WO2000016985A1 - Microcapsules contenant du solvant pour de la matiere chromogene - Google Patents

Microcapsules contenant du solvant pour de la matiere chromogene Download PDF

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Publication number
WO2000016985A1
WO2000016985A1 PCT/US1999/005079 US9905079W WO0016985A1 WO 2000016985 A1 WO2000016985 A1 WO 2000016985A1 US 9905079 W US9905079 W US 9905079W WO 0016985 A1 WO0016985 A1 WO 0016985A1
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WO
WIPO (PCT)
Prior art keywords
oil
solvent
microcapsules
diluent
weight
Prior art date
Application number
PCT/US1999/005079
Other languages
English (en)
Inventor
Peter C. Yao
Datta G. Mislankar
Glenn E. Bane
Original Assignee
The Mead Corporation
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 The Mead Corporation filed Critical The Mead Corporation
Priority to AU29909/99A priority Critical patent/AU2990999A/en
Publication of WO2000016985A1 publication Critical patent/WO2000016985A1/fr

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Classifications

    • 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
    • B41M5/28—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used using thermochromic compounds or layers containing liquid crystals, microcapsules, bleachable dyes or heat- decomposable compounds, e.g. gas- liberating
    • B41M5/287—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used using thermochromic compounds or layers containing liquid crystals, microcapsules, bleachable dyes or heat- decomposable compounds, e.g. gas- liberating using microcapsules or microspheres only
    • 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
    • B41M5/124—Duplicating or marking methods; Sheet materials for use therein using pressure to make a masked colour visible, e.g. to make a coloured support visible, to create an opaque or transparent pattern, or to form colour by uniting colour-forming components
    • B41M5/165—Duplicating or marking methods; Sheet materials for use therein using pressure to make a masked colour visible, e.g. to make a coloured support visible, to create an opaque or transparent pattern, or to form colour by uniting colour-forming components characterised by the use of microcapsules; Special solvents for incorporating the ingredients
    • B41M5/1655—Solvents

