A facile synthesis of soluble polyimides with high glass transition temperature and excellent mechanical properties due to intermolecular hydrogen bonds
Restricted accessResearch articleFirst published online April, 2020
A facile synthesis of soluble polyimides with high glass transition temperature and excellent mechanical properties due to intermolecular hydrogen bonds
An unsymmetrical heterocyclic diamine monomer containing proton donor (–NH–), 2-(4-aminophenyl)-5-aminobenzimidazole (PABZ), which can form hydrogen bond interactions with carbonyl functional group, was copolymerized with 4,4′-(hexafluoroisopropylidene)diphthalic anhydride (6FDA) and 2,2′-bis(trifluoromethyl)-4,4′-diaminobiphenyl (TFMB) through two-step synthetic methods to obtain a series of homo- and co-polyimide (PI). The corresponding homo- and co-PI both exhibited good solubility in aprotic polar solvents, such as N,N-dimethylacetamide, N-methyl-2-pyrrolidone, N,N-dimethylformamide, pyridine, and dimethyl sulfoxide. In addition, the PI-containing PABZ units showed excellent tensile strength ranging from 83 to 164 MPa, 130–260% higher than 6FDA/TFMB homo-PIa films. These PIs, especially PABZ/6FDA, showed very high glass transition temperatures, 430°C.
WuYFengCYangJ, et al.High thermally stable thermosetting polyimides derived from a carborane-containing tetramine. High Perform Polym2018; 31(5): 548–556.
2.
BaiseA. Optimizing polyimide cure using infrared spectroscopy and a factorial design. J Appl Polym Sci1986; 32: 4043–4048.
3.
LiFFangSGeJJ, et al.Diamine architecture effects on glass transitions, relaxation processes and other material properties in organo-soluble aromatic polyimide films. Polymer1999; 40: 4571–4583.
4.
HsiaoSHLinKH. Polyimides derived from novel asymmetric ether diamine. J Polym Sci A Polym Chem2005; 43: 331–341.
5.
Mehdipour-AtaeiSSarrafiYHatamiM. Novel thermally stable polyimides based on flexible diamine: synthesis, characterization, and properties. Eur Polym J2004; 40: 2009–2015.
6.
ZhangXLLiuXLWangQY, et al.Synthesis and characterization of novel fluorinated poly(ether imide)s containing pyridine and/or phenylphosphine oxide moieties. High Perform Polym2018; 31(5): 485–496.
7.
ZhangQLiSLiW, et al.Synthesis and properties of novel organosoluble polyimides derived from 1,4-bis[4-(3,4-dicarboxylphenoxy)]triptycene dianhydride and various aromatic diamines. Polymer2007; 48: 6246–6253.
8.
MayaELozanoADe AbajoJ, et al.Chemical modification of copolyimides with bulky pendent groups: effect of modification on solubility and thermal stability. Polym Degrad Stab2007; 92: 2294–2299.
9.
YamadaMKusamaMMatsumotoT, et al.Soluble polyimides with polyalicyclic structure. 2. Polyimides from bicyclo[2.2.1]heptane-2-exo-3-exo-5-exo-6-exo-tetracarboxylic 2,3:5,6-dianhydride. Macromolecules1993; 26: 4961–4963.
10.
LinSHLiFChengSZ, et al.Organo-soluble polyimides: synthesis and polymerization of 2,2′-bis (trifluoromethyl)-4,4′,5,5′-biphenyltetracarboxylic dianhydride. Macromolecules1998; 31: 2080–2086.
11.
GhoshABanerjeeS. Synthesis and characterization of new fluorinated polyimides derived from 9,10-bis[3′-trifluoromethyl-4′(4″-aminobenzoxy)benzyl]anthracene. High Perform Polym2009; 21: 173–186.
12.
LuQHYinJXuHJ, et al.Preparation and properties of organo-soluble polyimides based on 4,4 ′-diamino-3,3′-dimethyldiphenylmethane and conventional dianhydrides. J Appl Polym Sci, 1999; 72: 1299–1304.
13.
MatsuuraTHasudaYNishiS, et al.Polyimide derived from 2,2′-bis(trifluoromethyl)-4,4′-diaminobiphenyl. 1. Synthesis and characterization of polyimides prepared with 2,2′-bis(3,4-dicarboxyphenyl)hexafluoropropane dianhydride or pyromellitic dianhydride. Macromolecules1991; 24: 5001–5005.
