Amphiphilic copolymers of sucrose methacrylate and acrylic monomers: Bio-based materials from renewable resource

Oliveira, Heitor Fernando Nunes de; Felisberti, Maria I.

doi:10.1016/j.carbpol.2012.12.061

Cited by 18 publications

(40 citation statements)

References 33 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…All these reagents were of analytical grade and were used without any further purification or treatment. Protease Protin® NY100 provided by Amano (Nagoya, Japan) was treated with an aqueous solution of KOH at pH 10, followed by freeze‐drying, as described elsewhere …”

Section: Methodsmentioning

confidence: 99%

“…Esterification is commonly used to functionalize carbohydrates with vinylic or (meth)acrylic groups. These reactions can be performed by chemical or enzymatic routes . In general, chemical routes require multiple steps of selective protection and deprotection of the hydroxyls, with the aim of the selective (trans)esterification of one hydroxyl with a polymerizable group .…”

Section: Introductionmentioning

confidence: 99%

“…These reactions can be performed by chemical or enzymatic routes . In general, chemical routes require multiple steps of selective protection and deprotection of the hydroxyls, with the aim of the selective (trans)esterification of one hydroxyl with a polymerizable group . This route was first performed by Kimura and co‐workers for the synthesis of 3‐O‐methacryloyl‐D‐glucofuranose, with a yield of ∼24% for the unprotected methacrylated carbohydrate.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Enzymatic synthesis and structural characterization of methacryloyl‐D‐fructose‐ and methacryloyl‐D‐glucose‐based monomers and poly(methacryloyl‐D‐fructose)‐based hydrogels

Perin

Felisberti

2018

J of Chemical Tech & Biotech

Self Cite

View full text Add to dashboard Cite

BACKGROUND Carbohydrates are important renewable raw materials and their modification by enzymatic reactions with polymerizable groups is of great importance due the possibility of production of polymers with properties for biomedical applications. In this study, D‐fructose‐ and D‐glucose‐based monomers were prepared by enzymatic reactions and structurally characterized. Moreover, hydrogels based on poly(methacryloyl‐D‐fructose) were also prepared and characterized. RESULTS The conversions of 99% and 34% for D‐fructose and D‐glucose, respectively, were achieved using 2,2,2‐trifluoroethyl methacrylate as the methacrylic donor and commercial lipase Novozyme® 435 (EC 3.1.1.3) as enzymatic catalyst in t‐butanol. The molar ratios of D‐fructose and D‐glucose mono‐ and dimethacrylate were 57/43 and 87/13, respectively. These monomers are an isomeric mixture related to the tautomeric equilibrium of the carbohydrates in solution. Methacryloyl‐D‐fructose was polymerized in the presence of a controlled amount of ethyleneglycol dimethacrylate as crosslinker achieving hydrogels with different crosslinking densities which are mechanically stable when subject to compression–decompression cycles and have a high water swelling capability. CONCLUSION The combination of 2,2,2‐trifluoroethylmethacrylate and Novozym® 435 in a heterogeneous media lead to the continuous carbohydrate solubilization and reaction with the formation of carbohydrates‐based monomers. The control of the monomer functionality enables the synthesis of hydrogels with different crosslinking densities that tune their properties. © 2017 Society of Chemical Industry

show abstract

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Enzymatic synthesis and structural characterization of methacryloyl‐D‐fructose‐ and methacryloyl‐D‐glucose‐based monomers and poly(methacryloyl‐D‐fructose)‐based hydrogels

Perin

Felisberti

2018

J of Chemical Tech & Biotech

Self Cite

View full text Add to dashboard Cite

show abstract

“…organic copolymers [27][28][29][30][31][32] and various hydrogels [33][34][35][36][37][38][39]), but to our knowledge it is the first reported approach to pore size distribution estimation in swollen cross-linked polymers with the employment of thermogravimetric analysis combined with microscopic measurements. A standard procedure based on quasiisothermal programme of heating applied for desorption of liquid from porous solid and the Kelvin equation, along with a simple mathematic calculation, provides information concerning free spaces in the swollen material.…”

