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(12) United States Patent (10) Patent No.: US 8,895,679 B2 Havinka (45) Date of Patent: *Nov

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(12) United States Patent (10) Patent No.: US 8,895,679 B2 Havinka (45) Date of Patent: *Nov US008895679B2 (12) United States Patent (10) Patent No.: US 8,895,679 B2 Havinka (45) Date of Patent: *Nov. 25, 2014 (54) CATALYST COMPOSITIONS AND METHODS (Continued) OF MAKING AND USING SAME (71) Applicant: Chevron Phillips Chemical Company Primary Examiner — Rip A Lee LP, The Woodlands, TX (US) (74) Attorney, Agent, or Firm — Conley Rose, P.C.; Rodney (72) Inventor: Mark L. Hlavinka, Bartlesville, OK B. Carroll; Cheryl L. Huseman (US) (57) ABSTRACT (73) Assignee: Chevron Phillips Chemical Company LP, The Woodlands, TX (US) An imine phenol compound having Structure I: (*) Notice: Subject to any disclaimer, the term of this patent is extended or adjusted under 35 U.S.C. 154(b) by 77 days. Structure I This patent is Subject to a terminal dis claimer. (21) Appl. No.: 13/660,857 (22) Filed: Oct. 25, 2012 (65) Prior Publication Data R3 US 2014/O121343 A1 May 1, 2014 wherein O and N represent oxygen and nitrogen respectively; (51) Int. Cl. R comprises a halogen, a hydrocarbyl group, or a Substituted C08F 4/64 (2006.01) hydrocarbyl group; R and R can each independently be CSF 4/52 (2006.01) hydrogen, a halogen, a hydrocarbyl group, or a substituted so G'gif7 (2006.01) hydrocarbyl group; and Q is a donor group. A method com USPC ........... 526/161; 526/172; 526/160; 526/126; prising contacting a catalyst composition with a monomer 526/127; 526/129; 526/130; 556/51; 502/103; under conditions suitable for the formation of a polymer 502/104: 502/118: 502/119; 502/120 wherein the catalyst composition comprises a metal Saltcom (58) Field of Classification Search plex of an imine (bis)phenolate compound, a solid oxide, and USPC .............. 556/51; 526/172, 161; 502/103, 104 an optional metal alkyl and wherein the metal salt complex of See application file for complete search history. an imine (bis)phenolate compound has Structure XIV (56) References Cited Structure XIV U.S. PATENT DOCUMENTS OEt Bu Cln Y-Cl R 3,161,629 A 12/1964 Gorsich M 3,242,099 A 3/1966 Manyik et al. O1ANO (Continued) N FOREIGN PATENT DOCUMENTS N R2 CN 1030.121.96 4/2013 CN 103.01.2196. A 4/2013 where M is titanium, zirconium, or hafnium; OE is ethoxide, R comprises a halogen, a hydrocarbyl group, or a Substituted (Continued) hydrocarbyl group; and R comprises hydrogen, a halogen, a OTHER PUBLICATIONS hydrocarbyl group, or a substituted hydrocarbyl group. Maurya et al. Dalton Trans., 2006, 3561-3575.* 23 Claims, 7 Drawing Sheets US 8,895,679 B2 Page 2 (56) References Cited 5,587,501 12, 1996 Winter et al. 5,594,078 1/1997 Welch et al. U.S. PATENT DOCUMENTS 5,594,080 1/1997 Waymouth et al. 5,612,271 3, 1997 Zandona 3.248,179 4, 1966 Norwood 5,631,203 5, 1997 Welch et al. 3,533.738 10, 1970 Rundell et al. 5,631,335 5, 1997 Alt et al. 3,946,020 3, 1976 Minato et al. 5,643,847 7/1997 Walzer, Jr. 4,060,480 11, 1977 Reed et al. 5,646,322 7/1997 van Beek et al. 4,070,272 1, 1978 Rausch 5,648.439 7/1997 Bergmeister et al. 4,077,904 3, 1978 Noshay et al. 5,654.454 8, 1997 Peifer et al. 4,101,445 7, 1978 Levine et al. 5,668,230 9, 1997 Schertlet al. 4,279,780 T. 1981 Dombro 5,670,580 9, 1997 Tazaki et al. 4,452,910 6, 1984 Hopkins et al. 5,700,748 12, 1997 Murray 4476,243 10, 1984 Dombro 5,703, 181 12, 1997 Tashiro et al. 4,501.885 2, 1985 Sherk et al. 5,705,578 1, 1998 Peifer et al. 4,526,942 7, 1985 Chester et al. 5,705,579 1, 1998 Hawley et al. 4,547,551 10, 1985 Bailey et al. 5,714.425 2, 1998 Chabrand et al. 4,588,790 5, 1986 Jenkins, III et al. 5,714,555 2, 1998 Chabrand et al. 4,596,862 6, 1986 McDaniel et al. 5,719,241 