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
  • C09D11/10—Printing inks based on artificial resins
  • C09D11/106—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
  • G03G9/00—Developers
  • G03G9/08—Developers with toner particles
  • G03G9/12—Developers with toner particles in liquid developer mixtures
  • G03G9/13—Developers with toner particles in liquid developer mixtures characterised by polymer components
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
  • G03G9/00—Developers
  • G03G9/08—Developers with toner particles
  • G03G9/12—Developers with toner particles in liquid developer mixtures
  • G03G9/13—Developers with toner particles in liquid developer mixtures characterised by polymer components
  • G03G9/131—Developers with toner particles in liquid developer mixtures characterised by polymer components obtained by reactions only involving carbon-to-carbon unsaturated bonds
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
  • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
  • Y10S430/001—Electric or magnetic imagery, e.g., xerography, electrography, magnetography, etc. Process, composition, or product
  • Y10S430/105—Polymer in developer

Definitions

• a positive-working liquid toner composition comprising in an electrically insulating carrier liquid, a pigment, e.g. carbon black, a metal soap and a dispersing agent comprising an alkylated polymer of a heterocyclic N- vinyl monomer.
• the present invention relates to a liquid toner composition for use in electrostatic printing processes; more particularly, the present invention relates to a positiveworking liquid toner system comprising in addition to an electrically conductive carrier liquid, a pigment, and a metal soap, a dispersant comprising an alkylated polymer of a heterocyclic N-vinyl monomer.
• liquid toner compositions or systems for use in electrostatic printing processes have been disclosed in the literature, many of such compositions or systems have not been found completely satisfactory in view of their inability to remain in suspension adequately or to give copies which have uniform fill and are free from bleeding or similar streaking characteristics.
• a system comprising in an electrically insulating carrier liquid, a coloring agent, a metal soap, and a dispersing agent comprising an alkylated polymer of a heterocyclic N-vinyl monomer.
• a further object of the present invention comprises a positive-working electrostatic toner containing in an electrically insulating carrier liquid a coloring agent, a metal soap, and a dispersing agent.
• a still further object of the present invention comprises a new and improved liquid electrostatic toner having an improved ability to remain in suspension and yielding uniform prints and copies free from bleeding and streaking characteristics
• a colorng agent e.g. carbon black, a metal soap and a dispersing agent comprising an alkylated polymer of a heterocyclic 'N-vinyl monomer.
• a liquid positive-working electrostatic toner comprising an electrically insulating carrier liquid containing a coloring agent, e.g. carbon black, a metal-organic salt or soap and a dispersing agent comprising an alkylated polymer of a heterocyclic N-vinyl monomer.
• a coloring agent e.g. carbon black, a metal-organic salt or soap
• a dispersing agent comprising an alkylated polymer of a heterocyclic N-vinyl monomer.
• the liquid toner composition or system comprises as a base iluid any of the conventional electrically insulating carrier liquids generally employed in liquid developer and toner compositions.
• Such electrically insulating carrier liquids generally comprise hydrocarbon solvent materials having the necessary di-electric constant, e.g. less than 3 and volume resistivity, e.g. in excess of 10 ohm centimeter so as to be acceptably employed in the electrostatic reproduction process.
• the solvent can comprise various hydrocarbon solvents, e.g. toluene, kerosene and mixtures thereof as well as various commercial petroleum and hydrocarbon solvents, e.g. Isopar having a boiling range of from ISO-182 C.
• the coloring agent or pigment employed in accordance with the liquid electrostatic toner of the present invention can again comprise any of those conventionally employed in such conventional electrostatic toners.
• the coloring agent or pigment can comprise carbon black, channel black, alkali blue, nigrosine dyes,
• any conventional coloring agent or pigment which is dispersible in the carrier liquid can be employed in the liquid electrostatic toner of the present invention.
• the pigment e.g. carbon black suspended in the carrier liquid as the toner is employed in that amount necessary when attracted to the negative electrostatic lmage through the positive-working of the metal soap and dispersing agent in the toner system to be deposited on the image areas only and provide the desired positive print or copy.
• the pigment comprises from about .001% to about of the toner system or composition. Of course, slightly lesser or greater amounts can be employed where desired for particular purposes.
• the pigments would by themselves in the insulating carrier liquid assume fully or partially negative polarity in respect to the negative electrostatic latent image, such pigments would tend to deposit onto the non-image areas to a greater or lesser degree or would deposit both onto the image and non-image areas. For this reason, therefore, it is necessary to modify the characteristics of the pigmented insulated carrier liquid so as to provide a positive-working system wherein the pigment particles. are deposited only onto the image areas of the negative electrostatic latent image by assuming a positive electrostatic charge.
