Design and characterization of thermosetting polyimide structural adhesive and composite matrix systems

Tan, Bi-yi; Vasudevan, Venkatesh; Lee, Y. J.; Gardner, S.; Davis, Richey M.; Bullions, Todd A.; Loos, Alfred C.; Parvatareddy, H.; Dillard, David A.; McGrath, James E.; Cella, James A.

doi:10.1002/(sici)1099-0518(199710)35:14<2943::aid-pola15>3.0.co;2-j

Cited by 30 publications

(16 citation statements)

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“…Although the polyimides showed high thermostability, most of them had a glass transition temperature ( T g ) of below 400 °C, implying that they could be further improved. In many cases, an efficient strategy for enhancement of the heat resistance of polyimides is to attach crosslinkable groups to the backbones of the polyimides . However, too many crosslinkable groups may lead to a high crosslinking density in the polymers, which makes polyimides brittle.…”

Section: Resultsmentioning

confidence: 99%

“…In many cases, an effi cient strategy for enhancement of the heat resistance of polyimides is to attach crosslinkable groups to the backbones of the polyimides. [30][31][32][33][34][35][36][37] However, too many crosslinkable groups may lead to a high crosslinking density in the polymers, which makes polyimides brittle. Thus, to realize a balance between the mechanical properties and the thermal properties of the polyimides, attention is needed.…”

Section: The Application Of the New Diamine As A Modifi Er For The Enmentioning

confidence: 99%

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A Novel Thermo‐Polymerizable Aromatic Diamine: Synthesis and Application in Enhancement of the Properties of Conventional Polyimides

Luo

Sun

Wang

et al. 2016

Macro Chemistry & Physics

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Owing to their important application in the production of high performance materials, aromatic diamines have received interest in many areas for several years. However, most of the polymers derivated from diamines show poor processability due to their rigid backbone. Although much effort has been made, a balance between the solvent (or heat)-resistance and processability of the polymers still needs to be achieved. In this contribution, a new aromatic diamine is reported, which has both reactive amine groups and thermo-polymerizable benzocyclobutene moieties. Starting from the diamine can not only give the corresponding polymers, such as polyamides, polyimides, and polyurethanes, but can also provide new structural materials through the post-polymerization of the polymers. It is found that adding diamine into a conventional polyimide system can greatly improve the properties of the polyimide, such as T g , coeffi cient of thermal expansion, tensile strength, and storage modulus. When the content of the diamine is in the range ≈ 5-10 mol%, the tensile strength of the conventional polyimide is increased by up to 30%. The highest T g (> 400 °C) is observed when the content of the diamine is 40 mol%. the polymers derivated from diamines show poor processability, mainly due to the inherent rigid backbone of the diamine. For example, polyamides [ 1 ] based on aromatic diamines are insoluble in common organic solvents. Moreover, polyimides [2][3][4][5] derived from rigid diamines are infusible and partly soluble in solvents with strong polarity. In order to reduce the rigidity of aromatic diamines, a general strategy is to attach side chains to the backbone of the diamines [ 6 ] or introduce fl exible ether bonds to the molecules. [ 7 ] Nevertheless, an improvement in rigidity is usually accompanied by a decrease in the solvent resistance and heat resistance of the polymers. Hence, exploration and development of new aromatic diamines with excellent properties is necessary.Recently, we have found that postpolymerization is an effi cient and simple way to realize the balance

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Section: Resultsmentioning

confidence: 99%

Section: The Application Of the New Diamine As A Modifi Er For The Enmentioning

confidence: 99%

A Novel Thermo‐Polymerizable Aromatic Diamine: Synthesis and Application in Enhancement of the Properties of Conventional Polyimides

Luo

Sun

Wang

et al. 2016

Macro Chemistry & Physics

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“…Usually a cross‐linkable end capping group is necessary to be introduced into the reactive end capped polyimides. The reactive end capping agents which are commonly used in the polyimide matrix resins including maleic anhydride, nadic anhydride, and phenylethynylphthalic anhydride . However, for conventional cross‐linkable groups, the cross‐linking reaction could not produce thermoset with fully aromatic molecular structure because of the possible remaining of aliphatic residues in the final products.…”

