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: 4945170Abstract: A method for making polyimide polymers is provided by effecting reaction between an aliphatically unsaturated imide, such as maleimide, formaldehyde, and an organic polyamine, for example trimethylene bis(4-aminobenzoate), for example in refluxing ethanol. The polyimides produced by the simple one-step method are pure, and exhibit superior toughness, and reduced shrinkage upon cure by heating. The new product are useful as molding compounds, laminating resins, and the like, being especially suitable for airplane parts, advanced composites, high performance adhesives and printed circuit boards.Type: GrantFiled: May 30, 1986Date of Patent: July 31, 1990Assignee: American Cyanamid CompanyInventor: Dalip K. Kohli
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Patent number: 4945169Abstract: Novel homo bis-maleimide compounds containing sulfonate linkages are made by reacting an aromatic disulfonyl halide with m- or p-hydroxy phenyl maleimide and have the following formula: ##STR1## Similarly, co-bis-maleimides are made by reaching an aromatic disulfonyl halide, aromatic dihydroxy compound and m or p hydroxy phenyl maleimide having the structural formula: ##STR2## Herein R and R' are the same or different and are divalent radicals selected from the group consisting of meta arylene, para arylene, naphthalene and radicals of the formula A--A and A--Z--A wherein A is selected from the group consisting of meta arylene, para arylene and naphthalene and Z is selected from the group consisting of meta arylene, para arylene, naphthalene, carbonyl, sulfone, sulfide, sulfonyl, sulfonate, sulfoxide, ether, methylene, isopropyl, oxygen, alkyl, --CH.dbd.CH-- and --C.tbd.C-- and R.sub.1, R.sub.2, R.sub.3 and R.sub.Type: GrantFiled: July 6, 1988Date of Patent: July 31, 1990Assignee: Indspec Chemical CorporationInventor: Bojayan Durairaj
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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: 4924005Abstract: Substantially insoluble bismaleimide compositions consisting essentially of bismaleimides of the formula ##STR1## where R.sub.1 and R.sub.2 are independently hydrogen, methyl, ethyl or halogenated methyl. The phenyl groups may be substituted. The compositions, having a solubility in acetone of less than about 5% by wt., are useful as melt processable resins for high temperature resistant laminates.Type: GrantFiled: December 18, 1986Date of Patent: May 8, 1990Assignee: Monsanto CompanyInventor: Ronald H. Dahms
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Patent number: 4904801Abstract: The present invention provides a process for producing aromatic ether bismaleimides of the Formula (II) ##STR1## wherein A is a divalent mononuclear or polynuclear aromatic linking group. The process provides good yields and can be scaled up readily to commerical size runs.The present invention also provides compositions containing at least about 80 weight % of the bismaleimide of Formula (II) above.Type: GrantFiled: December 8, 1988Date of Patent: February 27, 1990Assignee: University of DaytonInventors: John M. Butler, Richard P. Chartoff, James A. Harvey
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Patent number: 4876358Abstract: Novel bismaleimides of the formula ##STR1## wherein n=1, 2, or 3 are formed in two steps by reacting a diamine and maleic anhydride to form a bismaleamic acid which is reacted with acetic anhydride in the presence of acetone to form the bismaleimide.The bismaleimide monomer and prepolymers and the polybismaleimides formed from them may have improved flexibility, processibility, toughness and solubility.Type: GrantFiled: November 25, 1987Date of Patent: October 24, 1989Assignee: Texaco Inc.Inventor: David C. Alexander
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Patent number: 4866185Abstract: The difunctional polyfluoroaromatic compounds represented by the formula ##STR1## wherein X and Y are identical and are selected from the class consisting of --COOR.sup.1, --CH.sub.2 NH.sub.2, --CH.sub.2 NCO and ##STR2## wherein R.sup.1 is --H, alkyl and R.sup.2 and R.sup.3 independently are either --H, X or alkyl and n is either 0 or 1 are disclosed. These compounds are derived from those wherein X and Y are --CN which are produced in a solvent specific reaction. The process comprises reacting pentafluorobenzonitrile with a Grignard reagent of the formula CH.sub.3 MgHal, wherein Hal is --Cl or --Br, in the presence of either tetrahydrofuran, 1,3-dioxolane, dimethoxyethane or diglyme. When the solvent employed is tetrahydrofuran, the cyano compound wherein n is 1 is obtained. When the solvent is 1,3-dioxolane, the cyano compound wherein n is 0 is obtained.Type: GrantFiled: September 6, 1988Date of Patent: September 12, 1989Assignee: ICI Americas Inc.Inventors: Ludwig A. Hartmann, John F. Stephen
