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Removal of Residual Acetaldehyde From (19) TZZ_Z_T (11) EP 1 784 440 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.: of the grant of the patent: C08G 63/02 (2006.01) C08G 63/88 (2006.01) 10.01.2018 Bulletin 2018/02 B01J 8/18 (2006.01) (21) Application number: 05792582.8 (86) International application number: PCT/US2005/030531 (22) Date of filing: 29.08.2005 (87) International publication number: WO 2006/028746 (16.03.2006 Gazette 2006/11) (54) REMOVAL OF RESIDUAL ACETALDEHYDE FROM POLYESTER POLYMER PARTICLES ENTFERNUNG VON VERBLEIBENDEM ACETALDEHYD AUS POLYESTER-POLYMER-ARTIKELN ELIMINATION D’ACETALDEHYDE RESIDUEL DE PARTICULES DE POLYMERES DE POLYESTER (84) Designated Contracting States: • COLHOUN, Frederick, Leslie AT BE BG CH CY CZ DE DK EE ES FI FR GB GR Kingsport, TN 37660 (US) HU IE IS IT LI LT LU LV MC NL PL PT RO SE SI • EKART, Michael, Paul SK TR Kingsport, TN 37660 (US) • DEBRUIN, Bruce, Roger (30) Priority: 02.09.2004 US 606660 P Lexington, SC 29072 (US) 21.12.2004 US 18358 (74) Representative: Tostmann, Holger Carl et al (43) Date of publication of application: Wallinger Ricker Schlotter Tostmann 16.05.2007 Bulletin 2007/20 Patent- und Rechtsanwälte Partnerschaft mbB Zweibrückenstrasse 5-7 (73) Proprietor: GRUPO PETROTEMEX, S.A. DE C.V. 80331 München (DE) San Pedro Garza Garcia, Nuevo Leon 66265 (MX) (56) References cited: (72) Inventors: DE-A1- 4 223 197 FR-A- 2 828 199 • ARMENTROUT, Rodney, Scott US-A- 4 230 819 US-A- 4 974 336 Kingsport, TN 37660 (US) US-A1- 2004 236 065 US-A1- 2005 196 566 Note: Within nine months of the publication of the mention of the grant of the European patent in the European Patent Bulletin, any person may give notice to the European Patent Office of opposition to that patent, in accordance with the Implementing Regulations. Notice of opposition shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention). EP 1 784 440 B1 Printed by Jouve, 75001 PARIS (FR) EP 1 784 440 B1 Description CROSS REFERENCE TO RELATED APPLICATIONS 5 [0001] This application claims the benefit of U.S. Provisional Application No. 60/606,660, filed September 2, 2004. 1. Field of the Invention [0002] This invention relates to the removal of residual acetaldehyde from polyester particles. 10 2. Background of the Invention [0003] A conventional process for the preparation of a polyethylene terephthalate based resin (PET) is characterized as a two stage process: a melt phase process which includes the esterification and polycondensation reactions, and a 15 solid state polymerization process for increasing the molecular weight of the polymer in the solid state rather than in the melt. In a solid state polymerization process, PET is exposed to temperatures of 200-230°C and a constant counter- current flow of nitrogen through the resin for a significant length of time. In such a conventional process, the molecular weight of the resin is increased in the melt phase up to an It.V. of about 0.55 to 0.65, followed by pelletization, after which the pellets are crystallized, and then solid state polymerized with an optional annealing step after crystallization. 20 [0004] In the melt phase, residual acetaldehyde is formed by degradation reactions occurring at the high temperatures experienced during the last stages of polycondensation. In a conventional process, attempting to further increase the molecular weight at these It.V. levels causes a marked increase in the formation of acetaldehyde. However, elevated temperatures in the melt phase are required to facilitate the polycondensation molecular weight building reactions. Accordingly, the polymer is made only to a low It.V. of about 0.55 to 0.60 dL/g in the melt phase, followed eventually by 25 the further increase in the molecular weight of the polymer in the solid state. [0005] During solid state polymerization, the particles are exposed to a counter-current flow of nitrogen gas to carry off ethylene glycol, water, and/or other condensates generated during polycondensation. The use of nitrogen also min- imizes the oxidative degradation of the PET resin at solid stating temperatures The nitrogen gas also helps safeguard against oxidation of antimony metal in resins containing reduced antimony as a reheat agent. Although the solid state 30 polymerization provides a product with limited degradation products, the process adds a considerable amount of cost (conversion and capital) to the PET manufacturing process. [0006] The French patent application FR 2 828 199 A1 discloses a polyester comprising at least 92.5 % units derived from terephthalic acid and ethylene glycol having an intrinsic viscosity of 0.45 to 0.70 dl/g and an acetaldehyde content below 3 ppm. The process for producing the same comprises