Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
  • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
• • B—PERFORMING OPERATIONS; TRANSPORTING
  • B43—WRITING OR DRAWING IMPLEMENTS; BUREAU ACCESSORIES
  • B43M—BUREAU ACCESSORIES NOT OTHERWISE PROVIDED FOR
  • B43M11/00—Hand or desk devices of the office or personal type for applying liquid, other than ink, by contact to surfaces, e.g. for applying adhesive
  • B43M11/06—Hand-held devices
  • B43M11/08—Hand-held devices of the fountain-pen type
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
  • C07C65/32—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups
  • C07C65/38—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups having unsaturation outside the aromatic rings
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
  • C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
  • C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
  • C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
  • C08B37/0012—Cyclodextrin [CD], e.g. cycle with 6 units (alpha), with 7 units (beta) and with 8 units (gamma), large-ring cyclodextrin or cycloamylose with 9 units or more; Derivatives thereof
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
  • C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
  • C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
  • C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
  • C08B37/0012—Cyclodextrin [CD], e.g. cycle with 6 units (alpha), with 7 units (beta) and with 8 units (gamma), large-ring cyclodextrin or cycloamylose with 9 units or more; Derivatives thereof
  • C08B37/0015—Inclusion compounds, i.e. host-guest compounds, e.g. polyrotaxanes
• • 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
  • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
  • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D11/00—Inks
  • C09D11/16—Writing inks
  • C09D11/17—Writing inks characterised by colouring agents
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D11/00—Inks
  • C09D11/30—Inkjet printing inks
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D11/00—Inks
  • C09D11/30—Inkjet printing inks
  • C09D11/36—Inkjet printing inks based on non-aqueous solvents
• • 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
• • 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
  • G03G9/0825—Developers with toner particles characterised by their structure; characterised by non-homogenuous distribution of components
• • 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
  • G03G9/087—Binders for toner particles
  • G03G9/08775—Natural macromolecular compounds or derivatives thereof
  • G03G9/08777—Cellulose or derivatives thereof
• • 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
  • G03G9/0926—Colouring agents for toner particles characterised by physical or chemical properties
• • 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
  • G03G9/097—Plasticisers; Charge controlling agents
  • G03G9/09708—Inorganic compounds
• • 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
  • G03G9/097—Plasticisers; Charge controlling agents
  • G03G9/09733—Organic compounds
• • 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
  • G03G9/097—Plasticisers; Charge controlling agents
  • G03G9/09733—Organic compounds
  • G03G9/09741—Organic compounds cationic
• • 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
  • G03G9/097—Plasticisers; Charge controlling agents
  • G03G9/09733—Organic compounds
  • G03G9/0975—Organic compounds anionic
• • 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
  • G03G9/097—Plasticisers; Charge controlling agents
  • G03G9/09733—Organic compounds
  • G03G9/09758—Organic compounds comprising a heterocyclic ring
• • 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
  • G03G9/097—Plasticisers; Charge controlling agents
  • G03G9/09733—Organic compounds
  • G03G9/09775—Organic compounds containing atoms other than carbon, hydrogen or oxygen
• • 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
  • G03G9/097—Plasticisers; Charge controlling agents
  • G03G9/09783—Organo-metallic compounds
  • G03G9/09791—Metallic soaps of higher carboxylic acids
• • G—PHYSICS
  • G06—COMPUTING; CALCULATING OR COUNTING
  • G06K—GRAPHICAL DATA READING; PRESENTATION OF DATA; RECORD CARRIERS; HANDLING RECORD CARRIERS
  • G06K1/00—Methods or arrangements for marking the record carrier in digital fashion
  • G06K1/12—Methods or arrangements for marking the record carrier in digital fashion otherwise than by punching
  • G06K1/121—Methods or arrangements for marking the record carrier in digital fashion otherwise than by punching by printing code marks
• • G—PHYSICS
  • G06—COMPUTING; CALCULATING OR COUNTING
  • G06K—GRAPHICAL DATA READING; PRESENTATION OF DATA; RECORD CARRIERS; HANDLING RECORD CARRIERS
  • G06K19/00—Record carriers for use with machines and with at least a part designed to carry digital markings
  • G06K19/06—Record carriers for use with machines and with at least a part designed to carry digital markings characterised by the kind of the digital marking, e.g. shape, nature, code
  • G06K19/06009—Record carriers for use with machines and with at least a part designed to carry digital markings characterised by the kind of the digital marking, e.g. shape, nature, code with optically detectable marking
  • G06K19/06046—Constructional details
• • B—PERFORMING OPERATIONS; TRANSPORTING
  • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
  • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
  • B41M3/00—Printing processes to produce particular kinds of printed work, e.g. patterns
  • B41M3/14—Security printing
• • 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
  • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
  • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
  • Y02P20/00—Technologies relating to chemical industry
  • Y02P20/50—Improvements relating to the production of bulk chemicals
  • Y02P20/582—Recycling of unreacted starting or intermediate materials

Definitions

• the present invention relates to a mutable colored composition, which, in some embodiments, may be employed in an electrophotographic toner, e.g., a toner employed in a photocopier which is based on transfer xerography.
• an electrophotographic toner e.g., a toner employed in a photocopier which is based on transfer xerography.
• Electrophotography is broadly defined as a process in which photons are captured to create an electrical image analog of the original.
• the electrical analog in turn, is manipulated through a number of steps which result in a physical image.
• transfer xerography The most common form of electrophotography presently in use is called transfer xerography. Although first demonstrated by C. Carlson in 1938, the process was slow to gain acceptance. Today, however, transfer xerography is the foundation of a multi-billion dollar industry.
• the heart of the process is a photoreceptor, usually the moving element of the process, which is typically either drum-shaped or a continuous, seamless belt.
• a corona discharge - 9 is typically used to form a photoreceptor.
• the device deposits gas ions on the photoreceptor surface.
• the ions provide a uniform electric field across the photoreceptor and a uniform charge layer on its surface.
• An image of an illuminated original is projected through a lens system and focused on the photoreceptor.
• Light striking the charged photoreceptor surface results in increased conductivity across the photoreceptor with the concomitant neutralization of surface charges. Unilluminated regions of the photoreceptor surface retain their charges.
• the resulting pattern of surface charges is the latent electrostatic image.
