CN101007778A - Chain-prolonged type fluorenyl bimaleimide and its preparation method - Google Patents
Chain-prolonged type fluorenyl bimaleimide and its preparation method Download PDFInfo
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- CN101007778A CN101007778A CN 200710036307 CN200710036307A CN101007778A CN 101007778 A CN101007778 A CN 101007778A CN 200710036307 CN200710036307 CN 200710036307 CN 200710036307 A CN200710036307 A CN 200710036307A CN 101007778 A CN101007778 A CN 101007778A
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Abstract
本发明属高分材料技术领域，具体为一种新结构的链延长型芴基双马来酰亚胺及其制备方法。具体过程为：在低温，惰性气体保护下，9，9－双(4－氨基苯基)芴溶解于N，N－二甲基乙酰胺等非质子极性溶剂中，搅拌下滴加等摩尔马来酸酐的N，N－二甲基乙酰胺溶液，滴加完毕反应2小时左右，直接加入等摩尔的二酐，继续搅拌反应3小时左右，加入醋酐及醋酸钾的混合物，室温搅拌，反应4小时左右，水中沉淀得到链延长型芴基双马来酰亚胺，收率超过95％。合成的产物在保持双马来酰亚胺的特性的同时，大幅度提高了溶解性及加工性能。The invention belongs to the technical field of high-resolution materials, in particular to a chain-extended fluorenyl bismaleimide with a new structure and a preparation method thereof. The specific process is: at low temperature and under the protection of an inert gas, 9,9-bis(4-aminophenyl)fluorene is dissolved in an aprotic polar solvent such as N,N-dimethylacetamide, and an equimolar The N, N-dimethylacetamide solution of maleic anhydride, react for about 2 hours after the dropwise addition, directly add equimolar dianhydride, continue stirring for about 3 hours, add the mixture of acetic anhydride and potassium acetate, stir at room temperature, After reacting for about 4 hours, the chain-extended fluorenyl bismaleimide is obtained by precipitation in water, and the yield exceeds 95%. The synthesized product greatly improves solubility and processability while maintaining the characteristics of bismaleimide.
Description
Technical field
The invention belongs to technical field of polymer materials, be specifically related to a kind of chain-prolonged type fluorenyl bimaleimide and preparation method thereof.
Background technology
Bimaleimide resin has excellent thermostability, high tensile strength and modulus, excellent chemical resistance and humidity resistance, thus be widely used as the advanced composite material matrix resin as the high-performance thermosetting resin.And by 9, two (4-aminophenyl) the fluorenes synthetic bismaleimide amine monomers 9 of 9-, two (the 4-dimaleoyl imino phenyl) fluorenes (seeing structural formula (A)) of 9-have the performance of many excellences, thermotolerance as excellence, high carbon residue rate, high limiting oxygen index(LOI) (LOI) and good flame retardant resistance etc. and cause that people pay attention to.But this monomer has very high fusing point, and its fusing point is above 300 ℃; And it all has very poor solvability in most organic solvent, thereby for the synthetic and processing of its bismaleimides unusual difficulty all, especially its application in tackiness agent and matrix material.
9, two (4-dimaleoyl imino phenyl) the fluorene structured formulas of 9-
For synthesizing of chain-prolonged type fluorenyl bimaleimide, document Journal of Polymer Science:PartA:Polymer Chemistry edition is only arranged at present, 1982,20 had report, and it has only mentioned and has contained 3,3 ', and the chain extension fluorenyl bimaleimide of 4 ' 4 '-benzophenone tetracarboxylic dianhydride structure, do not go through its synthetic and solvability etc., the chain-prolonged type fluorenyl bimaleimide of more not mentioned other structure.
Summary of the invention
The object of the present invention is to provide that a kind of solvability and processibility are good, the chain-prolonged type fluorenyl bimaleimide of fine heat-resisting performance and preparation method thereof.
Chain elongated fluorenyl bimaleimide provided by the invention, its structural formula is as follows:
Wherein, Ar represents aromatic series or aliphatics dianhydride.Ar specifically can be 3,3 ', 4 ' 4 '-oxygen supports adjacent pyromellitic dianhydride (ODPA), 3,3 ', 4 ' 4 '-benzophenone tetracarboxylic dianhydride (BTDA), bisphenol A-type dianhydride (BPADA), pyromellitic acid anhydride (PMDA), 3,3 ', 4,4 '-bibenzene tetracarboxylic dianhydride (BPDA) etc. also can be other aromatic series or aliphatics dianhydride.
The chain elongated fluorenyl bimaleimide synthetic route that the present invention proposes is as follows:
The synthetic route of chain-prolonged type fluorenyl bimaleimide
Preparation process of the present invention is: at low temperature; under the protection of inert gas; with 9; two (4-aminophenyl) fluorenes of 9-are dissolved in aprotic polar solvent (as N; N-N,N-DIMETHYLACETAMIDE (DMAc) etc.) in; stir the solution that drips the same aprotic polar solvent that waits the mole maleic anhydride down; dropwise; reacted 2.5-3.5 hour, and directly added equimolar aromatic series or aliphatics dianhydride then, continued stirring reaction 2.5-3.5 hour; the mixture that adds aceticanhydride and Potassium ethanoate at last; stirring at room 50-70 minute, 55-65 ℃ was reacted 3-5 hour, and precipitation promptly obtains chain-prolonged type fluorenyl bimaleimide in the water.
In this process, low temperature range can be between-20 ℃～+ 20 ℃, and aprotic polar solvent can also be N, N-dimethylformamide or N-Methyl pyrrolidone etc.
