Using Specific Adjuvant Other Than Radiation-sensitive Diazo Compound Patents (Class 430/169)
  • Patent number: 11573490
    Abstract: The present invention relates to a positive-type photosensitive resin composition and a cured film prepared therefrom. The positive-type photosensitive resin composition comprises a nonpolar organic solvent, thereby suppressing the reactivity of the epoxy group in the composition to reduce the production of diol compounds. When a cured film is prepared from the composition, an appropriate level of developability can be maintained to further enhance the pattern adhesiveness, resolution, and sensitivity. Further, since the composition of the present invention has a small difference in the film retention rates at room temperature and low temperatures, the composition may have stable stability over time.
    Type: Grant
    Filed: May 20, 2020
    Date of Patent: February 7, 2023
    Inventors: Ji Ung Kim, Geun Huh, Ju-Young Jung, JinKyu Im, Yeonok Kim
  • Patent number: 10563088
    Abstract: A curable composition includes a condensation product having a weight average molecular weight of 30,000 or less and a curing agent, the condensation product being obtained by hydrolysis and condensation of a first and second silane compound in the presence of a neutral salt catalyst. The condensation product also has a ratio Y/X of 0.2 or less, wherein X is the number of moles of an OR3 group directly bonded to silicon atoms of the first and second silane compounds, and Y is the number of moles of an OR3 group directly bonded to a silicon atom of the condensation product. The first silane compound is represented by R1—(SiR2a(OR3)3-a), and the second silane compound is represented by R4—(SiR2a(OR3)3-a).
    Type: Grant
    Filed: June 14, 2017
    Date of Patent: February 18, 2020
    Assignee: KANEKA CORPORATION
    Inventors: Hiroki Fukaumi, Youichi Matsuo, Atsushi Tsukao
  • Patent number: 10227505
    Abstract: An active energy ray-curable composition includes (A) a condensate having a weight average molecular weight of 20,000 or less, and (B) a photoacid generator, with the condensate (A) being obtained by hydrolysis/condensation of: (I) a silane compound containing a hydrolyzable silyl group represented by formula (I): R1—(SiR2a(OR3)3-a. A ratio (Y/X) of Y to X is 0.2 or less, where X represents the number of moles of OR3 groups directly bonded to silicon atoms in the silane compound (I) which is a starting material of the condensate (A) and Y represents the number of moles of OR3 groups directly bonded to silicon atoms in the condensate (A).
    Type: Grant
    Filed: June 23, 2014
    Date of Patent: March 12, 2019
    Assignee: KANEKA CORPORATION
    Inventors: Hiroki Fukaumi, Youichi Matsuo, Atsushi Tsukao, Shinji Kagitani
  • Patent number: 9611410
    Abstract: An adhesive resin composition includes an expandable sticky polymer having a structure derived from a Meldrum's acid derivative, or a Meldrum's acid derivative represented by the following general formula (1) and an adhesive resin.
    Type: Grant
    Filed: December 7, 2012
    Date of Patent: April 4, 2017
    Assignee: MITSUI CHEMICALS TOHCELLO, INC.
    Inventors: Shinichi Usugi, Noboru Kawasaki, Jun Kamada, Takuzo Aida
  • Patent number: 9240500
    Abstract: There is provided a novel material used for solar cells that can contribute to the improvement in maximum output of solar cells without using the conventional MPPT system. A film-forming material for forming a light-collecting film on a transparent electrode of a solar cell, including an aromatic group-containing organic polymer compound (A) and a cross-linker (B), wherein the film-forming material exhibits an index of refraction of 1.5 to 2.0 at a wavelength of 633 nm and a transmittance of 95% or more with respect to light having a wavelength of 400 nm, and a solar cell obtained by coating a cured film made from the film-forming material on a surface of a transparent electrode.
    Type: Grant
    Filed: December 1, 2011
    Date of Patent: January 19, 2016
    Assignee: NISSAN CHEMICAL INDUSTRIES, LTD.
