EP0319992B1 - Electrophotographic light-sensitive material - Google Patents

Electrophotographic light-sensitive material Download PDF

Info

Publication number
EP0319992B1
EP0319992B1 EP19880120607 EP88120607A EP0319992B1 EP 0319992 B1 EP0319992 B1 EP 0319992B1 EP 19880120607 EP19880120607 EP 19880120607 EP 88120607 A EP88120607 A EP 88120607A EP 0319992 B1 EP0319992 B1 EP 0319992B1
Authority
EP
European Patent Office
Prior art keywords
phenyl
compound
sensitive material
charge
light
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.)
Expired - Lifetime
Application number
EP19880120607
Other languages
German (de)
English (en)
French (fr)
Other versions
EP0319992A2 (en
EP0319992A3 (en
Inventor
Tomokazu Kobata
Yosuke Matsui
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.)
Bando Chemical Industries Ltd
Original Assignee
Bando Chemical Industries Ltd
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 Bando Chemical Industries Ltd filed Critical Bando Chemical Industries Ltd
Publication of EP0319992A2 publication Critical patent/EP0319992A2/en
Publication of EP0319992A3 publication Critical patent/EP0319992A3/en
Application granted granted Critical
Publication of EP0319992B1 publication Critical patent/EP0319992B1/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Images

Classifications

    • 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
    • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0601—Acyclic or carbocyclic compounds
    • G03G5/0612—Acyclic or carbocyclic compounds containing nitrogen
    • G03G5/0616—Hydrazines; Hydrazones

