Phenolic Reactant Contains At Least One Carboxylic Acid Group Or Is Derivative Thereof Patents (Class 528/206)
  • Patent number: 4380619
    Abstract: Oxy- and thio-aryl-phenylated aromatic heterocyclic polymers having the general formula ##STR1## wherein Ar is a monovalent aromatic radical containing an oxy- or thio-linkage, Ar' is a divalent aromatic radical, R is a monovalent aromatic radical, Z is a divalent heterocyclic radical and n is an integer equal to the number of repeating units, are prepared from biscyclopentadienones with diethynyl heterocyclic compounds.
    Type: Grant
    Filed: April 8, 1982
    Date of Patent: April 19, 1983
    Assignee: The United States of America as represented by the Secretary of the Air Force
    Inventors: Bruce A. Reinhardt, Fred E. Arnold
  • Patent number: 4374239
    Abstract: Described herein is a process for preparing polyarylates which comprises reacting a diester derivative of a dihydric phenol with an aromatic dicarboxylic acid in the presence of from about 10 to about 60 weight percent of at least one particular halogenated and/or etherated substituted aromatic or heteroaromatic compound, at a temperature of from about 260.degree. to about 350.degree. C.
    Type: Grant
    Filed: August 18, 1981
    Date of Patent: February 15, 1983
    Assignee: Union Carbide Corporation
    Inventors: Mitchell H. Berger, Louis M. Maresca, Ulrich A. Steiner
  • Patent number: 4374228
    Abstract: A novel wholly aromatic polyester is provided which exhibits an anisotropic melt phase and which is capable of readily undergoing melt processing. The polyester of the present invention consists essentially of the recurring units (a) paraoxybenzoyl moiety, (b) bromo-substituted-para-oxybenzoyl moiety, and (c) meta-oxybenzoyl moiety. The resulting polymer may be economically produced. Additionally, it may be melt processed at an advantageous temperature which makes possible the utilization of standard equipment such as that heretofore utilized for the melt processing of polyethylene terephthalate.
    Type: Grant
    Filed: August 3, 1981
    Date of Patent: February 15, 1983
    Assignee: Fiber Industries, Inc.
    Inventor: Jeffrey T. Langley
  • Patent number: 4366304
    Abstract: Novel copolyimides are prepared from mixtures of tetramethyl-cyclobutane-1,2,3,4-tetracarboxylic dianhydride and other aliphatic and aromatic dianhydrides. Their dianhydride mixtures are reacted with aliphatic or aromatic diamines to form copolyimides which are useful as engineering plastics.
    Type: Grant
    Filed: July 24, 1981
    Date of Patent: December 28, 1982
    Assignee: Standard Oil Company (Indiana)
    Inventors: Tayseer S. Nimry, Ellis K. Fields
  • Patent number: 4362859
    Abstract: Novel polyimides, copolyimides and molding compositions are prepared from novel dianhydrides such as bicyclo[4.2.0]octane-2,5 diphenyl-7,8-dimethyl,3,4,7,8-tetracarboxylic dianhydride and bicyclo[4.2.0]octane-7,8-dimethyl-3,4,7,8-tetracarboxylic acid dianhydride. The novel polyimides are useful as engineering plastics. The novel dianhydrides are useful for the preparation of the polyimides.
    Type: Grant
    Filed: August 19, 1981
    Date of Patent: December 7, 1982
    Assignee: Standard Oil Company (Indiana)
    Inventors: Tayseer S. Nimry, Ellis K. Fields
  • Patent number: 4361693
    Abstract: Poly(arylene ketones) are prepared by the reaction of difunctional aromatic compounds with derivatives of thio- or dithiocarbonic acids in the presence of a superacid catalyst system. In a preferred embodiment, diphenyl ether reacts with S-methyl chlorothioformate in HF/BF.sub.3 to produce poly(p-phenyleneoxy-p-phenylene carbonyl), i.e.
