Biorefinery Byproducts and Epoxy Biorenewable Monomers: A Structural Elucidation of Humins and Triglycidyl Ether of Phloroglucinol Cross-Linking.

Abstract:

:The need for thermosets from renewable resources is continuously increasing to find eco-friendly alternatives to petroleum-derived materials. Products obtained from biomass have shown to play an important role in this challenge. Here, we present the structural characterization of new biobased thermosets made of humins, a byproduct of lignocellulosic biorefinery, and glycidylated phloroglucinol coming from the biomass phenolic fraction. By employing attenuated total reflection-Fourier transform infrared and NMR spectroscopies, we elucidated the connections between these two systems, contributing to clarify their molecular structures and their reactivities. We demonstrated that the resin curing takes place through ether bond formation between humin hydroxyl functions and phloroglucinol epoxides. Besides cross-linking, humins show a complex rearrangement of their furanic structure through different concomitant chemical pathways depending on the reaction conditions.

journal_name

Biomacromolecules

journal_title

Biomacromolecules

authors

Cantarutti C,Dinu R,Mija A

doi

10.1021/acs.biomac.9b01248

subject

Has Abstract

pub_date

2020-02-10 00:00:00

pages

517-533

issue

2

eissn

1525-7797

issn

1526-4602

journal_volume

21

pub_type

杂志文章
  • Superstrong and Tough Hydrogel through Physical Cross-Linking and Molecular Alignment.

    abstract::Hydrogels are attracting increasing attention due to their potential use in various fields. However, most of the existing hydrogels have limitations in either dissipating mechanical energy or maintaining high stretchability under deformation, thus do not possess high mechanical properties. Herein, poly(vinyl alcohol) ...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/acs.biomac.9b01223

    authors: Chen W,Li N,Ma Y,Minus ML,Benson K,Lu X,Wang X,Ling X,Zhu H

    更新日期:2019-12-09 00:00:00

  • Altering the energy landscape of virus self-assembly to generate kinetically trapped nanoparticles.

    abstract::Controlling self-assembly is critical to the advancement of nanotechnology. A rugged or crenated assembly energy surface can redirect assembly off path. By using a defined starting point and an energy surface made rough by a strong association energy, we can impose entirely new assembly paths and products. Normally, t...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm901160b

    authors: Burns K,Mukherjee S,Keef T,Johnson JM,Zlotnick A

    更新日期:2010-02-08 00:00:00

  • Encapsulation of Doxorubicin in Furcellaran/Chitosan Nanocapsules by Layer-by-Layer Technique for Selectively Controlled Drug Delivery.

    abstract::Minimization of drug side effects is a hallmark of advanced targeted therapy. Herein we describe the synthesis of polysaccharide-based nanocapsules prepared from furcellaran and chitosan via layer-by-layer deposition using electrostatic interaction. Using doxorubicin as a model drug, prepared nanocapsules showed excel...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/acs.biomac.9b01175

    authors: Milosavljevic V,Jamroz E,Gagic M,Haddad Y,Michalkova H,Balkova R,Tesarova B,Moulick A,Heger Z,Richtera L,Kopel P,Adam V

    更新日期:2020-02-10 00:00:00

  • Synthesis and characterization of core-shell star copolymers for in vivo PET imaging applications.

    abstract::The synthesis of core-shell star copolymers via living free radical polymerization provides a convenient route to three-dimensional nanostructures having a poly(ethylene glycol) outer shell, a hydrophilic inner shell bearing reactive functional groups, and a central hydrophobic core. By starting with well-defined line...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm7014152

    authors: Fukukawa K,Rossin R,Hagooly A,Pressly ED,Hunt JN,Messmore BW,Wooley KL,Welch MJ,Hawker CJ

    更新日期:2008-04-01 00:00:00

  • Kinetic chain lengths in highly cross-linked networks formed by the photoinitiated polymerization of divinyl monomers: a gel permeation chromatography investigation.

    abstract::Highly cross-linked networks formed by the photoinitiated polymerization of multifunctional monomers are finding application in the field of biomaterials because of their chemical versatility, reaction control, and ability to polymerize under physiological conditions. Typically, degradation is introduced into these ne...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm025677o

    authors: Burdick JA,Lovestead TM,Anseth KS

    更新日期:2003-01-01 00:00:00

  • Preparation and characterization of nanoparticles shelled with chitosan for oral insulin delivery.

    abstract::Nanoparticles (NPs) composed of chitosan (CS) and poly(gamma-glutamic acid) (gamma-PGA) were prepared by a simple ionic-gelation method for oral insulin delivery. Fourier transform infrared (FT-IR) spectra indicated that CS and gamma-PGA were ionized at pH 2.5-6.6, while X-ray diffractograms demonstrated that the crys...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm0607776

    authors: Lin YH,Mi FL,Chen CT,Chang WC,Peng SF,Liang HF,Sung HW

    更新日期:2007-01-01 00:00:00

  • Molecular dynamics study of complexes of poly(glutamate) and dodecyltrimethylammonium.

