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United States Patent Office Patented Nov 3,477,999 United States Patent Office Patented Nov. 11, 1969 1. 2 3,477,999 powdery polymer which is rich in syndiotacticity and does METHOD FOR POLYMERIZATION OF not contain tetrahydrofuran-insoluble part or other im WNYL COMPOUNDS purities. It is still a further object of the present invention Saburo Takeda, 29-24. Mitsuzawashimocho, Hiromi Higa to provide a method for producing a polymer which shi, and Ryokichi Tarao, 44 Otsutomocho, Mikio Mi 5 affords a film Superior in transparency. It is still a further Zuno and Kazuyuki Watabe, 303 Termaecho, all of object of the present invention to provide a method which Kanazawa-ku Yokohamashi, Kanagawa-ken, Japan, can be applied to the copolymerization of vinyl chloride Michiaki Saito, 1938. Ookacho, Minami-ku, Yokohama or/and vinylidene chloride with a wide variety of polymer shi, Kanagawa-ken, Japan, Shigeo Namikawa, 44 Otsu izable unsaturated compounds while affording a homo tomocho, Kanazawa-ku, Yokohama-shi, Kanagawa-ken, Japan, and Takao Tsunoda, 28-15, 3-chome, Satae IO geneous copolymer containing hardly a homopolymer. machi, Tsurumi-ku, Yokohama-shi, Kanagawa-ken, These objects and other advantages can be attained by Japan the method of the present invention. No Drawing. Filed Apr. 11, 1967, Ser. No. 629,916 According to the method of the present invention, a Claims priority, application Japan, Apr. 11, 1966, lower aliphatic alcohol containing an amino radical, 41/22,794; Sept. 30, 1966, 41/64,536; Oct. 13, nitrile radical and a halogen atom as a substituent, is used 1966, 41/67,080; Oct. 22, 1966, 41/69,624; Dec. as a modifier of Ziegler type catalyst. In other words the 29, 1966, 42/323; Jan. 10, 1967, 42/1,908 present invention consists in a method for polymerizing or Int, C. C08g 1/56; B01j 1 1/84 copolymerizing a vinyl compound represented by a gen U.S. C. 260-78.5 12 Claims eral formula of 20 ABSTRACT OF THE DISCLOSURE A method for polymerizing or copolymerizing vinyl Yo! chloride or vinylidene chloride which comprises polymer wherein X is H or Cl atom, which comprises polymeriz izing or copolymerizing said compound by the use of a ing or copolymerizing said compound by the use of a modified Ziegler type catalyst consisting of a transition modified Ziegler type catalyst consisting of (a) a com metal compound, an organoaluminum compound and a pound of transition metal, (b) an organialuminum com lower aliphatic alcohol possessing, as a substituent, an pound and (c) a lower aliphatic alcohol possessing the amino radical, nitrile radical or a halogen atom, the cata above-mentioned substituent. lyst preferably consisting of a transition metal compound 30 The compound of transition metal, which is a constit and an isolated reaction product between an organo uent of the catalyst, includes halide, oxyhalide, alkoxide, aluminum compound and a lower alkanolamine. alkoxyhalide, alkoxyacetylacetonate, acetoxyhalide or acetylacetonate of titanium, vanadium, chromium, iron, cobalt, nickel, zirconium or manganese. This invention relates to a method for polymerizing 35 vinyl compound. More particularly it relates to a method Representative compounds are Ticli, Ticli, Ticlz, TiBra for polymerizing vinyl chloride or vinylidene chloride or copolymerizing vinyl chloride or/and vinylidene chlo ride in the presence of a modified Ziegler type catalyst. TiO(acac), Ti(ocochs).2cl2, VOCl3, Vcla, Vcla, Crcls, It has been known that the polymerization of vinyl 40 CrO2cl2, Cr(acac)3, Cocla, Co (acac)2, Co(acac)3, chloride or vinylidene chloride with a Ziegler type catalyst Fe(acac)2, Fe(acac)3, Ni(acac)2. Zrcla, Zrcla, yields a colored polymer due to the dehydrochlorination Zr(acac)4 acac is the abbreviation of acetylacetonate of the formed polymer. In order to overcome such a draw radical. The material such as Ticlis' /3 Alcla also is in back, the use of various modified Ziegler type catalysts cluded. - have been studied. With regard to such studies, collective 45 Illustrative oragnoaluminum compound includes com reports are found in "Vinyls and Polymers” (Japan), vol. pounds expressed by a general formula, AllRnX3-m, 5, No. 6, pp. 24–27 (1965) for vinyl chloride and “A.” wherein R is alkyl, cycloalkyl or aryl radical, X is halogen collection of lecture gists of the 14th discussion assembly and n is 3, 2, 1.5 or 1 such as trimethyl aluminum, on high molecular compounds' (Japan), pp. 281-286 triethyl aluminum, tricyclohexyl aluminum, triphenyl (1965) for vinylidene chloride. However it can hardly 50 aluminum diethyl aluminum chloride, ethyl aluminum say that anyone of the processes reported therein enables sesquichloride or ethyl aluminum dichloride. to overcome the above-mentioned drawback satisfactorily. The lower alcohol to be used in the present invention Accordingly, it is an object of the present invention to as a modifier contains halogen atom, nitrile radical or provide a method for producing a non-colored