Benzene Ring Bonded Directly To Ring Nitrogen Of The Five-membered Hetero Ring (e.g., N-phenylmaleimide, Etc.) Patents (Class 548/549)
  • Patent number: 5773630
    Abstract: N-Substituted cyclic imides are obtained by reacting a cyclic acid anhydride with an amine in the presence of a solvent and an acid catalyst at 80.degree. to 200.degree. C. and with removal of the water formed, it being particularly advantageous to carry out this reaction in the presence of a stabilizer and an inert, dipolar aprotic cosolvent, optionally to add an inert organic solvent of low or zero polarity to the reaction mixture present after the reaction, to add a non-aqueous base in an amount of 0.5 to 50% by weight, based on the cyclic anhydride of the formula (II) used, and to separate off the precipitate formed to give a filtrate containing the N-substituted cyclic imide.
    Type: Grant
    Filed: February 6, 1996
    Date of Patent: June 30, 1998
    Assignee: Bayer Aktiengesellschaft
    Inventors: Torsten Groth, Karl-Erwin Piejko, Winfried Joentgen, Josef Kasbauer, Bernd Alig, Werner Struver
  • Patent number: 5741913
    Abstract: A process for preparing N-substituted maleimide is disclosed, which includes reacting maleic anhydride with a primary amine using both a non-polar solvent and a protic polar solvent in the presence of an acid catalyst.
    Type: Grant
    Filed: January 28, 1997
    Date of Patent: April 21, 1998
    Assignee: Daihachi Chemical Industry Co., Ltd.
    Inventors: Masasuke Oda, Toshimitsu Noda
  • Patent number: 5734063
    Abstract: The present invention provides a method for preparation of a compound of the formula (I) useful as a fog restrainer for a silver halide light-sensitive material, especially for a heat-developing light-sensitive material and a synthetic intermediate for the fog restrainer. The method makes it possible to obtain the fog restrainer in good yield and in short steps. ##STR1## wherein, R.sup.1 is alkyl, cycloalkyl, or aryl, R.sup.2 and R.sup.3 are hydrogen atom or alkyl, R.sup.4 is hydrogen atom or acyl, and R.sup.1 and R.sup.4 may be bonded together to form 5- or 6-membered ring.
    Type: Grant
    Filed: October 24, 1996
    Date of Patent: March 31, 1998
    Assignee: Fuji Photo Film Co.,Ltd.
    Inventors: Katsuyoshi Yamakawa, Tadahisa Sato
  • Patent number: 5684163
    Abstract: A process for the preparation of a N-)ortho-alkylphenyl)-imide of the formula ##STR1## in which R.sup.1 to R.sup.9 is defined in the specification which comprises reacting a cyclic anhydride of the formula ##STR2## wherein R.sup.6 to R.sup.9 are difined in the specification with an amine of the formula ##STR3## optionally in the presence of an acid catalyst and optionally in the presence of a solvent which is immiscible or only slightly miscible with water but can form an azeotrope with water, at a temperature between 100.degree. to 200.degree. C. under conditions so that the water formed during the reaction is removed from the reaction mixture without the addition of a polymerization inhibitor or a dipolar solvent. The final products are used as intermediates to prepare heat-stable plastics as well as intermediates to prepare pharmaceutical and agricultural chemicals.
    Type: Grant
    Filed: February 5, 1996
    Date of Patent: November 4, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Torsten Groth, Bernd-Michael Konig, Josef Kasbauer, Michael Schwamborn
  • Patent number: 5609848
    Abstract: Haloaryl compounds are lithiated and thereafter metalated with one of the following organometallic groups: Sn(n--Bu).sub.3 or SnMe.sub.3. The resulting aryltin compound can be transmetalated in site-specific reaction with one of the following organometallic groups: HgX, Hg(OAc).sub.2, BX.sub.3, or BZ.sub.2, wherein X is Cl, Br, or I, and Z is alkyl or alkoxy. The metalated compounds are subsequently radiohalogenated via a demetalation reaction. A functional group suitable for conjugation to protein can be added subsequent or preferably prior to the radiohalogenation.Also compounds of the formula: R.sub.1 --Ar--R.sub.2, wherein R.sub.1 is either a radiohalogen or any one of the organometallic groups stated above, Ar is aromatic or heteroaromatic ring, and R.sub.2 is a short-chain substituent that does not activate the aromatic ring and that bears a functional group, or a precursor thereof, suitable for conjugation to protein under conditions that preserve the biological activity of the protein.
