CA2510518A1 - Multicolored photochromic display - Google Patents

Multicolored photochromic display Download PDF

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Publication number
CA2510518A1
CA2510518A1 CA002510518A CA2510518A CA2510518A1 CA 2510518 A1 CA2510518 A1 CA 2510518A1 CA 002510518 A CA002510518 A CA 002510518A CA 2510518 A CA2510518 A CA 2510518A CA 2510518 A1 CA2510518 A1 CA 2510518A1
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CA
Canada
Prior art keywords
marking particles
multicolored display
spiropyran
display
multicolored
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.)
Granted
Application number
CA002510518A
Other languages
French (fr)
Other versions
CA2510518C (en
Inventor
Naveen Chopra
Daniel A. Foucher
Raj D. Patel
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Xerox Corp
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Xerox Corp
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Filing date
Publication date
Application filed by Xerox Corp filed Critical Xerox Corp
Publication of CA2510518A1 publication Critical patent/CA2510518A1/en
Application granted granted Critical
Publication of CA2510518C publication Critical patent/CA2510518C/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K9/00—Tenebrescent materials, i.e. materials for which the range of wavelengths for energy absorption is changed as a result of excitation by some form of energy
    • C09K9/02—Organic tenebrescent materials
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/0126—Opto-optical modulation, i.e. control of one light beam by another light beam, not otherwise provided for in this subclass
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G9/00—Developers
    • G03G9/08—Developers with toner particles
    • G03G9/09—Colouring agents for toner particles
    • G03G9/0906—Organic dyes
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G9/00—Developers
    • G03G9/08—Developers with toner particles
    • G03G9/09—Colouring agents for toner particles
    • G03G9/0906—Organic dyes
    • G03G9/0916—Quinoline; Polymethine dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F2202/00—Materials and properties
    • G02F2202/14—Materials and properties photochromic

Abstract

A multicolored display and process for forming such a display is provided.
The multicolored display includes marking particles comprising a mixture of photochromic materials. The photochromic materials each exhibit a first "invisible" photochromic state at a first absorption spectrum and at least a second "visible" photochromic state at a second absorption spectrum. The second "visible" photochromic state of each photochromic material produces a different color relative to the other photochromic materials. In embodiments, the marking particles include a mixture of a spiropyran material and a dithienylethene material.

Claims (38)

1. A multicolored display comprising a substrate having uniformly situated thereon a coating of marking particles comprising a mixture of photochromic materials, wherein each of said photochromic materials is sensitive to a different wavelength of light relative to the other photochromic material and produces a different color relative to the other photochromic material when exposes to the appropriate wavelength.
2. The multicolored display of claim 1, wherein said photochromic materials are selected from the group consisting of spiropyrans, dithienylethenes, and combinations thereof.
3. The multicolored display of claim 1, wherein said marking particles comprise a mixture of spiropyrans.
4. The multicolored display of claim 1, wherein said marking particles comprise a mixture of a spiropyran material of the formula:

where n is an integer from 2 to 8, and R is -H or -CH=CH2; and a dithienylethene material of the formula:

where R = C6H13, X = Y = H

5. The multicolored display of claim 4, wherein the spiropyran material is of the formula:

6. The multicolored display of claim 4, wherein the spiropyran material is of the formula:

7. The multicolored display of claim 4, wherein the spiropyran material is of the formula:

8. The multicolored display of claim 4, wherein the spiropyran and dithienylethene material are present in the marking particles in an amount of at least about 0.01 percent by weight of the marking particles.
9. The multicolored display of claim 4, wherein the spiropyran and dithienylethene material is present in the marking particles in an amount of at least about 0.05 percent by weight of the marking particles, and the spiropyran material is present in the marking particles in an amount of no more than about 5 percent by weight of the marking particles.
10. The multicolored display of claim 1, wherein the marking particles further comprise a resin and a chelating agent.
11. The multicolored display of claim 1, wherein the marking particles further comprise a first polymer, a second polymer, and a chelating agent.
12. The multicolored display of claim 1, wherein the multicolored display is an addressable display.
13. The multicolored display of claim 1, wherein at least one of the photochromic materials exhibits multiple photochromic states, at least two of said multiple photochromic states producing a different color relative to each other at a different absorption spectrum or wavelength.
14. The multicolored display of claim 1, wherein the photochromic material with the multiple photochromic states produces different colors relative to the other photochromic material.
15. A multicolored display comprising a substrate having uniformly situated thereon a coating of marking particles, said marking particles comprising a first polymer, a second polymer, a chelating agent, and a mixture of photochromic materials, wherein said mixture of photochromic materials comprises a spiropyran material of the formula:

and a dithenylethene material of the formula:

wherein R is an integer representing the number of repeat -CH2- units, and R
is -H or -CH=CH2; and a dithenylethene of the formula:

where R = C6H13, X = Y = H

16. The multicolored display of claim 15, wherein the spiropyran material is of the formula:

wherein n is an integer of from about 2 to about 8.
17. The multicolored display of claim 15, wherein the spiropyran material is of the formula:

wherein n is an integer of from about 2 to about 8.
18. The multicolored display of claim 15, wherein the spiropyran material is of the formula:

