(o=s=o), E.g., Sulfuryl Or Sulfonyl Containing, Etc. Patents (Class 522/59)
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Patent number: 6737169Abstract: A polymer composition containing a specific silyl group-containing polymer, in which the maximum size of particles contained therein is 2 &mgr;m or less, and the number of particles having a size of 0.2 &mgr;m to 2 &mgr;m is 1,000 particles/ml or less. The composition may further contain a specific compound or at least one component selected from an organosilane represented by (R1)nSi(X)4-n, a hydrolyzate of the organosilane and a condensate of the organosilane. The composition is excellent in storage stability, high in hardness and excellent in mechanical strength such as wear resistance, so that a coating film having good taking-up properties even when no lubricant is contained, extremely smooth and having no difference in film thickness can be formed.Type: GrantFiled: January 30, 2002Date of Patent: May 18, 2004Assignee: JSR CorporationInventors: Mibuko Shimada, Nakaatsu Yoshimura, Yuichi Hashiguchi
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Patent number: 6703182Abstract: Compounds of formulae I, II or III wherein m is zero or 1; n is 1, 2 or 3; R1 inter alia is unsubstituted or substituted phenyl, or naphthyl, anthracyl, phenanthryl, a heteroaryl radical, or C2-C12alkenyl; R′1 inter alia is vinylene, phenylene, naphthylene, diphenylene or oxydiphenylene; R2 inter alia is CN, C1-C4haloalkyl, C2-C6alkoxycarbonyl, phenoxycarbonyl, or benzoyl; R3 inter alia is C1-C18alkylsulfonyl, phenyl-C1-C3alkylsulfonyl, camphorylsulfonyl, or phenylsulfonyl; R′3 inter alia is C2-C12alkylenedisulfonyl, phenylenedisulfonyl, naphthylenedisulfonyl, diphenylenedisulfonyl, or oxydiphenylenedisulfonyl; R4 and R5 inter alia are hydrogen, halogen, C1-C8alkyl, C1-C6alkoxy, C1-C4haloalkyl, CN, NO2, C2-C6alkanoyl, benzoyl, phenyl, —S-phenyl, OR6, SR9, NR7R8, C2-C6alkoxycarbonyl or phenoxycarbonyl; R6 inter alia is hydrogen, phenyl or C1-C12alkyl; R7 and R8 inter alia are hydrogen or C1-C12alkyl; R9 inter alia is C1-C12 alkyl; R10, R11 andType: GrantFiled: February 15, 2001Date of Patent: March 9, 2004Assignee: Ciba Specialty Chemicals CorporationInventors: Jean-Luc Birbaum, Toshikage Asakura, Hitoshi Yamato
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Patent number: 6645698Abstract: The invention provides photoresist compositions comprising a resin binder having acid labile blocking groups requiring an activation energy in excess of 20 Kcal/mol. for deblocking, a photoacid generator capable of generating a halogenated sulfonic acid upon photolysis and optionally, a base additive. It has found that linewidth variation is substantially reduced when using the halogenated sulfonic aced generator in a process involving a high temperature post exposure bake.Type: GrantFiled: December 22, 1999Date of Patent: November 11, 2003Assignee: Shipley Company, L.L.C.Inventors: James W. Thackeray, James F. Cameron, Roger F. Sinta
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Patent number: 6569603Abstract: There are disclosed a light-sensitive composition which comprises (A) a polymer having a phenyl group substituted by a vinyl group at a side chain, (B) a photopolymerization initiator and (C) a sensitizer which sensitizes the photo-polymerization initiator, or a light-sensitive composition which comprises (A′) a polymer, the above-mentioned (B) and (C), and (D) a monomer having at least two phenyl groups each of which is substituted by a vinyl group in the molecule of the monomer; and a method of forming a relief image which comprises coating the light-sensitive composition as mentioned above on a support, exposing the composition by exposure or scanning exposure and developing the same to form a relief image on the support.Type: GrantFiled: January 30, 2001Date of Patent: May 27, 2003Assignee: Mitsubishi Paper Mills LimitedInventor: Akira Furukawa
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Patent number: 6548565Abstract: A non-aqueous coating composition based on an oxidatively drying alkyd resin and a photo-initiator. An acid or latent acid and one or more compounds of the group of vinyl ethers, acetals, and alkoxysilanes which are reactive in the presence of an acid are incorporated into the coating composition. The vinyl ethers, acetals, and alkoxysilanes preferably are covalently bounded to the alkyd resin. The ratio of the number of oxidatively drying groups present in the alkyd resin to the number of groups reactive in the presence of an acid preferably is in the range of 1/10 to 15/1. The acid preferably is the phosphoric acid dibutyl ester.Type: GrantFiled: September 13, 2000Date of Patent: April 15, 2003Assignee: Akzo Nobel NVInventors: Keimpe Jan Van Den Berg, Huig Klinkenberg, Arie Noomen
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Patent number: 6515038Abstract: A polymer used in a chemically amplified resist is represented by the following formula: wherein R1, R3 and R5 are each independently selected from the group consisting of —H, and —CH3; R2 is selected from the group consisting of t-butyl, tetrahydropyranyl, and 1-alkoxyethyl; R4 is selected from the group consisting of —H, —CH3, t-butyl, tetrahydropyranyl, and 1-alkoxyethyl; x is an integer ranging from 1 to 4; and wherein l, m, and n are selected such that l/(l+m+n) ranges from 0.1 to 0.5, m/(l+m+n) ranges from 0.01 to 0.5, and (l+m)/(l+m+n) ranges from 0.1 to 0.7.Type: GrantFiled: July 26, 2001Date of Patent: February 4, 2003Assignee: Samsung Electronics Co., Ltd.Inventor: Sang-jun Choi
