Process Of Making Diazo Product Patents (Class 430/168)
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Patent number: 9599891Abstract: A method of manufacturing a nanopatterned biophotonic structure includes forming a customized nanopattern mask on a substrate using E-beam lithography, providing a biopolymer matrix solution, depositing the biopolymer matrix solution on the substrate, and drying the biopolymer matrix solution to form a solidified biopolymer film. A surface of the film is formed with the nanopattern mask, or a nanopattern is machined directly on a surface of the film using E-beam lithograpy such that the biopolymer film exhibits a spectral signature corresponding to the E-beam lithograpy nanopattern. The resulting bio-compatible nanopatterned biophotonic structures may be made from silk, may be biodegradable, and may be bio-sensing devices. The biophotonic structures may employ nanopatterned masks based on non-periodic photonic lattices, and the biophotonic structures may be designed with specific spectral signatures for use in probing biological substances, including displaying optical activity in the form of opalescence.Type: GrantFiled: November 5, 2008Date of Patent: March 21, 2017Assignees: TRUSTEES OF TUFTS COLLEGE, TRUSTEES OF BOSTON UNIVERSITYInventors: David L. Kaplan, Fiorenzo G. Omenetto, Luca Dal Negro
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Patent number: 7695875Abstract: The invention pertains to a photo-sensitive composition which comprises a photochemical initiator, a polyacid or a salt thereof, and a poly(3,4-alkylenedioxythiophene) wherein the alkylene moiety is —(CH2)n-, n being an integer from 1 to 3, or 1,2-cyclo-hexylene, which may optionally be substituted, characterized in that the photochemical initiator is a water-soluble polymer comprising at least two azide or diazonium groups. Preferably, the water-soluble polymer is chemically stable at pH 6 or less, more preferably at pH 2 or less.Type: GrantFiled: February 5, 2003Date of Patent: April 13, 2010Assignee: Koninklijke Philips ElectronicsInventor: Fredericus Johannes Touwslager
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Patent number: 7399569Abstract: A microcapsule produced by a method involving a primary dispersed particle and a secondary dispersed particle, the capsule formation occurring at the interface of the secondary dispersed particle. A microcapsule containing a diazonium salt represented by a specific formula. A recording material utilizing the microcapsule.Type: GrantFiled: February 18, 2005Date of Patent: July 15, 2008Assignee: FUJIFILM CorporationInventors: Mitsuyuki Tsurumi, Yasuhiro Mitamura
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Patent number: 7005227Abstract: In one embodiment, a photoactive compound may be attached to a polymer backbone. This embodiment may be more resistant to the generation of reactive outgassing components and may exhibit better contrast.Type: GrantFiled: January 21, 2004Date of Patent: February 28, 2006Assignee: Intel CorporationInventors: Wang Yueh, Heidi Cao
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Patent number: 6908717Abstract: The present invention provides a positve photosensitive resin composition of high sensitivity which can form a pattern of high resolution and high residual film ration and which can give a cured film superior in mechanical properties, adhesivity and water absorptivity. That is, the present invention lies in a positive photosensitve resin compostion comprising 100 parts by weight of an alkali-soluble resin, 1 to 100 parts by weight of a photosensitve diazoquinone compound (B) and a filler (C), characterized in that content F of the filler (C) represented by the following formula is 2 to 70% by weight.Type: GrantFiled: October 9, 2001Date of Patent: June 21, 2005Assignees: Sumitomo Bakelite Company Limited, Intel CorporationInventors: Takashi Hirano, Shusaku Okaaki, Michael D. Goodner, Robert P. Meagley
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Patent number: 6861196Abstract: The present invention includes an imageable element, which can be: (a) an imageable element comprising an imaging layer which comprises: an aromatic diazonium salt containing compound having an alkoxy substituent and an aromatic diazonium salt containing compound free of an alkoxy substituent; a polyvinyl acetal binder; and a sheet substrate; or (b) an imageable element comprising an imaging layer which comprises: an aromatic diazonium salt containing compound having an alkoxy substituent and an aromatic diazonium salt containing compound free of an alkoxy substituent; and a sheet substrate. The imaging layer includes a total aromatic diazonium salt containing compound content of at least 10 weight percent. The molar ratio of the aromatic diazonium salt containing compound having an alkoxy substituent to the aromatic diazonium salt containing compound that is free of an alkoxy substituent is from about 1.0:1 to 70:1. Upon imagewise exposure and development, an imaged element is obtained.Type: GrantFiled: September 17, 2003Date of Patent: March 1, 2005Assignee: Kodak Polychrome Graphics LLCInventors: Stephan J. Platzer, Maria T. Sypek, Paul Perron, Harald Baumann, Melinda Alden
