Phosphorus- Or Sulfur-containing Reactant Patents (Class 528/321)
  • Patent number: 4600770
    Abstract: Methods of making water soluble polyimide resin compositions. A carboxy terminated bisimide is prepared by reacting a suitable aromatic dianhydride with a suitable oxoimine. The bisimide is then mixed with a sufficient quantity of a water soluble solvent to dissolve the bisimide. Water is added to make a solution of the desired viscosity. An aromatic diamine is added to this water solution. To the mixture is added a suitable quantity of a tertiary amine to stabilize the resin. The solution is coated onto a surface and dried to produce a smooth, flexible coating. The coating can then be heated to an appropriate temperature to produce a fully polymerized coating which is thermally stable and resistant to oils and solvents.
    Type: Grant
    Filed: January 23, 1985
    Date of Patent: July 15, 1986
    Inventors: John Gagliani, John V. Long
  • Patent number: 4600769
    Abstract: Novel amine terminated bisaspartimides, especially 4,4'-bis{N.sup.2 -[4-(4-aminophenoxy)phenyl]aspartimido} diphenylmethane are prepared by a Michael-type reaction of an aromatic bismaleimide and an aromatic diamine in an aprotic solvent. These bisaspartimides are thermally polymerized to yield tough, resinous polymers cross-linked through --NH-- groups. Such polymers are useful in applications requiring materials with resistance to change at elevated temperatures, e.g., as lightweight laminates with graphite cloth, molding material prepregs, adhesives and insulating material.
    Type: Grant
    Filed: May 31, 1985
    Date of Patent: July 15, 1986
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventors: Devendra Kumar, George M. Fohlen, John A. Parker
  • Patent number: 4594409
    Abstract: A sequential polyamino acid resin having a remarkably high molecular weight and special amino acid sequence as repeating unit in the resin can be produced by conducting polycondensation of a peptide active ester acid salt in an aprotic polar solvent in the presence of a tertiary amine and phosphorus pentoxide.
    Type: Grant
    Filed: August 30, 1984
    Date of Patent: June 10, 1986
    Assignee: Nitto Boseki Co., Ltd.
    Inventors: Ikuo Hayashi, Tadao Itikawa, Kiyoshi Shimizu
  • Patent number: 4579782
    Abstract: Novel amine terminated bisaspartimides, especially 4,4'-bis{N.sup.2 -[4-(4-aminophenoxy)phenyl]aspartimido}diphenylmethane are prepared by a Michael-type reaction of an aromatic bismaleimide and an aromatic diamine in an aprotic solvent. These bisaspartimides are thermally polymerized to yield tough, resinous polymers cross-linked through --NH-- groups. Such polymers are useful in applications requiring materials with resistance to change at elevated temperatures, e.g., as lightweight laminates with graphite cloth, molding material prepregs, adhesives and insulating material.
    Type: Grant
    Filed: August 30, 1985
    Date of Patent: April 1, 1986
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventors: Devendra Kumar, George M. Fohlen, John A. Parker
  • Patent number: 4559400
    Abstract: Polymers of a polyfunctional epoxy compound, N,N,N',N'-tetraglycidyl-1,3-propylene bis(p-aminobenzoate), formed by reaction of such epoxy compound with aromatic polyamines. The disclosed polymers are useful as structural resins, e.g., as advanced composite matrix resins.
    Type: Grant
    Filed: February 6, 1985
    Date of Patent: December 17, 1985
    Assignee: American Cyanamid Company
    Inventors: David W. Wang, Daniel R. Draney
  • Patent number: 4546168
    Abstract: A thermosetting resin composition comprising (A) at least one dicyanamide compound and (B) at least one polyvalent imide having one or more unsaturated bonds and, if necessary (C) at least one polymerizable compound of epoxy compounds, phenolic compounds and triallyl isocyanurate compounds, and a prepolymer thereof obtained by subjecting the composition to a preliminary reaction with heating to the B stage can give a cured product having excellent heat resistance of class C and flexibility.
    Type: Grant
    Filed: August 9, 1984
    Date of Patent: October 8, 1985
    Assignee: Hitachi, Ltd.
    Inventors: Akio Takahashi, Takeshi Shimazaki, Motoyo Wajima, Hirosada Morishita
  • Patent number: 4544713
    Abstract: Thermally stable aromatic heterocyclic block copolymers are prepared by reacting a diamino monomer and terephthalic acid to form a carboxy-terminated rigid rod segment and then polymerizing a carboxy-monoamine monomer therewith to form flexible segments grafted onto the rigid rod segments.
