Patents by Inventor Roy Ray Odle

Roy Ray Odle has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).

  • Patent number: 11649322
    Abstract: A copolycarbonate includes 0.005-0.1 mole percent of sulfur-containing carbonate units derived from a sulfur-containing bisphenol monomer, 2-95 mole percent of high heat carbonate units derived from a high heat aromatic dihydroxy monomer, and 5-98 mole percent of a low heat carbonate units derived from a low heat aromatic monomer, each based on the sum of the moles of the carbonate units; and optionally, thioether carbonyl endcaps of the formula —C(?O)-L-S—R, wherein L is a C1-12 aliphatic or aromatic linking group and R is a C1-20 alkyl, C6-18 aryl, or C7-24 arylalkylene; wherein the sulfur content of the high heat copolycarbonate in the absence of the thioether endcaps is from 5-20 parts per million by weight.
    Type: Grant
    Filed: November 11, 2019
    Date of Patent: May 16, 2023
    Assignee: SHPP GLOBAL TECHNOLOGIES B.V.
    Inventors: Paul Dean Sybert, Roy Ray Odle, Jordi Calveras, Wei Zhao
  • Patent number: 11499011
    Abstract: A polyimide oligomer of formula (1a), (1b), a copolymer thereof, or a combination thereof wherein each G1 is independently the same or different, and is a cation group; each G2 is independently the same or different, and is an anion group; each D is independently the same or different, and is a single bond or C1-20 divalent hydrocarbon group; each V is independently the same or different, and is a tetravalent C4-40 hydrocarbon group; each R is independently the same or different, and is a C1-20 divalent hydrocarbon group; each n is independently the same or different, and is 1 to 1000, provided that the total of all values of n is greater than 4; and t is 2 to 1000.
    Type: Grant
    Filed: December 30, 2019
    Date of Patent: November 15, 2022
    Assignee: SHPP GLOBAL TECHNOLOGIES B.V.
    Inventors: Roy Ray Odle, Ke Cao, Guoliang Liu, Timothy Edward Long
  • Patent number: 11377521
    Abstract: A polyimide composition includes 1 to 99 weight percent, preferably 70 to 99 weight percent, more preferably 75 to 95 weight percent of a first polyimide; and 1 to 99 weight percent, preferably 1 to 30 weight percent, more preferably 2 to 25 weight percent of a second polyimide, wherein the first polyimide and the second polyimide are different, and wherein the polyimide composition has a melt flow rate that is greater than a melt flow rate of the first polyimide and less than a melt flow rate of the second polyimide; an apparent viscosity that is less than an apparent viscosity of the first polyimide and less than an apparent viscosity of the second polyimide; and a notched Izod impact strength that is greater than a notched Izod impact strength of the first polyimide and greater than a notched Izod impact strength of the second polyimide.
    Type: Grant
    Filed: December 29, 2017
    Date of Patent: July 5, 2022
    Assignee: SHPP GLOBAL TECHNOLOGIES B.V.
    Inventors: Roy Ray Odle, Peter Johnson, Manojkumar Chellamuthu, Hee Won Kong, Timothy Edward Long
  • Patent number: 11286347
    Abstract: A branched polyimide of the formula (I) wherein G is a group having a valence of t, present in an amount of 0.01 to 10 mol %, or 0.05 to 5 mol %, or 0.1 to 4 mol %, or 0.1 to 3 mol %, each of Q, M, D, V, and R are as defined herein, q is 0 or 1, m is 0 or 1, d is 0 or 1, p is 1 or 2, t is 2 to 6, preferably 2 to 4, and each n is independently the same or different, and is 1 to 1,000, provided that the total of all values of n is greater than 4, wherein the branched polyimide has a zero-shear viscosity in a range from 500 to 15,000 Pa·s, a rheology ratio of 1.1 to 5, and a strain hardening ratio of 1 to 6.
    Type: Grant
    Filed: December 29, 2017
    Date of Patent: March 29, 2022
    Assignee: SHPP GLOBAL TECHNOLOGIES B.V.
