And Monomeric Processing Ingredient Patents (Class 430/191)
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Patent number: 4721665Abstract: The invention features a lithographic composition fabricated from a process wherein an acidic novolak resin is neutralized in solution. The solution comprises a common compatible solvent with the other ingredients of the coating composition, such as a positive sensitizer, a color changing dye, and a light activated, acid-releasing compound.Type: GrantFiled: September 29, 1986Date of Patent: January 26, 1988Assignee: Polychrome CorporationInventors: Thomas Dooley, James Shelnut
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Patent number: 4719166Abstract: Positive-working photoresist elements are protected against reflection of activating radiation from the substrate by incorporation of certain butadienyl dyes in a photoresist layer, an anti-reflective layer or a planarizing layer. These dyes have superior resistance to thermal degradation or volatilization at temperatures of as high as 200.degree. C. or more. The dyes also exhibit good solubility in solvents commonly employed in processing semiconductor devices, thus permitting the dyes to be incorporated in photoresist elements in an amount sufficient to prevent resist image distortion caused by backscattered or reflected light.Type: GrantFiled: July 29, 1986Date of Patent: January 12, 1988Assignee: Eastman Kodak CompanyInventors: Richard W. Blevins, Robert C. Daly
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Patent number: 4707430Abstract: Disclosed herein is an optical recording medium which includes a recording layer composed of (a) an organometallic complex having an absorption maximum in the wavelength range of 600-1200 nm, (b) a resinous binder and (c) a sensitizer capable of generating radicals upon exposure to ultraviolet rays. The recording of information on the recording layer is effected with ease by exposure to ultraviolet rays. The reproduction of recorded information is effected by a laser beam having an oscillatory wavelength in the visible or near infrared wavelength range.Type: GrantFiled: February 26, 1986Date of Patent: November 17, 1987Inventors: Hiroshi Ozawa, Yoichi Hosono, Sumio Hirose, Katsuyoshi Sasagawa, Masao Imai
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Patent number: 4702992Abstract: The undercoating composition of the invention, useful for providing an undercoating layer for a top coat of a photosensitive resist layer on a substrate surface, comprises, as a principal ingredient thereof, a condensation product obtained by the condensation reaction between a hydroxy-substituted diphenylamine and a melamine compound substituted on the nitrogen atoms with methylol groups and/or alkoxymethyl groups. The undercoating obtained of the composition is highly resistant against the attack by the overcoating solution applied thereon so that the fidelity of the pattern reproduction by the photolithographic technique is greatly improved by virtue of the absence of any disorder at the interface between the undercoating and top coat layers. The advantage is further increased when the undercoating composition further comprises a photoextinctive agent, e.g. a dye, having absorptivity in the wave length region where the photosensitive resist of the top coat has sensitivity.Type: GrantFiled: March 6, 1985Date of Patent: October 27, 1987Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Wataru Ishii, Shozo Miyazawa, Shinji Tsuchiya, Hisashi Nakane, Akira Yokota
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Patent number: 4701399Abstract: A photosensitive composition containing a 2-halomethyl-5-substituted-1,3,4-oxadiazole compound represented by the following general formula (I): ##STR1## wherein A represents a substituted or unsubstituted aromatic residue; X represents a hydrogen atom, a cyano group, an alkyl group or an aryl group; Y represents a chlorine atom or a bromine atom; and n represents an integer of 1 to 3.The free radical generating agent represented by the general formula (I) has a photosensitive wavelength range from near ultraviolet range to visible range, high photo-decomposition sensitivity and good compatibility with other components present in the photosensitive composition.The photosensitive composition is suitable for use in light-sensitive printing plates or photo-resists.Type: GrantFiled: February 25, 1985Date of Patent: October 20, 1987Assignee: Fuji Photo Film Co., Ltd.Inventors: Teruo Nagano, Tadao Toyama, Akira Nagashima
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Patent number: 4699867Abstract: Disclosed is a radiation-sensitive composition, a recording material prepared therewith, and process therefor. The invention is suitable for the production of printing plates and photoresists. The composition contains a 1,2-quinonediazide or a combination of (1) a compound which, under the action of actinic radiation, forms a strong acid, and (2) a compound which possesses at least one acid-cleavable C--O--C bond, the solubility of which in a liquid developer is increased by the action of acid and, as the binder, a polymer having lateral crosslinking groups of the formula --CH.sub.2 OR, in which R is a hydrogen atom, a lower alkyl group, acyl group or hydroxyalkyl group. After being exposed and developed, the composition can be thermally cured and results in an image stencil exhibiting a clean background.Type: GrantFiled: November 22, 1985Date of Patent: October 13, 1987Assignee: Hoechst AktiengesellschaftInventors: Arnold Schneller, Ulrich Geissler
