US3385700A - Recording process - Google Patents

Recording process Download PDF

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Publication number
US3385700A
US3385700A US463029A US46302965A US3385700A US 3385700 A US3385700 A US 3385700A US 463029 A US463029 A US 463029A US 46302965 A US46302965 A US 46302965A US 3385700 A US3385700 A US 3385700A
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US
United States
Prior art keywords
solution
compound
cyclohexadienone
image
colour
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
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US463029A
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English (en)
Inventor
Willems Jozef Frans
Poot Albert Lucien
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Gevaert Photo Producten NV
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Gevaert Photo Producten NV
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Publication of US3385700A publication Critical patent/US3385700A/en
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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
    • G03C1/72—Photosensitive compositions not covered by the groups G03C1/005 - G03C1/705
    • G03C1/73—Photosensitive compositions not covered by the groups G03C1/005 - G03C1/705 containing organic compounds
    • 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
    • G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors

Definitions

  • the present invention relates to a process for recording optical information by means of a material containing a cyclohexadienone compound.
  • a light-sensitive system based on the phototransformation of a cyclohexadienone compound into a compound, which is reactive with a nucleophilic reagent, can be used for recording and reproducing optical information.
  • R represents an acetoxy group
  • R represents hydrogen, or a hydrocarbon group e.g. alkyl or aryl, an ether group or an acetoxy group,
  • each of R R R and R represents hydrogen, or a hydrocarbon group e.g. alkyl such as methyl, ethyl, n-propyl, isopropyl, n-butyl, tert. butyl, or isoamyl, an aryl group or substituted aryl group, acetyl or allyl,
  • alkyl such as methyl, ethyl, n-propyl, isopropyl, n-butyl, tert. butyl, or isoamyl, an aryl group or substituted aryl group, acetyl or allyl
  • R and R together may represent the atoms necessary to close an aromatic ring
  • R and R, as well as R, and R together may represent the atoms necessary to close a homocyclic saturated ring
  • each of R',, R ,R R' and R' represents hydrogen, alkyl or aryl
  • R represents an acetoxy group
  • the compounds formed on exposing the above-mentioned cyclohexadienone compounds are ketene intermediates.
  • a visible image can be produced in a photographic element containing one of said cyclohexadienone compounds, by image-wise or record-wise U.V.-irradiating said element thereby transforming said cyclohexadienone compound into a ketene compound, which is reactive with a nucleophilic reagent, and by allowing said ketene compound to react with said nucleophilic reagent to produce a condensation product, which can be detected by means of a colour reaction, thereby forming a coloured product on the exposed areas.
  • the ketene compound formed by exposure is allowed to react in the photographic element with water, resulting in the image-wise formation of a diene acid.
  • the image-wise formed acid can now be used to produce a visible image e.g. by detecting the acid with suitable pH-indicators, which undergo a colour change under the influence of the hydrogen atoms.
  • the image-wise formed acid can be used to neutralise abase image-wise, whereby the non-neutralised base on the unexposed areas can e.g. be detected by means of a pH-indicator.
  • Classes of pH-indicators are e.g. nitrophenols, azo compounds, phthaleins and sulphophthaleins.
  • the image-wise pH- difierentiation obtained according to one of the types of the foregoing photographic reproduction methods can in principle be used to produce image-Wise a pH-dependent colour reaction or to form substances building up an image by using the catalysing influence of the image-wise produced hydrogen ions or image-wise neutralised hydroxyl ions.
  • a visible image can be produced in a photographic element containing one of said cyclohexadienone compounds by image-wise or record-wise U.V.-irradiating said element thereby transforming said cyclohexadienone compound into a ketene compound, which on the exposed areas blocks the chemical reactivity of a reactant, which is incorporated in the said element before or after exposure, and after exposure allowing the residual reactant to react at the unexposed areas with a reaction agent to form a coloured product.
  • the ketene compound formed on exposing a cyclohexadienone compound is allowed to react with a colour coupler possessing a reactive function with respect to a-coupler coupling agent which may be incorporated in the same material.
  • the colour coupler is chosen such that the reactive radical thereof is blocked by reaction with the ketene compound formed on exposure and is thus excluded from any reaction with a colour coupling agent on the exposed parts.
  • Suitable colour couplers are colour couplers having a coupling function of the nucleophilic type e.g. colour couplers containing reactive hydrogen atoms in the coupling position, such as the colour-forming compounds containing a reactive methylene or phenolic hydroxyl group capable of reacting with the oxidation products of primary aromatic amino coupling developers.
  • Particularly suitable colour couplers are those of the phenol or naphthol type.
  • cyclohexadienone compounds used in the process of the present invention can be prepared according to known techniques. As an illustration thereof references of the preparation are given hereinafter.
  • the cyclohexadienone compounds used in the present invention are mainly U.V.-sensitive.
  • the rate of phototransformation is relatively the highest in the wavelength range of 300 m,u-432 me.
  • a photographic material for copying purposes according to one of the above-described recording and reproduction methods can be prepared by coating a cyclohexadienone compound from a solution or dispersion onto -a support, which may be more or less porous, e.g. a paper support or can be prepared by incorporating a cyclohexadienone compound into a liquid-permeable layer, preferably a water-permeable layer in order to allow the diffusion therein of chemical reactants.
  • a support which may be more or less porous, e.g. a paper support or can be prepared by incorporating a cyclohexadienone compound into a liquid-permeable layer, preferably a water-permeable layer in order to allow the diffusion therein of chemical reactants.
  • a support which may be more or less porous, e.g. a paper support or can be prepared by incorporating a cyclohexadienone compound into a liquid-permeable layer, preferably a water-
