Phosphorus- Or Sulfur-containing Reactant Patents (Class 528/321)
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Patent number: 4600770Abstract: 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: GrantFiled: January 23, 1985Date of Patent: July 15, 1986Inventors: John Gagliani, John V. Long
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Patent number: 4600769Abstract: 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: GrantFiled: May 31, 1985Date of Patent: July 15, 1986Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space AdministrationInventors: Devendra Kumar, George M. Fohlen, John A. Parker
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Patent number: 4594409Abstract: 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: GrantFiled: August 30, 1984Date of Patent: June 10, 1986Assignee: Nitto Boseki Co., Ltd.Inventors: Ikuo Hayashi, Tadao Itikawa, Kiyoshi Shimizu
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Patent number: 4579782Abstract: 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: GrantFiled: August 30, 1985Date of Patent: April 1, 1986Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space AdministrationInventors: Devendra Kumar, George M. Fohlen, John A. Parker
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Patent number: 4559400Abstract: 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: GrantFiled: February 6, 1985Date of Patent: December 17, 1985Assignee: American Cyanamid CompanyInventors: David W. Wang, Daniel R. Draney
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Patent number: 4546168Abstract: 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: GrantFiled: August 9, 1984Date of Patent: October 8, 1985Assignee: Hitachi, Ltd.Inventors: Akio Takahashi, Takeshi Shimazaki, Motoyo Wajima, Hirosada Morishita
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Patent number: 4544713Abstract: 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: GrantFiled: May 16, 1984Date of Patent: October 1, 1985Assignee: The United States of America as represented by the Secretary of the Air ForceInventors: Tsu-Tzu Tsai, Fred E. Arnold
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Patent number: 4537947Abstract: 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: GrantFiled: March 14, 1975Date of Patent: August 27, 1985Assignee: University of Notre Dame du LacInventor: Gaetano F. D'Alelio
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Patent number: 4535147Abstract: 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: GrantFiled: July 9, 1984Date of Patent: August 13, 1985Assignee: The B. F. Goodrich CompanyInventor: Ronald E. Myers
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Patent number: 4533724Abstract: 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: GrantFiled: September 17, 1982Date of Patent: August 6, 1985Assignee: SRI InternationalInventors: James F. Wolfe, Paul D. Sybert, Joanne R. Sybert, Blake Wilson
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Patent number: 4529793Abstract: 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: GrantFiled: June 20, 1983Date of Patent: July 16, 1985Assignee: Nitto Electric Industrial Co., Ltd.Inventors: Masao Abe, Akio Iwama, Yuzuru Noda, Hisashi Ichinose
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Patent number: 4526838Abstract: 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: GrantFiled: September 6, 1983Date of Patent: July 2, 1985Assignee: Hitachi Chemical Company, Ltd.Inventors: Atsushi Fujioka, Yasuo Miyadera, Tomio Fukuda
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Patent number: 4524166Abstract: 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: GrantFiled: September 14, 1984Date of Patent: June 18, 1985Assignee: Ciba-Geigy CorporationInventors: John D. Spivack, Stephen D. Pastor
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Patent number: 4518786Abstract: 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: GrantFiled: August 1, 1983Date of Patent: May 21, 1985Assignee: American Cyanamid CompanyInventors: David W. Wang, Daniel R. Draney
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Patent number: 4507467Abstract: 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: GrantFiled: August 29, 1983Date of Patent: March 26, 1985Assignee: Teijin LimitedInventors: Keizo Shimada, Hideharu Sasaki, Hiroshi Mera, Toru Sawaki, Akihiro Aoki
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Patent number: 4501880Abstract: Novel copolyoxadiazole-imides are disclosed. These copolyoxadiazole-imides are useful for the manufacture of fibers, films, felts, coatings and molded objects.Type: GrantFiled: December 30, 1983Date of Patent: February 26, 1985Assignee: Standard Oil Company (Indiana)Inventor: James R. Stephens
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Patent number: 4499245Abstract: 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: GrantFiled: July 15, 1983Date of Patent: February 12, 1985Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Nobuyuki Ikeguchi, Hidenori Kimbara
