Plural Chalcogens Bonded Directly To Ring Carbons Of Each Of The Two Five Membered Hetero Rings (e.g., Bisphthalimides, Etc.) Patents (Class 548/461)
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Patent number: 5252730Abstract: A polymer composition having intense magnetic properties and a method for preparation of same. A phthalimide compound and an aromatic dialiphatic acid are reacted in the presence of a metal catalyst at elevated temperatures to form a phenylenebis diphthalimidine compound. The phenylenebis diphthalimidine compound is then reacted with 3-benzylidine phthalimidine and a metal salt of an aliphatic acid at elevated temperatures under an inert gas to form the intensely magnetic polymer. The reactions may be carried out in the presence of a solvent.Type: GrantFiled: April 10, 1992Date of Patent: October 12, 1993Assignee: Northrop CorporationInventor: Jack D. Mackey
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Patent number: 5252536Abstract: Substituted indolinone compounds which are effective in the control of undesirable plant species are described. Also described are a method for the herbicidal use of the compounds and a method for their preparation.Type: GrantFiled: December 31, 1991Date of Patent: October 12, 1993Assignee: American Cyanamid CompanyInventors: Michael E. Condon, Gary M. Karp
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Patent number: 5229484Abstract: An N-substituted polyamide-imide essentially composed of identical or different repeating units of the formula I ##STR1## where R.sup.1 is one of the following tetravalent aromatic radicals ##STR2## and X is a bond or one of the following linkers ##STR3## where R.sup.2 and R.sup.4 are each, independently of one another, one of the following divalent aromatic radicals ##STR4## and where X has the abovementioned meanings and where R.sup.3 is hydrogen or a monovalent radical such as C.sub.1 -C.sub.6 -alkyl or phenyl, and the C.sub.1 -C.sub.6 -alkyl-, C.sub.1 -C.sub.6 -alkoxy-, aryl- or halogen-substituted derivatives thereof, and precursors (monomers) therefor, are described.Type: GrantFiled: January 17, 1992Date of Patent: July 20, 1993Assignee: BASF AktiengesellschaftInventors: Peter Wolf, Juergen Koch
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Patent number: 5208346Abstract: Method of preparing aromatic bisimides by effecting a reaction between a 3-substituted N-arylphthalimide and an aromatic dihydroxy dianion compound by refluxing in a non-polar organic solvent. Advantageously, the method eliminates the need for using a phase transfer catalyst or a dipolar aprotic solvent.Type: GrantFiled: March 16, 1992Date of Patent: May 4, 1993Assignee: General Electric CompanyInventor: Brent A. Dellacoletta
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Patent number: 5185451Abstract: Bis-imides of dioxydiphthalic or oxydiphthalic anhydride, are characterized by the formula ##STR1## where Z is H, alkyl of 1-12 carbon atoms, or ##STR2## A is H, Cl, F, NO.sub.2, OH, CF.sub.3, alkyl, alkoxy, alkylaryl or aryloxy, wherein the alkyl groups are 1-6 carbon atoms and the aryl groups are 6-14 carbon atoms; alkenyl or alkynyl of 2-6 carbon atoms; or benzoyl; and Y is H, Cl, F, NO.sub.2, OH, or CF.sub.3 ; X is halogen; X' is hydrogen or halogen; or X and X' together represent an oxygen atom, forming a second ether linkage.Type: GrantFiled: October 4, 1991Date of Patent: February 9, 1993Assignee: Occidental Chemical CorporationInventors: Jeffrey S. Stults, Willis T. Schwartz, Frank J. Dinan
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Patent number: 5175304Abstract: Polyetherimide oligomers having crosslinking end cap moieties which provide improved solvent-resistance to cured composites are generally represented by the formula: ##STR1## wherein X=--O-- or --S--; ##STR2## n=1 or 2; ##STR3## E=allyl or methallyl; R=a trivalent C.sub.(6-13) aromatic organic radical;R.sub.1 =any of lower alkyl, lower alkoxy, aryl, or substituted aryl;R'=a divalent C.sub.(6-30) aromatic organic radical;j=0, 1, or 2; andG=--CH.sub.2 --, --O--, --S--, or --SO.sub.2 --Blends generally comprise substantially equimolar amounts of the oligomers and a comparable, compatible, noncrosslinking, etherimide polymer of substantially the same backbone. The crosslinkable oligomers are made by reacting substituted phthalic anhydrides with hydroxyaryl amines and suitable crosslinking end cap reactants, or by self-condensation of phthalimide salts followed by capping the polymers.Type: GrantFiled: May 10, 1990Date of Patent: December 29, 1992Assignee: The Boeing CompanyInventors: Clyde H. Sheppard, Hyman R. Lubowitz
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Patent number: 5175305Abstract: This invention relates to a process for preparing and treating a product predominant in N,N'-bis(tetrabromophthalimide) so as to produce a bisimide product which has enhanced suitability for use in thermoplastic formulations as a result of reduction in volatile impurities and particle size.Type: GrantFiled: August 12, 1991Date of Patent: December 29, 1992Assignee: Ethyl CorporationInventors: Joseph W. Roos, Robert M. Moore, Jr.
