Synthesis and characterization of novel fluorine‐containing methacrylate copolymers: Reactivity ratios,thermal properties,and antimicrobial activity

The free‐radical‐initiated copolymerization of 2‐(4‐acetylphenoxy)‐2‐oxoethyl‐2‐methylacrylate (AOEMA) and 2‐(4‐benzoylphenoxy)‐2‐oxoethyl‐2‐methylacrylate (BOEMA) with 2‐[(4‐fluorophenyoxy]‐2‐oxoethyl‐2‐methylacrylate (FPEMA) were carried out in 1,4‐dioxane solution at 65°C using 2,2′‐azobisisobutyronitrile as an initiator with different monomer‐to‐monomer ratios in the feed. The monomers and copolymers were characterized by FTIR and ¹H‐ and ¹³C‐NMR spectral studies. ¹H‐NMR analysis was used to determine the molar fractions of AOEMA, BOEMA, and FPEMA in the copolymers. The reactivity ratios of the monomers were determined by the application of Fineman‐Ross and Kelen‐Tudos methods. The analysis of reactivity ratios revealed that BOEMA and AOEMA are less reactive than FPEMA, and copolymers formed are statistically in nature. The molecular weights (M _w and M _n) and polydispersity index of the polymers were determined using gel permeation chromatography. Thermogravimetric analysis of the polymers reveals that the thermal stability of the copolymers increases with an increase in the mole fraction of FPEMA in the copolymers. Glass transition temperatures of the copolymers were found to decrease with an increase in the mole fraction of FPEMA in the copolymers. © 2009 Wiley Periodicals, Inc. J Appl Polym Sci, 2009     

Using 1H‐NMR spectroscopy for the kinetic study of the in situ solution free‐radical copolymerization of styrene and ethyl acrylate

The free‐radical copolymerization of styrene and ethyl acrylate in benzene‐d₆ as the solvent in the presence of benzoyl peroxide as an initiator at 70°C was studied by online ¹H‐NMR spectroscopy. The chemical composition of the copolymer at different reaction times was calculated from the conversion of the monomers to the copolymer, and then the reactivity ratios of styrene and ethyl acrylate were determined at both low and high conversions. Data for the overall monomer conversion versus the time were used to estimate the ratio k_pk_t^?0.5 for different compositions of the initial feed (k_p is the propagation rate constant, and k_t is the termination rate constant). k_pk increased with an increasing molar fraction of ethyl acrylate in the initial feed. The monomer mixture and copolymer compositions versus the overall monomer conversion were calculated with the data of ¹H‐NMR spectra. The incorporation of the styrene monomer into the copolymer structure was more favored than that of the ethyl acrylate monomer. Reducing the molar fraction of styrene in the initial feed intensified this. Drawing the molar fraction of styrene (or ethyl acrylate) in the copolymer chains versus that in the initial feed showed a tendency of the system toward random copolymerization. © 2007 Wiley Periodicals, Inc. J Appl Polym Sci, 2007     

Nitroxide‐terminated poly(styrene‐co‐diethyl fumarates) and derived block copolymers

Copolymerization of styrene (S) and diethyl fumarate (DEF) at 125°C in the presence of 2,2,6,6‐ tetramethylpiperidin‐1‐yloxyl radical (TEMPO) and initiated with a thermal initiator, 2,2′‐azobisisobutyronitrile (AIBN), was studied. The molar fraction of DEF in the feed, F_DEF, varied within 0.1–0.9. An azeotropic composition, (F_DEF)_A = 0.38, was found for the copolymerization under study. At F_DEF = 0.1–0.4, a quasi‐living process was observed, transforming to a retarded conventional radical copolymerization at a higher content of DEF in the initial mixtures. The obtained TEMPO‐terminated S‐DEF copolymers were used to initiate polymerization of styrene. Poly(styrene‐ co‐diethyl fumarate)‐block‐polystyrene copolymers were prepared with molecular weight distributions depending on the amount of inactive polymer chains in macroinitiators, as indicated by size‐exclusion chromatography. A limited miscibility of the blocks in the synthesized block copolymers was revealed by using differential scanning calorimetry. © 2002 Wiley Periodicals, Inc. J Appl Polym Sci 84: 2432–2439, 2002     

Synthesis and characterization of alkali‐modified styrene‐maleic anhydride copolymer for dispersion of TiO2

