Oxirane Content Research Articles

Development of an oxirane/acrylate interpenetrating polymer network (IPN) resin system

ObjectiveDevelop a hydrophobic, degradation-resistant dental restorative based on an Oxirane-Acrylate IPN System (OASys) with low shrinkage-stress to substantially extend clinical lifetime. MethodsUnfilled OASys blends were prepared using dipenta-erythritol-hexaacrylate (DPHA) and p-cycloaliphatic-diepoxide (EP5000). Varying proportions of camphorquinone/iodonium photoinitiator, with a co-reactant oligomeric-diol, served as the experimental curing system. The effects of oxirane-acrylate ratio on the degree-of-cure (Durometer-D hardness), hydrophobicity (contact angle), mechanical properties (3-point bending), near-infrared FTIR degree-of-conversion (DoC), polymerization shrinkage, and shrinkage stress were determined. 70:30 BisGMA:TEGDMA resin served as control. ResultsOxirane tended to decrease hardness and increase hydrophobicity. 0:100, 25:75, 50:50 EP5000:DPHA are harder after 24h than control. 75:25 and 100:0 EP5000:DPHA increased in hardness over 24h, but were softer than control. All groups increased in contact angle over 24h. After 24h, 50:50, 75:25 and 0:100 EP5000:DPHA were more hydrophobic (∼75–84°) than the control (∼65°). Acrylate DoC was ∼60% across all experimental groups. Initial oxirane conversion varied from ∼42% in 100:0 EP5000:DPHA to ∼82% 75:25 EP5000:DPHA. However, oxirane DoC increased for 100:0 EP5000:DPHA to ∼73° over 24h, demonstrating dark cure. Moduli and ultimate transverse strengths of OASys groups were higher than for 0:100 EP5000:DPHA, with 50:50 EP5000:DPHA having higher modulus than other experimental groups. However, the control had higher modulus and UTS than all experimental groups. Volumetric shrinkage averaged 7% for experimental groups, but stress decreased dramatically with increasing oxirane content. SignificanceHydrophobic, low shrinkage-stress OASys resins are promising for development of composites that improve longevity and reduce the cost of dental care.

Gamma irradiation processed (epoxidized soybean fatty acids/ρ-substituted aromatic amines) adducts as corrosion inhibitors for UV–curable steel coatings

A novel method for the synthesis of anticorrosion agents for protection of mild steel substrates was introduced. The reaction of eco-friendly epoxidized soybean fatty acids (ESOF) with different ρ-substituted aromatic amines namely, ρ-methoxyphenylamine (ρ-MPA), ρ-acetylphenylamine (ρ-APA), and ρ-bromophenylamine (ρ-BPA) was carried out under the effect of gamma irradiation to produce ρ-MPA/ESOF, ρ-APA/ESOF, and ρ-BPA/ESOF adducts, respectively. The produced adduct compounds were characterized by oxirane content, acid value, viscosity, and FTIR-spectroscopy. Different concentrations of the adducts were incorporated into solvent free different UV curable coating formulations to estimate them as corrosion inhibitors. The anticorrosion properties of all UV cured coated films were measured in terms of degrees of rusting, blistering, adhesion failure at the scribe, corrosion rate, and weight loss measurements. Besides, the mechanical, physical, and chemical properties of cured coated panels were investigated as well. The results showed that the cured coating films, which contained the prepared adducts could protect the steel substrate from corrosion without any significant change in the properties of cured films and the corrosion inhibitor efficiency of the prepared adducts was arranged as follows: ρ-MPA/ESOF > ρ-APA/ESOF > ρ-BPA/ESOF. Also, the addition of (0.6 g/100 g coating) of all prepared inhibitors into the coating formulations strongly enhanced the corrosion resistance on the mild steel substrates. Thus, according to the obtained results, there is a possibility of using a 50 kGy of γ-irradiation to prepare a highly efficient, economically favorable and eco-friendly corrosion inhibitor, and this must be taken into consideration on an industrial scale.

