US3775130A - Photosensitive material comprising benzopyrylium dye sensitizer - Google Patents

Photosensitive material comprising benzopyrylium dye sensitizer Download PDF

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Publication number
US3775130A
US3775130A US00211743A US3775130DA US3775130A US 3775130 A US3775130 A US 3775130A US 00211743 A US00211743 A US 00211743A US 3775130D A US3775130D A US 3775130DA US 3775130 A US3775130 A US 3775130A
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United States
Prior art keywords
resinous binder
photosensitive material
binder solution
vinyl
group
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Expired - Lifetime
Application number
US00211743A
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English (en)
Inventor
T Enomoto
T Kawanishi
A Yasumori
T Shiga
Y Hirosawa
T Kubota
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Ricoh Co Ltd
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Ricoh Co Ltd
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Classifications

    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00—Photosensitive materials
    • G03C1/675—Compositions containing polyhalogenated compounds as photosensitive substances
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
    • G03F7/031—Organic compounds not covered by group G03F7/029
    • 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
    • Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
    • Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
    • Y10S430/1055—Radiation sensitive composition or product or process of making
    • Y10S430/114—Initiator containing
    • Y10S430/116—Redox or dye sensitizer
    • 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
    • Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
    • Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
    • Y10S430/1055—Radiation sensitive composition or product or process of making
    • Y10S430/127—Spectral sensitizer containing

