Plural Chalcogens Bonded Directly To Ring Carbons Of The Five-membered Hetero Ring (e.g., Cyclic Imides, Etc.) Patents (Class 548/435)
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Patent number: 6143902Abstract: A chemic compound having the formula: ##STR1## wherein P.sub.1 is a hydroxyl protecting group, R.sub.1 is an alkyl group, an olefinic group, an aromatic group, Ph, PhCH.sub.2, an O-alkyl group, an O-olefinic group, an O-aromatic group, O--Ph, or O--CH.sub.2 Ph, and wherein Z is an N-imido group. In particular, P.sub.1 may be selected from the group consisting of benzyl, benzyloxymethyl and benzoyl, and Z may be a heterocyclic N-imido group, preferably having 5 to 7 atoms in the ring and alternatively substituted with at least one electron withdrawing group, preferably selected from the group consisting of a chloro group, a fluoro group and a nitro group. In particular, it is contemplated that Z may be succinimido, phthalimido, 5-norbornene-2,3-dicarboxyimido, maleimido and substituted derivatives thereof.Type: GrantFiled: June 21, 1999Date of Patent: November 7, 2000Assignee: NaPro BioTherapeutics, Inc.Inventors: Jan Zygmunt, James D. McChesney, Madhavi C. Chander
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Patent number: 5872191Abstract: A process for producing a polyoxyalkylene derivative substituted with succinimidyl group which comprises reacting a polyoxyalkylene compound having carboxyl group at ends with N-hydroxysuccinimide in an inert solvent in the presence of dicyclohexylcarbodiimide; dissolving an obtained reaction product into chloroform, an amount by weight of chloroform being 0.5 to 10 times as much as an amount by weight of the polyoxyalkylene compound having carboxyl group at ends; and crystallizing the polyoxyalkylene derivative substituted with succinimidyl group by adding an aliphatic hydrocarbon having 5 to 8 carbon atoms to a resultant solution, an amount by weight of the aliphatic hydrocarbon being 2 to 10 times as much as an amount by weight of chloroform. Materials can be handled with safety, and a highly pure polyoxyalkylene derivative substituted with succinimidyl group which does not cause turbidity in an aqueous solution and has an excellent quality as a material for drugs can be produced.Type: GrantFiled: June 3, 1997Date of Patent: February 16, 1999Assignee: NOF CorporationInventors: Kouzoh Sanchika, Tohru Yasukohchi, Kei-ichi Maruyama, Syunsuke Ohhashi
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Patent number: 5693741Abstract: Low molecular weight resins that usually are aliphatic and that include crosslinking thermal functional groups are useful as liquid molding compounds for reaction injection molding or resin transfer molding. The compounds eliminate the need to handle solvents when preparing thermoset composites.Type: GrantFiled: March 15, 1988Date of Patent: December 2, 1997Assignee: The Boeing CompanyInventors: Clyde H. Sheppard, Hyman R. Lubowitz
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Patent number: 5672662Abstract: Active esters of PEG acids and related polymers are provided that have a single propionic or butanoic acid moiety and no other ester linkages. These polymer acids have a half life in water of from about 10 to 25 minutes. For example, alpha-methoxy, omega-propionic acid succinimidyl ester of PEG ("methoxy-PEG-SPA") has a nearly ideal reactivity with amino groups on proteins and other biologically active substances. The half life of methoxy-PEG-SPA is about 16.5 minutes in water. The invention also provides conjugates with proteins, enzymes, polypeptides, drugs, dyes, nucleosides, oligonucleotides, lipids, phospholipids, liposomes, and surfaces of solid materials that are compatible with living organisms, tissue, or fluid.Type: GrantFiled: October 2, 1995Date of Patent: September 30, 1997Assignee: Shearwater Polymers, Inc.Inventors: J. Milton Harris, Antoni Kozlowski
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Patent number: 5663256Abstract: A thermosetting aqueous-type emulsion of nadimide is disclosed. The emulsion comprises 1-70% by weight of an alkenyl-substituted nadimide, 0.1-20% by weight of protective colloid and/or surface-active agent and balance water. The emulsion is especially useful for making a paint, a coating material or an adhesive because the emulsion can easily be cured only by heating without forming any undesirable organic pollutants. In the past, various resins have been used together with organic solvents. However, because of the recent worldwide concern over the influence of organic solvents to pollution of the aerospace and underground environments, non-use or reduced-use of organic solvents is actively desired. Accordingly, developments of aqueous solution or aqueous-type emulsion of resins are desired. Until now there is no aqueous-type emulsion of a monomer of highly heat resistant polyimide.Type: GrantFiled: October 23, 1995Date of Patent: September 2, 1997Assignee: Maruzen Petrochemical Co., Ltd.Inventors: Hideya Ariga, Norio Futaesaku, Hiromitsu Baba