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Patent number: 5151487Abstract: Solvent resistance in polyimide, polyamide, and other resins can be improved by capping these resing with mono- or difunctional crosslinking end caps. Imidophenylamines of the general formula: ##STR1## R.sub.1 =lower alkyl, lower alkoxy, aryl, aryloxy, substituted alkyl, substituted aryl, halogen, or mixtures thereof;Me=methyl;T=allyl or methallyl;i=1 or 2;j=0, 1 or 2; andG=--CH.sub.2 --, --O--, --S--, or --SO.sub.2 --.comprise a new family of end cap monomers that are reactants in the synthesis of crosslinking, solvent resistant oligomers.Type: GrantFiled: November 26, 1991Date of Patent: September 29, 1992Assignee: The Boeing CompanyInventors: Hyman R. Lubowitz, Clyde H. Sheppard
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Patent number: 5137948Abstract: The invention relates to the preparation of halogenated imides derived from hydrazine and halogenated dicarboxylic acid anhydride and which can be used as flameproofing agents for plastics. The condensation of hydrazine and halogenated dicarboxylic acid anhydride is carried out in an aqueous medium, at a temperature ranging from 40.degree. to 225.degree. C., with a molar ratio of anhydride/hydrazine equal to between 0.5 and 3, preferably between 1 and 2.Type: GrantFiled: July 22, 1988Date of Patent: August 11, 1992Assignee: AtochemInventors: Evelyne Bonnet, Andre Gagnieur, Bernard Gurtner
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Patent number: 5136047Abstract: This invention relates to a process for preparing a white flame retardant product which principally contains a bisimide. The process comprises: providing an essentially water-free solution containing tetrabromophthalic anhydride and a solvent in a reaction vessel; forming a reaction mass by adding a diamine or a diamine salt to the solution at an addition rate such that, at the addition temperature, water formed during the addition is removed from the reaction mass substantially as it is formed; terminating the addition of the diamine when the molar ratio of the tetrabromophthalic anhydride initially present in the solution to the diamine or diamine salt added is at least about 2.00:1; maintaining the reaction mass at a temperature of at least 125.degree. C. for at least 0.5 hr after the addition; and recover from the reaction mass the flame retardant product.Type: GrantFiled: February 19, 1991Date of Patent: August 4, 1992Assignee: Ethyl CorporationInventors: Mo A. Khuddus, David R. Brackenridge
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Patent number: 5110986Abstract: This application relates to a process for preparing a N-t-alkyl-1,2-diacylhydrazine by reacting a 1,3,4-oxadiazole with a tertiary alkyl cation precursor in the presence of a strong acid catalyst. Preferably, the 1,3,4-oxadiazole is a 2,5-disubstituted-1,3,4-oxadiazole and more preferably a 2,5-diaryl-1,3,4-oxadiazole. The strong acid catalyst is preferably a sulfur containing acid and more preferably sulfuric acid.Type: GrantFiled: April 26, 1988Date of Patent: May 5, 1992Assignee: Rohm and Haas CompanyInventor: Martha J. Kelly
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Patent number: 5097034Abstract: Color formers of the formula ##STR1## in which X.sup.1 denotes hydroxyl, alkoxy, alkenyloxy, aralkoxy, cycloalkoxy, aryloxy or acyloxy,R.sup.1 denotes hydrogen, halogen, alkyl or alkoxy,R.sup.2 denotes hydrogen, alkoxy, aralkoxy, aryloxy or a radical of the formula ##STR2## Y.sup.1 and Y.sup.2, independently of one another, denote alkyl, cycloalkyl or aralkyl,R.sup.2 can form a heterocyclic ring with A in the o-position, in which a benzene ring can be additionally fused onto ring A in the o-/m-position with respect to R.sup.2,R.sup.3 denotes hydrogen, alkyl, alkenyl, aralkyl, cycloalkyl or aryl, or R.sup.3 is linked to ring B in the o-position with respect to the nitrogen,Z.sup.1 stands for the remaining members of a partially hydrogenated or completely hydrogenated ring, with the proviso that Z.sup.Type: GrantFiled: May 14, 1991Date of Patent: March 17, 1992Assignee: Bayer AktiengesellschaftInventor: Udo Eckstein
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Patent number: 5087701Abstract: Solvent resistance in polyimide, polyamide, and other resins can be improved by capping these resins with mono- or difunctional crosslinking end caps. Imidophenylamines of the general formula: ##STR1## R.sub.1 =lower alkyl, lower alkoxy, aryl, aryloxy, substituted alkyl, substituted aryl, halogen, or mixtures thereof;Me=methyl;T=allyl or methallyl;i=1 or 2;j=0, 1, or 2; andG=--CH.sub.2 --, --O--, --S--, or --SO.sub.2 --,comprise a new family of end cap monomers that are reactants in the synthesis of crosslinking, solvent resistant oligomers.Type: GrantFiled: March 5, 1990Date of Patent: February 11, 1992Assignee: The Boeing CompanyInventors: Hyman R. Lubowitz, Clyde H. Sheppard
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Patent number: 5076970Abstract: This invention relates to a process for preparing and treating a product predominant in N,N'-bis(tetrabromophthalimide) so as to produce a bisimide product which has enhanced suitability for use in thermoplastic formulations as a result of reduction in volatile impurities and particle size.Type: GrantFiled: May 29, 1990Date of Patent: December 31, 1991Assignee: Ethyl CorporationInventors: Joseph W. Roos, Robert M. Moore, Jr.
