WO2008103695A1 - Permanent ink compositions and writing instruments containing same - Google Patents

Permanent ink compositions and writing instruments containing same Download PDF

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Publication number
WO2008103695A1
WO2008103695A1 PCT/US2008/054364 US2008054364W WO2008103695A1 WO 2008103695 A1 WO2008103695 A1 WO 2008103695A1 US 2008054364 W US2008054364 W US 2008054364W WO 2008103695 A1 WO2008103695 A1 WO 2008103695A1
Authority
WO
WIPO (PCT)
Prior art keywords
oil
resins
ink composition
solvent
writing instrument
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/US2008/054364
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English (en)
French (fr)
Inventor
Xiaomang Wang
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.)
Sanford LP
Original Assignee
Sanford LP
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 Sanford LP filed Critical Sanford LP
Priority to AU2008218768A priority Critical patent/AU2008218768A1/en
Priority to GB0909274A priority patent/GB2456726B/en
Priority to DE112008001110.9T priority patent/DE112008001110B4/de
Priority to JP2009550981A priority patent/JP5602433B2/ja
Priority to CN200880005642.3A priority patent/CN101617005B/zh
Priority to MX2009008505A priority patent/MX2009008505A/es
Publication of WO2008103695A1 publication Critical patent/WO2008103695A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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
    • C09D11/16—Writing inks
    • C09D11/18—Writing inks specially adapted for ball-point writing instruments
    • 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
    • C09D11/16—Writing inks