• thermoplastic pigmented powder or toner the par ⁇ ticles of which bear a charge opposite to the surface charges on the photoreceptor, is brought close to the photoreceptor, thereby permitting toner particles to be attracted to the charged regions on the photoreceptor surface.
• the result is a physical image on the photoreceptor surface consisting of electrostatically held toner particles.
• a sheet of plain paper is brought into physical contact with the toner-bearing photoreceptor.
• a charge applied to the back side of the paper induces the attraction of the toner image to the paper.
• the image is a positive image of the original.
• the paper then is stripped from the photoreceptor, with the toner image clinging to it by electrostatic attraction.
• the toner image is permanently fused to the paper by an appropriate heating means, such as a hot pressure roll or a radiant heater.
• toner Because there is incomplete transfer of toner to the paper, it is necessary to clean the photoreceptor surface of residual toner. Such toner is wiped off with a brush, cloth, or blade. A corona discharge or reverse polarity aids in the removal of toner. A uniform light source then floods the photoreceptor to neutralize any residual charges from the previous image cycle, erasing the previous electrostatic image completely and conditioning the photoreceptor surface for another cycle.
• the toner generally consists of 1-15 micrometer average diameter particles of a thermoplastic powder.
• Black toner typically contains 5-10 percent by weight of carbon black particles of less than 1 micrometer dispersed in the thermoplastic powder.
• the carbon black may be replaced with cyan, magenta, or yellow pigments.
• the concentration and dispersion of the pigment must be adjusted to impart a conductivity to the toner which is appropriate for the development system.
• the toner is required to retain for extended periods of time the charge applied by contact electrification.
• the thermoplastic employed in the toner in general is selected on the basis of its melting behavior.
• thermoplastic must melt over a relatively narrow temperature range, yet be stable during storage and able to withstand the vigorous agitation which occurs in xerographic development chambers.
• electrophotography, and transfer xerography no doubt is a significant factor in the efficient distribution of information which has become essential in a global setting. It also contributes to the generation of vast quantities of paper which ultimately must either be disposed of or recycled.
• the conventional method for recycling paper comprises converting paper to pulp, and treating the pulp to remove ink, toner, and other colored materials, i.e., "de-inking" the paper, an expensive and not always completely successful operation.
• de-inking results in a sludge which typically is disposed of in a landfill.
• the resulting de-inked pulp then is used, often with the addition of at least some virgin pulp, to form paper, cardboard, cellulosic packaging materials, and the like.
• the present invention addresses the need for a simple, cost-effective, and environmentally sound method for recycling paper and for the for the multiple reuse of photocopy paper.
• the present invention provides, in general, a colorant system that is mutable by exposure to radiation. More particularly, the present invention provides a composition comprising a colorant which, in the presence of a radiation transorber, is mutable.
• the radiation transorber is capable of absorbing radiation and interacting with the colorant to effect a mutation of the colorant.
• the composition of the present invention includes a colorant and an ultraviolet radiation transorber.
• the colorant, in the presence of the ultraviolet radiation transorber is adapted, upon exposure of the transorber to ultraviolet radiation, to be mutable.
• the ultraviolet radiation transorber is adapted to absorb ultraviolet radiation and interact with the colorant to effect the irreversible mutation of the colorant.
• the ultraviolet radiation transorber absorb ultraviolet radiation at a wavelength of from about 4 to about 400 nanometers. It is even more desirable that the ultraviolet radiation transorber absorb ultraviolet radiation at a wavelength of 100 to 375 nanometers.
• the colored composition which comprises a colorant and an ultraviolet radiation transorber may also contain a molecular includant having a chemical structure which defines at least one cavity.
• the molecular includants include, but are not limited to, clathrates, zeolites, and cyclodextrins. Each of the colorant and ultraviolet radiation transorber is associated with one or more molecular includant.
• the colorant is at least partially included within a cavity of the molecular includant and the ultraviolet radiation transorber is associated with the molecular includant outside of the cavity. In some embodiments, the ultraviolet radiation transorber is covalently coupled to the outside of the molecular includant.
• the present invention also relates to a method of mutating the colorant in the composition of the present invention.
• the method comprises irradiating a composition containing a mutable colorant and an ultraviolet radiation transorber with ultraviolet radiation at a dosage level sufficient to mutate the colorant.
• the composition further includes a molecular includant.
• the composition is applied to a substrate before being irradiated with ultraviolet radiation. It is desirable that the mutated colorant is stable.
• the present invention is also related to a substrate having an image thereon that is formed by the composition of the present invention.
• the present invention is also related to an electrophotographic method that allows for the multiple reuse of a substrate such as photocopy paper.
• the method comprises exposing an image on a substrate as produced above, to ultraviolet radiation at a dosage level sufficient to irreversibly mutate the colorant.
• a second image is created on a photoreceptor surface, and a second toner is applied to the photoreceptor surface to form a toner image which replicates the second image.
• the second toner image of the second image is transferred to the substrate, and the second toner image is fixed to the substrate.
• the colorant in the second image may also be mutated by exposure to ultraviolet radiation, thus allowing the substrate to be reused for the fixation of a third image to the substrate.
• Figure 1 illustrates an ultraviolet radiation transorber/ mutable colorant/ molecular includant complex wherein the mutable colorant is malachite green, the ultraviolet radiation transorber is Irgacure 184 (1-hydroxycyclohexyl phenyl ketone), and the molecular includant is ⁇ -cyclodextrin.
• Figure 2 illustrates an ultraviolet radiation transorber/ mutable colorant/ molecular includant complex wherein the mutable colorant is victoria pure blue BO (Basic Blue 7) , the ultraviolet radiation transorber is Irgacure 184 (1 - hydroxycyclohexyl phenyl ketone), and the molecular includant is ⁇ -cyclodextrin.
• the mutable colorant is victoria pure blue BO (Basic Blue 7)
• the ultraviolet radiation transorber is Irgacure 184 (1 - hydroxycyclohexyl phenyl ketone
• the molecular includant is ⁇ -cyclodextrin.
• Figure 3 is an illustration of several 222 nanometer excimer lamps arranged in four parallel columns wherein the twelve numbers represent the locations where twelve intensity measurements were obtained approximately 5.5 centimeters from the excimer lamps.
• Figure 4 is an illustration of several 222 nanometer excimer lamps arranged in four parallel columns wherein the nine numbers represent the locations where nine intensity measurements were obtained approximately 5.5 centimeters from the excimer lamps.