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Patent number: 4826995Abstract: Novel bismaleimide derivatives of higher molecular weight polyoxyalkyleneamines of the formula: ##STR1## are prepared by reacting higher molecular weight polyoxyalkyleneamines with bismaleimides prepared from low molecular weight oxyethylenediamines. In another embodiment aromatic bismaleimides derivatives are prepared.Type: GrantFiled: November 25, 1987Date of Patent: May 2, 1989Assignee: Texaco Inc.Inventors: David C. Alexander, George P. Speranza
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Patent number: 4810638Abstract: Enzyme-labeled antibody reagents wherein the enzyme and an antibody reagent, e.g., whole polyclonal or monoclonal antibody or a fragment thereof, are covalently linked through a bis-maleimidopolyalkyleneglycol bridge group. The reagents are useful in immunoassay and other methods for detecting an antigen or hapten that can be bound by the antibody reagent. The conjugates are highly stable and water soluble, and are characterized by a high degree of immunoreactivity and enzyme activity.Type: GrantFiled: July 24, 1986Date of Patent: March 7, 1989Assignee: Miles Inc.Inventors: James P. Albarella, Robert T. Buckler
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Patent number: 4801586Abstract: This invention relates to a method for administering systemically active agents including therapeutic agents through the skin or mucosal membranes of humans and animals in a transdermal device or formulation comprising topically administering with said systemic agent an effective amount of a membrane penetration enhancer having the structural formula ##STR1## wherein X and Y, each, may represent sulfur, oxygen or two hydrogen atoms, A is a branched or a straight chain, divalent aliphatic radical having from 0 to 2 double bonds; R' is selected from the group consisting of H, a lower alkyl group having 1-4 carbon atoms, phenyl, lower alkyl or halogen substituted phenyl, acetamido, halogen, piperidinyl, lower alkyl or halogen substituted piperidinyl, carbalkoxy, carboxamide, and alkylformyl; m is 3-7; q is 2m-2x, wherein x equals the number of double bonds in the lactam ring and may be 1, 2 or 3, and R is CH.sub.3, ##STR2## wherein R" is H or halogen.Type: GrantFiled: October 7, 1986Date of Patent: January 31, 1989Assignee: Nelson Research & Development Co.Inventors: Gevork Minaskanian, James V. Peck
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Patent number: 4794190Abstract: Alpha-(4-maleimidophenyl)-alpha'-(4-isomaleimidophenyl) diisopropyl benzene, as a novel composition of matter. The compound, which may be used as a component of curable thermoset resins or as a unique, difunctional synthesis intermediate having non-symmetrical reactivity, may be prepared from the corresponding bis-maleamic acid by dehydrating at or below ordinary, ambient temperatures, using acetic anhydride or a similar dehydrating agent.Type: GrantFiled: January 28, 1987Date of Patent: December 27, 1988Assignee: Amoco CorporationInventors: Linda A. Domeier, Elke M. Clark
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Patent number: 4778900Abstract: N,N'-dimethyl aromatic diamines are prepared from the corresponding diprimary amines via a two step synthesis forming first the corresponding di-succinylimidomethylamine and then reductively cleaving the succinylimido group. The products are useful, e.g., as epoxy curing agents.Type: GrantFiled: February 5, 1986Date of Patent: October 18, 1988Assignee: American Cyanamid CompanyInventor: Dalip K. Kohli
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Patent number: 4761460Abstract: There is provided a novel polymaleimide compound represent by the formula (a) ##STR1## The present polymaleimide compound has a curability comparable to that of an epoxy resin. In addition, it is noted that a cured product prepared from the present polymaleimide compound is excellent in heat resistance and adhesion property and has a low linear expansion coefficient as compared with an epoxy resin. The above-mentioned excellent characteristics of the present polymaleimide compound are never observed with respect to conventional maleimide resins. There is also provided specific compositions containing the present polymaleimide compound for exerting the excellent effects of the present polymaleimide compound most effectively.Type: GrantFiled: March 4, 1987Date of Patent: August 2, 1988Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Masahiko Otsuka, Hidekazu Ishimura