    Type: Grant
    Filed: September 23, 1991
    Date of Patent: March 11, 1997
    Assignee: NeoRx Corporation
    Inventors: D. Scott Wilbur, Alan R. Fritzberg
  • Patent number: 5585484
    Abstract: 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: Grant
    Filed: April 19, 1995
    Date of Patent: December 17, 1996
    Assignee: Albert Einstein College of Medicine of Yeshiva University, A Division of Yeshiva University
    Inventors: A. Seetharama Acharya, Belur N. Manjula, Paul K. Smith
  • Patent number: 5556991
    Abstract: The present invention provides a stabilized maleimide compound which is hard to discolor during storage. The maleimide compound has a content of primary amines of not more than 500 ppm or further has a content of maleic anhydride in the range of 5 to 2,000 ppm or a content of 2-amino-N-substituted succinimide compounds of not more than 300 ppm. Furthermore, it is preferable that the content of chlorine compounds reduced as a chlorine atom is not more than 10 ppm and further the content of volatile components having a boiling point of not more than 200.degree. C. at normal pressure is not more than 2,000 ppm.
    Type: Grant
    Filed: September 22, 1994
    Date of Patent: September 17, 1996
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Yuichi Kita, Koichi Nakagawa, Kazuo Kishino
  • Patent number: 5554769
    Abstract: 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: Grant
    Filed: June 5, 1995
    Date of Patent: September 10, 1996
    Assignee: The Boeing Company
    Inventors: Clyde H. Sheppard, Hyman R. Lubowitz
  • Patent number: 5523414
    Abstract: In the production of an N-unsubstituted maleinimide by the ring-closing alcohol-removing treatment of an N-unsubstituted maleinamic ester for conversion into an imide, an acid catalyst or a mono(cyclo)alkyl sulfuric ester is used for the reaction. In this case, the alcohol concentration in the reaction solution is preferable to be adjusted to a low level. By using a maleinamic acid and an alcohol in conjunction with an inert solvent and an acid catalyst, a mixture of maleinamic acid with an acid catalyst, or a mono(cyclo)alkyl sulfuric ester, a corresponding maleinamic ester is obtained.
    Type: Grant
    Filed: May 9, 1994
    Date of Patent: June 4, 1996
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Yasuhiro Kume, Takehiko Morita, Kazuo Kishino, Yuichi Kita, Hitoshi Kanei
  • Patent number: 5508427
    Abstract: A bisimide compound of the following general formula (I). ##STR1## (wherein each of the R's is an alkyl group having 1 to 4 carbon atoms, a phenyl group or a phenyl group substituted with an alkyl or alkoxy group having 1 to 4 carbon atoms, a plurality of these R's may be the same or different, each of the Z's is ##STR2## a plurality of these Z's may be the same or different, Y is an arylene group or an aryleneoxy group whose terminal oxygen atom bonds to (CH.sub.2).sub.n, n is an integer of 0 to 20, and m is an integer of 1 to 30.), and a process for the production of the above bisimide compound, which comprises reacting a bisamic acid corresponding to this bisimide compound in a cyclodehydration reaction.
    Type: Grant
    Filed: April 6, 1994
    Date of Patent: April 16, 1996
    Assignee: Tomoegawa Paper Co., Ltd.
    Inventors: Toshio Tagami, Yukinori Sakumoto, Takeshi Hashimoto
  • Patent number: 5484948
    Abstract: 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: Grant
    Filed: August 2, 1994
    Date of Patent: January 16, 1996
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Keizaburo Yamaguchi, Tatsuhiro Urakami, Yoshimitsu Tanabe, Midori Yamazaki, Shoji Tamai, Norimasa Yamaya, Masahiro Ohta, Akihiro Yamaguchi
  • Patent number: 5475021
    Abstract: The present invention includes N-substituted maleimides (1(H)-Pyrrole-2,5-dione (Maleimide) analogs and succinimides which act as potent nonsteroidal anti-inflammatory drugs and are capable of dual inactivation or selective inactivation of the cyclooxygenase and the peroxidase activities of prostaglandin endoperoxide synthase (PGHS).
