WO1994014902A1 - Hot melt ink jet printing - Google Patents
Hot melt ink jet printing Download PDFInfo
- Publication number
- WO1994014902A1 WO1994014902A1 PCT/GB1993/002629 GB9302629W WO9414902A1 WO 1994014902 A1 WO1994014902 A1 WO 1994014902A1 GB 9302629 W GB9302629 W GB 9302629W WO 9414902 A1 WO9414902 A1 WO 9414902A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- alcohol component
- dihydric
- monohydric
- hot melt
- monohydric alcohol
- Prior art date
Links
Classifications
-
- 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
- C09D11/34—Hot-melt inks
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/2815—Monohydroxy compounds
- C08G18/283—Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds
- C08G18/2835—Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds having less than 5 ether groups
Definitions
- This invention is concerned with improvements in and relating to materials of compositions for use in hot melt ink jet printing processes.
- Ink jet printing generally comprises forming a patterned array of droplets of an ink upon a substrate to form the desired indicia on the substrate.
- the ink is one which is normally solid at ambient temperatures and which is applied to the substrate in molten form so that the droplets solidify on cooling on the substrate.
- the ink employed in hot melt ink jet printing comprises a fusible carrier together"with a colourant, i.e. a pigment or dyestuff.
- a colourant i.e. a pigment or dyestuff.
- Suitable materials for use as or in the vehicles for inks for hot melt ink jet printing should be relatively hard and non-tacky at ambient temperatures whilst being capable of melted to form inks. Suitably, they have a melting point of at least 65°C.
- a wide variety of materials have been proposed for use as vehicles in hot melt inks but there still remains a need for a good, thermally stable material having a relatively sharp melting point. It has now been found, in accordance with the present invention, that there may be used as hot melt ink vehicles reaction products obtained by reacting a diisocyanate with one or more monohydric alcohols, optionally in combination with a dihydric alcohol.
- a material suitable for use as a vehicle in a hot melt ink having a melting point of at least 65°C and obtainable by reacting an aliphatic or aromatic diisocyanate with an at least stoichiometric amount of:
- the monohydric alcohol component(s) comprising a monohydric aliphatic alcohol or an etherified or esterified dihydric aliphatic alcohol or dihydric polyalkylene glycol; and the dihydric alcohol component comprising a dihydric aliphatic alcohol or a dihydric polyalkylene glycol and being used in an amount not more than 50% of the stoichiometric amount of hydroxyl groups required to react with the isocyanate groups on the diisocyanate.
- the material obtained (hereinafter simply referred to as an "oligourethane") have a melting point of at least 65°C (The term 'melting point' as used herein means the melting point as determined by the ball and ring method) . It should be noted that by no means all materials obtainable in accordance with the process outlined above will have melting points of at least 65°C. Our experiments have shown that there is wide variation in melting point and attempts to predict whether a particular reaction product will have the desired melting point, for ' example having regard to the molecular weight of the component reactants or the possible molecular weight of the final product, simply do not yield meaningful results. However, of course, to determine the melting point of any particular material is a matter for simple routine experiment and trial.
- Suitable diisocyanates for use in the preparation of the oligourethane include toluene diisocyanate, diphenylmethane-4,4' -diisocyanate (MDI) , hexamethylene- 1,6-diisocyanate, napthylene-1,5-diisocyanate, 3,3' -dimethoxy-4,4' -biphenyldiisocyanate, 3,3' - dimethyl-4,4' -biphenyldiisocyanate, phenylene di ⁇ isocyanate, 4,4' -biphenyldiisocyanate, isophorone di ⁇ isocyanate (IPDI) , trimethylhexamethylene diisocyanate,and tetramethylene xylene diisocyanate.
- the aromatic diisocyanates are generally preferred and, in particular, isophorone diisocyanate has been found to give particularly useful oli
- a wide variety of monohydric aliphatic alcohols may be used to produce the oligourethanes, e.g. C to C_ 2 alcohols.
