US009102549B2 (12) United States Patent (10) Patent No.: US 9,102,549 B2 Alper (45) Date of Patent: Aug. 11, 2015 (54) PROCESS FOR PRODUCING (56) References Cited COMPOSITIONS FOR USE IN REMOVAL OF DISPERSED, SOLUBILIZED AND/OR U.S. PATENT DOCUMENTS EMULSIFIED UNDESRED SPECIES FROM 2,160,532 A 5, 1939 Barrett et al. WATER AND GASES 2,418,920 A 4/1947 Berger et al. 2,441,068 A 5, 1948 Hewitt et al. (75) Inventor: Hal Alper, Flowery Branch, GA (US) 3,067,154 A 12/1962 Sterling 3,755.448 A 8, 1973 Merianos et al. (73) Assignee: MYCELXTECHNOLOGIES (Continued) CORPORATION, Duluth, GA (US) FOREIGN PATENT DOCUMENTS (*) Notice: Subject to any disclaimer, the term of this patent is extended or adjusted under 35 BE 859836 2, 1978 U.S.C. 154(b) by 417 days. WO 99.48584 A1 9, 1999 (Continued) (21) Appl. No.: 13/494,410 OTHER PUBLICATIONS (22) Filed: Jun. 12, 2012 D. Swern, ed. Bailey's Industrial Oil and Fat Products vol. 1. Fourth (65) Prior Publication Data Edition (1979), pp. 687-816. US 2012/O316251A1 Dec. 13, 2012 (Continued) Related U.S. Application Data (60) Provisional application No. 61/520,646, filed on Jun. Primary Examiner — Vu A Nguyen 13, 2011. (74) Attorney, Agent, or Firm — Sutherland Asbill & Brennan LLP (51) Int. C. C09K3/00 (2006.01) CO2F I/28 (2006.01) (57) ABSTRACT AOIN 25/34 (2006.01) Disclosed is a method of making coagulant and viscoelastic AOIN 6L/00 (2006.01) compositions for use in removal of dispersed, solubilized, and C09D 5/14 (2006.01) emulsified oils and hydrocarbons and other noxious species C09D 9/00 (2006.01) from water and air. The composition comprises thermal reac CSF242/00 (2006.01) tion products of blends of fatty acids derived, isolated and CO2F I/OO (2006.01) purified from drying and semi-drying oils such as linseed, (52) U.S. C. safflower, and tung oil with a polymer Such as for example CPC ................ C02F I/285 (2013.01); A0IN 25/34 poly(isobutyl methacrylate) and can include a solvent. The (2013.01); A0IN 61/00 (2013.01); C08F product of the invention facilitates cohesion of oils and hydro 242/00 (2013.01); C09D 5/14 (2013.01); C09D carbons independent of agitation and temperature and may be 191/005 (2013.01); C02F I/001 (2013.01); used in both salt and fresh water, air and other gaseous C08L 2205/02 (2013.01) StreamS. (58) Field of Classification Search None See application file for complete search history. 10 Claims, 8 Drawing Sheets OCFAB = IBMAPOLYMERITATION TEMPERATURETRANSTION 2. 380 350 200 isP 250 200 150 OO 50 O O 50 OO 150 MINUTES US 9,102,549 B2 Page 2 (56) References Cited 5,919,944 A 7, 1999 Eldin 5,961,823. A 10/1999 Alper U.S. PATENT DOCUMENTS 6,001,244. A 12/1999 Salter et al. 6,168,714 B1 1/2001 Ilias et al. 3,776,864 A 12/1973 Woerner 6,180,010 B1 1/2001 Alper 3,821, 109 A 6/1974 Gilchrist et al. 6,337,016 B1 1/2002 Alper 3,835,049 A 9/1974 King 6,475,393 B2 11/2002 Alper 3,917,528 A 1 1/1975 Orban et al. 6,491,822 B2 12/2002 Alper 3,977,969 A 8, 1976 Zall 6,623,513 B2 9, 2003 Biel 4,156,040 A 5, 1979 Swider et al. 6,805,727 B2 10/2004 Alper 4,200,561 A 4/1980 Chang 6,883,321 B2 4/2005 Fornof 4,313,830 A 2f1982 Tulin et al. 7,264,721 B2 9/2007 Alper 4,316,730 A 2, 1982 Elbl 7,264,722 B2 9/2007 Alper 4.420,400 A 12/1983 Weitzen 7,449,119 B2 11/2008 Brown 4.420,573 A 12/1983 Fogg et al. 8, 187.459 B2 5/2012 Alper 4,502,975 A 3/1985 Kobayashi et al. 2001/0042720 A1 1 1/2001 Alper 4,519,918 A 5, 1985 Ericsson et al. 2007/0023357 Al 2, 2007 Brown 4,786,717 A 11, 1988 Bretches et al. 2010/0249267 A1 9/2010 Jiang et al. 4,810,395 A 3/1989 Levy et al. 4,964,987 A 10, 1990 Johnson FOREIGN PATENT DOCUMENTS 5,122.270 A 6/1992 Ruger et al. 5,213,689 A 5, 1993 Kafchinski et al. WO 2009/061462 A1 5.2009 5,259,952 A 1 1/1993 Lee WO 2010/089598 A1 8, 2010 5,326,394 A 7, 1994 Cobb 5,382.371 A 1/1995 Stahl et al. OTHER PUBLICATIONS 5,405,932 A 4/1995 Bender et al. 5,427,612 A 6, 1995 Bender D. Swern, ed. Bailey's Industrial Oil and Fat Products vol. 1. Fourth 5,429,741 A 7, 1995 Webb et al. Edition (1979), pp. 687-747. 