Butylene Oxide Research Articles

Polyester Adhesives via One-Pot, One-Step Copolymerization of Cyclic Anhydride, Epoxide, and Lactide.

Polyesters (PEs) are sustainable alternatives for conventional polymers owing to their potential degradability, recyclability, and the wide availability of bio-based monomers for their synthesis. Herein, we used a one-pot, one-step self-switchable polymerization linking the ring-opening alternating copolymerization (ROAC) of epoxides/cyclic anhydrides with the ring-opening polymerization (ROP) of L-lactide (LLA) to synthesize PE-based hot-melt adhesives with a high bio-based content. In the cesium pivalate-catalyzed self-switchable polymerization of glutaric anhydride (GA), butylene oxide (BO), and LLA using a diol initiator, the ROAC of GA and BO proceeded whereas the ROP of LLA simultaneously proceeded very slowly, resulting in a copolyester consisting of poly(GA-alt-BO) and poly(L-lactide) (PLLA) segments with tapered regions, that is, PLLA-tapered block-poly(GA-alt-BO)-tapered block-PLLA (PLLA-tb-poly(GA-alt-BO)-tb-PLLA). Additionally, a series of tapered-block or real-block copolyesters consisting of poly(anhydride-alt-epoxide) (A segment) and PLLA (B segment) with AB-, BAB-, (AB)3-, and (AB)4-type architectures of different compositions and molecular weights were synthesized by varying the monomer combinations, alcohol initiators, and initial feed ratios. The lap shear tests of these copolyesters revealed an excellent relationship between the adhesive strength and polymer structural parameters. The (AB)4-type star-block copolyester (poly(GA-alt-BO)-tb-PLLA)4 exhibited the best adhesive strength (6.74 ± 0.64 MPa), comparable to that of commercial products, such as PE-based and poly(vinyl acetate)-based hot-melt adhesives.

A comparative study of PEO-PBO content on the targeting and anti-glioma activity of annonaceous acetogenins-loaded nanomicelles

Annonaceous acetogenins (ACGs) have great potential in the treatment of gliomas, but are extremely insoluble and difficult for delivery in vivo. Poly(ethylene oxide)-b-poly(butylene oxide) (PEO-PBO) is an amphiphilic polymer and can reduce the clearance of nanoparticles by mononuclear phagocyte system. To explore an efficient and safe nanomedicine for glioma, ACGs-loaded nanomicelles (ACGs/EB-NCs) was constructed using PEO-PBO as a carrier, and the effect of PEO-PBO content on the targeting and anti-glioma activity were also compared. ACGs/EB5-NCs, ACGs/EB10-NCs and ACGs/EB20-NCs, the three nanomicellels prepared with different ACGs/EB feeding ratios, had average particle sizes of 148.8±0.5 nm, 32.7±4.1 nm, and 27.1±0.3 nm, respectively. The three ACGs/EB-NCs were spherical in shape, with drug loading content close to the theoretical drug loading content, encapsulation efficiency greater than 97 %, and good stability in physiological media. The cumulative release rates of ACGs/EB5-NCs, ACGs/EB10-NCs and ACGs/EB20-NCs were 78.2 %, 63.4 %, and 56.3 % within 216 hours, respectively. The inhibitory effects of three ACGs/EB-NCs on U87 MG cells were similar and stronger than free ACGs (P<0.05), with half inhibitory concentration of 0.17, 0.18, and 0.16 ng/mL (P>0.05), respectively. In U87 MG tumor‑bearing mice, ACGs/EB5-NC, ACGs/EB10-NCs and ACGs/EB20-NCs showed a similar tumor inhibition rate of 61.1±5.9 %, 56.2±8.6 % and 64.3±9.4 % (P>0.05), with good safety. Three ACGs/EB-NCs exhibited excellent liver escape ability and tumor targeting ability, with the tumor targeting index greater than 1.5. Three ACGs/EB-NCs were successfully prepared with strong anti-glioma activity and tumor targeting properties, which are expected to provide new options for the clinical treatment of gliomas. The content of PEO-PBO in micelles did not have a significant effect on the tumor targeting and anti-glioma activity of ACGs/EB-NCs.

Cooperative Dynamics of Highly Entangled Linear Polymers within the Entanglement Tube.

