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WO2008124415A1 - Compositions d'encre et de revêtements contenant des polymères de monoamine de polybutylèneoxyde - Google Patents

Compositions d'encre et de revêtements contenant des polymères de monoamine de polybutylèneoxyde Download PDF

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Publication number
WO2008124415A1
WO2008124415A1 PCT/US2008/059080 US2008059080W WO2008124415A1 WO 2008124415 A1 WO2008124415 A1 WO 2008124415A1 US 2008059080 W US2008059080 W US 2008059080W WO 2008124415 A1 WO2008124415 A1 WO 2008124415A1
Authority
WO
WIPO (PCT)
Prior art keywords
composition
polybutyleneoxide
dispersant
pigment
monoamine
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US2008/059080
Other languages
English (en)
Inventor
Duy T. Nguyen
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Huntsman Petrochemical LLC
Original Assignee
Huntsman Petrochemical LLC
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 Huntsman Petrochemical LLC filed Critical Huntsman Petrochemical LLC
Publication of WO2008124415A1 publication Critical patent/WO2008124415A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • 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
    • C09D17/00—Pigment pastes, e.g. for mixing in paints
    • C09D17/002—Pigment pastes, e.g. for mixing in paints in organic medium
    • 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
    • C09D11/02—Printing inks
    • C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
    • C09D11/037—Printing inks characterised by features other than the chemical nature of the binder characterised by the pigment
    • 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
    • C09D11/32—Inkjet printing inks characterised by colouring agents
    • C09D11/322—Pigment 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
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/41—Organic pigments; Organic dyes

