From Organic Nitrile Group-containing Compound Patents (Class 528/362)
-
Patent number: 6201096Abstract: A continuous process for the polymerization of omega-aminonitriles (e.g., 6-aminocapronitriles) which is introduced at the top of a vertical multistage reactor being swept countercurrently with steam and polyamide (e.g., nylon 6) is recovered near the bottom of the vertical multistage reactor. By virtue of independent temperature control at each of the vertical stages of the multistage reactor, the polyamide recovered is typically characterized as having unreacted nitrile end groups of less than 20 gram equivalents per million grams of polyamide, and less than 25 gram equivalents of secondary amine branching per million grams of polyamide.Type: GrantFiled: October 25, 1999Date of Patent: March 13, 2001Assignee: E. I. du Pont de Nemours and CompanyInventors: Ernest Keith Marchildon, Ahmut Turgut Mutel
-
Patent number: 6001926Abstract: A fiber-reinforced phthalonitrile composite is made by impregnating or coating a fibrous material with a phthalonitrile prepolymer mixture containing a phthalonitrile monomer and an aromatic amine curing agent that is thermally stable and nonvolatile at a temperature up to about 375.degree. C., and that contains at least one electron withdrawing substituent effective to reduce the reactivity of the aromatic amine curing agent with the phthalonitrile monomer.Type: GrantFiled: October 2, 1997Date of Patent: December 14, 1999Assignee: The United States of America as represented by the Secretary of the NavyInventors: Satya B. Sastri, Teddy M. Keller
-
Patent number: 5973033Abstract: Compounds containing two cyclic hydrocarbon moieties which are substituted to provide crosslinking functionality and which are linked to each other by secondary or tertiary oxycarbonyl containing moiety are basis for compositions which are cured to provide cured thermosets for encapsulation and underfill for electronic components that are thermally decomposable to allow repair, replacement, recovery or recycling of operative electronic components from assemblies that are inoperative.Type: GrantFiled: October 26, 1998Date of Patent: October 26, 1999Assignee: Cornell Research Foundation, Inc.Inventors: Christopher K. Ober, Hilmar Koerner
-
Patent number: 5942598Abstract: Perfluoroalkyleneethertriazine oligomer obtained by reacting a dinitrile compound NC-Rf.sup.0 --CN, where Rf.sup.0 is --(CFXOCF.sub.2).sub.a (CF.sub.2).sub.b (CF.sub.2 OCFX).sub.c --, where X is a fluorine atom or a CF.sub.3 group, a is an integer of 1 to 5, b is an integer of 1 to 2 and c is an integer of 1 to 5, or Rf.sup.0 is --CF.sub.2 O(CF.sub.2 O).sub.d CF.sub.2 --, where d is an integer of 1 to 8 with ammonia, further reacting the resulting diamizine compound with a dinitrile compound NC-Rf.sup.1 --CN, where Rf.sup.1 has the same meaning as that for Rf.sup.0 or Rf.sup.1 is a perfluoroalkylene group having 4 to 8 carbon atoms thereby obtaining a perfluoroalkyleneetherpolyimidoylamizine oligomer, then reacting the resulting oligomer with a perfluoronitrile compound Rf.sup.2 CN, where Rf.sup.2 is CF.sub.3 (OCF.sub.2).sub.e --, where e is an integer of 3 to 10, and then subjecting the resulting terminal-treated oligomer to a ring-closing reaction with a perfluoroacylating agent Rf.sup.3 COY, where Rf.sup.Type: GrantFiled: December 26, 1996Date of Patent: August 24, 1999Assignees: Nippon Mektron, Limited, S.V. LebedevInventors: Riichi Iwa, Haruyoshi Tatsu, Sokolov Sergey Vasilyevich, Kollar Alexander Nikolaevich
-
Patent number: 5939508Abstract: A copolymer is formed from reacting, within a melt, a phthalonitrile resin with an epoxy resin having at least three epoxy groups. In an alternative embodiment, a copolymer is formed by reacting a phthalonitrile resin with an epoxy resin, at least one of the epoxy and phthalonitrile resins having a perfluorinated carbon. The copolymers of the present invention have exceptional thermal stability and a low affinity for water.Type: GrantFiled: March 31, 1997Date of Patent: August 17, 1999Assignee: The United States of America as represented by the Secretary of the NavyInventor: Teddy M. Keller
-