14.
ChangJLiuWZhangM, et al.Structures and properties of polyimide fibers containing fluorine groups. RSC Adv2015; 5: 71425–71432.
15.
RussoSBianchiECongiuA, et al.A study on the N-allylation reaction of aromatic polyamides. 1. Poly (p-phenylene terephthalamide). Macromolecules2000; 33: 4390–4397.
16.
BodvikRDedinaiteAKarlsonL, et al.Aggregation and network formation of aqueous methylcellulose and hydroxypropyl methylcellulose solutions. Colloid Surface A2010; 354: 162–171.
17.
ZhangLRuanDGaoS. Dissolution and regeneration of cellulose in NaOH/thiourea aqueous solution. J Polym Sci B Polym Phys2002; 40: 1521–1529.
18.
VialeSJagerWFPickenSJ. Synthesis and characterization of a water-soluble rigid-rod polymer. Polymer2003; 44: 7843–7850.
19.
AhnTKKimMChoeS. Hydrogen-bonding strength in the blends of polybenzimidazole with BTDA-and DSDA-based polyimides. Macromolecules1997; 30: 3369–3374.
20.
LiuXGaoGDongL, et al.Correlation between hydrogen-bonding interaction and mechanical properties of polyimide fibers. Polym Adv Technol2009; 20: 362–366.
21.
SongGZhangYWangD, et al.Intermolecular interactions of polyimides containing benzimidazole and benzoxazole moieties. Polymer2013; 54: 2335–2340.
22.
LiJZhangGJingZ, et al.Synthesis and characterization of porous polyimide films containing benzimidazole moieties. High Perform Polym2017; 29: 869–876.
23.
DobbMMcIntyreJ. Properties and applications of liquid-crystalline main-chain polymers. In: PlatéNA (eds) Liquid crystal polymers II/III. Advances in polymer science. Berlin, Heidelberg: Springer, 1984, pp.61–98.
24.
LuoLWangYZhangJ, et al.The effect of asymmetric heterocyclic units on the microstructure and the improvement of mechanical properties of three rigid-rod co-PI Fibers. Macromol Mater Eng2016; 301: 853–863.
25.
ShenJLiXZhangY, et al.Synthesis and characterization of highly soluble and optically transparent polyimides derived from novel fluorinated pyridine-containing aromatic diamine. High Perform Polym2013; 25: 268–277.
26.
IshidaHWellinghoffSTBaerE, et al.Spectroscopic studies of poly [N,N′-bis(phenoxyphenyl)pyromellitimide]. 1. Structures of the polyimide and three model compounds. Macromolecules1980; 13: 826–834.
27.
MorsyMAl-KhaldiMSuwaiyanA. Normal vibrational mode analysis and assignment of benzimidazole by ab initio and density functional calculations and polarized infrared and Raman spectroscopy. J Phys Chem A2002; 106: 9196–9203.
28.
LuoLZhengYHuangJ, et al.High-performance copoly (benzimidazole-benzoxazole-imide) fibers: fabrication, structure, and properties. J Appl Polym Sci2015; 132.
29.
ArnoldFEJrBrunoKRShenD, et al.The origin of β relaxations in segmented rigid-rod polyimide and copolyimide films. Polym Eng Sci1993; 33: 1373–1380.
30.
GhaemyMAlizadehRBehmadiH. Synthesis of soluble and thermally stable polyimide from new diamine bearing N-[4-(9H-carbazol-9-yl)phenyl]formamide pendent group. Eur Polym J2009; 45: 3108–3115.
LiawDJChangFCLeungMK, et al.High thermal stability and rigid rod of novel organosoluble polyimides and polyamides based on bulky and noncoplanar naphthalene—biphenyldiamine. Macromolecules2005; 38: 4024–4029.
33.
SannigrahiAArunbabuDSankarRM, et al.Tuning the molecular properties of polybenzimidazole by copolymerization. J Phys Chem B2007; 111: 12124–12132.
34.
ZhuangYLiuXGuY. Molecular packing and properties of poly (benzoxazole-benzimidazole-imide) copolymers. Polym Chem2012; 3: 1517–1525.