    Inventor: Kazuya Ebara
  • Patent number: 7374856
    Abstract: A positive photosensitive siloxane composition having high photosensitivity and having such properties as high heat resistance, high transparency and low dielectric constant may be used to form a planarization film for a TFT substrate, an interlayer dielectrics or a core or cladding of an optical waveguide. The positive photosensitive siloxane composition includes a siloxane polymer, quinonediazide compound and solvent, and a cured film formed of the composition has a light transmittance per 3 ?m of film thickness at a wavelength of 400 nm of 95% or more.
    Type: Grant
    Filed: November 15, 2005
    Date of Patent: May 20, 2008
    Assignee: Toray Industries, Inc.
    Inventors: Mitsuhito Suwa, Takenori Fujiwara, Masahide Senoo, Hirokazu Iimori
  • Patent number: 7361444
    Abstract: Disclosed are multilayered resist structures including bilayer and top surface imaging which utilize tuned underlayers functioning as ARCs, planarizing layers, and etch resistant hard masks whose properties such as optical, chemical and physical properties are tailored to give a multilayer resist structure exhibiting high resolution, residue free lithography and methods of preparing these materials.
    Type: Grant
    Filed: February 23, 1999
    Date of Patent: April 22, 2008
    Assignee: International Business Machines Corporation
    Inventors: Marie Angelopoulos, Katherina E. Babich, Douglas Charles LaTulipe, Qinghuang Lin, David R. Medeiros, Wayne Martin Moreau, Karen E. Petrillo, John P. Simons
  • Patent number: 6815138
    Abstract: A heat-sensitive recording material includes a support having disposed thereon a heat-sensitive recording layer and a protective layer. The heat-sensitive recording layer contains at least two components that react to develop color by imagewise heating. At least one layer contains a compound represented by the following general formula (I). In the general formula (I), R represents a hydrophobic group or a hydrophobic polymer, and n represents an integer.
    Type: Grant
    Filed: September 16, 2002
    Date of Patent: November 9, 2004
    Assignee: Fuji Photo Film Co., Ltd.
    Inventor: Toshiaki Aono
  • Publication number: 20040063022
    Abstract: 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: Application
    Filed: September 17, 2003
    Publication date: April 1, 2004
    Applicant: Kodak Polychrome Graphics, LLC.
    Inventors: Stephan J. Platzer, Maria T. Sypek, Paul Perron, Harald Baumann, Melinda Alden
  • Publication number: 20040023147
    Abstract: A positive photosensitive resin composition having high sensitivity is provided which can form patterns with high resolution and high film thickness retention and can give by curing film excellent in mechanical characteristics, adhesion, and water absorption. This composition comprises 100 parts by weight of an alkali-soluble resin, 1 to 100 parts by weight of a photosensitive diazoquinone compound (B) and a filler (C), the content (F) of the filler(C) as defined by the following formula ranging from 2 to 70 wt %.
    Type: Application
    Filed: April 25, 2003
    Publication date: February 5, 2004
    Inventors: Takashi Hirano, Shusaku Okaaki
  • Patent number: 6683674
    Abstract: 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: Grant
    Filed: May 1, 2001
    Date of Patent: January 27, 2004
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Nobufumi Mori, Akinori Harada, Shintaro Washizu
  • Publication number: 20030143480
    Abstract: Provided is a polybenzoxazole precursor having a high purity which does not contain ionic by-products.
    Type: Application
    Filed: November 26, 2002
    Publication date: July 31, 2003
    Inventors: Mitsuru Ueda, Kazuya Ebara, Kenji Miyagawa, Kazuo Yamanaka, Yoichi Yonehara
  • Patent number: 6531257
    Abstract: Provided is a photosensitive copper paste permitting the formation of a fine and thick copper pattern having high adhesion to a substrate, and having excellent preservation stability without causing gelation, and a method of forming a copper pattern, a circuit board and a ceramic multilayer substrate using the photosensitive copper paste. The photosensitive copper paste includes a mixture of an organic binder having an acid functional group, a copper powder and a photosensitive organic component. The copper powder has a surface layer having a thickness of at least 0.1 &mgr;m from the surface composed CuO as a main component. The copper powder also has an oxygen content of about 0.8% to 5% by weight.