    Type: Grant
    Filed: May 16, 1984
    Date of Patent: October 1, 1985
    Assignee: The United States of America as represented by the Secretary of the Air Force
    Inventors: Tsu-Tzu Tsai, Fred E. Arnold
  • Patent number: 4537947
    Abstract: Aromatic polyimides with various functional end-groups such as --CH.dbd.CH.sub.2, --C.tbd.CH, --CN and --CHO are chain-extended (molecular weight increased) by reacting the functional groups with aromatic bis-dipoles. A representative bis-dipole is 1,4-benzene-dinitrile oxide. These polyimides can be shaped and formed prior to chain extending.The aromatic polyimides appropriate for chain-extending are formed by the reaction of aromatic dianhydrides, aromatic amines and monoamines which contain the functional groups.
    Type: Grant
    Filed: March 14, 1975
    Date of Patent: August 27, 1985
    Assignee: University of Notre Dame du Lac
    Inventor: Gaetano F. D'Alelio
  • Patent number: 4535147
    Abstract: A reaction product of a phosphazene and an amine terminated reactive liquid polymer. The phosphazene and the reactive liquid polymer are combined under agitation to produce a cured, cross-linked, reactive liquid polymer including bonded phosphazene groups providing a desirable elastomeric performance over a broad range of temperatures including temperatures substantially below freezing.
    Type: Grant
    Filed: July 9, 1984
    Date of Patent: August 13, 1985
    Assignee: The B. F. Goodrich Company
    Inventor: Ronald E. Myers
  • Patent number: 4533724
    Abstract: Novel compositions comprising a high concentration of poly(2,6-benzothiazole) and certain polyphosphoric acids are prepared. Such compositions are optically anisotropic (liquid crystalline), capable of exhibiting excellent cohesive strength, and are especially suited to the production of high molecular weight ordered polymer fibers by dry-jet wet spinning. These liquid crystalline compositions are capable of being drawn through long air gap distances and spun at exceptionally high spin draw ratios. Fibers, films and other articles formed from these liquid crystalline compositions exhibit exceptionally high physical and heat resistant properties.
    Type: Grant
    Filed: September 17, 1982
    Date of Patent: August 6, 1985
    Assignee: SRI International
    Inventors: James F. Wolfe, Paul D. Sybert, Joanne R. Sybert, Blake Wilson
  • Patent number: 4529793
    Abstract: A selective permeable membrane comprising a polyquinazolone-based polymer including a repeating unit represented by the formula ##STR1## wherein R.sup.1 is a tetravalent aromatic group, R.sup.2a and R.sup.2b are each independently, an alkyl group or aromatic group, and R.sup.3 is a divalent organic group.
    Type: Grant
    Filed: June 20, 1983
    Date of Patent: July 16, 1985
    Assignee: Nitto Electric Industrial Co., Ltd.
    Inventors: Masao Abe, Akio Iwama, Yuzuru Noda, Hisashi Ichinose
  • Patent number: 4526838
    Abstract: A curable polyamino-bis-imide resin, obtained by the thermal reaction of:(A) a bis-imide represented by the general formula I: ##STR1## wherein R.sub.1 stands for a divalent organic group having a carbon-carbon double bond and R.sub.2 for a divalent aromatic organic group having 1 to 3 benzene rings, with(B) a diamine represented by the general formula II: ##STR2## wherein X stands for one member selected from the group consisting of O, S, SO.sub.2, CH.sub.2, CO, COO, C(CH.sub.3).sub.2, CF.sub.2 and C(CF.sub.3).sub.2, providing that the three X's may be identical or not identical to one another and the hydrogen atoms attached to the benzene rings may be substituted by an inactive alkyl group, perfluoroalkyl group or halogen atom, a solution thereof, cross-linked resins therefrom and laminated boards therefrom.
    Type: Grant
    Filed: September 6, 1983
    Date of Patent: July 2, 1985
    Assignee: Hitachi Chemical Company, Ltd.
    Inventors: Atsushi Fujioka, Yasuo Miyadera, Tomio Fukuda
  • Patent number: 4524166
    Abstract: Primary or secondary amino substituted hindered phosphites of the formula ##STR1## are prepared by reaction of the appropriate phosphorus and phenol compounds, said hindered phosphites being useful as stabilizers of organic polymers and lubricating oils.
    Type: Grant
    Filed: September 14, 1984
    Date of Patent: June 18, 1985
    Assignee: Ciba-Geigy Corporation
    Inventors: John D. Spivack, Stephen D. Pastor
  • Patent number: 4518786
    Abstract: A polyfunctional epoxy compound, N,N,N',N'-tetraglycidyl-1,3-propylene bis(p-aminobenzoate) is disclosed useful as an epoxide resin. Also disclosed are polymers of such compound formed by reaction with aromatic polyamines which are useful as structural resins, e.g., as advanced composite matrix resins.
