US3672886A - Novolak resins in deformation imaging - Google Patents

Novolak resins in deformation imaging Download PDF

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Publication number
US3672886A
US3672886A US787260A US3672886DA US3672886A US 3672886 A US3672886 A US 3672886A US 787260 A US787260 A US 787260A US 3672886D A US3672886D A US 3672886DA US 3672886 A US3672886 A US 3672886A
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frost
phenol
resin
materials
image
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Joseph Mammino
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Xerox Corp
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Xerox Corp
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    • 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
    • C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
    • 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
    • C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
    • C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
    • C08G8/08—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ
    • C08G8/10—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ with phenol
    • 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
    • C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
    • C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
    • C08G8/08—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ
    • C08G8/12—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ with monohydric phenols having only one hydrocarbon substituent ortho on para to the OH group, e.g. p-tert.-butyl phenol
    • 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
    • C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
    • C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
    • C08G8/08—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ
    • C08G8/14—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ with halogenated phenols
    • 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
    • C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
    • C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
    • C08G8/08—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ
    • C08G8/20—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ with polyhydric phenols
    • C08G8/22—Resorcinol
    • 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
    • C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
    • C08G8/28—Chemically modified polycondensates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • 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
    • G03G5/022—Layers for surface-deformation imaging, e.g. frost imaging
    • 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
    • G03G5/0614—Amines
    • G03G5/06142—Amines arylamine

