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: 4520204Abstract: The yield of aromatic ether imides prepared by reacting a substituted phthalimide (such as 4-nitro-N-methylphthalimide) with an alkali metal salt of a hydroxyaromatic compound (such as the disodium salt of bisphenol A) in the presence of a phase transfer catalyst is improved by conducting the reaction in o-dichlorobenzene as diluent. When the reaction mixture is subsequently extracted with water and/or aqueous alkali, o-dichlorobenzene can also be used in recovery of the phase transfer catalyst from the aqueous phase by extraction thereof. Such recovery is improved by dissolving a substantial amount of inorganic salt in the aqueous phase and by conducting the o-dichlorobenzene extraction at elevated temperatures.Type: GrantFiled: April 25, 1983Date of Patent: May 28, 1985Assignee: General Electric CompanyInventor: Thomas L. Evans
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Patent number: 4499285Abstract: A method for making diarylthioethers including thioetherbis(phthalic anhydrides) and thioetherbis(phthalimides) in the absence of a solvent medium by the interaction of sulfide compounds, including alkali metal sulfides and alkali metal hydrogen sulfides, with molten organo-substituted aromatic compounds including phthalic anhydrides and phthalimides mediated by a phase transfer catalyst.Type: GrantFiled: November 1, 1982Date of Patent: February 12, 1985Assignee: General Electric CompanyInventor: Thomas L. Evans
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Patent number: 4476309Abstract: A method for making aromatic ether imides is provided by effecting the displacement of reactive radicals on a phthalimide nucleus with a mono- or bis-alkali metal phenoxide in the presence of a nonpolar solvent and a phase transfer catalyst, such as a triorganoborate. The aromatic ether imide made by the present invention are useful intermediates for making aromatic ether anhydrides and aromatic bis(ether anhydrides).Type: GrantFiled: March 21, 1983Date of Patent: October 9, 1984Assignee: General Electric CompanyInventors: John W. Verbicky, Jr., Elbridge A. O'Neil, Jr.
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Patent number: 4471125Abstract: A method is provided for making aromatic ether imides in the substantial absence of a solvent. A mixture of at least one halo-substituted phthalimide and at least one anhydrous alkali metal phenoxide salt is heated at a temperature at least sufficient to convert the halo-substituted phthalimide to the molten state and below the temperature at which the alkali metal phenoxide is thermally unstable.Type: GrantFiled: September 29, 1982Date of Patent: September 11, 1984Assignee: General Electric CompanyInventors: John W. Verbicky, Jr., Brent A. Dellacoletta
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Patent number: 4467097Abstract: A method is provided for making aromatic bis(etherimide)s by effecting reaction between an aromatic bisphenoxide salt and a nitro-substituted N-alkyl phthalimide in the presence of a non-polar organic solvent and an effective amount of a phase transfer catalyst. There is utilized as the phase transfer catalyst, a mixture of a dipolar aprotic solvent and a polyvalent metal salt such as zinc chloride.Type: GrantFiled: September 29, 1982Date of Patent: August 21, 1984Assignee: General Electric CompanyInventors: John W. Verbicky, Jr., James A. Cella, Elbridge A. O'Neil, Jr.
