Post-polymerization functionalization of polyolefins

Boaen, Nicole K.; Hillmyer, Marc A.

doi:10.1039/b311405h

Cited by 443 publications

(383 citation statements)

References 38 publications

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“…Since all polyolefins are aliphatic hydrocarbons consisting of only hydrogen and carbon atoms, they show poor wettability and adhesion characteristics. To overcome these limitations, the modification of polyolefins as a serious research area in polymer science has come into prominence [3,4]. Due to the absence of polar groups, semi-crystalline morphology, resistance to polar or ionic chemicals and limited chemical substitution, oxidation and free radical reactions, these modifications are quite challenging and usually are difficult to maintain [5].…”

Section: Introductionmentioning

confidence: 99%

Polypropylene-based graft copolymers via CuAAC click chemistry

Açık¹,

Sey²,

Taşdelen³

2018

Express Polym. Lett.

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Abstract. Graft copolymers from commercial chlorinated polypropylene (PP-Cl) possessing either poly(ethylene glycol) (PEG) or poly(ɛ-caprolactone) (PCL) grafts are synthesized by copper (I)-catalyzed azide-alkyne cycloaddition 'click' reaction (CuAAC). For this purpose, azido-functional polypropylene is prepared by nucleophilic substitution of chlorine groups of PP-Cl with azidotrimethylsilane-tetrabutylammonium fluoride. Whereas, the clickable alkyne end-functional PEG and PCL are independently synthesized by esterification reaction of poly(ethylene glycol) methyl ether with 4-pentyonic acid at room temperature and ring-opening polymerization of ε-caprolactone using stannous octoate as catalyst and propargyl alcohol as initiator. Finally, the corresponding graft copolymers, PP-g-PEG and PP-g-PCL, with different surface properties were successfully synthesized by CuAAC 'click' reaction under mild condition. Spectral, chromatographic and thermal analyses at various stages prove the formation of desired polypropylene-based graft copolymers with well-defined properties. Furthermore, the water contact angle values of PP-Cl, PP-g-PEG and PP-g-PCL are found as 90±1°, 78±1.8° and 83±2.1°, respectively.

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Section: Introductionmentioning

confidence: 99%

Polypropylene-based graft copolymers via CuAAC click chemistry

Açık¹,

Sey²,

Taşdelen³

2018

Express Polym. Lett.

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“…Incorporation of side chains, especially polar functional side chains, is desirable and often necessary to give the polymer desired properties and better performance. Due to the physical and chemical stability of PE, direct functionalization of PE is challenging [4]. Therefore, PE derivatives bearing functional side chains are typically produced by radical or coordination copolymerization of ethylene and functionalized olefin(s).…”

Section: Introductionmentioning

confidence: 99%

Functionalized regio-regular linear polyethylenes from the ROMP of 3-substituted cyclooctenes

et al. 2014

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We demonstrated that the ring-opening metathesis polymerization (ROMP) of 3-substituted cyclooctenes bearing polar substituents allows the synthesis of highly regio-and stereo-regular polymers. A series of polyalkenamers with 90-99 % head-to-tail/trans configuration were synthetized in good yields (33-87 % yield). Upon saturation of the backbone using diimide, these polymers represent a class of linear polyethylene derivatives where the polar side chain is located on every eighth carbon. The thermal properties of both the saturated and unsaturated polymers depend strongly on the size and polarity of the functional side groups. The results presented here demonstrate that the 3-substituted cyclooctenes can be used not only for the synthesis of precisely functionalized polyethylene derivatives, but also to participate in the ringopening metathesis copolymerization with unfunctionalized cyclic olefins to generate copolymers with tunable properties.

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“…1 While commercially successful, this strategy leads to poorly defined polymeric structures and requires highly optimized conditions, extra processing steps/additives, and significant energy input. In contrast, development of a synthesisdriven, molecular approach involving the controlled introduction of reactive functional groups into the backbone of PE and other commodity polyolefins would allow for precise tailoring of polymer reactivity and final physical properties.…”

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confidence: 99%

Ketene Functionalized Polyethylene: Control of Cross-Link Density and Material Properties

et al. 2010

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Abstract:The functionalization and cross-linking of polyethylene is synthetically challenging, commonly relying on highly optimized radical based postpolymerization strategies. To address these difficulties, a norbornene monomer containing Meldrum's acid is shown to be effectively copolymerized with polyethylene using a nickel R-iminocarbaxamidato complex, providing high-melting, semicrystalline polymers with a tunable incorporation of the functional comonomer. Upon heating the copolymer to common polyethylene processing temperatures, the thermolysis of Meldrum's acid to ketene provides the desired reactive group. This simple and versatile methodology does not require small molecule radical sources or catalysts, and the dimerization of the in situ generated ketenes is shown to provide tunable cross-linking densities in polyethylene. Subsequent rheological and tensile experiments illustrate the ability to tune cross-linked polyethylene properties by comonomer incorporation and elucidate valuable structure/property relationships in these materials. This study illustrates the power of well-defined and synthetically accessible functional groups in polyolefin synthesis and functionalization.

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Post-polymerization functionalization of polyolefins

Cited by 443 publications

References 38 publications

Polypropylene-based graft copolymers via CuAAC click chemistry

Polypropylene-based graft copolymers via CuAAC click chemistry

Functionalized regio-regular linear polyethylenes from the ROMP of 3-substituted cyclooctenes

Ketene Functionalized Polyethylene: Control of Cross-Link Density and Material Properties

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