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Patent number: 6512020Abstract: Compounds of formula I, II and III, wherein wherein R1 is for example hydrogen, C1-C12alkyl, C3-C30cycloalkyl, C2-C12alkenyl, C4-C8cycloalkenyl, phenyl, which is unsubstituted or substituted, naphthyl, anthracyl or phenanthryl, unsubstituted or substituted, heteroaryl radical which is unsubstituted or substituted; wherein all radicals R1 with the exception of hydrogen can additionally be substituted by a group having a —O—C-bond or a —O—Si-bond which cleaves upon the action of an acid; R′1 is for example phenylene, naphthylene, diphenylene or oxydiphenylene, wherein these radicals are unsubstituted or substituted; R2 is halogen or C1-C10haloalkyl; R3 is for example C1-C18alkylsulfonyl, phenylsulfonyl, naphthylsulfonyl, anthracylsulfonyl or phenanthrylsulfonyl, wherein the groups are unsubstituted or substituted, or R3 is e.g.Type: GrantFiled: March 28, 2001Date of Patent: January 28, 2003Assignee: Ciba Specialty Chemicals CorporationInventors: Toshikage Asakura, Hitoshi Yamato, Masaki Ohwa, Jean-Luc Birbaum, Kurt Dietliker, Junichi Tanabe
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Publication number: 20020013381Abstract: The invention relates to an ionic compound corresponding to the formula [R1X1(Z1)—Q−—X2(Z2)—R2]m Mm+ in which Mm+ is a cation of valency m, each of the groups Xi is S═Z3, S═Z4, P—R3 or P—R4; Q is N, CR5, CCN or CSO2R5, each of the groups Zi is ═O, ═NC≡N, ═C(C≡N)2, ═NS(═Z)2R6 or ═C[S(═Z)2R6]2, each of the groups Ri, is Y, YO—, YS—, Y2N— or F, Y represents a monovalent organic radical or alternatively Y is a repeating unit of a polymeric frame.Type: ApplicationFiled: August 17, 2001Publication date: January 31, 2002Inventors: Michel Armand, Christophe Michot, Yurii Yagupolskii, Lev Yagupolskii, Andrej Bezdudny, Natalya Kondratenko
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Patent number: 6342122Abstract: An solvent-based pressure sensitive adhesive (PSA) having improved shear adhesion is composed of an acrylic-based PSA resin, an ethylenically unsaturated polyester, an ultraviolet radiation (UV) photosensitizer, and fugative organic solvent for the acrylic-based PSA resin. The PSA is cured by evaporation of the fugative organic solvent coupled with heat and UV irradiation or UV irradiation alone. Such PSA has improved shear adhesion by dint of the addition of the ethylenically-unsaturated polyester and an ultraviolet radiation (UV) photosensitizer. A method for adhering two substrates using the PSA includes applying the PSA to one or both of substrates. The solvent in the PSA is evaporated from the applied PSA. Finally, the polyester component of the applied PSA is cured by exposure of the applied PSA to ultraviolet (UV) radiation.Type: GrantFiled: August 7, 2000Date of Patent: January 29, 2002Assignee: Ashland Chemical, Inc.Inventors: Daniel Joseph Riley, Raymond Scott Harvey, Harvey Joseph Richards, Peter Albert Yurcick
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Publication number: 20010037037Abstract: The invention relates to the use of oximesulfonic acid esters of formula I 1Type: ApplicationFiled: January 8, 2001Publication date: November 1, 2001Inventors: Kurt Dietliker, Martin Kunz
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Patent number: 6306926Abstract: Polymerizable compositions that include: (a) a cationically active functional group; (b) an initiation system capable of initiating cationic polymerization of the cationically active functional group; and (c) a filler composition that includes various radiopacifying fillers in an amount sufficient to render the polymerizable composition radiopaque. Components (a), (b), and (c) are selected such that the polymerizable composition polymerizes to form a polymerized composition having a Barcol hardness, measured using a GYZJ-935 meter, of at least 10 within 30 minutes following initiation of the cationically active functional group at a reaction temperature of 25° C.Type: GrantFiled: October 7, 1998Date of Patent: October 23, 2001Assignee: 3M Innovative Properties CompanyInventors: Kathyrn R. Bretscher, Richard P. Rusin, Bradley D. Craig, Sumita B. Mitra, Joel D. Oxman, Janis R. Gust, Cheryl A. Hayne, James W. Westberg, Matthew C. Trom, Brant U. Kolb, Dwight W. Jacobs, David A. Kaisaki, James A. Baker
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Patent number: 6261736Abstract: The pattern forming material of the present invention includes a polymer having a group which generates an acid when the polymer is irradiated with an energy beam or heated and a compound which generates a base when the compound is irradiated with an energy beam. The polymer is a binary polymer or a polymer of a higher degree obtained by polymerizing another group with a compound represented by the following general formula: where R1 indicates a hydrogen atom or an alkyl group, and R2 and R3 independently indicate a hydrogen atom, an alkyl group, a phenyl group or an alkenyl group, or together indicate a cyclic alkyl group, a cyclic alkenyl group, a cyclic alkyl group having a phenyl group or a cyclic alkenyl group having a phenyl group.Type: GrantFiled: October 12, 1999Date of Patent: July 17, 2001Assignee: Matsushita Electric Industrial Co., Ltd.Inventors: Masayuki Endo, Masamitsu Shirai, Masahiro Tsunooka
