Vinyl Alcohol Polymer Or Derivative Patents (Class 430/909)
  • Patent number: 6767688
    Abstract: New photoresist compositions are provided that contain a halogenated salt, particularly a halogenated counter ion of an ammonium or alkyl ammonium salt. Preferred photoresists of the invention are chemically-amplified positive resists and contain an ammonium or alkyl ammonium salt that has a halogenated anion component such as a halogenated alkyl sulfonate or carboxylate anion component. Inclusion of the halogenated organic salt in a photoresist composition can provide enhanced lithographic performance.
    Type: Grant
    Filed: December 20, 2002
    Date of Patent: July 27, 2004
    Assignee: Shipley Company, L.L.C.
    Inventors: Gary Ganghui Teng, James W. Thackeray, James F. Cameron
  • Patent number: 6764807
    Abstract: A planographic printing member precursor comprises a first component, for example a hydroxy group containing polymer, and a second component which may be a siloxane or a compound of general formula (I), wherein M represents a silicon or a titanium atom and each of R1, R2, R3 and R4 is independently selected from hydrogen or halogen atoms; a hydroxy group; an optionally substituted alkyl, alkenyl or alkynyl group; an optionally substituted alkoxy group; or an optionally substituted saturated or unsaturated cyclic or heterocyclic group. On exposure, the second component reacts with the first component to define an oleophobic/hydrophilic material in exposed areas and in non-exposed areas the second component is removed, on processing of the precursor.
    Type: Grant
    Filed: September 5, 2001
    Date of Patent: July 20, 2004
    Assignee: Kodak Polychrome Graphics LLC
    Inventors: Kevin Barry Ray, Mark John Spowage, Christopher David McCullough
  • Patent number: 6762007
    Abstract: The present invention provides a chemical amplification type positive resist composition comprising (A) resin having a phenol skeleton wherein the phenol skeleton has protective group which can be dissociated by the action of an acid, the phenol skeleton itself is insoluble or poorly soluble in an alkali aqueous solution and the phenol skeleton becomes soluble in an alkali aqueous solution after dissociation of the protective group, (B) resin obtained by protecting a part of hydroxyl group in poly(p-hydroxystyrene) with pivaloyl group and (C) an acid generator.
    Type: Grant
    Filed: March 19, 2003
    Date of Patent: July 13, 2004
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Katsuhiko Namba, Masumi Suetsugu, Koshiro Ochiai
  • Patent number: 6756179
    Abstract: A positive resist composition comprises (A) a resin capable of decomposing by the action of an acid to increase solubility in an alkali developer, and (B) a compound capable of generating an aromatic sulfonic acid substituted with at least one group containing a fluorine atom upon irradiation with one of an actinic ray and radiation.
    Type: Grant
    Filed: September 18, 2001
    Date of Patent: June 29, 2004
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Toru Fujimori, Kunihiko Kodama, Shinichi Kanna, Fumiyuki Nishiyama
  • Publication number: 20040121259
    Abstract: The present invention provides a resist pattern thickening material which can thicken a resist pattern to be thickened regardless of a material or a size thereof so as to form a fine space pattern, exceeding an exposure limit of exposure light. The resist pattern thickening material comprises: a resin; a crosslinking agent; and a nitrogen-containing compound. In a process for forming a resist pattern of the present invention, the resist pattern thickening material is applied on a surface of a resist pattern to be thickened, thereby forming a resist pattern. A process for manufacturing a semiconductor device of the present invention includes: applying the thickening material on a surface of a resist pattern to be thickened which is formed on an underlying layer, so as to thicken the resist pattern to be thickened and form a resist pattern; and patterning the underlying layer by etching using the resist pattern.
    Type: Application
    Filed: July 30, 2003
    Publication date: June 24, 2004
    Applicant: FUJIITSU LIMITED
    Inventors: Miwa Kozawa, Koji Nozaki, Takahisa Namiki, Junichi Kon
  • Patent number: 6740469
    Abstract: Anti-reflective compositions and methods of using these compositions to form circuits are provided. The compositions comprise a polymer dissolved or dispersed in a solvent system. In a preferred embodiment, the polymers of the composition include recurring units having the formula where X is a light-attenuating moiety, M is a metal, and each R is individually selected from the group consisting of hydrogen, alkyls, aryls, alkoxys, and phenoxys. The resulting compositions are spin bowl compatible (i.e., they do not crosslink prior to the bake stages of the microlithographic processes or during storage at room temperature), are wet developable, and have superior optical properties.
    Type: Grant
    Filed: June 25, 2002
    Date of Patent: May 25, 2004
    Assignee: Brewer Science Inc.
    Inventors: Vandana Krishnamurthy, Charles J. Neef, Juliet A. M. Snook
  • Patent number: 6737214
    Abstract: A chemical amplification positive resist composition comprising a polymeric mixture of a polyhydroxystyrene derivative having a Mw of 1000-500,000 and a copolymer of hydroxystyrene and (meth)acrylate having a Mw of 1000-500,000, as a base resin, has improved dry etching resistance, high sensitivity, high resolution, and process adaptability, and is suppressed in the slimming of pattern films after development with aqueous base.