    Type: Grant
    Filed: August 1, 1983
    Date of Patent: May 21, 1985
    Assignee: American Cyanamid Company
    Inventors: David W. Wang, Daniel R. Draney
  • Patent number: 4507467
    Abstract: High modulus shaped articles such as fibers and films, composed of a wholly aromatic copolyamide, are provided. The wholly aromatic copolyamide is comprised of recurring units of the formulae:--NH--AR.sub.1 --NH--CO--Ar.sub.2 --CO-- (A)and--NH--Ar.sub.3 --CO-- (B)wherein Ar.sub.1, Ar.sub.2 and Ar.sub.3 independently stand for divalent groups selected from ##STR1## in which X's independently stand for a group selected from halogeno, alkyl, aralkyl, aromatic, alkoxy, acetyl and cyano, n is 1 to 3 and Y is selected from ##STR2## in which R' stands for an 1-5C alkyl group, and the copolymerization ratio expressed by the molar ratio of the total of Ar.sub.1, Ar.sub.2 and Ar.sub.3 fails within the square hatched region in a triangular coordinate of FIG. 1, and said copolyamide has an intrinsic viscosity of at least 1.5.
    Type: Grant
    Filed: August 29, 1983
    Date of Patent: March 26, 1985
    Assignee: Teijin Limited
    Inventors: Keizo Shimada, Hideharu Sasaki, Hiroshi Mera, Toru Sawaki, Akihiro Aoki
  • Patent number: 4501880
    Abstract: Novel copolyoxadiazole-imides are disclosed. These copolyoxadiazole-imides are useful for the manufacture of fibers, films, felts, coatings and molded objects.
    Type: Grant
    Filed: December 30, 1983
    Date of Patent: February 26, 1985
    Assignee: Standard Oil Company (Indiana)
    Inventor: James R. Stephens
  • Patent number: 4499245
    Abstract: A curable resin composition comprising a mixture and/or a preliminary reaction product of (a) at least one cyanate compound selected from the group consisting of polyfunctional cyanate esters, prepolymers of the cyanate esters, coprepolymers of the cyanate esters and an amine and mixtures thereof, (b) a polyhydantoin resin and optionally (c) at least one maleimide compound selected from the group consisting of polyfunctional maleimides, prepolymer of the maleimides, coprepolymers of the maleimides and an amine and mixtures thereof is disclosed.
    Type: Grant
    Filed: July 15, 1983
    Date of Patent: February 12, 1985
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Nobuyuki Ikeguchi, Hidenori Kimbara
  • Patent number: 4496701
    Abstract: Cured polymers of bis- and tris-imides derived from tris(m-aminophenyl) phosphine oxides by reaction with maleic anhydride or its derivatives, and addition polymers of such imides, including a variant in which a mono-imide is condensed with a dianhydride and the product is treated with a further quantity of maleic anhydride prior to curing are disclosed and claimed. Such polymers are flame resistant. Also disclosed are an improved method of producing tris(m-aminophenyl) phosphine oxides from the nitro analogues by reduction with hydrazine hydrate using palladized charcoal or Raney nickel as the catalyst and fiber-reinforced cured resin composites.
    Type: Grant
    Filed: June 9, 1983
    Date of Patent: January 29, 1985
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventors: Indra K. Varma, George M. Fohlen, John A. Parker
  • Patent number: 4485234
    Abstract: An improved method of preparing polyamide acid for processing of semiconductors from a diamine and a tetracarboxylic acid dianhydride with a diaminocarbonamide, is provided (1) by reacting the components at below 40.degree. C. until the reduced viscosity reaches above 0.5 dl/g. at 30.degree. C., and then, (2) by adjusting the reduced viscosity to more than 0.3 dl/g, at 30.degree.0 C. and the solution viscosity to 500-3,000 cps at 25.degree. C. by heating at 50.degree.-100.degree. C. By applying the polyamide acid obtained by the method to semiconductor apparatus, they get sufficient heat-resistance without pin holes, and their reliability may be greatly improved.
    Type: Grant
    Filed: February 15, 1984
    Date of Patent: November 27, 1984
    Assignee: Hitachi Chemical Company, Ltd.
    Inventors: Daisuke Makino, Yasuo Miyadera
  • Patent number: 4482703
    Abstract: A thermosetting resin composition comprises (A) at least one dicyanamide compound and (B) at least one polyvalent imide having one or more unsaturated bonds and, if necessary (C) at least one polymerizable compound of epoxy compounds, phenolic compounds and triallyl isocyanurate compounds. A thermosetting prepolymer can be obtained by subjecting the composition to a preliminary reaction with heating to the B stage and this prepolymer can give a cured product having excellent heat resistance of class C and flexibility. An exemplary composition containing 60 parts by wt. of 4,4'-dicyanomidodiphenylmethane and 40 parts by wt. of N,N'-4,4'-diphenylmethane bismaleimide dissolved in methyl Cellosolve is reacted at 70.degree. to 110.degree. C. for about 40 minutes to obtain a prepolymer soluble in methyl ethyl ketone.
    Type: Grant
    Filed: October 20, 1982
    Date of Patent: November 13, 1984
    Assignee: Hitachi, Ltd.