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Patent number: 5610317Abstract: Thermomechanical and thermo-oxidative stabilities in resin composites across the range of aerospace "engineering thermoplastic" resins are improved by forming four crosslinks at each addition polymerization site in the backbone of the resin using crosslinking functionalities of the general formula: ##STR1## .beta.=the residue an organic radical selected from the group consisting of: ##STR2## R.sub.8 =a divalent organic radical; X=halogen;Me=methylT=allyl or methallyl.G=--CH.sub.2 --, --S--, --CO--, --SO--, --O--, --CHR.sub.3 --, or --C(R.sub.3).sub.2 --;i=1 or 2;R.sub.3 =hydrogen, lower alkyl, lower alkoxy, aryl, or aryloxy; and.THETA.=--C.tbd.N, --O--C.tbd.N, --S--C.tbd.N, or --CR.sub.3 .dbd.C(R.sub.3).sub.2.Type: GrantFiled: June 5, 1995Date of Patent: March 11, 1997Assignee: The Boeing CompanyInventors: Hyman R. Lubowtiz, Clyde H. Sheppard
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Patent number: 5594089Abstract: Thermomechanical and thermo-oxidative stabilities in heterocycle or heterocycle sulfone resin composites are improved by forming four crosslinks at each addition polymerization site in the backbone of the resin using crosslinking functionalities.Type: GrantFiled: October 21, 1994Date of Patent: January 14, 1997Assignee: The Boeing CompanyInventors: Hyman R. Lubowtiz, Clyde H. Sheppard
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Patent number: 5587105Abstract: Low molecular weight resins that usually are aliphatic and that include crosslinking thermal functional groups are useful as liquid molding compounds for reaction injection molding or resin transfer molding. The compounds eliminate the need to handle solvents when preparing thermoset composites.Type: GrantFiled: June 5, 1995Date of Patent: December 24, 1996Inventors: Clyde H. Sheppard, Hyman R. Lubowitz
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Patent number: 5554769Abstract: The solvent-resistance and thermal stability of polyamideimides of the general formulae: ##STR1## is improved by capping the amideimides with a crosslinking functionality (Y) containing a residue selected from the group of: ##STR2## wherein R.sub.1 =lower alkyl, lower alkoxy, aryl, aryloxy, substituted alkyl, substituted aryl (either including hydroxyl or halo-substituents), halogen, or mixtures thereof;j=0, 1, or 2;G=--CH.sub.2 --, --O--, --S--, --SO.sub.2 --, --SO--, --CO--, --CHR--, or --C(R).sub.2 --;R=hydrogen, lower alkyl, or phenyl;T=methallyl or allyl;Me=methyl;R.sub.2 =a trivalent organic radical; andR.sub.3 =a divalent organic radical.The amideimide oligomers may be linear or multidimensional, and can be processed into blends, prepregs, or composites. Methods of making these amideimides and intermediates useful in the syntheses are also described. One such intermediate has the general formula:Y.sub.i --CONH--R.sub.3 --NH.sub.2and is the focus of the present application.Type: GrantFiled: June 5, 1995Date of Patent: September 10, 1996Assignee: The Boeing CompanyInventors: Clyde H. Sheppard, Hyman R. Lubowitz
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Patent number: 5502207Abstract: An alkenyl-substituted bisnadimide represented by the following formula 1!: ##STR1## wherein R.sup.1 and R.sup.2 individually represent a hydrogen atom or a methyl group, and E is an alkylene.phenylene group or an alkylene.phenylene.alkylene group represented by the following formula 2!: ##STR2## (wherein a is an integer of 0 or 1, and R.sup.3' individually represent a C.sub.1 -C.sub.4 alkylene group or a C.sub.5 -C.sub.8 cycloalkylene group)!, a process for the preparation of the same and a process for curing the same are disclosed. Further, an adhesive material and a coating material containing the bisnadimide as a curing component are also disclosed. A cured material obtaind from the bisnadimide has excellent heat resistance, mechanical strength, toughness, adhesion property to many kinds of substrates, and so on. The adhesive material shows excellent heat resistance and the coating material shows excellent boiling water resistance.Type: GrantFiled: August 10, 1994Date of Patent: March 26, 1996Assignee: Maruzen Petrochemical Co., Ltd.Inventors: Norio Futaesaku, Hideo Fukuda, Yoshiharu Itou, Hiromitsu Baba, Isao Maruyama