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Patent number: 6852464Abstract: Methods of manufacturing multi-layer thermally imageable elements useful as lithographic printing plate precursors are disclosed. The elements comprise a substrate, an underlayer, and an imageable layer. The imageable layer comprises a first polymeric material and o-diazonaphthoquinone containing material. After the underlayer has been coated over the substrate and the imageable layer has been coated over the underlayer, the element is heated to between about 130° C. and about 200° C. for a time sufficient to decrease the sensitivity of the imageable element to the white light.Type: GrantFiled: January 10, 2002Date of Patent: February 8, 2005Assignee: Kodak Polychrome Graphics, LLCInventor: Paul Kitson
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Patent number: 6849372Abstract: The present invention provides methods of forming and using thermally imageable composite elements which may be developed into lithographic printing plates. More specifically, the present invention provides a method of forming thermally imageable composite elements which provide substantial developer resistance in desired regions, while maintaining white light desensitivity and durability.Type: GrantFiled: July 30, 2002Date of Patent: February 1, 2005Assignee: Kodak Polychrome GraphicsInventors: Kevin Ray, Anthony Paul Kitson, Jian Bing Huang
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Publication number: 20040063022Abstract: The present invention includes an imageable element, which can be: (a) an imageable element comprising an imaging layer which comprises: an aromatic diazonium salt containing compound having an alkoxy substituent and an aromatic diazonium salt containing compound free of an alkoxy substituent; a polyvinyl acetal binder; and a sheet substrate; or (b) an imageable element comprising an imaging layer which comprises: an aromatic diazonium salt containing compound having an alkoxy substituent and an aromatic diazonium salt containing compound free of an alkoxy substituent; and a sheet substrate. The imaging layer includes a total aromatic diazonium salt containing compound content of at least 10 weight percent. The molar ratio of the aromatic diazonium salt containing compound having an alkoxy substituent to the aromatic diazonium salt containing compound that is free of an alkoxy substituent is from about 1.0:1 to 70:1. Upon imagewise exposure and development, an imaged element is obtained.Type: ApplicationFiled: September 17, 2003Publication date: April 1, 2004Applicant: Kodak Polychrome Graphics, LLC.Inventors: Stephan J. Platzer, Maria T. Sypek, Paul Perron, Harald Baumann, Melinda Alden
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Patent number: 6683674Abstract: There is provided an image recording device which is compact and free of waste materials, which has a completely dry system and a simplified exposure system, and which can carry out high speed image recording. The image recording device includes, within a housing of the image recording device, an accommodating section for accommodating a light and heat sensitive recording material; a light recording section for exposing the light and heat sensitive recording material, which is supplied from the accommodating section, with light to record a latent image; a heat developing section for developing the latent image by applying heat; a light fixing section for irradiating light to fix the developed image; and a discharging section for discharging the light and heat sensitive recording material having an image recorded thereon. Exposure is carried out by a plurality of LEDs provided at a light source section of an exposure unit of the light recording section.Type: GrantFiled: May 1, 2001Date of Patent: January 27, 2004Assignee: Fuji Photo Film Co., Ltd.Inventors: Nobufumi Mori, Akinori Harada, Shintaro Washizu
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Patent number: 6645689Abstract: A radiation-sensitive composition for use in printing plates is described. The composition comprises: (a) at least one novolak; (b) at least one naphthoquinone diazide derivative; and (c) a copolymer comprising units A, B, and a unit C comprising a cyclic terminal urea group, wherein unit A is present in an amount of about 5 to about 50 mol % and has the formula wherein R1 is selected such that the homopolymer of A is alkali-soluble, unit B is present in an amount of about 20 to about 70 mol % and has the following formula wherein R2 is selected such that the homopolymer of B has a glass transition temperature greater than 100° C., preferably a glass transition temperature in the range from about 100 to about 380° C.Type: GrantFiled: March 13, 2002Date of Patent: November 11, 2003Assignee: Kodak Polychrome Graphics LLCInventor: Mathias Jarek
