Source: http://www.google.com/patents/US7544415?dq=patent:7076806
Timestamp: 2014-04-19 12:58:57
Document Index: 205025804

Matched Legal Cases: ['Application No. 03136785', 'Application No. 03136786', 'Application No. 03252761', 'Application No. 03252762', 'Application No. 03252761', 'Application No. 03252762']

Patent US7544415 - Polymer and method for using the polymer for solubilizing nanotubes - Google PatentsSearch Images Maps Play YouTube News Gmail Drive More »Sign inAdvanced Patent SearchPatentsA new, non-wrapping approach to solubilize nanotubes, such as carbon nanotubes, in organic and inorganic solvents is provided. In accordance with certain embodiments, carbon nanotube surfaces are functionalized in a non-wrapping fashion by functional conjugated polymers that include functional groups...http://www.google.com/patents/US7544415?utm_source=gb-gplus-sharePatent US7544415 - Polymer and method for using the polymer for solubilizing nanotubesAdvanced Patent SearchPublication numberUS7544415 B2Publication typeGrantApplication numberUS 11/775,633Publication dateJun 9, 2009Filing dateJul 10, 2007Priority dateMay 2, 2002Fee statusPaidAlso published asDE60336032D1, EP1359121A2, EP1359121A3, EP1359121B1, US7244407, US20040034177, US20040266939, US20080194737Publication number11775633, 775633, US 7544415 B2, US 7544415B2, US-B2-7544415, US7544415 B2, US7544415B2InventorsJian Chen, Haiying LiuOriginal AssigneeZyvex Performance Materials, Inc., University of Pittsburgh�of the Commonwealth System of Higher EducationExport CitationBiBTeX, EndNote, RefManPatent Citations (99), Non-Patent Citations (99), Referenced by (1), Classifications (29), Legal Events (3) External Links: USPTO, USPTO Assignment, EspacenetPolymer and method for using the polymer for solubilizing nanotubesUS 7544415 B2Abstract A new, non-wrapping approach to solubilize nanotubes, such as carbon nanotubes, in organic and inorganic solvents is provided. In accordance with certain embodiments, carbon nanotube surfaces are functionalized in a non-wrapping fashion by functional conjugated polymers that include functional groups for solubilizing such nanotubes. Various embodiments provide polymers that noncovalently bond with carbon nanotubes in a non-wrapping fashion. For example, various embodiments of polymers are provided that comprise a relatively rigid backbone that is suitable for noncovalently bonding with a carbon nanotube substantially along the nanotube's length, as opposed to about its diameter. In preferred polymers, the major interaction between the polymer backbone and the nanotube surface is parallel π-stacking. The polymers further comprise at least one functional extension from the backbone that are any of various desired functional groups that are suitable for solubilizing a carbon nanotube.
CROSS-REFERENCE TO RELATED APPLICATIONS This application is a continuation of U.S. patent application Ser. No. 10/895,161, filed Jul. 20, 2004, now U.S. Pat. No. 7,244,407, which is a continuation of U.S. patent application Ser. No. 10/255,122, filed Sep. 24, 2002, which application claimed priority to Provisional Patent Application Ser. No. 60/377,856, filed May 2, 2002 and Provisional Patent Application Ser. No. 60/377,920 filed May 2, 2002, the entire disclosures of which are hereby incorporated herein by reference.
TECHNICAL FIELD The present invention is related to solubilization of nanotubes, and more particularly to a polymer that is capable of solubilizing nanotubes.
Carbon nanotubes can also be solubilized in organic solvents and water by polymer wrapping. See Dalton, A. B. et al., J. Phys. Chem. B 2000, 104, 10012-10016, Star, A. et al. Angew. Chem., Int. Ed. 2001, 40, 1721-1725, and O'Connell, M. J. et al. Chem. Phys. Lett. 2001, 342, 265-271, the disclosures of which are hereby incorporated herein by reference. FIGS. 1A-1C show examples of such polymer wrapping of a carbon nanotube. In polymer wrapping, a polymer �wraps� around the diameter of a carbon nanotube. For instance, FIG. 1 shows an example of polymers 102A and 102B wrapping around single-walled carbon nanotube (SWNT) 101. FIG. 1B shows an example of polymer 103A and 103B wrapping around SWNT 101. FIG. 1C shows an example of polymers 104A and 104B wrapping around SWNT 101. It should be noted that the polymers in each of the examples of FIGS. 1A-1C are the same, and the FIGURES illustrate that the type of polymer-wrapping that occurs is random (e.g., the same polymers wrap about the carbon nanotube in different ways in each of FIGS. 1A-1C). One disadvantage of this approach is that the polymer is very inefficient in wrapping the small-diameter single-walled carbon nanotubes produced by the HiPco process because of high strain conformation required for the polymer. For example, such polymer wrapping approach can only solubilize the SWNTsHiPco (i.e., SWNTs produced by the HiPco process) at about 0.1 mg/ml in organic solvents. SWNTHiPco is the only SWNT material that can be currently produced at a large scale with high purity.
BRIEF SUMMARY OF THE INVENTION The present invention is directed to a method for solubilizing nanotubes, a polymer for solubilizing nanotubes, and resulting compositions of matter that may be formed using solubilized nanotubes. Embodiments of the present invention provide a new approach to solubilizing nanotubes, such as carbon nanotubes, in solvents. The solvents can be, in principle, any solvents. Solubilization of carbon nanotubes in accordance with embodiments of the present invention have been experimentally demonstrated in organic solvents and in water. In accordance with certain embodiments of the present invention, carbon nanotube surfaces are functionalized in a non-wrapping fashion by functional conjugated polymers that include functional groups for solubilizing such nanotubes. As used herein, �non-wrapping� means not enveloping the diameter of a nanotube. Thus, associating a polymer with a nanotube in a �non-wrapping fashion� encompasses any association of the polymer with the nanotube in which the polymer does not completely envelop the diameter of the nanotube. When describing certain embodiments of the present invention, the non-wrapping fashion may be further defined and/or restricted. For instance, in a preferred embodiment of the present invention, a polymer can associate with a nanotube (e.g., via π-stacking interaction therewith) wherein the polymer's backbone extends substantially along the length of the nanotube without any portion of the backbone extending over more than half of the nanotube's diameter in relation to any other portion of the polymer's backbone.