5,527.4665,437.793 A 8/19956, 1996 LiAlper et al. Internationalca Iona SearchCaC Reporteport anand Writtenritten UpinionOpinion forIor PCT/US2012/ 5,698,139 A 12/1997 Alper 042030 mailed Sep. 11, 2012. 5,746,925 A 5/1998 Alper International Search Report and Written Opinion for PCT/US2012/ 5,837,146 A 1 1/1998 Alper 042031 mailed Sep. 20, 2012. U.S. Patent Aug. 11, 2015 Sheet 1 of 8 US 9,102,549 B2 LOCFAB = IBMA POLYMERIZATION TEMPERATURETRANSITION 450 -380 OO MINUTES FIG. U.S. Patent Aug. 11, 2015 Sheet 2 of 8 US 9,102,549 B2 -0.24 0+ IBMA -0.26 S-028 s 0.2828J/g 5-0.30- FIRSIHEATRT-185°CATIOC/MIN ISOTHEMALAT 85°CFOR 5 MIN 185°C-60CATIOC/MIN 0.32 60ISOTHEMAAIGOCEORSMIN (-185°CATIOC/MIN logic INNITROGEN -0.34 20 40 60 80 100 120 40 160 180 TEMPERATURE (C) FIG2 U.S. Patent Aug. 11, 2015 Sheet 3 of 8 US 9,102,549 B2 -0.12 -0.14 FIRSTHEAT RT-185°CATIOC/MIN 13.6°C ISOTHEMALAT 85CFOR 5 MIN 124.30C 0.4886J/g -0.18- 185°C.60 (ATOC/MIN ISOTHEMALAT 60'CFOR 5 MIN 60°C-185°CAT IOC/MIN INNITROGEN -0.20 20 40 60 80 OO 120 40 60 180 TEMPERATURE (C) FIG 3 U.S. Patent Aug. 11, 2015 Sheet 4 of 8 US 9,102,549 B2 -0.4 TO + IBMA -0.6 s S-0.18 81.20 °C as 0.07632J/g s 80.2OC 5 FIRSIHEAT 85.98°C 83r RT-185°CAT 10°C/MIN ISOTHEMALAT 85°CFOR5 MIN 0.22-185°C- 60°CATIOC/MIN ISOTHEMALAT 60'CFOR 5 MIN 60'(-185°CATIOC/MIN INNITROGEN -0.24 20 40 60 80 100 120 40 60 180 TEMPERATURE (C) FIG.4 U.S. Patent Aug. 11, 2015 Sheet 5 of 8 US 9,102,549 B2 -0.24 -0.26 LOCFAB+ IBMA 0.28 s asS. 0.30 68.70°C 5 -0.32 77.8°C FIRSTHEAT 7.14°C -0.34 RT. 185°CATIOC/MIN '' ISOTHEMALAT 85°CFOR 5 MIN 185°C. 60°CATIOC/MIN -036- ISOTHEMALAT 60°CFOR5MIN 60°C. 185°CATIOC/MIN INNITROGEN -0.38 20 40 60 80 100 20 40 160 180 TEMPERATURE (C) FIG5 U.S. Patent Aug. 11, 2015 Sheet 6 of 8 US 9,102,549 B2 -0.24 SCOFAB+ IBMA -0.26 S-0.28 as 5-0.30 FIRSTHEAT RT-185°CATIOC/MIN ISOTHEMALAT 85CFOR 5 MIN -0.32–185°C- 60°CATIO'C/MIN ISOTHEMALAT 60'CFOR 5 MIN 60 (-185°CATIOC/MIN INNITROGEN -0.34 -40 -20 O 20 40 60 80 O 20 TEMPERATURE (C) FIG.6 U.S. Patent Aug. 11, 2015 Sheet 7 of 8 US 9,102,549 B2 -0.25 105.90 ( 0.9831 J/g 119.34°C -0.30 O5.40°C S s -0.35 5 FIRST HEAT RT-185°CATIOC/MIN 106.050 ISOTHEMALAT 85°CFOR 5 MIN -0.40 185°C-60CATO'C/MIN ISOTHEMALAT 60'CFOR 5 MIN TOCFAB+ IBMA 60 (-185°CATIOC/MIN INNITROGEN -0.45 20 40 60 80 100 120 40 160 180 TEMPERATURE (C) FIG.7 U.S. Patent US 9,102,549 B2 US 9,102,549 B2 1. 2 PROCESS FOR PRODUCING tion was a commercially available drying oil (comprised of COMPOSITIONS FOR USE IN REMOVAL OF poly-unsaturated glyceride esters of fatty acids containing DISPERSED, SOLUBILIZED AND/OR one or more double bonds, in which at least two of the fatty EMULSIFIED UNDESRED SPECIES FROM acids contain conjugated double bonds). These glycerides, WATER AND GASES Such as linseed oil or tung oil, may be derived from animal or Vegetable sources. The polymer component can be derived CROSS-REFERENCE TO RELATED from alpha and beta unsaturated carbonyl compounds. APPLICATIONS SUMMARY OF INVENTION This application claims priority from U.S. provisional 10 patent application Ser. No. 61/520,646, filed on Jun. 13, 2011, Now in accordance with the present invention, a method which is incorporated herein by reference in its entirety. has been found for producing a new and unexpectedly improved composition for use in removal of dispersed, solu FIELD OF INVENTION bilized, and emulsified oils, hydrocarbons, microbes, endot 15 oxins, triglycerides, and cholesterol, from water, and from air This invention relates to a composition and method for and other benign gases. The thermal reaction producing the producing same, the composition being for use in removal of PAACs, as is indicated above, have in most cases employed as dispersed, solubilized, and/or emulsified oils, hydrocarbons, the first reactant the aforementioned fatty acid esters, i.e.