Definitions

  • This invention relates to an electrophotographic light-sensitive material having a composite light-sensitive layer formed by a layer of a charge transporting substance and a layer of a charge producing substance on an electrically conductive support.
  • a light-sensitive material having a layer of selenium is low in flexibility and its handling involves quite a bit of difficulty, as selenium is a highly toxic substance.
  • a light-sensitive material having a layer of zinc oxide can only poorly be charged with electricity, shows a high degree of charge attenuation in the dark, and is low in sensitivity.
  • a light-sensitive material having an organic light-sensitive layer formed by a charge transfer complex composed of polyvinylcarbazole and trinitrofluorenone This material is also low in sensitivity and the toxicity of trinitrofluorenone presents a difficult problem, too.
  • a composite or laminated type electrophotographic light-sensitive material has been developed to improve the prior materials as hereinabove described.
  • This type of light-sensitive material is disclosed in, for example, Japanese Patent Publications Nos. 42380/1980 and 34099/1985. It comprises an electrically conductive support 3 having a layer of aluminum 2 deposited on a polyester film 1, a layer 4 of a charge producing substance formed on the aluminum layer 2, and a layer 5 of a charge transporting substance formed on the layer 4, as shown by way of example in FIGURE 18.
  • Examples of the charge transporting substance include p-N,N-dialkylaminobenzaldehyde-N′,N′-diphenylhydrazone, particularly p-N,N-diethylaminobenzaldehyde-N′,N′-diphenylhydrazone, p-N,N-diphenylaminobenzaldhyde-N′-methyl-N′-phenylhydrazone and p-N-ethyl-N-phenyl-aminobenzaldehyde-N′-methyl-N′-phenylhydrazone.
  • the layer of any such substance and the layer of a charge producing substance are laid on the electrically conductive support.
  • the layer of a charge transporting substance is formed by, for example, dissolving it in an organic solvent to prepare a solution containing a binding resin, which may further contain a plasticizer, etc. as required, applying the solution onto the support or the layer of a charge producing substance, and drying it, whereby a layer having a thickness of, say, 5 to 100 ⁇ m (microns) is formed.
  • the charge transporting substance has a decisive bearing on the performance or quality of any electrophotographic light-sensitive material of the type to which this invention pertains.
  • the manufacture of an electrophotographic light-sensitive material having high sensitivity requires the provision of a layer containing a charge transporting substance in a relatively high concentration and therefore the use of a charge transporting substance which is highly compatible with the resin used as a bonding agent.
  • the substance must also be one from which any such layer can be formed easily.
  • the charge transporting substance is required to have an appropriately low oxidation potential and a high charge transfer rate, so that the charge which is produced in the layer of the charge producing substance may be effectively injected into the layer of the charge transporting substance.
  • organic compounds having a low oxidation potential are generally liable to oxidation and unstable.
  • an object of this invention to provide an electrophotographic light-sensitive material of the composite or laminated type including a layer of a charge transporting substance which is highly compatible with a bonding agent, has an appropriately low oxidation potential, is stable and has a high charge transfer rate, and has a high degree of sensitivity.
  • the object of this invention is, therefore, attained by an electrophotographic light-sensitive material having a layer of a charge transporting substance and a layer of a charge producing substance formed on an electrically conductive support, wherein the charge transporting substance is an arylaldehydehydrazone derivative characterized in that the arylaldehydehydrazone is of the general formula: where R1, R2 and R3 are each an alkyl or aryl group.
  • the arylaldehydehydrazone derivative is highly compatible with an organic solvent and a resin used as a bonding agent, has an appropriately low oxidation potential, exhibits a completely reversible oxidation-reduction reaction and is, therefore, very stable, and also has a high charge transfer rate.
  • the electrophotographic light-sensitive material of this invention containing any such derivative as a charge transporting substance has, therefore, a high degree of sensitivity and a high degree of printing resistance.
  • the electrophotographic light-sensitive material of this invention contains as a charge transporting substance an arylaldehydehydrazone derivative of the general formula shown above, in which R1, R2 and R3 are each an alkyl or aryl group.
  • the alkyl group may, for example, be a methyl, ethyl, propyl, butyl, pentyl, hexyl, octyl, nonyl or dodecyl group. It may be in the form of a straight or branched chain.
  • the aryl group may, for example, be an unsubstituted or substituted phenyl, naphthyl, anthryl, pyrenyl, acenaphthenyl or fluorenyl group.
  • the substituent may, for example, be an alkyl group such as methyl, ethyl, propyl, butyl, pentyl, hexyl, octyl, nonyl, or dodecyl, an alkoxy group such as methoxy, ethoxy, propoxy or butoxy, a halogen such as chlorine, bromine or fluorine, an aryloxy group such as phenoxy or tolyloxy, or a dialkylamino group such as dimethylamino, diethylamino or dipropylamino.
  • an alkyl group such as methyl, ethyl, propyl, butyl, pentyl, hexyl, octyl, nonyl, or dodecyl
  • an alkoxy group such as methoxy, ethoxy, propoxy or butoxy
  • a halogen such as chlorine, bromine or fluorine
  • an aryloxy group such as phen
  • R1, R2 and R3 are each a methyl, ethyl, propyl, butyl, phenyl, tolyl or chlorophenyl group.