    Type: Grant
    Filed: March 8, 2001
    Date of Patent: May 18, 2004
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Takanobu Takeda, Osamu Watanabe, Kazuhiro Hirahara, Katsuya Takemura, Wataru Kusaki, Akihiro Seki
  • Patent number: 6737213
    Abstract: In the pattern formation method of this invention, a resist film is formed by applying, on a substrate, a pattern formation material containing a polymer including a first unit represented by Chemical Formula 1 and a second unit represented by Chemical Formula 2, and an acid generator, wherein R1 and R2 are the same or different and selected from the group consisting of an alkyl group, a chlorine atom and an alkyl group including a chlorine atom; and R3 is a protecting group released by an acid. Then, the resist film is irradiated with exposing light of a wavelength of a 1 nm through 30 nm band or a 110 nm through 180 nm band for pattern exposure, and a resist pattern is formed by developing the resist film after the pattern exposure.
    Type: Grant
    Filed: March 6, 2001
    Date of Patent: May 18, 2004
    Assignee: Matsushita Electric Industrial Co., Ltd.
    Inventors: Shinji Kishimura, Masaru Sasago, Masamitsu Shirai, Masahir Tsunooka
  • Publication number: 20040081911
    Abstract: Polymer materials are described that undergo a two-level three-dimensional crosslinking process. During this process, hydrophilic polymers are crosslinked at two levels, the first results in a low level of crosslinking which leads to a toughening of the layer preventing dissolution by the fountain solution but with the layer remaining hydrophilic. The second level of crosslinking is higher and is the result of exposure to a laser diode thermal imaging device. The crosslinking at this second level results in a loss of hydrophilicity and provides instead an oleophilic image capable of accepting and transferring oil-based ink. The polymer materials are particularly useful in lithographic printing systems where they may used in articles such as a printing plate comprising a substrate having coated thereon a layer that becomes less hydrophilic upon exposure to thermal energy (e.g.
    Type: Application
    Filed: August 25, 2003
    Publication date: April 29, 2004
    Inventors: Horst Noglik, Tibor Horvath, Joyce Diana Dewi Djauhari Lukas, David A. Morgan
  • Publication number: 20040072098
    Abstract: The present invention provides a resist pattern thickening material and the like which can thicken a resist pattern and form a fine space pattern, exceeding exposure limits of exposure light used during patterning. The resist pattern thickening material contains a resin and a surfactant. In a process for forming a resist pattern of the present invention, after a resist pattern to be thickened is formed, the resist pattern thickening material is coated on a surface thereof. A process for manufacturing a semiconductor device of the present invention includes: a step of, after forming a resist pattern to be thickened on an underlying layer, coating the thickening material on a surface of the resist pattern to be thickened so as to thicken the resist pattern to be thickened and form a resist pattern; and a step of patterning the underlying layer by etching by using the resist pattern.
    Type: Application
    Filed: September 26, 2003
    Publication date: April 15, 2004
    Applicant: FUJITSU LIMITED
    Inventors: Miwa Kozawa, Koji Nozaki
  • Publication number: 20040072097
    Abstract: A photosensitive composition of the present invention has excellent sensitivity and pattern profile, which comprises an acid generator having a specific structure.
    Type: Application
    Filed: September 24, 2003
    Publication date: April 15, 2004
    Applicant: FUJI PHOTO FILM CO., LTD.
    Inventor: Kunihiko Kodama
  • Patent number: 6709799
    Abstract: There is provided a resist composition containing a photosensitive resin and used in photolithography, said photosensitive resin having a transmittance of 40% or more for a light having a wavelength of 157 nm in applying to a thickness of 0.1 &mgr;m. The composition has a characteristic that it allows easy formation of a fine pattern having a good profile, particularly at a wavelength for exposure with an F2 excimer laser.
    Type: Grant
    Filed: December 22, 2000
    Date of Patent: March 23, 2004
    Assignee: Sumitomo Chemical Company, Limited
    Inventor: Kazuhiko Hashimoto
  • Patent number: 6706466
    Abstract: Imageable articles comprising positive working polymeric coatings on substrates are given a heat treatment as part of their manufacture, notably at a moderate temperature for an extended period. This heat treatment improves the development characteristics of the coatings in use. It has been found that by carrying out the heat treatment on articles wrapped in a water-impermeable material or in a humidity-enhanced oven, development characteristics may be further improved, especially adjacent to the edges of articles. The imageable articles include precursors for lithographic printing plates and for printed circuits.
