US3707402A - Method of manufacturing electronic recording material - Google Patents

Method of manufacturing electronic recording material Download PDF

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Publication number
US3707402A
US3707402A US828776A US3707402DA US3707402A US 3707402 A US3707402 A US 3707402A US 828776 A US828776 A US 828776A US 3707402D A US3707402D A US 3707402DA US 3707402 A US3707402 A US 3707402A
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United States
Prior art keywords
acid
weight
resin
emulsion
resin emulsion
Prior art date
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Expired - Lifetime
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US828776A
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English (en)
Inventor
Nario Yamaguchi
Sakae Shimizu
Kazuo Tubuko
Kishichiro Kondo
Hiroo Iwata
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Toagosei Co Ltd
Ricoh Co Ltd
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Toagosei Co Ltd
Ricoh Co Ltd
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    • 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
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/05—Organic bonding materials; Methods for coating a substrate with a photoconductive layer; Inert supplements for use in photoconductive layers
    • G03G5/0528—Macromolecular bonding materials
    • G03G5/0589—Macromolecular compounds characterised by specific side-chain substituents or end groups
    • 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
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/05—Organic bonding materials; Methods for coating a substrate with a photoconductive layer; Inert supplements for use in photoconductive layers
    • G03G5/0528—Macromolecular bonding materials
    • G03G5/0532—Macromolecular bonding materials obtained by reactions only involving carbon-to-carbon unsatured bonds
    • G03G5/0546—Polymers comprising at least one carboxyl radical, e.g. polyacrylic acid, polycrotonic acid, polymaleic acid; Derivatives thereof, e.g. their esters, salts, anhydrides, nitriles, amides