Back Cover: Eur. J. Lipid Sci. Technol. 7∕2017

European Journal of Lipid Science and TechnologyVolume 119, Issue 7 1770074 Back CoverFree Access Back Cover: Eur. J. Lipid Sci. Technol. 7∕2017 First published: 03 July 2017 https://doi.org/10.1002/ejlt.201770074AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat Graphical Abstract The use of ATR-FTIR spectroscopy to measure changes in the oxirane content and iodine value of vegetable oils during epoxidation Mohammad Hossein Tavassoli-Kafrani, Frederik R. van de Voort, and Jonathan M. Curtis DOI: 10.1002/ejlt.201600354 Monitoring changes in iodine value (IV) and oxirane oxygen content during the epoxidation of vegetable oils by ATR-FTIR. Volume119, Issue7July 20171770074 RelatedInformation

Photosynthesis of anticorrosive protective coatings for steel substrate based on acrylated oil containing unsaturated amino acid compounds

Novel environment friendly anticorrosive coating formulations for mild steel substrate based on acrylated oil were prepared by using unsaturated amino acid compounds. In the first, epoxidized soybean oil acrylate (ESOA) was hardened and modified by the different functionality of monomers to be used in anticorrosive coating formulations. In this article, new corrosion inhibitors were synthesized through two steps. In step one; renewable resource based palm oil was epoxidized under a well-established condition to form epoxidized triglyceride ester of palm oil (EPO). FTIR and oxirane content analysis were used to confirm the formation of the epoxidation reaction. In step two, the EPO was reacted chemically with 4-aminobenzoic acid (AB) and 2-aminoacrylic acid (AA) under controlled conditions of an inert atmosphere and high temperature to produce EPO/AB and EPO/AA adducts. The prepared adducts were characterized by FTIR-spectroscopy and oxirane content analysis. The adducts are evaluated as corrosion inhibitors via adding different concentrations of them to the ESOA coating formulations. Then all coating films were subjected to UV irradiation. Degrees of rusting, blistering, failure at scribe, and weight loss values were measured for all UV cured films, in addition to the chemical and mechanical measurements. The obtained experimental results revealed that the cured coating films containing EPO/AB inhibitor displayed higher resistance to corrosion on the mild steel substrate than EPO/AA without any effect on the mechanical and chemical properties of cured films. Also, the optimum concentration of the prepared inhibitors was to be 0.5%.

The use of ATR‐FTIR spectroscopy to measure changes in the oxirane content and iodine value of vegetable oils during epoxidation

A rapid attenuated total reflectance Fourier transform infrared (ATR‐FTIR) method was developed to simultaneously measure for vegetable oils both their oxirane oxygen content (OOC) and the change in their iodine values (IV) that occur during their epoxidation. The method uses the peak area of the epoxy functional group absorption (1497.3–1432.0 cm−1) to measure OOC and the HCabsorption associated with a carbon–carbon double bond (3017.5–3004.2 cm−1) to determine the relative changes in iodine value (ΔIV). Calibrations were developed by gravimetrically blending epoxidized canola oil (ECO) with unreacted canola oil (CO) to vary both OOC and IV. Oils including canola, camelina, and flaxseed were epoxidized, during which the OOC and ΔIV were tracked as a function of time using both the new ATR‐FTIR procedures and the standard ASTM methods. Both the OOC and ΔIV values measured by the ATR‐FTIR method correlate well to values from standard methods (R2 ≥ 0.992 and mean relative error of <3%). The FTIR procedure is simple and fast to perform and facilitates the determination of selectivity (conversion of double bonds into oxirane group) and the end‐point for the epoxidation reaction, which requires measurement of both OOC and IV.Practical applications: The ATR‐FTIR method described provides a simple, rapid, and accurate means for the measurement of OOC as well as changes in iodine value during the epoxidation of vegetable oils. This allows for the determination of the degree of conversion of lipid unsaturation into epoxides. This method can be employed by manufacturers and research laboratories to study, control, and optimize epoxidation processes.The ATR‐FTIR methods described in this paper provide a simple and rapid means of monitoring OOC and IV changes during the epoxidation of vegetable oils. These methods are calibrated against standard titrimetric procedures and have been shown to produce similar results. It is especially useful that OOC and ΔIV, the two measures that are most relevant for monitoring the progress of a triacylglycerol oil epoxidation reaction, can be obtained from a single analysis. This facilitates monitoring and optimizing epoxidation processes. If the initial IV of oil is known, the method can also be used to calculate the yield, conversion, and selectivity of the reaction, as well as a study the reaction kinetics.

