Butanediol Dimethacrylate Research Articles

On the Addition of Multifunctional Methacrylate Monomers to an Acrylic-Based Infusible Resin for the Weldability of Acrylic-Based Glass Fibre Composites

The melt strength of Elium® acrylic resin is an important factor to ensure limited fluid flow during welding. To provide Elium® with a suitable melt strength via a slight crosslink, this study examines the effect of two dimethacrylates, namely butanediol-di-methacrylate (BDDMA) and tricyclo-decane-dimethanol-di-methacrylate (TCDDMDA), on the weldability of acrylic-based glass fibre composites. The resin system impregnating a five-layer woven glass preform is a mixture of Elium® acrylic resin, an initiator, and each of the multifunctional methacrylate monomers in the range of 0 to 2 parts per hundred resin (phr). Composite plates are manufactured by vacuum infusion (VI) at an ambient temperature and welded by using the infrared (IR) welding technique. The mechanical thermal analysis of the composites containing multifunctional methacrylate monomers higher than 0.25 phr shows a very little strain for the temperature range of 50 °C to 220 °C. The quantity of 0.25 phr of both of the multifunctional methacrylate monomers in the Elium® matrix improves the maximum bound shear strength of the weld by 50% compared to those compositions without the multifunctional methacrylate monomers.

Environmental Profile and Technological Validation of New High-Tg Unsaturated Polyesters from Fully Bio-Based Monomers and Reactive Diluents

This study was focused on the synthesis and characterization of a fully bio-based unsaturated polyester resin (UPR) with good thermal properties suitable for the commercial production of composite polymers. UPRs based on different ratios of bio-based furan dicarboxylic acid (FDCA), itaconic acid, and diols were synthesized. The unsaturated polymers prepared were evaluated by differential scanning calorimetry, gel permeation chromatography, FTIR and 1H-NMR spectroscopy. The results showed positive effects of FDCA on the glass transition temperature (Tg) of these fully bio-based polyesters, especially when FDCA was combined with 1,2-propanediol. Optimal values of Tg were obtained in the range of 30–32 °C for UPRs synthesized starting with a higher concentration of FDCA in the monomer feed. The possibility of substituting styrene, which usually acts as a reactive diluent, with a greener and safer alternative during the crosslinking of UPRs, was also explored. Two bio-based reactive diluents were considered: dimethyl itaconate (DMI) and butanediol dimethacrylate. After crosslinking, an average Tg of 75 °C and a good crosslinking efficiency indicated by a gel content of 90% were achieved for the fully bio-based polyester obtained under milder reaction conditions and dilution with DMI. Life cycle assessment was performed on selected UPRs, and comparison with a reference fossil-based resin in terms of the calculated category indicator results confirmed the lower environmental impact of the newly prepared bio-based polyesters.

ON THE PREPARATION OF POLYACRYLIC BINDER via MINI-EMULSION POLYMERIZATION FOR LEATHER PERFORMANCE COATINGS

A partially crosslinked polyacrylic copolymer latex composed of butyl acrylate (BA), methyl methacrylate (MMA), methacrylic acid (MAA) and 1,4 butanediol dimethacrylate (BDMA) was synthesized via mini-emulsion polymerization technique. The obtained latex had good electrostatic stability with low average particle size (83 nm) and narrow size distributions (PDI= 0.12). The FTIR and DSC analysis verified the success of the copolymer’s synthesis. The latex was further used as a base coat binder for the coating of shoe upper leathers in a leather finishing application. The performed tests on finished leather showed good dry/wet rubbing performance of the coating as well as excellent flexing endurance. The synthesized latex seemed to be a good candidate as performance binder for leather finishing applications.

Mechanically improved sol-gel derived methacrylate-siloxane hybrid materials with urethane linkage

Ultraviolet (UV)-curable and highly condensed (>86%) methacrylate phenyl oligo-siloxane (MPO) was synthesized by non-hydrolytic sol–gel condensation reaction between methacrylate and phenyl silane precursor. The MPO resin was then cured by an UV-initiated free-radical polymerization to fabricate a transparent (>90% at 550 nm) methacrylate–siloxane hybrid material (methacrylate hybrimer). An urethane butanediol dimethacrylate (UBDM) monomer was synthesized as a cross-linker into the methacrylate hybrimer networks without micro-phase separation. The UBDM increased methacrylate conversion and mechanical properties due to the hydrogen bonding of the urethane linkage. The hardness, modulus, and strength were improved by UBDM insertion, the flexibility was even increased with 140% elongation, compared to neat MH. In addition, a storage modulus related to the thermo-mechanical properties was also enhanced by a denser cross-linkage with the urethane linkage.

