CA2501551A1 - Crosslinked polycyclooctene - Google Patents
Crosslinked polycyclooctene Download PDFInfo
- 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
- Authority
- 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.)
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3893—Low-molecular-weight compounds having heteroatoms other than oxygen containing silicon
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
- C08G61/04—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms
- C08G61/06—Macromolecular 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
- C08G61/08—Macromolecular 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L65/00—Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2230/00—Compositions 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.
absorption of a shape memory polymer according to claim 1 which comprises incorporating therein titanium dioxide as a filler.
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
ID=32096896
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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WO2004011525A1 (en) | 2002-07-30 | 2004-02-05 | University Of Connecticut | Nonionic telechelic polymers incorporating polyhedral oligosilsesquioxane (poss) and uses thereof |
US6966649B2 (en) * | 2002-08-12 | 2005-11-22 | John H Shadduck | Adaptive optic lens system and method of use |
US7794494B2 (en) * | 2002-10-11 | 2010-09-14 | Boston Scientific Scimed, Inc. | Implantable medical devices |
AU2003300377B2 (en) * | 2002-10-11 | 2009-04-02 | University Of Connecticut | Blends of amorphous and semicrystalline polymers having shape memory properties |
DE60336158D1 (en) * | 2002-10-11 | 2011-04-07 | Univ Connecticut | ON SEMICRISTALLINE THERMOPLASTIC POLYURETHANES BASED FOR NANOSTRUCTURED HARD SEGMENTS BASED FORM MEMORY PILARMERS |
EP1560881B1 (en) | 2002-10-11 | 2011-11-23 | University of Connecticut | Crosslinked polycyclooctene |
US7524914B2 (en) * | 2002-10-11 | 2009-04-28 | The University Of Connecticut | Shape memory polymers based on semicrystalline thermoplastic polyurethanes bearing nanostructured hard segments |
EP1648548B1 (en) | 2003-07-18 | 2008-06-11 | Boston Scientific Limited | Medical devices |
JP2005102953A (en) | 2003-09-30 | 2005-04-21 | Tomii Kk | Orthodontic appliance |
WO2006086011A2 (en) * | 2004-08-27 | 2006-08-17 | University Of Connecticut | Crosslinked liquid crystalline polymer, method for the preparation thereof, and articles derived therefrom |
-
2003
- 2003-10-10 EP EP03774759A patent/EP1560881B1/en not_active Expired - Lifetime
- 2003-10-10 AU AU2003282572A patent/AU2003282572B2/en not_active Ceased
- 2003-10-10 WO PCT/US2003/032138 patent/WO2004033553A1/en active Application Filing
- 2003-10-10 JP JP2005501155A patent/JP4530989B2/en not_active Expired - Fee Related
- 2003-10-10 AT AT03774759T patent/ATE534704T1/en active
- 2003-10-10 ES ES03774759T patent/ES2373650T3/en not_active Expired - Lifetime
- 2003-10-10 US US10/683,559 patent/US7173096B2/en not_active Expired - Fee Related
- 2003-10-10 CA CA2501551A patent/CA2501551C/en not_active Expired - Fee Related
-
2007
- 2007-01-09 US US11/651,276 patent/US7563848B2/en not_active Expired - Fee Related
-
2009
- 2009-06-09 US US12/480,957 patent/US7705098B2/en not_active Expired - Fee Related
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2010
- 2010-03-05 US US12/718,249 patent/US7906573B2/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
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US20070142562A1 (en) | 2007-06-21 |
ES2373650T3 (en) | 2012-02-07 |
JP2006503171A (en) | 2006-01-26 |
EP1560881B1 (en) | 2011-11-23 |
CA2501551C (en) | 2012-12-11 |
EP1560881A1 (en) | 2005-08-10 |
US20090275704A1 (en) | 2009-11-05 |
WO2004033553A1 (en) | 2004-04-22 |
US7173096B2 (en) | 2007-02-06 |
ATE534704T1 (en) | 2011-12-15 |
US7563848B2 (en) | 2009-07-21 |
US20100160522A1 (en) | 2010-06-24 |
AU2003282572A1 (en) | 2004-05-04 |
US20040122184A1 (en) | 2004-06-24 |
US7705098B2 (en) | 2010-04-27 |
AU2003282572B2 (en) | 2009-04-09 |
JP4530989B2 (en) | 2010-08-25 |
US7906573B2 (en) | 2011-03-15 |
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