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WO2006019377A1 - Compositions, systemes et procedes d'imagerie - Google Patents

Compositions, systemes et procedes d'imagerie Download PDF

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Publication number
WO2006019377A1
WO2006019377A1 PCT/US2004/023106 US2004023106W WO2006019377A1 WO 2006019377 A1 WO2006019377 A1 WO 2006019377A1 US 2004023106 W US2004023106 W US 2004023106W WO 2006019377 A1 WO2006019377 A1 WO 2006019377A1
Authority
WO
WIPO (PCT)
Prior art keywords
compound
activator
dye
color
antenna
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.)
Ceased
Application number
PCT/US2004/023106
Other languages
English (en)
Inventor
Makarand P. Gore
Marshall Field
Vladek P. Kasperchik
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Hewlett Packard Development Co LP
Original Assignee
Hewlett Packard Development Co LP
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 Hewlett Packard Development Co LP filed Critical Hewlett Packard Development Co LP
Priority to EP04778544A priority Critical patent/EP1773602A1/fr
Priority to KR1020047017775A priority patent/KR101116446B1/ko
Priority to CN2004800435845A priority patent/CN1989015B/zh
Priority to PCT/US2004/023106 priority patent/WO2006019377A1/fr
Publication of WO2006019377A1 publication Critical patent/WO2006019377A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M5/00—Duplicating or marking methods; Sheet materials for use therein
    • B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
    • B41M5/30—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used using chemical colour formers