• Figure 5 is an illustration of several 222 nanometer excimer lamps arranged in four parallel colums wherein the location of the number " 1 " denotes the location where ten intensity measurements were obtained from increasing distances from the lamps at that location. (The measurements and their distances from the lamp are summarized in Table 7.)
• the present invention relates in general to a colorant system that is mutable by exposure to radiation.
• the present invention relates to a composition comprising a colorant which, in the presence of a radiation transorber, is mutable.
• the radiation transorber is capable of absorbing radiation and interacting with the colorant to effect a mutation of the colorant.
• the composition of the present invention includes a colorant and an ultraviolet radiation transorber.
• the colorant in the presence of the ultraviolet radiation transorber, is adapted, upon exposure of the transorber to ultraviolet radiation, to be mutable.
• the ultraviolet radiation transorber is adapted to absorb ultraviolet radiation and interact with the colorant to effect the irreversible mutation of the colorant.
• composition and such variations as "colored composition” are used herein to mean a colorant, and an ultraviolet radiation transorber.
• composition-based is used as a modifier to indicate that the material, e.g., a toner, includes a colorant, an ultraviolet radiation transorber, and, optionally, a molecular includant.
• the term "colorant” is meant to include, without limitation, any material which, in the presence of an ultraviolet radiation transorber, is adapted upon exposure to ultraviolet radiation to be mutable.
• the colorant typically will be an organic material, such as an organic dye or pigment, including toners and lakes. Desirably, the colorant will be substantially transparent to, that is, will not significantly interact with, the ultraviolet radiation to which it is exposed.
• the term is meant to include a single material or a mixture of two or more materials.
• Organic dye classes include, by way of illustration only, triaryl methyl dyes, such as Malachite Green Carbinol base ⁇ 4-(dimethylamino)- ⁇ -[4-(dimethylamino)phenyl]- ⁇ -phenyl- benzene-methanol ⁇ , Malachite Green Carbinol hydrochloride ⁇ N-
• monoazo dyes such as Cyanine Black, Chrysoidine [Basic Orange 2; 4-(phenylazo)-l,3- benzenediamine monohydrochloride], and ⁇ -Naphthol Orange
• thiazine dyes such as Methylene Green, zinc chloride double salt
• oxazine dyes such as Lumichrome (7,8- dimethylalloxazine); naphthalimide dyes, such as Lucifer Yellow CH ⁇ 6-amino-2-[(hydrazinocarbonyl)amino]-2,3-dihydro-l ,3- dioxo-lH-benz[de]isoquinoline-5,8-disulfonic acid dilithium salt ⁇ ; azine dyes, such as Janus Green B ⁇ 3-(diethylamino)-7-[[4- (dimethylamino)phenyl]azo]-5-phenylphenazinium chloride ⁇ ; cyanine dyes, such as Indocyanine Green ⁇ Cardio-Green or Fox Green; 2-[7-[ 1 ,3-dihydro- 1 , 1 -dimethyl-3-(4-s
• azoic diazo dyes such as Fast Blue BB salt (Azoic Diazo No. 20; 4-benzoylamino-2,5- diethoxybenzene diazonium chloride, zinc chloride double salt); phenylenediamine dyes, such as Disperse Yellow 9 [N-(2,4- dinitrophenyl)-l ,4-phenylenediamine or Solvent Orange 53]; diazo dyes, such as Disperse Orange 13 [Solvent Orange 52; 1- phenylazo-4-(4-hydroxyphenylazo)naphthalene] ; anthraquinone dyes, such as Disperse Blue 3 [Celliton Fast Blue FFR; 1 - methylamino-4-(2-hydroxyethylamino)-9, 10-anthraquinone] , Disperse Blue 14 [Celliton Fast Blue B;
• xanthene dyes such as 2,7-dichlorofluorescein; proflavine dyes, such as 3 ,6-diaminoacridine hemisulfate (Proflavine); sulfonaphthalein dyes, such as Cresol Red (o_- cresolsulfonaphthalein); phthalocyanine dyes, such as Copper Phthalocyanine ⁇ Pigment Blue 15; (SP-4- l )-[29H,31H- phthalocyanato(2-)-N29 5 N30,N31,N32]copper ⁇ ; carotenoid dyes, such as tr ⁇ ns- ⁇ -carotene (Food Orange 5); car
• mutable with reference to the colorant is used to mean that the absorption maximum of the colorant in the visible region of the electromagnetic spectrum is capable of being mutated or changed by exposure to ultraviolet radiation when in the presence of the ultraviolet radiation transorber.
• absorption maximum it is only necessary that such absorption maximum be mutated to an absorption maximum which is different from that of the colorant prior to exposure to the ultraviolet radiation, and that the mutation be irreversible.
• the new absorption maximum can be within or outside of the visible region of the electromagnetic spectrum.
• the colorant can mutate to a different color or be rendered colorless.
• the latter is desirable when the colorant is used in a colored composition adapted to be utilized as a toner in an electrophotographic process which reuses the electrophotographic copy by first rendering the colored composition colorless and then placing a new image thereon.
• the term "irreversible" means that the colorant will not revert to its original color when it no longer is exposed to ultraviolet radiation.
• the mutated colorant will be stable, i.e., not appreciably adversely affected by radiation normally encountered in the environment, such as natural or artificial light and heat.
• a colorant rendered colorless will remain colorless indefinitely.
• ultraviolet radiation transorber is used herein to mean any material which is adapted to absorb ultraviolet radiation and interact with the colorant to effect the mutation of the colorant.
• the ultraviolet radiation transorber may be an organic compound.
• compound is intended to include a single material or a mixture of two or more materials. If two or more materials are employed, it is not necessary that all of them absorb ultraviolet radiation of the same wavelength.
• the present invention includes unique compounds that are capable of absorbing narrow ultraviolet wavelength radiation.
• the compounds are synthesized by combining a wavelength-selective sensitizer and a photoreactor.
• the photoreactors oftentimes do not efficiently absorb high energy radiation.
• the resulting compound is a wavelength specific compound that efficiently absorbs a very narrow spectrum of radiation. Examples of ultraviolet radiation transorbers are shown in Examples 5 and 9 herein.
• the ultraviolet radiation transorber may interact with the colorant in a variety of ways.
• the ultraviolet radiation transorber upon absorbing ultraviolet radiation, may be converted to one or more free radicals which interact with the colorant.