    Type: Grant
    Filed: December 3, 1993
    Date of Patent: December 12, 1995
    Assignee: Vanderbilt University
    Inventors: Lawrence J. Marnett, Amit S. Kalgutkar
  • Patent number: 5410069
    Abstract: A polymerzable compound represented by the general formula (1) X--R.sub.1 --Y where X is un unsaturated imide group having substituents R.sub.2 and R.sub.3, or an itacon imide group where R.sub.2 and R.sub.3 are selected from the group consisting of hydrogen, a lower alkyl group and an aromatic group having a substituent p which is hydrogen, a lower alkyl group, or an alkoxy group, and Y is a styryl group, and R.sub.1 is a divalent organic group.The polymerizable compounds is excellent in formability, and find a wide variety of applications because they have functional groups different in reactivity from each other and hence allow the curing conditions to control. The cured polymers are excellent in thermal durability, mechanical properties and electrical properties, making it possible to achieve higher performance, higher reliability, highly compact and lower weight of electric apparatuses and electronic parts.
    Type: Grant
    Filed: December 8, 1992
    Date of Patent: April 25, 1995
    Assignee: Hitachi, Ltd.
    Inventors: Shin Nishimura, Yoshinori Kawai, Satoru Amou, Akira Nagai, Masahiro Suzuki, Akio Takahashi, Akio Mukoh
  • Patent number: 5399673
    Abstract: Compounds containing at least one alkenyl group, at least one maleimide group and at least one rodlike mesogenic moiety are prepared by reacting one or more aminophenols containing one or more rodlike mesogenic moieties with a stoichiometric quantity of a maleic anhydride per amine group of said aminophenol and then alkenylating the resulting phenolic functional maleimide.
    Type: Grant
    Filed: February 9, 1993
    Date of Patent: March 21, 1995
    Assignee: The Dow Chemical Company
    Inventor: Robert E. Hefner, Jr.
  • Patent number: 5397708
    Abstract: A method for determining the concentration of sulfide in a process stream. The method comprises the steps of adding to a process stream a sulfide scavenger (probe) that changes electronic properties when it reacts with sulfide. One can then monitor the electronic properties of the sulfide scavenger in the process stream to determine the concentration of sulfide present. In a preferred embodiment, the sulfide scavenger is either fluorescent and when it reacts with sulfide becomes inactive or is inactive and when it reacts with sulfide becomes fluorescent.
    Type: Grant
    Filed: May 13, 1993
    Date of Patent: March 14, 1995
    Assignee: Nalco Chemical Company
    Inventors: Ronald B. Lessard, Manian Ramesh
  • Patent number: 5359087
    Abstract: The present invention provides bioactive compounds of the general formula: ##STR1## wherein R is H, (C.sub.1 -C.sub.4)alkyl, (C.sub.3 -C.sub.6)cycloalkyl, (C.sub.3 -C.sub.6)cycloalkyl(C.sub.1 -C.sub.4)alkyl, allyl, (C.sub.6 -C.sub.10)aryl or (C.sub.1 -C.sub.4)alkylCO.sub.2 Y; Y is H, (C.sub.1 -C.sub.4)alkyl or (C.sub.6 -C.sub.10)aryl; each X is individually H, (C.sub.1 -C.sub.4)alkyl, (C.sub.6 -C.sub.10)aryl, (C.sub.3 -C.sub.6)cycloalkyl(C.sub.1 -C.sub.4)alkyl, or (C.sub.3 -C.sub.6)cycloatkyl; the bond represented by--is present or is absent; and the pharmaceutically acceptable salts thereof, and methods for using said compounds to stimulate receptors in the mammalian nervous systems.
    Type: Grant
    Filed: June 3, 1993
    Date of Patent: October 25, 1994
    Assignee: Regents of the University of Minnesota
    Inventors: Rodney L. Johnson, Nalin L. Subasinghe, James F. Koerner
  • Patent number: 5329028
    Abstract: The invention is from the field of heterobifunctional cross-linking reagents. More particularly, the invention concerns cross-linking reagents which combine a nucleophilic hydrazide residue with an electrophilic maleimide residue, thereby allowing coupling of aldehydes to free thiols.
    Type: Grant
    Filed: August 5, 1992
    Date of Patent: July 12, 1994
    Assignee: Genentech, Inc.