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Patent number: 5463076Abstract: Multidimensional oligomers of the present invention are surprisingly useful for advanced composites because each generally has a use temperature greatly in excess of its curing temperature. The oligomers have essentially no arms, and comprise crosslinking phenylimide end caps condensed directly onto an aromatic hub (preferably, phenyl) through "commodity" polymeric linkages, such as amide, diimide, ether, or ester. For example, p-nadicimidobenzoylchloride can be condensed with triaminobenzene to yield a multidimensional, crosslinking amide oligomer. Short chains of ether/carbonyl aromatic chains can be included, if desired. Methods for making these high-performance oligomers with ether/carbonyl aromatic chains use an Ullmann ether synthesis followed by a Friedel-Crafts reaction.Type: GrantFiled: March 26, 1993Date of Patent: October 31, 1995Assignee: The Boeing CompanyInventors: Clyde H. Sheppard, Hyman R. Lubowitz
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Patent number: 5414013Abstract: Compounds of the formula ##STR1## wherein Z is ##STR2## proline, pipecolic acid, an indolecarboxylic acid or an isoquinolinecarboxylic acid. These compounds are useful as cardiovascular agents.Type: GrantFiled: March 26, 1993Date of Patent: May 9, 1995Assignee: E. R. Squibb & Sons, Inc.Inventors: Norma G. Delaney, George C. Rovnyak, Melanie J. Loots
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Patent number: 5414089Abstract: Provided is a long chain carboxylic acid imide ester (I) represented by the following general formula (I) ##STR1## wherein W is a divalent long chain hydrocarbon group which may optionally be interrupted by one or more groups each independently selected from the group consisting of an oxygen atom, a sulfur atom, and a group of --N(R.sup.1)-- (R.sup.1 being a lower alkyl group) and X represents a divalent hydrocarbon group which may optionally be substituted, or salts thereof. The above long chain carboxylic acid imide ester or its salts is useful for modifying enzymes or proteins having biological activities to give their derivatives which have, while retaining most of the original biological activities, an extremely prolonged plasma half-life as compared with the proteins and have no antigenecities and can be administered to animals.Type: GrantFiled: August 16, 1993Date of Patent: May 9, 1995Assignee: Kuraray Co., Ltd.Inventors: Iwao Ebashi, Tetsuo Takigawa, Masayasu Inoue
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Patent number: 5367083Abstract: The solvent-resistance and thermal stability of polyamideimides of the general formulae: ##STR1## is improved by capping the amideimides with a crosslinking functionality (Y) containing a residue selected from the group of: ##STR2## wherein R.sub.1 =lower alkyl, lower alkoxy, aryl, aryloxy, substituted alkyl, substituted aryl (either including hydroxyl or halo-substituents), halogen, or mixtures thereof;j=0, 1, or 2;G=--CH.sub.2 --, --0--, --S--, --SO.sub.2 --, --SO--, --CO--, --CHR--, or --CR.sub.2 --;R=hydrogen, lower alkyl, or phenyl;T=methallyl or allyl;Me=methyl;R.sub.2 =a trivalent organic radical; andR.sub.3 =a divalent organic radical.The amideimde oligomers may be linear or multidimensional, and can be processed into blends, prepregs, or composites. Methods of making these amideimides and intermediates useful in the syntheses are also described.Type: GrantFiled: April 6, 1993Date of Patent: November 22, 1994Assignee: The Boeing CompanyInventors: Clyde H. Sheppard, Hyman R. Lubowitz
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Patent number: 5324844Abstract: Poly(ethylene glycol)-N-succinimide carbonate and its preparation are disclosed. Polyethylene glycol (PEG) is converted into its N-succinimide carbonate derivative. This form of the polymer reacts readily with amino groups of proteins in aqueous buffers. The modified proteins have PEG-chains grafted onto the polypeptide backbone by means of stable, hydrolysis-resistant urethane (carbamate) linkages.Type: GrantFiled: January 8, 1992Date of Patent: June 28, 1994Assignee: Enzon, Inc.Inventor: Shmuel Zalipsky
