A series of molecular-weight-controlled aromatic copolyimides based on anhydrides 4,4′-oxydiphthalic anhydride (ODPA) or/and 2,3,3′,4′-biphenyltetracarboxylic dianhydride (α-BPDA) were prepared by polycondensation reaction with mixture of diamines 1,4-bis(4-amino-2-trifluoromethylphenoxy)benzene (6FAPB) and 4,4′-diaminodiphenylsulphone (DDS) in the presence of phthalic anhydride (PA) as end-capping agent. The effect of the chemical structure of the copolyimides on solubility, rheological behavior, thermal stabilities and adhesive properties was investigated. Experimental results suggested that the solubility and thermal properties of copolyimides could be improved by incorporation of asymmetric α-BPDA. The copolyimide TPI-B (α-BPDA/6FAPB-DDS/PA) exhibited better solubility with the solid content as high as 45 wt.% in N,N-dimethylacetamide and high thermal stability with the Tg of 306 °C. TPI-A (ODPA/6FAPB-DDS/PA) and TPI-C (α-BPDA-ODPA/6FAPB-DDS/PA) could be produced into glass-cloth-supported adhesive films. TPI-A adhesive film gave better adhesive properties at room temperature with lap shear strength of 16.41 MPa and T-peel strength of 2.1 kN m−1, which attributed to its flexible structure and good melt processability. TPI-C adhesive film exhibited higher adhesive properties at elevated temperature with the lap shear strength exceeding 9 MPa at 280 °C. The copolyimides with combination of rigid and flexible structures could afford good melt flow behavior and high thermal stability, which yielded good adhesive properties at high temperature.
MittalKL. Polyimides: Synthesis, characterization and applications. New York: Plenum Press, 1984.
3.
KricheldorfHR. Progress in polymer chemistry, advances in polymer science. Berlin: Springer, 1999.
4.
YuWXKoTM. Surface characterizations of potassium-hydroxide- modified Upilex-S-(R) polyimide at an elevated temperature. Eur Polym J2001; 37(9): 1791–1799.
5.
XieKLiuJGZhouHWZhangSYHeMHYangSY. Soluble fluoro-polyimides derived from 1,3-bis(4-amino-2-trifluoromethyl-phenoxy)benzene and dianhydrides. Polymer2001; 42(17): 7267–7274.
6.
WuJTYangSYGaoSQHuAJLiuJGFanL. Preparation, morphology and properties of nano-sized Al2O3/polyimide hybrid films. Eur Polym J2005; 41(1): 73–81.
7.
ZhaiFXGuoXXFangJHXuHJ. Synthesis and properties of novel sulfonated polyimide membranes for direct methanol fuel cell application. J Membr Sci2007; 296(1-2): 102–109.
8.
EllisonMMTaylorLT. Sulfur versus non-sulfur containing polyimide adhesives for bonding steel. J Adhes1997; 60(1-4): 51–69.
9.
ReeMParkYHShinTJNunesTLVolksenW. Self-adhesion of poly(4,4′-oxydiphenylene biphenyltetracarboximide) and its adhesion to substrates. Polymer2000; 41(6): 2105–2111.
10.
StClairTLProgarDJ. A novel addition polyimide adhesive. 1981, Hampton, VA, USA: NASAReport TM-1981-81976.
11.
StClairTLYamakiDA. A thermoplastic polyimidesulfone. 1982, Hampton, VA, USA: NASA, Report TM-1982-84574.
12.
OgliarusMARomanellMGBeckerEI. Chemistry of cyclopentadienones. Chem Rev1965; 65(3): 261–367.
13.
TanBVasudevanVLeeYJGardnerSDavisRMBullionsTDesign and characterization of thermosetting polyimide structural adhesive and composite matrix systems. J Polym Sci, Part A: Polym Chem1997; 35(14): 2943–2954.
14.
StClairAK. Aluminum ion-containing polyimide adhesives, 1981, US patent:4,204,461.
15.
ShawSJ. Adhesives in demanding applications. Polym Int1996; 41(2): 193–207.
16.
HergenrotherPMHavensSJ. Preliminary adhesive and composite properties of LARCTM-CPI 2, a new semicrystalline polyimide. High Perform Polym1993; 5: 177–185.
RattaVStancikEJAyambemAPavatareddyHMcGrathJEWilkesGL. A melt-processable semicrystalline polyimide structural adhesive based on 1,3-bis(4-aminophenoxy) benzene and 3,3′,4,4′-biphenyltetracarboxylic dianhydride. Polymer1999; 40(7): 1889–1902.
19.
SrinivasSCaputoFEGrahamMGardnerS.DavisRMMcGrathJE, Semicrystalline polyimides based on controlled molecular weight phthalimide end-capped 1,3-bis(4-aminophenoxy)benzene and 3,3′,4,4′- biphenyltetracarboxylic dianhydride: Synthesis, crystallization, melting, and thermal stability. Macromolecules1997; 30(4): 1012–1022.