Patent number: 5922807Abstract: A fiber-reinforced phthalonitrile composite is made by impregnating or coating a fibrous material with a phthalonitrile prepolymer mixture containing a phthalonitrile monomer and an aromatic amine curing agent that is thermally stable and nonvolatile at a temperature up to about 375.degree. C., and that contains at least one electron withdrawing substituent effective to reduce the reactivity of the aromatic amine curing agent with the phthalonitrile monomer.Type: GrantFiled: October 2, 1997Date of Patent: July 13, 1999Assignee: The United States of America as represented by the Secretary of the NavyInventors: Satya B. Sastri, Teddy M. Keller
-
Patent number: 5844066Abstract: The present invention provides a process for the preparation of a lactic acid-based polyester having an excellent moldability, storage stability and biodegradability which has a less residual lactide left therein and is less susceptible to decomposition of lactic acid-based polyester and attachment of sublimed lactide to the molding apparatus, etc. at the devolatilization step and molding step after the polymerization reaction of lactic acid-based polyester. In the present invention, an organic chelating agent is added to a lactic acid-based polyester to deactivate the esterification catalyst used in the preparation of the lactic acid-based polyester, making it possible to inhibit the decomposition of lactic acid-based polyester at the devolatilizing process and molding process after polymerization reaction.Type: GrantFiled: September 10, 1996Date of Patent: December 1, 1998Assignee: Dainippon Ink and Chemicals, Inc.Inventor: Yasutoshi Kakizawa
-
Patent number: 5834575Abstract: As a heteroaromatic compound made functional so as to be used in nonlinear optical materials, the present invention provides a heteroaromatic compound represented by the following Formula (1), (2), (3) or (4), a polymer obtained from any of these, a nonlinear optical element comprised of the polymer, an optical device having such an element, and a process for producing them. ##STR1## wherein Ar.sup.1, Ar.sup.2 and Ar.sup.3 each independently represent an aromatic group or an aromatic group having a substituent, R.sup.1, R.sup.2 and R.sup.3 each independently represent a hydrogen atom or a monovalent organic group, X represents a monovalent organic group, Y represents a hydrogen atom or a monovalent functional group, and n represents an integer of 2 to 10.Type: GrantFiled: November 13, 1996Date of Patent: November 10, 1998Assignee: Hitachi Chemical Company, Ltd.Inventors: Yutaka Honda, Iwao Fukuchi, Masato Taya, Kwan-Yue Alex Jen
-
Patent number: 5789532Abstract: Perfluoroalkyleneethertriazine oligomer obtained by reacting a dinitrile compound NC--RF.sup.0 --CN where Rf.sup. is --(CFXOCF.sub.2)a(CF.sub.2)b(CF.sub.2 OCFX)c--, where X is a fluorine atom or a CF.sub.3 group, a is an integer of 1 to 5, b is an integer of 1 to 2 and c is an integer of 1 to 5, or Rf.sup.0 is --CF.sub.2 O(CF.sub.2 O)dCF.sub.2 --, where d is an integer of 1 to 8, with ammonia, further reacting the resulting diamizine compound with a dinitrile compound NC--Rf.sup.1 --CN, Rf.sup.1 has the same meaning as that for Rf.sup.0 or Rf.sup.1 is a perfluoroalkylene group having 4 to 8 carbon atoms thereby obtaining a perfluoroalkyleneetherpolyimidoylamizine oligomer, then reacting the resulting oligomer with a perfluoronitrile compound Rf.sup.2 CN, Rf.sup.2 is CF.sub.3 (OCF.sub.2)e-- where e is an integer of 3 to 10 thereby treating the terminal groups thereof, and then subjecting the resulting terminal-treated oligomer to a ring-closing reaction with a perfluoroacylating agent RF.sup.3 COY, Rf.sup.Type: GrantFiled: December 26, 1996Date of Patent: August 4, 1998Assignees: Nippon Mektron, Limited, S.V. LebedevInventors: Riichi Iwa, Haruyoshi Tatsu, Sokolov Sergey Vasilyevich, Kollar Alexander Nikolaevich
-
Patent number: 5783659Abstract: Perfluoroalkyleneethertriazine oligomer obtained by reacting a dinitrile compound NC--Rf.sup.0 --CN, where Ff.sup.0 is --(CFXOCF.sub.2)a(CF.sub.2)b(CF.sub.2 OCFX)c--, where X is a fluorine atom or a CF.sub.3 group, a is an integer of 1 to 5, b is an integer of 1 to 2 and c is an integer of 1 to 5, or Rf.sup.0 is --CF.sub.2 O(CF.sub.2 O)dCF.sub.2 --, where d is an integer of 1 to 8, with ammonia, further reacting the resulting diamizine compound with a dinitrile compound NC--RF.sup.1 --CN, RF.sup.1 has the same meaning as that for Rf.sup.0 or Rf.sup.1 is a perfluoroalkylene group having 4 to 8 carbon atoms thereby obtaining a perfluoroalkyleneetherpolyimidoyamizine oligomer, then reacting the resulting oligomer with a perfluoronitrile compound Rf.sup.2 CN, Rf.sup.2 is CF.sub.3 (OCF.sub.2).sub.e -- where e is an integer of 3 to 10 thereby treating the terminal groups thereof, and then subjecting the resulting terminal-treated oligomer to a ring-closing reaction with a perfluoroacylating agent RF.sup.3 COY, Rf.Type: GrantFiled: December 26, 1996Date of Patent: July 21, 1998Assignees: Nippon Mektron, Limited, S.V. LebedevInventors: Riichi Iwa, Haruyoshi Tatsu, Sokolov Sergey Vasilyevich, Kollar Alexander Nikolaevich