We present a quantitative comparison of the dynamic structure factors from unentangled and strongly entangled poly(butylene oxide) (PBO) melts. As expected, the low molecular weight PBO displays Rouse dynamics, however, with very significant subdiffusive center-of-mass diffusion. The spectra from high molecular weight entangled PBO can be very well described by the dynamic structure factor based on the concept of local reptation, including the Rouse dynamics within the tube and allowing for non-Gaussian corrections. Comparing quantitatively the spectra from both polymers leads to the surprising result that their spectra differ only by the contribution of classical Rouse diffusion for the low molecular weight melt. The subdiffusive component is common for both the low and high molecular weight PBO melts, indicating that in both melts the same interchain potential is active, thereby supporting the validity of the Generalized Langevin Equation approach.

Synthesis and Application of a Novel Multi-Branched Block Polyether Low-Temperature Demulsifier.

In this paper, a low-temperature thick oil demulsifier with high polarity was prepared by introducing ethylene oxide, propylene oxide block, and butylene oxide using m-diphenol as a starting agent. The main reasons for the difficulty involved in the low-temperature emulsification of extractive fluids were explained by analyzing the synthetic influencing factors and infrared spectra of the star comb polymer (PR-D2) and by analyzing the four fractions, interfacial energies, and zeta potentials of crude oils from the Chun and Gao fields. The effects of PR-D2 surfactant on the emulsification performance of crude oil recovery fluids were investigated via indoor and field experiments. The experimental results indicate that the optimal synthesis conditions for this emulsion breaker are as follows: a quality ratio of ionic reaction intermediates and meso-diphenol of R = 10:1; 1 g of the initiator; a polymerization temperature of 80 °C; and a reaction time of 8 h. Colloidal asphaltenes in the crude oil were the main factor hindering the low-temperature demulsification of the Gao oilfield's extractive fluids, and the reason for the demulsification difficulty of the extractive fluids in the Chun oilfield is that the temperature of demulsification is lower than the wax precipitation point. The demulsification rate of the Chun oilfield's extractive fluids reached more than 98% when the PR-D2 concentration reached 150 mg/L at 43 °C. The demulsification rate of the Gao oilfield's extractive fluids reached more than 98% at a PR-D2 concentration of 150 mg/L at 65 °C. The field experiments show that the Chun oilfield's extractive fluids can still demulsify after the temperature is reduced to 43 °C in winter. The emulsification temperature of the Gao oilfield's extractive fluids was reduced from 73 °C to 68 °C, with an excellent demulsification effect.

Spectroscopic investigation into the oxidation of polyethylenimine for CO2 capture: Mitigation strategies and mechanism

One of the most critical challenges facing large-scale application of amine-based CO2 adsorbents is their long-term stability, particularly their oxidative degradation, which shortens their lifetime. Numerous oxidation mitigation strategies were proposed, notably functionalization by epoxybutane (EB) and addition of polyvinyl alcohol (PVA). However, neither the amine oxidation mechanism, nor the antioxidation mechanism of these additives are clear. Here, we investigated the oxidation of polyethylenimine (PEI) using electron paramagnetic resonance (EPR), nuclear magnetic resonance (NMR), mass spectrometry (MS), and thermogravimetric analysis (TGA). EPR data provided for the first time direct evidence for the occurrence of radical species during PEI oxidation, and their increased content in the presence of transition metal catalysts. Moreover, significant amounts of CO2, water and ammonia were detected by MS. Surprisingly, although EB and PVA enhanced the oxidation resistance of PEI, they did not reduce the amount of radical species. Theoretical calculations by DFT indicated that PEI is more prone to oxidation than EB-functionalized PEI and PVA, because its CH bonds are weaker. Consistent with experimental data, a mechanistic explanation to the slower amine oxidation in the presence of EB and PVA, was put forward, and clues for further improvement were proposed.

Synergetic catalytic effect in functionalized HP-MOF system for boosted catalytic performances

A collection of hierarchically porous Zr-based MOFs with precisely adjusted acid-base properties were synthesized and characterized using PXRD, FT-IR, NMR, and TGA techniques, confirming phase purity and structural integrity. The catalytic potential of these materials was investigated through CO2 cycloaddition with epoxides. The results indicated that increasing the mixed-ligand ratio to 1:1-NH2BDC/BDC gradually enhanced the catalytic activity, but further increasing NH2BDC had an inverse effect. The optimized mixed-ligand ratio suggests that HP-UiO-66(1:1) is among the top catalyst choices. The catalytic efficiency and effectiveness of HP-UiO-66(1:1) were further validated through reactions with six other organic epoxides, including epichlorohydrin, butylene oxide, isobutylene oxide, styrene oxide, 1,2-epoxydecane, and 1,2-epoxydodecane. All substrates exhibited notably high conversions and yields using HP-UiO-66(1:1) catalyst, demonstrating that strategically combining functionalized linkers enhances the catalytic performance and tunability of HP-UiO-66-based MOF catalysts.