    abstract::The supramolecular organization of self-assembled stoichiometric complexes formed by dodecyltrimethylammonium cations and ionized poly(gamma-glutamic) acid has been investigated in chloroform solution. Atomistic molecular dynamics simulations have been performed considering three different starting conformations for t...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm060927c

    authors: Zanuy D,Alemán C

    更新日期:2007-02-01 00:00:00

  • Novel biodegradable aliphatic poly(butylene succinate-co-cyclic carbonate)s bearing functionalizable carbonate building blocks: II. Enzymatic biodegradation and in vitro biocompatibility assay.

    abstract::In a previous study, we have reported chemical synthesis of novel aliphatic poly(butylene succinate-co-cyclic carbonate) P(BS-co-CC)s bearing various functionalizable carbonate building blocks, and this work will continue to present our new studies on their enzymatic degradation and in vitro cell biocompatibility assa...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm049705+

    authors: Yang J,Tian W,Li Q,Li Y,Cao A

    更新日期:2004-11-01 00:00:00

  • CO2-Responsive Water-Soluble Conjugated Polymers for In Vitro and In Vivo Biological Imaging.

    abstract::Water-soluble conjugated polymers (WCPs) composed of a hydrophobic polythiophene main chain with hydrophilic tertiary amine side-chains can directly self-assemble into sphere-like nano-objects in an aqueous solution due to phase separation between the hydrophilic and hydrophobic segments of the polymeric structure. Du...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/acs.biomac.0c01336

    authors: Cheng CC,Lai YC,Shieh YT,Chang YH,Lee AW,Chen JK,Lee DJ,Lai JY

    更新日期:2020-12-14 00:00:00

  • 1H NMR investigation of thermally triggered insulin release from poly(N-isopropylacrylamide) microgels.

    abstract::We describe investigations of insulin release from thermoresponsive microgels using variable temperature (1)H NMR. Microgel particles composed of poly(N-isopropylacrylamide) were loaded with the peptide via a swelling technique, and this method was compared to simple equilibrium partitioning. Variable temperature (1)H...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm060718s

    authors: Nolan CM,Gelbaum LT,Lyon LA

    更新日期:2006-10-01 00:00:00

  • Hydration of gluten: a dielectric, calorimetric, and fourier transform infrared study.

    abstract::The nature of the hydration of proteins and the subsequent implications for functionality is a matter of importance in both pharmaceutical and food applications. Most published studies rely on the use of one technique and attempt to characterize the system. Few studies have used combinations of techniques. In this pap...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm061206g

    authors: Almutawah A,Barker SA,Belton PS

    更新日期:2007-05-01 00:00:00

  • Tensile Reinforcement of Silk Films by the Addition of Telechelic-Type Polyalanine.

    abstract::An appropriate modification technique for silk materials is needed to effectively improve their physical properties for specific applications. A telechelic-type polyalanine (T-polyA) was synthesized by papain-catalyzed polymerization as a novel reinforcing agent for silk materials. A silk fibroin obtained from Bombyx ...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/acs.biomac.6b01891

    authors: Tsuchiya K,Masunaga H,Numata K

    更新日期:2017-03-13 00:00:00

  • An Injectable Hydrogel Prepared Using a PEG/Vitamin E Copolymer Facilitating Aqueous-Driven Gelation.

    abstract::Hydrogels have been widely explored for biomedical applications, with injectable hydrogels being of particular interest for their ability to precisely deliver drugs and cells to targets. Although these hydrogels have demonstrated satisfactory properties in many cases, challenges still remain for commercialization. In ...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/acs.biomac.6b01148

    authors: Zhang J,Muirhead B,Dodd M,Liu L,Xu F,Mangiacotte N,Hoare T,Sheardown H

    更新日期:2016-11-14 00:00:00

  • Polyrotaxane composed of poly-L-lactide and alpha-cyclodextrin exhibiting protease-triggered hydrolysis.

    abstract::Biodegradable polyrotaxanes (PRXs) were synthesized from bis-amino-terminated poly(L-lactide) (PLLA) and alpha-cyclodextrin (alpha-CD), combined with capping by bulky end groups at the amino-termini of PLLA through enzymatically cleavable peptide linkages. The crystalline structure of the PRXs in the solid state was i...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm900440v

    authors: Ohya Y,Takamido S,Nagahama K,Ouchi T,Katoono R,Yui N

    更新日期:2009-08-10 00:00:00

  • Wet-spinning of regenerated silk fiber from aqueous silk fibroin solution: discussion of spinning parameters.