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Publication number: 20030157422Abstract: Methods of manufacturing multi-layer thermally imageable elements useful as lithographic printing plate precursors are disclosed. The elements comprise a substrate, an underlayer, and an imageable layer. The imageable layer comprises a first polymeric material and o-diazonaphthoquinone containing material. After the underlayer has been coated over the substrate and the imageable layer has been coated over the underlayer, the element is heated to between about 130° C. and about 200° C. for a time sufficient to decrease the sensitivity of the imageable element to the white light.Type: ApplicationFiled: January 10, 2002Publication date: August 21, 2003Inventor: Paul Kitson
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Publication number: 20030099888Abstract: A coating solution useful in the preparation of printing plate precursors comprises:Type: ApplicationFiled: July 5, 2001Publication date: May 29, 2003Applicant: Kodak Polychrome Graphics L.L.C.Inventor: Mathias Jarek
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Patent number: 6475692Abstract: Radiation-sensitive compositions comprise at least one novolak, at least one naphthoquinone diazide derivative and a copolymer; the copolymer consisting of the units A, B and C wherein unit A is present in an amount of 5 to a maximum of 50 mol % and R1 and R4 are selected such that the homopolymer of A is alkali-soluble, B is present in an amount of 20 to 70 mol % and R2, R6 and R7 are selected such that the homopolymer of B has a high glass transition temperature, and C is present in an amount of 10 to 50 mol % and R3 and R5 are selected such that the homopolymer of C is water-soluble and that unit A is different from unit C. Furthermore, the invention describes printing plates produced therefrom.Type: GrantFiled: August 2, 2000Date of Patent: November 5, 2002Assignee: Kodak Polychrome Graphics LLCInventors: Mathias Jarek, Gerhard Hauck
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Patent number: 6346361Abstract: A method of coupling a diazonium salt with an organic polymer comprising, on order, the steps of: providing a polymer in one liquid phase; providing an diazonium salt in a separate liquid phase; contacting the separate phases, and thereby reacting the polymer and the diazonium salt.Type: GrantFiled: October 6, 1999Date of Patent: February 12, 2002Assignee: Clariant Finance (BVI) LimitedInventors: Jianhui Shan, Shuji Ding, Eleazar B. Gonzalez, Dinesh N. Khanna
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Patent number: 6338930Abstract: A method for preparing a positive photoresist layer is provided. In this method, a photoresist composition is drop-wise applied on an insulator layer or a conductive metal layer formed on a substrate. The photoresist composition includes a polymer resin, a sensitizer for changing solubility of the photoresist layer when exposed and a solvent. The coated substrate is rotated at the speed of 1,250 to 1,350 rpm for 4.2 to 4.8 seconds. The coated substrate is then dried and the dried substrate is exposed to some form of radiation. Next, the exposed portion is removed by using an alkaline developing solution. The solvent preferably includes 3-methoxybutyl acetate and 4-butyrolactone, or includes 3-methoxybutyl acetate, 2-heptanone, and 4-butyrolactone.Type: GrantFiled: September 5, 2000Date of Patent: January 15, 2002Assignee: Samsung Electronics Co., Ltd.Inventors: Jin-Ho Ju, Yu-Kyung Lee, Hong-Sik Park, Yun-Jung Nah, Ki-Soo Kim, Sung-Chul Kang
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Patent number: 6291134Abstract: There is described a method of preparing a lithographic plate which comprises coating on a lithographic support having a hydrophilic surface a layer of a radiation sensitive coating, imaging the coating then acting on the plate while on the press with aqueous fount solution to remove the unexposed areas of the coating, to reveal the hydrophilic surface of the plate and to leave an ink receptive image, wherein the radiation sensitive coating comprises a diazo salt of formula (I): wherein R1 is an anion, R2 and R3 represent optional substitution, R4 is —N— and —S— and R5 is a group which, after exposure of the plate renders the residue of the diazo salt oleophilic and fount solution insoluble.Type: GrantFiled: July 8, 1999Date of Patent: September 18, 2001Assignee: Kodak Polychrome Graphics LLCInventors: Kevin Barry Ray, Alison Jane Brooks, Gareth Rhodri Parsons, Deborah Jane Firth, Christopher David McCullough
