A novel epoxy resin containing trifluoromethyl and pendant polyfluorinted phenyl groups, 1,1-bis[4-(2,3-epoxypropoxy)phenyl]-1-(3,4,5-trifluorophenyl) -2,2,2-trifluoroethane (6FEP) was synthesized and characterized. The reactivtiy of 6FEP with two aromatic diamines, 4,4′-diaminodiphenyl methane (DDM) and 1,4-bis(4-amino-2-trifluoromethylphenoxy) benzene (6FAPB), and the properties of the cured 6FEP were investigated and compared with those of the commonly used epoxy resin diglycidyl ether of bisphenol A (DGEBA). The experimental results indicated that 6FEP showed lower reactivity than DGEBA. The cured 6FEP exhibited good thermal stabilities with decomposition temperature at 5% weight loss of 374–397°C, high glass transition temperature of 159–177°C and good mechanical properties. The cured 6FEP epoxy resin also showed low dielectric constants at 1 MHz in the range of 3.2–3.4 and dielectric dissipation factors (tan δ) in the range of 2.10–2.48 × 10−3. Moreover, the cured 6FEP epoxy resins exhibited higher surface hydrophobicity and lower moisture absorption compared with DGEBA. The improved dielectric properties and hydrophobic properties of the cured 6FEP epoxy resin could be attributed to the introduction of trifluoromethyl and pendant polyfluorinated phenyl groups into the molecular structure of the epoxy resin.
NagendiranSChozhanCKAlagarM. Inorganic/organic hybrid nanocomposites involving OMMT clay and cyanate ester-siloxane-modified epoxy resin: thermal, dielectric and morphological properties. High Perform Polym2008; 20: 323–347.
9.
ShiXMTuanANSuoZY. Effect of nanoparticles on the anticorrosion and mechanical properties of epoxy coating. Sur. Coat Technol2009; 204: 237–245.
10.
TaoZQYangSYGeZY. Synthesis and properties of novel fluorinated epoxy resins based on 1,1-bis(4-glycidylesterphenyl)-1-(3-tri fluoromethylphenyl)-2,2,2-trifluoroethane. Eur Polym J2007; 43: 550–560.
11.
MontefuscoFBongiovanniRSangermanoaM. New difunctional fluoro-epoxide monomers: synthesis, photopolymerization and characterization. Polymer2004; 45: 4663–4668.
12.
WangCZZuoY. Improvement of surface and moisture resistance of epoxy resins with fluorinated glycidyl ether. J Appl Polym Sci2009; 114: 2528–2532.
13.
ParkSJJinFLShinJS. Physicochemical and mechanical interfacial properties of trifluorometryl groups containing epoxy resin cured with amine. Mater Sci Eng A2005; 390: 240–245.
14.
PenoffMEPapagniGYanezMJ. Synthesis and characterization of an epoxy based thermoset containing a fluorinated thermoplastic. J Polym Sci, Part B: Polym Phys2007; 45: 2781–2792.
15.
NelsonEJFoulgerSHSmithJr DW. Semi-fluorinated epoxy thermoplastics containing the α-methylstilbene linkage. High Perform Polym2001; 13, 101–107.
HaywardDHollinsEJohncockP. The cure and diffusion of water in halogen containing epoxy/amine thermosets. Polymer1997; 38: 1151–1168.
21.
LeeJRJinFLParkSJstudy of new fluorine-containing epoxy resin for low dielectric constant. Surf Coat Technol2004; 180: 650–654.
22.
MasikiTHirohataTYoshiiM. Properties of networks obtained by internal plasticization of epoxy resin with aromatic and aliphatic glycidyl compounds. J Appl Polym Sci1989; 37: 2617–2623.
23.
SasakiS. Dielectric properties of cured epoxy resins containing the perfluorobutenyloxy group. J Polym Sci, Part C Polym Lett1986; 24: 249–252.
24.
GeZYTaoZQLiG. Synthesis and properties of novel fluorinated epoxy resins. J Appl Polym Sci2011; 120: 148–155.
25.
ZhaoXJLiuJGYangHX. Novel polyfluorinated polyimides derived from α,α-bis(4-amino-3,5-difluorophenyl) phenylmethane and aromatic dianhydrides: synthesis and characterization. Eur Polym J2008; 44: 808–820.
26.
ZhaoXJLiuJGRuiJM. Synthesis and characterization of organosoluble polyfluorinated polyimides derived from 3,3′,5,5′-tetrafluoro-4,4′-diaminodiphenylmethane and various aromatic dianhydrides. J Appl Polym Sci2007; 103: 1442–1449.
27.
YinDXLiYFYangHX. Synthesis and characterization of novel polyimides derived from 1,1-bis[4-(4′-aminophenoxy) phenyl]-1-[3′′,5′′-bis(trifluoromethyl)phenyl]-2,2,2-trifluoroethane. Polymer2005; 46: 3119–3127.
28.
XieKZhangSYLiuJG. Synthesis and characterization of soluble fluorine-containing polyimides based on 1,4-bis(4-amino-2-trifluoromethylphenoxy)benzene. J Polym Sci Part A: Polym Chem2001; 39: 2581–2589.
29.
LiuYLHsiueGHChiuYS. Synthesis, characterization, thermal, and flame retardant properties of phosphate-based epoxy resins. J Polym Sci, Part A: Polym Chem1997; 35: 565–574.
30.
ReinesSAGriffithJROrearJG. Effects of fluorine substitution upon glycidyl ether-dibutylamine reaction rates. J Org Chem1970; 35: 2772–2779.
31.
LeeJRJinFLParkSJ. Substitution effects of methyl and trifluoromethyl groups on the physicochemical properties of epoxy resins. J Appl Polym Sci2005; 98: 1860–1864.
32.
ZhangSHorrocksAR. A review of flame retardant polypropylene fibres. Prog Polym Sci2003; 28: 1517–1526.
33.
SpontonMRondaJCGaliaandM. Flame retardant epoxy resins based on giglycidyl ether of (2,5-dihydroxyphenyl)diphenyl phosphine oxide. J Polym Sci., Part A: Polym Chem2007; 45: 2142–2151.
34.
HoughamGTesoroGViehbeckA. Effects of fluorine substitution on polarization and dielectric properties of polyimides. Polym Prepr (Am Chem Soc Div Polym Chem)1993; 34: 375–376.
35.
ChernYTShiueHC. Low dielectric constants of soluble polyimides based on adamantine. Macromolecules1997; 30: 4646–4651.
36.
LinCHJiangZRWangCS. Low dielectric thermoset. II. Synthesis and properties of novel 2,6-dimethyl phenol–dipentene epoxy. J Polym Sci, Part A: Polym Chem2002; 40: 4084–4096.
37.
Van KrevelenDWHoftyzerPJ. Properties of Polymers. New York: Elsevier Publishing Co., 1976, p. 231.
38.
HanHS, Tan KL and Kang ET. fluorination of epoxy surfaces by a physical method. J Appl Polym Sci2000; 76: 296–04.
39.
BrostowWCassidyPEMacossayJ. Connection of surface tension with multiple tribological properties in epoxy + fluoropolymer systems. Polym Int2003; 52: 1498–1505.
40.
AnandMCohnREBaddourRF. Surface modification of low density polyethylene in a fluorine gas plasma. Polymer1981; 22: 361–371.
