A pair of benzoxazine isomers from o-allylphenol and 4,4′-diaminodiphenyl ether: Synthesis, polymerization behavior, and thermal properties

Liu, Yanfang; Zhang, Jie; Li, Zhi-Yun; Li, Xinxin; Jing, Sisi; Run, Mingtao

doi:10.1016/j.polymer.2014.02.017

Cited by 26 publications

(27 citation statements)

References 47 publications

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“…In this case, the ring‐opening polymerization would proceed through an attack by the less active para ‐positions on the activated methylene . The structure changes from benzoxazine monomers to polybenzoxazines can be described in Scheme …”

Section: Resultsmentioning

confidence: 99%

Shape memory polybenzoxazines based on a siloxane-containing diphenol

Liu

Zhang

et al. 2016

J. Polym. Sci. Part B: Polym. Phys.

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A siloxane‐containing diphenol is synthesized from 1,1,3,3‐tetramethyldisiloxane and o‐allylphenol, followed by the Mannich condensation with aniline, methylamine, and formaldehyde yielding two siloxane‐containing benzoxazines. The onset polymerization temperature of aniline‐based benzoxazine is higher than that of the methylamine counterpart. The dynamic mechanical properties of the polybenzoxazines depend on the structure of the starting primary amines. Both polybenzoxazines exhibit one‐way dual‐shape memory behavior in response to changes in temperature, and they show excellent shape fixity ratios in bending, tension, and tensile stress–strain tests, high shape recovery ratios in bending and tension tests, but relatively low shape recovery ratios in tensile stress–strain test. The network chain segments including the alkylsiloxane units serve as a thermal control switch based on the glass transition temperatures (39 and 53 °C) for the polybenzoxazines. © 2016 Wiley Periodicals, Inc. J. Polym. Sci., Part B: Polym. Phys. 2016, 54, 1255–1266

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Section: Resultsmentioning

confidence: 99%

Shape memory polybenzoxazines based on a siloxane-containing diphenol

Liu

Zhang

et al. 2016

J. Polym. Sci. Part B: Polym. Phys.

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“…Correspondingly, the absorption intensity of the peak at 3340–3370 cm −1 first increased and then decreased, which is attributed to the stretching vibrations of the phenolic hydroxyl of benzoxazine moieties and the aliphatic secondary hydroxyl of DGEBA units. The intensity of the peak at 3074 cm −1 decreased in the reaction because of the radical polymerization of the allyl groups . In addition, a new absorption peak appeared at 1655 cm −1 due to Schiff base, N=CH, a possible intermediate of ring‐opening polymerization of benzoxazines .…”

Section: Resultsmentioning

confidence: 99%

“…The copolymerization of benzoxazines and epoxy resins involves two ring‐opening reactions related to oxazine and oxirane rings, which is believed to be proceeding in a way that phenolic hydroxyl groups formed in the ring‐opening reaction of benzoxazines react with oxirane rings in epoxy resins . For o AP‐pea, radical polymerization reaction of allyl groups would occur along with the ring‐opening polymerization of oxazine rings . Figure S1 presents the FTIR spectra of benzoxazine/DGEBA blends and their polymerization products obtained at a temperature in air for various times.…”

Section: Resultsmentioning

confidence: 99%

Dynamic mechanical and shape memory properties of copolymers based on polyetheramine‐type benzoxazines and diglycidylether of bisphenol‐A

Shen

et al. 2018

J of Applied Polymer Sci

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Two series of benzoxazine/epoxy copolymers are prepared from polyetheramine-type benzoxazines and diglycidyl ether of bisphenol A (DGEBA) in various weight ratios. Each copolymer appears a single glass-transition temperature (T g ), and the T g shows a systematic increase with increasing DGEBA content for both copolymer systems, but copolymers with low DGEBA content show respectively lower T g s than the corresponding pristine polybenzoxazines. Compared to the corresponding pristine polybenzoxazines, the effect of DGEBA content on the variation in T g of the copolymers depends on the substituent structure of benzoxazines. The two series of copolymers exhibit one-way dual shape memory effect based on T g , and the shape memory effect is affected by both the substituent structure of benzoxazines and the content of DGEBA. Under motion constraints in tensile deformation mode, copolymers with low DGEBA content exhibit high shape recovery ratios (91.0-96.1%) over the corresponding polybenzoxazines (84.5%), whereas copolymers with high DGEBA content show relatively low shape recovery ratios (75.0-84.7%).

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“…In the 1 H NMR spectra, the resonances at 3.98–4.00 and 4.87–4.89 ppm correspond to the methylene protons of ArCH 2 N and OCH 2 N of the oxazine ring, respectively. The chemical shifts (ppm) at 0.06–0.09 correspond to the protons in the methyl groups of tetramethyldisiloxane (TMDS) and polydimethylsiloxane (PDMS) units, and 0.52–0.58, 1.56–1.63, and 2.70–2.76 are assigned to the protons of the aminopropyl group, whereas the chemical shifts (ppm) at 3.33–3.36, 5.02–5.08, and 5.96–6.04 correspond to the aliphatic protons in the allyl group . The peaks at 6.77–7.13 ppm are assigned to the aromatic protons.…”

Section: Resultsmentioning

confidence: 99%

“…In the C NMR spectra, the resonances at 54.51–54.66 and 82.46–82.53 ppm correspond to the methylene carbons of ArCH 2 N and OCH 2 N of the oxazine ring, respectively. The chemical shifts (ppm) at 0.08–0.97 correspond to the carbons in the methyl groups of TMDS and PDMS units, and 15.49–15.70, 21.87–22.06, and 50.19–50.37 are assigned to the carbons of the aminopropyl group, whereas the chemical shifts (ppm) at 33.48–33.57, 115.15–115.22, and 136.68–136.78 correspond to the aliphatic carbons in the allyl group . The detail assignments of other chemical shifts can be seen in Supporting Information Figures S1 and S2.…”

Section: Resultsmentioning

confidence: 99%

Dynamic mechanical and shape memory properties of polybenzoxazines based on aminopropyl‐terminated siloxanes

Song

Zhang

et al. 2016

J of Applied Polymer Sci

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Four siloxane-containing benzoxazine monomers and telechelic benzoxazine oligomers were synthesized from 1,3-bis(3aminopropyl)-1,1,3,3-tetramethyldisiloxane, a,x-bis(3-aminopropyl)polydimethylsiloxane, phenol, o-allylphenol, and formaldehyde. The length of the siloxane segment affects the polymerization reaction of the benzoxazine monomers and telechelic benzoxazine oligomers. The dynamic mechanical properties of the corresponding polybenzoxazines depend primarily on the structure of phenol and the length of the siloxane segment. The polybenzoxazines exhibit one-way dual-shape memory behavior in response to changes in temperature. The thermally induced shape memory effects of the polybenzoxazines were characterized by bending and tensile stress-strain tests with a temperature program based on their glass transition temperatures. V C 2016 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2016, 133, 44121.

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A pair of benzoxazine isomers from o-allylphenol and 4,4′-diaminodiphenyl ether: Synthesis, polymerization behavior, and thermal properties

Cited by 26 publications

References 47 publications

Shape memory polybenzoxazines based on a siloxane-containing diphenol

Shape memory polybenzoxazines based on a siloxane-containing diphenol

Dynamic mechanical and shape memory properties of copolymers based on polyetheramine‐type benzoxazines and diglycidylether of bisphenol‐A

Dynamic mechanical and shape memory properties of polybenzoxazines based on aminopropyl‐terminated siloxanes

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