Preparation and Polymerization of Acrylic Esters of Olefinic Alcohols

Rehberg, C. E.; Fisher, C. H.

doi:10.1021/jo01166a004

Cited by 48 publications

(15 citation statements)

References 2 publications

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“…Further transesterification reactions can be found in the literature, in which metal alkoxides [11][12][13][14][15][16] , aluminum isopropoxide [17][18][19] , tetraalkoxytitanium compounds [20][21][22] and organotin alkoxides 23,24 are applied as catalysts.…”

Section: General Aspects Of Transesterificationmentioning

confidence: 99%

Transesterification of vegetable oils: a review

Schuchardt¹,

Sercheli²,

Vargas³

1998

J. Braz. Chem. Soc.

946

539

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A transesterificação de óleos vegetais com metanol, bem como as principais aplicações de ésteres metílicos de ácidos graxos, são revisadas. São descritos os aspectos gerais desse processo e a aplicabilidade de diferentes tipos de catalisadores (ácidos, hidróxidos, alcóxidos e carbonatos de metais alcalinos, enzimas e bases não-iônicas, como aminas, amidinas, guanidinas e triamino(imino)fosforanos). Enfoque especial é dado às guanidinas, que podem ser facilmente heterogeneizadas em polímeros orgânicos. No entanto, as bases ancoradas lixiviam dos polímeros. Novas estratégias para a obtenção de guanidinas heterogeneizadas mais resistentes à lixiviação são propostas. Finalmente, são descritas várias aplicações para ésteres de ácidos graxos, obtidos por transesterificação de óleos vegetais.The transesterification of vegetable oils with methanol as well as the main uses of the fatty acid methyl esters are reviewed. The general aspects of this process and the applicability of different types of catalysts (acids, alkaline metal hydroxides, alkoxides and carbonates, enzymes and non-ionic bases, such as amines, amidines, guanidines and triamino(imino)phosphoranes) are described. Special attention is given to guanidines, which can be easily heterogenized on organic polymers. However, the anchored catalysts show leaching problems. New strategies to obtain non-leaching guanidine-containing catalysts are proposed. Finally, several applications of fatty acid esters, obtained by transesterification of vegetable oils, are described.

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Section: General Aspects Of Transesterificationmentioning

confidence: 99%

Transesterification of vegetable oils: a review

Schuchardt¹,

Sercheli²,

Vargas³

1998

J. Braz. Chem. Soc.

946

539

View full text Add to dashboard Cite

show abstract

“…where Tg is the copolymer glass transition temperature, WF and WH the average weight fraction of monomer units F and H in the copolymer chains, TgFF and TgHH the glass transition temperatures of both homopolymers, and TgFH that of the alternating copolymer; PFF, PFH, PHF, and PHH refer to the probabilities of having various linkages defined statistically according to eqs. ( 1 ) and (2). Figure 7 shows the linear diagram obtained after the appli- It is clear from these values that the alternating diad FH or HF presents a glass transition temperature lower than the arithmetical average of the Tg of both homopolymers.…”

Section: Thermal Transitions Of F-h Copolymersmentioning

confidence: 99%

Free radical copolymerization of furfuryl acrylate and 2‐hydroxyethyl‐methacrylate

Zaldívar

Péniche

Bulay³

et al. 1993

J. Polym. Sci. A Polym. Chem.

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Copolymers of furfuryl acrylate (F) and 2‐hydroxyethyl methacrylate (H) were prepared by free radical polymerization in DMF solution at 50°C, using 2,2′‐azobisisobutyronitrile (AIBN) as initiator. The reactivity ratios of both monomers were calculated according to the general copolymerization equation using the Fineman‐Ross and Kelen‐Tüdös linearization methods, as well as the Tidwell and Mortimer nonlinear least‐squares treatment. The reactivity ratios obtained were rF = 0.93 and rH = 1.42. The microstructure of copolymer chains is described on the basis of first‐order Markov statistics, and the copolymer glass transition temperatures were determined calorimetrically. The variation of Tg with the copolymer composition is discussed according to modern methods, considering the sequence distribution of monomeric units along the copolymer chains. Also the Tg of the corresponding homopolymers was determined giving the values Tg(F) = 321 K and Tg(H) = 358 K, whereas the Tg of the corresponding alternating diad has an average value of TgFH = 326 K. © 1993 John Wiley & Sons, Inc.

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“…[ 1,2 ] Even though the generally preferred strategy is to synthesize and copolymerize functional monomers to obtain envisioned macromolecules, this approach is limited by the restrictions imposed by the polymerization mechanism, e.g., undesired branching or crosslinking during radical polymerization of monomers bearing an additional unsaturation. [ 3–6 ] Post‐polymerization modifications provide, therefore, a complementary tool to overcome the limitations imposed by the polymerization mechanism. Furthermore, the modification of relatively simple polymeric precursor homopolymers is an attractive strategy to obtain a diverse set of functional copolymers as materials for advanced applications such as therapeutics, tissue engineering, adaptable or self‐healing materials.…”

Section: Figurementioning

confidence: 99%

Stoichiometric Control over Partial Transesterification of Polyacrylate Homopolymers as Platform for Functional Copolyacrylates

Guyse

Bernhard

Hoogenboom

2020

Macromol. Rapid Commun.

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Only recently, post‐polymerization modification reactions of unactivated polyacrylates have been emerging as an attractive alternative to utilizing reactive monomers, enabling the synthetic upcycling of these widely applied polymers. Within this contribution, the triazabicyclodecene‐catalyzed transesterification of polyacrylates is reported, including the reaction kinetics and the broad scope for macromolecular design of functional copolyacrylates. More specifically, the transesterification is performed under equilibrium conditions with a set of primary alcohols whereby the reaction kinetics and the obtained conversion as a function of stoichiometric excess of alcohol are evaluated. The results show that the obtained conversion is dependent on the polarity of the solvent and of the alcohol. Through this approach, the transesterification degree can be accurately controlled by stoichiometry, enabling the precise modulation of the macromolecular structure. Finally, the utility of this approach is demonstrated to incorporate functional side chains that are incompatible with radical polymerization, to facilitate Diels–Alder and thiol‐ene reactions, enabling access to a broad range of functional materials from simple polyacrylate homopolymer precursors.

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Preparation and Polymerization of Acrylic Esters of Olefinic Alcohols

Abstract: In connection with projects (1) concerned with the production and subsequent cross-linkage of unsaturated acrylic resins, various monomers containing two or more olefinic linkages were required. This paper describes the preparation of

Cited by 48 publications

References 2 publications

Transesterification of vegetable oils: a review

Transesterification of vegetable oils: a review

Free radical copolymerization of furfuryl acrylate and 2‐hydroxyethyl‐methacrylate

Stoichiometric Control over Partial Transesterification of Polyacrylate Homopolymers as Platform for Functional Copolyacrylates

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