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Isobutylene Polymer Having Unsaturated Group and Preparation

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Isobutylene Polymer Having Unsaturated Group and Preparation Europaisches Patentamt European Patent Office Office europeen des brevets (11) EP 0 452 875 B2 (12) NEW EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) |nt CI.6: C08F 10/10, C08F 2/42 of the opposition decision: 18.08.1999 Bulletin 1999/33 (45) Mention of the grant of the patent: 09.08.1995 Bulletin 1995/32 (21) Application number: 91106042.4 (22) Date of filing: 16.04.1991 (54) Isobutylene polymer having unsaturated group and preparation thereof Isobutylenpolymer mit ungesattigter Gruppe und seine Herstellung Polymere de I'isobutylene ayant un groupe insature et sa preparation (84) Designated Contracting States: (74) Representative: BE CH DE ES FR GB IT LI NL SE Hansen, Bernd, Dr. Dipl.-Chem. et al Hoffmann Eitle, (30) Priority: 16.04.1990 JP 10102990 Patent- und Rechtsanwalte, 29.11.1990 JP 33636490 Postfach 81 04 20 81904 Miinchen (DE) (43) Date of publication of application: 23.10.1991 Bulletin 1991/43 (56) References cited: EP-A- 0 265 053 EP-B- 0 322 241 (73) Proprietor: Kanegafuchi Chemical Industry Co., CA-A- 467 049 GB-A- 1 059 580 Ltd. US-A- 4 31 6 973 US-A- 4 327 201 Kita-ku Osaka-shi Osaka-fu (JP) US- A- 4 524 1 88 US-A- 4 758 63 1 US-A- 4 929 683 (72) Inventors: • Noda, Koji Remarks: Kobe-shi, Hyogo-ken (JP) The file contains technical information submitted • Fujisawa, Hiroshi after the application was filed and not included in this Kobe-shi, Hyogo-ken (JP) specification • Yonezawa, Kazuya Kobe-shi, Hyogo-ken (JP) CM DO 10 Is- 00 CM IO ^- o a. LU Printed by Jouve, 75001 PARIS (FR) EP 0 452 875 B2 Description [0001] The present invention relates to an isobutylene polymer having an unsaturated group and a process for pre- paring the same. 5 [0002] An isobutylene polymer having more than one unsaturated group per molecule on the average is cross linked and cured to produce a rubbery cured material. Such polymer can be modified by introducing a cross-linkable silicon group to form a moisture-curable polymer as disclosed in U.S. Patent No. 4,904,732 and Japanese Patent Kokai Publication No. 6041/1988. [0003] The isobutylene polymer having more than one unsaturated group per molecule on the average is disclosed 10 in U.S. Patent Nos. 3,644,315 and 4,524,187 and it is prepared by copolymerizing isobutylene and a compound having a conjugated double bond, so that it has double bonds in polymer chains and is poor in weather resistance, chemical resistance and reactivity. [0004] U.S. Patent Nos. 4,31 6,973 and 4,758,631 and Japanese Patent Kokai Publication No. 105005/1 988 disclose polymers having an unsaturated group at a chain end. The polymer of U.S. Patent Nos. 4,316,973 and 4,758,631 is is prepared by an Inifer method comprising cationically polymerizing isobutylene in the presence of 1 ,4-bis(a-chloroiso- propyl)benzene as a polymerization initiating and chain transfer agent and BCI3 as a catalyst and further reacting a formed polymer having a chlorine atom at a chain end. [0005] A polymer disclosed in Japanese Patent Kokai Publication No. 105005/1988 is prepared by synthesizing an isobutylene polymer having chlorine atoms at both chain ends by the Inifer method and, just after synthesis or purifi- 20 cation, reacting the isobutylene polymer with allyltrimethylsilane to obtain a polymer having allyl groups at both chain ends. [0006] However, the polymers disclosed in U.S. Patent No. 4,316,973 and Japanese Patent Kokai Publication No. 105005/1988 require multiple steps for the production and/or expensive raw materials. [0007] CA-467 049 discloses a copolymer of isoolefins (in particular isobutylene) with non-conjugated diolefins of 25 the formula CH2=CR-Cn-H2n.x wherin R is an alkyl group (preferably methyl), n is any whole number greater than 2 and x is any uneven number. The number of these unconjugated diene units is according to the examples in the order of 4.7 to 6.5. [0008] EP-B-0 322 241 relates to viscous polybutenes, having a number average molecular weight of 500 to 5000 and a total terminal double bond content of at least 40% based on the total theoretic unsaturation of the polybutene. 30 "Terminal" means terminal disubstituted or terminal trisubstituted. The polybutene product obtained is further charac- terized by the proportionate distribution of terminal disubstituted double bonds and tetrasubstituted double bonds present therein. Normally one does not detect the presence of monosubstituted double bonds in polybutene molecules like that of EP-B-0 322 241. 