Characterizing the epoxidation process conditions of canola oil for reactor scale-up

Novel epoxidized vegetable oils are of current interest for a variety of applications in coatings and polymeric materials. Samples are needed at quantities beyond gram scale to test such applications. However, scale-up of this very exothermic reaction requires an increased understanding of actual reaction temperature (Tr), which may be much higher than the water bath temperature (Tb). Canola oil (300g) was epoxidized at three H2O2 addition rates (4.6, 2.3, and 1.2gmin−1mol−1 unsaturation); at three Tb (55, 65, and 75°C); and at three reaction times (2.5, 4, and 5.5h). The addition rates were obtained by adding 180g of H2O2 over 0.5, 1, and 2h. Maximum ΔT (Tr–Tb) was attained within 30–40min of reaction time; thereafter, reactor temperatures gradually declined even though H2O2 addition continued. The maximum ΔT (8.7–15.8°C) increased as the Tb and H2O2 addition rate increased; but, no clear trend was observed in the time maximum ΔT values were attained. The ΔT vs time profile was a useful indicator of the extent of epoxidation and can be used as a criteria to stop epoxidation reaction. The greatest source of variation in oxirane content was from Tb and reaction time. Therefore, Tr must be maintained within the optimal range during the high exothermic periods, if high resin quality and minimal process time is to be achieved during scale-up.

Comparison study on the physicochemical properties of phosphate esters from epoxidised palm kernel oil and soybean oil

A series of phosphate esters from soybean oil and palm kernel oil has been synthesised by reacting each epoxidised soybean oil and epoxidised palm kernel oil with o-phosphoric acid in the presence of t-butyl alcohol as the solvent. The amount of o-phosphoric acid was varied at 0, 2.5, 5.0 and 7.5 wt-%. The hydrolysis was conducted at a temperature range of 80–90°C. The physiochemical properties of the phosphate esters were determined, that were, acid value, hydroxyl value, oxirane and moisture contents. The Fourier transform infrared spectroscopy analysis was carried out to confirm the formation of the phosphate ester (P–O–C). The oxirane content after hydrolysis was below 0.2%. Higher addition of phosphoric acid (7.5 wt-%) increased the moisture content and the acid value of the phosphate esters. These results were applicable for both soybean oil-based phosphate ester (SOPE) and the palm kernel oil-based phosphate ester (PKOPE). However, SOPE and PKOPE with 2.5 wt-% of phosphoric acid showed higher hydroxyl value.

Epoxidized rice bran oil (ERBO) as a plasticizer for poly(vinyl chloride) (PVC)