An example of a technique for solubilizing carbon nanotubes was performed using rigid functional conjugated polymers, poly(aryleneethynylene)s (also referred to as �1,� �3�, �4� herein). See Bunz, U. H. F. Chem. Rev. 2000, 100, 1605-1644 and McQuade, D. T. et al., J. Am. Chem. Soc. 2000, 122, 12389-12390, the disclosures of which are hereby incorporated herein by reference, and poly(3-decylthiophene) (also referred to as �2� herein). FIGS. 3A-3C show example polymer structures of embodiments of the present invention. More specifically, FIG. 3A shows an example poly(aryleneethynylene) (labeled �1�) polymer structure that may be used to noncovalently bond with a carbon nanotube in a non-wrapping fashion. The example polymer structure shown in FIG. 3A comprises functional extensions R1, R2, R3, and R4, which may, in alternative example implementations for solubilizing carbon nanotubes, be implemented as either 1a, 1b, 1c, or 1d shown hereafter:
In contrast to previous work, See Dalton, Star, and O'Connell, M. J. et al., the backbone of 1, 2, 3, and 4 described above is rigid and cannot wrap around the SWNTs, and the major interaction between the polymer backbone and the nanotube surface is parallel π-stacking. Further, the example backbones 5-18 described below are also rigid such that they do not wrap around the nanotube, and the major interaction between such polymer backbones and the nanotube surface is parallel π-stacking. Parallel π-stacking is one type of noncovalent bonding. See Chen, R. J. et al., J. Am. Chem. Soc., 2001, 123, 3838-3839, the disclosure of which is hereby incorporated herein by reference. The techniques disclosed herein utilize such polymers to enable the dissolution (or �solubilization�) of various types of carbon nanotubes in organic solvents (such as CHCl3, chlorobenzene etc), which represents the first example of solubilization of carbon nanotubes via π-stacking without polymer wrapping.
The new polymers (1a-1, naverage=19.5; 1a-2, naverage=13; 1b, naverage=19; 1c, naverage=19; 1d) were synthesized and characterized according to known methods. See Bunz, U. H. F. Chem. Rev. 2000, 100, 1605-1644, the disclosure of which is hereby incorporated herein by reference. Three types of SWNTs were used in this study: 1) purified HiPco-SWNTs (�SWNTsHiPco�, from Carbon Nanotechnologies, Inc.); 2) purified laser-grown SWNTs (�SWNTslaser�); and 3) purified electric arc-grown SWNTs (�SWNTsarc�). As an example preparation procedure for 1a-SWNTsHiPco complex: 14.7 mg of SWNTsHiPco was sonicated in 29.4 ml of CHCl3 for 30 minutes (�min�) to give an unstable suspension of visible insoluble solids. 14.7 mg of 1a was then added and most of the visible insoluble solids became soluble simply by vigorous shaking. The resulting solution was further sonicated for 10-30 min to give a black-colored stable solution with no detectable solid precipitation for over 10 days. Such resulting black-colored and unsaturated carbon nanotube solution was visually nonscattering and no precipitation occurred upon prolonged standing (e.g., over 10 days). The product was collected by PTFE membrane filtration (0.2-0.8 μm pore size), washed with CHCl3, and dried at room temperature under vacuum to give 20.6 mg of free-standing black solid film (bucky paper).
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Am. Chem. Soc. 1992, 114, 100024.Referenced byCiting PatentFiling datePublication dateApplicantTitleWO2011146151A2 *Feb 1, 2011Nov 24, 2011Applied Nanostructured Solutions, LlcFiber containing parallel-aligned carbon nanotubes* Cited by examinerClassifications U.S. Classification428/367, 423/445.00B, 428/408, 428/398, 525/416, 423/445.00R, 524/495, 423/460, 524/496International ClassificationB32B9/04, C08G61/12, C08G61/00, C08G61/02, C01B31/02Cooperative ClassificationB82Y40/00, C08G61/124, C08G61/126, C08G61/02, C08G61/122, C01B2202/02, C01B31/0273, B82Y30/00European ClassificationB82Y30/00, C01B31/02B4D6, B82Y40/00, C08G61/12D1F, C08G61/12D1B, C08G61/12D, C08G61/02Legal EventsDateCodeEventDescriptionOct 4, 2012FPAYFee paymentYear of fee payment: 4Jan 13, 2009ASAssignmentOwner name: VON EHR, JAMES R., II, TEXASFree format text: SECURITY AGREEMENT;ASSIGNOR:ZYVEX PERFORMANCE MATERIALS, INC., A DELAWARE CORPORATION;REEL/FRAME:022092/0502Effective date: 20090106Dec 20, 2008ASAssignmentOwner name: ZYVEX PERFORMANCE MATERIALS, INC., OHIOFree format text: MERGER;ASSIGNOR:ZYVEX PERFORMANCE MATERIALS, LLC;REEL/FRAME:022011/0352Effective date: 20080613RotateOriginal ImageGoogle Home - Sitemap - USPTO Bulk Downloads - Privacy Policy - Terms of Service - About Google Patents - Send FeedbackData provided by IFI CLAIMS Patent Services©2012 Google