Butanediol Diglycidyl Ether Research Articles

Hyaluronan based materials with catanionic sugar-derived surfactants as drug delivery systems.

In the present work novel drug delivery systems consisting in highly porous Hyaluronan foams for the administration of a non-steroidal anti-inflammatory drug (NSAID), ketoprofen, have been obtained. A sugar-derived surfactant associated with ketoprofen was prepared and incorporated into the porous hyaluronan materials. The association between a lactose derived surfactant, Lhyd12, and ketoprofen was obtained by acid-base reaction and its physicochemical properties were studied. Tensiometric and dynamic light scattering (DLS) determinations showed the formation of catanionic surfactant aggregates, Lhyd12/ketoprofen, in aqueous solution. Furthermore, the catanionic surfactants allowed greater solubilisation of ketoprofen. Hyaluronan porous materials were developed using butanediol diglycidyl ether as crosslinking agent. The profile release of Lhyd12/ketoprofen from hyaluronan based materials shows differences as a function of the aggregation state of catanionic surfactant.

Designing a multi-functionalized clay lamellar-co-graphene oxide nanosheet system: An inventive approach to enhance mechanical characteristics of the corresponding epoxy-based nanocomposite coating

Abstract Clay nano-platelets (NC) and Graphene oxide nanosheets (GO) are functionalized by the aid of 1,4- butanediol diglycidyl ether (BDDE) through an aminosilane coupling agent, i.e. 3-Triethoxysilyl propylamine (APTES). The products obtained from the modification process are characterized by visual assessment, FTIR, XRD, TGA, UV–vis, AFM and FE-SEM analyses. The results clearly demonstrate the epoxide ring of BDDE is chemically attached on the surface of the fillers. Furthermore, the process is causing the stacks of layers expand and d-spacing increases. The functionalized NC and GO, i.e. MNC and MGO, are then impregnated into an undiluted clear di-functional bisphenol A/epichlorohydrin derived liquid epoxy resin at 0.3% weight concentration by simple mechanical mixing. The films are also morphologically studied by FE-SEM. Dynamic and static mechanical properties are investigated by DMA and tensile testing. The outcomes demonstrate that there exists an optimum mixing ratio of MGO and MNC to obtain the best mechanical properties, i.e. MGN (70:30). Besides, almost all the modified samples show improved mechanical properties compared to their unmodified counterparts.

Cryogelation within cryogels: Silk fibroin scaffolds with single-, double- and triple-network structures

Mechanically strong silk fibroin cryogels with two generations of pores were produced by carrying out the cryogelation reactions within the pores of the initial single-network (SN) fibroin cryogels. In this way, cryogels with interpenetrated and interconnected double- (DN), and triple-network (TN) structures were produced from fibroin solutions frozen at −18 °C in the presence of butanediol diglycidyl ether cross-linker and N,N,N′,N′-tetramethylethylenediamine as a pH regulator. Cryogel scaffolds formed at fibroin concentrations above 25 wt% exhibit a Young's modulus between 66 and 126 MPa, and sustain around 90% compressions under 87–240 MPa stresses. These values are the largest reported so far for fibroin scaffolds and hence the materials have promising applications in bone tissue engineering. We also show that the improvement in the mechanical performance of cryogels after multiple-networking is due to their increased content of fibroin network. Both DN and TN cryogels have two generations of interconnected macropores with diameters 20–30 μm and 3–9 μm. The size of both large and small pores could be adjusted by the relative amounts of fibroin in the network components.

Structure and performance evaluation on aged SBS modified bitumen with bi- or tri-epoxy reactive rejuvenating system

To cater for the concept of global green development, it is of importance, in the bituminous road domain, to achieve the objective of the high-quality rejuvenation of waste bitumen. This paper investigates physical properties, rheological properties, morphology and molecular structure of rejuvenated SBS modified bitumen (SMB) with 1, 4-butanediol diglycidyl ether (BUDGE) or trimethylolpropane triglycidyl ether (TMPGE). The results of physical properties indicate that BUDGE and TMPGE can both improve the low-temperature ductility and penetration of aged SMB, and by contrast, BUDGE can make the aged SMB more flexible at low temperature. From the rheological properties, BUDGE or TMPGE can help restore the crack resistance at low temperature and somewhat decrease the rutting resistance at high temperature, which relies on the reduction of fatigue factor and rutting factor of aged SMB. FTIR spectra and fluorescence images show that the original structure of SBS can be partly rebuilt through the chemical reaction between the terminal groups on BUDGE or TMPGE and the oxygen-containing reactive groups on degraded SBS.

