Material Contains A Transition Metal Atom Patents (Class 528/234)
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Patent number: 9745400Abstract: A high-quality polyacetal produced by a process including supplying a raw material comprising trioxane, a comonomer capable of copolymerizing with trioxane and a non-volatile protonic acid to a reactor of a continuous stirring/mixing machine type; carrying out a polymerization reaction of the raw material to produce a reaction mixture; vaporizing an unreacted monomer to separate the unreacted monomer from the reaction mixture and supplying the unreacted monomer to the raw material supplying; collecting a polyacetal copolymer from the reaction mixture into a collection unit which is arranged downstream from a discharge port and is adjusted to have a gauge pressure of 0.2 kPa or more; and adding a basic compound to the collected polyacetal and then subjecting the resultant mixture to a melt-kneading treatment to deactivate the non-volatile protonic acid.Type: GrantFiled: December 10, 2014Date of Patent: August 29, 2017Assignee: POLYPLASTICS CO., LTD.Inventors: Hiroaki Nakao, Eiji Masuda
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Patent number: 9695265Abstract: A process for producing a polyacetal copolymer, the process making catalyst deactivation easy and efficient. Trioxane as a major monomer is copolymerized with one or more comonomers that are a cyclic ether and/or cyclic formal having at least one carbon-carbon bond, using a nonvolatile protonic acid as a polymerization catalyst at 100° C. or lower until the conversion reaches 50% and thereafter at a polymerization environment temperature of 115° C. to 140° C. This process includes: a crushing step in which a dry-process crusher is used to obtain a crude polyacetal copolymer crushed to such a degree that when the crude copolymer is screened with a sieve having an opening size of 11.2 mm, 90 parts by weight or more thereof passes therethrough; and a deactivation step in which a basic compound (e) is added to the crude copolymer and the mixture is melt-kneaded to thereby deactivate the polymerization catalyst.Type: GrantFiled: December 10, 2014Date of Patent: July 4, 2017Assignee: POLYPLASTICS CO., LTD.Inventors: Tadahiro Horiguchi, Eiji Masuda
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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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Publication number: 20110077378Abstract: The present invention relates to a process for the preparation of oxymethylene polymers as well as oxymethylene polymers obtainable therefrom. The process includes polymerization of a monomer, which forms —CH2—O— units in the presence of an acetal of formaldehyde or a polyhydric alcohol and an initiator for cationic polymerization. The initiator may be a heteropoly acid or an acid salt thereof which is dissolved in an alkyl ester of a polybasic carboxylic acid.Type: ApplicationFiled: May 26, 2010Publication date: March 31, 2011Applicant: TICONA GMBHInventors: Michael Haubs, Michael Hoffmockel, Jürgen Lingnau, Robert M. Gronner, Larson Lowell
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Publication number: 20090048416Abstract: The present invention relates to new high-functionality, highly branched or hyperbranched polylysines, to processes for preparing them, and to their use.Type: ApplicationFiled: November 15, 2006Publication date: February 19, 2009Applicant: BASF SEInventors: Bernd Bruchmann, Harm-Anton Klok, Markus Thomas Scholl
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Patent number: 7371808Abstract: A polymer treating method has the steps of: reacting a polymer compound with a reaction agent in a reaction vessel to generate a polymer treatment product; discharging the polymer treatment product containing the reaction agent from the reaction vessel; depressurizing the polymer treatment product; introducing the polymer treatment product into a degassing extruder; separating the reaction agent from the polymer treatment product through a vent box that is connected to upstream of the degassing extruder and that has a volume of equal to or more than that of the reaction vessel; and extruding the polymer treatment product from the degassing extruder.Type: GrantFiled: December 29, 2006Date of Patent: May 13, 2008Assignee: Hitachi Cable, Ltd.Inventors: Toshiharu Goto, Takanori Yamazaki