    Inventors: Avi J. Ashkenazi, Steven M. Chamow, Timothy P. Kogan
  • Patent number: 5324709
    Abstract: A tetrahydrofuran derivative represented by the following general formula [I]: ##STR1## wherein A represents direct bonding or a group represented by --B--CHR.sup.1 --(wherein B represents oxygen atom, sulfur atom or imino group; R.sup.1 represents hydrogen atom or an alkyl group); R represents hydrogen atom, halogen atom, hydroxyl group, an alkoxy group, benzyloxy group, an alkylsulfonyloxy group or a group represented by --O--COR.sup.2 (wherein R.sup.2 represents an alkyl group, a haloalkyl group, an alkenyl group, a cycloalkyl group, phenyl group, benzyl group, an alkoxy group, an alkylamino group or a dialkylamino group; X represents halogen atom; Y represents hydrogen atom or halogen atom) and the herbicide containing the same as the effective ingredient. The compounds of the present invention have exceedingly high herbicidal activity, and furthermore, the compounds are superior to the known similar compounds in terms of safety on crops. Thus, the compounds are useful as herbicides.
    Type: Grant
    Filed: November 20, 1992
    Date of Patent: June 28, 1994
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Natsume Bunji, Kyomura Nobuo, Suzuki Seiichi, Takahashi Yoji, Jikihara Tetsuo
  • Patent number: 5306828
    Abstract: In a process for the preparation of substituted maleimides the corresponding amines are reacted with maleic anhydride and the thermal imidization of the resulting substituted amic-acids is effected in a mixed apolar/polar aprotic solvent medium in the presence of an acid catalyst, a substantial portion of the apolar solvent is subsequently selectively removed from the reaction mixture and most of the final product is precipitated.
    Type: Grant
    Filed: February 13, 1992
    Date of Patent: April 26, 1994
    Assignee: Bromine Compounds Ltd.
    Inventors: Michel Adda, Chaim Eidelman, Leonard Shorr
  • Patent number: 5288694
    Abstract: The invention relates to new N-aryl-nitrogen heterocycles of the general formula (I) ##STR1## in which R.sup.1 represents hydrogen or halogen,R.sup.2 represents hydrogen or an in each case optionally substituted, straight-chain or branched radical from the series comprising alkyl, alkenyl or cycloalkyl andA represents one of the radicals or ##STR2## where R.sup.3 represents alkyl,R.sup.4 represents alkyl andR.sup.5 represents hydrogen or alkyl,a plurality of processes for their preparation, and their use as herbicides.
    Type: Grant
    Filed: November 23, 1992
    Date of Patent: February 22, 1994
    Assignee: Bayer Atkiengesellschaft
    Inventors: Otto Schallner, Klaus Lurssen, Hans-Joachim Santel, Robert R. Schmidt, Renate Vosswinkel
  • Patent number: 5274135
    Abstract: A process for preparing a 3- or 4-aminobenzocyclobutene comprises aminating a 3- or 4-halo- or sulfonyloxybenzocyclobutene reactant with an aminating agent by heating at a temperature from about 80.degree. C. to a temperature at which dimerization or oligomerization of a benzocyclobutene reactant or product is a significant side reaction, in the presence of a metal-containing catalyst, for a time sufficient to aminate the halo- or sulfonyloxybenzocyclobutene reactant. In another aspect, this invention relates to a process for making a 3- or 4-phthalimido- or maleimidobenzocyclobutene, comprising reacting a 3- or 4-halobenzocyclobutene reactant with a phthalimide or maleimide compound in the presence of a metal-containing catalyst. The resulting phthalimido- or maleimidobenzocyclobutene can be hydrolyzed to a 3- or 4-aminobenzocyclobutene.
    Type: Grant
    Filed: September 20, 1991
    Date of Patent: December 28, 1993
    Assignee: The Dow Chemical Company
    Inventors: Kenneth J. Bruza, Arnold E. Young, Kurt A. Bell
  • Patent number: 5250702
    Abstract: A compound of the formula II: ##STR1## wherein n is an integer of 2 to 10,A' is a bivalent linking group formed by reacting both the reactive groups of a cross linking reagent, andB is a residue of a polypeptide compound,and physiologically acceptable salts thereof are disclosed. Such compound is useful as a non-radioactive carrier for radioactive metal elements.
    Type: Grant
    Filed: April 26, 1991
    Date of Patent: October 5, 1993
    Assignee: Nihon Medi-Physics Co., Ltd.