Definitions

  • Materials that produce color change upon stimulation with energy such as light or heat may have possible applications in imaging.
  • such materials may be found in thermal printing papers and instant imaging films.
  • the materials and compositions known so far may require a multifilm structure and further processing to produce an image (e.g., instant imaging films such as Polaroid).
  • high energy input of greater than 1 J/cm 2 is needed to achieve good images.
  • the compositions in multifilm media may require control of diffusion of color-forming chemistry and further processing, and are in separate phases and layers.
  • Most thermal and facsimile paper coatings consist of coatings prepared by preparing fine dispersions of more than two components. The components mix and react upon application of energy, resulting in a colored material.
  • the particles need to contact across three or more phases or layers and merge into a new phase. Because of these multiple phases and layers, high energy is required to perform this process. For example, a relatively powerful carbon dioxide laser with an energy density of 3 J/cm 2 at times of much greater than 100 ⁇ s may be needed to produce a mark. In some instances, this high energy application may cause damage to the imaging substrate. In many situations, it may be desirable to produce a visible mark more efficiently using either a less intense, less powerful, and/or shorter energy application. Therefore, there is a need for fast marking coatings, possibly composed of fewer than three phases and in single layer. Single layer color-forming materials, initiated and addressable by radiation, particularly with energy density of less than 1 J/cm 2 delivered in less than 100 ⁇ s is hereto unknown.
  • the materials disclosed herein may include an antenna, a color former and an activator, all dispersed in a matrix.
  • the color former and the activator are present in the imaging material in two separate phases.
  • the antenna readily absorbs energy which may be applied imagewise to the imaging materials. This absorbed energy heats the mixture which causes the color former and the activator to mix and react, causing the color former to change color and a mark to be produced.
  • Figure 1 shows a method of preparing an imaging material according to an embodiment of the present invention.
  • Figure 2 shows an imaging medium according to an embodiment of the present invention.
  • activator is a substance which reacts with a leuco dye and causing the leuco dye to alter its chemical structure and change or acquire color.
  • activators may be phenolic or other proton donating species which can effect this change.
  • antienna means any radiation absorbing compound the antenna readily absorbs a desired specific wavelength of the marking radiation.
  • Embodiments of the invention include coatings that result in clear marks and excellent image quality when marked with a 780 nm laser operating at 45mw.
  • the materials used to produce color change upon stimulation by energy may include a color-former such as a fluoran leuco dye and an activator such as sulphonylphenol dispersed in a matrix such as radiation-cured acrylate oligomers and monomers and applied to a substrate.
  • a color-former such as a fluoran leuco dye and an activator such as sulphonylphenol dispersed in a matrix such as radiation-cured acrylate oligomers and monomers and applied to a substrate.
  • either the leuco dye or the activator may be substantially insoluble in the matrix at ambient conditions.
  • An efficient radiation energy absorber that functions to absorb energy and deliver it to the reactants is also present in this coating. Energy may then be applied by way of, for example, a laser or infrared light. Upon application of the energy, either the activ
  • Imaging medium 100 may comprise a substrate 120.
  • Substrate 120 may be any substrate upon which it is desirable to make a mark, such as, by way of example only, paper (e.g., labels, tickets, receipts, or stationary), overhead transparencies, or the labeling surface of a medium such as a CD-R/RW/ROM or DVD-R/RW/ROM.
  • Imaging composition 130 may comprise a matrix, an activator, a radiation absorbing compound such as a dye, and a color forming dye.
  • the activator and the color forming dye when mixed, may change color. Either of the activator and the color forming dye may be soluble in the matrix.
  • the other component activator or color forming dye
  • the imaging composition 130 may be applied to the substrate via any acceptable method, such as, by way of example only, rolling, spraying, or screen printing.
  • Energy 110 may be directed imagewise to imaging medium 100. The form of energy may vary depending upon the equipment available, ambient conditions, and desired result.
  • Examples of energy which may be used include IR radiation, UV radiation, x-rays, or visible light.
  • the antenna may absorb the energy and heat the imaging composition 130.
  • the heat may cause suspended particles 140 to reach a temperature sufficient to cause the interdiffusion of the color forming species initially present in the particles (e.g., glass transition temperatures (T 9 ) or melting temperatures (T m ) of particles 140 and matrix).
  • T 9 glass transition temperatures
  • T m melting temperatures
  • antenna 60 may be any material which effectively absorbs the type of energy to be applied to the imaging medium to effect a mark.
  • IR780 Aldrich 42,531-1) (1), IR783 (Aldrich 54,329-2) (2), Syntec 9/1 (3), Syntec 9/3 (4) or metal complexes (such as dithiolane metal complexes (5) and indoaniline metal complexes (6))
  • IR780 Aldrich 42,531-1) (1), IR783 (Aldrich 54,329-2) (2), Syntec 9/1 (3), Syntec 9/3 (4) or metal complexes (such as dithiolane metal complexes (5) and indoaniline metal complexes (6))
  • Mi is a transition metal
  • R 1 , R 2 , R 3 , and R 4 are alkyl or aryl groups with or without halo substituents
  • a 1 , A 2 , A 3 , and A 4 can be S, NH, or Se;
  • M 2 is Ni or Cu and R5 and R 6 are aryl or alkyl groups with or without halo substituents.
  • antennae can be found in "Infrared Absorbing Dyes", Matsuoka, Masaru, ed., Plenum Press (1990) (ISBN 0-306-43478-4) and "Near- Infrared Dyes for High Technology Applications", Daehne, S.; Resch-Genger, U.; Wolfbeis, O. ,Ed., Kluwer Academic Publishers (ISBN 0-7923-5101-0), both incorporated herein by reference.
  • the activator e.g., bisphenol-A
  • color-forming dye 90 e.g., BK-400
  • the activator and dye may be any two substances which when reacted together produce a color change. When reacted, the activator may initiate a color change in the dye or develop the dye.
  • One of the activator and the dye may be soluble in the matrix (e.g., lacquer 30) at ambient conditions.
  • the other may be substantially insoluble in the lacquer at ambient conditions.
  • substantially insoluble it is meant that the solubility of the other in the lacquer at ambient conditions is so low, that no or very little color change may occur due to reaction of the dye and the activator at ambient conditions.
  • the activator may be dissolved in the lacquer and the dye remains suspended as a solid in the matrix at ambient conditions
  • the color former may be dissolved in the matrix and the activator may remain as a suspended solid at ambient conditions.
  • Activators may include, without limitation, proton donors and phenolic compounds such as bisphenol-A and bisphenol-S.
  • Color formers may include, without limitation, leuco dyes such as fluoran leuco dyes and phthalide color formers as described in "The Chemistry and Applications of Leuco Dyes", Muthyala, Ramiah, ed., Plenum Press (1997) (ISBN 0-306-45459-9), incorporated herein by reference. Examples of acceptable fluoran leuco dyes comprise the structure shown in Formula (7)
  • a and R are aryl or alkyl groups.
  • Lacquer 30 may be any suitable matrix for dissolving and/or dispersing the activator, antenna, and color former.
  • Acceptable lacquers may include, by way of example only, UV curable matrices such as acrylate derivatives, oligomers and monomers, with a photo package.
  • a photo package may include a light absorbing species which initiates reactions for curing of a lacquer, such as, by way of example, benzophenone derivatives.
  • Other examples of photoinitiators for free radical polymerization monomers and pre-polymers include but are not limited to: thioxanethone derivatives, anthraquinone derivatives, acetophenones and benzoine ether types.
  • Matrices based on cationic polymerization resins may require photo- initiators based on aromatic diazonium salts, aromatic halonium salts, aromatic sulfonium salts and metallocene compounds.
  • An example of an acceptable lacquer or matrix may include Nor-Cote CDGOOO (a mixture of UV curable acrylate monomers and oligomers) which contains a photoinitiator (hydroxy ketone) and organic solvent acrylates (e.g., methyl methacrylate, hexyl methacrylate, beta-phenoxy ethyl acrylate, and hexamethylene acrylate).
  • Other acceptable lacquers or matrices may include acrylated polyester oligomers such as CN293 and CN294 available from Sartomer Co.
  • the method may comprise an activator melt 10, an activator/antenna solution 20, a UV curable lacquer solution 30, a lacquer/antenna/activator solution 40, and a two phase UV curable paste 50.
  • an activator melt 10 2 grams of dibenzyl oxalate was heated to melting ( ⁇ 85° C).
  • Twenty grams of activator bisphenol-A and one gram of antenna IR780 were dissolved in the melted dibenzyl oxalate.
  • the activator/antenna solution 20 was cooled and ground into a fine powder 70.

