High‐performance composites from polyimide matrix resins that utilize a cross linking reaction of biphenylene end‐caps with acetylene units in the main chain

Stoessel, S. J.; Takeichi, Tsutomu; Stille, J. K.; Alston, William B.

doi:10.1002/app.1988.070360811

Cited by 13 publications

(3 citation statements)

References 21 publications

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“…The synthesis of bis (4-ethynylphenyl) ether (4) was carried out by the palladiumcatalyzed reaction6) of bis (4-iodophenyl) ether with tributylethynylstannane. In addition, bis(acety1ene) monomer 5 was synthesized by the coupling reaction of bis (4-bromophenyl) ether with phenylacetylene in the presence of copper iodide and a palladium catalyst').…”

Section: Resultsmentioning

confidence: 99%

Synthesis of aromatic polymers by the reaction between monomers containing biphenylene and acetylene groups

1989

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The thermal reaction of a bis(bipheny1ene) monomer, N,N'-bis(biphenyIene-2-y1)-4,4'-hexafluoroisopropylidenediphthalimide (3, with either of two diacetylenic monomers, bis(4-ethynylphenyl) ether (4) or bis[4-(phenylethynyl)phenyl] ether (5). gave polymers that contain phenanthrene units as a result of the reaction of the biphenylene groups with the acetylene groups. The reaction could be carried out in solution or in the melt, and in the latter case, reaction exotherms were found at 367°C and 386"C, respectively, for 4 and 5. Polymer 6, obtained from the melt reaction of 3 with 5, is insoluble in all solvents and thermally stable, showing no weight loss in air up to 480°C and in argon up to 500°C.

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Section: Resultsmentioning

confidence: 99%

Synthesis of aromatic polymers by the reaction between monomers containing biphenylene and acetylene groups

1989

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“…We have introduced internal acetylene units into the backbone of polyimides [11][12][13][14][15][16][17] and oligoimides [18][19][20][21][22][23], and studied the crosslinking behaviour of the acetylene units and properties of the crosslinked polyimides. Crosslinking of the acetylene units gave polyimides that have high T g and excellent thermal stability.…”

Section: Introductionmentioning

confidence: 99%

Preparation and Properties of Poly(Amide-Imide) Containing Acetylene Units in the Main Chain

Takeichi

Suefuji²,

Zuo

2001

High Performance Polymers

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Poly(amide-imide) containing internal acetylene units in the backbone was prepared from trimellitic anhydride chloride and bis(3-aminophenyl)acetylene in N-methyl-2-pyrrolidone at room temperature, followed by thermal imidization.Differential scanning calorimetry measurements of the poly(amide-imide) showed an exotherm due to the crosslinking reaction of the internal acetylene units. With higher heat treatment, the exotherm shifted to higher temperatures and the amount of the exotherm decreased. The exotherm finally disappeared after 400 • C treatment. Viscoelastic measurements revealed that the crosslinked polymer had a higher glass transition temperature and maintained a storage modulus up to higher temperatures. The thermogravimetric analyses profile showed that the crosslinking of internal acetylene units gave a thermally stable structure.

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“…Imide oligomers containing "masked" dienes in the form of benzocyclobutene [14, 151 and biphenylene [16] have been reported. The reactive diene, oquinodimethane (2-xylylene), is generated by tKe thermal electrocyclic ring opening of the strained four-membered ring of benzocyclobutene.…”

Section: Introductionmentioning

confidence: 99%

Preparation of polyimides utilizing the Diels–Alder reaction, II: Bis[N‐(butadienyl‐2‐methyl)] amino arylenes with bismaleimides

Smith

Ottenbrite

1992

Polymers for Advanced Techs

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Four new bisdienes were prepared from 2-bromomethyl-1,3-butadiene and N,N'-diethyl benzidine; bis144Nethyl) aminophenyll-p-diisopropyl benzene, 1,4-diamino-2,3,5,6-tetramethylbenzene and a,a' bis(4-amino-3,5dimethyl pheny1)-p-diisopropyl benzene. Polyimides were synthesized by the Diels-Alder reaction of these bisdienes and bis(4-maleimidylpheny1)methane and bis(3maleimidylphenyl) sulfone. The polymers were soluble in m-cresol, dimethyl sulfoxide and chlorinated hydrocarbon solvents. Moderate thermal stability was observed by thermogravimetric analysis in air and nitrogen.

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High‐performance composites from polyimide matrix resins that utilize a cross linking reaction of biphenylene end‐caps with acetylene units in the main chain

Cited by 13 publications

References 21 publications

Synthesis of aromatic polymers by the reaction between monomers containing biphenylene and acetylene groups

Synthesis of aromatic polymers by the reaction between monomers containing biphenylene and acetylene groups

Preparation and Properties of Poly(Amide-Imide) Containing Acetylene Units in the Main Chain

Preparation of polyimides utilizing the Diels–Alder reaction, II: Bis[N‐(butadienyl‐2‐methyl)] amino arylenes with bismaleimides

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