EP0005334A1 - Composition de toner électrophotographique - Google Patents

Composition de toner électrophotographique Download PDF

Info

Publication number
EP0005334A1
EP0005334A1 EP79300655A EP79300655A EP0005334A1 EP 0005334 A1 EP0005334 A1 EP 0005334A1 EP 79300655 A EP79300655 A EP 79300655A EP 79300655 A EP79300655 A EP 79300655A EP 0005334 A1 EP0005334 A1 EP 0005334A1
Authority
EP
European Patent Office
Prior art keywords
toner
resin
terpolymer
toner composition
image
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP79300655A
Other languages
German (de)
English (en)
Inventor
Robert D. Bayley
N. Ganesh Kumar
Chin H. Lu
Robert A. Nelson
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Xerox Corp
Original Assignee
Xerox Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Xerox Corp filed Critical Xerox Corp
Publication of EP0005334A1 publication Critical patent/EP0005334A1/fr
Withdrawn legal-status Critical Current

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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
    • G03G9/087—Binders for toner particles
    • G03G9/08702—Binders for toner particles comprising macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • G03G9/08726—Polymers of unsaturated acids or derivatives thereof
    • G03G9/08728—Polymers of esters

Definitions

  • This invention relates to an electrophotographic toner composition which comprises a colorant and a resin.
  • a plate generally comprising a conductive backing upon which is placed a photoconductive insulating surface is uniformly charged and subsequently the photoconductive surface is exposed to a light image of the original to be reproduced.
  • the photoconductive surface is prepared in such a manner so as to cause it to become conductive under the influence of the light image in order that the electrostatic charge contained thereon can be selectively dissipated to produce a latent image which is developed by means of a variety of pigmented resin materials especially made for this purpose such as toner. It is this toner material that is electrostatically attracted to the latent image areas on the plate in proportion to the charge concentration thereof, thus in areas of high charge
  • This developed image can then be transferred to a final support material such as paper and affixed thereto.
  • U. S. Patent No. 3,635,704 There are many methods that are known for developing and fixing the resulting images, some of which are disclosed in U. S. Patent No. 3,635,704 and include for example, cascade development as described in U. S. Patent No. 2,618,552; magnetic brush development as described in U. S. Patents 2,874,063; 3,251,706; and 3,357,402; powder cloud development as described in U.S. Patent No. 2,221,776; and touchdown development as described .::in U. S. Patent No. 3,166,432.
  • the fixing can be either vapor fixing, heat fixing, pressure fixing or combinations thereof as described in U.S. Patent No. 3,539,161.
  • toner material_ that is used in a development system is very important as not only is the image quality a consideration, but cleaning and damage to machine components is a factor that must be contended with.
  • the powder image can be electrically transferred to the support surface by means of a corona generating device as described for example in U.S. Patent No. 2,777,957. Specifically, transfer is effected by such a device by imparting an electrostatic charge to attract the powder image from the drum to the support surface.
  • the polarity of the charge required to affect the transfer of the image depends upon the visual form of the original copy relative to the reproduction as well as the electroscopic characteristics of the developing.material employed to accomplish development.
  • a positive polarity corona when a positive reproduction is to be obtained from a positive original it is conventional to employ a positive polarity corona 'to affect the transfer of a negatively charged toner image to a support surface.
  • a positive reproduction from a negative original normally there is used a positively charged developing material which is repelled by the charged areas on the plate to the discharged areas thereon to form a positive image which may be transferred by negative polarity corona.
  • the type of charge that. is to be imparted to the toner material will depend on the charge on the photoconductive surface, thus if such charge is negative one would want a positive charge on the resulting toner or if such a charge is positive one would want a negative charge on the resulting toner.
  • additives While these additives are somewhat effective in controlling the toner charges, the additives used can adversely affect the system in that, for example, charge could migrate from the interior of the toner to the surface due to energy differences which results in causing the toner to change its charge property and to be less attracted to the electrophotographic latent images in some situations. Also, these additives are either water soluble or moisture sensitive; thus adversely affecting the toner and the quality of the image. Further, such additives are difficult to disperse or dissolve uniformly in the toner which results in particle to particle non-uniformity and wide distribution of electrical charges.
  • the invention as claimed is intended to provide a toner composition which is positively charged and which does not require the use of an additive to obtain such a charge.
  • This toner composition is characterised by the inclusion of a resin which is in an amine copolymer or terpolymer having the formula: or wherein M 1 is a monomeric unit, M 2 is a monomeric unit different from M 1 , R 1 and R 2 are independently selected from hydrogen, carbon containing radicals, hydrocarbon and substituted hydro- carbon radicals, R 3 is hydrogen or a hydrocarbon group, n is an integer between 50 and 100,000 and Y is an integer between 1 and 5, said copolymer or terpolymer being prepared by vinyl or addition polymerization.
