Free radical copolymerization of <i>N</i>,<i>N</i>‐dimethylaminoethyl methacrylate with styrene and methyl methacrylate: monomer reactivity ratios and glass transition temperatures

Šoljić, Ivana; Jukić, Ante; Janović, Zvonimir

doi:10.1002/pi.2626

Cited by 15 publications

(6 citation statements)

References 34 publications

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“…This suggested that there was a greater contribution to the T g from MMA in the resultant copolymer (cf., BMA). Which was supported by previous reports of the dependence of the T g values of MMA copolymers, on the proportion of MMA [ 23 , 24 , 25 , 26 , 27 ]. In contrast, when the mol% fraction of VP was lowered to ~30%, and the proportion of MMA increased commensurately in PVBM 30/50/20 (cf., PVBM 40/50/10), an increase in the T g value of ~5 °C was observed.…”

Section: Resultssupporting

confidence: 89%

Composition-Property Relationships of pH-Responsive Poly[(2-vinylpyridine)-co-(butyl methacrylate)] Copolymers for Reverse Enteric Coatings

Brewer

Blencowe

2023

Pharmaceutics

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The taste-masking of bitter-tasting active pharmaceutical ingredients is key to ensuring patient compliance when producing oral pharmaceutical formulations. This is generally achieved via the incorporation of pH-responsive, reverse enteric polymers, that prevent the dissolution of the formulation in the oral environment, but rapidly mediate it within the gastric environment. Reverse enteric polymers are commonly applied as coatings on oral dosage forms via spray atomisation (e.g., fluidised-bed spray coating), and generally exhibit the most efficient taste-masking. However, currently used reverse enteric coatings require high mass gains (% w/w) during coating to mediate taste-masking, and thereby exhibit delayed release within the gastric environment. Therefore, there remains a need for the development of new reverse enteric coatings, that can efficiently taste-mask at low mass gains and maintain rapid release characteristics within the gastric environment. Herein we report the synthesis and evaluation of a series of addition copolymers of 2-vinylpyridine and butyl methacrylate, methyl methacrylate and isobornyl methacrylate. The thermal, solubility, and water absorption properties of the copolymers were effectively tuned by altering the mol% fraction of the constitutive monomers. Based on their physical properties, selected copolymers were preliminarily evaluated for their compatibility with fluidised-bed spray coating, and effectiveness as taste-masking reverse enteric coatings. The copolymers poly[(2-vinylpyridine)-co-(butyl methacrylate)] (mol% ratio 40:60) and poly[(2-vinylpyridine)-co-(butyl methacrylate)-co-(methyl methacrylate)] (mol% ratio 40:50:10) were found to exhibit excellent taste-masking properties following fluidised-bed spray coating onto Suglets® sugar spheres. Suglets® bearing a film coating of either copolymer (5.2–6.5% w/w mass gain) were found to effectively impede the release of a model drug formulation for up to 72 h in a simulated salivary environment, and rapidly release it (<10 min) within a simulated gastric environment. The results demonstrated the potential of poly[(2-vinylpyridine)-co-(butyl methacrylate)] copolymers to form effectively taste-masked, reverse enteric dosage forms, and suggested that these copolymers may provide improved performance compared to currently available polymers.

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Section: Resultssupporting

confidence: 89%

Composition-Property Relationships of pH-Responsive Poly[(2-vinylpyridine)-co-(butyl methacrylate)] Copolymers for Reverse Enteric Coatings

Brewer

Blencowe

2023

Pharmaceutics

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“…The F–R equation represents one of the earliest attempts to linearize the copolymer composition equation :

G = r_{St} \cdot H - r_{FSt} .

…”

Section: Resultsmentioning

confidence: 99%

“…The K–T method introduces new parameters into the linearized copolymerization equation :

η = true(r_{St} + \frac{r_{FSt}}{α} true) \cdot ξ - \frac{r_{FSt}}{α},

where η and ξ are functions of the parameters G and H ,

η = \frac{G}{α + H} ξ = \frac{H}{α + H}

and α is a constant equals ( H max H min ) 1 / 2 where H max , H min are the highest and lowest values of H , respectively. The domain for the variation of ξ is between 0 and 1, whereas the domain for H is 0 and ∞.…”