12. Influence of Reaction Conditions on Polymer Morphology in Fused Silica Capillaries

Hydrophobic poly-(benzyl methacrylate-co-1,4 butanediol dimethacrylate) (pBMA) microtubes have been produced through in situ polymerization inside fused silica capillaries. Solvent polarity, reaction temperature and the number of successive polymerization reactions were varied in order to investigate their effect on microtube morphology. It was determined that altering the reaction temperature and solvent polarity enabled control over the degree of tubular morphology, such that the pBMA tubes became more tubular at lower temperatures and in more polar solvents. The thickness of the pBMA tubes increased through multiple successive polymerization reactions. It was determined that pBMA microtube thickness and degree of tubular morphology were controllable, which enables alteration of pBMA tube morphology to optimize their performance in a variety of microscale applications.

Toward replacement of styrene by bio-based methacrylates in unsaturated polyester resins

Several potentially bio-based methacrylate derivatives, namely (with mol.% of bio-based carbon), butanediol dimethacrylate (BDDMA) (33%), isobornyl methacrylate (IBOMA) (71%), lauryl methacrylate (LMA) (75%) have been evaluated as alternatives to styrene as reactive diluent of unsaturated polyester (UPR). First the compatibility of these compounds with SMC/BMC processes has been studied in terms of volatility, miscibility with UPR and viscosity. Based on these preliminary experiments, butanediol dimethacrylate (BDDMA) was selected as sole reactive diluent. The thermo-mechanical and mechanical properties of the resulting network were found to be very different from the ones of a UPR/MMA network prepared as a reference. Consequently, mixtures constituted of BDDMA and one monomethacrylate derivative (MMA, IBOMA and LMA) were then used as reactive diluents to yield networks owning a large range of mechanical behaviours.

Synthesis and characterization of novel vinylester prepolymers from cardanol

A novel thermosetting vinylester (VE) resin was prepared form cardanol, coming from cashew nut shell liquid (CNSL), a renewable resource and waste of the cashew industry. A VE cardanol‐based prepolymer was synthesized by reacting commercial cardanol diepoxy and methacrylic acid. The VE cardanol‐based prepolymer was polymerized by free radical polymerization to yield a thermoset resin with different monomers used as reactive diluents such as styrene (ST), isobornyl methacrylate (IBOMA), dibutyl itaconate (DBI), butanediol dimethacrylate (BDDMA), and hexanediol dimethacrylate (HDDMA). The resulting VE resin was characterized by TGA, DSC, and DMA analyses and compared to diglycidyl ether of bisphenol A (DGEBA)‐based VE resin. Cardanol‐based VE resins exhibit interesting mechanical and thermal properties for composite materials. The Tg value is 86°C with 40% by mass of ST and 116°C with 40% by mass of IBOMA. Around 70°C of Tg are lost compared to DGEBA‐based VE resin, whereas with an oil‐based VE resin the loss of Tg value is around 150°C.Practical application: The acrylated cardanol‐based monomer described in this contribution, that is, acrylated cardanol from CNSL, provided new biobased aromatic building blocks for further free radical polymerizations with various reactive diluents. The obtained VE materials are partially biobased and may be used as binders in composite applications.Biobased vinylester prepolymer (VE) was synthesized by acrylation of commercial di‐epoxy cardanol (Cardolite NC514), coming from CNSL. Vinylester materials were synthesized by free radical polymerization of VE with various monomers. Mechanical and thermal properties of obtained materials showed that synthesized vinylester material could lead to binders for composite application.

Butyl methacrylate based monoliths with different cross‐linking agents using DMF‐aqueous buffer as porogen

A simple porogen containing only DMF and aqueous buffer was used for synthesis of monolithic stationary media for CEC). Butyl methacrylate (BMA)-based capillary monoliths were obtained using proposed porogen together with acrylic/methacrylic cross-linking agents with different alkyl chain lengths. For this purpose, ethylene glycol dimethacrylate, butanediol dimethacrylate and hexanediol diacrylate (HDDA) were used. The monoliths with better electrochromatographic separation performance were obtained when the acrylic cross-linking agent with the longest alkyl chain length (i.e. HDDA) was used with the proposed porogen. The electrochromatographic separation of alkylbenzenes, phenols and benzoic acids were sucessfully performed in CEC particularly using poly(BMA-co-HDDA) monolithic stationary phase with the column efficiency up to 270 000 plates/m.