Definitions

  • This invention relates to recording systems such as pressure-sensitive copying systems and particularly to a solvent for solvating a color precursor useful in such systems.
  • Pressure-sensitive copying paper is well-known and is widely used in the production of business forms. In these systems a colorless chromogenic material dissolved in an oily solvent is encapsulated in a wall forming material to provide microcapsules which are then coated onto a paper substrate.
  • Two types of pressure-sensitive copying paper are known, namely, transfer and self-contained copy sheets. The most widely used is the transfer type.
  • a business forms set using the transfer type of pressure-sensitive copying paper comprises a top sheet (usually known as a "CB” sheet) coated on its lower or back surface with microcapsules containing a solution of at least one chromogenic material (alternatively termed a color former) and a bottom sheet (usually known as a "CF” sheet) coated on its upper or top surface with a Lewis acid or other color developer composition.
  • a top sheet usually known as a "CB” sheet
  • CF chromogenic material
  • CF CF sheet
  • Imaging pressure exerted on the sheets by writing, typing or impact printing ruptures the microcapsules, thereby releasing or transferring the chromogenic material solution onto the color developer composition and giving rise to a chemical reaction which develops the color of the chromogenic material and so produces a copy image.
  • the solvent is an important element in determining the performance of the pressure-sensitive copying system in terms of stability of the sheets to heat and storage time, rate of color development, extent of color development, and durability of image.
  • the color former solvent functions as a carrier for the color former and as a medium for the reaction between the color former and the acidic co-reactant material.
  • the solvent must be capable of holding the color former in solution within the microcapsule, of carrying the color former to the sensitized surface of the CF sheet when the microcapsule is ruptured, and of promoting or at least not inhibiting color development with the co-reactant.
  • the solvent should be non-injurious to skin, clothing or environment.
  • the color former solution be easily encapsulated by conventional techniques, that it have good shelf life in the encapsulated form, and that it be stable at moderately elevated temperatures. It is also important that the mark produced as a result of the reaction between the color former and the co-reactant develop rapidly, be fade resistant and be resistant to bleeding or feathering as a result of capillary action or other surface phenomena.
  • solvents used to dissolve the chromogenic materials in pressure-sensitive copying papers have typically been hydrocarbon products derived from petroleum or coal deposits, for example partially hydrogenated terphenyls, alkyl naphthalenes, diary lmethane derivatives, dibenzyl benzene derivatives or derivatives of hydrocarbon products, for example chlorinated paraffins.
  • solvents are usually mixed with cheaper diluents or extenders such as kerosene, which although of lesser solvating power, assist in carrying the color former to the developer and provide more cost- effective solvent compositions.
  • Vegetables oils have been disclosed as solvents for use in pressure-sensitive copying papers. See for example U.S. Patents 2,712,507; 2,730,457 and 3,016,308. More recent disclosures of the use of vegetable oil solvents in pressure-sensitive copying paper can be found in U.S. Patents 4,783,196 and 4,923,641, in European Patent Applications Nos. 86636A, 155593A , and, especially, in European Patent Application No. 262569A which discloses the use of triphenylmethane leuco dye chromogenic materials in conjunction with the vegetable, animal or mineral oils.
  • 5,585,051 discloses groups of solvents which include mixtures of vegetable oils with modified triglycerides and specifically discloses soybean oil in admixture with a modified triglyceride.
  • U.S. Patent No. 4,093,278 discloses that aryl esters and benzyl esters of benzoic acid, such as benzyl benzoate, are useful as solvents for conventional color formers.
  • the solvent may be employed in admixture with from 0 to 3 parts of a diluent such as a vegetable or mineral oil.
  • U. S. Patent No. 5,053,277 discloses the use of alkylated phenols, chlorinated paraffins, alkylated naphthalenes, partially hydrogenerated terphenyls, soya bean oil, ester alcohols (e.g., Ektasolve from Eastman Kodak) and mixtures thereof as a solvent for leuco chromogenic compounds.
  • ester alcohols e.g., Ektasolve from Eastman Kodak
  • 5,464,803 and 5,472,489 disclose a mixture of vegetable oil and a mono- or di-functional ester of a fatty acid or other acid composed of a non-aromatic, saturated or unsaturated, straight or branched hydrocarbon chain and a single terminal carboxyl group as a solvent for chromogenic materials in pressure sensitive copying papers.
  • U. S. Patent 3,934,069 discloses dissolving a color precursor in a C 8 to C 30 aliphatic carboxylic acid and diluting this solution with a high boiling aliphatic or araliphatic hydrocarbons, phthalic acid esters of C 3 to C 18 aliphatic alcohols or mixtures thereof as solvent for a dye base.
  • the solvents previously used to solvate chromogenic materials suffer from one or more drawbacks. They may be too slow in print speed, require complex mixtures, be environmentally unfriendly, or they may be irritants to eyes and skin. Certain prior art dye solvents have exhibited adequate print speed and color intensity on the widely used phenolic resin-coated CF sheets. In some cases, however, objectionable odors in the copying systems have been ascribed to the color precursor solvent itself. Such odors obviously detract from commercial acceptance of such copying systems even though the color precursor solvent performance is otherwise superior.
  • an esterified vegetable oils is employed as a solvent for the color precursor used in recording systems such as pressure- sensitive copying systems.