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Patent number: 4455431Abstract: A simplified method is provided for making aromatic bis-etherphthalimides by employing a polychlorinated C.sub.(1-3) alkane solution of nitro-N-organophthalimide directly with alkali metal bisphenoxide salt in a refluxing nonpolar organic solvent. After the polychlorinated C.sub.(1-3) alkane has completely distilled from the mixture, a phase transfer catalyst is added. As a result, the requirement for isolating and handling nitro-N-organophthalimide solids prior to condensation with alkali metal bisphenoxide salts is thereby eliminated.Type: GrantFiled: March 5, 1982Date of Patent: June 19, 1984Assignee: General Electric CompanyInventors: Frank J. Williams, III, Brent A. Dellacoletta
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Patent number: 4451402Abstract: Novel, unsaturated diacteylene-terminated polyimides and processes for their preparation are disclosed herein. These new polyimides are derivatives of anhydride-terminated aromatic polyimides from which they can be prepared by amidation to provide new unsaturated amide groups having a terminal group containing the structure --C.tbd.C--C.tbd.C--, hereinafter sometimes referred to as "conjugated diynes". These new compositions are more tractable than the original anhydride-terminated polyimides and can be converted at appropriate lower temperatures to crosslinked, insoluble, infusible polymers without by-product formation, thereby extending greatly the applications for which the aromatic polyimides can be employed. Moreover, these new polyimides can undergo the Diels-Alder type of addition with a large number of dienophiles. Certain monomeric materials are also described.Type: GrantFiled: March 2, 1982Date of Patent: May 29, 1984Assignee: Plastics Engineering CompanyInventors: Gaetano F. D'Alelio, deceased, Phillip A. Waitkus
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Patent number: 4436662Abstract: The present invention relates to compounds of the formula ##STR1## wherein R.sub.1 and R.sub.3 are selected from the group consisting of hydrogen, lower alkyl, hydroxy, lower alkoxy or acyloxy and R.sub.2 and R.sub.4 are hydrogen or R.sub.1 and R.sub.2 and/or R.sub.3 and R.sub.4 taken together are oxo groups with the proviso that at least one oxo group is present; R is selected from the group consisting of hydrogen, lower alkyl, C.sub.2 to C.sub.7 carboxylic acids and the esters and amides thereof, hydroxy C.sub.2 to C.sub.7 alkyl and amino C.sub.2 to C.sub.7 alkyl or mono- or di-lower alkyl amino C.sub.2 to C.sub.7 alkyl; R.sub.5 is halogen or hydrogen; and R.sub.6 is halogen with the proviso that when R.sub.1 or R.sub.3 is hydroxy, lower alkoxy or acyloxy, then R is lower alkyl or hydrogen and the N-oxides and the pharmaceutically acceptable salts thereof.Type: GrantFiled: March 31, 1983Date of Patent: March 13, 1984Assignee: Hoffmann-La Roche Inc.Inventors: Rodney I. Fryer, Eugene J. Trybulski, Armin Walser
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Patent number: 4413131Abstract: Disclosed are compounds of formula I, ##STR1## in which the R.sub.1 's, independently, are chlorine or bromine, andR.sub.2 is fluorine, chlorine, bromine, methyl, ethyl, ethoxy or tri-fluoromethyl,their production and use as pigments.Type: GrantFiled: July 11, 1977Date of Patent: November 1, 1983Assignee: Sandoz Ltd.Inventor: Dimitrios Karanatsios
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Patent number: 4409018Abstract: Novel compounds of the formula ##STR1## wherein R is a halogen, Q is hydrogen, a substituted or unsubstituted hydrocarbon, ##STR2## (wherein R.sub.1 is a substituted or unsubstituted hydrocarbon or ##STR3## R.sub.2 is hydrogen or a substituted or unsubstituted hydrocarbon, R.sub.3 is a substituted or unsubstituted hydrocarbon, R.sub.4 is a lower alkyl group, X is oxygen or an imino group which may be substituted by a lower alkyl, and each of Y and Z is oxygen or sulfur); which are useful as herbicides.Type: GrantFiled: May 28, 1981Date of Patent: October 11, 1983Assignee: Takeda Chemical Industries, Ltd.Inventor: Yasuo Ishida
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Patent number: 4404361Abstract: An additive flame retardant bisimide containing halogen atoms and ammonium acid tetrahalophthalate, e.g. N,N'-bis(2-ethylene tetrabromophthalimide) ammonium acid tetrabromophthalate. These compounds are useful in a variety of polymeric compositions and demonstrate increased thermal stability. They also foam on decomposition with the evolution of gas thus readily lending themselves to the preparation of flame retardant coatings.Type: GrantFiled: January 11, 1982Date of Patent: September 13, 1983Assignee: Saytech, Inc.Inventor: Henry J. Barda