2, 1998 Razavi et al. 4,657,998 4, 1987 Malpass 5,726.264 3, 1998 Jung et al. 4,659,685 4, 1987 Coleman, III et al. 5,739,220 4, 1998 Shamshoum et al. 4,788,171 11, 1988 Klendworth 5,780,659 7, 1998 Schmid et al. 4,794,096 12, 1988 Ewen 5,807,938 9, 1998 Kaneko et al. 4,803.253 2, 1989 McDaniel et al. 5,854,165 12, 1998 Yabunouchi et al. 4,806,513 2, 1989 McDaniel et al. 5,854,363 12, 1998 Jung et al. 4,808,561 2, 1989 Welborne, Jr. 5,861,352 1/1999 Gila et al. 4,892,851 1, 1990 Ewen et al. 5,866,497 2, 1999 Murray 4,939,217 7, 1990 Stricklen 5,883,036 3, 1999 Fujie et al. 4.969,522 11, 1990 Whitehurst et al. 5,886,202 3, 1999 Jung et al. 5,001.204 3, 1991 Klendworth et al. 5,906,955 5, 1999 Hamura et al. 5,010, 152 4, 1991 McDaniel et al. 5,907,021 5, 1999 Turner et al. 5,036,034 7, 1991 Ewen 5,919,983 7, 1999 Rosen et al. 5,037,911 8, 1991 McDaniel et al. 5,942.459 8, 1999 Sugano et al. 5,049,535 9, 1991 Resconi et al. 6,034,187 3, 2000 Maehama et al. 5,071,808 12, 1991 Antberg et al. 6,096,677 8, 2000 Wilson, Jr. 5,075.467 12, 1991 Desobry 6,107,230 8, 2000 McDaniel et al. 5,085,705 2, 1992 Withiam 6,114,477 9, 2000 Merrill et al. 5,162,278 11, 1992 Razavi 6,150,544 11, 2000 Seki et al. 5,171,798 12, 1992 McDaniel et al. 6,165,929 12, 2000 McDaniel et al. 5, 183,868 2, 1993 Nordquest 6,169,151 1, 2001 Waymouth et al. 5, 191,132 3, 1993 Patsidis et al. 6,174.981 1, 2001 Bergmeister et al. 5,210,352 5, 1993 Alt et al. 6,180,736 1, 2001 Muhle et al. 5,223,467 6, 1993 Razavi 6,187,880 2, 2001 Welch et al. 5,321, 105 6, 1994 Rekers et al. 6,201.077 3, 2001 Begmeister et al. 5,332,707 T. 1994 Karayannis et al. 6,204,346 3, 2001 Bergmeister et al. 5,347,026 9, 1994 Patsidis et al. 6,225.425 5/2001 Dolle et al. 5,352,749 10, 1994 DeChellis et al. 6,239,059 5/2001 Saudemont et al. 5,369,196 11, 1994 Matsumoto et al. 6,239,235 5/2001 Hottovy et al. 5,376,611 12, 1994 Shveima 6,262,191 T/2001 Hottovy et al. 5,399,636 3, 1995 Alt et al. 6,262,201 T/2001 Welch et al. 5,401,817 3, 1995 Palackal et al. 6,268.447 T/2001 Murray et al. 5,401,820 3, 1995 McDaniel et al. 6,274,684 8, 2001 Loveday et al. 5,416.228 5, 1995 Ewen et al. 6,291,699 9, 2001 Birmingham et al. 5,420,320 5, 1995 Zenk et al. 6,294,494 9, 2001 McDaniel et al. 5.434,116 7, 1995 Sone et al. 6,300,271 10, 2001 McDaniel et al. 5,436,304 7, 1995 Griffin et al. 6,300.451 10, 2001 Mehta et al. 5,436,305 7, 1995 Alt et al. 6,316,553 11, 2001 McDaniel et al. 5.439,995 8, 1995 Bailly et al. 6,333,389 12, 2001 Whiteker et al. 526, 161 5,444,134 8, 1995 Matsumoto 6,340,651 1, 2002 Licht et al. 5,451,649 9, 1995 Zenk et al. 6,340,652 1, 2002 Sugano et al. 5,455,314 10, 1995 Burns et al. 6,355,594 3, 2002 McDaniel et al. 5,461,127 10, 1995 Naganuma et al. 6,376,415 4, 2002 McDaniel et al. 5,468,702 11, 1995 Jejelowo 6,388,017 5/2002 McDaniel et al. 5483,014 1, 1996 Turner et al. 6,391,816 5/2002 McDaniel et al. 5,496,781 3, 1996 Geerts et al. 6,395,666 5/2002 McDaniel et al. 5,496,782 3, 1996 Zandona 6,462, 161 10, 2002 Cady et al. 5,498,581 3, 1996 Welch et al. 6,469,188 10, 2002 Miller et al. 5,527,867 6, 1996 Bergmeister 6,482.905 11, 2002 Schmidt et al. 5,534.473 T. 1996 Welch et al. 6,489,263 12, 2002 Murray et al. 5,541,272 T. 1996 Schmid et al. 6,509,427 1, 2003 Welch et al. 5,543,376 8, 1996 Bergmeister 6,515,086 2, 2003 Razavi 5,554,795 9, 1996 Frey et al. 6,524,987 2, 2003 Collins et al. 5,556,893 9, 1996 Costa et al. 6,531,565 3, 2003 Kellum et al. 5,563,284 10, 1996 Frey et al. 6,541,413 4/2003 Razavi et al. 5,565, 175 10, 1996 Hottovy et al. 6,548,441 4/2003 McDaniel et al. 5,565,592 10, 1996 Patsidis et al. 6,548.442 4/2003 McDaniel et al. 5,571,880 11, 1996 Alt et al. 6,573,344 6, 2003 Hawley et al. 5,575,979 11, 1996 Hanson 6,576.583 6, 2003 McDaniel et al.
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