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Patent number: 4686280Abstract: A positive type resist material with high oxygen plasma resistance and a process for forming high resolution resist patterns using the resist material are disclosed. The positive type resist material comprises a photoactive resin, an organic solvent, and 5 to 50% by weight of trimethylsilylnitrile.A compound of a phenol resin having phenolic hydroxyl groups and a photoactive compound, or phenolformaldehyde is used as an example of the photoactive resin. As the solvent, selected from the group consisting of 1,2-ethoxyl acetate, methyl ethyl ketone, xylene, and n-butyl acetate are used alone or in combination.Type: GrantFiled: April 25, 1985Date of Patent: August 11, 1987Assignee: Oki Electric Industry Co., Ltd.Inventor: Ken Ogura
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Patent number: 4681923Abstract: An electrodepositable photosensitive modified phenolic novolak resin of general formula ##STR1## where Ar.sup.1 represents a divalent aromatic group linked through aromatic carbon atoms to the indicated groups --OR.sup.2 and --CH(R.sup.1)--,Ar.sup.2 represents a trivalent aromatic group linked through aromatic carbon atoms to the indicated groups --OR.sup.2 and --CH(R.sup.1)--,R.sup.1 represents a hydrogen atom or an alkyl, aryl or carboxyl group,R.sup.2 represents a hydrogen atom, an alkyl group which may be substituted by a hydroxyl or alkoxy group, or a group of formula --CO--R.sup.3 --COOH, --SO.sub.2 R.sup.4, --COR.sup.5 or --SO.sub.2 R.sup.5, at least 1% of the groups R.sup.2 representing a group --CO--R.sup.3 --COOH and at least 4% of the groups R.sup.2 representing a group --SO.sub.2 R.sup.4,R.sup.3 denotes a divalent aliphatic, cycloaliphatic, aromatic or araliphatic group,R.sup.4 denotes a 1,2-benzoquinone diazide group or 1,2-naphthoquinone diazide groupR.sup.Type: GrantFiled: February 21, 1986Date of Patent: July 21, 1987Assignee: Ciba-Geigy CorporationInventors: Christopher G. Demmer, Edward Irving
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Radiation-sensitive composition and recording material based on compounds which can be split by acid
Patent number: 4678737Abstract: A radiation-sensitive composition is disclosed which comprises: (a) a polymeric binder comprised of an alkenyl phenol monomer; (b) a compound which forms a strong acid under the action of actinic radiation; and (c) a compound which contains at least one acid-cleavable C-O-C bond and has a solubility in a liquid developer which is increased by the action of acid. The composition yields positive-working recording layers which are more flexible than layers comprising known novolak binders.Type: GrantFiled: November 25, 1986Date of Patent: July 7, 1987Assignee: Hoechst AktiengesellschaftInventors: Arnold Schneller, Walter Herwig, Kurt Erbes -
Patent number: 4672021Abstract: This invention relates to a composition and method for enhancing the contrast of images of an underlying photolithographic layer. A photographic element, including a photoresist layer, is applied to a substrate. The photoresist layer contains a contrast-enhancing layer including at least one light-sensitive compound capable of producing acidic photoproducts upon exposure to actinic radiation, at least one indicator dye that changes color on exposure to acidic conditions and at least one polymeric binder soluble in water or weakly alkaline aqueous solutions. The photographic element is exposed to active radiation sufficient to cause photobleaching of the contrast enhancement layer and exposure of the photoresist layer. The photographic element is exposed to actinic radiation sufficient to cause photobleaching of the contrast enhancement layer and exposure of the photoresist layer.Type: GrantFiled: June 3, 1985Date of Patent: June 9, 1987Assignee: Fairmount Chemical CompanyInventors: David B. Blumel, Albert S. Deutsch
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Patent number: 4668606Abstract: There are disclosed antireflecting compounds and layers used in admixture with or adjacent to a positive-working, non-silver halide photosensitive layer. The resulting antireflecting layers have unexpected thermal resistances, needed for the thermal planarization usually given to such photoresists.Type: GrantFiled: November 20, 1985Date of Patent: May 26, 1987Assignee: Eastman Kodak CompanyInventors: Thap DoMinh, Donald R. Diehl