With environmental and toxicity concerns becoming more critical, there are increasing efforts to remove phthalates from polymer compounds around the globe more rapidly. Phthalates can be replaced by natural products; in particular, those obtained from vegetable oils and fats. In the present study, a natural-based plasticizer, synthesized by epoxidation of non-toxic rice bran oil (RBO) with peroxy acid generated in situ has been added to poly(vinyl chloride). The influence of various reaction parameters on epoxidation was studied by investigating the reaction ratio, temperature, reaction time and stirring speed. Epoxidized rice bran oil (ERBO) obtained from an optimized reaction condition was analyzed by iodine number and oxirane content. FTIR was used to analyze epoxy group formation. Product ERBO was obtained with 82 % oxirane conversion within 3 h of reaction period. PVC sheets were formulated using a conventional plasticizer di-(octyl) phthalate and was partially replaced by synthesized ERBO. The effect of ERBO addition was tested by mechanical properties (tensile strength, modulus, elongation-at-break, shore D hardness) and compared with commercially available ESBO (epoxidized soybean oil). ERBO presented fairly good incorporation and plasticizing performance, as demonstrated by the results of mechanical properties, exudation, migration tests, thermal stability by thermogravimetric analysis, T g values as shown by differential scanning calorimetry, replacing about 60 % of the total plasticizer.

Multi-Response Optimization of Epoxidation Process Parameters of Rapeseed Oil Using Response Surface Methodology (RSM)-Based Desirability Analysis

The primary efforts of this investigation stand focused on formulating a biodegradable lubricant with good thermo-oxidative stability and low pour point. Rapeseed oil was chosen to this end and was chemically modified via epoxidation, hydroxylation and transesterification processes. This study focuses on multi-response optimization of epoxidation of rapeseed oil with performic acid as oxygen carrier generated in situ. Experiments were conducted using full factorial central composite design. Response Surface methodology-based desirability analysis was employed for the optimization of process parameters namely reaction time and temperature based on the multiple performance characteristics including oxirane content and % conversion. The mathematical models were developed and tested for adequacy using analysis of variance, and other adequacy measures using the developed models. The main and interaction effects of the input variables on the predicted responses were also investigated. The optimization results showed that the reaction time of 3.23 h and the temperature of 70.74 °C were necessary to maximize oxirane content and % conversion in the epoxidation process.

Synthesis and Characterization of Palm Oil Based Polyol

In this study, palm oil-based polyols were prepared and characterized. In order to prepare the polyol, Epoxidized palm oil (EPO) was reacted with glycerol and undergoes ring opening reaction. The synthesized oil was characterized by oxygen oxirane content titration (OOC), hydroxyl value test (HV), fourier transform infrared (FTIR) and nuclear magnetic resonance (NMR). Based on the FTIR spectrum of polyols, the disappearance of epoxy groups at 825cm-1, 843cm-1 and the emergence of hydroxyl group at 3394cm-1 are obvious indicating that hydroxyl group of the polyols formed. In NMR, the presence of new signal at δ 3.46ppm (-CH-OH) showed the attachment of hydroxyl group onto the epoxidized palm oil.

Synthesis and Characterization of Non-Isocyanate Polyurethane from Epoxidized Linoleic Acid – A Preliminary Study

Non-isocyanate polyurethane (NIPU) was synthesized from epoxidized linoleic acid (ELA) from rubber seed oil. In this study, carboxylation method was used to synthesize a new monomer, carboxylated linoleic acid (CLA) to produce urethane inter-linkage polymer. ELA with tetrabutylammonium bromide (TBABr) as catalyst was purged with carbon dioxide as gas reactant. Pressure and temperature reactions were controlled at 10 psi and 150 °C. CLA was mixed with ethylenediamine (EDA) and the viscous mixture was cured in a covered mold in an oven at 100 °C and curing was performed after 12 hours. Tacky test was done to evaluate the curing. The initial epoxy value of ELA was 7.36 % and it was observed during synthesis to reduce via Oxygen Oxirane Content test, which illustrated the conversion of ELA to CLA. The formation of epoxy group in ELA to carboxylate functional group in CLA was characterized using Fourier Transform Infrared (FTIR) at absorption peak of 1803.69 cm-1that represent cyclic carbonate group. H-NMR was used to support the characterization of ELA and CLA.