20.
KreuzJAHsiaoBSRennerCAGoffDL. Crystalline homopolyimides and copolyimides derived from 3,3′,4,4′-biphenyltetracarboxylic dianhydride/1,3-bis(4-aminophenoxy)benzene/1,12-dodecanediamine. 1. materials, preparation, and characterization. Macromolecules1995; 28(20): 6926–6930.
21.
StClairAKStClairTL. Addition polyimide adhesives containing ATBN and silicone elastomers. Int J Adhes Adhes1981; 1(5): 249–255.
22.
BryantRGJensonBJHergenrotherPM. Chemistry and properties of a phenylethynyl-terminated polyimide. J Appl Polym Sci1996; 59(8): 1249–1254.
23.
ConnellJWSmithJGHergenrotherPMRommelML. Neat resin, adhesive and composite properties of reactive additive/PETI-5 blends. High Perform Polym2000; 12(2): 323–333.
24.
JensenBJChangAC. Synthesis and characterization of modified phenylethynyl imides. High Perform Polym1998; 10(2): 175–180.
25.
RobertoJCJensenBJ. Effect of molecular weight on adhesive properties of the phenylethynyl-terminated polyimide LARCTM-PETI-5. Hampton, VA, USA: NASA, 1994, Report TM-1994-111558.
26.
ProgarDJ. Adhesive evaluation of LARC-TPI and a water-soluble version of LARC-TPI. Int J Adhes Adhes1986; 6(1): 12–20.
27.
JensenBJHouTHWilkinsonSP. Adhesive and composite properties of adhesive and composite LARC(TM)-8515 polyimide. High Perform Polym1995; 7: 11–21.
28.
ProgarDJStClairTL. Adhesive bonding study of amorphous LARCTM-TPI. J Adhes Sci Technol1994; 8(1): 67–83.
29.
SaeedMBZhanMS. Adhesive strength of partially imidized thermoplastic polyimide films in bonded joints. Int J Adhes Adhes2007; 27(1): 9–19.
30.
ConnellJWSmithJGHergenrotherPM. Imide oligomers containing pendent and terminal phenylethynyl groups - II. High Perform Polym1998; 10(3): 273–283.
WangKYangSYFanLZhanMSLiuJG. Preparation and properties of molecular-weight-controlled polyimides derived from 1,4-bis(4′-amino-2′-trifluoromethylphenoxy)benzene and 4,4′-oxydiphthalic anhydride. J Polym Sci, Part A: Polym Chem2006; 44(6): 1997–2006.
33.
SmithJGConnellJWHergenrotherPMFordLACrissJM. Transfer molding imide resins based on 2,3,3′,4′-biphenyltetracarboxylic dianhydride. In: Proceedings of 4th International Symposium on Polycondensates, Hamburg, Germany, 2002, pp. 401–418.
34.
SasakiTMoriuchiHYanoSYokotaR. High thermal stable thermoplastic-thermo setting polyimide film by use of asymmetric dianhydride (α-BPDA). Polymer2005; 46(18): 6968–6975.
35.
HasegawaMShiZYokataRHeFFOzawaH. Thermo-processable polyimides with high Tg and high thermo-oxidative stability as derived from 2,3,3′,4′-biphenyltetracarboxylic dianhydride. High Perform Polym2001; 13(4): 355–364.
36.
XieKZhangSYLiuJGHeMHYangSY. 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(15): 2581–2590.
37.
MyungBYAhnCJYoonTH. Adhesion property of novel polyimides with 1-[3′,5′-bis(trifluoromethyl)phenyl. pyromellitic dianhydride. J Appl Polym Sci2005; 96(5): 1801–1809.
38.
ZhaoXJLiuJGYangHXFanLYangSY. Novel polyfluorinated polyimides derived from α,α-bis(4-amino-3,5-difluorophenyl) phenylmethane and aromatic dianhydrides: Synthesis and characterization. Eur Polym J2008; 44(3): 808–820.
39.
ProgarDJ. Processing study of a high temperature adhesive. Int J Adhes Adhes1984; 4(2): 79–86.
40.
HanYFangXZZuoXX. The influence of molecular weight on properties of melt-processable copolyimides derived from thioetherdiphthalic anhydride isomers. J Mater Sci2010; 45(7): 1921–1929.
41.
TongYJHuangWXLuoJDingMX. Synthesis and properties of aromatic polyimides derived from 2,2′,3,3′-biphenyltetracarboxylic dianhydride. J Polym Sci, Part A: Polym Chem1999; 37(10): 1425–1433.
42.
HergenrotherPMWatsonKASmithJGJrConnellJWYokotaR. Polyimides from 2,3,′4′-biphenyltetracarboxylic dianhydride and aromatic diamines. Polymer2002; 43(19): 5077–5093.
