Source: http://www.google.com/patents/US7547472?dq=6,108,703
Timestamp: 2015-07-04 15:54:15
Document Index: 296279410

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

Patent US7547472 - Polymer and method for using the polymer for noncovalently functionalizing ... - Google PatentsSearch Images Maps Play YouTube News Gmail Drive More »Sign inAdvanced Patent SearchPatentsA new, non-wrapping approach to functionalizing 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/US7547472?utm_source=gb-gplus-sharePatent US7547472 - Polymer and method for using the polymer for noncovalently functionalizing nanotubesAdvanced Patent SearchPublication numberUS7547472 B2Publication typeGrantApplication numberUS 11/775,005Publication dateJun 16, 2009Filing dateJul 9, 2007Priority dateMay 2, 2002Fee statusPaidAlso published asCN1257197C, CN1515598A, DE60328067D1, EP1359169A2, EP1359169A3, EP1359169B1, US6905667, US7241496, US20060002841, US20080187482Publication number11775005, 775005, US 7547472 B2, US 7547472B2, US-B2-7547472, US7547472 B2, US7547472B2InventorsJian 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 (3), Classifications (38), Legal Events (5) External Links: USPTO, USPTO Assignment, EspacenetPolymer and method for using the polymer for noncovalently functionalizing nanotubes
US 7547472 B2Abstract
1. A method of controlling the location of at least one functional group on a functionalized nanotube, comprising:
selecting at least one functional group,
selecting at least one polymer having a backbone portion capable of bonding to a nanotube in a non-wrapping fashion for controlling the location of the at least one functional group on the backbone portion,
interacting the at least one polymer and the at least one functional group to form a polymer having a backbone portion for noncovalently bonding with a nanotube in a non-wrapping fashion and having at least one functional group, and
interacting the polymer having a backbone portion for noncovalently bonding with a nanotube in a non-wrapping fashion and having at least one functional group and at least one carbon nanotube.
2. The method of claim 1 wherein the backbone portion comprises a portion selected from the group consisting of:
wherein at least one of R1-R8 in the above-listed backbone portions a)-q) represents a functional group; and wherein n is greater than or equal to 2.
3. The method of claim 1 wherein the polymer comprises poly(aryleneethynylene).
4. The method of claim 3 further comprising at least 4 functional portions (R1, R2, R3, and R4), wherein said functional portions comprise functional portions selected from the group consisting of:
a) R1=R4=H and R2=R3=OC10H21,
b) R1=R2=R3=R4=F,
c) R1=R4=H and R2=R3=
d) R1=R4=H and R2=R3=
5. The method of claim 1 wherein the polymer comprises poly(phenyleneethynylene).
6. The method of claim 1 wherein the polymer comprises poly(3-decyithiophene).
7. The method of claim 1 wherein the at least one functional group comprises at least one member selected from the group consisting of:
8. The method of claim 1 wherein the at least one functional group comprises a chemical handle.
9. The method of claim 1 wherein the at least one functional group comprises a sensor.
10. The method of claim 1 wherein the at least one functional group comprises an ionic functional group.
11. The method of claim 1 wherein the at least one functional group comprises a neutral functional group.
12. The method of claim 1 wherein the at least one functional group comprises an organic functional group.
13. The method of claim 1 wherein the nanotube is a carbon nanotube.
14. The method of claim 1 wherein the backbone portion is capable of interacting with the nanotube's surface via π-stacking. Description
This application is a continuation of U.S. patent application Ser. No. 10/894,738 filed Jul. 20, 2004 now U.S. Pat. No. 7,241,496, which is a continuation of U.S. patent application Ser. No. 10/318,730 filed Dec. 13, 2002, now U.S. Pat. No. 6,905,667 which issued on Jun. 14, 2005, which application claimed priority to Provisional Patent Application Ser. No. 60/377,920, filed May 2, 2002, the entire disclosures of which are hereby incorporated herein by reference.
Another technique for producing carbon nanotubes is the “electric arc” technique in which carbon nanotubes are synthesized utilizing an electric arc discharge. As an example, single-walled nanotubes (SWNTs) may be synthesized by an electric arc discharge under helium atmosphere with the graphite anode filled with a mixture of metallic catalysts and graphite powder (Ni:Y;C), as described more fully by C. Journet et al. in Nature (London), 388 (1997), 756. Typically, such SWNTs are produced as close-packed bundles (or “ropes”) with such bundles having diameters ranging from 5 to 20 nm. Generally, the SWNTs are well-aligned in a two-dimensional periodic triangular lattice bonded by van der Waals interactions. The electric arc technique of producing carbon nanotubes is further described by C. Journet and P. Bemier in Appl. Phys. A, 67, 1, the disclosure of which is hereby incorporated herein by reference. Utilizing such an electric arc technique, the average carbon nanotube diameter is typically approximately 1.3 to 1.5 nm and the triangular lattice parameter is approximately 1.7 nm. As with the laser vaporization technique, the electric arc production technique is generally a very low yield process that requires a relatively long period of time to produce small quantities of carbon nanotubes. For instance, one hour of electric arc processing typically results in approximately 100 milligrams of carbon nanotubes.