- Typical etherified dihydric alcoholic materials which may be used as monohydric alcoholic component include propylene glycol methyl ether (PGME) , dipropylene glycol methyl ether (DPGME) , ethylene glycol butyl ether (EGBE) , diethylene glycol butyl ether (DPGBE) , tripropylene glycol butyl ether (TPGBE) and propylene glycol phenyl ether (PPL) .
- PGME propylene glycol methyl ether
- DPGME dipropylene glycol methyl ether
- EGBE ethylene glycol butyl ether
- DGBE diethylene glycol butyl ether
- TPGBE tripropylene glycol butyl ether
- PPL propylene glycol phenyl ether
- the esterifying acid may be an ethylenically unsaturated acid (such as acrylic acid or methacrylic acid) , thereby introducing ethylenic unsaturation into the oligourethane and rendering it suitable for eventual further addition polymerisation (curing) after having been applied to a substrate by hot melt printing.
- Dihydric alcohols may be used include, for example, alcohols, ethylene glycol, polyethylene glycol (PEG 1500), polypropylene glycol (PPG 750, 1000 and 1500), trimethylene glycol, dipropylene glycol,methyl- propanediol and 1,6-hexanediol.
- the reaction between diurethane and monohydric/dihydric alcohol component is suitably carried out in the presence of a catalyst such as cobalt benzoate, lithium acetate, stannous octoate, ethylamine and dibutyl tin dilaurate.
- a catalyst such as cobalt benzoate, lithium acetate, stannous octoate, ethylamine and dibutyl tin dilaurate.
- the molecular weight of the final oligourethane is suitably from 250 to 2000,preferably from 250-750.
- the vehicles, the oligourethanes be clear. Again, it is virtually impossible to predict whether any particular oligourethane produced in accordance with the invention will, or will not, have the desired optical properties in this respect. However, here again it is a matter of simple routine trial and experiment and many of the oligourethanes do have the desired optical properties. Similarly, it is generally desirable that the oligourethanes should have relatively low viscosities (e.g. less than 50 cp at 125°C) and, here again, it is difficult to make predictions as to the viscosity of any particular oligourethane material.
- the oligourethanes of the invention are used as vehicles, or components of the vehicles, of hot melt inks and, in addition to the oligourethanes, such inks will generally comprise colourants such as pigments or dyestuffs. Further, other conventional additives such as antioxidants etc, may also be present.
- the vehicle (oligourethane) will form from 80 to 95% by weight, especially 90 to 95% by weight of any ink with viscosity and compatibility improving additives forming the bulk of the remainder and the other additives (colorants, etc.) being present in relatively small amounts, e.g. to a total of ' not more than 10% by weight of the ink.
- IPDI isophorone diisocyanate
- l g of dibutyl tin dila rate were charged to a dry, round bottomed reaction flask fitted with a stirrer and thermometer and heated, under an inert atmosphere, to 40°C.
- 240 g of isopropanol were slowly added to the mixture over a period of 3 hours, the reaction mixture being cooled to 60°C during this addition. Once a stable temperature of 60°C had been reached, the reaction mixture was heated to 110°C and maintained at this temperature until the residual isocyanate value had dropped to less than 30 PPM. The molten di-urethane was then discharged and allowed to cool.
- the material produced was a transparent, water white and tack-free solid with a ball and ring melting point of 71°C and a viscosity of 40 centipoise at 125°C (measured on an REL cone and plate viscometer) .
- the material displayed excellent stablity under hot conditions, remaining unchanged in clarity or viscosity after storage at 150°C for seven days.
- the reaction mixture was maintained at a temperature of 70°C by cooling. Once a steady temperature had been attained, 162 g of octadecanol were added and the batch carefully heated to 100°C. This temperature was then maintained until the residual isocyanate value had fallen below 30 ppm. The molten material was then discharged onto a tray to cool.
- the acrylate functional diurethane obtained was an opaque, tack-free solid with a ball and ring melting point of 95°C and a viscosity of 30 centipoise at 125°C (measured as an in Example 1) .