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Patent number: 4661436Abstract: A positive photoresist metal ion aqueous developer is provided that gives a high contrast to the photoresist.The developer disclosed comprises a formulation of aqueous alkali-base such as potassium hydroxide and a fluorocarbon surfactant. The incorporation of the fluorocarbon surfactant provides the unexpected increase in the contrast of the photoresist. The addition of the fluorocarbon surfactant increases the gamma from a typical photoresist gamma (.gamma.) of 3 or less to a gamma greater than 10.The high contrast photoresist provides linewidth control and affords improved process latitude in photoresist imaging. The linewidth control is particularly critical in cases where fine lines are to be defined in the resist that covers steps or topography on the coated substrate. The higher the contrast, the less affected the resist by the topography, provided the exposure is adequate to expose the resist.Type: GrantFiled: August 19, 1985Date of Patent: April 28, 1987Assignee: Petrarch System, Inc.Inventors: James M. Lewis, Robert A. Owens, Andrew J. Blakeney
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Patent number: 4654292Abstract: A photoresist composition comprising a conjugated diene polymer or its cyclized product, a photocuring agent soluble in an organic solvent and a pyrazole compound having a skeleton represented by the following formula. ##STR1## Also provided is a method of forming a photoresist pattern using the aforesaid composition.Type: GrantFiled: September 17, 1985Date of Patent: March 31, 1987Assignees: Nippon Zeon Co., Ltd., Fujitsu LimitedInventors: Masayuki Oie, Satoshi Ogawa, Sadao Sugimoto, Masahiro Yamazaki, Katsuhiro Fujino
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Patent number: 4650739Abstract: A process for manufacturing materials in the form of sheets, foils or webs comprising chemically, mechanically and/or electrochemically roughened and anodically oxidized aluminum or one of its alloys, wherein the resultant aluminum oxide layers are post-treated with an aqueous solution containing phosphoroxo anions, is performed such that a post-treatment of the aluminum oxide layers is effected by immersion in an aqueous solution containing hexametaphosphate anion. In a preferred embodiment, the aqueous solution is adjusted to a pH of 1 to 5 by addition of an acid. The resulting materials, which have reduced adsorption properties, are preferably employed as support materials for offset printing plates.Type: GrantFiled: May 15, 1985Date of Patent: March 17, 1987Assignee: Hoechst AktiengesellschaftInventors: Ulrich Simon, Reiner Beutel
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Patent number: 4650288Abstract: An electrically conductive photoresist electrode is formed by a combination of a photoresist and conductive black powder. This conductive photoresist has the properties of being photosensitive, electrically conductive, and black to avoid reflectivity by the electrode structure, as occurs in display devices.Type: GrantFiled: July 21, 1986Date of Patent: March 17, 1987Assignee: North American Philips CorporationInventor: Roger P. White
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Patent number: 4642283Abstract: A negative working light-sensitive lithographic plate requiring no dampening solution and a plate making process are described, the negative working light-sensitive lithographic plate comprising a support having, in sequence, on said support, (A) a light-sensitive layer containing (1) an o-quinonediazide compound and (2) a coupling component which causes a diazo coupling reaction under a basic environment, and (B) a silicone rubber layer, and the plate making process comprising imagewise exposing the negative working light-sensitive lithographic plate and developing said exposed plate to obtain a lithographic plate requiring no dampening solution, wherein a step of processing with base is carried out after imagewise exposure.Type: GrantFiled: March 14, 1985Date of Patent: February 10, 1987Assignee: Fuji Photo Film Co., Ltd.Inventors: Hiroshi Takahashi, Yasuhisa Narutomi, Yoshimasa Aotani, Keisuke Shiba
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Patent number: 4626492Abstract: Disclosed is a positive-working resist composition which demonstrates improved photospeed and rate of development. The resist composition contains a solvent and select proportions of a novolak resin, a naphthoquinone diazide sensitizer, a dye which absorbs light at a maximum wavelength of from about 330 to about 460 nm and an effective proportion of a trihydroxybenzophenone compound. Also disclosed is a method of forming a resist pattern on a substrate by employing the positive-working resist composition.Type: GrantFiled: June 4, 1985Date of Patent: December 2, 1986Assignee: Olin Hunt Specialty Products, Inc.Inventor: James N. Eilbeck
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Patent number: 4626491Abstract: Positive deep ultra-violet photoresists which are base developable comprise base soluble polymers and as photosensitive solubilizing agents oligomeric compounds of the formula ##STR1## wherein X is alkylene, arylene, alkoxyalkylene or aralkylene and n is a positive integer such that the molecular weight of the oligomeric compound is from about 500 to about 3000.Type: GrantFiled: September 12, 1985Date of Patent: December 2, 1986Assignee: J. T. Baker Chemical CompanyInventor: Gary M. Gray