  • the toner compositions of the invention have the advantages that they provide improved toners having the desired charge characteristics that are permanently retained and which allow the development of images of high quality especially when a negative charge is present on the photoreceptor used.
  • the colorant which can be a carbon black, magnetite or colorant pigment is present in amounts of from about 1 to about 70 percent by weight while the resin is present in amounts of from about 30 to 99 percent by weight. In order to achieve optimum results it is preferred that the colorant be present in amounts of from 4 to about 50 percent based on the weight of toner and the resin be present in amounts of from 50 to about 96 percent by weight.
  • any suitable pigment or dye may be employed as the colorant including for example carbon black, nigrosine dye, aniline blue, Calco Oil Blue, chrome yellow, ultramarine blue, DuPont Oil Red, methylene blue chloride, phthalocyanine blue, Rose Bengal, iron oxides such as Mapico Black, Mapico Yellows, Mapico Reds, Mapico Browns, Mapico Tans, and mixtures thereof.
  • the pigment or dye should be present in the toner in a sufficient quantity to render it colored so that it will form a clearly visible image on the recording surface and generally as indicated above the percent of colorant present varies from about 1 to about 70 percent.
  • the toner may comprise a black pigment such as carbon black or magnetite.
  • toner compositions of the present invention Numerous types of resin materials may be used for preparing toner compositions of the present invention with the provision that the resulting product contains an amino group which causes the toner to be positively charged in one preferred embodiment thus allowing it to be used in those situations where the photoreceptor, especially an organic photoreceptor, is negatively charged.
  • the resin of the invention may be illustrated by an amine copolymer having the following structure: wherein M 1 is a monomeric unit such as styrene methyl methacrylate, n-butyl methacrylate, isobutyl styrene; R 1 and R 2 are as defined below; R 3 is hydrogen or a hydrocarbon group, such group containing from about 1 to about 8 carbon atoms and including for example, methyl, ethyl, propyl, isopropyl, hexyl, octyl; n is an integer of from about 50 to 100,000; and y is an integer of from about 1 to 5.
  • the terpolymer would be of similar structure with the addition of an M 2 grouping, -M 1 -M 2 -CH 2 wherein M 2 is usually a different monomeric unit such as n-butyl methacrylate.
  • the hydrocarbon or substituted hydrocarbon can be aliphatic or aromatic with the aliphatic group containing from 1 to about 8 carbon atoms including for example, methyl, ethyl, propyl, isopropyl, hexyl, and octyl.
  • substituents in the hydro- carbon group include hydroxyl, halo chloride, bromide, nitro, amino, sulfonyl, while examples of aromatic groups include phenyl, benzyl phenyl, and heterocyclic such as nitrogen containing aromatics.
  • copolymers and terpolymers containing the amino group include styrene t-butyl amino ethyl methacrylate, styrene n-butyl methacrylate, t-butyl amino ethyl methacrylate, dimethylamino ethyl methacrylate.
  • the resins of the invention are vinyl or addition type copolymers or terpolymers containing amino groups.
  • Typical of such vinyl monomeric units include the following monomers and monomers containing amino groups: styrene; p-chlorostyrene; vinyl naphthalene; ethylenecally unsaturated mono-olefins such as ethylene, propylene, butylene, isobutylene and the like; vinyl esters such as vinyl chloride, vinyl bromide, vinyl fluoride, vinyl acetate, vinyl propionate, vinyl benzoate, vinyl butyrate and the like; esters of alphamethylene aliphatic monocarboxylic acids such as methyl acrylate, ethyl acrylate, n-butylacrylate, isobutyl acrylate, dodecyl acrylate, n-octyl acrylate, 2-chloroethyl acrylate, phenyl acrylate, methyl-alpha-chloro
  • the addition polymerization technique employed embraces known polymerization techniques such as free radical, anionic and cationic polymerization processes. Any of these vinyl resins may be blended with one or more other resins if desired, preferably other vinyl resins which insure good triboelectric stability and uniform resistance against physical degradation.
  • the carrier particles employed may be electrically conductive, insulating, magnetic or non-magnetic, as long as the carrier particles are capable of triboelectrically obtaining a charge of opposite polarity to that of the toner particles so that the toner particles adhere to and surround the carrier particles.
  • the carrier particle is selected so that the toner particles acquire a charge having a polarity opposite to that of the electrostatic latent image so that toner deposition occurs in image areas.
  • the carriers are selected so that the toner particles acquire a charge having the same polarity as that of the electrostatic latent image resulting in toner deposition in the non-image areas.
  • Typical carrier materials include: sodium chloride, ammonium chloride, aluminum potassium chloride, Rochelle salt, sodium nitrate, aluminum nitrate, potassium chlorate, granular zircon, granular silicon, methyl methacrylate, glass, steel, nickel, iron, ferrites, ferromagnetic materials, silicon dioxide and the like.
  • the carriers may be employed with or without a coating. Many of the foregoing and typical carriers are disclosed in U. S.
  • Patents 2,618,441; 2,638,552; 3,591,503 and 3,533,835 directed to electrically conductive carrier coatings