    Type: Grant
    Filed: November 30, 2001
    Date of Patent: March 11, 2003
    Assignee: Murata Manufacturing Co. Ltd
    Inventor: Masahiro Kubota
  • Patent number: 6346361
    Abstract: 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: Grant
    Filed: October 6, 1999
    Date of Patent: February 12, 2002
    Assignee: Clariant Finance (BVI) Limited
    Inventors: Jianhui Shan, Shuji Ding, Eleazar B. Gonzalez, Dinesh N. Khanna
  • Patent number: 6165689
    Abstract: 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: Grant
    Filed: September 28, 1998
    Date of Patent: December 26, 2000
    Assignee: AGFA-Gevaert, N.V.
    Inventors: Joan Vermeersch, Marc Van Damme, Dirk Kokkelenberg
  • Patent number: 5994031
    Abstract: 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: Grant
    Filed: September 4, 1997
    Date of Patent: November 30, 1999
    Assignee: Konica Corporation
    Inventors: Yoko Hirai, Yasuhisa Sugi
  • Patent number: 5866295
    Abstract: 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: Grant
    Filed: March 7, 1997
    Date of Patent: February 2, 1999
    Assignee: Clariant Finance (BVI) Limited
    Inventors: Joseph E. Oberlander, Dana L. Durham, Dinesh N. Khanna
  • Patent number: 5863700
    Abstract: 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: Grant
    Filed: September 29, 1997
    Date of Patent: January 26, 1999
    Assignee: Clariant Finance (BVI) Limited
    Inventors: M. Dalil Rahman, Ping-Hung Lu
  • Patent number: 5858627
    Abstract: Process for producing a photosensitizer comprising a diazo ester of a p-cresol oligomer where at least one of the hydroxy groups on the p-cresol ring has been esterified with diazo-sulfonyl chloride comprising from about 60 to 100 mole % 2,1,4 or 2,1,5-diazo sulfonyl chloride, or a mixture thereof; and a photoresist comprising an admixture of the photosensitizer, which is present in the photoresist composition in an amount sufficient to uniformly photosensitive the photoresist composition, a water insoluble, aqueous alkali soluble novolak resin, the novolak resin being present in the photoresist composition in an amount sufficient to form a substantially uniform photoresist composition, and a suitable solvent.
    Type: Grant
    Filed: August 29, 1997
    Date of Patent: January 12, 1999
    Assignee: Clariant Finance (BVI) Limited
    Inventors: M. Dalil Rahman, Dinesh N. Khanna, Daniel Aubin, Douglas McKenzie
  • Patent number: 5853947
    Abstract: A photosensitive positive working photosensitive composition suitable for use as a photoresist, which comprises an admixture of at least one water insoluble, aqueous alkali soluble, film forming novolak resin; at least one o-diazonaphthoquinone photosensitizer; and a photoresist solvent mixture comprising a propylene glycol alkyl ether acetate and 3-methyl-3-methoxy butanol and process for producing such a composition.
    Type: Grant
    Filed: December 21, 1995
    Date of Patent: December 29, 1998
    Assignee: Clariant Finance (BVI) Limited
    Inventors: Stanley F. Wanat, M. Dalil Rahman, Dinesh N. Khanna, Daniel P. Aubin, Sunit S. Dixit
  • Patent number: 5837417
    Abstract: Process for producing a photosensitizer comprising a diazo ester of a p-cresol oligomer where at least one of the hydroxy groups on the p-cresol ring has been esterified with diazo-sulfonyl chloride comprising from about 60 to 100 mole % 2,1,4 or 2,1,5-diazo sulfonyl chloride, or a mixture thereof; and a photoresist comprising an admixture of the photosensitizer, which is present in the photoresist composition in an amount sufficient to uniformly photosensitive the photoresist composition, a water insoluble, aqueous alkali soluble novolak resin, the novolak resin being present in the photoresist composition in an amount sufficient to form a substantially uniform photoresist composition, and a suitable solvent.
    Type: Grant
    Filed: December 30, 1994
    Date of Patent: November 17, 1998
    Assignee: Clariant Finance (BVI) Limited
    Inventors: M. Dalil Rahman, Dinesh N. Khanna, Daniel Aubin, Douglas McKenzie
  • Patent number: 5776654
    Abstract: 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 plastic film support in the order given (i) a uniform ink-repellant layer comprising a cross-linked hydrophilic binder 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: Grant
    Filed: September 30, 1996
    Date of Patent: July 7, 1998
    Assignee: Agfa-Gevaert N.V.