Section: Discussionmentioning

confidence: 99%

Swelling effects in cross-linked polymers by thermogravimetry

Sienkiewicz

Krasucka

Charmas

et al. 2017

J Therm Anal Calorim

View full text Add to dashboard Cite

The present study focuses on the mechanism of swelling and evaluates interactions between solvents of different chemical characters (polar-ethanol, nonpolarn-heptane) and commercially available porous Amberlite polymers (XAD4, XAD16, XAD7HP) by temperatureprogrammed desorption (TPD). The first two polymers are the product of copolymerization of styrene and divinylbenzene. Despite having the same chemical composition, they differ in pore size and volume. The Amberlite XAD7HP is composed of an acrylic matrix and has lower pore volume and specific surface area than XAD16 and XAD4. All three resins have the ability to swell, though the per cent of polymeric network expansion during this process varies depending on the solvent used (e.g. in tetraethyl orthosilicate, XAD4 and XAD16 spherical particles increase in volume by 20-30%, while XAD7HP particles can expand by more than 120%). The TPD experiment was performed in dynamic linear and quasistatic heating mode. Based on thermogravimetric data, the desorption energy of selected liquids and pore size distribution in the swollen state were estimated. The obtained results are discussed in terms of both mathematical modelling and low-temperature nitrogen adsorption-desorption experiment.

show abstract

“…Since the synthesis of carbohydrate‐based polymers and hydrogels by the chemo‐enzymatic route reported by Dordick and coworkers, many monomers, crosslinkers and polymeric materials based on carbohydrates (named glycopolymers) have been prepared . In this context, our research group has been investing great efforts in developing new polymeric materials based on carbohydrates, such as polymers, copolymers and hydrogels based on fructose, glucose and sucrose methacrylates …”

Section: Introductionmentioning

confidence: 99%

Macroporous hydrogels based on carbohydrates monomethacrylates and dimethacrylates: singular properties from carbohydrate‐based crosslinkers

Perin

Fonseca

Felisberti

2019

J of Chemical Tech & Biotech

Self Cite

View full text Add to dashboard Cite

BACKGROUND Readily available feedstock and biocompatibility make carbohydrate‐based hydrogels promising materials for biomedical applications. However, carbohydrate‐based crosslinkers are rather underexplored when compared with crosslinkers derived from fossil resources. In this study, novel fully bio‐based hydrogels derived from enzymatically produced d‐fructose and d‐glucose methacrylate monomers were synthesized with different amounts of d‐fructose dimethacrylate crosslinker. RESULTS The use of a carbohydrate‐based crosslinker endows hydrogels with high swelling coefficients, up to 2400%, and superior mechanical resistance (compressive modulus up to 9.5 kPa with a maximum stress up to 50 kPa) compared with conventional crosslinkers based on fossil resources. Hydrogels shape and crosslinking density influences hydrogel morphology, swelling behavior and mechanical resistance. Moreover, hydrogels presented cell viability, biodegradability and hydrolysis‐resistance over a wide range of pH. CONCLUSION The use of a highly hydrophilic crosslinker based on carbohydrate for hydrogels synthesis enables the use of high crosslinker concentration, which improves mechanical properties, however with minor loss of the water swelling capacity, compared with conventional fossil‐based crosslinkers. This is an important advantage over conventional crosslinkers based on fossil resources. Moreover, slab hydrogels hold higher stress under compression–decompression cycles, and present higher resistance to hydrolysis in basic medium due to the thicker pore walls than cylindrical ones. © 2019 Society of Chemical Industry

show abstract

Amphiphilic copolymers of sucrose methacrylate and acrylic monomers: Bio-based materials from renewable resource

Cited by 18 publications

References 33 publications

Enzymatic synthesis and structural characterization of methacryloyl‐D‐fructose‐ and methacryloyl‐D‐glucose‐based monomers and poly(methacryloyl‐D‐fructose)‐based hydrogels

Enzymatic synthesis and structural characterization of methacryloyl‐D‐fructose‐ and methacryloyl‐D‐glucose‐based monomers and poly(methacryloyl‐D‐fructose)‐based hydrogels

Swelling effects in cross-linked polymers by thermogravimetry

Macroporous hydrogels based on carbohydrates monomethacrylates and dimethacrylates: singular properties from carbohydrate‐based crosslinkers

Contact Info

Product

Resources

About