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(12) United States Patent (10) Patent No.: US 9,109,080 B2 Drake Et Al

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(12) United States Patent (10) Patent No.: US 9,109,080 B2 Drake Et Al US009 109080B2 (12) United States Patent (10) Patent No.: US 9,109,080 B2 Drake et al. (45) Date of Patent: *Aug. 18, 2015 (54) CROSS-LINKED ORGANIC POLYMER FOREIGN PATENT DOCUMENTS COMPOSITIONS AND METHODS FOR CONTROLLING CROSS-LINKING EP O251357 B1 1, 1988 REACTION RATE AND OF MODIFYING GB 2185114 7, 1987 SAME TO ENHANCE PROCESSABILITY (Continued) (71) Applicant: Delsper LP, Kulpsville, PA (US) OTHER PUBLICATIONS (72) Inventors: Kerry A. Drake, Red Hill, PA (US); Andrew F. Nordquist, Whitehall, PA Ladacki et al., “Studies of the Variations in Bond Dissociation Ener (US); Sudipto Das, Norristown, PA gies of Aromatic Compounds. I. Mono-bromo-aryles.” Proc. R. Soc. (US); William F. Burgoyne, Jr., Lond. a, r219, pp. 341-253 (1953). Bethlehem, PA (US); Le Song, Chalfont, (Continued) PA (US); Shawn P. Williams, North Wales, PA (US); Rodger K. Boland, Primary Examiner — Robert S. Loewe Levittown, PA (US) (74) Attorney, Agent, or Firm — Flaster/Greenberg P.C. (73) Assignee: Delsper LP, Kulpsville, PA (US) (*) Notice: Subject to any disclaimer, the term of this (57) ABSTRACT patent is extended or adjusted under 35 The invention includes a cross-linking composition compris U.S.C. 154(b) by 0 days. ing a cross-linking compound and a cross-linking reaction additive selected from an organic acid and/or an acetate com This patent is Subject to a terminal dis pound, wherein the cross-linking compound has the structure claimer. according to formula (IV): (21) Appl. No.: 14/059,064 (22) Filed: Oct. 21, 2013 (IV) (65) Prior Publication Data US 2014/0284.850 A1 Sep. 25, 2014 Related U.S. Application Data (60) Provisional application No. 61/833,351, filed on Jun. ) A. 10, 2013, provisional application No. 61/716,800, filed on Oct. 22, 2012. (51) Int. Cl. () C08G 65/48 (2006.01) C08G 16/00 (2006.01) wherein the cross-linking reaction additive is capable of reacting with the cross-linking compound to form a reactive (Continued) oligomer intermediate, which is capable of cross-linking an (52) U.S. Cl. organic polymer. Also included is an organic polymer com CPC ................ C08G 65/00 (2013.01); C07C35/38 position for use in forming a cross-linked organic polymer, (2013.01); C07C 43/275 (2013.01); C08G comprising a cross-linking compound of Formula (IV), a 65/48 (2013.01); C08L 71/00 (2013.01) cross-linking reaction additive and at least one organic poly (58) Field of Classification Search mer. In one embodiment, the at least one organic polymer has None at least one halogen-containing reactive group and is dehalo See application file for complete search history. genated by reacting with an alkali metal compound. Methods for making Such compositions as well as articles of manufac (56) References Cited ture formed from Such methods and organic polymer compo sitions, wherein the compositions and methods control the U.S. PATENT DOCUMENTS cross-linking reaction rate of a crosslinking compound for 3,092,191 A 6, 1963 Austin et al. use in cross-linking an organic polymer are also included. 3,512,592 A 5, 1970 Kellner (Continued) 65 Claims, 7 Drawing Sheets 5.9 20.3 35.0 30.0, 35.0 fine (min) US 9,109,080 B2 Page 2 (51) Int. Cl. 2002/0195739 A1 12/2002 Bagley et al. C08G 65/00 2003, OO32339 A1 2/2003 Bell et al. (2006.01) 2005, 0161212 A1 7/2005 Leismer et al. C07C35/38 (2006.01) 2006, O19991.0 A1 9, 2006 Walton et al. C07C 43/275 (2006.01) 2007/O142547 A1 6/2007 Vaidya et al. COSL 7L/00 2007,0296.101 A1 12/2007 DiPietro et al. (2006.01) 2010/0022718 A1 1/2010 Tu et al. ........................ 525/471 2010.0081007 A1 4/2010 Zheng et al. (56) References Cited 2010, 0126266 A1 5, 2010 Coenen 2011/O1394.66 A1 6, 2011 Chen et al. U.S. PATENT DOCUMENTS 2011/0260343 A1 10/2011 Burgoyne, Jr. et al. 2012fOO77935 A1 3/2012 Gurevich et al. 3,533,997 A * 10, 1970 Angelo ......................... 525,436 2012fOO971.94 A1 4/2012 Mcdaniel et al. 4,609,714 A 9, 1986 Harris et al. 2012/010O379 A1 4/2012 Luo et al. 4,708,994 A 11, 1987 Wong 2012/0130041 A1* 5, 2012 Han et al. ...................... 