Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing
Reexamination Certificate
2007-10-30
2007-10-30
Richter, Johann (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Amino nitrogen containing
C564S269000
Reexamination Certificate
active
11390777
ABSTRACT:
This invention provides aromatic diimines which have imino hydrocarbylidene groups with at least two carbon atoms, and aromatic secondary diamines which have amino hydrocarbyl groups with at least two carbon atoms. Both the aromatic diimines and the aromatic secondary diamines either are in the form of one phenyl ring, or are in the form of two phenyl rings connected by an alkylene bridge; each position ortho to an imino group or an amino group bears a hydrocarbyl group. When in the form of one phenyl ring, there are two imino groups on the ring or two amino groups on the ring; the imino groups or amino groups are meta or para relative to each other. When in the form of two phenyl rings connected by an alkylene bridge, there is either one imino group or one amino group on each phenyl ring. Also provided are processes for forming diimines and secondary diamines.
REFERENCES:
patent: 2380420 (1945-07-01), Emerson
patent: 2582128 (1952-01-01), Hurwitz et al.
patent: 2953579 (1960-09-01), Williams et al.
patent: 2965605 (1960-12-01), Reynolds et al.
patent: 3275567 (1966-09-01), Keith et al.
patent: 3336386 (1967-08-01), Dovell et al.
patent: 3350450 (1967-10-01), Dovell et al.
patent: 3414616 (1968-12-01), Summers
patent: 3538161 (1970-11-01), Dovell
patent: 3625710 (1971-12-01), Rizzi
patent: 3761425 (1973-09-01), Baessler et al.
patent: 3937730 (1976-02-01), Vogel et al.
patent: 3952056 (1976-04-01), Vogel et al.
patent: 3994975 (1976-11-01), Oude Alink et al.
patent: 4045486 (1977-08-01), Krall et al.
patent: 4140718 (1979-02-01), Symon
patent: 4161492 (1979-07-01), Weissel
patent: 4317916 (1982-03-01), Degischer et al.
patent: 4373107 (1983-02-01), Tahara et al.
patent: 4521624 (1985-06-01), Jackisch
patent: 4528363 (1985-07-01), Tominaga
patent: 4631298 (1986-12-01), Presswood
patent: 4663201 (1987-05-01), House et al.
patent: 4714512 (1987-12-01), House et al.
patent: 4760183 (1988-07-01), Papenfuhs et al.
patent: 4789691 (1988-12-01), Matzke et al.
patent: 4806616 (1989-02-01), Baumann et al.
patent: 4900868 (1990-02-01), Merten et al.
patent: 5001267 (1991-03-01), Speranza et al.
patent: 5002806 (1991-03-01), Chung
patent: 5006453 (1991-04-01), Nalepa et al.
patent: 5041668 (1991-08-01), Nalepa et al.
patent: 5145825 (1992-09-01), Deeba et al.
patent: 5312886 (1994-05-01), House et al.
patent: 5430188 (1995-07-01), Bader et al.
patent: 5470890 (1995-11-01), House et al.
patent: 5498585 (1996-03-01), Bartels et al.
patent: 5616799 (1997-04-01), Planker et al.
patent: 5646235 (1997-07-01), Zimmerman et al.
patent: 5744642 (1998-04-01), Lantzsch et al.
patent: 5847067 (1998-12-01), Gras
patent: 5859164 (1999-01-01), Gras et al.
patent: 6013755 (2000-01-01), Primeaux, II et al.
patent: 6156863 (2000-12-01), Wenning
patent: 6218480 (2001-04-01), Rappoport
patent: 6399736 (2002-06-01), Primeaux, II et al.
patent: 6403752 (2002-06-01), House et al.
patent: 6429338 (2002-08-01), Burdeniuc et al.
patent: 6444721 (2002-09-01), Schwalm et al.
patent: 6803445 (2004-10-01), Ishikawa et al.
patent: 2004/0015016 (2004-01-01), Su et al.
patent: 2004/0019238 (2004-01-01), Su et al.
patent: 2004/0054150 (2004-03-01), Murray
patent: 2004/0180778 (2004-09-01), Small
patent: 1218190 (1987-02-01), None
patent: 1352202 (2002-06-01), None
patent: 1163315 (1963-02-01), None
patent: 2940738 (1981-04-01), None
patent: 3728141 (1989-03-01), None
patent: 0014985 (1980-09-01), None
patent: 0469751 (1992-02-01), None
patent: 0779278 (1997-06-01), None
patent: 1067116 (2001-01-01), None
patent: 1229020 (2002-08-01), None
patent: 1320863 (1973-06-01), None
patent: 1478446 (1977-06-01), None
patent: 63052146 (1988-03-01), None
patent: 5274914 (1993-10-01), None
patent: WO-92/18575 (1992-10-01), None
patent: WO-97/01529 (1997-01-01), None
patent: WO-00/26181 (2000-05-01), None
patent: WO-03/018531 (2003-03-01), None
patent: WO-2004/073634 (2004-09-01), None
patent: WO-2005/033119 (2005-04-01), None
Kentoform reaction. Synthesis of hindered imines from 2,6-dialkylanilines and ketones, John T. Lai, Tetrahedron Letters 43 (2002) 1965-1967.
