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WO1996014364A1 - Impression a jets d'encre thermofusible - Google Patents

Impression a jets d'encre thermofusible Download PDF

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Publication number
WO1996014364A1
WO1996014364A1 PCT/GB1995/002572 GB9502572W WO9614364A1 WO 1996014364 A1 WO1996014364 A1 WO 1996014364A1 GB 9502572 W GB9502572 W GB 9502572W WO 9614364 A1 WO9614364 A1 WO 9614364A1
Authority
WO
WIPO (PCT)
Prior art keywords
primary
component
followed
hot melt
secondary monoamine
Prior art date
Application number
PCT/GB1995/002572
Other languages
English (en)
Inventor
Philippa Catherine Evans
Stephen Anthony Hall
Nicholas Eric Ivory
Original Assignee
Coates Brothers Plc
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 Coates Brothers Plc filed Critical Coates Brothers Plc
Priority to AU38103/95A priority Critical patent/AU3810395A/en
Publication of WO1996014364A1 publication Critical patent/WO1996014364A1/fr

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

Definitions

  • This invention is concerned with improvements in and relating to materials or 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.
  • reaction products obtained by reacting a monoisocyanate or diisocyanate with one or more primary or secondary monoamine optionally in combination with a diprimary diamine.
  • 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 mono- or di- isocyanate with an at least stoichiometric amount of:
  • oligourea a primary or secondary monoamine component, followed by an alcohol component; the diprimary diamine being used in an amount not more than 50% of the stoichiometric amount of amine groups required to react with the isocyanate group(s) on the isocyanate.
  • oligourea the material obtained (hereinafter simply referred to as an "oligourea”) 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 not all materials obtainable in accordance with the process outlined above will have melting points of at least 65°C.
  • Suitable isocyanates for use in the preparation of the oligourea include octadecylmonoisocyanate, 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) , dicyclohexylmethane 4,4' -diisocyanate, trimethylhexamethylene diisocyanate,and tetramethylene xylene diisocyanate.
  • IPDI is
  • the aliphatic diisocyanates are generally preferred and, in particular, isophorone diisocyanate, trimethylhexa- methylene diisocyanate and octadecylmonoisocyanate have been found to give particularly useful oligoureas.
  • a wide variety of primary and secondary amines may be used to produce the oligoureas, e.g. C. to C ? _ monoamines such as ethylamine, octylamine, hexadecylamine, octadecylamine, di-n-butylamine, neopentadiamine, di-n-tallow-amine, di-n-cocoamine and N-methyloctadecylamine.
  • monoamines such as ethylamine, octylamine, hexadecylamine, octadecylamine, di-n-butylamine, neopentadiamine, di-n-tallow-amine, di-n-cocoamine and N-methyloctadecylamine.
  • Suitable diprimary diamines include isophorone diamine, neopentane diamine, hexamethylene diamine, ethylene diamine, polyoxypropylene diamines, 2-methylpentamethylene diamine and 1,12-dodecane diamine.
  • the reaction between the isocyanate and the amine component is usually carried out in the absence of a catalyst, but catalysts such as dibutyl tin dilaurate and stannous octoate may be used to ensure that the reaction reaches completion.
  • the molecular weight of the final oligourea is suitably from 250 to 2000,preferably from 250-750.
  • the vehicles, the oligoureas be clear. Again, it is virtually impossible to predict whether any particular oligourea 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 oligoureas do have the desired optical properties.
  • the oligoureas should have relatively low viscosities (e.g. less than 200 cp at 125°C) and, here again, it is difficult to make predictions as to the viscosity of any particular oligourea material.
  • the oligoureas of the invention are used as vehicles, or components of the vehicles, of hot melt inks and, in addition to the oligoureas, 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 (oligourea) 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.
  • the following Examples are given by way of illustration only.
  • the resulting product had a ball and ring melting point; of 105°C a relative viscosity of 190 cp.; and was clear and stable at elevated temperature.
  • Example 3 1.6 molar parts of hexadecylamine, 0.4 molar parts of di-n-tallaow amine and 1 molar part of trimethylhexamethylene diisocyanate were reacted following the procedure described in Example 1. The resulting product had a ball and ring melting point of 79°C and a relative viscosity of 140 cp. The product was translucent and heat stable.
  • Example 3
  • Octadecylamine, octadecanol and trimethylhexamethylene diisocyanate were reacted in accordance with the procedure described in Example 1 except that stannous octoate was used as catalyst when adding the alcohol component to the reaction mixture.
  • the resulting product had a ball and ring melting point of 101°C and relative viscosity of 140 cp. It was a translucent product which was heat stable.
  • Example 2 2 molar parts of octadecylmonoisocyanate and 1 molar part of neopentadiamine were reacted following the procedure described in Example 1 to give a product having a ball ring melting point of 80°C and a relative viscosity of 10 cp.
  • the product was translucent and heat stable.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

