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United States Patent '0 Rice Patented Aug 1 3,597,403‘ United States Patent '0 rice Patented Aug. 3, 197]]. l 2 halides, (B) at least one compound selected from a group 3,597,403 NOVEL CATALYSTS FOR THE RING-OPENING consisting of molecular oxygen, chlorine, bromine, iodine POLYMERIZATION 0F UNSATIURATED ALllCY and cyanogen halides, and (C) at least one transition CLlC COMPDUNDS metal compound selected from the group consisting of Eilert A. Ofstead, Cuyahoga Falls, Ohio, assignor to The tungsten and molybdenum complexes corresponding to the Goodyear Tire & Rubber Company, Akron, Ohio formula M (CO),R Where M is tungsten and molybdenum, No Drawing. Filed Oct. 27, 1969, Ser. No. 869,909 C is carbon, 0 is oxygen and R is an unsaturated hydro lint. Cl. C08f 7/02, 15/04 carbon compound having at least two non-conjugated car US. Cl. 260-881 8 Claims bon-to-carbon double bonds and where R is attached to 10 the transition metal by coordination through two carbon to-carbon double bonds. ABSTRACT OF THE DISCLOSURE Representative examples of the compounds useful as the There is disclosed a process for the ring-opening polym (A) catalyst component include alkylaluminum dihalides erization of certain unsaturated alicyclic compounds such as ethylaluminum dichloride, isobutylaluminum di which comprises subjecting said unsaturated alicyclic com 15 chloride, propylaluminum dichloride, ethylaluminum di pounds to a catalyst system comprising (A) at least one bromide, ethylaluminum diiodide and the like; alkylalu compound selected from a group consisting of alkylalu minum sesquihalides such as ethylaluminum sesquichlo minum dihalides, alkylaluminum sesquihalides and alu ride, methylaluminum sesquichloride, methylaluminum minum halides, (B) at least one compound selected from sesq-uibromide and the like; and aluminum halides such the group consisting of molecular oxygen, chlorine, bro 20 as aluminum chloride, aluminum bromide and the like. mine, iodine and cyanogen halides, and (C) at least one Compounds useful as the (B) catalyst component of the transition metal compound selected from the group present invention include molecular oxygen, chlorine, bro consisting of tungsten and molybdenum carbonyl com mine, iodine and cyanogen halides representative of which plex compounds corresponding to the formula M(CO)4R are cyanogen chloride, cyanogen bromide and the like. where M is tungsten and molybdenum and R is an un 25 Representative examples of the compounds useful as the saturated hydrocarbon compound having at least two non (C) catalyst component de?ned above and Where R, the conjugated carbon-to-carbon double bonds and wherein R unsaturated hydrocarbon compound, is selected from a is attached to the transition metal by coordination through group consisting of alkapolyene, cycloalkapolyene and two carbon-to-carbon double bonds. polycycloalkapolyene compounds having at least two non 30 conjugated carbon~to~carbon double bonds include 1,5 hexadiene tungsten tetracarbonyl; 1,5 - cyclooctadiene This invention relates to a process for polymerizing un tungsten tetracarbonyl; norbornadiene tungsten tetracar saturated alicyclic compounds and to the products result bonyl; dicyclopentadiene tungsten tetracarbonyl; l,5~cyclo ing therefrom. In its broad aspect, the invention is directed octadiene molybdenum tetracarbonyl and norbornadiene to the preparation of polymers derived from unsaturated 35 molybdenum tetracarbonyl and the like. alicyclic compounds which contain at least one alicyclic Various unsaturated alicyclic compounds may be polym ring structure containing at least two carbon atoms con erized in the practice of this invention. Unsaturated ali nected through a double bond. It is also related to catalyst cyclic compounds useful in accordance with this invention systems useful in the process for polymerizing unsaturated are selected from the group consisting of (A) alicyclic alicyclic compounds. 40 compound corresponding to the formula: The polymerization process of this invention may be used to prepare novel solid polymers. The properties and CH=OH characteristics of the polymers can be “tailor made” to Q ?t a Wide variety of uses and fields of application. The properties and characteristics of the polymers resulting 45 (I) from the polymerization process of this invention can be varied over a Wide range dependnig on (1) the particular ‘ wherein: unsaturated alicyclic monomer chosen to be polymerized, (1) Q is a fragment which comprises a sequence of (2) the particular polymerization catalyst employed, and 50 at least 5 carbon atoms situated in linear succession be (3) the particular polymerization conditions employed. tween the methylene carbons which constitute the double The products resulting from the polymerization of this in bond; vention can be employed