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[75] Inventors: Herve M. Cheradame, Grignan, E. E. Inst S: S US005629394A United States Patent (19) 11 Patent Number: 5,629,394 Cheradame et al. 45 Date of Patent: May 13, 1997 54 DIRECTSYNTHESIS BY LIVING CATIONIC 4,952,739 8/1990 Chen ......................................... 585/18 POLYMERIZATION OF NTROGEN- 4,956,107 9/1990 Gutierrez et al... 252A47 CONTAINING POLYMERS 4,963,275 10/1990 Gutierrez et al. ......................... 252A47 5,017,299 5/1991 Gutierrez et al. .. 252/.515 R [75] Inventors: Herve M. Cheradame, Grignan, E. E. inst s: S. Frank J. Chen, Edison Jon E. 5,102,566 4/1992 Fetterman, Jr. et al. 252/32.7 E . Stanat Westfield, both of N.J.; 5,122,572 6/1992 Kennedy et al. ....................... 525/314 Hung A. Nguyen, La Kremlin Bicetre; 5,444,135 8/1995 Cheradame et al. ................. 526/219.2 Behrooz R. Tabar, Paris, both of France FOREIGN PATENT DOCUMENTS (73) Assignee: Exxon Chemical Patents Inc, Linden, oo:: E. St. Pat. Of.. N. 0341012A2 11/1989 European Pat. Off.. 984.409 2/1965 United Kingdom. 21 Appl. No.: 474,043 OTHER PUBLICATIONS (22 Filed: Jun. 7, 1995 Kennedy and Ivan, "Designed Polymers by Carbocationic Related U.S. Application Data Molecular Engineering", Theory and Practice, Hanser Pub lishers, Munich, Vienna, New York and Barcelona, Section I62 Division of Ser. No. 992.511, Dec. 17, 1992, Pat No. II.3.4., pp.39-42, (1992). 5,444,135. M. Miyamoto, M. Sawamoto, T. Higashimura, Macromol (51] Int. Cl. .............. Cos 400 C08F 12006, ecules, Vol. 17, pp. 265-268 (1984). C08F 130/08; C08F 12,08; CO8F 106 Discher, Modern Inorganic Pharmaceutical Chemistry, John 52 U.S. Cl. ...................... 2619.2.5.2220,526,260. Wiley & Sons, NYP33 (19) 526/267; 526/279; 526/346; 526/348.7 Kennedy et al., “Designed Polymers by Carbocationic Mac 58 Field of Search ................................. 52g/292,220. romolecularPublishers, 1992, Engineering": pp. 31 to 35.Theory and Practice, Hanser 526/260,267, 279, 346,348.7 Joseph P. Kennedy “Cationic Polymerization of Olefins, A Critical Inventory”, pp. 39 to 53, (John Wiley & Sons, 56 References Cited 1975). U.S. PATENT DOCUMENTS Billmeyer, Textbook of Polymer Science, Second Edition, pp. 81-84 (1971). Re. 26,433 8/1968 Le Suer ................................. 252/33.6 Bastide et al., Cycloaddition dipolaire 1-3, aux alcynes, 3,150,088 9/1964 Hunt et al. .. 25232T Bulletin De La Societe Chimique De France Nos. 7-8, pp. 3,150,089 9/1964 Hunt et al... ... 252/33 a aaaa. 252A35 2555-2579 (1973). 3,306,9083.271,310 2/19679/1966 Le Suer ...... 260/326.3 Bastide et al., Cycloaddition dipolaire-13a s aux alcynes, 3,331,776 7/1967 Krukziener. 252/56 Bulletin De La Societe Chimique De France, Nos. 9-10, pp. 3,381,022 4/1968 Le Suer ...... 260/4048 2871-2887 (1973). 3,445,441 5/1969 Rushton . ... 260/89.5 Kazankov et al., J. Org. Chem. USSR 77.451 (1975). 3,522,179 7/1970 Le Suer .. ... 252/51.5 "Palladium-catalyzed Decomposition of Azides". Bulletin 3,542,680 11/1970 Le Suer .................................... 252/57 Chemical Society of Japan, 49, pp. 506-509 (1976). 3,645,917 2/1972 Vandenberg ... 260/2A 3.684,713 8/1972 Piccelini.......... ... 252A7.5 (List continued on next page.) 3,697,428 10/1972 Meinhardt et al. 252A56 D 3,755,169 8/1973 Adams et al. ............................ 2S2/35 Primary Examiner-Joseph L. Schofer 3,836,469 9/1974 Miller ......... ... 252A10.5 Assistant Examiner Wu C. Cheng 3,836,4713,836,470 9/1974 Miller. 2,252/515A Attorney Agent, or Firm-Harvey L. Cohen 3,838,050 9/1974 Miller. ... 252/495 57 ABSTRACT 3,838,052 9/1974 Miller. ... 252A56R 3,879,308 4/1975 Miller. ... 252/56 R A method is provided for the direct synthesis by living 3,957,854 5/1976 Miller. 26082R cationic polymerization of novel polymeric materials func 3,957,855 5/1976 Miller .................................. 260/482 R. tionalized with desirable nitrogen-containing functional : Ag: tn 33. groups such as terminal azido, cyano, carbonylamino, 4,102,798 7/1978 Ryer et al. ...... "... cyanato, thiocyanato or thiocarbonylamino groups. Poly 4,113,639 9/1978 Lonstrup et al. 2525.5A merization and functionalization occur in a substantially 4,113,804 9/1978 Cotton et al. ... .26897 A simultaneous manner. All necessary reactants for the func 4,116,876 9/1978 Brois et al. ... 252A9.6 tionalization are present when polymerization is initiated. 4,151,113 4/1979 Thaler ........ 252/.429R The nitrogen-containing functional group is provided as a 4,268,450 5/1981 Frankel et al... ... 260/349 part of a molecule having a release moiety which is prefer 4,393,199 7/1983 Manser .................................... 528/406 ably resonance stabilized or a tertiary alkyl type and which 4,405,762 9/1983 Earl et al. ... 525/410 acts to aid the nitrogen-containing species in functioning as 4,483,978 11/1984. Manser .................................... 528/406 a leavin O 4,568,732 2/1986 Kennedy et al. ... 526/206 g group. 4,611,037 9/1986 Musch et al. ....... 526/135 4,857,217 8/1989 Gutierrez et al. ......................... 