  • arylaldehydehydrazone derivatives can be manufactured by reacting the corresponding arylaldehyde with hydrazine appropriately in accordance with any customary process that is employed for producing aldehydehydrazone.
  • the electrophotographic light-sensitive material of this invention can be manufactured if a solution or dispersion of a charge producing substance in an organic solvent containing a resin as a bonding agent, which may further contain a plasticizer, etc. as required, is applied onto an electrically conductive support and dried to form a charge producing layer, and if a solution of an arylaldehydehydrazone derivative in an organic solvent containing a resin as a bonding agent, which may further contain a plasticizer, etc. as required, is applied onto the charge producing layer and dried to form a charge transporting layer.
  • the order in which the two layers are formed can, however, be reversed, so that the charge transporting layer may be formed on the support.
  • the charge transporting layer preferably contains 10 to 60% by weight of the arylaldehydehydrazone derivative and has a thickness of 5 to 100 microns.
  • the charge producing layer may usually contain 5 to 50% by weight of the resin as a bonding agent, though its content had better be lowered as far as possible within that range. Its thickness is usually from 0.05 to 20 microns, and preferably from 0.1 to 10 microns.
  • the charge producing layer can also consist solely of a charge producing substance.
  • the resin used as a bonding agent is of the type which is soluble in an organic solvent and is highly compatible with a charge producing or transporting substance, so that a stable solution or dispersion thereof can be prepared easily. Moreover, it is preferable to use a resin which is inexpensive and can form a film of high mechanical strength, transparency and electrical insulating property.
  • Preferred examples of the resin are polycarbonate, polystyrene, polyester and polyvinyl chloride resins.
  • the organic solvent it is possible to use any solvent with any limitation in particular. Preferred examples of the organic solvent are, however, chloroform, 1,2-dichloroethane, 1,1,2,2-tetrachloroethane and tetrahydrofuran.
  • FIGURE 1 The infrared absorption spectrum of the compound is shown in FIGURE 1.
  • FIGURE 2 The results of its cyclic voltammetric analysis are shown in FIGURE 2 to show one of its electrochemical properties. It shows the complete reversibility of the compound in an oxidation-reduction reaction.
  • the solution was subjected twice to recrystallization from a mixed solvent consisting of benzene and ethanol in a ratio of 2:3, whereby the captioned compound was obtained as fine crystals having a light yellow color.
  • the compound weighed 50 g and showed, therefore, a yield of 46.1%.
  • FIGURE 3 The infrared absorption spectrum of the comppund is shown in FIGURE 3, and the results of its cyclic voltammetric analysis in FIGURE 4. It showed complete reversibility in a oxidation-reduction reaction.
  • FIGURE 5 shows the charge transfer rate of the composition which was obtained by dissolving the compound in polycarbonate in equal proportions by weight.
  • FIGURE 5 also shows the charge transfer rate of the polycarbonate composition which was likewise prepared by employing p-diethylaminobenzaldehydediphenylhydrazone as a charge transporting substance for the sake of comparison.
  • the compound (2) showed a higher charge transfer rate than that of the comparative composition.
  • the compound (2) further showed the following data: Melting point: 193.5°C to 195.0°C; Mass analysis: Molecular ion peak 634; Elemental analysis: C H N Calculated value 85.14 6.03 8.83 Measured value 85.16 6.08 8.76
  • FIGURE 6 The infrared absorption spectrum of the compound is shown in FIGURE 6, and the results of its cyclic voltammetric analysis in FIGURE 7. It showed complete reversibility in a oxidation-reduction reaction.
  • a compatibilized composition was prepared by dissolving the compound in polycarbonate in equal proportions by weight and its charge transfer rate is shown in TABLE 1 below.
  • FIGURE 8 The infrared absorption spectrum of the compound is shown in FIGURE 8, and the results of its cyclic voltammetric analysis in FIGURE 9. It showed complete reversibility in an oxidation-reduction reaction.
  • a compatibilized composition was prepared by dissolving the compound in polycarbonate in equal proportions by weight and its charge transfer rate is shown in TABLE 1.
  • the oily matter was refined and separated by silica gel chromatography employing a mixed solvent consisting of benzene and hexane in a ratio of 1:1. Then, it was recrystallized twice from a mixed solvent consisting of benzene and ethanol in a ratio of 3:2, whereby the captioned compound was obtained as fine crystals having a light yellow color. The compound weighed 95 g and showed, therefore, a yield of 72%.
  • FIGURE 10 The infrared absorption spectrum of the compound is shown in FIGURE 10, and the results of its cyclic voltammetric analysis in FIGURE 11. It showed complete reversibility in an oxidation-reduction reaction.
  • a compatibilized composition was prepared by dissolving the compound in polycarbonate in equal proportions by weight and its charge transfer rate is shown in TABLE 1.
  • FIGURE 12 The infrared absorption spectrum of the compound is shown in FIGURE 12, and the results of its cyclic voltammetric analysis in FIGURE 13. It showed complete reversibility in an oxidation-reduction reaction.
  • a compatibilized composition was prepared by dissolving the compound in polycarbonate in equal proportions by weight and its charge transfer rate is shown in TABLE 1.
  • the oily matter was refined and separated by silica gel chromatography employing a mixed solvent consisting of benzene and hexane in a ratio of 1:1. Then, it was recyrstallized from a mixed solvent consisting of benzene and ethanol in a ratio of 1:5, whereby the captioned compound was obtained as leaf-shaped crystals having a light yellow color.