Definitions

  • the invention relates to ink and coating compositions and more specifically to ink and coating compositions comprising a polybutyleneoxide monoamine polymer.
  • Salts are typically used as dispersing agents for non-aqueous ink applications such as in inkjets.
  • Such salts include metal salts of styrene-acrylic copolymers, metal salts of sulfonated styrene-acrylic copolymers, phosphonium salts or quaternary ammonium salts of styrene-acrylic copolymers.
  • Patent No. 7,022,172 discloses a non-aqueous ink containing a dispersant wherein the dispersant has a polyester amine and/or fatty acid amine structure. Such patents are incorporated by reference herein in their entirety. Drawbacks include that such conventional dispersants are typically not effective in the presence of a resin such as nitrocellulose.
  • nonaqueous pigmented inks and coatings include a pigment dispersant that is a polybutyleneoxide monoamine polymer.
  • the polybutyleneoxide monoamine polymer is included in nonaqueous pigmented inks for ink jet printers.
  • a composition comprises a non-aqueous carrier medium, a pigment, and a polybutyleneoxide monoamine polymer.
  • the composition may be an ink and/or coating composition.
  • a composition comprises a non-aqueous carrier medium, a pigment, a resin, and a polybutyleneoxide monoamine polymer.
  • the resin may be a nitrocellulose.
  • the composition may be an ink and/or coating composition.
  • a method is disclosed of reducing dispersion viscosity in a composition comprising the step of mixing a pigment, a non-aqueous carrier medium, and a polybutyleneoxide monoamine polymer.
  • the polybutyleneoxide monoamine polymer is a highly effective dispersant in reducing dispersion viscosity, which may result in higher pigment loading and reduced milling times.
  • the resulting dispersion may also be very stable.
  • the composition may contain one or more components other than the pigment, non-aqueous carrier medium, and polybutyleneoxide monoamine polymer.
  • such components may include a resin for fixing the pigment onto a substrate.
  • Figure 1 shows the difference in dispersion viscosity between Dispersants A-D and Conventional Dispersant E.
  • the samples had 27.5% pigment loading and 24% dispersant on pigment.
  • Figure 2 shows the difference in dispersion viscosity between Dispersants A-D and Conventional Dispersant E.
  • the chart measures the initial dispersion viscosity (1 day) in ethanol/nitrocellulose. The samples had 30% pigment loading and 20% dispersant on pigment.
  • Figure 3 shows dispersion viscosities of Dispersants A-D. The samples had 27.5% pigment loading and 24% dispersant on pigment. Because Conventional Dispersants E and F were too thick to grind, their results are not shown on this figure.
  • Figure 4 shows dispersion viscosities of Dispersants A-D and Conventional Dispersant E. The samples had 25% pigment loading and 20% dispersant on pigment.
  • Figure 5 shows dispersion viscosities of Dispersants A-D. The samples had 27.5% pigment loading and 24% dispersant on pigment. Because Conventional Dispersants E and F were too thick to grind, their results are not shown on this figure.
  • a composition comprises a polybutyleneoxide monoamine polymer, a pigment, a non-aqueous carrier medium.
  • a composition e.g., ink and coating composition
  • the polymer may be used as a dispersant in any amounts suitable to provide a desired composition.
  • the composition has a ratio of polymer to pigment from about 0.01:1 to about 15:1; alternatively from about
  • the polybutyleneoxide monoamine polymer has the following structure:
  • R' is H or CH 3 ; x is from 0 to 60, alternatively from 0 to 50, and alternatively from 0 to 30; and y is from 5 to 200, alternatively from 10 to 100.
  • R represents a substituted or unsubstituted alkyl group having from 1 to 30 carbon atoms, alternatively from 4 to 30 carbon atoms or an aryl group.
  • Such polybutyleneoxide monoamine polymer may be prepared by any suitable method.
  • the polybutyleneoxide monoamine polymer may be prepared by reacting the alcohol with polyalkylene oxides followed by reaction of ammonia over a catalyst.
  • the polymer may be prepared by reacting alkylphenol with butylene oxide, which may be followed by reaction of ammonia over a catalyst.
  • Embodiments of the present invention also include a pigment.
  • organic pigments include azo pigments (e.g., azo lakes, insoluble azo pigment, condensed azo pigments, and chelate azo pigments), polycyclic pigments (e.g., phtalocyanine pigments, perylenes and perylene pigments, anthraquinone pigments, quinacridone pigments, dioxazine pigments, thioindigo pigments, isoindolinone pigments, and quinophthalone pigments), lake pigments (e.g., base dye lakes and acid dye lakes), nitro pigments, nitroso pigments, and aniline black daylight fluorescent pigments.
  • azo pigments e.g., azo lakes, insoluble azo pigment, condensed azo pigments, and chelate azo pigments
  • polycyclic pigments e.g., phtalocyanine pigments, perylenes and perylene pigments, anthra
  • suitable inorganic pigments include carbon black, titanium oxides, and iron oxides.
  • other pigments may also be used such as pigments that are dispersed in a water phase or pigments with surfaces that have been treated with a surfactant or a polymeric dispersing agent (e.g., graphite carbon).
  • the amount of pigment in the composition may vary depending upon the structure.
  • the composition may contain pigment in an amount ranging from about 1.0 wt.% to about 40 wt.%, alternatively from about 2 wt.% to about 20 wt.% by weight of the composition (e.g., ink composition or coating composition).
  • the composition includes a non-aqueous carrier medium which may be a solvent.
  • a solvent Any solvents suitable for use with inks and coatings may be used.
  • the solvent may be polar organic and/or non-polar solvents. It is to be understood that selection of a suitable mixture depends on requirements and/or needs of the specific application such as desired surface tension and viscosity, the selected pigment, drying time of the pigmented ink jet ink, and type of paper onto which the ink may be printed. Any polar organic solvent suitable for use with inks and coatings may be used.
  • polar organic solvents include alcohols (e.g., methanol, ethanol, and propanol), ketones (e.g., acetone), ethers (e.g., dioxane), esters (e.g., ethyl acetate and propyl acetate), lactams (e.g., 2-pyrrolidone), polyhydric alcohols (e.g., ethylene glycol), propylene glycol, diols (e.g., butanediol and pentanediol), glycol esters (e.g., glycerol and propylene glycol laurate), polyalkyl glycols (e.g., polyethylene glycol), and lower alkyl ethers of polyhydric alcohols (e.g., ethylene glycol monomethyl, monoethyl, and monobutyl ether).
  • alcohols e.g., methanol, ethanol, and propanol
  • ketones
  • any non-polar solvent suitable for use with inks and coatings may be used.
  • suitable non-polar solvents include aliphatic solvents and aromatic solvents.
  • Any amount of solvent suitable for forming the composition may be used. In an embodiment, the amount of solvent is from about 50.0 wt.% to about 99.8 wt.%, alternatively from about 70.0 wt.% to about 99.8 wt.% based on the total weight of the composition.
  • the composition includes a resin.
  • the resin is a nitrocellulose.
  • One skilled in the art will recognize other suitable resins for use in the present invention.