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Patent number: 5322944Abstract: Process for preparing enantiomers of general formula (I): ##STR1## where Z, R.sub.1, R.sub.2, R.sub.3 and n are defined in the description. The compounds obtained according to the invention are useful as medicinal products.Type: GrantFiled: June 30, 1992Date of Patent: June 21, 1994Assignee: Adir et CompagnieInventors: Gerald Guillaumet, Claude Fugier, Jean-Claude J. Souvie, Gerard Adam, Pierre Renard, Daniel-Henri Caignard
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Patent number: 5315011Abstract: The present invention provides (1) curable polyamide monomers represented by the formula: R.sup.1 --A.sup.1 --B.sup.1 --A.sup.2 --B.sup.2 --A.sup.3 --R.sup.2 where R.sup.1 and R.sup.2 are radicals selected from the group consisting of maleimide, substituted maleimide, nadimide, substituted nadimide, ethynyl, and (C(R.sup.3).sub.2).sub.2 where R.sub.3 is hydrogen with the proviso that the two carbon atoms of (C(R.sup.3).sub.2).sub.2 are bound on the aromatic ring of A.sup.1 or A.sup.3 to adjacent carbon atoms, A.sup.1 and A.sup.3 are 1,4-phenylene and the same where said group contains one or more substituents selected from the group consisting of halo, e.g., fluoro, chloro, bromo, or iodo, nitro, lower alkyl, e.g., methyl, ethyl, and propyl, lower alkoxy, e.g., methoxy, ethoxy, or propoxy, and fluoroalkyl or fluoroalkoxy, e.g., trifluoromethyl, pentafluoroethyl and the like, A.sup.Type: GrantFiled: September 8, 1992Date of Patent: May 24, 1994Assignee: The United States of America as represented by the United States Department of EnergyInventors: Brian C. Benicewicz, Andrea E. Hoyt
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Patent number: 5248748Abstract: Disclosed is a diacetylene compound comprising, as structural units, (a) at least one member selected from diacetylene group-containing organic groups of the formulae (I) and (II):R.sup.I --C.tbd.C--C.tbd.C--R.sup.II -- (I)and--R.sup.III --C.tbd.C--C.tbd.C--R.sup.IV -- (II)wherein R.sup.I is hydrogen or a (C1-16) monovalent organic group, and R.sup.II, R.sup.III and R.sup.IV are a (C1-13) divalent organic group,(b) at least one organic group having at least one carbon-to-carbon double bond, and (c) at least one connecting group connecting the units (a) and (b) , which connecting group is selected from amide, imide, ester, ether, amino, imino, urethane, sulfonyl and carbonyl bonds. A cured shaped article made of this compound exhibits isotropically a high elastic modulus and has excellent mechanical properties.Type: GrantFiled: December 19, 1990Date of Patent: September 28, 1993Assignee: Dir. General of Agency of Industrial Science and TechnologyInventors: Katsuyuki Nakamura, Satoru Yamazaki, Jinichiro Kato, Kensaku Tokushige
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Patent number: 5210213Abstract: Multidimensional oligomers of the present invention are surprisingly useful for advanced composites because each generally has a use temperature greatly in excess of its curing temperature. The oligomers have essentially no arms, and comprise crosslinking phenylimide end caps condensed directly onto an aromatic hub (preferably, phenyl) through "commodity" polymeric linkages, such as amide, diimide, ether, or ester. For example, p-nadicimidobenzoylchloride can be condensed with triaminobenzene to yield a multidimensional, crosslinking amide oligomer. Short chains of ether/carbonyl aromatic chains can be included, if desired. Methods for making these high-performance oligomers with ether/carbonyl aromatic chains use an Ullmann ether synthesis followed by a Friedel Craft reaction.Type: GrantFiled: January 5, 1987Date of Patent: May 11, 1993Assignee: The Boeing CompanyInventors: Clyde H. Sheppard, Hyman R. Lubowitz
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Patent number: 5198551Abstract: The present invention provides (1) curable polyamide monomers represented by the formula: R.sup.1 -A.sup.1 -B.sup.1 -A.sup.2 -B.sup.2 -A.sup.3 -R.sup.2 where R.sup.1 and R.sup.2 are radicals selected from the group consisting of maleimide, substituted maleimide, nadimide, substituted nadimide, ethynyl, and (C(R.sup.3).sub.2).sub.2 where R.sup.3 is hydrogen with the proviso that the two carbon atoms of (C(R.sup.3).sub.2).sub.2 are bound on the aromatic ring of A.sup.1 or A.sup.3 to adjacent carbon atoms, A.sup.1 and A.sup.3 are 1,4-phenylene and the same where said group contains one or more substituents selected from the group consisting of halo, e.g., fluoro, chloro, bromo, or iodo, nitro, lower alkyl, e.g., methyl, ethyl, and propyl, lower alkoxy, e.g., methoxy, ethoxy, or propoxy, and fluoroalkyl or fluoroalkoxy, e.g., trifluoromethyl, pentafluoroethyl and the like, A.sup.Type: GrantFiled: June 7, 1991Date of Patent: March 30, 1993Assignee: The United States of America as represented by the United States Department of EnergyInventors: Brian C. Benicewicz, Andrea E. Hoyt
