Material Contains A Heavy Metal Atom Patents (Class 528/236)
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Patent number: 8586289Abstract: The aromatic hydrocarbon resin can be used as a coating material and a resist resin for a semiconductor, and has a high carbon concentration and a low oxygen concentration. A composition for forming an underlayer film for lithography that has excellent etching resistance as an underlayer film for a multilayer resist process, an underlayer film formed with the same, and a pattern forming method using the same are disclosed. An aromatic hydrocarbon is reacted with an aromatic aldehyde in the presence of an acidic catalyst, thereby providing an aromatic hydrocarbon resin that has a high carbon concentration of from 90 to 99.9% by mass and a low oxygen concentration of from 0 to 5% by mass. A composition for forming an underlayer film for lithography contains the resin and an organic solvent, an underlayer film is formed with the same, and a pattern forming method uses the same.Type: GrantFiled: September 14, 2010Date of Patent: November 19, 2013Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Ryuji Ideno, Seiji Kita, Masashi Ogiwara, Gou Higashihara
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Publication number: 20120171611Abstract: The aromatic hydrocarbon resin can be used as a coating material and a resist resin for a semiconductor, and has a high carbon concentration and a low oxygen concentration. A composition for forming an underlayer film for lithography that has excellent etching resistance as an underlayer film for a multilayer resist process, an underlayer film formed with the same, and a pattern forming method using the same are disclosed. An aromatic hydrocarbon is reacted with an aromatic aldehyde in the presence of an acidic catalyst, thereby providing an aromatic hydrocarbon resin that has a high carbon concentration of from 90 to 99.9% by mass and a low oxygen concentration of from 0 to 5% by mass. A composition for forming an underlayer film for lithography contains the resin and an organic solvent, an underlayer film is formed with the same, and a pattern forming method uses the same.Type: ApplicationFiled: March 24, 2011Publication date: July 5, 2012Inventors: Ryuji Ideno, Seiji Kita, Masashi Ogiwara, Gou Higashihara
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Patent number: 7064177Abstract: A process is described for preparing polyoxymethylene by contacting a formaldehyde source with a catalyst of the formula I [CpvMLw]m+Zm/nn???(I) where M is Ti, Zr, Hf, V, Nb, Ta, Cr, Mo, W, Mn, Re, Fe, Ru, Os, Co, Rh or Ir, Cp is a cyclopentadienyl ligand C5H(5-u)R1u, where u is from 0 to 5 and R1 is alkyl, alkenyl, aryl, heteroaryl, aralkyl, COOR2, COR2, CN or NO2, and R2 is H, alkyl, aryl or aralkyl, v is 1 or 2, each L is independently a nitrile, CO or a ligand displaceable by CO, w is an integer from 0 to 4, Z is an anion, and m and n are each independently an integer from 1 to 3.Type: GrantFiled: April 10, 2003Date of Patent: June 20, 2006Assignee: BASF AktiengesellschaftInventors: Hans-Helmut Görtz, Gerrit Luinstra, Wolfram Wielandt, Michael Henes, Ekkehard Lindner
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Patent number: 6335304Abstract: A metal (M) alkyl acid phosphate catalyst for the reaction of an epoxy compound with a carboxyl compound to provide a coating formulation that is stable at room temperature; that is humidity resistant, and non-yellowing, wherein the alkyl acid phosphate has the formula: (RO)n—(P═O)—(OH)m and wherein: a. each R is selected from the group consisting of: i) a C1 to C18 alkly, cycloalkyl, or aryl; ii) a linear or branched C6 to C18 alkyl substituted with —(O—CH2—CH2—)o or —(O—CH—CH3—CH2—)p, wherein o or p is from 1 to 20; iii) a &bgr;-hydroxyethyl compound, R′—X—CH2—CH—OH—CH2—, wherein R′ is a C6 to C18 alkyl or cycloalkyl or aryl, X is either —CH2—, —O— or —COO—; b. n+m=3 and n is between 2 to 1; and c. M is Zn or Sn (II) in a mole equivalent of 0.7 to 1.5 moles per mole of alkyl acid phosphate.Type: GrantFiled: November 9, 1999Date of Patent: January 1, 2002Assignee: KIng Industries, INCInventors: Zhiqiang Alex He, Werner J. Blank, Marie Emmanuelle Picci
