Classifications

• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
  • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
  • C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
  • C08G65/22—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring
  • C08G65/24—Epihalohydrins
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
  • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
  • C08G65/32—Polymers modified by chemical after-treatment
  • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
  • C08G65/333—Polymers modified by chemical after-treatment with organic compounds containing nitrogen
  • C08G65/33303—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing amino group
  • C08G65/33306—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing amino group acyclic
• • 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
  • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
  • Y10T428/00—Stock material or miscellaneous articles
  • Y10T428/31504—Composite [nonstructural laminate]
  • Y10T428/31971—Of carbohydrate
  • Y10T428/31993—Of paper

Definitions

• ammonium compound disclosed in US. Pat. No. 3,01 L918 to Silvernail et al.
• paper coated with these compounds suffers from an objectionably strong aminelike odor which can only be reduced by lowering the pH of the coating to a very acid range in which corrosion of the coating apl5 paratus is promoted.
• these compounds are expensive and a more economical, as well as satisfactory, electroconductive polymer has been sought.
• the invention relates to the manufacture of substrates having electroconductive properties useful when the substrate is employed as a recording element in an electrographic printing process. More particularly, this invention relates to paper having the electroconductive surface adapted for electrographic printing and containing a polymer comprised of quaternized polyepihalohydrin and preferably quaternized polyepichlorohydrin.
• the electroconductive water-dispersible polymer has the formula:
• R is methyl, and m is an integer from 20 to 100.
• This polymer can be easily prepared from the substantially complete quaternization of a trialkyl amine or a trioxyalkyl amine and polyepihalohydrin.
• the polyepihalohydrin is polyepichlorohydrin and this is quaternized with trimethyl amine.
• the polymer is substantially completely quaternized, meaning the the polymer contains from to 100 percent quaternary adducts having the formula:
• X is a halogen selected from the group consisting of chlorine, bromine, and iodine
• R is independently selected from the group consisting of methyl, ethyl, and (C,,H ,,O),,H, where y is an integer from 1 to 30, nis an integer from I to 4, and m is an integer from 5 to 2,000.
• y is an integer from 1 to 30
• n is an integer from I to 4
• m is an integer from 5 to 2,000.
• the quaternary polyepichlorohydrin of the desired molecular weight namely those having a molecular weight of from about 750 to 300,000, and preferably from 2,000 to 150,000, it is necessary to choose an appropriate molecular weight of the polyepihalohydrin.
• Polyepihalohydrins having molecular weights ranging from 450 to l80,000 have been tested and found to produce continuous films of coatings containing these polymers to paper without any operational difficulties.
• the epihalohydrin has a molecular weight ranging from about 1,200 to 100,000.
• the amine is preferably trimethyl or triethyl amine. But other amines could be used, such as methyl diethyl amine, ethoxy dimethyl amine, as well as mixtures of amines.
• the alkyl groups are independently selected from methyl, ethyl, and (C,,H ,,O),,H, where y is an integer from 1 to 30, n is an integer from 1 to 4, and m is an integer from 5 to 2,000.
• the method of preparing the electrographic recording member ofthis invention comprises the following steps.
• a substrate preferably paper
• the term dispersion includes solution, if the polymer is completely or partially water soluble.
• the electroconductive polymers of this invention can be applied as a continuous film to paper by coating, spraying dipping, brushing or by any other suitable application.
• the quaternized polymer is preferably applied to paper, as a coating, in the form of an aqueous dispersion or solution.
• the coated paper is then dried to produce a product having an electroconductive surface.
• Suitable or standard coating devices such as a blade coater, have been used and the coated paper has been dried by the use of radiant energy from heat lamps.