Un matériau approprié destiné à être utilisé dans une encre thermofusible a point de fusion d'au moins 65 °C et peut être obtenu par la réaction d'un mono- ou diisocyanate aliphatique ou aromatique avec au moins une quantité stoïchiométrique de: (i) un composant monoamine primaire ou secondaire; ou (ii) un composant monoamine primaire ou secondaire suivi d'un autre composant monoamine primaire différent; ou (iii) un composant monoamine primaire ou secondaire suivi d'un composant diamine diprimaire et d'un composant monoamine primaire ou secondaire; ou (iv) un composant monoamine primaire ou secondaire suivi d'un composant d'alcool; le composant diamine diprimaire étant utilisé dans une quantité ne dépassant pas 50 % de la quantité stoïchiométrique des groupes amine nécessaires pour réagir avec le(s) groupe(s) isocyanate du diisocyanate.
PCT/GB1995/002572 1994-11-08 1995-11-01 Impression a jets d'encre thermofusible WO1996014364A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU38103/95A AU3810395A (en) 1994-11-08 1995-11-01 Hot melt ink jet printing

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9422477A GB2294939A (en) 1994-11-08 1994-11-08 Hot melt ink jet printing composition comprising an oligourea
GB9422477.1 1994-11-08

Publications (1)

Publication Number Publication Date
WO1996014364A1 true WO1996014364A1 (fr) 1996-05-17

Family

ID=10764041

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB1995/002572 WO1996014364A1 (fr) 1994-11-08 1995-11-01 Impression a jets d'encre thermofusible

Country Status (3)

Country Link
AU (1) AU3810395A (fr)
GB (1) GB2294939A (fr)
WO (1) WO1996014364A1 (fr)

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EP1935950A1 (fr) 2006-12-18 2008-06-25 Xerox Corporation Encres de changement de phase contenant des éthers de dialkyle
EP1961793A1 (fr) 2007-02-06 2008-08-27 Xerox Corporation Encres de changement de phase contenant des composés de colorants
EP2000514A1 (fr) 2007-05-30 2008-12-10 Xerox Corporation Ensemble d'encre solide incorporant des matériaux naturellement dérivés et procédés associés
EP2107088A1 (fr) 2008-04-03 2009-10-07 Xerox Corporation Encres à changement de phase contenant des cires de Fischer-Tropsch
EP2130879A1 (fr) 2008-06-02 2009-12-09 Xerox Corporation Pigment par voie humide pour encre ? jet d'encre solide
US7758268B2 (en) 2005-12-20 2010-07-20 Xerox Corporation Hand held photochromic marking implement
EP2253680A1 (fr) 2009-05-18 2010-11-24 Xerox Corporation Encres de changement de phase pigmentées contenant des dispersants de sel d'ammonium quaternaire à faible poids moléculaire
EP2253611A1 (fr) 2009-05-18 2010-11-24 Xerox Corporation Dispersants de sel d'ammonium quaternaire à faible poids moléculaire
EP2261291A1 (fr) 2009-06-10 2010-12-15 Xerox Corporation Encres solides ou en phase avec des propriétés améliorées
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
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
US8696100B1 (en) 2012-10-02 2014-04-15 Xerox Corporation Phase change ink containing synergist for pigment dispersion
US8714724B2 (en) 2012-10-02 2014-05-06 Xerox Corporation Phase change inks containing novel synergist
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
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