Bifunctional Y/g-C3N4 promoted cycloaddition of CO2 to epoxide: Halogen-free and acid-base synergistic catalysis

Cycloaddition reaction of CO2 to epoxides is an important procedure for both CO2 conversion and cyclic carbonate synthesis. Homogeneous alkali halide and quaternary ammonium salt are the general catalysts, while they have the problems of halogen corrosion and residue, intricate separation, and catalyst recycling. Here, a series of heterogenous and halogen-free bifunctional yttrium-coordinated g-C3N4 were synthesized and employed to catalyze the cycloaddition of CO2 to butylene oxide. Excellent butylene oxide conversion (94.5%) and butene carbonate selectivity (95.0%) were achieved over the typical Y/g-C3N4-0.5 catalyst without any halogen addition. The characterizations demonstrate that the coordinated Y species function well as the preferred Lewis acid sites for epoxide ring opening and butene carbonate desorption, and the uncondensed amino groups are supplied as Lewis base sites to activate CO2. It is the synergistic effect based on acid-base duality that enhances the catalytic performance of Y/g-C3N4 to cycloaddition of CO2 with epoxide.

End block dynamics in unentangled polymers by dielectric spectroscopy

Dielectric spectroscopy measures the dynamics of polymer melts over a broad frequency range. Developing a theory for the spectral shape can extend the analysis of dielectric spectra beyond determining relaxation times from the peak maxima and adds physical meaning to shape parameters determined with empirical fit functions. Toward this goal, we use the experimental results on unentangled poly(isoprene), and unentangled poly(butylene oxide), polymer melts, to test whether the concept of end blocks could be one reason for the Rouse model deviating from experimental data. These end blocks have been suggested by simulations and neutron spin echo spectroscopy and are a consequence of the monomeric friction coefficient depending on the position of the bead in the chain. The concept of an end block is an approximation which partitions the chain in a middle and two end blocks to avoid overparameterization by a continuous position dependent change of the friction parameter. Analysis of dielectric spectra shows that the deviations of the calculated from the experimental normal mode cannot be related to the end block relaxation. However, the results do not contradict an end block hiding below the segmental relaxation peak. It seems that the results are compatible with an end block being the specific part of the sub-Rouse chain interpretation close to the chain ends.

Dimension and shape controllable ZIFs for highly-efficient chemical fixation of CO2 without solvent and co-catalyst

The cycloaddition of CO2 with epoxides is an important strategy to reach the goal of carbon neutral, at the same time high-value-added products can be obtained. The integration of Lewis acidic and alkaline sites makes ZIFs potential catalysts for the CO2 cycloaddition. Herein, through simply adjusting the water proportion in the synthesis solvent, a series of ZIF materials were prepared and applied in the CO2 cycloaddition. The transitional ZIF-(80)-Co combines the advantages of two-dimensional and three-dimensional ZIFs, namely the two-dimensional morphology, well-developed porous structures, higher CO2 adsorption capacity, and rich acidic/alkaline sites. The outstanding microstructures and surface properties of ZIF-(80)-Co contribute to its superior catalytic performance for the CO2 cycloaddition, and an epichlorohydrin (ECH) conversion of 96.9 % and a cyclic carbonate selectivity of 98 % are achieved without solvent and co-catalyst. Importantly, the cycloaddition of CO2 with ECH over ZIF-(80)-Co is faster than most of the reported ZIFs in literature. Furthermore, ZIF-(80)-Co also exhibits excellent catalytic performance in the CO2 cycloaddition with epoxy butane, allyl glycidyl ether, cyclohexene oxide and styrene oxide.

Engineering of ion permeable planar membranes and polymersomes based on β-cyclodextrin-cored star copolymers.

