Material Contains A Group Iva Metal Atom (ge, Sn, Pb) Patents (Class 528/283)
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Patent number: 6500915Abstract: The present invention relates to a polyester resin produced by polymerizing a dicarboxylic acid component comprising mainly an aromatic dicarboxylic acid or its ester forming derivative, and a diol component comprising mainly ethylene glycol in the presence of a catalyst containing a titanium compound, which polyester resin contains titanium atoms (Ti) in an amount of 0.002 to 1.0 mole based on one ton of the polyester resin and has the following properties: Intrinsic viscosity ([&eegr;], dl/g)≧0.70 Hunter's “b” value≦4 Acetaldehyde content (AA0, ppm)≦5.0.Type: GrantFiled: November 10, 2000Date of Patent: December 31, 2002Assignee: Mitsubishi Chemical CorporationInventors: Yoshihiro Fujimori, Shuuji Anno, Masahiro Nukui
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Patent number: 6489406Abstract: The invention relates unsaturated polyester resins for the manufacture of subzero flexible, weather-resistant products. The liquid unsaturated polyester resin comprises a linear unsaturated polyester obtained by reacting 5-30 mol % of one or more ethylenically unsaturated dicarboxylic acids (A), 20-45 mol % of one or more other aliphatic or aromatic acids (B) and 40-60 mol % of two or more polyhydric alcohols and 30-60 wt % of one or more reactive monomers. The linear unsaturated polyesters have a cone and plate viscosity (I.C.I.) of 2 ps/125° C.-20 ps/125° C. and a molecular weight Mw of 20,000-100,000. The invention also relates to a process for the manufacture of such unsaturated polyester resins and to the use of them in applications wherein good adhesion to supporting material and flexibility at ambient and especially at low temperatures are needed.Type: GrantFiled: March 29, 2001Date of Patent: December 3, 2002Assignee: Ashland Inc.Inventors: Paul Mahbub, Karri Airola, Eija Valtonen
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Patent number: 6489434Abstract: The present invention provides a manufacturing method of copolyester for low acetaldehyde content of PET bottles. The polyethylene terephthalate (PET) polymer is added with an appropriate modifier in order to decrease the production of acetaldehyde caused by pyrolysis side reaction during the blow molding process of PET bottles. The modifier comprises stabilizer and primary antioxidant, wherein the stabilizer is an inorganic phosphorous compound with an addition quantity of 0.003˜0.5 weight % based on the weight of the total copolyester copolymer and the primary antioxidant is a hindered phenolic antioxidant containing Ca+2 with an addition quantity of 0.005˜5.0 weight % based on the weight of the total copolyester copolymer. The present invention owns an improving effect of decreasing the production of side product—acetaldehyde at least 30% than those without the addition of said modifier.Type: GrantFiled: May 14, 2001Date of Patent: December 3, 2002Assignee: Nan Ya Plastics CorporationInventor: Zo-Chun Jen
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Patent number: 6472500Abstract: An improved process for the preparation of high molecular weight, linear polyester resins comprises reacting an aromatic dicarboxylic acid with an excess of an alkane diol under conditions effective to reach the clearing point of the reaction; pre-condensing the cleared reaction mixture under conditions effective to produce oligomers having an intrinsic viscosity measured in 60/40 phenol/1,1,2,2-tetrachloroethane at 25° C. of less than about 0.70 deciliters/gram and a carboxylic acid end group level of less than or equal to about 100 milliequivalents per kilogram; and polycondensing the oligomer under conditions effective to produce a linear polyester resin having an intrinsic viscosity less than or equal to about 2.0 dl/g as measured in 60/40 phenol/1,1,2,2-tetrachloroethane by weight at 25° C. and a carboxylic acid end group level of about 10 to about 40 milliequivalents per kilogram.Type: GrantFiled: June 13, 2001Date of Patent: October 29, 2002Assignee: General Electric CompanyInventors: Sandeep Dhawan, Gary Smith
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Patent number: 6426398Abstract: A poly(trimethylene terephthalate) polymer composition (a) comprising repeat units derived from terephthalic acid and 1,3- propanediol, (b) having a b value of less than about 10, and (c) having an intrinsic viscosity (IV) in the range from about 0.74 to about 2.0. The poly(trimethylene terephthalate) polymer composition does not contain a blue masking pigment. It is prepared by a process comnprising contacting, in the presence of a catalyst comprises tin and titanium. A copolymer that contains up to 20 mole percent of another acid and/or a second alcohol is also disclosed. Further disclosed is a composition of, or comprising, a bis (3-hydroxypropyl) terephthalalte prepolymer. The bis (3-hydroxypropyl) terephthalalte prepolymer and poly(trimethylene terephthalalte) can each contain 10 to 100 ppm tin and 10 to 200 ppm titanium relative to the terephthalic acid content.Type: GrantFiled: February 27, 2001Date of Patent: July 30, 2002Assignee: E. I. Du Pont De Nemours and CompanyInventors: Joseph V Kurian, Yuanfeng Liang, Donald Edward Putzig
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Patent number: 6417320Abstract: The production of linear polyester by the interchange of ester radicals or esterification and polycondensation of multivalent alcohols with multivalent carboxylic acids takes place by means of catalysts. In order that the catalyst features the lowest possible content of catalytically active metal compound, the carrier substance that forms the heterogeneous phase comprises particles of the finest grain and of porous structure and features a surface of great inner, reactive and/or coordinated centers, whereby a catalytically active metal compound is adsorbed in the pores.Type: GrantFiled: February 25, 2000Date of Patent: July 9, 2002Assignee: Zimmer AktiengesellschaftInventors: Brigitta Otto, Karl Ulrich Thiele, Xiaogang Guo
