Synthesis and physicochemical properties of hydroxypropyl tannins from maritime pine bark (Pinus pinaster Ait.)
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Danny E. García
Abstract
Simple derivatives of condensed tannins are described, which allow the tailoring of gelation (with aldehydes) and thermal degradation behaviors that have been obstacles to the commercial utilization of this abundant bioresource. Hydroxypropyl tannin (HPT) derivatives from bark of Pinus pinaster with varying degrees of substitution (DS 0.1–4.7) were analyzed with regard to molecular and physical characteristics, such as structure, molecular weight, thermal behavior, solubility and gelation. The modification reaction of tannin proceeds stoichiometrically to a mixture of oligomeric derivatives, mostly to trimers and tetramers, as demonstrated by 1H-nuclear magnetic resonance, elemental analysis, and gel permeation chromatography. The derivatives have an improved solubility in organic solvents and increased thermal stability. The glass transition temperature (Tg) was reduced by up to 37°C over unmodified tannin. At DS ≥1.0, the HPT lost the capacity to produce gel with formaldehyde. A structure-property relationship was established by means of multivariate analysis, and the derivatives could be grouped according to their physicochemical profile. HPTs are promising biomacromolecular building blocks for tannin-derived materials.
Acknowledgments
The authors acknowledge the Wood Wisdom-Net Research Program and ERA-NET Bioenergy for the support of the project entitled “Bark Valorization into Insulating Foams and Bioenergy” (BIOFOAMBARK). The project is funded by the Federal Ministry of Food, Agriculture and Consumer Protection through the Agency for Renewable Resources in Germany. The financial support of the DFG for a Mercator Guest Professorship to W.G. Glasser is acknowledged with gratitude. The authors are grateful to Mrs. Elke Stibal and Mr. Andreas Manuel for their technical assistance.
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©2014 by Walter de Gruyter Berlin/Boston
Artikel in diesem Heft
- Frontmatter
- Review
- Effects of induced drought and tilting on biomass allocation, wood properties, compression wood formation and chemical composition of young Pinus radiata genotypes (clones)
- Original Articles
- Multi-step degradation method for β-O-4 linkages in lignins: α-TSA method. Part 1: Reaction of non-phenolic dimeric β-O-4 model compound
- Pulp delignification with oxygen and copper(II)-polyimine complexes
- Enzyme pretreatment of dissolving pulp as a way to improve the following dissolution in NaOH/ZnO
- Formation of oxalic acid in alkaline peroxide treatment of different wood components
- Pretreatment of hardwood chips via autohydrolysis supported by acetic and formic acid
- Synthesis and physicochemical properties of hydroxypropyl tannins from maritime pine bark (Pinus pinaster Ait.)
- Analysis of lignin and extractives in the oak wood of the 17th century warship Vasa
- Esterification of wood with citric acid: The catalytic effects of sodium hypophosphite (SHP)
- Bio-based epoxy resins with low molecular weight kraft lignin and pyrogallol
- Influence of toasting treatment on permeability of six wood species for enological use
- Experimental study of wood acoustic absorption characteristics
- Appearance, corrosion properties, and leach resistance of spruce and pine wood treated with Mea modified micronized copper preservative (MCu)
- DNA barcoding for identification of the endangered species Aquilaria sinensis: comparison of data from heated or aged wood samples
- Meetings
- Meetings
Artikel in diesem Heft
- Frontmatter
- Review
- Effects of induced drought and tilting on biomass allocation, wood properties, compression wood formation and chemical composition of young Pinus radiata genotypes (clones)
- Original Articles
- Multi-step degradation method for β-O-4 linkages in lignins: α-TSA method. Part 1: Reaction of non-phenolic dimeric β-O-4 model compound
- Pulp delignification with oxygen and copper(II)-polyimine complexes
- Enzyme pretreatment of dissolving pulp as a way to improve the following dissolution in NaOH/ZnO
- Formation of oxalic acid in alkaline peroxide treatment of different wood components
- Pretreatment of hardwood chips via autohydrolysis supported by acetic and formic acid
- Synthesis and physicochemical properties of hydroxypropyl tannins from maritime pine bark (Pinus pinaster Ait.)
- Analysis of lignin and extractives in the oak wood of the 17th century warship Vasa
- Esterification of wood with citric acid: The catalytic effects of sodium hypophosphite (SHP)
- Bio-based epoxy resins with low molecular weight kraft lignin and pyrogallol
- Influence of toasting treatment on permeability of six wood species for enological use
- Experimental study of wood acoustic absorption characteristics
- Appearance, corrosion properties, and leach resistance of spruce and pine wood treated with Mea modified micronized copper preservative (MCu)
- DNA barcoding for identification of the endangered species Aquilaria sinensis: comparison of data from heated or aged wood samples
- Meetings
- Meetings
