Double Bond Between Ring Carbons In Each Of The Two Nitrogen Containing Hetero Rings (e.g., Bis-maleimides, Etc.) Patents (Class 548/521)
  • Patent number: 4945170
    Abstract: 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: Grant
    Filed: May 30, 1986
    Date of Patent: July 31, 1990
    Assignee: American Cyanamid Company
    Inventor: Dalip K. Kohli
  • Patent number: 4945169
    Abstract: 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: Grant
    Filed: July 6, 1988
    Date of Patent: July 31, 1990
    Assignee: Indspec Chemical Corporation
    Inventor: Bojayan Durairaj
  • Patent number: 4935523
    Abstract: 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: Grant
    Filed: May 4, 1987
    Date of Patent: June 19, 1990
    Assignee: The Boeing Company
    Inventors: Hyman R. Lubowitz, Clyde H. Sheppard
  • Patent number: 4924005
    Abstract: 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: Grant
    Filed: December 18, 1986
    Date of Patent: May 8, 1990
    Assignee: Monsanto Company
    Inventor: Ronald H. Dahms
  • Patent number: 4904801
    Abstract: 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: Grant
    Filed: December 8, 1988
    Date of Patent: February 27, 1990
    Assignee: University of Dayton
    Inventors: John M. Butler, Richard P. Chartoff, James A. Harvey
  • Patent number: 4876358
    Abstract: 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: Grant
    Filed: November 25, 1987
    Date of Patent: October 24, 1989
    Assignee: Texaco Inc.
    Inventor: David C. Alexander
  • Patent number: 4866185
    Abstract: 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: Grant
    Filed: September 6, 1988
    Date of Patent: September 12, 1989
    Assignee: ICI Americas Inc.
    Inventors: Ludwig A. Hartmann, John F. Stephen
  • Patent number: 4826995
    Abstract: 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: Grant
    Filed: November 25, 1987
    Date of Patent: May 2, 1989
    Assignee: Texaco Inc.
    Inventors: David C. Alexander, George P. Speranza
  • Patent number: 4810638
    Abstract: 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: Grant
    Filed: July 24, 1986
    Date of Patent: March 7, 1989
    Assignee: Miles Inc.
    Inventors: James P. Albarella, Robert T. Buckler
  • Patent number: 4801586
    Abstract: 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: Grant
    Filed: October 7, 1986
    Date of Patent: January 31, 1989
    Assignee: Nelson Research & Development Co.
    Inventors: Gevork Minaskanian, James V. Peck
  • Patent number: 4794190
    Abstract: 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: Grant
    Filed: January 28, 1987
    Date of Patent: December 27, 1988
    Assignee: Amoco Corporation
    Inventors: Linda A. Domeier, Elke M. Clark
  • Patent number: 4778900
    Abstract: 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: Grant
    Filed: February 5, 1986
    Date of Patent: October 18, 1988
    Assignee: American Cyanamid Company
    Inventor: Dalip K. Kohli
  • Patent number: 4761460
    Abstract: 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: Grant
    Filed: March 4, 1987
    Date of Patent: August 2, 1988
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Masahiko Otsuka, Hidekazu Ishimura
  • Patent number: 4755535
    Abstract: 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: Grant
    Filed: April 23, 1986
    Date of Patent: July 5, 1988
    Assignee: Nelson Research & Development Co.
    Inventors: Gevork Minaskanian, James V. Peck
  • Patent number: 4745197
    Abstract: 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: Grant
    Filed: June 30, 1987
    Date of Patent: May 17, 1988
    Assignee: BASF Aktiengesellschaft
    Inventors: Philipp Eisenbarth, Anton Hesse, Jan Holoch, Roland Peter
  • Patent number: 4709050
    Abstract: 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: Grant
    Filed: November 15, 1985
    Date of Patent: November 24, 1987
    Assignee: Ciba-Geigy Corporation
    Inventors: John D. Spivack, Stephen D. Pastor
  • Patent number: 4691025
    Abstract: 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: Grant
    Filed: December 22, 1983
    Date of Patent: September 1, 1987
    Assignee: Amoco Corporation
    Inventors: Linda A. Domeier, Hugh C. Gardner
  • Patent number: 4675414
    Abstract: 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: Grant
    Filed: March 8, 1985
    Date of Patent: June 23, 1987
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Albert A. DeFusco, Eugene C. Martin
  • Patent number: 4654407
    Abstract: 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: Grant
    Filed: August 2, 1985
    Date of Patent: March 31, 1987
    Assignee: Amoco Corporation
    Inventor: Linda A. Domeier
  • Patent number: 4629798
    Abstract: 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: Grant
    Filed: August 19, 1985
    Date of Patent: December 16, 1986
    Assignee: The B. F. Goodrich Company
    Inventor: Lee Traynor
  • Patent number: 4564683
    Abstract: 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: Grant
    Filed: April 10, 1984
    Date of Patent: January 14, 1986
    Assignee: The United States of America as Represented by the United States Department of Energy
    Inventors: Johnnie E. Adams, Donald R. Jamieson
  • Patent number: 4518755
    Abstract: 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: Grant
    Filed: May 30, 1979
    Date of Patent: May 21, 1985
    Assignee: Rhone-Poulenc Industries
    Inventors: Jean L. Locatelli, Bernard Rollet
  • Patent number: 4518754
    Abstract: 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: Grant
    Filed: May 30, 1979
    Date of Patent: May 21, 1985
    Assignee: Rhone-Poulenc Industries
    Inventors: Jean L. Locatelli, Bernard Rollet
  • Patent number: 4500719
    Abstract: 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: Grant
    Filed: August 13, 1982
    Date of Patent: February 19, 1985
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Masayuki Oba, Motoo Kawamata, Hikotada Tsuboi, Nobuhito Koga
  • Patent number: 4418181
    Abstract: 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: Grant
    Filed: May 26, 1981
    Date of Patent: November 29, 1983
    Assignee: Plastics Engineering Company
    Inventor: Walter J. Monacelli
  • Patent number: 4400519
    Abstract: 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: Grant
    Filed: February 4, 1980
    Date of Patent: August 23, 1983
    Assignee: Teijin Limited
    Inventors: Tsuneo Hagiwara, Akihiro Horike
  • Patent number: 4377673
    Abstract: 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: Grant
    Filed: March 2, 1982
    Date of Patent: March 22, 1983
    Assignee: Plastics Engineering Company
    Inventors: Gaetano F. D'Alelio, deceased, Phillip A. Waitkus
  • Patent number: 4377525
    Abstract: 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: Grant
    Filed: March 2, 1982
    Date of Patent: March 22, 1983
    Assignee: Plastics Engineering Company
    Inventors: Gaetano F. D'Alelio, deceased, Phillip A. Waitkus