    Inventors: Susumu Kondo, Miki Kurami, Makoto Azuma
  • Patent number: 5175309
    Abstract: 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: Grant
    Filed: December 8, 1989
    Date of Patent: December 29, 1992
    Assignee: Mitsui Toatsu Chemicals Inc.
    Inventors: Ryuichiro Tsumura, Kunimitsu Fukumura, Teruo Muraishi
  • Patent number: 5151487
    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## 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: November 26, 1991
    Date of Patent: September 29, 1992
    Assignee: The Boeing Company
    Inventors: Hyman R. Lubowitz, Clyde H. Sheppard
  • Patent number: 5143953
    Abstract: Thermal stability of vinyl halide polymers is enhanced by the use of dienophiles such as N-alkyl maleimides, and bis compounds thereof, disclosed herein. The maleimides and bis compounds thereof produce synergistic results in terms of thermal stability of vinyl halide polymers when used in conjunction with conventional metal-containing thermal stabilizers. Environmental concerns are abated and certain other advantages are realized if the maleimides disclosed herein are used in conjunction with conventional nonmetallic thermal stabilizers to stabilize vinyl halide polymers against heat deterioration. Bis compounds of the N-alkyl maleimides disclosed herein, when used as thermal stabilizers for vinyl halide polymers, promote crosslinking without degrading the vinyl halide polymer.
    Type: Grant
    Filed: December 28, 1990
    Date of Patent: September 1, 1992
    Assignee: The B. F. Goodrich Company
    Inventor: Naser Pourahmady
  • Patent number: 5136052
    Abstract: A process for the manufacture of N-phenylmaleimide which comprises reacting maleic anhydride with aniline in a single step at elevated temperature in the presence of a water-immiscible organic solvent capable of forming an azeotrope with water and of p-toluenesulfonic acis as catalyst.
    Type: Grant
    Filed: May 29, 1991
    Date of Patent: August 4, 1992
    Assignee: U C B, S.A.
    Inventors: August Van Gysel, Ivan Vanden Eynde, Jean-Claude Vanovervelt
  • Patent number: 5130378
    Abstract: The present invention relates to copolymers prepared from olefinically unsaturated compounds, having a molecular weight (M.sub.n) of 600 to 20,000 and containing 0.1 to 6.0% by weight of secondary amino groups, --NH--, in the form of structural units corresponding to formula I ##STR1## wherein R.sub.1 is a saturated aliphatic hydrocarbon radical containing 2 to 6 carbon atoms, provided that at least two carbon atoms are arranged between the two nitrogen atoms, andR.sub.2 is a methyl, ethyl or 2-hydroxyethyl group.The present invention also relates to a process for the production of these copolymers.
    Type: Grant
    Filed: August 28, 1990
    Date of Patent: July 14, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Harald Blum, Josef Pedain, Christian Wamprecht
  • Patent number: 5128484
    Abstract: The present invention is directed to an acrylonitrile maleimides solution composition of highly desirable shelf like, having the acid component in said acrylonitrile maleimides soltuion adjusted to a level of no more than 0.1% by weight based on the amount of said maleimides contained in said solution and having a polymerization inhibitor in said solution adjusted to a level in the range of 0.0001 to 1% by weight based on the amount of said solution, and a method for the production thereof.
    Type: Grant
    Filed: December 27, 1988
    Date of Patent: July 7, 1992
    Assignee: Sokubai Kagaku Kogyo, Co., Ltd.
    Inventors: Yuichi Kita, Kazuo Kishino, Masakazu Nakagawa, Hitoshi Kanei, Kentaro Sakamoto, Takeshi Okuno
  • Patent number: 5118849
    Abstract: Intermediates of the formula ##STR1## are new, whereR stands for alkyl, alkenyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, or cycloalkenylalkyl, in each case having up to 20 carbon atoms, in each case optionally branched and in each case interrupted by 1 to 4 oxygen atoms, andX stands for hydrogen or halogen, and are useful for synthesizing herbicidal and plant growth regulating compounds.
    Type: Grant
    Filed: April 16, 1991
    Date of Patent: June 2, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Otto Schallner, Reiner Fischer, Albrecht Marhold, Karl-Julius Reubke, Hans-Joachim Santel, Robert R. Schmidt, Klaus Lurssen, Harry Strang
  • Patent number: 5101041
    Abstract: A group of functionalized triamine chelants and their derivatives that form complexes with radioactive metal ions are disclosed. The complexes can be covalently attached to a protein or an antibody or antibody fragment and used for therapeutic and/or diagnostic purposes.