    Type: Grant
    Filed: July 8, 1981
    Date of Patent: November 30, 1982
    Assignee: Raychem Corporation
    Inventor: Viktors Jansons
  • Patent number: 4360657
    Abstract: Novel polyimides and molding compositions are prepared from tricyclo[6.4.0.0.sup.2,7 ]dodecane-1,8,2,7-tetracarboxylic acid dianhydride. Also a novel dianhydride-,tricyclo[6.4.0.0.sup.2,7 ]dodecane-1,8,2,7-tetracarboxylic acid dianhydride is prepared by a novel photodimerization of 1-cyclohexene-1,2-dicarboxylic anhydride. The polyimides are useful as engineering plastics.
    Type: Grant
    Filed: August 19, 1981
    Date of Patent: November 23, 1982
    Assignee: Standard Oil Company (Indiana)
    Inventors: Tayseer S. Nimry, Ellis K. Fields
  • Patent number: 4358580
    Abstract: Novel polyimides, copolyimides and molding compositions are prepared from novel dianhydrides such as tricyclo[6.4.0.0.sup.2,7 ] dodecane-3,6-diphenyl-1,8,4,5-tetracarboxylic acid dianhydride and tricyclo[6.4.0.0.sup.2,7 ] dodecane-1,8,4,5-tetracarboxylic acid dianhydride. The novel polyimides are useful as engineering plastics. The novel dianhydrides are useful for the preparation of the polyimides. Other dianhydrides can be mixed with our novel dianhydrides to make novel copolyimides useful as engineering plastics.
    Type: Grant
    Filed: August 19, 1981
    Date of Patent: November 9, 1982
    Assignee: Standard Oil Company (Indiana)
    Inventors: Tayseer S. Nimry, Ellis K. Fields
  • Patent number: 4358579
    Abstract: Novel polyimides and molding compositions are prepared from tetramethylcyclobutane-1,2,3,4-tetracarboxylic dianhydride and diamines. Also glass and graphite filled polyimides are prepared. The polyimides are useful as engineering plastics.
    Type: Grant
    Filed: July 24, 1981
    Date of Patent: November 9, 1982
    Assignee: Standard Oil Company (Indiana)
    Inventors: Tayseer S. Nimry, Ellis K. Fields
  • Patent number: 4358562
    Abstract: Novel copolyimides and molding compositions are prepared from tetramethylcyclobutane-1,2,3,4-tetracarboxylic dianhydride and mixtures of diamines. Also glass and graphite filled polyimides are prepared. The polyimides are useful as engineering plastics.
    Type: Grant
    Filed: July 24, 1981
    Date of Patent: November 9, 1982
    Assignee: Standard Oil Company (Indiana)
    Inventors: Edward E. Paschke, Tayseer S. Nimry, Ellis K. Fields
  • Patent number: 4358582
    Abstract: Novel polyimides and molding compositions are prepared from novel tricyclo[4.2.1.0.sup.2,5 ] nonane-3,4 dimethyl-3,4,7,8-tetracarboxylic acid dianhydride. The dianhydride is useful for the manufacture of polyimides which are useful as engineering plastics.
    Type: Grant
    Filed: August 19, 1981
    Date of Patent: November 9, 1982
    Assignee: Standard Oil Company (Indiana)
    Inventors: Tayseer S. Nimry, Ellis K. Fields
  • Patent number: 4355134
    Abstract: An improved wholly aromatic polyester is provided which exhibits an anisotropic melt phase and which is capable of readily undergoing melt processing. The wholly aromatic polyester consists essentially of the recurring units (a) p-oxybenzoyl moiety, (b) 2,6-dioxynaphthalene moiety, (c) 2,6-dioxyanthraquinone moiety, and (d) terephthaloyl moiety in the concentrations indicated. The resulting polymer is substantially free of aromatic rings possessing ring substitution and meta disposed linkages in the polymer chain. The present invention represents an improvement over the polyester of U.S. Pat. No. 4,184,996 since the melt phase may be formed at an advantageously reduced temperature thereby better facilitating the use of standard melt processing equipment when forming fibers, films, three-dimensional shaped articles, etc.