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Patent number: 5198526Abstract: Linear or multidimensional, crosslinking, solvent resistant oxazole, thiazole, or imidazole (i.e., heterocycle) oligomers and blends of the crosslinking oligomers and noncrosslinking comparable polymers are described. The oligomers are prepared by reacting tetraamines, diaminodiols, or diaminothiols (i.e. four-functional compounds) with poly-carboxylic acid halides, and crosslinking phenylimide end cap monomers in a suitable solvent under an inert atmosphere.Type: GrantFiled: June 26, 1992Date of Patent: March 30, 1993Assignee: The Boeing CompanyInventors: Hyman R. Lubowitz, Clyde H. Sheppard
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Patent number: 5191088Abstract: Aromatic monoanhydride-esters of the formula (I) ##STR1## wherein R.sup.1 is ##STR2## and R.sup.2 is hydrogen, C.sub.1 -C.sub.4 alkyl or --OCH.sub.3 are useful as endcapping agents for the synthesis of multifunctional high temperature resins such as polyimides, polyimide-esters, polyimide-ethers and polyimide-amides.Type: GrantFiled: November 13, 1991Date of Patent: March 2, 1993Assignee: Ciba-Geigy CorporationInventor: Yefim Blyakhman
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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: 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: 5149824Abstract: There is provided a method for the production of an arylamide bisnadimide. The arylamide bisnadimide is useful as a prepolymer. The method includes the step of: condensing a nadimide compound having the nitrogen of said nadimide substituted with a halogen substituted aromatic group, with a dinucleophile in the presence of carbon monoxide, a base and a palladium catalyst.Type: GrantFiled: July 1, 1991Date of Patent: September 22, 1992Assignee: Eastman Kodak CompanyInventors: S. Richard Turner, Robert J. Perry, Richard W. Blevins
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Patent number: 5132431Abstract: A process for the continuous preparation of imidoperoxycarboxylic acids of the formula ##STR1## in which A is C.sub.2 -C.sub.4 -alkylene, phenylene, naphthylene or a group of the formula ##STR2## and R is a group of the formula --COOH, --SO.sub.3 H or --Cl, and X is C.sub.1 -C.sub.19 -alkylene or arylene, in which a solution of imidocarboxylic acids of the formula ##STR3## in sulfuric acid or methanesulfonic acid and an aqueous solution of hydrogen peroxide are continuously metered into a static mixer, then the solution of the imidoperoxycarboxylic acid obtained in this way is treated with water and the precipitated product is isolated.Type: GrantFiled: February 1, 1991Date of Patent: July 21, 1992Assignee: Hoechst AktiengesellschaftInventors: Hermann Fuchs, Hanspeter Gethoffer, Walter Gilb
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Patent number: 5126363Abstract: Indole derivatives of formula (I) ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 may be hydrogen or lower alkyl optionally substituted by halogen; A.sup.1 represents a straight or branched alkylene chain containing from 2 to 4 carbon atoms; R.sup.5 is hydrogen or a straight or branched alkyl group; A.sup.2 is a straight or branched, saturated or unsaturated hydrocarbon chain containing from 2 to 6 carbon atoms; and R.sup.6 is selected from a group consisting of various structures, have been found to exhibit central nervous system activities.Type: GrantFiled: January 23, 1991Date of Patent: June 30, 1992Assignee: Novo Nordisk A/SInventors: Lone Jeppesen, Peter H. Andersen, Louis B. Hansen, Peter Faarup, John B. Hansen
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Patent number: 5122614Abstract: Poly(ethylene glycol)-N-succinimide carbonate and its preparation are disclosed. Polyethylene glycol (PEG) is converted into its N-succinimide carbonate derivative. This form of the polymer reacts readily with amino groups of proteins in aqueous buffers. The modified proteins have PEG-chains grafted onto the polypeptide backbone by means of stable, hydrolysis-resistant urethane (carbamate) linkages.Type: GrantFiled: April 19, 1990Date of Patent: June 16, 1992Assignee: Enzon, Inc.Inventor: Shmuel Zalipsky