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Patent number: 4624909Abstract: Disclosed is a novel novolak resin comprising structural units having a trimethylsilyl group. A resist material highly resistive to dry etching is obtained by adding a photosensitive diazo compound to this novolak resin. The resist material is useful in various lithography methods to form a positive resist pattern. This resist material is used in a pattern forming method of a two-layer type, in which a fine pattern is formed in a thin film of the resist material by lithography and then transferred into an underlying thick organic polymer layer by dry etching of the underlying layer with the resist pattern as mask. Curing of the resist pattern by irradiation with deep UV rays is effective for further improvement in the precision of the transferred pattern.Type: GrantFiled: April 18, 1985Date of Patent: November 25, 1986Assignee: NEC CorporationInventors: Yasushi Saotome, Hiroshi Gokan, Kazuhide Saigo, Masayoshi Suzuki, Yoshitake Ohnishi
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Patent number: 4622283Abstract: Positive deep ultra-violet photoresists which are base developable comprise base soluble polymers and as photosensitive solubilizing agents compounds of the formula ##STR1## wherein R.sup.1 and R.sup.2 can each individually be alkyl, aryl, alkoxy alkyl, aralkyl or haloalkyl radicals or R.sup.1 and R.sup.2 taken together can be an alkylene radical.Type: GrantFiled: September 12, 1985Date of Patent: November 11, 1986Assignee: J. T. Baker Chemical CompanyInventor: Gary M. Gray
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Patent number: 4606995Abstract: A developing solution for developing a light-sensitive lithographic plate having a o-quinonediazide compound-containing light-sensitive layer is disclosed. The developing solution is comprised of an aqueous solution containing alkali silicate and an alkali aqueous solution-soluble compound of a metal selected from the group consisting of Sn, Pb, Fe, Co and Ni. The developing solution provides excellent resolving power, has excellent development stability, processing capability and adaptability with respect to automatic developing machines.Type: GrantFiled: December 28, 1983Date of Patent: August 19, 1986Assignee: Fuji Photo Film Company, LimitedInventors: Nobuyuki Kita, Hiroshi Matsumoto, Hitoshi Hagiwara
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Patent number: 4598036Abstract: A print-out composition containing a leuco dye and a photooxidizing agent is described, said print-out composition containing at least one carbazomethane compound represented by formula (I) as the leuco dye ##STR1## wherein Y represents an amino group-substituted phenyl group represented by formula (Ia) ##STR2## or an indolyl group represented by formula (Ib) ##STR3## wherein X.sub.1 and X.sub.2 each represents a hydrogen atom, an unsubstituted alkyl group, or an alkyl group substituted by a halogen atom, a hydroxy group, a cyano group, or a lower alkoxy group, said alkyl group having up to 12 carbon atoms, a cycloalkyl group, a phenyl group, a benzyl group, or a phenyl or benzyl group substituted by a halogen atom, a lower alkyl group, or a lower alkoxy group, or said X.sub.1 and X.sub.2 together may form a 5-membered or 6-membered heterocyclic group together with the nitrogen atom bonded thereto; X.sub.Type: GrantFiled: September 10, 1984Date of Patent: July 1, 1986Assignee: Fuji Photo Film Co., Ltd.Inventors: Masayuki Iwasaki, Minoru Maeda, Fumiaki Shinozaki, Sadao Ishige
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Patent number: 4594306Abstract: This invention relates to an improvement in a light-sensitive copying material comprising a carrier and a light-sensitive copying layer which contains, as the light-sensitive compound, an o-quinone diazide sulfonic acid ester or an o-quinone diazide sulfonic acid amide, the improvement being that the layer also contains a compound with an aromatic or aliphatic hydroxy group which is capable of forming chelate compounds.Type: GrantFiled: August 17, 1984Date of Patent: June 10, 1986Assignee: Hoechst AktiengesellschaftInventors: Paul Stahlhofen, Rainer Beutel
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Patent number: 4588671Abstract: A photo- and electron resist distributed in an organic solvent, and including an additive which forms a donor-acceptor complex to eliminate luminescence effects and increase the stability of the resist.The photo- and electron resist can be used in microelectronics, optics, printing and precision machine building industry when resists are employed to manufacture structures of semiconductor devices and solid-state circuits.Type: GrantFiled: August 1, 1983Date of Patent: May 13, 1986Assignee: Institut Khimii Akademii Nauk SSSRInventors: Sergei P. Molodnyakov, Jury I. Fedorov, Vitaly A. Kuznetsov, Alexei N. Egorochkin, Tamara G. Birjukova, Grigory A. Razuvaev
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Patent number: 4587196Abstract: Cresol-formaldehyde novolak resins made from a mixture containing meta- and paracresol or ortho-, meta- and paracresol in a ratio selected from a given range for use in fast positive photoresist compositions together with one or more sensitizing compounds. When dissolved in a mixture of organic solvents, the photoresist compositions are suitable for application as a thin coating to a substrate. After the coating has been dried, the coated substrate can be exposed to image-wise modulated actinic radiation and developed in alkaline solution, yielding a relief pattern of resist on substrate useful for a number of applications.Type: GrantFiled: October 31, 1984Date of Patent: May 6, 1986Assignee: Philip A. Hunt Chemical CorporationInventor: Medhat A. Toukhy