  • These esters are preferably lower alkyl esters such as methyl or ethyl esters.
  • Esterified vegetable oils have been found to provide good solvating ability for the color precursors commonly employed in pressure-sensitive systems.
  • the solvent is used in admixture with a diluent and a cosolvent.
  • the invention further comprises microcapsules useful in pressure-sensitive copying systems, and microcapsule-containing pressure-sensitive copying systems, wherein the microcapsules comprise external encapsulating wall material having encapsulated therein a color precursor and a solvent for chromogenic material in accordance with the invention.
  • the solvents of the present invention are esterified vegetable oils.
  • Esterified vegetable oils are mixtures of esterified fatty acids. Esterified fatty acids can be illustrated by the formula:
  • R 1 is C r C 5 alkyl, C,-C 5 alkenyl, C,-C 5 alkynyl, C 7 -C 20 alkylaryl, C 7 -C 20 arylalkyl or C 6 -C 18 aryl; and R 2 is a C 10 to C 22 saturated or unsaturated hydrocarbon chain.
  • the solvent is a lower alkyl (C1-C5) derived from a vegetable oil such as rapeseed oil, sunflower oil, soybean oil, corn oil, coconut oil, palm kernel oil, palm oil, olive oil, peanut oil, sesame oil, cotton seed oil, safflower oil, linseed oil, castor oil, babasso oil, rung oil, jojoba oil, oiticica oil, and the like, and mixtures thereof.
  • rapeseed oil sunflower oil, soybean oil, corn oil, coconut oil, palm kernel oil, palm oil, olive oil, peanut oil, sesame oil, cotton seed oil, safflower oil, linseed oil, castor oil, babasso oil, rung oil, jojoba oil, oiticica oil, and the like, and mixtures thereof.
  • rapeseed oil sunflower oil, soybean oil, corn oil, coconut oil, palm kernel oil, palm oil, olive oil, peanut oil, sesame oil, cotton seed oil, safflower
  • soybean oil has a basic unsaturated fatty acid combination of 20-25% oleic acid, 48-53% linoleic acid, 5-9% linolenic acid, 3-5% stearic acid, 9-12% palmitic acid, and less than about 1 % myristic, arachidic, palmitoleic and lauric acids.
  • coconut oil contains mainly saturated fatty acids composed of 45-58% lauric acid, 17-20% myristic acid, 6-8% capric acid, 5-9% palmitic acid, 5-7% caprylic acid, 4-8% oleic acid, 2-5% stearic acid, and less than about 1 % arachidic and palmitoleic acids. These oils are esterified for use in the invention.
  • the vegetable oil ester is derived from a liquid fatty acid.
  • the solvent is a lower alkyl ester of coconut oil, rapeseed oil or soybean oil. Most preferably, the solvent is a methyl ester of coconut oil or soybean oil.
  • a particularly preferred solvent is the methyl ester of soybean oil such as SOYGOLD- 1100 available from AG Environmental Products L.L.C.
  • the esterified vegetable oil can be used alone as the sole solvent but typically it is combined with a cosolvent and/or a diluent.
  • the term "diluent" refers to liquids which are not solvents for the color precursor and are otherwise inert with respect to the other components in the microcapsules and the pressure-sensitive copying system.
  • the diluent typically functions to reduce cost.
  • the amount of esterified vegetable oil in the solvent plus diluent mixture ranges from about 10% to 100% by weight and preferably from about 50 to 100%.
  • the solvent mixture comprises about 75% by weight esterified vegetable oil and about 25% by weight diluent.
  • a cosolvent is used with the esterified vegetable oil
  • the diluent can be used in the aforesaid amounts. The addition of the cosolvent merely reduces the amount of the vegetable oil.
  • the diluent typically is kerosene, mineral oil, paraffin oil, mineral spirits or the like.
  • a preferred diluent is a mixture of paraffins such as EXXSOL D-l 10 available from Exxon.
  • Other diluents useful in formulating the internal phase of the microcapsules are described in U.S. Pat. No. 4,684,574 to Pietsch, the contents of which are incorporated herein by reference thereto.
  • cosolvent such as a conventional color precursor solvent in combination with the esterified vegetable oil to decrease cost or to reduce feathering, bleeding or fade.
  • the cosolvent can be used in an amount up to 90% and typically up to 75% and more typically up to 50% based on total solvent-cosolvent mixture.
  • alkylated naphthalenes such as di-isopropylnaphthalene, isobutyl biphenyl, chlorinated alpha-olefin, butyl diphenyl methane, butyl diphenylethane, as well as other biphenyls, naphthalenes, chlorinated compounds, benzene, alkylbezenes and halobenzenes.
  • the internal phase may also contain certain additives specifically intended to alter or control the final properties of the internal phase as for example viscosity control agents, vapor pressure control agents, freezing point depressants, odor masking agents, antioxidants, colored dyes and the like.
  • color precursors include flourans and phthalides in particular.
  • a particularly preferred class of color precursors includes compounds of the phthalide type such as crystal violet lactone (CVL) which is 3,3-bis (p- dimethylaminophenyl) -6-dimethylaminophthalide and malachite green lactone which is 3,3 - bis(p-dimethylamino-phenyl)phthalide.
  • phthalide derived color precursors include 3,3-bis(p-m-dipropylaminophenyl)phthalide, 3,3 -bis(p-methylaminophenyl)phthalide, 3- (phenyl)-3-indole-3-yl)phthalides such as 3-(p-dimethylaminophenyl)-3-(l,2-dimethylindol- 3yl) phthalide, 3,3-bis(phenylindol-3-yl)phthalides such as 3,3-bis-(l,2-dimethylindol-3- yl)phthalide, 3-(phenyl)-3-(heterocyclic-substituted)phthalides such as 3-(p- dimethy laminopheny l)-3 -(1-methy lpy rrol-2-y 1-6-dimethy laminophthalide , indole and carbazole-substituted phthalides such as 3,3 -bis(l,2-
  • color precursors useful in the practice of this invention include indole substituted pyromellitides such as 3,5-bis (p-dimethylaminophenyl) -3,5-bis (1, 2- dimethylindol-3-yl)pyromellitide; 3,7-bis (p-diethylaminophenyl) -3, 7-bis (1,2- dimethylindol-3yl)pycomellitude; 3,3,7,7-tetrakis-(l,2-dimethylindol-3-yl)pyromellitide and 3,3,5,5-tetrakis-(l,2-dimethylindol-3-yl)pyromellitide; and leucauramines and substituted leucauramines such as P-xylyl-leucauramine and phenyl-leucauramine.
