Novel bismaleimide with naphthalene side group. 1. From 1-naphthaldehyde and 2,6-dimethylaniline

Wang, Chun‐Shan; Leu, Tzong Shyng; Hsu, Kuo-Run

doi:10.1016/s0032-3861(97)10008-8

Cited by 69 publications

(46 citation statements)

References 17 publications

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“…stability of aromatic epoxy polymer, it is reasonable to expect that replacement of the classical phenyl with naphthyl group will result in some certain higher T g , and this result will be accompanied by no detriment to the desirable properties of epoxy monomer and crosslinked network such as processability and moisture-resistance. There have been several reports concerning fundamental studies of naphthalene-moiety-containing epoxy monomers and polyethers, [13][14][15][16][17] into which the stiff structural units are inserted or appended by chemical modification. It has been observed that the T g values of these polymers are markedly higher in comparison with those of phenyl-based analogues.…”

Section: Introductionmentioning

confidence: 99%

Structural Effect on Thermal Cure and Property of Naphthalene‐Based Epoxies: Preparation and Characterization

Xu¹,

Chen²,

Zhang³

et al. 2004

Macro Chemistry & Physics

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Summary: Three naphthalene‐based epoxy monomers containing different size of linkages between two naphthalene rings: CC covalent bond (1), methylene (2), cycloaliphatic hydrocarbon derived from limonene (3) were prepared, and the effect of molecular structure on thermal cure behavior and property analyzed. Judged from the combination of the dynamic DSC and isothermal FTIR results, the cure reactivities were found to increase in the order of 1 > 2 > 3 when dicyandiamide was used in the curing systems, and the situation was slightly different in the monomer/4,4′‐methylenedianiline systems. The differences in reactivity as well as in thermal and mechanical properties for the epoxies can be attributed to the differences of configuration and conformational changes during the formation of crosslinked networks. These thermosets exhibited high glass transition temperature (Tg) and had excellent thermal oxidative resistance.DSC thermograms for epoxy/dicyandiamide systems at a heating rate of 10 °C · min−1.magnified imageDSC thermograms for epoxy/dicyandiamide systems at a heating rate of 10 °C · min−1.

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Section: Introductionmentioning

confidence: 99%

Structural Effect on Thermal Cure and Property of Naphthalene‐Based Epoxies: Preparation and Characterization

Xu¹,

Chen²,

Zhang³

et al. 2004

Macro Chemistry & Physics

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“…The complete disappearance of the carboxylic proton signal at ca 11.0 ppm and the appearance of the ethylene proton signal at ca 6.82 ppm indicate the BMI monomers had been successfully synthesized. Figure 3 shows the 13 C NMR spectra of the BMIs in CDCl 3 . The characteristic signal of the carbonyl group of maleimide ring is seen at 169.6 ppm, whereas the rest of the carbons show good resolution.…”

Section: Resultsmentioning

confidence: 99%

“…Design and synthesis of new bismaleimide monomers is an effective way to improve the performance of the resins. Much of new chain-extended BMI monomers had been synthesized such as bismaleimides containing naphthalene, [2][3][4] phthalide, [5][6][7] polysiloxane, [8][9][10] rigid rod esters, [11] fluorine, [12] phosphorus, [13][14][15] and epoxy backbone. [16,17] 9,9-Bis(4-hydroxyphenyl)fluorene is a monomer, which usually used in polymer materials.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, and curing kinetics of novel bismaleimide monomers containing fluorene cardo group and aryl ether linkage