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Patent number: 4581321Abstract: A process for producing negative relief copies is disclosed in which a light-sensitive material, comprising (1) a light-sensitive ester or amide of a 1,2-quinone-diazide-sulfonic acid or of a 1,2-quinone-diazide-carboxylic acid and (2) a hexamethylol melamine ether is imagewise exposed, thereafter heated, and, after cooling, exposed again without an original, and subsequently developed by means of an aqueous-alkaline developer. The disclosed process permits the production of negative copies with the aid of a material which yields positive copies when it is processed in a conventional manner.Type: GrantFiled: July 2, 1984Date of Patent: April 8, 1986Assignee: Hoechst AktiengesellschaftInventor: Paul Stahlhofen
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Patent number: 4578341Abstract: A relief image-forming composition having an acidic pH comprises a photosensitive component and an indicator capable of existing in two states differing in actinic opacity dependent upon pH. A relief image is formed by (1) exposing to light selected areas of a layer of the composition, the indicator being in its state of lower actinic opacity, (2) removing layer material from the exposed areas or from the unexposed areas and (3) shifting the pH in the remaining layer material to a value at which the indicator exists in its state of higher actinic opacity. The resultant image can then be used as an intermediate original in diazotype copying processes.Type: GrantFiled: August 3, 1984Date of Patent: March 25, 1986Assignee: Sensitisers (Research) Ltd.Inventors: Peter B. Readings, Nandor Mihalik, Robin Taylor
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Patent number: 4568631Abstract: An optical photolithographic process in which resist lines having widths in the micron and sub-micron range are produced without the use of a fine line photomask. A positive photoresist having an additive for image reversal is applied to the surface of a semiconductor substrate. The photoresist is exposed through a photomask to ultraviolet light. The edges of the opaque sections of the mask diffract the ultraviolet light, forming partially exposed areas between the exposed and unexposed areas formed in the photoresist. After development in a solvent to remove the exposed areas, the photoresist undergoes an image reversal process. The photoresist is first baked at 100.degree. C. for 30 minutes. During this bake step, the photoactive decomposition products present in the partially exposed areas react, freezing the solubility of the partially exposed areas with respect to that of the unexposed areas.Type: GrantFiled: April 30, 1984Date of Patent: February 4, 1986Assignee: International Business Machines CorporationInventors: Dinesh A. Badami, Mark C. Hakey, Holger Moritz
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Patent number: 4560636Abstract: This invention relates to a light-sensitive copying material comprising a layer support and a positive-working light-sensitive layer thereon having a rough surface and a content of finely divided particles, wherein the smallest dimension of the particles corresponds at least to the thickness of the layer.Type: GrantFiled: April 13, 1984Date of Patent: December 24, 1985Assignee: Hoechst AktiengesellschaftInventor: Paul Stahlhofen
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Patent number: 4550069Abstract: The invention provides a positive working photosensitive composition which comprises at least one novolak resin, at least one o-quinone diazide and a propylene glycol alkyl ether acetate.Type: GrantFiled: June 11, 1984Date of Patent: October 29, 1985Assignee: American Hoechst CorporationInventor: Thomas R. Pampalone
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Patent number: 4544627Abstract: A negative-working image forming process which comprises uniformly exposing a photosensitive material comprising a support having thereon a sensitive layer comprising (i) an o-quinonediazide compound and (ii) a second compound, to actinic radiation which is able to convert the o-quinonediazide compound to the corresponding indenecarboxylic acid compound, and subsequent to said uniformly exposing imagewise exposing said exposed photosensitive material to a laser beam to thereby render the indenecarboxylic acid compound of the imagewise exposed areas convert to the corresponding indene compound and developing with an alkaline developing solution to dissolve out the unexposed area to the laser beam, wherein said second compound reduces the rate of dissolution of the laser exposed areas in the developing solution by converting the indenecarboxylic acid to the corresponding indene compound, whereby said image results.Type: GrantFiled: November 3, 1983Date of Patent: October 1, 1985Assignee: Fuji Photo Film Co., Ltd.Inventors: Yonosuke Takahashi, Hiromichi Tachikawa, Fumiaki Shinozaki, Tomoaki Ikeda