-
Patent number: 5708129Abstract: Described is a method of reducing resin bleed of a cyanate ester-containing die attach adhesive produced by curing a liquid resin system that contains cyanate ester monomer or mixtures that include cyanate ester monomer by adding an additive comprising at least one alkylene aromatic compound and curing the liquid resin system with the alkylene aromatic compound . Also disclosed is a die attach adhesive that comprises a resin system with an alkylene aromatic compound.Type: GrantFiled: July 17, 1996Date of Patent: January 13, 1998Assignee: Johnson Matthey, Inc.Inventors: My N. Nguyen, Kim-Chi Le
-
Patent number: 5681921Abstract: Perfluoroalkyleneethertriazine oligomer obtained by reacting a dinitrile compound NC--Ff.sup.0 --CN, where Ff.sup.0 is --(CFXOCF.sub.2)a(CF.sub.2)b(CF.sub.2 OCFX)c--, where X is a fluorine atom or a CF.sub.3 group, a is an integer of 1 to 5, b is an integer of 1 to 2 and c is an integer of 1 to 5, or Rf.sup.0 is --CF.sub.2 O(CF.sub.2 O)dCF.sub.2 --, where d is an integer of 1 to 8, with ammonia, further reacting the resulting diamizine compound with a dinitrile compound NC--Rf.sup.1 --CN, Rf.sup.1 has the same meaning as that for Rf.sup.0 or Rf.sup.1 is a perfluoroalkylene group having 4 to 8 carbon atoms thereby obtaining a perfluoroalkyleneetherpolyimidoylamizine oligomer, then reacting the resulting oligomer with a perfluoronitrile compound Rf.sup.2 CN, Rf.sup.2 is CF.sub.3 (OCF.sub.2).sub.e -- where e is an integer of 3 to 10 thereby treating the terminal groups thereof, and then subjecting the resulting terminal-treated oligomer to a ring-closing reaction with a perfluoroacylating agent RF.sup.3 COY, Rf.Type: GrantFiled: April 11, 1995Date of Patent: October 28, 1997Assignees: Nippon Mektron, Limited, S.V. LebedevInventors: Riichi Iwa, Haruyoshi Tatsu, Sokolov Sergey Vasilyevich, Kollar Alexander Nikolaevich
-
Patent number: 5641852Abstract: Disclosed is a thermosetting resin composition comprising cyanate resin, a compound containing at least one or more than one of a phenolic hydroxyl radical and an epoxy resin, wherein said resin has excellent adhesive and heat resistant properties while at the same time possessing a low hardening contraction rate and contributing to higher dimensional stability, and method of making the same.Type: GrantFiled: January 11, 1996Date of Patent: June 24, 1997Assignee: Kanegafuchi Kagaku Kogyo Kabushiki KaishaInventors: Hiroyuki Tsuji, Shoji Hara, Hirosaku Nagano
-
Patent number: 5621145Abstract: When a novel bisamidoxime compound represented by the following general formula: ##STR1## where R is an alkylidene group having 1 to 6 carbon atoms, or a perfluoroalkylidene group having 1 to 10 carbon atoms, is used as a vulcanizing agent for fluorine-containing elastomers having cyano groups as cross-linkable groups, the resulting vulcanizates having a satisfactory compression set are obtained without any problem of processability such as roll kneadability, etc.Type: GrantFiled: January 5, 1996Date of Patent: April 15, 1997Assignee: Nippon Mektron, LimitedInventors: Satoru Saito, Haruyoshi Tatsu, Lev Solomonovich, deceased, Ziefman Y. Vilovich, Postovoi S. Anatol'evich, Sterlin S. Rafailovich
-
Patent number: 5489637Abstract: Described is a flexible adhesive formulation for bonding a semiconductor device to a flexible substrate and a flexible card containing a semiconductor device which can be processed in a computer.Type: GrantFiled: February 22, 1995Date of Patent: February 6, 1996Assignee: Johnson Matthey IncInventors: My N. Nguyen, Yuan Y. Chien
-