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Patent number: 6399716Abstract: An aromatic group containing copolyester resin composition which has good biodegradability and physical properties, wherein; (i) 0.1 wt % to 30 wt % of an aliphatic prepolymers having number average molecular weight of from 300 to 30,000; (ii) one or a plurality of aromatic dicarboxylic acid (or an acid anhydride thereof which containing aromatic group in the molecule; (iii) one or a plurality of aliphatic (including cyclic type) dicarboxylic acid (or an acid anhydride thereof); and (iv) one or a plurality of aliphatic (including cyclic type) glycol, wherein the copolyester resin has number average molecular weight of from 30,000 to 90,000, weight average molecular weight of from 100,000 to 600,000, melting point of from 70° C. to 150° C., and melt index of from 0.1 to 50 g/10min. (190° C., 2,160 g), and the process for preparing and/or producing the same.Type: GrantFiled: December 13, 2000Date of Patent: June 4, 2002Assignee: IRE Chemical Ltd.Inventors: Hyun Soo Chung, Jae Wang Lee, Dong Hoon Kim, Do Youn Kim, Suok Woo Lee
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Patent number: 6392005Abstract: The present invention relates to a manufacturing method for decreasing the cyclic oligomer content in polyester which effectively restrains the production of the cyclic oligomer in ester chips and further decreases the amount of regenerated cyclic oligomer at the melting process stage by adding the additive, during the process of manufacturing polyethylene terephthalate, with the following structure:Type: GrantFiled: May 14, 2001Date of Patent: May 21, 2002Assignee: Nan Ya Plastics CorporationInventor: Zo-Chun Jen
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Publication number: 20020028904Abstract: An improved process for the preparation of high molecular weight, linear polyester resins comprises reacting an aromatic dicarboxylic acid with an excess of an alkane diol under conditions effective to reach the clearing point of the reaction; pre-condensing the cleared reaction mixture under conditions effective to produce oligomers having an intrinsic viscosity measured in 60/40 phenol/1,1,2,2-tetrachloroethane at 25° C. of less than about 0.70 deciliters/gram and a carboxylic acid end group level of less than or equal to about 100 milliequivalents per kilogram; and polycondensing the oligomer under conditions effective to produce a linear polyester resin having an intrinsic viscosity less than or equal to about 2.0 dl/g as measured in 60/40 phenol/1,1,2,2-tetrachloroethane by weight at 25° C. and a carboxylic acid end group level of about 10 to about 40 milliequivalents per kilogram.Type: ApplicationFiled: June 13, 2001Publication date: March 7, 2002Inventors: Sandeep Dhawan, Gary Smith
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Patent number: 6350851Abstract: A method of producing a polyester from high-purity bis-&bgr;-hydroxyethyl terephthalate as a raw material containing cations and anions in trace amounts. Polyester production raw materials including bis-&bgr;-hydroxyethyl terephthalate containing cations and anions in a total weight of not more than 50 ppm, ethylene glycol and antimony trioxide and/or germanium dioxide as a polymerization catalyst are heated without substantially distilling off ethylene glycol and then heated under reduced pressure to be polycondensed while ethylene glycol is distilled off.Type: GrantFiled: June 15, 2001Date of Patent: February 26, 2002Assignee: AIES Co., Ltd.Inventors: Shuji Inada, Kikuchi Sato
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Patent number: 6350850Abstract: The present invention is a process for producing a polyester from a dicarboxylic acid and a diol, which comprises polycondensing the dicarboxylic acid and the diol under the presence of a distannoxane catalyst. Also, the present invention is a process for producing a polyester which comprises melt polycondensing the dicarboxylic acid and the diol under normal pressure in the presence of the distannoxane catalyst, wherein an organic solvent which dose not dissolved any of the dicarboxylic acid, the diol and the polyester produced from the dicarboxylic acid the diol is present and, whereby, two phases are mainly present.Type: GrantFiled: July 12, 2000Date of Patent: February 26, 2002Assignee: Daicel Chemical Industries, Ltd.Inventors: Mitsuru Ueda, Hiroyuki Takahashi, Teruaki Hayakawa, Tadashi Teranishi
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Patent number: 6346070Abstract: The present invention provides a catalyst for polyester production capable of producing a polyester with high catalytic activity and a process for producing a polyester using the catalyst. The catalyst for polyester production comprises a solid titanium compound which is obtained by dehydro-drying a hydrolyzate obtained by hydrolysis of a titanium halide and which has a molar ratio (OH/Ti) of a hydroxyl group (OH) to titanium (Ti) exceeding 0.09 and less than 4. The present invention also provides a method to obtain a polyester having a small increase of the acetaldehyde content during the molding. This method comprises bringing a polyester, which is obtained by the use of a titanium compound catalyst and in which the reaction has been completed, into contact with a phosphoric ester aqueous solution or the like having a concentration of not less than 10 ppm in terms of phosphorus atom.Type: GrantFiled: December 22, 1999Date of Patent: February 12, 2002Assignee: Mitsui Chemicals IncInventors: Takeshi Ohmatsuzawa, Fujito Ehara, Hideshi Hori, Kazuo Toyota, Kenzaburou Fukutani, Junichi Imuta, Akiyoshi Shimizu, Takayuki Onogi, Seiji Noda, Masayuki Sakai, Shoji Hiraoka, Koji Nakamachi, Michio Tsugawa, Satoru Miyazoe