    Type: Grant
    Filed: June 4, 1981
    Date of Patent: October 19, 1982
    Assignee: Celanese Corporation
    Inventors: Larry F. Charbonneau, Gordon W. Calundann
  • Patent number: 4354018
    Abstract: A resinous linear polyester, poly(oxy-1,4-phenylene-3-oxotrimethylene), is made by the self-condensation of 3-(parahydroxyphenyl)propionic acid. The process is carried out interfacially or in an inert solvent by mixing 3-(parahydroxyphenyl)propionic acid with at least an equimolar proportion of thionyl chloride and maintaining the mixture at a reaction temperature for a time sufficient to allow substantially complete autocondensation. A base may be added in proportion at least about equivalent to the thionyl chloride. The autocondensate when purified is a white solid linear polyester not melting up to 360.degree. C. and may exhibit an intrinsic viscosity of at least 75 ml/g. It may be molded or pressed into a film.Co-condensed polyesters of 3-(parahydroxyphenyl)propionic acid with up to an equimolar proportion of parahydroxyphenylacetic acid may similarly be prepared.
    Type: Grant
    Filed: February 1, 1982
    Date of Patent: October 12, 1982
    Assignee: Michigan Molecular Institute
    Inventors: Hans-G. Elias, Robert J. Warner
  • Patent number: 4330668
    Abstract: In the production of an aromatic polyester by reacting at least one aromatic diester of the formula ##STR1## wherein R is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 8 carbon atoms; andAr.sub.2 is an arylene group,with at least one aromatic dicarboxylic acid of the formula ##STR2## wherein Ar.sub.2 is an arylene group,in the presence of a catalyst, the improvement which comprises employing a transition metal salt of naphthenic acid as the catalyst.
    Type: Grant
    Filed: May 16, 1980
    Date of Patent: May 18, 1982
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Sato Hideo, Takiguchi Teruo, Akimoto Norio, Ueno Ikuo
  • Patent number: 4324882
    Abstract: A method is provided for making polyimides resulting from aromatic organic dianhydride and organic diamine interaction in the presence of an alkali metal salt of an oxygenated phosphorus compound.
    Type: Grant
    Filed: September 19, 1980
    Date of Patent: April 13, 1982
    Assignee: General Electric Company
    Inventor: Tohru Takekoshi
  • Patent number: 4314051
    Abstract: Described herein is a process for preparing crystalline polyarylates which comprises (a) forming a crystalline polyarylate prepolymer having a reduced viscosity of from 0.05 to about 0.4 dl/g by reacting at least one diester derivative of a dihydric phenol with at least one aromatic dicarboxylic acid in the presence of a solvent, at a temperature of from about 250.degree. to about 300.degree. C., and (b) heating the prepolymer so formed below its melting point to form a crystalline polyarylate having a reduced viscosity of from about 0.45 to about 1.2 dl/g.
    Type: Grant
    Filed: May 5, 1980
    Date of Patent: February 2, 1982
    Assignee: Union Carbide Corporation
    Inventors: Mitchell H. Berger, Markus Matzner, James M. Tibbitt
  • Patent number: 4310655
    Abstract: The subject polymers are novel homopolymers and copolymers. The homopolymers are characterized by relatively high T.sub.g of about 120.degree. C. relative to their T.sub.m of about 250.degree. C., whereby they can readily be fabricated into fibers, films and like structures from the melt, and retain strength above 100.degree. C. The copolymers have T.sub.g 's intermediate between those of the homopolymers of the constituent monomers, and can be fabricated as for the subject homopolymers.Novel processes of obtaining the monomer, p-(1,1-dimethyl-2-hydroxyethyl)benzoic acid, are disclosed.
    Type: Grant
    Filed: May 27, 1980
    Date of Patent: January 12, 1982
    Assignee: Allied Corporation
    Inventors: Herbert K. Reimschuessel, Bruce T. DeBona
  • Patent number: 4296232
    Abstract: Described herein is a process for preparing polyarylates which comprises reacting a diester derivative of a dihydric phenol with an aromatic dicarboxylic acid in the presence of from about 10 to about 60 weight percent of a diphenyl ether compound at a temperature of from about 260.degree. to about 350.degree. C. and in the presence of a magnesium catalyst.