    Type: Grant
    Filed: June 6, 2000
    Date of Patent: March 16, 2004
    Assignee: Kodak Polychrome Graphics LLC
    Inventors: Martyn Lott, Colin Shoesmith, John David Riches, Gareth Rhodri Parsons
  • Patent number: 6653044
    Abstract: A chemical amplification type resist composition uses as the base resin a polymer having a molecular weight dispersity of 1.0 to 1.5 which is a polymer comprising recurring units of formula (1) and recurring units of formula (2) or a polymer comprising recurring units of formula (2) wherein R1 is alkyl, alkoxyalkyl, acetyl or carbonylalkoxy, 0<p/(p+q)≦1, R2 is hydrogen or methyl, and R3 is a tertiary hydrocarbon group of 4 to 30 carbon atoms. By virtue of the narrow dispersity effect of the polymer, the resist composition is improved in resolution as compared with prior art base resins having a wide dispersity. Advantages including a high resolution, good pattern profile and storage stability are obtained.
    Type: Grant
    Filed: January 17, 2001
    Date of Patent: November 25, 2003
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Takanobu Takeda, Osamu Watanabe, Jun Watanabe, Jun Hatakeyama, Tsunehiro Nishi, Takeshi Kinsho
  • Patent number: 6638689
    Abstract: Photoresist compositions, which can attain high-accuracy etching without causing separation and flexible printed wiring boards prepared with the photoresist compositions are disclosed. In order to etch a polyimide precursor layer on a conductive circuit, a photoresist composition comprising a photopolymerizable organic material (A), a water-soluble resin (B) and an amino-group-containing resin (C) is applied on the surface of the polyimide precursor layer to form a photoresist layer. Then, the photoresist layer is patterned by a photolithographic process. The polyimide precursor layer is etched and the pattern of the photoresist layer is transferred to the polyimide precursor layer. The amino-group-containing resin (C) in the photoresist layer is combined with an acid anhydride in the polyimide precursor layer to attain good adhesion and high-accuracy etching without causing separation of the photoresist layer.
    Type: Grant
    Filed: April 8, 1999
    Date of Patent: October 28, 2003
    Assignee: Sony Chemicals Corp.
    Inventors: Satoshi Takahashi, Akira Tsutsumi, Koichi Uno, Minoru Nagashima
  • Patent number: 6630281
    Abstract: Photoresist compositions for a Top-surface Imaging Process by Silylation (TIPS), and a process for forming a positive pattern according to the TIPS using the same. The photoresist composition for the TIPS comprises a cross-linker of following Formula 1 or 2. A protecting group of the cross-linker and a hydroxyl group of the photoresist polymer are selectively crosslinked in the exposed region, and the residual hydroxyl group reacts to a silylating agent in the non-exposed region by silylation. Thus, the non-exposed region only remains after the dry-development, thereby forming a positive pattern. In addition, the photoresist composition of the present invention is suitable for the TIPS lithography using light sources such as ArF (193 nm), VUV (157 nm) and EUV (13 nm). wherein, R1, R2, R3, R4, R5, R6 and R7 are as defined in the specification.
    Type: Grant
    Filed: July 10, 2001
    Date of Patent: October 7, 2003
    Assignee: Hynix Semiconductor Inc.
    Inventors: Cha Won Koh, Geun Su Lee, Ki Ho Baik
  • Publication number: 20030143482
    Abstract: The negative resist composition comprises (1) a film-forming polymer which is itself soluble in basic aqueous solutions, and contains a first monomer unit with an alkali-soluble group in the molecule and a second monomer unit with an alcohol structure on the side chain which is capable of reacting with the alkali-soluble group, and (2) a photo acid generator which, when decomposed by absorption of image-forming radiation, is capable of generating an acid that can induce reaction between the alcohol structure of the second monomer unit and the alkali-soluble group of the first monomer unit, or protect the alkali-soluble group of the first monomer unit. The resist composition can form intricate negative resist patterns with practical sensitivity and no swelling.
    Type: Application
    Filed: November 12, 2002
    Publication date: July 31, 2003
    Applicant: FUJITSU LIMITED
    Inventors: Koji Nozaki, Takahisa Namiki, Ei Yano, Junichi Kon, Miwa Kozawa
  • Patent number: 6596460
    Abstract: A copolymer useful in radiation sensitive compositions for lithographic printing plates comprises the units A, B, C and D, wherein A is present in an amount of 0.5 to 30 wt.-% and is of the formula wherein R is hydrogen, C1-C4 alkyl, —CH═COOH or B is present in an amount of 5 to 35 wt.-% and is of the formula C is present in an amount of 10 to 55 wt.
    Type: Grant
    Filed: December 29, 2000
    Date of Patent: July 22, 2003
    Assignee: Kodak Polychrome Graphics LLC
    Inventors: Hans-Joachim Timpe, Ursula Müller
  • Patent number: 6586155
    Abstract: The invention is to enable easy formation of a fine electroconductive film pattern with a composition utilizing aqueous solvent of easy handling and little environmental burden. An electroconductive film forming composition composed of a water-soluble photosensitive resinous component, a water-soluble organometallic compound component capable of forming an electroconductive film by baking, and an aqueous solvent component is coated on a substrate and, after exposure based on the necessary pattern of the electroconductive film and development, is baked to form the required electroconductive film.