The chain-prolonged type fluorenyl bimaleimide yield that adopts the present invention to make surpasses 95%%.Obtain confirming through infared spectrum, ultimate analysis and nuclear magnetic resonance spectroscopy product structure.The results are shown in Table 1:
The structural characterization of table 1 chain-prolonged type fluorenyl bimaleimide
| Sample | Molecular formula | FTIR(KBr) | 1H-NMR (DMSO-d6) | Ultimate analysis | Outward appearance |
| I | C 33H 20N 2O 4 | 1770，1707，1 378cm -1(imine structure), 1605cm -1(ethylene linkage) | 7.16 (4H, the alkene proton) 7.24-7.98 (16H, aromatic hydrocarbons proton) | Calculated value: C, 77.94; H, 3.96; N, 5.51 observed values: 6.83; H, 4.15; N, 5.42 | Bright orange |
| II | C 74H 42N 4O 9 | 1777，1716，1 371cm -1(imine structure), 1605 cm -1(ethylene linkage) | 7.16 (4H, the alkene proton) 7.25-7.98 (38H, aromatic hydrocarbons proton) | Calculated value: C, 78.57; H, 3.74; N, 4.95; Observed value: C, 77.08; H, 3.74; N, 4.65; | Yellow |
| III | C 75H 42N 4O 9 | 1778，1716，1 372cm -1(imine structure) 1618cm -1(ethylene linkage) | 7.16 (4H, the alkene proton) 7.24-8.16 (38H, aromatic hydrocarbons proton) | Calculated value: C, 78.80; H, 3.70; N, 4.90; Observed value: C, 74.38; H, 3.65; N, 4.35; | Yellow |
| IV | C 89H 56N 4O 1 0 | 1777，1716，1 370cm -1(imine structure) 1612cm -1(ethylene linkage) | 1.69 (6H, CH3) 7.10 (4H, the alkene proton) 7.11-7.98 (38H, aromatic hydrocarbons proton) | Calculated value: C, 79.69; H, 4.21; N, 4.18; Observed value: C, 78.01; H, 3.74; N, 4.18; | Yellow |
Wherein: (I) (II) (III) structural formula of (IV) is as follows:
All chain-prolonged type fluorenyl bimaleimides and 9, two (the 4-dimaleoyl imino phenyl) fluorenes of 9-are compared, and solvability has significantly raising (seeing Table 2).
The solvability of table 2 chain-prolonged type fluorenyl bimaleimide
| Sample | NMP | DMAc | CHCl 3 | CH 2Cl 2 | DMSO | THF | Acetone |
| I | Ins | Ins | Ins | Ins | S | Ins | Ins |
| II | S | S | S | S | S | S | Ins |
| III | S | S | S | S | S | S | Ins |
| IV | S | S | S | S | S | S | Ins |
A.S, the room temperature dissolving; Ins, insoluble;
Embodiment
In order to implement the present invention better, especially exemplified by example it is described, but is not limitation of the present invention.
Embodiment 1
17.4g (0.05mol) 9, two (4-aminophenyl) fluorenes of 9-are dissolved in 120ml N, in the N-N,N-DIMETHYLACETAMIDE (DMAc), ice bath is cooled to 0 ℃, constantly stir and drip the N that waits the mole maleic anhydride down, the N-dimethylacetamide solution, dropwise reaction after 3 hours, directly add equimolar 3,3 ', 4 ' 4 '-oxygen supports adjacent pyromellitic dianhydride (ODPA), continue stirring reaction after 3 hours, add the mixture of aceticanhydride and Potassium ethanoate, stirring at room 1 hour, 60 ℃ were reacted 4 hours, and precipitation obtains ether acid anhydride chain-prolonged type fluorenyl bimaleimide in the water.
Embodiment 2
Remove and use 0.05mol 3,3 ', outside 4 ' 4 '-benzophenone tetracarboxylic dianhydride, other prescription operation stepss and result and embodiment 1 are just the same, obtain ketone acid anhydride chain-prolonged type fluorenyl bimaleimide.
Embodiment 3
Except that using 0.05mol dihydroxyphenyl propane dianhydride, other prescription operation stepss and result and embodiment 1 are just the same, obtain dihydroxyphenyl propane dianhydride chain-prolonged type fluorenyl bimaleimide.
Thermogravimetric analysis result such as the table 3 and shown in Figure 4 of the fluorenyl bimaleimide that more than obtains after the thermal cyclization homopolymerization, as seen the resin thermostability after the curing of chain-prolonged type fluorenyl bimaleimide is better than the not monomer 9 of chain extension, the cured resin of two (the 4-dimaleoyl imino phenyl) fluorenes of 9-.Therefore, chain-prolonged type fluorenyl bimaleimide can improve processing characteristics and keep thermal stability, resin can be used for the interpolation component of various prepregs, matrix material and tackiness agent simultaneously, improves the thermotolerance of material.
Table 3 solidified chain-prolonged type fluorenyl bimaleimide thermogravimetic analysis (TGA) result
| Solidified sample | Tid (℃) | T5 (℃) | T max (℃) | Yc (％) |
| PI | 439 | 453 | 574 | 60 |
| PII | 455 | 484 | 596 | 58 |
| PIII | 478 | 500 | 598 | 65 |
| PIV | 477 | 485 | 541 | 57 |
The initial decomposition temperature that the Tid=extrapolation obtains
The temperature of T5=weightlessness 5%
T
Max=maximum decomposition temperature
Yc=800 ℃. the carbon residue rate
Claims (4)
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