    abstract::Regenerated silk fibroin (RSF) fibers were obtained by extruding a concentrated aqueous silk fibroin solution into an ammonium sulfate coagulation bath. A custom-made simplified industrial-type wet-spinning device with continuous mechanical postdraw was used. The effect of dope concentration, coagulation bath, extrusi...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm900840h

    authors: Yan J,Zhou G,Knight DP,Shao Z,Chen X

    更新日期:2010-01-11 00:00:00

  • Morphology of artificial silica matrices formed via autosilification of a silaffin/protein polymer chimera.

    abstract::Protein polymers (long-chain proteins in which a specific amino acid sequence "monomer" is repeated through the molecule) are found widely in nature, and these materials exhibit a diverse array of physical properties. One class of self-assembling proteins is hydrophobic-polar (HP) protein polymers capable of self-asse...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm701131x

    authors: Marner WD 2nd,Shaikh AS,Muller SJ,Keasling JD

    更新日期:2008-01-01 00:00:00

  • Supramolecular hydrogels from cisplatin-loaded block copolymer nanoparticles and α-cyclodextrins with a stepwise delivery property.

    abstract::A stepwise anticancer drug delivery system based on an injectable supramolecular hydrogel was presented. In this system, poly(ethylene glycol)-b-poly(acrylic acid) (PEG-b-PAA) block copolymer nanoparticles containing cisplatin were released by erosion of the hydrogels and then the cisplatin was released from the nanop...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm100889j

    authors: Zhu W,Li Y,Liu L,Chen Y,Wang C,Xi F

    更新日期:2010-11-08 00:00:00

  • Coiled coil peptides as universal linkers for the attachment of recombinant proteins to polymer therapeutics.

    abstract::We have designed, synthesized, and characterized peptides containing four repeats of the sequences VAALEKE (peptide E) or VAALKEK (peptide K). While the peptides alone adopt in aqueous solutions a random coil conformation, their equimolar mixture forms heterodimeric coiled coils as confirmed by CD spectroscopy. 5-Azid...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm200897b

    authors: Pechar M,Pola R,Laga R,Ulbrich K,Bednárová L,Maloň P,Sieglová I,Král V,Fábry M,Vaněk O

    更新日期:2011-10-10 00:00:00

  • Caspofungin Functionalized Polymethacrylates with Antifungal Properties.

    abstract::We describe the synthesis of hydrophilic poly(poly(ethylene glycol) methyl ether methacrylate) (PmPEGMA) and hydrophobic poly(methyl methacrylate) (PMMA) caspofungin conjugates by a post-polymerization modification of copolymers containing 10 mol % pentafluorophenyl methacrylate (PFPMA), which were obtained via revers...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/acs.biomac.0c00096

    authors: Alex J,González K,Kindel T,Bellstedt P,Weber C,Heinekamp T,Orasch T,Guerrero-Sanchez C,Schubert US,Brakhage AA

    更新日期:2020-06-08 00:00:00

  • Synthesis, characterization, and pH-triggered dethreading of alpha-cyclodextrin-poly(ethylene glycol) polyrotaxanes bearing cleavable endcaps.

    abstract::The synthesis, characterization, and degradation kinetics of three alpha-cyclodextrin (alpha-CD)-poly(ethylene glycol) (PEG) polyrotaxanes with endcaps that were installed using Cu(I)-catalyzed Huisgen cyclization is reported. PEG1500, azidated with azidoacetic acid, was threaded with alpha-CD to form a pseudopolyrota...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm0602076

    authors: Loethen S,Ooya T,Choi HS,Yui N,Thompson DH

    更新日期:2006-09-01 00:00:00

  • Hydrogels for osteochondral repair based on photocrosslinkable carbamate dendrimers.

    abstract::First generation, photocrosslinkable dendrimers consisting of natural metabolites (i.e., succinic acid, glycerol, and beta-alanine) and nonimmunogenic poly(ethylene glycol) (PEG) were synthesized divergently in high yields using ester and carbamate forming reactions. Aqueous solutions of these dendrimers were photocro...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm800658x

    authors: Degoricija L,Bansal PN,Söntjens SH,Joshi NS,Takahashi M,Snyder B,Grinstaff MW

    更新日期:2008-10-01 00:00:00

  • New approaches to the analysis of enzymatically hydrolyzed methyl cellulose. Part 1. Investigation of the influence of structural parameters on the extent of degradation.

    abstract::Six methyl celluloses (MCs), one with a degree of substitution (DS) of 1.32 and five with DS between 1.83 and 1.88, were thoroughly investigated. Monomer composition and methyl distribution in the polymer chain were analyzed after total or partial random hydrolysis and appropriate derivatization with gas chromatograph...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm050941+

    authors: Adden R,Melander C,Brinkmalm G,Gorton L,Mischnick P

    更新日期:2006-05-01 00:00:00

  • A Universal Approach to Render Nanomedicine with Biological Identity Derived from Cell Membranes.

