Classifications

• • 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
  • G03G9/135—Developers with toner particles in liquid developer mixtures characterised by stabiliser or charge-controlling agents
  • G03G9/1355—Ionic, organic compounds
• • 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
• • 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
  • C09D139/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Coating compositions based on derivatives of such polymers
  • C09D139/04—Homopolymers or copolymers of monomers containing heterocyclic rings having nitrogen as ring member
  • C09D139/06—Homopolymers or copolymers of N-vinyl-pyrrolidones
• • 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

Definitions

• a negative-working electrostatic toner composition capable of providing a reverse black and white image 1n an electrostatic reproduction process comprising an electrically insulating carrier liquid, a pigment or coloring agent, e.g. carbon black, and a polymeric material capable of imparting the negative-working characteristics to the electrostatic toner composition.
• a polymeric material preferably comprises an alkylated polymer of a heterocyclic N-vinyl monomer.
• the present invention relates to a liquid toner com position for use in electrostatic printing processes; more particularly, the present invention relates to a negativeworking liquid toner system comprising in addition to an electrically conductive carrier liquid, a pigment or coloring agent, and a polymer which contributes the negative-working characteristics to the toner composition.
• a liquid toner is generally employed.
• a first latent electrostatic image is produced generally on a photoconductive surface, e.g. zinc oxide, by a first application of an overall negative charge. This is followed by a discharging through light exposure so as to leave a negative charge in the unexposed areas. It is at this point that the liquid toner composition is applied.
• the particles of the toner composition comprising the pigment or coloring agent are positively charged, and accordingly, are directed to the negatively charged areas of the latent image.
• toner e.g. carbon black or similar pigment or coloring agent
• toner e.g. carbon black or similar pigment or coloring agent
• the positive polarity of the toner particles can be easily intensitied by the addition of various control agents to a dispersion or suspension of the pigments or coloring agents within the insulated carrier of the toner composition.
• a negative-working liquid toner system which comprises an electrically insulating carrier liquid containing a pigment or coloring agent and a polymeric material capable of providing the negative-working characteristics for the liquid toner composition.
• a further object of the present invention is to cornprise such a negative-working liquid toner system comprising an electrically insulating carrier liquid, a pigment or a coloring agent, and a polymeric material capable of imparting the negative-working characteristics to the liquid toner composition.
• a still further object of the present invention comprises such a negative-working liquid toner composition for use in electrostatic printing processes comprising an electrically insulating carrier liquid, a pigment, erg. carbon black, and a polymeric material capable of imparting the negative-working characteristics to the liquid toner composition, said polymeric material preferably comprising an alkylated polymer of a heterocyclic N-vinyl monomer.
• a liquid negative-working electrostatic toner comprising an electrically insulating carrier liquid containing a pigment or coloring agent, e.g. carbon black, and a polymeric material capable of imparting the negative-working characteristics to the toner composition, such polymeric material preferably comprising an alkylated polymer of a heterocyclic N-vinyl monomer.
• the liquid toner composition or system comprises as a base fluid 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 300-36 C., or Solveso 100 having a boiling range of from 160174 C., Shell X4 having a boiling range of from 5870 C., or Shell X55 having a boiling range of from 58140 C., can be effectively employed as the electrically insulating carrier liquid of the liquid toner system.
• the pigment or coloring agent employed in accordance with the negative-working liquid electrostatic toner composition of the present invention can comprise any of those conventionally employed in positive or negative-working electrostatic toners.
• the negative-working characteristics of the toner are associated with the particular polymeric materials that are included within the liquid system and thus, any conventional pigment or coloring agent can be advantageously employed.