- the reaction mixture was held at this temperature until the residual isocyanate value had fallen below 30 ppm.
- the molten oligourethane was discharged to a tray to cool.
- the material produced was a transparent, water-white, tack-free solid with a melting point of 102°C and a viscosity of 50 centipoise at 125°C.
- IPDI/t-butanol (1.50) /octadecanol (0.50); IPDE/PPh (2.00) ; IPDEI/t-butanol (2.00).
- the resulting clear yellow fluid was filtered through a 5 micron filter when cooled a translucent yellow solid with a viscosity of 55 centipoise at 1250°C was produced.
- a translucent yellow solid with a viscosity of 55 centipoise at 1250°C was produced.
- the ink When applied by thermal ink jet printing and by heated drawdown bar onto polyester (Mylar) sheet the ink showed excellent adhesion and resistance to flexing, but was slightly tacky.
- the ink was passed through a UV cure unit (to give it a cure of 1500 mJ/cm ) the surface became tack free, with improved rub resistance.
- the cured film was translucent.
- the oligourethane produced by the method described in Example 3 was heated to 140°C and mixed, using a silverson high speed stirrer, with stearamide (crodamide SR, Croda Ltd) , 5% w/w, stearone (5% w/w) and methylene blue dye (0.05% w/w) until a homogenous blue liquid was produced.
- This liquid was filtered through a 5 micron filter and cooled to give a clear blue solid ink with a viscosity of 25 centipoise at 125°C.
- This ink when applied to a polyester film substrate using a hot ink jet printer or a heated draw down bar coater gave a transparent blue film with good light transparency, adhesion and crease resistance.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
Description
Claims
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP94902935A EP0675927A1 (en) | 1992-12-23 | 1993-12-22 | Hot melt ink jet printing |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB9226772.3 | 1992-12-23 | ||
GB929226772A GB9226772D0 (en) | 1992-12-23 | 1992-12-23 | Hot melt ink jet printing |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1994014902A1 true WO1994014902A1 (en) | 1994-07-07 |
Family
ID=10727072
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/GB1993/002629 WO1994014902A1 (en) | 1992-12-23 | 1993-12-22 | Hot melt ink jet printing |
Country Status (3)
Country | Link |
---|---|
EP (1) | EP0675927A1 (en) |
GB (1) | GB9226772D0 (en) |
WO (1) | WO1994014902A1 (en) |
Cited By (66)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1996014364A1 (en) * | 1994-11-08 | 1996-05-17 | Coates Brothers Plc | Hot melt ink jet printing |
WO1997012003A1 (en) * | 1995-09-27 | 1997-04-03 | Coates Brothers Plc | Hot melt ink jet vehicles |
EP0816448A1 (en) * | 1996-06-28 | 1998-01-07 | Tektronix, Inc. | Phase change ink formulation using a urethane isocyanate-derived resin |
US5750604A (en) * | 1996-06-28 | 1998-05-12 | Tektronix, Inc. | Phase change ink formulation using a urethane isocyanate-derived resin |
US5777023A (en) * | 1996-10-01 | 1998-07-07 | Union Camp Corporation | Diamidediurethanes and hot-melt printing therewith |
US5780528A (en) * | 1996-06-28 | 1998-07-14 | Tektronix, Inc. | Isocyanate-derived colored resins for use in phase change ink jet inks |
US5783658A (en) * | 1996-06-28 | 1998-07-21 | Tektronix, Inc. | Phase change ink formulation using a urethane isocyanate-derived resin and a urethane isocyanate-derived wax |
US5782966A (en) * | 1996-06-28 | 1998-07-21 | Tektronix, Inc. | Isocyanate-derived materials for use in phase change ink jet inks |