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Publication number: 20010049430Abstract: A water slurry process is used to prepare a prepreg and to manufacture articles from macrocyclic polyester oligomers. In one embodiment, a process for preparing a water suspension of macrocyclic polyester oligomers includes the steps of contacting a macrocyclic polyester oligomer and a polymerization catalyst with water and a surfactant, and mixing the macrocyclic polyester oligomer and polymerization catalyst with water and the surfactant thereby forming a suspension. In another embodiment, a process for impregnating macrocyclic polyester oligomers for polymerization includes the steps of providing a suspension of a macrocyclic polyester oligomer and a polymerization catalyst in water, applying the suspension to a base material, drying to remove water from the suspension, and pressing the dried suspension to a desired form. In yet another embodiment, a composition of macrocyclic polyester oligomer includes a macrocyclic polyester oligomer, a polymerization catalyst, and water.Type: ApplicationFiled: January 4, 2001Publication date: December 6, 2001Inventors: Steven J. Winckler, Tohru Takekoshi
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Patent number: 6316584Abstract: For the production of polyesters and copolyesters, coprecipitates are used individually or in a mixture as polycondensation catalysts, the coprecipitates being prepared by simultaneous hydrolytic precipitation of a titanium compound and a metallic compound of a metal selected from the groups IA, IIA, VIIIA, IB, IIB, IIIB, and IVB, whereby the titanium compound and the metallic compound are, independently of one another, an alkylate, alcoholate, or carboxylate of titanium or the metal, respectively, and the molar ratio of the titanium compound to the metallic compound is ≧50:50 mol/mol. The coprecipitates exhibit a higher catalytic activity than Sb2O3 which results in a prefered amount of usage of only 10 to 100 ppm with respect to the esters or oligoesters to undergo polycondensation.Type: GrantFiled: December 9, 1999Date of Patent: November 13, 2001Assignee: Akzo Nobel NVInventors: Ulf Seidel, Michael Gerd Martl
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Patent number: 6281325Abstract: In one embodiment, the invention is a process for the preparation of poly(trimethylene terephthalate) comprising (a) contacting terephthalic acid with 1,3-propanediol in the presence of an organic tin catalyst to form a bis(3-hydroxypropyl)terephthalate monomer; and (b) polymerizing said monomer in the presence of organic titanate polycondensation catalyst to obtain the poly(trimethylene terephthalate). In another embodiment, the invention is a process for the preparation of poly(trimethylene terephthalate) containing less than 1.6 mol % of DPG said process comprising contacting terephthalic acid with a 1.6 to 1 to 2:1 molar amount of 1,3-propanediol in the presence of 20 to 120 ppm (as tin), by weight of the poly(trimethylene terephthalate), of a organic tin catalyst, to form a bis(3-hydroxypropyl)terephthalate monomer and polymerizing said monomer to obtain the poly(trimethylene terephthalate). The invention is also directed to poly(trimethylene terephthalate) produced by the processes.Type: GrantFiled: August 23, 2000Date of Patent: August 28, 2001Assignee: E. I. du Pont de Nemours and CompanyInventors: Joseph Varapadavil Kurian, Yuanfeng Liang
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Publication number: 20010016642Abstract: A process that can be used in an esterification and polycondensation processes to produce a polyester such as, for example, poly(trimethylene terephthalate) is disclosed. The process comprises contacting an acid with 1,3-propanediol in the presence of a catalyst comprising tin and titanium. A copolymer that contains up to 20 mole percent of another acid and/or a second alcohol is also disclosed. Further disclosed are a composition of, or comprising, a bis(3-hydroxypropyl) terephthalate prepolymer or a composition of, or comprising, a poly(trimethylene terephthalate) polymer. The bis(3-hydroxypropyl) terephthalate prepolymer and poly(trimethylene terephthalate) can each contain 10 to 100 ppm tin and 10 to 200 ppm titanium relative to the terephthalic acid content.Type: ApplicationFiled: February 27, 2001Publication date: August 23, 2001Inventors: Joseph V. Kurian, Yuanfeng Liang, Donald E. Putzig
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Patent number: 6268465Abstract: An aliphatic polyester amide which is hydrolysis-resistant includes a ternary polycondensation product of monomeric constituents composed of a monomeric constituent A which is at least one diol having a general formula: HO—R1—OH, where R1 is an aliphatic residue having 2-16 carbon atoms; a monomeric constituent B which is at least one dicarboxylic acid having a general formula: HOOC—R2—COOH, where R2 is an aliphatic residue having 1-14 carbon atoms; and a monomeric constituent C which is at least one diamine having a general formula: H2N—R3—NH2, where R3 is an aliphatic residue having 2-16 carbon atoms and is present in an amount of up to about 5% by weight based on total weight of the monomeric constituents, wherein polycondensation proceeds in the presence of a catalyst comprised of constituent D, which is a metal-containing catalyst, in combination with constituent E, which is at least one of an organic phosphorus compound and an inorganic phosphorus compound, and whereiType: GrantFiled: April 12, 1999Date of Patent: July 31, 2001Assignee: BK Giulini Chemie GmbH Co OHGInventors: Gudrun Chomiakow, Hasan Ulubay, Emil Wilding
