Double Bond Between Ring Carbons In Each Of The Two Nitrogen Containing Hetero Rings (e.g., Bis-maleimides, Etc.) Patents (Class 548/521)
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Patent number: 6153662Abstract: Aromatic maleimides and methods using the same are disclosed. Polymerization of compositions which include the compounds of the invention may be activated by irradiating the composition with radiation.Type: GrantFiled: May 26, 1998Date of Patent: November 28, 2000Assignees: University of Southern Mississippi, First Chemical Corp.Inventors: Christopher W. Miller, Charles E. Hoyle, E. Sonny Jonsson
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Patent number: 6063828Abstract: A curable underfill encapsulant composition, suitable for use in semiconductor packaging, comprises one or more mono- or polyfunctional maleimide compounds, or one or more mono- or polyfunctional vinyl compounds other than maleimide compounds, or a combination of maleimide and vinyl compounds, with a free radical curing agent, and optionally, one or more fillers.Type: GrantFiled: July 2, 1998Date of Patent: May 16, 2000Assignee: National Starch and Chemical Investment Holding CorporationInventors: Bodan Ma, Quinn K. Tong
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Patent number: 6057342Abstract: The present application describes amidinophenyl-pyrrolidines, -pyrrolines, and -isoxazolidines and derivatives thereof of formula I: ##STR1## or pharmaceutically acceptable salt forms thereof, wherein one of D and D' may be C(.dbd.NH)NH.sub.2 and the other H, and J.sup.1 and J.sup.2 may be O or CH.sub.2, which are useful as inhibitors of factor Xa.Type: GrantFiled: July 7, 1997Date of Patent: May 2, 2000Assignee: Dupont Pharmaceutical Co.Inventors: John Matthew Fevig, Donald Joseph Phillip Pinto, Mimi Lifen Quan, Petrus Fredericus Wilhelmus Stouten
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Patent number: 6017943Abstract: The present invention provides a class of compounds having the formula:Y--R--CH.sub.2 --CH.sub.2 --[O--CH.sub.2 --CH.sub.2 ].sub.n --R'--Y'wherein n is an integer from about 5 to about 200; R is carbamate, urea, or amide; R' is carbamate, urea, amide, or oxygen; Y is 4-phenylmalemimido or 3-phenylmaleimido; and Y' is 4-phenylmalemimido, 3-phenylmaleimido, methyl or hydrogen. The present invention also provides various hemoglobin compositions modified with the class of compounds of the present invention, processes for preparing these compositions, as well as pharmaceutical compositions comprising these compositions.Type: GrantFiled: February 4, 1998Date of Patent: January 25, 2000Assignee: Albert Einstein College of Medicine of Yeshiva UniversityInventors: A. Seetharama Acharya, Belur N. Manjula, Paul K. Smith
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Patent number: 5985815Abstract: New compounds useful as bleach activators as well as new percarboxylic acids, which may be formed as intermediates upon reaction of such activators with peroxygen bleach source in aqueous solution, include nitrogen-containing heterocyclic groups. Preferred activators are symmetrical derivatives of dibasic carboxylic acids, having N,N'diacyl N-heterocyclic groups usually lactams. They are produced by reaction of 2 moles of the lactam with one mole of dibasic acid chloride or anhydride.Type: GrantFiled: April 3, 1997Date of Patent: November 16, 1999Assignee: Warwick International Group LimitedInventors: John Townend, Jan Darrel Crowther
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Patent number: 5976783Abstract: Formation of an intramolecular cross-link in enzyme donor polypeptide fragments of .beta.-galactosidase, thereby forming a cyclic enzyme donor which is hindered from complementation with an enzyme acceptor fragment to form active of .beta.-galactosidase. The cyclic enzyme donor can be linearized by cleaving to restore complementation ability. Assays in which such cyclic enzyme donors are linearized by specific analytes are disclosed, as well as novel homobifunctional bis-maleimido cross-linking agents of the formula ##STR1## wherein R is hydroxy or acetate.Type: GrantFiled: June 26, 1997Date of Patent: November 2, 1999Assignee: Boehringer Mannheim CorporationInventors: Michael J. Powell, Lutz F. Tietze