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Patent number: 4402878Abstract: Novel, unsaturated diacteylene-terminated polyimides and processes for their preparation are disclosed herein. These new polyimides are derivatives of anhydride-terminated aromatic polyimides from which they can be prepared by amidation to provide new unsaturated amide groups having a terminal group containing the structure --C.tbd.C--C.tbd.C--, hereinafter sometimes referred to as "conjugated diynes". These new compositions are more tractable than the original anhydride-terminated polyimides and can be converted at appropriate lower temperatures to crosslinked, insoluble, infusible polymers without by-product formation, thereby extending greatly the applications for which the aromatic polyimides can be employed. Moreover, these new polyimides can undergo the Diels-Alder type of addition with a large number of dienophiles. Certain monomeric materials are also described.Type: GrantFiled: March 2, 1982Date of Patent: September 6, 1983Assignee: Plastics Engineering CompanyInventors: Gaetano F. D'Alelio, deceased, Phillip A. Waitkus
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Patent number: 4402879Abstract: Novel, unsaturated diacteylene-terminated polyimides and processes for their preparation are disclosed herein. These new polyimides are derivatives of anhydride-terminated aromatic polyimides from which they can be prepared by amidation to provide new unsaturated amide groups having a terminal group containing the structure --C.tbd.C--C.tbd.C--, hereinafter sometimes referred to as "conjugated diynes". These new compositions are more tractable than the original anhydride-terminated polyimides and can be converted at appropriate lower temperatures to crosslinked, insoluble, infusible polymers without by-product formation, thereby extending greatly the applications for which the aromatic polyimides can be employed. Moreover, these new polyimides can undergo the Diels-Alder type of addition with a large number of dienophiles. Certain monomeric materials are also described.Type: GrantFiled: March 2, 1982Date of Patent: September 6, 1983Assignee: Plastics Engineering CompanyInventors: Gaetano F. D'Alelio, deceased, Phillip A. Waitkus
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Patent number: 4400519Abstract: Benzil-di-(.beta.-succinimidoethyl)ketal of the following structural formula ##STR1## and novel benzil ketal derivatives thereof. The novel benzil ketal derivatives are characterized by having a structure in which a 5- or 6-membered cyclic imidecontaining group is bonded to each of the two oxygen atoms of ketal. Because these compounds have a high decomposition or sublimation temperature and the ability to initiate photopolymerization, they are useful as photopolymerization initiators in the production of photopolymerizable shaped articles from a molten blend of a photopolymerizable thermoplastic polymer composition.Type: GrantFiled: February 4, 1980Date of Patent: August 23, 1983Assignee: Teijin LimitedInventors: Tsuneo Hagiwara, Akihiro Horike
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Patent number: 4377673Abstract: Novel, unsaturated diacteylene-terminated polyimides and processes for their preparation are disclosed herein. These new polyimides are derivatives of anhydride-terminated aromatic polyimides from which they can be prepared by amidation to provide new unsaturated amide groups having a terminal group containing the structure --C.tbd.C--C.tbd.C--, hereinafter sometimes referred to as "conjugated diynes". These new compositions are more tractable than the original anhydride-terminated polyimides and can be converted at appropriate lower temperatures to crosslinked, insoluble, infusible polymers without by-product formation, thereby extending greatly the applications for which the aromatic polyimides can be employed. Moreover, these new polyimides can undergo the Diels-Alder type of addition with a large number of dienophiles. Certain monomeric materials are also described.Type: GrantFiled: March 2, 1982Date of Patent: March 22, 1983Assignee: Plastics Engineering CompanyInventors: Gaetano F. D'Alelio, deceased, Phillip A. Waitkus
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Patent number: 4377525Abstract: Novel, unsaturated diacetylene-terminated polyimides and processes for their preparation are disclosed herein. These new polyimides are derivatives of anhydride-terminated aromatic polyimides from which they can be prepared by amidation to provide new unsaturated amide groups having a terminal group containing the structure --C.tbd.C--C.tbd.C--, hereinafter sometimes referred to as "conjugated diynes". These new compositions are more tractable than the original anhydride-terminated polyimides and can be converted at appropriate lower temperatures to crosslinked, insoluble, infusible polymers without by-product formation, thereby extending greatly the applications for which the aromatic polyimides can be employed. Moreover, these new polyimides can undergo the Diels-Alder type of addition with a large number of dienophiles. Certain monomeric materials are also described.Type: GrantFiled: March 2, 1982Date of Patent: March 22, 1983Assignee: Plastics Engineering CompanyInventors: Gaetano F. D'Alelio, deceased, Phillip A. Waitkus