  • U. S. Patent 3,525,533 directed to methyl terpolymer coating carriers which are the reaction products or organo silanes, silanols or siloxanes with unsaturated polymerizable organic compounds ⁇ optimum among those disclosed are terpolymer coatings achieved with a terpolymer formed from the addition polymerization reaction between monomers or prepolymers of: styrene, methylmethacrylate and unsaturated organo silanes, silanols or siloxanes); and nickel berry carriers as disclosed in U. S. Patents 3,847,604 and 3,767,598.
  • Nickel berry carriers are modular carrier beads of nickel characterized by a surface of recurring recesses and protrusions giving the particles a relatively large external surface area.
  • An ultimate coated carrier particle diameter between about 50 microns to about 1000 microns is preferred because the carrier particles then possess sufficient density and inertia to avoid adherence to the electrostatic images during the cascade development process.
  • the carrier may be employed with the toner composition in any suitable combination, generally satisfactory results have been obtained when about 1 part toner is used with about 10 to about 200 parts by weight of carrier.
  • the toners of the present invention may be utilized in systems such as powder cloud development, cascade development, single component touchdown development and other types of development systems.
  • the toner compositions of the present invention can be prepared by any well known toner mixing and combination technique for example, the ingredients may be thoroughly mixed by blending, mixing and milling the components and thereafter micropulverizing the resulting mixture.
  • Another well known technique for forming toner particles is to spray-dry a ball milled toner composition comprising a colorant, a resin and a solvent.
  • the toner compositions of the present invention can be used to develop electrostatic latent images on any suitable electrostatic surface capable of retaining charge including conventional photoconductors such as inorganic or organic photoconductive materials.
  • Some typical materials include sulfur, selenium, zinc sulfide, zinc oxide, cadmium sulfide, polyvinyl carbazole, 4 dimethyl amino benzylidene, 3 amino carbazole, polyvinyl carbazole, tri-nitrofluoronone, charge transfer complexes, phthalocyanines, and the like.
  • the triboelectric charge of the developer was measured by the following procedure. One hundred (100) parts of the coated carrier and 3 parts of the toner were placed in an 8 oz. glass jar. The jar containing the developer was roll mixed at a linear speed of 90 ft/min for a specific time. The developer was placed in a stainless steel Faraday cage with a 35 micron screen. The triboelectric charge was measured by blowing off the toner from the developer, using an electrometer which is connected to the Faraday cage.
  • Toner A comprised of 6 percent Regal 330. carbon black from Cabot Corporation and 94 percent of a copolymer resin was prepared by Banbury blending followed by mechanical attrition.
  • the copolymer resin was prepared by polymerizing 65 percent styrene and 35 percent n-butyl methacrylate using benzyl peroxide as an initiator.
  • the triboelectric charge of this toner against a 0.35 percent PFA (perfluor alkoxy fluoro polymer from duPont Co.) coated Hoeganaes carrier was measured by the procedure outlined above with the following results.
  • the word 'tribo' is used hereafter to denote triboelectric charge.
  • the tribo decreased rapidly as the mixing time was increased. After 4 hours of mixing, the charge of the toner changed from positive to negative, indicating it was not a stable developer.
  • Toner B which is comprised of 6 percent Regal 330 carbon black and 94 percent of Terpolymer 1 resin was prepared by Banbury/jetting.
  • the Terpolymer 1 resin of this toner was prepared by polymerizing 60 percent styrene, 38 percent n-butyl methacrylate, and 2 percent t-butylamino ethyl methacrylate using benzoyl perioxide as an initiator.
  • the triboelectric measurements of this toner against a 0.35 percent PFA (perfluoro alkoxy fluoro polymer from DuPont Co.) coated Hoeganaes carrier were as shown in the following table: The charging rate of this toner was rapid and the tribo was rather high and stable.
  • PFA perfluoro alkoxy fluoro polymer from DuPont Co.
  • Toner C comprising 6 percent Regal'330 carbon black and 94 percent Terpolymer 2 resin was prepared by Banbury/jetting.
  • the Terpolymer 2 resin of this toner was prepared by polymerizing 60 percent styrene, 36 percent n-butyl methacrylate, and 4 percent t-butylamino ethyl methacrylate using benzoyl peroxide as initiator.
  • the tribos of this toner against a 0.35 percent PFA (perfluoro alkoxy fluoro polymer from duPont Co.) coated Hoeganaes carrier were as shown in the following table: The toner displayed fast charging rate and high and stable tribo.
  • Toner D comprising 6 percent Regal 330 carbon black and 94 percent Terpolymer 3 resin was prepared by Banbury/jetting.
  • the Terpolymer 3 resin of this toner was prepared by polymerizing 60 percent styrene, 34 percent n-butyl methacrylate and 6 percent t-butyl amino ethyl methacrylate using benzoyl peroxide as initiator.
  • the tribo of this toner against a 0.35 percent PFA (perfluoro alkoxy fluoro polymer from duPont Co.) coated Hoeganaes carrier were as shown in the following table: The toner displayed fast charging rate, high and stable tribo.
  • Toner E comprising 6 percent Regal 330 carbon black and 94 percent Terpolymer 4 resin was prepared by Banbury/jetting.
  • the Terpolymer 4 resin of this toner was prepared by polymerizing 50 percent methyl methacrylate, 45 percent n-butyl methacrylate, and 5
  • the toner displayed fast charging rate, high and stable tribo against uncoated steel carrier.