    Inventors: Akio Takahashi, Takeshi Shimazaki, Motoyo Wajima, Hirosada Morishita
  • Patent number: 4482683
    Abstract: Sulfur-containing polymers, such as polyphenylene sulfide are stabilized from releasing sulfur-containing exhaust gases by adding an additive polymer having at least one reactive radical selected from the group consisting of amino radicals, amido radicals, imido radicals, and keto radicals therein, and which is of approximate the same thermal stability as the sulfur-containing polymer, to such sulfur-containing polymer. In other embodiments of the invention, sulfur-stabilization is also achieved by incorporating suitable fundamental building blocks of the additive polymer into the sulfur-containing polymer chain in the form of reactive monomers. Further, in other embodiments, additive polymers or oligomers (so-called telecheles) having reactive radicals at their ends can be introduced into the sulfur-containing polymer chain as copolymers.
    Type: Grant
    Filed: December 1, 1983
    Date of Patent: November 13, 1984
    Assignee: Siemens Aktiengesellschaft
    Inventors: Ferdinand Quella, Hans-Friedrich Schmidt
  • Patent number: 4461886
    Abstract: A class of polyamides comprising recurring units having certain substituted-biphenylene or substituted-stilbene radicals is disclosed. The substituted radicals include substituents so as to confer a non-coplanar molecular configuration and a substantially cylindrical distribution of electron density about the long axis of the recurring units and the chain-extended polymers including such radicals.Molecularly oriented polymers of the invention exhibit optically uniaxial properties. The highly birefringent polymers are suited to application in optical filter and other devices where a refractive and birefringent material is desired.
    Type: Grant
    Filed: April 20, 1983
    Date of Patent: July 24, 1984
    Assignee: Polaroid Corporation
    Inventors: Howard G. Rogers, Russell A. Gaudiana, Jeannette S. Manello, Ronald A. Sahatjian
  • Patent number: 4442268
    Abstract: N-(Substituted phosphinyl) polyamides and a method for their production are disclosed. The N-(substituted phosphinyl) polyamides are characterized by the recurring unit structure represented by the formula ##STR1## wherein A is in part hydrogen and in part a substituted phosphinyl radical. One method of producing the N-(substituted phosphinyl) polyamides is treating N-chlorinated polyamide with substituted phosphinyl compounds. The disclosed N-(substituted phosphinyl) polyamides exhibit excellent thermal stability fire resistance, good processability, high water absorption and permeability. The N-(substituted phosphinyl) polyamides are useful for making flame resistant textile materials.
    Type: Grant
    Filed: August 4, 1981
    Date of Patent: April 10, 1984
    Inventor: Alexandros K. Tsolis
  • Patent number: 4429108
    Abstract: Novel Poly[N,N'-(alkyl or aryl)-bis(4,4'-phthalimido)-1,3,4-oxadiazole-2,5-diyls], compositions for fibers, films, coatings and molded objects featuring high strength and high thermal properties with formulation advantages.
    Type: Grant
    Filed: September 27, 1982
    Date of Patent: January 31, 1984
    Assignee: Standard Oil Company (Indiana)
    Inventor: James R. Stephens
  • Patent number: 4429109
    Abstract: Polyamides containing as much as 50 mole percent nylon-3 units in at least a partially alternating system and exhibiting high glass transition temperatures (Tg) can be prepared from N,N'-terephthaloyldi-beta-alanine and a diamine, such as bis(p-aminocyclohexyl)methane. Properties of such polyamides can be controlled by choice of the diamine and the preparation temperature without loss of the high Tg. The polyamides of this invention exhibit utility in comfort fiber applications.
    Type: Grant
    Filed: September 15, 1982
    Date of Patent: January 31, 1984
    Assignee: Standard Oil Company
    Inventors: Benedict S. Curatolo, Gerald P. Coffey
  • 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: 4414383
    Abstract: This invention provides a single stage melt polymerization process for the production of an improved type of high molecular weight polybenzimidazole, which involves the use of a phosphorus-containing polymerization catalyst.The process provides poly-2,2'-(m-phenylene)-5,5'-bibenzimidazole of improved color and plugging value, and is further characterized by an inherent viscosity of at least about 0.7 dl/g, and a weight average molecular weight of at least about 100,000.
    Type: Grant
    Filed: May 24, 1982
    Date of Patent: November 8, 1983
    Assignee: Celanese Corporation
    Inventors: Anthony B. Conciatori, Eui W. Choe, Henry K. Hall, Jr.