• the coating can be applied to paper at a range of from 0.5 to 2.5 pounds pickup per 3,000 square feet of paper.
• Other components can be formulated with this polymer such as clay, starch, pigments, etc.
• paper is preferred, including high wetstrength paper coated or uncoated, having a thickness of from 3 to 6 mils.
• Other electrically conductive or semiconductive materials may be used, such, for example, as plastic films including cellophane, cloth, and metallic foils, e.g., aluminum and copper foils.
• the water-dispersible quaternized polyepihalohydrin is polyepichlorohydrin quaternized with trimethyl amine.
• the extender is preferably polyvinyl alcohol but could be any extender well known in the art. In certain conditions the extender could be eliminated.
• the electrophotographic photoconductor is Zinc oxide, which is a well-known extender.
• photoconductors for use in the present process are inorganic products such as, for example, the oxides of antimony, aluminum, bismuth, cadmium, mercury, molybdenum and lead.
• inorganic products such as, for example, the oxides of antimony, aluminum, bismuth, cadmium, mercury, molybdenum and lead.
• zinc oxide preferred use is made of zinc oxide.
• the zinc oxide to be used should be as pure as possible and advantageously is a product prepared by the so called French method, that is to say by atmospheric oxidation of zinc vapor.
• the photoconductor should be finely divided and preferably have a particle size below 1 micron.
• polymers may be mixed with the quaternized polyepihalohydrin before application of the coating to a paper substrate.
• a polymer such as starch
• starch may be used as a component of the coating formulation to prevent strike through of the electroconductive polymer by keeping the latter on the surface of the paper. While the use of a polymer such as starch adds very little to the electroconductive properties of the coated paper, it may be used for the above-indicated purpose.
• the starch-quaternized polyepihalohydrin coating may contain any proportion of starch up to about a ratio of about 1:1, starch to electroconductive polymer.
• the electroconductive water-dispersible polymers are easily prepared.
• the following examples illustrate the preparation of the polymers.
• the kettle is then closed from the atmosphere and heated to 100 p.s.i.g. which should be approximately l00 C. Hold for 16 hours. Increase the temperature slowly keeping at p.s.i.g. and hold at 130l40 C. for 2 hours.
• the heat of reaction increased the temperature of the reaction mixture to 1 15 C. in 20 minutes. Temperature was maintained at 100 C. to C. for 1 /2 hours with cooling. During this time an increase in the apparent viscosity of the reaction mixture occurred. After the reaction subsided to the extent that cooling was no longer required, incremental catalyst addition was resumed at 75 to 100 C. and 12 parts was added during a 3-hour period with the temperature maintained by the heat of the reaction. The temperature was maintained at 90 to 100 C. for additional 1% hours.
• the residue was a pale amber viscous liquid which was soluble in toluene and xylene and insoluble in isopropyl alcohol.
• EXAMPLE III One hundred thirty-eight parts by weight of the product of Example 11 was placed in a pressure vessel equipped with agitation and heating along with parts of a 3-mole ethylene oxide adduct of dimethylamine and 182 parts of 25 percent solution of trimethylamine in water and heated at 100 C. for 17 hours, during which time the pressure fell from 47 p.s.i.g. to a slight vacuum in the reactor. The reaction mixture was neutralized to a pH of 5.1 with 23 parts of 30 percent hydrochloric acid.
• EXAMPLE IV Ninety-three parts by weight of the product of Example 11 was heater to C. with agitation and 177 parts of a 3-mole ethylene oxide adduct of dimethylamine added in portions over a l-hour period. The reaction mass was cooled to 110 C. and 50 parts water added. Heating was applied and the reaction mass held at reflux (1 12-1 16 C.) for 5 hours, at which time 50 parts water was added and the mixture neutralized to a pH of approximately 6 with 35 parts 30 percent hydrochloric acid.