35 SUMMARY OF THE INVENTION [0009] One object of the present invention is to provide a novel isobutylene polymer having an unsaturated group. [0010] Another object of the present invention is to provide a process for easily preparing such isobutylene polymer at a low cost. 40 [0011] According to a first aspect of the present invention, there is provided an isobutylene polymer comprising 1,1 to 5 units per molecule on the average of the formula CH2 - ChHj- 45 Q (I) 50 HC=CH2 wherein Q is a C-|-C30 divalent organic group and which has the unit of formula (I) at the polymer chain end(s). [0012] According to a second aspect of the present invention, there is provided a process for preparing the isobuty- 55 lene polymer having an unsaturated group as defined above, which comprises polymerizing a cationically polymerizable monomer containing isobutylene and a non-conjugated diene in the presence of a Lewis acid and a polymerization initiating and chain transfer agent of formula (III) as defined below. [0013] According to a third aspect of the present invention, there is provided a process for prepanng the isobutylene 2 EP 0 452 875 B2 polymer having an unsaturated group as defined above which comprises polymerizing a cationically polymerizable monomer containing isobutylene in the presence of a Lewis acid and a polymerization initiating and chain transfer agent of formula (III) as defined below, and reacting the resulting polymer with a non-conjugated diene. 5 Figs. 1 and 2 are the I R spectrum and the 1H-NMR spectrum of the polymer prepared in Example 1 , respectively and Figs. 3 and 4 are the I R spectrum and the 1H-NMR spectrum of the polymer prepared in Example 8, respectively. [0014] The group Q may be a straight or branched divalent organic group and preferably a straight or branched alkylene group such as a hexylene group. 10 [0015] The isobutylene polymer of the present invention is characterized in that it comprises the unit of the formula (I). The isobutylene polymer of the present invention usually has a number average molecular weight of from 500 to 500,000, preferably from 1000 to 50,000 and comprises at least 1.1 and not more than 5 units of the formula (I) on the average per molecule. [0016] The unit of the formula (I) is present at the end(s) of the polymer chain. Preferably, the isobutylene polymer is of the present invention has no unsaturated group in the polymer chain in view of properties of the polymer such as weather resistance. [0017] Typically, the isobutylene polymer of the present invention can be prepared by the following two processes. Process 1 20 [0018] A cationically polymerizable monomer containing isobutylene and a non-conjugated diene are polymerized in the presence of a Lewis acid and a polymerization and chain transfer agent of formula (III) as defined below. Process 2 25 [0019] A cationically polymerizable monomer containing isobutylene is polymerized in the presence of a Lewis acid and a polymerization and chain transfer agent of formula (III) as defined below, and then the resulting polymer is reacted with a non-conjugated diene. [0020] The "cationically polymerizable monomer" herein used is intended to include not only a pure isobutylene 30 monomer but also a monomer mixture comprising 50 % by weight or more of isobutylene and 50 % by weight or less of at least one other cationically polymerizable monomer which is copolymerizable with isobutylene. [0021] The other cationically polymerizable monomer copolymerizable with isobutylene includes C3-C12 olefins, con- jugated dienes, vinyl ethers, aromatic vinyl compounds, vinylsilanes. Among them, the C3-C12 olefins and conjugated dienes are preferred. In view of weather resistance of the polymer, the olefins other than the conjugated dienes are 35 preferred. [0022] Specific examples of the other cationically polymerizable monomers copolymerizable with isobutylene are propylene, 1-butene, 2-butene, 2-methyl-1-butene, 3-methyl-2-butene, pentene, 4-methyl-1-pentene, hexene, vinylcy- clohexane, butadiene, isoprene, cyclopentadiene, methylvinylether, ethylvinylether, isobutylvinylether, styrene, a- methylstyrene, dimethylstyrene, monochlorostyrene, dichlorostyrene, p-pinene, indene, vinyltrichlorosilane, vinylmeth- 40 yldichlorosilane, vinyldimethylchlorosilane, vinyldimethylmethoxysilane, vinyltrimethylsilane, divinyldichlorosilane, di- vinyldimethoxysilane, divinyldimethylsilane, 1 ,3-divinyl-1 ,1 ,3,3-tetramethyldisiloxane, trivinylmethylsilane, tetravinylsi- lane, y-methacryloyloxypropyltrimethoxysilane, y-methacryloyloxypropylmethyldimethoxysilane. Among them, propyl- ene, 1-butene, 2-butene, styrene, butadiene, isoprene and cyclopentadiene are preferred. They may be used inde- pendently or as a mixture of two or more of them. 45 [0023] The non-conjugated diene to be used in the present invention is a diene of the formula: CH2=CH-Q-CH=CH2 (II) wherein Q, is the same as defined above. [0024] As the non-conjugated diene, any of the compounds of the formula (II) can be used. Examples of the non- conjugated diene are 1 ,4-pentadiene, 1 ,5-hexadiene, 1 ,6-heptadiene, 1 ,7-octadiene, 1 ,8-nonadiene, 1 ,9-decadiene, 1,19-dodecadiene, 1 ,5,9-decatriene. Among them, a,co-dienes such as 1 ,4-pentadiene, 1 ,5-hexadiene, 1,6-heptadi- ene, 1 ,7-octadiene, 1 ,8-nonadiene, 1 ,9-decadiene and 1 ,19-dodecadiene are preferred in view of activity of the func- tional groups contained in the prepared polymer.
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