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Patent number: 5968640Abstract: The morphology of multidimensional, thermally stable oligomers is combined with the inclusion of charge carrier linkages within the polymer arms to produce thermally stable advanced composites from cured oligomers that are conductive or semiconductive if suitably doped.Type: GrantFiled: September 5, 1985Date of Patent: October 19, 1999Assignee: The Boeing CompanyInventors: Hyman R. Lubowitz, Clyde H. Sheppard, Larry P. Torre
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Patent number: 5965579Abstract: The invention relates to compounds of the formula: ##STR1## Compounds of the above formula have a great affinity for the neurotensin receptors.Type: GrantFiled: November 21, 1997Date of Patent: October 12, 1999Assignee: SanofiInventors: Bernard Labeeuw, Danielle Gully, Francis Jeanjean, Jean-Charles Molimard, Robert Boigegrain
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Patent number: 5948922Abstract: Compounds containing two cyclic hydrocarbon moieties which are substituted to provide crosslinking functionality and which are linked to each other by secondary or tertiary oxycarbonyl containing moiety are basis for compositions which are cured to provide cured thermosets for encapsulation and underfill for electronic components that are thermally decomposable to allow repair, replacement, recovery or recycling of operative electronic components from assemblies that are inoperative.Type: GrantFiled: February 20, 1997Date of Patent: September 7, 1999Assignee: Cornell Research Foundation, Inc.Inventors: Christopher K. Ober, Hilmar Koerner
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Patent number: 5939449Abstract: The invention relates to compounds of the formula: ##STR1## The compounds have great affinity for the neurotensin receptors.Type: GrantFiled: November 24, 1997Date of Patent: August 17, 1999Assignee: SanofiInventors: Bernard Labeeuw, Danielle Gully, Francis Jeanjean, Jean-Charles Molimard, Robert Boigegrain
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Patent number: 5919923Abstract: The invention provides for tripyrrane compounds of the formula ##STR1## wherein: each Q represents, typically, an alkyl group, cycloalkyl group, aryl group, or a heteroaryl group; and each R represents hydrogen, an alkyl group, alcohol group, or a carbonyl-containing group. Additionally, there are described methods to prepare such compounds, for example, comprising the steps of:(a) reacting a compound of the formula:Q--CHO or Q--CH(OS)(OS')wherein S and S' are independently lower alkyl, an aryl group containing from 5 to 14 ring atoms, and --(CH.sub.2).sub.n -- where n=2-4;with a stoichiometric excess of a pyrrole having the formula: ##STR2## in the presence of a catalytic amount of an acid; (b) removing the unreacted pyrrole or any other solvents used in (a) by evaporation to form a residue; and(c) treating the residue to remove high molecular weight polymeric materials and the corresponding dipyrromethane by-product, leaving the desired compound.Type: GrantFiled: May 19, 1998Date of Patent: July 6, 1999Inventors: Christian Bruckner, Ross W. Boyle, David Dolphin
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Patent number: 5849932Abstract: A novel bismaleimide compound having the following formula: ##STR1## is synthesized from 1,3-bis(aminomethyl)cyclohexane and maleic anhydride, and is readily soluble in a variety of ordinary low boiling point organic solvents.Type: GrantFiled: February 26, 1997Date of Patent: December 15, 1998Assignee: Nippon Mektron, LimitedInventor: Lin-chiu Chiang
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Patent number: 5750725Abstract: The present invention provides a class of compounds having the formula:Y--R--CH.sub.2 --CH.sub.2 --?O--CH.sub.2 --CH.sub.2 !.sub.n --R'--Y'wherein n is an integer from about 5 to about 200; R is carbamate, urea, or amide; R' is carbamate, urea, amide, or oxygen; Y is 4-phenylmalemimido or 3-phenylmaleimido; and Y' is 4-phenylmalemimido, 3-phenylmaleimido, methyl or hydrogen. The present invention also provides various hemoglobin compositions modified with the class of compounds of the present invention, processes for preparing these compositions, as well as pharmaceutical compositions comprising these compositions.Type: GrantFiled: September 26, 1996Date of Patent: May 12, 1998Assignee: Albert Einstein College of Medicine of Yeshiva University, a Division of YeshivaInventors: A. Seetharama Acharya, Belur N. Manjula, Paul K. Smith
