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WO1999044099A1 - Systeme d'imagerie utilisant une composition photosensible encapsulee - Google Patents

Systeme d'imagerie utilisant une composition photosensible encapsulee Download PDF

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Publication number
WO1999044099A1
WO1999044099A1 PCT/US1999/004131 US9904131W WO9944099A1 WO 1999044099 A1 WO1999044099 A1 WO 1999044099A1 US 9904131 W US9904131 W US 9904131W WO 9944099 A1 WO9944099 A1 WO 9944099A1
Authority
WO
WIPO (PCT)
Prior art keywords
microcapsules
photosensitive material
sensitive
complex
anion
Prior art date
Application number
PCT/US1999/004131
Other languages
English (en)
Inventor
Alex Polycarpov
Joseph C. Camillus
Original Assignee
Cycolor, Inc.
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Cycolor, Inc. filed Critical Cycolor, Inc.
Priority to KR1020007009297A priority Critical patent/KR20010041213A/ko
Priority to CA002319603A priority patent/CA2319603A1/fr
Priority to AU27902/99A priority patent/AU2790299A/en
Priority to JP2000533790A priority patent/JP2002505447A/ja
Priority to EP99908475A priority patent/EP1058864A1/fr
Priority to BR9907640-3A priority patent/BR9907640A/pt
Publication of WO1999044099A1 publication Critical patent/WO1999044099A1/fr

Links

Classifications

    • 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
    • G03F7/029—Inorganic compounds; Onium compounds; Organic compounds having hetero atoms other than oxygen, nitrogen or sulfur
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F22/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof
    • C08F22/36—Amides or imides
    • C08F22/40—Imides, e.g. cyclic imides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
    • C08G18/78—Nitrogen
    • C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
    • C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
    • C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/20—Compounding polymers with additives, e.g. colouring
    • C08J3/205—Compounding polymers with additives, e.g. colouring in the presence of a continuous liquid phase
    • C08J3/21—Compounding polymers with additives, e.g. colouring in the presence of a continuous liquid phase the polymer being premixed with a liquid phase
    • C08J3/215—Compounding polymers with additives, e.g. colouring in the presence of a continuous liquid phase the polymer being premixed with a liquid phase at least one additive being also premixed with a liquid phase
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B69/00—Dyes not provided for by a single group of this subclass
    • C09B69/02—Dyestuff salts, e.g. salts of acid dyes with basic dyes
    • C09B69/06—Dyestuff salts, e.g. salts of acid dyes with basic dyes of cationic dyes with organic acids or with inorganic complex acids
    • 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
    • G03F7/002—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor using materials containing microcapsules; Preparing or processing such materials, e.g. by pressure; Devices or apparatus specially designed therefor
    • 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
    • G03F7/0037—Production of three-dimensional images