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Patent number: 6506850Abstract: A polyoxymethylene copolymer having a melting point of 167° to 173° C. and containing a low molecular weight polyoxymethylene copolymer in an amount of not higher than 5000 ppm, and a composition thereof. The copolymer is obtainable by subjecting unstable terminal groups to heat treatment in the presence of 0.05 to 50 ppm by weight of a quaternary ammonium compound. Further, the above composition is used for working parts such as a gear and a cam; apparatuses for image, music and telecommunication; interior and exterior parts for an automobile; and the like.Type: GrantFiled: February 21, 2001Date of Patent: January 14, 2003Assignee: Asahi Kasei Kabushiki KaishaInventors: Noritaka Tanimura, Atushi Nanasawa
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Patent number: 6020452Abstract: A chiral biphenyl compound includes a hindered 2,2'-substituted-1,1'-biphenyl subunit and has the following formula: ##STR1## The chiral biphenyl compounds have been shown to be useful as catalysts in asymmetric reactions. For example, an organozinc species can be formed by reacting the chiral biphenyl compound with an organozinc compound, R.sup.14 R.sup.15 Zn and then used as a catalyst for the asymmetric alkylation of an aldehyde by an organozinc compound.Type: GrantFiled: August 26, 1997Date of Patent: February 1, 2000Assignee: North Dakota State UniversityInventors: Lin Pu, Wei-Sheng Huang, Qiao-Sheng Hu
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Patent number: 5929195Abstract: A branched or crosslinked polyacetal resin is excellent in blow moldability, has impact resistances such as plane impact resistance, and the smoothness of the inner surfaces of moldings produced therefrom, and is suitable for molding, particularly blow molding. It can be produced by the bulk polymerization of (A) trioxane with (B) a cyclic ether and/or cyclic formal and (C) a polyfunctional glycidyl ether compound in the presence of (D) a cationic polymerization catalyst, a mixture prepared by mixing the cyclic ether and/or cyclic formal (B) with the polyfunctional glycidyl ether compound (C) and the cationic polymerization catalyst (D) is added to trioxane (A) to conduct the polymerization.Type: GrantFiled: July 14, 1998Date of Patent: July 27, 1999Assignee: Polyplastics Co., Ltd.Inventors: Kuniaki Kawaguchi, Kaoru Yamamoto, Hajime Serizawa
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Patent number: 5889134Abstract: An organozinc species, useful in the reactions of aldehydes and ketones, is a reaction product of a) a biphenyl compound having one or more hindered 2,2'-substituted biphenyl subunits and b) an organozinc compound, such as diethylzinc. The organozinc species catalyzes the reduction of a ketone by a borane, as well as the epoxidation of .alpha.,.beta.-unsaturated compounds by an oxidizing agent, such as O.sub.2 or an alkyl hydroperoxide. The biphenyl compound may be chiral and may catalyze the formation of optically active reaction products.Type: GrantFiled: August 26, 1997Date of Patent: March 30, 1999Assignee: North Dakota State UniversityInventors: Lin Pu, Wei-Sheng Huang, Qiao-Sheng Hu
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Patent number: 5866670Abstract: A process for producing a polyacetal copolymer, which is extremely heat-stable and is extremely reduced in the quantity of unstable terminals even in a high polymerization yield in which trioxane as the principal monomer, comprises copolymerization of trioxane as the principal monomer with a cyclic ether or cyclic formal having at least one carbon-to-carbon bond as the comonomer by using a specific heteropoly-acid or acid salt thereof as a polymerization catalyst until the content of the remaining monomers is lowered to at most 10% by weight based on all the monomers fed, adding 0.01 to 10% by weight, based on the resulting crude polymer, of a solution containing a catalyst deactivator, or contacting a basic gas as the deactivator to deactivate the catalyst, and subjecting the crude polymer as such to heat melting treatment without washing thereof.Type: GrantFiled: August 15, 1996Date of Patent: February 2, 1999Assignee: Polyplastics Co., Ltd.Inventors: Akira Nakai, Kaoru Yamamoto, Eiji Masuda, Hiroyuki Kanai