Section: Resultsmentioning

confidence: 99%

“…These copolymers may be used as novel optical materials . Soljić et al presented copolymer of N , N ‐dimethylaminoethyl methacrylate and styrene with well‐defined properties, which can improve of rheological properties of lubricating mineral oils . In other work, authors surveyed sensitivity of poly(dioxolanylmethyl acrylate‐ co ‐styrene) to UV radiations and revealed that such copolymer may be used as photoresists .…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of polystyrene modified with fluorine atoms: Monomer reactivity ratios and thermal behavior

et al. 2013

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Homo‐ and copolymers of 4‐fluorostyrene (FSt) and styrene (St) were synthesized with different feed ratios using free radical bulk polymerization with azobisisobutyronitrile (AIBN) as initiator. It yielded series of (co)polymers with various amounts of included FSt, P(St‐co‐FSt) (5–50 mol%) and PFSt. The effect of the initiator concentration on the molecular weights of the homopolymers, that is, PSt and PFSt was investigated. Copolymer compositions were determined by nuclear magnetic resonance spectroscopy. The relative reactivity ratios of both comonomers were determined by applying the conventional linearization methods of Jaacks (J), Finemann–Ross (F–R), inverted Finemann–Ross (IF–R), and Kelen‐Tüdos (K–T). The reactivity ratios values of St and FSt obtained from J plot are 1.06 and 0.84, F–R plot are 1.18 and 1.06, IF–R 1.01 and 0.86, and K–T plot 1.04 and 0.88, respectively. Thermal properties of prepared (co)polymers, that is, glass transition temperature (Tg) and thermal stability, were determined from differential scanning calorimetry and thermogravimetrical measurements. The lack of significant influence of FSt comonomer content on Tg of (co)polymers was observed. Additionally, the thermal degradation kinetics of obtained PSt and PFSt was studied by thermogravimetric analysis. Kinetic parameters such as the thermal decomposition activation energy (E) and frequency factor (A) were estimated by Ozawa model [E(O) and A(O), respectively] and Kissinger model [E(K) and A(K), respectively]. The activation energy and the frequency factor of PFSt (253 kJ/mol) were higher than PSt (236 kJ/mol). The resulting activation energies estimated using the two methods were quite close. POLYM. ENG. SCI., 54:1170–1181, 2014. © 2013 Society of Plastics Engineers

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“…Since the late 1980's, several studies have been published regarding the use of multifunctional initiators in different polymerization processes, including characterization and applications of the obtained polymer materials and the mathematical modeling of the reaction system, although the vast majority of these studies has been focused on the PS production . Since the beginning of the 21 st century, experimental and modeling studies related to the use of multifunctional initiators (bi, tri, and tetrafunctional molecules) in polymerization processes have been extended to other styrene, methyl methacrylate (MMA), vinyl chloride, vinyl acetate, and styrene/MMA copolymerization systems . Despite that, it seems correct to say that the commercial use of multifunctional initiators in free radicals polymerization reactions is related primarily to styrene bulk polymerization reactions.…”

Section: Introductionmentioning

confidence: 99%

Solution styrene polymerizations performed with multifunctional initiators

Mermier

Castor

Pinto

2015

J of Applied Polymer Sci

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This paper analyzes the performance of multifunctional initiators frequently used in the literature and in the industry for the production of polystyrene (PS). Polymerizations of styrene in ethylbenzene were conducted in batch at high temperatures (120°C) until conversions around 70%, as frequent in industrial sites. Polymerizations were conducted in glass test ampoules with different concentrations and types of initiators, parameterized in terms of the active oxygen concentration. The results showed that when used at similar active oxygen concentrations, the use of the tetrafunctional initiator tetrakis(tertbutylperoxy carbonate) can allow for the production of polymer resins with significant higher average molar masses with similar polymerization rates, which can be very useful at plant site for the modification of polymer grades. Besides, the results show that the decomposition of one peroxide group of the analyzed multifunctional initiators does not affect the rates of decomposition of the remaining ones significantly, as reaction proceeds as initiated by a monofunctional initiator. Finally, although described in previous styrene polymerization studies, the use of the trifunctional initiator 3,6,9‐triethyl 3,6,9‐trimethyl‐1,4,7 triperoxonane is difficult to justify in commercial units, given its very high half‐life time. © 2015 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2015, 132, 42609.

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Free radical copolymerization of N,N‐dimethylaminoethyl methacrylate with styrene and methyl methacrylate: monomer reactivity ratios and glass transition temperatures

Cited by 15 publications

References 34 publications

Composition-Property Relationships of pH-Responsive Poly[(2-vinylpyridine)-co-(butyl methacrylate)] Copolymers for Reverse Enteric Coatings

Composition-Property Relationships of pH-Responsive Poly[(2-vinylpyridine)-co-(butyl methacrylate)] Copolymers for Reverse Enteric Coatings

Synthesis of polystyrene modified with fluorine atoms: Monomer reactivity ratios and thermal behavior

Solution styrene polymerizations performed with multifunctional initiators

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