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Patent number: 6255442Abstract: A process that can be used in an esterification and polycondensation processes to produce a polyester such as, for example, poly(trimethylene terephthalate) is disclosed. The process comprises contacting an acid with 1,3-propanediol in the presence of a catalyst comprising tin and titanium. A copolymer that contains up to 20 mole percent of another acid and/or a second alcohol is also disclosed. Further disclosed are a composition of, or comprising, a bis(3-hydroxypropyl) terephthalate prepolymer or a composition of, or comprising, a poly(trimethylene terephthalate) polymer. The bis(3-hydroxypropyl) terephthalate prepolymer and poly(trimethylene terephthalate) can each contain 10 to 100 ppm tin and 10 to 200 ppm titanium relative to the terephthalic acid content.Type: GrantFiled: February 8, 2000Date of Patent: July 3, 2001Assignee: E. I. du Pont de Nemours and CompanyInventors: Joseph V Kurian, Yuanfeng Liang, Donald Edward Putzig
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Patent number: 6242558Abstract: A 1,3-propanediol-based aromatic polyester such as polytrimethylene terephthalate is modified by reaction with a hindered phenolic acid or ester to provide an endcapped polyester which has improved resistance to generation of acrolein when heated in air.Type: GrantFiled: November 27, 1996Date of Patent: June 5, 2001Assignee: Shell Oil CompanyInventor: Donald Ross Kelsey
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Patent number: 6143801Abstract: A method of forming an esterification product Comprises providing (1) a material selected from the group consisting of ester monomers, ester oligomers, ester polymers, and mixtures thereof, and (2) a catalyst selected from the group consisting of: ##STR1## and mixtures thereof. wherein D is selected from the group consisting of carbon and silicon; Q is selected from the group consisting of O, S, and NR; M is selected from the group consisting of sodium, lithium, potassium, rubidium, and cesium; R, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R', R", and R'" are each independently selected from the group consisting of H, O, halogen, Si, N, S, P, C.sub.1 to C.sub.20 linear or branched alkyl, C.sub.3 to C.sub.10 cycloalkyl, and aromatic; and reacting the material in the presence of the catalyst to form an esterification product.Type: GrantFiled: December 18, 1997Date of Patent: November 7, 2000Assignee: The University of North Carolina at Chapel HillInventors: Michel R. Gagne', Michael R. Korn
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Patent number: 6140458Abstract: The invention provides a process for producing high-molecular aliphatic polyesters capable of being substitutes for general-purpose resins that are required to have high toughness, in a simplified manner and at a high volume efficiency. Specifically, in the process, used as the starting material is an easily-available, low-molecular aliphatic polyester prepolymer to be prepared through polycondensation of inexpensive materials of an aliphatic hydroxycarboxylic acid such as lactic acid, glycolic acid or the like, an aliphatic polyalcohol such as butanediol or the like, and an aliphatic polycarboxylic acid such as succinic acid or the like, and the starting prepolymer is crystallized and thereafter polycondensed in a solid phase in the presence of a catalyst to give the intended, tough and high-molecular aliphatic polyester.Type: GrantFiled: April 27, 1999Date of Patent: October 31, 2000Assignee: Mitsui Chemicals, Inc.Inventors: Yuji Terado, Hiroshi Suizu, Masatoshi Takagi, Masanobu Ajioka, Shoji Hiraoka, Masayuki Sakai, Hiroyuki Suzuki, Ryo Shinagawa, Shinji Ogawa, Yasushi Kotaki
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Patent number: 6129961Abstract: A polyester resin comprising a polyester resin chip (A) and a polyester resin fine particle (B) which has the same composition as the (A) and which passes through a 10.5 mesh screen in a proportion of 0.1-300 ppm, wherein a cyclic trimer increases in a proportion of not more than 0.30 wt % upon melting at a temperature of 290.degree. C. for 60 minutes; a polyester resin characterized in that a cyclic trimer increases in a proportion of not more than 0.30 wt % upon melting at a temperature of 290.degree. C. for 60 minutes, and the contents of Na, Ca, Mg and/or Si in the polyeser resin is 0.001-5 ppm and the total of these contents is not more than 10 ppm; and production methods thereof.Type: GrantFiled: August 27, 1999Date of Patent: October 10, 2000Assignee: Toyo Boseki Kabushiki KaishaInventors: Hirotoshi Sonoda, Atsushi Hara, Mitsuhiro Harada, Yoshio Araki, Shouji Kikuchi, Takashi Hashimoto, Keisuke Suzuki, Hitoshi Furusaki, Kazuki Yamauchi, Yoshinao Matsui, Osamu Kimura, Yoshitaka Eto
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Patent number: 6114458Abstract: A branched radial block copolymer including the reaction product of a dendritic macromolecular initiator, and one or more chain extending monomers.Type: GrantFiled: September 23, 1998Date of Patent: September 5, 2000Assignee: International Business Machines CorporationInventors: Craig Jon Hawker, James Lupton Hedrick, Olof Mikael Trollsas
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Patent number: 6075115Abstract: The invention provides a process that can be used for producing a bis-glycolate ester of 5-sulfo isophthalate metal salt. The process comprises contacting a 5-sulfo isophthalate a metal salt or a dialkyl ester of 5-sulfo isophthalate metal salt, in the presence of a catalyst, with a glycol. The catalyst comprises (1) a titanium compound, a solubility promoter, a phosphorus source, and optionally a solvent, (2) a titanium compound, a complexing agent, a phosphorus source, and optionally a solvent, a sulfonic acid, or combinations thereof, or (3) combinations of (1) and (2). The solubility promoter can be selected from the group consisting of ortho silicates, ortho zirconates and combinations thereof. The phosphorus source is selected from the group consisting of a phosphonic acid, a phosphinic acid, a phosphine, and combinations of two or more thereof. The complexing agent can be selected from the group consisting of hydroxycarboxylic acids, aminocarboxylic acids, and combinations thereof.Type: GrantFiled: October 19, 1999Date of Patent: June 13, 2000Assignee: E. I. du Pont de Nemours and CompanyInventors: Donald Edward Putzig, William G Peet