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Patent number: 6165689Abstract: According to the present invention there is provided a method for making lithographic printing plates including the following steps:a) preparing a light sensitive imaging element having on a lithographic base with a hydrophilic surface a first layer including a polymer, soluble in an aqueous alkaline solution and a top layer on the same side of the lithographic base as the first layer which top layer is unpenetrable for an alkaline developer containing SiO.sub.2 as silicate;b) exposing imagewise said light sensitive imaging element to actinic light;c) developing said imagewise exposed light sensitive imaging element with said alkaline developer so that the exposed areas of the top layer and the underlying areas of the first layer are dissolved and the unexposed areas of the first layer remain undissolved characterized in that said top layer includes a diazonium salt and for at least 20% of its weight one or more non-proteinic hydrophilic film-forming polymers.Type: GrantFiled: September 28, 1998Date of Patent: December 26, 2000Assignee: AGFA-Gevaert, N.V.Inventors: Joan Vermeersch, Marc Van Damme, Dirk Kokkelenberg
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Patent number: 6080521Abstract: A diazotype reproduction material is a fibrous paper base having at least one overcoat, which is an acidic diazotype layer and a layer strata below the overcoat containing an anionic compound to minimize deep penetration of diazotype diazonium salts.Type: GrantFiled: June 15, 1998Date of Patent: June 27, 2000Assignee: Andrews Paper & Chemical Co., Inc.Inventors: Peter Muller, Sidney G. Garnish, Ronny L. Gonzalez
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Patent number: 5998084Abstract: A positive-working, radiation-sensitive recording material capable of being used for the production of planographic printing plates, comprising: an aluminum support and a radiation-sensitive layer coated thereon, whereinthe aluminum support has been grained in nitric acid, then cleaned in sulfuric acid, anodized in sulfuric acid, and subsequently hydrophilized with a compound comprising at least one unit with a phosphonic acid or phosphonate group; andthe radiation-sensitive layer comprisesa) a radiation-sensitive 1,2-naphthoquinone-2-diazide-4- or -5-sulfonic acid ester of a polycondensate having phenolic hydroxy groups, said polycondensate being obtained by reacting a phenolic compound with an aldehyde or ketone,b) a novolak or a polycondensation product obtained by reacting a polyphenol with an aldehyde or ketone, as an alkali-soluble resin,c) a vinyl-type polymer comprising at least one unit having a lateral hydroxyphenyl group,d) a clathrate-forming compound,e) a low-molecular weight compound which comprType: GrantFiled: November 15, 1996Date of Patent: December 7, 1999Assignee: Agfa-Gevaert N.V.Inventors: Andreas Elsaesser, Raimund Haas, Guenter Hultzsch, Peter Lehmann, Rudolf Neubauer, Rudolf Zertani
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Patent number: 5994031Abstract: Disclosed is a method of processing an exposed presensitized planographic printing plate employing an automatic processor, the method comprising the steps of developing the exposed presensitized planographic printing plate with a developer; and washing the developed printing plate with a washing water, wherein the ratio W/D of the washing time W to the cross-over time D taken from completion of the developing step to the beginning of the washing step is 3 or more.Type: GrantFiled: September 4, 1997Date of Patent: November 30, 1999Assignee: Konica CorporationInventors: Yoko Hirai, Yasuhisa Sugi
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Patent number: 5962183Abstract: The present invention provides methods for producing a photoresist having a very low level of metal ions, utilizing a treated chelating ion exchange resins to make the neutral ammonium salt or acid form. A method is also provided for producing semiconductor devices using such photoresist compositions.Type: GrantFiled: November 27, 1995Date of Patent: October 5, 1999Assignee: Clariant Finance (BVI) LimitedInventors: M. Dalil Rahman, Daniel P. Aubin
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Patent number: 5928836Abstract: The present invention provides a method for producing a film forming, fractionated novolak resin copolymer exhibiting fast photospeed and superior performance in a photoresist composition. A method is also provided for producing photoresist composition from such a fractionated novolak resin copolymer and for producing semiconductor devices using such a photoresist composition.Type: GrantFiled: September 29, 1997Date of Patent: July 27, 1999Assignee: Clariant Finance (BVI) LimitedInventors: M. Dalil Rahman, Stanley F. Wanat, Michelle M. Cook, Douglas S. McKenzie, Sunit S. Dixit
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Patent number: 5922511Abstract: According to the present invention there is provided a method for making a lithographic printing plate comprising the steps of:(1) image-wise exposing an imaging element having on a support in the order given (i) a uniform ink-repellant layer comprising a hydrophilic binder cross-linked by means of a hydrolysed tetra-alkylorthosilicate and (ii) a photosensitive layer comprising a diazonium salt or a diazo resin;(2) and developing a thus obtained image-wise exposed imaging element by mounting it on a print cylinder of a printing press and supplying an aqueous dampening liquid and/or ink to said photosensitive layer.Type: GrantFiled: October 11, 1996Date of Patent: July 13, 1999Assignee: Agfa-Gevaert, N.V.Inventors: Joan Vermeersch, Dirk Kokkelenberg, Johan Van Hunsel, Guido Hauquier