Definitions

  • the disclosure is generally related to permanent ink compositions and to writing instruments containing such ink compositions.
  • Dry out occurs because the ink composition contained in a writing instrument can evaporate from an exposed writing point, and leave a solid residue behind.
  • the left over residue can result in the formation of a deposit that is capable of preventing a writing point, e.g., a ball point, from functioning properly, thereby causing the ball pen to write poorly or even fail.
  • the left over residue can clog the capillary tubes of fibrous ink reservoirs and/or fibrous nibs in writing instruments that rely upon capillary action, thereby causing such writing instruments to write poorly or even fail.
  • One embodiment of the disclosure provides permanent ink compositions having reduced rates of ink evaporation (at least relative to other, comparable solvent-dye based ink compositions). Another embodiment of the disclosure provides writing instruments containing such ink compositions. Yet another embodiment provides methods of making written markings with the disclosed ink compositions.
  • the disclosed ink compositions may be used in various writing instruments.
  • the ink compositions may be used in various pens including but not limited to ball pens (e.g., ball point pens, gel pens, and roller ball pens) and fountain pens.
  • the disclosed inks are also well-suited for delivery from writing instruments comprising fibrous ink reservoirs and/or fibrous nibs writing instruments, such as felt tip pens and markers (e.g., "free-ink” markers and markers comprising fibrous reservoirs).
  • the ink compositions provide permanent written marks on both porous and non-porous substrates, and good color intensity on porous and non-porous substrates.
  • the ink compositions comprise at least one solvent, at least one colorant, and at least one oil.
  • the ink compositions may optionally further comprise a resin and one or more additives.
  • the solvent may be any suitable solvent (or combination thereof), but its interaction with the oil contained in the ink composition is related to obtaining desired performance. Specifically, the oil should not be more than about 50 weight percent ("wt.%") soluble in the employed solvent(s).
  • the ink compositions typically comprise from about 20 wt.% to about 98 wt.%, about 30 wt.% to about 97 wt.%, about 40 wt.% to about 95 wt.%, and/or about 50 wt.% to about 94 wt.% of the solvent(s).
  • Representative solvents for use in the ink compositions include but are not limited to glycol ethers including but not limited to ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, ethylene glycol monophenyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monobutyl ether, propylene glycol monophenyl ether, and similar solvents, alcohols including but not limited to ethanol, propanols (e.g., n-propanol and isopropanol), butanols
  • glycol ethers including but not limited to ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, ethylene glycol monophenyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monobutyl ether, prop
  • . "> . e.g., M-butanol, sec-butanol. isobutanol, tcrt-butanol).
  • octanols, and similar solvents ketones including but not limited to 4-hydro. ⁇ y-4-methyl-2-pentanone (also known as diacetonc alcohol), methyl isobutyl ketone, methyl isopropyl ketone, 2-pentanone, and similar solvents, and mixtures thereof.
  • the colorant need not be specifically limited and may comprise at least one dye, at least one pigment (cither "dry” or as a dispersion), or a combination of at least one dye and at least one pigment; however, dyes are generally preferred for use in the ink compositions.
  • a solvent dye, a polymeric dye, and/or an encapsulated dye e.g., microsphere encapsulated dyes
  • Pigments and/or dyes can be added to the formulation as dried powders, pigment concentrate chips, granules, and/or (pre-dispersed) dispersions.
  • Suitable pigments which can be used include but are not limited to titanium dioxide pigments, e.g., titanium dioxide pigments available under the TlPURE*' trade name (Du Pont de Nemours, DE), the KRONOS * trade name (Kronos Inc, Houston, TX), and the TIOXIDE R ' trade name (Huntsman Tioxide, IL).
  • Preferred titanium pigments include TIPURE" R-931 , KRONOS TM 2131 , KRONOS TM 2102, TIOXIDE" R-XL, and TIOXIDE”' TR50, but of course other titanium pigments may also be used.
  • organic pigments may be used. Suitable organic pigments include but are not limited to red, green, blue, yellow, orange, and carbon black pigments (BASF Corporation, NJ; Clariant Corporation, NC; Emerald Hilton Davis, OH; Ciba Specialty Chemicals, Switzerland; Degussa Corporation, NJ; Cabot Corporation, MA; and, Columbian Chemicals Company, GA). Of course, any suitable organic pigment may be used.
  • Aluminum pigments and bronze pigments are exemplary metallic pigments (Schlenk-BOTH Metallic Pigments, MA; Wolstenholme International Inc., IL; Silberline Manufacturing Co., Inc., PA; Zuxing Enterprise Co., Ltd., China; and, Echart GmbH & Co. KG, Germany).
  • pearlescent and other special effect pigments may be used (BASF Corporation, NJ; Ciba Specialty Chemicals, Switzerland; and Taizhu, China).