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Publication number: 20010049430Abstract: A water slurry process is used to prepare a prepreg and to manufacture articles from macrocyclic polyester oligomers. In one embodiment, a process for preparing a water suspension of macrocyclic polyester oligomers includes the steps of contacting a macrocyclic polyester oligomer and a polymerization catalyst with water and a surfactant, and mixing the macrocyclic polyester oligomer and polymerization catalyst with water and the surfactant thereby forming a suspension. In another embodiment, a process for impregnating macrocyclic polyester oligomers for polymerization includes the steps of providing a suspension of a macrocyclic polyester oligomer and a polymerization catalyst in water, applying the suspension to a base material, drying to remove water from the suspension, and pressing the dried suspension to a desired form. In yet another embodiment, a composition of macrocyclic polyester oligomer includes a macrocyclic polyester oligomer, a polymerization catalyst, and water.Type: ApplicationFiled: January 4, 2001Publication date: December 6, 2001Inventors: Steven J. Winckler, Tohru Takekoshi
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Patent number: 5908912Abstract: An electrodepositable coating composition is provided comprising (a) an active hydrogen-containing, cationic salt group-containing resin electrodepositable on a cathode; (b) a curing agent for transurethanation, transamidation or transesterification curing like at least a partially capped polyisocyanate curing agent; and (c) a catalytic mixture of bismuth and an amino acid or amino acid precursor. Optionally, an auxiliary acid may be present to increase the effectiveness of the amino acid in the mixture with bismuth.Type: GrantFiled: June 3, 1997Date of Patent: June 1, 1999Assignee: PPG Industries Ohio, Inc.Inventors: Raphael O. Kollah, Matthew S. Scott, Gregory J. McCollum, Joseph A. Bethoski
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Patent number: 5770678Abstract: A process for polymerizing oxiranes, oxetanes, oxepanes, dioxolanes, trioxanes, and tetrahydrofurans to their respective polymers by contacting them with a selected metal compound is disclosed; and also a process for depolymerizing polytetrahydrofurans to monomeric tetrahydrofurans by contacting the polymer with a selected metal compound at a temperature of about 100.degree. C. to about 250.degree. C. The catalysts may be in solution or part of a heterogeneous solid, and selected organic compounds are used as accelerators in the polymerizations. The polymeric products, some of which are novel, may be used as polyether monomers for further polymerization, as by reaction with isocyanates to produce polyurethanes, and other useful polymers. Some of the polymeric products are relatively high in molecular weight and are suitable for direct use, for instance as spandex fibers.Type: GrantFiled: December 9, 1996Date of Patent: June 23, 1998Assignee: E. I. du Pont de Nemours and CompanyInventors: Neville Everton Drysdale, Richard Edmund Bockrath, Norman Herron, Joel David Citron
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Patent number: 5641853Abstract: A process for polymerizing oxepanes, dioxolanes, trioxanes, and tetrahydrofurans to their respective polymers by contacting them with a selected metal compound and an accelerator which is a selected vinyl ester or a selected phosphorous compound.Type: GrantFiled: February 28, 1996Date of Patent: June 24, 1997Assignee: E. I. Du Pont de Nemours and CompanyInventor: Neville Everton Drysdale
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Patent number: 5500477Abstract: A moulding composition based on linear polyoxymethylene copolymers and customary additives with a melt index MFI (2,16 kg, 190.degree. C.) of .ltoreq.0,8, preferably .ltoreq.0,5 and especially .ltoreq.0,2 g/10 min has an extraordinary high toughness, which eliminates an addition of elastomer modifiers. In its preparation Lewis acids or protonic acids are used as initiators.Type: GrantFiled: April 26, 1995Date of Patent: March 19, 1996Assignee: Hoechst AktiengesellschaftInventors: Gerhard Reuschel, Dietrich Fleischer, Kaoru Yamamoto, Shuichi Chino
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Patent number: 5374697Abstract: Sulfonium compounds of formula 1 or 2 ##STR1## wherein R is a mononuclear cycloalkyl radical containing 3 to 8 ring carbon atoms or a mononuclear cycloalkyl radical which contains 3 to 8 ring carbon atoms and to which at least one further ring containing carbon atoms is fused,X is a non-nucleophilic anion, andZ is a single bond, an oxygen or sulfur atom, a group of formula >S.sup..sym. --R X.sup..crclbar., wherein R and X are as defined above, or is >C.dbd.O or a methylene bridge,which sulfonium compounds are either unsubstituted or carry one or more than substituent selected from the group consisting of halogen, nitro, C.sub.1 -C.sub.8 alkyl, phenyl, hydroxyl, C.sub.1 -C.sub.8 alkoxy, phenoxy, benzyloxy, alkoxycarbonyl containing 1 to 4 carbon atoms in the alkoxy moiety or acyl of 1 to 12 carbon atoms.Type: GrantFiled: July 14, 1993Date of Patent: December 20, 1994Assignee: Ciba-Geigy CorporationInventor: Beat Muller