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Patent number: 4496701Abstract: 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: GrantFiled: June 9, 1983Date of Patent: January 29, 1985Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space AdministrationInventors: Indra K. Varma, George M. Fohlen, John A. Parker
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Patent number: 4485234Abstract: 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: GrantFiled: February 15, 1984Date of Patent: November 27, 1984Assignee: Hitachi Chemical Company, Ltd.Inventors: Daisuke Makino, Yasuo Miyadera
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Patent number: 4482703Abstract: 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: GrantFiled: October 20, 1982Date of Patent: November 13, 1984Assignee: Hitachi, Ltd.Inventors: Akio Takahashi, Takeshi Shimazaki, Motoyo Wajima, Hirosada Morishita
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Patent number: 4482683Abstract: 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: GrantFiled: December 1, 1983Date of Patent: November 13, 1984Assignee: Siemens AktiengesellschaftInventors: Ferdinand Quella, Hans-Friedrich Schmidt
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Patent number: 4461886Abstract: 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: GrantFiled: April 20, 1983Date of Patent: July 24, 1984Assignee: Polaroid CorporationInventors: Howard G. Rogers, Russell A. Gaudiana, Jeannette S. Manello, Ronald A. Sahatjian
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Patent number: 4442268Abstract: 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: GrantFiled: August 4, 1981Date of Patent: April 10, 1984Inventor: Alexandros K. Tsolis
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Patent number: 4429108Abstract: 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: GrantFiled: September 27, 1982Date of Patent: January 31, 1984Assignee: Standard Oil Company (Indiana)Inventor: James R. Stephens
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Patent number: 4429109Abstract: 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: GrantFiled: September 15, 1982Date of Patent: January 31, 1984Assignee: Standard Oil CompanyInventors: Benedict S. Curatolo, Gerald P. Coffey
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Patent number: 4418181Abstract: The compositions described herein comprise polyimides having bis-maleimide terminal groups and having the formula: ##STR1## wherein Q is a trivalent aromatic radical, Ar is a divalent aromatic radical, Ar" is a tetravalent aromatic radical and n has a value of 0-20. Derivatives may be made of these compounds by homopolymerization, copolymerization with other copolymerizable materials and by reaction with Diels-Alder reactable materials.Type: GrantFiled: May 26, 1981Date of Patent: November 29, 1983Assignee: Plastics Engineering CompanyInventor: Walter J. Monacelli
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Patent number: 4414383Abstract: 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: GrantFiled: May 24, 1982Date of Patent: November 8, 1983Assignee: Celanese CorporationInventors: Anthony B. Conciatori, Eui W. Choe, Henry K. Hall, Jr.
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Patent number: 4413114Abstract: 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: GrantFiled: March 30, 1982Date of Patent: November 1, 1983Assignee: Teijin LimitedInventors: Keizo Shimada, Hiroshi Mera, Noriaki Sasaki, Akihiro Aoki
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Patent number: 4393188Abstract: 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: GrantFiled: February 12, 1981Date of Patent: July 12, 1983Assignee: Hitachi Chemical Company, Ltd.Inventors: Akio Takahashi, Motoyo Wajima, Ritsuro Tada, Hirosada Morishita, Yutaka Mizuno, Shunya Yokozawa, Kenji Tsukanishi
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Patent number: 4391968Abstract: 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: GrantFiled: February 20, 1981Date of Patent: July 5, 1983Assignee: Montedison S.p.A.Inventors: Gianfranco Merani, Giuseppe Anzuino
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Patent number: 4385169Abstract: 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: GrantFiled: May 21, 1981Date of Patent: May 24, 1983Assignee: Teijin LimitedInventors: Yoshinori Kato, Hisashi Fukushima, Takeshi Hara
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Patent number: 4373086Abstract: 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: GrantFiled: February 3, 1981Date of Patent: February 8, 1983Assignee: Mitsubishi Gas Chemical Company, Inc.Inventor: Nobuyuki Ikeguchi
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Patent number: 4370467Abstract: 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: GrantFiled: July 3, 1980Date of Patent: January 25, 1983Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Morio Gaku, Nobuyuki Ikeguchi