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Patent number: 5844059Abstract: To prepare a thermally very stable polyacetal copolymer containing a very small amount of unstable parts in a high yield according to a simple process wherein an isopolyacid or an acid salt thereof is used as the polymerization catalyst in the copolymerization of trioxane as the principal monomer with a comonomer copolymerizable therewith, and wherein deactivation of the catalyst can be effected simply without fail through contact with a basic gas after polymerization without the necessity for any washing step. In the preparation of a polyacetal copolymer by the copolymerization of trioxane as the principal monomer with a cyclic ether or cyclic formal having at least one carbon--carbon bond as a comonomer, the copolymerization is effected using an isopolyacid or an acid salt thereof as the polymerization catalyst, followed by contact with a basic gas as a deactivator to deactivate the catalyst, and subsequent heat-melting treatment of the resulting crude polymer intact without washing thereof.Type: GrantFiled: January 27, 1997Date of Patent: December 1, 1998Assignee: Polyplastics Co., Ltd.Inventors: Kaoru Yamamoto, Hiroyuki Kanai
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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: 5763560Abstract: A method of producing styrene derivatives expressed the general formula (2) by reacting a benzaldehyde derivative expressed by the general formula (1) with dibromomethane under the existence of zinc metal as well as an active chloride for producing various types of oxystyrene which are polymerized monomers as a photoresist material used in a high density integrated circuit process from easily available materials which also can easily be handled: ##STR1## (wherein R indicates a an alkyl group, alkoxyalkyl group, an alkylcarbonyl group, an alkoxycarbonyl group, a 5 or 6-atom heterocylclic groups, or an alkylsilyl group); ##STR2## (wherein R indicates any of the same substituents as those described above.Type: GrantFiled: May 3, 1996Date of Patent: June 9, 1998Assignees: Honshu Chemical Industry Co., Ltd., Osaka Municipal GovernmentInventors: Kenzo Tsujimoto, Yoshiharu Ayabe, Fujihisa Matsunaga, Ikuzo Nishiguchi, Yoshio Ishino
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Patent number: 5728798Abstract: In preparing a polyacetal copolymer through copolymerization of trioxane as the principal monomer with a cyclic ether or cyclic formal having at least one carbon-carbon bond as the comonomer, 0.05 to 100 ppm (on the weight basis), based on the total amount of the monomers, of a heteropoly-acid or an acidic salt thereof is used as a polymerization catalyst, and a liquid mixture preliminarily prepared by mixing at least part or the whole of the comonomer with the polymerization catalyst is added to trioxane to effect copolymerization. According to such the process, the polymerization yield and the degree of polymerization (molecular weight) are enhanced, and a polyacetal copolymer having an improved stability can be obtained.Type: GrantFiled: March 7, 1997Date of Patent: March 17, 1998Assignee: Polyplastics Co., Ltd.Inventors: Akira Nakai, Kaoru Yamamoto
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Patent number: 5726276Abstract: The present invention provides a process for preparing a thermally very stable polyacetal copolymer having very small unstable terminals even at a high polymerization yield, by the copolymerization of trioxane as the principal monomer with a comonomer copolymerizable therewith, wherein an isopolyacid or an acidic salt thereof is used as a polymerization catalyst; the catalyst can simply be deactivated in a small amount of a deactivator solution after the polymerization; and a washing step is not required. The copolymerization is effected with an isopolyacid or an acidic salt thereof used as a polymerization catalyst until the remaining monomers account for at most 10% by weight of all the fed monomers, and a solution containing a deactivator for the above catalyst is added in an amount of 0.01 to 10% by weight based on the resulting crude polymer to deactivate the catalyst, followed by subjecting the crude polymer intact to a heat-melting treatment without washing it.Type: GrantFiled: October 1, 1996Date of Patent: March 10, 1998Assignee: Polyplastics Co., Ltd.Inventors: Akira Nakai, Eiji Masuda, Kaoru Yamamoto