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US5750604A (en) * 1996-06-28 1998-05-12 Tektronix, Inc. Phase change ink formulation using a urethane isocyanate-derived resin
US6018005A (en) * 1996-06-28 2000-01-25 Tektronix, Inc. Phase change ink formulation using urethane isocyanate-derived resins and a polyethylene wax
US5830942A (en) * 1996-06-28 1998-11-03 Tektronix, Inc. Phase change ink formulation using a urethane and urethane/urea isocyanate-derived resins
US6180692B1 (en) 1996-06-28 2001-01-30 Xerox Corporation Phase change ink formulation with organoleptic maskant additive
US5780528A (en) * 1996-06-28 1998-07-14 Tektronix, Inc. Isocyanate-derived colored resins for use in phase change ink jet inks
EP0816447B1 (fr) * 1996-06-28 2003-09-10 Xerox Corporation Formulation d'encre à changement de phase en utilisant une résine d'uréthane et de cire dérivée d'isocyanate
US6028138A (en) * 1996-06-28 2000-02-22 Tektronix, Inc. Phase change ink formulation using urethane isocyanate-derived resins, a polyethylene wax and toughening agent
US5827918A (en) * 1996-06-28 1998-10-27 Tektronix, Inc. Phase change ink formulation using urea and urethane isocyanate-derived resins
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
US6048925A (en) * 1996-06-28 2000-04-11 Xerox Corporation Urethane isocyanate-derived resins for use in a phase change ink formulation
US5782966A (en) * 1996-06-28 1998-07-21 Tektronix, Inc. Isocyanate-derived materials 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
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
US6015847A (en) * 1998-02-13 2000-01-18 Tektronix, Inc. Magenta phase change ink formulation containing organic sulfonic acid
US6133353A (en) 1999-11-11 2000-10-17 3D Systems, Inc. Phase change solid imaging material
US6395811B1 (en) 1999-11-11 2002-05-28 3D Systems, Inc. Phase change solid imaging material
US6860930B2 (en) 2003-06-25 2005-03-01 Xerox Corporation Phase change inks containing branched triamides
US20080187664A1 (en) 2007-02-06 2008-08-07 Xerox Corporation Phase change inks containing colorant compounds
US7997712B2 (en) 2007-02-06 2011-08-16 Xerox Corporation Phase change inks containing colorant compounds
US8163074B2 (en) 2007-02-06 2012-04-24 Xerox Corporation Phase change inks containing colorant compounds
US7749315B2 (en) 2007-04-04 2010-07-06 Xerox Corporation Phase change inks containing colorant compounds
US7811368B2 (en) 2007-04-04 2010-10-12 Xerox Corporation Phase change inks containing colorant compounds
US8791202B2 (en) 2007-09-21 2014-07-29 Xerox Corporation Phase change ink compositions
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
US8646896B2 (en) 2011-03-17 2014-02-11 Xerox Corporation Phase change magnetic ink comprising surfactant coated magnetic nanoparticles and process for preparing same
US8702217B2 (en) 2011-03-17 2014-04-22 Xerox Corporation Phase change magnetic ink comprising polymer 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
US8980406B2 (en) 2012-08-28 2015-03-17 3D Systems, Inc. Color stable inks and applications thereof
US9657186B2 (en) 2012-09-13 2017-05-23 3D Systems, Inc. Opaque inks and applications thereof
US9422440B2 (en) * 2013-12-06 2016-08-23 Xerox Corporation Bis-ureas as amorphous materials for phase-change ink

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JPS62179580A (ja) * 1986-01-31 1987-08-06 Asahi Chem Ind Co Ltd ワツクス状組成物
EP0404493A2 (fr) * 1989-06-22 1990-12-27 Xerox Corporation Composition d'encre thermofusible
WO1994014902A1 (fr) * 1992-12-23 1994-07-07 Coates Brothers Plc Impression a jet d'encre thermofusible

