Terpene/isoolefin copolymers having substantially heterogeneous compositional distribution and displaying thermoplastic elastomeric properties

Patent metadata

Field	Value
Publication number	US-9790301-B2
Application number	US-201514701640-A
Country	US
Kind code	B2
Filing date	May 1, 2015
Priority date	Jan 18, 2012
Publication date	Oct 17, 2017
Grant date	Oct 17, 2017

Abstract

Copolymers having a substantially heterogeneous composition distribution and strong UV absorption are the direct reaction product of an isoolefin and at least one terpene having the molecular formulae of (C 5 H 8 )n where n is equal to or greater than two, and optionally additional monomers. More specifically, the invention relates to copolymers of isobutylene and alloocimene that exhibit thermoplastic elastomeric properties and exhibit strong filler interaction. The present invention also relates to methods for producing copolymers of at least one isoolefin and at least one terepene by a two-phase living polymerization that produces a substantially linear triblock and multiblock copolymer having substantially heterogeneous distribution of the isoolefin and terpene units.

First claim

What is claimed is:

1. A thermoplastic elastomer (TPE), comprising a linear triblock or linear multiblock copolymer or any combination thereof, having repeat units derived from at least one isoolefin monomer having from 4 to about 7 carbon atoms, and having repeat units derived from at least one terpene monomer having the formula (C 5 H 8 )n, wherein n is 2 or more; and optionally repeat units derived from one or more dienes, styrene or a derivative thereof, indene or a derivative thereof, or any combination thereof, wherein said terpene is selected from the group consisting of alloocimene, neo-alloocimene, and any combination thereof.

2. The TPE of claim 1 , wherein the weight average molecular weight of said block copolymer is at least about 1,000 to about 5,000,000 g/mol.

3. The TPE of claim 2 , wherein said weight average molecular weight is from about 200,000 to about 1,000,000 g/mol, wherein said isoolefin is 2-methyl propene (isobutylene), 2-methyl-1-butene, 3-methyl-1-butene, 2-methyl-2-butene, 4-methyl-1-pentene and any combination thereof.

4. The TPE of claim 3 , wherein said weight average molecular weight is from about 300,000 to about 800,000 g/mol.

5. The TPE of claim 3 , further comprising a filler.

6. The TPE of claim 1 , wherein said TPE has a UV adsorption at about 240 nanometers and said UV adsorption is at least twice as intense as that of the polymer made in the absence of said terpene.

7. The TPE of claim 1 , wherein said optional repeat units are present and are selected from the group consisting of 2-methyl-butadiene-1,3 (isoprene), butadiene, 2-methylbutadiene, 2,4-dimethylbutadiene, piperyline, β-pinene, 3-methyl-1,3-pentadiene, 2,4-hexadiene, 2-neopentylbutadiene, 2-methyl-1,5-hexadiene, 2,5-dimethyl-2,4-hexadiene, 2-methyl-1,4-pentadiene, 2-methyl-1,6-heptadiene, cyclopenta-diene, methylcyclopentadiene, cyclohexadiene, 1-vinyl-cyclohexadiene, styrene, p-methylstyrene, α-methylstyrene, p-chlorostyrene, p-methoxystyrene, indene, indene derivatives, or any combination thereof.

8. The TPE of claim 5 , wherein said filler is selected from the group consisting of silica, carbon black, carbon nanotubes, starch, cellulose, fullerene, nanoclay, and combinations thereof.

9. The TPE of claim 8 , wherein the amount of said filler is from about 1 to about 50 parts by weight based upon the total weight of all said triblock, or multiblock copolymers.

10. A biomedical composition comprising the TPE of claim 1 .

11. A drug eluting coating or fiber mat comprising the composition of claim 1 .

12. An inner tube or a tubeless tire comprising the composition of claim 1 .

13. A thermoplastic elastomer (TPE), comprising a linear triblock or linear multiblock copolymer or any combination thereof having repeat units derived from at least one isoolefin monomer having from 4 to about 7 carbon atoms, and having repeat units derived from at least one terpene monomer having the formula (C 5 H 8 )n, wherein n is 2 or more; and optionally repeat units derived from one or more dienes, styrene or a derivative thereof, indene or a derivative thereof, or any combination thereof, wherein the isoolefin is isobutylene and the terpene is alloocimene, wherein the copolymer includes a polyisobutylene block between two alloocimene polymer blocks.

14. A biomedical composition comprising the TPE of claim 13 .

Assignees

• Univ Akron

Inventors

• Puskas Judit E

Classifications

• C08F236/22

  the radical having three or more carbon-to-carbon double bonds · CPC title

• C08F297/00

  Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer · CPC title

• C08L23/22

  Copolymers of isobutene; Butyl rubber; Homopolymers or copolymers of other iso-olefins · CPC title

• C08F210/12 Primary

  with conjugated diolefins, e.g. butyl rubber · CPC title

• Y10T428/1386

  Natural or synthetic rubber or rubber-like compound containing · CPC title