Behaviors of polyelectrolyte AAm/AMPS/bentonite composite hydrogels in uptake of uranyl ions from aqueous solutions

Uranyl ion (UO22+) sorption properties of polyelectrolyte composite hydrogels made by the polymerization of acrylamide (AAm) with 2-acrylamido-2-methyl-1-propanesulfonic acid (AMPS) and clay such as bentonite (Bent) were investigated as a function of composition to find materials with swelling and uranyl ion sorption properties. Highly swollen AAm/AMPS hydrogels and AAm/AMPS/Bent composite hydrogels were prepared by free radical solution polymerization in aqueous solutions of AAm with AMPS as co-monomer and two multifunctional crosslinkers such as ethylene glycol dimethacrylate (EGDMA) and 1,4 butanediol dimethacrylate (BDMA). Swelling experiments were performed in water at 25°C, gravimetrically. The influence of AMPS content in hydrogels was examined. Uranyl ion adsorption from aqueous solutions was studied by batch sorption technique at 25°C. The effect of uranyl ion concentration and mass of AMPS on the uranyl ion adsorption were examined. Finally, adsorption capacity (the amount of sorbed uranyl ion per gram of dry hydrogel) (q) was calculated to be 0.67 × 10−3–2.11 × 10−3 mol uranyl ion per gram for the hydrogels. Removal effiency of uranyl ions (RE%) was changed range 9.05–29.92%. The values of partition ratio (Kd) of uranyl ions was calculated to be 0.10–0.43 for AAm/AMPS hydrogels and AAm/AMPS/Bent composite hydrogels, respectively. POLYM. COMPOS., 2011. © 2011 Society of Plastics Engineers

Equilibrium Swelling Studies of Highly Swollen Acrylamide/Thiosinamine Hydrogels

Highly swollen water absorbent copolymers on acrylamide (AAm) and thiosinamine (ThA) have been studied as a function of copolymer composition. AAm/ThA hydrogels were prepared by free radical solution polymerization in aqueous solution of AAm with ThA as hydrophilic comonomer and two multifunctional crosslinkers such as 1,4 butanediol dimethacrylate (BDMA) and trimethylolpropane triacrylate (TMPTA). Swelling experiments were performed in water at 25°C, gravimetrically. The influence of ThA content in hydrogels was examined. Swelling of AAm/ThA hydrogels was increased up to 2156% (for containing 20 mg ThA and crosslinked by TMPTA) and 3139% (for containing 20 mg ThA and crosslinked by BDMA), while AAm hydrogels swelled up to 1155% (crosslinked by TMPTA) − 1417% (crosslinked by BDMA). The values of equilibrium water content of the hydrogels are 0.9203-0.9691. Diffusion behavior was investigated. Water diffusion into hydrogels was found to be non-Fickian in character.

Behaviors of Chemically Crosslinked CAAMPS Hydrogels in Uptake of Uranyl Ions from Aqueous Solutions

Uranyl ion adsorption from aqueous solutions has been investigated by chemically crosslinked (C) polyelectrolyte acrylamide/2-acrylamido-2-methyl-1-propanesulfonic acid (CAAMPS) hydrogels. CAAMPS hydrogels with various compositions were prepared from ternary mixtures of acrylamide (A), 2-acrylamido-2-methyl-1-propanesulfonic acid (AMPS), and water by free radical polymerization in an aqueous solution using multifunctional crosslinkers such as ethylene glycol dimethacrylate (EGDMA) and 1,4 butanediol dimethacrylate (BDMA). The swelling equilibrium of polyelectrolyte copolymer gels containing of CAAMPS hydrogels has been studied as a function of copolymer composition. Swelling experiments were performed in water at 25°C, gravimetrically. The influence of AMPS content in hydrogels was examined. The weight-swelling ratio of CAAMPS hydrogels was increased up to 127.03 (for 300 mg AMPS and crosslinked by EGDMA) and 93.32 (for 300 mg AMPS and crosslinked by BDMA), while acrylamide hydrogels swelled up to 10.27 (crosslinked by EGDMA) and 10.06 (crosslinked by BDMA). Uranyl ion adsorption from aqueous solutions was studied by batch sorption technique at 25°C. The effect of uranyl ion concentration and mass of AMPS on the uranyl ion adsorption were examined. In the experiments of the sorption, L type sorption in the Giles classification system was found. Finally, the amount of sorbed uranyl ion per gram of dry hydrogel (q) was calculated to be 0.67 × 10−3–2.11 × 10−3 mol uranyl ion per gram for CAAMPS hydrogels. Removal effiency of uranyl ions (RE%) was changed range 9.05–29.92%. The values of partition ratio, (K d ) of uranyl ions was calculated to be 0.10–0.43 for CAAMPS hydrogels.