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Patent number: 5879861Abstract: According to the present invention there is provided a method for making a lithographic printing plate comprising the steps of:providing an imaging element comprising on a support having a hydrophilic surface a photosensitive layer and a thermosensitive layer, said thermosensitive layer being opaque to light for which said photosensitive layer has spectral sensitivity and said thermosensitive layer comprising an infrared pigment dispersed in a binder;mounting said imaging element on a drum;image-wise exposing said imaging element by means of an infrared laser in an internal or external drum configuration thereby ablating said thermosensitive layer and rendering it image-wise transparent;overall exposing said imaging element with light to which said photosensitive layer has spectral sensitivity;developing said imaging element to leave an ink accepting image of said photosensitive layer on said support.Type: GrantFiled: April 16, 1997Date of Patent: March 9, 1999Assignee: Agfa-Gevaert, N.V.Inventors: Marc Van Damme, Joan Vermeersch
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Patent number: 5866295Abstract: The present invention relates to novel photosensitive quinolone compounds, specifically novel 3-diazo 2,4-quinolinedione compounds, that may be used in a variety of applications, such as, photosensitive coating compositions, pharmaceuticals, agricultural, amongst others. The invention further relates to a process for making the novel photosensitive 3-diazo 2,4-quinolinedione compounds. These compounds are particularity useful as a photoactive component in a positive working photoresist composition, particularity for use as a deep ultraviolet (UV) photoresist.Type: GrantFiled: March 7, 1997Date of Patent: February 2, 1999Assignee: Clariant Finance (BVI) LimitedInventors: Joseph E. Oberlander, Dana L. Durham, Dinesh N. Khanna
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Patent number: 5863700Abstract: The present invention provides a method for producing a water insoluble, aqueous alkali soluble novolak resins having consistent molecular weight and superior performance in photoresist composition, by isolating such novolak resin without high temperature distillation. A method is also provided for producing photoresist composition from such a novolak resin and for producing semiconductor devices using such a photoresist composition.Type: GrantFiled: September 29, 1997Date of Patent: January 26, 1999Assignee: Clariant Finance (BVI) LimitedInventors: M. Dalil Rahman, Ping-Hung Lu
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Patent number: 5753404Abstract: A photosensitive recording material is described which has a layer base, a negative-working photosensitive layer containing a diazonium salt and a water-insoluble polymeric binder which is soluble or swellable in aqueous alkaline solutions, and a discontinuous top layer which forms a rough surface and which is composed of particles of a water-insoluble polymer which is dispersible in water in the presence of anionic or anionic/nonionic dispersants and which has a content of free acid groups or acid groups neutralized by salt formation of less than 0.8 mmol/g, the mean height of the particles being 2 to 6 .mu.m, the maximum height less than 10 .mu.m, the mean horizontal diameter less than 40 .mu.m, the maximum diameter less than 80 .mu.m and the number of particles being 100 to 10,000 per cm.sup.2. The material is suitable for the production of planographic printing plates and requires only short vacuum times in a vacuum-operated copying frame.Type: GrantFiled: October 31, 1995Date of Patent: May 19, 1998Assignee: Agfa-Gevaert AGInventors: Andreas Elsaesser, Otfried Gaschler, Werner Frass, Klaus-Peter Konrad
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Patent number: 5739265Abstract: A process for producing a water insoluble, aqueous alkali soluble, film forming novolak resin having low metal ions, made by the fractionation of a phenol formaldehyde condensation product, a process for producing a resin a photoresist composition of superior quality containing such novolak resin, and a method for producing a semiconductor device using such photoresist composition.Type: GrantFiled: September 20, 1995Date of Patent: April 14, 1998Assignee: Clariant Finance (BVI) Ltd.Inventors: M. Dalil Rahman, Daniel P. Aubin, Dinesh N. Khanna, Sunit S. Dixit
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Patent number: 5693749Abstract: A process for producing a water insoluble, aqueous alkali soluble, film forming novolak resin fraction having a low metal ion content, made by the fractionation of a phenol formaldehyde condensation product, a process for producing a photoresist compositions containing such a novolak resin, and a method for producing a semiconductor device using such a photoresist composition.Type: GrantFiled: September 20, 1995Date of Patent: December 2, 1997Assignee: Hoechst Celanese CorporationInventors: M. Dalil Rahman, Daniel P. Aubin, Dinesh N. Khanna, Sunit S. Dixit