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Patent number: 6207728Abstract: Disclosed is a photo-curable composition comprising the following components (A) to (C): (A) hydrolyzable silane compound represented by the general formula (1) or a hydrolyzate thereof: (R1)pSi(X)4−p (1) wherein R1 is a non-hydrolyzable organic group having 1 to 12 carbon atoms, X is a hydrolyzable group, and p is an integer of 0 to 3; (B) photo acid generator; and (C) dehydrating agent. By such constitution, it is possible to provide a photo-curable composition which has a rapid photo-curable rate, is excellent in characteristics such as storage stability, heat resistance, weather-ability, scratch resistance and the like, and is applicable to base materials having low heat resistance such as plastics, as well as a cured product obtained therefrom.Type: GrantFiled: June 17, 1999Date of Patent: March 27, 2001Assignee: JSR CorporationInventors: Manabu Sekiguchi, Naoki Sugiyama, Hozumi Sato
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Patent number: 6162841Abstract: New betaketosulfonic derivatives, the process for their preparation, the photopolymerizable systems containing the same and their application as polymerization photoinitiators for inks, and particularly for inks having high content of pigments are described.Type: GrantFiled: March 3, 1998Date of Patent: December 19, 2000Assignee: Lamberti S.p.A.Inventors: Paola Giaroni, Piero Di Battista, Giuseppe Li Bassi
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Patent number: 6156815Abstract: 1,2-Disulfones are particularly suitable as thermally and photochemically activatable latent acid catalysts for binder systems which contain at least one acid-curable component.Type: GrantFiled: June 10, 1999Date of Patent: December 5, 2000Assignee: Ciba Specialty Chemicals CorporationInventors: Ekkehard Bartmann, Jorg Ohngemach
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Patent number: 6130269Abstract: A thermosetting pressure-sensitive adhesive comprising a photopolymerization product of a composition containing a) 100 parts by weight of a (meth) acrylic acid alkyl ester wherein the average carbon atom number of the alkyl group is from 2 to 14 and from 30 to 1% by weight of a monoethylenically unsaturated acid copolymerizable with the ester, b) from 0.02 to 5 parts by weight of a polyfunctional (meth)acrylate as a crosslinking agent, c) from 0.01 to 4 parts by weight of a photopolymerization initiator, and d) from 5 to 30 parts by weight of an epoxy resin, and not substantially containing a curing agent for the epoxy resin, and an adhesive sheet using the thermosetting type pressure-sensitive adhesive.Type: GrantFiled: November 24, 1998Date of Patent: October 10, 2000Assignee: Nitto Denko CorporationInventors: Kazuhito Hosokawa, Shigeki Muta, Hitoshi Takahira, Takao Yoshikawa
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Patent number: 6114406Abstract: A UV-curable ink jet composition comprises a polyfunctional alkoxylated or polyalkoxylated acrylate monomer (80% to 95% by weight), a photoinitiator (e.g. from 1 to 15% by weight) and preferably a colorant (e.g. 1% to 10% by weight).Type: GrantFiled: December 3, 1998Date of Patent: September 5, 2000Assignee: Coates Brothers PLCInventors: Nigel Antony Caiger, Hartley David Selman
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Patent number: 6071980Abstract: Exposing to visible light atom transfer radical polymerizations of vinyl monomers that use transition metal compounds often results in faster polymerizations and/or the need for less transition metal compound. Disclosed is a process for the polymerization of vinyl monomers by atom transfer radical polymerization using a first compound containing a transition metal and a second compound capable of radically transferring an atom or group to said first compound, wherein the improvement comprises, irradiating with visible light with an intensity of at least about 5 mW/cm.sup.2 a liquid in which said polymerization is taking place. The polymers made are useful for molding resins and coatings.Type: GrantFiled: August 18, 1998Date of Patent: June 6, 2000Assignee: E. I. du Pont de Nemours and CompanyInventors: Zhibin Guan, Bruce Edmund Smart
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Patent number: 6057078Abstract: Compounds of the formula I ##STR1## in which n and o are a number from 0 to 50, m is a number from 1 to 50, u and v are 0 or 1, and at least one of the indices u and v is 1, R.sub.1, R.sub.2, R.sub.2a, R.sub.3 and R.sub.4 independently of one another are, for example, aromatic hydrocarbons, R.sub.5, if n and o are 0, is for example C.sub.1 -C.sub.12 alkyl and, if n and/or o are greater than 0, or if n and o are 0 and at the same time only one index u or v is 1, R.sub.5 may additionally, for example, be an aromatic hydrocarbon, at least one of the radicals R.sub.1, R.sub.2, R.sub.2a, R.sub.3, R.sub.4 and R.sub.5 being an aromatic hydrocarbon radical which is sterically hindered ortho to the boron atom, X is, for example, C.sub.1 -C.sub.20 alkylene, phenylene, biphenylene, etc., and Z is a radical which is able to form positive ions, are suitable as photoinitiators, both the compounds per se and their combination with dyes or other electron acceptors.Type: GrantFiled: July 23, 1998Date of Patent: May 2, 2000Assignee: Ciba Specialty Chemicals CorporationInventors: Allan Francis Cunningham, Martin Kunz, Hisatoshi Kura