Patent number: 5405916Abstract: Terpolymers of polyolefin/acrylic acid or substituted acrylic acid/acrylonitrile are prepared by combining a polyolefin/acrylic acid or substituted acrylic acid copolymer with at least one dinitrile to form a mixture and reacting the mixture at a temperature of at least 200.degree. C. for a time sufficient to form the terpolymer. Copolymers of polyolefin/acrylonitrile are obtained when the reaction is carried to completion. The total reaction masses obtained comprising terpolymer or copolymer, cyclic imide, solvent, when used, and any unreacted dinitrile find use as pour point depressants in heavy hydrocarbon oils.Type: GrantFiled: October 22, 1993Date of Patent: April 11, 1995Assignee: Conoco Inc.Inventors: Kenneth W. Pober, Charles M. Starks
-
Patent number: 5386000Abstract: Described is a flexible adhesive formulation for bonding a semiconductor device to a flexible substrate and a flexible card containing a semiconductor device which can be processed in a computer.Type: GrantFiled: December 3, 1993Date of Patent: January 31, 1995Assignee: Johnson Matthey Inc.Inventor: My N. Nguyen
-
Patent number: 5371178Abstract: Described is a rapidly curing adhesive formulation and a method of reducing the curing time of an adhesive formulation containing cyanate ester.Type: GrantFiled: December 3, 1993Date of Patent: December 6, 1994Assignee: Johnson Matthey Inc.Inventor: My N. Nguyen
-
Patent number: 5350828Abstract: Dithioether-linked phthalonitrile monomer are prepared by a substitution reaction between 4-nitrophthalonitrile and a dimercaptan and are polymerized to a high-temperature, oxidation-resistant polymer by heating them at a temperature above their melting point. The rate of polymerization is increased by the addition of an amine. Electrical conductivity of the polymer can be increased to the conductor range by heating the polymer above about 400.degree. C.Type: GrantFiled: December 18, 1992Date of Patent: September 27, 1994Assignee: The United States of America as represented by the Secretary of the NavyInventors: Teddy M. Keller, Thomas R. Price, deceased
-
Patent number: 5304625Abstract: Phosphazene-containing amines having at least one amine or substituted amine moiety reactive with nitrile groups of the phthalonitrile monomers or oligomeric resins are useful curing agents for phthalonitriles. Typically, the phosphazene-containing amines useful as curing agents in the present invention have the formula: ##STR1## wherein each of X.sub.1-6 is a hydrogen, an unsubstituted amine group, or an amine group substituted with C.sub.1 -C.sub.12 alkyl groups or aromatic groups, at least one of X.sub.1-6 includes an amine group, and each of R'.sub.1-6 is an alkyl, aromatic, or alkyl-substituted aromatic moiety, or a linear polymer of the phosphazene-based amine monomer. The curing agents enhance the speed of cure and also add flame retardancy to the cured polymers.Type: GrantFiled: February 19, 1993Date of Patent: April 19, 1994Assignee: The United States of America as represented by the Secretary of the NavyInventor: Teddy M. Keller
-
Patent number: 5292854Abstract: Imide-containing phthalonitrile monomers are prepared from a phthalonitrile and an aromatic dianhydride. The monomer and a method for preparing the monomer is disclosed. These monomers are synthesized into heat resistant polymers and copolymers with aromatic ring structure incorporating imide and ether linkages. The synthesis of the high temperature thermosetting polymers and copolymers is also disclosed.Type: GrantFiled: July 30, 1992Date of Patent: March 8, 1994Assignee: The United States of America as represented by the Secretary of the NavyInventor: Teddy M. Keller
-
Patent number: 5284924Abstract: Terpolymers of polyolefin/acrylic acid or substituted acrylic acid/acrylonitrile are prepared by combining a polyolefin/acrylic acid or substituted acrylic acid copolymer with at least one dinitrile to form a mixture and reacting the mixture at a temperature of at least 200.degree. C. for a time sufficient to form the terpolymer. Copolymers of polyolefin/acrylonitrile are obtained when the reaction is carried to completion. The total reaction masses obtained comprising terpolymer or copolymer, cyclic imide, solvent, when used and any unreacted dinitrile find use as pour point depressants in heavy hydrocarbon oils.Type: GrantFiled: October 23, 1991Date of Patent: February 8, 1994Assignee: Conoco Inc.Inventors: Kenneth W. Pober, Charles M. Starks
-