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Patent number: 5635593Abstract: A brandykinin antagonist of the formula:X(BKA).sub.nwherein BKA is the peptide chain of a bradykinin antagonist peptide, X is a linking group and n is a whole number greater than 1. The BKA substituents may be the same or different. Monomeric antagonists of the formula X(BKA) are also disclosed. Also disclosed are bradykinin antagonists of the formula:(Y)(X)(BKA)where X and BKA have the meanings indicated above and Y is the peptide chain of an antagonist or agonist for a non-bradykinin receptor.Type: GrantFiled: May 12, 1995Date of Patent: June 3, 1997Assignee: Cortech, Inc.Inventors: John C. Cheronis, James K. Blodgett, Eric T. Whalley, Shadrach R. Eubanks, Lisa G. Allen, Khe T. Nguyen
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Patent number: 5602205Abstract: Novel polyfunctional maleimides as well as novel compositions based on mono- and polyfunctional maleimides are provided. Also provided are heat resistance resin compositions and curable compositions incorporating the same. The monofunctional maleimide is N-(2,3-dimethylphenyl)maleimide, and the polyfunctional maleimides are bis- and higher functional variations thereof.Type: GrantFiled: April 27, 1995Date of Patent: February 11, 1997Assignee: Cytec Technology Corp.Inventors: Balwant Singh, Robert J. Tynik
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Patent number: 5585484Abstract: The present invention provides a class of compounds having the formula:Y--R--CH.sub.2 --CH.sub.2 --[O--CH.sub.2 --CH.sub.2 ].sub.n --R'--y'wherein n is an integer from about 5 to about 200; R is carbamate, urea, or amide; R' is carbamate, urea, amide, or oxygen; Y is 4-phenylmalemimido or 3-phenylmaleimido; and Y' is 4-phenylmalemimido, 3-phenylmaleimido, methyl or hydrogen. The present invention also provides various hemoglobin compositions modified with the class of compounds of the present invention, processes for preparing these compositions, as well as pharmaceutical compositions comprising these compositions.Type: GrantFiled: April 19, 1995Date of Patent: December 17, 1996Assignee: Albert Einstein College of Medicine of Yeshiva University, A Division of Yeshiva UniversityInventors: A. Seetharama Acharya, Belur N. Manjula, Paul K. Smith
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Patent number: 5525704Abstract: Disclosed is an aromatic diamine compound represented by the formula (I) ##STR1## wherein R is H or CH.sub.3. Also disclosed is a bismaleimide compound represented by the formula (IV) ##STR2## wherein R is H or CH.sub.3, A resin forming composition comprising these compounds is also disclosed. The compounds are useful as raw materials for resins, and the resin forming composition and the resin can provide excellent heat resistance and impact resistance and low hygroscopicity.Type: GrantFiled: October 24, 1995Date of Patent: June 11, 1996Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Shoji Tamai, Norimasa Yamaya, Masahiro Ohta, Akihiro Yamaguchi
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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: 5444165Abstract: An unsaturated imide compound represented by formula (1): ##STR1## wherein Q is an alicyclic structure-containing hydrocarbon group having 4-20 carbon atoms; each of R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.i and R.sub.j represents a hydrogen atom, a halogen atom, a hydrocarbon group having 1-6 carbon atoms or a halogen-containing hydrocarbon group having 1-6 carbon atoms; each of a, b, c, d, e and f represents an integer of 0 to 4 satisfying a+b.ltoreq.4, c+d.ltoreq.4 and e+f.ltoreq.4 and D represents a divalent organic group having 2-24 carbon atoms and an ethylenically unsaturated double bond, a process for producing the unsaturated imide compound of formula (1) and intermediates for producing the unsaturated imide compound of formula (1). The unsaturated imide compound of formula (1) is well soluble in organic solvents and can give cured products excellent in heat resistance, low water absorption and flexibility.Type: GrantFiled: February 25, 1994Date of Patent: August 22, 1995Assignee: Sumitomo Chemical Company, LimitedInventors: Yasuhiro Hirano, Yasuhiro Endo, Kazuo Takebe, Mitsuhiro Shibata, Shuichi Kanagawa, Yutaka Shiomi, Masatsugu Akiba, Shinichiro Kitayama