• the metal soaps or salts employed in accordance with the present invention are the hydrocarbon solvent soluble salts of the metals cerium, iron, nickel, cobalt, zirconium, cadmium, lithium, magnesium, manganese, calcium, barium, strontium, chromium and indium, the salts or soaps of such metals in the liquid toner system of the present invention providing copies having no tendency to bleed or streak.
• the salts or soaps generally employed in accordance with the present invention are those which are soluble in the carrier liquid which is generally a hydrocarbon fraction.
• suitable soaps include the metal linoleates, naphthenates, resinates, palmetates, stearates, oleates, octoates, etc.
• alkylated polymers of heterocyclic N-vinyl monomers are utilized as the dispersants.
• These dispersants are those prepared by alkylation of a homopolymer or copolymer of a heterocyclic N-vinyl monomer, preferably an N-vinyl lactam monomer and most preferably an N-vinyl pyrrolidone monomer with an alpha-olefin containing from 2 carbon atoms to 2000 carbon atoms, preferably in the range of from 2 to 200 carbon atoms, and most preferably in the range of from 8 to 42 carbon atoms, said alkylation process being more fully described in General Aniline & Film Corporations co-pending patent application, Ser. No.
• heterocyclic N-vinyl monomers which contain a carbonyl function adjacent to the nitrogen in the heterocyclic moiety
• alkylated polymer derivatives produced as described in said applications, Ser. Nos. 508,547 and 525,374 may be employed in practicing the present invention, that may be mentioned are N-vinyl succinimide, N-vinyl diglycolylimide, N-vinyl glutarimide, N-vinyl-3-morpholinone, N-vinyl-S-methyl 3-morpholinone, N-vinyl-5-ethyl-3-morpholinone, N-vinyl oxazolidone, etc., and N-vinyl ring-oxygenated lactams as disclosed in U.S. Pat. 3,231,548, and especially the N-vinyl 5-, 6- and 7-membered lactams, particularly N- vinyl pyrrolidone, characterized by the following formula:
• R and R are selected from the group consisting of hydrogen, methyl and ethyl, n is an integer of from 1 to 3, and m represents the average molecular weight as determined by relative viscosity measurements which are designated as K values.
• alkylated polymers of comparable monomers of N-vinyl 5-, 6- and 7-membered thiolactams, N-acryloylpyrrolidone, -piperidone and -caprolactam; N-acryloyl 5 methyl-pyrrolidone, N-acryloyl-6- methyl piperidone and N-acryloyl-7-methyl caprolactam and their corresponding 5-, 6- and 7-ethyl derivatives; N-acryloxy-methyl-pyrrolidone, -piperidone and -caprolactam; N-methacryloxy ethyl-pyrrolidone, -piperidione and -caprolactam; N-methacryloxy-methyl-5-methyl pyrrolidone, -6-methyl-piperidone and -7-methyl-caprolactam; N-methacrylamido-methyh, N-methacrylamidoethyl-, N-methacrylamido
• the homopolymers of the N-vinyl lactams characterized by the foregoing formula are readily obtained by homopolymerizing N-vinyl pyrrolidone; N-vinyl-5-methyl pyrrolidone; N-vinyl-S-ethyl pyrrolidone; N-vinyl-5,5-dimethyl pyrrolidone; N-vinyl-5,5-diethyl pyrrolidone and N-vinyl-S-methyl-S-ethyl pyrrolidone; N-vinyl piperidone; N-vinyl-6-methyl piperidone; N-vinyl-6-ethyl piperidone; N-vinyl-6,6-dimethyl piperidone; N-vinyl-6,6-diethyl piperidone and N-vinyl-6-methyl
• I employ alkylated derivatives of homopolymers of heterocyclic N- vinyl monomers having a K value from about 10 to 140, preferably from about 30 to 100.
• These homopolymers are readily obtained by conventional homopolymerization procedures of the foregoing heterocyclic N-vinyl monomers described in U.S. Pats. 2,265,450; 2,3l7,804; 2,335,- 454 and many others too numerous to mention in which working examples are given.
• Copolymers obtained by copolymerizing to 99 mole percent of the foregoing heterocyclic N-vinyl monomers with 1 to 95 mole percent of a monoethylenically unsaturated polymerizable monomer and having a K value from about to 140 are readily alkylated in accordance with the present invention to yield products having solubility characteristics dictated by the end use.
• alkylated copolymers suitable for use in practicing the present invention include vinyl esters such as vinyl acetate, vinyl propionate, vinyl butyrate, vinyl isobutyrate, vinyl lactate, vinyl caproate, vinyl caprylate, vinyl oleate and vinyl stearate; acrylonitrile; vinyl ketones; vinyl cyclohexane; styrene; 2-vinyl pyridine, 4-vinyl pyridine; acrylic acid, acrylate ester monomers of the formula:
• CH CHCOOR wherein R represents either a straight or branched alkyl of from 1 to 18 carbon atoms or an alkoxyalkyl in which the total number of carbon atoms in the alkyl groups range from 3 to 6.
• acrylate esters examples include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, s-butyl, Z-methyl-l-butyl, 3-methyl-1-butyl, 2-ethyll-butyl, amyl, 3-pentyl, Z-methyl-l-pentyl, 4-methyl-2- pentyl, hexyl, 2-ethyl-hexyl, heptyl, 2-heptyl, octyl, 2-octyl, nonyl, 5-ethyl-2-nonyl, decyl, 2-methyl-7-ethyl-4-undecyl, dodecyl, tetradecyl, hexadecyl, octadecyl, 2-methoxyethyl, 2-ethoxyethyl and 2-butoxyethyl acrylate; me
• a different heterocyclic N-vinyl monomers such as for example, N-vinyl lactam with either N-vinyl succinimide, N-vinyl-3-morpholinone, and the like, may also be copolymerized and the resulting copolymer alkylated for use in the present invention.
