Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
  • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
  • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D213/72—Nitrogen atoms
  • C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
• • B—PERFORMING OPERATIONS; TRANSPORTING
  • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
  • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
  • B41M5/00—Duplicating or marking methods; Sheet materials for use therein
  • B41M5/20—Duplicating or marking methods; Sheet materials for use therein using electric current
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
  • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
  • C08F20/10—Esters
  • C08F20/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
  • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
  • C08F20/52—Amides or imides
  • C08F20/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
  • C08F20/60—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing nitrogen in addition to the carbonamido nitrogen
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
  • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
  • G03G5/10—Bases for charge-receiving or other layers
  • G03G5/105—Bases for charge-receiving or other layers comprising electroconductive macromolecular compounds
  • G03G5/107—Bases for charge-receiving or other layers comprising electroconductive macromolecular compounds the electroconductive macromolecular compounds being cationic
• • 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
  • Y10S526/00—Synthetic resins or natural rubbers -- part of the class 520 series
  • Y10S526/923—Ethylenic monomers containing at least one salt group
• • 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
  • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
  • Y10T428/00—Stock material or miscellaneous articles
  • Y10T428/27—Web or sheet containing structurally defined element or component, the element or component having a specified weight per unit area [e.g., gms/sq cm, lbs/sq ft, etc.]
  • Y10T428/273—Web or sheet containing structurally defined element or component, the element or component having a specified weight per unit area [e.g., gms/sq cm, lbs/sq ft, etc.] of coating
  • Y10T428/277—Cellulosic substrate

