加成型酚醛改性双马树脂及其复合材料性能

姜伟芳; 王林祥; 郑庆; 袁荞龙; 黄发荣

doi:10.13801/j.cnki.fhclxb.20220321.004

加成型酚醛改性双马树脂及其复合材料性能

doi: 10.13801/j.cnki.fhclxb.20220321.004

1.
华东理工大学　材料科学与工程学院特种功能高分子材料及相关技术教育部重点实验室，上海 200237
2.
上海新力动力设备研究所，上海 200125

基金项目: 上海航天科技创新基金(SAST2019-106)；中央高校基本科研业务费专项资金(JKD01211701)Shanghai Aerospace Science and Technology Innovation Fund (SAST2019-106); Fundamental Research Funds for the Central Universities (JDK01211701)

详细信息

通讯作者:
袁荞龙，博士，教授，研究方向为耐高温树脂的制备改性及其复合材料性能研究　E-mail: qlyuan@ecust.edu.cn

中图分类号: TB332
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出版历程
- 收稿日期: 2022-01-04
- 修回日期: 2022-01-28
- 录用日期: 2022-02-19
- 网络出版日期: 2022-03-22
- 刊出日期: 2023-02-15

Properties of bismaleimide resin modified by addition-curing phenolic and their composites

1.
Key Laboratory of Specially Functional Polymeric Materials and Related Technology of the Ministry of Education, School of Materials Science and Engineering, East China University of Science and Technology, Shanghai 200237, China
2.
Shanghai Xinli Power Equipment Institute, Shanghai 200125, China

摘要

摘要: 双马来酰亚胺(BMI)树脂因其优异的性能已在航空航天、电子和其他工业领域获得应用，为满足其在高速飞行器结构件中需求，用加成型酚醛树脂改性BMI体系以改善其热-力学性能。通过Williamson醚化反应合成了炔丙基醚化酚醛树脂(PN)和烯丙基醚化酚醛树脂(AN)，采用熔融共混法分别与N, N’-(4, 4’-亚甲基二苯基)双马来酰亚胺(BDM)和2, 2’-二烯丙基双酚A(DABPA)树脂体系(BD)共混，制备了三元热固性树脂：PN改性BD(BDPN)和AN改性BD(BDAN)。研究了两种加成型酚醛树脂改性的BD树脂体系的加工工艺性和固化行为的变化，并对改性前后固化树脂及其复合材料的热、力学性能进行了研究。结果表明：共混树脂体系都在极性溶剂中有好的溶解性，加工窗口都有50℃以上。BDPN和BDAN固化反应只有一个放热峰，最高放热峰值温度比BD树脂低。用FTIR跟踪验证了BD、BDPN和BDAN树脂体系发生的Ene、Diels-Alder、Claisen重排和炔基与马来酰亚胺环的聚合反应。PN热氧稳定性好，改性的BDPN固化树脂空气中质量损失5wt%的温度(T_d5)高于400℃，800℃残留率(Y_r800℃)由3.7%提升至23.1%。BD、BDPN和BDAN固化物的极限氧指数(LOI)分别为30.2%、32.5%和31.0%，都属难燃材料。BDPN和BDAN树脂浇铸体冲击强度和弯曲模量分别提高了19%和30%，但弯曲强度都因交联密度的下降而有所下降。BDPN和BDAN固化物的吸水率都低于BD树脂，沸水中40 h时BDPN和BDAN分别比BD树脂降低了8.6%和14%。室温下T300碳纤维增强BDAN复合材料(T300CF/BDAN)弯曲强度、弯曲模量和层间剪切强度(ILSS)高于BD基复合材料；200℃下T300CF/BDPN的弯曲强度达575 MPa，保留率高达98.6%。炔丙基醚化酚醛树脂改性双马来酰亚胺树脂体系有望应用于耐200℃的复合材料结构件，为耐热双马来酰亚胺树脂的制备提供新的途径。
- 炔丙基醚化酚醛 /
- 烯丙基醚化酚醛 /
- 双马来酰亚胺树脂 /
- 改性共混 /
- 热-物理性能
Abstract: Bismaleimide (BMI) resin has been widely used in aerospace, electronics and other industrial fields because of its excellent properties. In order to meet the needs of structural components for high-speed aircraft, the additional phenolic modifier is introduced to improve the thermo-mechanical properties of BMI resin. The propargyl etherified novolac (PN) and allyl etherified phenolic (AN) as an addition modifier were synthesized by Williamson etherification. The PN and AN were used to modify N, N'-(4, 4'-diphenylmethylane) bismaleimide (BDM)/2, 2'-diallyl bisphenol A (DABPA) resin system (BD) in melting mixing to obtain the ternary blended resins of BDPN and BDAN. The processability and cure reactions of the BDPN and BDAN were studied. The thermal property and mechanical property of the cured BD, BDPN and BDAN were further investigated. The results show that the ternary blended resins exhibit good solubility and meltability, and have an above 50℃ of process window. There is only a single exothermal peak in DSC curves of BDPN and BDAN. The peak temperatures of BDPN and BDAN are lower than that of BD. The Fourier transform infrared (FTIR) was used to monitor the curing reactions of BD, BDPN and BDAN resins. The reactions of Ene, Diels-Alder, Claisen rearrangement and addition of alkyne and maleimido group were detected during curing. The cured PN resin has good thermo-oxidative stability. The residual yield at 800℃ (Y_r800℃) of cured BD in air increases from 3.7% to 23.1% after the BD resin was modified with PN resin. The temperature of 5wt% mass loss (T_d5) of the cured BDPN in air is higher than 400℃. The limited oxygen index (LOI) of the cured BD, BDPN and BDAN resins are 30.2%, 32.5% and 31.0%, respectively. The cured resins are nonflammable. The impact strength and flexural modulus of the cured BD resin increase with addition of PN and AN resins. The impact strength and flexural modulus of the cured AN modified BD resin increase by 19% and 30% respec-tively. However, the flexural strength of the BDPN and BDAN resins decrease since the crosslinked density of the cured modified resins decline. The water absorption in boiling water of the cured BDPN and BDAN resins are lower than that of the cured BD resin, and decrease by 8.6% and 14% after 40 h. The flexural strength, flexural modulus and interlaminar shear strength (ILSS) of the T300 carbon fiber cloth (T300CF) reinforced BDAN composite (T300CF/BDAN) at room temperature are higher than that of the T300CF reinforced BD composite. The flexural strength of the T300CF/BDPN at 200℃ retains a 98.6% retention, reaches to 575 MPa. The propargyl etherified novolac can used to improve the heat properties of bismaleimide which is a new approach for modification of bismaleimides, and promising to be utilized in preparation of the structural components of composite with heat-resistance at 200℃.
- propargyl etherified novolac /
- allyl etherified novolac /
- bismaleimide resin /
- blending modification /
- thermo-physical property

