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(12) United States Patent (10) Patent No.: US 6,323,302 B1 Sasaki Et Al

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(12) United States Patent (10) Patent No.: US 6,323,302 B1 Sasaki Et Al USOO63233O2B1 (12) United States Patent (10) Patent No.: US 6,323,302 B1 Sasaki et al. (45) Date of Patent: Nov. 27, 2001 (54) CARBONIC ACID DIESTER, AROMATIC 5,276,129 1/1994 Sakashita et al. ................... 528/198 POLYCARBONATE AND FACILITIES, AND 5,399.659 3/1995 Kiihling et al. ...................... 528/199 PREPARATION THEREOF 5,444,148 8/1995 Alewelt et al. 5,455,324 10/1995 Nukui et al.. (75) Inventors: Katsushi Sasaki; Wataru Funakoshi; 5,466,775 11/1995 Kanno et al. ........................ 528/199 Toru Sawaki, Masumi Hirata; 5,495,038 2/1996 Buysch et al. ....................... 558/274 Hiroaki Kaneko, Masanori Abe; 5,516,878 5/1996 Sasaki et al. Masasi Simonaru; Hidemi Takemoto; 5,519,106 5/1996 Nukui et al. ......................... 528/199 Jyuhou Matsuo; Yoshiki Matsuoka, 5,525,701 6/1996 Tominari et al. .................... 528/198 all of Yamaguchi (JP) 5,527,875 6/1996 Yokoyama et al. 5,548,041 8/1996 Yamato et al. ........................ 526/62 (73) Assignee: Teijin Limited, Osaka (JP) 5,578,694 11/1996 Yokoyama et al. 5,717.057 2/1998 Sakashita et al. ................... 528/196 (*) Notice: Subject to any disclaimer, the term of this 5,739,258 4/1998 Zaby et al. ........................... 528/198 patent is extended or adjusted under 35 5,929,192 7/1999 Miyauli et al.. U.S.C. 154(b) by 0 days. (21) Appl. No.: 09/445,824 FOREIGN PATENT DOCUMENTS (22) PCT Filed: Apr. 22, 1999 O 400 7329 1/1992 (EP). (86) PCT No.: PCT/JP99/02141 (List continued on next page.) S371 Date: Dec. 14, 1999 S 102(e) Date: Dec. 14, 1999 Primary Examiner Terressa M. Boykin (74) Attorney, Agent, or Firm-Sughrue, Mion, Zinn, (87) PCT Pub. No.: WO99/55764 Macpeak & Seas, PLLC PCT Pub. Date: Nov. 4, 1999 (57) ABSTRACT (30) Foreign Application Priority Data Aromatic polycarbonate having a reduced discoloration and Apr. 27, 1998 (JP) ................................................. 10–116864 Jul. 16, 1998 (JP) ... ... 10-201695 improved heat Stability, hue, etc. is provided by keeping a Sep. 14, 1998 (JP) ... ... 10-260102 preSSure in a raw material melting vessel and the linear Sep. 14, 1998 (JP) ... ... 10-260103 Velocity of a gas in a transporting piping in a Specific range, Sep. 22, 1998 (JP) ... ... 10-268231 keeping the concentration of a nitrogen-containing basic Feb. 26, 1999 (JP) ................................................. 11-05O174 compound in a specific range, recycling a byproduct con taining Specific amounts of impurities, Suppressing the (51) Int. Cl." ................................................. C08G 64/00 amounts of a nitrogen-containing basic compound, metallic (52) U.S. Cl. ... ... 528/196; 528/198 elements and a Silicic acid derivative in the carbonic acid (58) Field of Search ...................................... 528/196, 198 diester at Specific valueS or less, prescribing the material (56) References Cited quality of the reaction facilities, and/or forming an oxide layer at the inner wall Surfaces of the reaction facilities. U.S. PATENT DOCUMENTS 4,383,092 5/1983 Ko et al.. 32 Claims, 1 Drawing Sheet obsessf-1-1-1M - it i? O 5 O 15 2O 25 30 Sputter life (Tin) US 6,323,302 B1 Page 2 FOREIGN PATENT DOCUMENTS 6-056984 3/1994 (JP). 6-06.5367 3/1994 (JP). O 512 223 A1 11/1992 (EP). 6-200008 7/1994 (JP). 529 O93 3/1993 (EP). 6-234845 8/1994 (JP). O 577 849 A1 1/1994 (EP). 6-345860 12/1994 O 608778A2 (JP). 8/1994 (EP). T-070307 3/1995 O 622 418 A2 11/1994 (EP). (JP). 629 646 12/1994 (EP). 7-188116 7/1995 (JP). O 633 241A1 1/1995 (EP). 7-268,091 10/1995 (JP). O 702 583 O 1/1995 (EP). O8-OO5957 1/1996 (JP). O 667366 A2 8/1995 (EP). 8-O59975 3/1996 (JP). O 719 816 A2 7/1996 (EP). 9-241370 9/1997 (JP). O 745 580 A1 12/1996 (EP). 10-036497 2/1998 (JP). O 764 673A2 3/1997 (EP). 10-226723 8/1998 (JP). O 779 312 A2 6/1997 (EP). 4-106125 4/1992 (JP) - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - CO8G/64/30 O 819 717 A1 1/1998 4-142329 5/1992 - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - CO8G/64/30 (EP). (JP) 61-087724 5/1986 (JP). 6-491.97 2/1994 (JP) ... ... CO8G/64/30 61-087725 5/1986 (JP). 6-65367 3/1994 (JP) ... ... CO8G/64/30 4-OO7328 1/1992 (JP). 6-179744 6/1994 (JP) ... ... CO8G/64/30 4-OO7329 1/1992 (JP). T-70307 3/1995 (JP) ... ... CO8G/64/30 5-239334 9/1993 (JP). 8-277327 10/1996 (JP) ... ... CO8G/64/30 6-0491.97 2/1994 (JP). 