Research progress in low⁃temperature curing systems of cyanate esters

doi:10.19491/j.issn.1001-9278.2024.09.020

Abstract

CLC Number:

TQ323.4

LI Ruichao, ZHU Guangming, ZHANG Xuebei, GUO Xinyi. Research progress in low⁃temperature curing systems of cyanate esters[J]. China Plastics, 2024, 38(9): 123-128.

Figures/Tables 5

Fig.1. Cyanate autocatalytic mechanism

Fig.2. Catalytic curing mechanism of cyanate by o⁃DMAP

Fig.3. Catalytic curing mechanism of transition metal complexes for cyanates

Fig.4. Curing mechanism of cyanate by dicyanamide⁃based ionic liquids

Fig.5. Catalytic mechanism of ［OMIm］［BF4］ ionic liquids on cyanates

References 45

1	Snow A W， Bauer M， Bauer J，et al. Chemistry and technology of cyanate ester resins［M］. Springer Science & Business Media， 2012：29⁃125.
2	Li X， Huang W， Sui Y， et al. Curing behaviors and thermomechanical properties of novolac cyanate⁃polyhedral oligomeric silsesquioxane copolymers［J］. Composites Communications， 2021， 28： 100932.
3	Bauer M， Bauer J， Kühn G. Kinetics and modelling of thermal polycyclotrimerization of aromatic dicyanates［J］. Acta Polymerica， 1986， 37（11/12）： 715⁃719.
4	Galukhin A， Vyazovkin S. Cyanate ester polymerization： overview of mechanistic and kinetic aspects［J］. Macromolecular Chemistry and Physics， 2023， 224（3）： 2200384.
5	Simon S L， Gillham J K. Cure kinetics of a thermosetting liquid dicyanate ester monomer/high‐Tg polycyanurate material［J］. Journal of Applied Polymer Science， 1993， 47（3）： 461⁃485.
6	Galukhin A， Nosov R， Taimova G， et al. Mechanistic and kinetic insights into phenol⁃catalyzed cyclotrimerization of cyanate esters［J］. Thermochimica Acta， 2022， 718： 179382.
7	Koh H C Y， Dai J， Tan E， et al. Catalytic effect of 2， 2′‐diallyl bisphenol A on thermal curing of cyanate esters［J］. Journal of Applied Polymer Science， 2006， 101（3）： 1 775⁃1 786.
8	Koh H C Y， Dai J， Tan E. Curing behavior and thermal mechanical properties of cyanate ester blends［J］. Journal of Applied Polymer Science， 2006， 102（5）： 4 284⁃4 290.
9	Pei S， Han Y， Guo Y， et al. Thermal and water absorption properties of cyanate ester resins modified by fluoride‐containing and silicone‐containing components［J］. Polymers for Advanced Technologies， 2020， 31（6）： 1 245⁃1 255.
10	Izu K， Tokoro Y， Oyama T. Curing acceleration of cyanate ester resin by a phenolic compound having a tertiary amino group at the ortho⁃position［J］. Polymer Journal， 2020， 52（11）： 1 245⁃1 252.
11	Bauer J， Bauer M. Curing of cyanates with primary amines［J］. Macromolecular Chemistry and Physics， 2001， 202（11）： 2 213⁃2 220.
12	欧秋仁，唐中华，嵇培军，等. 一种低温固化剂体系、氰酸酯树脂体系及制备方法：中国，201811516830.4［P］. 2019⁃05⁃07.
13	Bauer J， Bauer M. Cyanate ester based resin systems for snap⁃cure applications［J］. Microsystem Technologies， 2002， 8（1）： 58⁃62.
14	Ueyama J， Ogawa R， Tsuge A， et al. Investigation of the hardener with latent and rapid curing based on phenol‐amine salts for applications to cyanate ester resins［J］. Journal of Applied Polymer Science， 2021， 138（43）： 51286.
15	Hong S G， Yeh C S. Catalytic effects of copper oxides on the curing and degradation reactions of cyanate ester resin［J］. Journal of Applied Polymer Science， 2007， 104（1）： 442⁃448.
16	戴善凯，顾嫒娟，梁国正，等.氰酸酯树脂的固化催化研究新进展［J］.材料导报，2009，23（09）：57⁃64.
	DAI S K， GU A J， Liang G Z， et al. New research progress on catalytic curing of cyanate ester resin［J］. Materials Reports，2009，23（09）：57⁃64.
17	Mathew D， Nair C P R， Krishnan K， et al. Catalysis of the cure reaction of Bisphenol A dicyanate. A DSC study［J］. Journal of Polymer Science Part A： Polymer Chemistry， 1999， 37（8）： 1 103⁃1 114.
18	Simon S L， Gillham J K. Cure kinetics of a thermosetting liquid dicyanate ester monomer/high‐Tg polycyanurate material［J］. Journal of Applied Polymer Science， 1993， 47（3）： 461⁃485.
19	Hou D， Ma H， Li X， et al. Preparation and properties of 4， 4′‐（hexafluoroisopropylidene） diphenol cured 2， 2‐bis （4‐cyanatophenyl） propane［J］. Journal of Applied Polymer Science， 2017， 134（8）.
20	He J， Hou D， Ma H， et al. Preparation of phosphorus⁃containing cyanate resin with low curing temperature while excellent flame resistance and dielectric properties［J］. Journal of Macromolecular Science， Part A， 2019， 56（7）： 629⁃639.
21	Wang D， Hou D， Chen Z， et al. Effects of trace phenolic hydroxyl groups on the cure behaviours and properties of cyanate esters［J］. High Performance Polymers， 2020， 32（7）： 775⁃783.
22	Liu H， George G A. Mechanism and kinetics of polymerization of a dicyanate ester resin photocatalysed by an organometallic compound［J］. Polymer， 1996， 37（16）： 3 675⁃3 682.