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  • Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • General Physics & Mathematics (AREA)
  • Developing Agents For Electrophotography (AREA)
EP79300655A 1978-04-28 1979-04-20 Composition de toner électrophotographique Withdrawn EP0005334A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US90096178A 1978-04-28 1978-04-28
US900961 1978-04-28

Publications (1)

Publication Number Publication Date
EP0005334A1 true EP0005334A1 (fr) 1979-11-14

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ID=25413367

Family Applications (1)

Application Number Title Priority Date Filing Date
EP79300655A Withdrawn EP0005334A1 (fr) 1978-04-28 1979-04-20 Composition de toner électrophotographique

Country Status (3)

Country Link
EP (1) EP0005334A1 (fr)
JP (1) JPS54143647A (fr)
BR (1) BR7902613A (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2515374A1 (fr) * 1981-10-28 1983-04-29 Kao Corp Developpateur sec pour l'electrophotographie
FR2539237A1 (fr) * 1983-01-12 1984-07-13 Kao Corp Composition de developpateur sec
GB2159970A (en) * 1984-04-27 1985-12-11 Canon Kk Electrophotographic toner
US4656111A (en) * 1983-04-12 1987-04-07 Canon Kabushiki Kaisha Pressure-fixable toner comprising combination of a compound having hydrocarbon chain and a compound having amino group
EP0655657A1 (fr) * 1993-11-19 1995-05-31 Mita Industrial Co., Ltd. Révélateur pour un agent de développement magnétique du type à deux composants ayant une action salissante réduite