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Patent number: 4339383Abstract: The invention relates to alkanolamido-.beta.-carboxylic acid esters of the formula I ##STR1## A full definition of the above formula will be found in claim 1 of the specification. These compounds are useful stabilizers for chlorinated thermoplastics.Type: GrantFiled: July 2, 1980Date of Patent: July 13, 1982Assignee: Ciba-Geigy CorporationInventors: Wolfgang Wehner, Klaus-Peter Michaelis, Rainer Schneider
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Patent number: 4334069Abstract: Chemiluminescent-labeled conjugates of the formula: ##STR1## wherein one of R.sup.1 and R.sup.2 is hydrogen and the other is --NR.sup.3 R.sup.4 ; R.sup.3 is hydrogen or straight chain alkyl containing 1-4 carbon atoms and R.sup.4 isL(CO--HN--CH.sub.2).sub.nwherein n=2-8 and L(CO)-- is a hapten bound through an amide bond. The labeled conjugates are useful as reagents in specific binding assays for determining haptens or their specific binding partners in liquid media.Type: GrantFiled: July 24, 1978Date of Patent: June 8, 1982Assignee: Miles Laboratories, Inc.Inventors: Robert T. Buckler, Hartmut R. Schroeder
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Patent number: 4331601Abstract: Novel, unsaturated diacetylene-terminated polyimides and processes for their preparation are disclosed herein. These new polyimides are derivatives of anhydride-terminated aromatic polyimides from which they can be prepared by amidation to provide new unsaturated amide groups having a terminal group containing the structure --C.tbd.C--C.tbd.C--, hereinafter sometimes referred to as "conjugated diynes". These new compositions are more tractable than the original anhydride-terminated polyimides and can be converted at appropriate lower temperatures to crosslinked, insoluble, infusible polymers without by-product formation, thereby extending greatly the applications for which the aromatic polyimides can be employed. Moreover, these new polyimides can undergo the Diels-Alder type of addition with a large number of dienophiles. Certain monomeric materials are also described.Type: GrantFiled: October 22, 1980Date of Patent: May 25, 1982Assignee: Plastics Engineering CompanyInventors: Gaetano F. D'Alelio, deceased, Phillip A. Waitkus
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Patent number: 4331794Abstract: Novel, unsaturated diacetylene-terminated polyimides and processes for their preparation are disclosed herein. These new polyimides are derivatives of anhydride-terminated aromatic polyimides from which they can be prepared by amidation to provide new unsaturated amide groups having a terminal group containing the structure --C.tbd.C--C.tbd.C--, hereinafter sometimes referred to as "conjugated diynes". These new compositions are more tractable than the original anhydride-terminated polyimides and can be converted at appropriate lower temperatures to crosslinked, insoluble, infusible polymers without by-product formation, thereby extending greatly the applications for which the aromatic polyimides can be employed. Moreover, these new polyimides can undergo can be employed. Moreover, these new polyimides can undergo the Diels-Alder type of addition with a large number of dienophiles. Certain monomeric materials are also described.Type: GrantFiled: October 22, 1980Date of Patent: May 25, 1982Assignee: Plastics Engineering CompanyInventors: Gaetano F. D'Alelio, deceased, Phillip A. Waitkus
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Patent number: RE30922Abstract: The products of the invention are vinyl end-capped oligomers which are prepared from 2,4-bis (p-aminobenzyl) aniline and a vinyl substituted aromatic monoamine, the principal component of which is the compound whose structure is shown in FIG. 3. The products are prepared from either of two (2) precursors. The first precursor is a compound whose structure is shown in FIG. 2 and which is prepared from 2,4-bis (p-aminobenzyl) aniline, a dianhydride of an aromatic tetracarboxylic acid such as 3,3'4,4'-benzophenonetetracarboxylic acid (BTDA) and a vinyl substituted aromatic monoamine, such as 3-aminophenyl-ethylene (APE). The second precursor is a complex amine salt having the structure shown in FIG. 6 and which is prepared from 2,4-bis-(p-aminobenzyl) aniline, a dialkyl ester of BTDA and APE.Type: GrantFiled: August 25, 1980Date of Patent: May 4, 1982Assignee: Gulf Oil CorporationInventors: William J. Heilman, Daniel J. Hurley