A copolymer of styrene and maleic anhydride was synthesized by free radical polymerization at 80°C using N,N‐dimethylformamide (DMF) as solvent and benzoylperoxide as initiator. The monomer feed ratio of styrene to maleic anhydride was varied in the range of 1 : 1 : to 3 : 1. The polymer yield was found to decrease with increase in styrene in the feed. The molecular weight of copolymers which were formed by taking styrene to maleic anhydride ratio of 1 : 1, 2 : 1, and 3 : 1, as determined by Ostwald Viscometery were about 1862, 2015, and 2276 respectively. The acid values of abovementioned three copolymers were found to be 480, 357, and 295, respectively. The typical viscosity values of 20% solids in ammonical solution of copolymers formed by taking feed ratios of Sty : MAn as 1 : 1 and 2 : 1 were 26 and 136 cp, respectively. For the feed ratio 3 : 1, a gel was formed. The synthesized copolymers were hydrolyzed by alkalis, namely, NaOH, KOH, and NH₄OH. The dispersing ability of hydrolyzed styrene‐maleic anhydride (SMA) copolymers for dispersion of titanium dioxide was studied. The modified SMA copolymers were found to be effective dispersants for TiO₂. Among the three alkalis studied, the Sodium salts of SMA were found to give better dispersion. The copolymer having a 1 : 1 feed ratio showed the best dispersing ability for TiO₂ particles among the three ratios studied. © 2006 Wiley Periodicals, Inc. J Appl Polym Sci 103: 3194–3205, 2007     

Investigation of styrene/1‐hexene copolymerization by homogeneous and heterogeneous bisindenyl ethane zirconium dichloride catalyst system

Homogeneous copolymerization of styrene and 1‐hexene was carried out in toluene at room temperature using bisindenyl ethane zirconium dichloride/methylaluminoxane (MAO). The supported catalyst was prepared with immobilization of Et(Ind)₂ZrCl₂/MAO on silica (calcinated at 500°C) with premixed method. Heterogeneous copolymerization of styrene/1‐hexene with different mole ratios was carried out in the presence of supported catalyst system. The copolymers obtained from homogeneous and heterogeneous catalyst system were characterized by ¹H NMR and ¹³C NMR. Composition of the resulting copolymers was determined by ¹H NMR data. Analysis of ¹³C NMR spectra of obtained copolymers by homogeneous and heterogeneous catalyst systems present isotactic olefin‐enriched copolymers. Molecular weight and thermal behavior of resulting copolymers was investigated. © 2007 Wiley Periodicals, Inc. J Appl Polym Sci 104: 4008–4014, 2007     

Synthesis of well‐defined comb‐like amphiphilic copolymers with protonizable units in the pendent chains: 1. Preparation of narrow polydispersity copolymers of methyl methacrylate and 2‐hydroxyethyl methacrylate by atom‐transfer radical polymerization

Well‐defined methyl methacrylate (MMA) and 2‐(trimethylsiloxy)ethyl methacrylate (Pro‐HEMA) copolymers were prepared by atom‐transfer radical polymerization(ATRP), using CuCl/2,2′‐bipyridine as catalytic system and p‐toluenesulfonyl chloride as initiator. ATRP process of MMA and Pro‐HEMA was monitored by ¹H NMR, and the kinetic curves of the MMA/Pro‐HEMA copolymerization were plotted in terms of the ¹H NMR data. At low content of Pro‐HEMA in the feed composition, the copolymerization can be well controlled with the molecular weight, polydispersity and the monomer distribution in the copolymer chain. With the increase of Pro‐HEMA content in the feed mixture, the composition of the final copolymer deviates from the composition of the feed mixture gradually, and gradient copolymers of MMA/Pro‐HEMA can be obtained. Through the hydrolysis process, well‐defined copolymers of MMA/HEMA were obtained from poly(MMA/Pro‐HEMA). Copyright © 2003 Society of Chemical Industry     

Copolymerization of styrene with an α‐olefin via atom transfer radical polymerization

