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United States Patent (10) Patent No.: US 9,175,136 B2 Louis (45) Date of Patent: *Nov

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United States Patent (10) Patent No.: US 9,175,136 B2 Louis (45) Date of Patent: *Nov US009 175136B2 (12) United States Patent (10) Patent No.: US 9,175,136 B2 Louis (45) Date of Patent: *Nov. 3, 2015 (54) METHOD FOR THE MANUFACTURE OF 4,636,557 A 1/1987 Deckers POLY(ARYL ETHER KETONE)S IN THE is's A : f E. SE tal. 3. 35 PRESENCE OF SODIUM CARBONATE 4,766,197- J. A * 8/1988 ClendinningcMaster et etal..... al. ........ 528/125 4,767,837 A * 8/1988 Jansons .............. 528,125 (75) Inventor: Chantal Louis, Alpharetta, GA (US) 4,774.311 A * 9/1988 Kelsey ... 528,125 4,855.388 A * 8/1989 Kelsey ........ 528,125 (73) Assignee: Solvay Advanced Polymers, L.L.C., 4,867,912 A * 9/1989 Heinz et al. ................... 528,125 4,868,273 A 9, 1989 Daniels Alpharetta, GA (US) 4,906.784.- WW A * 3, 1990 SkolOCT . 528,125 4,908.425. A * 3/1990 Robeson et al. 528,125 (*) Notice: Subject to any disclaimer, the term of this 4,952,665 A * 8/1990 Ebata et al. ... 528,219 patent is extended or adjusted under 35 4,999.414 A * 3/1991 Genz et al. .................... 528,125 U.S.C. 154(b) by 243 days. 5,081,214. A 1/1992 Schneller 5,116,933 A * 5/1992 Newton ........................ 528,125 This patent is Subject to a terminal dis- 5,120,818. A * 6/1992 Robeson et al. .............. 528/125 claimer. 5, 122,587 A * 6/1992 Heinz et al. ... ... 528,126 5,122,588 A * 6/1992 Koch et al. .. 528, 179 (21) Appl. No.: 13/125,537 9 * 238; star 528,125 5.312.278 A * 5/1993 Praendner et al. ... 528,171 (22) PCT Filed: Oct. 23, 2009 5,268.444 A * 12, 1993 Jenseneral. 528,125 5,362,836 A * 1 1/1994 Helmer (86). PCT No.: PCT/EP2009/064O11 Metzmann et al. ........... 528,125 5,373,081 A * 12/1994 Yang et al. ..... 528,125 S371 (c)(1), 5,523,384 A * 6/1996 Memeger et al. ............. 528/392 (2), (4) Date: Apr. 21, 2011 5,580,948 A * 12/1996 Neufeld et al. 528,125 6,593.445 B2* 7/2003 Schwab ......... 528, 175 (87) PCT Pub. No.: WO2010/046484 2002fOO 10307 A1* 1 2002 Schwab ......... 528,174 2009,024.0020 A1* 9, 2009 Gharda et al. ... 528,126 PCT Pub. Date: Apr.p 29,9 2010 2011/0201775 A1 8, 2011 Louis et al. ................... 528,126 (65) Prior PublicationO O Data (Continued) US 2011/0213095 A1 Sep. 1, 2011 FOREIGN PATENT DOCUMENTS CN 101215365. A T 2008 Related U.S. Application Data DE 4121139 A1 1, 1993 EP OOO1879 A1 5.1979 (60) Provisional application No. 61/108,096, filed on Oct. 24, 2008, provisional application No. 61/108,097, (Continued) filed on Oct. 24, 2008, provisional application No. 61/140,205, filed on Dec. 23, 2008. OTHER PUBLICATIONS U.S. Appl. No. 13/125,508, filed Apr. 21, 2011, Chantal Louis et al. (51) Int. Cl. U.S. Appl. No. 13/125,523, filed Apr. 21, 2011, Chantal Louis. C08G 65/40 (2006.01) Zhuo, Ni, etal "Characterization and Spectra Studies of Peek Pre C07C35/06 (2006.01) pared by Two Salting Ways'. Polymer Materials Science and Engi C08G 8/02 (2006.01) neering, 1989, n° 3. p. 64-68; 5. pgs: Includes abstract in English. COSG 75/23 (2006.01) Nassau Kurt "Color”. Kirk-Othmer Encyclopedia of Chemical (52) U.S. Cl. Technology, 2004, vol. 7, p. 303-341, John Wiley & Sons, Inc.; 39 CPC .......... C08G 65/4093 (2013.01); C07C315/06 E.ovay PProcess, ”, Wikipedia,1Kipedia, thee Free Encyclopedia, "http://ife. 65/4oS 852.2% s wikipedia.org/wiki/Solvay process”, Nov. 21, 2008; 8 pgs. C08G 75/23 (2013.01); C08G 2261/3444 (Continued) (2013.01) (58) Field of Classification Search Primary Examiner — Liam J Heincer CPC ........... C08G 2650/40: C08G 65/4087;65/4012 C08G (74) Attorney,y Agent, or Firm — Osha Liang LLP USPC ............................................ 528/219, 86, 222 See application file for complete search history. (57) ABSTRACT (56) References Cited Sodium carbonate (Na2CO) having a certain particle size distribution and its use in preparing poly(aryl ether ketone)S. U.S. PATENT DOCUMENTS especially PEEK. Poly(aryl ether ketone)s made using the described sodium carbonate. A method for providing a 3,655,331 A * 4/1972 Seglin et al. .................. 423, 207 3,904,733. A * 9/1975 Gancy et al. ... 423,206.2 Sodium carbonate having a certain particle size distribution, 4,113,698 A * 9/1978 Staniland ...................... 528,481 which is especially well suited for the preparation of poly 4,151,261 A * 4, 1979 Poncha et al. ... ... 423,206.2 (aryl ether ketone)s. 4,176,222 A * 1 1/1979 Cinderey et al. .............. 528,126 4,320,224. A 3, 1982 Rose et al. 4.331,798 A 5, 1982 Staniland 13 Claims, No Drawings US 9,175,136 B2 Page 2 (56) References Cited OTHER PUBLICATIONS International Search Report and Written Opinion issued Feb. 15. U.S. PATENT DOCUMENTS 2010 in corresponding International Application No. PCT/EP2009/ 064011 (10 pages). 