Definitions

  • the frost method may involve the electrophotographic process whereby a latent electrostatic image is produced on a thin dielectric thermoplastic film. This film is then deformed either concurrently with or subsequent to charging, by heating, or exposure to an atmosphere of solvent vapors which produce a solid area visible image.
  • a charge pattern can be created which control selective wrinkling or frosting of the deformable layer to form the solid area image.
  • the frost image may be erased by reexposing the imaged ma terial to the beforesaid heat or vapor sources thus permitting the deformable layer to return to its prefrosted condition.
  • compositions for use in either or both frost and relief are rather restricted.
  • Certain thermoplastic materials, for example, that may have the desirable physical properties for commercial relief processes have been found unsuitable for frost imaging.
  • many compositions, although apparently possessing all the desirable physical and electrical properties necessary for commercial utility as deformable recording media, have demonstrated that the resulting frost or relief images in a number of instances are of poor quality and considerably less suitable than others for commercial application.
  • the choice of surface deformable materials for either process above disclosed has been limited to a comparatively small number.
  • thermoplastics Since the deformable thermoplastic must be softened to form either type of image and since discharge begins to take place by ion migration when the thermoplastics are softened, some thermoplastics cannot form frost images according to presently known techniques inasmuch as too much charge is lost from the surfaces of these films before they are sufiiciently softened for deformation to take place. This problem has significantly limited the choice of materials which may be employed in the frost process, eliminating many otherwise highly desirable materials as possible selections.
  • Another object of this invention is to provide a surface deformable imaging process utilizing a wider variety of surface deformable materials.
  • Still a further object of this invention is to provide a novel process for producing images of comparatively high quality on materials previously found to be unsuitable for such use.
  • Still another object of this invention is to provide a novel surface deformable imaging system.
  • Still another object of this invention is to provide a novel method of frost imaging utilizing prior substantially non-frostable materials.
  • the preferred range for producing the highest quality images is from about /3 part to about parts additive per 1 part resin.
  • the additives employed are generally solid under ambient conditions (at a room temperature of about 70 F.) such that they do not bleed from the composition during storage and preferably do not have a melting point significantly higher than 185 C.
  • the resins used in the present invention generally fall in the class of phenol-aldehyde type resins of the novolak variety. Any suitable phenol-aldehyde resin may be used.
  • Typical phenols useful in making the resins herein the subject of the present invention are phenol, cresol, xylenol, alkyl phenols, such as p-tertiary butyl phenol, p-cyclohexyl phenol, aryl phenols such as p-phenyl phenol, triphenyl-phydroxy phenol, alkenyl phenols such as para, and ortho-l S-di and 1,3-di-butenyl phenol, 1,3,5 tributenyl phenol, halogenated phenols such as mono, di, tri and tetra chlorinated phenol, resorcinol, hydroquinone, and mixtures thereof; sulfonated phenols such as p-hydroxy-terbutylbenzene s
  • polynuclear phenols such as alpha and beta naphthol, anthracene phenol, dihydroxy-di-phenyl alkanes such as bisphenol A and mixtures thereof. Any suitable substituted phenol as set out above may be used in the course of the present invention. 7
  • Typical aldehydes includes formaldehyde,
  • the resins of this invention may be described according to the following generic structural formula, as a composition having repeating units: OH mu I R@-R Y)m z 0H Y)n /() ⁇ R-@X v 4Y)m R is a residue of a member selected from the group wherein:
  • Y is a member selected from the group consisting of hydrogen, OH, lower alkyl (up to 6 carbon atoms), halogen and mixtures thereof;
  • X is a member selected from the group consisting of the above R and oxygen;
  • Z is an integer having a value of at least 2;
  • n as an integer having a value of from 1 to 4
  • Y m is an integer having a value of from 1 to 3.
  • the major structural feature of a phenol that determines its reactivity with aldehydes is its functionality. This may be defined as the total number of unsubstituted positions in the benzene ring that are in ortho and para position to the hydroxyl group. An ortho-para directing group in the meta position enhances the reactivity of the phenol.
  • Typical of the thermoplastic type resin which falls into the desirable category for purposes of the present invention are the novolak resins.
  • a typical modified phenol-formaldehyde resin of this kind is a diphenyl-oxide modified novolak resin identified as ET 395 and manufactured by the 'Dow Chemical Co.
  • This modified novolak is the product resulting from the reaction of dimethyl-diphenyloxide with phenol under conditions which allow for the formation of a novolak structure.
  • Typical properties for this material are:
  • the softening point and molecular weight may be controlled by the ratio of phenol to dimethyl-diphenyl oxide reaction mixture.
  • any suitable aromatic compound or mixtures thereof may be used as the additive in this invention.
  • Typical aromaticcompounds include: durene; pentamethylbenzene; hexamethylbenzene; hexaethylbenzene; diphenylmethane; triphenylmethane; diphenyl; pterphenyl; 1,3,5-triphenylbenzene, naphthalene; acenaphthene; fluorene; phenanthrene; fluoranthrene; tetraphenylethylene; isoquinoline; indole; acridine; phenyl carbonate and mixtures thereof.
  • Typical aromatic amines include: p-toluidine, 0-, m-, and p-, nitroaniline, o-, m-, and p-, phenylenediamine, p-anisidine, p-chloroaniline, pbromoaniline, 2,4,6-trichloraniline, 2,4,6-tribromoaniline, diphenylamine, triphenylamine, 2-methyltriphenylamine, 3-methyl-4'-nitrrotriphenylamine, 4 dimethlylaminotriphenylamine, o-tolidine, o-dianisidine, and mixtures thereof.
  • a preferred class of additives comprises arylamines such as triphenylamine and substituted triphenylamines. These are particularly preferred because they have a relatively high melting point and will, therefore, not bleed from the final film to which they are added, but on the other hand, produce a synergistic effect in this film.
  • arylamines such as triphenylamine and substituted triphenylamines. These are particularly preferred because they have a relatively high melting point and will, therefore, not bleed from the final film to which they are added, but on the other hand, produce a synergistic effect in this film.
  • arylamines such as triphenylamine and substituted triphenylamines.
  • the electrostatic charge pattern may I be applied to the phenol aldehyde resin by a number dispersed therethrough as a photoconductive particle in the film to make up a photoconductive film similar to the photoconductive pigment-insulating binder film, as de scribed in US. Pat. 3,121,007 to Middleton.
  • Typical photoconductive materials include: sulfur, selenium, polyvinyl carbazole, anthracene, polyvinyl anthracene, anthraquinone, acylhydrazone derivatives such as 4-dimethylamino-benzylidenebenzylhydrazide; oxadiazole derivatives such as 2,5-bis-(p-aminophenyl-(1)), 1,3,4-oxadiazole; triazole derivatives such as- 2,5-bis-(4'-dimethylaminophenyl), 1,3,4-triazole; pyrazoline derivatives such as 1,3 diphenyl 5-(p-dimethylaminophenyl) pyrazoline; imidazolone derivatives such as 4 (p-dimethylaminophenyl)-5-phenyl-imidazolone; imidazoletione derivatives such as 4 (p-trimethylaminophenyl)-5-phenylimidazolethione, 2 (4-me
  • the phenol aldehyde resin itself may be rendered photocond-uctive by complexing it with any suitable Lewis acid.