    Inventors: Roy Ray Odle, Peter Johnson, Manojkumar Chellamuthu, Hee Won Kong
  • Patent number: 11279692
    Abstract: A method for producing an aromatic bisimide includes reacting a dialkali metal salt of a dihydroxy aromatic compound with an N-alkyl nitrophthalimide to form a product mixture including the aromatic bisimide. The N-alkyl nitrophthalimide includes 4-nitro-N—(C1-13 alkyl)phthalimide, 3-nitro-N—(C1-13 alkyl)phthalimide, or a combination including at least one of the foregoing, and 4-hydroxy-3,5-dinitro-N—(C1-13 alkyl)phthalimide in an amount of 1-10000 ppm. The aromatic bisimide can be obtained in a yield of greater than 75%, or 90-99.8%. A method for the manufacture of a polyetherimide, a polyetherimide, and an article including the polyetherimide are also disclosed. A mixed acid nitration process for the preparation of an N-alkyl nitrophthalimide is also described.
    Type: Grant
    Filed: December 29, 2016
    Date of Patent: March 22, 2022
    Assignee: SHPP GLOBAL TECHNOLOGIES B.V.
    Inventors: Thomas Link Guggenheim, Roy Ray Odle, Mani Raj Chaulagain
  • Patent number: 11142643
    Abstract: A method of manufacture of a polyetherimide copolymer composition includes contacting a substituted phthalic anhydride and an organic diamine in the presence of diphenyl sulfone, sulfolane, or a combination comprising at least one of the foregoing solvents at a temperature of greater than 130° C. to provide a bis(phthalimide) composition comprising diphenyl sulfone, sulfolane, or a combination comprising at least one of the foregoing solvents and a bis(phthalimide); and copolymerizing the bis(phthalimide), a substituted aromatic compound, and an alkali metal salt of a dihydroxy aromatic compound in the presence of diphenyl sulfone, sulfolane, or a combination comprising at least one of the foregoing to form a polyetherimide copolymer. The method does not require any catalyst either for the imidization or the polymerization.
    Type: Grant
    Filed: August 7, 2019
    Date of Patent: October 12, 2021
    Assignee: SHPP GLOBAL TECHNOLOGIES B.V.
    Inventors: Mani Raj Chaulagain, Roy Ray Odle
  • Publication number: 20210309849
    Abstract: Provided are copolycarbonate compositions including a stabilizer package which comprise a phosphorous-containing acid, an ester of phosphorous-containing acid, and an organosulfonic stabilizer where the phosphorous-containing acid and the ester of a phosphorous-containing acid are present in a molar ratio of 1 to 2. The total stabilization package is for example, in the amount by weight of 4 to 32 ppm, 8 to 24 ppm, or 8 to 16 ppm and the organosulfonic stabilizer is, e.g., of 2 to 30 ppm, or 4 to 24 ppm, or 8 to 16 ppm.
    Type: Application
    Filed: July 31, 2019
    Publication date: October 7, 2021
    Inventors: Wei ZHAO, Roy Ray ODLE, Paul Dean SYBERT
  • Patent number: 11130843
    Abstract: A method of manufacture of a polyetherimide composition includes contacting a substituted phthalic anhydride and an organic diamine in the presence of diphenyl sulfone, sulfolane, or a combination comprising at least one of the foregoing solvents at a temperature of greater than 130° C. to provide a bis(phthalimide) composition comprising diphenyl sulfone, sulfolane, or a combination comprising at least one of the foregoing solvents and a bis(phthalimide); and polymerizing the bis(phthalimide) and an alkali metal salt of a dihydroxy aromatic compound in the presence of diphenyl sulfone, sulfolane, or a combination comprising at least one of the foregoing to form a polyetherimide. The method does not require any catalyst either for the imidization or the polymerization.
    Type: Grant
    Filed: September 9, 2019
    Date of Patent: September 28, 2021
    Assignee: SHPP GLOBAL TECHNOLOGIES B.V.