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图 1 炔丙基醚化和烯丙基醚化酚醛树脂合成路径

Figure 1. Synthesis routes of propargyl novolac and allyl novolac

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图 2 N, N’-(4, 4’-亚甲基二苯基)双马来酰亚胺(BDM)-2, 2’-二烯丙基双酚A(BD)、BD-炔丙基醚化酚醛树脂(PN)(BDPN)和BD-烯丙基醚化酚醛树脂(AN)(BDAN)共混树脂的黏温曲线

Figure 2. Viscosity of the N, N'-(4, 4'-diphenylmethylane)bismaleimide (BDM)-2, 2'-diallyl bisphenol A (BD), BD-propargyl etherified novolac (PN) (BDPN) and BD-allyl etherified phenolic (AN) (BDAN) blended resins against temperature

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图 3 PN、AN (a) 和共混树脂 (b) 的DSC曲线

Figure 3. DSC curves of PN, AN (a) and blended resins (b)

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图 4 共混树脂的固化机制 (a) 和BD (b)、BDPN (c)、BDAN (d) 共混树脂的FTIR图谱

Figure 4. Proposed curing reactions in the blended resins (a) and FTIR spectras of BD (b), BDPN (c) and BDAN (d) resins

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图 5 PN、AN和共混树脂固化物在N₂ (a) 和空气 (b) 气氛下的TGA及DTG曲线；共混树脂未固化前的DSC曲线 (c) 和共混树脂固化后的DMA曲线 (d)

Figure 5. TGA and DTG curves of the cured PN, AN and blended resin in N₂ (a) and air (b) atmosphere; DSC curves of uncured blended resins (c) and DMA curves of cured blended resins (d)

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图 6 共混树脂BD (a)、BDPN (b) 和BDAN (c) 浇铸体的冲击断面SEM图像及BDPN (d) 和BDAN (e) 浇铸体断面EDS能谱图

Figure 6. SEM images of fracture surfaces of cured BD (a), BDPN (b) and BDAN (c) resins and EDS images of fracture surfaces of cured BDPN (d) and BDAN (e) resins

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图 7 共混树脂固化物吸水率随时间的变化曲线

Figure 7. Changes curves of water absorption of the cured blended resins with time

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图 8 T300CF/BD、T300CF/BDPN和 T300CF/BDAN复合材料在室温下 ((a)~(c)) 和200℃下 ((d)~(f)) 断面的SEM图像

