Synthesis and characterization of new soluble polyamides from Acenaphtohydrazinomercaptotriazole diamine

Mighani, Hossein; Kia, Najmeh

doi:10.1590/0104-1428.1912

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Seção Técnica • Polímeros 25 (4) • Jul-Aug 2015 • https://doi.org/10.1590/0104-1428.1912 copy

Synthesis and characterization of new soluble polyamides from Acenaphtohydrazinomercaptotriazole diamine

Authorship SCIMAGO INSTITUTIONS RANKINGS

Abstract

A diamine Acenaphtohydrazinomercaptotriazole (AHTD) was synthesized in one step from acenaphthoqinone and 4-amino-3-hydrazino-5-mercapto-1,2,4-triazole. The diamin was characterized by FTIR, ¹HNMR, ¹³CNMR and melting point. Diamin was used to prepare novel polyamides. The low temperature solution polycondensation of diamin with tow aromatic and tow aliphatic diacid chlorides afforded diamin-containing polyamides with inherent viscosities of 0.38–0.47 dl/g in DMF at 25 °C. The polyamides were generally soluble in a wide range of solvents such as dimethylformamide(DMF), N-Methylpyrolidone(NMP), tetrachloroethane (TCE), dimethylsulfoxide(DMSO) and H₂SO₄. Thermal analysis showed that these polyamides were practically crustily and with T_g under 100 °C.

Keywords:
polyamides; thermalstability; polycondensation; acenaphthoqinone

Substrate	IR (KBr, cm_1)	NMR (DMSO-d6, δ, ppm)	Elemental analysis
			Calc.			Found
			C	H	N	C	H	N
AHTD	3150-3446 cm^–1 (NH and NH₂ asymmetric and symmetric stretch), 2980 (C-H aromatic ring), 1638(C=N), 1590 (C=C), 908(C-S)	12.7-12.9(NH), 7.78, 8.3(CH,Aromatic), 5.7(NH2), 1.1(SH)	43.84	3.19	38.35	44.12	3.25	37.92
PA1	3430(N-H), 3100 (C-H aromatic), 1790 (C=O), 1631 (C=N), 1527(C=C aromatic), 910(C-S)	12.7(NH), 7.8 - 8.8 (CH Aromatic), 1.1(SH)	50.70	2.82	29.57	51.02	2.98	28.98
PA2	3300(N-H), 3117 (N-H), 2965 (C-H aromatic), 1636 (C=O), 1560 (C=N), 1508(C=C aromatic), 910(C-S)	12.7(NH), 7.8 - 8.8 (CH Aromatic), 1.1(SH)	50.70	2.82	29.57	51.32	3.02	28.83
PA3	3210(N-H), 3000 (C-H aromatic), 2800(C-H aliphatic) 1638 (C=O), 1590 (C=N), 1476(C=C aromatic), 910(C-S)	12.8(NH), 7.1 - 8.4 (CH Aromatic), 1.9 – 2.1(CH2), 1.1(SH)	48.17	3.65	30.65	47.92	3.56	31.03
PA4	3430(N-H), 2900 (C-H aliphatic) 1636 (C=O), 1570(C=N), 1505(C=C aromatic), 910(C-S)	12.8(NH), 7.1 - 8.4 (CH Aromatic), 1.9 - 2.8(CH2), 1.1(SH)	51.65	4.64	27.81	51.89	4.35	28.12

Polym. code	NMP	DMF	DMSO	TCE	THF	H2SO₄	HMPA	DMAC	Aceton	Ethanol	Methanol	CHCl₃
AHTD	+	+	+	+	+	+	+	+	+	+	+	±
PA1	+	+	+	±	+	+	+	+	-	±	-	±
PA2	+	+	+	±	+	+	+	+	-	±	-	±
PA3	+	+	+	±	+	+	±	+	-	±	-	±
PA4	+	+	+	±	+	+	±	+	-	±	-	±

Compound code	T_g	T_c	T_m	T₁₀(°C)^a a 10% weight loss.	T₂₅(°C)^b b 25% weight loss.	T₅₀(°C)^c	%Ch. Y. ^d d Char yield percent at 600 °C, obtained from TGA.	η_inh (dl/g)^e e Measured in DMF at 25 °C (c=0.5 g/dl).
AHTD	-	-	260	-	-	-	-	0.04
PA1	90	251	320	230	320	420	42	0.38
PA2	65	251	330	230	400	-	60	0.42
PA3	55	251	310	220	310	450	38	0.45
PA4	50	240	310	180	290	340	16	0.47

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[1] * h.mighani@gu.ac.ir