High-strength silk fibroin scaffolds with anisotropic mechanical properties

In contrast to isotropic morphologies of synthetic hydrogels, many biological tissues possess anisotropic hierarchical morphologies leading to extraordinary mechanical properties that cannot be mimicked by synthetic materials. Here, we report preparation of anisotropic silk fibroin cryogels and scaffolds exhibiting a Young's modulus in the range of MPa that sustain up to 20 MPa compressive stresses. The cryogels were prepared by a combined directional freezing – cryogelation process starting from an aqueous 4.2 wt% fibroin solution containing butanediol diglycidyl ether cross-linker and N,N,N′,N′-tetramethylethylenediamine. In the first step, the reactor containing the aqueous solution of fibroin, cross-linker, and TEMED was immersed into liquid nitrogen at a controlled rate to create a directionally frozen ice template. In the second step, cryogelation reactions were conducted in this frozen solution at −18 °C whereby the cryo-concentrated fibroin in the unfrozen microzones of the reaction system forms a 3D fibroin network. The scaffolds exhibit anisotropic microstructure and hence anisotropic mechanical properties, e.g., the Young's modulus is 3.4 ± 0.5 MPa and 0.8 ± 0.3 MPa when measured along the directions parallel and vertical to the freezing direction, respectively. All the cryogels could completely be compressed due to squeezing out of water from their pores. Upon removal of the load, the compressed cryogels immediately recover their original dimensions and mechanical properties by absorbing the released water into their pores.

Reversibility of strain stiffening in silk fibroin gels

We investigate the linear and nonlinear viscoelastic properties as well as the reversibility of strain-stiffening behavior of silk fibroin gels. The gels are prepared from 4.2w/v% fibroin solution in the presence of butanediol diglycidyl ether and N,N,N',N'-tetramethylethylenediamine (TEMED) as a cross-linker and catalyst, respectively. By changing the concentration of TEMED in the gelation system, fibroin gels exhibiting a storage modulus G’ between 10−1–105Pa and a loss factor tan δ between 10−2 and 10° could be obtained. We observe a strong stiffening (up to 900%) in fibroin gels with increasing strain above 10% deformation, but reversibly if the strain is removed, the gel recovers its initial viscoelastic properties. The strain induced formation of transient intermolecular domains acting as reversible cross-links are responsible for the stiffening behavior of fibroin gels. These additional cross-links formed in the hardened fibroin gels have a temporary nature with lifetimes of the order of seconds. The nonlinear behavior of fibroin gels can be reproduced by a wormlike chain model taking into account the entropic elasticity of fibroin molecules and the strain induced increase in the cross-link density of fibroin gels.

Effect of modification of cyclic butylene terephthalate on crystallinity and properties after ring-opening polymerisation

Ring-opening polymerisation of the macro-cyclic oligomer of butylene terephthalate at elevated temperatures was found to produce high molecular weight polybutylene terephthalate that was both highly crystalline and brittle. The impact of reactive and non-reactive additives on the polymerisation, crystallisation and final crystal structure was extensively studied using differential scanning calorimetry and rheological methods and correlated with observed improvements in fracture toughness and tensile properties for both the neat resin and mode I and II fracture toughness of the fibre-reinforced composites. The reactive modifiers used were bi-functional epoxy resins, namely diglycidyl ether of bis phenol A, butanediol diglycidyl ether and bis[(glycidyl ether)phenyl)]-m-xylene, while the non-reactive modifiers were selected β nucleants and the ductile thermoplastic, polyethylene glycidyl methacrylate.

Evaluation of in-vitro degradation rate of hyaluronic acid-based hydrogel cross-linked with 1, 4-butanediol diglycidyl ether (BDDE) using RP-HPLC and UV–Vis spectroscopy

A hyaluronic acid (HA) was cross-linked with 1, 4-butanediol diglycidyl ether to produce nine BDDE-HA hydrogels. The degradation rates of six hydrogels were evaluated by HPLC and UV–Visible spectroscopy. The percentage amount of N-acetyl glucosamine NAG obtained after one-day enzymatic digestion to the total amount obtained after complete digestion was an indicative of the degradation rate of each hydrogel. The results were calculated with 95% confidence interval and showed 62.6% ± 12.3 w/w, precision value % R.S.D = 7.95, average recovery = 81.0%, LOD = 6.4 μg/ml for HPLC and 63.3 ± 13.9 w/w, precision value % R.S.D = 8.83, average recovery = 83.1%, LOD = 5.4 μg/ml for UV method. The two methods showed also good linearity with correlation coefficients R2 of 0.998 and 0.9995 for HPLC and UV method respectively. For a comparison purpose, the other three hydrogels were rated using the conventional weight loss method which showed relatively higher degradation rates with an average of 73.4% ± 5.7 w/w, % R.S.D = 3.13. Statistical analysis revealed that there was no significant difference between HPLC and UV–Visible methods, however, these values differed significantly (p < 0.05) from the value obtained from the weight loss method.