US5827918A (en) * | 1996-06-28 | 1998-10-27 | Tektronix, Inc. | Phase change ink formulation using urea and urethane isocyanate-derived resins |
US5830942A (en) * | 1996-06-28 | 1998-11-03 | Tektronix, Inc. | Phase change ink formulation using a urethane and urethane/urea isocyanate-derived resins |
US5919839A (en) * | 1996-06-28 | 1999-07-06 | Tektronix, Inc. | Phase change ink formulation using an isocyanate-derived wax and a clear ink carrier base |
EP0931673A2 (en) * | 1998-01-26 | 1999-07-28 | Tektronix, Inc. | Phase change inks and methods of printing |
EP0936256A1 (en) * | 1998-02-13 | 1999-08-18 | Tektronic Inc | Phase change ink formulation using urethane isocyanate-derived resins |
EP0936257A1 (en) * | 1998-02-13 | 1999-08-18 | Tektronic Inc | Phase change ink formulation using urethane isocyanate-derived resins and a toughening agent |
US6015847A (en) * | 1998-02-13 | 2000-01-18 | Tektronix, Inc. | Magenta phase change ink formulation containing organic sulfonic acid |
US6048925A (en) * | 1996-06-28 | 2000-04-11 | Xerox Corporation | Urethane isocyanate-derived resins for use in a phase change ink formulation |
US6133353A (en) * | 1999-11-11 | 2000-10-17 | 3D Systems, Inc. | Phase change solid imaging material |
US6180692B1 (en) | 1996-06-28 | 2001-01-30 | Xerox Corporation | Phase change ink formulation with organoleptic maskant additive |
EP1085063A2 (en) * | 1999-09-20 | 2001-03-21 | Xerox Corporation | Colorless compounds, solid inks, and printing methods |
US6270561B1 (en) | 1999-10-15 | 2001-08-07 | American Dye Source, Inc. | Hot melt ink compositions for inkjet printing applications |
US6395811B1 (en) | 1999-11-11 | 2002-05-28 | 3D Systems, Inc. | Phase change solid imaging material |
US6730150B1 (en) | 1996-06-28 | 2004-05-04 | Xerox Corporation | Phase change ink formulation containing a combination of a urethane resin, a mixed urethane/urearesin, a mono-amide and a polyethylene wax |
US6759450B2 (en) | 2001-10-26 | 2004-07-06 | Milliken & Company | Toned black offset inks exhibiting excellent chromatic characteristics |
US6960248B2 (en) | 2003-05-22 | 2005-11-01 | Arizona Chemical Company | Cyclic bisamides useful in formulating inks for phase-change printing |
US7022879B2 (en) | 1996-06-28 | 2006-04-04 | Xerox Corporation | Phase change ink formulations, colorant formulations, and methods of forming colorants |
US7084189B2 (en) | 2003-02-20 | 2006-08-01 | Xerox Corporation | Phase change inks with isocyanate-derived antioxidants and UV stabilizers |
ES2294965A1 (en) * | 2007-05-07 | 2008-04-01 | Antonio Oliva Gurgui | Urethane and oligourethane derivatives and corresponding uses and methods for producing water marks using the offset printing technique |
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EP1961794A1 (en) | 2007-02-06 | 2008-08-27 | Xerox Corporation | Phase change inks containing colorant compounds |
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US7449515B2 (en) | 2005-11-30 | 2008-11-11 | Xerox Corporation | Phase change inks containing compounds derived from isocyanate, unsaturated alcohol, and polyol |
EP2000514A1 (en) | 2007-05-30 | 2008-12-10 | Xerox Corporation | Solid Ink Set Incorporating Naturally Derived Materials and Processes Thereof |
US7541406B2 (en) | 2005-11-30 | 2009-06-02 | Xerox Corporation | Phase change inks containing curable isocyanate-derived compounds |
EP2107088A1 (en) | 2008-04-03 | 2009-10-07 | Xerox Corporation | Phase change inks containing Fischer-Tropsch Waxes |
EP2130879A1 (en) | 2008-06-02 | 2009-12-09 | Xerox Corporation | Flush pigment for solid inkjet ink |