  • Inorganic colored pigments may also be used.
  • Preferred inorganic colored pigments include but are not limited to colored titanium dioxide pigments available under the FI(X) trade name (Hcubach, Germany) and colored mixed metal oxides inorganic pigments (Heubach, Germany and Cerdec Corporation, PA).
  • Other suitable inorganic colored pigments such as colored aluminum pigments can also be used (Showa Aluminum Powder, K. K., Japan),
  • any pigment dispersion in oil or relatively non-polar solvent may be used.
  • Pigment dispersions can either be prepared or purchased (commercially available pigment dispersions).
  • the ink compositions generally comprise about 0.1 wt.% to about 60 wt.%, about 0.1 wt.% to about 50 wt.%, and/or about 0.5 wt.% to about 45 wt.% of the pigment (solids), when present.
  • pigment dispersions include but are not limited to alkyd pigment dispersions available under the TINT-AYD R AL trade name (Elementis Specialty, NJ), long oil alkyd dispersions (e.g., Formulator 24 A pigment dispersions available from Emerald Hilton-Davis, LLC, OH), short or medium oil alkyd dispersions (e.g.. Industrial 42 A alkyd dispersions available from Emerald Hilton-Davis, LLC, OH), and any other suitable pigment dispersion in oil(s) or hydrocarbon solvent(s), with or without polymer and/or additional dispersing agents.
  • TINT-AYD R AL trade name Elementis Specialty, NJ
  • long oil alkyd dispersions e.g., Formulator 24 A pigment dispersions available from Emerald Hilton-Davis, LLC, OH
  • short or medium oil alkyd dispersions e.g.. Industrial 42 A alkyd dispersions available from Emerald Hilton-Davis, LLC, OH
  • suitable pigment dispersions can be prepared by dispersing one or more pigments in a relatively non-polar solvent and/or oil.
  • the pigments dispersions can optionally include a polymer and/or a dispersing agent.
  • Many of the pigments e.g., metallic pigments and pearlescent pigments
  • Suitable dyes include but are not limited to anionic and cationic dyes.
  • the dyes can be basic dyes, direct dyes, solvent dyes, disperse dyes, or reactive dyes.
  • the ink composition typically comprises about 0.01 wt.% to about 30 wt.%, about 0.10 wt.% to about 25 wt.%, about 0.20 wt.% to about 20 wt.%, and/or about 0.50 wt.% to about 20 wt.% of the dye (actives), when present.
  • suitable dyes include but are not limited to direct black dyes (e.g., direct black dye nos. 4, 14, 17, 22, 27, 38, 51, 1 12, 1 17, 154, 168, and the like); direct blue dyes (e.g., direct blue dye nos. 1 , 6, 8, 14, 15, 25, 71 , 76, 78, 80. 86, 90, 106, 108, 123, 163, 165, I W, 226, and the like); direct red dyes (e.g., direct red dye nos. 1 , 2, 16, 23, 24, 28, 39. 62, 72, 227, 236, and the like); direct yellow dyes (e.g., direct yellow dye nos. 4, 1 1 , 12, 27. 28.
  • direct black dyes e.g., direct black dye nos. 4, 14, 17, 22, 27, 38, 51, 1 12, 1 17, 154, 168, and the like
  • direct blue dyes e.g., direct blue dye nos. 1 , 6, 8, 14, 15, 25, 71 , 76, 78, 80. 86, 90
  • anthraquinone d ⁇ es monoa/o dyes; disa/o dyes; phthalocyanine derivatives, including, for example, various phthalocyanine sulfonate salts; aza annulcncs; forma/an copper complexes; triphcnodioxa/incs; various reactive dyes, including but not limited to reactive black dyes, reactive blue dyes, reactive red dyes (e.g., reactive red dye nos. 4, 56, 180, and the like), reactive yellow dyes (e.g., reactive yellow dye no.
  • solvent dyes including but not limited to solvent yellow dyes (e.g., solvent yellow dye nos. 62, 82, 90, 162, and the like), solvent orange dyes (e.g., solvent orange dye nos. 54, 56, 58, 99, and the like), solvent red dyes (e.g., solvent red dye nos. 89, 1 19, 122, 132, 160, and the like), solvent blues dyes (e.g., solvent blue dye nos. 45, 48, 70, and the like), solvent black dyes (e.g., solvent black dye nos, 27, 29, and the like), and mixtures thereof.
  • solvent yellow dyes e.g., solvent yellow dye nos. 62, 82, 90, 162, and the like
  • solvent orange dyes e.g., solvent orange dye nos. 54, 56, 58, 99, and the like
  • solvent red dyes e.g., solvent red dye nos. 89, 1 19, 122, 132, 160, and the like
  • solvent blues dyes e.g.,
  • NEOPEN ® trade name BASF Corp., WI
  • VALIFAST ® trade name Orient Corporation of America, NJ
  • MORFAST ® and NAVIPON ® trade names Sunbelt Corporation, SC
  • SEPISOL trade name Bima 83, FR
  • Polymeric dyes also are also suitable colorants.
  • the selected oil(s) typically has the solubility property mentioned above relative to the ink composition solvent(s), but otherwise need not be limited. It is generally suitable when the oil has a solubility in the solvent(s) of 0 wt.% to about 50 wt.%, about 1 wt.% to about 40 wt.%, about 2 wt.% to about 30 wt.%, about 3 wt.% to about 25 wt.%, about 5 wt.% to about 20 wt.%, and/or about 10 wt.% to about 20 wt.%.
  • the oil may have a solubility in the solvent of less than about 40 wt.%, less than about 30 wt.%, less than about 25 wt.%, less than about 20 wt.%, less than about 15 wt.%, less than about 10 wt.%, less than about 5 wt.%, less than about 5 wt.%, less than about 2.5 wt.%, and/or less than about 1 wt.%.
