WO2005044934A1 - Imide d'ester d'huile vegetale comme agent de dispersion du noir de carbone dans des encres a base d'huile - Google Patents

Imide d'ester d'huile vegetale comme agent de dispersion du noir de carbone dans des encres a base d'huile Download PDF

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Publication number
WO2005044934A1
WO2005044934A1 PCT/US2004/035105 US2004035105W WO2005044934A1 WO 2005044934 A1 WO2005044934 A1 WO 2005044934A1 US 2004035105 W US2004035105 W US 2004035105W WO 2005044934 A1 WO2005044934 A1 WO 2005044934A1
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WO
WIPO (PCT)
Prior art keywords
oil
carbon black
ink composition
ink
dispersant
Prior art date
Application number
PCT/US2004/035105
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English (en)
Inventor
Olgierd Wasilewski
Neil Young
Albert A. Kveglis
Original Assignee
Sun Chemical 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 Sun Chemical Corporation filed Critical Sun Chemical Corporation
Publication of WO2005044934A1 publication Critical patent/WO2005044934A1/fr

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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
    • C09D11/00—Inks
    • C09D11/02—Printing inks
    • C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
    • 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
    • C09D11/06—Printing inks based on fatty oils

Definitions

  • This invention relates to oil based inks containing dispersed carbon black.
  • Description of the Related Art [0002]News inks are prepared by mechanically dispersing carbon black in mineral oil. The oil serves as a vehicle for the carbon particles. The properties of the dispersion are very important in the ultimate use of the ink.
  • Black no-heat news inks are formed from conventional furnace carbon blacks by dispersing the black in ordinary mineral oils to a concentration required for good printing, which usually is in the range of 10 to 20% by weight of the carbon black particles.
  • Carbon blacks tend to chain together to form a dispersion having undesirable properties when conventional furnace carbon blacks are dispersed in ordinary mineral oils to a concentration required for good printing. This can be overcome by adding more oil to the dispersion, but it would ordinarily make the pigmentation too weak. It is customary, instead, to give the ink the required "length" by making use of mineral oil containing resinous compounds or substances, or asphaltic still bottoms rich in polar compounds, which will coat the carbon particles and reduce their tendency to chain together. [0004]
  • One of the problems present in the existing art is that no heat litho inks based on mineral oils exhibit a marked tendency, especially in blacks to rub off on handling newsprint.
  • Wax can be mixed or ground into the batch along with pigments or may be introduced during the final blending operations.
  • the wax may be compounded into a "wax media" by dispersing or melting the wax into varnishes and/or solvents and adding these to the ink.
  • the results of optimized dispersion include, at a fixed pigment loading, the following: better color strength, lowered viscosity and increased flow. This increased flow is believed to contribute to reduced rub-off due to increased penetration of the ink into the porous newsprint paper.
  • U.S. Pat. No. 4,747,964 describes the use of alkenyl succinirnides as components of dispersing additive compositions for lubricating oils.
  • E. S. Forbes and E. L. Newstadter's publication in Tribology, (April 1972, pp. 72-77) elucidates the mechanics of the action of polyisobutylene succinimide in stabilizing the suspension of carbonaceous matter and to prevent the formation of sludge in motor lubricating oils.
  • Polyisobutylene succinimide was therefore described as exhibiting good adsorption affinity towards particulates of carbon black. The rational is that long chains of surfactant extended from the surface of particles sterically hinder flocculation and the formation of agglomerates.
  • a poly-isobutylene succinimide such as Lubrizol 2155 available from Lubrizol Corp., has heretofore been employed as a dispersant (i.e., surfactant) for the carbon black particles of an oil-based news ink with good results. Even so, the rub off problem continues to exist in news prints to a undesirable degree.
  • the present invention addresses the rub-off problems that exist in prior oil- based printing inks by combining the oil with an additive comprising the reaction product of a maleated vegetable oil with various mono or polyamines.
  • the resulting oil based printing ink exhibits improved pigment wetting and flow as well as reduced viscosity when incorporated into black no-heat news inks.
  • a significant benefit of the current invention is the ability to form a oil-based printing ink that has improved rub-off characteristics.
  • One aspect of the invention relates to an oil based printing ink that exhibits improved pigment wetting and flow as well as reduced viscosity when incorporated into black no-heat news inks.
  • Figure 1 is a viscosity versus sheer rate profile for oil based ink without any additive and for the ink with each of four different additives.
  • Curve A is that of the ink with wood rosin ester dispersant prepared according to U.S.
  • curve B is that of the ink with polymerized linseed oil ester imide of Example 2 as the additive
  • curve C is that of the ink with coffee bean oil ester imide of Example 1 as the additive
  • c rve D is that of the ink with poly-isobutylene succinimide, commercially available as Lubrizol 2155, as the additive.
  • Ink formulations for news ink generally comprise news ink grade carbon " black of from about 12 to about 20 wt.%, an ink base of refined mineral oil or vegetable oil of from about 70 to about 80 wt.%, surfactants, flow aids and/or anti-spray compounds of from about 3 to about 5 wt.% and distillate of from about 3 to about 5 wt.%.