US7674842B2 (en) | 2005-11-30 | 2010-03-09 | Xerox Corporation | Phase change inks containing curable isocyanate-derived compounds and phase change inducing components |
US7749315B2 (en) | 2007-04-04 | 2010-07-06 | Xerox Corporation | Phase change inks containing colorant compounds |
US7758268B2 (en) | 2005-12-20 | 2010-07-20 | Xerox Corporation | Hand held photochromic marking implement |
US7811368B2 (en) | 2007-04-04 | 2010-10-12 | Xerox Corporation | Phase change inks containing colorant compounds |
EP2253680A1 (en) | 2009-05-18 | 2010-11-24 | Xerox Corporation | Pigmented phase change inks containing low molecular weight quaternary ammonium salt dispersants |
EP2253611A1 (en) | 2009-05-18 | 2010-11-24 | Xerox Corporation | Low molecular weight quaternary ammonium salt dispersants |
EP2261291A1 (en) | 2009-06-10 | 2010-12-15 | Xerox Corporation | Solid or phase change inks with improved properties |
US8029861B2 (en) | 2008-09-23 | 2011-10-04 | Xerox Corporation | Ink carriers containing low viscosity functionalized waxes, phase change inks including same, and methods for making same |
US8123344B2 (en) | 2008-08-04 | 2012-02-28 | Xerox Corporation | Ink carriers containing surface modified nanoparticles, phase change inks including same, and methods for making same |
US8177897B2 (en) | 2008-11-17 | 2012-05-15 | Xerox Corporation | Phase change inks containing graphene-based carbon allotrope colorants |
US8348409B2 (en) | 2008-11-17 | 2013-01-08 | Xerox Corporation | Ink jet inks containing nanodiamond black colorants |
US8360546B2 (en) | 2010-12-22 | 2013-01-29 | Xerox Corporation | Phase change magnetic ink and process for preparing same |
US8544999B2 (en) | 2010-12-22 | 2013-10-01 | Xerox Corporation | Phase change magnetic ink and process for preparing same |
US8616693B1 (en) | 2012-11-30 | 2013-12-31 | Xerox Corporation | Phase change ink comprising colorants derived from plants and insects |
US8647422B1 (en) | 2012-11-30 | 2014-02-11 | Xerox Corporation | Phase change ink comprising a modified polysaccharide composition |
US8646896B2 (en) | 2011-03-17 | 2014-02-11 | Xerox Corporation | Phase change magnetic ink comprising surfactant coated magnetic nanoparticles and process for preparing same |
US8657431B2 (en) | 2011-03-17 | 2014-02-25 | Xerox Corporation | Phase change magnetic ink comprising carbon coated magnetic nanoparticles and process for preparing same |
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US8714724B2 (en) | 2012-10-02 | 2014-05-06 | Xerox Corporation | Phase change inks containing novel synergist |
US8791202B2 (en) | 2007-09-21 | 2014-07-29 | Xerox Corporation | Phase change ink compositions |
US8911543B2 (en) | 2012-12-18 | 2014-12-16 | Xerox Corporation | Phenylcyclohexanol derivatives as wax modifiers and gelators |
US8974047B2 (en) | 2012-11-27 | 2015-03-10 | Xerox Corporation | Phase change ink containing ethylene vinyl acetate |
US8980406B2 (en) | 2012-08-28 | 2015-03-17 | 3D Systems, Inc. | Color stable inks and applications thereof |
US9090777B2 (en) | 2013-04-04 | 2015-07-28 | Xerox Corporation | Low cost process for solid ink using dry flushed pigments |
US9090758B2 (en) | 2012-11-30 | 2015-07-28 | Xerox Corporation | Phase change ink comprising modified naturally-derived colorants |
US9157002B2 (en) | 2013-07-12 | 2015-10-13 | Xerox Corporation | Phase change ink pigment dispersion process |
US9410051B2 (en) | 2014-09-25 | 2016-08-09 | Markem-Imaje Corporation | Hot melt inks |
US9657186B2 (en) | 2012-09-13 | 2017-05-23 | 3D Systems, Inc. | Opaque inks and applications thereof |