  • the cyclohexadienone compound is incorporated in non-migratory form into a liquid-permeable layer or support.
  • Example 1 A mixture of the following composition:
  • the dried layer is treated with a solution of 0.4 g. of sodium hydroxide and 1 g. of lauryl sulphate as wetting agent in a mixture of 90 cm. of ethanol and 10 cm. of water. After having been dried to the air, the photographic material has a yellow colour.
  • the photographic material is exposed for 2 min. through a black-and-white diapositive of a line original with the aid of a Philips ultra-violet-radiating bulb of watts placed at a distance of 10 cm.
  • Example 2 A mixture of the following composition:
  • Example 3 A mixture of the following composition:
  • the dried layer is treated with an alkaline solution as described in Example 1.
  • Example 2 During exposure as described in Example 1, the exposed parts turned from red to colourless. In this way a positive image is obtained.
  • Example 4 A mixture of the following composition:
  • the dried layer is exposed as described in Example 1.
  • Example 5 A mixture of the following composition:
  • the dried layer is exposed as described in Example 1 but for 5 min.
  • Example 6 A mixture of the following composition:
  • the colour of the exposed areas turned from colourless to blue.
  • Example 7 A mixture of the following composition:
  • Example 10 A mixture of the following composition:
  • the material dried to the air is exposed as described in Example 1, but for 1 min. only. A green positive image is formed. A visually detectable image-differentiation is already present after an exposure time of 5 seconds.
  • Example 11 A mixture of the following composition:
  • Example 12 A mixture of the following composition:
  • the dried layer is exposed as described in Example 1, except that the exposure time is only 1 min.
  • the exposed material is developed in a solution of potassium hexacyanofer-rate'(III) in water/ethanol .(80/20). A greenish positive image is obtained.
  • Example 15 A mixture of the following composition:
  • Example 16 A mixture of the following composition:
  • Example 2 The dried layer is exposed as described in Example 1 and developed by dipping in a 5% aqueous iron(III) chloride solution. First a positive image is obtained. By rinsing with water and drying to the air the image is reversed:
  • Example 17 A mixture of the following composition:
  • the dried layer is exposed as described in Example 1.
  • the exposed material is developed with an ammoniacal silver nitrate solution. Immediately after the contact with said solution, a positive image is formed, which, however, disappears very rapidly in favour of a reversal image.
  • Example 18 A mixture of the following composition:
  • Example 12 After having been dried to the air, the layer is exposed as described in Example 1 and treated with an alkaline coupling solution as described in Example 12.
  • a stable positive brown image is obtained.
  • the background has a pale brown colour.
  • Example 20 A mixture of the following composition:
  • the dried layer is exposed and developed as described in Example 13.
  • Example 21 A mixture of the following composition:
  • Example 22 A mixture of the following composition:
  • the dried layer is exposed and developed as described in Example 13.
  • the invention permits positive copies to be obtained directly from positive original documents, or from negative originals, according to the ingredients of the recording material.
  • the invention is, of course, not only applicable to the making of images of readable matter but can be applied for recording any selective exposure pattern such as optical signals.
  • a photographic process comprising the step of image-wise or record-wise exposing to U.V.-radiation an element containing as U.V.-sensitive compound a 3,5- cyclohexadienone compound containing in ortho-position to the oxo group at least one acetoxy group or a 2,5- cyclohexadienone compound containing a para-position to the oxo group at least one acetoxy group.
  • R represents an acetoxy group
  • R represents a member selected from the group consisting of hydrogen, a hydrocarbon group, an ether group and an acetoxy group
  • each of R R R and R represents a member selected from the group consisting of hydrogen and a hydrocarbon group
  • each of R' R R' R' and R' represents a member selected from the group consisting of hydrogen, an alkyl and an aryl group,
  • R' represents an acetoxy group, and wherein R and R may represent the atoms necessary to close an aromatic ring, and
  • R and R as well as R, and R together may represent the atoms necessary to close a homocyclic saturated ring.
  • a photographic process according to claim 1, com prising the further step of detecting by colour reaction the reaction product formed by reaction between a nucleophilic reagent and the compound formed on exposing to U.V.-radiation said cyclohexadienone compound.
  • nucleophilic reagent is reagent is reacted in situ with the compound formed by interaction of actinic light on the cyclohexadienone compound, and the unreacted nucleophilic reagent is reacted with another compound to produce a product absorbing visible light.
  • nucleophilic reagent is water and the detection of the reaction product is carried out by means of a pH-indicator.
  • nucleophilic reagent is a colour coupler having a reactive hydrogen atom in the coupling position.
  • nucleophilic reagent is a colour coupler having a reactive methylene or phenolic hydroxyl group capable of reacting with the oxidation products of a primary aromatic amino coupling developer.
  • nucleophilic reagent is a carbinol base.
  • nucleophilic reagent is a phenolic hydroxyl groupcontaining photographic developer and the exposed material is developed by means of an ammoniacal silver nitrate solution.
  • a recording material comprising a layer, that incorporates a 3,5-cyclohexadienone compound containing in ortho-position to the oxo group at least one acetoxy group or a 2,5-cyclohexadienone compound containing in para-position to the OX0 group at least one acetoxy group and that also incorporates a nucleophilic agent in the form of a colour coupler with groups that can react directly or indirectly with a ketene formed by exposure of the cyclohexadienone compound to ultra-violet radiation and thereby cease to be available for reaction with a colour coupling agent.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Color Printing (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Printing Plates And Materials Therefor (AREA)
  • Photosensitive Polymer And Photoresist Processing (AREA)
US463029A 1964-06-12 1965-06-10 Recording process Expired - Lifetime US3385700A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB24520/64A GB1070863A (en) 1964-06-12 1964-06-12 Light-sensitive photographic materials
GB50828/64A GB1080380A (en) 1964-06-12 1964-12-14 Manufacture of printing plates by photographic methods

