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. 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