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Patent number: 6060579Abstract: A method for producing polybutylene terephthalate comprising continuously esterifying a dicarboxylic acid component consisting essentially of terephthalic acid with a diol component consisting essentially of 1,4-butanediol followed by polycondensing the resulting oligomer, wherein the esterification is effected in a molar ratio, P, of the diol component to the dicarboxylic acid component to fall between 1.1 and 1.6, in the presence of a combination of an organic titanium compound and an organic tin compound that satisfies the following requirement:amount of organic titanium compound (mol %).ltoreq.0.08.times.P-0.07where P=molar ratio of diol component to dicarboxylic acid component, and is followed by the polycondensation.Type: GrantFiled: March 25, 1998Date of Patent: May 9, 2000Assignee: Toray Industries, Inc.Inventors: Hiroyuki Ohme, Motoki Hiratsuka, Katsuo Nogami
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Patent number: 6048931Abstract: Polycarbonate resin compositions comprising (A) a composition comprising a polycarbonate resin (A-1) and a specific polyethylene terephthalate resin polymerized by using a germanium catalyst (A-2) in an (A-1)/(A-2) ratio of 99/1 to 40/60 by weight, (B) 1 to 10 parts by weight, per 100 parts by weight of the composition (A), of an olefin-alkyl (meth)acrylate copolymer having an MI of 0.1 to 300 g/10 minutes and optionally (C) 2 to 10 parts by weight, per 100 parts by weight of the composition (A), of a graft copolymer in which at least one monomer selected from an aromatic vinyl compound, a vinyl cyanide compound, an acrylic acid ester, a methacrylic acid ester and vinyl compounds copolymerizable therewith is copolymerized with a rubbery elastomer. The polycarbonate resin compositions can meet recent demand of high level solvent resistance and also have excellent heat stability and flow property in molding.Type: GrantFiled: May 6, 1998Date of Patent: April 11, 2000Assignee: Kaneka CorporationInventors: Katsutoyo Fujita, Yoshitaka Ono
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Patent number: 6040417Abstract: A process for preparing polyethylene naphthalate polymer by using a composite catalyst. The process comprises the steps of esterifying a dicarboxylic acid containing 2,6-NDCA, a dicarboxylic ester containing 2,6-NDC or derivatives thereof, with ethylene glycol or a glycol containing ethylene glycol to produce esterification polymers containing bis(beta-hydroxyethyl)naphthalate; continuously polycondensing the obtained esterification polymers to prepare a polymers of polyethylene naphthalate; and wherein the process includes using a composite polymerization catalyst, said composite polymerization catalyst comprising a titanium compound, a phosphorous compound and optionally an antimony compound. The process can considerably reduce both the esterification time and the polycondensation time and provides a good color and excellent physical characteristics.Type: GrantFiled: September 14, 1999Date of Patent: March 21, 2000Inventors: Hyun Nam Cho, Jae Min Hong, Young Chan Ko, Il Seok Choi, Young Jin Heo
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Patent number: 6034202Abstract: The invention provides non-antimony containing polymerization catalysts for the condensation of polyesters. The catalyst is in the form of a clear chlorine and/or bromine containing solution of a metal glycoxide and a metal glycolate having a pH in the range of from 0 to about 1, and containing chlorine and/or bromine atoms at a number ratio of chlorine and/or bromine to total metal cations in the catalyst ranging from about 0.5:1 to about 3:1. Polyesters produced with this catalyst have improved melt elasticity, and higher melt viscosity. The former property is desirable for the preparation of large and complex shaped polyester containers, and the latter property is desirable for melt spinning of industrial grade fibers and tire cords.Type: GrantFiled: March 1, 1999Date of Patent: March 7, 2000Assignee: AlliedSignal Inc.Inventors: Shaul Moshe Aharoni, Konstantin Nikolaev Goranov
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Patent number: 6020455Abstract: A copolymer containing vinyl-3,4-cyclohexanediol and at least one monomer selected from acrylic acid, methacrylic acid, alkyl acrylate, alkyl methacrylate, styrene, acrylonitrile, butadiene, isoprene, vinyl acetate, maleic anhydride, ethylene, vinyl chloride, vinylidene dichloride, methyl styrene, vinyl toluene, acrylic and methacrylic acid, vinyl acetate, maleic anhydride, fumarate esters, maleate esters, vinylidene difluoride, vinyl fluoride, acrylic or methacrylic esters of the formula (I)H.sub.2 C.dbd.CHCOOR or H.sub.2 C.dbd.CCH.sub.3 COOR (I)where R is a aromatic or aliphatic hydrocarbon group containing 20 or fewer carbons and optionally containing oxygen, sulfur, or phosphorous, and mixtures thereof. A resin composition containing vinyl-3,4-cyclohexanediol, at least one carboxylic acid or ester thereof or anhydride, and optionally a polyol or diol other than vinyl-3,4-cyclohexanediol.Type: GrantFiled: February 11, 1998Date of Patent: February 1, 2000Assignee: BP Amoco CorporationInventors: Wayne Robert Pretzer, Matthew Albert Kulzick, Paul Alan Koning, Asare Nkansah, Maria Curry-Nkansah
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Patent number: 6020421Abstract: A poly(ethylene terephthalate) polyester composition which is decreased in the amount of a cyclic trimer of ethylene terephthalate formed in melting, and a method for producing the same.Type: GrantFiled: September 1, 1998Date of Patent: February 1, 2000Assignee: Unitika Ltd.Inventors: Yasumasa Fukushima, Kiwamu Yuki, Tsunetoshi Matsuda