Publications (1)

Publication Number Publication Date
US3385700A true US3385700A (en) 1968-05-28

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US463033A Expired - Lifetime US3385703A (en) 1964-06-12 1965-06-10 Recording process
US463029A Expired - Lifetime US3385700A (en) 1964-06-12 1965-06-10 Recording process

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US (2) US3385703A (de)
BE (1) BE665367A (de)
CH (1) CH458057A (de)
DE (1) DE1285877B (de)
FR (1) FR1477432A (de)
GB (2) GB1070863A (de)
NL (1) NL6507549A (de)

Cited By (42)

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US3537856A (en) * 1965-08-26 1970-11-03 Sankyo Co Light-sensitive photographic composition
US4101323A (en) * 1975-03-27 1978-07-18 Hoechst Aktiengesellschaft Radiation-sensitive copying composition
US4902603A (en) * 1987-10-05 1990-02-20 Olin Corporation Photoresist compositions containing selected 6-acetoxy cyclohexadienone photosensitizers and novolak resins
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
US5685754A (en) * 1994-06-30 1997-11-11 Kimberly-Clark Corporation Method of generating a reactive species and polymer coating applications therefor
US5700850A (en) * 1993-08-05 1997-12-23 Kimberly-Clark Worldwide Colorant compositions and colorant stabilizers
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
US6017661A (en) 1994-11-09 2000-01-25 Kimberly-Clark Corporation Temporary marking using photoerasable colorants
US6017471A (en) 1993-08-05 2000-01-25 Kimberly-Clark Worldwide, Inc. Colorants and colorant modifiers
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
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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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US3102810A (en) * 1961-04-05 1963-09-03 Horizons Inc Print-out cyanine and styryl dye bases and process of producing litho masters and the like therewith