producing a polyester with an intrinsic viscosity below 0.8 35 dl/g by melt polymerization, forming granules of the polyester, crystallizing the granules, and heat-treating the granules at 130 to 200 °C to reduce the acetaldehyde content below 3 ppm and to give an intrinsic viscosity below 0.7 dl/g. [0007] The German patent application DE 4 223 197 A1 discloses a process for a simultaneous removal of an aldehyde, a solid-phase postcondensation and a drying of the linear polyesters and the copolyesters by an after-treating of the polyester pellets with a diffusion surface of 1.95 to 2.90 m 2/kg, an individual pellet weight of 5 to 15 mg and a bulk density 40 3 of 750 to 900 kg/m at 140 to 210 °C. with a flow of a dry gas mixture consisting of 60 to 90 vol % N 2, 5 to 21 % O2 and 0.1 to 25 % CO2 at a quantity ratio of 0.5 to 2.5 kg/h gas mixture per kg/h polyester. [0008] The US patent application US 4 230 819 A discloses a removal of acetaldehyde from crystalline polyethylene terephthalate granules by passing a dry inert gas through a bed of resin at a temperature of 170 °C. to 250 °C for a time sufficient to remove the aldehydes. 45 [0009] The USpatent application US2005/196566 A1 discloses polyester polymer particleshaving an intrinsic viscosity, a surface, and a center, wherein the intrinsic viscosity at the surface of the particles is less than 0.25 dL/g higher than the intrinsic viscosity at the center of the particles. The polyester polymer particles are crystalline to prevent the particle s from sticking to each other while drying, and they contain less than 10 ppm acetaldehyde. [0010] The US patent application US 2004/236065 A1 discloses polyethyleneterephthalate resins used for making 50 hollow containers. The polyester comprises at least 92.5 % in number of recurrent units derived from terephthalic acid of aliphatic diols having an intrinsic viscosity ranging between 0.45 dl/g and 0.70 dl/g, and an acetaldehyde content less than 3 ppm. [0011] The US patent application US 4 974 336 A discloses a method for use in drying particulate matter employing a drier comprising a cylindrical upper section, a frustoconical lower section, a rotatable shaft extending substantially the 55 entire length of the interior of the drier, a plurality of axially spaced arrays of circumferentially spaced, radially extendin g stirring arms appended to the shaft, and at least two perforated frustoconical separators mounted within the drier in fixed, inverse and spaced apart relation to each other, and means for introducing a heated gas into the drier for contacting and drying the particulate matter, the stirring arms and separators cooperating to retard agglomeration of the particulate 2 EP 1 784 440 B1 matter. [0012] It would be desirable to eliminate the step of solid state polymerization by the manufacture of a polyester polymer resin in the melt phase having a high It.V. while minimizing the level of residual acetaldehyde, while also providing a crystallized particle to reduce the agglomeration of the particles in dryers feeding extruders for the formation of articles 5 such as preforms and sheet. 3. Summary of the Invention [0013] The subject matter of the present invention is defined in claims 1-27 as attached. Embodiments described 10 herein which are not covered by the claims merely serve to illustrate the technical context of the present invention. [0014] In one embodiment, there is provided a process comprising introducing polyester polymer particles containing residual acetaldehyde into a vessel at a temperature within a range of 130°C to 195°C to form a bed of particles within the vessel, flowing a gas through at least a portion of the particle bed, and withdrawing finished particles from the vessel having a reduced amount of residual acetaldehyde. The gas is introduced into said vessel at a temperature of 70°C or 15 less and 10°C or more, wherein the hot particles introduced into the vessel at a temperature range from 130°C to 195°C provide the heat energy transferred to the gas to provide a gas temperature within the vessel sufficient to effectuate acetaldehyde stripping. In this process, it is not necessary to introduce a hot flow of gas at high flow rates otherwise required to heat up cool particles to a temperature sufficient to strip cetaldehyde. Rather, this process provides a benefit in that, if desired, gas introduced, into the vessel at low flow rates and low temperatures can nevertheless be effective 20 to strip acetaldehyde in a reasonable time because the hot particles quickly heat the low flow of gas to the particle temperature. [0015] In a variety of other embodiments, the polyester polymer forming the particles is polymerized in the melt phase to an It V.
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