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Patent number: 5677102Abstract: Proposed is a method for the preparation of a photoresist composition in the form of a solution which is free from the troubles due to formation of particles in the solution after prolonged storage. The method comprises the steps of (a) preparing a solution by dissolving an alkali-soluble resin and a quinone diazide group-containing compound in an organic solvent; and (b) subjecting the solution to a heat treatment at 75.degree. to 85.degree. C. for such a length of time that the solution diluted with ethyleneglycol monomethyl ether in a solid concentration of 0.2% has an absorbance of light in the range from 0.05 to 0.75 at a wavelength of 500 nm for an optical path length of 1 cm.Type: GrantFiled: March 20, 1996Date of Patent: October 14, 1997Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventor: Kouji Shiihara
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Patent number: 5656413Abstract: The present invention provides methods for producing TPPA having low level of metal ions, utilizing treated ion exchange resins. A method is also provided for producing photoresist composition having a very low level of metal ions from such TPPA for producing semiconductor devices using such photoresist compositions.Type: GrantFiled: September 28, 1995Date of Patent: August 12, 1997Assignee: Hoechst Celanese CorporationInventors: M. Dalil Rahman, Daniel P. Aubin
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Patent number: 5618649Abstract: The present invention provides an imaging element comprising on a hydrophilic support a light sensitive layer containing a diazo resin or a diazonium salt characterized in that said light sensitive layer contains pullulan. The obtained imaging element shows an improved storage stability.Type: GrantFiled: May 6, 1996Date of Patent: April 8, 1997Assignee: AGFA-Gevaert, N.V.Inventors: Joan Vermeersch, Guido Hauquier, Dirk Kokkelenberg
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Patent number: 5587267Abstract: Changing (varying, irregular) resist thickness on semiconductor wafers having irregular top surface topography or having different island sizes, affects the percent reflectance (and absorption efficiency) of incident photolithographic light, and consequently the critical dimensions of underlying features being formed (e.g., polysilicon gates). A low solvent content resist solution that can be applied as an aerosol provides a more uniform thickness resist film, eliminating or diminishing photoresist thickness variations. A top antireflective coating (TAR) also aids in uniformizing reflectance, despite resist thickness variations. The two techniques can be used alone, or together. Hence, better control over underlying gate size can be effected, without differential biasing.Type: GrantFiled: June 5, 1995Date of Patent: December 24, 1996Assignee: LSI Logic CorporationInventor: Mario Garza
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Patent number: 5547806Abstract: The invention is directed to a process for producing microcapsules containing a diazonium salt compound by the steps of (i) adding a dialkyl sulfate compound represented by the formula: RO--SO.sub.2 --OR, where R is an alkyl or cycloalkyl group having up to 24 carbon atoms, to an organic solvent solution containing a diazonium salt compound and a polyfunctional isocyanate compound, (ii) emulsifying the resulting organic solvent solution into an aqueous solution of ,a water-soluble polymer, and then (iii) polymerizing the polyfunctional isocyanate compound to form microcapsule walls. The invention also discloses the recording material produced by the process.Type: GrantFiled: December 21, 1994Date of Patent: August 20, 1996Assignee: Fuji Photo Film Co., Ltd.Inventors: Hiroshi Kamikawa, Sadao Ishige
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Patent number: 5543263Abstract: The present invention provides methods for producing photoresist compositions having a very low level of metal ions, utilizing specially treated ion exchange resins. A method is also provided for producing semiconductor devices using such photoresist compositions.Type: GrantFiled: June 17, 1994Date of Patent: August 6, 1996Assignee: Hoechst Celanese CorporationInventors: M. Dalil Rahman, Dana L. Durham
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Patent number: 5492789Abstract: A process for producing microcapsules containing a diazonium salt compound, and a photofixation thermal recording material employing the same. The process comprises adding an organic solvent solution containing both the diazonium salt compound and a polyfunctional isocyanate compound to an aqueous solution of a water-soluble polymer, emulsifying the organic solvent solution into the aqueous solution using an emulsifying agent, and then polymerizing the polyfunctional isocyanate compound to form microcapsule walls, said emulsifying agent comprising an alkyl glucoside represented by formula (I): ##STR1## wherein n is an integer of 0 to 2 and R represents a linear or branched alkyl group having 4 to 18 carbon atoms.Type: GrantFiled: October 26, 1994Date of Patent: February 20, 1996Assignee: Fuji Photo Film Co., Ltd.Inventors: Akira Igarashi, Sadao Ishige