Definitions

  • the present invention relates to a photosensitive material for producing a photographic recording material useful in the reproduction of an original image thereon by photopolymerization.
  • the dye sensitizers which have hitherto been sugested to be used in the photosensitive layer of such photographic recording materials as mentioned above are generally obtainable on the market and include the following dyes: triphenylmethyl dyes (such as Malachite Green, Crystal Violet, etc), Rhodamine B, Eosine B, Cyanin dyes (such as pinacyanol, Ethyl Red, Quinaldine Red, etc.), Styryl dyes [4- (p-dimethylaminostyryl )quinoline, etc. Acridine dyes, Thiazine dyes, etc. Rhodamine B- and Styryl dyes are said to be most satisfactory. However, the perfumance of the aforementioned dye sensitizers are not completely satisfactory in meeting the requirements of photographic recording materials.
  • the present invention provides photosensitive materials for producing photographic recording materials having improved properties due to the use of novel dye sensitizers.
  • the dye sensitizers utilized in the photosensitive products of the present invention are salts selected from the group consisting benzopyrylium salts having a chemical structure expressed by formula-(I) and double complex salts formed as reaction products of said benzopyrylium salts and decolorized derivatives thereof having a chemical structure expressed by the formula-(II).
  • Y is a radical selected from the group consisting of hydrogen, halogen, nitro radical, nitrile radical and carboxyl; radical;
  • R is a radical selected from the group consisting of hydrogen and alkyl radicals having I to 4 carbon atoms; 1 y
  • R is a radical selected from the group consisting of hydrogen and phenyl radical
  • R and R each is a radical selected from the group consisting of hydrogen, alkyl radicals having 1 to 2 carbon atoms and alkoxyl radicals having I to 2 carbon atoms; n and n each is an integer of l to 2; and Z is an anionic functional group.
  • dye sensitizers comprising a benzopyrylium salt or a double complex salt consisting essentially of said benzopyrylium salt and its decolorized derivative have properties which remarkably contribute to the improvement of photo sensitivity of the photosensitive layer extending over a very wide region of wave length ranging approximately from 400 my. to 800 mu. They are crystalline substances which are violet bluish violet blue in color when dissolved in an organic solvent.
  • the benzopyrylium salt having the formula-(I) is prepared by reacting a substituted 2-hydroxybenzaldehyde having the formula-(II'):
  • the reaction which takes place between the compounds having respectively the formula-(II') and (Ill) forms an aldehyde acetone derivative having the formula resonance structure with the formula-(V) where R,, R R X and n are as defined above.
  • aldehyde having the formula-(IV) By adding aldehyde having the formula-(IV) to the previous product, a condensation cyclic reaction takes place.
  • the mineral acid hydrochloric acid is used; and for the solvent, such organic acids as formic acid, acetic acid, etc., are used.
  • the quantity of the mineral acid added in this reaction is from 2 to 6 moles per mole of substituted 2-hydroxybenzaldehyde.
  • the anionic functional group which corresponds to Z in the formula-(I) can be obtained either by selecting the acid which is introduced at the time of the condensation cyclic reaction or by reacting an acid or a salt having the desired functional group with the product mentioned above.
  • Typical acids or salts for this reaction include perchloric acid, periodic acid, phosphoric acid, hydrochloric acid, sulfuric acid, oxalic acid, sodium borofluoride, potassium iodide, sodium iodide, potassium bromide, sodium bromide, dimethylphos-- phate, diphenylphosphate, etc.
  • substituted 2-hydroxybenzaldehyde having the formula-(ll') can be readily prepared, either by chlorinating or brominating the corresponding aldehyde or by formylating phenols.
  • the substituted 2-hydroxybenzaldehyde thus prepared may be reacted with the acetone derivative having the formula-(Ill) in a mixed acid consisting of acetic acid and formic acid, or with the addition of any of the aforementioned acids, in the presence of a mineral acid or acids.
  • the over-all reaction required for the preparation of the benzopyrylium salts can be conducted in succession in one reactor at room temperature.