Patent number: 5262514Abstract: Substituted and unsubstituted di-phthalonitrile monomers devoid of ether /or phenoxy groups are solid at room temperature and which monomers are defined by the following general formula: ##STR1## where R is an aromatic tetravalent radical, thermoplastic prepolymers and thermosetting polymers which polymers are solid at room temperature and have a defined glass transition temperature if said polymers are cured at a temperature below a critical temperature or are devoid of a glass transition temperature if said polymers are postcured at a temperature exceeding said critical temperature.Type: GrantFiled: March 12, 1992Date of Patent: November 16, 1993Assignee: The United States of America as represented by the Secretary of the NavyInventor: Teddy M. Keller
-
Patent number: 5250600Abstract: Described is a flexible adhesive formulation for bonding a semiconductor device to a flexible substrate and a flexible card containing a semiconductor device which can be processed in a computer.Type: GrantFiled: May 28, 1992Date of Patent: October 5, 1993Assignee: Johnson Matthey Inc.Inventors: My N. Nguyen, Yuan Y. Chien
-
Patent number: 5247060Abstract: Curing of phthalonitrile monomers and prepolymers is accelerated by inclusion of an acid curing agent. Cured phthalonitrile polymers have high thermal oxidative stability and are useful as resins in various compositions and as adhesives.Type: GrantFiled: January 9, 1992Date of Patent: September 21, 1993Assignee: The United States of America as represented by the Secretary of the NavyInventor: Teddy M. Keller
-
Patent number: 5239052Abstract: Aromatic sulfides including diarylsulfides and poly(arylene sulfides) are produced in a novel synthesis in high yield under moderate conditions by heating an aromatic disulfide in the presence of aromatic halide, in which the halide is chloride, bromide or iodide; the diaryl sulfides are useful precursors and starting materials for a range of compounds and the poly(arylene sulfides) are important high temperature engineering thermoplastics.Type: GrantFiled: September 14, 1992Date of Patent: August 24, 1993Inventors: Allan S. Hay, Zhi Y. Wang
-
Patent number: 5237045Abstract: Polymerization or cure of di-phthalonitrile monomers or prepolymers by a curing agent selected from (a) an acid and an amine, (b) a salt of an acid and an amine, and (c) mixtures of (a) and (b). In a preferred embodiment, the curing agents are amine salts which are reaction products of an aromatic amine and an aromatic sulfonic acid. The use of the novel curing agents enhances curing rates and results in polymers which have high Tg.Type: GrantFiled: January 9, 1992Date of Patent: August 17, 1993Assignee: The United States of America as represented by the Secretary of the NavyInventors: Peter J. Burchill, Teddy M. Keller
-
Patent number: 5210179Abstract: Hydroxyterminated prepolymers, used in curing reactions with isocyanates to produce elastomers, are prepared by continuously adding over periods of 12-50 hours an oxetane monomer to a reaction mixture containing a diol initiator and a catalyst capable of catalyzing the cationic quasi-living cationic polymerization of the monomer, the rate of addition to maintain stoichiometric excess over the monomer. Polymerization is terminated by adding brine. Polymers of increased molecular weight and reduced impurity levels result.Type: GrantFiled: January 28, 1992Date of Patent: May 11, 1993Assignee: The Secretary of State for Defence in her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern IrelandInventor: Malcolm J. Stewart
-
Patent number: 5208318Abstract: Phosphazene-containing amines having at least one amine or substituted amine moiety reactive with nitrile groups of the phthalonitrile monomers or oligomeric resins are useful curing agents for phthalonitriles. Typically, the phosphazene-containing amines useful as curing agents in the present invention have the formula: ##STR1## wherein each of X.sub.1-6 is a hydrogen, an unsubstituted amine group, or an amine group substituted with C.sub.1 -C.sub.12 alkyl groups or aromatic groups, at least one of X.sub.1-6 includes an amine group, and each of R'.sub.1-6 is an alkyl, aromatic, or alkyl-substituted aromatic moiety, or a linear polymer of the phosphazene-based amine monomer. The curing agents enhance the speed of cure and also add flame retardancy to the cured polymers.Type: GrantFiled: March 15, 1991Date of Patent: May 4, 1993Inventor: Teddy M. Keller
-