polymer or amino radical. Exemplary lower alcohols containing copolymer of vinyl chloride or vinylidene chloride which 55 halogen or nitrile are ethylene chlorohydrine, ethylene does not accompany the dehydrochlorination. It is another bromohydrine and ethylene cyanohydrine. object of the present invention to provide a method for The lower alcohols containing amino radical are producing the above-mentioned polymer or copolymer alkanolamine possessing N-substituted or non-substituted having a higher molecular weight by using a catalyst amino radical. As N-substituted radical, N-alkyl, N-cyclo possessing a sufficiently high activity even at a relatively 60 alkyl, N-aryl radical are useful and one or two substitu low temperature which can be handled safely and affords tions are possible. a high polymerization rate. It is a further object of the As alkanolamines possessing N-substituted amino radi present invention to provide a method for producing a cal, monoethanol amines possessing, as N-substituent, one 3,477,999 3 4. or two radicals such as N-methyl, N,N-dimethyl, N-ethyl, forms a stabilized catalyst system which can be handled N, N-diethyl, N-butyl, N, N-dibutyl, N-cyclohexyl, N, safely. N-dicyclohexyl, N-phenyl, N,N-diphenyl or the like are The polymerization can be carried out even at a tem perature generally used in the polymerization with a com illustrated.As alkanolamine possessing non-substituted aminoO mon radical polymerization catalysts. However since the radical, mono-ethanol amine (MEA), n-propanol amine catalytic system of the present invention is considerably (nPA), isopropanol amine (iPA), diethanolamine stable to heat, it exhibits a sufficient catalyst activity even (DEA), triethanolamine (TEA) or the like are illustrated. at a temperature of 80 C. or more. The reaction is car Hydrochloric acid salts, and sulfuric acid salts of the ried out generally at -20° C. to 100° C., preferably at above-mentioned alkanol amines are also useful. 30° 70° C. In the polymerization, the above-mentioned three Con IO The reaction system shows grey, pale yellow or bright ponents (a), (b) and (c) can be added to the polyn violet color and does not show black color as in the case erization system as a mixed catalyst. It is also possible to of Ziegler type catalyst merely modified with a common react an organoaluminum compound with a substituted alcohol. When the catalyst activity is compared by using lower alcohol in advance and to use the isolated reaction 5 the polymerization velocity as a barometer, the present product together with a compound of a transition metal, catalytic system enables to complete the reaction in a as a catalysts. In order to attain the object of the present time considerably shorter than other catalytic systems. invention, the latter process is preferable. Such reaction Namely, reaction proceeds sufficiently in several to 10 products of organoaluminum compound with a substi hours with the present catalytic system. tuted lower alcohol include reaction products consisting 20 The polymerization reaction is carried out in the pres of AlMe-MEA (mol ratio 1:1), AEt3-MEA (1:1), ence or in the practical absence of solvent. As a solvent AlEt-nPA (1:1), AlEta-iPA (1:1), AlEta-MEA (1:2), to be used, a halogenated hydrocarbon is preferred. For AEt.-DEA (1:1), AlEta-DEA (2:1), AlBta-(N-MeMEA) example, carbon tetrachloride, chloroform, tetrachloro (1:1), AlEta-(N,N-MeMEA) (1:1), AlEta-(N-EtMEA) ethylene, trichloroethylene, 1,2-dichloroethylene, 1,2-di (1:1), AlEt-(N,N-EtMEA) (1:1), AlEta-(N-PhMEA) chloroethane, amyl chloride, monochlorobenzene, mono (1:1), AlEta (N, N-Ph2MEA) (1:1), AlEta-(N-cyclo bromobenzene, dichlorobenzene or the like is used. Be hexyl MEA) (1:1), AlEta-(N, N-(cyclohexyl)2 MEA) sides halogenated hydrocarbon, tetrahydrofuran, n-hep 1:1). tane dimethyl formamide, acetone, ethyl acetate, acetyl ( Wii, regard to the mol ratio of these catalyst constitu acetone or the like is also useful, but the yield is generally ents, explanation is given in the case where an alkanol 30 lower than the case where chlorinated hydrocarbon is amine is selected as a (c)-constituent. used. Further when vinyl chloride and vinylidene chloride First of all, the organoaluminum compound is used gen is to be copolymerized, one of them as a comonomer, erally in a mol ratio of one or more relative to a con itself, can be used also as a solvent to perform simul pound of a transition metal. When an organoaluminum taneous function. If such a case is expressed by another compound is used in the form of isolated reaction product way, it is called the case of non-solvent polymerization. with an alkanol amine, the mol ratio of said reaction Not only in the case of copolymerization reaction, such product relative to a compound of a transition metal is a non-solvent polymerization reaction can be applied also in the range of one or more, preferably in the neighbour to the case of homopolymerization.
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