Definitions

• This invention relates to electroconductive paper, and particularly to electroconductive paper useful in electrostatic image reproduction techniques, and which has certain high molecular weight polymer coatings formed of chain units with pendant quaternary ammonium radicals.
• Electroconductive paper may be used to distribute electrical stresses in various insulating products; see, for instance, United States Patent No. 3,148,107. Where electrically conductive paper is to be used for nonimpact printing, a substrate, backing, impregnation coating, or layer of electrically conductive material is usually provided. See, e.g., Vaurio and Fird, Electrically Conductive Paper for Nonimpact Printing, TAPPI, December 1964, vol. 47, No. 12, 163A-l65A.
• non-impact printing processes such as electrostatographic, electrophotographic, electrographic, Electrofax, and other processes.
• electrostatographic, electrophotographic, electrographic, Electrofax, and other processes call for the placement of an electric charge on the paper. This may be accomplished by a corona discharge, for example, and in most processes, the electrical charge is placed on the paper in darkness.
• the paper may also be provided with or contain a photoresponsive or photoconductive material or layer. At present there is popularly used a specially treated zinc oxide coating on the paper. Where light strikes portions of the paper treated with such a light-sensitive material, the electrical charge is dissipated in those areas exposed to the light. As a result, there is left a pattern of charged and uncharged areas.
• the charged area will then -be elfective to attract an oppositely charged powdered, or other usually particulated, image-forming material.
• a powder will not be attracted to the light-affected discharged areas, and the powder may thus be deposited on the paper in a pattern to correspond with charged areas.
• an image-forming material may then be fused, or otherwise treated, on the paper to make the image permanent.
• a material presently used, is a Wax-coated finely divided carbon black, which will fuse when heated on the paper.
• the present invention provides improvements in and to the use of paper having electroconductive coatings for use in the aforesaid electrostatic copy reproduction methods.
• polymers generally having pendant quaternary ammonium g oups attached to an essentially linear ethylene polymer chain through an amido or ester linkage, are of special value to provide a paper substrate with an electroconductive coating.
• the polymers which may be used will generally have a molecular weight sufiicient to form clear self-supporting film of perhaps /2 to 2 microns thickness, when dried from an aqueous solution, with repeating groups of the formula:
• R may represent hydrogen or a lower alkyl group such as methyl; R may represent quaternized N- methylpyridyl group or a quaternary ammonium dior trimethylene radical, e.g.:
• R may also represent a quaternized ammonium grouping of aliphatic nature such as:
• X may be halogen or methosulfate.
• R could be represented as 3)s wherein A is a lower alkylene group which may be substituted by an hydroxy or lower alkyl group, and R is a lower alkyl group, and, of course, it need not be the same in alkyl substituents in the quaternary group.
• acrylic monomers from which the above repeating units are derived, can be polymerized in an aqueous medium using a redox catalyst, as in the polymerization of acrylamide, by well-known techniques.
• N-(3-dimethyl amino-propyl) acrylamide may be prepared by the reaction of acrylyl chloride (see J.A.C.S. vol. 72, pt. 2, pp. 2299-2300, May 1950) and a propylene diamine (see United States Patent No. 2,595,907). This first reaction is:
• Trimethylamine 4 gram nitrilotrispropionamide (NTP). The pH was adjusted to 6.5 and the solution purged for 1 hour at 50 C. After the purge, ammonium persulfate (0.075 gram) was added, and 2 minutes later a solution of sodium metabisulfate (0.75 gram) and copper sulfate pentahydrate (0.0587 gram) diluted to one liter, was pumped in at 0.1 ml. per minute. The polymerization exothermed from 48 C. to 73 C. in 60 minutes, and became extremely thick. The solution was held at 75 C. for 1 hour. The polymer solution was then diluted with water and precipitated from acetone and vacuum dried. The resulting polymer was white and extremely hydroscopic, and had an intrinsic viscosity of 3.10 in 1 N NaCl at 30 C.
• EXAMPLE II Homopolymer of Z-methacryloxyethyl trimethyl ammonium chloride This monomer was prepared by adding dimethyl sulfate to dimethylaminoethyl methacrylate and then passing a solution of the methosulfate quaternary through an ion exchange column to place the monomer in the chloride form.
• EXAMPLE III Homopolymer of 2-acryloyloxyethyl diethyl methyl ammonium chloride This monomer was prepared by adding dimethyl sulfate to diethylaminoethylacrylate, and passing a solution of the methosulfate quaternary through an ion exchange column to place the monomer in the chloride form:
• the above monomer (100 g.) was dissolved in water (400 g.). To this solution was added EDTA (0.0322 g.), sodium salicylate (0.32 g.) and NTP (0.163 g.). The pH was adjusted to 6.5, and the solution purged for 1 hour at 50 C. After the purge, ammonium persulfate (0.077 g.) was added and one minute later, a solution of sodium metabisulfite (0.803 g.) and copper sulfate pentahydrate (0.063 g.) diluted to a liter, was pumped in at 0.1 ml. per minute. The polymerization exothenned from 50 C. to 58 C. in 100 minutes, and became thick.
• the solution was held at 60 C. for /2 hour, and then precipitated 5 from acetone and vacuum dried in a heated dessicator to yield a solid brownish polymer, which had an intrinsic viscosity of 0.604 in 1 N NaCl at 30 C.
• EXAMPLE IV Homopolymer of 3-acrylamidopropyl trimethyl ammonium chloride This monomer was prepared by adding acrylyl chloride to N,N-dimethylamino propylamine, quaternizing with dimethyl sulfate and then ion exchanging to get the monomer to the chloride form.