Swelling characterization of novel ternary semi‐IPNs: acrylamide/1‐vinylimidazole/PEG hydrogels

AbstractNew ternary semi interpenetrating polymer networks (semi‐IPNs) systems containing acrylamide (AAm), 1‐vinylimidazole (VI) and poly (ethylene glycol) (PEG) have been prepared. AAm/VI hydrogels and semi‐IPN's, poly (AAm/VI/PEG) with 0.25, 0.50, 0.75 and 1.00 g of PEG (per 1.00 g AAm) were prepared by free radical solution polymerization in aqueous solution of AAm with VI as comonomer and a multifunctional crosslinker such as 1,4 butanediol dimethacrylate (BDMA). Swelling experiments were performed in water at 25°C, gravimetrically. The influence of VI and PEG content in hydrogels were examined. AAm/VI and AAm/VI/PEG hydrogels showed large extents of swelling in aqueous media, the swelling being highly dependent on the chemical composition of the hydrogels. Percentage swelling ratio of AAm/VI hydrogels and AAm/VI/PEG hydrogels was shown as 650–4167%. The values of equilibrium water content (EWC) of the hydrogels are between 0.8990 and 0.9750. Diffusion behavior was investigated. Water diffusion into hydrogels was found to be non‐Fickian in character. Copyright © 2007 John Wiley & Sons, Ltd.

Uptake of Basic Blue 17 from aqueous solutions by using chemically crosslinked polyelectrolyte AAm/AASS hydrogels

In this study, the removal of a cationic thiazin dye such as Basic Blue 17 (Toluidin Blue, BB 17) by chemically crosslinked acrylamide (AAm)/acrylic acid sodium salt (AASS) hydrogels was investigated. Super water retainer AAm/AASS hydrogels with various compositions were prepared from ternary mixtures of AAm, AASS and water by free radical polymerization in aqueous solution using multifunctional crosslinkers such as ethylene glycol dimethacrylate (EGDMA), N,N′ methylenebisacrylamide (NMBA), 1,4 butanediol dimethacrylate (BDMA) and trimethylolpropane triacrylate (TMPTA). Adsorption of Basic Blue 17 from aqueous solutions was studied by batch sorption technique at 25∘C. The effect of Basic Blue 17 concentration and mass of adsorbent on the dye adsorption were examined.

Isobornyl Methacrylate as a Reactive Solvent of Polyethylene

Solutions containing 15 wt, -% of a low-molar-mass polyethylene (PE) in isobornyl methacrylate (IBoMA), containing 0, 5 or 10 wt.-% of 1,4 butanediol dimethacrylate (BDDMA) as crosslinker, were polymerized using either benzoyl peroxide (BPO), at 80°C, or dicumyl peroxide (DCPO), with a thermal cycle attaining 150°C, as initiators. Phase separation of an amorphous PE-rich phase took place when carrying out the reaction at temperatures higher than the PE melting temperature. Partial crystallization of PE was observed when cooling to room temperature. Depending on the initial amount of BDDMA, the fraction of PE that was phase separated varied between 57 and 66% of the initial amount, with crystalline fractions in the range of 15 to 42 %. The use of IBoMA as a reactive solvent of PE has two main advantages over other reactive solvents reported in the literature: a) it has a very low vapor pressure, and b) its free-radical polymerization gives a polymer with a relatively high glass transition temperature.

Preparation of protected peptides by gel-phase synthesis on butanediol dimethacrylate cross-linked polystyrene support

Abstract: Preparation of fully protected peptide C-terminal esters in high yield and purity by making use of gel-phase synthesis on chloromethyl butanediol dimethacrylate (BDODMA) crosslinked polystyrene is described. The C-terminal amino acid of the peptide was incorporated by cesium salt method and the step-wise synthesis was carried out using HOBt active ester coupling procedure. The protected peptides were cleaved from the support by trans-esterification. The crude peptides were purified by HPLC and characterized by amino acid analysis, tic and MALDI TOF MS.