For polymersome-based nanoreactor purposes, we herein present the synthesis and characterization of well-defined star amphiphilic copolymers composed of a beta-cyclodextrin (βCD) core and seven poly(butylene oxide)-block-polyglycidol (PBO-PGL) arms per side (βCD-(PBO-PGL)14). The self-assembly behavior of 14-armed βCD-(PBO-PGL)14 and PGL-PBO-PGL (linear analogues without the βCD segment) was investigated using scattering techniques for comparison. The morphologies, including vesicles and micelles, are governed by the hydrophobic-to-hydrophilic (weight) ratio, regardless of the polymer architecture (linear or star). Interestingly, despite notable differences in polymer conformation, the produced supramolecular structures were evidenced to be fairly similar on the structural point of view. We subsequently investigated the ion permeability of the membranes of the self-assemblies focusing on the impact of the presence of βCD. The results demonstrated that the βCD-containing vesicular membranes are less permeable to H+, compared with βCD-free vesicular membranes. The presence of βCD in planar membranes also influences the K+Cl- permeability to some extent. Thus, βCD-containing membranes can be considered as potential candidates in designing nano-containers towards applications where precise changes in environmental pH are required.

Rheo-Dielectric Behavior of Unentangled Poly(butylene oxide) under Steady Shear: Preliminary Evaluation of Non-Equilibrium Parameters at the Onset of Nonlinearity

Rheo-Dielectric Behavior of Unentangled Poly(butylene oxide) under Steady Shear: Preliminary Evaluation of Non-Equilibrium Parameters at the Onset of Nonlinearity

Functional and degradable copolyesters by ring-opening copolymerization of epoxides and anhydrides

The ring-opening copolymerization (ROcoP) of epoxides and anhydrides is exploited to afford 4 structurally diverse and functional copolyesters. Mixtures of 2 epoxides (allyl glycidyl ether and butylene oxide) with 1 anhydride (succinic, glutaric, phthalic and homo phthalic anhydride) are copolymerized in the presence of bis(triphenylphosphine)iminium chloride (PPNCl) as organocatalyst. All monomer combinations yield vinyl-functionalized materials with alternating epoxide-anhydride units, statistical incorporation of both epoxides along the polymer chain and molar masses up to 28.3 kg/mol. The copolyesters are amorphous with a Tg between –39 °C and 38 °C. Together with the molar mass, the anhydride dictates the thermal stability of the copolyesters with glutaric anhydride resulting in a remarkably high thermal stability up to 310 °C. In a post-polymerization step, the pendant double bonds are radically crosslinked to gels with swelling ratios above 1500 % and comparable to enhanced thermal stability with respect to the non-crosslinked, parent copolyesters. The degradation of the 4 copolyesters (before and after crosslinking) is tested in abiotic and enzymatic conditions: The highest degradation rates are observed for the non-crosslinked materials in enzymatic conditions with a mass loss of up to 60 % after 27d. After crosslinking, the gels are more stable against degradation under both conditions, although a decrease in the gel content and a decrease in mass indicates that degradation still takes place.

End functionalization of polyisoprene and polymyrcene obtained by anionic polymerization via one-pot ring-opening mono-addition of epoxides

End-functionalization of polyisoprene and polymyrcene were successfully synthesized using anionic polymerization in THF. A number of epoxides, propylene oxide (PO), butylene oxide (BO), allyl glycidyl ether (AGE), 1,2-epoxy-5-hexene (EH) and N,N-dibenzyl amino glycidol (DBAG), were utilised as terminating agents for the induction of hydroxyl functional group in the final products. Polymers were fully hydrogenated following epoxide termination. The functional polymers were characterized by 1H and 13C NMR showing high levels of regioselective termination, SEC showing good control over molecular weight to polymers with narrow molecular weight distributions, MALDI-ToF MS confirming very high levels of functionalisation and thermal analysis (TGA & DSC).

Sustained Release of a Polymeric Wetting Agent from a Silicone-Hydrogel Contact Lens Material.

Uptake and release kinetics are investigated of a dilute aqueous polymeric-surfactant wetting agent, (ethylene oxide)45—(butylene oxide)10 copolymer, also referred to as poly(oxyethylene)-co-poly(oxybutylene), impregnated into a newly designed silicone-hydrogel lens material. Transient scanning concentration profiles of the fluorescently tagged polymeric surfactant follow Fick’s second law with a diffusion coefficient near 10–11 cm2/s, a value 3–4 orders smaller than that of the free surfactant in bulk water. The Nernst partition coefficient of the tagged polymeric wetting agent, determined by fluorescence microscopy and by methanol extraction, is near 350, a very large value. Back-extraction of the polymeric-surfactant wetting agent releases only ∼20% of the loaded amount after soaking the fully loaded lens for over 7 days. The remaining ∼80% is irreversibly bound in the lens matrix. Reverse-phase liquid chromatography of the lens-loaded and lens-extracted surfactant demonstrates that the released wetting agent is more hydrophilic with a higher polarity. Aqueous poly(oxyethylene)-co-poly(oxybutylene) is hypothesized to attach strongly to the lens matrix, most likely to the lens silicone domains. Strong binding leads to slow transient diffusion, to large uptake, and to significant irreversible retention. These characteristics indicate the suitability of using a poly(oxyethylene)-co-poly(oxybutylene) nonionic polymeric surfactant to maintain enhanced lens wettability over time. Methodology and findings from this study provide useful insights for designing sustained-release contact-lens wetting agents and materials.