  • Patent number: 4413114
    Abstract: An aromatic copolyamide comprising recurring units (A) of the formula (I), (B) of the formula (II) and (C) of the formula (III): ##STR1## wherein in (I), (II) and (III), Ar.sub.1 is phenylene, naphthylene or biphenylene radicals, each having two valence bonds oriented meta; Ar.sub.2 is phenylene, naphthylene or biphenylene radicals, each having two valence bonds oriented coaxially or in parallel to each other and radicals of the formula (IV): ##STR2## wherein Y.sub.1 and Y.sub.2 are independently ##STR3## and; X.sub.1, X.sub.2, X.sub.3, X.sub.4, X.sub.5 and X.sub.6 respectively are independently --NH-- and --CO-- radicals, connected to each other to form an amide bond (--NHCO-- or --CHNH--), and the molar proportions of said recurring units (A), (B), and (C) fall within a quadrilateral defined by the co-ordinates P, Q, R and S or on a twice-turned line defined by the co-ordinates Q, R, S and P:P (A 50, B 5, C 45)Q (A 5, B 5, C 90)R (A 5, B 40, C 55) andS (A 50, B 15, C 35)on a triangular composition diagram.
    Type: Grant
    Filed: March 30, 1982
    Date of Patent: November 1, 1983
    Assignee: Teijin Limited
    Inventors: Keizo Shimada, Hiroshi Mera, Noriaki Sasaki, Akihiro Aoki
  • Patent number: 4393188
    Abstract: A process for preparing a thermosetting maleimide type prepolymer which comprises reacting (A) a polyfunctional maleimide compound, (B) a bis-maleimide, (C) a diamine and (D) an epoxy compound. The maleimide type prepolymer prepared according to the process of the present invention has rapid curability and excellent solubility in low boiling point solvents such as acetone, methyl ethyl ketone and methyl cellosolve, which are available at low cost. Accordingly, the prepolymer is advantageously used especially for the production of laminated boards having good heat resisting properties, low moisture absorption and good adhesion to various substrates such as a copper foil.
    Type: Grant
    Filed: February 12, 1981
    Date of Patent: July 12, 1983
    Assignee: Hitachi Chemical Company, Ltd.
    Inventors: Akio Takahashi, Motoyo Wajima, Ritsuro Tada, Hirosada Morishita, Yutaka Mizuno, Shunya Yokozawa, Kenji Tsukanishi
  • Patent number: 4391968
    Abstract: Polyamides having a modified dye affinity are disclosed as prepared by polymerizing polyamide-forming monomers with a mixture consisting or consisting essentially of a dicarboxylic acid having the general formula HOOC--R--COOH, in which R is an aromatic, cyclo-aliphatic or aliphatic radical, and of a salt of a sulphonic dicarboxylic acid having the general formula: ##STR1## in which R has the meaning specified hereinbefore, X is an alkali or alkaline earth metal or ammonium, and n is a whole number from 1 to 4.
    Type: Grant
    Filed: February 20, 1981
    Date of Patent: July 5, 1983
    Assignee: Montedison S.p.A.
    Inventors: Gianfranco Merani, Giuseppe Anzuino
  • Patent number: 4385169
    Abstract: A reactive polymer having the degree of polymerization in the range of 5 to 3,000, with 60 mole % or more of the whole constituent units comprising the constituent units expressed by formula (I) ##STR1## wherein Z indicates a hydrogen atom or a univalent cation; m is an integer 1 to 4:and has an active group expressed by formula (II) at the carboxyl end of the main chain ##STR2## wherein X indicates a hydrogen atom or a group which can form an active disulfide linkage together with a neighboring sulfur atom; W is a divalent organic group; and R.sub.1 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
    Type: Grant
    Filed: May 21, 1981
    Date of Patent: May 24, 1983
    Assignee: Teijin Limited
    Inventors: Yoshinori Kato, Hisashi Fukushima, Takeshi Hara
  • Patent number: 4373086
    Abstract: A curable resin composition comprising a mixture and/or a preliminary reaction product of (a) at least one cyanate compound selected from the group consisting of polyfunctional cyanate esters, prepolymers of said cyanate esters, coprepolymers of said cyanate esters and an amine and mixtures thereof, (b) at least one compound having two or more acrylic ester groups represented by the formula ##STR1## wherein R.sup.1 is organic group comprising as member constituting a main chain or ring C and optionally O and/or N and optionally as a pendant hydroxy and/or halogen, when R.sup.1 contains aromatic group, R.sup.1 has 6-35 carbon atoms, and when R.sup.1 contains no benzene ring, R.sup.1 has 1-15 carbon atoms, X is hydrogen or methyl, n is integer of 2, 3, 4, 5 or 6 and valency of R.sup.1 is the same as n, and optionally (c) at least one compound selected from the group consisting of polyfunctional maleimides, prepolymers of the maleimides or coprepolymers of the maleimides and an amine is disclosed.