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Patent number: 4536465Abstract: A positive-working photosensitive composition comprising (a) an o-quinonediazide compound and (b) a condensed resin containing a condensation unit composed of an aromatic compound having a carboxylic group and a phenolic ahydroxyl group, and an aldehyde or ketone is disclosed. Said condensation unit has the following formula (I): ##STR1## wherein R.sub.1 is a hydrogen atom, a hydroxyl group, an acyloxy group, an alkyl group, an alkoxy group or a halogen atom, which may be the same or different when n is 2; R.sub.2 and R.sub.3 are each a hydrogen atom, a lower alkyl group having 1 to 4 carbon atoms, a phenyl group or a substituted phenyl group, which may be the same or different; and n is 1 or 2.Type: GrantFiled: January 7, 1983Date of Patent: August 20, 1985Assignee: Konishiroku Photo Industry Co., Ltd.Inventors: Masafumi Uehara, Atsuo Yamazaki, Kazuhiro Shimura
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Patent number: 4526856Abstract: A novel photoresist formulation is provided which provides low striations and excellent wetting properties. The photoresist composition may be applied by spin casting on various substrates used in integrated circuit manufacture. The essential component in this invention is the solvent composition which consists of cyclopentanone (or cyclopentanone-cyclohexanone blend) in combination with an aliphatic alcohol of 5-12 carbon atoms. These solvent components when used in certain specific ratios provide unexpectedly good wetting of various substrates and low striation films.Type: GrantFiled: May 23, 1983Date of Patent: July 2, 1985Assignee: Allied CorporationInventors: James M. Lewis, Robert A. Owens, Richard F. Sweeney, Ronald W. Wake, Robert E. Rinehart
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Patent number: 4515885Abstract: Vesicular imaging films have good speed and stable latent images when comprised of a diazonium compound, nitrate salt, and binder comprising gelatin or poly(vinyl alcohol). The film can even have highly stable final images when the binder comprises poly(vinyl alcohol).Type: GrantFiled: August 1, 1983Date of Patent: May 7, 1985Assignee: Minnesota Mining and Manufacturing CompanyInventors: Kenneth G. Gatzke, John M. Winslow
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Patent number: 4504567Abstract: The invention provides a light-sensitive lithographic printing plate containing a light-sensitive composition which has a different degree of solubility in an exposed area of said printing plate than in an unexposed area of said printing plate when said printing plate is developed in a developing solution. This printing plate is produced by a process which comprises coating on a support a solution prepared by dissolving a light-sensitive composition containing a light-sensitive material and at least one fluorinated surfactant having Formula (I) in a quantity of between 0.005% by weight and 0.05% by weight based on the weight of said composition, in at least one solvent having (A) a solubility parameter of at least 8(cal/cm.sup.3)1/2, and (B) a boiling point within the range of from 100.degree. to 200.degree. C. Said Formula (I) is Rf-A-Y, wherein Rf is a partially or completely fluorinated hydrophobic alkyl moiety, A is a single bind or bivalent moiety and Y is a hydrophilic moiety.Type: GrantFiled: August 9, 1984Date of Patent: March 12, 1985Assignee: Konishiroku Photo Industry Co., Ltd.Inventors: Takeshi Yamamoto, Kiyoshi Goto
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Patent number: 4497888Abstract: A light-sensitive printing plate precursor is disclosed. The printing plate precursor is comprised of an aluminum support base having provided on a grained and anodized surface. The surface is coated with a layer which is comprised of a positive working light-sensitive composition and an oxonol dye. The printing plate has high printing durability, high water retention ability and high color stain resistance. When used the plate precursor provides an image having high contrast. The plate precursor forms less color stain than conventional plates whether used with a fresh developing solution or a fatigued developing solution. The plate precursor does not result in causing uneven development when using manual development methods.Type: GrantFiled: June 21, 1983Date of Patent: February 5, 1985Assignee: Fuji Photo Film Co., Ltd.Inventors: Akira Nishioka, Yoshimasa Aotani, Kotaro Yamasue
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Patent number: 4493884Abstract: A light-sensitive composition containing a high molecular compound and a light-sensitive o-naphthoquinonediazide compound is disclosed. The high molecular compound includes a structure unit represented by the general formula (I): ##STR1## wherein R is a hydrogen atom or a methyl group, and Y is a phenylene group, a substituted phenylene group, a naphthylene group or a substituted naphthylene group. The light-sensitive composition makes possible the production of a light-sensitive material which can be developed under a wide range of development conditions to provide a lithographic printing plate having high printing durability.Type: GrantFiled: May 23, 1983Date of Patent: January 15, 1985Assignee: Fuji Photo Film Co., Ltd.Inventors: Teruo Nagano, Akira Nagashima