• Such free radical-generating compounds typically are hindered ketones, some examples of which include, but are not limited to: benzildimethyl ketal (available commercially as Irgacure® 651, Ciba-Geigy Corporation, Hawthorne, New York); 1-hydroxycyclohexyl phenyl ketone (Irgacure® 500); 2-methyl-l- [4-(methylthio)phenyl]-2-morpholino-propan-l-one] (Irgacure® 907); 2-benzyl-2-dimethylamino-l-(4-mo holinophenyl)butan-l- one (Irgacure® 369); and 1 -hydroxycyclohexyl phenyl ketone (Irgacure® 184).
• benzildimethyl ketal available commercially as Irgacure® 651, Ciba-Geigy Corporation, Hawthorne, New York
• the ultraviolet radiation may initiate an electron transfer or reduction-oxidation reaction between the ultraviolet radiation transorber and the colorant.
• the ultraviolet radiation transorber may be, but is not limited to, Michler's ketone (p-dimethylaminophenyl ketone) or benzyl trimethyl staimate.
• the ultraviolet radiation transorber could be, for example, bis[4-(diphenylsulphonio)phenyl)] sulfide bis- (hexafluorophosphate) (Degacure® KI85, Ciba-Geigy Corporation, Hawthorne, New York); Cyracure® UVI-6990 (Ciba-Geigy Corporation), which is a mixture of bis[4- (diphenylsulphonio)phenyl] sulfide bis(hexafluorophosphate) with related monosulphonium hexafluorophosphate salts; and 5-2,4-
• ultraviolet radiation is used herein to mean electromagnetic radiation having wavelengths in the range of from about 4 to about 400 nanometers.
• the especially desirable ultraviolet radiation range for the present invention is between approximately 100 to 375 nanometers.
• the term includes the regions commonly referred to as ultraviolet and vacuum ultraviolet.
• the wavelength ranges typically assigned to these two regions are from about 180 to about 400 nanometers and from about 100 to about 180 nanometers, respectively.
• the molar ratio of ultraviolet radiation transorber to colorant generally will be equal to or greater than about 0.5.
• the more efficient the ultraviolet radiation transorber is in absorbing the ultraviolet radiation and interacting with, i.e., transferring absorbed energy to, the colorant to effect irreversible mutation of the colorant the lower such ratio can be.
• Current theories of molecular photo chemistry suggest that the lower limit to such ratio is 0.5, based on the generation of two free radicals per photon. As a practical matter, however, ratios higher than 1 are likely to be required, perhaps as high as about 10.
• the present invention is not bound by any specific molar ratio range. The important feature is that the transorber is present in an amount sufficient to effect mutation of the colorant.
• the colorant, and ultraviolet radiation transorber are likely to be solids. However, any or all of such materials can be a liquid.
• the effectiveness of the ultraviolet radiation transorber is improved when the colorant and ultraviolet radiation transorber are in intimate contact. To this end, the thorough blending of the two components, along with other components which may be present, is desirable. Such blending generally is accomplished by any of the means known to those having ordinary skill in the art.
• the colored composition includes a polymer, blending is facilitated if the colorant and the ultraviolet radiation transorber are at least partly soluble in softened or molten polymer. In such case, the composition is readily prepared in, for example, a two-roll mill.
• the colored composition can be a liquid because one or more of its components is a liquid.
• the colored composition of the present invention typically will be utilized in paniculate form.
• the particles of the composition should be very small.
• the particles of a colored composition adapted for use as a toner in an electrophotographic process typically consist of 7-15 micrometer average diameter particles, although smaller or larger particles can be employed. It is important to note that the particles should be as uniform in size as possible. Methods of forming such particles are well known to those having ordinary skill in the art.
• Photochemical processes involve the absorption of light quanta, or photons, by a molecule, e.g., the ultraviolet radiation transorber, to produce a highly reactive electronically excited state.
• a molecule e.g., the ultraviolet radiation transorber
• the photon energy which is proportional to the wavelength of the radiation, cannot be absorbed by the molecule unless it matches the energy difference between the unexcited, or original, state and an excited state. Consequently, while the wavelength range of the ultraviolet radiation to which the colored composition is exposed is not directly of concem, at least a portion of the radiation must have wavelengths which will provide the necessary energy to raise the ultraviolet radiation transorber to an energy level which is capable of interacting with the colorant.
• the absorption maximum of the ultraviolet radiation transorber ideally will be matched with the wavelength range of the ultraviolet radiation in order to increase the efficiency of the mutation of the colorant. Such efficiency also will be increased if -the wavelength range of the ultraviolet radiation is relatively narrow, with the maximum of the ultraviolet radiation transorber coming within such range.
• especially suitable ultraviolet radiation has a wavelength of from about 100 to about 375 nanometers.
• Ultraviolet radiation within this range desirably may be incoherent, pulsed ultraviolet radiation from a dielectric barrier discharge excimer lamp.
• incoherent, pulsed ultraviolet radiation has reference to the radiation produced by a dielectric barrier discharge excimer lamp (referred to hereinafter as “excimer lamp”).
• excimer lamp a dielectric barrier discharge excimer lamp
• excimer lamp Such a lamp is described, for example, by U. Kogelschatz, "Silent discharges for the generation of ultraviolet and vacuum ultraviolet excimer radiation,” Pure & Appl. Chem., 62, No. 9, pp. 1667-1674 (1990); and E. Eliasson and U. Kogelschatz, "UV Excimer Radiation from Dielectric-Barrier
• excimer lamps were developed originally by ABB Infocom Ltd., Lenzburg, Switzerland. The excimer lamp technology since has been acquired by Haraus Noblelight AG, Hanau, Germany. The excimer lamp emits radiation having a very narrow bandwidth, i.e., radiation in which the half width is of the order of 5-15 nanometers. This emitted radiation is incoherent and pulsed, the frequency of the pulses being dependent upon the frequency of the alternating current power supply which typically is in the range of from about 20 to about 300 kHz.
• An excimer lamp typically is identified or referred to by the wavelength at which the maximum intensity of the radiation occurs, which convention is followed throughout this specification. Thus, in comparison with most other commercially useful sources of ultraviolet radiation which typically emit over the entire ultraviolet spectrum and even into the visible region, excimer lamp radiation is substantially monochromatic.