Molecular engineering (e.g., cutting, solubilization, chemical functionalization, chromatographic purification, manipulation and assembly) of single-walled carbon nanotubes (SWNTs) is expected to play a vital role in exploring and developing the applications of carbon nanotubes. Noncovalent functionalization of carbon nanotubes has received particular growing interest recently, because it offers the potential to add a significant degree of functionalization to carbon nanotube surfaces (sidewalls) while still preserving nearly all of the nanotubes' intrinsic properties. For example, SWNTs can be solubilized in organic solvents and water by polymer wrapping (see e.g., (a) Dalton, A. B.; et al. J. Phys. Chem. B 2000, 104, 10012-10016; (b) Star, A.; et al. Angew. Chem., Int. Ed. 2001, 40, 1721-1725; (c) O'Connell, M. J.; et al. Chem. Phys. Lett. 2001, 342, 265-271; and published U.S. Patent Application Numbers 2002/0046872, 2002/0048632, and 2002/0068170 by Richard E. Smalley, et al., each titled “POLYMER-WRAPPED SINGLE WALL CARBON NANOTUBES”), and nanotube surfaces can be noncovalently functionalized by adhesion of small molecules for protein immobilization (see e.g., Chen, R. J.; et al. J. Am. Chem. Soc. 2001, 123, 3838-3839).
Compared to preparing polymer-wrapped carbon nanotubes (of FIGS. 1A-1C), the non-wrapping approach of embodiments of the present invention should allow better control over the distance between functional groups on the carbon nanotube surface by precisely varying the length and constitution of 1's backbone (or other selected backbone) and side chain. This strategy open the door to the (semi-)site-controlled noncovalent functionalization of carbon nanotube surfaces. Such functionalization may introduce numerous neutral and ionic functional groups onto the carbon nanotube surfaces. It may provide “chemical handles” for manipulation and assembly of carbon nanotubes, enabling applications in a variety of areas such as chemical and biological sensing.
As an example of a technique for functionalizing carbon nanotubes, we have conducted a study in which we used 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, be implemented as either 1a, 1b, 1c, or 1d shown hereafter:
R1═R4═H, R2═R3═OC10H21 (1a)
R1═R2═R3═R4═F (1b)
The example polymer structures of FIGS. 3A-3C may be implemented for noncovalently bonding with a carbon nanotube in a non-wrapping fashion, as with the example shown in FIGS. 2A-2B. Indeed, the example molecular model of FIGS. 2A-2B illustrates an example of implementation 1a, described above, of the polymer of FIG. 3A, and more specifically it shows an example of implementation 1an=1.5-SWNT(6,6) complex (i.e., armchair SWNT), wherein n is the repeat number. It should be understood that the present invention is not intended to be limited solely to the example functional groups of 1a, 1b, 1c, and 1d (or the functional groups of polymer structures 3 and 4) shown above for functionalizing carbon nanotubes, but rather any such functional group now known or later developed for functionalizing carbon nanotubes may be used in accordance with embodiments of the present invention. Preferably, the functional group(s) included in the polymer do not substantially alter the intrinsic properties of the carbon nanotube. Further, it should be understood that while the example functional groups 1a-1d solubilize a carbon nanotube, various other types of functional groups may be included for functionalizing a nanotube in any of various other ways, for example for implementing a chemical handle, performing biological sensing, etc.
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. Certain techniques disclosed herein utilize such polymers to enable functionalization of various types of carbon nanotubes in organic solvents (such as CHCl3, chlorobenzene etc).
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).
The procedures followed in my study for 2-SWNTsHiPco, 1c-SWNTsHiPco, 1b-SWNTsHiPco, 1d -SWNTsHiPco, 3-SWNTsHiPco, 1a-SWNTslaser and 1a-SWNTsarc are similar to that described above for 1a-SWNTsHiPco. The as-prepared SWNTsHiPco and CVD-grown multi-walled carbon nanotubes (MWNTs) can also be functionalized (e.g., solubilized) in CHCl3 by a similar procedure. The as-prepared SWNTsarc, however, form an unstable suspension using a similar procedure, presumably due to the amorphous carbon coating on nanotubes that prevents the efficient π-π interaction between 1 and the nanotube surfaces.