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Patent number: 5124417Abstract: Disclosed are novel compounds which are useful as initiators for cationically polymerizable monomers. The novel compounds comprise a carbon containing cation (e.g., trimethyloxonium) which is capable of initiating cationic polymerization and a non-nucleophilic counterion which is an at least partially fluorinated hydrocarbylsulfonato metallate (e.g. perfluoroethylsulfonato-aluminate). The disclosed initiators are capable of initiating the cationic polymerization of a wide variety of monomers such as epoxides, tetrahydrofuans, oxazolines, vinyls, lactones, and the like.Type: GrantFiled: September 3, 1991Date of Patent: June 23, 1992Assignee: Minnesota Mining and Manufacturing CompanyInventor: Omar Farooq
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Patent number: 5055547Abstract: The present invention relates to copolyethers comprising copolymers of 7,oxa-bicyclo(2,2,1)heptane, and its alkyl-derivatives, with one or more single-ring or condensed-rings cycloaliphatic ethers, comprising the characteristic group; ##STR1## wherein R' is hydrogen and R" is H, a halogen, or an alkyl radical containing a small number of carbon atoms, and which may also be halogen-substituted.If the ether contains one ring only, it contains from 5 to 12 atoms in the ring, and if it contains a condensed-ring system, it contains a total number of from 10 to 18 atoms in the rings.Those copolyethers show a anisotropic behaviour in the molten state, and therefore have liquid-crystal properties.Type: GrantFiled: May 10, 1989Date of Patent: October 8, 1991Assignee: Montedison S.p.A.Inventors: Leonardo Fiore, Giuseppe Motroni, Mauro Maritano
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Patent number: 5011907Abstract: Highly conjugated organic polymers typically have large non-resonant electronic susceptibilities, which give the molecules unusual optical properties. To enhance these properties, "defects" are introduced into the polymer chain. Examples include light doping of the conjugated polymer and synthesis, conjugated polymers which incorporate either electron donating or accepting groups, and conjugated polymers which contains a photoexcitable species capable of reversibly transferring its electron to an acceptor. Such defects in the chain permit enhancement of the second hyperpolarizability by at least an order of magnitude.Type: GrantFiled: October 10, 1989Date of Patent: April 30, 1991Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space AdministrationInventor: David N. Beratan
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Patent number: 4847332Abstract: Cyclic formals, other than trioxane, form macromers with an olefinically unsaturated alcohol which functions as a propagating species to form a macromer of polyformal having a molecular weight generally less than about 10,000. A cationically ring-openable ether may be used to provide a polyether spacer in the alkenyl alcohol so that the macromer of polyformal formed contains a polyether block. Thus, the polyformal macromer may have a acryloyl, allyl, or styryl head group. Macromers of polyformal block copolymers are formed sequentially by first forming the block of first formal and then without isolating the macromer so formed, sequentially polymerizing a second formal monomer to form the second formal block. A macromer of randon copolymer may be formed with one or more cyclic formals or a cyclic ether. Macromers of random copolymers may also be formed with formaldehyde or trioxane.Type: GrantFiled: December 7, 1987Date of Patent: July 11, 1989Assignee: The B. F. Goodrich CompanyInventor: Simon H. Yu
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Patent number: 4839457Abstract: A developing composition and a sheet for a pressure-sensitive copy paper comprising a phenolic resin as a main component which is obtained by condensating with formaldehyde using a p-substituted phenol with a 2,4-di-substituted and/or 2,6-di-substituted phenol, and zinc oxide which may be added thereto, as occasion demands.Type: GrantFiled: March 18, 1988Date of Patent: June 13, 1989Assignee: Mitsubishi Petrochemical Co., Ltd.Inventors: Kazuhide Hayama, Yukio Saitoh
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Patent number: 4764585Abstract: Cationic fixing agents based on the reaction products of(a) a monofunctional or polyfunctional amine having one or more primary and/or secondary and/or tertiary amino groups and(b) cyanamide, dicyandiamide, guanidine or bisguanidinegive improved results when the reaction takes place in the presence of a catalyst (K) selected from metals, metal salts and heterocyclic nitrogen-containing organic bases, particularly zinc chloride.Type: GrantFiled: September 15, 1987Date of Patent: August 16, 1988Assignee: Sandoz Ltd.Inventors: Jurg Heller, Bruno Kissling, Curt Muller, Tibor Robinson, Salvatore Valenti