  • the decolorized derivatives which form the double complex salts of the present invention are prepared by refluxing a benzopyrylium salt of formula-(l), in an alkaline solvent, for instance, a mixed solvent of methanol-benzene containing sodium bicarbonate. The solution is then concentrated and the reaction product is poured into a mixture of crashed ice and water to precipitate the crystals.
  • the amount of alkali such as sodium bicarbonate and sodium carbonate employed is from 60 to wt. percent based on the weight of the reactants.
  • the double complex salt consisting essentially of the benzopyrylium salt and its decolorized derivative is prepared by means of a chemical reaction wherein the decolorized derivative obtained according to the aforementioned method and indicated by the formula-(ll) is admixed with the benzopyrylium salt having the formula-(I) and reacted in a suitable solvent.
  • the resultant double complex salt demonstrates excellent sensitivity when used in the photosensitive materials.
  • Reaction solvents utilized in combining a decolorized den'vative having the formula-( ll) with a benzopyrylium salt having the formula-(l) may be selected from the group consisting of dichloroethane, toluene, xylene and tetrahydrofuran.
  • the reaction takes place under reflux conditions at a temperature from 50 to C, preferably at 50 60C. After completion of the reaction, the solvent is removed by distillation under reduced pressure and the reaction product is added to ether to precipitate the desired crystalline product.
  • the reaction mixture thus prepared was added dropwise to 180 ml of 15 percent l-lClO which had been cooled to 10C or below with stirring during a period of about 2 hours.
  • the resultant precipitate was filtered by suction and was washed with 300 400 ml of ethyl ether. Recrystalization was effected with acetic acid to obtain 15 g of desired crystalline product.
  • the melting point of this product ranged between 214 and 216C.
  • the absorption maximum wave length ()t max.) measured with the product in dichloroethane solution was 577 my.
  • the present invention provides photosensitive mate- The color tone of the image developed on the photorials comprising a resinous binder solution for produc- 15 graphic recording material made of the photosensitive ing a photographic recording material wherein a dye sensitizer comprising either a benzopyrylium salt which is obtained according to the aforementioned synthetic method or its double complex salt dye sensitizer is utilized in the place of previously known dye sensitizers such as Rhodamine B or Styryl dye which have been used in conventional photographic recording materials.
  • the supports, photo-active agents, vinyl monomers, and other materials such as solvents utilized in this invention are which have been conventionally employed. Binders utilized in this invention are not necessarily limited to water soluble resins, but include various kinds of resins and natural high polymeric substances.
  • Typical examples include, cellulose acetate, cellulose acetate propionate, ethylcellulose, cellulose nitrate, polyvinylchloride, polyvinylidene chloride, polyvinylacetate, polyvinyl acetal, polyvinyl alcohol, polymethyl methacrylate, polystyrene, rubber hydrochloride, gelatin, casein, carboxymethyl cellulose gun arabic, etc.
  • Useful photo-active agents include, in addition to the conventional aliphatic halides, such alicyclic compounds as benzene hexachloride, etc., and an aromatic halides such as polychlorobiphenyl, etc.
  • Typical photo-active halides include those selected from the group consisting of chloroform, carbon tetrachloride, carbon tetrabromide, iodoform, hexachloroethane, hexachlorobenzene, tetrabromobutane, tetrachlorotetrahydronaphthalene and polychlorobiphenyl.
  • any of monomers such as N-vinylindole, N- vinylcarbazole, N-vinyl-phenyl-a-naphthylamine, N- vinylpyrrole, N-vinylpyrrolidone, N- vinyldiphenylamine, N-vinylsuccinimide, N- vinylphthalimide, N-vinyl-N-phenylacetamide, N-vinyl- N-methylacetamide, N-vinyl-diglycollylimide and 3,o-dibromo-N-vinylcarbazole, can be used in the present invention.
  • monomers such as N-vinylindole, N- vinylcarbazole, N-vinyl-phenyl-a-naphthylamine, N- vinylpyrrole, N-vinylpyrrolidone, N- vinyldiphenylamine, N-vinylsuccinimide, N- vinylphthalimide, N-vinyl-N-phenylace
  • Typical liquids which serve as solvents or dispersion media for use in the invention include water, methylethylketone, ethylacetate, acetone, toluene, trichloroethylene and methylalcohol.
  • a photosensitive material comprising a resinous binder solution containing the aforementioned resinous binder and photosensitive materials is applied to the surface of a support, made of film or paper to form a photosensitive layer
