Acyclic Diene Metathesis with a Monomer from Renewable Resources: Control of Molecular Weight and One‐Step Preparation of Block Copolymers

Rybak, Anastasiya; Meier, Michael A. R.

doi:10.1002/cssc.200800047

Cited by 121 publications

(123 citation statements)

References 34 publications

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“…18,19 Unlike the related ring-opening metathesis polymerization (ROMP), which is a chain-growth process driven by the release of ring strain, ADMET is driven by the removal of the ethylene gas generated as a by-product. ADMET chemistry has been used recently in the synthesis of both all-carbon polyolefins [20][21][22] as well as polyethylene-like polymers containing heteroatoms [23][24][25][26][27][28][29] or aromatic rings [30][31][32] in the main chain. ADMET offers an interesting alternative for the incorporation of aliphatic sulfonate esters into the polymer backbone, which are rare in the literature.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of poly(sulfonate ester)s by ADMET polymerization

et al. 2014

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Many hydrocarbon polymers containing heteroatom defects in the main chain have been investigated as degradable polyethylene-like materials, including aliphatic polyesters. Here, acyclic diene metathesis (ADMET) polymerization was used for the synthesis of aliphatic poly(sulfonate ester)s. The requisite sulfonate ester containing α,ω-diene monomers with varying numbers of methylene groups were synthesized, and their polymerization in the presence of ruthenium-N-heterocyclic (Ru-NHC) alkylidene catalysts was studied. A clear negative neighboring group effect (NNGE) was observed for shorter dienes , either inhibiting polymerization or resulting in low-molecular-weight oligomers. The effect was absent when undec-10-en-1-yl undec-10-ene-1-sulfonate was employed as the monomer, and its ADMET polymerization afforded polymers with appreciable number-average molecular weights of up to 37,000 g/mol and a dispersity Đ of 1.8. These polymers were hydrogenated to afford the desired polyethylene-like systems. The thermal and morphological properties of both saturated and unsaturated polymers were investigated. The incorporation of sulfonate ester groups in the polymer backbone offers an interesting alternative to other heteroatoms and helps further the understanding of the effects of these defects on the overall polymer properties.

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Section: Introductionmentioning

confidence: 99%

Synthesis of poly(sulfonate ester)s by ADMET polymerization

et al. 2014

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“…[1] Especially castor oil is a very versatile renewable feedstock for all kinds of polymeric materials, including, e.g., polyesters, polyamides, polyurethanes, and many others. [2] One of the commercially available castor oil derived platform chemicals, 10-undecenoid acid 1, [2,3] was recently used to prepare polyamides X,20, [4] a variety of acyclic diene metathesis derived polyesters, [5][6][7] as well as different cross-linked materials, [8][9][10] thus demonstrating its broad range of application possibilities. Moreover, methyl 10-undecenoate 2 was shown to be a suitable starting material for the preparation of a,v-bisfunctional fatty acids for polycondensation polymers via cross-metathesis with methyl acrylate, [11] acrylonitrile, [12] and allyl chloride.…”

Section: Introductionmentioning

confidence: 99%

Fatty Acid Derived Monomers and Related Polymers Via Thiol‐ene (Click) Additions

Türünç

Meier

2010

Macromol. Rapid Commun.

174

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Thiol‐ene additions of methyl 10‐undecenoate, a castor oil derived renewable platform chemical, were studied with the goal of preparing a set of renewable monomers. Good to excellent yields were obtained for these solvent and initiator free thiol‐ene additions. The resulting monomers were then polymerized using TBD as a catalyst, to linear as well as hyperbranched polyesters that also contain thio‐ether linkages. All thus prepared polymers were fully characterized (NMR, GPC, DSC, and TGA) and the results of these investigations will be discussed within this contribution. The thermal analysis of these polymers revealed melting points in the range from 50 to 71 °C. Moreover, no significant weight loss was observed below 300 °C.magnified image

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“…[106] Recently, ADMET and ATMET bulk polymerizations of vegetable oil based undecyl undecenoate and glyceryl triundec-10-enoate, respectively, were investigated by Meier and co-workers using Grubbs' and Hoveyda-Grubbs' ruthenium catalysts, leading to high-molecular-weight triblock and branched polyesters. [104,105] Moreover, the molecular weight of the resulting polyesters can be controlled by adjusting the ratio of the monomer and the chain stopper of the vinyl monomer in a one-step, one-pot procedure.…”

Section: Olefin Metathesis Polymerization Of Vegetable Oilsmentioning

confidence: 99%

“…Olefin metathesis has also been employed in polymer synthesis, primarily through ring-opening metathesis polymerization (ROMP), [102] acyclic diene metathesis polymerization (ADMET), [103,104] or acyclic triene metathesis polymerization (ATMET) [105] . The Grubbs' ruthenium catalyst has been used for the ADMET polymerization of soybean oil, resulting in a variety of materials from sticky oils to rubbers.…”

Section: Olefin Metathesis Polymerization Of Vegetable Oilsmentioning

confidence: 99%

Novel Polymeric Materials from Vegetable Oils and Vinyl Monomers: Preparation, Properties, and Applications

2009

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Veggie-based products: Vegetable-oil-based polymeric materials, prepared by free radical, cationic, and olefin metathesis polymerizations, range from soft rubbers to ductile or rigid plastics, and to high-performance biocomposites and nanocomposites. They display a wide range of thermophysical and mechanical properties and may find promising applications as alternatives to petroleum-based polymers.Vegetable oils are considered to be among the most promising renewable raw materials for polymers, because of their ready availability, inherent biodegradability, and their many versatile applications. Research on and development of vegetable oil based polymeric materials, including thermosetting resins, biocomposites, and nanocomposites, have attracted increasing attention in recent years. This Minireview focuses on the latest developments in the preparation, properties, and applications of vegetable oil based polymeric materials obtained by free radical, cationic, and olefin metathesis polymerizations. The novel vegetable oil based polymeric materials obtained range from soft rubbery materials to ductile or rigid plastics and to high-performance biocomposites and nanocomposites. These vegetable oil based polymeric materials display a wide range of thermophysical and mechanical properties and should find useful applications as alternatives to their petroleum-based counterparts.

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Acyclic Diene Metathesis with a Monomer from Renewable Resources: Control of Molecular Weight and One‐Step Preparation of Block Copolymers

Cited by 121 publications

References 34 publications

Synthesis of poly(sulfonate ester)s by ADMET polymerization

Synthesis of poly(sulfonate ester)s by ADMET polymerization

Fatty Acid Derived Monomers and Related Polymers Via Thiol‐ene (Click) Additions

Novel Polymeric Materials from Vegetable Oils and Vinyl Monomers: Preparation, Properties, and Applications

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