Thermosetting Polyimide Resins and Composites Derived from 2-Phenyl-4,4'-oxydianiline†

doi:10.7503/cjcu20160243

Abstract

Abstract:

A series of imide oligomers with a degree of polymerization of 1, 2 and 3 was synthesized via a conventional two-step procedure, using 2-phenyl-4,4'-oxydianiline(p-ODA) and isomeric oxydiphthalic anhydrides as the monomers, and 4-phenylethynyl phthalic anhydride(4-PEPA) as the end-capping reagent. These imide oligomers were fully characterized in terms of solubility, melt viscosity, and thermal properties of cured resins. The solubility of imide oligomers based on 2-phenyl-4,4'-oxydianiline were higher than 30% in common organic solvents, such as N,N-dimethylacetamide(DMAc), tetrahydrofuran(THF), and 1,4-dioxane. The minimum melt viscosities for these oligomers were lower than 10 Pa·s, which was indicative of their excellent processability. Furthermore, the cured resins possessed good thermal properties, with glass transition temperatures(T_g) and 5% weight loss temperatures(T_5%) being up to 300 and 545 ℃, respectively. These resins were then formulated into carbon-fiber-reinforced composites, and the composite properties were studied. Composite PIC-4,4'-ODPA-2 displayed the best mechanical properties at both ambient and elevated temperatures.

Key words: Polyimide, 2-Phenyl-4, 4'-oxydianiline, Solubility, Mechanical property, Carbon-fiber-reinforced composite

CLC Number:

O633.2

TrendMD:

FAN Weifeng, LIU Xiuju, YAN Jingling, MENG Xiangsheng, LIU Jingfeng, WANG Zhen. Thermosetting Polyimide Resins and Composites Derived from 2-Phenyl-4,4'-oxydianiline^†[J]. Chem. J. Chinese Universities, 2016, 37(10): 1926.

Figures/Tables 9

References 28

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Oligomer	M_nC	M_n	M_w	PDI
PI-4,4'-ODPA-1	1287	1476	2385	1.62
PI-4,4'-ODPA-2	1838	2042	3777	1.85
PI-4,4'-ODPA-3	2388	2557	5041	1.97
PI-3,4'-ODPA-1	1287	1192	1669	1.40
PI-3,4'-ODPA-2	1838	1683	2677	1.59
PI-3,4'-ODPA-3	2388	1707	2735	1.60
PI-3,3'-ODPA-1	1287	1325	2218	1.67
PI-3,3'-ODPA-2	1838	1746	2971	1.70
PI-3,3'-ODPA-3	2388	2195	4202	1.91

Oligomer	M_nC	M_n	M_w	PDI
PI-4,4'-ODPA-1	1287	1476	2385	1.62
PI-4,4'-ODPA-2	1838	2042	3777	1.85
PI-4,4'-ODPA-3	2388	2557	5041	1.97
PI-3,4'-ODPA-1	1287	1192	1669	1.40
PI-3,4'-ODPA-2	1838	1683	2677	1.59
PI-3,4'-ODPA-3	2388	1707	2735	1.60
PI-3,3'-ODPA-1	1287	1325	2218	1.67
PI-3,3'-ODPA-2	1838	1746	2971	1.70
PI-3,3'-ODPA-3	2388	2195	4202	1.91

Oligomer	Acetone	THF	1,4-Dioxane	DMF	DMAc	DMSO	NMP
PI-4,4'-ODPA-1	±	++	++	++	++	++	++
PI-4,4'-ODPA-2	-	++	++	++	++	++	++
PI-4,4'-ODPA-3	-	++	++	++	++	++	++
PI-3,4'-ODPA-1	±	++	++	++	++	++	++
PI-3,4'-ODPA-2	±	++	++	++	++	++	++
PI-3,4'-ODPA-3	±	++	++	++	++	++	++
PI-3,3'-ODPA-1	±	++	++	++	++	++	++
PI-3,3'-ODPA-2	±	++	++	++	++	++	++
PI-3,3'-ODPA-3	±	++	++	++	++	++	++

Oligomer	Acetone	THF	1,4-Dioxane	DMF	DMAc	DMSO	NMP
PI-4,4'-ODPA-1	±	++	++	++	++	++	++
PI-4,4'-ODPA-2	-	++	++	++	++	++	++
PI-4,4'-ODPA-3	-	++	++	++	++	++	++
PI-3,4'-ODPA-1	±	++	++	++	++	++	++
PI-3,4'-ODPA-2	±	++	++	++	++	++	++
PI-3,4'-ODPA-3	±	++	++	++	++	++	++
PI-3,3'-ODPA-1	±	++	++	++	++	++	++
PI-3,3'-ODPA-2	±	++	++	++	++	++	++
PI-3,3'-ODPA-3	±	++	++	++	++	++	++

Polymer	Imide oligomer		Cured resin
Polymer	T_g/℃(DSC)	Minimum melt viscosity/(Pa·s)	T_g/℃(DSC)	T_g/℃(DMA)	T_5%/℃(N₂)
PI-4,4'-ODPA -1	146	1.7(312 ℃)	300	337	541
PI-4,4'-ODPA -2	170	6.9(326 ℃)	285	313	540
PI-4,4'-ODPA -3	184	7.4(341 ℃)	271	292	545
PI-3,4'- ODPA -1	142	0.6(309 ℃)	279	308	520
PI-3,4'- ODPA -2	166	1.2(320 ℃)	255	283	528
PI-3,4'- ODPA -3	172	3.1(324 ℃)	239	265	539
PI-3,3'- ODPA -1	156	3.4(300 ℃)	283	310	519
PI-3,3'- ODPA -2	179	2.8(325 ℃)	265	275	519
PI-3,3'- ODPA -3	198	4.0(355 ℃)	266	276	524