Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Mixing of two or more solid polymers; mixing of solid...
Reexamination Certificate
1998-12-04
2001-04-17
Seidleck, James J. (Department: 1711)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Mixing of two or more solid polymers; mixing of solid...
C525S319000, C526S348700
Reexamination Certificate
active
06218475
ABSTRACT:
TECHNICAL FIELD
The present invention relates to an alkenyl-group-containing isobutylene group block copolymer and a reactive-silicon-group-containing isobutylene group block copolymer. More particularly, the invention relates to a novel process for producing an alkenyl-group-containing isobutylene group block copolymer and a reactive-silicon-group-containing isobutylene group block copolymer.
PRIOR ART
The isobutylene group block copolymer, though not crosslinked, is comparable to closslinked rubber in strength and elasticity, having high impact resistance and flexibility, and as easy to mold as a thermoplastic resin. Therefore, attempts have been made to exploit it as an elastomer material or an impact resistance improving agent for a thermoplastic resin.
Japanese Kokoku koho Hei-7-100763, for instance, discloses a composition comprising an isobutylene group block copolymer and a thermoplastic resin. In a composition of this type, however, the compatibility of the thermoplastic resin with the isobutylene group block copolymer is not sufficiently high depending on the type of the resin, and therefore, the composition cannot exhibit sufficiently useful physical properties such as impact resistance and mechanical strength.
As a process for avoiding the above disadvantage, there is known a process which comprises introducing a functional group into an isobutylene group block copolymer. Japanese Kokai Publication Hei-6-271751, for instance, discloses a composition comprising a hydroxy-terminated isobutylene group block copolymer and a polyester resin. Japanese Kokai Publication Hei-6-271751 further discloses, as an intermediate of said hydroxy-terminated isobutylene group block copolymer, an alkenyl-terminated isobutylene group block copolymer available upon dehydrochlorination of a chlorine-terminated block copolymer synthesized in the system comprising 1,4-di-(2-methoxy-2-propyl)benzene and titanium tetrachloride as an initiator.
However, because those technologies have the disadvantage that they need stringent reaction conditions and that enhancing the reaction rate is difficult, the rate of introduction of the alkenyl group is not sufficiently high. Furthermore, because the alkenyl group that can be introduced is limited to groups of the isopropenyl type, the alkenyl function introduced is not sufficiently reactive and cannot be easily converted to other functional groups.
SUMMARY OF THE INVENTION
The present invention has for its object to provide an isobutylene group block copolymer which can be easily synthesized with a high alkenyl introduction rate and insuring a high reactivity of the alkenyl group so introduced and a reactive-silicon-group-containing isobutylene group block copolymer, and an expedient process for producing these copolymers.
The present invention, therefore, relates to an alkenyl-group-containing isobutylene group block copolymer comprising a polymer block derived from (a) a monomer component containing isobutylene group as a predominant monomer and a polymer block derived from (b) a monomer component not containing isobutylene group as a predominant monomer, said copolymer containing an alkenyl group of general formula (1);
wherein a plurality of R
1
may be the same or different and each represents hydrogen, halogen, or a substituted or unsubstituted monovalent organic group.
The present invention relates to a process for producing an alkenyl-group-containing isobutylene group block copolymer which comprises adding an alkenyl-group-containing silicon compound in the course of the polymerization of (a) a monomer component containing isobutylene group as a predominant monomer with (b) a monomer component not containing isobutylene group as a predominant monomer in the presence of a polymerization initiator of the following general formula (2);
wherein a plurality of R
2
may be the same or different and each represents hydrogen or a monovalent hydrocarbon group containing 1 to 6 carbon atoms; R
3
represents a mono- or poly-valent aromatic hydrocarbon group or a mono- or poly-valent aliphatic hydrocarbon group; X represents halogen or an alkoxy or acyloxy group containing 1 to 6 carbon atoms; and n represents an integer of 1 to 6, with providing that n is equal to two or more, the plurality of X may be the same or different.
Further, the present invention relates to a reactive-silicon-group-containing isobutylene group block copolymer comprising a polymer block derived from (a) a monomer component containing isobutylene group as a predominant monomer and a polymer block derived from (b) a monomer component not containing isobutylene group as a predominant monomer, said copolymer containing a reactive silicon group of general formula (4);
wherein a plurality of R
6
may be the same or different and each represents hydrogen, halogen, or a substituted or unsubstituted monovalent organic group; R
7
represents a monovalent organic group of 1 to 5 carbon atoms, and when two of R
7
are contained, these may be the same or different; Y represents a halogen atom or alkoxy group, and providing that more than two of Y are contained, these may be the same or different; and a represents an integer of 0 to 2.
Furthermore, the present invention relates to a process for producing a reactive-silicon-group-containing isobutylene group block copolymer which comprises subjecting the compound represented by the following general formula (5) to hydrosilylation reaction with an alkenyl group of an alkenyl-group-containing isobutylene group block copolymer comprising a polymer block derived from (a) a monomer component containing isobutylene group as a predominant monomer and a polymer block derived from (b) a monomer component not containing isobutylene group as a predominant monomer.
wherein R
7
represents a monovalent organic group of 1 to 5 carbon atoms, and when two of R
7
are contained, these may be the same or different; Y represents a halogen atom or alkoxy group, with providing that more than two of Y are contained, these may be the same or different; and a represents an integer of 0 to 2.
DETAILED DESCRIPTION OF THE INVENTION
The present invention is directed to an alkenyl-group-containing isobutylene group block copolymer comprising a polymer block derived from (a) a monomer component containing isobutylene group as a predominant monomer and a polymer block derived from (b) a monomer component not containing isobutylene group as a predominant monomer, said alkenyl-group-containing isobutylene group block copolymer containing an alkenyl group of general formula (1).
The alkenyl group of the above general formula (1) may be located either in the polymer block derived from (a) a monomer component containing isobutylene group as a predominant monomer or in the polymer block derived from (b) a monomer component not containing isobutylene group as a predominant monomer, although it is preferably located in the polymer block derived from (b) a monomer component not containing isobutylene group as a predominant monomer.
The polymer block derived from (a) a monomer component containing isobutylene group as a predominant monomer may or may not contain any monomer component other than isobutylene group as a comonomer component unit. The monomer other than isobutylene group which can be used is not particularly restricted provided that it is a monomer capable of cationic polymerization, but includes aliphatic olefins, aromatic vinyl compounds, dienes, vinyl ethers, silanes, vinylcarbazole, &bgr;-pinene, and acenaphthylene, among other monomers. Those monomers may be used each alone or in combination.
The aliphatic olefinic monomers which can be used are not particularly restricted but include propylene, 1-butene, 2-methyl-1-butene, 3-methyl-1-butene, pentene, hexene, cyclohexene, 4-methyl-1-pentene, vinylcyclohexene, octene, and norbornene, among others. Those monomer components can be used each alone or in combination.
The aromatic vinyl monomers which can be used are not particularly restricted but include styrene, o-, m-, or p-methylstyrene, &agr;-methylstyrene, &bg
Aoyama Taizo
Hiiro Tomoki
Ozawa Shinji
Asinovsky Olga
Connolly Bove Lodge & Hutz
Kaneka Corporation
Seidleck James J.
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