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(12) United States Patent (10) Patent No.: US 7,772,211 B2 Tsai Et Al

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(12) United States Patent (10) Patent No.: US 7,772,211 B2 Tsai Et Al USOO7772211 B2 (12) United States Patent (10) Patent No.: US 7,772,211 B2 Tsai et al. (45) Date of Patent: *Aug. 10, 2010 (54) PRODUCTION OF CARRAGEENAN AND 4,859.484 A 8, 1989 Bielskis et al. CARRAGEENAN PRODUCTS 4,950,752 A 8, 1990 Whitaker 5,089,307 A 2/1992 Ninomiya et al. (75) Inventors: Albert G. Tsai, New Castle, DE (US); 5,275,803 A 1/1994 Dawson Linnea K. S. Ledwith, Rockport, ME 5,275,834 A 1/1994 Thibault et al. (US); Robert Kopesky, Camden, ME 5,342,626 A 8/1994 Winson, Jr. et al. (US); Maurice Gerard Lynch, Waterloo 5,496,936 A 3, 1996 Thami et al. (BE); William Ross Blakemore, 5,502,179 A 3, 1996 Larsen SpyMESS; Peter J. Riley, 5,662,840 A 9/1997 Thomas et al. s 5,756,123 A 5/1998 Yamamoto et al. (73) Assignee: FMC Corporation, Philadelphia, PA 5,777,102 A * 7, 1998 Larsen ....................... 536,124 (US) 5,801,240 A 9, 1998 RideOut et al. 6,042,854 A 3/2000 Morris et al. ( c ) Notice: Subject to any disclaimer, the term of this 6,045,780 A * 4/2000 Bixler et al. .................. 424/49 patent is extended or adjusted under 35 6,063,915 A 5, 2000 Hansen et al. U.S.C. 154(b) by 616 days. 6,146,570 A 1 1/2000 Stern et al. 6,214,376 B1 4/2001 Gennadios This patent is Subject to a terminal dis- 6,268,191 B1 7/2001 Prudhomme et al. claimer. 6,331.205 B1 12/2001 Paris et al. 6,375,981 B1 4/2002 Gilleland et al. (21) Appl. No.: 11/542,936 6,387.354 B1 5/2002 Bixler et al. (22) Filed: Oct. 4, 2006 6.479,649 B1 * 1 1/2002 Tsai et al. .................. 536,111 6,528,088 B1 3/2003 Gilleland et al. (65) Prior Publication Data 6,582,727 B2 6/2003 Tanner et al. 6,635,275 B1 10/2003 Scott et al. US 2007/O112184 A1 May 17, 2007 6,685,978 B1 2/2004 Hauksson ................... 426,573 Related U.S. Application Data 7,018,635 B2* 3/2006 Tsai et al. .............. 424,195.18 (60) Division of application No. 10/450,107, filed as appli cation No. PCT/US01/47020 on Dec. 10, 2001, now Pat. No. 7,189,843, which is a continuation-in-part of (Continued) application No. 09/798.012, filed on Mar. 2, 2001, now Pat. No. 6,479,649. FOREIGN PATENT DOCUMENTS (60) Provisional application No. 60/255.279, filed on Dec. CL 125-96 9, 1996 13, 2000. (51) Int. Cl. A6 IK3I/73 (2006.01) (Continued) C7H I/06 (2006.01) OTHER PUBLICATIONS C7H I/08 (2006.01) (52) U.S. Cl. ...................................... 514/54:536/123.1 Stancioff D. Carrageenans: Versatile Food Ingredients, Foods Food (58) Field of Classification Search ....................... None Ingredients J.Japan, 167, 37-47, 1996. See application file for complete search history. (Continued) (56) References Cited Primary Examiner Eric S Olson U.S. PATENT DOCUMENTS (57) ABSTRACT 2,620,334 A 12/1952 Nielson et al. 2,620,335 A 12/1952 Nielson et al. 2,624,727 A 1/1953 Le Gloahec 3,094,517 A 6/1963 Stanley The methods of the present invention prepare carrageenan 3,176,003 A 3, 1965 Stancioff products from processed seaweed material having a solids 3,280,102 A 10/1966 Gordon et al. content of less than 25% by weight Solids, using shear stress 3,342,612 A 9, 1967 Foster et al. treatment. The carrageenan products comprise at least about 3,849,395 A 1 1/1974 Moirano et al. 60% by weight of carrageenan and at least about 2% by 3.855,149 A 12, 1974 Bielskis weight of acid insoluble material. The carrageenan products 3,901,873. A 8, 1975 Doi et al. of the present invention are useful as components in food 3,907,770 A 9, 1975 Strong products, such as, dairy products, meats, and dessert gels as 4,112,223. A 9, 1978 Lin et al. well as non-food products, such as, toothpaste formulations, 4,443,486 A 4/1984 Guiseley cosmetics, paints, films and delivery capsules 4,765,886 A 8, 1988 Whitaker s s 4,816,278 A 3, 1989 Sasmoto et al. 4,851,394 A 7, 1989 Kudodera 5 Claims, 1 Drawing Sheet US 7,772,211 B2 Page 2 U.S. PATENT DOCUMENTS WO WO90,04333 5, 1990 WO WO94,22921 10, 1994 7,189,843 B2 * 3/2007 Tsai et al. ................... 536,114 WO WO94,22922 10, 1994 2002, 0071861 A1 6, 2002 Blanchin et al. WO WO 98.40412 9, 1998 WO WO99/47249 9, 1999 FOREIGN PATENT DOCUMENTS WO WOOOO6609 2, 2000 EP 0432835 * 6/1991 WO WOOOf 10538 3, 2000 EP O 598 141 A1 5, 1994 WO WOO1,03677 1, 2001 EP O 812545. A 12/1997 WO WOO1? 