Vegetable oil-derived epoxy monomers and polymer blends: A comparative study with review

Glycidyl esters of epoxidized fatty acids derived from soybean oil (EGS) and linseed oil (EGL) have been syn- thesized to have higher oxirane content, more reactivity and lower viscosity than epoxidized soybean oil (ESO) or epoxi- dized linseed oil (ELO). The EGS and ESO, for comparison, were used neat and in blends with diglycidyl ether of bisphenol A (DGEBA). Thermosetting resins were fabricated with the epoxy monomers and either BF3 catalyst or anhy- dride. The curing behaviors, glass transition temperatures, crosslink densities and mechanical properties were tested. The results indicated that polymer glass transition temperatures were mostly a function of oxirane content with additional influ- ence of glycidyl versus internal oxirane reactivity, pendant chain content, and chemical structure and presence of saturated components. EGS provided better compatibility with DGEBA, improved intermolecular crosslinking and glass transition temperature, and yielded mechanically stronger polymerized materials than materials obtained using ESO. Other benefits of the EGS resin blend systems were significantly reduced viscosities compared to either DGEBA or ESO-blended DGEBA counterparts. Therefore, EGS that is derived from renewable sources has improved potential for fabrication of structural and structurally complex epoxy composites, e.g., by vacuum-assisted resin transfer molding.

Plasticising and Stabilising Effect of Novel Epoxidised Mee Oil on PVC

The plasticising and stabilising effects of novel epoxidised Mee oil (EMO) and its derivatives on poly (vinyl chloride) were investigated. Peroxymethanoic acid was used to epoxidise Mee oil and the product was characterised by FTIR, iodine value, and oxirane content. Solubility parameter values were also determined. Plasticising effects of PVC incorporating EMO were evaluated using tensile and mechanical properties as well as FTIR. It was found that substantial levels of 100% epoxidised oil derivatives of Mee oil (E100M) could be added to PVC; typically about 50 phr E100M with 30 phr of DOP. It was observed that increasing levels of E100M with DOP enhanced the plasticising efficiency; flexibility, percentage elongation, softness, and MFI. The stability provided by EMO in terms of changes in elastic modulus during high-temperature ageing was modelled kinetically, and it was found that the kinetic model obeyed a law of the form: ln (log Ea – log E) = kt + C Activation energy values for the change in elastic modulus of PVC suggest some degree of synergism between EMO and Ca/Zn stearate system. Clearly E100M may be regarded as an effective secondary plasticiser as well as a stabiliser; perhaps more so than the other oil derivatives of Mee oil.

PREPARATION AND CHARACTERIZATION OF HYDROPHILIC MAGNETIC POLYMER MICROSPHERES CONTAINING OXIRANES

Spherical hydrophilic magnetic polymer(MGM) containing oxiranes was synthesized by designing the inverse suspension polymerization system in which formamide was employed as the dispersant of magnetic Fe_3O_4 microcrystal.Scanning electron microscopy(SEM),FT-IR spectroscopy,X-ray diffraction(XRD),vibrating sample magnetometer(VSM),low temperature N_2 adsorption and chemical analysis methods were used to characterize the properties of the polymer.The results showed that MGM had good spherical shape and narrow size distribution,and the particles with diameters ranging from 0.13 mm to 0.28 mm were about 91 wt%.The surface hydrophilicity of Fe_3O_4 microcrystal was improved by formamide dispersing treatment.The gel particles made by the copolymerization of glycidyl methacrylate and N,N′methylene bisacrylamide could encapsule Fe_3O_4 microcrystal to produce colloid cores,and uniform and stable MGM microspheres were formed by the conglomeration of the colloid cores.The saturated magnetization of MGM reached 6.5 emu/g while the Fe_3O_4 content were 6.17%.The specific surface area,average pore diameter and pore volume and oxirane content was 117.6 m~2/g,15.6 nm,0.46 cm~3/g and 0.53(mmol/g,)respectively.Penicillin G acylase(PGA) was immobilized on MGM microspheres by the covalent coupling between the reactive oxiranes of MGM and amino groups of PGA under mild conditions.The apparent activity of the immobilized PGA reached 502 IU/g for hydrolyzing penicillin G potassium to 6-aminopenicillanic acid at 37℃.There was no agglomeration of the magnetic particles in applications .