  • indole substituted pyromellitides such as 3,5-bis (p-dimethylaminophenyl) -3,5-bis (1,
  • orthohydroxybenzoacetophenone 2,4-bis [p- (p-dimethy laminopheny lazo) aniline] -6-hydroxy-symtrazine; N,3,3-trimethylindolinobenzospiropyrans; and N,3,3- trimethylindolino- beta -naphthospiropiranes.
  • An auxiliary coloring agent can be employed with the above color precursors to provide fade resistance where fading is a problem.
  • Many phthalide compounds such as crystal violet lactone for example, are characterized by rapid color development but have a tendency to fade during the course of time.
  • One suitable auxiliary coloring agent is benzoyl leuco methylene blue which oxidizes when released on the paper to slowly form a permanent blue color.
  • the combination of a phthalide color former and such a colorless oxidizable auxiliary coloring agent provides a composition having both rapid color development and fade resistance.
  • the color precursor is typically dissolved in a selected solvent or solvent/ cosolvent/diluent mixture in an amount of about 2 to 10% by weight.
  • the color developer can be any compound within the definition of a Lewis acid, i.e., an electron acceptor with reference to the chromogen, which promotes the polarization of the chromogen into a colored form.
  • the solid acidic material further serves as an adsorbent of the marking fluid to receive the transferred image.
  • acidic materials include acid clays and acidic organic polymeric materials such as phenolic polymers, phenolacetylene polymers, maleic acid-rosin resins, partially or wholly hydrolyzed styrene-maleic anhydride copolymers and ethylene-maleic anhydride copolymers, carboxy polymethylene and wholly or partially hydrolyzed vinyl methyl ether, maleic anhydride copolymer, salicylates, zincated forms of the aforementioned developers, and mixtures thereof. Superior results are achieved herein with the phenolic type acidic materials, i.e., phenolic resin CF sheet.
  • the internal phase can be microencapsulated according to procedures well known and broadly described in the art.
  • the microcapsules may be produced by coacervation of gelatin and one or more other polymers, e.g. as described in U.S. Pat. Nos. 2,800,457; 2,800,458; or 3,041,289; or by in situ polymerization of polymer precursor material, e.g. as described in U.S. Pat. Nos. 4,001,140; 4,100,103; 4,105,823 and 4,396,670, or by interfacial techniques such as disclosed in U.S. Pat. Nos. 4,379,071; 4,428,983; 4,412,959; 4,402,856; 4,253,682 or 4,181,639.
  • While the carbonless capsule solvent of the present invention has shown many improvements over prior art solvents, in some instances and in some compositions undesirably high permeability through the capsule may be experienced, particularly when a gelatin-type capsule is used. It has been found that this effect may be lessened by using a novel processing method wherein rinse water is pumped into the reactor immediately following emulsification. In this method, as opposed to prior art methods, this rinse water is not recirculated following the initial charge on the belief that the recirculation of the rinse water may worsen capsule permeabilities due to agglomeration of the emulsion droplets. Utilizing this method, permeabilities have been shown to improve in some instances. Furthermore, it has also been found that high capsule permeabilities may be improved by utilizing solvent compositions having a 50% or less concentration of esterified vegetable oil. These improved permeabilities have been realized even when prior art processing methods are used.
  • the pressure-sensitive copying systems utilizing esterified vegetable oils in accordance with the present invention may be prepared according to well known conventional procedures. Descriptions of methods for manufacturing the CB sheet and the CF sheet are to be found in the literature. Coating of the developer coreactant material, whether inorganic clay or organic polymer type, is conducted according to such established procedures. Similarly, formation and application of microcapsules onto the CB sheet is fully disclosed in the literature.
  • the solvents of this invention may be substituted for conventional dye solvents in order to produce improved pressure-sensitive copying systems according to such conventional procedures.
  • esterified vegetable oils as color precursor solvents is illustrated below in Table 1 where image intensity after imaging is reported for carbonless CB sheets made with 100% SOYGOLD-1100 and mixtures of 75% SOYGOLD-1100 and 25% EXXSOLD-110. The intensity is reported as a percentage of the final image intensity.
  • the table shows that the esterified vegetable oil provides over 90% of its final intensity within one-half minute of development as compared to 74-79% for conventional solvent (SAS-310 - a mixture of diphenylalkyls available from Nisseki Chemical Texas Inc.).
  • the invention is also useful in other recording systems which employ encapsulated color precursors such as heat-sensitive and photosensitive systems.
  • the capsules (62%) were mixed with starch binder (12.2%) and stilts (25.8%) to prepare coating compositions which were coated in an amount of 4.9 g/m 2 (or 1.3 lb. bond basis weight) on a base stock to prepare a CB sheet.
  • the CB sheet was assembled with a commercial Trans Rite development (CF) sheet (available from Mead Corporation) and passed through the nip of a pressure roll.
  • the reflectance (%) of the developer sheet was measured 0.25, 0.50, 1, 2 and 5 minutes after development to observe the speed with which the image developed on the developer sheet. The results are shown in Table 3. The lower the reflectance is, the more intense the image.
  • Table 3 shows that a consistent increase in intensity and development speed is achieved with increasing amounts of SOYGOLD 1100 .
  • the capsules were also tested for smudge resistance by rubbing the CB sheets lightly and measuring transmittance 10 minutes later.