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Patent number: 5989663Abstract: The invention relates to a copolyester, having (a) a repeat unit of a dicarboxylic acid component, having from 80 to 100 mole % terephthalic acid or the corresponding ester thereof, and from 0 to 20 mole % of a modifying aromatic dicarboxylic acid having less than or equal to 20 carbon atoms or the corresponding ester thereof, wherein the total mole % of dicarboxylic acid component is equal to 100 mole %; and (b) a repeat unit of a glycol component, having from 5 to 85 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol, ethylene glycol of from 15 to 95 mole %, and at least 1 mole % of a modifying glycol having from 3 to 16 carbon atoms, wherein the total mole % of glycol component is equal to 100 mole %. The invention also relates to a method of making the copolyester described above. The invention also relates to articles made from the copolyesters described above. The invention further relates to a method of determining the melt strength and sag of a polyester.Type: GrantFiled: December 23, 1997Date of Patent: November 23, 1999Assignee: Eastman Chemical CompanyInventors: John C. Morris, James R. Bradley, Kab Sik Seo
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Patent number: 5990266Abstract: Degradable polyesters useful in packaging, packing, agricultural, biomedical, and other applications are made by reacting amine-protected glutamic acid with diols or epoxy compounds. The polyesters include a thermoplastic main chain aliphatic polyester, a thermoset heterochain polyester and a thermoset heterochain aromatic polyester. Each of these polyesters can be hydrolyzed into monomers using a biological catalyst such as the enzyme lipase. The thermoplastic main chain aliphatic polyester and the thermoset heterochain polyester can be degraded to respiratory gases and biomass with a mixed culture of Rhizopus, chinesis, Rhizopus delemar, Penecillium pinophilum, Aspergillus niger and Pseudomonas aeruginosa microorganisms. This mixed culture of microorganisms can also be used to degrade other polyesters containing hydrolyzable backbone polyesters.Type: GrantFiled: December 2, 1998Date of Patent: November 23, 1999Assignee: University of NebraskaInventors: Raef M. Tadros, Delmar C. Timm
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Patent number: 5990197Abstract: An organic solvent based polyester ink formulation having a fluorescing compound therein is suitable for ink jet printing applications. The ink is useful for producing invisible printing/markings on the surface of a variety of materials for identification, authentication, sorting, etc. Suitable printing substrates include porous and non-porous materials such as plastic, film, sheeting, fabric, paper, high gloss paper; metal, foils, plates; rubber; glass; cellophane; wood; and the like. The ink formulation contains at least one organic soluble polyester, having at least one near infrared fluorophore copolymerized therein, dissolved in an organic solvent. Suitable organic solvents include a C.sub.3 -C.sub.6 carbon ketone, a C.sub.3 -C.sub.6 carbon organic ester, a C.sub.1 -C.sub.3 carbon alcohol, or a combination thereof. In a preferred embodiment, the polyester containing the copolymerized near infrared fluorophore is dissolved in a solvent comprising a C.sub.3 -C.sub.6 carbon ketone and a C.sub.1 -C.sub.Type: GrantFiled: January 5, 1998Date of Patent: November 23, 1999Assignee: Eastman Chemical CompanyInventors: Nelson Zamora Escano, James John Krutak, Sr., Max Allen Weaver
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Patent number: 5981690Abstract: Poly(alkylene arylates) having excellent optical properties are disclosed and can be prepared using an organic titanate-ligand catalyst solution containing organic silicates and/or zirconates and, preferably, certain phosphorus compounds.Type: GrantFiled: April 15, 1999Date of Patent: November 9, 1999Assignee: E. I. du Pont de Nemours and CompanyInventors: Steven Raymond Lustig, Robert Ray Burch
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Patent number: 5922164Abstract: A method of thermally laminating a substrate with a polyester film characterized in that said film has a melting point of 150-250.degree. C., contains 0.01-1% by weight of diethylene glycol component and not more than 0.8% by weight of cyclic trimers, and has an intrinsic viscosity ?.eta.! of not less than 0.7. The film has good formability and physical properties such as impact resistance, which are hitherto not attained, and the film is excellent in adhesiveness and taste characteristics, so that the film is suited as a wrapping material and as an inner liner of containers.Type: GrantFiled: August 27, 1997Date of Patent: July 13, 1999Assignee: Toray Industries, Inc.Inventors: Masahiro Kimura, Hideyuki Yamauchi, Kenji Tsunashima, Shiro Imai
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Patent number: 5905136Abstract: The subject is a class of catalyzers to be used in the stage of polycondensation of the synthesis of poly(ethylene terephtalate), consisting of metal and non-metal derivatives in composition with sulfonic acids mixed with titanium compounds so that the final polymer contains a sulfur quantity of 5-60 ppm and a quantity of metals between 2 and 100 ppm.Type: GrantFiled: June 19, 1997Date of Patent: May 18, 1999Assignees: Montefibre S.p.A., Inca International S.p.A.Inventors: Riccardo Po, Luigi Pelosini
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Patent number: 5898058Abstract: A continuous process for producing polyethylene terephthalate polyester from terephthalic acid and ethylene glycol uses a stabilizer, preferably containing phosphorous, to produce a high quality polyethylene terephthalate polyester which is relatively free of the acetaldehyde and discoloration which are associated with the post-polymerization activity of a polymerization catalyst. The stabilizer is preferably added at or after the end of the polymerization reaction prior to polymer processing to deactivate the polymerization catalyst and can increase the throughput of the polyester without adversely affecting the thermal stability of the polyethylene terephthalate polyester. Alternatively, the late addition of the stabilizer can increase the thermal stability of the polyester without adversely affecting the throughput of the polyethylene terephthalate polyester.Type: GrantFiled: May 20, 1996Date of Patent: April 27, 1999Assignee: Wellman, Inc.Inventors: Carl S. Nichols, Tony Clifford Moore, Walter Lee Edwards