  • the composition may be prepared by any suitable method.
  • the composition may be prepared by mixing the components in a blender, hi some embodiments, a surfactant may be added to the composition.
  • the surfactant may be added to wet the pigment and modify the surface tension of the ink to control penetration of the ink into the paper.
  • examples of surfactants include nonionic, amphoteric and ionic surfactants.
  • Other additives such as binders (e.g., resins), biocides, humectants, chelating agents, viscosity modifiers, and defoamers may also be added to the composition.
  • a method of reducing dispersion viscosity in a composition comprising the step of mixing a pigment, a non-aqueous carrier medium, and a polybutyleneoxide monoamine polymer.
  • a resin is also mixed in the composition.
  • polybutyleneoxide monoamine polymer as a dispersant in compositions such as ink and coating compositions may provide unexpected and surprising results and advantages.
  • the polybutyleneoxide monoamine polymers may defloculate pigments and provide steric stabilization.
  • compositions that include the polybutyleneoxide monoamine polymer exhibit lower dispersion viscosity than those of compositions using conventional dispersants under controlled experimental conditions. This reduction in dispersion viscosity may result in higher pigment loading and shorter milling times for the composition.
  • Dispersant A was prepared by mixing 1 mole of dodecylphenol with 18 moles of butylene oxide followed by animating the mixture.
  • Dispersant B was prepared by mixing 1 mole of methanol with 6 moles of ethylene oxide and 36 moles of butylene oxide followed by animating the mixture.
  • Dispersant C was prepared by mixing 1 mole of dodecylphenol with 42 moles of butylene oxide followed by animating the mixture.
  • Dispersant D was prepared by mixing 1 mole of nonylphenol with 20 moles of butylene oxide followed by aminating the mixture.
  • Dispersion 1 A yellow dispersion was prepared by mixing the following ingredients: 12.38 grams (g) MAGRUDER® YE1400 pigment (CI. Pigment Yellow 14), 2.97 g of Dispersant A, 8.84 g nitrocellulose (35% active), and 20.82 g n-propanol.
  • MAGRUDER® YE 1400 pigment is commercially available from Magruder Color Company, Inc. of Elizabeth, New Jersey. MAGRUDER is a registered mark of the Magruder Color Company, Inc.
  • the SPEEDMIXERTM lab mixer is commercially available from FlackTek, Inc. of Landrum, South Carolina.
  • SPEEDMIXER is a mark of FlackTek, Inc.
  • the BOHLIN® rheometer is commercially available from Malvern Instruments, Inc. of Worcestershire, United Kingdom.
  • BOHLIN is a registered mark of Malvern Instruments, Inc.
  • Control Dispersion 1 The following ingredients were mixed in an attempt to make a yellow dispersion: 12.38 g MAGRUDER® YE1400 pigment, 6.91 g amine terminated polyether dispersant (43% active; which is disclosed in U.S. Patent No. 6,258,155, and which is incorporated by reference herein in its entirety), 8.84 g nitrocellulose (35% active), and 16.88 g n-propanol.
  • the amine terminated polyether dispersant is commercially available from BYK-Chemie GmbH of Konstanz, Germany under the tradename of DISPERB YK® 182 dispersing agent. DISPERBYK is a registered mark of BYK-Chemie GmbH.
  • Control Dispersion 2 The following ingredients were mixed in an attempt to make a yellow dispersion: 12.38 g MAGRUDER® YE1400 pigment, 2.97 g methyloxirane polymer with oxirane, mono (diethylamino)alkyl ether (100% active), 8.84 g nitrocellulose (35% active), and 20.82 g n-propanol. Methyloxirane polymer with oxirane, mono (diethylamino)alkyl ether is commercially available from The Lubrizol Corporation of Wickliffe, Ohio under the tradename of SOLSPERSE® 20000 polymeric dispersant. SOLSPERSE is a registered mark of The Lubrizol Corporation.
  • composition having polybutyleneoxide monoamine exhibited much lower dispersion viscosity than those using conventional dispersants.
  • Example 2 The formulation shown below in Table 4 was used to compare the performance of Dispersant A, Dispersant B, Dispersant C, and Dispersant D with Conventional Dispersant E.
  • Conventional Dispersant E is a methyloxirane polymer with oxirane, mono (diethylamino)alkyl ether and is commercially available from The Lubrizol Corporation under the tradename SOLSPERSE® 20000 dispersing agent. The components were mixed at 3,000 rpm for 3 minutes and then milled with 40 g of 2 mm glass beads at 3,000 rpm for 5 minutes in a SPEEDMIXERTM lab mixer. The viscosity was then measured via a BOHLIN® rheometer. Results are shown in Figure 1. As illustrated, Dispersants A-D each showed lower dispersion viscosities than Conventional Dispersant E.
  • Example 3 The formulation shown below in Table 5 was used to compare the performance of Dispersant A, Dispersant B, Dispersant C, and Dispersant D with Conventional Dispersant E.
  • the dispersant and nitrocellulose were mixed in a conventional kitchen blender for 1 minute. Pigment was then added in three parts and mixed for 3 minutes. 60 g of the above premix was then milled with 40 g of 2 mm glass beads using the SPEEDMIXERTM lab mixer at 3,000 rpm for 5 minutes. The viscosity of the dispersion was then measured via a BOHLIN® rheometer. Results are shown in Figure 2. As shown, Dispersants A-D each showed lower dispersion viscosities than Conventional Dispersant E.
  • Example 4 The formulation shown below in Table 6 was used to compare the performance of Dispersant A, Dispersant B, Dispersant C, and Dispersant D with Conventional Dispersant E and Conventional Dispersant F.
  • Conventional Dispersant F is a (tertiary) amine salt of an acrylic copolymer and is commercially available from BYK- Chemie GmbH of Konstanz, Germany under the tradename of DISPERBYK® 2050 dispersing agent. The components were mixed at 3,000 rpm for 3 minutes and then milled with 40 g of 2 mm glass beads at 3,000 rpm for 5 minutes in a SPEEDMIXERTM lab mixer. The viscosity was measured via a BOHLIN® rheometer. Results are shown in Figure 3. Dispersions using Conventional Dispersant E and Conventional Dispersant F were too thick to grind, and the results therefore did not show in Figure 3. As shown, Dispersants A-D produced relatively low dispersion viscosities.
  • Example 5 The formulation shown below in Table 7 was used to compare the performance of Dispersant A, Dispersant B, Dispersant C, and Dispersant D with Conventional Dispersant E.
  • the dispersant and nitrocellulose were mixed in a conventional kitchen blender for 1 minute. Pigment was then added in three parts and mixed for 3 minutes. 60 g of the above premix was milled with 40 g of 2 mm glass beads using the
  • Dispersants A-D each showed lower dispersion viscosities than Conventional Dispersant E.
  • Example 6 The formulation shown below in Table 8 was used to compare the performance of Dispersant A, Dispersant B, Dispersant C, and Dispersant D with Conventional Dispersant E and Conventional Dispersant F. The components were mixed at 3,000 rpm for 3 minutes and then milled with 40 g of 2 mm glass beads at 3,000 rpm for 5 minutes in a SPEEDMIXERTM lab mixer. The viscosity was measured via a BOHLIN® rheometer. Results are shown in Figure 5. Dispersions using Conventional Dispersant E and Conventional Dispersant F were too thick to grind and the results therefore did not show in Figure 5. As shown, Dispersants A-D produced relatively low dispersion viscosities.