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Patent number: 4547565Abstract: A trioxane copolymer is manufactured by adding to trioxane and a co-monomer, 0.0001 to 2.0 percent by weight, based on the total weight of the monomers, of one or more sterically hindered phenols, then co-polymerizing the resultant mixture in the presence of a cation-active catalyst, and then treating the resultant copolymer by heating it at a temperature which is higher than the melting point of the copolymer to melt the copolymer and decompose and remove unstable parts of the copolymer.Type: GrantFiled: June 8, 1984Date of Patent: October 15, 1985Assignee: Polyplastics Company, Ltd.Inventors: Takuzo Kasuga, Takeshi Asano, Yukio Ikenaga, Masami Yamawaki, Yasuyuki Takeda, Koichi Ichimura
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Patent number: 4399272Abstract: A process for producing a polyacetal copolymer, which comprises copolymerizing formaldehyde and a compound selected from the group consisting of alkylene oxides, poly(alkylene oxides), cyclic formals and poly (cyclic formals) in the presence of a Lewis acid and an anionic polymerization catalyst with the exception of metal chelate compounds.Type: GrantFiled: November 4, 1980Date of Patent: August 16, 1983Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Hisaya Sakurai, Minoru Hamada, Kazuhiko Matsuzaki, Muneaki Aminaka
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Patent number: 4398014Abstract: New aromatic sulfonylsulfoxonium salts are of formula ##STR1## where q is 1 to 4,R denotes an aliphatic, cycloaliphatic, or aromatic group,R.sup.6 denotes H, an alkyl or aralkyl group, or a group --COR.sup.9, --CO--NH--(CO).sub.r --R.sup.10, or --SO.sub.2 --R.sup.11, where r is zero or 1,one, but not both, of R and R.sup.6 denoting an aromatic group,R.sup.7 denotes an alkyl, alkenyl, cycloalkyl, cycloalkylalkyl, or aralkyl group,R.sup.8 has the same meaning as R.sup.7 but may alternatively represent a dialkylamino group or, if R.sup.7 denotes alkyl, it may alternatively represent an arylamino group,R.sup.9, R.sup.10, and R.sup.11 each denote an alkyl, aryl, or aralkyl radical of 1 to 25 carbon atoms,t is 1, 2, or 3, andZ.sup.- denotes a t-valent anion of a protic acid.The salts, e.g., dimethyl-p-toluenesulfonylmethylsufoxonium hexafluorophosphate, are useful as catalysts for the polymerization of cationically polymerizable materials by means of actinic radiation and/or heat.Type: GrantFiled: October 23, 1981Date of Patent: August 9, 1983Assignee: Ciba-Geigy CorporationInventors: George E. Green, Edward Irving, Bernard P. Stark
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Patent number: 4382130Abstract: Certain aryloxyphosphonium salts have been found to be effective as curing agents for various cationically polymerizable organic materials, such as epoxy resins, when incorporated into such materials. The materials are found to be moisture curable coating compositions.Type: GrantFiled: October 14, 1981Date of Patent: May 3, 1983Assignee: General Electric CompanyInventors: Robert H. Ellison, Martin A. Byrne
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Patent number: 4377667Abstract: A polyacetal suitable for moldings which are excellent in lubricity, wear and antistatic properties, which has at least one terminal of its linear polymer molecule capped with an alkylene oxide adduct of an alcohol or a carboxylic acid, which adduct is of the formula ##STR1## wherein R.sub.o is a hydrogen atom, alkyl group, substituted alkyl group, aryl group, or substituted aryl group, R.sub.o 's may be the same or different, R.sub.1 is an alkyl group, substituted alkyl group, aryl group, or substituted aryl group, R.sub.2 is a hydrogen atom, alkyl group, substituted alkyl group, aryl group, or substituted aryl group, m is from 2 to 6, and n is from 1 to 1,000; the number average molecular weight of said polyacetal being in the range from 10,000 to 500,000 excluding the terminal group.Type: GrantFiled: June 4, 1981Date of Patent: March 22, 1983Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Hisaya Sakurai, Minoru Hamada, Kazuhiko Matsuzaki