  • the oil should not be emulsified into the ink composition. Generally, lower (oil(s) in solvent(s)) solubility values are more preferred for obtaining desired performance.
  • Suitable oils include but are not limited to semi-drying oils such as soybean oils, cottonseed oils, corn oils, and sesame oils, non-drying oils such as olive oils, peanut oils, mineral oils, and castor oils, petroleum-based oils such as napthenic process oils and
  • the oil typically comprises about 0.1 vvt.% to about 15 vvt.%. about 0.5 wt.% to about I U wt.%, about 1 ⁇ vt.°o to about 8 wt.%. and/or about 1 wt.'O to about 5 wt.% of the ink compositions.
  • oils include oils available under the FELURA * trade name (ExxonMobil Lubricants and Petroleum Specialties Co., a division of ExxonMobil Corporation, TX), TUFFLO R trade name (Citgo Petroleum Corporation, FX), and various mineral oils (Penreco, TX).
  • the ink compositions may optionally further comprise a resin.
  • Suitable resins include but are not limited to rosin and modified rosin resins, alkyd resins, hydrocarbon resins, ketone resins, phenolic resins, acrylic resins, terpene resins, polyamide resins, and combinations thereof.
  • the resin typically comprises about 0.1 wt.% to about 50 wt.%, about 0.5 wt.% to about 35 wt.%, about 1 wt.% to about 25 wt.%, and/or about 2 wt.% to about 20 wt.% of the ink compositions.
  • the resin is soluble in the oil of the ink composition, and this can be beneficial for obtaining markings having good permanency.
  • the resin has a solubility of greater than about 0.01 grams/niL oil, greater than about 0.05 grams/mL oil, greater than about 0.10 grams/mL oil, greater than about 0.15 grams/mL oil, greater than about 0.20 grams/mL oil, greater than about 0.25 grams/mL oil, and/or greater than about 0.30 grams/mL oil.
  • Exemplary resins include acrylic resins available under the JONCRYL * trade name (BASF Corp., WI), phenolic resins available under the Bakelite trade name (various), other suitable phenolic resins, e.g., CK-2103, CK-2400, CK-2432, and CK-2500 (Georgia Pacific Resins, Inc., a division of Georgia Pacific, Corp., GA), rosin resins and modified rosin resins available under the SYLVACOTE" and S YLVAPRlNT R trade names (Arizona Chemical, FL), hydrocarbon resins available under the SYLVAPRINT R trade name (Arizona Chemical, FL), polyamide resins available under the UNI-REZ R trade name (Arizona Chemical, FL), and mixtures thereof.
  • CK-2103, CK-2400, CK-2432, and CK-2500 Georgia Pacific Resins, Inc., a division of Georgia Pacific, Corp., GA
  • the ink compositions may optionally further comprise one or more additives.
  • the addithe(s) can be selected from the group consisting of plastici/ers. biocides, surface tension modifiers, wetting agents, synergic resins, dispersing agents, defoamers, surfactants, humectants, viscosity modifiers (e.g., thickeners), How additives, and other additives known in the art.
  • the additives can be added to the ink compositions in an amount such that the overall desired performance of the ink compositions is not adversely affected in any aspect.
  • Preferred surfactants include polydimcthylsiloxane surfactants such as those available under the SILWET R/ trade name (GE Silicones, a division of General Electric Company, CT).
  • Including slow evaporating solvents e.g., solvents having boiling points greater than about 1 15"C
  • humectants such as glycerine and propylene glycol
  • the ink compositions are substantially free of such humectants.
  • the term "substantially free” means that the ink compositions disclosed herein contain less than 2 wt.%, less than 1 wt.%, and/or less than 0.50 wt.% of a referenced component or ingredient.
  • various ink compositions may be formulated, and their viscosities varied from very low values, for example, such as in free ink marker systems and other marker systems (e.g., comprising a fibrous reservoir), to very high values such as in gel pens and in ball point pens.
  • the ink composition When the ink composition is intended for delivery from a marker system, it generally has a viscosity value at 200 rotations per minute of about 1 centipoise to about 40 centipoises (cps) and/or about 2 cps to about 15 cps.
  • ink composition When ink composition is intended for delivery from a ball pen, it generally has a viscosity value of at least about 750 cps and more typically at least about 1000 cps.
  • 10031 1 ⁇ n ink composition was made by dissolving 5.0 grams of a phenolic resin, 7.0 grams of a first dye, and 5.0 grams of a second dye, into a solvent solution comprising 40.20 grams of n-propyl alcohol and 40 grams of ethyl alcohol (200 proof).
  • the ink had a viscosity value (at 200 RPM) of about 2.8.
  • the ink composition was loaded into a marker (comprising a fibrous reservoir in fluid communication with a fibrous nib) and the marker wrote well.
  • An ink composition was made by dissolving 3.8 grams of a phenolic resin and 4.5 grams of a dye into a solvent solution comprising 44.3 grams of n-propyl alcohol and 44.5 grams of ethyl alcohol (200 proof).
  • the ink had a viscosity value (at 200 RPM) of about 2.2.
  • the ink composition was loaded into a marker (comprising a fibrous reservoir in fluid communication with a fibrous nib) and the marker wrote well.