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Patent number: 5122613Abstract: This invention relates to novel fluorinated N,N-bis-imides of the formula ##STR1## wherein R is a bivalent radical of the formula ##STR2## The compounds are particularly useful as monomers in the preparation of high performance polymer.Type: GrantFiled: May 31, 1991Date of Patent: June 16, 1992Assignee: Occidental Chemical CorporationInventors: Robert A. Buchanan, Robert L. Ostrozynski, Henry C. Lin
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Patent number: 5120857Abstract: Bisimides of the formula I ##STR1## in which, for example, R.sup.1 is hydrogen, x is 1, y is zero and R is bis-(1,4-phenylene)-methane are intermediates for the preparation of polymers having excellent physical properties, and are suitable for the production of mouldings, coatings and adhesive joints and, in particular, for the production of prepregs and heat-resistant composite materials.Type: GrantFiled: February 20, 1990Date of Patent: June 9, 1992Assignee: Ciba-Geigy CorporationInventors: Andreas Kramer, Sameer H. Eldin
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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: 5082905Abstract: Linear or multidimensional, crosslinking, solvent resistant oxazole, thiazole, or imidazole (i.e., heterocycle) oligomers and blends of the crosslinking oligomers and noncrosslinking comparable polymers are described. The oligomers are prepared by reacting tetraamines, diaminodiols, or diaminothiols (i.e. four-functional compounds) with poly-carboxylic acid halides, and crosslinking phenylimide end cap monomers in a suitable solvent under an inert atmosphere.Type: GrantFiled: May 6, 1991Date of Patent: January 21, 1992Assignee: The Boeing CompanyInventors: Hyman R. Lubowitz, Clyde H. Sheppard
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Patent number: 5075456Abstract: Imides of the formula I ##STR1## In which R.sub.1, R.sub.2 and R.sub.4 independently of one another are hydrogen or methyl, R.sub.3 is a direct bond or a C.sub.2 -C.sub.20 aliphatic radical which can be interrupted by O atoms or a mononuclear or polynuclear C.sub.5 -C.sub.20 cycloaliphatic or C.sub.6 -C.sub.20 aromatic radical or is a group of the formula II ##STR2## in which T is methylene, isopropylidene, CO, O, S or SO.sub.2 and R.sub.5 is hydrogen or phenyl, can be crosslinked either photochemically or by heat and produce polymers having excellent properties, in particular a very high resistance to heat. They are particularly suitable for the production of heat-resistant photolithographs or as matrix resins for the production of composite materials.Type: GrantFiled: February 27, 1990Date of Patent: December 24, 1991Assignee: Ciba-Geigy CorporationInventors: Alfred Renner, Christian Vonlanthen, Edward Irving, Christopher P. Banks
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Patent number: 5071941Abstract: The solvent resistance of polyethersulfone oligomers is enhanced by using difunctional imidophenol end-cap monomers to provide improved crosslinking. The imidophenol monomers include two unsaturated functionalities capable of cross-linking upon thermal or chemical activation. Blends, pregregs, and composites using the novel end caps are described for linear or multidimensional polyethersulfone oligomers.Type: GrantFiled: March 6, 1989Date of Patent: December 10, 1991Assignee: The Boeing CompanyInventors: Hyman R. Lubowitz, Clyde H. Sheppard
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Patent number: 5068356Abstract: Phenolic N-(amido) imides are provided which are useful as antioxidant stabilizers for organic materials, including a large variety of synthetic polymers, typically subject to thermooxidative degradation. The antioxidant effectiveness of the phenolic N-(amido)imide stabilizers is enhanced by the deactivating potential of the amido-imide moiety towards metals or metal ions that frequently contaminate polymer compositions and serve to catalyze thermal degradation.Type: GrantFiled: February 20, 1990Date of Patent: November 26, 1991Assignee: Atochem North America, Inc.Inventor: Jerome Wicher
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Patent number: 5026871Abstract: The invention provides a compound of the general formula I ##STR1## in which R.sub.1 is hydrogen or methyl and R.sub.2 is C.sub.1 -C.sub.12 alkyl, preferably methyl or ethyl.Type: GrantFiled: October 22, 1990Date of Patent: June 25, 1991Assignee: Ciba-Geigy CorporationInventor: Mark R. Southcott