• Excimers are unstable molecular complexes which occur only under extreme conditions, such as those temporarily existing in special types of gas discharge. Typical examples are the molecular bonds between two rare gaseous atoms or between a rare gas atom and a halogen atom. Excimer complexes dissociate within less than a microsecond and, while they are dissociating, release their binding energy in the form of ultraviolet radiation. Known excimers, in general, emit in the range of from about 125 to about 360 nanometers, depending upon the excimer gas mixture.
• the colorant and the ultraviolet radiation transorber have been described as separate compounds, they can be part of the same molecule. For example, they can be covalently coupled to each other, either directly, or indirectly through a relatively small molecule, or spacer.
• the colorant and ultraviolet radiation transorber can be covalently coupled to a large molecule, such as an oligomer or a polymer, particularly when the solid colored composition of the present invention is adapted to be utilized as a toner in an electrophotographic process.
• the colorant and ultraviolet radiation transorber may be associated with a large molecule by van der Waals forces, and hydrogen bonding, among other means. Other variations will be readily apparent to those having ordinary skill in the art.
• the composition further comprises a molecular includant.
• molecular includant is intended to mean any substance having a chemical structure which defines at least one cavity. That is, the molecular includant is a cavity-containing structure.
• the term “cavity” is meant to include any opening or space of a size sufficient to accept at least a portion of one or both of the colorant and the ultraviolet radiation transorber.
• the cavity can be a tunnel through the molecular includant or a cave-like space in the molecular includant.
• the cavity can be isolated or independent, or connected to one or more other cavities.
• the molecular includant can be inorganic or organic in nature.
• the chemical structure of the molecular includant is adapted to form a molecular inclusion complex.
• molecular includants are, by way of illustration only, clathrates or intercalates, zeolites, and cyclodextrins.
• cyclodextrins include, but are not limited to, alpha-cyclodextrin, beta-cyclodextrin, gamma- cyclodextrin, hydroxypropyl beta-cyclodextrin, hydroxyethyl beta-cyclodextrin, sulfated beta-cyclodextrin, and sulfated gamma-cyclodextrin.
• the molecular includant is a cyclodextrin. More particularly, in some embodiments, the molecular includant is an alpha-cyclodextrin.
• the molecular includant is a beta- cyclodextrin.
• the closer the transorber molecule is to the mutable colorant on the molecular includant the more efficent the interaction with the colorant to effect mutation of the colorant.
• the molecular includant with functional groups that can react with and bind the transorber molecule and that are close to the binding site of the mutable colorant are the more desirable molecular includants.
• the colorant and the ultraviolet radiation transorber are associated with the molecular includant.
• the term "associated" in its broadest sense means that the colorant and the ultraviolet radiation transorber are at least in close proximity to the molecular includant.
• the colorant and/or the ultraviolet radiation transorber can be maintained in close proximity to the molecular includant by hydrogen bonding, van der Waals forces, or the like.
• either or both of the colorant and the ultraviolet radiation transorber can be covalently bonded to the molecular includant.
• the colorant will be associated with the molecular includant by means of hydrogen bonding and/or van der Waals forces or the like, while the ultraviolet radiation transorber is covalently bonded to the molecular includant.
• the colorant is at least partially included within the cavity of the molecular includant, and the ultraviolet radiation transorber is located outside of the cavity of the molecular includant.
• the colorant and the ultraviolet radiation transorber are associated with the molecular includant, the colorant is cyrstal violet, the ultraviolet radiation transorber is a dehydrated phthaloylglycine-2959, and the molecular includant is beta-cyclodextrin.
• the colorant and the ultraviolet radiation transorber are associated with the molecular includant, the colorant is crystal violet, the ultraviolet radiation transorber is
• the colorant and the ultraviolet radiation transorber are associated with the molecular includant
• the colorant is malachite green
• the ultraviolet radiation transorber is Irgacure 184
• the molecular includant is beta- cyclodextrin as shown in Figure 1.
• the colorant and the ultraviolet radiation transorber are associated with the molecular includant
• the colorant is victoria pure blue BO
• the ultraviolet radiation transorber is Irgacure 184
• the molecular includant is beta-cyclodextrin as shown in Figure 2.
• Examples 5 through 9 disclose a method of preparing and associating these colorants and ultraviolet radiation transorbers to beta-cyclodextrins. It is to be understood that the methods disclosed in Examples 5 through 9 are merely one way of preparing and associating these components, and that many other methods known in the chemical arts may be used. Other methods of preparing and associated such components, or any of the other components which may be used in the present invention, would be known to those of ordinary skill in the art once the specific components have been selected.
• the colorant, ultraviolet radiation transorber, and molecular includant are likely to be solids. However, any or all of such materials can be a liquid.
• the colored composition can be a liquid either because one or more of its components is a liquid, or, when the molecular includant is organic in nature, a solvent is employed.
• Suitable solvents include, but are not limited to, amides, such as N,N- dimethylformamide; sulfoxides, such as dimethylsulfoxide; ketones, such as acetone, methyl ethyl ketone, and methyl butyl ketone; aliphatic and aromatic hydrocarbons, such as hexane, octane, benzene, toluene, and the xylenes; esters, such as ethyl acetate; water; and the like.
• amides such as N,N- dimethylformamide
• sulfoxides such as dimethylsulfoxide
• ketones such as acetone, methyl ethyl ketone, and methyl butyl ketone
• aliphatic and aromatic hydrocarbons such as
• the present invention also relates to a method of mutating the colorant in the composition of the present invention.
• the method comprises irradiating a composition containing a mutable colorant and an ultraviolet radiation transorber with ultraviolet radiation at a dosage level sufficient to mutate the colorant.
• the composition further includes a molecular includant.
• the composition is applied to a substrate before being irradiated with ultraviolet radiation.
• the amount or dosage level of ultraviolet radiation that the colorant of the present invention is exposed to will generally be that amount which is necessary to mutate the colorant.
• the amount of ultraviolet radiation necessary to mutate the colorant can be determined by one of ordinary skill in the art using routine experimentation.
• Power density is the measure of the amount of radiated electromagnetic power traversing a unit area and is usually expressed in watts per centimeter squared (W/cm 2 ).
• the power density level range is between approximately 5 mW/cm 2 and 15 mW/cm 2 , more particularly 8 to 10 mW/cm 2 .
• the dosage level typically is a function of the time of exposure and the intensity or flux of the radiation source which irradiates the colored composition.