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Cited By (59)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3537856A (en) * 1965-08-26 1970-11-03 Sankyo Co Light-sensitive photographic composition
US4101323A (en) * 1975-03-27 1978-07-18 Hoechst Aktiengesellschaft Radiation-sensitive copying composition
US4902603A (en) * 1987-10-05 1990-02-20 Olin Corporation Photoresist compositions containing selected 6-acetoxy cyclohexadienone photosensitizers and novolak resins
US6127073A (en) 1993-08-05 2000-10-03 Kimberly-Clark Worldwide, Inc. Method for concealing information and document for securely communicating concealed information
US6060200A (en) 1993-08-05 2000-05-09 Kimberly-Clark Worldwide, Inc. Photo-erasable data processing forms and methods
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
US5908495A (en) 1993-08-05 1999-06-01 Nohr; Ronald Sinclair Ink for ink jet printers
US5683843A (en) * 1993-08-05 1997-11-04 Kimberly-Clark Corporation Solid colored composition mutable by ultraviolet radiation
US5643701A (en) * 1993-08-05 1997-07-01 Kimberly-Clark Corporation Electrophotgraphic process utilizing mutable colored composition
US6054256A (en) 1993-08-05 2000-04-25 Kimberly-Clark Worldwide, Inc. Method and apparatus for indicating ultraviolet light exposure
US5700850A (en) * 1993-08-05 1997-12-23 Kimberly-Clark Worldwide Colorant compositions and colorant stabilizers
US6066439A (en) 1993-08-05 2000-05-23 Kimberly-Clark Worldwide, Inc. Instrument for photoerasable marking
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
US5865471A (en) 1993-08-05 1999-02-02 Kimberly-Clark Worldwide, Inc. Photo-erasable data processing forms
US5858586A (en) 1993-08-05 1999-01-12 Kimberly-Clark Corporation Digital information recording media and method of using same
US5773182A (en) 1993-08-05 1998-06-30 Kimberly-Clark Worldwide, Inc. Method of light stabilizing a colorant
US6211383B1 (en) 1993-08-05 2001-04-03 Kimberly-Clark Worldwide, Inc. Nohr-McDonald elimination reaction
US5616443A (en) * 1993-08-05 1997-04-01 Kimberly-Clark Corporation Substrate having a mutable colored composition thereon
US6120949A (en) 1993-08-05 2000-09-19 Kimberly-Clark Worldwide, Inc. Photoerasable paint and method for using photoerasable paint
US6060223A (en) 1993-08-05 2000-05-09 Kimberly-Clark Worldwide, Inc. Plastic article for colored printing and method for printing on a colored plastic article
US6017471A (en) 1993-08-05 2000-01-25 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
US6090236A (en) 1994-06-30 2000-07-18 Kimberly-Clark Worldwide, Inc. Photocuring, articles made by photocuring, and compositions for use in photocuring
US6242057B1 (en) 1994-06-30 2001-06-05 Kimberly-Clark Worldwide, Inc. Photoreactor composition and applications therefor
US5709955A (en) 1994-06-30 1998-01-20 Kimberly-Clark Corporation Adhesive composition curable upon exposure to radiation and applications therefor
US5686503A (en) * 1994-06-30 1997-11-11 Kimberly-Clark Corporation Method of generating a reactive species and applications therefor
US5685754A (en) * 1994-06-30 1997-11-11 Kimberly-Clark Corporation Method of generating a reactive species and polymer coating applications therefor
US6008268A (en) 1994-10-21 1999-12-28 Kimberly-Clark Worldwide, Inc. Photoreactor composition, method of generating a reactive species, and applications therefor