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Patent number: 5405918Abstract: Novel polysulfide-containing polycitraconimides and polyitaconimides are disclosed. Further, a process for the sulfur-vulcanization of rubber using these novel compounds is also disclosed. Also, a sulfur-vulcanized rubber product and articles of manufacture embodying this product are disclosed. Finally, the use of the novel polysulfide-containing polycitraconimides and polyitaconimides as anti-reversion coagents in the sulfur-vulcanization of rubber is also disclosed.Type: GrantFiled: April 28, 1993Date of Patent: April 11, 1995Assignee: Akzo Nobel N.V.Inventors: Andreas H. Hogt, Auke G. Talma, Rudolf F. de Block
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Patent number: 5399715Abstract: The polyamino oligomers of this invention are obtained by reacting diisopropenylbenzenes or bis(.alpha.-hydroxyisopropyl)benzenes and anilines in the presence of an acid catalyst and characterized by the recurring unit having an indane skeleton. These polyamino oligomers can be used as curing agent for laminate resins. Also, they can be reacted with maleic anhydride to prepare polymaleimide compounds of this invention.The polymaleimide compounds of this invention are low in melting point (or softening point) and, in combination with a substance producing three-dimensional crosslinkage such as triallyl isocyanurate, aromatic diamine, etc., can provide thermosetting resin compositions suited for producing copper-clad laminates. The copper-clad laminates obtained from the thermosetting resin compositions of this invention are low in dielectric constant, heat-resistant and also low in water absorptivity, so that they are useful for multi-layer printed boards.Type: GrantFiled: June 2, 1993Date of Patent: March 21, 1995Assignee: Sumitomo Chemical Company, LimitedInventors: Shigeki Naitoh, Yasuhiro Endo, Youichi Ueda, Kunimasa Kamio
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Patent number: 5393887Abstract: A mixed bisimide having the formula: ##STR1## wherein D, A and Z are as defined in the specification, produced by reacting a diamine with an ethylenically unsaturated dicarboxylic acid anhydride and a halogenated compound containing an anhydride group and aromatic or bicyclo groups to form a bisamic acid composition and then dehydrating such composition to ring close the end groups. The halogenated end groups (Z) of the mixed bisimide component render the bisimide reaction product of the ring closing reaction flame retardant.Type: GrantFiled: October 4, 1993Date of Patent: February 28, 1995Assignee: Monsanto CompanyInventor: Christian J. Petit
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Patent number: 5380873Abstract: A coupling agent useful in conducting immunoassays, particularly assays for B12, is disclosed. The coupling agent has the formula ##STR1## Z and Z' can be the same or different and each is ##STR2## k, m and n are integers from 1 to 10, X is an alkylene group, a cycloalkylene group, an alkylcycloalkylene group, a bivalent aromatic group, or an aminoalkylene group, R and R' can be the same or different, and each is a substituted or unsubstituted aminoalkylene group having from 1 to 10 carbon atoms or a cycloalkylene or alkylcycloalkylene group having from 5 to 20 carbon atoms. Z and Z' are the same except that they can be the same or different when both are ##STR3## A method for purifying an aqueous intrinsic factor solution which contains R-protein is disclosed.Type: GrantFiled: December 22, 1992Date of Patent: January 10, 1995Assignee: Abbott LaboratoriesInventors: Christopher Bieniarz, Christopher Welch
