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United States Patent Office Patented Jan 3,424,736 United States Patent Office Patented Jan. 28, 1969 2 tadiene in a solvent at a temperature between -10 and 3,424,736 90 C. with a catalyst containing titanium essentially in the DENE POLYMERIZATION PROCESS AND CATALYST THEREFOR tetravalent state and prepared by reaction of an organo Walter Nudenberg, West Caldwell, Dudley Bruce Merri magnesium compound, titanium tetrahalide and butadiene. field, Basking Ridge, and Edward Axel Delaney, Morris 5 The active catalyst for cis-polybutadiene manufacture pro Plains, N.J., assignors to Texas-U.S. Chemical Com duced by the reaction of an ether-free organomagnesium pany, Port Neches, Tex., a corporation of Delaware compound, titanium tetrahalide and butadiene is a free No Drawing. Continuation-in-part of abandoned applica radical having the formula CHTiX, wherein X is halo tion Ser. No. 288,877, June 19, 1963, which is a con gen, or a reaction product thereof having the formula tinuation of application Ser. No. 38,417, June 24, 1960. TiXCH-CHTiX or the formula TiXCHTiX. The This application Dec. 5, 1966, Ser. No. 599,671 O U.S. C. 260-94.3 12 Claims reaction product TiXCH-CHTiX is a dimer of the Int, C. C08d 1/14, 1/16, 3/08 CAHsTix8" free radical while the reaction product TiXCHTIX 5 is formed by reaction of the CHTiX free radical with ABSTRACT OF THE DISCLOSURE a TiX free radical. A process for the controlled orientation polymerization A feature of this invention involves the use of a of butadiene characterized by contacting the butadiene in C3-C6 monoolefin as a component of the solvent mixture a solvent with catalyst consisting of the components (1) in which the butadiene polymerization is effected. The Grignard composition reacted with (2) a titanium tetra 20 use of Cs-C monoolefins which have high heat capacity halide in (3) a complex form under conditions such as as cosolvents with an aromatic hydrocarbon solvent has the titanium is maintained tetravalent, for a time and at a the advantage of reducing the solution viscosity with the low temperature, sufficient to induce completion of polym result that it is possible to obtain better heat transfer erization, and thereafter recovering the polymer. during the polymerization and to continue the polymeriza 25 tion to a higher solution solids content. The use of a Cs-C6 monoolefin as a cosolvent also results in the forma This invention relates to a process for polymerizing tion of cis-14 polybutadiene with less tendency to flow butadiene to produce cis-polybutadiene of controlled 1,4 during storage and having a narrow molecular weight structure. More particularly, this invention is directed to a range. Another advantage resulting from the use of the process for polymerizing butadiene to polybutadiene of 30 C3-C6 monoolefin as a cosolvent with an aromatic hydro cis-1,4 structure employing a novel catalyst and to carbon solvent is increased catalyst efficiency. Employing methods of preparation of this novel catalyst. Cs-C6 monoolefins as cosolvents, it is possible to reduce The subject application is a continuation-in-part of our the catalyst requirement by 4 to 4 of that required if commonly-assigned, copending application Ser. No. the polymerization process of the invention is effected in 38,417, filed June 24, 1960, now abandoned, and a con a solvent consisting of aromatic hydrocarbons. It is not tinuation of our application Ser. No. 288,877 filed June 19, feasible to substitute alkanes for the C-C monoolefins as 1963, now abandoned. cosolvents because their use results in substantial insolu Conjugated diolefin polymers of controlled structure bility of the active catalyst resulting from the reaction of have been prepared with catalyst systems comprising mix the organomagnesium compound, titanium tetrahalide and tures of aluminum alkyls and titanium tetrahalide. Cis-1,4 40 butadiene and a corresponding decrease in catalyst effec polybutadiene prepared with aluminum alkyl-titanium tiveness. iodide catalyst systems have recently been made available The preferred monoolefin cosolvent is isobutylene but in commercial quantities and are being widely used as other monoolefins such as propylene, butene-2, pentene-1, blending agents for SBR and natural rubber. A serious pentene-2, 2-methylbutene-2, hexene-1,3-methyl pentene limitation of the aluminum alkyl system is its temperature 45 2, 2-ethyl butene-2 and mixtures thereof can be employed sensitivity. At polymerization temperature above 20° C., as the cosolvents with the aromatic hydrocarbons. The the cis content of the polymer decreases and molecular C3-C6 monoolefin cosolvent is employed in a concentra weight control is difficult to attain with aluminum alkyl tion equivalent to 0.2 to 1.0 volumes per volume of aro Systems. Aluminum alkyl-titanium halide catalyst systems matic hydrocarbon solvent. In order to prevent formation and other catalyst systems containing titanium halides in 50 of cis-polybutadiene-olefin copolymers, the concentration combination with reducing agents are useful for the polym of the C3-Cs cosolvent should not exceed approximately