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Patent number: 5898060Abstract: A copolyester for molding a bottle which comprises 95 to 87 mol % of naphthalenedicarboxylic acid and 5 to 13 mol % of terephthalic acid as dicarboxylic acid components and a diol component consisting essentially of ethylene glycol, has an acetaldehyde content of 20 ppm or less and an intrinsic viscosity of 0.40 to 0.85 dl/g, and produces acetaldehyde in an amount of 30 ppm or less when the copolyester is kept molten with stirring at 300.degree. C. for 5 minutes.Type: GrantFiled: August 14, 1998Date of Patent: April 27, 1999Assignee: Teijin LimitedInventors: Minoru Suzuki, Kimihiko Sato
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Patent number: 5891985Abstract: A soluble mono-alkyl Stannoic Acid/glycol liquid phase catalyst produced from the reaction of a mono-alkyl Stannoic Acid and a glycol at a temperature of from at least 180.degree. C., and its use in preparing high molecular weight polyester polymers.Type: GrantFiled: October 1, 1997Date of Patent: April 6, 1999Assignee: E. I. du Pont de Nemours and CompanyInventor: Edward Gus Brugel
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Patent number: 5886088Abstract: There are provided a polyethylene terephthalate resin composition in which to 100 parts by weight of a polyethylene terephthalate resin (A) polymerized by use of a germanium catalyst and having at least 80% of an ethylene terephthalate repetition unit, 0.05 to 30 parts by weight of a compound selected from the group consisting of an epoxy compound having at least two intramolecular epoxy groups without any intramolecular ester linkage and a carbodiimide compound (B) is formulated, and resin compositions in which a fibrous reinforcing material (C), a block copolymer (D) and an inorganic nucleating agent (E) are further formulated in the above mentioned composition. The resin composition of the present invention is excellent in moist heat resistance, fluidity and mechanical strength, and in addition, can be subjected to high cycle molding even in a mold of a low temperature to yield a molded article with improved surface characteristics.Type: GrantFiled: October 21, 1996Date of Patent: March 23, 1999Assignee: Kanegafuchi Kagaku Kogyo Kabushiki KaishaInventors: Kazuaki Matsumoto, Masahiko Mihoichi, Youichi Ohara, Kazushi Hirobe, Kenji Mogami, Tadashi Koyama
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Patent number: 5880224Abstract: A process for producing an aliphatic polyester carbonate which comprises reacting (1) an aliphatic dicarboxylic acid compound containing succinic acid as a main component, (2) an aliphatic dihydroxy compound containing 1,4-butanediol as a main component, and (3) (a) a polyhydric alcohol having 3 or more hydroxyl groups in a molecule, (b) a polybasic carboxylic acid compound having 3 or more carboxyl groups in a molecule, or (c) a polybasic carboxylic acid having one or more hydroxyl groups in a molecule to obtain an aliphatic polyester oligomer and reacting the obtained aliphatic polyester oligomer and a carbonate compound, wherein the aliphatic polyester carbonate has a melt tension of 1.5 g or more at 190.degree. C.Type: GrantFiled: July 28, 1997Date of Patent: March 9, 1999Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Mitsuo Miura, Kyohei Takakuwa, Takayasu Fujimori, Maki Ito
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Patent number: 5869543Abstract: The invention comprises a method for synthesizing polyethylene terephthalate from waste polyethylene terephthalate by cleavage with ethylene glycol and separation of bis(hydroxyethylene) terephthalate from the cleavage mixture with a specific temperature program, recrystallization from water, and esterification and polycondensation with the addition of terephthalic acid.The invention further comprises a method for synthesis of polyethylene naphthalate from waste polyethylene naphthalate in a similar manner.Type: GrantFiled: August 29, 1997Date of Patent: February 9, 1999Assignee: Zimmer AktiengesellschaftInventors: Frank Boos, Norman Schnittker, Joachim Seelig
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Patent number: 5852164Abstract: A polyester comprises a dicarboxylic acid moiety comprising terephthalic acid or its ester forming derivative and a diol moiety comprising ethylene glycol and 1,4-cyclohexanedimethanol of 10 to 60 mol % based on the whole diol moiety, the intrinsic viscosity of the polyester being 0.68 to 0.95 dl/g, the "b" value of color tone of the produced pellets of polyester being -5 to 5, the number of the carboxylic acid terminals being not more than 30 eq/ton, and the sum of the numbers of the vinyl terminals, the vinylidene terminals and the methylcyclohexene terminals being not more than 25 eq/ton.Type: GrantFiled: April 15, 1997Date of Patent: December 22, 1998Assignee: Mitsubishi Chemical CorporationInventors: Hideko Akai, Katsuji Tanaka, Masahiko Fujimoto, Noboru Sato
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Patent number: 5851612Abstract: A container formed from a copolyester composition which comprises a copolyester containing 80 to 95 mol % of terephthalic acid and 20 to 5 mol % of 2,6-naphthalenedicarboxylic acid as acid components and ethylene glycol as a glycol component, wherein catalyst metals of a calcium compound, magnesium compound and cobalt compound are contained in the copolyester in such amounts that satisfy all the following expressions (1) to (4) based on the total of the whole acid component of the polymer:0<Ca.ltoreq.35(mmol %) (1)0<Mg.ltoreq.80(mmol %) (2)40.ltoreq.(Mg+Ca).ltoreq.90(mmol %) (3)0.ltoreq.Co.ltoreq.15(mmol %) (4).The above polyester container is excellent in gas barrier property, ultraviolet light screening property, hot water resistance, hue and transparency, is not whitened and has a small content of aldehyde.Type: GrantFiled: December 24, 1997Date of Patent: December 22, 1998Assignee: Teijin LimitedInventors: Masami Umeda, Kimihiko Sato