    Type: Grant
    Filed: February 7, 2001
    Date of Patent: July 1, 2003
    Assignee: Canon Kabushiki Kaisha
    Inventors: Tsuyoshi Furuse, Masahiro Terada, Shosei Mori
  • Patent number: 6576398
    Abstract: In the pattern formation method of this invention, a resist film is formed by applying, on a substrate, a pattern formation material containing a polymer including a first unit represented by Chemical Formula 1 and a second unit represented by Chemical Formula 2, and an acid generator, wherein R1 and R2 are the same or different and selected from the group consisting of an alkyl group, a chlorine atom and an alkyl group including a chlorine atom; and R3 is a protecting group released by an acid. Then, the resist film is irradiated with exposing light of a wavelength of a 1 nm through 30 nm band or a 110 nm through 180 nm band for pattern exposure, and a resist pattern is formed by developing the resist film after the pattern exposure.
    Type: Grant
    Filed: March 6, 2001
    Date of Patent: June 10, 2003
    Assignee: Matsushita Electric Industrial Co., Ltd.
    Inventors: Shinji Kishimura, Masaru Sasago, Masamitsu Shirai, Masahiro Tsunooka
  • Patent number: 6569602
    Abstract: This invention discloses compositions that can be polymerized/crosslinked imagewise upon exposure to ionization radiation such as x-ray, electron beam, ion beam, and gamma-ray. This invention also discloses methods of use for these compositions for microfabrication of ceramics, for stereolithography, and for x-ray, e-beam, and ion-beam lithography which can be used for photoresists.
    Type: Grant
    Filed: May 18, 1999
    Date of Patent: May 27, 2003
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Ying Wang
  • Publication number: 20030096191
    Abstract: A phenolic resin/silicone resin hybrid compound is obtained by effecting hydrolytic condensation of an organooxysilane in the co-presence of a phenolic resin. The hybrid compound is used as the base polymer in a resist for endowing a resist film with excellent adhesion to a metal substrate.
    Type: Application
    Filed: October 11, 2002
    Publication date: May 22, 2003
    Inventors: Hideto Kato, Tomoyoshi Furihata
  • Patent number: 6566036
    Abstract: A chemically amplified resist including base resin represented by a general formula [1], a radiation-sensitive acid generator; polystyrene acting as a filler and a solvent dissolving the resin, the acid generator and the filler; wherein a content of the resin is between 10 and 20% in weight with respect to the entire chemically amplified resist, contents of the acid generator and the filler are between 1 and 15% in weight and between 0.5 and 6.0% in weight, respectively, with respect to the resin, and a balance is the solvent.
    Type: Grant
    Filed: December 26, 2000
    Date of Patent: May 20, 2003
    Assignee: NEC Electronics Corporation
    Inventor: Mitsuharu Yamana
  • Patent number: 6551763
    Abstract: A composition used as a resist in the manufacture of electronic parts, for example printed circuits, and which is rendered soluble in a developer by pattemwise delivery of heat, comprises a polymer and optionally an infrared absorbing compound. However in contrast to conventional compositions no compound is present which alters the solubility of the polymer in an aqueous developer.
    Type: Grant
    Filed: June 2, 2000
    Date of Patent: April 22, 2003
    Assignee: Kodak Polychrome Graphics LLC
    Inventors: Anthony Paul Kitson, Peter Andrew Reath Bennett, Christopher David McCullough, Stuart Bayes, Kevin Barry Ray
  • Publication number: 20030064318
    Abstract: The present invention relates to a polymerizable coating composition suitable for the manufacture of printing plates developable on-press. The coating composition comprises (i) a polymerizable compound and (ii) a polymeric binder comprising polyethylene oxide segments, wherein the polymeric binder is selected from the group consisting of at least one graft copolymer comprising a main chain polymer and polyethylene oxide side chains, a block copolymer having at least one polyethylene oxide block and at least one non-polyethylene oxide block, and a combination thereof. The invention is also directed to an imageable element comprising a substrate and the polymerizable coating composition.
    Type: Application
    Filed: April 10, 2002
    Publication date: April 3, 2003
    Inventors: Jianbing Huang, Heidi M. Munnelly, Shashikant Saraiya, Socrates Peter Pappas
  • Patent number: 6541181
    Abstract: A positive acting, composition that can be heat-sensitive is presented, either coated on a lithographic base, or on a printing circuit board base, and comprises a water soluble heat-sensitive resin, a novel adhesion promoter and a radiation absorbing agent—a dye or a pigment. An excellent film forming polymer that comprises acetal units directly pendant from the polymer polyvinyl alcohol backbone may be the only binder resin, when other resins being optional. The solubility of the coated material in the areas exposed to near -IR laser radiation in mild alkaline developers becomes considerably higher, allowing to obtain high resolved patterns of the etch-resistant material on printing circuit boards or lithographic printing plates. The composition can be applied on the substrate from a liquid of laminated as a dry film. Sensitizers may be added to render the composition sensitive to radiation in a non-thermal sense.