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JP3206094B2 (ja) * 1992-03-16 2001-09-04 株式会社リコー ホットメルトインク組成物及びこれを用いた記録方法

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JPS62179580A (ja) * 1986-01-31 1987-08-06 Asahi Chem Ind Co Ltd ワツクス状組成物
EP0404493A2 (fr) * 1989-06-22 1990-12-27 Xerox Corporation Composition d'encre thermofusible
WO1994014902A1 (fr) * 1992-12-23 1994-07-07 Coates Brothers Plc Impression a jet d'encre thermofusible

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US7758268B2 (en) 2005-12-20 2010-07-20 Xerox Corporation Hand held photochromic marking implement
EP1935950A1 (fr) 2006-12-18 2008-06-25 Xerox Corporation Encres de changement de phase contenant des éthers de dialkyle
EP1961793A1 (fr) 2007-02-06 2008-08-27 Xerox Corporation Encres de changement de phase contenant des composés de colorants
EP2000514A1 (fr) 2007-05-30 2008-12-10 Xerox Corporation Ensemble d'encre solide incorporant des matériaux naturellement dérivés et procédés associés
US7677713B2 (en) 2007-05-30 2010-03-16 Xerox Corporation Solid ink set incorporating naturally derived materials and processes thereof
EP2107088A1 (fr) 2008-04-03 2009-10-07 Xerox Corporation Encres à changement de phase contenant des cires de Fischer-Tropsch
EP2130879A1 (fr) 2008-06-02 2009-12-09 Xerox Corporation Pigment par voie humide pour encre ? jet d'encre solide
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
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
US8348409B2 (en) 2008-11-17 2013-01-08 Xerox Corporation Ink jet inks containing nanodiamond black colorants
US8177897B2 (en) 2008-11-17 2012-05-15 Xerox Corporation Phase change inks containing graphene-based carbon allotrope colorants
US8118922B2 (en) 2009-05-18 2012-02-21 Xerox Corporation Pigmented phase change inks containing low molecular weight quaternary ammonium salt dispersants
EP2253680A1 (fr) 2009-05-18 2010-11-24 Xerox Corporation Encres de changement de phase pigmentées contenant des dispersants de sel d'ammonium quaternaire à faible poids moléculaire
US8101801B2 (en) 2009-05-18 2012-01-24 Xerox Corporation Low molecular weight quaternary ammonium salt dispersants
EP2253611A1 (fr) 2009-05-18 2010-11-24 Xerox Corporation Dispersants de sel d'ammonium quaternaire à faible poids moléculaire
US8915993B2 (en) 2009-06-10 2014-12-23 Xerox Corporation Solid or phase change inks with improved properties
EP2261291A1 (fr) 2009-06-10 2010-12-15 Xerox Corporation Encres solides ou en phase avec des propriétés améliorées
US8696100B1 (en) 2012-10-02 2014-04-15 Xerox Corporation Phase change ink containing synergist for pigment dispersion
US8714724B2 (en) 2012-10-02 2014-05-06 Xerox Corporation Phase change inks containing novel synergist
US8974047B2 (en) 2012-11-27 2015-03-10 Xerox Corporation Phase change ink containing ethylene vinyl acetate
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
US9090758B2 (en) 2012-11-30 2015-07-28 Xerox Corporation Phase change ink comprising modified naturally-derived colorants
US8911543B2 (en) 2012-12-18 2014-12-16 Xerox Corporation Phenylcyclohexanol derivatives as wax modifiers and gelators
US9090777B2 (en) 2013-04-04 2015-07-28 Xerox Corporation Low cost process for solid ink using dry flushed pigments
US9157002B2 (en) 2013-07-12 2015-10-13 Xerox Corporation Phase change ink pigment dispersion process

Also Published As

Publication number Publication date
GB2294939A (en) 1996-05-15
GB9422477D0 (en) 1995-01-04
AU3810395A (en) 1996-05-31

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