Figure 8. SEM images of fracture surfaces of T300CF/BD, T300CF/BDPN and T300CF/BDAN composites at room temperature ((a)-(c)) and 200℃ ((d)-(f))

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表 1 AN、PN和共混树脂的DSC数据结果

Table 1. DSC results of the AN, PN and blended resins

Resin	T_i/℃	T_p1/℃	T_p2/℃	T_f/℃	ΔH/(J·g⁻¹)	ΔH-cured/(J·g⁻¹)	Retention of ΔH/%
PN	188	253	−	329	659.3	−	−
AN	175	221	349	383	288.7	−	−
BD	145	196	248	287	402.0	49.9	12.4
BDPN	182	232	−	306	392.0	25.3	6.5
BDAN	175	235	−	289	299.3	13.5	4.5
Notes: T_i—Initial exothermic temperature; T_p1—First exothermic peak temperature; T_p2—Second exothermic peak temperature; T_f —End exothermic temperature; ΔH—Exothermic enthalpy of uncured resins; ΔH-cured—Exothermic enthalpy of cured resins.

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表 2 PN、AN和共混树脂固化物的TGA、DTG、DMA及未固化树脂DSC数据结果

Table 2. TGA, DTG and DMA results of the cured PN, AN and blended resins and DSC results of the uncured resins

Resin	N₂			Air			T_g-uncured/℃	T_g-cured/℃	M_C
Resin	T_d5/℃	Y_r800℃/%	T_dmax/℃	T_d5/℃	Y_r800℃/%	T_dmax/℃	T_g-uncured/℃	T_g-cured/℃	M_C
PN	406	58.47	432	409	30.76	412	–	–	–
AN	403	45.46	450	419	0.81	445	–	–	–
BD	399	32.70	451	418	3.70	443	11.93	313	129.54
BDPN	403	45.84	438	408	23.13	438	20.32	320	130.14
BDAN	407	35.89	452	409	11.84	450	23.95	240	180.51
Notes: T_d5—Temperature at 5wt% mass loss; Y_r800℃—Residual yield at 800℃; T_dmax—Maximum temperature of thermogravimetric rate; T_g-uncured—Glass transition temperature of uncured resins; T_g-cured—Glass transition temperature of cured resins; M_C—Average molecular mass of polymer between cross-linked nodes.

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表 3 共混树脂的极限氧指数(LOI)

Table 3. Limit oxygen index (LOI) of the cured blended resins

Cured resin	Y_r600℃/%	LOI (Van K-H)	Real LOI
BD	44.32	35.2	30.2
BDPN	51.58	38.1	32.5
BDAN	46.76	36.2	31.0
Notes: Y_r600℃—Char yield at 600℃; Van K-H—An empirical equation used to reckon LOI value.

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表 4 共混树脂浇铸体的力学性能

Table 4. Mechanical properties of blended resins

Cured resin	Impact strength /(kJ·m⁻²)	Flexural strength /MPa	Flexural modulus /GPa
BD	14.70±1.35	151.00±5.48	3.00±0.24
BDPN	14.80±0.11	146.10±13.39	3.90±0.04
BDAN	17.50±0.79	139.00±7.07	3.90±0.06

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表 5 T300碳纤维(T300CF)/共混树脂复合材料在室温及200℃下的力学性能

Table 5. Mechanical properties of T300 carbon fiber cloth (T300CF)/blended resin composites at room temperature and 200℃

Matrix	Temperature/ ℃	Flexural strength/MPa	Retention of flexural strength/%	Flexural modulus/ GPa	ILSS/ MPa	Retention of ILSS/ %
BD	25	572.10±3.70	—	53.10±1.34	44.30±1.13	—
BDPN		583.10±17.84	—	54.10±2.50	40.40±2.47	—
BDAN		639.30±14.01	—	54.90±0.64	46.00±0.69	—
BD	200	563.30±16.67	98.5	—	39.20±0.30	88.5
BDPN		575.00±10.00	98.6	—	32.10±0.44	79.4
BDAN		543.30±6.67	85.0	—	26.40±0.29	57.4
Note: ILSS—Interlaminar shear strength.

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表 6 共混树脂的DMA分析结果

Table 6. DMA analysis results of blended resins

Cured resin	E_g/MPa	E_r/MPa	E_g/E_r
BD	1494.4	297.4	5.0
BDPN	399.1	212.2	1.9
BDAN	560.7	75.5	7.4
Notes: E_g—Modulus at the temperature T₁(T₁=T_g–20℃) obtained from DMA data; E_r—Modulus at the temperature T₂(T₂=T_g+20℃) obtained from DMA data; T_g—glass transition temperature.

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