Plural Halo-c(=o)o- Groups Attached Indirectly To Each Other By Nonionic Bonding Patents (Class 558/281)
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Patent number: 9540461Abstract: A compound of formula CF2?CFCF2OSF5 and polymers comprising recurring units deriving from CF2?CFCF2OSF5 are disclosed as well as processes for their preparation.Type: GrantFiled: June 15, 2012Date of Patent: January 10, 2017Assignee: SOLVAY SPECIALTY POLYMERS ITALY S.P.A.Inventors: Cristiano Monzani, Vito Tortelli
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Patent number: 8344092Abstract: A dihydric phenol compound represented by the following formula (2), a phosgene compound, and an aliphatic tertiary amine are mixed together using a hydrophobic organic solvent to produce bischloroformate that is represented by the following formula (1) and has an average number of repeating units (n) of 1.99 or less. In the formulae (1) and (2), Ar is a divalent aromatic group.Type: GrantFiled: June 25, 2010Date of Patent: January 1, 2013Assignee: Idemitsu Kosan Co., Ltd.Inventors: Takaaki Hikosaka, Hideyuki Miyamoto, Hiroichi Hokari, Chikayuki Chiba, Hitoshi Takemoto
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Publication number: 20120101292Abstract: A dihydric phenol compound represented by the following formula (2), a phosgene compound, and an aliphatic tertiary amine are mixed together using a hydrophobic organic solvent to produce bischloroformate that is represented by the following formula (1) and has an average number of repeating units (n) of 1.99 or less. In the formulae (1) and (2), Ar is a divalent aromatic group.Type: ApplicationFiled: June 25, 2010Publication date: April 26, 2012Inventors: Takaaki Hikosaka, Hideyuki Miyamoto, Hiroichi Hokari, Chikayuki Chiba, Hitoshi Takemoto
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Patent number: 7297754Abstract: A method for preparing an aromatic chloroformate comprising, introducing a mixture of at least one aromatic hydroxyl compound, phosgene, at least one solvent, and at least one organic base into a flow reactor to obtain a unidirectionally flowing reaction mixture. The unidirectionally flowing reaction mixture is maintained at a temperature between about 0° C. and about 60° C. to produce a single product stream comprising an aromatic chloroformate.Type: GrantFiled: June 28, 2005Date of Patent: November 20, 2007Assignee: General Electric CompanyInventors: Gary Charles Davis, James Manio Silva, Joshua James Stone
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Patent number: 7232865Abstract: A method is provided for making siloxane polycarbonate copolymers and blends of other polycarbonates with such copolymers wherein the copolymers and blends have excellent transparency and physical characteristic.Type: GrantFiled: March 10, 2004Date of Patent: June 19, 2007Assignee: General Electric CompanyInventors: James Louis DeRudder, Niles Richard Rosenquist, Gary Charles Davis, Matthew Robert Pixton, Mark Erik Nelson, Zhaohui Su
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Patent number: 6613929Abstract: A process for the preparation of fluoroformates of the formula wherein R1 is a saturated or unsaturated, substituted or unsubstituted and primary or secondary aliphatic, a saturated or unsaturated, substituted or unsubstituted secondary cycloaliphatic or a substituted or unsubstituted aromatic or heteroaromatic, and n is equal to 1, 2 or 3, comprising reacting a corresponding chloroformate of formula I with an alkali metal fluoride in ethylene carbonate at a temperature wherein the ethylene carbonate is liquid whereby it is possible to very rapidly obtain the fluoroformates with excellent yields and high purity.Type: GrantFiled: December 18, 2002Date of Patent: September 2, 2003Assignee: IsochemInventors: Alphonse Alarcon-Lorca, Thierry Malfroot, Jean-Pierre Senet
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Patent number: 6479690Abstract: The invention concerns a method for phosgenation of monohydroxy alcohol's and/or polyols characterised in that it consists of treating alcohol and or polyol, whether in the presence of solvent or not, with a molar excess of phosgene, preferably 2 to 30 times more phosgene than the hydroxyl groups, at temperatures ranging between 0 and 200° C. and at pressure levels ranging between 2 and 60 bar, preferably in the absence of any catalyst. The method is further characterised in that pressure is further used to facilitate the separation of hydrochloric acid from phosgene, in a column external to the reactor.Type: GrantFiled: March 6, 2000Date of Patent: November 12, 2002Assignee: Societe Nationale des Poudres et ExplosifsInventors: Laurent Garel, François Metz