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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)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Pigments, Carbon Blacks, Or Wood Stains (AREA)

Abstract

Cette invention a trait à une encre pigmentaire. Dans un mode de réalisation, l'encre pigmentaire comprend une suspension de particules pigmentaires, un milieu porteur non aqueux et un polymère de monoamine de polybutylèneoxyde.
PCT/US2008/059080 2007-04-03 2008-04-02 Compositions d'encre et de revêtements contenant des polymères de monoamine de polybutylèneoxyde Ceased WO2008124415A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US92155707P 2007-04-03 2007-04-03
US60/921,557 2007-04-03

Publications (1)

Publication Number Publication Date
WO2008124415A1 true WO2008124415A1 (fr) 2008-10-16

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20020198289A1 (en) * 2001-02-14 2002-12-26 Gummeson Joel J. Waterfast ink jet inks containing a UV curable resin
US6548572B1 (en) * 1999-12-07 2003-04-15 Dupont Canada Inc. Surface printing inks and coatings for use
US6653412B2 (en) * 2000-03-23 2003-11-25 Bakelite Ag Monoamine or polyamine reacted with polyepoxide/monoamine or polyamine precursor, epoxy resin and epoxide thinner
US6916505B2 (en) * 2003-03-04 2005-07-12 Air Products And Chemicals, Inc. Mannich based adducts as water based epoxy curing agents with fast cure capabilities for green concrete application

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6548572B1 (en) * 1999-12-07 2003-04-15 Dupont Canada Inc. Surface printing inks and coatings for use
US6653412B2 (en) * 2000-03-23 2003-11-25 Bakelite Ag Monoamine or polyamine reacted with polyepoxide/monoamine or polyamine precursor, epoxy resin and epoxide thinner
US20020198289A1 (en) * 2001-02-14 2002-12-26 Gummeson Joel J. Waterfast ink jet inks containing a UV curable resin
US6916505B2 (en) * 2003-03-04 2005-07-12 Air Products And Chemicals, Inc. Mannich based adducts as water based epoxy curing agents with fast cure capabilities for green concrete application

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