Zhang

Chen

Gao

et al. 2014

Designed Monomers and Polymers

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Two novel bismaleimide (BMI) monomers containing fluorene cardo group and aryl ether linkage, that is, 9,9-bis [4-(4-maleimidophenoxy)phenyl] fluorene (PF-BMI) and 9,9-bis[4-(4-maleimidophenoxy)-3-methylphenyl] fluorene (MPF-BMI) based on 9,9-bis(4-hydroxyphenyl)fluorene and its derivative were designed and synthesized. The chemical structures of the monomers were confirmed from 1 H NMR, 13 C NMR spectroscopy, and Fourier transform infrared spectroscopy. Both monomers obtained are readily soluble in common organic solvents, such as acetone, dichloromethane, and chloroform, enabling an easy solution processing. The thermal curing behavior of the monomers and their non-isothermal thermal curing processes were investigated using differential scanning calorimetry, displaying that both monomers have lower melt points and broad thermal processing windows. The corresponding kinetic data, for example, activation energy (E a ), pre-exponential factor (A), and the order of the reaction (n), were obtained by the Kissinger and Ozawa method. The BMI resins based on these new monomers have good thermal stability seen from the thermogravimetric analysis results.

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“…Wang et al suggested that these properties might be improved, along with moisture absorption and chemical resistance characteristics, by incorporating naphthalene groups into BMI monomers as either 'in chain' as part of the backbone, or as a pendant group ( Figure 13) [45,46]. In the case of the 'in chain' monomer, it was found that the Tg of the material was improved compared to a phenyl-substituted analogue, and the processing window was widened thanks to lower melting temperatures.…”

Section: Improving High Temperature Performance Of Cured Bmismentioning

confidence: 99%

Modern advances in bismaleimide resin technology: A 21st century perspective on the chemistry of addition polyimides

Iredale¹,

Ward

Hamerton

2017

Progress in Polymer Science

242

152

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General rightsThis document is made available in accordance with publisher policies. Please cite only the published version using the reference above. Full terms of use are available: http://www.bristol.ac.uk/pure/about/ebr-terms Hamerton, E-mail: ian.hamerton@bristol.ac.uk This review is respectfully and affectionately dedicated to Dr Horst D Stenzenberger, who has been an inspirational figure in modern BMI chemistry, always happy to share his extensive knowledge of this field. ABSTRACT:The chemistry of bismaleimides (BMIs), their blends and copolymers is reviewed critically with particular emphasis placed on the development of the field after 1990, which was marked by several comprehensive review articles. A general introduction to the structure property relationships of BMIs is presented, outlining the development of the preparative chemistry, and the early strategies adopted to address the inherent brittleness of the cured 'first generation' BMI polymers. 'Second generation', diallylbisphenol-toughened BMIs, form the basis of the benchmark commercial systems, and the polymerization mechanism is discussed. The current review is placed in context, addressing the issues of cost, processing and precursor toxicity, the major barriers to wider acceptance of BMIs. The main body of the review evaluates a number of observations made by Dr Horst Stenzenberger in 1990, for the future development of BMI technology. Hence, the synthesis of novel bismaleimide building blocks, incorporation of new thermoplastics and additives, and blending with new thermosetting comonomers are all discussed in detail. The aforementioned review had been written before the concept of nanocomposites or shape memory polymers had been explored with BMIs, but the fields have since grown (especially in the case of the former topic) and are reviewed herein. The application of BMIs to continuous fibre composites is one of the proposed fields of commercial development. The topic falls a little beyond the scope of the present review of BMI chemistry, and is the subject of another publication, but a brief discussion of the most recent developments is presented. The review is concluded with some thoughts about the future outlook for BMI chemistry.

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Novel bismaleimide with naphthalene side group. 1. From 1-naphthaldehyde and 2,6-dimethylaniline

Cited by 69 publications

References 17 publications

Structural Effect on Thermal Cure and Property of Naphthalene‐Based Epoxies: Preparation and Characterization

Structural Effect on Thermal Cure and Property of Naphthalene‐Based Epoxies: Preparation and Characterization

Synthesis, characterization, and curing kinetics of novel bismaleimide monomers containing fluorene cardo group and aryl ether linkage

Modern advances in bismaleimide resin technology: A 21st century perspective on the chemistry of addition polyimides

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