02-22 Agents d'enregistrement et leurs procédés de fabrication
AT147561A AT250405B (de) 1960-02-26 1961-02-23 Verfahren zur Herstellung von Mikrokapseln
DEJ19475A DE1209999B (de) 1960-02-26 1961-02-23 Verfahren zur Herstellung von Mikrokapseln
AT605363A AT251612B (de) 1960-02-26 1961-02-23 Druckempfindliches Aufzeichnungsmaterial
GB7051/61A GB898668A (en) 1960-02-26 1961-02-27 Process for producing microcapsules and record members coated therewith
GB19443/61A GB984632A (en) 1960-02-26 1961-05-30 Process for producing microcapsules
DEJ20137A DE1243643B (de) 1960-02-26 1961-06-24 Verfahren zur Herstellung von Mikrokapseln

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US1134160A 1960-02-26 1960-02-26
US11286A US3173878A (en) 1960-02-26 1960-02-26 Process of making microcapsules
US11287A US3111407A (en) 1960-02-26 1960-02-26 Methods for making record materials
US3915060A 1960-06-27 1960-06-27

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DE (2) DE1209999B (ro)
GB (2) GB898668A (ro)
IT (1) IT631615A (ro)

Cited By (116)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3202510A (en) * 1961-07-11 1965-08-24 Frederick Post Co Production of encapsulated light-sensitive diazotype compositions and coatings
US3242122A (en) * 1961-09-18 1966-03-22 Ncr Co Thermo-colorable record copy sheet and coating composition
US3272629A (en) * 1962-01-25 1966-09-13 Nashua Corp Photosensitive diazotype materials
US3281244A (en) * 1962-01-27 1966-10-25 Keuffel & Esser Co Heat-developable two-component diazotype reproduction material
US3306747A (en) * 1962-12-26 1967-02-28 Polaroid Corp Diffusion transfer product with microcapsules containing glycerin-water solutions
US3360371A (en) * 1962-12-29 1967-12-26 Keuffel & Esser Co Heat-developable two-component diazotype reproduction material
US3377165A (en) * 1964-01-22 1968-04-09 Minnesota Mining & Mfg Process of copying utilizing a blush lacquer coating and a photodecomposable progenitor of a plasticizer
US3393155A (en) * 1964-02-28 1968-07-16 Degussa Predominantly aqueous compositions in a fluffy powdery form approximating powdered solids behavior and process for forming same
US3405071A (en) * 1963-12-30 1968-10-08 Ibm Process of making microcapsules
US3907558A (en) * 1973-12-28 1975-09-23 Xerox Corp Manifold imaging utilizing silica gel activating layer
US4081188A (en) * 1973-09-13 1978-03-28 Wiggins Teape Limited Paper having microcapsules deposited in depressions on a surface thereof has improved smudge-resistance characteristics
US4198470A (en) * 1975-06-09 1980-04-15 Western Litho Plate & Supply Co. Base plate and lithographic plate prepared by sensitization thereof
US4252879A (en) * 1978-08-08 1981-02-24 Dai Nippon Insatsu Kabushiki Kaisha Image recording material having optically different particles
US4272604A (en) * 1975-06-09 1981-06-09 Western Litho Plate & Supply Co. Base plate and lithographic plate prepared by sensitization thereof
US4399209A (en) * 1981-11-12 1983-08-16 The Mead Corporation Transfer imaging system
US4416966A (en) * 1982-08-25 1983-11-22 The Mead Corporation Capsular imaging system comprising decolorizing agent
US4440846A (en) * 1981-11-12 1984-04-03 Mead Corporation Photocopy sheet employing encapsulated radiation sensitive composition and imaging process
US4482624A (en) * 1983-02-15 1984-11-13 The Mead Corporation Photosensitive material employing encapsulated radiation sensitive composition and process for improving sensitivity by sequestering oxygen
US4497887A (en) * 1981-06-09 1985-02-05 Ricoh Compay, Ltd. Thermal development type diazo copying material with hydrophobic resin encapsulated coupler particle
EP0139543A2 (en) * 1983-10-27 1985-05-02 Kureha Kagaku Kogyo Kabushiki Kaisha Partially pressure-sensitive recording paper
US4522910A (en) * 1975-06-19 1985-06-11 Napp Systems (Usa), Inc. Photosensitive graphic arts article
US4562137A (en) * 1982-12-30 1985-12-31 The Mead Corporation Photosensitive material employing encapsulated radiation sensitive composition
DE3530562A1 (de) * 1984-08-28 1986-03-06 Mitsubishi Paper Mills, Ltd., Tokio/Tokyo Biokapsel
EP0224214A2 (en) 1985-11-21 1987-06-03 Fuji Photo Film Co., Ltd. Light-sensitive microcapsule containing polymerizable compound and silver halide, and light-sensitive material employing the same
EP0232865A2 (en) 1986-02-07 1987-08-19 Fuji Photo Film Co., Ltd. Light-sensitive material containing silver halide, reducing agent and polymerizable compound
US4758495A (en) * 1985-03-26 1988-07-19 Fuji Photo Film Co., Ltd. Diazo microcapsule recording material prepared using ion exchange treatment
US4822714A (en) * 1981-11-12 1989-04-18 The Mead Corporation Transfer imaging system
US4842976A (en) * 1982-01-18 1989-06-27 Mead Corp. Color image-forming process
US4871193A (en) * 1985-12-19 1989-10-03 Woerndli Gerhard A Process for irreversible recording, recording carrier, as well as use of the process or of the recording carrier
US5047308A (en) * 1987-06-22 1991-09-10 Fuji Photo Film Co., Ltd. process for preparing photo- and heat-sensitive recording material
US5089371A (en) * 1988-07-21 1992-02-18 Fuji Photo Film Co., Ltd. Heat development type diazo copying material containing a light insensitive intermediate layer provided between the support and the photosensitive layer
US5221713A (en) * 1991-10-07 1993-06-22 Rohm And Haas Company Co-microagglomeration of emulsion polymers (encapsulated core/shell additives for pvc)
US5236800A (en) * 1988-04-12 1993-08-17 Fuji Photo Film Co., Ltd. Heat-developable light-sensitive copying material comprising microcapsules having substantially no solvent
US5466556A (en) * 1993-05-14 1995-11-14 Brother Kogyo Kabushiki Kaisha Photosensitive microencapsulated toner
US5470683A (en) * 1993-07-28 1995-11-28 Brother Kogyo Kabushiki Kaisha Photosensitive microcapsule toner
US20040265589A1 (en) * 2003-04-25 2004-12-30 Fuji Photo Film Co., Ltd. Microcapsule and manufacturing method thereof
EP1506855A2 (en) 2003-08-15 2005-02-16 Fuji Photo Film Co., Ltd. Lithographic printing plate precursor and lithographic printing method
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DE1243643B (de) 1967-07-06
IT631615A (ro)
GB984632A (en) 1965-03-03
GB898668A (en) 1962-06-14
DE1209999B (de) 1966-02-03

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