  • a transparent photosensitive film or photosensitive recording paper of light yellow light bluish violet color is obtained and its sensitivity is much better than conventional ones as seen from the examples.
  • the photosensitive material prepared according to the present invention varies depending upon the kind of the resinous binder admixed with the aforementioned photosensitive materials.
  • the developed image takes on a color tone of deep reddish purple; in case where polystyrene, ethyl cellulose, cellulose nitrate, rubber hydrochloride, cellulose acetate, polyvinylchloride, celluslose acetate propionate and polyvinylidene chloride are used, the developed image devlops the color tone of greenish brown or blackish green.
  • polyvinyl acetate the developed image presents the light brown color tone; and when polymethylmethacrylate is used, the developed image shows the color tone of light grey.
  • the resinous binder in the range between 50 and 100 parts by weight in a proper solvent, a photoactive agent between 5 and 100 parts by weight, and a dye sensitizer between 0.001 and 1.0 part by weight respectively per 100 parts by weight of N-vinyl monomer contained in said proper olvent.
  • a control photosensitive recording material was prepared according to the same method except for the use of Rhodamine B in the place of the dye sensitizer No. l. It'required about five minutes exposure to the light source to obtain the same density of the reproduced image as was obtained with the photosensitive recording material according to the present invention. 7
  • Example 1 5 g of polyvinylidene chloride weredissolved in 20 ml of methylethylketone, to which 5 g of N-vinyl carbazole monomer and 20 mg of the complex dye sensitizer No. 4 shown in Table-1. The same procedures were used as in Example 1 to obtain a photographic recording material. A greenish-brown image was produced in the photosensitive layer of the resultant photographic recording material when developed by the same method as that of Example Example 3.
  • the photographic recording materials were prepared by usingthe respective benzopyrylium salts obtained according to the aforementioned examples. (A) through (E) for preparing the benzopyrylium salts in the place of the respective complex dye sensitizers which were used as a-dye sensitizer in Examples 1 3 with similar conditions and procedures.
  • a photosensitive material for producing a photographic recording material comprising a resinous binder solution containing dispersed therein a .photo-polymerizable N-vinyl monomer, a photo-active wherein X is a radical selected from the group consisting of hydrogen, halogen, nitro radical and nitrile radical;
  • Y is a radical selected from the group'consisting of hydrogen, halogen, nitro radical, nitrile radical and carboxyl radical;
  • R is a radical selected from the group consisting of hydrogen and alkyl radicals having 1 m4 carbon atoms;
  • R is a radical selected from the group consisting of hydrogen and phenyl radical
  • R and R each is a radical selected from the group consisting of hydrogen, alkyl radicals having 1 to 2 carbon atoms and alkoxyl radicals having 1 to 2 carbon atoms; n and n each is an integer of l to 2; and Z is an anionic functional group; and
  • N-vinyl monomer is a member selected from the group consisting of N- vinylindole, N-vinylcarbazole, N-vinyl-phenyl-anaphthylamine, N-vinylpyrrole, N-vinylpyrrolidone, N-vinyldiphenylaminc, N-vinylsuccinimide, N- vinylphthaliumide, N-vinyl-N-phenylacetamide, N- vinyl-N-methylacctamide, N-vinyldigly-collylimide and 3,6-dibromo-N-vinylcarbazolei 3.
  • a photosensitive material in which a resinous binder dissolved in said resinous binder solutions is a member selected from the group consisting of cellulose acetate, cellulose acetate propionate, ethylcellulose, cellulose nitrate, polyvinylchloride, polyvinylidene chloride, polyvinylacetate, polyvinyl acetal, polyvinyl alcohol, polymethyl methacrylate, polystyrene, rubber hydrochloride, gelatine, casein,, carboxymethyl cellulose and gum arabi, and a mixing ratio of said resinous binder against said N-vinyl monomer contained in said resinous binder solution is in the range of from 50 to 500 partsby weight per parts by weight of said N-vinyl monomer.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
  • Heat Sensitive Colour Forming Recording (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Polymerisation Methods In General (AREA)
  • Pyrane Compounds (AREA)
US00211743A 1970-12-28 1971-12-23 Photosensitive material comprising benzopyrylium dye sensitizer Expired - Lifetime US3775130A (en)