• the latter is effected by the distance of the composition from the source and, depending upon the wavelength range of the ultraviolet radiation, can be effected by the atmosphere between the radiation source and the composition. Accordingly, in some instances it may be appropriate to expose the composition to the radiation in a controlled atmosphere or in a vacuum, although in general neither approach is desired.
• the colorant of the present invention is mutated by exposure to 222 nanometer excimer lamps. More particularly, the colorant crystal violet is mutated by exposure to 222 nanometer lamps. Even more particularly, the colorant crystal violet is mutated by exposure to
• nanometer excimer lamps located approximately 5 to 6 centimeters from the colorant, wherein the lamps are arranged in four parallel columns approximately 30 centimeters long as shown in Figures 3 and 4. It is to be understood that the arrangement of the lamps is not critical to this aspect of the invention. Accordingly, one or more lamps may be arranged in any configuration and at any distance which results in the colorant mutating upon exposure to the lamp's ultraviolet radiation. One of ordinary skill in the art would be able to determine by routine experimentation which configurations and which distances are appropriate. Also, it is to be understood that different excimer lamps are to be used with different ultraviolet radiation transorbers. The excimer lamp used to mutate a colorant associated with an ultraviolet radiation transorber should produce ultraviolet radiation of a wavelength that is absorbed by the ultraviolet radiation transorber.
• the colored composition of the present invention can be utilized on or in any substrate. If the composition is present in a substrate, however, the substrate should be substantially transparent to the ultraviolet radiation which is employed to mutate the colorant. That is, the ultraviolet radiation will not significantly interact with or be absorbed by the substrate. As a practical matter, the composition typically will be placed on a substrate, with the most common substrate being paper. Other substrates, including, but not limited to, woven and nonwoven . webs or fabrics, films, and the like, can be used, however.
• Another aspect of the present invention is the substrate having an image thereon that is formed by the composition of the present invention.
• a desirable substrate is paper.
• Especially desirable substrates include, but are not limited to, photocopy paper and facsimile paper.
• the composition of the present invention can be incorporated into a toner adapted to be utilized in an electrophotographic process.
• the toner includes the colorant, ultraviolet radiation transorber, and a carrier.
• the carrier can be a polymer, and the toner may further contain a charge carrier.
• the electrophotographic process comprises the steps of creating an image on a photoreceptor surface, applying toner to the photoreceptor surface to form a toner image which replicates the image, transferring the toner image to a substrate, and fixing the toner image to the substrate. After the toner has been fixed on the substrate, the colorant in the composition is mutated by irradiating the substrate with ultraviolet radiation at a dosage level sufficient to irreversibly mutate the colorant.
• the ultraviolet radiation used in the method to mutate the colorant will have wavelengths of from about 100 to about 375 nanometers.
• the ultraviolet radiation is incoherent, pulsed ultraviolet radiation produced by a dielectric barrier discharge excimer lamp.
• the toner may further comprise a molecular includant.
• the carrier will be a polymer, typically a thermosetting or thermoplastic polymer, with the latter being the more common.
• thermoplastic polymers include, but are not limited to: end-capped polyacetals, such as p o l y ( o xyme th y lene ) o r p o l yfo rma l deh yde , poly(trichloroacetaldehyde), poly(tz -v aleraldehyde ) , poly(acetaldehyde), poly(propionaldehyde), and the like; acrylic polymers, such as polyacrylamide, poly(acrylic acid), poly(methacrylic acid), poly(ethyl acrylate), poly(methyl methacrylate), and the like; fluorocarbon polymers, such as poly(tetrafluoroethylene), perfluorinated ethylenepropylene copolymers, ethylenetetrafluoroethylene copolymers, poly- (chlorotrifluoroethylene), ethylene-chlorotrifluoroethylene copolymers, poly(vinyliden
• polystyrene pyromellitimido-l,4-phenylene
• polyolefins such as polyethylene, polypropylene, poly(l -butene), poly(2-butene), poly(l -pentene), poly(2-pentene), poly(3-methyl-l-pentene), poly(4-methyl-l-pentene), l,2-poly-l,3-butadiene, l,4-poly-l,3- butadiene, polyisoprene, polychloroprene, polyacrylonitrile, poly(vinyl acetate), poly(vinylidene chloride), polystyrene, and the like; and copolymers of the foregoing, such as acrylonitrile- butadienestyrene (ABS) copolymers, styrene- «-butylmethacrylate copolymers, ethylene-vinyl acetate copolymers, and the like
• thermoplastic polymers include styrene- ⁇ -butyl methacrylate copolymers, polystyrene, styrene-/2 -butyl acrylate copolymers, styrene- butadiene copolymers , polycarbonates, poly(methyl methacrylate), poly(vinylidene fluoride), polyamides (nylon- 12), polyethylene, polypropylene, ethylene-vinyl acetate copolymers, and epoxy resins.
• thermosetting polymers include, but are not limited to, alkyd resins, such as phthalic anhydride-glycerol resins, maleic acid-glycerol resins, adipic acid-glycerol resins, and phthalic anhydride-pentaerythritol resins; ally lie resins, in which such monomers as diallyl phthalate, diallyl isophthalate diallyl maleate, and diallyl chlorendate serve as nonvolatile cross- linking agents in polyester compounds; amino resins, such as aniline-formaldehyde resins, ethylene urea-formaldehyde resins, dicyandiamide-formaldehyde resins, melamine-formaldehyde resins, sulfonamide-formaldehyde resins, and urea-formaldehyde resins; epoxy resins, such as cross -linked epichlorohydrin- bisphenol A resins; phenolic resins, such as
• the colored composition of the present invention also can contain additional components, depending upon the application for which it is intended.
• a composition which is to be utilized as a toner in an electrophotographic process optionally can contain, for example, charge carriers, stabilizers against thermal oxidation, viscoelastic properties modifiers, cross-linking agents, plasticizers, and the like.
• a composition which is to be utilized as a toner in an electrophotographic process optionally can contain charge control additives such as a quaternary ammonium salt; flow control additives such as hydrophobic silica, zinc stearate, calcium stearate, lithium stearate, polyvinylstearate, and polyethylene powders; and fillers such as calcium carbonate, clay and talc, among other additives used by those having ordinary skill in the art.
• the charge carrier will be the major component of the toner. Charge carriers, of course, are well known to those having ordinary skill in the art and typically are polymer-coated metal particles. The identities and amounts of such additional components in the colored composition are well known to one of ordinary skill in the art.
• the toner of the present invention can also include a molecular includant as described above.
