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United States Patent Office Patented Mar 3,720,654 United States Patent Office Patented Mar. 13, 1973 2 DESCRIPTION OF THE PREFERRED 3,720,654 EMBODEMENTS MOELECULAR SZING PROCESS FOR PREPAIR. NG LOW MOLECULAR ISOBUTYLENE-CONSU As indicated above, the butyl-type copolymer which GATED POLYENE CORPOLYMERS is treated in accordance with the present invention may Jerome Robert Oechowski, Trenton, N.S., assignor to be any isobutylene-conjugated polyene copolymer having Cities Service Company, New York, N.Y. a combined polyene content of about 1-5 mol percent. No Drawing. Fied May 2, 1971, Ser. No. 145,957 The combined polyene units may be derived from any Int, C. CO8d 5/00 CO86 1/88 conjugated polyene monomers containing at least four U.S. C. 260-85.3 R 20 Claims carbon atoms and at least two ethylenic double bonds. O Ordinarily, however, the units are derived from one or more aliphatic or cycloaliphatic monomers containing 4 ABSTRACT OF THE DESCLOSURE to 18 carbon atoms and 2 to 4 conjugated double bonds, Low molecular weight butyl-type copolymers having e.g., butadiene, isoprene, piperylene, 2,3-dimethylbutadi narrow molecular weight distributions are prepared by ene, cyclooctadiene, cyclododecatriene, cyclooctadecatet contacting a higher molecular weight butyl-type copoly 5 raene, etc. The copolymers having a content of about 1. mer, e.g., a butyl rubber, with a catalyst composition to 3 mol percent of a combined aliphatic conjugated diene comprising a transition metal salt, an organometallic com containing 4 to 6 carbon atoms, especially isoprene, are pound of a metal of Group I-A, II-A, II-B, or III-A of preferred. the Periodic Table, a proton donor, and hydrogen. The Although the copolymer may be a low molecular weight catalyst composition preferably comprises a halide of 20 copolymer having a broad molecular weight distribution, tungsten, molybdenum, or rhenium, an alkyl aluminum e.g., a copolymer prepared by the process of the afore halide, a lower alkanol, and hydrogen. mentioned copending application or a copolymer prepared by thermal scission of a butyl-type rubber, it is preferably a butyl-type rubber, i.e., a copolymer having a viscosity BACKGROUND OF THE INVENTION 25 average molecular weight of about 300,000-500,000. However, the product is a copolymer having a lower Field of the invention molecular weight than the starting material and a narrow molecular weight distribution, regardless of whether the This invention relates to low molecular weight butyl starting material has a high or low molecular weight or a type copolymers having narrow molecular weight distribu 30 broad or narrow molecular weight distribution. tions and more particularly relates to a process for pre The transition metal Salt employed as a component of paring such copolymers by the molecular sizing of higher the catalyst system may be one or more salts of a transi molecular weight butyl-type copolymers, such as butyl tion metal such as lanthanum, titanium, zirconium, haf type rubbers. nium, Vanadium, niobium, tantalum, chromium, molyb 35 denum, tungsten, manganese, rhenium, ruthenium, osmi Description of the prior art um, rhodium, iridium, or palladium. Preferably the salt is a halide, more preferably a chloride, but other salts As disclosed in copending application S.N. 139,255, Such as the oxyhalides, sulfates, nitrates, phosphates, ace filed Apr. 30, 1971, in the name of Jerome Robert Ole tates, propionates, benzoates, acetylacetonates, etc. are chowski, low molecular weight butyl-type copolymers use 40 also utilizable. ful in sealants, coatings, electrical encapsulants, blends, Exemplary of Such salts are lanthanum trichloride, tita and binders and as intermediates for the production of nium tetrachloride, titanium trichloride, zirconium tri low molecular weight chlorobutyl-type copolymers may chloride, hafnium tetrachloride, vanadium oxytrichloride, be prepared by the molecular sizing of butyl-type rubbers niobium pentabromide, tantalum pentaiodide, chromic with a catalyst composition comprising a transition metal 45 chloride, molybdenum pentachloride, molybdenum penta salt, an organometallic compound of a Group I-A, I-A, fluoride, molybdenum hexabromide, molybdenum dichlo II-B, or III-A metal, and a proton donor. The products ride, molybdenum oxytetrachloride, molybdenum nitrate, of this process are generally satisfactory but have broader molybdenum acetate, molybdenum propionate, molybde molecular weight distributions than are desirable for some numbenzoate, molybdenum acetylacetonate, molybdenum applications. For example, these products typically have 50 Sulfate, molybdenum phosphate, tungsten hexachloride, weight average molecular weight/number average molec tungsten dichloride, tungsten pentabromide, tungsten hex ular weight ratios (Mw/M) higher