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Patent number: 5070163Abstract: Compounds of the formula I ##STR1## in which a is 1, 2 or 3, b is 0, 1, or 2, R.sup.1 and R.sup.2, independently of one another are hydrogen or methyl, R.sup.3 is C.sub.1 -C.sub.6 alkyl, R.sup.4 is selected from the group consisting of the formulas IIa, IIb, IIc, IId, IIe or IIf ##STR2## X is --O--, --S--, --CO--, --COO--, --CO--NR.sup.5 -- or --CR.sup.6 R.sup.7 --, Z.sup.1 is --CR.sup.6 R.sup.7 --, Z.sup.2 is --SO.sub.2 -- or --CO--, Y is a direct C--C bond, --O--, --S--, --SO--, --SO.sub.2 --, --CO--, --P(O)R.sup.9 --, --COO--, --CO--NR.sup.5 --, --C.sub.n H.sub.2n -- or --CR.sup.10 R.sup.11 --, n is an integer from 1 to 12, R.sup.5 is hydrogen or C.sub.1 -C.sub.6 alkyl, R.sup.6 and R.sup.7, independently of one another, are hydrogen, or C.sub.1 -C.sub.6 alkyl, --CF.sub.3, cyclohexyl or phenyl, or R.sup.6 and R.sup.7 together with the common C atom are a cycloalkylidene radical having 5 to 7 ring carbon atoms, R.sup.8 is C.sub.1 -C.sub.6 alkyl, chlorine or bromine, R.sup.Type: GrantFiled: August 31, 1989Date of Patent: December 3, 1991Assignee: Ciba-Geigy CorporationInventors: Friedrich Stockinger, Andreas Kramer
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Patent number: 5068352Abstract: Liquid crystalline polyesteretherimides are prepared by a transesterification reaction involving terephthalic acid and acylated derivatives of 4-hydroxybenzoic acid and of certain bisimidodiphenols, or from the free bisimidodiphenol and aryl esters of the acids. In addition to being liquid crystalline, the polyesterethermides are crystalline in the solid state and have relatively high glass transition temperatures.Type: GrantFiled: October 31, 1990Date of Patent: November 26, 1991Assignee: General Electric CompanyInventors: David N. Schissel, Deborah A. Haitko
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Patent number: 5068353Abstract: Aromatic bis(ether phthalimide) compounds of the formula (I): ##STR1## are synthesized by reacting a phthalimide of the formula (II): ##STR2## with a stoichiometric excess of an alkali metal diphenoxide salt of the formula (III):M--O--R.sub.2 --O--M (III)in the presence of a catalytic amount of a phase transfer catalyst, in a anhydrous nonpolar organic solvent under ether-forming conditions. Impurities are removed by solid-liquid separation techniques, such as filtering at a temperature at which the compound of formula (I) is substantially completely soluble while alkali metal salt impurities are substantially insoluble. The compound of formula (I) is recovered from the filtrate in high yields and at high purity.Type: GrantFiled: December 31, 1986Date of Patent: November 26, 1991Assignee: General Electric CompanyInventor: Brent A. Dellacoletta
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Patent number: 5049601Abstract: This invention relates to a process for enhancing the properties of alkylene(C.sub.1 -C.sub.6)-bis-(tetrabromophthalimide) or bis-(tetrabromophthalimide) produced by the bromination, respectively, of alkylene(C.sub.1 -C.sub.6)-bis-(phthalimide) or bis-(phthalimide) with a brominating agent in the presence of oleum, the process comprising curing the alkylene(C.sub.1 -C.sub.6)bis-(tetrabromophthalimide) or bis-(tetrabromophthalimide) at a temperature above about 150.degree. C. and below the melting point of the tetrabromophthalimide being cured for a period of from about 36 hours to about 5 hours. This enhanced product and its use in molding and extrusion compositions and in molded and extruded articles is also disclosed.Type: GrantFiled: July 24, 1989Date of Patent: September 17, 1991Assignee: Ethyl CorporationInventor: Mo A. Khuddus
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Patent number: 5037847Abstract: Novel 3-aryl-4-cyanopyrrole derivatives of the general formula ##STR1## wherein R.sub.1 and R.sub.2 are each independently of the other unsubstituted or halogen-substituted alkyl, halogen, nitro or hydrogen, or R.sub.1 and R.sub.2, when taken together, are --OCF.sub.2 O,R.sub.3 is alkyl, cycloalkyl or benzyl, andR.sub.4 is hydrogen or an alkali metal or alkaline earth metal.The novel compounds are used for controlling harmful microorganisms, in particular phytopathogenic fungi. They can be used together with suitable formulation assistants as compositions, and are also suitable for preventing infestation of cultivated plants by harmful microorganisms.Type: GrantFiled: March 6, 1990Date of Patent: August 6, 1991Assignee: Ciba-Geigy CorporationInventor: Marius Sutter