This investigation reports the preparation of styrene–α‐olefinic random copolymers, using 1‐octene as an α‐olefin, via atom transfer radical polymerization. Atom transfer radical copolymerization of styrene with 1‐octene was successfully carried out using phenylethyl bromide as initiator and CuBr as catalyst in combination with N, N, N′, N″, N″‐pentamethyldiethylenetriamine as ligand. The copolymers had controlled molecular weight, narrow dispersity and well‐defined end groups with significant 1‐octene incorporation in the polymer. Incorporation of 1‐octene in the copolymers was confirmed using ¹H NMR and matrix‐assisted laser desorption ionization time‐of‐flight mass spectroscopy. An increase in 1‐octene content in the monomer feed led to an increase in the level of incorporation of the α‐olefin in the copolymer. An increase in the concentration of 1‐octene led to a decrease in the rate of polymerization and an increase in dispersity. The glass transition temperature of the copolymer gradually decreased as the incorporation of 1‐octene increased. Copyright © 2011 Society of Chemical Industry     

Binary copolymerization of 4‐methyl‐1,3‐pentadiene with styrene,butadiene and isoprene catalysed by a titanium [OSSO]‐type catalyst

Binary copolymerization of 4‐methyl‐1,3‐pentadiene (4MPD) with styrene, butadiene and isoprene promoted by the titanium complex dichloro{1,4‐dithiabutanediyl‐2,2′‐bis[4,6‐bis(2‐phenyl‐2‐propyl)phenoxy]}titanium activated by methylaluminoxane is reported. All the copolymers are obtained in a wide range of composition and the molecular weight distributions obtained from gel permeation chromatographic analysis of the copolymers are coherent with the materials being copolymeric in nature. The copolymer microstructure was fully elucidated by means of ¹H NMR and ¹³C NMR spectroscopy. Differential scanning calorimetry shows an increase of glass transition temperature (T_g) with the amount of 4MPD in the copolymers with butadiene and isoprene, while in the copolymers with styrene T_g is increased on increasing the amount of styrene. © 2016 Society of Chemical Industry     

Synthesis and chain extension of nitroxide‐terminated styrene–maleimide copolymers

Thermal radical copolymerization of styrene (S) and maleimide (MI) at 125°C in diglyme in the presence of 2,2,6,6‐tetramethylpiperidin‐1‐yloxyl radical (TEMPO) was studied. Mole fractions of maleimide in the feed, F_MI, varied in the range 0.1–0.9. A quasiliving reaction process proceeded yielding copolymers with a low polydispersity (M_w/M_n = 1.17–1.41). The found azeotropic composition, (F_MI)_A = 0.46, did not differ substantially from that (0.5) in the conventional radical S‐MI copolymerization. At a higher conversion or MI content in the feed, deactivation of the copolymer chains occurred. The obtained TEMPO‐terminated S‐MI copolymers readily initiated polymerization of styrene; chain extension of the macroinitiators took place, giving poly(S‐co‐MI)‐block‐poly(S) diblock copolymers. The synthesized copolymers containing S and MI units were characterized by elemental analysis, NMR spectroscopy, size‐exclusion chromatography, and differential scanning calorimetry. © 2004 Wiley Periodicals, Inc. J Appl Polym Sci 92: 1863–1868, 2004     

Copolymerization of n‐butylacrylate with styrene by a novel photoinitiator, 1‐(bromoacetyl)pyrene

A comparative study on photoinitiated solution copolymerization of n‐butylacrylate (BA) with styrene (Sty) using pyrene (Py), 1‐acetylpyrene (AP), and 1‐(bromoacetyl)pyrene (BP) as initiators showed that the introduction of a chromophoric moiety, bromoacetyl (? COCH₂Br), significantly increased the photoinitiating ability of pyrene. The kinetics and mechanism of copolymerization of BA with Sty using BP as photoinitiator have been studied in detail. The system follows nonideal kinetics (R_p ∝ [BP]^0.34 [BA]^1.07 [Sty]^0.97). The nonideality was attributed to both primary radical termination and degradative initiator transfer. The monomer reactivity ratios of Sty and BA have been estimated by the Finemann–Ross and Kelen–Tudos methods, by analyzing copolymer compositions determined by ¹H NMR spectra. The values of r₁ (Sty) and r₂ (BA) were found to be 0.78 and 0.25, respectively, which suggested the high concentration of alternating sequences in the random copolymers obtained. © 2006 Wiley Periodicals, Inc. J Appl Polym Sci 102: 3233–3239, 2006     

Hyperbranched copolymers of p‐(chloromethyl)styrene and N‐cyclohexylmaleimide synthesized by atom transfer radical polymerization