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Patent number: 6017675Abstract: The invention relates to the use of oximesulfonic acid esters of formula I ##STR1## m is 0 or 1 and x is 1 or 2; R.sub.1 is, for example, substituted phenyl, R.sub.2 has, for example, one of the meanings of R.sub.1 or is unsubstituted phenyl, C.sub.1 -C.sub.6 alkanoyl, unsubstituted or substituted benzoyl, C.sub.2 -C.sub.6 alkoxycarbonyl or phenoxycarbonyl; or R.sub.1 and R.sub.2, if necessary together with the CO group, form a ring, R.sub.3, when x is 1, is, for example, C.sub.1 -C.sub.18 alkyl, phenyl or phenanthryl, the radicals phenyl and phenanthryl being unsubstituted or substituted, or R.sub.3, when x is 2, is, for example, C.sub.2 -C.sub.12 alkylene, phenylene or oxydiphenylene, the radicals phenylene and oxydiphenylene being unsubstituted or substituted, as latent acid donors, especially at wavelengths over 390 nm, and to the use of the compounds in the production of photoresists.Type: GrantFiled: October 28, 1996Date of Patent: January 25, 2000Assignee: Ciba Specialty Chemials CorporationInventors: Kurt Dietliker, Martin Kunz
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Patent number: 6017976Abstract: Process for producing coatings or moldings by radiation curing, which involves using high-energy light to irradiate radiation-curable compositions containing 1-100% by weight, based on the total amount of free-radically or cationically polymerizable compounds, of compounds A) containing at least one cationically polymerizable 2,3-dihydrofuran structure.Type: GrantFiled: October 22, 1996Date of Patent: January 25, 2000Assignee: BASF AktiengesellschaftInventors: Wolfgang Reich, Reinhold Schwalm, Erich Beck, Lukas Haussling, Oskar Nuyken, Roman-Benedikt Raether
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Patent number: 6008265Abstract: An ionic compound comprising at least one group A.sup.+ X.sup.-, comprising:a cationic group A.sup.+ selected from the group consisting of biaryliodonium, arylsulfonium, arylacylsulfonium, diazonium and organometallic cations comprising a transition metal complexed with at least one unsaturated cyclic compound comprising 4-12 carbon atoms, said cationic group being part of a polymer chain; whereinX.sup.- is an imide anion, [FSO.sub.2 NSO.sub.2 R'.sub.F ].sup.- or [R.sub.F CH.sub.2 OSO.sub.2 NSO.sub.2 R'.sub.F ].sup.- or [(R.sub.F).sub.2 CHOSO.sub.2 NSO.sub.2 R'.sub.F ].sup.-, or a methylide anion [FSO.sub.2 C(Q)SO.sub.2 R'.sub.F ].sup.-, or a [R.sub.F CH.sub.2 OSO.sub.2 C(Q)SO.sub.2 R'.sub.F ].sup.- or [(R.sub.F).sub.2 CHOSO.sub.2 C(Q)SO.sub.2 R'.sub.F ].sup.31 .Type: GrantFiled: October 3, 1997Date of Patent: December 28, 1999Assignees: Hydro-Quebec, Centre National de la Recherche ScientifiqueInventors: Alain Vallee, Michel Armand, Xavier Ollivrin, Christophe Michot
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Patent number: 5985950Abstract: 1,2-Disulfones are particularly suitable as thermally and photochemically activatable latent acid catalysts for binder systems which contain at least one acid-curable component.Type: GrantFiled: January 21, 1998Date of Patent: November 16, 1999Assignee: Ciba Specialty Chemicals CorporationInventors: Ekkehard Bartmann, Jorg Ohngemach
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Patent number: 5891529Abstract: Curable compositions comprising a substance that produces a base when exposed to radiation and a polymer molecule that contains silicon-hydrogen bonds which react with hydroxyl groups under the action of the base to form silicon-oxygen bonds (Si--O) and hydrogen molecules. These compositions cure when exposed to radiation. A pattern can be formed by placing a mask between a coating of the composition and the radiation source during this exposure episode and thereafter dissolving the uncured composition. The compositions have little weight loss during their cure, they can be cured by low intensity radiation, and they yield heat-resistant cured products.Type: GrantFiled: May 18, 1998Date of Patent: April 6, 1999Assignee: Dow Corning Asia, Ltd.Inventors: Brian Robert Harkness, Mamoru Tachikawa
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Patent number: 5882835Abstract: A chemical amplified positive photoresist composition including a resin having the repeating unit of Formula I and a photoacid generator. The resin ranges, in polystyrene-reduced molecular weight, from about 2,000 to 1,000,000. In Formula I, k and l each represent a mole ratio satisfying the condition of k+l=l. R.sub.1 is a hydrogen atom or a methyl group. R.sub.2 and R.sub.3 are independently either a hydrogen atom, a halogen atom, an alkyl group or an alkoxy group. R.sub.4 is an acetate group, a t-butoxycarbonyl group, a benzyl group, a trialkylsilyl group or an alkyl group. The photoacid generator which generates an acid by radiation.Type: GrantFiled: September 17, 1997Date of Patent: March 16, 1999Assignee: Korea Kumho Petrochemical Co., Ltd.Inventors: Joo-Hyeon Park, Seong-Ju Kim, Ki-Dae Kim, Sun-Yi Park