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  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Color Printing (AREA)

Abstract

Microcapsules dans lesquelles est encapsulée une phase interne contenant une matière chromogène et un solvant pour la solvatation de la matière chromogène, ledit solvant étant une huile végétale estérifiée.
PCT/US1999/005079 1998-09-23 1999-03-08 Microcapsules contenant du solvant pour de la matiere chromogene WO2000016985A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU29909/99A AU2990999A (en) 1998-09-23 1999-03-08 Microcapsules comprising solvent for chromogenic material

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US15929998A 1998-09-23 1998-09-23
US09/159,299 1998-09-23

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WO2000016985A1 true WO2000016985A1 (fr) 2000-03-30

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US7541119B2 (en) 2007-06-13 2009-06-02 Xerox Corporation Inkless reimageable printing paper and method
US7553603B2 (en) 2007-06-13 2009-06-30 Xerox Corporation Inkless printing paper and method
US7569316B2 (en) 2007-06-13 2009-08-04 Xerox Corporation Inkless reimageable printing paper and method
US7572569B2 (en) 2007-06-13 2009-08-11 Xerox Corporation Inkless printing paper and method
US7572560B2 (en) 2007-06-13 2009-08-11 Xerox Corporation Inkless reimageable printing paper and method
US7582398B2 (en) 2007-06-13 2009-09-01 Xerox Corporation Inkless reimageable printing paper and method
US7588878B2 (en) 2007-06-13 2009-09-15 Xerox Corporation Inkless printing paper and method
US7645558B2 (en) 2007-06-13 2010-01-12 Xerox Corporation Inkless reimageable printing paper and method
US7645560B1 (en) 2008-09-08 2010-01-12 Xerox Corporation Inkless reimageable printing paper and method
US7655366B2 (en) * 2007-06-13 2010-02-02 Xerox Corporation Inkless reimageable printing paper and method
US7666558B2 (en) 2007-06-13 2010-02-23 Xerox Corporation Inkless reimageable printing paper and method
US7718325B2 (en) 2007-06-13 2010-05-18 Xerox Corporation Photochromic material, inkless reimageable printing paper, and methods
EP2065459A3 (fr) * 2007-11-05 2010-08-25 Sunbelt Corporation Formulations liquides de colorants dans des systèmes de solvants non dérivés du pétrole
US7852366B2 (en) 2007-06-13 2010-12-14 Xerox Corporation System and method for printing reimageable transient documents
US7867672B2 (en) 2007-06-13 2011-01-11 Xerox Corporation Reimageable paper protected against UV light

