CA2501551A1 - Crosslinked polycyclooctene - Google Patents

Crosslinked polycyclooctene Download PDF

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Publication number
CA2501551A1
CA2501551A1 CA002501551A CA2501551A CA2501551A1 CA 2501551 A1 CA2501551 A1 CA 2501551A1 CA 002501551 A CA002501551 A CA 002501551A CA 2501551 A CA2501551 A CA 2501551A CA 2501551 A1 CA2501551 A1 CA 2501551A1
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CA
Canada
Prior art keywords
shape memory
memory polymer
polymer according
shape
polycyclooctene
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CA002501551A
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French (fr)
Other versions
CA2501551C (en
Inventor
Patrick T. Mather
Changdeng Liu
Seung B. Chun
E. Bryan Coughlin
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University of Connecticut
University of Massachusetts UMass
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Individual
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Publication of CA2501551A1 publication Critical patent/CA2501551A1/en
Application granted granted Critical
Publication of CA2501551C publication Critical patent/CA2501551C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30Low-molecular-weight compounds
    • C08G18/38Low-molecular-weight compounds having heteroatoms other than oxygen
    • C08G18/3893Low-molecular-weight compounds having heteroatoms other than oxygen containing silicon
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/02Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
    • C08G61/04Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms
    • C08G61/06Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds
    • C08G61/08Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds of carbocyclic compounds containing one or more carbon-to-carbon double bonds in the ring
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L65/00Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Compositions of derivatives of such polymers
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2230/00Compositions for preparing biodegradable polymers

Abstract

Chemically crosslinked polycyclooctene having excellent shape recovery properties and a method for its synthesis via ring-opening methathesis polymerization of cyclooctene using the dihydroimidazolylidene-modified Grub bs catalyst are disclosed. The polycyclooctene products, following curing with dicumyl peroxide can be shaped, the shape memorized, a new shape imparted wi th the original shape being recoverable by suitable temperature adjustment. The dependence of shape memory characteristics on degree of crosslinking was established. In addition to polycyclooctene, blends thereof with other materials such as SBR, EVA, polyurethane rubbers, and inorganic fillers can be utilized to provide chemically crosslinked products having excellent and tailored shape memory properties.

Claims (31)