    Inventors: Mani Raj Chaulagain, Thomas Link Guggenheim, Roy Ray Odle
  • Publication number: 20210206747
    Abstract: A method for producing an aromatic bisimide includes reacting a dialkali metal salt of a dihydroxy aromatic compound with an N-alkyl nitrophthalimide to form a product mixture including the aromatic bisimide. The N-alkyl nitrophthalimide includes 4-nitro-N—(C1-13 alkyl)phthalimide, 3-nitro-N—(C1-13 alkyl)phthalimide, or a combination including at least one of the foregoing, and 4-hydroxy-3,5-dinitro-N—(C1-13 alkyl)phthalimide in an amount of 1-10000 ppm. The aromatic bisimide can be obtained in a yield of greater than 75%, or 90-99.8%. A method for the manufacture of a polyetherimide, a polyetherimide, and an article including the polyetherimide are also disclosed. A mixed acid nitration process for the preparation of an N-alkyl nitrophthalimide is also described.
    Type: Application
    Filed: December 29, 2016
    Publication date: July 8, 2021
    Inventors: Thomas Link Guggenheim, Roy Ray Odle, Mani Raj Chaulagain
  • Patent number: 10995180
    Abstract: A polyetherimide composition includes a polyetherimide and two or more of a residual metal content, a sulfate anion, a phosphate anion, a nitrite anion, a nitrate anion, or a combination including at least one of the foregoing, a residual solvent content, a phosphorus-containing stabilizer, and alkali metal halide, alkaline earth metal halide, alkali metal carbonate, or a combination including at least one of the foregoing, wherein each of the aforementioned components, when present, is included in the composition in a particular amount. The resulting polyetherimide composition exhibits two or more useful properties. The polyetherimide composition can optionally further be combined with a polymer different from the polyetherimide to provide a thermoplastic composition. Methods of making the polyetherimide composition and articles including the polyetherimide composition are also described.
    Type: Grant
    Filed: December 29, 2016
    Date of Patent: May 4, 2021
    Assignee: SHPP GLOBAL TECHNOLOGIES B.V.
    Inventors: Mark A. Sanner, Thomas Link Guggenheim, Roy Ray Odle
  • Publication number: 20200207916
    Abstract: A polyimide oligomer of formula (1a), (1b), a copolymer thereof, or a combination thereof wherein each G1 is independently the same or different, and is a cation group; each G2 is independently the same or different, and is an anion group; each D is independently the same or different, and is a single bond or C1-20 divalent hydrocarbon group; each V is independently the same or different, and is a tetravalent C4-40 hydrocarbon group; each R is independently the same or different, and is a C1-20 divalent hydrocarbon group; each n is independently the same or different, and is 1 to 1000, provided that the total of all values of n is greater than 4; and t is 2 to 1000.
    Type: Application
    Filed: December 30, 2019
    Publication date: July 2, 2020
    Inventors: Roy Ray Odle, Ke Cao, Guoliang Liu, Timothy Edward Long
  • Publication number: 20200207913
    Abstract: A polyimide oligomer of the formula wherein G is a group having a valence of t and is connected by a covalent bond or an ionic bond, each Q is independently the same or different, and is a cation or a substituted or unsubstituted divalent C1-60 hydrocarbon group, each M is independently the same or different, and is a substituted or unsubstituted divalent C1-60 hydrocarbon group, —O—, —C(O)—, —OC(O)—, —OC(O)O—, —NHC(O)—, —(O)CNH—, —S—, —S(O)—, or —S(O)2—, D is a phenylene, each V is independently the same or different, and is a tetravalent C4-40 hydrocarbon group, each R is independently the same or different, and is a C1-20 divalent bridging group, a C1-20 alkylene-XA, or a C6-30 arylene-XA wherein XA is a cation-anion complex, provided that at least one R is C1-20 alkylene-XA or C6-30 arylene-XA, q, m, d, p, t, and n are as provided herein.
