Benzene-1,3,5-triyl tribenzoate (TBB), both 3,5-bis(benzoyloxy)benzoate-terminated poly (aryl ether ketone) oligomers (BPAPK and TMPK), containing active ester (Ph−O−(C=O)− structure), were prepared and served as curing agents for dicyclopentadiene novoalc epoxy (DCPD). The curing kinetics and properties of three epoxy thermosets were systematically investigated. The model reaction of TBB and glycidyl phenyl ether was designed to understand the curing mechanism of oxirane ring with active ester. TMPK/DCPD displays the lowest reaction activation energy, which is the result of the combined influence of free volume and diffusion. In addition, TMPK/DCPD has the highest Tg value (218°C), which enhances 34.6% and 42.5% compared with BPAPK/DCPD and TBB/DCPD, respectively. Meanwhile, TMPK/DCPD also shows superior dielectric and water resistance properties due to no secondary alcohol generated after curing and hydrophobic tetramethyl-substituted biphenyl structure. Herein, TMPK/DCPD as high-performance epoxy thermosets has potential applications in electronic packaging fields.
JinFLLiXParkSJ. Synthesis and application of epoxy resins: a review. J Ind Eng Chem2015; 29: 1–11.
4.
QuZWuKMengW, et al.Surface coordination of black phosphorene for excellent stability, flame retardancy and thermal conductivity in epoxy resin. Chem Eng J2020; 397: 125416.
5.
ChenCXueYLiX, et al.High-performance epoxy/binary spherical alumina composite as underfill material for electronic packaging. Compos A Appl Sci Manuf2019; 118: 67–74.
6.
YeoH. Curing kinetics of liquid crystalline 4,4'-diglycidyloxybiphenyl epoxy with various diamines. Polymer2019; 168: 209–217.
7.
DingCMatharuAS. Recent developments on biobased curing agents: a review of their preparation and use. ACS Sustain Chem Eng2014; 2: 2217–2236.
8.
Fernández-FrancosXKonurayAOBelmonteA, et al.Sequential curing of off-stoichiometric thiol–epoxy thermosets with a custom-tailored structure. Poly Chem2016; 7: 2280–2290.
9.
KomarovaLSalazkinSBulgakovaI, et al.Journal of Polymer Science: Polymer Chemistry Edition1978; 16: 1643–1657.
10.
NishikuboTShimokawaTHiranoT, et al.A novel insertion reaction of epoxy compounds into phenyl ester linkages in polymer chains. J Poly Sci A Poly Chem1989; 27: 2519–2530.
11.
NishikuboTSaitaSFujiiT. New thermo-crosslinking reactions of polymers containing pendant epoxide groups with various polyfunctional active esters. J Polym Sci A Polym Chem1987; 25: 1339–1351.
12.
NakamuraSArimaM. Characterization of the network structure o epoxy resins cured with active esters. Int J Polym Anal Char1995; 1: 75–86.
13.
NishikuboTSaitaSFujiiT. New thermo-crosslinking reactions of polymers containing pendant epoxide groups with various polyfunctional active esters. ACS Omega2018; 3: 4295–4305.
14.
ChenCHLinCMJuangTY, et al.The reaction of activated esters with epoxides for self-curable, highly flexible, A 2 B 2- and A 3 B 3-type epoxy compounds. Poly Chem2019; 10: 3983–3995.
15.
ChenCHLiuCHAriramanM, et al.Phosphinated poly (aryl ether) s with acetic/phenyl methacrylic/vinylbenzyl ether moieties for high-t g and low-dielectric thermosets. ACS Omega2018; 3: 6031–6038.
16.
TianNNingRKongJ. Self-toughening of epoxy resin through controlling topology of cross-linked network. Poly2016; 99: 376–385.
17.
QuanDMurphyNIvankovicA. Fracture behaviour of epoxy adhesive joints modified with core-shell rubber nanoparticles. Eng Fract Mech2017; 182: 566–576.
18.
XuXGaoSZhangD, et al.Mechanical behavior of liquid nitrile rubber-modified epoxy resin: experiments, constitutive model and application. Inter J Mech Sci2019; 151: 46–60.
19.
SuCCWooEM. Chemical interactions in blends of bisphenol A polycarbonate with tetraglycidyl-4, 4’-diaminodiphenylmethane epoxy. Macromolecules1995; 28: 6779–6786.
20.
ZhaoQWangXYHuYH. The application of highly soluble amine-terminated aromatic polyimides with pendent tert-butyl groups as a tougher for epoxy resin. Chinese J Polym Sci, 2015; 33: 1359–1372.
21.
Di PasqualeGMottoORoccaA, et al.New high-performance thermoplastic toughened epoxy thermoset. Polymer1997; 38: 4345–4348.
22.
LinCHWangYRFengYR, et al.An approach of modifying poly (aryl ether ketone) to phenol-containing poly (aryl ether) and its application in preparing high-performance epoxy thermosets. Polymer2013; 54: 1612–1620.
23.
LiuXXuXLiuZ. Synthesis and characterization of novel fluorinated naphthalene-based poly (arylene ether ketone) s with low dielectric constants. J Mater Sci: Mater Electron2019; 30: 16369–16375.
24.
BennettGFarrisRThompsonS. Amine-terminated poly (aryl ether ketone)-epoxy/amine resin systems as tough high performance materials. Polymer1991; 32: 1633–1641.
25.
FrancisBThomasSAsariGV, et al.Synthesis of hydroxyl-terminated poly (ether ether ketone) with pendent tert-butyl groups and its use as a toughener for epoxy resins. J Polym Sci B Polym Phys2006; 44: 541–556.