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Patent number: 5882842Abstract: An active energy ray-curable resin composition, particularly an active energy ray-curable coating composition, both comprising:(A) a resin having oxetane functional groups and epoxy groups in the molecule, and(B) a photo-induced cationic polymerization initiator.Type: GrantFiled: February 12, 1997Date of Patent: March 16, 1999Assignee: Kansai Paint Co., Ltd.Inventors: Yu Akaki, Fumio Yamashita, Yasuo Takaya, Osamu Isozaki
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Patent number: 5849808Abstract: A polymer which is insoluble in aqueous-alkaline developer solutions, and comprises structural units of the formula (I): ##STR1## in which R.sub.2 is hydrogen, C.sub.1 -C.sub.18 alkyl, C.sub.5 -C.sub.10 cycloalkyl, C.sub.5 -C.sub.14 aryl, C.sub.6 -C.sub.30 aralkyl, R.sub.3 is C.sub.1 -C.sub.18 alkyl, C.sub.5 -C.sub.10 cycloalkyl, C.sub.5 -C.sub.14 aryl, or C.sub.6 -C.sub.30 aralkyl, it being possible for the alkyl, cycloalkyl, aryl, or aralkyl groups to be substituted if desired by one or more hydroxyl groups or nitro groups or by one or more halogen atoms, and X is a k+1 valent organic radical, k being a number from 1 to 5, and 1 is a number from 0 to 4, in a quantity such that the cleavage products obtained by reaction with an acid are soluble in aqueous-alkaline developer solutions, is suitable as a binder for DUV photoresists of high processing stability, high contrast, and good resolution.Type: GrantFiled: April 19, 1996Date of Patent: December 15, 1998Assignee: Olin Microelectronic Chemicals, Inc.Inventors: Hans-Thomas Schacht, Norbert Muenzel
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Patent number: 5837746Abstract: Compounds of the formulaRG--A--INwherein IN is a photoinitiator basic structure A is a spacer group and RG is a functional reactive group can be employed as coreactive photoinitiators for photo-polymerization of systems containing ethylenically unsaturated compounds.Type: GrantFiled: June 23, 1997Date of Patent: November 17, 1998Assignee: Ciba Specialty Chemicals CorporationInventors: Manfred Kohler, Jorg Ohngemach, Eike Poetsch, Rudolf Eidenschink, Gerhard Greber, Dieter Dorsch, Jurgen Gehlhaus, Konrad Dorfner, Hans Ludwig Hirsch
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Patent number: 5811218Abstract: An N-aryl-.alpha.-amino acid (I), which is a novel compound, is effective as a photoinitiator. The photoinitiator composition including this photoinitiator is effective for improving photosensitive properties of photosensitive materials containing poly(amic acid) and an addition polymerizable compound used for pattern formation. Further, a photoinitiator composition (A) comprising an N-aryl-.alpha.-amino acid (I) or (I'), a 3-substituted coumarin (II) and/or an azabenzalcyclohexanone (III), or a photoinitiator composition (B) comprising an N-aryl-.alpha.-amino acid (I) or (I'), a 3-substituted coumarin (II) and a titanocene (IV), or a photoinitiator composition (C) comprising a 3-substituted coumarin (II), a titanocene (IV) and an oxime ester (V), is effective for improving photosensitive properties of photosensitive materials containing poly(amic acid) and an addition polymerizable compound used for pattern formation.Type: GrantFiled: July 17, 1995Date of Patent: September 22, 1998Assignee: Hitachi Chemical Company, Ltd.Inventors: Makoto Kaji, Yasunori Kojima, Shigeki Katogi, Masataka Nunomura, Hideo Hagiwara, Dai Kawasaki, Mitsumasa Kojima, Hiroshi Suzuki, Hidetaka Satou
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Patent number: 5807905Abstract: Compounds of the formula I ##STR1## in which n and o are a number from 0 to 50, m is a number from 1 to 50, u and v are 0 or 1, and at least one of the indices u and v is 1, R.sub.1, R.sub.2, R.sub.2a, R.sub.3 and R.sub.4 independently of one another are, for example, aromatic hydrocarbons, R.sub.5, if n and o are 0, is for example C.sub.1 -C.sub.12 alkyl and, if n and/or o are greater than 0, or if n and o are 0 and at the same time only one index u or v is 1, R.sub.5 may additionally, for example, be an aromatic hydrocarbon, at least one of the radicals R.sub.1, R.sub.2, R.sub.2a, R.sub.3, R.sub.4 and R.sub.5 being an aromatic hydrocarbon radical which is sterically hindered ortho to the boron atom, X is, for example, C.sub.1 -C.sub.20 alkylene, phenylene, biphenylene, etc., and Z is a radical which is able to form positive ions, are suitable as photoinitiators, both the compounds per se and their combination with dyes or other electron acceptors.Type: GrantFiled: November 21, 1996Date of Patent: September 15, 1998Assignee: Ciba Specialty Chemicals CorporationInventors: Allan Francis Cunningham, Martin Kunz, Hisatoshi Kura