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Patent number: 6175017Abstract: A process for the preparation of carbonates containing aromatic ester groups is disclosed. The process entails reacting aromatic monohydroxy componds with phosgene or with chlorocarbonic acid esters of aromatic monohydroxy compounds at a temperature of 50 to 350° C. and in the presence of active carbon as catalyst.Type: GrantFiled: August 18, 1993Date of Patent: January 16, 2001Assignee: Bayer AktiengesellschaftInventors: Hans-Josef Buysch, Norbert Schön, G{umlaut over (u)}nther Jeromin
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Patent number: 5162564Abstract: Oligomeric carbonate bischloroformates are prepared with low phosgene usage by phosgenating a dihydroxyaromatic compound in an interfacial reaction in the presence of small amounts of trialkylamine, preferably, triethylamine. In this invention, the molar ratio of phosgene to dihydroxyaromatic compound, hydrolysis of phosgene, formation of such byproducts as monochloroformates and hydroxyl-terminated polycarbonate oligomers, and batch time are minimized and consumption of the dihydroxylaromatic compound is substantially complete.Type: GrantFiled: April 3, 1989Date of Patent: November 10, 1992Assignee: General Electric CompanyInventors: James M. Silva, Thomas J. Fyvie
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Patent number: 5144055Abstract: Liquid crystalline bis-chlorocarbonic acid esters are 4-hydroxybenzoic acid-(4'-hydroxyphenyl) esters corresponding to the following formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 denote, independently of one another, hydrogen, a halogen atom or a C.sub.1 to C.sub.6 alkyl group. Preparation of (I) and liquid crystalline N-alkyl polyurethanes and polycarbonates prepared from (I) are other invention embodiments.Type: GrantFiled: June 26, 1990Date of Patent: September 1, 1992Assignee: Bayer AktiengesellschaftInventors: Hanns P. Muller, Bernhard Jansen, Wolfgang Calaminus, Rolf Dhein
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Patent number: 5142088Abstract: Ester polyphenols such as the tris(bisphenol A) ester of trimellitic acid are prepared by the reaction of the corresponding aromatic poly(acyl halide) with a dihydroxyaromatic compound such as bisphenol A. They may be employed in the preparation of branched polycarbonates via chloroformate oligomer compositions.Type: GrantFiled: January 28, 1991Date of Patent: August 25, 1992Assignee: General Electric CompanyInventors: Peter D. Phelps, Eugene P. Boden, Paul W. Buckley
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Patent number: 5011966Abstract: Aromatic bischloroformates are prepared by the reaction of a dihydroxyaromatic compound such as bisphenol A with phosgene in the presence of water, base and an organic liquid such as methylene chloride. Initially, a mixture of the bisphenol, organic liquid and about 5-15% of the total base is prepared, and phosgene is passed into said mixture. The remainder of the base is added initially at a constant rate, and then only when the measured pH of the aqueous mixture is below a targeted value in the range of about 8-11 and in about 5-10% excess with respect to the phosgene then being introduced. This method minimizes hydrolysis of phosgene and formation of such by-products as monochloroformates and hydroxy-terminated polycarbonate oligomers.Type: GrantFiled: July 22, 1988Date of Patent: April 30, 1991Assignee: General Electric CompanyInventors: James M. Silva, Thomas J. Fyvie
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Patent number: 5011967Abstract: Bischloroformate oligomer compositions are prepared by passing phosgene into a heterogeneous aqueous-organic mixture containing at least one dihydroxyaromatic compound, with simultaneous introduction of a base at a rate to maintain a specific pH range and to produce a specific volume ratio of aqueous to organic phase. By this method, it is possible to employ a minimum amount of phosgene. The reaction may be conducted batchwise or continuously. The bischloroformate composition may be employed for the preparation of cyclic polycarbonate oligomers or linear polycarbonate, and linear polycarbonate formation may be integrated with bischloroformate composition formation in a batch or continuous process.Type: GrantFiled: December 4, 1987Date of Patent: April 30, 1991Assignee: General Electric CompanyInventors: James M. Silva, Robert A. Pyles
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Patent number: 4994595Abstract: Bischloroformate compositions are prepared from spirobiindane bisphenols by phosgenation in a substantially inert organic liquid in a two-step reaction. The pH during the first step is maintained in the range of about 8-14 by addition of aqueous base. In the second step, the pH is in the range of about 2-6. This method produces compositions containing a substantial amount of monomeric bischloroformate and avoids gelling problems.Type: GrantFiled: November 4, 1986Date of Patent: February 19, 1991Assignee: General Electric CompanyInventors: Daniel J. Brunelle, Thomas G. Shannon