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Patent number: 5034540Abstract: Liquid crystalline polyesteretherimides are prepared by a transesterification reaction involving hydroquinone, 4,4'-biphenol or 2,6-dihydroxynaphthalene and esters of certain bisimidodicarboxylic acids, or from the free bisimidodicarboxylic acids and esters of the dihydroxyaromatic compounds. In addition to being liquid crystalline, the polyesteretherimides are crystalline in the solid state and have relatively high glass transition temperatures.Type: GrantFiled: September 17, 1990Date of Patent: July 23, 1991Assignee: General Electric CompanyInventors: Deborah A. Haitko, David N. Schissel
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Patent number: 5013848Abstract: A novel aromatic bismaleimide of the formula (I): ##STR1## wherein X is ##STR2## where R.sub.1 R.sub.2, R.sub.3 and R.sub.4 are a hydrogen atom or a methyl group. The bismaleimide is prepared by reacting an aromatic diamine having the formula (II): ##STR3## wherein X is the same as in the formula (I), with maleic anhydride and then conducting the ring-closing reaction of the resultant aromatic bismaleamic acid.Type: GrantFiled: July 22, 1987Date of Patent: May 7, 1991Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Yukihiro Yoshikawa, Midori Yamazaki, Keizaburo Yamaguchi, Kenichi Sugimoto, Yoshimitsu Tanabe, Akihiro Yamaguchi
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Patent number: 5003078Abstract: Imide-containing phthalonitrile monomers are prepared from a phthalonitrile and an aromatic dianhydride. The monomer and a method for preparing the monomer is disclosed. These monomers are synthesized into heat resistant polymers and copolymers with aromatic ring structure incorporating imide and ether linkages. The synthesis of the high temperature thermosetting polymers and copolymers is also disclosed.Type: GrantFiled: May 16, 1989Date of Patent: March 26, 1991Assignee: The United States of America as represented by the Secretary of the NavyInventor: Teddy M. Keller
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Patent number: 4997953Abstract: This invention concerns a process for producing N,N'-bis(tetrabromophthalimide) by: forming a reaction mass from at least (i) tetrabromophthalic anhydride, (ii) hydrazine or a hydrazine provider compound, and (iii) concentrated sulfuric acid; and maintaining the so-formed reaction mass at a temperature within the range of from about 100.degree. C. to about 300.degree. C. for a period up to about 20 hours.Type: GrantFiled: October 23, 1989Date of Patent: March 5, 1991Assignee: Ethyl CorporationInventor: Michael G. McKenna
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Patent number: 4994580Abstract: 3,3'-Thiobis(2,5-dihydrothiophene-1,1-dioxides) on heating with a reactive Diels-Alder dienophile undergo a reaction producing thioethers having two six-membered alicyclic rings in the molecule, such as 4,4'-thiobis(3,6-dihydrophthalic acids) or the esters, anhydrides or imides thereof, and 4,4'-thiobis(1,2,3,6-tetrahydrophthalic acids) or the esters, anhydrides or imides thereof. Both rings of the dihydrothiophene dioxides participate in the reaction, apparently by forming a tetraene structure which co-reacts with two equivalents of the dienophile to form an adduct in which each six-membered ring has one or two olefinic double bonds. During the course of the reaction, the thioether bridge remains intact. Some of the bis(alicyclic) thioethers are readily converted to the corresponding bis(aromatic)thioethers by use of known aromatization methods and systems. Various utilities for the products of the foregoing reactions are described.Type: GrantFiled: October 26, 1989Date of Patent: February 19, 1991Assignee: Ethyl CorporationInventor: G. Patrick Stahly
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Patent number: 4994579Abstract: The new aromatic ether imides corresponding to the following formula ##STR1## may be used for the production of plastics which in turn may be worked up into moulded articles, films, sheet products and filaments. The plastics produced from the new aromatic ether imides are distinguished by their exceptional dimensional stability under heat.Type: GrantFiled: October 4, 1989Date of Patent: February 19, 1991Assignee: Bayer AktiengesellschaftInventors: Knud Reuter, Dieter Freitag, Gunther Weymans, Rolf Dhein