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5950448A (ja) * 1982-09-17 1984-03-23 Mitsui Toatsu Chem Inc 静電荷像現像用乾式トナ−
JPS59157655A (ja) * 1983-02-28 1984-09-07 Kao Corp 圧力定着型トナ−組成物
JPH0697347B2 (ja) * 1983-04-07 1994-11-30 キヤノン株式会社 現像方法
JPH0673022B2 (ja) * 1983-04-21 1994-09-14 キヤノン株式会社 現像方法
JPH079547B2 (ja) * 1983-09-22 1995-02-01 キヤノン株式会社 現像方法
JPS60227274A (ja) * 1984-04-26 1985-11-12 Canon Inc 現像方法
JPH0640223B2 (ja) * 1984-07-12 1994-05-25 富士ゼロックス株式会社 一成分現像剤
JPS6123160A (ja) * 1984-07-12 1986-01-31 Fuji Xerox Co Ltd 一成分現像剤
JPS61105562A (ja) * 1984-10-29 1986-05-23 Kao Corp 電子写真現像剤組成物
JPH081522B2 (ja) * 1985-02-28 1996-01-10 キヤノン株式会社 正荷電性トナ−
JPH06103405B2 (ja) * 1985-02-28 1994-12-14 キヤノン株式会社 静電荷像現像用正帯電性トナ−
JPH0680464B2 (ja) * 1985-02-28 1994-10-12 キヤノン株式会社 静電荷像現像用正帯電性トナー

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1597861A1 (de) * 1966-11-21 1970-08-13 Ricoh Kk Entwickler fuer Elektrophotographie
DE1772439A1 (de) * 1967-05-15 1971-03-04 Ricoh Kk Fluessigentwickler fuer die Elektrophotographie
JPS48102633A (fr) * 1972-04-10 1973-12-24
GB1352804A (en) * 1972-05-30 1974-05-15 Konishiroku Photo Ind Electrophotographic process employing a toner composition
DE2512112A1 (de) * 1974-03-20 1975-10-02 Hitachi Chemical Co Ltd Fluessigentwickler fuer die elektrophotographie
US3968044A (en) * 1974-02-01 1976-07-06 Rank Xerox Ltd. Milled liquid developer

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1597861A1 (de) * 1966-11-21 1970-08-13 Ricoh Kk Entwickler fuer Elektrophotographie
DE1772439A1 (de) * 1967-05-15 1971-03-04 Ricoh Kk Fluessigentwickler fuer die Elektrophotographie
JPS48102633A (fr) * 1972-04-10 1973-12-24
GB1352804A (en) * 1972-05-30 1974-05-15 Konishiroku Photo Ind Electrophotographic process employing a toner composition
US3968044A (en) * 1974-02-01 1976-07-06 Rank Xerox Ltd. Milled liquid developer
DE2512112A1 (de) * 1974-03-20 1975-10-02 Hitachi Chemical Co Ltd Fluessigentwickler fuer die elektrophotographie

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, Vol. 81, No. 6, August 12, 1974, Abstract No. 31850d, page 440, column 1 Columbus, Ohio (US) TOMARI, SEIJI: "Electrographic dry developer toner containing charge controlling polymers"; & JP-A-48 102 633 (CANON K.K.) * the entire Abstract * *

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2515374A1 (fr) * 1981-10-28 1983-04-29 Kao Corp Developpateur sec pour l'electrophotographie
FR2539237A1 (fr) * 1983-01-12 1984-07-13 Kao Corp Composition de developpateur sec
GB2133169A (en) * 1983-01-12 1984-07-18 Kao Corp Dry developer composition
US4845005A (en) * 1983-01-12 1989-07-04 Kao Corporation Dry developer composition comprising polymer binder resin and colorant
US4656111A (en) * 1983-04-12 1987-04-07 Canon Kabushiki Kaisha Pressure-fixable toner comprising combination of a compound having hydrocarbon chain and a compound having amino group
GB2159970A (en) * 1984-04-27 1985-12-11 Canon Kk Electrophotographic toner
EP0655657A1 (fr) * 1993-11-19 1995-05-31 Mita Industrial Co., Ltd. Révélateur pour un agent de développement magnétique du type à deux composants ayant une action salissante réduite
US5521045A (en) * 1993-11-19 1996-05-28 Mita Industrial Co., Ltd. Toner for a two-component-type magnetic developing agent having excellent spent resistance

Also Published As

Publication number Publication date
JPS54143647A (en) 1979-11-09
BR7902613A (pt) 1979-10-30

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Inventor name: NELSON, ROBERT A.

Inventor name: KUMAR, N. GANESH

Inventor name: LU, CHIN H.

Inventor name: BAYLEY, ROBERT D.