    Type: Grant
    Filed: August 27, 1979
    Date of Patent: October 20, 1981
    Assignee: Union Carbide Corporation
    Inventors: Louis M. Maresca, Peter J. Gill, Mitchell H. Berger
  • Patent number: 4294956
    Abstract: Described herein is a process for preparing polyarylates which comprises reacting a diester derivative of a dihydric phenol with an aromatic dicarboxylic acid in the presence of from about 10 to about 60 weight percent of a diphenyl ether compound at a temperature of from about 260.degree. to about 350.degree. C.
    Type: Grant
    Filed: August 27, 1979
    Date of Patent: October 13, 1981
    Assignee: Union Carbide Corporation
    Inventors: Mitchell H. Berger, Peter J. Gill, Louis M. Maresca
  • Patent number: 4279803
    Abstract: A novel polyester is provided which has been found to exhibit an optically anisotropic melt phase at a temperature which enables it readily to undergo melt processing to form quality fibers, films, molded articles, etc. The polyester contains substantial concentrations of recurring 3-phenyl-4-oxybenzoyl and/or 2-phenyl-4-oxybenzoyl moieties in combination with 4-oxybenzoyl and/or 6-oxy-2-naphthoyl moieties in the proportions indicated. The wholly aromatic polyester is capable of forming the desired anisotropic melt at a temperature below approximately 350.degree. C.
    Type: Grant
    Filed: March 10, 1980
    Date of Patent: July 21, 1981
    Assignee: Celanese Corporation
    Inventor: Gordon W. Calundann
  • Patent number: 4267304
    Abstract: An aromatic copolyester capable of forming an anisotropic melt containing up to 75 mole % of recurring units of formula ##STR1## wherein R may be hydrogen, chlorine, bromine or alkyl groups containing from 1 to 4 carbon atoms.
    Type: Grant
    Filed: July 18, 1979
    Date of Patent: May 12, 1981
    Assignee: Imperial Chemical Industries Limited
    Inventors: Ronald G. Feasey, Brian P. Griffin
  • Patent number: 4259471
    Abstract: Polyphthalocyanine resins are obtained by heating, at a temperature from ut 240.degree. C. to 305.degree. C., one or more bisorthodinitriles of the general formula: ##STR1## wherein x is from 1 to 10 and the phenyl groups are attached at the meta or para position. These resins have exceptional thermal stability and oxidative resistance making them particularly useful in high-temperature structural composites.
    Type: Grant
    Filed: May 24, 1979
    Date of Patent: March 31, 1981
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Teddy M. Keller, James R. Griffith
  • Patent number: 4247682
    Abstract: A polymer of the general formula: R'--M--Ar--B--Ar'--MArBAr'--.sub.k-2 M--Ar--B--Ar'--R wherein M and D, which can be the same or different, are independently ##STR1## wherein each Ar is independentlyR'--M--Ar--D--Ar'[--MArDAr'--].sub.k-2 M--Ar--D--Ar'--R"wherein L is ##STR2## phenyleneoxy, ##STR3## a covalent bond or T, wherein T is as defined belowand each Ar' is independently ##STR4## wherein T is O, S, phenyleneoxy, or --CR.sub.2 -- wherein R is as defined below, or --O--Ar--O-- wherein Ar can have any of the values set forth above and wherein R' and R" are independently ##STR5## wherein X is a covalent bond, --O--, --S--, or --CR.sub.2 -- wherein each R is independently hydrogen, an alkyl or fluoroalkyl group, preferably of 1 to 10 carbons, phenyl or an electron withdrawing group substituted phenyl, Y is CN, NO.sub.2, ##STR6## or if X is a covalent bond, Y can be hydrogen as well as any of the foregoing; or Ar"CO-- or Ar"SO.sub.
    Type: Grant
    Filed: May 7, 1979
    Date of Patent: January 27, 1981
    Assignee: Raychem Corporation
    Inventor: Klaus J. Dahl
  • Patent number: 4238601
    Abstract: A bisorthodinitrile of the formula: ##STR1## wherein R' and R" are perfluorinated alkyls having from 1 to 4 carbon at, and the phenyl groups are attached at the para position. A polyphthalocyanine resin is prepared by heating one or more of these bisorthodinitriles at a temperature from about 260.degree. C. to about 295.degree. C. These resins are particularly useful in high-temperature structural composites used in high-temperature, moist or corrosive environments.