• the composition-based toner can be used to form a first image on a virgin paper sheet.
• the sheet then can be recycled by exposing the sheet to ultraviolet radiation in accordance with the present invention to render the colorant, and, as a consequence, the composition, colorless.
• a second image then can be formed on the sheet.
• the second image can be formed from a standard, known toner, or from a composition-based toner which is either the same as or different from the composition-based toner which was used to form the first image. If a composition-based toner is
• Each steel plate was 3 x 5 inches (7.6 cm x 12.7 cm) and was obtained from Q- Panel Company, Cleveland, Ohio.
• the film on the steel plate was estimated to have a thickness of the order of 10-20 micrometers.
• the colorant was Malachite Green oxalate (Aldrich Chemical Company, Inc., Milwaukee, Wisconsin), referred to hereinafter as Colorant A for convenience.
• UVRT ultraviolet radiation transorber
• Irgacure® 500 UVRT A
• Irgacure® 651 UVRT B
• Irgacure® 907 UVRT C
• the polymer was one of the following: an epichlorohydrin-bisphenol A epoxy resin ("Polymer A”), Epon® 1004F (Shell Oil Company, Houston, Texas); a poly(ethylene glycol) having a weight-average molecular weight of about 8,000 (“Polymer B”), Carbowax 8000 (Aldrich Chemical Company); and a poly(ethylene glycol) having a weight-average molecular weight of about 4,600 (“Polymer C”), Carbowax 4600 (Aldrich Chemical Company).
• a control film was prepared which consisted only of colorant and polymer. The compositions of the films are summarized in Table 1.
• each film was exposed to ultraviolet radiation.
• the steel plate having the film sample on its surface was placed on a moving conveyor belt having a variable speed control.
• Three different ultraviolet radiation sources, or lamps, were used.
• Lamp A was a 222- nanometer excimer lamp and Lamp B was a 308-nanometer excimer lamp, as already described.
• Lamp C was a fusion lamp system having a "D" bulb (Fusion Systems Corporation, Rockville, Maryland).
• the excimer lamps were organized in banks of four cylindrical lamps having a length of about 30 cm, with the lamps being oriented normal to the direction of motion of the belt.
• the lamps were cooled by circulating water through a centrally located or inner tube of the lamp and, as a consequence, they operated at a relatively low temperature, i.e., about 50°C.
• the power density at the lamp's outer surface typically is in the range of from about 4 to about 20 joules per square meter (J/m2).
• the table records the number of passes under a lamp which were required in order to render the film colorless.
• the table records the number of passes tried, with the film in each case remaining colored (no change).
• UV radiation Transorber UV radiation Transorber
• This example describes the preparation of solid colored compositions adapted to be utilized as toners in an electrophotographic process.
• the toner included Colorant A as described in Example 1 ; a polymer, DER 667, an epichlorohydrin-bisphenol A epoxy resin (Polymer D), Epon® 1004F (Dow Chemical Company, Midland, Michigan); and a charge carrier, Carrier A, which consisted of a very finely divided polymer-coated metal.
• UVRT ultraviolet radiation transorber
• UVRT D Irgacure® 369
• Irgacure® 184 UVRT E
• a second polymer also was present, styrene aery late 1221 , a styrene-acrylic acid copolymer (Hercules Incorporated, Wilmington, Delaware).
• Toner Type _g_ Carrier (g A A 8.4 210 B B 8.4 210 C C 8.4 210 D D 8.4 210
• Each toner was placed separately in a Sharp Model ZT- 50TD1 toner cartridge and installed in either a Sharp Model Z-76 or a Sharp Model Z-77 xerographic copier (Sharp Electronics Corporation, Mahwah, New Jersey). Images were made in the usual manner on bond paper (Neenah Bond). The image-bearing sheets then were exposed to ultraviolet radiation from Lamp B as described in Example 1. In each case, the image was rendered colorless with one pass.
• This example describes the preparation of a ⁇ -cyclodextrin molecular includant having (1) an ultraviolet radiation transorber covalently bonded to the eyclodextrin outside of the cavity of the cyclodextrin and (2) a colorant associated with the eyclodextrin by means of hydrogen bonds and/or van der Waals forces.
• Lamp A was a 222-nanometer excimer lamp assembly organized in banks of four cylindrical lamps having a length of about 30 cm.
• the lamps were cooled by circulating water through a centrally located or inner tube of the lamp and, as a consequence, they operated at a relatively low temperature, i.e., about 50°C.
• the power density at the lamp's outer surface typically is in the range of from about 4 to about 20 joules per square meter (J/m 2 ). However, such range in reality merely reflects the capabilities of current excimer lamp power supplies; in the future, higher power densities may be practical.
• Lamp B was a 500-watt Hanovia medium pressure mercury lamp (Hanovia Lamp Co., Newark, New Jersey). The distance from Lamp B to the sample being irradiated was about 15 cm.
• Colorant A and beta-cyclodextrin in N,N-dimethylformamide was not decolorized by Lamp A.
• a second control sample consisting of Colorant A and 1-hydroxycyclohexyl phenyl ketone in N,N- dimethylformamide was decolorized by Lamp A within 60 seconds. On standing, however, the color began to reappear within an hour.
• this example describes the preparation of a beta-cyclodextrin molecular includant having (1) a colorant at least partially included within the cavity of the eyclodextrin and associated therewith by means of hydrogen bonds and/or van der Waals forces and (2) an ultraviolet radiation transorber covalently bonded to the eyclodextrin outside of the cavity of the eyclodextrin.
• reaction mixture was heated to 50°C and 0.5 ml of triethylamine added.
• the reaction mixture was maintained at 50° C for an hour and allowed to cool to ambient temperature.
• the reaction mixture then was worked up as described in Part A, above, to give 14.2 g of beta-cyclodextrin-transorber Colorant A inclusion complex, a blue-green powder.
• This Example describes a method of preparing an ultraviolet radiation transorber designated phthaloylglycine-2959.
• the following was admixed in a 250ml 3 -necked round bottomed flask fitted with a Dean & Stark adapter with condenser and two glass stoppers: 20.5g (O.lmole) of the wavelength selective sensitizer, phthaloylglycine (Aldrich); 24.6g (O.lmole) of the photoreactor, DARCUR 2959 (Ciba-Geigy, Hawthorne, NY); 100 ml of benzene (Aldrich); and 0.4g p-toluene sulfonic acid (Aldrich).