Definitions

  • ABSTRACT OF THE DISCLOSURE A method of manufacturing an electronic recording material, which comprises the step of forming on a support a recording layer or a photoconductive layer consisting of a highly insulating resin or a material composed of said highly insulating resin and a photoconductive substance contained therein, said resin being a resin emulsion of vinyl copolymers having an epoxide radical or a hydroxyl group.
  • the present invention relates to a method of manufacturing an improved electronic recording material for use in electrophotography.
  • the electrophotographic material includes one prepared by forming a photoconductive layer consisting of a highly insulating resin containing a metallic oxide such as zinc oxide, titanium oxide and the like and one prepared by forming a recording layer consisting of a highly insulating resin only.
  • the former is intended for developing the electrostatic latent image obtained by means of exposure through an original subsequent to impression of an electric charge by corona discharge on a photoconductive layer, while the latter is intended for developing the electrostatic latent image obtained by means of direct electrification of a recording layer like an original.
  • the highly insulating resin to be employed for such electronic recording materials is required to function as a binder to firmly fix a photoconductive layer or a recording layer onto a support
  • resins of a highly insulating property and which are soluble in organic solvents have hitherto been in general use.
  • the foregoing electronic copying materials are prepared by coating the resinous binder dispersed in organic solvents on the support, so that costly equipment is necessary for preventing harm to humans and fires or explosions during vaporization of the organic solvent employed.
  • the resinous binder is either water soluble or water dispersible
  • the electronic recording materials prepared by employing those resinous binders have such drawbacks that. the electrostatic properties of photoconductive layers are deficient as evidenced by the low potential charged at the time of corona discharge and the tremendous dark decay thereof when left in a dark place subsequent to electrification, whereas when a recording layer has been provided therefor through direct electrification, a change in humidity is apt to give rise to fogging because of the highly insulating resin employed for said recording layer.
  • the present invention is based on the findings resulting from examination of the electrostatic characteristics, image properties and so on of various electronic recording materials provided with a photoconductive layer or a recording layer formed on the support thereof, respectively, by means of varieties of water soluble resins and resinous emulsions obtained by emulsion polymerization.
  • the present invention relates to a method of manufacturing an electronic recording material by means of forming, on a support such as paper and the like, a recording layer or a photoconductive layer comprising a highly insulating resin or a material composed of said highly insulating resin and a photoconductive sub stance contained therein, said method being characterized by the fact that the highly insulating resin employed therefor is a resin emulsion comprising any vinyl copolymers having an epoxide radical or a hydroxyl group at the end of a long chain molecule or vinyl copolymers containing carboxylic acid as well as said hydroxyl group bonded at the end of a long chain molecule.
  • the electronic recording material according to the present invention has proved to be particularly superb in the weather-proofing property thereof.
  • the resinous binder to be employed for the present invention includes, for instance, the resin emulsions of vinyl copolymers obtained by copolymerizing at least one member of the group consisting of glycidyl methacrylate, glycidyl acrylate, hydroxyethyl-methacrylate, 2-hydroxyethylacrylate, hydroxypropyl methacrylate, hydroxypropylacrylate, S-hydroxypentylvinyl ether and the like with at least one member selected from the group of unsaturated monoand di-carboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, itaconic acid, maleic acid, fumaric acid, and at least one member selected from the group consisting of (1) acrylic esters and methacrylic esters such as ethyl acrylate, propyl, acrylate, butyl acrylate, isobutyl acrylate, hexyl acrylate, 2-ethylhexyl acryl
  • a substance obtained by simultaneously copolymerizing a derivative of acrylic acid having B-hydroxyl radical with the foregoing monomers is applicable, and a substance obtained by mixing several prepared emulsion polymers to form a polymer blend is also applicable. Furthermore, a latex obtained by blending epoxide resin in the monomer at the time of emulsion polymerization may also be employed.