  • the compound weighed 7.3 g and showed, therefore, a yield of 48%.
  • FIGURE 14 The infrared absorption spectrum of the compound is shown in FIGURE 14, and the results of its cyclic voltammetric analysis in FIGURE 15. It showed complete reversibility in an oxidation-reduction reaction.
  • a compatibilized composition was prepared by dissolving the compound in polycarbonate in equal proportions by weight and its charge transfer rate is shown in TABLE 1.
  • FIGURE 16 The infrared absorption spectrum of the compound is shown in FIGURE 16, and the results of its cyclic voltammetric analysis in FIGURE 17. Its oxidation-reduction reactions were completely reversible.
  • a compatibilized composition was prepared by dissolving the compound in polycarbonate in equal proportions by weight and its charge transfer rate was as shown in TABLE 1 above.
  • a laminated light-sensitive material was made by following the procedures of EXAMPLE 1, except that p-[(p-phenyl-p-tolylamino)phenyl)-p-tolyl]aminobenzaldehydediphenylhydrazone [Compound (2)] was used as the charge transporting substance.
  • a laminated light-sensitive material was made by following the procedures of EXAMPLE 1, except that N,N-diethylaminobenzaldehydediphenylhydrazone was used as the charge transporting substance.
  • a solution was prepared by dissolving six parts by weight of p-[(p-diphenylaminophenyl)phenyl]aminobenzaldehydediphenylhydrazone [Compound (1)] and six parts by weight of polycarbonate (the same product as had been used in EXAMPLE 1) in 88 parts by weight of chloroform. It was applied onto the charge producing layer by a doctor blade having a clearance of 100 microns. After the coating had been allowed to dry at room temperature, it was dried by heating at 80°C for an hour to form a charge transporting layer having a thickness of 15 microns, whereby a laminated light-sensitive material was obtained.
  • a laminated light-sensitive material was made by following the procedures of EXAMPLE 3, except that p-[(p-(phenyl-p-tolylamino)phenyl)-p-tolyl]aminobenzaldehydediphenylhydrazone [Compound (2)] was used as the charge transporting substance.
  • a laminated light-sensitive material was made by repeating EXAMPLE 3, except that N,N-diethylaminobenzaldehydediphenylhydrazone was used as the charge transporting substance.
  • a laminated light-sensitive material was made by repeating EXAMPLE 3, except that p-[(p-(diphenylaminophenyl)phenyl]aminobenzaldehydemethylphenylhydrazone [Compound (5)] was used as the charge transporting substance.
  • a laminated light-sensitive material was made by repeating EXAMPLE 3, except that p-[(p-(phenyl-p-tolylamino)phenyl)-p-tolyl]aminobenzaldehydemethylphenylhydrazone [Compound (4)] was used as the charge transporting substance.
  • a laminated light-sensitive material was made by repeating EXAMPLE 3, except that p-[(p-(phenyl-p-chlorophenyl)phenyl)-p-chlorophenyl]aminobenzaldehydediphenylhydrazone [Compound (8)] was used as the charge transporting substance.
  • a laminated light-sensitive material was made by repeating EXAMPLE 3, except that p-[(p-(phenyl-p-chlorophenyl)phenyl)-p-chlorophenyl]aminobenzaldehydemethylphenylhydrazone [Compound (9)] was used as the charge transporting substance.
  • a laminated light-sensitive material was made by repeating EXAMPLE 9, except that p-[(p-(phenyl-p-tolylamino)phenyl)-p-tolyl]aminobenzaldehydemethylphenylhydrazone [Compound (4)] was used as the charge transporting substance.
  • a laminated light-sensitive material was made by repeating EXAMPLE 9, except that p-[(p-(phenyl-p-chlorophenyl)phenyl)-p-chlorophenyl]aminobenzaldehyde diphenylhydrazone [Compound (8)] was used as the charge transporting substance.
  • a laminated light-sensitive material was made by repeating EXAMPLE 9, except that p-[(p-(phenyl-p-chlorophenyl)phenyl-p-chlorophenyl]aminobenzaldehydemethylphenylhydrazone [Compound (9)] was used as the charge transporting substance.
  • a laminated light-sensitive material was made by repeating EXAMPLE 9, except that N,N-diethylaminobenzaldehydediphenylhydrazone was used as the charge transporting substance.
  • a laminated light-sensitive material was made by repeating EXAMPLE 9, except that p-[(p-(methylphenylamino)phenyl)methyl]aminobenzaldehydediphenylhydrazone [Compound (10)] was used as the charge transporting substance.
  • the light-sensitive materials which had been prepared as hereinabove described were each evaluated for electrostatic charging characteristics by means of an electrostatic copying paper testing device (Model SP428 of Kawaguchi Electric Machine Mfg. Co., Ltd.).
  • the surface of each material was negatively charged with a corona discharge of -6 kV.
  • Some materials were each irradiated with white light having an illumination of 5 lux, and some with monochromatic light having a wavelength of 750 nm and a luminous intensity of 0.5 ⁇ W/cm2.
  • the length of time was measured until the point at which the surface potential of each material dropped to a half of its initial value, and the half-life exposure E 1/2 of each material to that point of time was determined as its light sensitivity.
  • TABLE 4 shows the initial potential and half-life exposure of each of the materials according to EXAMPLES 9 to 13 and COMPARATIVE EXAMPLE 3.
  • the electrophotographic light sensitive materials according to this invention as well as the materials of the COMPARATIVE EXAMPLES, were tested for electrophotographic reproduction. All of the materials according to this invention could reproduce an image which was superior to what was obtained by any of the materials according to the COMPARATIVE EXAMPLES.
  • the materials according to this invention were also excellent in printing resistance, as no change was found in the quality of image even after reproduction had been repeated several thousand times.