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Patent number: 4988792Abstract: Liquid crystalline polyesteretherimides are prepared by a transesterification reaction involving terephthalic acid and acylated derivatives of 4-hydroxybenzoic acid and of certain bisimidodiphenols, or from the free bisimidodiphenol and aryl esters of the acids. In addition to being liquid crystalline, the polyesteretherimides are crystalline in the solid state and have relatively high glass transition temperatures.Type: GrantFiled: January 19, 1990Date of Patent: January 29, 1991Assignee: General Electric CompanyInventors: David N. Schissel, Deborah A. Haitko
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Patent number: 4988821Abstract: Liquid crystalline polyesteretherimides are prepared by a transesterification reaction involving hydroquinone, 4,4'-biphenol or 2,6-dihydroxynaphthalene and esters of certain bisimidodicarboxylic acids, or from the free bisimidodicarboxylic acids and esters of the dihydroxyaromatic compounds. In addition to being liquid crystalline, the polyesteretherimides are crystalline in the solid state and have relatively high glass transition temperatures.Type: GrantFiled: August 23, 1989Date of Patent: January 29, 1991Assignee: General Electric CompanyInventors: Deborah A. Haitko, David N. Schissel
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Patent number: 4985568Abstract: Solvent resistance in polyimide, polyamide, and other resins can be improved by capping these resing with mono- or difunctional crosslinking end caps. Imidophenylamines of the general formula: ##STR1## R.sub.1 =lower alkyl, lower alkoxy, aryl, aryloxy, substituted alkyl, substituted aryl, halogen, or mixtures thereof;Me=methyl;T=allyl or methallyl;i=1 or 2;j=0, 1, or 2; andG=--CH.sub.2 --, --O--, --S--, or --SO.sub.2 --.comprise a new family of end cap monomers that are reactants in the synthesis of crosslinking, solvent resistant oligomers. The imidophenylamines are prepared by reacting the corresponding acid halide with ammonia to form an amic acid and rearranging the amic acid to the amine.Type: GrantFiled: April 28, 1989Date of Patent: January 15, 1991Assignee: The Boeing CompanyInventors: Hyman R. Lubowitz, Clyde H. Sheppard
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Patent number: 4973707Abstract: Polyimides made by reacting 1,2-acetylene-4,4'-di(phthalic anhydride) with an aromatic diamine are useful in high temperature applications that require solvent resistance. Applications include components of combustion engines.Type: GrantFiled: July 31, 1989Date of Patent: November 27, 1990Assignee: General Electric CompanyInventor: Susan A. Nye
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Patent number: 4960903Abstract: An aromatic compound having sulfonyl groups, as an intermediate or raw material of polyimides having a good and well-balanced heat resistance and moldability is effectively produced by reacting a compound represented by the general formula,R--Ar--Rwherein Ar is ##STR1## Y is a bond, oxygen atom, sulfur atom, SO.sub.2, CH.sub.2 or ##STR2## and R is a hydrogen atom or --SO.sub.2 X and X is a halogen atom or alkali metal, with a compound represented by the following general formula, ##STR3## wherein X.sup.1 and X.sup.2 are simultaneously methyl groups or form ##STR4## and Z is a hydrogen atom, alkyl group having 1 to 6 carbon atoms or aryl group having 6 to 8 carbon atoms and R.sup.1 is a hydrogen atom, --SO.sub.2 X, halogen atom or nitro group, X is a halogen atom or alkali metal and R and R.sup.1 are not same simultaneously, either of which contains --SO.sub.2 X group as a necessary group.Type: GrantFiled: December 8, 1986Date of Patent: October 2, 1990Assignee: Toa Nenryo Kogyo Kabushiki KaishaInventors: Yoshio Taguchi, Chichiro Imai, Yoshio Imai
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Patent number: 4945168Abstract: Aryl-(1-phthalimido)-alkyl ketones of the general formula ##STR1## are prepared by reacting a suitable aromatic compound with ##STR2## at least one hydrogen atom on the aromatic nucleus in an inert solvent and in the presence of iron-(III)-chloride with an N-phthaloyl-2-amino carboxylic acid chloride of the general formula ##STR3## They can be converted into corresponding 2-phenethanolamines or 2-phenethylamines by reduction of the keto group.Type: GrantFiled: August 22, 1988Date of Patent: July 31, 1990Assignee: Degussa AktiengesellschaftInventors: Franz Effenberger, Dieter Steegmuller
