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(12) United States Patent (10) Patent No.: US 8,093,320 B2 Freitag Et Al

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(12) United States Patent (10) Patent No.: US 8,093,320 B2 Freitag Et Al USOO8093320B2 (12) United States Patent (10) Patent No.: US 8,093,320 B2 Freitag et al. (45) Date of Patent: *Jan. 10, 2012 (54) COMPOSITIONS COMPRISING 3,442,854 A 5, 1969 Curtius et al. POLYPHOSPHONATES AND ADDITIVES 3,719,727 A 3, 1973 Masai et al. 3,829,405 A 8, 1974 Cohen et al. THAT EXHIBITAN ADVANTAGEOUS 3,830,771 A 8, 1974 Cohen et al. COMBINATION OF PROPERTIES, AND 3,919,363 A 11/1975 Ura et al. METHODS RELATED THERETO 3,925.303 A 12/1975 Rio et al. 3,932,351 A 1/1976 King 3,932,566 A 1/1976 Reader (75) Inventors: Dieter Freitag, Chelmsford, MA (US); 3,946,093 A 3, 1976 Koto et al. Pin Go, Lowell, MA (US); Gad Stahl, 3,952,072 A 4, 1976 Yonemitsu et al. Kibbutz Kfar-Aza (IL) 4,033,927 A 7, 1977 Borman 4,048,106 A 9, 1977 Hermans 73) AssigSS19. FRX PolyOlymers, Inc., UnelmChelmsford, SIOrd, MA 4,064,107 A 12/1977 Stackman et al. 4,078,016 A 3, 1978 Kramer (US) 4,093,582 A 6, 1978 Market al. 4,152,373 A 5/1979 Honig et al. *) NotOt1Ce: Subjubject to anyy d1Sclaimer,disclai theh term off thisthi 4,223,104 A 9, 1980 Kim et al. patent is extended or adjusted under 35 4,229,552 A 10, 1980 Shiozaki et al. U.S.C. 154(b) by 0 days. 4,254,177 A 3, 1981 Fulmer 4,258,153 A 3/1981 Yomamoto et al. This patent is Subject to a terminal dis 4,322.520 A 3, 1982 Schmidt et al. claimer. 4.322,530 A 3/1982 Jachimowicz 4.328,174 A 5, 1982 Schmidt et al. 4.331,614 A 5, 1982 Schmidt et al. (21) Appl. No.: 12/699,376 4.332.921 A 6, 1982 Schmidt et al. 4,350,793 A 9, 1982 Schmidt et al. (22) Filed: Feb. 3, 2010 4,374,971 A 2f1983 Schmidt et al. 4,377,537 A 3, 1983 Blocket al. (65) Prior Publication Data 4,401,802 A 8, 1983 Schmidt et al. 4,408,033. A 10/1983 Hefner, Jr. US 2010/0204354 A1 Aug. 12, 2010 4.415,719 A 11/1983 Schmidt et al. Related U.S. Application Data (Continued) (63) Continuation of application No. 1 1/549,789, filed on FOREIGN PATENT DOCUMENTS Oct. 16, 2006, now Pat. No. 7,666,932. EP OOTT493 B1 3, 1987 (60) Provisional application No. 60/727,466, filed on Oct. (Continued) 17, 2005. OTHER PUBLICATIONS (51) Int. Cl. C08G 8/77 (2006.01) Billmeyer, Textbook of Polymer Science, 2" Ed., Wiley Interscience, CSK 3/34 (2006.01) New York (1971), 45-52. CSK 5/5 (2006.01) Cotter, Engineering Plastics: A Handbook of Polyarylethers, Science CSK5/00 (2006.01) Publ. S.A., Switzerland (1995), TOC (Gordon and Breach Publish ers). CSK 5/3 (2006.01) Groggins, Unit Processes in Organic Synthesis, 4" Ed., McGraw-Hill C07F 9/6574 (2006.01) Book Company, Inc. (1952), 616-620. C07F 9/40 (2006.01) C07C37/20 (2006.01) (Continued) CSF II/00 (2006.01) CSF I4/00 (2006.01) A6DF 3/5 (2006.01) Primary Examiner — Timothy J. Kugel (52) U.S. Cl. ........ 524/115:524/101:524/110:524/117; Assistant Examiner — Atnaf Admasu 524/131:524/291; 524/343; 524/344; 524/349; (74) Attorney, Agent, or Firm — Pepper Hamilton LLP 521/143:521/146; 521/149; 521/282; 521/155 (58) Field of Classification Search .................. 521/143, (57) ABSTRACT 521/146, 149, 155, 182: 524/101, 110, 115, 524/117, 131, 291, 343, 344, 349 Disclosed are new compositions consisting of polyphospho See application file for complete search history. nates and specific additive compositions that exhibit Superior resistance to degradation due to exposure to air, high tem (56) References Cited perature and air, moisture or combinations thereof. Also dis closed are polymer mixtures or blends comprising these poly U.S. PATENT DOCUMENTS phosphonates/additive compositions and commodity and 2,534,242 A 12/1940 Cusie engineering plastics and articles produced therefrom. Further 2.435.252 A 2/1948 Toy disclosed are articles of manufacture produced from these 2,682,522 A 6, 1954 Coover et al. 2,716, 101 A 8, 1955 Coover et al. materials, such as fibers, films, coated Substrates, moldings, 2,891,915 A 6, 1959 McCormacket al. foams, fiber-reinforced articles, or any combination thereof. 