  • the emulsifier for the aforesaid resin emulsion to be employed in the present invention it is required to have such properties as dispersibility for zinc oxide, water resisting property of the film formed thereby and capability of enhancing the efiiciency of the electronic recording materials to be produced.
  • an emulsifier to meet said requirements there can be used natural resins containing resin acid, synthetic resins containing acid radical such as carboxylic acid, aliphatic carboxylic acid, aromatic carboxylic acid, alicyclic carboxylic acid, or some substances obtained by salifying them with a volatile base are desirable, and, as occasion demands, a small amount of anionic or nonionic field activator may be added thereto.
  • said natural resin containing resin acid includes elemi, gurjun, jalap, scammonium, bdellium, sagapenum, euphorbium, myrrhe, opopanax, guajak, tacamahac, galbanum, gamboge, olibanum, ammoniacum, asafetida, benzoin, sandarac, kawa kawa, a variety of balsarns such as Canada balsam, Mecca balsam, true balsam,copaiba balsam and Peru balsam, a variety of dammars such as benak, dead dammar, melanty, chn, yan, panoun, and Papuan dammar, a variety of kopals such as kauri kopal, soft Manila kopal, hard manila kopal, Congo kopal, Benguela kopal, Angora kopal, Demerara kopal, Madagascar kopal, hard
  • said aliphatic carboxylic acid includes the group of saturated monocarboxylic acids expressed by the general formula C H COOH and having or more carbons, such as valeric acid, isovaleric acid, caproic acid, enanthic acid, pelargonic acid, caprylic acid, undecanoic acid, lauric acid and tridecanoic acid, the group of olefin monocarboxylic acids expressed by the general formula and having 5 or more carbons, such as angelica acid, tiglic acid, l-pentenoic acid, 2-hexenoic acid, Z-heptenoic acid, 2-octenoic acid, 2-nonenoic acid, 4-tecenoic acid, linderic acid, elaidic acid and oleic acid, the group of acetylene monocarboxylic acids expressed by the general formula C Hz cEC(CH COOH and having 5 or more carbons, such as ethylpropiolic acid, n-propyl
  • the former includes the group of benzoic acids such as toluylic acid, dimethyl benzoic acid and ethylbenzoic acid, the group of benzene-dicarboxylic acids such as phthalic acid, n-phthalic acid and terephthalic acid, the group of benzene-tricarboxylic acids such as hemimellitic acid, trimellitic acid and trimesic acid, the group of sulfocarboxylic acids such as orthosulfocarboxylic acid, meta-sulfocarboxylic acid and para-sulfocarboxylic acid, the group of alkylbenzene-sulfocarboxylic acids such as 2-methylbenzenesulfocarboxylic acid and 2- and 6-dimethylbenzenesulfocarboxylic acid, the group of hydroxycarboxylic acids such as hydroxybenzoic acid, methylsalicyclic acid and
  • alicyclic carboxylic acid includes the group of cyclopropanecarboxylic acids such as 3 oz hydroxybenzyl 2 phenylcyclopropanecarboxylic acid, 3-benzoyl-2-phenylcyclopropanecarboxylic acid and dicyclopropane-l,l-dicarboxylic acid, the group of cyclobutanecarboxylic acid such as cyclobutanecarboxylic acid, Z-methylcyclobutanecarboxylic acid and cyclobutane-l,1- dicarboxylic acid, the group of cyclopentanecarboxylic acids such as methylcyclopentanecarboxylic acid, l-isopropylether-Z-methylcyclopentanecarboxylic acid, 1- and 2-cyclopentane-dicarboxylic acid, cyclopentane acetic acid, naphthenic acid and 1-hydroxypentanecarboxylic acid, the group of cyclohe
  • anion field activator to be employed in combination with the foregoing acids or such substances as obtained by neutralizing said acids with a volatile base, it includes, for example, sodium stearate, potassium laurate, sodium laurate, Z-ethylhexylsodiumsulfate, triethylamine xylenesulfonate, diethylamine xylenesulfonate, triethanolamine alkylbenzenesulfonate, diethylamine alkylbenzenesulfonate and tri ethylamine alkylbenzenesulfonate.
  • the vinyl polymer latex obtained through an ordinary emulsion polymerization by employing the above-stated monomer composition and emulsifier has a pH value in the range of 1.5-3.5, but, due to neutralization by means of a volatile alkali aqueous solution such as ammonia, morpholine, cyclohexylamine, an aliphatic primary amine, e.g. methylamine, ethylamine, and isopropylamine, an aliphatic secondary amine, e.g. dimethylamine, diethylamine and dipropylamine, an aliphatic tertiary amine, e.g.
  • a volatile alkali aqueous solution such as ammonia, morpholine, cyclohexylamine, an aliphatic primary amine, e.g. methylamine, ethylamine, and isopropylamine, an aliphatic secondary amine, e.g. dimethylamine, dieth
  • the volatile base is easily evaporated by air heating at the time of forming a film.
  • the aforesaid polymer latex contains quite a small amount or none of an intensively hydrophilic field activator and has excellent Water-resisting qualities ascribable to a multiplied effect of natural resin acid, fatty acid, aromatic alicyclic-carboxylic acid, etc. having a large number of carbons, and especially has such an advantage that it can provide a film of a superb electric-insulating property which is hardly influenced by humidity.