Tailoring a Solvent-Assisted Method for Solid-Supported Hybrid Lipid-Polymer Membranes.

Combining amphiphilic block copolymers and phospholipids opens new opportunities for the preparation of artificial membranes. The chemical versatility and mechanical robustness of polymers together with the fluidity and biocompatibility of lipids afford hybrid membranes with unique properties that are of great interest in the field of bioengineering. Owing to its straightforwardness, the solvent-assisted method (SA) is particularly attractive for obtaining solid-supported membranes. While the SA method was first developed for lipids and very recently extended to amphiphilic block copolymers, its potential to develop hybrid membranes has not yet been explored. Here, we tailor the SA method to prepare solid-supported polymer–lipid hybrid membranes by combining a small library of amphiphilic diblock copolymers poly(dimethyl siloxane)–poly(2-methyl-2-oxazoline) and poly(butylene oxide)-block–poly(glycidol) with phospholipids commonly found in cell membranes including 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine, 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphoethanolamine, sphingomyelin, and 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine-N-(glutaryl). The optimization of the conditions under which the SA method was applied allowed for the formation of hybrid polymer–lipid solid-supported membranes. The real-time formation and morphology of these hybrid membranes were evaluated using a combination of quartz crystal microbalance and atomic force microscopy. Depending on the type of polymer–lipid combination, significant differences in membrane coverage, formation of domains, and quality of membranes were obtained. The use of the SA method for a rapid and controlled formation of solid-supported hybrid membranes provides the basis for developing customized artificial hybrid membranes.

Nanostructural Changes Correlated to Decay Resistance of Chemically Modified Wood Fibers

Reactive chemical modifications have been shown to impart decay resistance to wood. These modifications change hydroxyl availability, water uptake, surface energy, and the nanostructure of wood. Because fungal action occurs on the micro and nano scale, further investigation into the nanostructure may lead to better strategies to prevent fungal decay. The aim of this article is to introduce our findings using small angle neutron scattering (SANS) to probe the effects of chemical modifications on the nanostructure of wood fibers. Southern pine wood fiber samples were chemically modified to various weight percentage gains (WPG) using propylene oxide (PO), butylene oxide (BO), or acetic anhydride (AA). After modification, the samples were water leached for two weeks to remove any unreacted reagents, homopolymers or by-products and then the equilibrium moisture content (EMC) was determined. Laboratory soil-block-decay evaluations against the brown rot fungus Gloeophyllum trabeum were performed to determine weight loss and decay resistance of the modifications. To assist in understanding the mechanism behind fungal decay resistance, SANS was used to study samples that were fully immersed in deuterium oxide (D2O). These measurements revealed that modifying the fibers led to differences in the swollen wood nanostructure compared to unmodified wood fibers. Moreover, the modifications led to differences in the nanoscale features observed in samples that were exposed to brown rot fungal attack compared to unmodified wood fibers and solid wood blocks modified with alkylene oxides.

Zr(IV) Catalyst for the Ring-Opening Copolymerization of Anhydrides (A) with Epoxides (B), Oxetane (B), and Tetrahydrofurans (C) to Make ABB- and/or ABC-Poly(ester-alt-ethers).