Section: Introductionmentioning

confidence: 99%

Fully aromatic macrocycle‐terminated polyimide: synthesis and cross‐linking

Zhang

Jiang

et al. 2013

Polymers for Advanced Techs

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This study reported a method to prepare fully aromatic macrocycle‐terminated polyimides (MC‐PI). The macrocycle of aryl ether ketones was prepared from (4‐amino)phenylhydroquinone and a di‐fluoro monomer under pseudo high dilution condition. Novel aromatic fully MC‐PI oligomers were successfully prepared by the reaction of 2,3,3′,4′‐biphenyltetracarboxylic diandhydride with 2,5‐bis(4′‐aminophenoxy)‐biphenyl and sulfur‐containing macrocycle of aryl ether ketone. The MC‐PI oligomers were cross‐linkable in the heating, and the glass transition temperatures of the polyimides increased after thermally cured. The cross‐linking reaction of MC‐PI could form fully aromatic thermosetting polyimide by ring‐opening reaction. After cross‐linking, these polyimides showed higher glass transition temperatures and excellent thermal stability. Copyright © 2013 John Wiley & Sons, Ltd.

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“…General Electric Co. has developed methods leading to PEIs. [17][18][19] The research resulted in the commercial polymer designated as Ultem 1000, which was made from bisphenol A and 1,3-bis(nitrophthalimido)benzene or bisphenol A-derived bis(ether anhydride) and m-phenylenediamine. The medium glass-transition temperature of Ultem is an advantage and is beneficial for commercialization.…”

Section: Introductionmentioning

confidence: 99%

Syntheses and properties of organosoluble poly(ether imide)s from 1,1‐bis[4‐(3,4‐dicarboxyphenoxy)phenyl]cyclohexane dianhydride and aromatic diamines

Yang¹,

Yu²

2001

J. Polym. Sci. A Polym. Chem.

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A bis(ether anhydride) monomer, 1,1-bis [4-(3,4-dicarboxyphenoxy)phenyl-]cyclohexane dianhydride (IV-A), was synthesized from the nitro displacement of 4-nitrophthalodinitrile by the phenoxide ion of 1,1-bis(4-hydroxyphenyl)cyclohexane (I-A), followed by alkaline hydrolysis of the intermediate bis(ether dinitrile) and dehydration of the resulting bis(ether acid). A novel series of organosoluble poly(ether imide)s (VI a-i )(PEIs) bearing cyclohexylidene cardo groups was prepared from the bis(ether anhydride) IV-A with various aromatic diamines V a-i via a conventional two-stage process. The PEIs had inherent viscosities in the range of 0.48 -1.02 dL/g and afforded flexible and tough films by solution-casting because of their good solubilities in organic solvents. Most PEIs showed yield points in the range of 89 -102 MPa at stress-strain curves and had tensile strengths of 78 -103 MPa, elongations at breaks of 8 -62%, and initial moduli of 1.8 -2.2 GPa. The glass-transition temperatures (T g 's) of these PEIs were recorded between 200 -234°C. Decomposition temperatures of 10% weight loss all occurred above 490°C in both air and nitrogen atmospheres, and their residues were more than 43% at 800°C in nitrogen atmosphere. The cyclohexane cardo-based PEIs exhibited relatively higher T g 's, better solubilities in organic solvents, and better tensile properties as compared with the corresponding Ultem PEI system.

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Design and characterization of thermosetting polyimide structural adhesive and composite matrix systems

Cited by 30 publications

References 1 publication

A Novel Thermo‐Polymerizable Aromatic Diamine: Synthesis and Application in Enhancement of the Properties of Conventional Polyimides

A Novel Thermo‐Polymerizable Aromatic Diamine: Synthesis and Application in Enhancement of the Properties of Conventional Polyimides

Fully aromatic macrocycle‐terminated polyimide: synthesis and cross‐linking

Syntheses and properties of organosoluble poly(ether imide)s from 1,1‐bis[4‐(3,4‐dicarboxyphenoxy)phenyl]cyclohexane dianhydride and aromatic diamines

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