Optimization of butanediol dimethacrylate crosslinked polystyrene: A novel polymeric support for solid phase peptide synthesis

Studies leading to optimization of butanediol dimethacrylate-crosslinked polystyrene supports (BDDMA-PS) for solid phase peptide synthesis are delineated. BDDMA-PS copolymers with different crosslink densities were prepared and functionalised with chloromethyl groups. The reactivity of the Lys(2-Cl−Z)−OH residue bound to these polymers through a benzyl ester linkage was investigated by following the kinetics of acylation by the HOBt active ester of Boc-Alanine. From the results it was observed that the rate of peptide bond formation was maximum for a 2% BDDMA crosslinked resin. This resin was compared with a 2% DVB-crosslinked polystyrene resin (DVB-PS). Synthesis of an extremely insoluble, hydrophobic, antiparallel β-sheeted difficult sequence peptide LMVGGVVIA (β 34–42), C-terminal fragment of β-amyloid protein, β (1–42), was carried out on both 2% DVB-PS and 2% BDDMA-crosslinked polystyrene supports. The synthesis of the peptide was carried out using Boc amino acid strategy. Greater extent of swelling of the resino peptide, increased coupling efficiency during the assembly of amino acids and relatively high purity of synthesised peptide were observed in the case of 2% BDDMA-PS polymer.

Synthesis, Characterization, and Application of Butanediol Dimethacrylate Cross-Linked Polystyrene: A Flexible Support for Gel Phase Peptide Synthesis

We have developed a new cross-linked polymeric support by the copolymerization of styrene and butanediol dimethacrylate (BDODMA) for the solid-phase synthesis of peptides. The resin support was synthesized in various cross-linking densities by radical aqueous suspension polymerization. The copolymer was characterized by IR and 13C NMR techniques. The shape, size, and morphological features of the cross-linked polymer bead were analyzed by scanning electron microscopy. PS-BDODMA polymer support showed excellent swelling properties in all types of solvents that are used in solid-phase peptide synthesis (SPPS). The stability of polymer in various reagents and solvents was tested by IR. The polymer does not show any change in its IR spectrum even after 48 h treatment with TFA, 20% piperidine in DMF, aqueous NaOH, hydroxylamine in aqueous MeOH, and liquor ammonia. The resin can be functionalized with chloromethyl, aminomethyl, and hydroxymethyl groups under various reaction conditions. The efficiency of this new support was demonstrated by the synthesis of few model peptides with very high purity and yield. These peptides were characterized by MALDI TOF MS and amino acid analysis.

Synthesis and metal binding behavior of hydroxamic acid resins from poly(ethyl acrylate) crosslinked with divinylbenzene and hydrophilic crosslinking agent

AbstractPorous poly(hydroxamic acid) chelating resin was prepared by the reaction with poly(ethyl acrylate) crosslinked with divinylbenzene and hydrophilic crosslinking agent, and hydroxylamine. The hydrophilic crosslinking agents and diluent used in this article were ethylene glycol dimethacrylate or butanediol dimethacrylate, and 2,2,4‐trimethyl pentane, respectively. The characterization of this type chelating resin was carried out by IR spectroscopy, density measurement, and scanning electron microscopy. Various metal binding properties such as extraction, kinetics, and selectivity were investigated with atomic absorption spectrometer and inductively coupled plasma spectrometer. Poly(hydroxamic acid) resins crosslinked with mixed crosslinking agents showed better metal extraction properties and faster adsorption rate than those crosslinked with divinylbenzene alone. And alkali treatment enhances the binding rate for metal ions because of the formation of other chelating ligands or micropores. © 1995 John Wiley & Sons, Inc.

Encapsulation of benzil in the cavities of crosslinked styrene‐based copolymers and its conversion to benzilic acid

AbstractCrosslinking copolymerization of styrene with divinylbenzene, butanediol dimethacrylate and ethyleneglycol dimethacrylate in the presence of benzil in the dissolved state results in benzil‐encapsulated crosslinked polymers. Resins with various crosslink densities were prepared by adjusting the monomer/crosslinker ratio. The benzil entrapped in the cavities was subjected to benzil‐benzilic acid rearrangement. The precursor resins and the rearrangement products were characterized by IR and 13C NMR spectroscopy. The surface properties of polystyrene and benzil‐encapsulated polystyrene were compared by scanning electron micrography.

Properties of poly(2-hydroxyethyl acrylate) networks

Hydrogels, based on poly(2-hydroxyethyl acrylate) cross-linked with 1,4 butanediol dimethacrylate, were studied in respect to their swelling and mechanical behaviour. The determination of Young's modulus at r.t. permitted the calculation of average molecular weight between cross-links. This value could, in turn, be correlated with water-swelling data to give indicative values of the interaction parameter for the system poly(2-hydroxyethyl acrylate)-water.