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Patent number: 5646235Abstract: A method is provided for the preparation of tertiary polyamines by alkylating a polyamine having at least two primary amino groups without the use of excess solvent. More particularly, a tertiary amine is produced by reductively alkylating a polyamine with a carbonyl compound, such as formaldehyde, in a reaction zone while in the presence of a hydrogenation catalyst and hydrogen under reductive conditions. The carbonyl compound is continuously supplied to the reaction zone.Type: GrantFiled: June 18, 1996Date of Patent: July 8, 1997Assignee: Huntsman Petrochemical CorporationInventors: Robert LeRoy Zimmerman, Wheeler Conrad Crawford, Rodney Frederick Lloyd
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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: 5608030Abstract: Process for continuous preparation of homo- and copolyoxymethylenes with stable end groups in a homogeneous phase, in which in a tubular reactor with static mixing elements cyclic formaldehyde oligomers are polymerized in the presence of protonic acids as initiators in amounts of 0.005 to 500 ppm in a polymerization zone, in which the residence time of the reaction components in this zone is 0.1 to 10 min and in which the initiator is deactivated immediately after polymerization, there being a fluid transition between the polymerization and deactivator zones which is determined solely by the addition of deactivator, and in which, besides deactivation, stabilization of the chain ends is carried out in the presence of residual monomers, with the volatile constituents being removed from the reaction mixture in a subsequent vent unit. Stabilization is carried out in the presence of alkaline substances, either at temperatures of 150.degree. C. to 250.degree. C.Type: GrantFiled: August 15, 1994Date of Patent: March 4, 1997Assignee: Hoechst AktiengesellschaftInventors: Michael Hoffmockel, Karl-Friedrich M uck, Helmut Schlaf, Karlheinz Burg
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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: 5115083Abstract: The present invention relates to a curable composition comprising:(A) at least one aminoplast resin; and(B) an amount effective to cure the composition of at least one catalyst selected from the group consisting of(B-1) an acid, or an anhydride, ester, ammonium salt or metal salt of the acid that is represented by one of the formulae ##STR1## (B-2) an acid, or an ester, a metal salt or ammonium salt of a sulfo compound represented by the formula: ##STR2## (B-3) an acid, or an ammonium or metal salts of a reaction product prepared by the reaction of at least one amine and sulfo compound of (B-2); and mixtures thereof;where in Formulae I and IIeach R.sub.1 and R.sub.2 is independently a hydrocarbyl, hydrocarbyloxy or hydrocaryltho group;where in Formulae I, II and IIIX.sub.1 and X.sub.2 are each independently sulfur or oxygen;R.sub.3 is a divalent hydrocaryl group,each R.sub.4 and R.sub.Type: GrantFiled: April 15, 1991Date of Patent: May 19, 1992Assignee: The Lubrizol CorporationInventors: Carlos A. Piedrahita, Robert E. Quinn, John S. Perz
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Patent number: 5025085Abstract: The present invention relates to a curable composition comprising:(A) at least one aminoplast resin; and(B) an amount effective to cure the composition of at least one catalyst which is a sulfo acid, or an anhydride, ester, ammonium salt or metal salt of the acid.The sulfo acid can be exemplified by sulfonic acids, such as 2-acrylamido-2-methylpropane sulfonic acid, or a reaction product of the sulfonic acid and a phosphorus acid or salt, such as a dihydrocarbyl phosphorodithioic acid.The catalyst allows curing of aminoplast resins to be accomplished at low temperatures, while imparting a high degree of water resistance to the cured coating.Type: GrantFiled: November 6, 1989Date of Patent: June 18, 1991Assignee: The Lubrizol CorporationInventors: Carlos A. Piedrahita, Robert E. Quinn, John S. Perz
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Patent number: 4956445Abstract: Acetal polymer having a high degree of polymerization is obtained using a catalyst of a heteropoly acid or an acid salt thereof in a small amount. The catalyst is represented by formula:H.sub.x [M.sub.m .multidot.M'.sub.n O.sub.l ]yH.sub.2 O (1)whereinM: a central element constituted of at least one member selected from among P, B, Si, Ge, Sn, As, Sb, U, Mn, Re, Cu, Ni, Ti, Co, Fe, Cr, Th and Ce,M': at least one ligand element selected from among W, Mo, V and Nb, m: 1 to 10, n: 6 to 40, l: 10 to 100, x: an integer of 1 or above, and y: 0 to 50.Type: GrantFiled: December 12, 1988Date of Patent: September 11, 1990Assignee: Polyplastics Co., Ltd.Inventors: Kaoru Yamamoto, Hiroyuki Sano, Shuichi Chino