• any a-olefins having a molecular weight from about 28 to as high as about 28,000 may be employed as the alkylating agent for the alkylated polymers of the various heterocyclic N-vinyl monomers.
• ethylene propylene, l-butene, l-pentene, 2-ethyl-1-butene, 2-methyl-l-pentene, l-hexane, 5-methyl-l-hexene, 2-methyl-l-pentene, 3-ethyl-1-pentene, l-heptene, l-octene, l-nonene, 2-ethyl-l-hexene, l-decone, 1- dodecone, l-tetradecene, l-hexadecene, l-heptadecene, loctadecene, l-nonadecene, l-eicosene, l-docosene, l-tetracosene, l-pentacosene and polybutenes of molecular weight of 400 to
• linear u-olefins are preferred because of their commercial availability, numerous isomers of a-olefins ranging from l-pentene to l-pentacosene as well as polybutenes may also be employed in the alkylation reaction. The only requirement in such case is that the isomer contained in ethylenic unsaturation in the a-position thereof.
• a mixture of commercially available linear ocolefins produced by cracking petroleum wax or by polymerizing lower olefins may also be used as the alkylating agent.
• Alpha-olefins in the carbon range of from C -C C -C C11; C -C and C -C are commercially available and may be used.
• a mixture of a-olefins containing from 65 to percent of a-olefins of from C to C carbon atoms having an average molecular weight of 366 is also commercially available and such mixture is employed in the alkylation reaction.
• the quantity of the alkylated polymers of the heterocyclic N-monomonomers employed for a given amount of pigment or coloring agent is not critical in accordance with the present invention, such dispersing agent need only be employed in that amount sufficient to provide a stable suspension or dispersion of the pigment.
• the dispersing agent is employed in the range of 0.01 to 2-3 times the weight of the pigment, and preferably within the range of 1 to parts per 100 parts of the pigment employed.
• the dispersing agents employed in accordance with the present invention act to provide a stable, uniform dispersion of the pigment particles within the liquid electrostatic toner system so as to provide a copy having a uni form fill and free from bleeding or streaking characteristics. It is theorized that the salts or soaps employed im part strong, electrical charges to the toner or pigment particles by being absorbed on the particle surfaces thus causing the particles to be drawn to the sensitized paper with suflicient attraction to firmly fix the particles on the image.
• a dispersing agent comprising an alkylated polymer of a heterocyclic N-vinyl monomer it is possible to employ a metal soap in an amount ranging from about 0.5% to about 3% by weight.
• a metal soap in an amount ranging from about 0.5% to about 3% by weight.
• the manner by which the dispersion is produced is in no way critical.
• 3-roll mill, ball mills, colloid mills, high speed shear mixers, etc. are all applicable in the production of the dispersions employed in the liquid electrostatic toner systems of the present invention.
• the expression coloring agent is meant to embrace all and any pigments and dyestuffs applicably employed in the present and like electrostatic liquid toner systems.
• such term embraces carbon blacks including furnace blacks, lamp blacks, channel blacks and other black materials made by processes well known in the art.
• colored pigments including the phosphotungstate and phosphomolybdate colors, alkali blue and many azo pigments as well as nigrosine dyestuffs and triphenylmethine dyes in particular.
• any and all pigments and dyestuifs capable of yielding color copies when attracted to the negative latent image by the action of the metal soaps and dispersing agents can be advantageously employed.
• EXAMPLE I The following materials were mixed on a 3-roll mill to obtain a uniform dispersion as a heavy ink.
• Cerium naphthanate (0.6%) 1 Strontium naphthenate (0.6%) Chromium naphthenate (0.6%) Indium naphthenate (0.6%) Nickel octoate (1.0%) Zirconium octoate 0.6%) Cadmium octoate (1.6%) Magnesium naphthenate (1%) Manganese naphthenate (0.6%) Barium octoate (0.6%)
• This toner when tested at a concentration of about 6 cc.
• EXAMPLE V The following materials were mixed and passed over a 3-roller mill to make an ink.
• the ink was adjusted to 5% pigment concentration with additional petroleum solvent.
• a positive working electrostatic liquid toner comprising (a) an electrically insulating carrier liquid having a dielectric constant of less than three and a volume resistivity in excess of 10 ohm centimeter; (b) a coloring agent dispersible in said carrier liquid and capable of yielding color copies when attracted to a negative latent image; (c) a metal soap of a fatty acid soluble in said carrier liquid; and (d) as a dispersant for said coloring agent an alkylated polymer of a heterocyclic N-vinyl monomer in which the alkyl radical of said polymer contains from 2 to 2000 carbon atoms, and said polymer has a K value of about 10 to 140.
• alkylated polymer is an alkylated polymer of an N-vinyl pyrrolidone monomer.
• said metal soap comprises a soap selected from the group consisting of the linoleates, naphthenates, resinates, palmetates, stearates, oleates and octoates of a metal selected from the group consisting of cerium, iron, nickel, cobalt, zirconium, cadmium, lithium, magnesium, manganese, calcium, barium, strontium, chromium and indium.