  • Typical Lewis acids are: phenyl acetic acid, 6- methyl-cumaryl-acetic acid-(4), maleic acid, cinnamic acid, benzoic acid, 1-( 4-diethylamino benzoyD-benzene 2 carbocyclic acid, phthalic acid, tetrachloropththalic acid, .organic sulfonic acids, such as 4-toluene sulfonic acid, benzene sulfonic acid, organic phosphonic acids, such as 4-chloro-3-nitro-3-benzene phosphonic acid, 4- m'trophenol, picric acid, acetic anhydride, succinic anhydride,'maleic anhydride, phthalic anhydride, tetrachlorophthalic anhydride, chrysene-2, 3,8,9 tetracarbox
  • EXAMPLE I One gram of a diphenyl oxide modified p-tertiary butyphenol-formaldehyde resin, available from the Dow Chemical Company under the designation NO-ET 693, having a melting point of about 110 C., is dissolved in 9 grams of toluene with stirring. To this solution, there is added one half gram of triphenylamine (melting point 126 C.), and then it is applied to a conductive substrate of aluminum and force dried at about 60 C. for of an hour. This coating is then charged negatively to about 300 volts DC in the dark with a corona discharge electrode which is scanned across its surface and heated to about 90 C. at which point a uniform, dense frost deformation pattern appears on its surface.
  • NO-ET 693 diphenyl oxide modified p-tertiary butyphenol-formaldehyde resin
  • Example II The procedure of Example I is repeated with the exception that gram of 2,4,7-trinitrofluorenone is added to the coating formulation and after charging of the dried film, it is exposed to a light image with an exposure of 15 foot candle seconds and then heated in the dark to a temperature of about 100 C., at which point a frost image in the pattern of the light image is seen to form on the surface of the coated film.
  • Example HI The procedure of Example I is repeated with the exception that the triphenylamine is not employed in the coating formulation. Heating as high as 120C. only produces an extremely faint deformation pattern on the surface of the coated film which is poor in definition and low density.
  • Example IV The procedure of Example II is repeated with the exception that the triphenylamine is eliminated from the coating formulation with the result that a very spotty image of extremely low density is produced when the film is heated to 115 C.
  • Example V The procedure of Example H is repeated with the exception that one half gram of phenylcarbonate is used to replace the triphenylamine. Although the image produced is not quite so dense as the one produced in Example II, it has markedly higher density than the Example II film and the deformation pattern produced is very uniform.
  • Example VI The procedure of Example I is repeated using one half gram of triphenylmethane in place of the triphenylamine. Here again, density and uniformity of the deformation pattern are much improved over that produced in Example III.
  • EXAMPLE VII One part of a p-phenylphenol-formaldehyde resin having a melting point of about C. is dissolved in 9 parts of a 50/50% mixture of toluene and methylethyl ketone with stirring. This solution is then applied to an aluminum sheet and force dried at about 60 C. for of an hour. The dried coating is then charged negatively to about 300 volts DC with a corona discharge electrode which is scanned across its surface in the dark. The coating is then heated to C. at which point an extremely faint, spotty frost deformation pattern forms on its surface.
  • Example VIII To the coating solution of Example VII, there is added 0.4 part by Weight of triphenylamine (M.P. 126 C.) which is then coated on the same type of aluminum substrate as in Example VII, charged at 300 volts DC in the dark with the same corona discharge electrode and heated to about 87 C. whereupon a uniformly, dense frost deformation pattern appears on its surface.
  • triphenylamine M.P. 126 C.
  • Example IX The procedure of Example VIII is repeated with the exception that 0.25 part of 2,4,7-trinitrofluorenone is added to the coating solution. Prior to heating, the coating is exposed to an image with a visible light source. Here again, a uniform, high density frost pattern occurs upon heating to about 87 C., but it forms only in unexposed areas of the coating.
  • Example VII The coating solution of Example VII is again formulated and 0.5 part of diphenylamine is added thereto prior to coating. After charging and heating to about 77 C., as described above, a uniform, frost pattern of high density is found to form across the surface of the charged coating.
  • Example XI To the coating solution of Example VII, there is added 0.4 gram of o-phenylene diamine. After charging and heating, as in Example VII, it is found that a uniform high density frost image with slightly lower density than Example X is formed at about 100 C.
  • EXAMPLE XIII 0.35 part by weight of diphenyl are added to a reformulation of the Example XI solution and this coating is then applied to an aluminum substrate, force dried, charged and heated in the same manner as employed in connection with Example XII. A uniform, high density frost pattern is found to occur at about 82 C.v
  • EXAMPLE XIV 0.5 part of triphenylamine are added to a re-formulation of the coating solution of Example XII, and this coating material is then applied to the aluminum substrate, force dried, charged and heated in the same manner as in Example XII. It is found that a uniform, very high density frost pattern forms across the whole surface of the coating at about 105 C.
  • EXAMPLE XV About 0.25 part of 2,4,7-trinitrofluorenone are added to a re-formulation of the coating solution of Example XIV and after force drying and charging, according to the same procedure employed in Example XIV, the coating is exposed to an image pattern with a visible light source and is then heated as in Example XIV.
  • a high density frost deformation pattern is formed but it only appears in unexposed areas.
  • Example XVI The procedure of Example XII is repeated with the exception that 0.4 part of naphthalene are added to the coating solution. This is found to result in the'production of a uniform, high density, frost pattern on the surface of the coating upon heating to about 80 C.
  • any of the above listed typical materials may be substituted where suitable in the above examples with similar results being obtained.
  • other steps or modifications may be used, if desirable.
  • the frost image formed may be fixed, erased and then refrosted at least more than one time.
  • other materials may be incorporated in the surface deformable material and additive which will enhance, synergize, or otherwise desirably effect the properties of these materials for their present use.
  • a frost imaging process comprising forming an electrostatic charge pattern on the surface of a surface deformable material which comprises a phenol-aldehyde novolak resin and an additive, said phenolaldehyde' constituent having the following generic structure with repeating units:
  • R is a residue selected from at least onemember of the group consisting of formaldehyde, paraformaldehyde, furfural, aminoformaldehyde, acrolein, benzaldehyde, chloral, oxoaldehydes, acetaldehyde, glyoxal, propionaldehyde, butyraldehyde, isobutyraldehyde, N-valeraldehyde, isovaleraldehyde, n-caproaldehyde, n-heptaldehyde, stearaldehyde, and crotonaldehyde;
  • Y is selected from at least one member of the-group consisting of hydrogen, hydroxyl, lower alkyl'(up to 6 carbon atoms), and halogen;
  • X is selected from at least one member of the group consisting of the above R and oxygen;
  • Z is an integer having a value of at least 2;
  • said additive being selected from at least one member of the group consisting of triphenylamine,triphenylmethane, diphenylamine, 2 methyl triphenylamine, 3 methyl-4' nitro-triphenylamine, 4 dimethylamino triphenylamine, tetra-phenylethylene, naphthalene, diphenyl, o-phenylenediamine, and phenylcarbonate, said additive having a melting point of between about F. and C. and softening said surface deformable material at a temperature' lower than the melting point of saidresin to form a frost deformable pattern thereon.
  • said surface deformable material further comprises a photoconductive insulating material and said electrostatic charge pattern is formed by uniformly charging the surface of said surface deformable material and selectively exposing said charged surface to a lightimage.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Photoreceptors In Electrophotography (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
US787260A 1964-12-28 1968-12-26 Novolak resins in deformation imaging Expired - Lifetime US3672886A (en)