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Patent number: 5371236Abstract: A non-crystalline ether-imide type high purity bismaleimide composition represented by formula (I): ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, and R.sup.4 each represent a hydrogen atom, a halogen atom, or an alkyl group having from 1 to 4 carbon atoms; R.sup.5 represents a hydrogen atom or a methyl group; and R.sup.6 represents a hydrogen atom, a methyl group or a phenyl group. The non-crystalline bismaleimide (I) has a purity of 95 wt % or higher, a melting point of not higher than 130.degree. C., and exhibits excellent solubility in a solvent.Type: GrantFiled: June 18, 1993Date of Patent: December 6, 1994Assignee: Mitsubishi Petrochemical Co., Ltd.Inventors: Kaoru Kanayama, Tadao Takeyama, Takeshi Nakato, Yoshinobu Ohnuma, Hiromi Chiba
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Patent number: 5364700Abstract: Described herein are novel rubber modified bismaleimide resins and prepregable resin compositions comprising these bismaleimides and one or more liquid co-reactants and optionally, one or more other additives.Type: GrantFiled: December 27, 1985Date of Patent: November 15, 1994Assignee: Amoco CorporationInventor: Linda A. Domeier
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Patent number: 5329022Abstract: The present invention relates to an improved synthesis method for the making of citraconimides wherein a citraconic anhydride is reacted with 0.5 to 2.0 equivalents of at least one amine salt. This process may be carried out in a solvent and generally leads to excellent yields of the citraconimides with high selectivity and easy purification. The present inventional so relates to a process for the production of citraconic anhydride from itaconic anhydride with an amine or phosphine catalyst and in a cosolvent.Type: GrantFiled: January 16, 1992Date of Patent: July 12, 1994Assignee: Akzo America Inc.Inventors: Auke G. Talma, Hendrika P. M. Hooft, Anna G. van de Bovenkamp-Bouwman
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Patent number: 5326881Abstract: An unsaturated imide compound represented by formula (1): ##STR1## wherein Q is an alicyclic structure-containing hydrocarbon group having 4-20 carbon atoms; each of R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.i and R.sub.j represents a hydrogen atom, a halogen atom, a hydrocarbon group having 1-6 carbon atoms or a halogen-containing hydrocarbon group having 1-6 carbon atoms; each of a, b, c, d, e and f represents an integer of 0 to 4 satisfying a+b.ltoreq.4, c+d.ltoreq.4 and e+f.ltoreq.4 and D represents a divalent organic group having 2-24 carbon atoms and an ethylenically unsaturated double bond, a process for producing the unsaturated imide compound of formula (1) and intermediates for producing the unsaturated imide compound of formula (1). The unsaturated imide compound of formula (1) is well soluble in organic solvents and can give cured products excellent in heat resistance, low water absorption and flexibility.Type: GrantFiled: October 28, 1993Date of Patent: July 5, 1994Assignee: Sumitomo Chemical Company Ltd.Inventors: Yasuhiro Hirano, Yasuhiro Endo, Kazuo Takebe, Mitsuhiro Shibata, Shuichi Kanagawa, Yutaka Shiomi, Masatsugu Akiba, Shinichiro Kitayama
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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: 5274119Abstract: A group of functionalized linking agents are disclosed. The linking agents contain thiol reactive functionalities for the covalent reaction with sulfhydryl groups from the hinge-region of antibody fragments. The linking agents also contain masked aldehyde functionalities for covalent attachment of amine-containing therapeutic agents by Schiff base formation. Carrier systems capable of delivering compounds to targeted sites in vivo based on antigen-antibody interactions are constructed from these linking agents.Type: GrantFiled: April 1, 1991Date of Patent: December 28, 1993Assignee: The Dow Chemical CompanyInventors: Kevin A. Frazier, Margaret E. Schott
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Patent number: 5262524Abstract: The present invention is directed to a method for extending the length of one of the three linker arms of the compound of Formula I in the production of novel trifunctional antibody-like compounds. Formula I is defined as follows: ##STR1## wherein X is ##STR2## wherein k=1 or 0; wherein Z is ##STR3## wherein s=1 or 0; wherein n=1 or 0;wherein q=1 or 0;wherein Y is ##STR4## wherein Y' is ##STR5## wherein p or m may be the same or different and are integers ranging from 0 to 20 with the provisos that when n=0, the sum of m and p is an integer ranging from 1 to 20, whereas when n=1, p and m are each an integer that is at least 1 and the sum of p and m is an integer ranging from 2 to 20;wherein R.sup.1 is straight or branched chain lower alkyl having from 1 to 6 carbon atoms or lower alkoxy having from 1-6 carbon atoms; andwherein R.sup.Type: GrantFiled: November 15, 1991Date of Patent: November 16, 1993Assignee: Hybritech IncorporatedInventors: Leslie D. Anderson, Clarence N. Ahlem, Ann E. Huang