• the coloring agent or pigment can comprise carbon black and various analogous forms thereof, e.g. channel black, furnace black, lamp black and other black materials made by processes well known in the art, colored pigments including the phosphotungstates and phosphomolybdate colors, alkali blue, and many azo pigments as well as m'grosine dyestuffs and triphenyl methane dyes in particular.
• these materials are those which are conventionally employed in positive-working and negative-Working electrostatic toner compositions.
• the pigment or coloring agent e.g. carbon black when suspended in the carrier liquid as the toner is employed in that amount necessary when attracted to the background of the negative electrostatic image through the negativeworking characteristics of the polymeric material which also acts as a dispersing agent because of the surface active characteristics thereof to be deposited on the background areas and provide desired negative print or copy.
• the pigment comprises from about 0.01% to about of the toner system or composition. Of course, slightly lesser or greater amounts can be employed when desired for particular purposes.
• the negative-working characteristics of the liquid toner composition of the present in- N611ti011 are achieved through the use of certain polymeric materials which are capable of providing the necessary negative-working characteristics.
• polymeric materials preferably comprise alkylated polymers of heterocyclic N-vinyl monomer.
• These materials are those prepared by alkylation of a homopolymer or copolymer of a heterocyclic N-vinyl monomer, preferably a N-vinyl lactam monomer and most preferably a 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. 508,547, filed Nov. 18, 1965 and now U.S. Pat. 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-5-methyl-3- morpholinone, N-vinyl-5-methyl-3-morpholinone, N-vinyl-S-ethyl- 3-morpholinone, N-vinyl oxazolidone, etc., and N-vinyl ringoxygenated 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
• I CH CH2 rn wherein 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.
• c is the concentration in grams per 100 ml. of polymer in solution and the 7 is the viscosity of the solution compared to solvent.
• alkylated polymers of comparable monomers of N-vinyl 5-, 6- and 7-membered thiolactams, N-acryloylpyrrolidone, -piperidone and -caprolactam; N-acryloyl-S-methyl-pyrrolidone, N-acryloyl-6- methyl piperidine and N-acryloyl-7-methyl caprolactam and their corresponding 5-, 6- and 7-ethyl derivatives; N- acyloxy-methyl-pyrrolidone, -piperidone and -caprolac tam; N-rnethacryloxy-ethyl-pyrrolidone, -piperidone and -caprolactam; N-methacryloxy-methyl-5-methyl pyrrolidone, -6-methyl-piperidone and -7-methyl-caprolactam; N methacrylamido-methyl-, N-methacrylamidoethyl-, N- methacryla
• the homopolymers of the N-vinyl lactams characterized by the foregoing formula are readily obtained by homopolymerizing N-vinyl pyrrolidone; N-vinyl-S-methyl pyrrolidone; N-vinyl-S-ethyl pyrrolidone; N-vinyl-'5,5-dimethyl pyrrolidone; N-vinyl-5,5-diethyl pyrrolidone and N- vinyl-5-methyl-5-ethyl pyrrolidone; N-vinyl piperidone; N- vinyl-methyl piperidone; N-vinyl-6-ethyl piperidone; N- vinyl-6,6-dimethyl piperidone; N-vinyl-6,6-diethyl piperidone and N-vinyl-6-methyl-6-ethyl piperidone;
• 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; 2,317,804; 2,335,454 and many other too numerous to mention in which working examples are given.
• Copolymers obtained by copolymerizing 5 to 99 mole percent of the foregoing heterocyclic N-vinyl monomers with 1 to 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:
• 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, 2-methyl-1-butyl, 3-methyl-1-butyl, Z-ethyll-butyl, amyl, 3-pentyl, 2-methyl-1-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; methacrylic
• a different heterocyclic N-vinyl monomer such as for example, N-vinyl lactam with either N-vinyl succinimide, N-vinyl-3-morpholinone, and the like
• a-olefins employed for producing the alkylated polymers used in practicing this invention it is to be noted at the outset that 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.
• a-olefins examples include ethylene, propylene, l-butene, l-pentene, 2-ethyl-l-butene, 2-methyl-l-pentene, l-hexene, S-methyl-l-hexene, Z-methyl-l-pentene, 3-ethyl-1-pentene, l-heptene, l-octene, l-nonene, 2-ethyl-1-hexene, l-decone, 1- dodecene, l-tetradecene, l-hexadecene, l-heptadecene, loctadecene, 1-nonadecene, l-eicosene, l-docosene, l-tetracosene, l-pentacosene and polybutenes of molecular weight of 400
• linear a-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 a-olefins 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 C6-C7; CIT-C9; Cg-C11; C11C15' and C5-C2) are commercially available and may be used.