    Type: Grant
    Filed: July 26, 2000
    Date of Patent: April 1, 2003
    Assignee: Creo IL. Ltd.
    Inventors: Moshe Levanon, Emmanuel Lurie, Sergei Malikov, Oleg Naigertsik, Larisa Postel
  • Publication number: 20030022104
    Abstract: A photosensitive resin composition which includes a photosensitive saponified PVA having a pendant group derived from a quaternary styrylpyridinium or styrylquinolinium, or a derivative thereof.
    Type: Application
    Filed: July 12, 2002
    Publication date: January 30, 2003
    Inventors: Masahiro Takano, Shin Utsunomiya, Nobuji Sakai, Noriaki Tochizawa
  • Patent number: 6511785
    Abstract: A chemically amplified positive resist composition comprising a base resin and a compound containing two to six functional groups, specifically alkenyloxy, acetal and ortho-ester groups in the molecule is suitable for forming a contact hole pattern by the thermal flow process.
    Type: Grant
    Filed: November 13, 2000
    Date of Patent: January 28, 2003
    Assignee: Shin Etsu Chemical Co., Ltd.
    Inventors: Katsuya Takemura, Kenji Koizumi, Tatsushi Kaneko, Toyohisa Sakurada
  • Publication number: 20020136987
    Abstract: A photosensitive lithographic printing plate comprising: a support; and a photosensitive layer, wherein the photosensitive layer comprises: a polyurethane resin binder comprising an aliphatic cyclic structure which has a carboxyl group as a substituent directly or indirectly attached to the structure; or a polyvinyl alcohol resin binder modified with an acetal skeleton comprising an aliphatic cyclic structure.
    Type: Application
    Filed: November 6, 2001
    Publication date: September 26, 2002
    Inventor: Yasuhito Oshima
  • Patent number: 6455226
    Abstract: The present invention provides photoresist polymers and photoresist compositions comprising the same. In one aspect, the photoresist polymer is of the Formula: where Y, R1, a, b and c are as described herein. Photoresist compositions of the present invention have good transmittance at wavelengths of 193 nm and 157 nm, etching resistance, heat resistance, and adhesiveness. In addition, photoresist compositions of the present invention can be developed easily in aqueous TMAH solution, and are therefore suitable for lithography processes using VUV (157 nm) and EUV (13 nm) wavelength-light sources for fabricating a minute circuit of a high integration semiconductor device.
    Type: Grant
    Filed: November 1, 2000
    Date of Patent: September 24, 2002
    Assignee: Hyundai Electronics Industries Co., Ltd.
    Inventors: Geun Su Lee, Jae Chang Jung, Hyeong Soo Kim, Ki Ho Baik
  • Patent number: 6444395
    Abstract: A resist material including a base polymer having a group for producing an active methylene group through decomposition in the presence of an acid and an acid generator for generating an acid through irradiation with light is applied on a substrate, thereby forming a resist film. The resist film is irradiated with exposing light of a wavelength of a 1 nm through 180 nm band for pattern exposure, and is developed with an alkaline developer after the pattern exposure, thereby forming a resist pattern.
    Type: Grant
    Filed: March 10, 2000
    Date of Patent: September 3, 2002
    Assignee: Matsushita Electric Industrial Co., Ltd.
    Inventors: Shinji Kishimura, Akiko Katsuyama, Masaru Sasago
  • Patent number: 6440635
    Abstract: A photoresist having both positive and negative tone components resulting in a lower “k” factor than the single tone photoresist is disclosed. The hybrid resist may either have the negative tone resist or the positive tone resist as the major portion, while the other tone is a relatively minor portion. For examples, a positive tone resist may include a minor portion of a negative tone cross-linker or a negative tone resist may include positively acting functional groups. The hybrid resist of the present invention allows for wider exposure dosage windows, therefore increasing the yield or performance and line density.
    Type: Grant
    Filed: September 29, 2000
    Date of Patent: August 27, 2002
    Assignee: International Business Machines Corporation
    Inventors: Steven J. Holmes, Ahmad D. Katnani, Niranjan M. Patel, Paul A. Rabidoux
  • Patent number: 6423456
    Abstract: A composition used as a resist in the manufacture of electronic parts, for example printed circuits, and which is rendered soluble in a developer by patternwise delivery of heat, comprises a polymer of general formula (I), wherein R1 represents a hydrogen atom or alkyl group, R2 represents a hydrogen atom or alkyl group, R3 represents a hydrogen atom or alkyl group, and R4 represents hydroxyalkyl group, and wherein the ratio n/m is in the range 10/1 to 1/10.
    Type: Grant
    Filed: April 9, 2001
    Date of Patent: July 23, 2002
    Assignee: Kodak Polychrome Graphics LLC
    Inventors: Anthony Paul Kitson, Peter Andrew Reath Bennett, Kevin Barry Ray
  • Publication number: 20020090566
    Abstract: A polyvinyl acetal copolymer compound comprises the units A, B, C and D, wherein A is present in an amount of 0.5 to 30 wt.
