Hyperbranched aliphatic polyethers obtained from environmentally benign monomer: glycerol carbonate

Rokicki, Gabriel; Rakoczy, Paweł; Parzuchowski, Paweł G.; Sobiecki, Marcin

doi:10.1039/b501597a

Cited by 310 publications

(245 citation statements)

References 36 publications

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“…The chemical shift of central hydrogen was observed in the spectrum of triacetin, 20,21 and it was attributed to hydrogen connected to secondary carbon for glycerol carbonate. The same displacement was observed in simulate structures.…”

Section: Resultsmentioning

confidence: 98%

Synthesis and characterization of polyesters from glycerol by-product of biodiesel production

Moura¹,

Nunes²,

Neto³

et al. 2012

J. Braz. Chem. Soc.

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resinas do tipo uréia/formaldeído ou fenol/formaldeído para melhorar as qualidades de aderência e resistência à umidade dessas resinas. Neste trabalho, foram sintetizados seis tipos de resinas derivadas do glicerol, sendo nomeadas GAA (glicerol/ácido adípico), GAAU (glicerol/ácido adípico/uréia), GAF (glicerol/ácido ftálico), GU (glicerol/uréia), GUF (glicerol/uréia/formaldeído) e GF (glicerol/formaldeído). As resinas derivadas dos ácidos carboxílicos tiveram melhor estabilidade térmica (até 350 ºC) do que as resinas derivadas do formaldeído (até 200 ºC). As massas moleculares médias das resinas foram determinadas por espectrometria de massas por tempo de vôo acoplada à ionização dessortiva de matriz por laser (MALDI-TOF MS) e cromatografia de permeação em gel (GPC), e encontram-se na faixa de 1800-2800 Da, sendo portanto, oligômeros, e os índices de polidispersão no intervalo de 1,3 a 1,8. As técnicas de ressonância magnética nuclear (NMR) de 1 H e 13 C foram usadas para identificar as estruturas das resinas.Glycerol, a by-product from biodiesel production can react with di-carboxylic organic acids, resulting in polyesters, and can be used in the composition of urea/formaldehyde or phenol/ formaldehyde resins to improve the qualities of adhesion and moisture resistance of them. In this work, six kinds of resins derived from glycerol, named as GAA (glycerol/adipic acid), GAAU (glycerol/adipic acid/urea), GAF (glycerol/phtalic acid), GU (glycerol/urea), GUF (glycerol/ urea/formaldehyde) and GF (glycerol/formaldehyde), were synthesized. The resins derived from carboxylic acids had better thermal stability (up to 350 ºC) than those derived from formaldehyde (up to 200 ºC). The average molecular weights of the resins were determined by matrix assisted laser desorption ionization time-of-flight mass spectrometry (MALDI-TOF MS) and gelpermeation chromatography (GPC), and are in the range of 1800-2800 Da, being oligomers, and the polydispersity indexes are in the range of 1.3 to 1.8. The 1 H and 13 C nuclear magnetic resonance (NMR) techniques were used to identify the structure of the resins.

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Section: Resultsmentioning

confidence: 98%

Synthesis and characterization of polyesters from glycerol by-product of biodiesel production

Moura¹,

Nunes²,

Neto³

et al. 2012

J. Braz. Chem. Soc.

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“…Tin dibutyl dilaurate was used as catalyst. Glycerol carbonate (4-hydroxymethyl-1,3-dioxolane-2-on) was synthesized from glycerol and dimethyl carbonate according the procedure described by Rokicki et al (2005).…”

Section: Methodsmentioning

confidence: 99%

“…Also, one can see that these two parameters were manifested in the obtained strengths values. The degree of branching of the polyglycerols has been neglected in this discussion, since it is assumed to be close to ~ 0.5 for high conversion degrees (Rokicki et al 2005). …”

Section: Performance Of the Adhesive Systemsmentioning

confidence: 99%

Hyperbranched Polyglycerols With Bisphenol a Core as Glycerol-Derived Components of Polyurethane Wood Adhesives

Mamiński¹,

Szymański²,

Parzuchowski³

et al. 2012

BioResources

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a Two hyperbranched polyglycerols (HBPGs) and one oligoglycerol containing bisphenol A in the core of the molecule were synthesized from glycerol carbonate and applied as polyols in 2-component polyurethane adhesive systems. It was shown that mechanical performance of the joints made in solid wood depended on the hydroxyl functionality of the polyglycerol as well as on the type of the isocyanate used as a crosslinker. The shear strengths of the best-performing joints exceeded that of the substrate. Eventually, it was proved that hyperbranched polyglycerols might be convenient glycerol-derived raw materials for polyurethane adhesives.

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“…Besides the use of glycidol, the environmentally benign monomer glycerol carbonate (4-hydroxymethyl-1,3-dioxolan-2-one) was also used in ROMBP to generate hbPG (M n ¼ 800-1100 g mol À1 , M w /M n < 1.3), which is formed under decarboxylation. 76 In another work, the microwave-assisted polymerization of glycerol carbonate only led to the formation of PG oligomers. 77 To sum up, almost 90 years after the first reported ''polymerization'' of glycidol, the synthesis of hbPG by ROMBP using the slow monomer-addition (SMA) technique and other methods has become a versatile method for the synthesis of these hyperbranched polyether polyols with control over molecular weight, polydispersity, and DB.…”

Section: Polyglycerolmentioning

confidence: 99%

Hyperbranched aliphatic polyether polyols

Schömer

Schüll

Frey

2012

J. Polym. Sci. A Polym. Chem.

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Hyperbranched polymers, dendritic macromolecules with branch-on-branch structures, have become an important polymer class since the early 1990s. They combine several advantages of the perfectly branched dendrimers with easy accessibility, typically in a one-step synthesis. Hyperbranched polyethers are a particularly interesting class of chemically stable and often biocompatible materials. Multifunctional hyperbranched polyethers with controllable molar mass and comparably low polydispersities can been prepared using hydroxyl-functional epoxides or oxetanes for polymerization via anionic and cationic polymerization mechanisms. Here, we review the progress in the preparation, characterization, and application of these uniquely versatile aliphatic polyether polyols. Their unusual mechanical, thermal, and solution properties render them useful for a variety of applications, for example, as building blocks for various complex macromolecular architectures or in biomedical applications.

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Hyperbranched aliphatic polyethers obtained from environmentally benign monomer: glycerol carbonate

Cited by 310 publications

References 36 publications

Synthesis and characterization of polyesters from glycerol by-product of biodiesel production

Synthesis and characterization of polyesters from glycerol by-product of biodiesel production

Hyperbranched Polyglycerols With Bisphenol a Core as Glycerol-Derived Components of Polyurethane Wood Adhesives

Hyperbranched aliphatic polyether polyols

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