Melamine Derivatives - A Review on Synthesis and Application

Bretterbauer, Klaus; Schwarzinger, Clemens

doi:10.2174/157017912801270612

Cited by 39 publications

(21 citation statements)

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“…More recent investigations, however, primarily focus on properties and application of these materials . For a long time, the application of carbon nitride type materials was mostly limited to the use of the molecular compound melamine in melamine foams, flame retardants, and mostly in melamine‐formaldehyde resins which find broad application as coating materials, tableware or laminate flooring . These products are well established.…”

Section: Introductionsupporting

confidence: 54%

Structure Elucidation of a Melam–Melem Adduct by a Combined Approach of Synchrotron X‐ray Diffraction and DFT Calculations

Kessler¹,

Burow²,

Savaşçı

et al. 2019

Chemistry A European J

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, an adduct compound that can be obtained from dicyandiamide in autoclave reactions at 450 8Ca nd elevateda mmonia pressure, had previously been describedbased on mass spectrometry and NMR spectroscopy,b ut only incompletelyc haracterized. The crystal structure of this compound has now been elucidated by means of synchrotron microfocus diffraction and subsequent quantum-chemical structure optimization applying DFT methods. The structure was refinedi nt riclinic space group P1 based on X-ray data. Cell parameters of a = 4.56(2), b = 19.34(8), c = 21.58(11) , a = 73.34(11)8, b = 89.1(2)8,a nd g = 88.4(2)8 were experimentally obtained. The resulting cell volumes agree with the DFT optimized value to within 7%.M olecular units in the structure form stacks that are interconnectedb yavastarray of hydrogen bridge interactions. Remarkably large melam dihedral angles of 48.48 were found that allow melam to interact with melem molecules from differents tack layers,t hus forming a3 Dn etwork. p-stacking interactions appear to play no major role in this structure.Supporting information and the ORCID identification number(s) for the author(s) of this articlecan be found under: https://doi.

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Section: Introductionsupporting

confidence: 54%

Structure Elucidation of a Melam–Melem Adduct by a Combined Approach of Synchrotron X‐ray Diffraction and DFT Calculations

Kessler¹,

Burow²,

Savaşçı

et al. 2019

Chemistry A European J

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“…This approach protects the flame retardant from exuding outside the polymer and from volatility; and (3) combinatorial materials, where the additives and reactive materials are combined together to generate a synergistic effect and improve the flame-retarding or antagonistic force. 18 Triazine-based FR additives can act in both the gas and the condensed phases simultaneously, 19 besides triazine compounds are themselves good char forming agent. 20 Significant effort is directed toward FR combinations, where halogen-free FRs such as phosphorus-nitrogen (P-N)-based compounds have gained more attraction and are accepted as one of the promising candidates for further studies.…”

Section: Introductionmentioning

confidence: 99%

Recent developments in s-triazine holding phosphorus and nitrogen flame-retardant materials

Mishra

Vasava

2020

Journal of Fire Sciences

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Flame retardants are chemical compounds when mixed or incorporated in to polymers provide varying degrees of flammability protection. Flammable polymeric materials are ubiquitous with a wide array of applications. However, recent studies have shown potential environmental and health concerns with certain halogen-containing flame retardants. Thus, it has now become a necessity to explore new and effective materials that are safer and environmentally benign. In this context, halogen-free phosphorus- and nitrogen-containing flame retardants have attracted much attention worldwide. Moreover, s-triazine is the central focus because of its excellent charring effect. General strategies for synthesizing s-triazine compounds mostly via nucleophilic substitution reaction have been highlighted. This review provides a comprehensive description on design and synthesis of flame-retardant materials with significant flammability performance.

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“…Moreover, the ability to replace the chlorine atom (Cl) in the presence of an acid scavenger was found to produce mono-, di-, and tri-substituted s-triazines [3]. The first displacement of a Cl atom happens between 0 °C to ambient temperature, and the subsequent replacement of Cl occurs at higher reaction temperatures [2,6]. The phosphorus-bearing azaheterocyclic compounds have received great attention because of their different applications in medicinal chemistry and agrochemicals [7].…”

Section: Introductionmentioning

confidence: 99%

“…The synergism of P,N-containing flame retardants was extensively investigated, for enhancing both the gas- and condensed-phase mode of action [17,27]. Triazine-based flame-retardant additives can act in both the gas and condensed phases simultaneously [6,9]. Notwithstanding, the triazine compound itself was found to be a good char forming agent [12,17,19,21,26,28,29].…”

Section: Introductionmentioning

confidence: 99%

Insight into the Synthesis and Characterization of Organophosphorus-Based Bridged Triazine Compounds

et al. 2019

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In this article, we report the synthesis of 2,4,6-substituted s-triazine-based organophosphorus compounds via a two-step process, which enables their production in high yields, and with a high purity as solids. In the first step, a Michaelis–Arbuzov rearrangement of cyanuric chloride with triethyl phosphite afforded 2,4,6-trisdiethoxyphosphinyl-1,3,5-triazine (HEPT). Subsequently, the nucleophilic substitution reaction on the triazine carbon was achieved, owing to the electron-withdrawing ability of the phosphonate groups. This characteristic of HEPT facilitated its derivatization with bi-functional amines, producing novel P–C containing bridged triazine organophosphorus compounds. The molecular structures of all of the compounds were confirmed by NMR spectroscopy, CHN elemental analysis, and single crystal X-ray analysis. In the thermogravimetric analysis in an N2 environment, >33% char formation was observed for the bridged compounds. The chemical composition analysis of the char obtained under the oxidative thermal decomposition of the bridged compounds confirmed the presence of phosphorus- and nitrogen-enriched species, which indicate their function in the condensed phase. Comparatively, the detection of HPO and H–C≡P in the gas phase during the pyrolysis of the bridged compounds can act as a source for PO•, which is known for its gas phase flame inhibition reactions. The synergy of significant char formation and the generation of intermediates leading to PO• during pyrolysis makes these molecules promising flame-retardant additives.

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Melamine Derivatives - A Review on Synthesis and Application

Cited by 39 publications

References 0 publications

Structure Elucidation of a Melam–Melem Adduct by a Combined Approach of Synchrotron X‐ray Diffraction and DFT Calculations

Structure Elucidation of a Melam–Melem Adduct by a Combined Approach of Synchrotron X‐ray Diffraction and DFT Calculations

Recent developments in s-triazine holding phosphorus and nitrogen flame-retardant materials

Insight into the Synthesis and Characterization of Organophosphorus-Based Bridged Triazine Compounds

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