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JP45125987A JPS509178B1 (enExample) 1970-12-28 1970-12-28

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JP (1) JPS509178B1 (enExample)
DE (1) DE2164395A1 (enExample)
FR (1) FR2121030A5 (enExample)
GB (1) GB1378870A (enExample)

Cited By (48)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3899338A (en) * 1972-02-09 1975-08-12 Horizons Inc Photosensitive material suitable for use as a photoresist
US4251619A (en) * 1977-06-08 1981-02-17 Konishiroku Photo Industry Co., Ltd. Process for forming photo-polymeric image
EP0223587A1 (en) * 1985-11-20 1987-05-27 The Mead Corporation Photosensitive materials containing ionic dye compounds as initiators
US4772530A (en) * 1986-05-06 1988-09-20 The Mead Corporation Photosensitive materials containing ionic dye compounds as initiators
US4800149A (en) * 1986-10-10 1989-01-24 The Mead Corporation Photohardenable compositions containing a dye borate complex and photosensitive materials employing the same
US4874450A (en) * 1987-01-29 1989-10-17 The Mead Corporation Laminating transparent or translucent materials using ionic dye-counter ion complexes
US4971891A (en) * 1987-10-13 1990-11-20 Fuji Photo Film Co., Ltd. Photopolymerizable compositions containing organoboron compounds and pyrylium or thiopyrylium dyes
US4977511A (en) * 1985-11-20 1990-12-11 The Mead Corporation Photosensitive materials containing ionic dye compound as initiators
US5418113A (en) * 1988-11-18 1995-05-23 Canon Kabushiki Kaisha Photosensitive resin composition and method of preparing volume type phase hologram member using same
US5616443A (en) 1993-08-05 1997-04-01 Kimberly-Clark Corporation Substrate having a mutable colored composition thereon
US5643356A (en) 1993-08-05 1997-07-01 Kimberly-Clark Corporation Ink for ink jet printers
US5645964A (en) 1993-08-05 1997-07-08 Kimberly-Clark Corporation Digital information recording media and method of using same
US5681380A (en) 1995-06-05 1997-10-28 Kimberly-Clark Worldwide, Inc. Ink for ink jet printers
US5700850A (en) 1993-08-05 1997-12-23 Kimberly-Clark Worldwide Colorant compositions and colorant stabilizers
US5709955A (en) 1994-06-30 1998-01-20 Kimberly-Clark Corporation Adhesive composition curable upon exposure to radiation and applications therefor
US5721287A (en) 1993-08-05 1998-02-24 Kimberly-Clark Worldwide, Inc. Method of mutating a colorant by irradiation
US5733693A (en) 1993-08-05 1998-03-31 Kimberly-Clark Worldwide, Inc. Method for improving the readability of data processing forms
US5739175A (en) 1995-06-05 1998-04-14 Kimberly-Clark Worldwide, Inc. Photoreactor composition containing an arylketoalkene wavelength-specific sensitizer
US5747550A (en) 1995-06-05 1998-05-05 Kimberly-Clark Worldwide, Inc. Method of generating a reactive species and polymerizing an unsaturated polymerizable material
US5773182A (en) 1993-08-05 1998-06-30 Kimberly-Clark Worldwide, Inc. Method of light stabilizing a colorant
US5782963A (en) 1996-03-29 1998-07-21 Kimberly-Clark Worldwide, Inc. Colorant stabilizers
US5786132A (en) 1995-06-05 1998-07-28 Kimberly-Clark Corporation Pre-dyes, mutable dye compositions, and methods of developing a color
US5798015A (en) 1995-06-05 1998-08-25 Kimberly-Clark Worldwide, Inc. Method of laminating a structure with adhesive containing a photoreactor composition
US5811199A (en) 1995-06-05 1998-09-22 Kimberly-Clark Worldwide, Inc. Adhesive compositions containing a photoreactor composition
US5837429A (en) 1995-06-05 1998-11-17 Kimberly-Clark Worldwide Pre-dyes, pre-dye compositions, and methods of developing a color
US5849411A (en) 1995-06-05 1998-12-15 Kimberly-Clark Worldwide, Inc. Polymer film, nonwoven web and fibers containing a photoreactor composition
US5855655A (en) 1996-03-29 1999-01-05 Kimberly-Clark Worldwide, Inc. Colorant stabilizers
US5865471A (en) 1993-08-05 1999-02-02 Kimberly-Clark Worldwide, Inc. Photo-erasable data processing forms
US5885337A (en) 1995-11-28 1999-03-23 Nohr; Ronald Sinclair Colorant stabilizers
US5891229A (en) 1996-03-29 1999-04-06 Kimberly-Clark Worldwide, Inc. Colorant stabilizers
US6008268A (en) 1994-10-21 1999-12-28 Kimberly-Clark Worldwide, Inc. Photoreactor composition, method of generating a reactive species, and applications therefor
US6017471A (en) 1993-08-05 2000-01-25 Kimberly-Clark Worldwide, Inc. Colorants and colorant modifiers
US6017661A (en) 1994-11-09 2000-01-25 Kimberly-Clark Corporation Temporary marking using photoerasable colorants
US6033465A (en) 1995-06-28 2000-03-07 Kimberly-Clark Worldwide, Inc. Colorants and colorant modifiers
US6071979A (en) 1994-06-30 2000-06-06 Kimberly-Clark Worldwide, Inc. Photoreactor composition method of generating a reactive species and applications therefor
US6099628A (en) 1996-03-29 2000-08-08 Kimberly-Clark Worldwide, Inc. Colorant stabilizers
US6211383B1 (en) 1993-08-05 2001-04-03 Kimberly-Clark Worldwide, Inc. Nohr-McDonald elimination reaction
US6228157B1 (en) 1998-07-20 2001-05-08 Ronald S. Nohr Ink jet ink compositions
US6242057B1 (en) 1994-06-30 2001-06-05 Kimberly-Clark Worldwide, Inc. Photoreactor composition and applications therefor
US6265458B1 (en) 1998-09-28 2001-07-24 Kimberly-Clark Worldwide, Inc. Photoinitiators and applications therefor
US6277897B1 (en) 1998-06-03 2001-08-21 Kimberly-Clark Worldwide, Inc. Photoinitiators and applications therefor
US6294698B1 (en) 1999-04-16 2001-09-25 Kimberly-Clark Worldwide, Inc. Photoinitiators and applications therefor
US6331056B1 (en) 1999-02-25 2001-12-18 Kimberly-Clark Worldwide, Inc. Printing apparatus and applications therefor
US6368395B1 (en) 1999-05-24 2002-04-09 Kimberly-Clark Worldwide, Inc. Subphthalocyanine colorants, ink compositions, and method of making the same
US6368396B1 (en) 1999-01-19 2002-04-09 Kimberly-Clark Worldwide, Inc. Colorants, colorant stabilizers, ink compositions, and improved methods of making the same
US6486227B2 (en) 2000-06-19 2002-11-26 Kimberly-Clark Worldwide, Inc. Zinc-complex photoinitiators and applications therefor
US6503559B1 (en) 1998-06-03 2003-01-07 Kimberly-Clark Worldwide, Inc. Neonanoplasts and microemulsion technology for inks and ink jet printing
US6524379B2 (en) 1997-08-15 2003-02-25 Kimberly-Clark Worldwide, Inc. Colorants, colorant stabilizers, ink compositions, and improved methods of making the same