528,125 4,710,948 A 12, 1987 Withjack 2012fO252218 A1 10, 2012 Kori et al. 4,731,442 A 3, 1988 Lindley et al. 2013, OO12635 A1 1/2013 Ren et al. 4,827,761 A 5, 1989 Vinegar et al. 2013/0130529 A1* 5/2013 Ayers ............................ 439,271 4,861,810 A 8, 1989 Dewhirst 2014/0213742 A1 7/2014 Drake et al. 5,108,840 A 4, 1992 Mercer 2014/0316079 A1 10/2014 Drake et al. 5,114,780 A 5, 1992 Mercer et al. 5,134,207 A 7, 1992 McGrath et al. FOREIGN PATENT DOCUMENTS 5,145,936 A 9, 1992 Mercer 5,155, 175 A * 10, 1992 Mercer et al. ................. 525/390 5,173,542 A 12, 1992 Lau et al. WO WOOO61667 A1 10, 2000 5,179,188 A 1, 1993 Mercer et al. WO WO 01/16232 A1 3, 2001 5,204,416 A 4, 1993 Mercer et al. WO WO 2009021999 A1 2, 2009 5,235,044 A 8, 1993 Mercer et al. WO WO 2010/O19488 A1 2, 2010 5,270,453 A 12, 1993 Lau et al. WO WO 2011071619 A2 6, 2011 5,658,994 A 8, 1997 Burgoyne, Jr. et al. WO WO 2013074120 A1 5, 2013 5,668.245 A 9, 1997 Marrocco, III et al. OTHER PUBLICATIONS 5,886, 130 A 3, 1999 Trimmer et al. 6,060, 170 A 5, 2000 Burgoyne, Jr. C.-M. Chan et al., “Crosslinking of Poly(arylene ether ketones). II. 6,184,284 B1 2, 2001 Stokich, Jr. et al. Crystallization Kinetics.” J. of Polymer Science: Part B: Polymer 6,339,966 B1 1, 2002 Kalidindi Physics, vol. 25, pp. 1655-1665 (1987). 6,582,251 B1 6, 2003 Burke et al. Hendrick, "Elastomeric behavior of Crosslinked poly(aryl ether 6,716,955 B2 4, 2004 Burgoyne, Jr. ketone)s at elevated temperatures.” Polymer, vol. 22, No. 23, pp. 6,855,774 B2 2, 2005 Kawasaki et al. 5094-5097, (1992). Butterworth-Heinimann Ltd. 6,878,778 B1 4, 2005 Kawasaki et al. Yi-Chi Chien et al., “Fate of Bromine in Pyrolysis of Printed Circuit 6,914,119 B2 7/2005 Yoshida et al. Board Wastes.” ChemoSphere, vol. 40, pp. 383-387 (2000). 7,001,678 B2 2, 2006 Casasabta, III et al. Burke et al., “High Pressure/High Temperature Technology and 7,087,701 B2 8, 2006 Londergan Introduction of LHT a New High Temperature Plastic.” MERL, 26 7,101,957 B2 9, 2006 Huang et al. pages (Sep. 2010). 7,109,249 B2 9, 2006 Bruza et al. Drake, “High Temperature Hybrid Elastomers.” PhD Thesis, (2011). 7,115,531 B2 10, 2006 Shaffer, II et al. 7,189,795 B2 3, 2007 Burgyyne, Jr. et al. International Search Report and Written Opinion for PCT/US 13/ 7,196,155 B2 3, 2007 Chen et al. 65977, mailed Apr. 17, 2014—15 pages. 7,249,971 B2 7/2007 Burke et al. International Search Report and Written Opinion for PCT/US14/ 7,307,137 B2 12/2007 Lau et al. 13246, mailed Apr. 30, 2014—16 pages. 7,589,228 B2 9, 2009 Nishichi et al. International Search Report and Written Opinion for PCT/US14/ 7,696,275 B2 4, 2010 Slay et al. 30666, mailed Aug. 13, 2014—19 pages. 7.919,825 B2 4, 2011 Kretz et al. Written Opinion for PCT/US14/30666, mailed Jan. 30, 2015–3 8,096.353 B2 1, 2012 Ver Meer pageS. 8,367,776 B2 2, 2013 Noguchi et al. 8,502.401 B2 8, 2013 Burgoyne, Jr. et al. * cited by examiner U.S. Patent Aug. 18, 2015 Sheet 1 of 7 US 9,109,080 B2 4.000E3. 3,500E6; 3,55 O-2 Crosslinker Not treated with glacial acetic acid 2.000E5. 15OOES 1.000E5 bio-2 Crosslinker Treated with glacial acetic acid (5.06.050. 20.025,036,035.046,045,656.0 time (min) F.G. 1 U.S. Patent Aug. 18, 2015 Sheet 2 of 7 US 9,109,080 B2 4:5 3,505 3.500 3,500S hio-2 Crossiker Not treated with glacial acetic acid 2.000E5 C. iii.5 .000E5 feates with OA: it cyclohexafore 4 r. fefix Oil-2 . s / treated with CAC in cyclohexandre 6. refix 65,000 15026,025,036,035.046,045,056.0 time (min) FG. 2 Cure Time, 380C, Oligomer Method 4000----------------------------------------------------------------------- 35 3000 2500 c f 2. g 50 OOO al t :enoopooooooooooo. ---------------------------- (.00 2.0 4, 8, 8.O.O. O. 2.OO 14.00 8.00 reactic irre tooooooo fectic Poiri oooooo G', G" Crossover FG. 2A U.S. Patent Aug. 18, 2015 Sheet 3 of 7 US 9,109,080 B2 OCES 3.500E5 3,500E3 3500E8 OOO No lithin acetate hydrate s 2.OOOES adde: & 1.500E5 1.000E5 500 t try're-cirrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrt S. O. 3.O. 23. 35.0 3.0 38.) 40 45. 80.0 time (min) FG. 3 Delay in Cure vs. '%. Additive 1 5 O {} O e p .8% .50% 50%, 2.0% 2.50%, 3.8% 3.50% %. Additive see G', G" Crossoverroio infection; Point FG. 3A U.S. Patent Aug. 18, 2015 Sheet 4 of 7 US 9,109,080 B2 FG. 4A FG.
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