    Inventors: Joan Vermeersch, Eric Verschueren, Guido Hauquier, Willem Cortens
  • Patent number: 5776653
    Abstract: 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 of a flexible film support in the order given (i) a uniform ink-repellant layer comprising a cross-linked hydrophilic binder 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 wiping it with a disposable absorbing tissue moistened with water or fountain solution.
    Type: Grant
    Filed: December 4, 1996
    Date of Patent: July 7, 1998
    Assignee: AGFA-Gevaert, N.V.
    Inventors: Joan Vermeersch, Eric Verschueren, Dirk Kokkelenberg
  • Patent number: 5753404
    Abstract: 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: Grant
    Filed: October 31, 1995
    Date of Patent: May 19, 1998
    Assignee: Agfa-Gevaert AG
    Inventors: Andreas Elsaesser, Otfried Gaschler, Werner Frass, Klaus-Peter Konrad
  • Patent number: 5753403
    Abstract: The present invention provides an imaging element comprising on a hydrophilic base a light-sensitive layer containing polyvinyl alcohol hydrolyzed to at least an extent of 95% by weight, a cationic surfactant and a diazo resin and/or a diazonium salt characterized in that the light-sensitive layer comprises metal-free phthalocyanine.The present invention also provides a method for obtaining an imaging element as defined in any of the claims 1 to 6 bypreparing a dispersion of metal-free phthalocyanine in water in the presence of a cationic surfactant in an amount ranging from 0.24 g/l to 24 g/l;preparing a light-sensitive composition by mixing said dispersion, polyvinyl alcohol hydrolyzed to at least an extent of 95% by weight and a diazo resin and/or a diazonium salt andcoating said light-sensitive composition on a hydrophilic base, characterized in that said dispersion comprises polyvinyl alcohol hydrolyzed to at least an extent of 95% by weight in an amount ranging from 4.0 g/l to 200 g/l.
    Type: Grant
    Filed: April 9, 1996
    Date of Patent: May 19, 1998
    Assignee: Agfa-Gevaert, N.V.
    Inventors: Joan Vermeersch, Dirk Kokkelenberg, Luc Vanmaele, Jan Gilleir
  • Patent number: 5739265
    Abstract: 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: Grant
    Filed: September 20, 1995
    Date of Patent: April 14, 1998
    Assignee: Clariant Finance (BVI) Ltd.
    Inventors: M. Dalil Rahman, Daniel P. Aubin, Dinesh N. Khanna, Sunit S. Dixit
  • Patent number: 5725903
    Abstract: A conformal, substantially uniform thickness layer of photoresist is deposited on a semiconductor wafer by causing photoresist solids to "sediment" out of solution or suspension. Generally, the more conformal the layer, the more uniform the reflectance of the layer and the less variation in underlying feature critical dimension (cd). In order to accommodate possible resulting deviations in photoresist layer thickness causing undesirable reflectance nonuniformities (and cd variations), a top antireflective coating may be applied to the photoresist layer. In the case of a point-by-point lithography process, such as e-beam lithography, the thickness/reflectance variations can be mapped, and exposure doses adjusted accordingly.
    Type: Grant
    Filed: August 16, 1995
    Date of Patent: March 10, 1998
    Assignee: LSI Logic Corporation
    Inventor: Michael D. Rostoker
  • Patent number: 5719003
    Abstract: A photoresist composition comprising an alkali soluble resin and an ortho-naphthoquinone diazide sulfonic acid ester of a polyhydroxy alcohol. The photoresist is characterized by having at least a portion of its free hydroxyl groups on the photoactive compound blocked with an acid labile blocking group that generates a hydroxide upon cleavage.
    Type: Grant
    Filed: September 27, 1995
    Date of Patent: February 17, 1998
    Assignee: Shipley Company, L.L.C.
