Air dried cross-linkable polymeric vehicles which include acetylenic groups

US005556921A United States Patent ~191 Dirlikov et al. [45] [54] AIR DRIED CROSS-LINKABLE POLYMERIC VEHICLES WHICH INCLUDE ACETYLENIC GROUPS [75] Inventors: Stoil Dirlikov; Zhao Chen, both of Ypsilanti, Mich. [73] Assignee: Eastern Michigan University, Ypsilanti, Mich. [21] Appl. No.: 195,545 [22] Filed: Feb. 14, 1994 (Under 37 CFR 1.47) [51] Int. CL6 ..................................CO8K 3/10; C08J 3124 [52] U.S. C1. .......................... 5251245; 5251246; 5251275; 5251328.1; 5251279; 526193; 5261147; 5261172; 5261285 Field of Search ..................................... 5251245, 246, 1581 525275, 328.1; 526193, 147, 172, 285 [561 [li] References Cited U.S. PATENT DOCUMENTS 411964 211971 211971 711971 1011980 1111987 1211989 811993 311994 Miller ...................................... 5261284 D' Alelio ................................. 5251153 D'Alelio .............................. 5251328.1 Hay ......................................... 4301270 Picklesimer ............................. 5581419 Lau et al. ................................ 5251275 Inbasekaran et al. .................. 5681631 Yamada et al. ......................... 5261285 D'Alelio ................................. 5281353 OTHER PUBLICATIONS A. S. Hay (1969) J Polym. Sci A-I, vol. 7, 1625-1634. Wu et al., "Coatings Curable with Low-Emission Radiation," in Radiation Curing of Polymeric Materials, ACS Symposium Series 417, Washington, D.C. (1990). Owen, "Olefinic Acids. Part I. The Reactivity of a-Bromocrotonic Acid." J. Am. Chem. Soc. 385 (1945). Raphael, Acetylenic Compounds in Organic Synthesis, 127, Butterworths Scientific Publications (1955). Rutledge, Acetylenes and Allenes, Reinhold Book Corp., New York, 283 (1969). Patent Number: Date of Patent: 5,556,921 Sep. 17,1996 Kruse et al., "N,N-Dialkyl-1,l-dimethyl-2-butynylamines by the Reaction of Propyne with Secondary Aliphatic Amines," 83 J. Am. Chem. Soc. 213 (1961). Kruse et al., "Ethylidenimies by the Reaction of Acetylene with Primary Aliphatic Amines," 83 J. Am. Chem. Soc. 216 (1961). McMullen et al., "Elimination-Addition. Part Vm. Structures of Acetylene-Arnine Adducts," (B) J. Chem. Soc. 1217 (1966). Hay, "Oxidative Coupling of Acetylenes," 25 J. Org. Chem. 1275 (1960). Hay, "Oxidative Coupling of Acetylenes LI," 27 J. Org. Chem. 3320 (1962). Hennion et al., "A Proposed Mechanism for Mercury Catalysis in Acetylene Addition Reactions", 1 J. Org. Chem. 159 (1936). Glaser, 154 Ann. 137 (1870). Glaser, 2 Ber. 422 (1869). Hay et al., "Photosensitive Polyacetylenes," 8 Polymer Letters 97 (1970). Dirlikov, "Propargyl-Terminated Resins-A Hydrophobic Substitute for Epoxy Resins," 2(1) High Performance Polymers 67 (1990). Eglington et al., "The Coupling of Acetylenic Compounds" in Advances in Organic Chemistry, 225-263, Interscience Publishers, N.Y. (1963). Feng et al., "Mechanism of B-Staging and Curing of Propargyl Terminated Resins," 60 Polymer Mat. Sci. Eng. 618 (1989). Bowden et al., "Researches on Acetylenic Compounds Part Vm. Miscellaneous Addition Reactions of Ethynyl Ketones," J. Am. Chem. Soc. 945 (1946). Chen et al., "Air-Drying Mechanism of Propargyl Terrninated Resins; I. Cobalt Drier," 69 Polym. Mater. Sci. Eng. 388 (1993). Dirlikov, "A Review on Propargyl Terminated Resins," 62 Proc. Polym. Mat. Sci. Eng. 603 (1990). Primary Examiner-Mark Nagumo Attorney, Agent, or Finn-Fitch, Even, Tabin & Flannery [571 ABSTRACT This invention is directed to a fast curing polymer composition which does not require baking or thermosetting to provide a cross-linked coating binder. The composition comprises a polymer which is a homopolymer or copolymer