9-255772 9/1997 (JP) - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - CO8G/64/30 U.S. Patent Nov. 27, 2001 US 6,323,302 B1 F.G. x 10 3 2.5 O1 2 Fe3 --~~~------ C 1.5 --1 M G -- \,-- 1 1 A. Y. y -1 W \- -/ f Cr (TFA) f -N-N---- f Si1 O.5 N s-sects Olese -- vot ---- O 5 10 15 2O 25 3O Sputter Tiite (Tin) US 6,323,302 B1 1 2 CARBONIC ACID DIESTER, AROMATIC polycarbonate, a method for directly reacting an aromatic POLYCARBONATE AND FACILITIES, AND dihydroxy compound Such as bisphenol with phosgene (an PREPARATION THEREOF interfacial method), and a method for performing an ester interchange reaction of an aromatic dihydroxy compound FIELD OF THE INVENTION Such as bisphenol with a carbonic acid diester Such as Some of the present invention relates to a method for diphenyl carbonate (a molten method) are known. producing an aromatic polycarbonate, more particularly Among Such production methods, the method for produc relates to a method for Stably and economically producing ing an aromatic polycarbonate by the ester interchange an aromatic polycarbonate having a good quality by a melt reaction of an aromatic dihydroxy compound with a car polycondensation reactions bonic acid diester is drawing attention because it is a method benevolent to the environment without using harmful phos Further, Some other part of the present invention relates to gene or methylene chloride, and also because it is pointed a method for producing an aromatic polycarbonate excellent out that there is a possibility that this method is better in in heat Stability and hue. view of its cost than the interfacial method. Further, Some other part of the present invention relates to 15 However, as to the quality of the aromatic polycarbonate a method for producing an aromatic polycarbonate by recy obtained by the melting method, it is difficult to obtain an cling a monohydroxy compound produced as a byproduct excellent quality material because of deteriorated color tone, from the Said melt polycondensation reaction and using as a etc., due to Severe reaction conditions, etc. In recent years, Solvent for a catalyst in producing the aromatic polycarbon further improvements in color tone and heat Stability are ate by the melt polycondensation reaction. required for the aromatic polycarbonate used for a Substrate Further, Some other part of the present invention relates to of an optical information recording medium Such as DVD, the production of a carbonic diester as a raw material for the CD, MO, etc., since a discoloration due to the lack of heat production of an aromatic polycarbonate and of an aromatic Stability and a gelation due to a thermal transformation, polycarbonate produced therefrom, more particularly, to the directly affect optical characteristics Such as a block error carbonic acid diester good in Storing Stability, and an aro 25 rate, etc., and mechanical characteristics Such as tensile, matic polycarbonate having an improved quality and color flexural properties, toughness, etc. tone, which is produced from the Said carbonic acid diester. Further, as to the carbonic acid diester used as a raw Further, Some other part of the present invention relates to material for the aromatic polycarbonate, diphenyl carbonate a method for producing a polycarbonate, more particularly is preferably used, but diphenyl carbonate has been conven to a method for producing an aromatic polycarbonate, the tionally produced by reading phosgene with phenol in the generation of foreign materials being Suppressed, by using presence of an acid capturing agent, preferably using a basic reaction facilities composed of a Stainless alloy containing a catalyst. specific amount of a specific metal in producing the aromatic Diphenyl carbonate produced by the above method usu polycarbonate by an ester interchange reaction of a dihy ally contains chlorine compounds derived from phosgene droxy compound with a carbonic acid diester compound. 35 used as the raw material or an intermediate chloroformate, Further, Some other part of the present invention relates to but Since the chlorine compounds give adverse effect on the facilities for producing an aromatic polycarbonate, more color tone of the polymer, attention has been drawn to the particularly to facilities having a specific oxide film layer. chlorine compounds and various purification processes have The facilities disclosed in the present invention are prefer been proposed to decrease them. able for producing an aromatic polycarbonate by the melt 40 For example, various purification processes were pro ester interchange method and Suitable for producing an posed in Japanese Patent Publication Sho 38-18686; Method aromatic polycarbonate containing a reduced amount of for producing diphenyl carbonate using a basic catalyst Such foreign materials, typically fine foreign materials, in the as an amine, Japanese Patent Publication Sho 41-10812; polymer. Removal of chloroformate by a surfactant, Plastic Material In the Statement of the present description and claims, 45 Course (vol. 17), page 4-47, published by Nikkan Kogyou "aromatic dihydroxy compound” is Sometimes called as Shinbunsha, etc. However, the diphenyl carbonate produced "aromatic diol compound”, “catalyst deactivation agent' is or purified by Such a method usually contains, as an Sometimes called as “catalyst inactivation agent', and "end impurity, a nitrogen-containing compound having used as capping agent' is Sometimes called as "terminal blocking the catalyst.
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