Patent number: 5206321Abstract: Novel polycyanate compositions containing one or more mesogenic moieties as lateral substituents are disclosed which provide improved processability relative to polycyanates containing one or more mesogenic moieties in the main chain of the molecule. Molecular level ordering of the resulting thermosets is maintained much similar to that found thermosets of polycyanates which have one or more mesogenic moieties in the main chain.Type: GrantFiled: October 3, 1991Date of Patent: April 27, 1993Assignee: The Dow Chemical CompanyInventors: Robert E. Hefner, Jr., Jimmy D. Earls
-
Patent number: 5202414Abstract: Dithioether-linked phthalonitrile monomer are prepared by a substitution reaction between 4-nitrophthalonitrile and a dimercaptan and are polymerized to a high-temperature, oxidation-resistant polymer by heating them at a temperature above their melting point. The rate of polymerization is increased by the addition of an amine. Electrical conductivity of the polymer can be increased to the conductor range by heating the polymer above about 400.degree. C.Type: GrantFiled: October 19, 1990Date of Patent: April 13, 1993Assignee: The United States of America as Represented by the Secretary of the NavyInventors: Teddy M. Keller, Thomas R. Price, deceased
-
Patent number: 5189134Abstract: Novel nonlinearly optically active polymers, well suited for electrooptical applications, are prepared by copolymerizing a first difunctional monomer with a second difunctional comonomer, with at least one of such difunctional monomers including a polar charge transfer moiety containing at least one electron acceptor group and at least one electron donor group (D), and further wherein the polymerizable functional groups are borne by the one or more electron donor groups (D).Type: GrantFiled: September 18, 1989Date of Patent: February 23, 1993Assignee: Rhone-Poulenc ChimieInventors: Gerard Mignani, Pascal Barthelemy, Remi Meyrueix
-
Patent number: 5177183Abstract: Aromatic sulfides including diarylsulfides and poly(arylene sulfides) are produced in a novel synthesis in high yield under moderate conditions by heating an aromatic disulfide in the presence of aromatic halide, in which the halide is chloride, bromide or iodide; the diaryl sulfides are useful precursors and starting materials for a range of compounds and the poly(arylene sulfides) are important high temperature engineering thermoplastics.Type: GrantFiled: August 30, 1990Date of Patent: January 5, 1993Inventors: Allan S. Hay, Zhi Y. Wang
-
Patent number: 5159054Abstract: Imide-containing phthalonitrile monomers are synthesized into heat resistant polymers and copolymers with aromatic ring structure incorporating imide and ether linkages. The synthesis of the high temperature thermosetting polymers and copolymers is also disclosed.Type: GrantFiled: January 10, 1991Date of Patent: October 27, 1992Assignee: The United States of America as represented by the Secretary of the NavyInventor: Teddy M. Keller
-
Patent number: 5132396Abstract: Highly aromatic oligomeric imide-containing phthalonitriles are prepared by reacting an aromatic dianhydride with an aromatic or aliphatic diamine and endcapping the resulting reaction product with 4-aminophthalonitrile. The prepolymers are highly stable to storage. When heated above their melting or softening points, they polymerize to a thermosetting polymeric material useful as an advanced matrix material. In the case where the oligomeric monomers are produced by reacting dianhydrides with aromatic diamines, they polymerize to form high-temperature adhesives.Type: GrantFiled: April 30, 1990Date of Patent: July 21, 1992Assignee: The United States of America as represented by the Secretary of the NavyInventor: Teddy M. Keller
-
Patent number: 5093468Abstract: The invention relates to high molecular weight, substantially linear copolyarylene sulfides predominantly containing biphenylene sulfide units, which are produced by reaction of aromatic halogen compounds and halobiphenylenes with sulfur donors in dipolar aprotic solvents, and to their use for moldings, films and fibers exposed to high temperatures and--preferably in reinforced form--as injection molding compounds.Type: GrantFiled: September 4, 1990Date of Patent: March 3, 1992Assignee: Bayer AktiengesellschaftInventor: Karl-Heinz Kohler
-