66O73 A2 9, 2001 EP O812545 * 12/1997 JP 11252 8, 1958 OTHER PUBLICATIONS JP S48-0912S6 11, 1973 DeRuiter G. Carrageenan Biotechnology, Trends in Food Science & JP 55-12234 3, 1980 Tech 8(12)389-395, Dec. 1997. JP S55-12234 3, 1980 Prakash, J., “Proceedings of the Regional Workshop on Seaweed JP S57-2O875 12/1982 Culture and Marketing.” South Pacific Aquaculture Development JP S59-1795O2 10, 1984 Project, Adams, T., et al. (Eds.), Nov. 14-17, 1989, 1-86. JP S60-055O39 3, 1985 Stanley, N., "Chapter 3: Production, properties and uses of car JP 61254.146 11, 1986 rageenan.' Food and Agriculture Organization of the United Nations, JP S62-29.947 2, 1987 FAO Fisheries Technical Paper No. 288, McHugh, D.J. (Ed.), 1987, JP S62-186754 8, 1987 116-146. JP S63-164858 T 1988 Meiji, et al., “Treating seaweed to enable utilisation of components - JP S63-216442 9, 1988 by crushing, adjusting water content and extruding.” Derwent Pub JP H1-211463 8, 1989 lications Ltd., London, XP002 196719, Nov. 28, 1973. 1 page JP HO3-0 12231 1, 1991 (Abstract). JP HO3-053873 3, 1991 PCT International Search Report dated Jun. 11, 2002 (PCT/US01/ JP 2 572611 1, 1997 47020). JP H10-025302 1, 1998 WO WO 84/00761 3, 1984 * cited by examiner U.S. Patent Aug. 10, 2010 US 7,772.211 B2 FIGURE 1 Brabender Profile V. Feed Moisture Content E. Cottonii, Examples 1-3 S 200 1 5 2. 1 g 3 R O 70,00 75.00 80,00 85.00 90.00 %MC in feed amOn 1st Brabenber Peak, (2nd Brabender Peak admTemp of 1st Peak"C. IrarTerp. of 2nd Peak C US 7,772,211 B2 1. 2 PRODUCTION OF CARRAGEENAN AND or by oxidative depolymerization upon treatment with hydro CARRAGEENAN PRODUCTS gen peroxide. Upon cleavage of the polymer chains, carrag eenan products having optimum gelling properties and vis RELATED APPLICATIONS cosity can be obtained. In a typical process for making pure carrageenan, crude This application is a divisional application of U.S. appli seaweed is first washed with cold water to remove sand and cation Ser. No. 10/450,107, filed Oct. 14, 2003 now U.S. Pat. other particulates that may be present after the seaweed has No. 7,189,843 allowed May 9, 2006, incorporated herein by been harvested. Carrageenan typically does not Swell during reference, which is the U.S. National Phase or PCT/US01/ the cold wash, primarily because carrageenan in seaweed is 47020, filed Dec. 10, 2001, which is a continuation in part of 10 associated with the structural components of the seaweed, U.S. application Ser. No. 09/789,012, filed Mar. 2, 2001 now generally cellulose. Depending on the seaweed species, fol U.S. Pat. No. 6,479,649 which claims priority on U.S. Provi lowing the cold wash a hot water extraction procedure is sional Application 60/255.279, filed Dec. 13, 2000. typically performed in which the extracted carrageenan is treated with aqueous base at high temperature. Generally, the FIELD OF THE INVENTION 15 base used is an alkali or alkaline earth metal hydroxide Such as, for example, NaOH, Ca(OH), or KOH. This high tem The present invention is directed to carrageenan products, perature aqueous base modification leads to the formation of methods of preparing Such carrageenan products, and to for 3,6-anhydro linkages in the galactose units of the carrageenan mulations containing carrageenan products according to the polysaccharide. After base modification, the hot extract is present invention. filtered to remove insoluble material such as cellulose, hemi BACKGROUND OF THE INVENTION cellulose and other particulates, and acid is added to adjust the pH to 9 or lower. The filtrate can then be concentrated to Carrageenan is a complex mixture of sulfated polysaccha about4% carrageenan for further processing. Optional proce dural steps after extraction may include centrifugation and rides comprising linear polymers of 1.3 bound C-D-galactose 25 units and 1.4 bound C-D-galactose units with the general bleaching. Pure carrageenan is typically obtained by precipi tation of the extract from the aqueous solution with KCl oran formula: alcohol Such as isopropanol. Preparation of pure carrageenan by extraction on a com 30 mercial scale is expensive because of viscosity and gelling wherein A and B represent galactose residues derived from properties that limit the rate at which Such carrageenan prod two different groups. ucts can be processed. After the extraction step, a hot aqueous Carrageenan is extracted from red seaweeds and consti stream can typically only contain low concentrations of car tutes the principal structure of the seaweed.
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