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Patent number: 5849849Abstract: An atmospheric pressure process for the continuous production of polyester is disclosed wherein a melt of bis(3-hydroxy propyl) terephthalate, or its low molecular oligomers, obtained by esterifying terephthalic acid or transesterifying dimethyl terephthalate with propylene glycol, is intimately contacted with an inert gas to facilitate polymerization and removal of the reaction by-products. The propylene glycol evolved and the inert gas are recycled.Type: GrantFiled: April 23, 1997Date of Patent: December 15, 1998Assignee: E. I. du Pont de Nemours and CompanyInventor: Kamlesh Kumar Bhatia
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Patent number: 5847070Abstract: New compounds including bis-.beta.-hydroxy ethyl bibenzoate containing less than 2.5%, and preferably less than 1%, diethylene glycol and a process for the production of the bis-.beta.-hydroxy ethyl bibenzoate by the condensation of 4,4'-biphenyl dicarboxylic acid and ethylene glycol at low temperature and pressure in the presence of a catalyst are disclosed. Use of the compounds to produce polyesters is also disclosed.Type: GrantFiled: December 1, 1994Date of Patent: December 8, 1998Assignee: Monsanto CompanyInventors: Jawed Asrar, David J. Weinkauff, A. Hameed Bhombal
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Patent number: 5844068Abstract: A process for the preparation of a readily hydrolyzable and/or biodegradable polyhydroxycarboxylic acid resin which can be used in agricultural materials, gardening materials, fishery materials, caking materials, medical instruments and materials, etc. and, even when discarded after use, which undergoes hydrolysis and/or is biodegraded into carbon dioxide, water, etc. Also disclosed are a hydrolyzable and/or biodegradable polyhydroxycarboxylic acid resin composition having an increased resin strength and melt viscosity, and a process for the preparation thereof.Type: GrantFiled: March 12, 1997Date of Patent: December 1, 1998Assignee: Nishikawa Rubber Co., Ltd.Inventors: Junzo Otera, Toru Yano, Hirokazu Yamamoto, Nobuyuki Sakuda
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Patent number: 5834118Abstract: Hyperbranched polyester of a polyol with 3 to 10 reactive hydroxyl groups, preferably of equivalent reactivity, and an aromatic polycarboxylic anhydride with 2 to 4 carboxyl groups, preferably 3 carboxyl groups, each hydroxyl group of the polyol forming an ester linkage with one anhydride group of the polycarboxylic anhydride, and further glycidyl (meth)acrylate or allyl glycidyl ether forming ester linkages with the remaining carboxyl groups of the anhydride and free hydroxyl groups. Further in the hyperbranched polyester (meth)acrylic anhydride and/or an aliphatic carboxylic anhydride form ester linkages with the free hydroxyl groups. The invention also comprises a process for the production of hyperbranched polyesters and such polyesters obtainable by the process. The hyperbranched polyesters can be used as resins, curable by UV irradiation, for the production of coatings, adhesives, laminates, foils and thin films and fibre-reinforced composites.Type: GrantFiled: May 9, 1997Date of Patent: November 10, 1998Assignee: Neste Oy of KeilaniemiInventors: Bengt R.ang.nby, Shi Wenfang
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Patent number: 5830981Abstract: A process for producing a polyethylene terephthalate in which the amount of the oligomers, such as cyclic trimer etc., is lower and which causes metal mold staining to occur difficultly. The process comprises an esterification stage in which dicarboxylicacids including mainly terephthalic acid or ester-forming derivatives of such acids are esterified with glycols including mainly ethylene glycol or with ester-forming derivatives of such glycols; a liquid phase polycondensation stage in which the esterified product obtained in the esterification stage is subjected to a polycondensation in a liquid phase containing a polycondensation catalyst and having a content of an alkaline solubilizing agent of 0.Type: GrantFiled: December 9, 1996Date of Patent: November 3, 1998Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Hiroshi Koreishi, Yasuhiro Tanaka, Kimiyoshi Miura
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Patent number: 5811513Abstract: In the production of polyethylene naphthalate of the present invention, the esterification reaction between naphthalenedicarboxylic acid and ethylene glycol is conducted while causing water to be present in a reaction system from a start of reaction, in the presence of at least one catalyst selected from the group consisting of nitric, carboxylic, phosphoric and hydrogenphosphoric acid metal salts and alkyl amines according to necessity, to thereby attain an esterification ratio of 45 to 80%, so that a liquid mixture of naphthalenedicarboxylic acid esterification reaction products containing naphthalenedicarboxylic acid, carboxyl-hydroxyethoxycarbonylnaphthalene and bis(hydroxyethoxycarbonyl)naphthalene is obtained. Subsequently, a crystallized reaction product is separated from this liquid mixture to thereby obtain a mixture of esterification reaction products. Thereafter, this mixture having ethylene glycol added thereto according to necessity is subjected to polycondensation.Type: GrantFiled: July 9, 1997Date of Patent: September 22, 1998Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Hiroshi Iwasaki, Masayasu Ishibashi, Hiromi Ueki, Shoji Hiraoka, Toru Matsuyoshi, Satoshi Inoki