Chemistry of inorganic compounds – Carbon or compound thereof – Elemental carbon
Reexamination Certificate
2006-10-24
2010-06-22
Mayes, Melvin C (Department: 1793)
Chemistry of inorganic compounds
Carbon or compound thereof
Elemental carbon
C423S460000, C977S745000, C977S748000
Reexamination Certificate
active
07740826
ABSTRACT:
A method for functionalizing the wall of single-wall or multi-wall carbon nanotubes involves the use of acyl peroxides to generate carbon-centered free radicals. The method allows for the chemical attachment of a variety of functional groups to the wall or end cap of carbon nanotubes through covalent carbon bonds without destroying the wall or endcap structure of the nanotube. Carbon-centered radicals generated from acyl peroxides can have terminal functional groups that provide sites for further reaction with other compounds. Organic groups with terminal carboxylic acid functionality can be converted to an acyl chloride and further reacted with an amine to form an amide or with a diamine to form an amide with terminal amine. The reactive functional groups attached to the nanotubes provide improved solvent dispersibility and provide reaction sites for monomers for incorporation in polymer structures. The nanotubes can also be functionalized by generating free radicals from organic sulfoxides.
REFERENCES:
patent: 2003/0086858 (2003-05-01), Niu et al.
patent: 2004/0009114 (2004-01-01), Margrave et al.
patent: 2004/0202603 (2004-10-01), Fischer et al.
patent: WO 98/39250 (1998-09-01), None
patent: WO 00/17101 (2000-03-01), None
patent: WO 02/16257 (2002-02-01), None
patent: WO 02/064868 (2002-08-01), None
patent: WO 02/064869 (2002-08-01), None
Kirk-Othmer; Encyclopedia of Chemical Technology; Peroxides and Peroxide Compounds, Organic Peroxides; 1996.
Mickelson, E.T., et al., “Fluorination of single-wall carbon nanotubes”, Chem. Phys. Lett. 296 (1998), pp. 188-194.
Boul, P.J., et al., “Reversible sidewall functionalization of buckytubes”, Chem. Phys. Lett. 310 (1999), pp. 367-372.
Saini, R.K., et al., “Covalent Sidewall Functionalization of Single Wall Carbon Nanotubes”, J. Am. Chem. Soc. 125 (2003), pp. 3617-3621.
Mickelson, E.T., et al., “Solvation of Fluorinated Single-Wall Carbon Nanotubes in Alcohol Solvents”, J. Phys. Chem. B., vol. 103 (1999), pp. 4318-4322.
Khabashesku, V.N., et al., “Fluorination of Single-Wall Carbon Nanotubes and Subsequent Derivatization Reactions”, Acc. Chem. Res. 35 (2002) pp. 1087-1095.
Khabashesku, V.N., et al., “Chemistry of carbon nanotubes”, vol. 1, The Encyclopedia of Nanoscience and Nanotechnology, S. Nalwa, Ed., American Scientific Pub. (2004), pp. 1-47.
Stevens, J.L., et al., “Sidewall Amino-Functionalization of Single-Wall Carbon Nanotubes through Fluorination and Subsequent . . . ”, Nano Lett. 3 (2003), pp. 331-336.
Bahr, J.L., et al., “Functionalization of Carbon Nanotubes by Electrochemical Reduction of Aryl Diazonium Salts: A . . . ”, J. Am. Chem. Soc. 123 (2001), pp. 6536-6542.
Georgakilas, V., et al., “Organic Functionalization of Carbon Nanotubes”, J. Am. Chem. Soc. 124 (2002), pp. 760-761.
Georgakilas, V., et al., “Purification of HiPCO Carbon Nanotubes via Organic Functionalization”, Chem. Commun. (2002), pp. 14318-14319.
Pantarotto, D., et al., “Synthesis, Structural Characterization, and Immunological Properties of Carbon Nanotubes . . . ”, J. Am. Chem. Soc. 125 (2003), pp. 6160-6164.
Chen, Y., et al., “Chemical attachment of organic functional groups to single-walled carbon nanotube material”, J. Mater. Res. 13 (1998), pp. 2423-2431.
Chen, J., et al, “Solution Properties of Single-Walled Carbon Nanotubes”, Science 282 (1998), pp. 95-98.
Holzinger, M., et al., “Sidewall Functionalization of Carbon Nanotubes”, Angew. Chem. Int. Ed. 40 (2001), pp. 4002-4005.
Peng, H., et al., “Sidewall functionalization of single-walled carbon nanotubes with organic peroxides”, Chem. Commun. (2003), pp. 362-363.
Ying, Y., et al., “Functionalization of Carbon Nanotubes by Free Radicals”, Org. Lett. 5 (2003), pp. 1471-1473.
Kini, V.U., et al., “Two new synthetic routes to polyhydroxylated nanotubes”, Rice Quantum Institute Sixteenth Annual Summer Research Colloquium (Aug. 9, 2002), Abtr. p. 25.
Bahr, J.L., et al., “Highly Functionalized Carbon Nanotubes Using in Situ Generated Diazonium Compounds”, Chem. Mater. 13 (2001), pp. 3823-3824.
Kooi, S.E., et al., “Electrochemical Modification of Single Carbon Nanotubes”, Angew. Chem. Int. Ed. 48 (2002), pp. 1353-1355.
Tagmatarchis, N., et al., “Sidewall functionalization of single-walled carbon nanotubes through electrophilic addition”, Chem. Commun. (2002), pp. 2010-2011.
Pekker, S., et al., “Hydrogenation of Carbon Nanotubes and Graphite in Liquid Ammonia”, J. Phys. Chem. B. 105 (2001), pp. 7938-7943.
Fontana, F., et al., “New General and Convenient Sources of Alkyl Radicals, Useful for Selective Syntheses”, Tetrahedron Lett. 29 (1988), pp. 1975-1978.
Chiang, I.W., et al., “Purification and Characterization of Single-Wall Carbon Nanotubes (SWNTs) Obtained from the Gas-Phase . . . ”, J. Phys. Chem. B 105 (2001), pp. 8297-8301.
Arndt, S., et al., “Quinone—Annonaceous Acetogenins: Synthesis and Complex I Inhibition Studies of a New Class of Natural . . . ”, Chem. Eur. J. 7 (2001), pp. 993-1005.
Gu, Z., et al., “Cutting Single-Wall Carbon Nanotubes through Fluorination”, Nano Lett. 2 (2002), pp. 1009-1013.
Clover, A.M., et al, “The Action of Hydrogen Peroxide Upon Anhydrides and the Formation of Organic Acid, Peroxides, and Peracids”, 32 (1904), pp. 43-68.
Billups Wilbur Edward
Khabashesku Valery N.
Margrave John L.
Margrave, legal representative Mary Lou
Peng Haiqing
Gregorio Guinever S
Mayes Melvin C
William Marsh Rice University
Winstead PC
LandOfFree
Method for functionalizing carbon nanotubes utilizing peroxides does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Method for functionalizing carbon nanotubes utilizing peroxides, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Method for functionalizing carbon nanotubes utilizing peroxides will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-4179946