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Patent number: 5476750Abstract: The present invention provides methods for producing water insoluble, aqueous alkali soluble novolak resins having a very low level of metal ions and a substantially consistent molecular weight. A method is also provided for producing photoresist composition from such novolak resins and for producing semiconductor devices using such photoresist compositions.Type: GrantFiled: December 29, 1992Date of Patent: December 19, 1995Assignee: Hoechst Celanese CorporationInventors: M. Dalil Rahman, Ping-Hung Lu, Daniel P. Aubin, Ralph R. Dammel, Dana L. Durham
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Patent number: 5401604Abstract: A positive-type photosensitive resin composition containing a resin which results from reactions between a specific polyepoxide compound, a carboxylic acid compound having a specific phenolic hydroxyl group, a carboxylic acid compound having no specific phenolic hydroxyl group, and 1,2-quinone diazide sulfonyl halide. The resin composition has high exposure sensitivity, is capable of inhibiting swell or dissolution of unexposed areas during the stage of development, and yet retains other favorable properties. The resin composition has also attained short developing time.Type: GrantFiled: January 31, 1994Date of Patent: March 28, 1995Assignee: Nippon Paint Co., Ltd.Inventors: Chikayuki Otsuka, Mamoru Seio, Kiyomi Sakurai, Kazuyuki Kawamura
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Patent number: 5382495Abstract: It has surprisingly been found that a protective coating composition for diazo-containing materials can be prepared from a cellulose ester, a hydroxylated resin, a crosslinking agent, microcrystalline silica and an acid catalyst. The coating compositions of the invention provide improved protection for diazo-containing materials from physical and chemical damage. The protective coating compositions of the invention are particularly effective for protecting the diazo-containing materials from chemical attack from solvents. The invention further relates to photographic elements and phototools provided with the protective coating composition and a method for providing the coating composition.Type: GrantFiled: May 1, 1991Date of Patent: January 17, 1995Assignee: Rexham Graphics, Inc.Inventors: Thomas C. Niziolek, George Hodgins, Marie B. Ray
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Patent number: 5376504Abstract: Photoresists are disclosed that display increased sensitivity, measured as lithographic potential, when compared to known photoresists that contain melamine resin as a crosslinker. The melamine resin in these photoresists contains a higher percent by weight of monomeric hexamethoxymethylmelamine than in known resists.Type: GrantFiled: August 27, 1992Date of Patent: December 27, 1994Assignee: Rohm and Haas CompanyInventors: Karen A. Graziano, Leonard E. Bogan, Jr., Robert J. Olsen, Susan E. Anderson
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Patent number: 5358823Abstract: A radiation-sensitive composition is disclosed comprising a polymeric binder which is insoluble in water, but soluble or at least swellable in aqueous alkaline solution and a 2,3,4,4'-tetrahydroxybenzophenone which is partially esterified with (1,2-naphthoquinone 2-diazide)-4- and/or -5-sulfonic acid, which additionally contains either a dihydroxybenzophenone which is completely esterified with (1,2-naphthoquinone 2-diazide)-4- and/or -5-sulfonic acid or a trihydroxybenzophenone which is partially or completely esterified with (1,2-naphthoquinone 2-diazide)-4- and/or -5-sulfonic acid. The weight ratio of esterified 2,3,4,4'-tetrahydroxybenzophenone to esterified di- or trihydroxybenzophenone varies between about 4:6 and 7:3 and the esterified hydroxybenzophenones, as a whole, are present in a proportion of 5 to 40% by weight, based on the total weight of solids contained in the composition.Type: GrantFiled: April 1, 1992Date of Patent: October 25, 1994Assignee: Hoechst AktiengesellschaftInventors: Wolfgang Zahn, Hans-Joachim Merrem, Fritz Erdmann, Axel Schmitt
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Patent number: 5340681Abstract: Photopolymeric printing plates are presented wherein and electrochemically etched and anodized, silicated aluminum substrate has a single photosensitive coating thereon composed of a photopolymerizable combination which includes a photopolymerizable pigment dispersion, a photosensitive lithographic diazonium resin, multifunctional acrylate oligomer, multifunctional acrylate monomer, photopolymerizable binder and photoinitiator to yield a non-tacky, mar resistant, easily developed durable plate. In a preferred embodiment, an additional aqueous, non-photosensitive overcoat is applied over the initial coating to retard oxygen inhibition.Type: GrantFiled: November 5, 1993Date of Patent: August 23, 1994Assignee: International Paper CompanyInventors: Maria T. Sypek, Paul A. Perron, Gary V. Grosclaude