    Type: Grant
    Filed: February 3, 1981
    Date of Patent: February 8, 1983
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventor: Nobuyuki Ikeguchi
  • Patent number: 4370467
    Abstract: A curable resin composition comprising (i) a catalytic composite comprising a peroxide and other catalytic component and (ii) a mixture or a preliminary reaction product of (a) a polyfunctional cyanate ester, prepolymer of the cyanate ester or coprepolymer of the cyanate ester and an amine and (b) a polyfunctional maleimide, prepolymer of the maleimide or coprepolymer of the maleimide and an amine and optionally (c) other component is disclosed. The composition cures rapidly at a low temperature and is preferable from view point of quantity production and workability. The composition is excellent in respect of adhering property, heat-resistance, moisture-resistance and chemical-resistance, and is useful for preparing laminated products, molded products, paint, powder paint, adhesive or varnish.
    Type: Grant
    Filed: July 3, 1980
    Date of Patent: January 25, 1983
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Morio Gaku, Nobuyuki Ikeguchi
  • Patent number: 4365068
    Abstract: New crosslinkable bis-imidyl derivatives are described which can be produced by reaction of imidylphthalic acid derivatives, such as maleimidyl-phthalic acid anhydrides, with monomeric, oligomeric or polymeric diamines. The new crosslinkable bis-imidyl derivatives can be used for producing crosslinked polymers which are distinguished, in particular, by their stability to oxidation and to heat.
    Type: Grant
    Filed: November 14, 1980
    Date of Patent: December 21, 1982
    Assignee: Ciba-Geigy Corporation
    Inventors: Roland Darms, Vratislav Kvita, Gerd Greber
  • Patent number: 4355151
    Abstract: An aromatic copolyamide comprising recurring units (A) of the formula (I), (B) of the formula (II) and (C) of the formula (III): ##STR1## wherein in (I), (II) and (III) Ar.sub.1 is phenylene, naphthylene or biphenylene radicals, each having two valence bonds oriented meta; Ar.sub.2 is phenylene, naphthylene or biphenylene radicals, each having two valence bonds oriented coaxially or in parallel to each other and radicals of the formula (IV): ##STR2## wherein Y.sub.1 and Y.sub.2 are independently; ##STR3## and; X.sub.1, X.sub.2, X.sub.3, X.sub.4, X.sub.5 and X.sub.6 respectively are independently --NH-- and --CO-- radicals, connected to each other to form an amide bond (--NHCO-- or --CHNH--), and the molar proportions of said recurring units (A), (B) and (C) fall within a quadrilateral defined by the co-ordinates P, Q, R and S or on a twice-turned line defined by the co-ordinates Q,R,S, and P:P (A 50, B 5, C 45)Q (A 5, B 5, C 90)R (A 5, B 40, C 55) andS (A 50, B 15, C 35)on a triangular composition diagram.
    Type: Grant
    Filed: February 13, 1980
    Date of Patent: October 19, 1982
    Assignee: Teijin Limited
    Inventors: Keizo Shimada, Hiroshi Mera, Noriaki Sasaki, Akihiro Aoki
  • Patent number: 4350810
    Abstract: A process for the production of branched polymers of arylene sulfide in which a reaction mixture of (1) at least one p-dihalobenzene, (2) at least one alkali metal sulfide, (3) at least one organic amide, (4) water in an amount of about 1.0 mole to about 2.4 moles per mole of alkali metal sulfide, and (5) at least one alkali metal carboxylate is contacted under polymerization conditions for a time sufficient to form arylene sulfide polymer and the arylene sulfide polymer formed in said reaction mixture is contacted under polymerization conditions with a polyhaloaromatic compound having more than two halogen substituents per molecule for a time having a range of up to about 75 minutes before entering upon termination of the polymerization process. An embodiment of the process in which the alkali metal sulfide is produced in situ by the reaction of an excess of alkali metal hydroxide with alkali metal hydrosulfide.
    Type: Grant
    Filed: May 8, 1981
    Date of Patent: September 21, 1982
    Assignee: Phillips Petroleum Company
    Inventors: Dale O. Tieszen, Lacey E. Scoggins
  • Patent number: 4321198
    Abstract: Novel compositions comprising acetylenic polyhemi-amic acid compositions and processes for their preparation are disclosed herein. These new compositions are primarily derivatives of anhydride-terminated aromatic polyimides from which they are prepared by amidation to provide acetylenic amide groups having terminal .dbd.C.tbd.CH groups as hemi-amic acid groups of their derivatives. 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. Also included are monomeric compounds containing acetylenic amide groups derived from monomeric tetracarboxylic dianhydrides. These are particularly useful as crosslinking agents.
    Type: Grant
    Filed: January 25, 1980
    Date of Patent: March 23, 1982
    Assignee: Plastics Engineering Company
    Inventors: Gaetano F. D'Alelio, Phillip A. Waitkus
  • Patent number: 4320217
    Abstract: Novel compositions comprising polymerization products of polyimide derivatives having terminal acetylenic amide groups and processes for their preparation are disclosed herein. These new compositions are primarily polymers of derivatives of anhydride-terminated aromatic polyimides from which these derivatives are prepared by amidation to provide acetylenic amide groups having terminal --C.tbd.CH groups as hemi-amic acid groups or their derivatives. These derivative compositions are more tractable than the original anhydride-terminated polyimides and can be converted at appropriate lower temperatures and in accordance with the practice of this invention to crosslinked, insoluble, infusible polymers without by-product formation thereby extending greatly the applications for which the aromatic polyimides can be employed. Also included are polymers from monomeric compounds containing acetylenic amide groups derived from monomeric tetracarboxylic dianhydrides.