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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: 5206383Abstract: This invention concerns novel o,o'-bismaleimide resins which have good processibility, novel o,o'-diamines used to prepare the resins, and the novel o,o'-bismaleimide polymers prepared by curing these resins. The polymers have thermo-oxidative and tensile properties which rival conventional p,p'- and m,m'-bismaleimide resin systems.The o,o'-bismaleimide resins of this invention have the following structure: ##STR1## wherein Y--G--Y is a bridging group with Y selected from the group consisting of oxygen, sulfur, and selenium, and G selected from a number of structures having aromatic and/or siloxane character. R.sub.a and R.sub.b are independently selected from the group consisting of hydrogen, an alkyl containing up to 4 carbon atoms, the corresponding alkoxy groups, chlorine, and bromine, or R.sub.a and R.sub.b together form a fused 6-membered aromatic ring.Type: GrantFiled: January 28, 1992Date of Patent: April 27, 1993Assignee: Allied-Signal Inc.Inventor: Raymond J. Swedo
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Patent number: 5196550Abstract: The present invention is directed to a reactive diluent comprising a backbone portion and a pendant group portion. The backbone portion comprises at least two polymerizable sites, and the pendant group portion comprising a functional group having the following formula: ##STR1## wherein Z is an ethylenically unsaturated hydrocarbyl or substituted hydrocarbyl group containing from 2 to about 12 carbon atoms and wherein said pendant group is capable of a (2+2) cyclo-addition with another like pendant group of the above formula. The chain extending reaction site is preferably used in a polymerization reaction to provide a polymeric material, and the cross-linking reactive site is preferably used to create cross-linking as needed or desired.Type: GrantFiled: April 30, 1990Date of Patent: March 23, 1993Assignee: The B. F. Goodrich CompanyInventors: Carl J. Long, II, William F. Masler, William R. Wilbur, Gary L. Julian, Julius Farkas
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Patent number: 5194545Abstract: Bismaleimides of the formula I ##STR1## wherein R denotes a radical of the formula II ##STR2## and polyimides which can be prepared from these bismaleimides, if appropriate with the addition of an aromatic diamine. The polyimides are optionally reinforced with fibers.Type: GrantFiled: November 6, 1991Date of Patent: March 16, 1993Assignee: Petrochemie Danubia Gesellschaft m.b.H.Inventors: Heinz Horacek, Gerd Greber
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Patent number: 5175309Abstract: A process for the preparation of N-substituted maleimides by conducting heat-dehydration and dehydrating imidization of N-substituted maleamic acids under azeotropic distillation of generated water in a solvent mixture containing a solvent capable of forming water azeotrope and an organic aprotic polar solvent, in the presence as catalyst of a zinc salt of a maleamic acid, metallic zinc or a zinc compound which forms a zinc salt of the N-substituted maleamic acid in the reaction system.Type: GrantFiled: December 8, 1989Date of Patent: December 29, 1992Assignee: Mitsui Toatsu Chemicals Inc.Inventors: Ryuichiro Tsumura, Kunimitsu Fukumura, Teruo Muraishi