The PTFE membrane filtration and CHCl3 washing steps were used to remove free 1a. According to the weight gain, the weight ratio (WRfinal) of 1a:SWNTsHiPco in the final product is estimated to be about 0.38-0.40, which is independent of WRinitial. For example, the WR data in three 1a:SWNTsHiPco reactions are as follows: 1) WRinitial=1.00, WRfinal=0.40; 2) WRinitial=0.40, WRfinal=0.38; 3) WRinitial=0.40, WRfinal=0.39. Although this estimate is still rough, it strongly suggests that 1 could form stable and irreversibly bound complexes with carbon nanotubes in CHCl3, instead of a simple mixture.
The example molecular structure of 1a-SWNT(6,6) shown in FIGS. 2A-2B was obtained by modeling. The 1an=1.5-SWNT(6,6) complex's structure was fully optimized using the UFF empirical potential. According to this model and considering the steric effect, it is most likely that one polymer complexes one SWNTHiPco (0.7-0.8 nm in diameter) per length of one polymer. The calculated WR of 1a: SWNTHiPco based on this assumption is about 0.5-0.6, which is slightly higher than the experimental value WRfinal (0.38-0.40). The difference may arise from the existence of nanotube ropes and impurities such as metal catalyst in SWNTsHiPco. In the case of SWNTslaser (1.1-1.3 nm in diameter) and SWNTsarc (1.3-1.5 nm in diameter), it is possible that two polymers complex one SWNT per length of one polymer. Compared to SWNTsHiPco, the SWNTslaser and SWNTsarc are less pure.
As shown in FIG. 5, compared to that of free 1a (δ 4.05), 1H NMR spectrum of 1a-SWNTsHiPco shows a significant upfield shift (δ 3.51) of the CH2 group (C1) that is closest to the aromatic group and nanotube surface. That is, FIG. 5 shows a first graph 501 showing the 1H NMR spectra (300 MHz, CDCl3) of free 1a and a second graph 502 showing the resulting 1H NMR spectra (300 MHz, CDCl3) of 1a-SWNTsHiPco. There is prior theoretical evidence for the existence of large diamagnetic ring currents in carbon nanotubes. Due to the presence of trace water, we did not determine the chemical shift of the C2 group. No substantial change is observed for the other CH2 groups, indicating that, although the polymer backbone is tightly attached to the nanotube surface via π-stacking, the side chain (C3-C10) of 1a is relatively free in solution. The signal of the phenylene group that is closely associated with the nanotube surface is too broad to be detected. The 1H NMR spectrum of 1a-SWNTslaser gives a similar result.
As shown in Table 1, the bucky paper made of 1-SWNTsHiPco complex (Tensile strength=28.3 MPa; Young's modulus=4.5 GPa) demonstrates a significant improvement in mechanical properties compared to those of bucky paper made of pure SWNTsHiPco (Tensile strength=9.74 MPa; Young's modulus=0.26 GPa). Both types of bucky papers were produced by the same room temperature membrane filtration process (without any high temperature annealing) for better comparison. This shows that 1 can increase the adhesion between nanotubes via more efficient π-π interactions. Accordingly, the resulting bucky paper dissolves more slowly in CHCl3 at a lower concentration (approximately 0.1-0.2 mg/ml of 1a-SWNTsHiPco in CHCl3). For applications that require high nanotube concentration (for example, polymer composites), using 1-SWNTs (W=0.4) solution in CHCl3 prepared in situ without filtration is recommended.
In the above backbones 5-18, n is preferably greater than or equal to 2, and R represents any organic functional group, such as R=OC10H21, R=C10H21, or other desired functional group. It should be recognized that the example backbones 5-15 are poly(aryleneethynylene)s, backbone 16 is a polyphenylene, backbone 17 is a polypyrrole, and backbone 18 is a polythiophene.
Mechanical properties of polycarbonate (PC)
alone and PC/1a-SWNTsHiPco nanocomposite.
PC Neat
Soluble 1a-SWNTsHiPco complex significantly improves the mechanical properties of commercial polymers. For example and as shown in Table 2, the tensile strength and break strain of pure poly(bisphenol A carbonate) are 26 MPa and 1.23%, respectively; 3.8 wt % of SWNTsHiPco filling results in 68% and 1453% increases in tensile strength (43.7 MPa) and break strain (19.1%) of poly(bisphenol A carbonate) (average Mw approximately 64,000), respectively.