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Patent number: 4935523Abstract: Solvent resistance in polyimide, polyamide, and other resins can be improved by capping these resing with mono- or difunctional crosslinking end caps. Imidophenylamines of the general formula: ##STR1## wherein Y= ##STR2## R.sub.1 =lower alkyl, lower alkoxy, aryl, aryloxy, substituted alkyl, substituted aryl, halogen, or mixtures thereof;Me=methyl;T=allyl or methallyl;i=1 or 2;j=0, 1, or 2; andG=--CH.sub.2 --, --O--, --S--, or --SO.sub.2 --.comprise a new family of end cap monomers that are reactants in the synthesis of crosslinking, solvent resistant oligomers.Type: GrantFiled: May 4, 1987Date of Patent: June 19, 1990Assignee: The Boeing CompanyInventors: Hyman R. Lubowitz, Clyde H. Sheppard
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Patent number: 4933469Abstract: A method is provided for preparing oxybisphthalimides by heating a nitrophthalimide compound in the presence of an alkali metal carboxylate, a phase transfer catalyst and a nonpolar organic solvent.Type: GrantFiled: December 16, 1988Date of Patent: June 12, 1990Assignee: General Electric CompanyInventors: Donald R. Berdahl, Pamela A. Matsch, Susan A. Nye
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Patent number: 4916235Abstract: Resins are prepared by Diels-Alder polymerization of compounds of the formula ##STR1## where R is a divalent linking group.Type: GrantFiled: November 26, 1986Date of Patent: April 10, 1990Assignee: University of DaytonInventors: Loon-Seng Tan, Fred E. Arnold
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Patent number: 4914212Abstract: This invention relates to a process for preparing a white flame retardant product which principally contains a bisimide. The process comprises: providing an essentially water-free solution containing tetrabromophthalic anhydride and a solvent in a reaction vessel; forming a reaction mass by adding a diamine or a diamine salt to the solution at an addition rate such that, at the addition temperature, water formed during the addition is removed from the reaction mass substantially as it is formed; terminating the addition of the diamine when the molar ratio of the tetrabromophthalic anhydride initially present in the solution to the diamine or diamine salt added is at least about 2.00:1; maintaining the reaction mass at a temperature of at least 125.degree. C. for at least 0.5 hr after the addition; and recovering from the reaction mass the flame retardant product.Type: GrantFiled: June 23, 1988Date of Patent: April 3, 1990Assignee: Ethyl CorporationInventors: Mo A. Khuddus, David R. Brackenridge
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Patent number: 4866184Abstract: 3,3'-Thiobis(2,5-dihydrothiophene-1,1-dioxides) on heating with a reactive Diels-Alder dienophile undergo a reaction producing thioethers having two six-membered alicyclic rings in the molecule, such as 4,4'-thiobis(3,6-dihydrophthalic acids) or the esters, anhydrides or imides thereof, and 4,4'-thiobis(1,2,3,6-tetrahydrophthalic acids) or the esters, anhydrides or imides thereof. Both rings of the dihydrothiophene dioxides participate in the reaction, apparently by forming a tetraene structure which co-reacts with two equivalents of the dienophile to form an adduct in which each six-membered ring has one or two olefinic double bonds. During the course of the reaction, the thioether bridge remains intact. Some of the bis(alicyclic) thioethers are readily converted to the corresponding bis(aromatic)thioethers by use of known aromatization methods and systems. Various utilities for the products of the foregoing reactions are described.Type: GrantFiled: May 23, 1988Date of Patent: September 12, 1989Assignee: Ethyl CorporationInventor: G. Patrick Stahly
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Patent number: 4798900Abstract: 3,3'-Thiobis(2,5-dihydrothiophene-1,1-dioxides) on heating with a reactive Diels-Alder dienophile undergo a reaction producing thioethers having two six-membered alicyclic rings in the molecule, such as 4,4'-thiobis(3,6-dihydrophthalic acids) or the esters, anhydrides or imides thereof, and 4,4'-thiobis(1,2,3,6-tetrahydrophthalic acids) or the esters, anhydrides or imides thereof. Both rings of the dihydrothiophene dioxides participate in the reaction, apparently by forming a tetraene structure which co-reacts with two equivalents of the dienophile to form an adduct in which each six-membered ring has one or two olefinic double bonds. During the course of the reaction, the thioether bridge remains intact. Some of the bis(alicyclic) thioethers are readily converted to the corresponding bis(aromatic)thioethers by use of known aromatization methods and systems. Various utilities for the products of the foregoing reactions are described.Type: GrantFiled: October 10, 1986Date of Patent: January 17, 1989Assignee: Ethyl CorporationInventor: G. Patrick Stahly
