The polymerization behavior and thermal properties of benzoxazine based on o-allylphenol and 4,4′-diaminodiphenyl methane

Liu, Yanfang; Liao, Chunyan; Hao, Zhanzhan; Li, Xinxin; Jing, Sisi; Run, Mingtao

doi:10.1016/j.reactfunctpolym.2013.12.001

Cited by 33 publications

(20 citation statements)

References 49 publications

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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%

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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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Section: Resultsmentioning

confidence: 99%

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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“…Various functional groups such as cyano, [11][12][13][14] allyl, 7,[15][16][17][18] acetylene, [19][20][21][22] aldehyde, 23,24 carboxyl, 25,26 and hydroxyl 27,28 have been introduced into benzoxazines, and the properties of the corresponding polybenzoxazines were improved to varying degrees.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and curing of amino‐containing benzoxazine as a novel hardener for diglycidyl ether of bisphenol‐A

Ren

Zhang

Zhao

et al. 2019

Polymers for Advanced Techs

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Benzoxazines containing various additional functional groups have been extensively reported to improve the properties of polybenzoxazines. In this work, a novel amino‐containing benzoxazine (PDETDA‐NH2) was conveniently synthesized from diethyltoluenediamine (DETDA), 2‐hydroxybenzaldehyde, and paraformaldehyde and was used as a hardener for diglycidyl ether of bisphenol‐A (DGEBA). The curing behaviors of PDETDA‐NH2 and PDETDA‐NH2/DGEBA systems were studied by DSC, FT‐IR, and 1H NMR. When curing, PDETDA‐NH2 was firstly polymerized to N,O‐acetal‐type polymer and then rearranged to Mannich‐type polymer at elevated temperature, while the addition reaction between amino and benzoxazine was discouraged because of the steric hindrance of alkyl substituents. During PDETDA‐NH2/DGEBA curing, it was found that the reactions happened in the order of addition polymerization of amino and epoxide, ring‐opening polymerization of benzoxazine, etherification between phenolic hydroxyl of the polymerized benzoxazine, and epoxide. Compared with DETDA cured DGEBA, PDETDA‐NH2 cured DGEBA showed higher modulus, higher char yield, and much lower water uptake.

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“…Benzoxazine is a new type of thermosetting resin synthesized from phenols, primary amines, and formaldehyde through Mannich condensation . Benzoxazine has attractive properties, which include a wide range of raw materials sources, flexible molecular design, absence of byproducts, and near‐zero shrinkage during curing .…”

Section: Introductionmentioning

confidence: 99%

Curing reaction mechanism and heat resistance properties of hexa‐(4‐carboxyl‐phenoxy)‐cyclotriphosphazene/bisphenol A aniline benzoxazine blends

et al. 2018

J of Applied Polymer Sci

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A blend system of hexa‐(4‐carboxyl‐phenoxy)‐cyclotriphosphazene (HCPCP) and bisphenol A aniline benzoxazine (BA‐a) was prepared, and its curing reaction mechanism and heat resistance properties were studied. The curing reaction mechanism of the blend was explored by differential scanning calorimetry, Fourier transform infrared spectroscopy, and modeling software using model compounds Ar‐COOH and hexachlorocyclotriphosphazene (HCCP). The heat resistance properties of the cured blends were studied by thermogravimetric analysis and dynamic mechanical analysis. The polymerization of benzoxazine was catalyzed by HCPCP through phosphazene ring and acid groups, and phosphazene played a predominant role. Compared with the materials with a single functional group (Ar‐COOH and HCCP), HCPCP containing two functional groups (phosphazene ring and acid) exhibited weaker catalytic effects, mainly due to the high molecular weight of HCPCP obstructing movement and causing steric hindrance. In addition, HCPCP had a positive effect on the thermal stability of polybenzoxazine from 250 to 400 °C. When the HCPCP content reached 3%, the cured blend had the highest glass‐transition temperature (222.2 °C), which is higher by 20 °C than that of cured benzoxazine. © 2018 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2018, 135, 46389.

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The polymerization behavior and thermal properties of benzoxazine based on o-allylphenol and 4,4′-diaminodiphenyl methane

Cited by 33 publications

References 49 publications

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 copolymers based on polyetheramine‐type benzoxazines and diglycidylether of bisphenol‐A

Synthesis and curing of amino‐containing benzoxazine as a novel hardener for diglycidyl ether of bisphenol‐A

Curing reaction mechanism and heat resistance properties of hexa‐(4‐carboxyl‐phenoxy)‐cyclotriphosphazene/bisphenol A aniline benzoxazine blends

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