    Type: Application
    Filed: December 29, 2000
    Publication date: July 11, 2002
    Applicant: Kodak Polychrome Graphics LLC.
    Inventors: Hans-Joachim Timpe, Ursula Muller
  • Publication number: 20020086235
    Abstract: A planographic printing member precursor comprises a first component, for example a hydroxy group containing polymer, and a second component which may be a siloxane or a compound of general formula (I), wherein M represents a silicon or a titanium atom and each of R1, R2, R3 and R4 is independently selected from hydrogen or halogen atoms; a hydroxy group; an optionally substituted alkyl, alkenyl or alkynyl group; an optionally substituted alkoxy group; or an optionally substituted saturated or unsaturated cyclic or heterocyclic group. On exposure, the second component reacts with the first component to define an oleophobic/hydrophilic material in exposed areas and in non-exposed areas the second component is removed, on processing of the precursor.
    Type: Application
    Filed: September 5, 2001
    Publication date: July 4, 2002
    Inventors: Kevin Barry Ray, Mark John Spowage, Christopher David McCullough
  • Patent number: 6399271
    Abstract: A planographic printing member precursor comprises a first component, for example a hydroxy group containing polymer, and a second component which may be a siloxane or a compound of general formula (I): wherein M represents a silicon or a titanium atom and each of R1, R2, R3 and R4 is independently selected from hydrogen or halogen atoms; a hydroxy group, an optionally substituted alkyl, alkenyl or alkynyl group; an optionally substituted alkoxy group; or an optionally substituted saturated or unsaturated cyclic or heterocyclic group. On exposure, the second component reacts with the first component to define an oleophobic/hydrophilic material in exposed areas and in non-exposed areas the second component is removed, on processing of the precursor.
    Type: Grant
    Filed: March 2, 2000
    Date of Patent: June 4, 2002
    Assignee: Kodak Polychrome Graphics LLC
    Inventors: Kevin Barry Ray, Mark John Spowage, Christopher David McCullough
  • Patent number: 6387587
    Abstract: Disclosed is a novel positive-working chemical-amplification photoresist composition capable of giving an extremely finely patterned resist layer in the manufacturing process of semiconductor devices. The photoresist composition comprises: (A) 100 parts by weight of a copolymeric resin consisting of from 50 to 85% by moles of (a) hydroxyl group-containing styrene units, from 15 to 35% by moles of (b) styrene units and from 2 to 20% by moles of (c) acrylate or methacrylate ester units each having a solubility-reducing group capable of being eliminated in the presence of an acid; and (B) from 1 to 20 parts by weight of a radiation-sensitive acid-generating agent which is an onium salt containing a fluoroalkyl sulfonate ion having 3 to 10 carbon atoms as the anion such as bis(4-tert-butylphenyl) iodonium nonafluorobutane sulfonate.
    Type: Grant
    Filed: April 14, 1999
    Date of Patent: May 14, 2002
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Katsumi Oomori, Hiroto Yukawa, Ryusuke Uchida, Kazufumi Sato
  • Publication number: 20020022194
    Abstract: A photosensitive resin composition developable with water or a diluted alkali solution comprises the following components (A) to (D). That is, the component (A) is a water-soluble photosensitive resin selected from the group consisting of a first resin obtained by introducing a styryl pyridinium group into a polyvinyl alcohol polymer, a second resin obtained by introducing a styryl quinolinium group into the polyvinyl alcohol polymer, and a third resin obtained by adding N-alkylol(meth)acrylamide to the polyvinyl alcohol polymer. The component (B) is a photosensitive prepolymer having a carboxyl group and at least two ethylenically unsaturated groups in molecule. The component (C) is a photopolymerization initiator. The component (D) is water. The photosensitive resin composition will be preferably used as a photoresist ink for manufacturing printed wiring boards.
    Type: Application
    Filed: August 14, 2001
    Publication date: February 21, 2002
    Applicant: GOO CHEMICAL CO., LTD.
    Inventor: Toshio Morigaki
  • Patent number: 6346570
    Abstract: Provided are a water resistant composition comprising a uniform mixture of (A) at least one of modified polyvinyl alcohol containing either from 1 to 20 mol % of &agr;-olefin units with not more than 4 carbon atoms, from 0.01 to 1 mol % of silyl groups, or from 1 to 20 mol % of &agr;-olefin units with not more than 4 carbon atoms and from 0.01 to 1 mol % of silyl groups and (B) an organotitanium compound having a chelating ligand, in a blend ratio of component (A) to the component (B) between 99.99/0.01 and 60/40 by weight; a coating agent comprising the composition; a thermal recording material having a coat layer of the composition; and an ink-jet recording material having an ink-absorbing layer of the composition.
    Type: Grant
    Filed: August 22, 2000
    Date of Patent: February 12, 2002
    Assignee: Kuraray Co., Ltd.