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Patent number: 4487823Abstract: The present invention describes a light-sensitive copying material comprising a support and a light-sensitive layer which contains from 0.01 to 10 percent by weight of a non-ionic ester which is obtained by reacting a perfluoro-carboxylic acid with a polyalkylene glycol or of an ether which is obtained by reacting a highly fluorinated or a perfluorinated alkanol with a polyalkylene glycol. By the addition of the fluorinated compound, a more uniform coating is achieved, even when one solvent alone is used for the coating solution.Type: GrantFiled: October 29, 1982Date of Patent: December 11, 1984Assignee: Hoechst AktiengesellschaftInventors: Peter Lehmann, Dieter Mohr, Kurt Reiss
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Patent number: 4477553Abstract: There is disclosed a photosensitive composition comprising an o-quinonediazide compound and, as a binder resin, a resin containing in the molecule the unit represented by the following formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 have the same meanings as defined in the specification.The photosensitive composition according to the present invention has excellent resistance to chemicals and long press-life, and is excellent in alkali-solubility and difficult to form scumming.Type: GrantFiled: December 29, 1983Date of Patent: October 16, 1984Assignee: Konishiroku Photo Industry Co., Ltd.Inventors: Takeshi Yamamoto, Kiyoshi Goto, Masafumi Uehara
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Patent number: 4467025Abstract: A photosensitive composition containing an o-naphthoquinonediazido compound of Formula I ##STR1## wherein X is an oxy or amino group, Y is a cyano or nitro group, and n is an integer of 2 to 5, and an organic dye capable of changing its color when the photosensitive composition is exposed.Type: GrantFiled: February 15, 1983Date of Patent: August 21, 1984Assignee: Konishiroku Photo Industry Co., Ltd.Inventors: Kiyoshi Goto, Hiroh Kawada, Noriyasu Kita
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Patent number: 4464458Abstract: A resist system for semiconductor device fabrication comprised of bottom positive resist layer of a diazoquinone/novolak resist applied to a substrate and overcoated with a like or different diazoquinone/novolak top resist layer which has been sensitized with pyrene and/or its derivatives.Type: GrantFiled: December 30, 1982Date of Patent: August 7, 1984Assignee: International Business Machines CorporationInventors: Ming-Fea Chow, Edward C. Fredericks, Wayne M. Moreau
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Patent number: 4460674Abstract: A posi-type photosensitive composition having enhanced sensitivity is prepared by incorporating a specific sensitizer selected from gallic acid, its derivative, naphthoquinone compound and its derivative in a quinonediazide type photosensitive material. The composition is free from lowering in development tolerance and other properties.Type: GrantFiled: January 4, 1982Date of Patent: July 17, 1984Assignee: Konishiroku Photo Industry Co., Ltd.Inventors: Masafumi Uehara, Takeshi Yamamoto, Atsuo Yamazaki, Tohru Aoki
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Patent number: 4458000Abstract: Disclosed is a light-sensitive mixture comprising (a) a 1,2-quinonediazide or a mixture of (a.sup.1) a compound forming an acid on exposure and (a.sup.2) a compound having at least one C--O--C bond cleavable by acid; (b) a water-insoluble binder soluble in aqueous-alkaline solutions; (c) a photolytically cleavable organic halogen compound of one of the formulae ##STR1## in which R.sup.1 denotes an aromatic radical bonded directly or via a conjugated chain, and X denotes a halogen atom; and (d) an azo dyestuff containing at least one nitro group in the molecule. Also disclosed are light-sensitive copying materials produced from these mixtures.Type: GrantFiled: September 28, 1982Date of Patent: July 3, 1984Assignee: Hoechst AktiengesellschaftInventor: Paul Stahlhofen
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Patent number: 4457999Abstract: Disclosed is a light-sensitive mixture comprising (a) a 1,2-quinonediazide or a mixture of (a.sup.1) a compound forming an acid on exposure and (a.sup.2) a compound having at least one C--O--C bond cleavable by acid; (b) a water-insoluble binder soluble in aqueous-alkaline solutions; (c) an organic compound forming an acid on exposure of the general formula I ##STR1## in which X is a single bond or one of the groups CO, SO.sub.2, N=N or CR.sup.7 R.sup.8, R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are hydrogen atoms, halogen atoms or nitro groups, with not more than two of these radicals being hydrogen atoms and at least one thereof being a nitro group, R.sup.5 and R.sup.6 are hydrogen atoms or 1,2-naphthoquinone-2-diazide-4-sulfonyloxy radicals, with R.sup.5 and R.sup.6 being always different from each other, and R.sup.7 and R.sup.8 are hydrogen atoms or lower alkyl radicals, and (d) an azo dyestuff containing at least one nitro group in the molecule.Type: GrantFiled: September 28, 1982Date of Patent: July 3, 1984Assignee: Hoechst AktiengesellschaftInventor: Paul Stahlhofen