  • the mineral oil may be hydro- refined, solvent treated, naphthenic or a high viscosity specialist mineral oil.
  • the mineral oil can be made up of a combination of viscosity grades ranging from 0.5 to over 100 poise.
  • a vegetable oil it may, for example, be refined soya oil used in combination with a phenolic resin cooked in gelled Alkyd resin and soya oil
  • the carbon black is usually rubber grade, intermediate particle-size furnace blacks.
  • the grades of carbon black and of the oils that are suitable for production of no-heat news inks are well known to those of ordinary skill in the art and need no further description.
  • a poly-isobutylene succinimide such as Lubrizol 2155, has heretofore been employed as a dispersant (i.e., surfactant) for the carbon black particles with good results.
  • a dispersant i.e., surfactant
  • This invention comprises the discovery of a dispersing agent for the carbon black that may replace the poly-isobutylene succinimide dispersing agent, or may be used in conjunction therewith, to reduce the flow and rub-off problems heretofore experienced.
  • the dispersant so discovered comprises the reaction product of a maleated vegetable oil with various mono or polyamines. This reaction product is believed to be an ester imide derivative of the maleated vegetable oil.
  • Any vegetable oil that is capable of undergoing a reaction with maleic anhydride may be used in this invention.
  • the vegetable oil is reacted with 3-10 parts maleic anhydride or a derivative thereof per 100 parts vegetable oil, usually at an elevated temperature of about 200° C, for a time sufficient to allow for complete reaction of the maleic anhydride.
  • the maleated vegetable oil is thereafter reacted with a dialkylene amine or a trialkylene tetraamine, in an amount stoichiometric to the formation of the desired vegetable oil-based polymaleimide. This reaction may be carried out at elevated temperatures in the range of 140° to about 200° C for a time sufficient to allow for complete reaction of the amine reagent.
  • Illustrative of the vegetables oils that may be used are coffee bean oil and the natural drying oils such as linseed oil, soybean oil, safflower oil, rung oil, dehydrated castor oils, polymerized linseed oil, polymerized soyabean oil, polymerized safflower oil an the like. Of these, polymerized linseed oil and coffee bean oil are preferred.
  • Polymerized linseed oil is itself well known and is made by heating pure linseed oil in an airtight oxygen-free environment at about 288° C for about half a day. It is very viscous and is a very bright and clear honey-like substance that has a relatively slow drying time and a low acid content.
  • Coffee bean oil comprises about 75% of triglycerides and about 20% of fatty acid monoesters of two diterpene alcohols, namely caffestol and kahweol.
  • the mono and polyamines that may be used in a practice of this invention may of the following formula: R- -N- -R or
  • each R may be the same or different alkyl group of from one to six carbon atoms
  • R' and R" are the same or different alkylene group of from one to six carbon atoms and x is a value of 1 to 6.
  • each R is an ethyl group and each R' and R" is an ethylene group and x is 2.
  • the preferred monoamine is diethylamine and the preferred polyamine is triethylenetetramine.
  • Example 1 [0019]88.5 parts of refined coffee bean oil was charged into a four-neck round bottom flask and heated to 205° C under a nitrogen blanket. To this, 7.0 parts of maleic anhydride was added. This mixture was then held for 3 hours at 205° C for reaction. Thereafter the mixture was cooled to 145° C. Then 4.5 parts of triethylenetetramine was added and this mixture was held for 1 hour at 145° C. After 1 hour the material was heated to 205° C and held at this temperature for an amine number below 3.0 and an acid number below 7.0.
  • Example 2 [0020J87.5 parts of a polymerized linseed oil was charged into a four-neck round bottom flask and heated to 200° C under a nitrogen blanket. To this, 4.0 parts of maleic anhydride was added. This mixture was then held for 1 1/2 hours at 200° C for reaction. Thereafter the mixture was cooled to 145° C. Then 8.5 parts of diethylamine was added over 45 minutes and this mixture was held for 1 1/2 hour at 145° C. After this time the material was heated to 200° C and held at this temperature for an amine number of 0. The product of this reaction was then cooled to 100° C and discharged.
  • Example 3 A cold set news ink based on a high structure carbon black, Elftex 115 from Cabot, asphaltic still bottoms from Ziegler, and 2400 SUS mineral oil from San Joaquin, wasprepared in a conventional manner according to the following formula:
  • curve 1 is that of the ink without any additive
  • curve A is that of the ink with wood rosin ester dispersant prepared according to U.S. Patent RE 32,411 as the additive
  • curve B is that of the ink with polymerized linseed oil ester imide of Example 2 as the additive
  • curve C is that of the ink with coffee bean oil ester imide of Example 1 as the additive
  • curve D is that of the ink with poly-isobutylene succinimide, commercially available as Lubrizol 2155, as the additive.
  • the polymerized linseed oil ester imide of Example 2 and the coffee bean oil ester imide of Example 1 are powerful wetting compounds for carbon black in a mineral oil system. These materials have a strong affinity for carbon black and produce a strong deflocculating effect which manifest itself in a depressed low shear viscosity. Their use allows the desired dispersion quality to be attained in a shorter period of time and/or a higher pigment concentration to be carried during the dispersion process.
  • the present invention has been described in detail, including the preferred embodiments thereof. However, it will be appreciated that those skilled in the art, upon consideration of the present disclosure, may make modifications and/or improvements on the invention that fall within the scope and spirit of this invention as set forth in the following claims.