Formulation and properties' evaluation of PVC/(dioctyl phthalate)/(epoxidized rubber seed oil) plastigels

AbstractEpoxidized rubber seed oil (4.5% oxirane content, ERSO) was prepared by treating the oil with peracetic acid generated in situ by reacting glacial acetic acid with hydrogen peroxide. The thermal behavior of the ERSO was determined by differential scanning calorimetry. The effect of the epoxidized oil on the thermal stability of poly (vinyl chloride) (PVC) plastigels, formulated to contain dioctyl phthalate (DOP) plasticizer and various amounts of the epoxidized oil, was evaluated by using discoloration indices of the polymer samples degraded at 160°C for 30 min and thermogravimetry at a constant heating rate of 10°C/min up to 600°C. The thermal behavior of the ERSO was characterized by endothermic peaks at about 150°C, which were attributed to the formation of network structures via epoxide groups, and at temperatures above 300°C, which were due to the decomposition of the material. Up to 50% of the DOP plasticizer in the PVC plastisol formulation could be substituted by ERSO without a marked deleterious effect on the consistency of the plastigel formed. In the presence of the epoxidized oil, PVC plastigel samples showed a marked reduction in discoloration and the number of conjugated double bonds, as well as high temperatures for the attainment of specific extents of degradation. These results showed that the ERSO retarded/inhibited thermal dehydrochlorination and the formation of long (n > 6) polyene sequences in PVC plastigels. The plasticizer efficiency/permanence of ERSO in PVC/DOP plastigels was evaluated from mechanical properties' measurements, leaching/migration tests, and water vapor permeability studies. The results showed that a large proportion of DOP could be substituted by ERSO in a PVC plastisol formulation without deleterious effects on the properties of the plastigels. J. VINYL ADDIT. TECHNOL., 2008. © 2008 Society of Plastics Engineers.

The effect of bio-based plasticizer on the permanence and water vapor transport properties of PVC plastigels

Novel formulations of PVC plastisols based on blends of bio-based and synthetic plasticizers were prepared and characterized. A traditional phthalate plasticizer, dioctylphthalate, was replaced in the plastisols studied by the epoxidized rubber seed oil (4.5 % oxirane content). The plastisols formed were processed into plastigels and characterized in terms of permanence properties using leaching and migration tests and water vapour barrier properties. It was found that the permanence properties of PVC/DOP plastigels were maintained in the presence of up to 50 % ERSO, and that blending with DOP did not impair the water barrier properties of PVC plastigels.

Epoxidation of karanja (Pongamia glabra) oil catalysed by acidic ion exchange resin

AbstractKaranja oil with an iodine value of 89 g/100 g was epoxidised in situ with aqueous hydrogen peroxide and acetic acid in the presence of Amberlite IR‐120 acidic ion exchange resin as catalyst. The effect of the operating variables on the oxirane oxygen content, as well as on the oxirane ring stability and the iodine value of the epoxidised karanja oil, were determined. The variables studied were stirring speed, hydrogen peroxide‐to‐ethylenic unsaturation molar ratio, acetic acid‐to‐ethylenic unsaturation molar ratio, temperature, and catalyst loading. The effects of these parameters on the conversion to the epoxidised oil were studied and the optimum conditions for the maximum oxirane content were established. The proposed kinetic model takes into consideration the two side reactions, namely, epoxy ring opening involving the formation of hydroxy acetate and hydroxyl groups, and the reaction between the peroxyacid and the epoxy group. The kinetic and adsorption constants of the rate equations were estimated by the best fit using Marquardt's algorithm. Good agreement between experimental and predicted data validates the proposed kinetic model. From the estimated kinetic constants, the apparent activation energy for the epoxidation reaction was found to be 11 kcal/mol.