Patent number: 5066773Abstract: A poly Ressert can be formed by first reacting benzimidazole with an aliphatic diacid chloride to form bisbenzimidazole and then reacting the bisbenzimidazole with an aliphatic diacid chloride and cyanide to form the poly Reissert.Type: GrantFiled: October 6, 1989Date of Patent: November 19, 1991Assignee: Virginia Tech Intellectual Properties, Inc.Inventors: Harry W. Gibson, Yajnanarayana H. R. Jois
-
Patent number: 5053478Abstract: Production of polyenaminonitriles including those which can be cyclized to very stable poly(aminoquinolines) without the evolution of any small molecules and thus in a manner free of volatiles. The polyenaminonitriles are polymers which have desirable dielectric properties, and include those which can be cyclized to poly(aminoquinolines) without the evolution of volatiles to make defect-free films and composites of similar dielectric properties because of this characteristic.Type: GrantFiled: August 2, 1990Date of Patent: October 1, 1991Inventors: James A. Moore, Douglas Robello
-
Patent number: 5051493Abstract: Bis-phthalonitrile resins are cured using ionic metal phthalocyanine acceators. The ionic metal phthalocyanines are nontoxic and accelerate the cure rate of the resins without adversely affecting cured polymer strength. Di-Na, di-Li, Mg and Cd phthalocyanines in particular provide excellent cure acceleration. Also, the metal phthalocyanine can be made soluble in the resin by appropriate substitution of the aromatic rings, thus providing for homogenous polymerization.Type: GrantFiled: May 31, 1990Date of Patent: September 24, 1991Assignee: The United States of America as represented by the Secretary of the NavyInventor: Theodore R. Walton
-
Patent number: 5004801Abstract: Dithioether-linked phthalonitrile monomer are prepared by a substitution reaction between 4-nitrophthalonitrile and a dimercaptan and are polymerized to a high-temperature, oxidation-resistant polymer by heating them at a temperature above their melting point. The rate of polymerization is increased by the addition of an amine. Electrical conductivity of the polymer can be increased to the conductor range by heating the polymer above about 400.degree. C.Type: GrantFiled: November 21, 1988Date of Patent: April 2, 1991Assignee: The United States of America as represented by the Secretary of the NavyInventors: Teddy M. Keller, Thomas R. Price, deceased
-
Patent number: 5003039Abstract: High temperature polymeric materials, which are easily process into void-free components, are needed for use in composites for advanced aerospace applications. These materials could bridge the gap between currently-used polymeric materials and ceramics or metal. Phthalonitrile resins can be used as high temperature polymeric material and 1,3-bis(3-aminophenoxy)benzene can be used as a curing agent to reduce voids and benzene can be used as a curing agent to reduce voids and blisters formed from volatiles during polymerization.Type: GrantFiled: November 18, 1988Date of Patent: March 26, 1991Assignee: The United States of America as represented by the Secretary of the NavyInventor: Teddy M. Keller
-
Patent number: 4980454Abstract: Reaction of a dihalogenobenzonitrile and a dihalogenobenzene with a thioetherifying agent provides a poly(arylene thioether) copolymer which is both thermoplastic and thermosetting in nature. Utilization of these dual properties results in products of improved physical properties.Type: GrantFiled: April 14, 1989Date of Patent: December 25, 1990Assignee: Tosoh CorporationInventors: Tomoji Tamai, Tetsuya Asahi, Yozo Kondo
-
Patent number: 4973663Abstract: A novel thermoplastic poly(arylene thioether) copolymer which may be cross-linked is provided. The copolymer may be prepared by reacting a dihalogenobenzonitrile, a dihalogenophenyl sulfone and a thioetherifying agent in a suitable organic solvent.Type: GrantFiled: April 14, 1989Date of Patent: November 27, 1990Assignee: Tosoh CorporationInventors: Tomoji Tamai, Tetsuya Asahi, Yozo Kondo
-
Patent number: 4966954Abstract: Production of polyenaminonitriles including those which can be cyclized to very stable poly(aminoquinolines) without the evolution of any small molecules and thus in a manner free of volatiles. The polyenaminonitriles are polymers which have desirable dielectric properties, and include those which can be cyclized to poly(aminoquinolines) without the evolution of volatiles to make defect-free films and composites of similar dielectric properties because of this characteristic.Type: GrantFiled: May 23, 1988Date of Patent: October 30, 1990Assignee: Rensselaer Polytechnic InstituteInventors: James A. Moore, Douglas Robello