23	Liu H， George G A. Determination of thermal cure kinetics of thin films of photocatalysed dicyanate ester by FTIR emission spectroscopy［J］. Polymer International， 2000， 49（11）： 1 505⁃1 512.
24	Liu H， George G A， Halley P J. Studies on the gelation of photocatalysed dicyanate ester resins［J］. Polymer， 1997， 38（12）： 2 997⁃3 002.
25	Mathew D， Nair C P R， Krishnan K， et al. Catalysis of the cure reaction of Bisphenol A dicyanate. A DSC study［J］. Journal of Polymer Science Part A： Polymer Chemistry， 1999， 37（8）： 1 103⁃1 114.
26	Li W， Liang G， Xin W. Triazine reaction of cyanate ester resin systems catalyzed by organic tin compound： Kinetics and mechanism［J］. Polymer International， 2004， 53（7）： 869⁃876.
27	Guenthner A J， Wright M E， Chafin A P， et al. Mechanisms of decreased moisture uptake in ortho⁃methylated di （cyanate ester） networks［J］. Macromolecules， 2014， 47（22）： 7 691⁃7 700.
28	Vashchuk A， Fainleib A M， Starostenko O， et al. Application of ionic liquids in thermosetting polymers： Epoxy and cyanate ester resins［J］. Express Polymer Letters， 2018， 12（10）： 898⁃917.
29	Throckmorton J， Palmese G. Acceleration of cyanate ester trimerization by dicyanamide RTILs［J］. Polymer， 2016， 91： 7⁃13.
30	Fainleib A， Grigoryeva O， Starostenko O， et al. Acceleration effect of ionic liquids on polycyclotrimerization of dicyanate esters［J］. Express Polymer Letters， 2016， 10（9）： 722.
31	Vashchuk A， de Anda A R， Starostenko O， et al. Structure- Property relationships in nanocomposites based on cyanate ester resins and 1⁃heptyl pyridinium tetrafluoroborate ionic liquid［J］. Polymer， 2018， 148： 14⁃26.
32	Fainleib A， Grigoryeva O， Vashchuk A， et al. Effect of ionic liquids on kinetic parameters of dicyanate ester polycyclotrimerization and on thermal and viscoelastic properties of resulting cyanate ester resins［J］. Express Polymer Letters， 2019， 13（5）： 469⁃483.
33	Lin Y， Stone C A， Shaw S J， et al. Effect of carbon nanotubes on the curing dynamics and network formation of cyanate ester resin［J］. Journal of Polymer Research， 2013， 20（3）： 1⁃12.
34	Shen Y， Gu A， Liang G， et al. High performance CaCu₃Ti₄O₁₂/cyanate ester composites with excellent dielectric properties and thermal resistance［J］. Composites Part A： Applied Science and Manufacturing， 2010， 41（11）： 1 668⁃1 676.
35	Wang X， Jin J， Song M. Cyanate ester resin/graphene nanocomposite： curing dynamics and network formation［J］. European Polymer Journal， 2012， 48（6）： 1 034⁃1 041.
36	Gu X， Zhang Z， Yuan L， et al. Developing high performance cyanate ester resin with significantly reduced postcuring temperature while improved toughness， rigidity， thermal and dielectric properties based on manganese⁃Schiff base hybridized graphene oxide［J］. Chemical Engineering Journal， 2016， 298： 214⁃224.
37	Cai T， Yuan L， Liang G， et al. Surface⁃covalent functionalized graphene oxide sheets with hyperbranched polysiloxane and Mn ion for cyanate ester resin： towards lower curing temperature and higher performance［J］. Materials Chemistry and Physics， 2019， 234： 67⁃74.
38	Lian Z， Huimin L， Zhiyu L. Mechanism and dynamic thermomechanical analysis of ZIF-61/bisphenol⁃A cyanate ester （BCE） composites［J］. Materials Letters， 2016， 175： 48⁃51.
39	Li X， Hu X， Liu X， et al. A novel approach to obtain low⁃dielectric materials： changing curing mechanism of bismaleimide–triazine resin with ZIF-8［J］. Journal of Materials Science， 2021， 56（28）： 15 767⁃15 781.
40	Zhang Z， Liang G， Wang X， et al. Curing behavior and dielectric properties of amino⁃functionalized polyhedral oligomeric silsesquioxane/cyanate ester resin hybrids［J］. High Performance Polymers， 2013， 25（4）： 427⁃435.
41	Lin Y， Jin J， Song M， et al. Curing dynamics and network formation of cyanate ester resin/polyhedral oligomeric silsesquioxane nanocomposites［J］. Polymer， 2011， 52（8）： 1 716⁃1 724.
42	Zhang S， Yan Y， Li X， et al. A novel ultra low⁃k nanocomposites of benzoxazinyl modified polyhedral oligomeric silsesquioxane and cyanate ester［J］. European Polymer Journal， 2018， 103： 124⁃132.
43	Li X， Liu X， Liu H， et al. The low⁃k epoxy/cyanate nanocomposite modified with epoxy⁃based POSS： The effect of microstructure on dielectric properties［J］. Reactive and Functional Polymers， 2023， 184： 105522.
44	Bijlard A C， Hansen A， Lieberwirth I， et al. A Nanocapsule‐Based Approach Toward Physical Thermolatent Catalysis［J］. Advanced Materials， 2016， 28（30）： 6 372⁃6 377.
45	Chen F， Yuan L， Gu A， et al. Low‐temperature cure high‐performance cyanate ester resins/microencapsulated catalyst systems［J］. Polymer Engineering & Science， 2013， 53（9）： 1 871⁃1 877.