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• Chemical & Material Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Physics & Mathematics (AREA)
• General Physics & Mathematics (AREA)
• Life Sciences & Earth Sciences (AREA)
• Engineering & Computer Science (AREA)
• Materials Engineering (AREA)
• Wood Science & Technology (AREA)
• Organic Chemistry (AREA)
• Liquid Developers In Electrophotography (AREA)
• Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

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Cited By (20)

Citations (2)

• 1968
  • 1968-06-19 US US738127A patent/US3542682A/en not_active Expired - Lifetime
• 1969
  • 1969-06-05 SE SE8002/69A patent/SE341725B/xx unknown
  • 1969-06-13 BR BR209731/69A patent/BR6909731D0/pt unknown
  • 1969-06-16 CH CH917569A patent/CH531035A/de not_active IP Right Cessation
  • 1969-06-17 CA CA054,552,A patent/CA951557A/en not_active Expired
  • 1969-06-17 GB GB30614/69A patent/GB1279154A/en not_active Expired
  • 1969-06-18 NO NO02512/69A patent/NO128838B/no unknown
  • 1969-06-18 FR FR6920293A patent/FR2011210A1/fr not_active Withdrawn
  • 1969-06-18 DE DE19691930784 patent/DE1930784A1/de active Pending
  • 1969-06-18 BE BE734737D patent/BE734737A/xx unknown
  • 1969-06-18 BE BE734738D patent/BE734738A/xx unknown
  • 1969-06-19 NL NL6909360A patent/NL6909360A/xx unknown

Patent Citations (2)

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