in a variety of applications; for (2) The carbon atoms in the linear succession of Q example, they may be employed to produce ?nished rub~ may be interconnected by both carbon-to-carbon single ber articles such as pneumatic tires, molded goods and 55 bonds and carbon-to-carbon double bonds; the like or they may be materials Which are useful to man (3) Any of the carbon atoms in the linear succession of ufacture articles such as ?lms and ?bers. They may also Q may be substituted by at least one member from the be employed to form ?nished products by molding tech group of alkyl, aryl, alkenyl, aralkyl, alkaryl, cycloalkyl, niques. cycloalkenyl, bicycloalkyl and bicycloalkenyl radicals; This invention comprises polymerizing at least one ali 60 (4) Any of said carbon atoms in the linear succession cycilc compound selected from the group consisting of (1) of Q may be constituents of aromatic rings and alicyclic unsaturated alicyclic compounds containing at least four rings; and and not more than ?ve carbon atoms in the cyclic ring (5) Said alicyclic unsaturated hydrocarbon contains and containing one carbon-to-carbon double bond in the no conjugated double bonds; (B) alicyclic compounds cyclic ring, and (2) unsaturated alicyclic compounds con 65 corresponding to the formula: taining at least seven carbon atoms in the cyclic ring and wherein: containing at least one carbon-to-carbon double bond in CH—CH the cyclic ring, by subjecting said alicyclic compounds to ring-opening polymerization conditions, in the presence P of a catalyst system comprised of (A) at least one com 70 (11) pound selected from a group consisting of alkylaluminum wherein: dihalides, alkylaluminum sesquihalides and aluminum (1) P is a fragment which comprises a sequence of 3,597,403 at least 2 and not more than 3 carbon atoms situated in a manner that they are not adjacent and are non-conju linear succession between the methylidene carbons which gated. Representative examples of such preferred materials constitute the double bond; are cyclobutene, cyclopentene, cyclooctene, cyclododecene, (2) The carbon atoms in linear succession of P are and 1,5-cyclooctadiene, 1,5,9-cyclododecatriene and connected by carbon~to~carbon single bonds; 1,9,17-cyclotetracosatriene. (3) Any of the carbons in the linear succession of P Representative examples of substituted alicyclic com may be substituted by at least one substituent member pounds are alkyl-substituted compounds such as l-methyl from the group of alkyl, aryl, alkenyl, aralkyl, alkaryl, 1,5-cyclooctadiene; aryl-substituted compounds such as cycloalkyl, cycloalkenyl, bicycloalkyl and bicycloalkenyl 3-phenyl-l-cyclooctene; aralkyl-substituted compounds radicals; 10 such as 3-benzyl-1-cyclooctene; alkaryl-substituted com (4) Any of said carbons in linear succession of P may pounds such as 3-tolyl-l-cycooctene and halogen-substi be constituents of aromatic rings and alicyclic rings, and tuted compounds such as as 5-chloro-l-cyclooctene, l (5) Said alicyclic unsaturated hydrocarbon compound chloro-1,5-cyclooctadiene; S-chloro-l-cyclododecene and contains no conjugated double bonds; and (C) alicyclic 5,6-dichloro-l-cyclooctene. Mixtures of the unsaturated compounds corresponding to the formula: 15 alicyclic compounds may be polymerized including both substituted, unsaturated alicyclic compounds and the un substituted unsaturated alicyclic compounds. 01 The catalysts employed in this invention are prepared by mixing the components by known techniques. Thus, 20 the catalysts may be prepared by “preformed” or “in situ” techniques. By “preformed” is meant the manner in which the catalyst components are mixed together prior to ex where Z represents: posure of any of the catalyst components to the monomer (1) A vinylene double bond of the formula to be polymerized. By “in situ” is meant that the catalyst 25 components are added separately to the monomer to be --CH=CH—; polymerized. The catalyst components can be mixed either or as pure compounds or as suspensions or solutions in liquids ‘(2) A hydrocarbon fragment containing: which do not adversely affect the ring-opening polymeriz (a) At least four carbon atoms situated in a linear ation. Representative of such liquids are saturated hydro~ succession between carbons 3 and 5 of (III); 30 carbons such as hexane, pentane and the like; alicyclic (b) At least one —CI-Ir= CH—- grouping, said hydrocarbons such as cyclohexane, cyclooctane and the like; and aromatic hydrocarbons such as benzene, toluene and the like. grouping being a constituent of at least one 4 or 5 or 7 However, for both the “preformed” and the “in situ” or larger membered ring; 35 techniques of catalyst addition, certain orders of addition (c) Any remaining carbon in the linear succession of the three catalyst components
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