    Type: Grant
    Filed: April 26, 1989
    Date of Patent: March 31, 1992
    Assignee: The Curators of the University of Missouri
    Inventors: David E. Troutner, Christy S. John, Maroor R. A. Pillai
  • Patent number: 5087701
    Abstract: 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: Grant
    Filed: March 5, 1990
    Date of Patent: February 11, 1992
    Assignee: The Boeing Company
    Inventors: Hyman R. Lubowitz, Clyde H. Sheppard
  • Patent number: 5079331
    Abstract: Heat-resistant epoxy resin composition obtained by incorporation of 2-(4-hydroxyphenyl)-2-(4-maleimidophenyl)propane in a resin composition consisting esssentially of epoxy resin and an epoxy hardener is disclosed.
    Type: Grant
    Filed: May 23, 1990
    Date of Patent: January 7, 1992
    Assignee: Mitsui Toatsu Chemical, Inc.
    Inventors: Mikio Kitahara, Koichi Machida, Takayuki Kubo, Motoyuki Torikai, Koutarou Asahina, Yoshimitsu Tanabe, Keizaburo Yamaguchi, Akihiro Yamaguchi
  • Patent number: 5039334
    Abstract: Herbicidal and plant growth-regulating substituted N-aryl nitrogen heterocycles of the formula ##STR1## in which Het stands for ##STR2## where A stands for ##STR3## where R.sup.1 and R.sup.2 in each case independently of one another stand for hydrogen, halogen, halogenoalkyl or alkyl,Y.sup.1 and Y.sup.2 in each case stand for oxygen or sulphur andZ stands for hydrogen, hydroxyl or chlorine,R stands for alkyl, alkenyl, cycloalkyl, cycloalkenyl, cycloalylalkyl, or cycloalkenylalkyl, in each case optionally branched and in each case interrupted by at least one oxygen atom, andX stands for hydrogen or halogen.Intermediates of the formula ##STR4## are also new.
    Type: Grant
    Filed: May 19, 1989
    Date of Patent: August 13, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Otto Schallner, Reiner Fischer, Albrecht Marhold, Karl-Julius Reubke, Hans-Joachim Santel, Robert R. Schmidt, Klaus Lurssen, Harry Strang
  • Patent number: 5028619
    Abstract: Provided are microbiocidal solutions comprising an aryl alkanol solvent and a microbiocidal compound dissolved therein. The solutions may be used to impart microbiocidal properties to polymer compositions.
    Type: Grant
    Filed: January 25, 1989
    Date of Patent: July 2, 1991
    Assignee: Morton International, Inc.
    Inventors: Nuno M. Rei, Ronald C. Wilson
  • Patent number: 5024694
    Abstract: Herbicidal and plant growth-regulating N-aryl heterocycles of the formula ##STR1## where A represents one of the groupings ##STR2## where R.sup.1 and R.sup.2 in each case independently of one another represent hydrogen, halogen, halogenoalkyl or alkyl,Y.sup.1 and Y.sup.2 in each case represent oxygen or sulphur andZ represents hydrogen, hydroxyl or chlorine, R represents in each case optionally branched alkyl, alkenyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl or cycloalkenylalkyl in each case interrupted by at least one oxygen atom and in each case substituted by at least one fluorine atom,X represents hydrogen or halogen andY represents hydrogen or halogen.
    Type: Grant
    Filed: February 6, 1990
    Date of Patent: June 18, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Otto Schallner, Michael Negele, Hans-Joachim Santel, Klaus Lurssen, Robert R. Schmidt, Birgit Krauskopf
  • Patent number: 5013848
    Abstract: 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: Grant
    Filed: July 22, 1987
    Date of Patent: May 7, 1991
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Yukihiro Yoshikawa, Midori Yamazaki, Keizaburo Yamaguchi, Kenichi Sugimoto, Yoshimitsu Tanabe, Akihiro Yamaguchi
  • Patent number: 4994557
    Abstract: N-(m-radiohalophenyl) maleimide can be conjugated with a reduced antibody having a mercapto group to provide a radiolabelled half-antibody having immunological specific binding characteristics of whole antibody.