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0520639A1 (fr) * 1991-06-18 1992-12-30 The Wiggins Teape Group Limited Compositions de solvant pour le papier de copie sensible à la pression
EP0593192A2 (fr) * 1992-10-15 1994-04-20 The Wiggins Teape Group Limited Composition chromogène pour l'utilisation dans un matériau d'enregistrement sensible à la pression
EP0633144A1 (fr) * 1993-07-03 1995-01-11 The Wiggins Teape Group Limited Matériau d'enregistrement sensible à la pression
EP0672540A1 (fr) * 1994-03-18 1995-09-20 Bayer Ag Matériau d'enregistrement sensible à la préssion contenant des huiles naturelles ou leur dérivés
EP0697292A1 (fr) * 1994-07-20 1996-02-21 The Wiggings Teape Group Limited Matériau d'enregistrement sensible à la pression
EP0697293A1 (fr) * 1994-07-26 1996-02-21 Copigraph Nouveau solvant organique pour microcapsules utiles notamment pour la réalisation de papier autocopiant sensible à la pression et papier sensible à la pression revêtu de telles microcapsules
WO1999002349A2 (fr) * 1997-07-07 1999-01-21 Cognis Deutschland Gmbh Utilisation d'esters d'alkyle inferieur d'acide gras alcoxyles

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0520639A1 (fr) * 1991-06-18 1992-12-30 The Wiggins Teape Group Limited Compositions de solvant pour le papier de copie sensible à la pression
US5472489A (en) * 1991-06-18 1995-12-05 The Wiggins Teape Group Limited Solvent compositions for use in pressure-sensitive copying paper
EP0593192A2 (fr) * 1992-10-15 1994-04-20 The Wiggins Teape Group Limited Composition chromogène pour l'utilisation dans un matériau d'enregistrement sensible à la pression
EP0633144A1 (fr) * 1993-07-03 1995-01-11 The Wiggins Teape Group Limited Matériau d'enregistrement sensible à la pression
EP0672540A1 (fr) * 1994-03-18 1995-09-20 Bayer Ag Matériau d'enregistrement sensible à la préssion contenant des huiles naturelles ou leur dérivés
EP0697292A1 (fr) * 1994-07-20 1996-02-21 The Wiggings Teape Group Limited Matériau d'enregistrement sensible à la pression
EP0697293A1 (fr) * 1994-07-26 1996-02-21 Copigraph Nouveau solvant organique pour microcapsules utiles notamment pour la réalisation de papier autocopiant sensible à la pression et papier sensible à la pression revêtu de telles microcapsules
WO1999002349A2 (fr) * 1997-07-07 1999-01-21 Cognis Deutschland Gmbh Utilisation d'esters d'alkyle inferieur d'acide gras alcoxyles

Cited By (17)

* Cited by examiner, † Cited by third party
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US7588878B2 (en) 2007-06-13 2009-09-15 Xerox Corporation Inkless printing paper and method
US7553603B2 (en) 2007-06-13 2009-06-30 Xerox Corporation Inkless printing paper and method
US7569316B2 (en) 2007-06-13 2009-08-04 Xerox Corporation Inkless reimageable printing paper and method
US7572569B2 (en) 2007-06-13 2009-08-11 Xerox Corporation Inkless printing paper and method
US7572560B2 (en) 2007-06-13 2009-08-11 Xerox Corporation Inkless reimageable printing paper and method
US7582398B2 (en) 2007-06-13 2009-09-01 Xerox Corporation Inkless reimageable printing paper and method
US7852366B2 (en) 2007-06-13 2010-12-14 Xerox Corporation System and method for printing reimageable transient documents
US7645558B2 (en) 2007-06-13 2010-01-12 Xerox Corporation Inkless reimageable printing paper and method
US7867672B2 (en) 2007-06-13 2011-01-11 Xerox Corporation Reimageable paper protected against UV light
US7655366B2 (en) * 2007-06-13 2010-02-02 Xerox Corporation Inkless reimageable printing paper and method
US7666558B2 (en) 2007-06-13 2010-02-23 Xerox Corporation Inkless reimageable printing paper and method
US7718325B2 (en) 2007-06-13 2010-05-18 Xerox Corporation Photochromic material, inkless reimageable printing paper, and methods
US7541119B2 (en) 2007-06-13 2009-06-02 Xerox Corporation Inkless reimageable printing paper and method
EP2065459A3 (fr) * 2007-11-05 2010-08-25 Sunbelt Corporation Formulations liquides de colorants dans des systèmes de solvants non dérivés du pétrole
US7842102B2 (en) 2007-11-05 2010-11-30 Sunbelt Corporation Liquid dye formulations in non-petroleum based solvent systems
US8529639B2 (en) 2007-11-05 2013-09-10 Sunbelt Corporation Liquid dye formulations in non-petroleum based solvent systems
US7645560B1 (en) 2008-09-08 2010-01-12 Xerox Corporation Inkless reimageable printing paper and method

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