    Type: Grant
    Filed: January 25, 1980
    Date of Patent: March 16, 1982
    Assignee: Plastics Engineering Company
    Inventors: Gaetano F. D'Alelio, Phillip A. Waitkus
  • Patent number: 4319019
    Abstract: Water-soluble polyamines which are obtainable by reacting(A) one or more water-soluble or water-dispersible basic polyamides which have been prepared by condensation of aliphatic polyamines containing at least two primary amino groups and at least one secondary or tertiary amino group, or of mixtures of these polyamines and of aliphatic, cycloaliphatic, araliphatic or heterocyclic polyamines containing two primary or two secondary amino groups or one primary and one secondary amino group, with saturated aliphatic dicarboxylic acids containing 4-10 carbon atoms, or with functional derivatives thereof and optionally with .omega.-aminocarboxylic acids containing at least 3 carbon atoms, or lactams thereof,(B) one or more polyalkylenepolyamines of the general formula ##STR1## in which R denotes H or CH.sub.
    Type: Grant
    Filed: July 14, 1980
    Date of Patent: March 9, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wolfgang Lehmann, Friedhelm Muller, Gunther Cramn, Knut Hammerstrom, Wilfried Lobach
  • Patent number: 4316845
    Abstract: Novel compositions comprising acetylenic polyimide-polyamides and processes for their preparation are disclosed herein. These new compositions are primarily derivatives of anhydride-terminated aromatic polyimides from which they are prepared by amidation to provide acetylenic amide groups having terminal --C.dbd.CH groups. 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. Also included are monomeric compounds containing acetylenic amide groups derived from monomeric tetracarboxylic dianhydrides. These are particularly useful as crosslinking agents.
    Type: Grant
    Filed: January 25, 1980
    Date of Patent: February 23, 1982
    Assignee: Plastics Engineering Company
    Inventors: Gaetano F. D'Alelio, Phillip A. Waitkus
  • Patent number: 4316843
    Abstract: Novel compositions comprising unsaturated polyimide-polyamides and processes for their preparation are disclosed herein. These new compositions are primarily derivatives of anhydride-terminated aromatic polyimides from which they are prepared by amidation to provide unsaturated amide groups having terminal --CH.dbd.CH.sub.2 groups. 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. Also included are monomeric compounds containing unsaturated amide groups derived from monomeric tetracarboxylic dianhydrides. These are particularly useful as crosslinking agents.
    Type: Grant
    Filed: January 25, 1980
    Date of Patent: February 23, 1982
    Assignee: Plastics Engineering Company
    Inventors: Phillip A. Waitkus, Gaetano F. D'Alelio
  • Patent number: 4316844
    Abstract: Novel compositions comprising unsaturated polyhemi-amic acid compositions and processes for their preparation are disclosed herein. These new compositions are primarily derivatives of anhydride-terminated aromatic polyimides from which they are prepared by amidation to provide unsaturated amide groups having terminal --CH.dbd.CH.sub.2 groups as hemi-amic acid groups or their derivatives. 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. Also included are monomeric compounds containing unsaturated amide groups derived from monomeric tetracarboxylic dianhydrides. These are particularly useful as crosslinking agents.
    Type: Grant
    Filed: January 25, 1980
    Date of Patent: February 23, 1982
    Assignee: Plastics Engineering Company
    Inventors: Phillip A. Waitkus, Gaetano F. D'Alelio
  • Patent number: 4303779
    Abstract: Novel imide resins are prepared by reacting a mixture of a bisimide of an unsaturated dicarboxylic acid and a monoimide with a dihydrazide of a dicarboxylic acid, preferably in an organic solvent or diluent at elevated temperature for a period of time insufficient to yield an insoluble, infusible, fully cured imide resin. Solutions of the resulting prepolymerization product are stable at room temperature and their viscosity remains substantially unchanged for a prolonged period of time. Fully cured imide resins and articles thereof of a high heat resistance are obtained by heating said prepolymerized imide resin or materials such as fibers, metal wire webs, and others impregnated therewith, if desired, in the presence of curing catalysts, inhibitors, fillers and other materials to curing temperature up to 350.degree. C.
    Type: Grant
    Filed: November 27, 1979
    Date of Patent: December 1, 1981
    Assignee: Technochemie GmbH-Verfahrenstechnik
    Inventor: Horst Stenzenberger
  • Patent number: 4283521
    Abstract: A prepolymer is comprised of the reaction product of at least one aliphatic bismaleimide, at least one aromatic amine and at least one aromatic bismaleimide in combination with an aromatic and/or a cycloaliphatic epoxy resin providing at least two functional epoxy groups to provide a low temperature curable composition. The cured products are strongly adherent to a variety of substrates.