    Type: Grant
    Filed: January 29, 1988
    Date of Patent: February 19, 1991
    Assignee: President and Fellows of Harvard College
    Inventors: Amin I. Kassis, Leslie A. Khawli
  • Patent number: 4985568
    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## 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: Grant
    Filed: April 28, 1989
    Date of Patent: January 15, 1991
    Assignee: The Boeing Company
    Inventors: Hyman R. Lubowitz, Clyde H. Sheppard
  • Patent number: 4981994
    Abstract: 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: Grant
    Filed: July 31, 1989
    Date of Patent: January 1, 1991
    Assignee: Shell Oil Company
    Inventor: Roy J. Jackson
  • Patent number: 4980483
    Abstract: A method for the production of a maleimide, which comprises effecting a former-stage reaction by adding maleic anhydride and a primary amine in amounts such that the molar ratio of said maleic anhydride to said primary amine is less than 1 under application of heat to a water-insoluble or water-immisible inert organic solvent containing an acid catalyst and subsequently carrying out a latter-stage reaction by adding to the reaction system maleic anhydride in an amount such that the molar ratio of the total amount of maleic anhydride to be added to said reaction system to the total amount of said primary amine added to said reaction system exceeds 1.
    Type: Grant
    Filed: February 14, 1989
    Date of Patent: December 25, 1990
    Assignee: Nippon Shokubai Kagaku Kogyo Co., Ltd.
    Inventors: Yuichi Kita, Masakazu Nakagawa, Hitoshi Kanei, Akio Fukui
  • Patent number: 4962205
    Abstract: Method for the transportation or storage of N-phenyl maleimide, which method comprises mixing N-phenyl maleimide with maleic anhydride in a ratio of 1 to 90 parts by weight of N-phenyl maleimide to 99 to 10 parts by weight of maleic anhydride and handling the resultant mixture in a molten state in the presence of a polymerization inhibitor, and a composition of liquid state.
    Type: Grant
    Filed: August 11, 1989
    Date of Patent: October 9, 1990
    Assignee: Nippon Shokubai Kagaku Kogyo, Co., Ltd.
    Inventors: Yuichi Kita, Kazuo Kishino, Akio Fukui
  • Patent number: 4937356
    Abstract: Acetylene terminated aspartimides are prepared using two methods. In the first, an amino-substituted aromatic acetylene is reacted with an aromatic bismaleimide in a solvent of glacial acetic acid and/or m-cresol. In the second method, an aromatic diamine is reacted with an ethynyl containing maleimide, such as N-(3-ethynylphenyl)maleimide, in a solvent of glacial acetic acid and/or m-cresol. In addition, acetylene terminated aspartimides are blended with various acetylene terminated oligomers and polymers to yield composite materials exhibiting improved mechanical properties.
    Type: Grant
    Filed: August 10, 1989
    Date of Patent: June 26, 1990
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventors: Paul M. Hergenrother, John W. Connell, Stephen J. Havens
  • Patent number: 4929272
    Abstract: Novel derivatives of N-phenylmaleic acid imide and N-phenylsuccinimide have good pre- and post-emergence selective herbicidal properties and they influence plant growth. The compounds correspond to the formula I in which.vertline.: represents a single or double bond,R.sup.1 represents hydrogen or fluorine,R.sup.2 represents halogen,Y represents C.sub.1 -C.sub.8 -alkyl,Z represents hydrogen or C.sub.1 -C.sub.8 -alkyl, andA represents hydrogen or a group ##STR1## wherein R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7 and R.sup.8 represent customary organic radicals and X represents oxygen, sulphur, SO, SO.sub.2, NH, alkylimino or alkenylimino.
    Type: Grant
    Filed: December 8, 1988
    Date of Patent: May 29, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Hans Moser, Georg Pissiotas, Hans-Georg Brunner, Beat Bohner, Marcus Baumann
  • Patent number: 4923997
    Abstract: Bis-maleimide compounds of the formula: ##STR1## where R' is an alkenylene or alkylene group; the R" groups are independently hydrocarbon or halohydrocarbon groups; and n is an integer, are hydrolytically stable compounds which may be thermally cured, or co-cured with other radically cureable monomers, to provide crosslinked polymer with good thermal properties. Compounds of the formula where n is above about 9 can be used as additives for radically cureable silicone formulations.