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Patent number: 4931535Abstract: Acetal polymer and copolymer are prepared by polymerizing formaldehyde or its cyclic oligomer as a principal monomer, or copolymerizing the principal monomer with a comonomer copolymerizable therewith, using an isopoly acid or an acid salt thereof as a polymerization catalyst.Type: GrantFiled: May 1, 1989Date of Patent: June 5, 1990Assignee: Polyplastics Co., Ltd.Inventors: Kaoru Yamamoto, Toshiaki Kitano, Hiroyuki Sano
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Patent number: 4904516Abstract: A process for preparing a water soluble phenol-formaldehyde resole resin having improved storage stability employs a calcium compound to catalyze the condensation reaction which occurs under basic conditions. Sulfamic acid is used to neutralize the resole solution, yielding a soluble calcium salt which will not settle out of the solution or clog transfer lines or spray nozzles as may a calcium salt precipitated during the neutralization. Glass fiber insulation produced using a binder prepared with the aqueous resole solution shows enhanced thickness recovery and lower odor potential.Type: GrantFiled: January 12, 1988Date of Patent: February 27, 1990Inventor: Albert W. Creamer
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Patent number: 4405771Abstract: There are provided metal containing polymeric coordination compounds which are prepared by a process which comprises reacting metal salts with polydentate ligand molecules obtained by the condensation of aromatic dialdehydes with .beta.-hydroxy-.alpha.,.gamma.-diamines. The above are electrical semiconductors. Such polymers containing platinum have a biological activity.Type: GrantFiled: October 16, 1981Date of Patent: September 20, 1983Assignee: Yeda Research & Development Co., Ltd.Inventor: Joseph Jagur
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Patent number: 4398034Abstract: The present invention provides a process for the preparation of low molecular weight polyesters directly from hydroxypivaldehyde. The process comprises reacting dry hydroxypivaldehyde with a diester, a multifunctional ester, a diacid, a polyester, or a mixture thereof at a temperature of about 100.degree. C. to 230.degree. C. in the presence of a transesterification catalyst. Optionally, modifying glycols, triols, or polyols may also be added. Suitable catalysts include tetraisopropyl titanate, dibutyltin oxide, lithium hydroxide, and lithium alkoxide, with tetraisopropyl titanate being especially preferred. The reaction is preferably accomplished in two stages by heating the reaction mixture to about 130.degree. C. for about three hours and subsequently heating the reaction mixture to about 190.degree.-230.degree. C. until the reaction is essentially complete.Type: GrantFiled: October 28, 1981Date of Patent: August 9, 1983Assignee: Eastman Kodak CompanyInventors: William L. Edmonson, Anthony W. McCollum
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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
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Patent number: 4133801Abstract: A process for the preparation of polyesters by reacting a di-lower alkyl ester of a dicarboxylic acid consisting mainly of terephthalic acid with an alkylene glycol consisting mainly of ethylene glycol or tetramethylene glycol and thereafter polycondensing an obtained di-glycol ester of the dicarboxylic acid and/or a low molecular weight condensate thereof, in the presence of (A) a lower alkyl p-formylbenzoate in an amount of about 50 - 1000 ppm, (B) a di-lower alkyl isophthalate in an amount of about 50 - 1000 ppm and (C) p-toluic acid and/or a mono-lower alkyl terephthalate in an amount of more than about 30 ppm, wherein the total amount of the compounds (A), (B) and (C) is not more than about 2000 ppm, to thereby form polyesters which have good qualities and excellent melt-forming properties.Type: GrantFiled: January 19, 1978Date of Patent: January 9, 1979Assignee: Teijin LimitedInventors: Yasuo Morimatsu, Toshio Tanaka, Nobuya Okumura, Takeshi Horiuchi