3,153,008 A 10, 1964 Fox 3,271,329 A 9, 1966 Coover, Jr. et al. 3,326,852 A 6, 1967 Thomas et al. 15 Claims, No Drawings US 8,093,320 B2 Page 2 U.S. PATENT DOCUMENTS 2005.0020800 A1 1/2005 Levchik et al. 2005/0222370 A1 10/2005 Freitaget al. 4.474,937 10, 1984 Bales 2006, OO2O104 A1 1/2006 Freitag 4,481,350 11, 1984 Schmidt et al. 4,508,890 4, 1985 Schmidt et al. FOREIGN PATENT DOCUMENTS 4,594.404 6, 1986 Kawakami et al. 4,719,279 1, 1988 Kauth et al. EP O 383 978 * 8/1990 4,762.905 8, 1988 Schmidt et al. EP 1026,191 A1 8, 2000 4,782,123 11, 1988 Kauth et al. GB 2043083. A 10, 1980 4,788,259 11, 1988 Nielinger et al. WO WO99/46315 9, 1999 5,003,029 3, 1991 Ueda et al. WO WOO3,O29258 A1 4/2003 5,034,056 7, 1991 Von Bonin WO WO2004/076536 A1 9, 2004 5,039,775 8, 1991 Oyaizu WO WO2004/076537 A1 9, 2004 5,086,153 2, 1992 Oyaizu 5,216,113 6, 1993 Schulz-Schlitte et al. OTHER PUBLICATIONS 5,256,714 10, 1993 Liu et al. 5,319,058 6, 1994 Hattori et al. Legrand, et al., Handbook of Polycarbonate Science and Technol 5,334,692 8, 1994 Hess et al. ogy, Marcel Dekker, Inc., New York (2000), TOC. 5,334,694 8, 1994 Jung et al. Levchik, et al., Overview of recent developments in the flame 5,362.783 11, 1994 Eiffler et al. retardancy of polycarbonates, Polym Int (Mar. 22, 1995), 54:981 5,525,681 6, 1996 Barron et al. 998. 5,639,800 6, 1997 Von Bonin et al. 5,719,200 2, 1998 Staendeke et al. Morgan, Condensation Polymers: By Interfacial and Solution Meth 5,919,844 7, 1999 Shimizu et al. ods, Interscience Publishers, New York, (1965), 217-223. 6,066,700 5, 2000 König et al. Schmidt, et al., Aromatische Polyphosphonate: Thermoplastisehe 6,288,210 9, 2001 Shobha et al. Polymere von extremer Brandwidrigkeit, Die Angewadte 6,291,630 9, 2001 König et al. Makromolekulare Chemie (1985) 132(Nr. 165): 1-18. 6,861,499 3, 2005 Vinciguerra et al. Polymeric Materials Encyclopedia, vol. 1, Editor-in-Chief Joseph C. 6,872,797 3, 2005 Ueno et al. Salamone, pp. 316-320, by CRC Press, 1996. 7,666,932 2, 2010 Freitaget al. 2004O167284 8, 2004 Vinciguerra et al. * cited by examiner US 8,093,320 B2 1. 2 COMPOSITIONS COMPRISING Successful in producing high molecular weight polyphospho POLYPHOSPHONATES AND ADDITIVES nates that exhibited improved toughness, but processability THAT EXHIBITAN ADVANTAGEOUS was sacrificed. Another disadvantage for this process is that it COMBINATION OF PROPERTIES, AND requires high purity monomers, preferably greater than METHODS RELATED THERETO 99.7% (see e.g., U.S. Pat. No. 4.331,614) that make it expen sive. Another shortcoming of both the linear and branched RELATED APPLICATIONS polyphosphonates was the lack of hydrolytic stability and haze. This application is a continuation of U.S. patent applica Recently, the development of a method to produce tion Ser. No. 1 1/549,789, filed Oct. 16, 2006, now U.S. Pat. 10 branched polyphosphonates with a Superior combination of No. 7,666,932, issued Feb. 23, 2010, which claims priority to properties was disclosed (“Branched Polyphosphonates that U.S. Provisional Application No. 60/727,466 filed Oct. 17, Exhibit an Advantageous Combination of Properties, and 2005 titled “COMPOSITIONS COMPRISING POLY PHOSPHONATES AND ADDITIVES THAT EXHIBITAN Methods Related Thereto'. 2004 0167284 A1, published 15 Aug. 26, 2004, Ser. No. 10/374,829, filing date Feb. 24, ADVANTAGEOUS COMBINATION OF PROPERTIES, 2003). In practice, these materials are stable for more than 5 AND METHODS RELATED THERETO, the contents of hours at 300° C. under vacuum (<0.5 mm Hg) but can expe which are incorporated hereby by reference. rience degradation upon exposure to high temperature (>250 TECHNICAL FIELD C.) and air, air (oxygen), moisture or combinations thereof. The polyphosphonates are exposed to Such conditions not The present invention relates generally to new composi during the final stages of synthesis, but when melt mixing tions consisting of polyphosphonates and specific additive with other polymers or during molding processes. The deg compositions that exhibit Superior resistance to degradation radation is manifested by reduction in molecular weight that due to exposure to air, high temperature and air, moisture or in turn causes loss of mechanical properties such as strength, combinations thereof. It also relates to polymer mixtures or 25 modulus and toughness. In addition, the fire resistance is blends comprising these polyphosphonates/additive compo negatively affected by this reduction in molecular weight. As sitions, and flame retardant coatings and articles produced the molecular weight decreases, the melt flow of the material therefrom. increases so that in a flame, the material propensity to drip increases significantly. Thus, additives that can prevent any BACKGROUND 30 unwanted degradation of polyphosphonates during thermal treatment are needed. The production of linear, aromatic polyphosphonates by A list of patents on both linear and branched polyphospho condensing aryl phosphonic acid dichlorides and aromatic nates is provided below.
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