Definitions

  • imaging system employs a layer of photosensitive microcapsules.
  • the microcapsules are prepared by microencapsulating a free radical polymerizable composition which contains an electron donating color precursor.
  • the image system assumes two forms.
  • the imaging system is a transfer system in which a support carrying a layer of photosensitive microcapsules is image-wise exposed to radiation and assembled with a developer sheet, e.g., a sheet containing a layer of a Lewis acid such as a phenolic resin.
  • the imaging system is a self-contained imaging system in which the photosensitive microcapsules and the Lewis acid are carried on the surface of a common substrate in one layer or in juxtaposed layers.
  • a layer containing photosensitive microcapsules and a developer material is interposed between two plastic films, at least one of which is transparent. Using a combination of an adhesive and a subbing layer, the films are permanently sealed to provide a film unit. This construction is advantageous because it prevents the chemical reactants in the imaging system from coming into contact with the user.
  • the imaging system is preferably a full color imaging system in which three different sets of microcapsules are used in combination and each set of microcapsules is sensitive to a distinct wavelength band.
  • This full color system is described in U.S. Patent 4,842,976.
  • three sets of microcapsules respectively containing cyan, magenta and yellow color precursors are respectively sensitive to red, green and blue light are employed.
  • these microcapsules are sensitized using a so-called "dye-borate photoinitiator" of the type described in U.S. Patent 4,772,530 to Gottschalk.
  • photoinitiators in one embodiment, are complexes of cationic cyanine dyes and a boranyl anion such as a triphenylbutylboranyl anion.
  • a boranyl anion such as a triphenylbutylboranyl anion.
  • printers can be designed which employ radiation sources which emit at wavelengths outside the visible spectrum, for example, in the infrared region. This presents an opportunity to minimize the problems associated with cross-talk since it is no longer necessary to restrict the sensitivity range of a photosensitive material to the visible region, the sensitivity of the imaging system can be extended into the infrared region at one end of the spectrum and optionally the ultraviolet region at the other end.
  • the foregoing imaging system and, more particularly, the imaging system described in U.S. Patent 4,772,530 is modified to include one or more infrared photosensitive compositions and, more particularly, to include one or more photosensitive compositions in which the photoinitiator is a complex between an infrared-sensitive dye and a boranyl anion of the type mentioned above.
  • one embodiment of the invention resides in an imaging system comprising a support having a layer of at least one set of photosensitive microcapsules on the surface thereof, said microcapsules being sensitive to distinct band of radiation and containing a complex of an infrared sensitive cationic dye and a boranyl anion.
  • the imaging system includes cyan forming, magenta forming and yellow forming capsules and at least one set of capsules includes an infrared sensitive dye borate compound as a photoinitiator.
  • at least one other set includes a visible light sensitive dye borate compound or an ultraviolet initiator.
  • all three sets of microcapsules contain a photohardenable composition containing a complex of a cationic infrared sensitive dye and a boranyl anion.
  • infrared-sensitive photoinitiators which can be employed in the imaging system of the present invention are described in Japanese Published Applications 3- 221506; 4-261405; 8-100011; 8-100012; and 8-34808, all of which are incorporated herein by reference for a description of the cationic dyes and methods for obtaining the photoinitiators.
  • a table of the infrared sensitive cationic dyes described in the aforementioned patents is provided in the following Table 1 where "Ph" indicates a phenyl group:
  • the infrared dyes in Table 1 are complexed with a borate anion.
  • a borate anion Any of the borate anions described in U.S. Patent 4,772,530 can be used in this invention.
  • the preferred boranyl anion is a triphenyl n-butylboranyl anion.
  • the anions can be represented by the general formula (I):
  • R 1 , R 2 , R 3 , and R 4 are independently selected from the group consisting of alkyl, aryl, alkaryl, allyl, aralkyl, alkenyl, alkynyl, alicyclic and saturated or unsaturated heterocyclic groups.
  • triphenylalkylborate and trianisylalkylborate anions such as triphenylbutylborate and trianisylbutylborate anions because they readily dissociate to triphenylborane or trianisylborane and a butyl radical.
  • tetrabutylborate anion does not work well presumably because the tefrabutylborate radical is not stable and it readily accepts an electron back from the dye in a back electron transfer and does not dissociate efficiently.
  • tetraphenylborate anion is very poor because the phenyl radical is not easily formed.
  • R 1 , R 2 , R 3 , and R 4 is an alkyl group.
  • R 1 , R 2 , R 3 , and R 4 is an alkyl group.
  • R 1 , R 2 , R 3 , and R 4 can contain up to 20 carbon atoms, and they typically contain 1 to 7 carbon atoms. More preferably R'-R 4 are a combination of alkyl group(s) and aryl group(s) or aralkyl group(s) and still more preferably a combination of three aryl groups and one alkyl group.
  • alkyl groups represented by R'-R 4 are methyl, ethyl, propyl, butyl, pentyl, hexyl, octyl, stearyl, etc. and can be straight or branched chain and possibly cyclic.
  • the alkyl groups may be substituted, for example, by one or more halogen, cyano, acyloxy, acyl, aryl, alkoxy or hydroxy groups.
  • aryl groups represented by R0R 4 include phenyl, naphthyl and substituted aryl groups such as anisyl.
  • Alkaryl groups include methylphenyl, dimethylphenyl, etc.
  • Representative examples of aralkyl groups represented by groups include benzyl.
  • Representative alicyclic groups include cyclobutyl, cyclopentyl, and cyclohexyl groups. Examples of an alkynyl group are propynyl and ethynyl, and examples of alkenyl groups include a vinyl group.
  • an infrared sensitive dye borate in at least one set of the microcapsules enable the sensitivities of the microcapsules to be spaced apart to minimize overlap in their sensitivity curves and thereby minimize crosstalk.
  • Infrared sensitive borates can be used in any or all of the cyan, magenta or yellow forming microcapsules.
  • an imaging system can be designed in which the microcapsules are sensitive at 750, 850 and 1050 nm.
  • the red sensitive capsules described in U.S. Patent 4,772,530 (Gottschalk) are replaced with infrared sensitive microcapsules prepared using one of the dyes in the appendix such as the dye #5 in Table 1.
  • an imaging system can be designed in which the microcapsules are sensitive at 800, 900 and 1100 nm.
  • the cyan, magenta and yellow forming microcapsules are sensitive at 450, 550, 650 nm respectively.
  • any of 450, 550, and 650 sensitizers is replaced with an infrared dye.
  • the magenta 550 initiator is replaced with an infrared dye to achieve the most separation in the absorptions.
  • a 450, 840, 650 nm system might be used.
  • the infrared sensitive compositions can be modified to include an autoxidizer such as N,N-dimethylaniline as described in U.S. Patent 4,772,530 which is incorporated herein by reference.
  • an autoxidizer such as N,N-dimethylaniline as described in U.S. Patent 4,772,530 which is incorporated herein by reference.
  • the ultraviolet initiator can be selected from among those that are known in the art. Some examples are provided in U.S. Patent 4,399,209.
  • the infrared sensitive dye is normally used in an amount up to 1 % by weight based on the weight of the photopolymenzable species and more typically in an amount of about 0.2 to 0.5% by weight. However, those skilled in the art will recognize that the amount is easily adjusted to achieve the desired sensitivity and photographic response in the photosensitive material.