Landscapes

  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Photoreceptors In Electrophotography (AREA)
EP19880120607 1987-12-10 1988-12-09 Electrophotographic light-sensitive material Expired - Lifetime EP0319992B1 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP313805/87 1987-12-10
JP31380587 1987-12-10
JP25425588A JPH01257850A (ja) 1987-12-10 1988-10-07 電子写真感光体
JP254255/88 1988-10-07

Publications (3)

Publication Number Publication Date
EP0319992A2 EP0319992A2 (en) 1989-06-14
EP0319992A3 EP0319992A3 (en) 1989-11-29
EP0319992B1 true EP0319992B1 (en) 1993-04-14

Family

ID=26541597

Family Applications (1)

Application Number Title Priority Date Filing Date
EP19880120607 Expired - Lifetime EP0319992B1 (en) 1987-12-10 1988-12-09 Electrophotographic light-sensitive material

Country Status (3)

Country Link
EP (1) EP0319992B1 (enrdf_load_stackoverflow)
JP (1) JPH01257850A (enrdf_load_stackoverflow)
DE (1) DE3880277T2 (enrdf_load_stackoverflow)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0351855A (ja) * 1989-07-19 1991-03-06 Bando Chem Ind Ltd 積層型有機感光体
JPH03129356A (ja) * 1989-07-28 1991-06-03 Bando Chem Ind Ltd 積層型有機感光体

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3201202A1 (de) * 1982-01-16 1983-07-28 Basf Ag, 6700 Ludwigshafen Neue phenylhydrazone und deren verwendung
JPS62244060A (ja) * 1986-04-17 1987-10-24 Canon Inc 電子写真感光体