    Type: Grant
    Filed: June 25, 1979
    Date of Patent: December 9, 1980
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Teddy M. Keller, James R. Griffith
  • Patent number: 4234712
    Abstract: Polyphthalocyanine resins are obtained by heating one or more bisorthodiniles of the general formula: ##STR1## wherein R represents ##STR2## at temperature at or above the melting point thereof. The resins are useful in high-temperature structural composites and adhesives.
    Type: Grant
    Filed: September 14, 1979
    Date of Patent: November 18, 1980
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Teddy M. Keller, James R. Griffith
  • Patent number: 4230817
    Abstract: Thermotropic polyesters derived from ferulic acid exhibit an anisotropic melt. The polyesters may be comprised of all ferulic acid, but they preferably include one or more additional monomers. Preparation of the polyesters is typically accomplished by melt polymerization of the esterified monomer or monomers. The polymers may be melt processed into fibers, films or other molded articles which may include conventional fillers and/or reinforcing agents.
    Type: Grant
    Filed: March 2, 1979
    Date of Patent: October 28, 1980
    Assignee: Celanese Corporation
    Inventor: Larry F. Charbonneau
  • Patent number: 4229564
    Abstract: The molecular weight of highly aromatic polymers made by the Friedel-Crafts polymerization of EN monomers of the formula Ar--L--Ar.sup.1 --X, wherein X is selected from SO.sub.2 Y or COY, Y being a radical selected from --OH, halogen, or alkyl, wherein Ar and Ar.sup.1 are independently ##STR1## wherein L is --CO--, --SO.sub.2 --, phenyleneoxy, --NHCO--, a covalent bond, --O--, or --CR.sub.2 --, wherein each R is independently hydrogen, an alkyl or fluoroalkyl group, phenyl or a phenyl group substituted by an electron withdrawing group such as halogen, NO.sub.2 or --CN, is controlled by including in the reaction mixture an acylatable aromatic compound whose rate of acylation under Friedel-Crafts conditions is at least about 150 times that of benzene. The molecular weight of other polymers made from EN type monomers by Friedel-Crafts catalysis can also be controlled in this way.
    Type: Grant
    Filed: April 26, 1976
    Date of Patent: October 21, 1980
    Assignee: Raychem Corporation
    Inventor: Klaus J. Dahl
  • Patent number: 4223123
    Abstract: Polyphthalocyanine resins are obtained by heating, at a temperature from ut 260.degree. C. to about 295.degree. C., one or more bisorthodinitriles of the general formula: ##STR1## wherein R' is an alkyl radical with 1 to 6 carbon atoms, R" is hydrogen or an alkyl radical with 1 to 6 carbon atoms, and the phenyl groups are attached at the meta or para position. These resins are particularly useful in high-temperature structural composites.
    Type: Grant
    Filed: May 29, 1979
    Date of Patent: September 16, 1980
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Teddy M. Keller, James R. Griffith
  • Patent number: 4219629
    Abstract: A p-oxybenzoyl copolyester which is flexible and soluble in organic solvents has recurring moieties of the formulas ##STR1## wherein the carbonyl groups of (B) are meta or para to each other and the oxygen atoms of (C) are meta or para to the sulfur atom thereof. Also described are organic solvent solutions of the p-oxybenzoyl copolyesters, molded articles made thereof and flexible coatings of such copolyesters on substrates.
    Type: Grant
    Filed: November 9, 1978
    Date of Patent: August 26, 1980
    Assignee: Dart Industries Inc.
    Inventor: Roger S. Storm
  • Patent number: 4200697
    Abstract: Unsaturated polyester resins will form foamed or solid plastics with water-binding agents containing an oxidated silicon compound in the presence of an initiator.
