In this study, we report the preparation of thermosetting polyimides (PIs) based on carborane-containing tetramine and their characterizations. The novel tetramine 1,2-bis(4-(3,5-diaminobenzoic acid phenyl ester))carborane (CBNH) was synthesized and characterized firstly. Then, it was used in the preparation of two kinds of branched imide oligomers via the method of thermal imidization. The cure behavior of the obtained phenylethynyl-terminated oligomers was investigated by differential scanning calorimetry. The effect of carborane substituent on the thermal properties of PIs was studied by comparing with a similar structure without the carborane group. The thermal properties of PIs and carbon fiber/PI composites were investigated by thermal gravimetric analysis and dynamic mechanical analysis, respectively. Because of the introduction of high steric hindrance of carborane structure, the resulting thermosets and carbon fiber/PI composites had excellent thermal property with a high char yield at 800°C (>66.5%) and a high glass transition temperature (up to 500°C), respectively.
LiuJGShenDXYangSY. Recent research and development of matrix resins for high temperature polymer composites. Aeros Mater Technol2013; 4: 8–13.
2.
TamaiSKurokiTShibuyaA. Synthesis and characterization of thermally stable semicrystalline polyimide based on 3,4′-oxydianiline and 3,3′,4,4′-biphenyltetracarboxylic dianhydride. Polymer2001; 42: 2373–2378.
3.
LoTYWangYJLiuDM. Surface characteristics and biofunctionality of a novel high-performance, hydrophilic Jeffamine-added fluoro-containing polyimide for biomedical applications. J Polym Res2015; 22: 4. DOI: 10.1007/s10965-014-0628-8.
4.
ShahramMAYousefN. New fluorine-based thermally stable five- and six-membered rings polyimides with enhanced solubility. J Appl Polym Sci2012; 124: 2891–2901.
5.
YangYFanLQuX. Fluorinated phenylethynyl-terminated imide oligomers with reduced melt viscosity and enhanced melt stability. Polymer2011; 52: 138–148.
6.
LiangZMYinJXuHJ. Polyimide/montmorillonite nanocomposites based on thermally stable, rigid-rod aromatic amine modifiers. Polymer2003; 44: 1391–1399.
7.
LuoLBPangYWJiangX. Preparation and characterization of novel polyimide films containing amide groups. J Polym Res2012; 19: 9783. DOI: 10.1007/s10965-011-9783-3.
8.
StankoVIChapovskiiYABrattsevVA. The chemistry of decaborane and its derivatives. Russ Chem Rev1965; 34: 424–439.
9.
BregadzeVI. Dicarba-closo-dodecaboranes C2Bl0H12 and their derivatives. Chem Rev1992; 92: 209–223.
10.
VinogradovaSVValetskiiPMKabachiiYA. Polymers with arylenedicarbadodecaborane fragments in the chain. Russ Chem Rev1995; 64: 365–388.
11.
ParrottMCValliantJFAdronovA. Thermally induced phase transition of carborane-functionalized aliphatic polyester dendrimers in aqueous media. Langmuir2006; 22: 5251–5255.
12.
HanGYangZYangX. Synthesis, characterization and thermal stability of novel carborane-containing epoxy novolacs. Chin J Polym Sci2016; 9: 1103–1116.
13.
MenXChengYChenG. Curing behaviour and thermal properties of epoxy resin cured by aromatic diamine with carborane. High Perform Polym2014; 27: 497–509.
14.
LuoYLuYLiN. Synthesis, structure, and properties of segmented carborane-containing polyurethanes. J Appl Polym Sci2015; 132: 42227–42238.
15.
LiNZengFLWangYu. Synthesis and characterization of fluorinated polyurethane containing carborane in the main chain: thermal, mechanical and chemical resistance properties. Chin J Polym Sci2018; 36: 85–97.
16.
ZhangXKongLDaiL. Synthesis, characterization, and thermal properties of poly(siloxane-carborane)s. Polymer2011; 52: 4777–4784.
17.
LiNZengFLQuDZ. Synthesis and characterization of carborane-containing polyester with excellent thermal and ultrahigh char yield. J Appl Polym Sci2016; 133: 44202. DOI: 10.1002/APP.44202.
WuYEYangJPChenG. Synthesis and characterization of a carborane-containing monofunctional imide monomer as a modifier for imide oligomer. High Perform Polym2017. DOI: 10.1177/0954008317731504.
23.
ChengSHanJWangX. Oxidatively stable thermosets derived from thermal copolymerization of acetylene-terminated imide monomer with an acetylenic monomer containing carborane. Polymer2017; 115: 96–105.
24.
KricheldorfHRBruhnCRussanovA. LC-polyimides. IX. Poly(ester-imide)s of N-(4’-carboxyphenyl)trimellitimide containing carborane 1,7-dicarboxylic acid, or isophthalic acid. J Appl Polym Sci1993; 31: 279–282.
PatelJPXiangZGHsuSL. Characterization of the crosslinking reaction in high performance adhesives. Int J Adhes Adhes2017; 78: 256–262.
27.
MengXSYanJL. Thermosetting polyimides and composites based on highly soluble phenylethynyl-terminated isoimide oligomers. RSC Adv2014; 4: 37458–37469.
28.
HuangXZhangQ. Greatly enhanced thermo-oxidative stability of polybenzoxazine thermoset by incorporation of m-carborane. J Polym Sci A Polym Chem2015; 53: 973–980.
29.
ChuangKC, Bowman LC and Tsotsis TK. 6F-polyimides with phenylethynyl endcap for 315-370°C applications. High Perform Polym2003; 15: 459–472.
30.
YokotaRYamamotoSYanoS. Molecular design of heat resistant polyimides having excellent processability and high glass transition temperature. High Perform Polym2001; 13: S61–S72.