[1]	. Preparation and Characterization of Bisphenol A Cyanate Ester Foam [J]. China Plastics, 2016, 30(04): 55-60 .
[2]	. Study on BN particles reinforced cyanate ester resin composites [J]. China Plastics, 2012, 26(09): 42-46 .
[3]	Mengmeng ZHANG Hongxia YAN Xinghua GUAN Qianqian WANG. Study on Curing Kinetics of Cyanate Ester/Polyphenylene Oxide/Nano-SiO2 Electronic Encapsulating Material [J]. China Plastics, 2012, 26(04): 40-44 .
[4]	Kun WANG Guangming ZHU Ximin LI Lei NIU. Development of Toughening Modification of Cyanate Ester Resin [J]. China Plastics, 2012, 26(03): 17-22 .
[5]	Guanglei WU Kaichang KOU Min CHAO Longhai ZHUO Yang JIANG. Curing Kinetics of Studying on Modified Bismaleimide and Cyanate Ester System with Different Epoxy Resins by Non-isothermal Method [J]. China Plastics, 2011, 25(12): 47-50 .
[6]	LIU Nai-liang . Progress in CTBN toughening modification of thermosetting resins [J]. China Plastics, 2011, 25(03): 18-24 .
[7]	ZHANG Xue-ying, ZHANG Wen-gen, HU Bao-lin, WANG Jun-long, LIANG Guo-zheng . Research on Modification and Function Mechanism of Cyanate Ester Resin by Nano-SiC [J]. China Plastics, 2009, 23(01): 43-46 .
[8]	LIU Lin, DAI Guang-Yu, LI Wen-feng. Application and Development of Nigh Performance Thermosetting Matrix Resin in Aviation and Aerospace Fields [J]. China Plastics, 2008, 22(04): 9-12 .