• phthaloyl glycine-2959 had the following physical parameters:
• This Example describes a method of dehydrating the phthaloylglycine-2959 produced in Example 5.
• This Example describes a method of producing a beta- cyclodextrin having dehydrated phthaloylglycine-2959 groups from Example 6 covalently bonded thereto.
• the beta-cyclodextrin molecule has several primary alcohols and secondary alcohols with which the phthaloylglycine-2959 can react.
• the above representative reaction only shows a single phthaloylglycine-2959 molecule for illustrative purposes.
• This example describes a method of associating a colorant and an ultraviolet radiation transorber with a molecular includant.
• this Example describes a method of associating the colorant crystal violet with the molecular includant beta- cyclodextrin covalently bonded to the ultraviolet radiation transorber phthaloylglycine-2959 of Example 7.
• the following was placed in a 100ml beaker: 4.0 g beta- cyclodextrin having a dehydrated phthaloylglycine-2959 group; and 50ml of water. The water was heated to 70°C at which point the solution became clear. Next, 0.9g (2.4 mmole) crystal violet (Aldrich Chemical Company, Milwaukee, WI) was added to the solution, and the solution was stirred for 20 minutes. Next, the solution was then filtered. The filtrand was washed with the filtrate and then dried in a vacuum oven at 84° C. A violet-blue powder was obtained having 4.1g (92%) yield. The resulting reaction product had the folowing physical parameters:
• This Example describes a method of producing the ultraviolet radiation transorber 4(4-hydroxyphenyl) butan-2-one- 2959 (chloro substituted) .
• the ultraviolet radiation transorber produced in this Example 4(4-hydroxyphenyl) butan-2-one-2959 (chloro substituted), may be associtated with beta-cyclodextrin and a colorant such as crystal violet, using the methods described above in F.xam-nle.s 6 thrnuuh 8 wherein 4C4-hvrirnxvnhenvl ⁇ h ⁇ tan-9- one-2959 (chloro substituted) would be substituted for the dehydrated phthaloylglycine-2959 in the methods in Examples 6 through 8.
• the lamp 10 comprises a lamp housing 15 with four excimer lamp bulbs 20 positioned in parallel, the excimer lamp bulbs 20 are approximately 30 cm in length.
• the lamps are cooled by circulating water through a centrally located or inner tube (not shown) and, as a consequence, the lamps are operated at a relatively low temperature, i.e., about 50°C.
• the power density at the lamp's outer surface typically is in the range of from about 4 to about 20 joules per square meter (J/m 2 ).
• Table 5 summarizes the intensity readings which were obtained by a meter located on the surface of the substrate.
• the readings numbered 1, 4, 7, and 10 were located approximately 7.0 centimeters from the left end of the column as shown in Figure 3.
• the readings numbered 3, 6, 9, and 12 were located approximately 5.5 centimeters from the right end of the column as shown in Figure 3.
• the readings numbered 2, 5, 8, and 11 were centrally located approximately 17.5 centimeters from each end of the column as shown in Figure 3.
• the excimer lamp 10 comprises a lamp housing 15 with four excimer lamp bulbs 20 positioned in parallel, the excimer lamp bulbs 20 are approximately 30 cm in length.
• the lamps are cooled by circulating water through a centrally located or inner tube (not shown) and, as a consequence, the lamps are operated at a relatively low temperature, i.e., about 50°C.
• the power density at the lamp's outer surface typically is in the range of from about 4 to about 20 joules per square meter
• Table 6 summarizes the intensity readings which were obtained by a meter located on the surface of the substrate.
• the readings numbered 1, 4, and 7 were located approximately 7.0 centimeters from the left end of the columns as shown in Figure 4.
• the readings numbered 3, 6, and 9 were located approximately 5.5 centimeters from the right end of the columns as shown in Figure 4.
• the readings numbered 2, 5, 8 were centrally located approximately 17.5 centimeters from each end of the columns as shown in Figure 4.
• the excimer lamp 10 comprises a lamp housing 15 with four excimer lamp bulbs 20 positioned in parallel, the excimer lamp bulbs 20 are approximately 30 cm in length.
• the lamps are cooled by circulating water through a centrally located or inner tube (not shown) and, as a consequence, the lamps are operated at a relatively low temperature, i.e., about 50°C.
• the power density at the lamp's outer surface typically is in the range of from about 4 to about 20 joules per square meter (J/m 2 ).
• Table 7 summarizes the intensity readings which were obtained by a meter located on the surface of the substrate at position 1 as shown in Figure 5. Position 1 was centrally located approximately 17 centimeters from each end of the column as shown in Figure 5.

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• Molecular Biology (AREA)
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• Polymers & Plastics (AREA)
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• Spectroscopy & Molecular Physics (AREA)
• Developing Agents For Electrophotography (AREA)
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Citations (8)

• 1994
  • 1994-07-29 AU AU75173/94A patent/AU7517394A/en not_active Withdrawn
  • 1994-07-29 ES ES94925143T patent/ES2107396T1/es active Pending
  • 1994-07-29 EP EP94925143A patent/EP0712506A1/en not_active Withdrawn
  • 1994-07-29 PL PL94312835A patent/PL312835A1/xx unknown
  • 1994-07-29 BR BR9407181A patent/BR9407181A/pt not_active IP Right Cessation
  • 1994-07-29 SK SK152-96A patent/SK15296A3/sk unknown
  • 1994-07-29 CA CA002168727A patent/CA2168727A1/en not_active Abandoned
  • 1994-07-29 WO PCT/US1994/008588 patent/WO1995004955A1/en not_active Application Discontinuation
  • 1994-07-29 DE DE0712506T patent/DE712506T1/de active Pending
  • 1994-07-29 JP JP7506457A patent/JPH09502031A/ja active Pending
  • 1994-07-29 HU HU9600241A patent/HUT73681A/hu unknown
  • 1994-07-29 CN CN94193454A patent/CN1131468A/zh active Pending
  • 1994-07-29 CZ CZ96275A patent/CZ27596A3/cs unknown
  • 1994-07-29 RU RU96104352/28A patent/RU2152636C1/ru not_active IP Right Cessation
• 1996
  • 1996-02-02 NO NO960455A patent/NO960455L/no unknown
  • 1996-02-02 FI FI960483A patent/FI960483A/sv not_active Application Discontinuation

Patent Citations (8)

Non-Patent Citations (4)

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