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Patent number: 5165977Abstract: An adhesive patch for a composite structure, an adhesive for that patch and a method for forming the adhesive patch for the composite structure are described. The adhesive includes three uncured components of a bismaleimide polymeric mixture. Two of these components are liquid. The liquids include a liquid vinyl-terminated rubber monomer and a liquid bis(alkenylaromatic)aryl or bis(alkenylaromatic)alkyl monomer. The further component is a solid bismaleimide monomer that is intimately mixed and suspended in the liquid bis(alkenylaromatic)aryl or bis(alkenylaromatic)alkyl monomer and liquid vinyl-terminated rubber.Type: GrantFiled: August 2, 1990Date of Patent: November 24, 1992Assignee: Northrop CorporationInventors: Paul J. Dynes, Laura A. Hunter
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Patent number: 5160642Abstract: A clayish formation, such as encountered in rock surrounding an oil well bore, is stabilized with a quaternary ammonium salt of an imide of polymaleic anhydride. The invention is particularly relevant to hydraulic fracturing fluids used for enhanced oil recovery.Type: GrantFiled: May 25, 1990Date of Patent: November 3, 1992Assignee: Petrolite CorporationInventors: John A. Schield, Michael I. Naiman, Gary A. Scherubel
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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: 5130444Abstract: Bismaleimides of the formula I ##STR1## wherein R denotes a radical of the formula II ##STR2## and polyimides which can be prepared from these bismaleimides, if appropriate with the addition of an aromatic diamine. The polyimides are optionally reinforced with fibers.Type: GrantFiled: April 24, 1990Date of Patent: July 14, 1992Assignee: PCD Polymere Gesellschaft m.b.H.Inventors: Heinz Horacek, Gerd Greber
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Patent number: 5112989Abstract: A process for producing an unsaturated dicarboxylic acid imide compound of formula (I): ##STR1## wherein D represents a divalent organic group having at least one carbon/carbon double bond; R.sup.1 represents an n-valent organic group having at least one carbon atom; and n is an integer of 1 or above, which comprises reacting an unsaturated amide acid compound of formula (II): ##STR2## wherein D, R.sup.1, and n are as defined above, with an orthoester of formula (III): ##STR3## wherein R.sup.2 and R.sup.3, which may be the same or different, each represents a monovalent organic group having at least one carbon atom, to form an unsaturated dicarboxylic acid amide acid ester compound of formula (IV): ##STR4## wherein D, R.sup.1, R.sup.3, and n are as defined above, and then imidating the compound of formula (IV).Type: GrantFiled: March 20, 1989Date of Patent: May 12, 1992Assignee: Matsushita Electric Works Ltd.Inventors: Tatsuo Yonemoto, Eiichiro Saito, Masahiro Matsumura
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Patent number: 5091542Abstract: The present invention is directed to a compound for use as an intermediate in the production of novel trifunctional antibody-like compounds. More particularly, the present invention is directed to a compound of the formula: ##STR1## wherein X is ##STR2## wherein k=1 or 0;wherein Z is ##STR3## wherein s=1 or 0;wherein n=1 or 0;wherein q=1 or 0;wherein Y is ##STR4## wherein Y', is ##STR5## wherein p or m may be the same or different and are integers ranging from 0 to 20 with the proviso that when n=0, the sum of m and p is an integer ranging from 1 to 20, whereas when n=1, p and m are each an integer that is at least 1 and the sum of p and m is an integer ranging from 2 to 20;wherein R.sup.1 is straight or branched chain lower alkyl having from 1 to 6 carbon atoms or lower alkoxy having from 1-6 carbon atoms; andwherein R.sup.2 is hydrogen, phenyl, --COOH, or straight or branched chain lower alkyl having from 1-6 carbon atoms, with the proviso that the lower alkyl moiety may be mono substituted by --NH.sub.Type: GrantFiled: March 9, 1990Date of Patent: February 25, 1992Assignee: Hybritech IncorporatedInventors: Clarence Ahlem, Ann E. Huang
