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(12) United States Patent (10) Patent No.: US 7413,813 B2 Gosse Et Al

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(12) United States Patent (10) Patent No.: US 7413,813 B2 Gosse Et Al USOO7413813B2 (12) United States Patent (10) Patent No.: US 7413,813 B2 Gosse et al. (45) Date of Patent: Aug. 19, 2008 (54) PLASTICISED POLYVINYL CHLORIDE 2,489,103 A 1 1/1949 Morris et al. 2,535,643 A 12, 1950 Mack (75) Inventors: Claudius Gosse, Brussels (BE); Thomas 2,759,836 A 8, 1956 Caldwell Marshall Larson, Bellaire, TX (US); 2,794,811 A 6, 1957 Winstrom Pierre Jean Paul Legrand, Brussels 2,828,335 A 3/1958 Ferstandig et al. 2,848,412 A 8/1958 Easley (BE); Raphael Frans Caers, Edegem 2.888.484 A 5/1959 Dehmet al. (BE); Paul H. Daniels, League City, TX 3027.398 A 3/1962 Foohey (US); Allen D. Godwin, Seabrook, TX 3.085.078 A 4, 1963 Fath (US); Didier Naert, Brussels (BE) 3,135,740 A 6/1964 Brannocket al. 3,152,096 A 10/1964 Darby (73) Assignee: ExxonMobil Chemical Patents Inc., 3,169,975 A 2, 1965 Schulz Houston, TX (US) 3.224,994. A 12/1965 Lundberg et al. 3,251,771 A 5, 1966 Benoit (*) Notice: Subject to any disclaimer, the term of this 3,296,180 A 1/1967 Raether patent is extended or adjusted under 35 3,308,086 A 3, 1967 Wartman U.S.C. 154(b) by 0 days. 3,326,972 A 6/1967 Schenk et al. 3,334,149 A 8, 1967 Marlet al. (21) Appl. No.: 11/846,879 3,403,170 A 9, 1968 Corson et al. 3,428,668 A 2, 1969 Huelsmann et al. (22) Filed: Aug. 29, 2007 3,444,237 A 5/1969 Jaffe T864,003 I4 7, 1969 Foster (65) Prior Publication Data 3,520,921 A 7/1970 Appell T883,022 I4 2f1971 Strickland et al. US 2007/O293646A1 Dec. 20, 2007 3,607,917 A 9, 1971 Bulls O O 3,730,931 A 5, 1973 Simoneau et al. Related U.S. Application Data 3,745,179 A 7/1973 Ibing et al. (63) Continuation of application No. 10/490,760, filed as 3,876,671 A 4, 1975 Turner application No. PCT/EP02/10945 on Sep. 25, 2002. 3,892,796 A 7, 1975 Leibfried (30) Foreign Application Priority Data (Continued) Sep. 25, 2001 (GB) - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - O1230184 FOREIGN PATENT DOCUMENTS Sep. 25, 2001 (GB) ... ... O123019.2 Sep. 25, 2001 (GB) ... O123O2O.O CN 1037350 11, 1989 Sep. 25, 2001 (GB) ... O1230218 Sep. 25, 2001 (GB) O123022.6 (Continued) Sep. 25, 2001 (GB) ... O123134.9 Sep. 25, 2001 (GB) ... ... O1232214 OTHER PUBLICATIONS Sep. 25, 2001 (GB) - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - O2O1188.0 J.R. Grace. A.A. Avodam. T.M. Knowlton, “Circulating Fluidized Beds”. Blackie Academic & Professional, p. 336-337. (51) Int. Cl. B32B 27/06 (2006.01) (Continued) (52) U.S. Cl. ........................ 428/518; 524/289; 524/569 Primary Examiner Peter Szekely (58) Field of Classification Search ................. 524/289, (74) Attorney, Agent, or Firm—Andrew B. Griffis 524/569; 428/518, 520, 522; 604/616 See application file for complete search history. (57) ABSTRACT (56) References Cited Esters of cyclohexane polycarboxylic acids are used as plas U.S. PATENT DOCUMENTS ticisers for polyvinyl chloride to enable products with com 1,628, 190 A 5/1927 Rainey parable mechanical properties to be obtained using less poly 1,850,144 A 3, 1932 Stolz et al. vinyl chloride. Use of these esters also produces formulations 1877,991 A 9, 1932 Schwenk et al. with increased stability to ultra-violet light, improved low 1905,516 A 4, 1933 Smith temperature properties, lower viscosity and improved pro 2,005,414 A 6/1935 Dykstra cessability as well as reduced Smoke on burning. The esters of 2,015,239 A 9, 1935 Schrauth cyclohexane polycarboxylic acids may be used alone or