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Patent number: 5011905Abstract: Polyimide oligomers include (1) linear, monofunctional crosslinking oligomers prepared by condensing a monoanhydride end cap with a diamine that includes alternating ether and "sulfone" (--SO.sub.2 --, --S--, --CO--, --(CF.sub.3).sub.2 C--, or --(CH.sub.3).sub.2 C--) linkages connecting alternating aromatic radicals and with a dianhydride (or dianhydride mixture), particularly the unsaturated, aliphatic dianhydride commonly known as MCTC; (2) linear, mono- or difunctional crosslinking oligomers prepared by condensing an amine end cap with a diamine and a dianhydride; and (3) multidimensional, crosslinking oligomers having an aromatic hub and at least three radiating arms connected to the hub, each arm including a crosslinking end cap at its distal end and at least one imide linkage.Blends, prepregs, and composites can be prepared from the oligomers.Type: GrantFiled: August 13, 1990Date of Patent: April 30, 1991Assignee: The Boeing CompanyInventors: Hyman R. Lubowitz, Clyde H. Sheppard
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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: 4980481Abstract: High performance composites can be made from linear or multidimensional oligomer or blends that include unsaturated hydrocarbon crosslinking functionalities linked to a pyrimidine radical on the terminal ends of the polymeric backbones of the oligomers. The oligomers are made by condensing pyrimidine-based end-cap monomers of the formula: ##STR1## wherein Z=--OH or halogen;Y= ##STR2## wherein R.sub.1 =lower alkyl, lower alkoxy, aryl, aryloxy, substituted alkyl, substituted aryl, halogen, or mixtures thereof;j=0, 1, or 2;G=--CH.sub.2 --, --O--, --S--, --SO--, --CO--, --CHR--, --CR.sub.2 --, or --SO.sub.2 --;T=methallyl or allyl;Me=methyl; andR=hydrogen, lower alkyl, or phenyl,with suitable polymeric precursors.Type: GrantFiled: March 14, 1988Date of Patent: December 25, 1990Assignee: The Boeing CompanyInventors: Hyman R. Lubowitz, Clyde H. Sheppard
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Patent number: 4973662Abstract: A compound represented by the following general formula [1]: ##STR1## wherein R.sub.3 and R.sub.4 are independently selected from hydrogen and alkyl groups having 1 to 4 carbon groups,is valuable as an endcapping agent for a polyimide. Namely, a PMR polyimide varnish comprising this compound, a dialkyl tetracarboxylate represented by the following general formula [2]: ##STR2## wherein R.sub.1 is a direct bond or stands for CH.sub.2, O, CO, SO.sub.2, S or C(CH.sub.3).sub.2 and X stands for an alkyl group having 1 to 4 carbon atoms,and a diamine represented by the following general formula [3]: ##STR3## wherein R.sub.2 is a direct bond or stands for CH.sub.2, O, CO, SO.sub.2 S or C(CH.sub.3).sub.2,has a good storage stability and is especially valuable as a matrix resin to be incorporated in a fiber-reinforced composite material.Type: GrantFiled: September 8, 1988Date of Patent: November 27, 1990Assignee: Director General of Agency of Industrial Science and TechnologyInventors: Nobuyuki Odagiri, Kuniaki Tobukuro
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Patent number: 4965336Abstract: Linear or multidimensional, crosslinking, solvent resistant oxazole, thiazole, or imidazole (i.e., heterocycle) oligomers and blends of the crosslinking oligomers and noncrosslinking comparable polymers are described. The oligomers are prepared by reacting tetraamines, diaminodiols, or diaminothiols (i.e. four-functional compounds) with poly-carboxylic acid halides, and crosslinking phenylimide end cap monomers in a suitable solvent under an inert atmosphere.Type: GrantFiled: November 3, 1987Date of Patent: October 23, 1990Assignee: The Boeing CompanyInventors: Hyman R. Lubowitz, Clyde H. Sheppard
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Patent number: 4958031Abstract: Polyetherimide oligomers having crosslinking end cap moieites 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; 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 --The crosslinkable oligomers are made by reacting substituted phthalic anhydrides with hydroxyaryl amines and suitable crosslinking and cap reactants, or by self-condensation of phthalimide salts followed by capping the polymers.Type: GrantFiled: July 5, 1988Date of Patent: September 18, 1990Assignee: The Boeing CompanyInventors: Clyde H. Sheppard, Hyman R. Lubowitz