The hyperbranched copolymers were obtained by the atom transfer radical copolymerization of p‐(chloromethyl)styrene (CMS) with N‐cyclohexylmaleimide (NCMI) catalyzed by CuCl/2,2′‐bipyridine (bpy) in cyclohexanone (C₆H₁₀O) or anisole (PhOCH₃) with CMS as the inimer. The influences of several factors, such as temperature, solvent, the concentration of CuCl and bpy, and monomer ratio, on the copolymerization were subsequently investigated. The apparent enthalpy of activation for the overall copolymerization was measured to be 37.2 kJ/mol. The fractional orders obtained in the copolymerization were approximately 0.843 and 0.447 for [CuCl]₀ and [bpy]₀, respectively. The monomer reactivity ratios were evaluated to be r_NCMI = 0.107 and r_CMS = 0.136. The glass transition temperature of the resultant hyperbranched copolymer increases with increasing f_NCMI, which indicates that the heat resistance of the copolymer has been improved by increasing NCMI. The prepared hyperbranched CMS/NCMI copolymers were used as macroinitiators for the solution polymerization of styrene to yield star‐shaped poly(CMS‐co‐NCMI)/polystyrene block copolymers by atom transfer radical polymerization. © 2000 John Wiley & Sons, Inc. J Appl Polym Sci 78: 1992–1997, 2000     

Synthesis,characterizations and thermal behavior of methyl methacrylate and N‐(p‐carboxyphenyl) methacrylamide/acrylamide copolymers

The synthesis, characterization, and thermal properties of copolymers of methyl methacrylate (MMA) and N‐(p‐carboxyphenyl) methacrylamide/acrylamide (CPMA/CPA) are described. The copolymerization was carried out in solution by taking different mole fractions (0.1–0.5) of CPMA/CPA in the initial feed using azobisisobutyronitrile as an initiator and dimethylformamide as a solvent at 60°C. The copolymer composition was determined from ¹H‐NMR spectra by taking the ratio of the proton resonance signal due to the  OCH₃ of MMA (δ = 3.59 ppm) and the aromatic protons (δ = 7.6–7.8 ppm) of CPMA/CPA. The monomer reactivity ratios of MMA:CPMA and MMA:CPA were determined using the Fineman Ross and Kelen Tudos methods and were found to be 1.32 ± 0.01 [MMA], 1.11 ± 0.02 [CPMA], 2.60 ± 0.01 [MMA], and 0.20 ± 0.01 [CPA]. Incorporation of these comonomers in the MMA backbone resulted in an improvement in the glass‐transition temperature and thermal stability. The percent char also increased with the increase of CPMA/CPA content in the copolymers. © 2000 John Wiley & Sons, Inc. J Appl Polym Sci 78: 259–267, 2000     

Novel synthesis of branched polystyrenes by quasi‐living radical copolymerization using photofunctional inimer

Branched polystyrenes were prepared by quasi‐living radical copolymerization of N,N‐diethylaminodithiocarbamoylmethylstyrene (inimer: DTCS) with styrene under UV irradiation. DTCS monomers play an important role in this copolymerization system as an inimer capable of initiating living radical polymerization of the vinyl group. Two monomers (DTCS and styrene) showed equal reactivity toward both propagating species, and the copolymer composition was the same as the comonomer feed. This result means that both the branching and chain length of the hyperbranched molecules can be controlled statistically by the feed monomer ratios. The compact nature of the branched macromolecules is demonstrated by viscosity measurements compared to the linear analogues. © 2001 Society of Chemical Industry     

Radiation polymerization of acrylonitrile in a viscous system with styrene

Radiation polymerization of acrylonitrile in a viscous system with styrene was performed at ambient temperature by using γ‐rays. It is found that the overall rate of polymerization was accelerated after critical conversion due to the gel effect. As the molar fraction of styrene in monomer feed (f_St) is increased, both the total polymer conversion and molar fraction of acrylonitrile in the copolymer feed (F_AN) were decreased. The monomer reactivity ratios for acrylonitrile and styerne were determined to be r₁ (AN) = 0.25 and r₂ (St) = 2.0, respectively. The copolymers obtained were characterized by Fourier transformed infrared spectra (FTIR), X‐ray diffraction (XRD), scanning electron microscopy (SEM), ¹H‐NMR, and pyrolysis mass spectrometry (PMS). It was found that the slight addition of styrene to acrylonitrile strongly changes crystallinity, morphology, and thermal decomposition of the resulting polymer. ¹H‐NMR measurment of AN/St copolymer showed the appearance of aromatic proton signals and shifted the resonance of the methylene proton to lower chemical shifts. The mass spectra of AN/St copolymers showed fragments of pyrolysates corresponding to oligonitriles with styrene end groups. © 2002 Wiley Periodicals, Inc. J Appl Polym Sci 84: 268–275, 2002; DOI 10.1002/app.10324     