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Patent number: 4973729Abstract: Bischloroformates of bisphenol compositions comprising hydroquinone or a hydroquinone-bisphenol A mixture are prepared by passing phosgene into a vigorously agitated mixture of water, an alkaline earth metal hydroxide, the bisphenols and a substantially inert, water-immiscible organic liquid such as methylene chloride. The molar ratio of water to alkaline earth metal hydroxide is in the range of about 3-8:1. The bisphenols and at least a portion of the organic liquid are preferably initially present in the reaction mixture, and the alkaline earth metal hydroxide is preferably added during phosgenation.Type: GrantFiled: January 19, 1989Date of Patent: November 27, 1990Assignee: General Electric CompanyInventors: Daniel J. Brunelle, David K. Bonauto
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Patent number: 4904810Abstract: Aqueous bischloroformates are prepared by the reaction of a dihydroxyaromatic compound (e.g., bisphenol A) with phosgene in a substantially inert organic liquid (e.g., methylene chloride) and in the presence of an aqueous alkali metal or alkaline earth metal base, at a pH below about 8. After all solid dihydroxyaromatic compound has been consumed, the pH is raised to a higher value in the range of about 7-12, preferably 9-11, and maintained in said range until a major proportion of the unreacted phosgene has been hydrolyzed. At the same time, any monochloroformate in the product may be converted to bischloroformate.Type: GrantFiled: July 25, 1988Date of Patent: February 27, 1990Assignee: General Electric CompanyInventors: Daniel J. Brunelle, Thomas G. Shannon
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Patent number: 4814420Abstract: A method is provided for determining the stoichiometric end point of phosgenation reactions which produce polycarbonates and chloroformates, respectively, by monitoring the rate of heat generated by the reaction mixture per unit of phosgene utilized.Type: GrantFiled: November 25, 1987Date of Patent: March 21, 1989Assignee: General Electric CompanyInventors: Daniel J. Brunelle, Thomas G. Shannon, Philip G. Kosky, Paul W. Buckley, James M. Silva
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Patent number: 4810813Abstract: A method is provided for making reaction products of phosgene and dihydric phenol under interfacial reaction conditions. The dihydric phenol such as BPA is introduced into the reactor in the form of a stable suspension which reduces phosgene hydrolysis, minimizes phosgene escape and effects improved BPA metering into the reactor.Type: GrantFiled: July 24, 1987Date of Patent: March 7, 1989Assignee: General Electric CompanyInventors: Philip G. Kosky, James M. Silva, Thomas J. Fyvie
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Patent number: 4767877Abstract: Bisamide and bisurethane bisphenols and bishaloformates are prepared by the reaction of amines with dicarboxylic acid halides or bisphenol bishaloformates. They are useful as intermediates for the preparation of cyclic heterocarbonates, which may in turn be converted to linear copolycarbonates.Type: GrantFiled: July 28, 1986Date of Patent: August 30, 1988Assignee: General Electric CompanyInventors: Thomas G. Shannon, Daniel J. Brunelle
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Patent number: 4722995Abstract: A method is provided for determining the stoichiometric end point of phosgenation reactions which produce polycarbonates and chloroformates, respectively, by monitoring the rate of heat generated by the reaction mixture per unit of phosgene utilized.Type: GrantFiled: April 25, 1986Date of Patent: February 2, 1988Assignee: General Electric CompanyInventors: Daniel J. Brunelle, Thomas G. Shannon, Philip G. Kosky, Paul W. Buckley, James M. Silva
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Patent number: 4701544Abstract: A method is provided for making reaction products of phosgene and dihydric phenol, such as bischloroformates and polycarbonates utilizing a reactor with an overhead condenser. Reduced phosgene blow-by is achieved by using an absorber for phosgene which is connected in series to the overhead condenser.Type: GrantFiled: August 4, 1986Date of Patent: October 20, 1987Assignee: General Electric CompanyInventor: James M. Silva
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Patent number: 4649210Abstract: A method is provided for reducing the reflux temperatures of methylene chloride in phosgenation reactions by introducing a second inert vaporizable component to the reaction medium. This second inert vaporizable component has a lower vaporization temperature than the methylene chloride so as to reduce the temperature of vaporization of the mixture. More efficient use of phosgene is obtained when polymerizing aromatic dihydroxy compounds to polycarbonates and higher yields of monomeric and dimeric bischloroformates are obtained.Type: GrantFiled: September 23, 1985Date of Patent: March 10, 1987Assignee: General Electric CompanyInventors: Philip G. Kosky, James M. Silva, Daniel J. Brunelle, Thomas G. Shannon