  • said resin emulsion when employed as a binder to be dispersed in Water together with a photoconductive substance and a sensitizer, exhibits an excellent dispersion etfect, and, not only that, a sensitive layer formed by coating the resultant dispersion on the surface of a support and drying thereafter, can be provided with another excellent character.
  • the epoxide radical or hydroxyl group contained in a resinous binder gives rise to a bridge-making reaction with the acidic component of the copolymer .or the carboxylic acid contained in an emulsifier during the hot-drying process at the time of forming a sensitive layer and easily forms reticulations among molecules or within molecules, to thereby bring about a superb weather-proofing property.
  • a recording material according to the present invention can display such properties and copied images are by no means inferior to those obtained in an atmosphere of high humidity. This is presumably attributable to the fact that, owing to the reticulations of a resinous binder formed within a sensitive layer, it becomes difiicult for the photoconductive substance to absorb the moisture of the atmosphere.
  • the present invention relates to an electronic recording material comprising a support and a photoconductive layer or a recording layer formed on the surface of said support, and has been successful particularly in effecting a novel improvement of the above stated binders to thereby provide a sensitive layer with weather-proofing qualities so as to enhance the unsusceptibility of the electric resistance of said sensitive layer to the humidity of the atmosphere as required for an electrophotograph, and also in eliminating all such defects are attributable to those binders which used to be dissolved in organic solvents only, as in case of the electronic recording materials in the prior art.
  • EXAMPLE 1 (A-resin emulsion)
  • sensitizing dye viz a methanol solution containing 1% of Bromophenol Blue, 0.5% of Fluorescein and 0.1% of Rose Bengal
  • aqueous ammonia and dispersing the resultant mixture with a homomixer electrophotographic sensitive liquids were prepared.
  • said sensitive liquid were respectively coated on the surfaces of an art paper, whose back had been processed for conductivity, to the extent that the weight of the sensitive layer, when dried, was 25 g./m. and was dried.
  • the resultant surface electric potential (as expressed by V 30 seconds after the impression of voltage (6 kv.) was as shown in the following Table 1.
  • product A of the present invention could bring about an image of good contrast if it was under a high temperature and humidity or under a normal temperature, whereas product B prepared for comparsons sake could hardly exhibit any image-formability.
  • EXAMPLE 2 (C-resin emulsion)
  • styrene 50 parts by weight of styrene, 30 parts by weight of methyl-ester methacrylate, 18 parts by weight of hydroxypropylacrylate, 2 parts by weight of acrylic acid, 3 parts by weight of kauri kopal, 0.01 part by weight of dialkylsulfosuccinate, 0.2 part by weight of ammonium persulfate and parts by weight of water were employed.
  • Kauri kopal was first thoroughly dissolved in the monomers, and then all the material was put in the flask as the foregoing Example 1 to effect 7 hours polymerization under the reaction temperature of 70 C.
  • the resultant resin emulsion contained 40% of solid matters and had a pH value of 2.6.
  • E-resin emulsion In this case, by employing 45 parts by weight of ethylester acrylate, 30 parts by weight of acrylonitrile, 10 parts by weight of 2-hydroxyethylacrylate, 2 parts by weight of acrylic acid, 13 parts by weight of abietic acid, 0.09 part by weight of dodecylbenzenesulfonic acid, 0.2 part by weight of ammonium persulfate, 150 parts by weight of water and 5 cc. of triethylamine, said abietic acid was salified. Then, all the material was brought in the flask for 5 hours polymerization at a temperature of 70 C. The resultant resin emulsion contained 40.5% of solid matters and had a pH value of 8.5.
  • the electric charge of the insulating layer of E-resin emulsion under the present invention was 68(V)(V /,u), while F-resin emulsion prepared for use in comparison was 26 (V) (V r), and when these emulsions were respectively employed for preparing an electrostatic recording paper, the insulating layer of E-resin emulsion under the present invention exhibited a remarkable image-formability even under a high temperature and humidity, whereas F-resin emulsion could produce but an image of low concentration.
  • EXAMPLE 4 (G-resin emulsion)
  • the material comprising 50 parts by weight of styrene, 45 parts by weight of butyl-ester acrylate, 5 parts by weight of acrylic acid, 4 parts by weight of oleic acid, 0.3 part by weight of diethylaminedodecylbenzenesulfonate, 0.2 part by weight of ammonium persulfate and 150 parts by weight of water was put in the flask for 5 hours polymerization at a temperature of 63 C.
