A GC-MS study of the addition reaction of aryl amines with acrylic monomers

Farahani, Masoumeh; Antonucci, Joseph M.; Karam, Lisa R.

doi:10.1002/(sici)1097-4628(19980228)67:9<1545::aid-app6>3.0.co;2-d

Cited by 19 publications

(32 citation statements)

References 2 publications

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“…2 and 3). Based on the present data and previously reported work [18,19,21], possible routes for the conduct of the spontaneous and photo polymerizations of the HAp-incorporated model self-etch adhesives were proposed in Fig. 7.…”

Section: Discussionmentioning

confidence: 53%

“…Therefore, in order to proceed to the second step, that was, decomposition of the complex to generate the free radicals, involvement of external additives such as HAp was required. This proposed route is distinct from the reported studies [18,19,25] that employed carboxylic acids and NPG (or its analogs). In those systems, the interaction of the carboxylic acids with NPG produced rather unstable complex, probably due to the special chemical structure of NPG that combined both acid and amine groups.…”

Section: Discussionmentioning

confidence: 83%

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Hydroxyapatite induces spontaneous polymerization of model self-etch dental adhesives

Zhang

Bai

et al. 2013

Materials Science and Engineering: C

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The objective of this study is to report for the first time the spontaneous polymerization phenomenon of self-etch dental adhesives induced by hydroxylapatite (HAp). Model self-etch adhesives were prepared by using a monomer mixture of bis[2-(methacryloyloxy)ethyl] phosphate (2MP) with 2-hydroxyethyl methacrylate (HEMA). The initiator system consisted of camphorquinone (CQ, 0.022 mmol/g) and ethyl 4-dimethylaminobenzoate (4E, 0.022–0.088 mmol/g). HAp (2–8 wt.%) was added to the neat model adhesive. In a dark environment, the polymerization was monitored in-situ using ATR/FT-IR, and the mechanical properties of the polymerized adhesives were evaluated using nanoindentation technique. Results indicated that spontaneous polymerization was not observed in the absence of HAp. However, as different amounts of HAp were incorporated into the adhesives, spontaneous polymerization was induced. Higher HAp content led to higher degree of conversion (DC), higher rate of polymerization (RP) and shorter induction period (IP). In addition, higher 4E content also elevated DC and RP and reduced IP of the adhesives. Nanoindentation result suggested that the Young's modulus of the polymerized adhesives showed similar dependence on HAp and 4E contents. In summary, interaction with HAp could induce spontaneous polymerization of the model self-etch adhesives. This result provides important information for understanding the initiation mechanism of the self-etch adhesives, and may be of clinical significance to strengthen the adhesive/dentin interface based on the finding.

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Section: Discussionmentioning

confidence: 53%

Section: Discussionmentioning

confidence: 83%

Hydroxyapatite induces spontaneous polymerization of model self-etch dental adhesives

Zhang

Bai

et al. 2013

Materials Science and Engineering: C

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“…On one hand, as a redox system is utilized to initiate the polymerization, formation of a complex among both DMPT-BPO and DEAEMA-BPO is expected, and aromatic branching units and terminal groups derived from the toluidine free radicals are also expected. On the other hand, it has been shown that tertiary amine can induce deprotonation of carboxylic acid functionalities and this in turn leads to free radical polymerization of acrylic monomers [11,12]. For the bone cements prepared in this work, a certain extent of stereocontrol can be expected because the principles of template polymerization are involved.…”

Section: Nmr Characterizationmentioning

confidence: 87%

Characterization of bone cements prepared with functionalized methacrylates and hydroxyapatite

Me¹,

Jm²,

Vargas-Coronado³

et al. 2001

Journal of Biomaterials Science, Polymer Edition

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Bone cements prepared with methyl methacrylate and either methacrylic acid or diethyl amino ethyl methacrylate as comonomers were characterized by infrared spectroscopy, nuclear magnetic resonance, gel permeation chromatography, dynamic mechanical thermal analysis, and mechanical testing. Selected formulations containing these functionalized methacrylates were filled with hydroxyapatite and studied in terms of their properties in tension, compression and bending, and X-ray diffraction. It was found that residual monomer was not greatly affected by the presence of either acid or basic comonomers in the unfilled bone cements. In contrast, molecular weight, curing times, and glass transition temperature were composition dependent. For samples with acidic comonomer, a faster curing time, higher molecular weight, and higher glass transition temperatures were observed with respect to those with the basic comonomer. X-ray diffraction revealed that the crystalline structure was not affected by the nature of comonomer in the bone cement while scanning electron microscopy showed that hydroxyapatite remained as clusters in the bone cement. The mechanical properties of filled bone cements depended mainly on composition and type of testing. Hydroxyapatite-filled bone cements fullfilled the minimum compressive strength (70 MPa) required for bone cement use. However, the minimum tensile strength (30 MPa) was only fullfilled by cements prepared without comonomer and those containing methacrylic acid. The minimum bending strength requirement (50 MPa) was not satisfied by any of the formulations studied.

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“…Poly(propylmethylacrylate ethyleneimine) was prepared via reaction of poly(ethyleneimine) with methyl acrylate (known as 'Michael addition' reaction) [43][44][45]. Prior to the reaction, poly-(ethyleneimine) hydrochloric salt was first neutralized with aqueous NaOH solution.…”

Section: Synthesis Of Poly(propylmethylacrylate Ethyleneimine) Ppmaeimentioning

confidence: 99%

Influence of tert-amine groups on the solubility of polymers in CO2

Kilic

Wang

Johnson

et al. 2009

Polymer

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a b s t r a c tThere is a need to develop new, non-fluorous polymers that are highly soluble in CO 2 . Experimental evidence indicates that tertiary amine and pyridine groups may exhibit favorable Lewis acid-Lewis base type interactions with CO 2 . It is therefore reasonable to assume that incorporation of tertiary amines into the side chain or backbone of non-fluorous polymers may impart a degree of CO 2 -solubility to the polymer. We present experimental results for eight different tert-amine-containing polymers. Of these polymers, only propyl dimethylamine-functionalized poly(dimethylsiloxane) is soluble in CO 2 at temperatures and pressures accessible in our experiments, but even this polymer is less soluble than non-functionalized poly(dimethylsiloxane) at the same chain length. We have performed ab initio calculations on tertiary amine-containing moieties representative of some of the polymers examined experimentally. Our calculations confirm that amine-CO 2 interactions are indeed energetically favorable. However, we also find that the moiety self-interactions are typically more favorable than the CO 2 -moiety interactions. This indicates that the lack of solubility of amine-containing polymers in CO 2 is a direct result of strong polymer-polymer interactions.

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A GC-MS study of the addition reaction of aryl amines with acrylic monomers

Cited by 19 publications

References 2 publications

Hydroxyapatite induces spontaneous polymerization of model self-etch dental adhesives

Hydroxyapatite induces spontaneous polymerization of model self-etch dental adhesives

Characterization of bone cements prepared with functionalized methacrylates and hydroxyapatite

Influence of tert-amine groups on the solubility of polymers in CO2

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