    Type: Grant
    Filed: February 7, 1979
    Date of Patent: April 29, 1980
    Inventor: David H. Blount
  • Patent number: 4184996
    Abstract: A wholly aromatic polyester is provided which unlike the aromatic polyesters normally encountered in the prior art is not intractable or difficultly tractable and readily undergoes melt processing with ease. The aromatic polyester of the present invention consists essentially of the recurring units (a) p-oxybenzoyl moiety, (b) 2,6-dioxynaphthalene moiety, and (c) terephthaloyl moiety, and is free of units which possess ring substitution. The resulting polyester exhibits a melting point below approximately 325.degree. C., preferably below 300.degree. C., and most preferably below approximately 290.degree. C. The ability of the wholly aromatic polyester to readily undergo melt processing can be attributed to its atypical inherent propensity to form a thermotropic melt phase at relatively low temperatures. The wholly aromatic polyester may be formed by a variety of procedures including a slurry polymerization technique (as defined) or a melt polymerization technique.
    Type: Grant
    Filed: February 15, 1978
    Date of Patent: January 22, 1980
    Assignee: Celanese Corporation
    Inventor: Gordon W. Calundann
  • Patent number: 4161470
    Abstract: A novel polyester is provided which has been found to exhibit a thermotropic melt phase at a temperature which enables it readily to undergo melt processing to form quality fibers, molded articles, etc. The polyester of the present invention is formed primarily of recurring 6-oxy-2-naphthoyl and p-oxybenzoyl moieties in the proportions indicated. The hydrogen atoms present upon the aromatic rings of these moieties optionally may be at least partially substituted (as described). Also, minor amounts of other ester-forming moieties may be included in the polyester so long as the thermotropic character and ease of melt processability is retained. In a preferred embodiment the wholly aromatic polyester is capable of undergoing melt processing at a temperature below approximately 325.degree. C., and in a particularly preferred embodiment at a temperature of approximately 280.degree. to 300.degree. C.
    Type: Grant
    Filed: October 20, 1977
    Date of Patent: July 17, 1979
    Assignee: Celanese Corporation
    Inventor: Gordon W. Calundann
  • Patent number: 4118535
    Abstract: This invention is concerned with a new class of polyetheramide-imide epoxy resin blends. More particularly, the invention is concerned with polyetheramide-imide epoxy resin blends which exhibit melt viscosities suitable for solventless-dry powder coating and curing of polyetherimide insulating films on various substrates. The polyetheramide-imide epoxy resin blends are also suitable for the manufacture of filaments, fibers, films, molding compounds, coatings, etc.
    Type: Grant
    Filed: November 3, 1975
    Date of Patent: October 3, 1978
    Assignee: General Electric Company
    Inventors: Eugene G. Banucci, Edith M. Boldebuck
  • Patent number: 4107143
    Abstract: The present invention provides a substantially linear aromatic polyester carbonate consisting essentially of hydroxybenzoic acid unit, hydroquinone unit, and carbonate unit as well as, depending on the circumstances, aromatic carboxylic acid unit, and having an inherent viscosity of at least 0.5. The present invention also provides an industrially advantageous method for producing such linear aromatic polyester carbonate through the process steps of melt-polycondensation, and, if necessary, followed by a further polycondensation in solid phase.Such aromatic polyester carbonate which the present invention provides exhibits excellent melt-forming property and melt anisotropy, hence any shaped article obtained by melt-forming of this aromatic polyester carbonate exhibits superior mechanical properties, in particular, excellent Young's modulus of longitudinal elasticity, and so on, which is highly useful as the material for industrial applications.
    Type: Grant
    Filed: February 3, 1977
    Date of Patent: August 15, 1978
    Assignees: Teijin Limited, Teyin Limited
    Inventors: Hiroo Inata, Tsuto Morinaga, Takatoshi Kuratsuji, Takanori Urasaki, Shoji Kawase
  • Patent number: 4101487
    Abstract: A heat curable coating medium for use in the formation of a cured, highly cross-linked, polymeric coating on a substrate. The coating medium comprises an aromatic diamide diacid diamine formed as the reaction product of an aromatic diamine and an aromatic dianhydride, in the molar ratio of two-to-one respectively, in a solvent.
    Type: Grant
    Filed: August 13, 1976
    Date of Patent: July 18, 1978
    Assignee: General Electric Company
    Inventor: Marvin A. Peterson