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>3.0.co;2-#

Cited by 14 publications

(1 citation statement)

References 24 publications

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“…While efficient, the resulting polymers are limited to acrylate or methacrylate backbones. Mathias et al in 1987 pioneered the synthesis and polymerization of methyl-α-hydroxymethyl acrylate (MHMA), and later studied the polymerization behavior of various ester − and ether , derivatives of MHMA, as well as of higher alkyl α-hydroxymethyl acrylate analogues . Recent studies by Joy et al further explored analogous hydroxymethylation of acrylic monomers in the α-position to increase polymer backbone diversity.…”

Section: Introductionmentioning

confidence: 99%

Charge-Shifting Polycations with Tunable Rates of Hydrolysis: Effect of Backbone Substituents on Poly[2-(dimethylamino)ethyl acrylates]

et al. 2018

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While polycations based on 2-(dimethylamino)ethyl methacrylate and 2-(dimethylamino)ethyl acrylate are used in applications ranging from biomaterials to wastewater treatment, few studies have considered the remarkable differences in the hydrolytic stabilities of the respective ester groups. Here, we describe how the nature of nonmethyl α-substituents affect the rates of ester hydrolysis of such polymers, with an emphasis on the resulting shift of net polymer charge from cationic toward anionic. We introduce 2-(dimethylamino)ethyl 2-hydroxymethyl acrylate (DHMA) as a new, very hydrolytically labile, cationic monomer that can be used to form homopolymers as well as a means to tune copolymer hydrolysis. DHMA synthesis and free radical polymerization are described, including reactivity ratios for hydroxyl-protected derivatives of DHMA and 2-(dimethylamino)ethyl acrylate (DMAEA). Hydrolyses of PDHMA, P[DHMA-co-DMAEA], PDMAEA, and PDMAEMA in pH 5 and 7 buffer are reported. The presence of the hydroxymethyl α-substituent in PDHMA led to rates of hydrolysis 2−3 orders of magnitude faster than the already rapid hydrolysis of PDMAEA. Furthermore, hydrolysis rates of P[DHMA-co-DMAEA] copolymers were shown to increase as the DHMA mole fraction increased. As a result, a new route to adjusting the charge-shifting rates of such polycations in aqueous media is described.

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Section: Introductionmentioning

confidence: 99%

Charge-Shifting Polycations with Tunable Rates of Hydrolysis: Effect of Backbone Substituents on Poly[2-(dimethylamino)ethyl acrylates]

et al. 2018

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Photopolymerized low‐surface‐energy coatings based on a novel fluorinated ether acrylate

Shemper

Mathias

2004

J of Applied Polymer Sci

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ABSTRACT:The synthesis, characterization, and polymerization of a perfluoroalkyl ether substituted methacrylic acid (C8F7) were investigated. C8F7 was photopolymerized at different temperatures, higher double-bond conversions being achieved at higher polymerization temperatures. The polymerization rates were fast in comparison with those of typical methacrylate esters. Thermogravimetric analysis of the obtained polymers showed thermal stabilities up to 270 -290°C. The initial degradation at 200°C involved the loss of water and the partial loss of the perfluoroalcohol via the intramolecular formation of anhydride and lactone groups. The surface properties of coatings obtained with C8F7 coatings on various substrates were evaluated with water and hexadecane contact-angle measurements, which confirmed that low-surface-energy polymeric coatings were obtained.

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Synthesis and characterization of copolymers of bromoacrylated methyl oleate

Eren¹,

Küsefoǧlu²

2004

J of Applied Polymer Sci

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ABSTRACT:In this study, methyl oleate was bromoacrylated in the presence of N-bromosuccinimide and acrylic acid in one step. Homopolymers and copolymers of bromoacrylated methyl oleate (BAMO) were synthesized by free radical bulk polymerization and photopolymerization techniques. Azobisisobutyronitrile (AIBN) and 2,2-dimethoxy-2-phenyl-acetophenone were used as initiators. The new monomer BAMO was characterized by FTIR, GC-MS, 1 H, and 13 C-NMR spectroscopy. Styrene (STY), methylmethacrylate (MMA), and vinyl acetate (VA) were used for copolymerization. The polymers synthesized were characterized by FTIR, 1 H-NMR, 13 C-NMR, and differential scanning calorimetry (DSC). Molecular weight and polydispersities of the copolymers were determined by GPC analysis. Ten different feed ratios of the monomers STY and BAMO were used for the calculation of reactivity ratios. The reactivity ratios were determined by the Fineman-Ross and Kelen-Tudos methods using 1 H-NMR spectroscopic data. The reactivity ratios were found to be r sty ϭ 0.891 (FinemanRoss method), 0.859 (Kelen-Tudos method); r bamo ϭ 0.671 (Fineman-Ross method), 0.524 (Kelen-Tudos method).

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

Cited by 14 publications

References 24 publications

Charge-Shifting Polycations with Tunable Rates of Hydrolysis: Effect of Backbone Substituents on Poly[2-(dimethylamino)ethyl acrylates]

Charge-Shifting Polycations with Tunable Rates of Hydrolysis: Effect of Backbone Substituents on Poly[2-(dimethylamino)ethyl acrylates]

Photopolymerized low‐surface‐energy coatings based on a novel fluorinated ether acrylate

Synthesis and characterization of copolymers of bromoacrylated methyl oleate

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