• the quaternary salt (95 g.) was diluted with water (380 g.). To this solution was added EDTA (0.0374 g.), sodium salicylate (0.373 g.), and NTP (0.19 g.). The pH of the solution was adjusted to 6.5 and purged at 50 C. for 1 hour. After the purge, ammonium 'persulfate (0.0945 g.) was added and two minutes later a solution of sodium metabisulfate (0.945 g.) and copper sulfate pentahydrate (0.0742 g.) diluted to a liter, was pumped in at 0.1 ml. per minute. The polymerization exothermed from 51 to 65 C. in 80 minutes, and was too thick to stir. The viscous solution was held at 70 C. for 1 hour, and then precipitated by addition of acetone and vacuum dried to produce a white, hydroscopic solid, which had an intrinsic viscosity of 3.45 in 1 N NaCl at 30 C.
• a solution of the above monomer (30%, 204.4 grams or 0.442 mole) was prepared and adjusted to pH of 6.5 and then purged at C. for 1 hour. After the purge was terminated, a solution of ammonium persulfate (5 X l0 mole catalyst/mole monomer per minute) was pumped in at 0.1 ml. per minute for 100 minutes. The polymerization exothermed from 80 to C. The solution was held at 85 C. for 1 hour and then the polymer was precipitated by addition of methanol-ether to yield a light brown solid which had an intrinsic viscosity of 0.259 in l N NaCl at 30 C.
• the polymers prepared in accordance with the foregoing examples may be employed to prepare an electroconductive paper which is useful in the aforesaid electrostatic copying techniques.
• the polymers of this invention may be applied to the paper, or cellulosic web, by the conventional methods used for that purpose, e.g., coating, dipping, brushing, or by wet end addition, etc.
• the amount of polymer applied to the paper will generally vary within the range of about 0.5-3.0 pounds per 3,000 square feet, depending upon the particular polymer and paper combination used and the degree of electroconductivity which is desired. In some cases, still less might be used, such as, as little as 0.1 pound per 3000 square feet. There seems to be no operative upper limit to the amount of polymer applied, except to the extent this is determined by economics. It will therefore be appreciated and understood that the overall range of from about 0.1 to about 3.0 pounds per 3000 square feet is simply a statement of the required amount of polymer to confer electroconductivity properties to the cellulosic web substrate.
• PROCEDURE FOR TESTING SURFACE RESISTIVITY The following method was employed to test the resistance to the flow of electrical current across the surface of a flat piece of material, in this case, paper.
• a solution of the polymer to be tested was prepared, and filmed on paper suitable for applying electro-conductive coatings (such as Bergstroms copy paper base stock 20 lb./ream (1300 ft?) by means of a Meyer wire-wound draw rod.
• electro-conductive coatings such as Bergstroms copy paper base stock 20 lb./ream (1300 ft?) by means of a Meyer wire-wound draw rod.
• the amount of polymer actually coated can thus be varied by the size of the draw rod used.
• the coated paper is then dried in an oven at 105 C. until dry to the touch.
• the coated paper After the coated paper is dry, it is conditioned in a constant conditions room for at least 16 hours.
• the coated paper is placed into an environmental chamber at the desired relative humidity, and again conditioned for 24 hours.
• the coated paper is then placed into the Keithly Resistivity Adapter, coated side down, a voltage (usually v.) is applied, and the electrical current passing across the surface (surface resistivity) of the sheet is read using a Keithly Electrometer.
• the electrical current is read in amperes, and the following formula used to find surface resistivity:
• the salt humectant treatment noted in the first entrles R stands f hydrogen or lower alkyl; of the table is a conventional coating which has been R1 represents a member of the Class Composed f employed, and consists of an aqueous solution of 8% R potassium chloride and 0.1% hydroxyethyl cellulose (as 0 g a the composition is applied to the paper). or
• the polymer coatings according to the present inventron were la1d down on the paper from an aqueous solu- R2 Stands for non having a concentration of about 4% polymer.
• this invention provides an advantageously improved electroconductive paper which has h t A t 1 1k 1 incorporated thereon a coating composition which con- W g a k ll'epresen 10:, l 'k l gb t Pt t g tains as the essential electroconductive component thereof i l a y ens t 2' y 2 S 1 i a high molecular weight, water soluble, cationic polymer gig 3;?
• y ens group an 3 S an S r a Wer a y e hain units of the formula: havm repeated 6 wherem said coated paper has a surface res1st1v1ty at about 50% relative humidity of the order of about I" R I l- R "I 10 -10 ohms/square; a surface resistivity at about g J; 22% relative humidity of the order of about10 l() or ohms/ square; and a surface resistivity at about 5% humidity of the order of about 10 -10 ohms/ I I square.
• R1 )1 Ba x 2.
• the coated paper of claim 1 wherein said polymer is of the formula: I
• the symbols R and R have the sigon; "I nificance already indicated above, and the symbol x signifies the number of such chain units in the polymer 6 molecule.
• the mode of application of such electrocon- O C O CHZCHOHQHQN M: ductive polymer component to the paper does not form 3.
• sa1d polymer is of the formula:
• coated paper of claim 1 wherein said polymer 8.
• said coated paper of claim 1 wherein said polymer is of the formula: is presented in the coating in a required amount of from about 0.1 to about 3.0 pounds per 3000 surface square -CHgCH-- feet of said paper.

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• Polymers & Plastics (AREA)
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Cited By (17)

Citations (6)

• 1967
  • 1967-03-13 US US622443A patent/US3486932A/en not_active Expired - Lifetime
• 1968
  • 1968-02-26 BE BE711310D patent/BE711310A/xx unknown
  • 1968-02-27 AT AT187068A patent/AT278521B/de not_active IP Right Cessation
  • 1968-02-27 DE DE1968C0044719 patent/DE1671528B2/de active Granted
  • 1968-03-12 NL NL6803477.A patent/NL161896C/xx not_active IP Right Cessation
  • 1968-03-12 FR FR1566640D patent/FR1566640A/fr not_active Expired
  • 1968-03-13 SE SE03319/68A patent/SE357783B/xx unknown

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