US6017661A (en) 1994-11-09 2000-01-25 Kimberly-Clark Corporation Temporary marking using photoerasable colorants
US6235095B1 (en) 1994-12-20 2001-05-22 Ronald Sinclair Nohr Ink for inkjet printers
US5681380A (en) 1995-06-05 1997-10-28 Kimberly-Clark Worldwide, Inc. Ink for ink jet printers
US5739175A (en) * 1995-06-05 1998-04-14 Kimberly-Clark Worldwide, Inc. Photoreactor composition containing an arylketoalkene wavelength-specific sensitizer
US6063551A (en) 1995-06-05 2000-05-16 Kimberly-Clark Worldwide, Inc. Mutable dye composition and method 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
US5837429A (en) 1995-06-05 1998-11-17 Kimberly-Clark Worldwide Pre-dyes, pre-dye compositions, and methods of developing a color
US5811199A (en) * 1995-06-05 1998-09-22 Kimberly-Clark Worldwide, Inc. Adhesive compositions containing a photoreactor composition
US5747550A (en) * 1995-06-05 1998-05-05 Kimberly-Clark Worldwide, Inc. Method of generating a reactive species and polymerizing an unsaturated polymerizable material
US5798015A (en) * 1995-06-05 1998-08-25 Kimberly-Clark Worldwide, Inc. Method of laminating a structure with adhesive containing a photoreactor composition
US5786132A (en) 1995-06-05 1998-07-28 Kimberly-Clark Corporation Pre-dyes, mutable dye compositions, and methods of developing a color
US6033465A (en) 1995-06-28 2000-03-07 Kimberly-Clark Worldwide, Inc. Colorants and colorant modifiers
US6168655B1 (en) 1995-11-28 2001-01-02 Kimberly-Clark Worldwide, Inc. Colorant stabilizers
US5885337A (en) 1995-11-28 1999-03-23 Nohr; Ronald Sinclair Colorant stabilizers
US6168654B1 (en) 1996-03-29 2001-01-02 Kimberly-Clark Worldwide, Inc. Colorant stabilizers
US5891229A (en) 1996-03-29 1999-04-06 Kimberly-Clark Worldwide, Inc. Colorant stabilizers
US5782963A (en) 1996-03-29 1998-07-21 Kimberly-Clark Worldwide, Inc. Colorant stabilizers
US5855655A (en) 1996-03-29 1999-01-05 Kimberly-Clark Worldwide, Inc. Colorant stabilizers
US6099628A (en) 1996-03-29 2000-08-08 Kimberly-Clark Worldwide, Inc. Colorant stabilizers
US6524379B2 (en) 1997-08-15 2003-02-25 Kimberly-Clark Worldwide, Inc. Colorants, colorant stabilizers, ink compositions, and improved methods of making the same
US6277897B1 (en) 1998-06-03 2001-08-21 Kimberly-Clark Worldwide, Inc. 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
US6228157B1 (en) 1998-07-20 2001-05-08 Ronald S. Nohr Ink jet ink compositions
US6265458B1 (en) 1998-09-28 2001-07-24 Kimberly-Clark Worldwide, Inc. Photoinitiators and applications therefor
US6368396B1 (en) 1999-01-19 2002-04-09 Kimberly-Clark Worldwide, Inc. Colorants, colorant stabilizers, ink compositions, and improved methods of making the same
US6331056B1 (en) 1999-02-25 2001-12-18 Kimberly-Clark Worldwide, Inc. Printing apparatus and applications therefor
US6294698B1 (en) * 1999-04-16 2001-09-25 Kimberly-Clark Worldwide, Inc. Photoinitiators 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
US6486227B2 (en) 2000-06-19 2002-11-26 Kimberly-Clark Worldwide, Inc. Zinc-complex photoinitiators and applications therefor

Also Published As

Publication number Publication date
NL6507549A (de) 1965-08-25
CH458057A (de) 1968-06-15
FR1477432A (fr) 1967-04-21
DE1285877B (de) 1968-12-19
GB1080380A (en) 1967-08-23
US3385703A (en) 1968-05-28
GB1070863A (en) 1967-06-07
BE665367A (de) 1965-12-14

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