252/47 20 Claims, No Drawings 5,629,394 Page 2 OTHER PUBLICATIONS Photodecomposition of Alykl Azides, J. Am. Chem. Soc. 93, "Base Decomposition of Azides Leading to Nitriles". Jour pp. 1537-1538, (1971). nal Org. Chem., vol. 44, No. 16, pp. 2951-2952, (1979). Lwowski, Nitrenes, Wiley-Interscience, p. 112. Knudsen et al., A Convenient One-Step Conversion of Lansbury, "Nitrenium Cations", in Lwowski, Nitrens, Aromatic Nitro Compounds to Phenols, J. Org. Chem., vol. Wiley-Interscience, pp. 405-419. 39, No. 23, pp. 3343-3346. Facile Reaction of Dialkylchloroboranes with Organic "The Reaction of Organic Azides with Carbon Monoxide.” Azides, The J. Am. Chem. Soc. 94, pp. 2114-2115, (1973). J. Am. Chem. Soc. 90, pp. 3295-3296, (1968). Facile Reaction of Alkyland Aryldichloroboranes with "Addition of Aryl Nitrenes to Olefins”. The J.C.S. Chem. Organic Acids, The J. Am. Chem. Soc. 95, pp. 2394-2396, Comm., pp. 1160-1161, (1972). (1973). Anderson et al., Addition of Nitrenes to Acetylene, Antiaro Morton, Rubber Technology, Second Edition, Chapter 17, maticity of I-H Azirines, Chemical Communications, p. 147 pp. 440-458, van Nostrand Reinhold Co., (1973). (1969). Chemical Abstracts, vol. 117, No. 1, 13 Jul. 1992, Colum Moriarty et al., The Direct and Photosensitized Decompo bus, Ohio, U.S.; Abstract No. 8706q, Kuznetsova, M. B. sition of Alkyl Azides, Tetrahedron, 26 pp. 1379-1392, “Manufacture of Polyisobutylene in Presence of Chain (1970). Transfer Agents” p. 15. 5,629,394 1. 2 DIRECT SYNTHESS BY LIVING CATIONC European Patent No. 341,012 which relates to the produc POLYMERIZATION OF NTROGEN tion of uniform molecular weight polymers. This process CONTAINING POLYMERS involves a monomer, a solvent, an initiator component having an acetate, an etherate, a hydroxyl group or a halogen This is a continuation of application Ser. No. 992,511, 5 function of a benzylic type initiator, a Lewis acid and an electron donor component having an electron donor number filed Dec. 17, 1992, U.S. Pat. No. 5,444,135. of from 25 to 50. BACKGROUND OF THE INVENTION Chain end functionalization may result from transfer reactions such as those described in U.S. Pat. No. 4,568,732 1. Field of the Invention which relates to a continuous process for forming telechelic This invention relates to a method for direct synthesis, by 10 halogenated polymers wherein a cationically polymerizable living cationic polymerization, of nitrogen-containing monomer and an inifer (initiator-transfer agent) are con polymers, and particularly to the production of nitrogen tacted with a boron chloride solvent solution. Disclosed containing polymeric materials in a single step Friedel monomers are olefins of from 4 to 12 carbon atoms, e.g. Crafts polymerization of olefinic materials containing sub isobutylene. Suitable inifers are halogenated aromatic or stantial amounts of isobutylene. 15 aliphatic hydrocarbons, vinyl halides, silane-substituted 2. Description of Related Art hydrocarbyl halides, dicyclopentadienyl halides, alpha A review of carbocationic macromolecular engineering is chlorostyrene homopolymers, and 2-chloro-propene provided in Kennedy and Ivan, Designed Polymers by homopolymers and copolymers, wherein the halide is F, Cl Carbocationic Molecular Engineering: Theory and 20 or Sr. In this patent, the polydispersity index of the polymer Practice, Hanser Publishers, Munich, Vienna, New York and was not particularly low, and the terminal function was a Barcelona, Section II.3.4 which relates to mechanistic con tertiary chloride which necessitates subsequent chemical siderations: a comprehensive view of living carbocationic steps in order to obtain the desired nitrogen-containing polymerization and the spectrum of ionicities of active function. species. At page 32, living polymerizations are defined as 25 Polymers, particularly polyolefin substrates, having ideal living polymerization in which charge transfer and nitrogen-containing functional groups such as the azide, termination are absent, and quasi-living polymerizations are cyano, carbonylamino or thiocarbonylamino groups are use defined as having rapidly reversible charge transfer and/or ful since the functional group is polar, and imparts desirable termination present wherein the rate of these processes is properties to a polyolefinic Substrate. Also, these groups may faster than that of propagation. In either case the living 30 act as a reactive site for further modification of the polymer. behavior of the polymer results in a polymer in which charge Nitrogen-containing polyisobutylenes have applications transfer and termination are absent. For the purpose of the such as lube additives, compatibilizers, emulsifiers, and the present invention, living polymers are therefore defined as like. For example, azide terminal polymers may be further polymers which have substantially and preferably no appar modified by phthalamidation or reduction of the azide group ent chain transfer and termination.
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