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Patent number: 5302490Abstract: The invention relates to radiation sensitive compositions having high uniformity when deposited as thick films. The compositions of the invention comprise a radiation sensitive component and a resin binder blend. The resin binder blend is a mixture of an aliphatic novolak resin component and an aromatic novolak resin component.Type: GrantFiled: April 1, 1993Date of Patent: April 12, 1994Assignee: Shipley Company Inc.Inventors: Theodore H. Fedynyshyn, Marc Connelly
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Patent number: 5242780Abstract: An electrophoretic positive working photosensitive composition for producing a photoresist pattern on metal base plate comprises a photosensitive compound, in which a photosensitive quinone diazide group is grafted on a polyester, and an acrylic copolymer containing carboxyl group, the composition forms a smooth photoresist film on the plate and has a good adhesion to the surface that no pinehole is found.Type: GrantFiled: October 18, 1991Date of Patent: September 7, 1993Assignee: Industrial Technology Research InstituteInventors: Hsien-Kuang Lin, Jim-Chyuan Shieh, Dhei-Jhai Lin
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Patent number: 5217840Abstract: A process for converting a normally positive working photosensitive composition to a negative working composition. One forms a composition containing an alkali soluble resin, a 1,2 quinone diazide-4-sulfonyl compound and an acid catalyzed crosslinker in a solvent mixture. After drying and imagewise exposing, the composition is baked and developed to produce a negative image.Type: GrantFiled: May 25, 1990Date of Patent: June 8, 1993Assignee: Hoechst Celanese CorporationInventors: Mark A. Spak, Donald Mammato, Dana Durham, Sangya Jain
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Patent number: 5200291Abstract: A polymeric compound having the formula ##STR1## wherein x ranges from about 0.05 to about 0.5y ranges from about 0.80 to about 0.35z ranges from about 0.10 to about 0.25n ranges from about 50 to about 1500R is selected from the group consisting of phenyl and C.sub.1 to C.sub.4 alkyl substituted phenyl;K is selected from the group consisting of ##STR2## --S--, --O--, and --CH.sub.2 --, or is absent; P and P.sub.1 are selected from the group consisting of C.sub.1 to C.sub.4 alkyl, methoxy, ethoxy, butoxy, and H; andP.sub.1 may be the same as P or different.Type: GrantFiled: April 11, 1991Date of Patent: April 6, 1993Assignee: Hoechst Celanese CorporationInventor: Stanley F. Wanat
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Patent number: 5192640Abstract: A process for preparing 7-hydroxy-1,2-naphthoquinone-2-diazide-4-sulfonic acid or salts thereof, of the general formula Z ##STR1## is disclosed in which X=hydrogen, a metal or an ammonium group, preferably an alkali metal or alkaline earth metal, especially sodium or potassium and the ammonium group.The compounds can be used as much or as intermediates or starting materials for the production of light-sensitive compounds and radiation-sensitive mixtures and materials.Type: GrantFiled: August 9, 1990Date of Patent: March 9, 1993Assignee: Hoechst AktiengesellschaftInventors: Siegfried Scheler, Gerhard Buhr, Klaus Bergmann
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Patent number: 5166036Abstract: The invention provides an aqueous electrodeposition coating composition for a positive working resist and an image-forming method using the same. The coating composition is very stable under storage conditions and is capable of resulting in a positive working resist which is specifically useful in the preparation of a printed circuit board with mini-via-holes.Type: GrantFiled: July 9, 1991Date of Patent: November 24, 1992Assignee: Nippon Paint Co., Ltd.Inventors: Mamoru Seio, Takeshi Ikeda, Kanji Nishijima, Katsukiyo Ishikawa
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Patent number: RE41083Abstract: A radiation-sensitive composition for use in printing plates is described. The composition comprises: (a) at least one novolak; (b) at least one naphthoquinone diazide derivative; and (c) a copolymer comprising units A, B, and a unit C comprising a cyclic terminal urea group, wherein unit A is present in an amount of about 5 to about 50 mol % and has the formula is represented by wherein R1 is selected such that the homopolymer of A is alkali-soluble, unit B is present in an amount of about 20 to about 70 mol % and has the following formula is represented by wherein R2 is selected such that the homopolymer of B has a glass transition temperature greater than 100° C., preferably a glass transition temperature in the range from about 100 to about 380° C.Type: GrantFiled: July 26, 2005Date of Patent: January 19, 2010Assignee: Eastman Kodak CompanyInventor: Mathias Jarek