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Patent number: 4365068Abstract: 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: GrantFiled: November 14, 1980Date of Patent: December 21, 1982Assignee: Ciba-Geigy CorporationInventors: Roland Darms, Vratislav Kvita, Gerd Greber
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Patent number: 4355151Abstract: 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: GrantFiled: February 13, 1980Date of Patent: October 19, 1982Assignee: Teijin LimitedInventors: Keizo Shimada, Hiroshi Mera, Noriaki Sasaki, Akihiro Aoki
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Patent number: 4350810Abstract: 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: GrantFiled: May 8, 1981Date of Patent: September 21, 1982Assignee: Phillips Petroleum CompanyInventors: Dale O. Tieszen, Lacey E. Scoggins
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Patent number: 4321198Abstract: 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: GrantFiled: January 25, 1980Date of Patent: March 23, 1982Assignee: Plastics Engineering CompanyInventors: Gaetano F. D'Alelio, Phillip A. Waitkus
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Patent number: 4320217Abstract: 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: GrantFiled: January 25, 1980Date of Patent: March 16, 1982Assignee: Plastics Engineering CompanyInventors: Gaetano F. D'Alelio, Phillip A. Waitkus
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Patent number: 4319019Abstract: 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: GrantFiled: July 14, 1980Date of Patent: March 9, 1982Assignee: Bayer AktiengesellschaftInventors: Wolfgang Lehmann, Friedhelm Muller, Gunther Cramn, Knut Hammerstrom, Wilfried Lobach
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Patent number: 4316845Abstract: 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: GrantFiled: January 25, 1980Date of Patent: February 23, 1982Assignee: Plastics Engineering CompanyInventors: Gaetano F. D'Alelio, Phillip A. Waitkus
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Patent number: 4316843Abstract: 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: GrantFiled: January 25, 1980Date of Patent: February 23, 1982Assignee: Plastics Engineering CompanyInventors: Phillip A. Waitkus, Gaetano F. D'Alelio
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Patent number: 4316844Abstract: 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: GrantFiled: January 25, 1980Date of Patent: February 23, 1982Assignee: Plastics Engineering CompanyInventors: Phillip A. Waitkus, Gaetano F. D'Alelio
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Patent number: 4303779Abstract: 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: GrantFiled: November 27, 1979Date of Patent: December 1, 1981Assignee: Technochemie GmbH-VerfahrenstechnikInventor: Horst Stenzenberger
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Patent number: 4283521Abstract: 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: GrantFiled: February 14, 1979Date of Patent: August 11, 1981Assignee: TRW Inc.Inventor: Robert J. Jones
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Patent number: 4283522Abstract: 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: GrantFiled: August 31, 1979Date of Patent: August 11, 1981Assignee: Hitachi Chemical Company, Ltd.Inventors: Akio Takahashi, Yutaka Itoh, Motoyo Wajima, Hirosada Morishita, Kenji Tsukanishi
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Patent number: 4282347Abstract: 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: GrantFiled: August 14, 1979Date of Patent: August 4, 1981Assignee: Phillips Petroleum CompanyInventors: Dale O. Tieszen, Lacey E. Scoggins
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Patent number: 4280946Abstract: 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: GrantFiled: December 3, 1979Date of Patent: July 28, 1981Assignee: Ciba-Geigy CorporationInventors: Roland Darms, Vratislav Kvita, Gerd Greber
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Patent number: 4275185Abstract: 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: GrantFiled: September 24, 1979Date of Patent: June 23, 1981Assignee: ICI Americas Inc.Inventor: Robert T. Lu
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Patent number: 4273916Abstract: 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: GrantFiled: June 13, 1980Date of Patent: June 16, 1981Assignee: TRW Inc.Inventor: Robert J. Jones
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Patent number: 4250299Abstract: 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: GrantFiled: December 15, 1978Date of Patent: February 10, 1981Assignee: Bayer AktiengesellschaftInventors: Wolfgang Lehmann, Friedhelm Muller, Gunther Cramm, Knut Hammerstrom, Wilfried Lobach