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Patent number: 5789460Abstract: Curable compositions comprising a substance that produces a base when exposed to radiation and a polymer molecule that contains silicon-hydrogen bonds which react with hydroxyl groups under the action of the base to form silicon-oxygen bonds (Si--O) and hydrogen molecules. These compositions cure when exposed to radiation. A pattern can be formed by placing a mask between a coating of the composition and the radiation source during this exposure episode and thereafter dissolving the uncured composition. The compositions have little weight loss during their cure, they can be cured by low intensity radiation, and they yield heat-resistant cured products.Type: GrantFiled: January 24, 1996Date of Patent: August 4, 1998Assignee: Dow Corning Asia, Ltd.Inventors: Brian Robert Harkness, Mamoru Tachikawa
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Patent number: 5759750Abstract: A radiation-sensitive mixture essentially consisting of(a) a water-insoluble binder or binder mixture and(b) a compound which forms a strong acid on exposure to radiation,component (a) being a phenolic resin in which some or all of the phenolic hydroxyl groups have been replaced with groups (IA) or (IB) ##STR1## where R.sup.1, R.sup.2 and R.sup.3 are each alkyl or R.sup.1 together with R.sup.2 forms a ring and X is CH.sub.2, O, S, SO.sub.2 or NR.sup.4, is suitable for the production of relief structures.Type: GrantFiled: April 18, 1997Date of Patent: June 2, 1998Assignee: BASF AktiengesellschaftInventors: Horst Binder, Reinhold Schwalm, Dirk Funhoff
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Patent number: 5726217Abstract: A tetraphenol compound represented by the formula (I): ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 represent hydrogen 1,2-naphthoquinonediazide-4-sulfonyl or 1,2-naphthoquinonediazide-5-sulfonyl and a method for producing the compound are provided, and the compound can be used as a photosensitizer for a positive resist which exhibits superior properties.Type: GrantFiled: March 8, 1996Date of Patent: March 10, 1998Assignee: Sumitomo Chemical Company, LimitedInventors: Koji Ichikawa, Haruyoshi Osaki, Jun Tomioka
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Patent number: 5717003Abstract: 1,2-Disulfones are particularly suitable as thermally and photochemically activatable latent acid catalysts for binder systems which contain at least one acid-curable component.Type: GrantFiled: August 28, 1992Date of Patent: February 10, 1998Assignee: Ciba Specialty Chemicals CorporationInventors: Ekkehard Bartmann, Jorg Ohngemach
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Patent number: 5716756Abstract: Sulfonic acid esters are used as (a) compounds for forming a strong acid on irradiation in radiation-sensitive, positive or negative working mixtures also comprising (b) either a compound with at least one acid-decomposable C--O--C or C--O--Si bond (for positive working mixtures) or a compound with at least acid-cross-linkable groups (for negative working mixtures) and c) a binder which is insoluble in water but soluble or at least swellable in aqueous alkaline solutions, wherein said sulfonic acid esters are formula?R.sup.1 --CR.sup.2 (CF.sub.3)--O--SO.sub.2 --!.sub.n R.sup.3(I)orR.sup.1 ?--CR.sup.2 (CF.sub.3)--O--SO.sub.2 --R.sup.3 !m (II)wherein R.sup.1, R.sup.2, R.sup.3, n and n are defined with the body of the disclosure. These mixtures are particularly suitable for exposure to deep UV radiation in the formation of recording materials suitable for the production of photoresists, electronic components, and printing plates.Type: GrantFiled: May 30, 1995Date of Patent: February 10, 1998Assignees: Hoechst Aktiengesellschaft, Herberts GmbHInventors: Georg Pawlowski, Walter Spiess, Horst Roeschert, Wolfgang Appel, Walter Herr
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Patent number: 5707777Abstract: A positive-working light-sensitive composition which comprises:(a) 0.5 to 80% by weight of a compound which has at least one group capable of being decomposed by an acid and whose solubility in an alkaline developer is increased by an acid;(b) 0.01 to 20% by weight of a disulfone compound represented by the following formula (I);R.sup.1 --SO.sub.2 --SO.sub.2 --R.sup.2 (I)wherein R.sup.1 and R.sup.2 may be the same or different and represent a substituted or unsubstituted alkyl, alkenyl or aryl group; and(c) 5 to 99.49% by weight of a resin insoluble in water and soluble in an alkaline water,wherein the compound of the component (a) has a molecular weight of not more than 2,000 and a boiling point of not less than 150.degree. C. and wherein a film of the composition having a thickness of 1 .mu.m has an optical density determined at 248 nm of not more than 1.4 before exposure to light and the optical density of the composition determined at 248 nm is reduced by exposure to light of 248 nm.Type: GrantFiled: June 6, 1995Date of Patent: January 13, 1998Assignee: Fuji Photo Film Co., Ltd.Inventors: Toshiaki Aoai, Tadayoshi Kokubo
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Patent number: 5698369Abstract: Disclosed is a photosensitive composition comprising a sulfonimide compound represented by formula (I):R.sub.1 --SO.sub.2 --NR.sub.3 --SO.sub.2 --R.sub.2 (I)wherein R.sub.1, R.sub.2 and R.sub.3 each represents an unsubstituted or substituted aromatic group or an unsubstituted or substituted alkyl group.Type: GrantFiled: June 7, 1995Date of Patent: December 16, 1997Assignee: Fuji Photo Film Co., Ltd.Inventors: Koichi Kawamura, Fumikazu Kobayashi, Tsukasa Yamanaka
