Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From sulfur-containing reactant
Reexamination Certificate
2006-08-29
2006-08-29
Gorr, Rachel (Department: 1711)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From sulfur-containing reactant
C528S378000, C528S379000, C528S380000
Reexamination Certificate
active
07098294
ABSTRACT:
The present invention relates to polythiophenes, particularly regioregular head-to-tail poly(3-alkylthiophenes) (HT-PATs), block copolymers made therefrom, and their methods of formation. The present invention provides HT-PATs with well-defined, specific end-groups, functionalization of the defined HT-PATs, and incorporation of end group functionalized HT-PATs into block copolymers with structural polymers. The intrinsically conductive diblock and triblock copolymers, formed from the HT-PATs, have excellent conductivity and low polydispersities that are useful in a number of applications. The block copolymers of the present invention have been found to exhibit conductivities that range from a low of 10−8S/cm for certain applications to as high as several hundred S/cm or more.
REFERENCES:
patent: 4508639 (1985-04-01), Camps et al.
patent: 4521589 (1985-06-01), Yamamoto et al.
patent: 4711742 (1987-12-01), Jen et al.
patent: 4929388 (1990-05-01), Wessling
patent: 4935164 (1990-06-01), Wessling et al.
patent: 5028354 (1991-07-01), Smith et al.
patent: 5185100 (1993-02-01), Han et al.
patent: 5217649 (1993-06-01), Kulkarni et al.
patent: 5227092 (1993-07-01), Han
patent: 5281363 (1994-01-01), Shacklette et al.
patent: 5358546 (1994-10-01), Rieke
patent: 5391622 (1995-02-01), Ho et al.
patent: 5427855 (1995-06-01), Heeger et al.
patent: 5476612 (1995-12-01), Wessling et al.
patent: 5571454 (1996-11-01), Chen et al.
patent: 5756653 (1998-05-01), Rieke
patent: 5965241 (1999-10-01), Mehta
patent: 6025462 (2000-02-01), Wang et al.
patent: 6166172 (2000-12-01), McCullough et al.
patent: 6190846 (2001-02-01), Majumdar et al.
patent: 6887965 (2005-05-01), McCullough et al.
patent: 2004/0051084 (2004-03-01), Wessling
patent: 2005/0187370 (2005-08-01), McCullough et al.
McCullough, “The Chemistry of Conducting Polythiophenes”,Advanced Materials, vol. 10, No. 2, pp. 93-116 (1999).
Guillerez et al. “New Convenient Synthesis of Highly Regloregular Poly(3-octylthiphene)Based on the Suzuki Coupling Reaction”,Synthetic Metals, vol. 93, pp. 123-126 (1998).
Iraqi et al., “Synthesis and Characterisation of the Telechelic Regioregular Head-to-Tail Poly (3-Alkylthiophenes)”,Mater. Chem., vol. 8, No. 1, pp. 25-29 (1998).
Shirakawa et al., “Cross-Coupling Reaction of Organostannanes with Aryl Halides Catalyzed by Nickel-Triphenylosphine or Nickel-Lithium Halide Complex”,Synthesis, pp. 1544-1549 (Oct. 1998).
Boymond et al., “Preparation of Highly Functionalized Grignard Reagents by an Iodine-Magnesium Exchange Reaction and its Application in Solid-Phase Synthesis”,Agnew Chem. Int. Ed., vol. 37, No. 12, pp. 1701-1703 (1998).
Bao et al., “Soluble and Processable Regioregular Poly(3-hexylthiophene) for Thin Film Field-Effect Transistor Applications with High Mobility”,Appl. Phys. Lett., vol. 69 (26), pp. 4108-4110 (1995).
Chen et al., “Regiocontrolled Synthesis of Poly(3-alkylthiophenes) Mediated by Rleke Zinc: Their Characterization and Solid-State Properties”,J. Am. Chem. Soc., vol. 117, pp. 233-244 (1995).
Mao et al., “Synthesis and Structure-Property Relationships of Regioirregular Poly(3-hexylthiophenes)”,Macromolecules, vol. 26. pp. 1163-1169 (1993).
McCullough et al., “Design, Synthesis, and Control of Conducting Polymer Architectures: Structurally Homogeneous Poly(3-alkylthiophenes)”,J. Org. Chem.