Chiral copolymers of (R)‐N‐(1‐phenylethyl) methacrylamide and 2‐hydroxyethyl methacrylate: copolymerization characteristics and chiroptical properties

The aim of this investigation was the copolymerization of a chiral monomer, (R)‐N‐(1‐phenylethyl) methacrylamide, with an achiral monomer, 2‐hydroxyethyl methacrylate (HEMA). The copolymerization characteristics as well as the chiroptical properties (optical rotation and circular dichroism) and their variation with copolymer composition and temperature are discussed. The copolymers are statistical and enriched in HEMA. The monomer reactivity ratio of the chiral monomer (r₁) is 0.133 whereas that of HEMA (r₂) is 1.042 based on the Kelen–Tudos method. The sequence of consecutive chiral monomer units predominates for a feed composition between 0.5 and 0.9 (mole fraction). On the other hand, the sequence of HEMA is uniform and it predominates for a feed composition of around 0.5 (mole fraction). The chiroptical properties of the copolymers do not vary linearly with the content of chiral units in the copolymers. The optical rotation and circular dichroism attain optimum values above 30–40 mol% of chiral monomer units in the copolymers. However, the circular dichroism of the copolymers varies linearly with the temperature. The chiral monomer being a more bulky structure is less reactive than HEMA. The nonlinear variation of chiroptical properties of the copolymers with the content of chiral units may be due to the secondary interaction in the copolymers associated with the hydrogen bonding involving the amide linkage (CONH) present in the pendant chromophore of the chiral monomer as well as the hydroxyl pendant group of HEMA and also the aromatic π–π interaction. Copyright © 2009 Society of Chemical Industry     

Reactivity ratios and copolymer properties of 2‐(diisopropylamino)ethyl methacrylate with methyl methacrylate and styrene

Free radical copolymerization kinetics of 2‐(diisopropylamino)ethyl methacrylate (DPA) with styrene (ST) or methyl methacrylate (MMA) was investigated and the corresponding copolymers obtained were characterized. Polymerization was performed using tert‐butylperoxy‐2‐ethylhexanoate (0.01 mol dm^?3) as initiator, isothermally (70 °C) to low conversions (<10 wt%) in a wide range of copolymer compositions (10 mol% steps). The reactivity ratios of the monomers were calculated using linear Kelen–Tüd?s (KT) and nonlinear Tidwell–Mortimer (TM) methods. The reactivity ratios for MMA/DPA were found to be r₁ = 0.99 and r₂ = 1.00 (KT), r₁ = 0.99 and r₂ = 1.03 (TM); for the ST/DPA system r₁ = 2.74, r₂ = 0.54 (KT) and r₁ = 2.48, r₂ = 0.49 (TM). It can be concluded that copolymerization of MMA with DPA is ideal while copolymerization of ST with DPA has a small but noticeable tendency for block copolymer building. The probabilities for formations of dyad and triad monomer sequences dependent on monomer compositions were calculated from the obtained reactivity ratios. The molar mass distribution, thermal stability and glass transition temperatures of synthesized copolymers were determined. Hydrophobicity of copolymers depending on the composition was determined using contact angle measurements, decreasing from hydrophobic polystyrene and poly(methyl methacrylate) to hydrophilic DPA. Copolymerization reactivity ratios are crucial for the control of copolymer structural properties and conversion heterogeneity that greatly influence the applications of copolymers as rheology modifiers of lubricating oils or in drug delivery systems. © 2015 Society of Chemical Industry     

Separation of ethylbenzene from C7+‐cut naphtha

A fractional distillation process for separating ethylbenzene (EB) from a feed mixture C7⁺‐cut naphtha, comprising nonaromatics, BTX, EB, styrene, and C8⁺ fraction, was used. Primarily, 29.63 wt % EB in the bottom was obtained. Redistillation of the bottom component produced 63.98 wt % EB in the 2nd cut; finally, this cut was used as a feed to distillation process and 83.21 wt % EB was obtained in distillate, and this feed was used directly for dehydrogenation process to produce styrene monomer. All of the distilled fractions were analyzed by gas chromatography instrument. © 2006 Wiley Periodicals, Inc. J Appl PolymSci 102: 2795–2798, 2006     