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Patent number: 4352923Abstract: Undesirable deposition of polyoxymethylene onto the inner wall of a polymerization reactor and onto a stirrer, which deposition is observed in the slurry polymerization of formaldehyde carried out in an inert organic liquid medium, can be minimized by carrying out the slurry polymerization in the presence of a polymerization catalyst prepared by bringing a metal chelate compound into contact with polyoxymethylene in an inert organic liquid medium in the presence of formaldehyde. Preferably, the slurry polymerization is carried out in the presence of, in addition to the above-mentioned polymerization catalyst, at least one polyvalent metal salt of an alkylsalicylic acid or of a dialkyl ester of sulfosuccinic acid. It is also preferable to use a tubular closed loop reactor equipped with an impeller wherein gaseous formaldehyde is blown into the reactor in a position located downstream from the impeller, while the catalyst-containing slurry is circulated therethrough.Type: GrantFiled: November 5, 1980Date of Patent: October 5, 1982Assignee: Ube Industries, Ltd.Inventors: Hisashi Kono, Kenji Terai, Masaki Hisadomi, Katumi Uemura, Sumio Ohta, Yoshiichi Yamamoto
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Patent number: 4339567Abstract: Substances (I) capable of being converted into higher-molecular weight materials under the influence of a cationic catalyst, such as 1,2-epoxides, aminoplasts, vinyl monomers or prepolymers, or phenoplasts, are so converted by exposure to actinic radiation in the presence of a sulphoxonium salt (II) of formula ##STR1## where P denotes zero or 1,R.sup.6 denotes an arylene or aralkylene group,R.sup.7 denotes --H or a group of formula ##STR2## R.sup.8 denotes an alkyl, alkenyl, cycloalkyl, cycloalkylalkyl, aryl, or aralkyl group,R.sup.9 has the same meaning as R.sup.8 but may alternatively represent a dialkylamino group or, if R.sup.8 represents an alkyl group, R.sup.9 may represent an arylamino group,R.sup.10 and R.sup.11 each independently have the same meaning as R.sup.8 but may also each denote --H,r represents 1, 2, or 3,Z.sup.r- denotes an r-valent anion of a protic acid, and q denotes zero when p denotes zero, or zero or 1 when p denotes 1.Type: GrantFiled: February 23, 1981Date of Patent: July 13, 1982Assignee: Ciba-Geigy CorporationInventors: George E. Green, Edward Irving
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Patent number: 4332930Abstract: Undesirable deposition of polyoxymethylene onto the inner wall of a polymerization vessel and onto a stirrer, which deposition is observed in the slurry polymerization of formaldehyde carried out in an inert organic liquid medium in the presence of a polymerization catalyst, can be minimized by carrying out the slurry polymerization in the presence of at least one polyvalent metal salt selected from polyvalent metal salts of alkylsalicylic acids and polyvalent metal salts of dialkyl esters of sulfosuccinic acid. Optionally, a polyethylene glycol monoether may be used in addition to the polyvalent metal salt.Type: GrantFiled: August 22, 1980Date of Patent: June 1, 1982Assignee: UBE Industries, Ltd.Inventors: Takami Ishii, Naohisa Takikawa, Kiyoaki Tokunaga, Nobuhiro Ogawa
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Patent number: 4299938Abstract: Substances (I) capable of being converted into higher-molecular weight materials under the influence of a cationic catalyst, such as 1,2-epoxides, aminoplasts, vinyl monomers or prepolymers, or phenoplasts, are so converted by exposure to actinic irradiation or by heating in the presence of an aryloxysulfoxonium salt of formula ##STR1## where either R.sup.6 and R.sup.7 separately denote lower alkyl (optionally substituted by halogen and interrupted in the chain by --O-- or --SO.sub.2 --), or an aryl or aryloxy group, or R.sup.6 and R.sup.7 together denote a divalent group forming with the S atom a heterocyclic radical; R.sup.8 denotes an aryl group; M denotes an atom of a metal or metalloid; X denotes a halogen atom; and n is 4, 5, or 6, for instance,p-chlorophenoxy-p-tolyl-p-phenoxysulfoxonium hexafluorophosphate and 1-phenoxy-1-oxidotetrahydrothiophenium tetrafluorborate.Type: GrantFiled: June 9, 1980Date of Patent: November 10, 1981Assignee: Ciba-Geigy CorporationInventors: George E. Green, Edward Irving
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Patent number: 4173551Abstract: Aromatic onium salts, such as diaryliodonium salts, have been found to be effective thermal initiators for the polymerization of a variety of cationically polymerizable materials including epoxides, cyclic ethers, phenol formaldehyde resins, etc., when used in combination with various cocatalysts such as organic acids and copper salts.Type: GrantFiled: December 16, 1977Date of Patent: November 6, 1979Assignee: General Electric CompanyInventor: James V. Crivello