  • the resultant resin emulsion contained 41.3% of solid matters, and had a pH value of 2.6.
  • H-resin emulsion The material comprising 50 parts by weight of styrene, 40 parts by weight of butyl-ester acrylate, parts by weight of glycidyl methacrylate, 4 parts by weight of ammonium oleate, 0.2 part by weight of ammonium persulfate and 150 parts by weight of water was put in the flask for 4 hours polymerization at a temperature of 68%.
  • the resultant resin emulsion contained 40% of solid matters, and had a pH value of 7.7.
  • a copying paper prepared by applying a blended emulsion comprising the foregoing G-resin emulsion and H-resin emulsion according to the present invention at the rate of 1:1 could produce a clear-cut image even under a high temperature and humidity, whereas a copying paper prepared by applying a blended emulsion comprising said G-resiu emulsion and I-resin emulsion, which was intended for use in comparison, at the rate of 1:1 had a very poor imageformability under a high humidity.
  • EXAMPLE 5 J-resin emulsion
  • the material comprising 50 parts by weight of styrene, 35 parts by weight of ethyl-ester acrylate, 5 parts by weight of acrylic acid, 10 parts by weight of epoxide resin (Epikote 1001 manufactured by Shell International Chemicals Corp.), 1 g. of ammonium dodecylbenzenesulfonate 0.5 part by weight of ammonium persulfate and 150 parts by weight of Water was put in the flask for 7 hours polymerization at a temperature of 75 C.
  • the resultant resin emulsion contained 40% of solid matters, and a pH value of- 2.6.
  • EXAMPLE 6 (L-resin emulsion)
  • the material comprising 20 parts by weight of 2-ethy1- hexylester acrylate, 65 parts by weight of styrene, 10 parts by weight of methylester methacrylate, 6 parts by weight of glycidyl methacrylate, 1 part by weight of acrylic acid, 3 parts by weight of phthalic acid, 0.5 part by weight of triethanolamine palmitate, 0.2 part by weight of ammonium persulfate and parts by weight of water was put in the flask for 5 hours polymerization at a temperature of 70 C.
  • the resultant resin emulsion contained 40.5% of solid matters, and had a pH value of 4.0.
  • a process for preparing a dielectric recording material comprising a support having an insulating layer on one surface thereof, comprising the steps of:
  • a reaction mixture consisting essentially of water having dispersed or dissolved therein (1) at least one monomer selected from the group consisting of glycidyl methacrylate, glycidyl acrylate, hydroxyethyl methacrylate, 2-hydroxyethylacrylate, hydroxypropyl methacrylate, hydroxypropyl acrylate and S-hydroxy pentylvinyl ether,
  • At least one acidic compound selected from the group consisting of aliphatic carboxylic acids, aromatic carboxylic acids, alicyclic carboxylic acids and natural resins containing resin acid,
  • reaction mixture further contains a surface active agent selected from the group consisting of sodium stearate, potassium laurate, sodium laurate, 2-ethylhexylsodiumsulfate, trietnyiaminexylenesulfonate, diethylamine xylenesulfonate, triethanolaminealkylbenzenesulfonate, diethylamine alkylbenzenesulfonate, triethylamine alkylbenzenesulfonate, dialkylsulfosuccinate, dodecylbenzene sulfonic acid, triethanolamine palmitate and ammonium dodecylbenzene sulfonate.
  • a surface active agent selected from the group consisting of sodium stearate, potassium laurate, sodium laurate, 2-ethylhexylsodiumsulfate, trietnyiaminexylenesulfonate, diethylamine xylenesul
  • a process for preparing an electrophotographic copying material comprising an electroconductive support having a photoconductive layer on one surface thereof, comprising the steps of:
  • a water-emulsified resinous binder by subjecting to emulsion polymerization to a reaction mixture consisting essentially of water having dispersed or dissolved therein (1) at least one monomer selected from the group consisting of glycidyl methacrylate, glycidyl acrylate, hydroxyethyl methacrylate, 2-hydr0xyethylacrylate, hydroxypropyl methacrylate, hydroxypropyl acrylate and S-hydroxy pentylvinyl ether,
  • reaction mixture further contains a surface active agent selected from the group consisting of sodium stearate, potassium laurate, sodium laurate, 2-ethylhexylsodiumsulfate, triethylaminexylenesulfonate, diethylamine xylenesulfonate, triethanolamine alkylbenzenesulfonate, diethylamine alkylbenzenesulfonate, triethylamine alkylbenzenesulfonate, dialkylsulfosuccinate, dodecylbenzene sulfonic acid, triethanolamine palmitate and ammonium dodecylbenzene sulfonate.
  • a surface active agent selected from the group consisting of sodium stearate, potassium laurate, sodium laurate, 2-ethylhexylsodiumsulfate, triethylaminexylenesulfonate, diethylamine xylenesulfon