    Inventors: Somemiya Kazuyuki, Sadahiko Shiraga, Naoki Fujuwara, Atsushi Jikihara, Toshiyuki Akasawa
  • Patent number: 6333133
    Abstract: A positive planographic printing material which is capable of recording a digital data from a computer and the like, using a solid laser or a semiconductor laser emitting infrared rays. The positive planographic printing material comprises at least the following components (A) to (C): (A) a polyfunctional amine compound, (B) a polymer which is water-insoluble and aqueous alkali solution-soluble and (C) an infrared absorber.
    Type: Grant
    Filed: February 14, 2000
    Date of Patent: December 25, 2001
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Ippei Nakamura, Kazuto Kunita
  • Patent number: 6312870
    Abstract: A resist composition containing a polymer of t-butyl cinnamate, a photacid generator, and a solvent. Optionally, the resist composition may include a basic compound. The polymer of t-butyl cinnamate has the monomeric units: wherein a=0.3 to 0.9, b=0.1 to 0.7, and c=0 to 0.3; R1=H, methyl, or CH2OR4; R4=H or C1-C4 alkyl group; R2=H, methyl, CH2OR4, CH2CN, or CH2X; X=Cl, I, Br, F, or CH2COOR5; R5=C1-C4 alkyl group; and R3=isobomyl, cyclohexyl methyl, cyclohexyl ethyl, benzyl, or phenethyl.
    Type: Grant
    Filed: July 19, 2000
    Date of Patent: November 6, 2001
    Assignee: Arch Specialty Chemicals, Inc.
    Inventors: Sanjay Malik, Lawrence Ferreira, Jeffrey Eisele, Whewell Allyn
  • Patent number: 6303267
    Abstract: A negative-working, radiation-sensitive mixture is provided which contains an organic polymeric binder and a substance which converts radiant energy into heat, wherein the polymeric binder essentially comprises units of the formula (I): in which R1 is a hydrogen atom or a (C1-C4) alkyl radical, X is a single bond or a (q+1)-valent radical of a (C4-C10) alkane, in which individual methylene groups may be replaced by hetero atoms, of a (C2-C8) alkene or of an isocyclic or heterocyclic, saturated or unsaturated, mono- or polycyclic (C6-C10) ring or ring system, n is from 40 to 80 mol %, m is from 15 to 30 mol %, p is from 1 to 10 mol % and q is an integer from 1 to 3, where q is equal to 1 when X is a single bond, and the polymeric binder has an acid number of from 5 to 150. A recording material comprising a substrate and a layer of this mixture, and a process for the production of a color proof are also provided.
    Type: Grant
    Filed: October 6, 1999
    Date of Patent: October 16, 2001
    Assignee: Agfa-Gevaert
    Inventors: Martin Benzing, Dieter Mohr, Holger Schembs, Daniela Clausen
  • Patent number: 6303263
    Abstract: The present invention is directed to a high-performance irradiation sensitive resists and to a polymer resin composition useful for making the same. In accordance to the present invention, the polymer resin comprises a dual blocked polymer resins. Specifically, the dual blocked polymer resin comprises at least two different acid labile protecting groups which block some, but not all, of the polar functional groups of the polymer resin. a chemically amplified resist system comprising said dual blocked polymer resin; at least one acid generator; and a solvent is also provided herein.
    Type: Grant
    Filed: February 25, 1998
    Date of Patent: October 16, 2001
    Assignee: International Business Machines Machines
    Inventors: Kuang-Jung Chen, Ronald A. DellaGuardia, Wu-Song Huang, Ahmad D. Katnani, Mahmoud M. Khojasteh, Qinghuang Lin
  • Publication number: 20010024765
    Abstract: A resist composition is prepared by reacting an alkali-soluble polymer having a phenolic hydroxyl or carboxyl groups with a vinyl ether compound in an aprotic solvent, such as propylene glycol monomethyl ether acetate, in the presence of an acid catalyst, suspending the reaction by the addition of a base, and directly adding a photoacid generator to the reaction solution. When a dialkyl dicarbonate is used in stead of the vinyl ether compound, a resist composition is prepared by carrying out the reaction in the presence of a basic catalyst and adding a photoacid generator directly to the reaction. Thus resist compositions can be prepared without isolating or purifying an alkali-soluble polymer which has been substituted by a catalytic reaction.
    Type: Application
    Filed: April 2, 2001
    Publication date: September 27, 2001
    Inventors: Hiroshi Okazaki, Georg Pawlowski, Satoru Funato, Yoshiaki Kinoshita, Yuko Yamaguchi
  • Patent number: 6291060
    Abstract: The present invention concerns a water-developable plate package comprising water-developable plates packaged in a laminated state. The water-developable plate is a sheet-like plate comprising a photosensitive layer made of a photosensitive resin composition having water-developability and protective films covering both surfaces of this photosensitive layer. The package of the present invention is obtained by sandwiching an open cell foamed sheet (2) between a water-developable plate (1) and between a water-developable plate (1) to make a laminate (3), packaging the laminate (3) with a light-screening film and fixing the packaging ends with a tape. The subject of the present invention is to prevent the occurrence of deformation of the plates in the package during transportation or storage at a high temperature and high humidity in summer, without complicating the operations at the time of use or packaging of the plates and without increasing the cost remarkably.