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Patent number: 5693452Abstract: A positive chemically amplified resist composition is disclosed, comprising (a) a compound which generates an acid upon irradiation with active light or radiant ray; (b) a resin insoluble in water but soluble in an aqueous alkali solution; and (c) a low molecular acid-decomposable dissolution inhibitor having a molecular weight of 3,000 or less and containing an acid-decomposable alkyl ester group represented by formula (I), and which increases its solubility in an alkali developer by the action of an acid, and having a sodium content and a potassium content each of 30 ppb or less. Also disclosed is a positive chemically amplified resist composition comprising the foregoing compound (a) and (d) a resin having an acid-decomposable alkyl ester group represented by formula (I), and which increases its solubility in an alkali developer by the action of an acid, and having a sodium content and a potassium content each of 30 ppb or less. Still further disclosed are methods for producing the compounds (c) and (d).Type: GrantFiled: October 26, 1995Date of Patent: December 2, 1997Assignee: Fuji Photo Film Co., Ltd.Inventors: Toshiaki Aoai, Toru Fujimori
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Patent number: 5679496Abstract: A chemically amplified positive resist composition contains a novel trifluoromethanesulfonic or p-toluenesulfonic acid sulfonium salt having at least one tert-butoxycarbonylmethoxy group as an acid labile group. The composition is highly sensitive to high energy radiation, especially KrF excimer laser and has high sensitivity, resolution and plasma etching resistance while the resulting resist pattern is heat resistant.Type: GrantFiled: December 4, 1995Date of Patent: October 21, 1997Assignees: Shin-Etsu Chemical Co., Ltd., Nippon Telegraph and Telephone Corp.Inventors: Youichi Ohsawa, Satoshi Watanabe, Katsuyuki Oikawa, Akinobu Tanaka, Yoshio Kawai, Jiro Nakamura
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Patent number: 5629095Abstract: The present invention relates to radiation curable silicone vinyl ethers and methods for preparing silicone vinyl ethers. More particularly, the present invention relates compositions containing vinyl ether functional silicones and to the preparation and use of silicone vinyl ethers which are curable by addition of photocleavable acids and exposure to ultraviolet or electron beam radiation.Type: GrantFiled: May 18, 1995Date of Patent: May 13, 1997Assignee: Dow Corning CorporationInventors: Valerie J. Bujanowski, Shedric O. Glover, Susan V. Perz, Maris J. Ziemelis, Gary R. Homan, Michael W. Skinner
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Patent number: 5627006Abstract: A photoresist composition comprising (a) a difficultly alkali-soluble special resin, (b) a photo-sensitive compound capable of generating a carboxylic acid, and (c) a solvent, is effective for pattern formation using deep ultraviolet light, KrF excimer laser beams, etc.Type: GrantFiled: April 18, 1995Date of Patent: May 6, 1997Assignees: Wako Pure Chemical Industries, Ltd., Matsushita Electric Industrial Co., Ltd.Inventors: Fumiyoshi Urano, Keiji Oono, Hirotoshi Fujie
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Patent number: 5627011Abstract: The invention relates to the use of oxime sulfonates of formula 1 ##STR1## wherein R is naphthyl, ##STR2## Ar is an unsubstituted aryl group or an aryl group which carries one or more than one substituent selected from the group consisting of nitro, chloro, bromo, hydroxyl, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 perfluoroalkyl, C.sub.1 -C.sub.4 alkoxy and acid degradable substituents;R.sub.0 is either a R.sub.1 --X group or R.sub.2 ;X is an oxygen or a sulfur atom;R.sub.1 is hydrogen, C.sub.1 -C.sub.4 alkyl or unsubstituted phenyl or phenyl which is substituted by a member selected from the group consisting of chloro, bromo, C.sub.1 -C.sub.4 alkyl and C.sub.1 -C.sub.4 alkoxy, andR.sub.2 is hydrogen, C.sub.1 -C.sub.Type: GrantFiled: May 12, 1995Date of Patent: May 6, 1997Assignee: Ciba-Geigy CorporationInventors: Norbert Munzel, Reinhard Schulz, Heinz Holzwarth, Stephan Ilg
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Patent number: 5565500Abstract: The invention relates to mixtures containing:a) a cationically polymerizable compound andb) a compound of the formula I[R.sup.1 (Fe.sup.II R.sup.2).sub.a ].sub.q.sup..sym.an anX.sup..crclbar.q (I)in which a is 1 or 2, n is 1 or 2, R.sup.1 is a substituted or unsubstituted .pi.-arene, R.sup.2 is a substituted or unsubstituted .pi.-arene or cyclopentadienyl anion or indenyl anion, q is an integer from 1 to 3 and X is FSO.sub.3.sup.- or a q-valent anion of an organic sulfonic acid or of a carboxylic acid; R.sup.1 can also be a polymeric, aromatic ligand. The invention also relates to the novel compounds of the formula I. The curable mixtures can be processed in particular for the production of coatings having a good resistance to heat.Type: GrantFiled: September 22, 1994Date of Patent: October 15, 1996Assignee: Ciba-Geigy CorporationInventors: Kurt Meier, Roger P. Salvin