    abstract::Biomimetic nanoengineering built through integrating the specific cell membrane with artificially synthetic nanomedicines represents one of the most promising directions for the actualization of personalized therapy. For addressing the technical hurdle against the development of this biomimetic technology, the present...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/acs.biomac.8b00242

    authors: Zhu J,Zhang M,Zheng D,Hong S,Feng J,Zhang XZ

    更新日期:2018-06-11 00:00:00

  • In situ forming reduction-sensitive degradable nanogels for facile loading and triggered intracellular release of proteins.

    abstract::In situ forming reduction-sensitive degradable nanogels were designed and developed based on poly(ethylene glycol)-b-poly(2-(hydroxyethyl) methacrylate-co-acryloyl carbonate) (PEG-P(HEMA-co-AC)) block copolymers for efficient loading as well as triggered intracellular release of proteins. PEG-P(HEMA-co-AC) copolymers ...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm400206m

    authors: Chen W,Zheng M,Meng F,Cheng R,Deng C,Feijen J,Zhong Z

    更新日期:2013-04-08 00:00:00

  • Synthesis, characterization, and antibacterial activities of novel methacrylate polymers containing norfloxacin.

    abstract::A novel methacrylate monomer containing a quinolone moiety was synthesized and homopolymerized in N,N-dimethylformamide (DMF) by using azobisisobutyronitrile (AIBN) as an initiator. The new monomer was copolymerized with poly(ethylene glycol) methyl ether methacrylate (MPEGMA) in DMF using the same initiator. The mono...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm049383+

    authors: Dizman B,Elasri MO,Mathias LJ

    更新日期:2005-01-01 00:00:00

  • Sericin Promotes Fibroin Silk I Stabilization Across a Phase-Separation.

    abstract::Natural silk spinning offers several advantages over the synthetic fiber spinning, although the underlying mechanisms of this process are yet to be fully elucidated. Silkworm silks, specifically B. mori, comprise two main proteins: fibroin, which forms the fiber, and sericin, a coextruded coating that acts as a matrix...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/acs.biomac.7b00549

    authors: Kwak HW,Ju JE,Shin M,Holland C,Lee KH

    更新日期:2017-08-14 00:00:00

  • Multifunctional Polymeric Micelles with Amplified Fenton Reaction for Tumor Ablation.

    abstract::Relative to normal cells, tumor cells lack adequate capability of reactive oxygen scavenging. Thus, tumor cells can be selectively killed by increasing the concentration of reactive oxygen species in tumor tissue. In this report, we construct an integrated multifunctional polymeric nanoparticle which can selectively i...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/acs.biomac.7b01777

    authors: Wang Y,Yin W,Ke W,Chen W,He C,Ge Z

    更新日期:2018-06-11 00:00:00

  • Artificial forisomes are ideal models of forisome assembly and activity that allow the development of technical devices.

    abstract::Forisomes are protein polymers found in leguminous plants that have the remarkable ability to undergo reversible "muscle-like" contractions in the presence of divalent cations and in extreme pH environments. To gain insight into the molecular basis of forisome structure and assembly, we used confocal laser scanning mi...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm3008499

    authors: Groscurth S,Müller B,Schwan S,Menzel M,Diekstall F,Senft M,Kendall A,Kommor BA,Neumann U,Kalischuk M,Kawchuk LM,Krzyzanek V,Heilmann A,Stubbs G,Twyman RM,Prüfer D,Noll GA

    更新日期:2012-10-08 00:00:00

  • Hydrothermal Gelation of Aqueous Cellulose Nanocrystal Suspensions.

    abstract::We report the facile preparation of gels from the hydrothermal treatment of suspensions of cellulose nanocrystals (CNCs). The properties of the hydrogels have been investigated by rheology, electron microscopy, and spectroscopy with respect to variation in the temperature, time, and CNC concentration used in preparati...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/acs.biomac.6b00906

    authors: Lewis L,Derakhshandeh M,Hatzikiriakos SG,Hamad WY,MacLachlan MJ

    更新日期:2016-08-08 00:00:00

  • Highly filled bionanocomposites from functionalized polysaccharide nanocrystals.

    abstract::Cellulose and starch nanocrystals obtained from the acid hydrolysis of ramie fibers and waxy maize starch granules, respectively, were subjected to isocyanate-mediated reaction to graft polycaprolactone (PCL) chains with various molecular weights on their surface. Grafted nanoparticles were characterized by X-ray diff...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm8001717

    authors: Habibi Y,Dufresne A

    更新日期:2008-07-01 00:00:00