19. The multicolored display of claim 15, wherein the spiropyran and dithienylethene material are present in the marking particles in an amount of at least about 0.01 percent by weight of the marking particles.
20. The multicolored display of claim 15, wherein the spiropyran and dithienylethene material is present in the marking particles in an amount of at least about 0.05 percent by weight of the marking particles, and wherein the spiropyran material is present in the marking particles in an amount of no more than about 5 percent by weight of the marking particles.
21. The multicolored display of claim 15, wherein the chelating agent is a metal salt in the +2 state.
22. The multicolored display of claim 15, wherein the chelating agent is a salt of calcium, magnesium, zinc, or a transition metal.
23. The multicolored display of claim 15, wherein the chelating agent is present in the marking particles in an amount relative to the spiropyran material of at least about 1 mole of chelating agent for every 1 mole of spiropyran material.
24. The multicolored display of claim 15, wherein the chelating agent is present in the marking particles in an amount relative to the spiropyran material of at least about 2 moles of chelating agent for every 1 mole of spiropyran material.
25. The multicolored display of claim 24, wherein the chelating agent is present in the marking particles in an amount relative to the spiropyran material of no more than about 10 moles of chelating agent for every 1 mole of spiropyran material.
26. The multicolored display of claim 15, wherein the spiropyran material is incorporated into the backbone of the first polymer or the second polymer.
27. The multicolored display of claim 15, wherein the first polymer is a polymer comprising monomers selected from styrene, .alpha.-methylstyrene, vinyl toluene, n-alkyl methacrylates, n-alkyl acrylates, branched alkyl methacrylates, branched alkyl acrylates, chlorinated olefins, vinyl-phenolic materials, alkoxy alkoxy alkyl acrylates, alkoxy alkoxy alkyl methacrylates, cyano alkyl acrylates, cyano alkyl methacrylates, alkoxy alkyl acrylates, alkoxy alkyl methacrylates, methyl vinyl ether, maleic anhydride, butadiene, ethylene, vinylacetate, isobutylene, isoprene, or mixtures thereof.
28. A multicolored display of claim 15, wherein the second polymer is prepared by interfacial polymerization of (a) an organic soluble shell monomer selected from the group consisting of sebacoyl chloride, terephthaloyl chloride, phthaloyl chloride, isophthaloyl chloride, azeloyl chloride, glutaryl chloride, adipoyl chloride, hexamethylene diisocyanate, 4,4'-dicyclohexylmethane diisocyanate, 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, trans-1,4-cyclohexane diisocyanate, 4,4'-methyldiphenyl diisocyanate, 1,3,5-benzenetricarboxylic acid chloride, 4,4'-methyldiphenyl diisocyanate, tris(isocyanatophenyl) thiophosphate, or mixtures thereof, and (b) an aqueous soluble monomer selected from the group consisting of 1,6-hexanediamine, 1,4-bis(3-aminopropyl)piperazine, 2-methylpiperazine, m-xylene-.alpha.,.alpha.'-diamine, 1,8-diamino-.RHO.-menthane, 3,3'- diamino-N-methyldipropylamine, 1,3-cyclohexanebis(methylamine), 1,4- diaminecyclohexane, 2-methylpentanediamine, 1,2-diaminocyclohexane, 1,3-diaminopropane, 1,4-diaminobutane, 2,5-dimethylpiperazine, piperazine, fluorine-containing 1,2-diaminobenzenes, N,N'-dimethylethylenediamine, diethylenetriamine, bis(3-aminopropyl)amine, tris(2-aminoethyl)amine, or mixtures thereof.
29. The multicolored display of claim 15, wherein the second polymer is selected from the group consisting of polyureas, polyurethanes, polyesters, thermotropic liquid crystalline polyesters, polycarbonates, polyamides, polysulfones, poly(urea-urethanes), poly(ester-amides), poly(urea-amides), or mixtures thereof.
30. The multicolored display of claim 15, wherein the first polymer is present in an amount of from about 35 to about 90 percent of the marking particles and wherein the second polymer is present in an amount of from about to about 50 percent by weight of the marking particles.
31. The multicolored display of claim 15, further comprising a charge control agent.
32. The multicolored display of claim 15, further comprising a colorant.
33. A developer composition comprising marking particles according to claim 15 attached to a carrier particle.
34. A multicolored display comprising marking particles according to claim 33 wherein the marking particles are present in an amount of at least about 1 percent by weight of the carrier particles, and wherein the marking particles are present in an amount of no more than about 5 percent by weight of the carrier particles.
35. A process for forming a display, said process comprising:
generating an electrostatic latent image on an imaging member, and developing the latent image by contacting the imaging member with marking particles, said marking particles comprising a mixture of photochromic materials, wherein each of said photochromic materials is sensitive to a different wavelength of light relative to the other and produces a different color relative to the other photochromic material when exposed to the appropriate wavelength of light.
36. A process according to claim 35, further comprising effecting a photochromic change in at least some of the marking particles in the developed image from a first invisible state corresponding to a first absorption spectrum to a second visible state corresponding to a second absorption spectrum.
37. The process according to claim 35, wherein a first portion of the marking particles is caused to shift from the first state to the second state and a second portion of the marking particles remains in the first state.
38. The process according to claim 35, wherein the marking particles in the second state subsequently are caused to undergo another photochromic change, thereby returning them to the first visible state.
CA2510518A 2004-06-30 2005-06-22 Multicolored photochromic display Expired - Fee Related CA2510518C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US10/881,682 2004-06-30
US10/881,682 US7410750B2 (en) 2004-06-30 2004-06-30 Multicolored photochromic display

Publications (2)

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CA2510518A1 true CA2510518A1 (en) 2005-12-30
CA2510518C CA2510518C (en) 2010-06-01

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JP (1) JP4476882B2 (en)
CA (1) CA2510518C (en)

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Also Published As

Publication number Publication date
US20060001944A1 (en) 2006-01-05
CA2510518C (en) 2010-06-01
US7410750B2 (en) 2008-08-12
JP2006023737A (en) 2006-01-26
JP4476882B2 (en) 2010-06-09

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