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Synthesis and interfacial behavior o...

University of Massachusetts Amherst., Polymer Science & Engineering.

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Synthesis and interfacial behavior of functional amphiphilic graft copolymers prepared by ring-opening metathesis polymerization.

Record Type:	Electronic resources : Monograph/item
Title/Author:	Synthesis and interfacial behavior of functional amphiphilic graft copolymers prepared by ring-opening metathesis polymerization./
Author:	Breitenkamp, Kurt E., II.
Description:	221 p.
Notes:	Adviser: Todd S. Emrick.
Contained By:	Dissertation Abstracts International70-03B.
Subject:	Chemistry, Organic. -
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3349710
ISBN:	9781109059205

Synthesis and interfacial behavior of functional amphiphilic graft copolymers prepared by ring-opening metathesis polymerization.
Breitenkamp, Kurt E., II.

Synthesis and interfacial behavior of functional amphiphilic graft copolymers prepared by ring-opening metathesis polymerization. - 221 p.

Adviser: Todd S. Emrick.

Thesis (Ph.D.)--University of Massachusetts Amherst, 2009.

This thesis describes the synthesis and application of a new series of amphiphilic graft copolymers with a hydrophobic polyolefin backbone and pendent hydrophilic poly(ethylene glycol) (PEG) grafts. These copolymers are synthesized by ruthenium benzylidene-catalyzed ring-opening metathesis polymerization (ROMP) of PEG-functionalized cyclic olefin macromonomers to afford polycyclooctene- graft-PEG (PCOE-g-PEG) copolymers with a number of tunable features, such as PEG graft density and length, crystallinity, and amphiphilicity. Macromonomers of this type were prepared first by coupling chemistry using commercially available PEG monomethyl ether derivatives and a carboxylic acid-functionalized cycloctene. In a second approach, macromonomers possessing a variety of PEG lengths were prepared by anionic polymerization of ethylene oxide initiated by cyclooctene alkoxide. This methodology affords a number of benefits compared to coupling chemistry including an expanded PEG molecular weight range, improved hydrolytic stability of the PEG-polycyclooctene linkage, and a reactive hydroxyl end-group functionality for optional attachment of biomolecules and probes.

ISBN: 9781109059205Subjects--Topical Terms:

516206
Chemistry, Organic.

Synthesis and interfacial behavior of functional amphiphilic graft copolymers prepared by ring-opening metathesis polymerization.
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020 $a 9781109059205
035 $a (UMI)AAI3349710
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040 $a UMI $c UMI
100 1 $a Breitenkamp, Kurt E., II. $3 1064666
245 1 0 $a Synthesis and interfacial behavior of functional amphiphilic graft copolymers prepared by ring-opening metathesis polymerization.
300 $a 221 p.
500 $a Adviser: Todd S. Emrick.
500 $a Source: Dissertation Abstracts International, Volume: 70-03, Section: B, page: 1697.
502 $a Thesis (Ph.D.)--University of Massachusetts Amherst, 2009.
520 $a This thesis describes the synthesis and application of a new series of amphiphilic graft copolymers with a hydrophobic polyolefin backbone and pendent hydrophilic poly(ethylene glycol) (PEG) grafts. These copolymers are synthesized by ruthenium benzylidene-catalyzed ring-opening metathesis polymerization (ROMP) of PEG-functionalized cyclic olefin macromonomers to afford polycyclooctene- graft-PEG (PCOE-g-PEG) copolymers with a number of tunable features, such as PEG graft density and length, crystallinity, and amphiphilicity. Macromonomers of this type were prepared first by coupling chemistry using commercially available PEG monomethyl ether derivatives and a carboxylic acid-functionalized cycloctene. In a second approach, macromonomers possessing a variety of PEG lengths were prepared by anionic polymerization of ethylene oxide initiated by cyclooctene alkoxide. This methodology affords a number of benefits compared to coupling chemistry including an expanded PEG molecular weight range, improved hydrolytic stability of the PEG-polycyclooctene linkage, and a reactive hydroxyl end-group functionality for optional attachment of biomolecules and probes.
520 $a The amphiphilic nature of these graft copolymers was exploited in oil-water interfacial assembly, and the unsaturation present in the polycyclooctene backbone was utilized in covalent cross-linking reactions to afford hollow polymer capsules. In one approach, a bis-cyclooctene PEG derivative was synthesized and co-assembled with PCOE-g-PEG at the oil-water interface. Upon addition of a ruthenium benzylidene catalyst, a cross-linked polymer shell is formed through ring-opening cross-metathesis between the bis-cyclooctene cross-linker and the residual olefins in the graft copolymer. By incorporating a fluorescent-labeled cyclooctene into the graft copolymer, both oil-water interfacial segregation and effective cross-linking were confirmed using confocal laser scanning microscopy (CLSM). In a second approach, reactive functionality capable of chemical cross-linking was incorporated directly into the polymer backbone by synthesis and copolymerization of phenyl azide and acyl hydrazine-functional cyclooctene derivatives. Upon assembly, these reactive polymers were cross-linked by photolysis (in the phenyl azide case) or by addition of glutaraldehyde (in the acyl hydrazine case) to form mechanically robust polymer capsules with tunable degradability (i.e. non-degradable or pH-dependent degradability). This process permits the preparation of both oil-in-water and water-in-oil capsules, thus enabling the encapsulation of hydrophobic or hydrophilic reagents in the capsule core. Furthermore, the assemblies can be sized from tens of microns to the 150 nm - 1 microm size range by either membrane extrusion or ultrasonication techniques. These novel capsules may be well-suited for a number of controlled release applications, where the transport of encapsulated compounds can be regulated by factors such as cross-link density, hydrolytic stability, and environmental triggers such as changes in pH.
590 $a School code: 0118.
650 4 $a Chemistry, Organic. $3 516206
650 4 $a Chemistry, Polymer. $3 1018428
690 $a 0490
690 $a 0495
710 2 $a University of Massachusetts Amherst. $b Polymer Science & Engineering. $3 1018485
773 0 $t Dissertation Abstracts International $g 70-03B.
790 $a 0118
790 1 0 $a Coughlin, E. Bryan $e committee member
790 1 0 $a Dinsmore, Anthony D. $e committee member
790 1 0 $a Emrick, Todd S., $e advisor
791 $a Ph.D.
792 $a 2009
856 4 0 $u http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3349710