    Type: Grant
    Filed: February 21, 1989
    Date of Patent: May 8, 1990
    Assignee: Loctite Corporation
    Inventor: Philip Klemarczyk
  • Patent number: 4916235
    Abstract: Resins are prepared by Diels-Alder polymerization of compounds of the formula ##STR1## where R is a divalent linking group.
    Type: Grant
    Filed: November 26, 1986
    Date of Patent: April 10, 1990
    Assignee: University of Dayton
    Inventors: Loon-Seng Tan, Fred E. Arnold
  • Patent number: 4904803
    Abstract: N-substituted maleimides are prepared by reacting maleic anhydride with an amine in the presence of Cu or a copper compound and purifying the maleimide produced in the absence of presence of said Cu or copper compound. N-substituted maleimides are widely useful or starting materials or intermediates for medicines, agricultural chemicals, dyes, macromolecular compounds, and the like.
    Type: Grant
    Filed: February 16, 1989
    Date of Patent: February 27, 1990
    Assignees: Nitto Chemical Industry Co., Ltd., Mitsubishi Rayon Co., Ltd.
    Inventors: Takeyuki Fujita, Tuyoshi Irie, Yasuyuki Takayanagi, Takeshi Narita, Yuya Yano
  • Patent number: 4883883
    Abstract: Novel N-[(meth)allyloxy-mono-/di(meth)allylphenyl]maleimides, in admixture with at least one N-[(meth)allyloxyphenyl]maleimide, are reacted with at least one bismaleimide, and optionally a hydroxylated organosilicon compound, in the presence of an imidazole compound, to obtain mechanically improved thermosetting imido copolymerizates well adapted for the production of, e.g., coatings, adhesive bondings, laminates and composites.
    Type: Grant
    Filed: December 17, 1987
    Date of Patent: November 28, 1989
    Assignee: Rhone-Poulenc Chimie
    Inventors: Pascal Barthelemy, Michel Crochemore
  • Patent number: 4873338
    Abstract: Compounds corresponding to Formula I ##STR1## wherein R.sup.1 denotes an acyl group andX denotes hydrogen, halogen, alkoxy, aroxy, SO.sub.3 H or a heterocyclic group attached through --O-- or --N<are prepared form a compound corresponding to Formula II ##STR2## wherein X has the meaning already indicated and Q denotes the group required for completing a dicarbonimide ringby reduction of the said compound to the amino compound and acylation into a compound corresponding to Formula III ##STR3## wherein X, Q and R.sup.1 have the meanings indicatedfollowed by conversion of the compound corresponding to Formula III into a compound corresponding to Formula I by hydrazinolytic or hydrolytic decomposition of the dicarbonimide ring.
    Type: Grant
    Filed: November 23, 1987
    Date of Patent: October 10, 1989
    Assignee: Agfa-Gevaert Aktiengesellschaft
    Inventors: Heinz Wiesen, Erich Wolff
  • Patent number: 4851547
    Abstract: A method for the production of a maleimide by dehydration and ring-closure of maleinamic acid obtained by the reaction of maleic anhydride with an amine, which method is characterized by effecting ring-closure imidation of said maleinamic acid by heating said maleinamic acid in a water-insoluble or water-immiscible inert organic non-polar solvent in the presence of a catalyst of an amine salt produced from the amine and an acid, a mixture of the amine salt and the acid, or a supported catalyst on a solid carrier the catalyst or the acid.
    Type: Grant
    Filed: December 23, 1988
    Date of Patent: July 25, 1989
    Assignee: Nippon Shokubai Kagaku Kogyo Co., Ltd.
    Inventors: Yuichi Kita, Koichi Nakagawa, Kentaro Sakamoto, Akio Fukui, Masao Baba, Yoichi Nakagawa
  • Patent number: 4826997
    Abstract: The invention is a compound which comprises an unsaturated cyclic imide moiety and an aryl cyclobutene moiety, wherein the cyclobutene moiety is fused to the aryl radical, and wherein the imide nitrogen is connected to the aryl radical by a direct bond or a bridging member. Another aspect of this invention is a polyimide polymeric composition which results from the polymerization of the above-described compounds.
    Type: Grant
    Filed: August 4, 1986
    Date of Patent: May 2, 1989
    Assignee: The Dow Chemical Company
    Inventor: Robert A. Kirchhoff