than 5, whereas it afluoride, tungsten oxytetrachloride, tungsten sulfate, man is frequently desirable that the copolymers have M/M ganese trichloride, rhenium heptachloride, rhenium hexa ratios lower than 4. chloride, rhenium hexafluoride, rhenium pentachloride, 55 ruthenium sesquichloride, osmium tetrachloride, rhodium SUMMARY OF THE INVENTION Sesquichloride, iridic chloride, palladous iodide, etc. The primary object of this invention is to prepare low The preferred salts are the halides of tungsten, molyb molecular weight butyl-type copolymers having narrow denum, and rhenium, especially tungsten hexachloride, molecular weight distributions from higher molecular molybdenum pentachloride, and rhenium pentachloride. weight butyl-type copolymers. 60 Ordinarily the transition metal salt is employed in an amount Such as to provide about 0.0002-0.01, preferably This and other objects are attained by contacting an about 0.0003-0.0004, mole of transition metal per mol isobutylene-conjugated polyene copolymer having a com of copolymer being treated. bined polyene content of about 1-5 mol percent with The organometallic component of the catalyst system a catalyst composition comprising (1) a transition metal 65 may be one or more organometallic compounds of metals salt, (2) an organometallic compound of a metal of of Groups I-A, II-A, II-B, and III-A of the Periodic Group I-A, I-A, II-B, or III-A of the Periodic Table, Table of Elements. The Periodic Table to which ref. (3) a proton donor selected from glycols and compounds erence is made is Deming's Periodic Table, which may corresponding to the formula ROH wherein R is hydro be found in Lange, "Handbook of Chemistry,” ninth ed., gen, alkyl, aryl, alkaryl, or aralkyl and wherein any alkyl 70 McGraw-Hill Book Company, Inc. (New York To group contains up to five carbon atoms and any ary ronto-London), 1956, pages 56-57. When the metal group is phenyl or naphthyl, and (4) hydrogen. of the organometallic compound is multivalent, any 3,720,654 3 4. valence not satisfied by an organic group may be sati higher than 60° C. are usually undesirable because they fied by hydrogen, chlorine, bromine, iodine, or fluorine. may cause excessive molecular sizing. The reaction may The organic groups in these compounds are preferably be conducted at atmospheric, subatmospheric, or super alkyl groups containing 1-10 carbon atoms or aryl groups atmospheric pressure. such as phenyl, tolyl, or naphthy. Ordinarily the butyl-type copolymer is maintained in Exemplary of the organometallic compounds are contact with the catalyst composition for about 30 sec methyl lithium, butyl lithiums, phenyl lithium, naphthyl onds to about five hours. Longer contact times are usually lithiums, ethyl sodium, propyl potassiums, butyl rubi undesirable bacause of the excessive degree of molecular diums, pentyl cesiums, octyl beryllium chlorides, dimethyl sizing which may be obtained when the contact time magnesium, methyl magnesium bromide, diethyl calcium, 10 exceeds about five hours. When the temperature is main ethyl calcium iodide, dipentyl strontiums, naphthyl stron tained at about 20-60° C., contact times in the range of tium fluorides, dipropyl bariums, phenyl barium chloride, about 30 seconds to about two hours, especially about dihexyl Zincs, ethyl zinc chloride, dioctyl cadmiums, one hour, have been found to be particularly satisfactory. butyl cadium chlorides, trimethyl borine, phenyl boron The molecular sizing reaction is conducted in the sub dibromide, pentyl gallium bromides, hexyl indium chlo 5 stantial absence of catalyst poisons such as oxygen and rides, heptyl thallium chlorides, trimethyl aluminum, carbon dioxide, suitably in a hydrogen atmosphere. To triethyl aluminum, tripropyl aluminums, tributyl alumi facilitate temperature control it is usually desirable to nums, tripentyl aluminums, trihexyl aluminums, triheptyl conduct the reaction in an inert diluent, e.g., a liquid aluminums, trioctyl aluminums, trinonyl aluminums, tri Saturated aliphatic hydrocarbon such as n-hexane, iso decyl aluminums, triphenyl aluminum, trinaphthyl alu 20 octane, cyclohexane, etc., an aromatic hydrocarbon such minums, tritolyl aluminums, trimethylnaphthyl alumi as benzene, toluene, Xylene, etc., or a ring-halogenated nums, the corresponding hydrocarbyl aluminum hydrides aromatic hydrocarbon such as chlorobenzene, chloro and dihydrides, and the corresponding hydrocarbyl alu toluene, etc. minum chlorides, dichlorides, bromides, dibromides, When the desired degree of molecular sizing is attained, iodides, di-iodides, fluorides, and difluorides, etc. 25 Preferably the organometallic compound is an alumi the reaction may be terminated by any conventional tech num compound, more preferably an alkyl aluminum nique, e.g., by addition of
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