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  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Organic Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • General Physics & Mathematics (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Materials For Photolithography (AREA)
  • Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
  • Polymerisation Methods In General (AREA)

Abstract

La présente invention concerne une matière photosensible comprenant un support qui contient sur sa surface une couche de microcapsules auxquelles est associé un agent imageur qui renferme une phase interne comportant une composition photodurcissable. Cette composition comprend un composé polymérisable et réticulable d'addition de radicaux libres, un complexe constitué par un colorant cationique sensible aux infrarouges et un anion boranyle capable d'absorber le rayonnement infrarouge et produire des radicaux libres qui déclenchent la polymérisation ou la réticulation radicalaires du composé polymérisable et réticulable.
PCT/US1999/004131 1998-02-25 1999-02-25 Systeme d'imagerie utilisant une composition photosensible encapsulee WO1999044099A1 (fr)

Priority Applications (6)

Application Number Priority Date Filing Date Title
KR1020007009297A KR20010041213A (ko) 1998-02-25 1999-02-25 캡슐화된 방사선 민감성 조성물을 사용하는 화상 시스템
CA002319603A CA2319603A1 (fr) 1998-02-25 1999-02-25 Systeme d'imagerie utilisant une composition photosensible encapsulee
AU27902/99A AU2790299A (en) 1998-02-25 1999-02-25 Imaging system employing encapsulated radiation sensitive composition
JP2000533790A JP2002505447A (ja) 1998-02-25 1999-02-25 カプセルに封入した放射線感光性組成物を使用した画像形成システム
EP99908475A EP1058864A1 (fr) 1998-02-25 1999-02-25 Systeme d'imagerie utilisant une composition photosensible encapsulee
BR9907640-3A BR9907640A (pt) 1998-02-25 1999-02-25 Material fotossensìvel

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US7589298P 1998-02-25 1998-02-25
US60/075,892 1998-02-25

Publications (1)

Publication Number Publication Date
WO1999044099A1 true WO1999044099A1 (fr) 1999-09-02

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1999/004131 WO1999044099A1 (fr) 1998-02-25 1999-02-25 Systeme d'imagerie utilisant une composition photosensible encapsulee

Country Status (8)

Country Link
EP (1) EP1058864A1 (fr)
JP (1) JP2002505447A (fr)
KR (1) KR20010041213A (fr)
CN (1) CN1289415A (fr)
AU (1) AU2790299A (fr)
BR (1) BR9907640A (fr)
CA (1) CA2319603A1 (fr)
WO (1) WO1999044099A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7172991B2 (en) 2001-10-11 2007-02-06 Hewlett-Packard Development Company, L.P. Integrated CD/DVD recording and labeling
US8465973B2 (en) 2004-09-14 2013-06-18 Estee Lauder Coordination Center N.V. Topical compositions containing phosphorylated polyphenols

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0223587A1 (fr) * 1985-11-20 1987-05-27 The Mead Corporation Matériaux photosensitifs contenant des colorants ioniques comme initiateurs
EP0408227A1 (fr) * 1989-06-30 1991-01-16 The Mead Corporation Compositions photodurcissables ou photoadoucissables
EP0438123A2 (fr) * 1990-01-16 1991-07-24 Showa Denko Kabushiki Kaisha Initiateur de polymérisation utilisable dans l'infrarouge proche
JPH04261405A (ja) * 1991-02-15 1992-09-17 Showa Denko Kk 光重合開始剤

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0223587A1 (fr) * 1985-11-20 1987-05-27 The Mead Corporation Matériaux photosensitifs contenant des colorants ioniques comme initiateurs
EP0408227A1 (fr) * 1989-06-30 1991-01-16 The Mead Corporation Compositions photodurcissables ou photoadoucissables
EP0438123A2 (fr) * 1990-01-16 1991-07-24 Showa Denko Kabushiki Kaisha Initiateur de polymérisation utilisable dans l'infrarouge proche
JPH04261405A (ja) * 1991-02-15 1992-09-17 Showa Denko Kk 光重合開始剤

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Section Ch Week 9244, Derwent World Patents Index; Class A60, AN 92-360898, XP002106181 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7172991B2 (en) 2001-10-11 2007-02-06 Hewlett-Packard Development Company, L.P. Integrated CD/DVD recording and labeling
US7501172B2 (en) 2001-10-11 2009-03-10 Hewlett-Packard Development Company, L.P. Integrated recording and labeling with optical recording device
US8465973B2 (en) 2004-09-14 2013-06-18 Estee Lauder Coordination Center N.V. Topical compositions containing phosphorylated polyphenols

Also Published As

Publication number Publication date
KR20010041213A (ko) 2001-05-15
CN1289415A (zh) 2001-03-28
BR9907640A (pt) 2000-11-14
EP1058864A1 (fr) 2000-12-13
JP2002505447A (ja) 2002-02-19
AU2790299A (en) 1999-09-15
CA2319603A1 (fr) 1999-09-02

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