Modulation of biomechanical properties of hyaluronic acid hydrogels by crosslinking agents.

Modulation of both mechanical properties and biocompatibilities of hyaluronic acid (HA) hydrogels is very importance for their applications in biomaterials. Pure HA solution was converted into a hydrogel by using butanediol diglycidyl ether (BDDE) as a crosslinking agent. Mechanical properties of the HA hydrogels have been evaluated by adding up different amount of BDDEs. While the mechanical properties of the obtained HA hydrogels were evaluated by measuring their crosslinking degrees, elastic modulus and viscosity, their in vitro biocompatibilities were done by measuring the degrees of anti-inflammatory reactions, cell viabilities and cytotoxicity. The degrees of anti-inflammatory reactions were determined by measuring the amount of nitric oxides (NOs) released from lipopolysaccharide(LPS)(+)-induced macrophages; cell viability was evaluated by observing differences in the behaviors of fibroblasts covered with the HA hydrogels, compared with those covered with the films of Teflon and Latex. Cytotoxicity of the HA hydrogels was also evaluated by measuring the degrees of viability of the cells exposed on the extracts of the HA hydrogels over those of Teflon, Latex and pure HA solutions by the assays of thiazoly blue tetrazolium bromide (MTT), neutral reds, and bromodeoxyuridine (BrdU). The results showed that employment of BDDEs beyond critical amounts showed lower biocompatibility of the crosslinked HA hydrogels but higher crosslinking degrees and mechanical properties, indicating the importance of controlling the HA concentrations, BDDE amounts and their reaction times for the synthesis of the crosslinked HA hydrogels for their clinical applications as biomaterials.

Productivity Model for Separation of Proteins Using Ceramic Monoliths As a Stationary Phase

The compact geometry and outstanding mechanical properties of ceramic monoliths are valuable features when designing reusable standard affinity chromatography columns. High throughput protein separations are becoming standard industrial practice. Column reuse is an important consideration for the development of separation processes when production rate per unit volume of column is taken into account. Due to the cost and downtime needed to regenerate chromatographic columns, throughput depends on the use of the same column for several adsorption–desorption cycles without a significant loss in adsorption. An adsorption–desorption dynamic model was developed and used to estimate the optimum reuse of ceramic monolith columns in affinity chromatography. The model experimental metal chelate affinity chromatography (IMAC) system is a ceramic monolith covered with agarose type D-5 activated with 1.4 butanediol diglycidyl ether as spacer arm, iminodiacetic acid as chelating agent, and Cu2+ as ligand. The effect of performing several adsorption/elution cycles on column performance was evaluated using five monoliths at different flow rates, for a total of five cycles each. The strategy used to interpret experimental results leads to a theoretical model for successive monolith reuses that can be readily used to determine the optimal reuse of monoliths on the basis of maximum production rate per volume of chromatographic columns.

Behavior of human immunoglobulin G adsorption onto immobilized Cu(II) affinity hollow‐fiber membranes

Iminodiacetic acid (IDA) and tris(2-aminoethyl)amine (TREN) chelating ligands were immobilized on poly(ethylene vinyl alcohol) (PEVA) hollow-fiber membranes after activation with epichlorohydrin or butanediol diglycidyl ether (bisoxirane). The affinity membranes complexed with Cu(II) were evaluated for adsorption of human immunoglobulin G (IgG). The effects of matrix activation and buffer system on adsorption of IgG were studied. Isotherms of batch IgG adsorption onto finely cut membranes showed that neither of the chelates, IDA-Cu(II) or TREN-Cu(II), had a Langmuirean behavior with negative cooperativity for IgG binding. A comparison of equilibrium and dynamic maximum capacities showed that the dynamic capacity for a mini-cartridge in a cross-flow filtration mode (52.5 and 298.4 mg g(-1) dry weight for PEVA-TREN-Cu(II) and PEVA-IDA-Cu(II), respectively) was somewhat higher than the equilibrium capacity (9.2 and 73.3 mg g(-1) dry weight for PEVA-TREN-Cu(II) and PEVA-IDA-Cu(II), respectively). When mini-cartridges were used, the dynamic adsorption capacity of IDA-Cu(II) was the same for both mini-cartridge and agarose gel.