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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: 4871475Abstract: Polysulfone and polyethersulfone oligomers are made by the condensation of phenols and halogenated moieties and exhibit improved solvent resistance when capped with crosslinkable end cap imidophenols. Composites made with a blend of the oligomers and corresponding polymers formed from the phenols and halogenated moieties, but without end caps, exhibit superior impact resistance while retaining the desired solvent resistance. Conductive or semiconductive oligomers (or their composites) can be formed by doping suitable oligomers, especially those prepared from Schiff base diols.Type: GrantFiled: October 7, 1985Date of Patent: October 3, 1989Assignee: The Boeing CompanyInventors: Hyman R. Lubowitz, Clyde H. Sheppard
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Patent number: 4868270Abstract: High thermal stabilities are achievable in linear or multidimensional sulfone, solvent resistant oligomers by incorporating oxazole, thiazole, or imidazole linkages into the oligomer backbone. Blended oligomers of crosslinking oligomers and noncrosslinking compatible polymers are also described. The oligomers include residues of four-functional compounds of the formula: ##STR1## wherein M=--CO--, --S--, --O--, --SO.sub.2 -- or --(CF.sub.3).sub.2 C--; andY=--OH, --SH, or --NH.sub.2.In an improved method, the reactants are condensed at or below ambient temperature in the presence of pyridine in a suitable solvent such as N,N'-dimethylacetamide (DMAC).Type: GrantFiled: November 17, 1987Date of Patent: September 19, 1989Assignee: The Boeing CompanyInventors: Hyman R. Lubowitz, Clyde H. Sheppard, Ronald R. Stephenson
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Patent number: 4851495Abstract: 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: February 20, 1987Date of Patent: July 25, 1989Assignee: The Boeing CompanyInventors: Clyde H. Sheppard, Hyman R. Lubowitz
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Patent number: 4851501Abstract: The solvent resistance of polyethersulfone oligomers is enhanced by using difunctional imidophenol end-cap monomers to provide improved crosslinking. The imidophenol monomers include two unsaturated functionalities capable of cross-linking upon thermal or chemical activation. Blends, pregregs, and compositions using the novel end caps are described for linear or multidimensional polyethersulfone oligomers.Type: GrantFiled: December 17, 1987Date of Patent: July 25, 1989Assignee: The Boeing CompanyInventors: Hyman R. Lubowitz, Clyde H. Sheppard
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Patent number: 4778898Abstract: Compounds of formula ##STR1## wherein E and R' are each independently of the other a hydrogen atom or a methyl group,X is ##STR2## and R is --C.sub.m H.sub.2m --, in which m is 2 to 20, --C.sub.n H.sub.2n O--, in which n is 2 to 6, m- or p-phenylene, m- or p-oxyphenylene, in which the oxygen atom is attached to the group X, or X is ##STR3## and R is m- or p-phenylene, or X is ##STR4## and R is --(CH.sub.2 CH.sub.2 O).sub.q --, --(CH.sub.2 CH.sub.2 CH.sub.2 O).sub.q -- or --[CH.sub.2 CH(CH.sub.3)O].sub.q --, in which q is 1 to 6, m- or p-oxyphenylene, in which the oxygen atom is attached to the group X, or X is ##STR5## and R is --C.sub.r H.sub.2r --, in which r is 2 to 4, or m- or p-phenylene,are suitable for the preparation of crosslinked polymers.Type: GrantFiled: October 22, 1986Date of Patent: October 18, 1988Assignee: Ciba-Geigy CorporationInventors: Christian Vonlanthen, Andreas Kramer, Alfred Renner
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Patent number: RE36359Abstract: Provided is a long chain carboxylic acid imide ester (I) represented by the following general formula (I) ##STR1## wherein W is a divalent long chain hydrocarbon group which may optionally be interrupted by one or more groups each independently selected from the group consisting of an oxygen, atom, a sulfur atom, and a group of --N(R.sup.1)-- (R.sup.1 being a lower alkyl group) and X represents a divalent hydrocarbon group which may optionally be substituted, or salt thereof. The above long chain carboxylic acid imide ester or its salts is useful for modifying enzymes or proteins having biological activities to give their derivatives which have, while retaining most of the original biological activities, an extremely prolonged plasma half-life as compared with the proteins and have no antigenecities and can be administered to animals.Type: GrantFiled: May 1, 1997Date of Patent: October 26, 1999Assignee: Kuraray Co., Ltd.Inventors: Iwao Ebashi, Tetsuo Takigawa, Masayasu Inoue