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Patent number: 4451550Abstract: Novel, coatable, highly long-chain branched, ungelled, most preferably endblocked, non-linear phenoxy resins of random structure devoid of regularly recurring units, with the average distance between the branch sites thereof being essentially of the same order of magnitude as the average branch length, such resins advantageously comprising the copolymerization product of:(i) at least one dihydric phenol, e.g., sulfonyl diphenol;(ii) an epoxy comonomer having two epoxy functional groups, e.g., resorcinol diglycidyl ether;(iii) a branching agent comprising an epoxy or phenolic compound having a functionality greater than 2, and preferably at least 3, wherein the amount of branching agent is sufficient to provide at least 10 mole percent branch sites in the polymer resin, and, most preferably;(iv) a monofunctional phenol or epoxide as an endblocker compound.The branched phenoxy resins are well adapted as matrices for enhanced film speed vesicular films.Type: GrantFiled: July 29, 1982Date of Patent: May 29, 1984Assignee: James River Graphics, Inc.Inventors: Everett W. Bennett, Ahmad Arfaei
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Patent number: 4444869Abstract: An improved positive-working resist material capable of forming on a substrate either a positive resist pattern or a negative resist pattern. The positive-working resist material comprises a positive-working resist resin having incorporated therein one or more photochromic compounds, such as spiropyrans, triphenylmethane dyes, anils and the like. A positive or negative resist pattern having a remarkably improved definition can be obtained. The use of such a positive-working resist material in the formation of a negative resist pattern on the substrate is also disclosed.Type: GrantFiled: November 25, 1981Date of Patent: April 24, 1984Assignee: Fujitsu LimitedInventors: Tsunehiro Chonan, Akira Morishige
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Patent number: 4442195Abstract: A photosensitive composition for making lithographic printing plate and for use as a photoresist material which comprises a photosensitive o-quinone diazide compound, an alkali-soluble resin, and 0.5 to 20% by weight 6-membered cyclic acid anhydride.Type: GrantFiled: July 7, 1982Date of Patent: April 10, 1984Assignee: Konishiroku Photo Industry Co., Ltd.Inventors: Takeshi Yamamoto, Kiyoshi Goto
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Patent number: 4431725Abstract: A light-sensitive material having on a support a light-sensitive layer containing an o-quinonediazide compound as a main component and, additionally, a particular compound represented by the following general formula (I): ##STR1## wherein Z represents the nonmetallic atoms forming a 5-membered ring; X represents S, O, ##STR2## or .dbd.N--R.sub.c (where R.sub.a, R.sub.b and R.sub.c are each a hydrogen atom or an organic group other than a carboxylic acid group); and Y is a hydrogen atom or an organic group other than a carboxylic acid group, is disclosed. This material can provide both positive and negative working images having high resolution and good adhesiveness to the support. A process for producing positive working images includes the steps of imagewise exposure and development processing, while a process for producing negative working images includes the steps of imagewise exposure, heating, uniform (overall) exposure and development processing.Type: GrantFiled: July 19, 1982Date of Patent: February 14, 1984Inventors: Hiromichi Tachikawa, Yohnosuke Takahashi, Fumiaki Shinozaki, Tomoaki Ikeda
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Patent number: 4424270Abstract: A light-sensitive mixture comprising a water-insoluble binder soluble in aqueous alkaline solutions, and the reaction product of a naphthoquinonediazidesulfonyl halide with a mixture composed of a low molecular weight compound having a definite structure and molecular size containing at least one phenolic hydroxyl group, and of a polymeric compound having recurring units, each of which contains at least one phenolic hydroxyl group. The mixture is useful in producing printing plates and photoresists and has the advantage that the naphthoquinonediazidesulfonic acid ester contained therein is non-explosive.Type: GrantFiled: December 22, 1981Date of Patent: January 3, 1984Assignee: Hoechst AktiengesellschaftInventors: Fritz Erdmann, Ulrich Simon
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Patent number: 4411978Abstract: A photosensitive recording material which includes in a supported layer a mixture of photosensitive substances in admixture with one or more polymers that are soluble in an alkaline aqueous liquid, characterized in that such mixture of photosensitive substances essentially consists of:(A) at least one photosensitive nitrone of the formula: ##STR1## in which: R is an aromatic hydrocarbon group including a substituted aromatic hydrocarbon group,R.sup.Type: GrantFiled: March 13, 1978Date of Patent: October 25, 1983Assignee: AGFA-Gevaert N.V.Inventors: Urbain L. Laridon, Hendrik E. Kokelenberg, Rafael P. Samijn