Solid phase extraction and preconcentration of Ni(II) using 1-(2-pyridylazo)-2-naphthol) (PAN) modified β-cyclodextrin butanediol diglycidyl ether polymer as a solid phase extractant

A sensitive, simple and selective preconcentration method was developed for the preconcentration of trace amounts of Ni(II) ions using 1-(2-pyridylazo)-2-naphthol (PAN) modified β-cyclodextrin butanediol diglycidyl ether polymer as a solid phase extractant. Potential factors affecting the sorption of Ni(II) were investigated. Meanwhile, the optimum conditions were established. The sorbed Ni(II) was eluted using 5 ml of 2 M HCl. The preconcentrtion factor was 70. The detection limit for Ni(II) was 1.18 ng/ml. The relative standard deviation (RSD %) was &gt;1%. The developed method was successfully applied for the determination of trace Ni(II) in different water and potato chip samples as well as reference alloy samples.

Functionalization and Characterization of Immobilized Metal Affinity Hydrogel Membranes

Previous studies have shown that functionalization of hydrogel membranes with metal affinity ligands increases the separation potential of the membranes for purification of biological systems. To achieve separation, histidines that are exposed on the proteins surface are attracted and attach to the metal ion within the IMA membrane matrix. The effectiveness of these membranes depends on several factors including, but not limited to, type of chelating group, the metal ion, and solution buffer. This paper is concerned with crosslinking of poly (vinyl) alcohol (PVA) with varied degrees of crosslinking that was subsequently functionalized with the immobilized metal affinity (IMA) group, that included a spacing element, (1, 4 Butanediol Diglycidyl ether (1,4 BDE)), chelator (NTA (Nitrilotriacetic acid)), and metal (Nickel (Ni2+). The impact of chelating ligand and glutaraldehyde concentration on the swelling and bound metal content was determined. Additionally, Fourier-transform infrared spectroscopy (FTIR) was used to examine the functional groups for the control (without metal attached) and affinity (with metal attached) membranes. Ultimately, this study suggests that crosslinking membranes with a higher glutaraldehyde percentage yielded a higher content of bound nickel.

Preparation, characterization, and release properties of hydrogels based on hyaluronan for pharmaceutical and biomedical use

ABSTRACTHyaluronic acid (HA) is a natural polysaccharide that is widely distributed in the human body. Its physicochemical properties and high biocompatibility make it a good candidate for biomedical and pharmaceutical uses. In the present work, we report HA‐based hydrogels that could be applied as drug delivery systems or as implants for the treatment of joint diseases. We use butanediol diglycidyl ether as a chemical crosslinker to obtain HA hydrogels. Using a new dissolution tester and ketoprofen (KP) as a model drug, we study the release properties of the hydrogels. We obtain homogeneous and transparent hydrogels with high strength and elasticity. The swelling ratio (SR) depends on the crosslinker concentration and pH of the medium. We also reveal differences between the release profile of KP from swollen and unswollen hydrogels. The characteristics and differences in KP release profiles depending on the SR suggest the possibility of obtaining controlled release from HA‐based hydrogels. © 2013 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 130: 1377‐1382, 2013

IN VITRO EVALUATION OF BUBALINE ACELLULAR SMALL INTESTINAL MATRIX

In this study, a decellularization process was employed to remove the cellular components from small intestine of buffalo ( Bubalus bubalis ) using 2% ionic biological detergent. The acellular matrix then was cross linked with 0.6% glutaraldehyde (GA), 1% 1, 4-butanediol diglycidyl ether (BDDGE) and 1% 1- ethyl- 3 - (3 - dimethylaminopropyl) carbodiimide (EDC). The physical properties of cross linked samples were compared, in vitro , to those of the acellular counterparts on the basis of gross observations, degradation tests, free protein contents, free amino group contents, fixation index, free hydroxyproline contents determination, moisture percent and SDS-PAGE analysis. GA treated tissue showed highest resistance to nonenzymatic, enzymatic degradation and significant reduction (P<0.05) of free protein contents, free amino groups contents and moisture percentage. SDS-PAGE analysis revealed that GA treated acellular small intestinal matrix expressed highest cross-linking, followed by EDC, and BDDGE treated tissues.

