Calixarene–based cyanate ester resin for high-temperature material

Abstract

p-tert-Butylcalix[4]arene-derived cyanate ester resins, both single and binary systems, were synthesized and studied for their thermal properties. The results showed that pure calixarene cyanate ester can be thermally cured at comparatively high temperature, which remains in original powder state after thermally cured. So the pure calixarene cyanate ester resin fails to meet the processing demands of resin-matrixed composite. In this work, p-tert-butylcalix[4]arene cyanate ester was chemically functionalized to have highly decreased thermal cure temperature (by copolymerization with epoxy, bisphenol A cyanate ester (BPACE), and polysilazane (PSZ), respectively). The binary resins were thermally cured into monolithic materials. The optimal acceleration of thermal cure reaction was achieved with an addition of 10% PSZ. The addition of epoxy resin decreased thermal resistance and carbon yield of p-tert-butylcalix[4]arene cyanate ester and addition of BPACE slightly decreased thermal resistance and carbon yield, while PSZ highly improved thermal resistance and carbon yield. Glass transition temperature of the co-cured resin of calixarene cyanate ester with 10% PSZ was much higher than that of conventional BPACE. Calixarene cyanate ester possesses much better property than that of conventional BPACE resin.

Keywords

Calixarene cyanate ester resin thermal cure nanoporous thermal stability

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References

Huang

Yang

. Research progress in calixarene chemistry. Prog Chem 1994; 6(3): 173–177.

Gutsche

Iqbal

. p-tert-Butylcalix[4]arene. Org Synth 1990; 68: 234–236.

Mokhtari

Pourabdollah

Dalali

. Analytical applications of calixarenes from 2005 up-to-date. J Incl Phenom Macrocycl Chem 2011; 69(1–2): 1–55.

Dozol

Macias

. Extraction of Strontium and Cesium by Dicarbollides, Crown Ethers and Functionalized Calixarenes. J Incl Phenom Macro 2000; 38(1–4): 1–22.

Mokhtari

Pourabdollah

Dallali

. A review of calixarene applications in nuclear industries. J Radioanal Nucl Chem 2011; 287(3): 921–934.

Jipa

Zaharescu

Setnescu

. Effect of calixarenes on thermal stability of polyethylenes. Polym Degrad Stab 2003; 80(2): 203–208.

Zhu

Gou

Shen

. Synthesis and application of calixarene containing polymers. Prog Chem 2008; 20(5): 720–728.

Guo

Liu

. Calixarene-based supramolecular polymerization in solution. Chem Soc Rev 2012; 41(18): 5907.

Zhang

Chen

. Preparation and study of two polysiloxanes with pendant hand-basket type calixarene stationary phases for capillary gas chromatography. J Chromatogr A 1999; 840(2): 225–233.

10.

Shen

. Study on low viscosity and high char yield phenolic resins modified by calixarenes. PhD dissertation, Sichuan University, China, 2004 [in Chinese].

11.

Boehmer

Kai

Schoen

. Direct synthesis of calix[4]arenes with two different phenolic units in alternating order. J Org Chem 1992; 57(2): 790–792.

12.

Kudo

Nishikubo

. Model reactions of calixarenes and their esterified derivatives with glycidyl phenyl ether for thermal curing reactions of epoxy resins. Polym J 2010; 42(6): 456–463.

13.

Kudo

Nishikubo

. Thermal cured epoxy resins using certain calixarenes and their esterified derivatives as curing agents. J Polym Sci Polym Chem 2010; 48(9): 1931–1942.

14.

Zhang

Wang

. Synthesis and properties of novel 4,4′-biphenylene-bridged flame-retardant cyanate ester resin. J Appl Polym Sci 2011; 122(4): 2609–2615.

15.

Zaldivar

Kim

Steckel

. Surface preparation for adhesive bonding of polycyanurate-based fiber-reinforced composites using atmospheric plasma treatment. J Appl Polym Sci 2011; 120(2): 921–931.

16.

Wang

Gao

. Preparation and characterization of novel film adhesives based on cyanate ester resin for bonding advanced radome. Int J Adhes 2016; 68: 80–86.

17.

Dinakaran

Alagar

. Preparation and characterization of bismaleimide (N,N′-bismaleimido-4,4′-diphenyl methane)–unsaturated polyester modified epoxy intercrosslinked matrices. J Appl Polym Sci 2002; 85(14): 2853–2861.

18.

Anbazhagan

Alagar

Gnanasundaram

. Synthesis and characterization of organic-inorganic hybrid clay filled and bismaleimide—siloxane modified epoxy nanocomposites. Int J Plast Technol 2011; 15(1): 30–45.

19.

Steffen

Bauer

Decker

. Fire-retardant hybrid thermosetting resins from unsaturated polyesters and polysilazanes. J Appl Polym Sci 2014; 131(12): 469–474.

20.

Keller

Laskoski

. Synthesis of oligomeric cyanate esters. US Patent, US 7,348,395 B2, 2008-3-25.

21.

Vergnaud

Bouzon

. Cure of thermosetting resins. London: Springer, 1992.

22.

Ahn

Seferis

. Prepreg processing science and engineering. Polym Eng Sci 2010; 33(18): 1177–1188.

23.

Kumar

KSS

Nair

CPR

Ninan

. Investigations on the cure chemistry and polymer properties of benzoxazine–cyanate ester blends. Eur Polym J 2009; 45(2): 494–502.

24.

Kim

. Effect of cyanate ester on the cure behavior and thermal stability of epoxy resin. J Appl Polym Sci 2015; 65(1): 85–90.

25.

Zhang

Pei

Chen

. Preparation and Dielectric Properties of POSS-NH2/Cyanate Ester Resin Organic-Inorganic Hybrids. Adv Mater Res 2011; 216: 635–639.

26.

Luo

Han

. Preparation and properties of novel hybrid resins based on acetylene-functional benzoxazine and polyvinylsilazane. J Appl Polym Sci 2013; 130(5): 3794–3799.

27.

Becker

Jensen

Lukacs

III A

. Metal-nitrogen polymer compositions comprising organic electrophiles. US Patent, US 5,616,650. 1997-4-1.