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Patent number: 5563022Abstract: A positive-working UV-sensitive mixture containing(a1) an organic binder containing acid-labile ether, ester or carbonate groups or(a2) a polymeric binder which is insoluble in water but soluble in aqueous alkaline solutions and(a2.1) an organic compound whose solubility in an aqueous alkaline developer is increased by the action of an acid, or(a2.2) an organic compound whose solubility in an aqueous alkaline developer is increased by the action of an acid and which contains one or more acid-cleavable groups and in addition a group which forms an acid under the action of radiation, or a mixture of the organic compounds (a2.1) and (a2.2) and(b) an arylsulfonic ester, is suitable for the production of relief patterns.Type: GrantFiled: October 29, 1992Date of Patent: October 8, 1996Assignee: BASF AktiengesellschaftInventors: Horst Binder, Reinhold Schwalm, Dirk Funhoff
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Patent number: 5468589Abstract: A resist composition comprising (a) a polymer having at least repeating units of the formulae: ##STR1## (b) a photoacid generator and (c) a solvent, has high sensitivity to light, excellent heat resistance, adhesiveness to a substrate and suitable for pattern formation with high resolution.Type: GrantFiled: June 15, 1992Date of Patent: November 21, 1995Assignees: Wako Pure Chemical Industries, Ltd., Matsushita Electric Industrial Co., Ltd.Inventors: Fumiyoshi Urano, Hirotoshi Fujie, Keiji Oono, Takaaki Negishi
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Patent number: 5466722Abstract: Polymerization of ethylenically unsaturated monomers such as methyl methacrylate can be initiated in solutions containing monomer and a special non-polymeric initiator with intense ultrasound. The number average molecular weight of the poly(methyl methacrylate) that forms is about 300,000 gmol.sup.-1 as compared with polystyrene standards. The conversion of the polymerization is about 50% for poly(methyl methacrylate). Variations of the polymerization rate with time and the amount of the initiator are explained by a simple reaction mechanism.Type: GrantFiled: January 27, 1994Date of Patent: November 14, 1995Inventors: James O. Stoffer, Oliver C. Sitton
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Patent number: 5403695Abstract: Disclosed herein is a resist for forming patterns, which is greatly sensitive to ultraviolet rays an ionizing radiation, and which can therefore form a high-resolution resist pattern if exposed to ultra violet rays or an unionizing radiation. Hence, the resist is useful in a method of manufacturing semicon ductor devices having high integration densities. The resist comprises tert-butoxycarbonyl methoxypolyhydroxy styrene and an o-quinonediazide compound.Type: GrantFiled: April 30, 1992Date of Patent: April 4, 1995Assignee: Kabushiki Kaisha ToshibaInventors: Rumiko Hayase, Yasunobu Onishi, Hirokazu Niki, Naohiko Oyasato, Yoshihito Kobayashi, Shuzi Hayase
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Patent number: 5393641Abstract: A novel radiation-sensitive resin composition having high sensitivity and high O.sub.2 -RIE resistance is otained by blending 0.5 g of poly(di-t-butoxysiloxane), 50 mg of triphenylsulfonium trifluoromethanesulfonate as acid-producing agent, and 4 ml of 2-methoxyethyl acetate as solvent.Type: GrantFiled: June 6, 1994Date of Patent: February 28, 1995Assignee: Oki Electric Industry Co., Ltd.Inventors: Toshio Ito, Miwa Sakata
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Patent number: 5384229Abstract: The present invention provides photoimageable compositions, processes and articles of manufacture. In particular, the invention provides a process comprising electrophoretically applying a coating layer of a photoimageable composition onto a conductive surface, the composition comprising a material that contains one or more photoacid labile groups. The photoimageable compositions of the invention preferably comprise a photoacid generator, a material that contains one or more acid-clearable functional groups, and a carrier resin that contains one or more functional groups that are, or can be treated to be, at least partially ionized.Type: GrantFiled: May 7, 1992Date of Patent: January 24, 1995Assignee: Shipley Company Inc.Inventors: Daniel Y. Pai, Stephen S. Rodriguez, Roger F. Sinta
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Patent number: 5350660Abstract: A resist material comprising (a) a polymer having a monomer unit having a special functional group, a monomer unit having a phenolic hydroxyl group, and if necessary a third monomer unit, (b) a photoacid generator, and (c) a solvent can provide a resist film excellent in heat resistance and adhesiveness to a substrate when exposed to light with 300 nm or less such as deep UV light, KrF excimer laser light, etc., and is suitable for forming ultrafine patterns.Type: GrantFiled: January 28, 1991Date of Patent: September 27, 1994Assignee: Wako Pure Chemical Industries, Ltd.Inventors: Fumiyoshi Urano, Masaaki Nakahata, Hirotoshi Fujie, Keiji Oono