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Patent number: 5089628Abstract: The invention provides novel fluorine-containing bismaleimides represented by the general formula shown below. The bismaleimides are obtained by dehydrating and cyclizing reaction of corresponding bismaleamic acids which are also novel compounds. For example, maleic anhydride is used for preparing the bismaleamic acids. A mixture of a bismaleimide of the invention and a diamine is useful as a thermosetting resin composition. At 100.degree.-300.degree. C. the resin composition undergoes addition polymerization to turn into a solid resin which are high in moisture resistance and low in dielectric constant. For use in the resin composition it is preferable that both R.sup.1 and R.sup.2 in the general formula of the bismaleimide are --CF.sub.3. ##STR1## wherein A represents a divalent organic group having an ethylenic unsaturated bond; Rf represents fluorine atom or a perfluoroalkyl group; R.sup.1 and R.sup.Type: GrantFiled: September 21, 1989Date of Patent: February 18, 1992Assignee: Central Glass Company, LimitedInventors: Masamichi Maruta, Akihiro Fukui
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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: 5068357Abstract: A process for the preparation of N-substituted maleimides by conducting heat-dehydration and dehydrating imidization of N-substituted maleamic acids under azeotropic distillation of generated water in a solvent mixture containing a solvent capable of forming water azeotrope and an organic aproptic polar solvent, in the presence as catalyst of metallic tin, tin oxide, a tin salt of a maleamic acid or a tin compound which forms a thin salt of the N-substituted maleamic acid in the reaction system.Type: GrantFiled: June 11, 1990Date of Patent: November 26, 1991Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Ryuichiro Tsumura, Teruo Muraishi, Keiichi Ideda, Jin-Kai Wang
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Patent number: 5053520Abstract: Novel polyamino acid based coupling agents are disclosed. These reagents are useful for conjugating proteins (e.g. antibodies to enzymes) for use in diagnostic assays.Type: GrantFiled: October 1, 1989Date of Patent: October 1, 1991Assignee: Abbott LaboratoriesInventors: Christopher Bieniarz, Christopher J. Welch, Grady Barnes
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Patent number: 5026872Abstract: Novel aromatic ether ketone diamine compounds and methods for their preparation are disclosed which comprise from about 3 to 8 aromatic rings interspersed with ether and ketone linkages. The novel ether ketone diamine compounds are useful as monomeric starting materials for the preparation of useful intermediates and useful thermoplastic and high temperature resistant polymers. In preferred embodiments, the novel ether ketone diamines are useful as curing agents for epoxy resin compositions and composite materials.Type: GrantFiled: February 1, 1984Date of Patent: June 25, 1991Assignee: American CyanamidInventor: Dalip K. Kohli
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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: 4981978Abstract: Thermosettable prepolymers or resins are prepared by reacting (1) a pyrazine compound containing at least two substituent groups which have a hydrogen atom attached to a carbon atom which is attached to the ring such as tetramethylpyrazine, (2) a material containing at least two aromatic aldehyde groups, and (3) at least one of (a) a nitrogen containing aromatic heterocyclic compound containing at least one hydrogen atom attached to a carbon atom attached to the ring and a polymerizable unsaturated group such as 2-methyl-5-vinylpyridine or (b) an aldehyde containing at least one polymerizable unsaturated group such as 4-isopropenyl-1-cyclohexene-1-carboxaldehyde. These prepolymers or resins are curable to thermoset products having good mechanical and thermal properties by heat and pressure or by homopolymerization or copolymerization with N,N'-bis-imides such as 1,1'-(methylenedi-4,1-phenylene)-bismaleimide. The prepolymers are suitable for preparing composites.Type: GrantFiled: January 16, 1990Date of Patent: January 1, 1991Assignee: The Dow Chemical CompanyInventor: Duane S. Treybig
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Patent number: 4981994Abstract: A base-catalyzed process is provided for the preparation of cyanate esters, the process including the step of pre-reacting a phenolic starting material with the basic catalyst and then reacting the pre-reaction product with a cyanogen halide. The process permits the preparation of cyanate esters in high yields at reaction temperatures above room temperature.Type: GrantFiled: July 31, 1989Date of Patent: January 1, 1991Assignee: Shell Oil CompanyInventor: Roy J. Jackson