26.
ZhangYZhaoCLiuJ, et al.Preparation and characterization of ultralow dielectric and fibrous epoxy thermoset cured with poly (arylene ether ketone) containing phenolic hydroxyl groups. Eur Polym J2018; 109: 110–116.
27.
GuoHLZhengJGanJQ, et al.Relationship between crosslinking structure and low dielectric constant of hydrophobic epoxies based on substituted biphenyl mesogenic units. RSC Adv2015; 5: 88014–88020.
28.
GuoHLLiYWZhengJ, et al.High thermo-responsive shape memory epoxies based on substituted biphenyl mesogenic with good water resistance. RSC Adv2015; 5: 67247–67257.
29.
RenSLiangLLanY, et al.Synthesis, phase behaviors, and mechanical properties of biphenyl-type epoxy resins and composites. J Appl Polym Sci2007; 106: 2917–2924.
30.
ChenCHTungSHJengRJ, et al.A facile strategy to achieve fully bio-based epoxy thermosets from eugenol. Polymer2018; 140: 225–232.
31.
Dell’ErbaIEWilliamsRJ. Homopolymerization of epoxy monomers initiated by 4-(dimethylamino) pyridine. Polym Eng Sci2006; 46: 351–359.
32.
KissingerHE. Variation of peak temperature with heating rate in differential thermal analysis. J Res Nat Bur Stand1956; 57: 217–221.
33.
OzawaT. A new method of analyzing thermogravimetric data. Bull Chem Soc Japan1965; 38: 1881–1886.
34.
MacedoPBLitovitzTA. On the relative roles of free volume and activation energy in the viscosity of liquids. J Chem Phys1965; 42: 245–256.
35.
QinJZhangGSunR, et al.Synthesis of aromatic amine curing agent containing non-coplanar rigid moieties and its curing kinetics with epoxy resin. J Therm Anal Calorim2014; 117: 831–843.
36.
VyazovkinSSbirrazzuoliN. Mechanism and kinetics of epoxy− amine cure studied by differential scanning calorimetry. Macromolecules1996; 29: 1867–1873.
37.
StutzHMertesJ. Influence of the structure on thermoset cure kinetics. J Polym Sci A Polym Chem1993; 31: 2031–2037.
38.
WanJLiCBuZY, et al.Acrylonitrile-capped poly (propyleneimine) dendrimer curing agent for epoxy resins: model-free isoconversional curing kinetics, thermal decomposition and mechanical properties. Mater Chem Phys2013; 138: 303–312.
39.
AldridgeMWinemanAWaasA, et al.In situ analysis of the relationship between cure kinetics and the mechanical modulus of an epoxy resin. Macromolecules2014; 47: 8368–8376.
40.
WanJGanBLiC, et al.A sustainable, eugenol-derived epoxy resin with high biobased content, modulus, hardness and low flammability: synthesis, curing kinetics and structure–property relationship. Chem Eng J2016; 284: 1080–1093.
41.
ZhangZLiJZhangY, et al.Kinetics of partially depolymerized lignin as co-curing agent for epoxy resin. Int J Biol Macromol2020; 150: 786–792.
42.
LarsenALHansenKSommer-LarsenP, et al.Elastic properties of nonstoichiometric reacted PDMS networks. Macromolecules2003; 36: 10063–10070.
43.
LuMLiuYDuX, et al.Cure kinetics and properties of high performance cycloaliphatic epoxy resins cured with anhydride. Ind Eng Chem Res2019; 58: 6907–6918.
44.
NumataSFujisakiKKinjoN. Re-examination of the relationship between packing coefficient and thermal expansion coefficient for aromatic polyimides. Polymer1987; 28: 2282–2288.
45.
HasegawaMSakamotoYTanakaY, et al.Poly (ester imide) s possessing low coefficients of thermal expansion (CTE) and low water absorption (III). Use of bis (4-aminophenyl) terephthalate and effect of substituents. Eur Polym J2010; 46: 1510–1524.
46.
LiuMWuPDingY, et al.Study on diffusion behavior of water in epoxy resins cured by active ester. Phys Chem Chem Phys2003; 5: 1848–1852.
47.
KumarKSKumarVNairCR. Bulk superhydrophobic materials: a facile and efficient approach to access superhydrophobicity by silane and urethane chemistries. RSC Adv2014; 4: 2969–2973.
48.
QianCBeiRZhuT, et al.Facile strategy for intrinsic low-K dielectric polymers: molecular design based on secondary relaxation behavior. Macromolecules2019; 52: 4601–4609.
49.
BurgoonHCyrusCSkilskyjD, et al.Photopatterning of low dielectric constant cycloolefin polymers using azides and diazirines. ACS Appl Polym Mater2020; 2: 1819–1826.
50.
ZhaoLHeCLuZ, et al.Synthesis and characterization of rigid-chain liquid–crystalline polymers containing laterally attached side rods. J Polym Sci A Polym Chem2001; 39: 1288–1294.
51.
TaoZYangSGeZ, et al.Synthesis and properties of novel fluorinated epoxy resins based on 1, 1-bis (4-glycidylesterphenyl)-1-(3′-trifluoromethylphenyl)-2, 2, 2-trifluoroethane. Eur Polym J2007; 43: 550–560.
52.
ShangWJiangH. Preparation and properties of a novel fluorinated epoxy resin/DGEBA blend for application in electronic materials. High Perform Polym2020; 32: 793–800.
53.
KongLChengYJinY, et al.Low k epoxy resin containing cycloaliphatic hydrocarbon with high crosslinking density. J Appl Polym Sci2016; 133: 43456.