• a mixture of u-olefins containing from 65 to 75 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 materials in accordance with the present invention can comprise natural hydrocarbon polymers, e.g. Gilsonite resins, thermoplastic polymers of unsaturated hydrocarbons derived from petroleum cracking, e.g. Piccopale resins and oil-soluble C-alkyl succinyl derivatives of polyethyleneimine, e.g. penta or tetra-ethylene imine wherein the alkyl group contains 50 or more carbon atoms, e.g.
• Oronite resins for example, Oronite 1200 as disclosed in US. Pats. 3,219,666 and 3,163,603. All of such materials possess surface active characteristics and thus provide the necessary dispersion of the toner particles in the liquid toner system. More importantly, however, all of such materials possess the property of converting the toner system or composition into a negative-working composition effectively employable in electrostatic printing processes for producing reverse or negative reproductions.
• the polymeric materials employed in accordance with the present invention to provide the necessary negative-working characteristics to the liquid toner composition are generally those selected from the group consisting of alkylated polymers of N-vinyl monomers, e.g. alkylated polymers of N-vinylpyrrolidone polymers, natural hydrocarbon polymers, e.g. natural bitumen, thermoplastic polymers of unsaturated hydrocarbons from petroleum cracking, and oil-soluble C-alkyl succinyl derivatives of polyethylene imines.
• the amount of such material capable of imparting the negative-working characteristics to the liquid toner composition employed for a given amount of pigment or color ing agent is not critical in accordance with the present invention, such material being employed only in that amount necessary to provide the necessary negative-Working characteristics while maintaining a stable suspension or dispersion of the toner. Generally, such material is employed in the range of 0.01-2-3 times the weight of the pigment or coloring agent, and preferably within the range of 1 to parts per 100 parts of the pigment employed.
• liquid toner composition in accordance with the present invention, is in no way critical and, accordingly, such composition can be prepared by conventional methods well known in the art.
• a 3-roll mill, ball mill, colloid mills, high speed shear mixers, etc. are all applicable in the production of the dispersions employed in the liquid electrostatic toner system of the present invention.
• it is conventional to produce a concentrate or ink of the toner and material capable of imparting negative-working characteristics to the composition in an insulating carrier liquid, and subsequently adding such concentration or ink to further insulated carrier liquid to provide the liquid toner composition employed in the electrostatic reproduction process.
• the ink was adjusted to carbon black content with the addition of a further amount of the electrically insulating carrier liquid and, the final toner system was provided by adding 7 cc. of the 5% toner to 1 liter of addi tional aliphatic petroleum solvent.
• the toner composition was then employed in a conventional electrostatic copier to produce a negative electrostatic reproduction.
• the print produced by the use of the toner composition of the present invention was found to give a clear reproduction of the original having a reverse image, that is, the background areas of the reproduction were black whereas the printed material on the original was white. A copy having good fill and substantially no tendency to streak was obtained.
• Gilsonite 4 An olefin-alkylated polyvinylpyrrolidone of an average olefin carbon chain length of 20 carbon atoms and 20% vinylpyrrolidone residue.
• thermoplastic polymer of an unsaturated hydrocarbon der1ved from petroleum.
• a natural hydrocarbon polymer-natural bitumen A natural hydrocarbon polymer-natural bitumen.
• a negative-working electrostatic liquid toner consisting essentially of (a) an electrically insulating carrier liquid having a dielectric constant of less than 3 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 repelled ⁇ by a negative latent image; and
• a toner as defined in claim 1 wherein said alkylated polymer is an alkylated polymer of an N-vinylpyrrolidone monomer.

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Cited By (13)

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Citations (5)

• 1968
  • 1968-07-10 US US743592A patent/US3542681A/en not_active Expired - Lifetime
• 1969
  • 1969-06-05 SE SE08001/69A patent/SE351305B/xx unknown
  • 1969-06-13 BR BR209736/69A patent/BR6909736D0/pt unknown
  • 1969-06-16 CH CH917469A patent/CH532647A/de not_active IP Right Cessation
  • 1969-06-17 GB GB30613/69A patent/GB1279153A/en not_active Expired
  • 1969-06-18 DE DE19691930783 patent/DE1930783A1/de active Pending
  • 1969-06-18 FR FR6920294A patent/FR2012623A1/fr not_active Withdrawn
  • 1969-06-19 NL NL6909418A patent/NL6909418A/xx unknown

Patent Citations (5)

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