    Inventors: Roger F. Sinta, Daniel Y. Pai, Timothy G. Adams
  • Patent number: 5693749
    Abstract: 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: Grant
    Filed: September 20, 1995
    Date of Patent: December 2, 1997
    Assignee: Hoechst Celanese Corporation
    Inventors: M. Dalil Rahman, Daniel P. Aubin, Dinesh N. Khanna, Sunit S. Dixit
  • Patent number: 5688627
    Abstract: A water soluble diazonium salt composition made by the condensation of diazoaryl amines and aldehydes and precipitated to form a polymeric anionic species having both ZnCl.sub.4.sup.= and HSO.sub.4.sup.- moieties. These composition are blended with suitable binders, colorants and other optional components to produce light sensitive coating compositions. When applied to aluminum substrates, these light sensitive coating compositions form lithographic printing plates that are especially stable under high humidity conditions. Such plates may be developed by either water alone or by water which contains surfactants and/or a small amount of an organic solvent.
    Type: Grant
    Filed: July 2, 1996
    Date of Patent: November 18, 1997
    Assignee: Precision Lithograining Corp.
    Inventor: Albert S. Deutsch
  • Patent number: 5670294
    Abstract: The present invention relates to an aqueous alkaline developing solution comprising an alkaline mixture of an alkali metal silicate and/or an alkali metal metasilicate, wherein the M.sub.2 O/SiO.sub.2 molar ratio of said alkaline mixture is in the range of from 0.5 to 1.2, the total content of said alkaline mixture being in the range of from 6 to 15% by weight of the total developing solution, and wherein said developing solution comprises a non-ionic surfactant and at least another surfactant selected from the group consisting of anionic surfactants and amphoteric surfactants. An alkali metal hydroxide can be optionally added to the alkaline mixture. Also claimed is the concentrated developing solution to be diluted to the desired strength.
    Type: Grant
    Filed: August 29, 1996
    Date of Patent: September 23, 1997
    Assignee: Imation Corp
    Inventor: Mario Piro
  • Patent number: 5656413
    Abstract: 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: Grant
    Filed: September 28, 1995
    Date of Patent: August 12, 1997
    Assignee: Hoechst Celanese Corporation
    Inventors: M. Dalil Rahman, Daniel P. Aubin
  • Patent number: 5637436
    Abstract: Ternary mixtures of C.sub.4 to C.sub.8 alkyl acetate, C.sub.4 to C.sub.8 alkyl alcohol, and water, formulated to have a flash point of above 100.degree. F., are disclosed, particularly for use in edge residue removal processes in the fabrication of integrated circuits and like products.
    Type: Grant
    Filed: April 4, 1995
    Date of Patent: June 10, 1997
    Assignee: Hoechst Celanese Corporation
    Inventor: Donald W. Johnson
  • Patent number: 5618655
    Abstract: A process of removing trace metal impurities from an impure resist component solution comprising the steps of:(1) forming an impure resist component solution containing trace amounts of dissolved metallic impurities, the resist component solvent selected from the group consisting of ethyl lactate, ethyl 3-ethoxypropionate, methyl 3-methoxypropionate, propylene glycol methyl ethyl acetate, or mixtures thereof;(2) contacting said impure resist component solution with a mixture of cyclohexane and isopropyl acetate and with an aqueous acidic solution for a sufficient amount of time to form a first two-phase reaction mixture comprising a first aqueous phase containing metallic impurities extracted from said impure resist component solution and a first organic phase containing said resist component solution with a reduced amount of trace metal impurities;(3) separating said first aqueous phase from said first organic phase;(4) contacting said first organic phase with a mixture of water and resist component solvent
    Type: Grant
    Filed: July 17, 1995
    Date of Patent: April 8, 1997
    Assignee: Olin Corporation
    Inventor: James M. Davidson
  • Patent number: 5614349
    Abstract: The present invention provides methods for producing water insoluble, aqueous alkali soluble novolak resins having a precise and consistent molecular weight, by adjusting the concentration of Lewis base. A method is also provided for producing photoresist composition from such novolak resins and for producing semiconductor devices using such photoresist compositions.
