Novel chemistries for the replacement of methylenedianiline in composites

Owen M. Stecca, Kevin M. Schmalbach, Jayson D. Cosgrove, Alexander W. Bassett, William S. Eck, Craig M. Paquette, Joshua M. Sadler, John J. La Scala, Joseph Stanzione

Research output: Contribution to conferencePaper

Abstract

4,4′ Methylenedianiline (MDA) is utilized to produce high performance composites; however, MDA is a known carcinogen and liver toxin. The concerns over exposure to MDA have resulted in added safety measures that increase costs for manufacturing, driving the search for potential MDA replacements. Alternatives to MDA have not gained significant traction due to reduced performance, reduced confidence in the material, and they offer a small, if any, reduction in toxicity. In this paper, we present our work on developing structure-property-toxicity relationships of various substituted dianilines by examining the effect of molecular architecture on overall polymer performance and toxicity. Novel dianilines derived from both petroleum and biomass with different numbers and types of methyl and methoxy substituents on the aromatic ring were synthesized to eliminate toxicity and carcinogenic aspects of the resulting material while maintaining thermal and mechanical integrity. Structure-toxicity relationships indicate that multiple substituents on the aromatic ring are necessary to severely reduce the toxicity of the dianiline. Structure-property relationships show that methoxy groups reduce the glass transition temperature and thermal degradation temperature while methyl groups only slightly affect these properties.

Original languageEnglish (US)
Pages1143-1152
Number of pages10
StatePublished - Jan 1 2017
EventSAMPE Seattle 2017 Conference - Seattle, United States
Duration: May 22 2017May 25 2017

Other

OtherSAMPE Seattle 2017 Conference
CountryUnited States
CitySeattle
Period5/22/175/25/17

Fingerprint

Toxicity
Composite materials
Carcinogens
Liver
Biomass
Pyrolysis
Crude oil
Polymers
Costs
Temperature

All Science Journal Classification (ASJC) codes

  • Mechanics of Materials
  • Mechanical Engineering
  • Materials Science(all)

Cite this

Stecca, O. M., Schmalbach, K. M., Cosgrove, J. D., Bassett, A. W., Eck, W. S., Paquette, C. M., ... Stanzione, J. (2017). Novel chemistries for the replacement of methylenedianiline in composites. 1143-1152. Paper presented at SAMPE Seattle 2017 Conference, Seattle, United States.
Stecca, Owen M. ; Schmalbach, Kevin M. ; Cosgrove, Jayson D. ; Bassett, Alexander W. ; Eck, William S. ; Paquette, Craig M. ; Sadler, Joshua M. ; La Scala, John J. ; Stanzione, Joseph. / Novel chemistries for the replacement of methylenedianiline in composites. Paper presented at SAMPE Seattle 2017 Conference, Seattle, United States.10 p.
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Stecca, OM, Schmalbach, KM, Cosgrove, JD, Bassett, AW, Eck, WS, Paquette, CM, Sadler, JM, La Scala, JJ & Stanzione, J 2017, 'Novel chemistries for the replacement of methylenedianiline in composites' Paper presented at SAMPE Seattle 2017 Conference, Seattle, United States, 5/22/17 - 5/25/17, pp. 1143-1152.

Novel chemistries for the replacement of methylenedianiline in composites. / Stecca, Owen M.; Schmalbach, Kevin M.; Cosgrove, Jayson D.; Bassett, Alexander W.; Eck, William S.; Paquette, Craig M.; Sadler, Joshua M.; La Scala, John J.; Stanzione, Joseph.

2017. 1143-1152 Paper presented at SAMPE Seattle 2017 Conference, Seattle, United States.

Research output: Contribution to conferencePaper

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AU - Stecca, Owen M.

AU - Schmalbach, Kevin M.

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AU - Eck, William S.

AU - Paquette, Craig M.

AU - Sadler, Joshua M.

AU - La Scala, John J.

AU - Stanzione, Joseph

PY - 2017/1/1

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N2 - 4,4′ Methylenedianiline (MDA) is utilized to produce high performance composites; however, MDA is a known carcinogen and liver toxin. The concerns over exposure to MDA have resulted in added safety measures that increase costs for manufacturing, driving the search for potential MDA replacements. Alternatives to MDA have not gained significant traction due to reduced performance, reduced confidence in the material, and they offer a small, if any, reduction in toxicity. In this paper, we present our work on developing structure-property-toxicity relationships of various substituted dianilines by examining the effect of molecular architecture on overall polymer performance and toxicity. Novel dianilines derived from both petroleum and biomass with different numbers and types of methyl and methoxy substituents on the aromatic ring were synthesized to eliminate toxicity and carcinogenic aspects of the resulting material while maintaining thermal and mechanical integrity. Structure-toxicity relationships indicate that multiple substituents on the aromatic ring are necessary to severely reduce the toxicity of the dianiline. Structure-property relationships show that methoxy groups reduce the glass transition temperature and thermal degradation temperature while methyl groups only slightly affect these properties.

AB - 4,4′ Methylenedianiline (MDA) is utilized to produce high performance composites; however, MDA is a known carcinogen and liver toxin. The concerns over exposure to MDA have resulted in added safety measures that increase costs for manufacturing, driving the search for potential MDA replacements. Alternatives to MDA have not gained significant traction due to reduced performance, reduced confidence in the material, and they offer a small, if any, reduction in toxicity. In this paper, we present our work on developing structure-property-toxicity relationships of various substituted dianilines by examining the effect of molecular architecture on overall polymer performance and toxicity. Novel dianilines derived from both petroleum and biomass with different numbers and types of methyl and methoxy substituents on the aromatic ring were synthesized to eliminate toxicity and carcinogenic aspects of the resulting material while maintaining thermal and mechanical integrity. Structure-toxicity relationships indicate that multiple substituents on the aromatic ring are necessary to severely reduce the toxicity of the dianiline. Structure-property relationships show that methoxy groups reduce the glass transition temperature and thermal degradation temperature while methyl groups only slightly affect these properties.

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Stecca OM, Schmalbach KM, Cosgrove JD, Bassett AW, Eck WS, Paquette CM et al. Novel chemistries for the replacement of methylenedianiline in composites. 2017. Paper presented at SAMPE Seattle 2017 Conference, Seattle, United States.