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US3300314A (en) * 1963-02-01 1967-01-24 Eastman Kodak Co Nonsilver, light-sensitive photographic elements
US3503745A (en) * 1963-05-06 1970-03-31 Bell & Howell Co Dye sensitization of light sensitive systems
US3607266A (en) * 1963-05-06 1971-09-21 Bell & Howell Co Image intensification process for sensitized film
US3600179A (en) * 1968-03-14 1971-08-17 Bell & Howell Co Organic photo-material of increased contrast

Cited By (64)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3899338A (en) * 1972-02-09 1975-08-12 Horizons Inc Photosensitive material suitable for use as a photoresist
US4251619A (en) * 1977-06-08 1981-02-17 Konishiroku Photo Industry Co., Ltd. Process for forming photo-polymeric image
EP0223587A1 (en) * 1985-11-20 1987-05-27 The Mead Corporation Photosensitive materials containing ionic dye compounds as initiators
US4977511A (en) * 1985-11-20 1990-12-11 The Mead Corporation Photosensitive materials containing ionic dye compound as initiators
US4772530A (en) * 1986-05-06 1988-09-20 The Mead Corporation Photosensitive materials containing ionic dye compounds as initiators
US4800149A (en) * 1986-10-10 1989-01-24 The Mead Corporation Photohardenable compositions containing a dye borate complex and photosensitive materials employing the same
US4874450A (en) * 1987-01-29 1989-10-17 The Mead Corporation Laminating transparent or translucent materials using ionic dye-counter ion complexes
US4971891A (en) * 1987-10-13 1990-11-20 Fuji Photo Film Co., Ltd. Photopolymerizable compositions containing organoboron compounds and pyrylium or thiopyrylium dyes
US5418113A (en) * 1988-11-18 1995-05-23 Canon Kabushiki Kaisha Photosensitive resin composition and method of preparing volume type phase hologram member using same
US5908495A (en) 1993-08-05 1999-06-01 Nohr; Ronald Sinclair Ink for ink jet printers
US6211383B1 (en) 1993-08-05 2001-04-03 Kimberly-Clark Worldwide, Inc. Nohr-McDonald elimination reaction
US5643701A (en) 1993-08-05 1997-07-01 Kimberly-Clark Corporation Electrophotgraphic process utilizing mutable colored composition
US5645964A (en) 1993-08-05 1997-07-08 Kimberly-Clark Corporation Digital information recording media and method of using same
US6120949A (en) 1993-08-05 2000-09-19 Kimberly-Clark Worldwide, Inc. Photoerasable paint and method for using photoerasable paint
US5683843A (en) 1993-08-05 1997-11-04 Kimberly-Clark Corporation Solid colored composition mutable by ultraviolet radiation
US5700850A (en) 1993-08-05 1997-12-23 Kimberly-Clark Worldwide Colorant compositions and colorant stabilizers
US6054256A (en) 1993-08-05 2000-04-25 Kimberly-Clark Worldwide, Inc. Method and apparatus for indicating ultraviolet light exposure
US5721287A (en) 1993-08-05 1998-02-24 Kimberly-Clark Worldwide, Inc. Method of mutating a colorant by irradiation
US5733693A (en) 1993-08-05 1998-03-31 Kimberly-Clark Worldwide, Inc. Method for improving the readability of data processing forms
US5643356A (en) 1993-08-05 1997-07-01 Kimberly-Clark Corporation Ink for ink jet printers
US5865471A (en) 1993-08-05 1999-02-02 Kimberly-Clark Worldwide, Inc. Photo-erasable data processing forms
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Also Published As

Publication number Publication date
DE2164395A1 (de) 1972-07-13
FR2121030A5 (enExample) 1972-08-18
JPS509178B1 (enExample) 1975-04-10
GB1378870A (en) 1974-12-27
DE2164395C3 (enExample) 1974-05-02
DE2164395B2 (enExample) 1973-10-11

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