Landscapes

  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Optics & Photonics (AREA)
  • Heat Sensitive Colour Forming Recording (AREA)
  • Paints Or Removers (AREA)

Abstract

Cette invention concerne compositions, un procédé et un système permettant d'enregistrer une image. Ce système comprend un matériau d'imagerie multiphase (130), dans lequel l'énergie (110) est absorbée par un matériau d'antenne. L'énergie absorbée produit la réaction d'un activateur et d'un matériau de formation de couleur (140).
PCT/US2004/023106 2004-07-15 2004-07-15 Compositions, systemes et procedes d'imagerie Ceased WO2006019377A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EP04778544A EP1773602A1 (fr) 2004-07-15 2004-07-15 Compositions, systemes et procedes d'imagerie
KR1020047017775A KR101116446B1 (ko) 2004-07-15 2004-07-15 영상화를 위한 조성물, 시스템 및 방법
CN2004800435845A CN1989015B (zh) 2004-07-15 2004-07-15 用于成像的组合物、系统及方法
PCT/US2004/023106 WO2006019377A1 (fr) 2004-07-15 2004-07-15 Compositions, systemes et procedes d'imagerie

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/US2004/023106 WO2006019377A1 (fr) 2004-07-15 2004-07-15 Compositions, systemes et procedes d'imagerie

Publications (1)

Publication Number Publication Date
WO2006019377A1 true WO2006019377A1 (fr) 2006-02-23

Family

ID=34958354

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2004/023106 Ceased WO2006019377A1 (fr) 2004-07-15 2004-07-15 Compositions, systemes et procedes d'imagerie

Country Status (4)

Country Link
EP (1) EP1773602A1 (fr)
KR (1) KR101116446B1 (fr)
CN (1) CN1989015B (fr)
WO (1) WO2006019377A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008076642A1 (fr) * 2006-12-16 2008-06-26 Hewlett-Packard Development Company, L.P. Revêtement pour enregistrement optique

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110105786A (zh) * 2019-05-07 2019-08-09 西南交通大学 一种克酮酸菁染料及其应用

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0304936A2 (fr) * 1987-08-27 1989-03-01 Kao Corporation Papier sensible à la chaleur
EP0372878A2 (fr) * 1988-12-07 1990-06-13 Oji Paper Company Limited Papier d'enregistrement thermosensible
US5354724A (en) * 1992-08-05 1994-10-11 Basf Aktiengesellschaft Heat sensitive recording materials with polymer enrobed sensitizer
EP1375182A1 (fr) * 2001-04-04 2004-01-02 Nippon Soda Co., Ltd. Mat riau et feuille d'enregistrement
WO2004067653A2 (fr) * 2003-01-24 2004-08-12 Hewlett-Packard Development Company, L.P. Jeu d'encres pour jet d'encre combinant des charges pigmentaires claires et des charges pigmentaires foncees
WO2004067289A1 (fr) * 2003-01-24 2004-08-12 Hewlett-Packard Development Company L.P. Systeme d'etiquetage de substrats et procede d'etiquetage de disques optiques

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5409797A (en) * 1991-03-04 1995-04-25 Fuji Photo Film Co., Ltd. Heat-sensitive recording material for laser recording
CA2371443A1 (fr) * 1999-04-28 2000-11-09 Yasuhisa Tsutsumi Materiau pour thermogravure
US6740465B2 (en) * 2000-06-01 2004-05-25 Sipix Imaging, Inc. Imaging media containing heat developable photosensitive microcapsules
CN1280920A (zh) * 2000-08-10 2001-01-24 上海天臣新技术有限公司 一种可逆热敏显示材料及其制备方法

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0304936A2 (fr) * 1987-08-27 1989-03-01 Kao Corporation Papier sensible à la chaleur
EP0372878A2 (fr) * 1988-12-07 1990-06-13 Oji Paper Company Limited Papier d'enregistrement thermosensible
US5354724A (en) * 1992-08-05 1994-10-11 Basf Aktiengesellschaft Heat sensitive recording materials with polymer enrobed sensitizer
EP1375182A1 (fr) * 2001-04-04 2004-01-02 Nippon Soda Co., Ltd. Mat riau et feuille d'enregistrement
WO2004067653A2 (fr) * 2003-01-24 2004-08-12 Hewlett-Packard Development Company, L.P. Jeu d'encres pour jet d'encre combinant des charges pigmentaires claires et des charges pigmentaires foncees
WO2004067289A1 (fr) * 2003-01-24 2004-08-12 Hewlett-Packard Development Company L.P. Systeme d'etiquetage de substrats et procede d'etiquetage de disques optiques

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008076642A1 (fr) * 2006-12-16 2008-06-26 Hewlett-Packard Development Company, L.P. Revêtement pour enregistrement optique
US7892619B2 (en) 2006-12-16 2011-02-22 Hewlett-Packard Development Company, L.P. Coating for optical recording

Also Published As

Publication number Publication date
EP1773602A1 (fr) 2007-04-18
CN1989015A (zh) 2007-06-27
CN1989015B (zh) 2011-06-15
KR20070030965A (ko) 2007-03-19
KR101116446B1 (ko) 2012-03-07

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