Farina et al., “Palladium-Catalyzed Coupling of Arylstannanes with Organic Sulfonates: A Comprehensive Study”,J. Org. Chem., vol. 58, pp. 5434-544 (1993).
Yamamoto et al., “Preparation of π-Conjugated Poly(thiophene-2,5-diyl), Poly(p-phenylene), and Related Polymers Using Zerovalent Nickel Complexes. Linear Structure and Properties of the π-Conjugated Polymers”,Macromolecules, vol. 25, pp. 1214-1223 (1992).
Liu et al., “Employing MALDI-MS on Poly (alkylthiophenes): Analysis of Molecular Weights, Molecular Weight Distributions, End-Group Structures, and End-Group Modifications”,Macromolecules, vol. 32, pp. 5777-5785 (1999).
Alkan, S., L. Toppare, Y. Hepuzer and Y. Ya{hacek over (g)}ci, “Synthesis and characterization of conducting block copolymers of thiophene-ended polystyrene with polypyrrole,”Synthetic Metals, 2001, 119, 133-134.
U.S. Appl. No. 11/197,727, filed Aug. 4, 2005, McCullough et al.
Liu et al., “End Group Modification of Regioregular Polythiophene through Postpolymerization Functionalization,”Macromolecules, 2002, 35, 9882-9889.
Liu et al., “Tuning the Electrical Conductivity and Self-Assembly of Regioregular Polythiophene by Block Copolymerization: Nanowire Morphologies in New Di- and Triblock Copolymers,”Angew. Chem. Int. Ed.,2002, 41, No. 2, pp. 329-332.
Liu et al., “End Group-Functionalization of Regioregular Head-to-Tail Poly(3-alkylthiophenes),”Polymer Preprints, 2000, 41(2), 1235-1236.
Liu et al., “ATRP approach to synthesize well-defined diblock copolymers containing regioregular heat-to-tail poly(3-hexylthiophene)s,”Polymeric Materials Science and Engineering, 2001, 84, 662-663.
Langeveld-Voss et al., “End-Group Modification of Regioregular Poly(3-alkylthiophene)s,”Chem. Commun., 2000, 81-82.
Francois et al., “Block-Copolymers with Conjugated Segments: Synthesis and Structural Characterization,”Synthetic Metals, 69, 1995, 463-466.
Yang et al., “A Soluble Blue-Light-Emitting Polymer,”Macromolecules, 1993, 26, 1188-1190.
Widawski et al., “Self-Organized Honeycomb Morphology of Star-Polymer Polystyrene Films,”Nature, vol. 369, Jun. 2, 1994, 387-389.
Jenekhe et al., “Self-Assembled Aggregates of Rod-Coil Block Copolymers and Their Stabalization and Encapsulation of Fullerenes,”Science, vol. 279, Mar. 20, 1998, 1903-1907.
Wang et al., “Synthesis of Amphiphilic Diblock Copolymers Containing a Conjugated Block and Their Self-Assembling Properties,”J. Am. Chem. Soc., 2000, 122, 6855-6861.
Li et al., “Synthesis of Oligophenylenevinylenes-Polyisoprene Diblock Copolymers and their Microphase Separation,”Macromolecules, 1999, 32, 3034-3044.
Hempenius et al., “A Polystyrene-Oligothiophene-Polystyrene Triblock Copolymer,”J. Am. Chem. Soc., 1998, 120, 2798-2804.
Greve et al., “Synthesis and Characterisation of Novel Regioregular Polythiophenes—Tuning the Redox Properties,”Eur. J. Org. Chem., 2001, 3437-3443.
McCullough, Poster Session, “End-group functionalization of regioregular head-to-tail(3-alkylthiophenes),” Paper 122; Aug. 20, 2000, 220th American Chemical Society National Meeting, Washington, DC.
Alkan, S. et al., Abstract of “Synthesis and characterization of conducting block copolymers of thiophene-ended polystyrene with polypyrrole,”Synthetic Metals, 2001, 119(1-3), 133-134.
Ewbank Paul C.
Liu Jinsong
McCullough Richard D.
Sheina Elena E.
Carnegie Mellon University
Gorr Rachel
Kirkpatrick & Lockhart Nicholson & Graham LLP
LandOfFree
Polythiophenes, block copolymers made therefrom, and methods... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Polythiophenes, block copolymers made therefrom, and methods..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Polythiophenes, block copolymers made therefrom, and methods... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3639097