erization of olefins such as ethylene and propylene. In five times the concentration of the butadiene monomer. As these catalyst Systems the active catalyst component is said disclosed in our copending application Ser. No. 163,855, to require solid TiX or some other reduced form of filed Jan. 2, 1962, abandoned and continued as Ser. No. titanium in which the titanium is in a valence state of 3 or 55 473,497, issued Dec. 19, 1967 as U.S. Patent 3,357,960, below. Various metal alkyls and metal hydrides such as cis-polybutadiene - isobutylene copolymers are formed aluminum alkyls, dialkyl magnesium compounds, dialkyl using the catalyst obtained by reaction of an organomag Zinc compounds, Gignard reagents, lithium hydride, etc. nesium compound, titanium tetrahalide and butadiene em are used to reduce the titanium tetrahalide to a valence ploying a monomer reaction mixture containing 5 or more state below 4, that is, to a valence state of 2 or 3. The 60 volumes of isobutylene per volume of butadiene. subject invention involves the discovery that reduced The organomagnesium compound, which reacts with forms of titanium halides containing titanium in a valence butadiene and titanium tetrahalide to form the active cata state below 4 in admixture with organomagnesium com lyst containing tetravalent titanium, has the formula pounds are completely inactive for cis polymerization of RMgX or R2Mg wherein R is a hydrocarbyl radical con butadiene and that polymerization of butadiene to a poly 65 taining 1 to 30 carbon atoms and X is a halogen which mer of cis 1,4 structure is effected with a catalyst con may be either chlorine, bromine, iodine or fluorine. The taining titanium essentially in a tetravalent state and pre R radical is preferably an alkyl or aryl hydrocarby radi pared by reaction of an organomagnesium compound, cal containing 6 or more carbon atoms and the X is pref. titanium tetrahalide and butadiene. erably iodine, bromine or chlorine in the RMgX formula. In accordance with this invention, polybutadiene having 70 Examples of the organomagnesium compounds which re a cis content above 70% is prepared by polymerizing bu act with butadiene and titanium tetrahalide to form the 3,424,736 3 4 CHTiX free radical which catalyzes butadiene polym best expressed in mols of total catalyst, i.e. mols of tita erization are the following: nium tetrahalide plus mols of Grignard compound, per Effective Grignard reagents are dodecyl magnesium mol of butadiene reactant. The broad catalyst concentra iodide, dodecyl magnesium bromide, stearyl magnesium tion on this basis falls between 0.00001 and 0.01 mol of iodide, ethyl magnesium bromide, ethyl magnesium iodide, catalyst per mol of butadiene with catalyst concentrations methyl magnesium iodide, nonyl magnesium iodide, between 0.00001 and 0.004 mol of catalyst per mol of naphthyl magnesium bromide, phenyl magnesium bro butadiene being recommended. mide, phenyl magnesium chloride, tolyl magnesium bro The preferred procedure for preparing a CHTiX free mide, n-octyl magnesium iodide, t-octyl magnesium bro radical catalyst and its reaction products in which titanium mide, hexadecyl magnesium chloride and propargyll mag is essentially in the tetravalent state is the "in situ' pro nesium bromide. 10 cedure in which the organomagnesium compound and Effective dihydrocarby magnesium compounds are di titanium tetrahalide are contacted in a hydrocarbon mix dodecyl magnesium, diphenyl magnesium, di-tolyl mag ture containing the butadiene reactant. Usually the or nesium, di-2-ethylhexyl magnesium, di-naphthyl mag ganomagnesium compound is dispersed and/or dissolved nesium, phenyl naphthyl magnesium and phenyl benzyl 5 in a mixture comprising butadiene and hydrocarbon sol magnesium. vent and a hydrocarbon solution of titanium tetrahalide Titanium tetrahalides employed in preparing the active is added to the mixture comprising butadiene, organo free radical CHTX3 catalysts and its reaction products magnesium compound and solvent. As pointed out pre are exemplified by the following: titanium tetraiodide, viously, the organomagnesium compound-titanium tetra titanium tetrabromide, titanium tetrachloride, titanium 20 halide-butadiene reaction mixture contains butadiene tetrafluoride, mixtures thereof and also mixed titanium monomer in amount equivalent to at least 300 mols and tetrahalides such as titanium dichloride diiodide, titanium preferably at least 500 mols of butadiene per mol of dibromide diiodide and titanium monobromide triiodide. titanium tetrahalide reactant. The use of the butadiene The titanium iodides are preferably used when a high cis reactant in such large mol excess assures the production content polymer is a desired product of the butadiene 25 of the active CAHTiX3 free radical catalyst and prevents polymerization as will be pointed out hereafter. reduction of the titanium halide by the organomagnesium The formation of the active catalyst, the CHTiX free compound to an inactive solid polymeric trihalide in which radical or its reaction products, is effected by reaction of titanium is essentially in the trivalent state.
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