    Type: Grant
    Filed: February 25, 2000
    Date of Patent: September 18, 2001
    Assignee: Asahi Kasei Kabushiki Kaisha
    Inventors: Takeshi Oyoshi, Yoshifumi Araki
  • Patent number: 6255033
    Abstract: A positive acting, heat-sensitive composition is presented, either coated on a lithographic base, or on a printing circuit board base, and comprises a water insoluble heat-sensitive resin, a novel adhesion promoter and a radiation absorbing agent—a dye or a pigment. An excellent film forming polymer that comprises acetal units directly pendant from the polymer polyvinyl alcohol backbone may be the only binder resin, when other resins being optional. The solubility of the coated material in the areas exposed to near-IR laser radiation in mild alkaline developers becomes considerably higher, allowing to obtain high resolved patterns of the etch-resistant material on printing circuit boards or lithographic printing plates. The composition can be applied on the substrate from a liquid or laminated as a dry film.
    Type: Grant
    Filed: July 30, 1999
    Date of Patent: July 3, 2001
    Assignee: Creo, Ltd.
    Inventors: Moshe Levanon, Emmanuel Lurie, Sergei Malikov, Oleg Naigertsik, Larisa Postel
  • Patent number: 6251562
    Abstract: An antireflective composition includes a polyphenolic polymer which has a first repeating unit and a second repeating unit of the formula: wherein each of R1, R2, R3, R4, and R5 is individually a hydroxy group, hydrogen or an azo dye and only one of R1, R2, R3, R4, and R5 is a hydroxy group.
    Type: Grant
    Filed: December 23, 1998
    Date of Patent: June 26, 2001
    Assignee: International Business Machines Corporation
    Inventors: Gregory Breyta, Thomas Carl Clarke, Daniel Joseph Dawson, Ronald P. Esch, Alfred Floyd Renaldo
  • Patent number: 6248498
    Abstract: Disclosed are photoresist compositions comprising a polymeric backbone and a quaternary heterocyclic pendant group, particularly usefull in the preparation of screen printing and sandblast etching photoresists. The pendant groups comprise furanyl substituted quaternary heterocyclic groups, as seen in the formula: where n ranges from 0 to 4 and Z denotes the atoms necessary to complete a substituted or unsubstituted nitrogen containing heterocyclic ring.
    Type: Grant
    Filed: December 7, 1999
    Date of Patent: June 19, 2001
    Assignee: The Chromaline Corporation
    Inventor: Alexander S. Gybin
  • Patent number: RE37179
    Abstract: A radiation sensitive resin composition which comprises (A) a polymer which becomes alkali-soluble in the presence of an acid and (B) a radiation sensitive acid generator which generates an acid upon irradiation with a radiation, said polymer (A) comprising two recurring units represented by the general formulas (1) and (2) and a recurring unit which acts to reduce the solubility of the polymer is an alkali developer after the irradiation: wherein R1 represents a hydrogen atom or a methyl group and R2 represents a hydrogen atom or a methyl group. Said composition provides a chemically amplified positive resist which can give a fine pattern with a good pattern shape, and said resist is freed from volume shrinkage, peeling failure and adhesive failure, is excellent in dry etching resistance and effectively reacts with various radiations to give a good pattern shape which is excellent in photolithographic process stability, said pattern shape having no thinned portion at the upper part.
    Type: Grant
    Filed: October 21, 1999
    Date of Patent: May 15, 2001
    Assignee: JSR Corporation
    Inventors: Mikio Yamachika, Eiichi Kobayashi, Akira Tsuji, Toshiyuki Ota
  • Patent number: RE38256
    Abstract: Disclosed are a safe slurry photosensitive composition superior in image formation capabilities such as resolution and sensitivity and containing no harmful compound, and a safe water-soluble photosensitive composition capable of being dissolved in water without using any organic solvent while maintaining a sufficient sensitivity as a resist and containing no harmful substance. The slurry photosensitive composition contains a compound which generates an acid when irradiated with light or ionizing radiation, at least one type of a resin with acid-crosslinkability or acid-decomposability, and a powder. Various devices can be manufactured by forming a layer of this photosensitive composition on a substrate, exposing the layer to light in accordance with a desired pattern, and heating the layer. The water-soluble photosensitive composition contains a compound which generates an acid when irradiated with light or ionizing radiation, and an acetal resin.
    Type: Grant
    Filed: November 24, 1999
    Date of Patent: September 23, 2003
    Assignee: Kabushiki Kaisha Toshiba
    Inventors: Toru Ushirogouchi, Naomi Shida, Takuya Naito, Koji Asakawa, Akinori Hongu, Makoto Nakase, Hirokazu Niki