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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)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)

Abstract

L'invention concerne une composition d'encre contenant le produit réactionnel d'une huile végétale traitée au maléate avec plusieurs monoamines ou polyamines. La présente invention porte également sur des compositions d'encre à journal au noir de carbone et sur des procédés pour les préparer. Les propriétés rhéologiques améliorées de ces encres les rendent mieux adaptées aux nécessités de l'impression. Ces encres sont perfectionnées en termes de mouillage des pigments et d'écoulement et elles sont moins visqueuses lorsqu'elles sont incorporées dans des encres à journal noires non thermiques, l'écoulement amélioré se traduisant par un meilleur effacement par frottement.
PCT/US2004/035105 2003-10-29 2004-10-25 Imide d'ester d'huile vegetale comme agent de dispersion du noir de carbone dans des encres a base d'huile WO2005044934A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US69568703A 2003-10-29 2003-10-29
US10/695,687 2003-10-29

Publications (1)

Publication Number Publication Date
WO2005044934A1 true WO2005044934A1 (fr) 2005-05-19

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008048590A1 (fr) * 2006-10-13 2008-04-24 Sun Chemical Corporation Encres à l'eau offset stables contenant des tensio-actifs polymères non solubles dans l'eau
EP2086934A2 (fr) * 2006-11-03 2009-08-12 Sun Chemical Corporation Stabilisateurs d'émulsion ayant une tolérance à l'eau
CN101547979B (zh) * 2006-10-13 2013-04-17 太阳化学公司 非水溶性聚合物表面活性剂

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4747964A (en) * 1985-08-14 1988-05-31 Institut Francais Du Petrole Dispersing additive compositions for lubricating oils and their manufacture
US6187085B1 (en) * 1999-07-26 2001-02-13 Sun Chemical Corporation Carbon black concentrates for news ink

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4747964A (en) * 1985-08-14 1988-05-31 Institut Francais Du Petrole Dispersing additive compositions for lubricating oils and their manufacture
US6187085B1 (en) * 1999-07-26 2001-02-13 Sun Chemical Corporation Carbon black concentrates for news ink

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101547979B (zh) * 2006-10-13 2013-04-17 太阳化学公司 非水溶性聚合物表面活性剂
EP2074180A1 (fr) * 2006-10-13 2009-07-01 Sun Chemical Corporation Tensio-actifs polymères non solubles dans l'eau
JP2015014010A (ja) * 2006-10-13 2015-01-22 サン ケミカル コーポレイション 非水溶性ポリマー界面活性剤
AU2007308079B2 (en) * 2006-10-13 2013-05-02 Sun Chemical Corporation Non-water soluble polymeric surfactants
JP2010528117A (ja) * 2006-10-13 2010-08-19 サン ケミカル コーポレイション 非水溶性ポリマー界面活性剤を含有する安定なオフセット用エマルションインキ
US7909924B2 (en) 2006-10-13 2011-03-22 Sun Chemical Corporation Stable offset emulsion inks containing non-water soluble polymeric surfactants
WO2008048590A1 (fr) * 2006-10-13 2008-04-24 Sun Chemical Corporation Encres à l'eau offset stables contenant des tensio-actifs polymères non solubles dans l'eau
EP2074180A4 (fr) * 2006-10-13 2011-04-20 Sun Chemical Corp Tensio-actifs polymères non solubles dans l'eau
US7985820B2 (en) 2006-10-13 2011-07-26 Sun Chemical Corporation Non-water soluble polymeric surfactants
EP2086934A4 (fr) * 2006-11-03 2011-04-13 Sun Chemical Corp Stabilisateurs d'émulsion ayant une tolérance à l'eau
US8013034B2 (en) 2006-11-03 2011-09-06 Sun Chemical Corporation Stable offset emulsion inks containing water tolerant emulsion stabilizer
AU2007317661B2 (en) * 2006-11-03 2012-09-06 Sun Chemical Corporation Water tolerant emulsion stabilizers
US8013033B2 (en) 2006-11-03 2011-09-06 Sun Chemical Corporation Water tolerant emulsion stabilizers
JP2010509456A (ja) * 2006-11-03 2010-03-25 サン ケミカル コーポレイション 水耐容性エマルジョン安定剤を含有する安定なオフセットエマルジョンインキ
EP2086934A2 (fr) * 2006-11-03 2009-08-12 Sun Chemical Corporation Stabilisateurs d'émulsion ayant une tolérance à l'eau

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