    Type: Grant
    Filed: December 29, 1992
    Date of Patent: March 25, 1997
    Assignee: Hoechst Celanese Corporation
    Inventors: M. Dalil Rahman, Daniel P. Aubin, Dana L. Durham, Ralph R. Dammel
  • Patent number: 5580691
    Abstract: The invention provides toner for a two-component type developer containing toner particles including a binder resin and magnetic powder dispersed in the binder resin. The binder resin in the toner is made of a composition including a low molecular weight polymer and a high molecular weight polymer both having an anionic group. The magnetic powder is contained in the toner particles in the range of 0.1 to 5 parts by weight per 100 parts by weight of the binder resin.
    Type: Grant
    Filed: December 27, 1994
    Date of Patent: December 3, 1996
    Assignee: Mita Industrial Co., Ltd.
    Inventors: Masatomi Funato, Yoshitake Shimizu, Seijiro Ishimaru, Norio Kubo, Kazuya Nagao, Terumichi Asano
  • Patent number: 5547806
    Abstract: 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: Grant
    Filed: December 21, 1994
    Date of Patent: August 20, 1996
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Hiroshi Kamikawa, Sadao Ishige
  • Patent number: 5492789
    Abstract: 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: Grant
    Filed: October 26, 1994
    Date of Patent: February 20, 1996
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Akira Igarashi, Sadao Ishige
  • Patent number: 5476750
    Abstract: 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: Grant
    Filed: December 29, 1992
    Date of Patent: December 19, 1995
    Assignee: Hoechst Celanese Corporation
    Inventors: M. Dalil Rahman, Ping-Hung Lu, Daniel P. Aubin, Ralph R. Dammel, Dana L. Durham
  • Patent number: 5457003
    Abstract: A resist material comprises a polysiloxane obtained by hydrolysis and condensation with dehydration of one or more alkoxysilanes having an oxirane ring, or of a mixture of the alkoxysilane(s) having an oxirane ring and one or more alkoxysilanes having no oxirane ring, and an acid generator. The resist material may contain one or more of a spectral sensitizer, an organic polymer having a hydroxyl group or an epoxy compound. Resist patterns are formed by coating an organic polymer on a substrate and then the resist material on the film of the organic polymer to form a two layer resist having a bottom layer of the organic polymer and top layer of the resist material, prebaking, imagewise exposing high radiation, postbaking, and developing the resist with alkaline solutions to remove an unexposed portion of the top layer, and dry etching the bottom layer using the relic of the resist material as a mask. the temperature of the post baking is preferably lower than that of the prebaking.
    Type: Grant
    Filed: July 30, 1993
    Date of Patent: October 10, 1995
    Assignee: Nippon Telegraph and Telephone Corporation
    Inventors: Akinobu Tanaka, Hiroshi Ban, Jiro Nakamura, Takao Kimura, Yoshio Kawai
  • Patent number: 5439774
    Abstract: A positive-type photosensitive electrodeposition coating composition comprising a water-soluble or water-dispersible resin having an ionic group and containing at least one modified quinonediazidesulfone unit represented by the following formula (I) or (II) ##STR1## wherein R.sub.1 represents ##STR2## R.sub.2 represents a hydrogen atom, an alkyl group, a cycloalkyl group or an alkyl ether group, andR.sub.3 represents an alkylene group, a cycloalkylene group, an alkylene ether group,a phenylene group which may optionally be substituted with an alkyl group having 1 to 20 carbon atoms, or an alkylene, cycloalkylene or alkylene ether group containing in its chain a phenylene group which may optionally be substituted with an alkyl group having 1 to 20 carbon atoms, in the molecule.
    Type: Grant
    Filed: September 28, 1994
    Date of Patent: August 8, 1995
    Assignee: Kansai Paint Co., Ltd.
    Inventors: Naozumi Iwasawa, Junichi Higashi
  • Patent number: 5426017
    Abstract: Ternary mixtures of C.sub.4 to C.sub.8 alkyl acetate, C.sub.4 to C.sub.8 alkyl alcohol, and water, formulated to have a flash point of above 100.degree. F., are disclosed, particularly for use in edge residue removal processes in the fabrication of integrated circuits and like products.