Development of Monoclonal Antibody Based Heterologous Immunoassay for Ractopamine Residue

This study aimed to develop a monoclonal antibody based icELISA method for Ractopamine (Rac) residue. For this purpose, mixed anhydride method was employed to synthesize the immunogen of Rac-BSA and 1, 4-butanediol diglycidyl ether was used to prepare the coating antigen of Rac-OVA, thus pursue the heterologous sensitivity. Through cell fusion technology, four Hybridoma named R1-B5, R2-B3, R2-C6, and R4-C8 were screened out, and the Kas of all mAbs were between 2.7 and 4.8×109 L/mol. Based on the R1-B5 mAb, a heterologous icELISA standard curve was developed. The working range was from 0.013 to 33.7 ng/mL, with LOD and IC50 value of 0.007 ng/mL and 0.67 ng/mL, respectively. Therefore, this icELISA can be used for detecting Rac residue in animal products.

Improvement of hyaluronic acid enzymatic stability by the grafting of amino-acids

Injection of hyaluronic acid (HA)-based hydrogels has proven to provide many therapeutic benefits. To increase the stability of HA-based products against enzymatic digestion, we modified hyaluronic acid by grafting various amino acids on its carboxylic group and then evaluated the enzymatic stability of the various conjugates in presence of a hyaluronidase. Our results showed that all amino acid-modified HA polymers were more resistant to degradation compared to the native HA albeit with variation according to the amino acids. Amino acids with carboxylate groups such as aspartic acid or with hydroxyl functions (threonine, serine or tyrosine) conferred a particularly strong resistance to HA towards enzymatic digestion. The HA-amino acid products were then cross-linked with butanediol diglycidyl ether (BDDE). The swelling properties of the formed hydrogels appeared close to native HA whereas the increased resistance towards hyaluronidase digestion remained. These results suggest that amino acid-modified HA derivatives can become promising material for viscosupplementation or drug delivery.

Comparative study of a new dermal filler Uma Jeunesse® and Juvéderm®

Innovation in technology has resulted in the emergence of better, longer-lasting hyaluronic acid implants with fewer side effects. The new dermal implant Uma Jeunesse® was compared to Juvéderm® in this split-face study. Uma Jeunesse® is crosslinked with butanediol diglycidyl ether (BDDE) using a new crosslinking technology. Uma Jeunesse® and Juvéderm® Ultra 3 were injected in a split-face study on 17 healthy volunteers, whose ages ranged from 33-58 years. There were 14 women and three men with medium to deep nasolabial folds. All subjects randomly received either Uma Jeunesse® or Juvéderm®) Ultra 3 on one half of their face. Patients were followed up for 9 months. Juvéderm® was easier to inject with lesser injection pain because of lidocaine, but late postinjection pain was much less with Uma Jeunesse® as compared to Juvéderm®. Overall rate of early and late complications as well as adverse events was lower with Uma Jeunesse® than Juvéderm(®) . After 9 months of follow-up, Uma Jeunesse® lasted in tissues for longer as compared to Juvéderm(®) even in patients injected for the first time (P<0.0001). Patient acceptability rate of Uma Jeunesse® was also much higher. Perception of pain during injection was lesser with Juvéderm® probably because of the presence of lidocaine. The new dermal implant Uma Jeunesse® is a safe and patient-friendly product which resides in the tissues for longer with maintenance of aesthetic effect over and beyond 6 months, reaching 9 months in over 80% of patients, and Juvéderm® injection is less painful.

Extraction of Azo Dye Molecules from Aqueous Solution using Polyamidoamine Dendrimer Based Polymeric Network

Synthesis of novel polyamidoamine (PAMAM) dendrimer based network polymer 2 based on the reaction between an amine-terminated PAMAM dendrimer 1 (G = 3, ethylenediamine core) and butanediol diglycidylether has been achieved. The divergent approach has been employed for the synthesis of the PAMAM dendrimer 1. This polyamidoamine (PAMAM) dendrimer based network polymer 2 has been successfully characterised by means of FT-IR spectroscopy and elemental analyses and the extraction of methyl orange dye molecules from aqueous solution has been investigated.

Functionalised supports with sugar dendritic ligand

Functionalised supports with sugar dendritic ligand were obtained from chemical modification on poly(hydroxylated polybutadienic-hydroxyethyl methacrylate) [poly(PB-HEMA)] matrix. The matrix was activated with 1,4 butanediol diglycidyl ether (BDGE) or epichlorohydrin (ECH). Later, a dendritic molecule was immobilised and submitted to react with glucose (GLU) using a carbodiimide reagent. Then, glucose-containing supports were used as sorbents to retain Concanavalin A (Con A). Properties such as equilibrium volume swelling ratios ( q v), extent of conversion of functional groups, amount of bound dendritic molecule and amount of coupled glucose were analysed.