US9944806B2 (en) | 2014-09-25 | 2018-04-17 | Markem-Imaje Corporation | Urethane compounds |
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-
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- 1993-12-22 WO PCT/GB1993/002629 patent/WO1994014902A1/en not_active Application Discontinuation
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Cited By (99)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1996014364A1 (en) * | 1994-11-08 | 1996-05-17 | Coates Brothers Plc | Hot melt ink jet printing |
US6255432B1 (en) | 1995-09-27 | 2001-07-03 | Coates Brothers Plc | Hot melt ink jet vehicles |
WO1997012003A1 (en) * | 1995-09-27 | 1997-04-03 | Coates Brothers Plc | Hot melt ink jet vehicles |
US6180692B1 (en) | 1996-06-28 | 2001-01-30 | Xerox Corporation | Phase change ink formulation with organoleptic maskant additive |
US7520222B2 (en) | 1996-06-28 | 2009-04-21 | Xerox Corporation | Phase change ink formulation containing a combination of a urethane resin, a mixed urethane/urearesin, a mono-amide and a polyethylene wax |
EP0816445A1 (en) * | 1996-06-28 | 1998-01-07 | Tektronix, Inc. | Isocyanate-derived materials for use in phase change ink jet inks |
EP0816446A1 (en) * | 1996-06-28 | 1998-01-07 | Tektronix, Inc. | Phase change ink formulation using a urethane and urethane urea isocyanate derived resins |
US5750604A (en) * | 1996-06-28 | 1998-05-12 | Tektronix, Inc. | Phase change ink formulation using a urethane isocyanate-derived resin |
US6730150B1 (en) | 1996-06-28 | 2004-05-04 | Xerox Corporation | Phase change ink formulation containing a combination of a urethane resin, a mixed urethane/urearesin, a mono-amide and a polyethylene wax |
US5780528A (en) * | 1996-06-28 | 1998-07-14 | Tektronix, Inc. | Isocyanate-derived colored resins for use in phase change ink jet inks |
US5783658A (en) * | 1996-06-28 | 1998-07-21 | Tektronix, Inc. | Phase change ink formulation using a urethane isocyanate-derived resin and a urethane isocyanate-derived wax |
US5782966A (en) * | 1996-06-28 | 1998-07-21 | Tektronix, Inc. | Isocyanate-derived materials for use in phase change ink jet inks |
US5827918A (en) * | 1996-06-28 | 1998-10-27 | Tektronix, Inc. | Phase change ink formulation using urea and urethane isocyanate-derived resins |
US5830942A (en) * | 1996-06-28 | 1998-11-03 | Tektronix, Inc. | Phase change ink formulation using a urethane and urethane/urea isocyanate-derived resins |
US7022879B2 (en) | 1996-06-28 | 2006-04-04 | Xerox Corporation | Phase change ink formulations, colorant formulations, and methods of forming colorants |
US5919839A (en) * | 1996-06-28 | 1999-07-06 | Tektronix, Inc. | Phase change ink formulation using an isocyanate-derived wax and a clear ink carrier base |
US7985865B2 (en) | 1996-06-28 | 2011-07-26 | Xerox Corporation | Phase change ink formulations, colorant formulations, and methods of forming colorants |
EP0816449A1 (en) * | 1996-06-28 | 1998-01-07 | Tektronix, Inc. | Phase change ink formulation using urea and urethane isocyanante derived resins |
US6620228B1 (en) | 1996-06-28 | 2003-09-16 | Xerox Corporation | Isocyanate-derived materials for use in phase change ink jet inks |
US7064230B2 (en) | 1996-06-28 | 2006-06-20 | Xerox Corporation | Phase change ink formulation containing a combination of a urethane resin, a mixed urethane/urearesin, a mono-amide and a polyethylene wax |
US5994453A (en) * | 1996-06-28 | 1999-11-30 | Tektronix, Inc. | Phase change ink formulation containing a combination of a urethane resin, a mixed urethane/urea resin, a mono-amide and a polyethylene wax |
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