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US42161364A 1964-12-28 1964-12-28
US78726068A 1968-12-26 1968-12-26

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US3672886A true US3672886A (en) 1972-06-27

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US (1) US3672886A (enrdf_load_stackoverflow)
DE (1) DE1497229B2 (enrdf_load_stackoverflow)
FR (1) FR1469081A (enrdf_load_stackoverflow)
GB (1) GB1133772A (enrdf_load_stackoverflow)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3892567A (en) * 1971-04-13 1975-07-01 Xerox Corp Electrostatically deformable materials
US4150985A (en) * 1974-12-13 1979-04-24 International Business Machines Corporation Image forming process involving phase change
US5023311A (en) * 1985-12-06 1991-06-11 Toray Industries, Inc. High-molecular-weight soluble novolak resin and process for preparation thereof
CN100375924C (zh) * 2001-12-21 2008-03-19 佳能株式会社 酚类化合物、甲阶酚醛树脂、其固化物、电子照相感光体、处理盒和电子照相装置

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3892567A (en) * 1971-04-13 1975-07-01 Xerox Corp Electrostatically deformable materials
US4150985A (en) * 1974-12-13 1979-04-24 International Business Machines Corporation Image forming process involving phase change
US5023311A (en) * 1985-12-06 1991-06-11 Toray Industries, Inc. High-molecular-weight soluble novolak resin and process for preparation thereof
CN100375924C (zh) * 2001-12-21 2008-03-19 佳能株式会社 酚类化合物、甲阶酚醛树脂、其固化物、电子照相感光体、处理盒和电子照相装置

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FR1469081A (fr) 1967-02-10
DE1497229C3 (enrdf_load_stackoverflow) 1975-08-14
DE1497229B2 (de) 1975-01-09
DE1497229A1 (de) 1969-05-14
GB1133772A (en) 1968-11-20

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