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Patent number: 4780544Abstract: A method is provided for making oxybisphthalimides by heating an N-organonitrophthalimide in the presence of an aprotic organic solvent in an alkali metal carboxylate.Type: GrantFiled: July 2, 1986Date of Patent: October 25, 1988Assignee: General Electric CompanyInventor: Donald R. Berdahl
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Patent number: 4757149Abstract: Bis(N-substituted phthalimide)ethers are synthesized in a one-step process by heating a compound of the formula (I): ##STR1## with a catalytic amount of an alkali or alkaline earth metal carbonate in a polar aprotic solvent under ether-forming conditions, and recovering the bis(N-substituted phthalimide)ether from the reaction mixture. R.sub.1 is hydrogen; a monovalent organic radical selected from a lower alkyl group having from 1 to about 10 carbon atoms, preferably from 1 to about 5 carbon atoms; or an aromatic hydrocarbon radical, or halogenated derivative thereof, having from about 6 to about 20 carbon atoms. X is a leaving group.Type: GrantFiled: December 31, 1986Date of Patent: July 12, 1988Assignee: General Electric CompanyInventor: Louis M. Maresca
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Patent number: 4757150Abstract: Polyetherimide bisphenols and bischloroformates are prepared by the reaction of dianhydrides or certain bisimides with aminophenols or mixtures thereof with diamines. They are useful as intermediates for the preparation of cyclic heterocarbonates, which may in turn be converted to linear copolycarbonates. The bisphenols can also be converted to salts which react with cyclic polycarbonate oligomers to form block copolyetherimidecarbonates.Type: GrantFiled: July 31, 1986Date of Patent: July 12, 1988Assignee: General Electric CompanyInventors: Thomas L. Guggenheim, Joseph W. Guiles, John W. Verbicky, Jr.
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Patent number: 4711964Abstract: Resins are prepared by polymerization of compounds of the formula ##STR1## where R is a divalent linking group. Blends of a compound of the formula (I) as defined above and a bis-maleimide of the formula ##STR2## where Ar' is an aromatic linking group.Type: GrantFiled: May 8, 1986Date of Patent: December 8, 1987Assignee: University of DaytonInventors: Loon-Seng Tan, Fred E. Arnold
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Patent number: 4681949Abstract: Novel bis-aminopyridinium salts are useful as phase transfer catalysts in the preparation of aromatic ethers by the reaction of hydroxyaromatic compound alkali metal salts (e.g., bisphenol A disodium salt) with activated halo- or nitro-substituted aromatic compounds (e.g., 4-nitro-N-methylphthalimide). The bis-aminopyridinium salts may be prepared by the reaction of aminopyridines with bis-carbonium ion-generating compounds such as dibromoalkanes.Type: GrantFiled: April 30, 1986Date of Patent: July 21, 1987Assignee: General Electric CompanyInventor: Daniel J. Brunelle
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Patent number: 4636575Abstract: Compounds of formula II and X ##STR1## wherein X is O, S, SO.sub.2, methylene, isopropylidene or NCOR.sub.7 where R.sub.7 is alkyl or phenyl, Y is a direct bond or methylene, n is 1 or 2, R.sub.4 is alkyl, phenyl, naphthyl, cycloalkyl, aralkyl, camphoryl, CF.sub.3, CCl.sub.3, F or NH.sub.2 ; or is alkylene, phenylene or naphthylene, R.sub.5 is hydrogen or halogen, R.sub.6 is hydrogen, alkyl, phenyl or cyano, R.sub.8 is substituted phenyl, substituted naphthyl, anthryl or phenanthryl, R.sub.9 is alkyl R.sub.10 is alkyl or substituted phenyl, and R.sub.11 is alkyl, substituted phenyl, naphthyl, camphoryl, alkylene, phenylene or naphthylene, are latent curing catalysts for acid-curable stoving lacquers. They are distinguished by satisfactory solubility in the acid-curable resin systems, can be stored virtually indefinitely in the dark and, when exposed to shortwave light, make it possible to cure the resins by acid catalysts at a relatively low temperature.Type: GrantFiled: December 17, 1984Date of Patent: January 13, 1987Assignee: Ciba-Geigy CorporationInventor: Rudolf Kirchmayr