As a result of π-π interactions between the polymer backbone and the nanotube surface, the major absorption bands of 1a are significantly broadened in the 1a-SWNTsHiPco complex, as shown in FIGS. 7A-7B. More specifically, FIG. 7A shows room-temperature solution-phase (CHCl3) fluorescence spectra (excitation wavelength: 400 nm) of 1a and the 1a-SWNTsHiPco complex, and FIG. 7B shows the ultra-violet (UV)-visible spectra of 1a and the 1a-SWNTsHiPco complex. The strong fluorescence of 1a is efficiently quenched in the 1a-SWNTsHiPco complex by nanotube surfaces, which is further confirmed by fluorescence microscopy. Energy transfer quenching between molecules and for molecules on metal surfaces is well known.
Functionalizing nanotubes through use of a non-wrapping polymer in accordance with embodiments of the present invention may provide several advantages. For example, solubilization of nanotubes allows for their use in enhancing the properties of various compositions of matter, including, as one example, plastics. Insoluble nanotubes cannot be dispersed homogeneously in commercial plastics and adhesives; therefore the polymer composites made by the addition of insoluble nanotubes gave little improvement in mechanical performance of plastics (Ajayan, P. M. et al., Adv. Mater. 2000, 12, 750; Schadler, L. S. et al. Appl. Phys. Lett. 1998, 73, 3842). In contrast, soluble nanotubes can significantly improve the mechanical performance of plastics, for example. For example, the tensile strength and break strain of pure poly(bisphenol A carbonate) are 26 MPa and 1.23%, respectively; 3.8 wt % of SWNTsHiPco filling results in 68% and 1453% increases in tensile strength (43.7 MPa) and break strain (19.1%) of poly(bisphenol A carbonate) (average Mw approximately 64,000), respectively.
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Am. Chem. Soc. 1992, 114, 100024.Referenced byCiting PatentFiling datePublication dateApplicantTitleUS8943641 *May 30, 2011Feb 3, 2015Linden Photonics, Inc.Method and apparatus for cleaning a fiber optic connector end faceUS20110297184 *May 30, 2011Dec 8, 2011Amaresh MahapatraMethod and apparatus for cleaning a fiber optic connector end faceUS20130076371 *Feb 25, 2011Mar 28, 2013TuTech Innoovation GmbHAdhesive with anisotropic electrical conductivity and methods of producing and using same* Cited by examinerClassifications U.S. Classification428/367, 423/445.00R, 428/408, 423/460, 525/416, 524/495, 428/398, 524/496, 423/445.00BInternational ClassificationC08G61/02, B32B9/04, D01F11/14, C08G61/12, C01B31/02, C08G61/00Cooperative ClassificationY10T428/2918, Y10T428/2975, Y10T428/30, B82Y30/00, Y10S977/847, Y10S977/737, C01B2202/02, D01F11/14, C01B2202/28, C08G61/124, C08G61/122, C08G61/126, B82Y40/00, C08G61/02, C01B31/0273European ClassificationB82Y30/00, C01B31/02B4D6, B82Y40/00, C08G61/12D, C08G61/02, C08G61/12D1B, D01F11/14, C08G61/12D1FLegal EventsDateCodeEventDescriptionDec 20, 2008ASAssignmentOwner name: ZYVEX PERFORMANCE MATERIALS, INC., OHIOFree format text: MERGER;ASSIGNOR:ZYVEX PERFORMANCE MATERIALS, LLC;REEL/FRAME:022011/0352Effective date: 20080613Jan 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: 20090106May 3, 2011CCCertificate of correctionOct 4, 2012FPAYFee paymentYear of fee payment: 4Jul 28, 2014ASAssignmentOwner name: ZYVEX CORPORATION, TEXASFree format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:CHEN, JIAN;REEL/FRAME:033403/0869Effective date: 20030204Owner name: THE UNIVERSITY OF OF PITTSBURGH, PENNSYLVANIAFree format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:LIU, HAIYING;REEL/FRAME:033403/0828Effective date: 20030130Owner name: ZYVEX PERFORMANCE MATERIALS, LLC, TEXASFree format text: NUNC PRO TUNC ASSIGNMENT;ASSIGNOR:ZYVEX CORPORATION;REEL/FRAME:033404/0010Effective date: 20070521RotateOriginal ImageGoogle Home - Sitemap - USPTO Bulk Downloads - Privacy Policy - Terms of Service - About Google Patents - Send FeedbackData provided by IFI CLAIMS Patent Services