Photopolymerization studies of alkyl and aryl ester derivatives of ethyl α‐hydroxymethylacrylate

Avcı, Duygu; Mathias, Lon J.; Thigpen, Kevin

doi:10.1002/(sici)1099-0518(19961115)34:15<3191::aid-pola9>3.3.co;2-h

Cited by 10 publications

(15 citation statements)

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“…The photo‐DSC plots of this monomer showed a shoulder on the initial peak indicating autoacceleration due to diffusion‐controlled termination. Similar behavior was observed for the ester derivatives of alkyl α‐hydroxymethyl acrylates giving high molecular weight polymers 38. Previously, the relative reactivities of the various ester derivatives in photopolymerizations were compared, and aromatic ester derivatives were found to be more reactive than nonaromatic ester derivatives, with all ester derivatives being faster than free alcohol.…”

Section: Resultssupporting

confidence: 64%

Synthesis and copolymerization of new phosphorus‐containing acrylates

Avcı

Albayrak

2003

J. Polym. Sci. A Polym. Chem.

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Two phosphorus-containing acrylate monomers were synthesized from the reaction of ethyl ␣-chloromethyl acrylate and t-butyl ␣-bromomethyl acrylate with triethyl phosphite. The selective hydrolysis of the ethyl ester monomer with trimethylsilyl bromide (TMSBr) gave a phosphonic acid monomer. The attempted bulk polymerizations of the monomers at 57-60°C with 2,2Ј-azobisisobutyronitrile (AIBN) were unsuccessful; however, the monomers were copolymerized with methyl methacrylate (MMA) in bulk at 60°C with AIBN. The resulting copolymers produced chars on burning, showing potential as flame-retardant materials. Additionally, ␣-(chloromethyl)acryloyl chloride (CMAC) was reacted with diethyl (hydroxymethyl)phosphonate to obtain a new monomer with identical ester and ether moieties. This monomer was hydrolyzed with TMSBr, homopolymerized, and copolymerized with MMA. The thermal stabilities of the copolymers increased with increasing amounts of the phosphonate monomer in the copolymers. A new route to highly reactive phosphorus-containing acrylate monomers was developed. A new derivative of CMAC with mixed ester and ether groups was synthesized by substitution, first with diethyl (hydroxymethyl)phosphonate and then with sodium acetate. This monomer showed the highest reactivity and gave a crosslinked polymer. The incorporation of an ester group increased the rate of polymerization. The relative reactivities of the synthesized monomers in photopolymerizations were determined and compared with those of the other phosphorouscontaining acrylate monomers. Changing the monomer structure allowed control of the polymerization reactivity so that new phosphorus-containing polymers with desirable properties could be obtained.

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Section: Resultssupporting

confidence: 64%

Synthesis and copolymerization of new phosphorus‐containing acrylates

Avcı

Albayrak

2003

J. Polym. Sci. A Polym. Chem.

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“…In this study, we focused on assessing the effect of substituting ethyl α-hydroxymethylacryate (EHMA), unique isomer of HEMA ( Fig. 1, [9,10]), for HEMA in Bis-GMA and in Bis-GMA/ TEGDMA resins. Hypothetically, compared to HEMA-containing resins, EHMA-containing resins should exhibit considerably more intra-molecular than inter-molecular hydrogen bonding and are, thus, expected to have lower water solubility.…”

Section: Introductionmentioning

confidence: 99%

Effect of ethyl-α-hydroxymethylacrylate on selected properties of copolymers and ACP resin composites

Antonucci

Fowler

Weir

et al. 2008

J Mater Sci: Mater Med

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There is an increased interest in the development of bioactive polymeric dental composites and related materials that have potential for mineralized tissue regeneration and preservation. This study explores how the substitution of ethyl alpha-hydroxymethylacryate (EHMA) for 2-hydroxyethyl methacrylate (HEMA) in photo-activated 2,2-bis[p-(2'-hydroxy-3'-methacryloxypropoxy)phenyl]propane (Bis-GMA) and Bis-GMA/tri(ethylene glycol) dimethacrylate (TEGDMA) resins affected selected physicochemical properties of the polymers and their amorphous calcium phosphate (ACP) composites. Rate of polymerization and the degree of conversion (DC) of polymers {EHMA (E), HEMA (H), Bis-GMA/EHMA (BE), Bis-GMA/HEMA (BH), Bis-GMA/TEGDMA/EHMA (BTE) and Bis-GMA/TEGDMA/HEMA (BTH)} were assessed by photo-differential scanning calorimetry and Fourier-Transform Infrared (FTIR) spectroscopy. ACP/BTE and ACP/BTH composites were evaluated for DC, biaxial flexure strength (BFS), water sorption (WS) and mineral ion release. Mid-FTIR and near-IR measurements revealed the following order of decreasing DC: [E, H polymers (97.0%)] > [BE copolymer (89.9%)] > [BH copolymer (86.2%)] > [BTE, BTH copolymers (85.5%)] > [ACP/BTH composite (82.6%)] > [ACP/BTE composite (79.3%)]. Compared to HEMA, EHMA did not adversely affect the BFS of its copolymers and/or ACP composites. Lower WS of BTE copolymers and composites (28% and 14%, respectively, compared to the BTH copolymers and composites) only marginal reduced the ion release from ACP/BTE composites compared to ACP/BTH composites. More hydrophobic ACP composites with acceptable ion-releasing properties were developed by substituting the less hydrophilic EHMA for HEMA.

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“…For example, various benzoate ester derivatives of ethyl a-hydroxymethylacrylate (EHMA) were synthesized and found to display unexpectedly rapid photopolymerizations [23]. In a previous article, we evaluated the influence of long-chain flexible linking units between double bonds of diacrylates and dimethacrylates on the rates of polymerization of materials based on RHMAs, hydroxyethyl acrylate (HEA) and hydroxyethylmethacrylate (HEMA) monomers [24].…”

Section: Introductionmentioning

confidence: 99%