Direct incorporation of gaseous carbon dioxide into solid‐state copolymer containing oxirane and quaternary ammonium halide structure as self‐catalytic function

AbstractWe established a self‐catalyst system for solid phase incorporation of gaseous carbon dioxide into terpolymers prepared by polymerization of glycidyl methacrylate, N‐benzyl‐N‐[2‐(methacryrolroxy)ethyl]‐N,N‐dimethylammonium bromide, and methyl methacrylate. Terpolymer composition affected the incorporation behavior where the terpolymer with higher oxirane content exhibited higher efficiency of carbon dioxide incorporation. © 2004 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 42: 4941–4947, 2004

Polymer supported iminodipropylene glycol functions for removal of boron

Polymer supported iminodipropylene glycol functions have been shown to be efficient in chelation with boric acid and can be used for removal of boric acid at ppm levels. Glycidyl methacrylate (GMA)–methyl methacrylate (MMA)–DVB (divinyl benzene) terpolymer beads have been prepared and used as support. The polymer support with 3.4 mmol g −1 oxirane content can be readily modified by reacting with an excess of ethylene diamine, in high conversion yields (99.1%). Reaction of the latter with glycidol gives corresponding resin with aminopropylene glycol functions. The resulting resin has been demonstrated to be an efficient sorbent for removal of boron. The resin has 3 mmol g −1 of boron loading capacity and shows reasonably rapid sorption ability so that boron in 10 ml of H 3BO 3 solution (50 ppm) can be removed almost completely in less than 12 min of contact time by 0.5 g of polymer sample. Splitting of sorbed boron can be achieved by simple acid leaching (4 M HCl) and regenerated by NaOH solution (0.1 M).

Properties of modified hydroxyl-terminated polybutadiene based polyurethane membrane

One hydroxyl-terminated polybutadiene (HTPB) based polyurethane (PU) solution was prepared by reacting equal equivalent of 4,4-methylene diphenyl diisocyanate (MDI) and HTPB with 1,4-butanediol (BDO) as chain extender. The PU was then cast into membrane. The kinetic of epoxidation of HTPB-based PU membrane by an in situ generated peracid method was studied by infrared spectroscopy. The epoxidized PU membrane was named as EPU. The other HTPB-based PU with different molar ratios of dimethyol propionic acid (DPA) and 1,4-BDO as chain extender were synthesized by solution polymerization. The present PU was then cast into a membrane and named as PUDPA. 1-Ethyl-3-(3-dimethyamino propyl) carbodiimide (EDAC) was used in the linking reaction to graft heparin to PUDPA to get heparin containing PUDPA membrane and named as PUDPA-Hep. The membranes were subsequently characterized by the Fourier transform infrared spectroscopy and electron spectroscopy for chemical analysis (ESCA). The properties of PU such as density and gas permeation test were measured. Wettability and protein adsorption on the membranes were also evaluated from the water content, contact angle, and protein adsorptions of fibrinogen and albumin on the PU membrane. The diffusion coefficient of water in the membrane was determined in accordance with the Fickian diffusion mechanism. By using Kaelble’s equation and the contact angle data, the surface energy of PU membrane was determined. The protein adsorption of fibrinogen and albumin on PU membranes was evaluated. It was found that oxirane content in the EPU membrane increased with epoxidation time. The surface energy of EPU and PUDPA membranes increased with the increasing of oxirane content and DPA content on the EPU and PUDPA membrane, respectively, whereas the contact angle decreased inversely. The surface tension of wet EPU and PUDPA membrane was higher than that of dry EPU and PUDPA membrane, respectively. The adsorption of albumin and fibrinogen decreased with increasing the degree of epoxidation and the DPA content, respectively. After heparin treatment, the contact angel and protein absorption on PUDPA-Hep were lower than those on PUDPA.