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  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Photoreceptors In Electrophotography (AREA)
US828776A 1968-06-08 1969-05-28 Method of manufacturing electronic recording material Expired - Lifetime US3707402A (en)

Applications Claiming Priority (1)

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JP43039348A JPS51450B1 (enrdf_load_stackoverflow) 1968-06-08 1968-06-08

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US3707402A true US3707402A (en) 1972-12-26

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US (1) US3707402A (enrdf_load_stackoverflow)
JP (1) JPS51450B1 (enrdf_load_stackoverflow)
BE (1) BE734262A (enrdf_load_stackoverflow)
DE (1) DE1928453B2 (enrdf_load_stackoverflow)
FR (1) FR2010421A1 (enrdf_load_stackoverflow)
GB (1) GB1278092A (enrdf_load_stackoverflow)
NL (1) NL6908641A (enrdf_load_stackoverflow)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3793021A (en) * 1969-05-28 1974-02-19 Ricoh Kk Electronic recording material
US3849188A (en) * 1971-04-05 1974-11-19 Kohjin Co Electrostatic image-recording medium and method of making same
US3861954A (en) * 1973-03-16 1975-01-21 Eastman Kodak Co Receiver sheets for electrostatic recording
US3885961A (en) * 1972-08-01 1975-05-27 Mitsubishi Rayon Co Polymeric binder material for use in a photoconductive layer employed in electrophotography
US6099997A (en) * 1992-06-04 2000-08-08 Agfa-Gevaert, N.V. Photoconductive recording material comprising a crosslinked binder system
CN115484698A (zh) * 2022-09-15 2022-12-16 上海爱可家科技有限公司 一种电热膜表面改性处理方法和环保型电热膜

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5660443A (en) * 1979-10-23 1981-05-25 Copyer Co Ltd Lamination type electrophotographic receptor

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3793021A (en) * 1969-05-28 1974-02-19 Ricoh Kk Electronic recording material
US3849188A (en) * 1971-04-05 1974-11-19 Kohjin Co Electrostatic image-recording medium and method of making same
US3885961A (en) * 1972-08-01 1975-05-27 Mitsubishi Rayon Co Polymeric binder material for use in a photoconductive layer employed in electrophotography
US3861954A (en) * 1973-03-16 1975-01-21 Eastman Kodak Co Receiver sheets for electrostatic recording
US6099997A (en) * 1992-06-04 2000-08-08 Agfa-Gevaert, N.V. Photoconductive recording material comprising a crosslinked binder system
CN115484698A (zh) * 2022-09-15 2022-12-16 上海爱可家科技有限公司 一种电热膜表面改性处理方法和环保型电热膜

Also Published As

Publication number Publication date
GB1278092A (en) 1972-06-14
DE1928453B2 (de) 1974-05-30
FR2010421A1 (enrdf_load_stackoverflow) 1970-02-13
DE1928453A1 (de) 1970-08-20
JPS51450B1 (enrdf_load_stackoverflow) 1976-01-08
DE1928453C3 (enrdf_load_stackoverflow) 1975-01-02
BE734262A (enrdf_load_stackoverflow) 1969-11-17
NL6908641A (enrdf_load_stackoverflow) 1969-12-10

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