Preparation of poly(styrene‐co‐isobornyl methacrylate) beads having controlled glass transition temperature by suspension polymerization

The styrene (St) and isobornyl methacrylate (IBMA) random copolymer beads with controlled glass transition temperature (T_g), in the range of 105–158°C, were successfully prepared by suspension polymerization. The influence of the ratios of IBMA in monomer feeds on the copolymerization yields, the molecular weights and molecular weight distributions of the produced copolymers, the copolymer compositions and the T_gs of these copolymers was investigated systematically. The monomer reactivity ratios were r₁ (St) = 0.57 and r₂ (IBMA) = 0.20 with benzyl peroxide as initiator at 90°C, respectively. As the mass fraction of IBMA in monomer feeds was about 40 wt %, it was observed that the monomer conversion could be up to 90 wt %. The fractions of IBMA unit in copolymers were in the range of 35–40 wt % and T_gs of the corresponding copolymers were in the range of 119.6–128°C while the monomer conversion increased from 0 to greater than 90 wt %. In addition, the effects of other factors, such as the dispersants, polymerization time and the initiator concentration on the copolymerization were also discussed. © 2012 Wiley Periodicals, Inc. J. Appl. Polym. Sci., 2013     

Photocrosslinkable copolymers based on 4‐acryloyloxyphenyl‐3′‐chlorostyryl ketone and methyl methacrylate: synthesis,comonomer reactivity ratios and UV photosensitivity

A new photosensitive acrylate monomer having a pendant chlorocinnamoyl moiety (APCSK) was copolymerized with methyl methacrylate (MMA) in different feed compositions in ethyl acetate solution at 70°C using benzoyl peroxide as a free‐radical initiator. The newly synthesized copolymers were characterized by FTIR, ¹H and ¹³C nuclear magnetic resonance (NMR) spectral techniques, as well as by size‐exclusion chromatography. Their thermal behaviour was assessed by thermogravimetric analysis in air and differential scanning calorimetry under nitrogen atmosphere. The copolymers exhibit no phase separation since there is only one glass transition temperature (T_g) value in the region of copolymer composition studied. The reactivity ratios of the comonomers were calculated by adopting linearization methods such as the Fineman–Ross (F‐R), Kelen–Tudos (K‐T) and extended Kelen–Tudos (ExtK‐T) methods, and by a non‐linear error‐in‐variables model method (EVM) using a computer program (RREVM). The results suggest that MMA is more reactive than APCSK and that their copolymerization leads to the formation of random copolymers. The photosensitivity of the copolymer samples was studied in solution as well as in thin films through UV irradiation. The influence of different factors, including solvent nature, concentration, temperature, photosensitizer and copolymer composition, on the rate of photocrosslinking of the photoreactive copolymers was investigated for effective industrial application of these polymers as negative photoresists. Copyright © 2004 Society of Chemical Industry     

Synthesis and polymerization of a new iodine‐containing monomer

A new iodine‐containing methacrylate monomer, 3,4,5‐triiodobenzoyloxyethyl methacrylate (TIBEM), was synthesized by coupling 2‐hydroxyethyl methacrylate (HEMA) with 3,4,5‐triiodobenzoic acid. The monomer was characterized by ¹H nuclear magnetic resonance, infrared (IR), and ultraviolet spectra. Homopolymerization and copolymerization of the monomer with methyl methacrylate (MMA) were carried out using 2,2′‐azobis isobutyronitrile as the initiator. A terpolymer of TIBEM, MMA, and HEMA was also synthesized. The copolymers were characterized by IR, gel permeation chromatography, differential thermal analysis, and thermogravimetric analysis (TGA). High molecular weight polymers were produced with MMA at different feed compositions of TIBEM. The polymers were found to be freely soluble in common solvents for acrylic polymers. TGA showed little decomposition of the copolymer below 280°C. Copolymers showed good radiopacity at 25 wt % of TIBEM in the feed. These copolymers could find applications in medical and dental areas where radiopacity is a desirable feature of the implants. © 2003 Wiley Periodicals, Inc. J Appl Polym Sci 88: 2580–2584, 2003