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Patent number: 4755535Abstract: This invention provides compositions comprising a physiologically-active agent and an azacycloalkene having at least one double bond in the ring and of the general formula ##STR1## wherein X and Y, each, may represent sulfur, oxygen or two hydrogen atoms, A is a straight or branched chain, divalent aliphatic radical having from 0 to 2 double bonds; R' is selected from the group consisting of H, a lower alkyl group having 1-4 carbon atoms, phenyl, lower alkyl or halogen substituted phenyl, acetamido, halogen, piperidinyl, lower alkyl or halogen substituted piperidinyl, carbalkoxy, carboxamide, and alkylformyl; m is 3-7; q is 2m-2x, wherein x equals the number of double bonds in the lactam ring and may be 1, 2 or 3; and R is --CH.sub.3, ##STR2## wherein R" is H or halogen in an amount effective to enhance the penetration of the physiologically-active agent through the skin or other membrane of the body of an animal.Type: GrantFiled: April 23, 1986Date of Patent: July 5, 1988Assignee: Nelson Research & Development Co.Inventors: Gevork Minaskanian, James V. Peck
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Patent number: 4745197Abstract: Bismaleimides having the general formula ##STR1## in which n is a whole number between 5 and 70 and --X-- is --O-- or --NH-- are prepared through the reaction of the corresponding amino-terminated polyoxybutylenes with 2 moles of maleic anhydride. They are suited as toughening agents in high grade reactive resins.Type: GrantFiled: June 30, 1987Date of Patent: May 17, 1988Assignee: BASF AktiengesellschaftInventors: Philipp Eisenbarth, Anton Hesse, Jan Holoch, Roland Peter
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Patent number: 4709050Abstract: Substituted-(hydroxyphenyl)-pyrrolidine-2,5-dione derivatives of the formula ##STR1## are prepared by the reaction of the appropriate maleimide and phenolic compounds and are useful as stabilizers for organic polymers.Type: GrantFiled: November 15, 1985Date of Patent: November 24, 1987Assignee: Ciba-Geigy CorporationInventors: John D. Spivack, Stephen D. Pastor
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Patent number: 4691025Abstract: Described herein are novel bismaleimides and prepregable resin compositions comprising these bismaleimides and one or more liquid coreactants and optionally, one or more other additives.Type: GrantFiled: December 22, 1983Date of Patent: September 1, 1987Assignee: Amoco CorporationInventors: Linda A. Domeier, Hugh C. Gardner
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Patent number: 4675414Abstract: Aliphatic polyethers having at least two N-methylmaleimide groups chemica joined thereto by a carbonate linkage are provided and a method for making such compounds. The hydroxy-terminated aliphatic polyether, such as polypropylene glycol, is initially reacted with carbonyl chloride to form the chloroformate. The polyether chloroformate derivative is then reacted with N-hydroxymethylmaleimide yielding the bis or tris(maleimidomethyl)carbonate of said polyether.Type: GrantFiled: March 8, 1985Date of Patent: June 23, 1987Assignee: The United States of America as represented by the Secretary of the NavyInventors: Albert A. DeFusco, Eugene C. Martin
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Patent number: 4654407Abstract: Described herein are novel bismaleimides and prepregable resin compositions comprising these bismaleimides and one or more liquid coreactants and optionally, one or more other additives. The novel bismaleimides, such as alpha, alpha-bis-(4-maleimidophenyl)-meta-diisopropylbenzene, are characterized by the presence of three aromatic rings in the molecular structure and in some respects optimize the desirable characteristics of the one or two and four aromatic ring-containing bismaleimides in resins prepared therefrom.Type: GrantFiled: August 2, 1985Date of Patent: March 31, 1987Assignee: Amoco CorporationInventor: Linda A. Domeier