Poly(ester-alt-ethers) can combine beneficial ether linkage flexibility and polarity with ester linkage hydrolysability, furnishing fully degradable polymers. Despite their promising properties, this class of polymers remains underexplored, in part due to difficulties in polymer synthesis. Here, a catalyzed copolymerization using commercially available monomers, butylene oxide (BO)/oxetane (OX), tetrahydrofuran (THF), and phthalic anhydride (PA), accesses a series of well-defined poly(ester-alt-ethers). A Zr(IV) catalyst is reported that yields polymer repeat units comprising a ring-opened PA (A), followed by two ring-opened cyclic ethers (B/C) (−ABB– or −ABC−). It operates with high polymerization control, good rate, and successfully enchains epoxides, oxetane, and/or tetrahydrofurans, providing a straightforward means to moderate the distance between ester linkages. Kinetic analysis of PA/BO copolymerization, with/without THF, reveals an overall second-order rate law: first order in both catalyst and butylene oxide concentrations but zero order in phthalic anhydride and, where it is present, zero order in THF. Poly(ester-alt-ethers) have lower glass-transition temperatures (−16 °C < Tg < 12 °C) than the analogous alternating polyesters, consistent with the greater backbone flexibility. They also show faster ester hydrolysis rates compared with the analogous AB polymers. The Zr(IV) catalyst furnishes poly(ester-alt-ethers) from a range of commercially available epoxides and anhydride; it presents a straightforward method to moderate degradable polymers’ properties.

Lipid Membrane Binding and Cell Protection Efficacy of Poly(1,2-butylene oxide)-b-poly(ethylene oxide) Copolymers.

Poloxamers consisting of poly(ethylene oxide) (PEO) and poly(propylene oxide) segments can protect cell membranes against various forms of stress. We investigated the role of the hydrophobic block chemistry on polymer/membrane binding and cell membrane protection by comparing a series of poly(butylene oxide)-b-PEO (PBO-b-PEO) copolymers to poloxamer analogues, using a combination of pulsed-field-gradient (PFG) NMR experiments and a lactate dehydrogenase (LDH) cell assay. We found that the more hydrophobic PBO-b-PEO copolymers bound more significantly to model liposomes composed of 1-palmitol-2-oleoyl-glycero-3-phosphocholine (POPC) compared to poly(propylene oxide) (PPO)/PEO copolymers. However, both classes of polymers performed similarly when compared by an LDH assay. These results present an important comparison between polymers with similar structures but with different binding affinities. They also provide mechanistic insight as enhanced polymer/lipid membrane binding did not directly translate to increased cell protection in the LDH assay, and therefore, additional factors need to be considered when trying to achieve greater membrane protection efficacy.

Fundamental investigation on controlling factors of reverse solute flux of branched thermo-responsive oligomer in forward osmosis process

Forward osmosis (FO) has attracted research attention as the energy-effective water separation process. For a FO process, it is important to prevent leakage of a solute of the DS. As a low-leakage solute, a branched thermo-responsive oligomer, pentaerythritol-oligo(ethylene oxide)m-b-(butylene oxide)n oligomers (PEBs), had been reported. In this study, the relationship between the chemical structure and the permeability of the PEBs through a FO membrane had been investigated in detail. For the detailed investigation, the mole fraction of each component having different absolute molecular weights in the PEBs was determined by the MALDI/TOF-MS, then the permeabilities of the components through the FO membrane were independently quantified. As the result, for the PEBs with low absolute molecular weight, the permeability of the PEBs was strongly affected by the molecular weight of the PEBs. On the other hand, for the PEBs with high absolute molecular weight, it was confirmed that the permeability of the PEBs was affected by the hydrophobicity of the PEBs. Conclusively, it was indicated that not only the molecular weight but also the affinity between the PEBs and the FO membrane is important for the reverse solute flux.

Small Angle Neutron Scattering Reveals Wood Nanostructural Features in Decay Resistant Chemically Modified Wood

While it is known that modifying the hydroxyls in wood can improve the decay resistance; what is often missing in the literature is whether these modifications alter wood nanostructure, and how these changes correlate to the improved decay resistance. Here, we used small angle neutron scattering (SANS) to probe the effects of alkylene oxide modifications on wood nanostructure. Southern pine wood samples were chemically modified to various weight percentage gains (WPG) using four different alkylene oxides: propylene oxide (PO), butylene oxide (BO), epichlorohydrin (EpH), and epoxybutene (EpB). After modification, the samples were water leached for 2 weeks to remove any unreacted reagents or homopolymers and then equilibrium moisture content (EMC) was determined at 90% relative humidity (RH) and 27°C. Laboratory soil block decay evaluations against the brown rot fungus Gloeophyllum trabeum were performed to determine weight loss and biological efficacy of the modifications. To assist in understanding the mechanism, SANS was used to study samples that were fully immersed in deuterium oxide (D2O). These measurements revealed that the modifications altered the water distribution inside the cell wall, and the most effective modifications reduced the microfibril swelling and preserved the microfibril structure even after being subject to 12 weeks of brown rot exposure.