    Type: Application
    Filed: December 30, 2019
    Publication date: July 2, 2020
    Inventors: Roy Ray Odle, Guoliang Liu, Timothy Edward Long, Ke Cao
  • Patent number: 10696792
    Abstract: A ureido-pyrimidinone oligomer having the formula (I) wherein each Z? is independently the same or different, and is a substituted or unsubstituted straight or branched chain C1-10 alkyl, each R1 is independently the same or different, and is a substituted or unsubstituted straight or branched chain C1-20 alkylene, substituted or unsubstituted C2-20 alkenylene, substituted or unsubstituted C3-8 cycloalkylene, or substituted or unsubstituted C6-18 arylene, each V is independently the same or different, and is a substituted or unsubstituted tetravalent C4-40 hydrocarbon group, each R is independently the same or different, and is a substituted or unsubstituted C1-24 divalent hydrocarbon group; and n has an average value of 2 to 50, preferably 3 to 40, more preferably 5 to 30.
    Type: Grant
    Filed: November 16, 2017
    Date of Patent: June 30, 2020
    Assignee: SABIC GLOBAL TECHNOLOGIES B.V.
    Inventors: Roy Ray Odle, Guoliang Liu, Ke Cao, Timothy Edward Long, Joseph Michael Dennis
  • Publication number: 20200172665
    Abstract: A copolycarbonate includes 0.005-0.1 mole percent of sulfur-containing carbonate units derived from a sulfur-containing bisphenol monomer, 2-95 mole percent of high heat carbonate units derived from a high heat aromatic dihydroxy monomer, and 5-98 mole percent of a low heat carbonate units derived from a low heat aromatic monomer, each based on the sum of the moles of the carbonate units; and optionally, thioether carbonyl endcaps of the formula —C(?O)-L-S—R, wherein L is a C1-12 aliphatic or aromatic linking group and R is a C1-20 alkyl, C6-18 aryl, or C7-24 arylalkylene; wherein the sulfur content of the high heat copolycarbonate in the absence of the thioether endcaps is from 5-20 parts per million by weight.
    Type: Application
    Filed: November 11, 2019
    Publication date: June 4, 2020
    Inventors: PAUL DEAN SYBERT, ROY RAY ODLE, JORDI CALVERAS, WEI ZHAO
  • Publication number: 20200123323
    Abstract: A one-pot method for making a polyetherimide includes contacting in a reaction vessel a reactive substituted phthalic anhydride and an organic diamine in a polar aprotic solvent to provide a reaction mixture including a substituted bisphthalimide. The method further includes adding to the reaction mixture in the same reaction vessel an aromatic dihydroxy compound, a base, and optionally, a phase transfer catalyst to provide a product mixture including the polyetherimide. A polyetherimide made by the method is also described.
    Type: Application
    Filed: December 29, 2017
    Publication date: April 23, 2020
    Applicant: SABIC Global Technologies B.V.
    Inventors: Mani Raj CHAULAGAIN, Roy Ray ODLE, Thomas Link GUGGENHEIM
  • Publication number: 20200115501
    Abstract: A branched polyimide of the formula (I) wherein G is a group having a valence of t present in an amount 0.01 to 20 mol %, each Q is independently the same or different, and is a divalent C1-60 hydrocarbon group, each M is independently the same or different, and is —O—, —C(O)—, —OC(O)—, —OC(O)O—, —NHC(O), —(O)CNH—, —S—, —S(O)—, or —S(O)2—, D is a phenylene, each V is independently the same or different, and is a tetravalent C4-40 hydrocarbon group, each R is independently the same or different, and is a C1-20 divalent hydrocarbon group, q is 0 or 1, m is 0 or 1, d is 0 or 1, p is 1 or 2, t is 2 to 6, and each n is independently the same or different, and is 1 to 1,000, provided that the total of all values of n is greater than 4.