in 2,070,770 A 2f1937 Amend admixture with other plasticisers when the esters of cyclo 2,088,633. A 8/1937 Bousquet et al. hexane polycarboxylic acids may act as Viscosity depres 2,101,227 A 12/1937 Werntset al. 2,189,722 A 2f1940 Winans sants. Fast fusing plasticisers may also be included. The for J. V-1 mulations are particularly useful in the production of a range 2,385,531.2,311,259 A 9,2, 19451943 Osterhofetal.Staff et al. of goodsg from semi-rigidrig to highlyy flexibleIlexible materials and are 2.385,532 A 9/1945 Cheyney et al. particularly useful in the production of medical materials 2.385,533 A 9/1945 Cheyney et al. Such as blood bags and tubing. 2.385,534 A 9/1945 Cheyney et al. 2,385,535 A 9/1945 Cheyney et al. 2 Claims, 7 Drawing Sheets US 7413,813 B2 Page 2 U.S. PATENT DOCUMENTS 5,986,154 A 1 1/1999 Mignard et al. 6,022.606 A 2/2000 Nakano 3,926,889 A 12/1975 Duchesneau, Jr. 6,063,846 A 5/2000 Weng et al. 4,004,894 A 1/1977 Nohe et al. 6.255,530 B1 7/2001 Albach et al. 4,027,081 A 5, 1977 Turner 6,284.917 B1 9/2001 Brunner et al. 4,067,915 A 1/1978 Yasuhara et al. 6,291,706 B1 9/2001 Sumner, Jr. et al. 4,113,689 A 9, 1978 Modena et al. 6,326,426 B1 12/2001 Ellul 4.212,990 A 7/1980 Yasuhara et al. 6,388,149 B2 5/2002 Rihl et al. 4,317,760 A 3, 1982 Tsuda et al. 6,432,861 B1 8/2002 Breitscheidel et al. 4,398,019 A 8, 1983 Cox et al. 2002/00 19559 A1 2/2002 Brunner et al. 4.421,885. A 12/1983 Tsuda et al. 4,436,859 A 3, 1984 Stein et al. FOREIGN PATENT DOCUMENTS 4,447,569 A 5, 1984 Brecker et al. 4,464,277 A 8, 1984 Cousineau et al. CN 1067062 12/1992 4,469,590 A 9, 1984 Schucker et al. CN 1072428 5, 1993 4,514,190 A 4, 1985 Cousineau et al. DE 497 629 5, 1930 4,528,396 A 7, 1985 Sanderson et al. DE 513 771 11, 1930 4,539.358 A 9, 1985 Liu DE 855 400 11, 1952 4,562,240 A 12/1985 Goel et al. DE 1254 624 8, 1963 4,578,210 A 3, 1986 Praefcke et al. DE 1233, 870 8, 1964 4,605,490 A 8/1986 Balinsky et al. DE 1263. 296 8, 1964 4,610,779 A 9/1986 Markley et al. DE 1910 911 5, 1969 4,617,325 A 10/1986 Knobel et al. DE 2823 165 5, 1978 4,618,630 A 10/1986 Knobel et al. DE 196.24 485 6, 1996 4,670,013 A 6, 1987 Barnes et al. DE 19756913 6, 1999 4,708,971. A 1 1/1987 Goel et al. DE 19927 979 10, 2000 4,734,522 A 3, 1988 Praefcke et al. DE 2 OO 21356 12/2000 4,754,064 A 6, 1988 Lillwitz DE 19927 977 12/2000 4,758,373 A 7, 1988 Praefcke et al. DE 19927 978 12/2000 4,894,181 A 1/1990 Praefcke et al. DE 20021356 * 3, 2001 4,980,331 A 12/1990 Hoxmier et al. DE 298 24 628 1, 2002 5,030,779 A 7, 1991 Hoxmeier et al. EP 0 005 738 5, 1979 5,047.380 A 9, 1991 Tour et al. EP O O23 363 2, 1981 5,089,463 A 2, 1992 Johnson EP O O13 2.75 7, 1982 5,093,535 A 3, 1992 Harrison et al. EP O O7O 394 1, 1983 5,104,741 A 4, 1992 Greenlee et al. EP O 1278O3 12, 1984 5,118,841 A 6, 1992 Cook et al. EP O 191 138 8, 1986 5,162.380 A 1 1/1992 Hori et al. EP O 220 480 9, 1986 5,171,911. A 12/1992 Tour et al. EP O 212449 3, 1987 5,216,053 A 6, 1993 Jones et al. EP 0 288 723 3, 1988 5,231,125 A 7, 1993 Kitazawa et al. EP O3O3 136 8, 1988 5,232,967 A 8, 1993 Worschechet al. EP O 184382 6, 1989 5,247,019 A 9, 1993 Cozens et al. EP O 358598 9, 1989 5,258.232 A 1 1/1993 Summers et al. EP O 366 089 4f1994 5,264,408 A 1 1/1993 Tour et al. EP O 769 539 9, 1996 5,269,965 A 12/1993 Matsumura et al. EP O 698 073 12/1996 5,286,898 A 2, 1994 Gustafson et al. EP O 814098 6, 1997 5,290,886 A 3, 1994 Elul EP O 703896 4f1998 5,298,542 A 3, 1994 Nakamura et al. EP O 603 825 9, 1998 5,319,028 A 6, 1994 Gustafson et al. EP O926 173 6, 1999 5,319,129 A 6, 1994 Gustafson et al. 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