-
Patent number: 4918159Abstract: Novel styrene-based polymers and a process for efficient production thereof are disclosed. The styrene-based polymers have a branching nucleus represented by the general formula: R(S).sub.k or R(A-S).sub.k (wherein all the symbols are as defined in the appended claims), and have a sulfur content of 6 to 550 ppm, a weight average molecular weight of 450,000 to 1,300,000, and a weight average molecular weight/number average molecular weight (Mw/Mn) ratio of 2:1 to 15:1. The styrene-based polymers are greatly improved in impact resistance while maintaining sufficiently high fluidity and moldability and thus when injection or extrusion molded, can provide moldings having an excellent mechanical strength.Type: GrantFiled: August 29, 1988Date of Patent: April 17, 1990Assignee: Idemitsu Petrochemical Co., Ltd.Inventors: Shinichi Nakamura, Hideo Teshima, Eiichi Terada
-
Patent number: 4900807Abstract: There are disclosed a nitrile-terminated Schiff compound represented by the formula X--Z--Y--C.tbd.N).sub.m (I) wherein n is 1 or 2, Z is --CH.dbd.N-- or --N.dbd.CH-- and Y is a divalent organic group such as phenylene and the like, and X is the same as Y when n=2 or H, lower alkyl group etc. when n=1; polymers obtained by polymerizing said Schiff compound alone or together with other monomers, and a process for preparing such a polymer therefrom.Type: GrantFiled: February 2, 1988Date of Patent: February 13, 1990Assignee: Hitachi, Ltd.Inventors: Akio Nishikawa, Toru Koyama, Hideki Asano, Toshikazu Narahara
-
Patent number: 4841016Abstract: An additive composition for enhancing curing and color clarity properties of polyester resins. The additive comprises from about 50 to 75 parts by weight of a mercaptan, and from about 50 to about 25 parts by weight of a quaternary ammonium salt. From about 0.5 to about 25 parts by weight of a polymerization initiator can be incorporated into the additive when the polyester resin is utilized as a gel coat. Resinous compositions formulated with the additive consist essentially of from about 50 to about 99.5 parts by weight of a polyester resin, from about 0.5 to about 35 parts by weight of the mercaptan, from about 0.1 to about 15 parts by weight of the quaternary ammonium salt, and a minor effective amount of an oxidizing agent for the polyester resin.Type: GrantFiled: March 16, 1988Date of Patent: June 20, 1989Inventor: Bill R. Edwards
-
Patent number: 4824932Abstract: The invention relates to aromatic polyamides and polyamidimides, and a method of manufacturing these by transamidation of aromatic biasmides of carboxylic acids, using aromatic di- and/or tricarboxylic acids or their anhydrides, in the melt, at temperatures between 220.degree. to 390.degree. C.Type: GrantFiled: December 30, 1986Date of Patent: April 25, 1989Assignee: Huls AktiengesellschaftInventors: Juergen Finke, Martin Bartmann
-
Patent number: 4804424Abstract: Polyethers are formed by polymerizing oxetanes having one or two pendant groups which contain cyano moieties, particularly 3-cyanomethyl-3-methyl oxetane and 3,3-Bis(cyanomethyl) oxetane. The polyethers may also contain mer units derived from other cyclic ethers, including other oxetanes and tetrahydrofurans. The cyano group gives the polyether improved compatibility with nitrate ester plasticizers. The polyethers are curable with polyfunctional isocyanates to form binders for propellants, explosives or the like.Type: GrantFiled: June 3, 1988Date of Patent: February 14, 1989Assignee: Morton Thiokol, Inc.Inventor: Jerald C. Hinshaw
-
Patent number: 4764586Abstract: Internally plasticized elastomeric binders for projectile propellants are cured polyethers containing THF, CYMMO plus BMEMO, BEEMO and/or OMMO mer units. The polyethers are fluid at room temperature and are miscible with nitrate ester plasticizers. Propellant binders prepared from these polyethers are curable, have low T.sub.g 's, good mechanical properties, and I.sub.sp 's comparable to PEG-based binders.Type: GrantFiled: October 29, 1986Date of Patent: August 16, 1988Assignee: Morton Thiokol, Inc.Inventors: Gerald E. Manser, Graham C. Shaw, III