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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)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Pens And Brushes (AREA)
PCT/US2008/054364 2007-02-21 2008-02-20 Permanent ink compositions and writing instruments containing same Ceased WO2008103695A1 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
AU2008218768A AU2008218768A1 (en) 2007-02-21 2008-02-20 Permanent ink compositions and writing instruments containing same
GB0909274A GB2456726B (en) 2007-02-21 2008-02-20 Permanent ink compositions and writing instruments containing same
DE112008001110.9T DE112008001110B4 (de) 2007-02-21 2008-02-20 Permanenttintenzusammensetzungen, Verwendung derselben und Schreibgeräte, die diese enthalten
JP2009550981A JP5602433B2 (ja) 2007-02-21 2008-02-20 パーマネントインク組成物及び当該組成物を含む筆記用具
CN200880005642.3A CN101617005B (zh) 2007-02-21 2008-02-20 永固油墨组合物和含其的书写工具
MX2009008505A MX2009008505A (es) 2007-02-21 2008-02-20 Composiciones de tinta permanente e instrumentos de escritura que contienen las mismas.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US11/677,453 2007-02-21
US11/677,453 US8741039B2 (en) 2007-02-21 2007-02-21 Permanent ink compositions and writing instruments containing same

Publications (1)

Publication Number Publication Date
WO2008103695A1 true WO2008103695A1 (en) 2008-08-28

Family

ID=39475772

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2008/054364 Ceased WO2008103695A1 (en) 2007-02-21 2008-02-20 Permanent ink compositions and writing instruments containing same

Country Status (9)

Country Link
US (1) US8741039B2 (enExample)
JP (1) JP5602433B2 (enExample)
CN (1) CN101617005B (enExample)
AU (1) AU2008218768A1 (enExample)
DE (1) DE112008001110B4 (enExample)
GB (1) GB2456726B (enExample)
MX (1) MX2009008505A (enExample)
TW (1) TW200842170A (enExample)
WO (1) WO2008103695A1 (enExample)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2943540B1 (en) 2013-03-15 2018-11-14 Sanford, L.P. Metallic ink composition and writing instruument containing same

Families Citing this family (9)

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Publication number Priority date Publication date Assignee Title
USD641785S1 (en) 2010-04-09 2011-07-19 Sanford, L.P. Writing instrument
USD641784S1 (en) 2010-04-09 2011-07-19 Sanford, L.P. Writing instrument
USD641782S1 (en) 2010-04-09 2011-07-19 Sanford, L.P. Writing instrument
USD641783S1 (en) 2010-04-09 2011-07-19 Sanford, L.P. Writing instrument
CN102618121B (zh) * 2012-03-23 2014-08-20 西安理工大学 一种金色圆珠笔笔墨组合物及其制备方法
CN104109418A (zh) * 2014-07-21 2014-10-22 常熟市协新冶金材料有限公司 圆珠笔用油墨
CN104530826A (zh) * 2014-12-18 2015-04-22 无锡伊诺永利文化创意有限公司 一种具有保健功能的走珠笔用油墨
CN104530825A (zh) * 2014-12-18 2015-04-22 无锡伊诺永利文化创意有限公司 一种走珠笔用植物源速干油墨
CN105400288A (zh) * 2015-12-28 2016-03-16 王璐 一种书写流畅的中性笔油墨

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US20080196620A1 (en) 2008-08-21
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US8741039B2 (en) 2014-06-03

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