Adams et al., “Restricted Rotation in Aryl Amines. XIV. Isopropyl Derivatives of Dibenzenesulfonamidomesitylene”, J. Am. Chem. Soc., 1950, pp. 5077-5079, vol. 72.
Barmetter, “Acid-Catalyzed [3,3]-Sigmatropic Rearrangements of N-Propargylanilines”, Helvetica Chimica Acta, 1990, pp. 1515-1573, vol. 73, Verlag Helvetica Chimica Acta, Basel, CH.
Billaud et al., “Quantitative Analysis of Epoxy Resin Cure Reaction: A Study By Near-Infrared Spectroscopy”, Applied Spectroscopy, 2002, pp. 1413-1421, vol. 56(11).
Borges-Lopes et al., “Synthesis and Characterization of New Methyl-Substituted Azomethine-Siloxane Liquid Crystal Macrocycles Influence of the Methyl-Substitution on the Cycle Formation”, Polymer Bulletin, 1995, pp. 523-530, vol. 34, Springer, Heidelberg, Berlin, DE.
Campbell et al., “The Preparation of Unsymmetrical Secondary Aliphatic Amines”, J. Am. Chem. Soc., 1944, pp. 82-84, vol. 66.
Childs et al., “Assembly of a Nanoscale Chiral Ball Through Supramolecular Aggregation of Bowl-Shaped Triangular Helicates”, Angewandte Chemie, 2002, pp. 4244-4247, vol. 41, VCH Verlagsgesellschaft, Weinheim, DE.
Childs et al., “Using Noncovalent Intra-strand and Inter-strand Interactions to Prescribe Helix Formation within a Metallo-supramolecular System”, Chem. Cur. J., 2004, pp. 4291-4300, vol. 10(17).
Deschenaux et al., “Structural Isomerism in Polycondensates. IV. Synthesis and Characterization of Liquid Crystalline Poly(azomethines) and Low Molecular Weight Model Compounds”, Helvetica Chimica Acta, 1986, pp. 1349-1355, vol. 69(6).
Distefano, “Reinvestigation of the Formaldehyde-Aniline Condensation. Part 4. Ultraviolet Photoelectron and Electron Transmission Spectra of N-Methyleneaniline and its Symmetric Dimethyl Ring-substituted Homologues and Semiempirical Theoretical Evaluations”, J. Chem. Soc. Perkin Trans II, 1985, pp. 1623-1627.
Dovell & Greenfield, “Platinum Metal Sulfides as Heterogeneous Hydrogenation Catalysts”, J. Am. Chem. Soc., 1965, pp. 2767-2768, vol. 87.
Dvolaitzky et al., “Stable N,N′-di-tert-butyl-meta-phenylenebisnitroxides-Unexpected Ground-State Singlets”, Angewandte Chemie Int. Ed. Engl., 1992; pp. 180-181, vol. 31(2).
Emerson et al., “The Reductive Alkylation of Hindred Aromatic Primary Amines”, J. Am. Chem. Soc., 1941, pp. 972-974, vol. 63.
Hine et al., “Polar Effects on the Formation of Imines from Isobutyraldehyde and Primary Aliphatic Amines”, The Journal of Organic Chemistry, 1970, pp. 340-344, vol. 85.
Jie et al., “Bridged Bis-Pyridinylimino Dinickel (II) Complexes: Syntheses, Characterization, Ethylene Oligomerization and Polymerization”, Journal of Organometallic Chemistry, 2005, pp. 1739-1749, vol. 690, Elsevier-Sequola S.A. Lausanne, CH.
Lai, J.T., “Ketoform Reaction. Synthesis of Hindered Imines from 2,6-dialkylanilines and Ketones”, Tetrahedron Letters, 2002, p. 1965-1967; 1996, vol. 43, Elsevier Science Publishers, Amsterdam, NL.
Layer, Robert W.; “The Chemistry of Imines”, Chemical Reviews; 1963; vol. 63; pp. 489-510.
Luo et al., “New Bi-nuclear and Multi-nuclear α-diimine
ickel Catalysts For Ethylene Polymerization”, Journal of Molecular Catalysts, 2005, pp. 153-161, vol. 227.
March, “Reactions, Mechanisms, and Structure”, Advanced Organic Chemistry, 1992, pp. 896-900, 4thEd., John Wiley & Sons, US.
Mi et al., “Homo- and Copolymerization of Norbomene and Styrene with Pd- and Ni-Based Novel Bridged Dinuclear Diimine Complexes and MAO”, Macromol. Chem. Phys., 2003, pp. 868-876, vol. 204(5/6).
Pal et al., “Schiff Base Linked Ferrocenyl Complexes for Second-Order Nonlinear Optics”, Journal of Organometallic Chemistry, 2000, pp. 248-259, vol. 604, Elsevier-Sequoia S.A., Lausanne, CH.
Parker, et al., “Reaction Chemistry of Tri-Substituted Mesityl
Brandt Vernon O.
Lee John Y.
Orgad Judit
Sabahi Mahmood
Wiggins Paul L.
Albemarle Corporation
Cho Jennifer
Kliebert Jeremy J.
Richter Johann
LandOfFree
Diimines and secondary diamines does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Diimines and secondary diamines, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Diimines and secondary diamines will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3897504