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Patent number: 4638077Abstract: Chloroformate compositions, particularly bischloroformate compositions, are prepared by the reaction of phosgene with a hydroxy compound, preferably a dihydroxy compound such as bisphenol A, in a heterogeneous mixture, while adding a hydrogen chloride scavenger comprising aqueous base as necessary and maintaining a pH of 0.5-8 during the phosgene addition. When a polyhydroxy compound is employed and the temperature is above 30.degree. C., the phosgene addition rate is maintained at a level high enough to effect rapid and complete reaction with dissolved hydroxy compound. This method uses substantially less phosgene than methods involving a higher pH.Type: GrantFiled: October 24, 1985Date of Patent: January 20, 1987Assignee: General Electric CompanyInventors: Daniel J. Brunelle, Thomas G. Shannon, Niles R. Rosenquist
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Patent number: 4614829Abstract: Process for the preparation of .alpha.-chlorinated chloroformates with the formula ##STR1## where R is H, an aliphatic or aromatic hydrocarbon radical or heterocyclic radical, substituted or non-substituted and n an integer.The process consists of reacting ClCOOCCl.sub.3 or Cl.sub.3 COCOOCCl.sub.3 with an aldehyde with formula R--(CHO).sub.n in the presence of a compound, which in the medium releases a pair of ions, the anion of which being a halide which can attack the aldehyde function, because of the weak attractive power of the cation of this compound.Type: GrantFiled: August 17, 1984Date of Patent: September 30, 1986Assignee: Societe Nationale des Poudres et ExplosifsInventors: Thierry A. Malfroot, Jean-Pierre G. Senet
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Patent number: 4601858Abstract: Bischloroformate compositions are prepared by passing gaseous phosgene into an agitated aqueous solution of a di-(alkali metal) salt of an organic dihydroxy compound such as bisphenol A, while maintaining said solution at a temperature within the range of about 0.degree.-50.degree. C. Phosgene passage and agitation are continued until the bischloroformate composition has precipitated. The reaction is typically complete when the pH of the aqueous phase drops below 7.Type: GrantFiled: June 13, 1985Date of Patent: July 22, 1986Assignee: General Electric CompanyInventors: Thomas G. Shannon, Daniel J. Brunelle
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Patent number: 4592874Abstract: Process for the synthesis of .alpha.-chlorinated chloroformates, and new .alpha.-chlorinated chloroformates.The invention relates to a new process for the manufacture of .alpha.-chlorinated chloroformates and, to new .alpha.-chlorinated chloroformates as new industrial products.The process according to the invention consists of a synthesis, by catalytic phosgenation, of .alpha.-chlorinated chloroformates of the formula: ##STR1## in which: R represents a substituted or unsubstituted hydrocarbon radical and m represents an integer superior or equal to one, this synthesis consisting in reacting phosgene with the aldehyde R--CHO).sub.m, in the presence of a catalyst which is an organic or inorganic substance which is capable in a medium containing an aldehyde of the formula R--CHO).sub.Type: GrantFiled: May 6, 1981Date of Patent: June 3, 1986Assignee: Societe Nationale des Poudres et ExplosifsInventors: Guy C. Cagnon, Marc D. Piteau, Jean-Pierre G. Senet, Roy A. Olofson, Jonathan T. Martz
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Patent number: 4592872Abstract: Process for the synthesis of .alpha.-chlorinated chloroformates, and new .alpha.-chlorinated chloroformates.The invention relates to a new process for the manufacture of .alpha.-chlorinated chloroformates and, to new .alpha.-chlorinated chloroformates as new industrial products.The process according to the invention consists of a synthesis, by catalytic phosgenation, of .alpha.-chlorinated chloroformates of the formula: ##STR1## in which: R represents a substituted or unsubstituted hydrocarbon radical and m represents an integer superior or equal to one, this synthesis consisting in reacting phosgene with the aldehyde R--CHO).sub.m, in the presence of a catalyst which is an organic or inorganic substance which is capable in a medium containing an aldehyde of the formula R--CHO).sub.Type: GrantFiled: January 22, 1982Date of Patent: June 3, 1986Assignee: Societe Nationale des Poudres et ExplosifsInventors: Guy C. Cagnon, Marc D. Piteau, Jean-Pierre G. Senet, Roy A. Olofson, Jonathan T. Martz