Synthesis of highly polymerizable 1,3‐benzoxazine assisted by phenyl thio ether and hydroxyl moieties

Kawaguchi, Asei William; Sudo, Atsushi; Endō, Takeshi

doi:10.1002/pola.25923

Cited by 29 publications

(24 citation statements)

References 39 publications

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“…Amines, thiols, and elemental sulfur are typical examples of such catalysts. [40][41][42][43][44][45][46] Similarly, lithium salts and HCl salts of some amines were also reported to be alternative and cheap catalysts for the purpose. [47,48] The ability of the salts to reduce the ROP temperatures, for example, below ≈180 °C, may lead to expanded industrial applications of polybenzoxazines.…”

Section: Introductionmentioning

confidence: 99%

Counterion Effect of Amine Salts on Ring‐Opening Polymerization of 1,3‐Benzoxazines

Akkus

Kışkan

Yaǧcı

2018

Macro Chemistry & Physics

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The effect of nucleophilicity of counterions of amine HX salts as catalysts on the ring‐opening polymerization (ROP) of 1,3‐benzoxazines is investigated. The significant reduction observed for the ROP temperature is related to the nucleophilicity of counterions and found to show a general trend as I− > Br− > Cl−, as studied by differential scanning calorimetry and Fourier transform infrared spectroscopy. Moreover, the latent character of the amine salts is also demonstrated by tracking the benzoxazine–amine salt mixtures using 1H NMR spectroscopy. The spectral analysis gives evidences for the dormant nature of the amine HX salts toward benzoxazine at room temperature in solvent. Besides, thermal stabilities of the cured benzoxazine monomers with and without catalysts are investigated by thermogravimetric analysis.

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Section: Introductionmentioning

confidence: 99%

Counterion Effect of Amine Salts on Ring‐Opening Polymerization of 1,3‐Benzoxazines

Akkus

Kışkan

Yaǧcı

2018

Macro Chemistry & Physics

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“…Besides, we examined another route for the target benzoxazine 1 , which relied on the transformation of 4‐aminopyridine into the corresponding triazine derivative and its use. Recently this “triazine‐route” has been successfully applied to the efficient synthesis of benzoxazines . Accordingly, we attempted to synthesize the triazine with varying reaction conditions such as solvent, temperature, and concentration; however, under all the conditions we surveyed, the triazine was not obtained.…”

Section: Resultsmentioning

confidence: 99%

“…applied to the efficient synthesis of benzoxazines. 33 Accordingly, we attempted to synthesize the triazine with varying reaction conditions such as solvent, temperature, and concentration; however, under all the conditions we surveyed, the triazine was not obtained. Instead, the product we got was (4-Py)-NH-CH 2 -NH-(4-Py), the 2:1 adduct of 4aminopyridine and formaldehyde.…”

Section: Journal Of Polymer Sciencementioning

confidence: 99%

Functional 1,3‐benzoxazine bearing 4‐pyridyl group: Synthesis and thermally induced polymerization behavior

Kawaguchi

Sudo

Endō

2013

J. Polym. Sci. Part A: Polym. Chem.

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1,3‐benzoxazine 1, bearing 4‐pyridyl moiety on the nitrogen atom, was synthesized from p‐cresol, 4‐aminopyridine, and paraformaldehyde. The efficient synthesis was achieved by adding acetic acid to suppress the strong basicity caused by the presence of 4‐aminopyridine derivatives. Upon heating 1 at 180 °C, it underwent the thermally induced ring‐opening polymerization. The resulting polymer was composed of two types of repeating unit, i.e., (1) Mannich‐type one (‐phenol‐CH2‐NR‐CH2‐) that can be expected from the general ring‐opening polymerization of conventional benzoxazines and (2) a typical phenolic resin‐type one (‐phenol‐CH2‐phenol‐) induced by release of 4‐aminopyridine and paraformaldehyde (unit B). Another structural feature of the polymer was that it possessed a benzoxazine moiety at the chain end. © 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2014, 52, 410–416

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“…Accordingly, there has been a massive work on new monomers to improve thermal and mechanical performance of polybenzoxazines and also develop new application fields by taking advantage of design flexibility of benzoxazine monomers coming from simple preparation by using inexpensive and commercially available phenols, primary amines, and formaldehyde [13][14][15][16][17][18][19][20][21][22] (see Scheme 2).…”

Section: Introductionmentioning

confidence: 99%

Thermally curable main-chain benzoxazine prepolymers via polycondensation route

Demir

Kışkan

Aydoğan

et al. 2013

Reactive and Functional Polymers

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Synthesis of highly polymerizable 1,3‐benzoxazine assisted by phenyl thio ether and hydroxyl moieties

Cited by 29 publications

References 39 publications

Counterion Effect of Amine Salts on Ring‐Opening Polymerization of 1,3‐Benzoxazines

Counterion Effect of Amine Salts on Ring‐Opening Polymerization of 1,3‐Benzoxazines

Functional 1,3‐benzoxazine bearing 4‐pyridyl group: Synthesis and thermally induced polymerization behavior

Thermally curable main-chain benzoxazine prepolymers via polycondensation route

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