Also Published As

Publication number Publication date
JPH01257850A (ja) 1989-10-13
EP0319992A2 (en) 1989-06-14
DE3880277T2 (de) 1993-08-26
DE3880277D1 (de) 1993-05-19
JPH0466506B2 (enrdf_load_stackoverflow) 1992-10-23
EP0319992A3 (en) 1989-11-29

Similar Documents

Publication Publication Date Title
US4624904A (en) Photoconductive imaging members with unsymmetrical squaraine compounds containing an hydroxyl group
US4092162A (en) Nitrogen containing polymers aelements
JPS5857739B2 (ja) ヒカリデンドウセイソセイブツ
US4365017A (en) Telluropyrylium electron accepting dye sensitizers for electron donating photoconductive compositions
US4751327A (en) Photoconductive imaging members with unsymmetrical squaraine compounds
US4396695A (en) Electrophotographic medium with heterocyclic azo photoconductor
US4700001A (en) Novel squarylium compound and photoreceptor containing same
GB2151367A (en) Electrophotographic elements
US4814245A (en) Electrophotographic photoreceptor containing a phthalocyanine pigment and a bishydrazone compound
US4889785A (en) Electrophotographic light-sensitive material
US3705913A (en) Electrophotographic sensitizers
EP0319992B1 (en) Electrophotographic light-sensitive material
US4396694A (en) Organic electrophotographic sensitive materials
JPH0120741B2 (enrdf_load_stackoverflow)
US4357405A (en) Fluorinated dye sensitized organic electron donor compound
DE3521652C2 (enrdf_load_stackoverflow)
US3647431A (en) Substituted bis(p-diakylaminophenyl) methane photoconductors
US4634553A (en) Novel 4H-tellurin tellurane electron-accepting sensitizers for electron-donating photoconductive compositions
US4752650A (en) Photoreceptor for electrophotography
US5223362A (en) Laminated organic photosensitive material
US3872046A (en) Sulfonated phenol (sulfo) phthalein
US3615416A (en) 9 10-substituted acridines as sensitizers in electrophotographic systems
US4666811A (en) Organic photoconductors having improved pre-exposure fatigue resistance and blooming properties
JPH03113459A (ja) 電子写真用感光体
US3755310A (en) Substituted bis(p-dialkylaminophenyl)methane photoconductors

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

AK Designated contracting states

Kind code of ref document: A2

Designated state(s): BE DE FR GB IT NL

PUAL Search report despatched

Free format text: ORIGINAL CODE: 0009013

AK Designated contracting states

Kind code of ref document: A3

Designated state(s): BE DE FR GB IT NL

17P Request for examination filed

Effective date: 19900426

17Q First examination report despatched

Effective date: 19920601

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): BE DE FR GB IT NL

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: NL

Effective date: 19930414

Ref country code: FR

Effective date: 19930414

Ref country code: BE

Effective date: 19930414

Ref country code: IT

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRE;WARNING: LAPSES OF ITALIAN PATENTS WITH EFFECTIVE DATE BEFORE 2007 MAY HAVE OCCURRED AT ANY TIME BEFORE 2007. THE CORRECT EFFECTIVE DATE MAY BE DIFFERENT FROM THE ONE RECORDED.SCRIBED TIME-LIMIT

Effective date: 19930414

REF Corresponds to:

Ref document number: 3880277

Country of ref document: DE

Date of ref document: 19930519

EN Fr: translation not filed
NLV1 Nl: lapsed or annulled due to failure to fulfill the requirements of art. 29p and 29m of the patents act
PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

26N No opposition filed
PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: GB

Payment date: 19941205

Year of fee payment: 7

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: DE

Payment date: 19941228

Year of fee payment: 7

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GB

Effective date: 19951209

GBPC Gb: european patent ceased through non-payment of renewal fee

Effective date: 19951209

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: DE

Effective date: 19960903