2011/0213115 A1 9, 2011 Louis ............................ 528,126 International Preliminary Report on Patentability issued Apr. 26. 2011/0224399 A1* 9, 2011 Louis et al. ................... 528,126 2011 in corresponding International Application No. PCT/EP2009/ 064011 (7 pages). FOREIGN PATENT DOCUMENTS Communication pursuant to Article 94(3) EPC issued Feb. 2, 2012 in corresponding European application No. 09 737 003.5 (5 pages). EP O194062 A2 9, 1986 Communication pursuant to Article 94(3) EPC issued Jan. 10, 2013 in EP 211693 A1 2, 1987 corresponding European application No. 09 737 003.5 (3 pages). EP O3O3389 A2 2, 1989 Sodium carbonate—a versatile material; published by the Royal EP 2292673 A1 3, 2011 Society of Chemistry; “Manufacturing sodium carbonate—an over GB 2217322. A 10, 1989 view for teachers' (2 pages). WO 95.315O2 A1 11, 1995 Sodium Carbonate; SIDS Initial Assessment Report for SIAM 15; WO WOO1666.20 A2 9, 2001 Boston, USAA, Oct. 22-25, 2002; UNEP Publications (22 pages). WO WO 2009021918 A1 2, 2009 Technical Data Sheet—Light Sodium Carbonate; NovaCarb; Jan. WO WO 2010046482 A1 4/2010 2004 (2 pages). WO WO 2010046483 A1 4/2010 WO WO 2010046487 A1 4, 2010 * cited by examiner US 9, 175,136 B2 1. 2 METHOD FOR THE MANUFACTURE OF For example, U.S. Pat. No. 4,320.224 (Rose et al.) POLY(ARYL ETHER KETONE)S IN THE describes the preparation of PEEK by reacting 4,4'-difluo PRESENCE OF SODIUM CARBONATE robenzophenone with p-hydroquinone in the presence of at least one alkali metal carbonate orbicarbonate. In particular, CROSS-REFERENCE TO RELATED Rose's Example 3 (which was submitted for comparison APPLICATIONS purposes) describes a polymerization process for making The present application is a U.S. national stage entry under PEEK using a certain anhydrous Sodium carbonate as sole 35 U.S.C. S371 of International Application No. PCT/ alkali metal carbonate or bicarbonate; the PEEK made EP2009/064011 filed Oct. 23, 2009, which claims the priority accordingly suffered from a low IV (equal to 0.48) and a benefit to U.S. provisional application No. 61/108,096 filed rather dark color (absorbance of 0.20). Precisely, Rose on Oct. 24, 2008, to U.S. provisional application No. 61/108, teaches, notably on col. 7, 1.46-50, that the formation of low 097 filed on Oct. 24, 2008, and to U.S. provisional application molecular weight, dark-colored, brittle PEEK, results from No. 61/140,205 filed on Dec. 23, 2008, the whole content of all these applications being herein incorporated by reference the use of sodium carbonate or bicarbonate alone, and pro 15 poses, as Sole remedies, to use instead a higher alkali metal for all purposes. carbonate orbicarbonate (such as KCO) either alone, or in FIELD OF THE INVENTION admixture with NaCO. Unfortunately, Rose's proposed remedies are generally not as Suitable as desired; indeed, the The present invention relates to the use of a sodium car use of KCO or another higher alkali metal has also some bonate (Na,CO) having a certain particle size distribution in negative influence on polymer properties (resulting in gels preparing poly(aryl ether ketone)s, especially PEEK. Poly and discolored polymer), as described in ICI Patent applica (aryl ether ketone)s made using said sodium carbonate also tion EP001879, and in Zhuo N., Yubin Z., Zhongwen W., make up a part of the invention, as well as compositions of Xinyi T. Polymer Materials Science and Engineering, 1989, matters and shaped articles comprising said poly(aryl ether N3, P64-68. These ones are completely overlooked by Rose. ketone)S. 25 Besides, Rose provides no information on the particle size The present invention relates also to a method for providing distribution of the sodium carbonate of Example 3, except a sodium carbonate having a certain particle size distribution, that that has been sieved through a 500 um sieve; as a matter which is especially well suited for the preparation of poly of fact, based on the low IV and dark color of the resulting (aryl ether ketone)s. PEEK, it can be concluded a posteriori, accounting for the 30 Applicant's present contribution, that the Sodium carbonate BACKGROUND OF THE INVENTION used by Rose had very likely a Doo well above 250 um. More precisely, considering that that the most broadly available Poly(aryl ether ketone)s (i.e., PAEKs) are a well known Sodium carbonates are by far dense sodium carbonates (of class of engineering polymers useful in various fields of which the Ds are typically of about 400 um), it is very likely endeavor.
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