• EXAMPLE V One hundred seventy-six parts by weight of the product of Example 11 was heated at 150 C. with agitation and 251 parts of a 5-mole ethylene oxide adduct of dimethylamine was added overal hour period. The temperature was held at 128 C. for 4 hours, afterwhich 100 parts water was added and the reaction mixtureneutralized to a pH of about 6 with 29 parts 30 percent hydrochloric acid.
• EXAMPLE Vl Onehundred twenty-one parts by weight of the product of Example .1 was heated with 520 parts of 25 percent trimethylaminerin water in a pressure vessel with agitation for 16 hours at 100C. Five hundred forty-nine parts of this product was neutralized to a-pH of about 6 with 24 parts 30 percent hydrochloric acid.
• EXAMPLE Vll Forty-two parts by weight of the product of Example 11 was heated with 81 parts of 7-mole ethylene oxide adduct of dimethylamine and 59 parts 25 percent aqueous trimethylamine in a pressure vessel with agitation for 16 hours at 100 C. Five hundred fifteen parts of this product was neutralized to a pH of about 6 with 51 parts 30 percent hydrochloric acid.
• EXAMPLE Vlll Seventy parts by weight of the product of Example 11 was heated with agitation .to 145 C. and 199 parts of a 7-mole ethylene oxide adduct of dimethylamine was added over a 30- minute period. The reaction mass was held at 130 to 140 C. for 4 hours and 50 parts water added. Heating was continued at reflux (1 12 C.) for an additional 2 hours. Fifty parts water was added and the reaction mass neutralized to a pH of approximately 6 with 32 parts 30 percent hydrochloric acid.
• Polyepibromohydrin and other amines may also be used to produce similar products.
• ELECTROCONDUCTIVITY TEST The coated substrate is tested for surface resistivity by a standard procedure substantially like that described in Standard Methods of Test for Insulation Resistance of Electrical Insulation Materials," A.S.T.M. designation: D257-46.
• the papers used designated as No. 1 and No. 2 were standard papers used in the industry for eleetrophotography.
• the paper weighs grams per square meter and is made from a moderately beaten papermaking furnish of bleached chemical wood pulp, ground wood, and chemical clay filler and fiber, rosin size precipitated by aluminum sulfate.
• ()thcr quatcrnizcd polyepihalohydrins of the examples may he used and give good results as clcctroconductive polymers.
• other substrates such as cellophane. cloth, and metallic foils could he used.
• X is a halogen selected from the group consisting of chlorine, bromine, and iodine
• R is independently selected from the group consisting of methyl, ethyl and (C,,H ,,0), H where y is an integer from 1 to 30, n is an integer from 1 to 4, and m is an integer from 5 to 2,000
• water-dispersible polymer comprises of from 80 to 100 percent quaternary adducts where X is chlorine, R is methyl and m is an integer of from 20 to 100.
• a method of producing an electrophotographic-recording member which comprises the steps of:
• an electrophotographic photoconductor selected from the group consisting of the oxides, iodides, selenides, sulfides, and tellurides of zinc, antimony, aluminum, bismuth, cadmium, mercury, molybdenum and lead; selenium; arsenic trisulfide; lead chromate; and cadmium arsenide to form a final electrophotographic recording member.
• the water-dispersible polymer comprises of from 80 to 100 percent quaternary adducts where X is chlorine, R is methyl and m is an integer of from 20 to 100.

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• Chemical & Material Sciences (AREA)
• Physics & Mathematics (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Health & Medical Sciences (AREA)
• Spectroscopy & Molecular Physics (AREA)
• Medicinal Chemistry (AREA)
• Polymers & Plastics (AREA)
• Organic Chemistry (AREA)
• General Physics & Mathematics (AREA)
• General Chemical & Material Sciences (AREA)
• Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
• Paper (AREA)
• Photoreceptors In Electrophotography (AREA)

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Cited By (19)

Citations (9)

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• 1970
  • 1970-01-07 US US3640766D patent/US3640766A/en not_active Expired - Lifetime
  • 1970-12-03 CA CA099782A patent/CA929803A/en not_active Expired
  • 1970-12-22 GB GB6097670A patent/GB1341840A/en not_active Expired
• 1971
  • 1971-01-06 DE DE2100917A patent/DE2100917C3/de not_active Expired
  • 1971-01-07 JP JP21271A patent/JPS5129655B1/ja active Pending
  • 1971-01-07 FR FR7100352A patent/FR2075298A5/fr not_active Expired

Patent Citations (9)

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