    Type: Grant
    Filed: March 10, 1993
    Date of Patent: June 20, 1995
    Assignee: Hoechst Celanese Corporation
    Inventor: Donald W. Johnson
  • Patent number: 5422221
    Abstract: In a resist composition, a novolak resin including at least one recurring unit of the formula (1): ##STR1## wherein n is an integer of 1 to 4 and m is an integer of 0 to 3, having a weight average molecular weight of 1,000 to 10,000 calculated as polystyrene, and having the hydrogen atom of a hydroxyl group therein replaced by a 1,2-naphthoquinonediazidosulfonyl group in a proportion of 0.03 to 0.27 mol per hydrogen atom serves as an alkali-soluble resin and a photosensitive agent. The composition is uniform in that the photosensitive agent is uniformly incorporated in the novolak resin, and thus forms a uniform resist film. It is a useful positive resist having improved sensitivity, resolution, heat resistance, and film retentivity.
    Type: Grant
    Filed: February 16, 1994
    Date of Patent: June 6, 1995
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Satoshi Okazaki, Mitsuo Umemura, Hiroshi Kanbara, Jun Hatakeyama, Tetsuya Inukai, Kazuhiro Nishikawa
  • Patent number: 5401604
    Abstract: 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: Grant
    Filed: January 31, 1994
    Date of Patent: March 28, 1995
    Assignee: Nippon Paint Co., Ltd.
    Inventors: Chikayuki Otsuka, Mamoru Seio, Kiyomi Sakurai, Kazuyuki Kawamura
  • Patent number: 5376504
    Abstract: 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: Grant
    Filed: August 27, 1992
    Date of Patent: December 27, 1994
    Assignee: Rohm and Haas Company
    Inventors: Karen A. Graziano, Leonard E. Bogan, Jr., Robert J. Olsen, Susan E. Anderson
  • Patent number: 5340681
    Abstract: 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: Grant
    Filed: November 5, 1993
    Date of Patent: August 23, 1994
    Assignee: International Paper Company
    Inventors: Maria T. Sypek, Paul A. Perron, Gary V. Grosclaude
  • Patent number: 5328797
    Abstract: The present invention relates to a process for producing a negative-working photosensitive lithographic printing form, in which a negative-working photosensitive mixture which is dissolved in a solvent mixture and which contains a negative-working photosensitive compound and a polymeric binder which is insoluble in water but soluble in aqueous alkaline solution is applied to a base and the layer obtained is subsequently dried, which process comprises using a mixture of more than 2% by weight of at least one monoether of diethylene glycol with one or more organic solvent(s) having a boiling point below 200.degree. C. as the solvent mixture.
    Type: Grant
    Filed: December 23, 1992
    Date of Patent: July 12, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Rudolf Neubauer, Roman Keiper, Siegfried Nuernberger, Sabine Pilger
  • Patent number: 5326826
    Abstract: Radiation-sensitive polymers, a mixture containing these radiation-sensitive polymers as binder, and a process for the preparation of the radiation-sensitive polymer binders are disclosed. A positive radiation-sensitive recording material containing the radiation-sensitive polymer is also disclosed.
    Type: Grant
    Filed: February 26, 1992
    Date of Patent: July 5, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Horst Roeschert, Hans-Joachim Merrem, Georg Pawlowski, Juergen Fuchs, Ralph Dammel
  • Patent number: 5320864
    Abstract: A conformal, substantially uniform thickness layer of photoresist is deposited on a semiconductor wafer by causing photoresist solids to "sediment" out of solution or suspension. Generally, the more conformal the layer, the more uniform the reflectance of the layer and the less variation in underlying feature critical dimension (cd). In order to accommodate possible resulting deviations in photoresist layer thickness causing undesirable reflectance nonuniformities (and cd variations), a top antireflective coating may be applied to the photoresist layer. In the case of a point-by-point lithography process, such as e-beam lithography, the thickness/reflectance variations can be mapped, and exposure doses adjusted accordingly.
    Type: Grant
    Filed: June 29, 1992
    Date of Patent: June 14, 1994
    Assignee: LSI Logic Corporation
    Inventor: Michael D. Rostoker
  • Patent number: 5302490
    Abstract: 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: Grant
    Filed: April 1, 1993
    Date of Patent: April 12, 1994
    Assignee: Shipley Company Inc.
    Inventors: Theodore H. Fedynyshyn, Marc Connelly