    Type: Grant
    Filed: February 14, 1979
    Date of Patent: August 11, 1981
    Assignee: TRW Inc.
    Inventor: Robert J. Jones
  • Patent number: 4283522
    Abstract: A process for preparing a thermosetting maleimide type prepolymer which comprises heating (A) a polyfunctional maleimide compound derived from a polyamine prepared from aniline and formalin, (B) a bis-maleimide and (C) a diamine. The thermosetting maleimide type prepolymer prepared according to the process of the present invention is excellent in solubility in low boiling point solvents such as acetone, methyl ethyl ketone and methyl cellosolve, which are available at low cost. Accordingly, the prepolymer is advantageously used especially for the production of laminated boards having excellent heat resisting properties.
    Type: Grant
    Filed: August 31, 1979
    Date of Patent: August 11, 1981
    Assignee: Hitachi Chemical Company, Ltd.
    Inventors: Akio Takahashi, Yutaka Itoh, Motoyo Wajima, Hirosada Morishita, Kenji Tsukanishi
  • Patent number: 4282347
    Abstract: A process for the production of branched polymers of arylene sulfide in which a reaction mixture of (1) at least one p-dihalobenzene, (2) at least one alkali metal sulfide, (3) at least one organic amide, (4) water in an amount of about 1.0 mole to about 2.4 moles per mole of alkali metal sulfide, and (5) at least one alkali metal carboxylate is contacted under polymerization conditions for a time sufficient to form arylene sulfide polymer and the arylene sulfide polymer formed in said reaction mixture is contacted under polymerization conditions with a polyhaloaromatic compound having more than two halogen substituents per molecule for a time having a range of up to about 75 minutes before entering upon termination of the polymerization process. An embodiment of the process in which the alkali metal sulfide is produced in situ by the reaction of an excess of alkali metal hydroxide with alkali metal hydrosulfide.
    Type: Grant
    Filed: August 14, 1979
    Date of Patent: August 4, 1981
    Assignee: Phillips Petroleum Company
    Inventors: Dale O. Tieszen, Lacey E. Scoggins
  • Patent number: 4280946
    Abstract: New crosslinkable bis-imidyl derivatives are described which can be produced by reaction of imidylphthalic acid derivatives, such as maleimidyl-phthalic acid anhydrides, with monomeric, oligomeric or polymeric diamines. The new crosslinkable bis-imidyl derivatives can be used for producing crosslinked polymers which are distinguished, in particular, by their stability to oxidation and to heat.
    Type: Grant
    Filed: December 3, 1979
    Date of Patent: July 28, 1981
    Assignee: Ciba-Geigy Corporation
    Inventors: Roland Darms, Vratislav Kvita, Gerd Greber
  • Patent number: 4275185
    Abstract: Polyimide polymers of improved physical properties and thermal stability may be prepared by reacting an N,N'-bismaleimide with an activated methylene compound in a nonreactive organic solvent system. The polymers are useful in producing films, moldings, and laminates or other composites.
    Type: Grant
    Filed: September 24, 1979
    Date of Patent: June 23, 1981
    Assignee: ICI Americas Inc.
    Inventor: Robert T. Lu
  • Patent number: 4273916
    Abstract: A prepolymer comprised of the reaction product of at least one aliphatic bismaleimide, at least one aromatic amine and at least one aromatic bismaleimide is combined with at least one cycloaliphatic epoxy resin having a melting point less than about 120.degree. F. and at least two functional epoxy groups to provide a low temperature curable composition. The cured products are strongly adherent to a variety of substrates.
    Type: Grant
    Filed: June 13, 1980
    Date of Patent: June 16, 1981
    Assignee: TRW Inc.
    Inventor: Robert J. Jones
  • Patent number: 4250299
    Abstract: Water-soluble polyamines which are obtainable by reacting(A) one or more water-soluble or water-dispersible basic polyamides which have been prepared by condensation of aliphatic polyamines containing at least two primary amino groups and at least one secondary or tertiary amino group, or of mixtures of these polyamines and of aliphatic, cycloaliphatic, araliphatic or heterocyclic polyamines containing two primary or two secondary amino groups or one primary and one secondary amino group, with saturated aliphatic dicarboxylic acids containing 4-10 carbon atoms, or with functional derivatives thereof and optionally with .omega.-aminocarboxylic acids containing at least 3 carbon atoms, or lactams thereof,(B) one or more polyalkylenepolyamines of the general formula ##STR1## in which R denotes H or CH.sub.
    Type: Grant
    Filed: December 15, 1978
    Date of Patent: February 10, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wolfgang Lehmann, Friedhelm Muller, Gunther Cramm, Knut Hammerstrom, Wilfried Lobach