    Type: Application
    Filed: December 29, 2017
    Publication date: April 16, 2020
    Inventors: Roy Ray ODLE, Thomas Link GUGGENHEIM, Lioba Maria KLOPPENBURG, Timothy Edward LONG, Joseph Michael DENNIS
  • Publication number: 20200115502
    Abstract: A branched polyimide of the formula (I) wherein G is a group having a valence of t, present in an amount of 0.01 to 10 mol %, or 0.05 to 5 mol %, or 0.1 to 4 mol %, or 0.1 to 3 mol %, each of Q, M, D, V, and R are as defined herein, q is 0 or 1, m is 0 or 1, d is 0 or 1, p is 1 or 2, t is 2 to 6, preferably 2 to 4, and each n is independently the same or different, and is 1 to 1,000, provided that the total of all values of n is greater than 4, wherein the branched polyimide has a zero-shear viscosity in a range from 500 to 15,000 Pa·s, a rheology ratio of 1.1 to 5, and a strain hardening ratio of 1 to 6.
    Type: Application
    Filed: December 29, 2017
    Publication date: April 16, 2020
    Inventors: Roy Ray ODLE, Peter JOHNSON, Manojkumar CHELLAMUTHU, Hee Won KONG
  • Patent number: 10619010
    Abstract: A polyimide oligomer of the formula wherein G is a group having a valence of t, each R is independently a C1-30 divalent bridging group, a C1-20 alkylene-X, or a C6-30 arylene-X wherein —X is —O-M?, —C(O)O-M?, —OC(O)O-M?, —S-M?, —S(O)2-M?, —S(O)3-M?, —OS(O)3-M?, or —OP(O)3-M? wherein each M? is independently Li, Na, K, Cs, Mg, Ca, Sr, Cr, Mn, Fe, Co, Ni, Cu, Zn, Cd, B, Al, Ga, In, Ge, Sn, Pb, As, or Sb, provided that at least one R is C1-20 alkylene-X or C6-30 arylene-X, q is 0 or 1, m is 0 or 1, d is 0 or 1, p is 1 or 2, t is 1 to 6, and each n is independently 1 to 1,000, the total of all values of n is greater than 4, the polyimide oligomer is thermoplastic, and Q, M, D, and V are as provided herein.
    Type: Grant
    Filed: December 31, 2018
    Date of Patent: April 14, 2020
    Assignee: SABIC GLOBAL TECHNOLOGIES B.V.
    Inventors: Roy Ray Odle, Ke Cao, Guoliang Liu, Timothy Edward Long, Joseph Michael Dennis
  • Publication number: 20190390013
    Abstract: A method of manufacture of a polyetherimide composition includes contacting a substituted phthalic anhydride and an organic diamine in the presence of diphenyl sulfone, sulfolane, or a combination comprising at least one of the foregoing solvents at a temperature of greater than 130° C. to provide a bis(phthalimide) composition comprising diphenyl sulfone, sulfolane, or a combination comprising at least one of the foregoing solvents and a bis(phthalimide); and polymerizing the bis(phthalimide) and an alkali metal salt of a dihydroxy aromatic compound in the presence of diphenyl sulfone, sulfolane, or a combination comprising at least one of the foregoing to form a polyetherimide. The method does not require any catalyst either for the imidization or the polymerization.
    Type: Application
    Filed: September 9, 2019
    Publication date: December 26, 2019
    Inventors: MANI RAJ CHAULAGAIN, THOMAS LINK GUGGENHEIM, ROY RAY ODLE
  • Publication number: 20190359826
    Abstract: A method of manufacture of a polyetherimide copolymer composition includes contacting a substituted phthalic anhydride and an organic diamine in the presence of diphenyl sulfone, sulfolane, or a combination comprising at least one of the foregoing solvents at a temperature of greater than 130° C. to provide a bis(phthalimide) composition comprising diphenyl sulfone, sulfolane, or a combination comprising at least one of the foregoing solvents and a bis(phthalimide); and copolymerizing the bis(phthalimide), a substituted aromatic compound, and an alkali metal salt of a dihydroxy aromatic compound in the presence of diphenyl sulfone, sulfolane, or a combination comprising at least one of the foregoing to form a polyetherimide copolymer. The method does not require any catalyst either for the imidization or the polymerization.
    Type: Application
    Filed: August 7, 2019
    Publication date: November 28, 2019
    Inventors: Mani Raj Chaulagain, Roy Ray Odle