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Patent number: 4625037Abstract: A method is provided for making thioether-(bisphthalimide)s from an alkali metal hydrogen sulfide and an N-organo substituted halophthalimide or nitrophthalimide.Type: GrantFiled: February 2, 1984Date of Patent: November 25, 1986Assignee: General Electric CompanyInventor: Thomas L. Evans
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Patent number: 4623732Abstract: Compounds which are bis-(N-alkylphthalimides) are prepared by a new process in which a halogen-containing precursor is heated in the presence of a nickel compound, a reducing agent, for example, metallic zinc, and an organic solvent. The resulting compound is useful in a process for the preparation of a copolymer, in which the compound is reacted with alkali to form a tetraacid, the acid is dehydrated to form a dianhydride, and the dianhydride is reacted with a second dianhydride and a diamine under copolymer-forming conditions.Type: GrantFiled: November 18, 1983Date of Patent: November 18, 1986Assignee: General Electric CompanyInventor: Edward N. Peters
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Patent number: 4609741Abstract: Novel phthalic acid derivatives are described which are substituted by 2-propynyloxy groups, of the formula I ##STR1## in which Q.sub.1, and Q.sub.2 independently of one another are --OH or --O.sup.- M.sup.+, or Q.sub.1 and Q.sub.2 together form the grouping --O--, [O.sup.- ].sub.2 M.sub.1.sup.++ or --N(R.sub.2)--, M.sup.+ is an alkali metal ion, a trialkyl ammonium ion having 3-24 carbon atoms or a quaternary ammonium ion and M.sub.1.sup.++ is an alkaline earth metal ion, R.sub.2 is an alkyl group or an unsubstituted or substituted aryl group, n is 1 or 2 and R.sub.1 is hydrogen, if n is 1, or a direct bond, if n is 2, are described. The phthalic anhydrides which are substituted by 2-propynyloxy, of the formula I, can be used for curing epoxy resins, cured products with outstanding physical properties being obtained.Type: GrantFiled: August 9, 1984Date of Patent: September 2, 1986Assignee: Ciba-Geigy CorporationInventors: Roland Darms, Vratislav Kvita, Charles E. Monnier
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Patent number: 4588786Abstract: A process for producing a water-soluble dicarboxylic acid imide compound which comprises adding a primary amine compound to an aqueous solution of a water-soluble salt of a dicarboxylic acid compound containing at least one dicarboxylic acid unit capable of forming a 5-membered cyclic acid imide linkage and heating the mixture to introduce an acid imide linkage into the molecule.Type: GrantFiled: October 5, 1984Date of Patent: May 13, 1986Assignee: Nippon Zeon Co., Ltd.Inventors: Hiromitsu Kadono, Tadao Natsuume
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Patent number: 4577033Abstract: Heterocyclic quaternary ammonium salts such as N,N-di-n-butylpiperidinium bromide are excellent phase transfer agents for the preparation of aromatic ethers, as by the reaction of the disodium salt of bisphenol A with 4-nitro-N-methylphthalimide.Type: GrantFiled: January 14, 1985Date of Patent: March 18, 1986Assignee: General Electric CompanyInventors: John W. Verbicky, Jr., Alice M. Colley
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Patent number: 4555563Abstract: Imide functional polyphenols are prepared by reacting an excess of a phenol with an unsaturated diimide which is prepared by reacting an unsaturated polycycloaliphatic dicarboxylic acid anhydride with a diamine.These materials are useful in the preparation of castings, coatings, laminates and the like.Type: GrantFiled: December 7, 1984Date of Patent: November 26, 1985Assignee: The Dow Chemical CompanyInventors: Robert E. Hefner, Jr., Mary N. White
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Patent number: 4554357Abstract: Bis-quaternary ammonium and phosphonium salts such as bis(tri-n-butyl)-1,6-hexylenediammonium dibromide are excellent phase transfer agents for the preparation of aromatic ether imides, as by the reaction of the disodium salt of bisphenol A with 4-nitro-N-methylphthalimide.Type: GrantFiled: October 14, 1983Date of Patent: November 19, 1985Assignee: General Electric CompanyInventors: John W. Verbicky, Jr., Elbridge A. O'Neil, Jr.