1. A shape memory polymer comprising chemically cross-linked polycyclooctene synthesized from cis-cyclooctene having a high trans double bond content.
2. A shape memory polymer according to claim 1 which has been cured by adding dicumyl peroxide to the polycyclooctene.
3. A shape memory polymer according to claim 2 further cured through chemical crosslinking upon heating.
4. A shape memory polymer according to claim 3 which after curing is cooled to room temperature.
5. A shape memory polymer according to claim 1 having a molecular weight ranging (kg/mol) of about 120 to about 325.
6. A shape memory polymer according to claim 2 having a tunable transition temperature (T m of PCO) of about 19 to about 61 °C.
7. A shape memory polymer according to claim 2 having a melting point T m of about 16 to about 61 °C.
8. A shape memory polymer according to claim 2 having a crystallization point T c of about 16 to about 39 °C.
9. A shape memory polymer according to claim 2 having a melting enthalpy .DELTA.H/J g-1 of about 22 to about 63.
10. A shape memory polymer according to claim 2 having a melting point T m of about 16 to about 61 °C, a crystallization point T c of about 16 to about 39 °C and a melting enthalpy .DELTA.H/J g of about 22 to about 63.
11. A shape memory polymer according to claim 2 having a degree of crystallinity at room temperature of from about 2.6% to about 25.5%.
12. A shape memory polymer according to claim 2 evidencing rapid shape memory behavior.
13. A shape memory polymer according to claim 12 wherein the primary stress-free shape of the polymer is recovered within about 1 second on exposure to temperatures above the melting point of the crystalline polymer phase.
14. A shape memory polymer comprising a blend of a polymer according to claim 1 with a member selected from the group consisting styrene butadiene, EVA and polyurethane.
15. A shape memory polymer molded article formed from a chemically crosslinked polycyclooctene according to claim 1.
16. A shape memory polymer molded article formed from the blend according to claim 14.
17. Method of forming a shape memory polymer comprising conducting a ring opening metathesis polymerization of cis-cyclooctene in the presence of a Grubbs catalyst and reacting the polycyclooctene formed with dicumyl peroxide at an elevated temperature to cure the polycyclooctene.
18. Method according to claim 17 wherein said catalyst is RuCl2(=CHPh)(PCy3)2.
19. Method according to claim 17 wherein said catalyst is a dihydroimidazolyidene-modified Grubbs catalyst.
20. Method according to claim 17 wherein said curing is carried out in a mold.
21. A shape memory polymer produced by the process of claim 17.
22. An impression material for molding, duplication, rapid prototyping, and embossing comprising a shape memory polymer according to claim 2.
23. A temperature sensor comprising a shape memory polymer according to claim 2.
24. A medical impression material for dentistry, orthopedics and podiatry comprising a shape memory polymer according to claim 2.
25. A shape memory polymer according to claim 1 containing a member selected from the group consisting of finely divided organic and inorganic fillers.
26. A shape memory polymer according to claim 25 wherein said filler is a member selected from the group consisting of born nitride, silica, titanium dioxide, montmullinite, clay, Kevlar, staple, aluminum nitride, barium and bismuth subcarbonate.
27. A shape memory polymer according to claim 26 wherein said filler is boron nitride.
28. A shape memory polymer according to claim 27 wherein said filler is titanium dioxide.
29. Method for increasing the shape recovery rate of a shape memory polymer according to claim 1 which comprises incorporating therein boron nitride as a filler.
30. Method for decreasing the temperature for shape recovery of a shape memory polymer according to claim 1 which comprises incorporating therein boron nitride as a filler.
31. Method for simultaneously increasing the body-temperature modulus and the UV
absorption of a shape memory polymer according to claim 1 which comprises incorporating therein titanium dioxide as a filler.
CA2501551A 2002-10-11 2003-10-10 Crosslinked polycyclooctene Expired - Fee Related CA2501551C (en)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
US41802302P 2002-10-11 2002-10-11
US60/418,023 2002-10-11
US41950602P 2002-10-18 2002-10-18
US60/419,506 2002-10-18
US48832303P 2003-07-18 2003-07-18
US60/488,323 2003-07-18
PCT/US2003/032138 WO2004033553A1 (en) 2002-10-11 2003-10-10 Crosslinked polycyclooctene

Publications (2)

Publication Number Publication Date
CA2501551A1 true CA2501551A1 (en) 2004-04-22
CA2501551C CA2501551C (en) 2012-12-11

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
CA2501551A Expired - Fee Related CA2501551C (en) 2002-10-11 2003-10-10 Crosslinked polycyclooctene

Country Status (8)

Country Link
US (4) US7173096B2 (en)
EP (1) EP1560881B1 (en)
JP (1) JP4530989B2 (en)
AT (1) ATE534704T1 (en)
AU (1) AU2003282572B2 (en)
CA (1) CA2501551C (en)
ES (1) ES2373650T3 (en)
WO (1) WO2004033553A1 (en)

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ATE534704T1 (en) 2011-12-15
US7906573B2 (en) 2011-03-15
AU2003282572A1 (en) 2004-05-04
US20090275704A1 (en) 2009-11-05
US7705098B2 (en) 2010-04-27
EP1560881A1 (en) 2005-08-10
CA2501551C (en) 2012-12-11
US20040122184A1 (en) 2004-06-24
US20070142562A1 (en) 2007-06-21
ES2373650T3 (en) 2012-02-07
JP4530989B2 (en) 2010-08-25
WO2004033553A1 (en) 2004-04-22
AU2003282572B2 (en) 2009-04-09
US7173096B2 (en) 2007-02-06
JP2006503171A (en) 2006-01-26
US7563848B2 (en) 2009-07-21
EP1560881B1 (en) 2011-11-23
US20100160522A1 (en) 2010-06-24

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