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Patent number: 4629798Abstract: Organic polymers which are "hydroxyphenyl-substituted" and "ether-substituted" polypyrroles ("PP") linked through N-adjacent C atoms, are disclosed which are compactable, extrudable and are also electrical conductors. When such PPs are prepared by electrochemical deposition with an appropriate electrolyte, they are also soluble in commonly available solvents, provided at least one of the 3- or 4-positions of the pyrrole nucleus is substituted with a substituent having either a hydroxyphenyl, or an ether structure. By choice of the hydroxyphenyl and/or ether substituent on one of the substitutable positions (3- or 4-) of the pyrrole nucleus, or both, the PP may be tailored for use either as a semiconductor having a conductivity in the range from about 10.sup.-5 to about 10.sup.-2 S/cm, or a relatively good conductor having a conductivity in the range from about 10.sup.-2 to about 10.sup.2 S/cm.Type: GrantFiled: August 19, 1985Date of Patent: December 16, 1986Assignee: The B. F. Goodrich CompanyInventor: Lee Traynor
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Patent number: 4564683Abstract: Bismaleimides of the formula ##STR1## wherein R.sub.1 and R.sub.2 each independently is H, C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy, C1 or Br, orR.sub.1 and R.sub.2 together form a fused 6-membered hydrocarbon aromatic ring,with the proviso that R.sub.1 and R.sub.2 are not t-butyl or t-butoxy;X is O, S or Se;n is 1-3; andthe alkylene bridging group, optionally, is substituted by 1-3 methyl groups or by fluorine,form polybismaleimide resins which have valuable physical properties.Uniquely, these compounds permit extended cure times, i.e., they remain fluid for a time sufficient to permit the formation of a homogeneous melt prior to curing.Type: GrantFiled: April 10, 1984Date of Patent: January 14, 1986Assignee: The United States of America as Represented by the United States Department of EnergyInventors: Johnnie E. Adams, Donald R. Jamieson
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Patent number: 4518755Abstract: Novel imido copolymers are prepared by copolymerizing:[i] a bis-maleimide of the structural formula: ##STR1## with [ii] a (meth)acrylic acid amide.The subject copolymers are applicable to the production of a variety of useful shaped articles, coatings, laminates, foams, and the like.Type: GrantFiled: May 30, 1979Date of Patent: May 21, 1985Assignee: Rhone-Poulenc IndustriesInventors: Jean L. Locatelli, Bernard Rollet
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Patent number: 4518754Abstract: Novel imido copolymers are prepared by copolymerizing:[i] a bis-maleimide of the structural formula: ##STR1## [ii] an olefinically unsaturated comonomer copolymerizable therewith. The subject copolymers are applicable to the production of a variety of useful shaped articles, coatings, laminates, foams, and the like.Type: GrantFiled: May 30, 1979Date of Patent: May 21, 1985Assignee: Rhone-Poulenc IndustriesInventors: Jean L. Locatelli, Bernard Rollet
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Patent number: 4500719Abstract: Disclosed are novel alkenylphenylmaleimide derivatives having the general formula ##STR1## where R is an alkenyl radical of from 3 to 12 carbon atoms, R' is a hydrogen atom, a halogen atom, or a straight-chain or branched alkyl radical of from 1 to 4 carbon atoms, and n is a whole number of from 1 to 4, and linear dimers thereof as well as a process for the preparation of such maleimide compounds.Type: GrantFiled: August 13, 1982Date of Patent: February 19, 1985Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Masayuki Oba, Motoo Kawamata, Hikotada Tsuboi, Nobuhito Koga
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Patent number: 4418181Abstract: The compositions described herein comprise polyimides having bis-maleimide terminal groups and having the formula: ##STR1## wherein Q is a trivalent aromatic radical, Ar is a divalent aromatic radical, Ar" is a tetravalent aromatic radical and n has a value of 0-20. Derivatives may be made of these compounds by homopolymerization, copolymerization with other copolymerizable materials and by reaction with Diels-Alder reactable materials.Type: GrantFiled: May 26, 1981Date of Patent: November 29, 1983Assignee: Plastics Engineering CompanyInventor: Walter J. Monacelli
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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