Glyceryl ether compounds and their use

Details Glyceryl ether compounds and their use Glyceryl ether compounds and their use

2011-05-20

2011-12-27

Solola, Taofiq A (Department: 1622)

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acid esters

Reexamination Certificate

active

08084635

ABSTRACT:
Glyceryl ether compounds prepared by the reaction of glycerol and olefin epoxides are disclosed. The compounds are renewable biomass-based surfactants useful as detergents and emulsifiers in formulations for cleaning, laundry, personal care, cosmetics, and industrial uses.

REFERENCES:
patent: 4465866 (1984-08-01), Takaishi et al.
patent: 5362494 (1994-11-01), Zysman et al.
patent: 5442082 (1995-08-01), Uphues et al.
patent: 5539001 (1996-07-01), Waldmann-Laue et al.
patent: 5627144 (1997-05-01), Urfer et al.
patent: 6211329 (2001-04-01), Rehnberg et al.
patent: 2003/0167681 (2003-09-01), Puche
patent: 2004/0077904 (2004-04-01), Nagasawa et al.
patent: 0524548 (1993-01-01), None
patent: 54145224 (1979-11-01), None
patent: 4217972 (1992-08-01), None
patent: 2007/016018 (2007-01-01), None
patent: WO92/08685 (1992-05-01), None
Baskaran, S., et al., “An Efficient and Stereoselective Synthesis of (2R,2'S)-1-O-(2'-hydroxy-hexadecyl)glycerol and its Oxo Analogs: Potential Antitumor Compounds from Shark Liver Oil”, Tetrahedron, vol. 52, No. 18, pp. 6437-6452 (Apr. 29, 1996).
Blank, M.L., et al., The Biosynthesis of Plasmalogens from Labeled 0-Alkyl-glycerols in Ehrlich Ascites Cells, Biochimica and Biophysica Acta, vol. 210, pp. 442-427 (1970).
Blute, I., et al., Phase behaviour of alkyl glycerol ether sufactants, Tenside, Surfactants, Detergents, vol. 35, No. 3, pp. 207-212 (1998).
European Search Report for PCT/US2006/045191, mailed Jun. 9, 2011, 12 pages.
Karabina, E. and Borredon, M.E, “Synthesis of Hydroxyethers from Glycerol and Fatty Chains Epoxyalkanes in the Absence of Organic Solvent”, Synthetic Communications, vol. 24, No. 21, pp. 3009-3019 (1994).
Muramatsu, T. and Schmid, H.H.O., “1-O-2'-Hydroxyalkyl and 1-O-2'-Ketoalkyl Glycerols”, Chemistry and Physics of Lipids, vol. 9, No. 1, pp. 123-132 (Oct. 1, 1972).
Salager, J.L., Surfactants Types and Uses, FIRP Booklet #E300-A, Teaching Aid in Surfactant Science and Engineering, Universidad de Los Andes, Merida-Venezuela, Version #2, 50 pages, (2002).
International Preliminary Report on Patentability PCT/US2006/045191 issued May 27, 2008 with Written Opinion of the International Searching Authority completed Aug. 27, 2007, 6 pages.
Biswas et al., “Synthesis of Diethylamine Functionalized Soybean Oil.”J. Agric. Food Chem(2005) 53, 9485-9490.
Blee, et al., “Soybean Epoxide Hydrolase: Identification of the Catalytic Residues and Probing of the Reaction Mechanism with Secondary Kinetic Isotope Effects.”Journal of Biological Chemistry(2004) JBC Papers in Press, Published Dec. 13, 2004 as Manuscript M411366200.
Bournay, et al., “New Heterogeneous Process for Biodiesel Production: A way to Improve the Quality and the Value of the Crude Glycerin Produced by Biodiesel Plants.”Catalysis Today(2005) 106, 190-192.
Corma, et al., “Chemical Routes for the Transformation of Biomass into Chemicals.”Chem. Rev.(2007) 107, 2411-2502.
Di Serio, et al., “Transesterification of Soybean Oil to Biodiesel by Using Heterogeneous Basic Catalysts.”Ind. Eng. Chem. Res.(2006) 45, 3009-3014.
Du, et al., “Catalytic Epoxidation of Methyl Linoleate.”JAOCS(2004) 81.
Lanza, et al., eds., “Biofuels: Opportunity or Threat?” Environmental Grantmakers Association 2006.
Hazimah, et al., “Recovery of Glycerol and Diglycerol from Glycerol Pitch.”Journal of Oil Palm Research(2003) 15(1), 1-5.
Kim, et al., “Transesterification of Vegetable Oil to Biodiesel Using Heterogeneous Base Catalyst.”Catalysis Today(2004) 93, 95, 315-320.
Ma, et al., “Biodiesel Production: A Review.”Bioresource Technology(1999) 70, 1-15.
Manzer, et al., “Biomass Derivatives: A Sustainable Source of Chemicals.” NSF Workshop on Catalysis for Renewables Conversion, Washington D.C., Apr. 13-14, 2004.
Meher, et al., “Technical Aspects of Biodiesel Production by Transesterification: A Review.” RSER 194 (2004) 18:41, 1-21.
Miller, et al., “Biorenewable Fuels and Chemicals via Reactive Distillation.” Dept. Chemical Engineering an Materials Science presentation, Michigan University May 11, 2006.
Muturi, et al., “Epoxidized Vegetable Oils as Reactive Diluents I. Comparison of Vernonia, Epoxidized Soybean and Epoxidized Linseed Oils.”Progress in Organic Coatings(1994) 25, 85-94.
Natl. Renewable Energy Laboratory, NREL/BR-510-39436, “From Biomass to Biofuels” (Aug. 2006).
Ono, et al., “Preparation, Surface-Active Properties and Acid Decomposition Profiles of a New ‘Soap’ Bearing a 1,3-Dioxolane Ring.”JAOCS(1993) 70, 1.
Ono, et al., “Synthesis and Properties of Soap Types of Double-Chain Cleavable Surfactants Derived from Pyruvate.”J. Oleo Sci.(2004) 53 (2), 89-95.
Rios, et al., “Textural and Chemical Characterization of Crystalline Ti-SiO2Catalysts Used in the Epoxidation of Fatty Esters.” DYNA, Universidad Nacional de Colombia (2006) 73(148), 95-101. ISSN: 0012-7353.
Samuelsson, et al., “A Study of Fatty Acid Methyl Esters with Epoxy or Alkyne Functionalities.”JAOCS(2001) 78(12), 1191-1196.
Sarnacke, S., “Soy Beans as Polymer Building Blocks.” Omni Tech International, Ltd. presentation to United Soybean Board, Aug. 16, 2007.
Srivastava, et al., “Synthesis, Characterization and Curing Behaviour of Partial Esters of Cycloaliphatic Epoxy Resins.”Designed Monomers and Polymers(2005) 8(4), 319-334.
Suppes, et al., “Calcium Carbonate Catalyzed Alcoholysis of Fats and Oils.”JAOCS(2001) 78, 2, 139-146.
Thompson, et al., “Characterization of Crude Glycerol from Biodiesel Production from Multiple Feedstocks.”American Society of Agricultural and Biological Engineers(2006) 22(2), 261-265.
Wedmid, et al., “Long-Chain Stereomeric 2-Alkyl-4-methoxycarbonyl-1,3-dioxolanes in Glycerol Acetal Synthesis.”J. Org. Chem.(1977) 42(22), 3624-3626.

Affiliated with

Also associated with

Rating

Glyceryl ether compounds and their use does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Glyceryl ether compounds and their use, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Glyceryl ether compounds and their use will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-4259382