Quinone-amine polyurethanes: novel corrosion-inhibiting coupling agents for bonding epoxy to steel

Vaideeswaran, Karthik; Bell, James P.; Nikles, David E.

doi:10.1163/156856199x00055

Cited by 6 publications

(4 citation statements)

References 27 publications

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“…These polyurethanes were shown to inhibit the corrosion of the commercial iron particles used in state‐of‐the‐art metal particle tape 10–13. We also demonstrated that amine–quinone polyurethanes promote the adhesion of epoxy to steel 14, 15…”

Section: Introductionmentioning

confidence: 61%

“…The amine–quinone polyurethanes and the amine–quinone polyimides provide an opportunity to test this model. We have already shown that amine–quinone polyurethanes promote adhesion of epoxy to steel 14, 15. We speculate that the amine–quinone polymers chemisorb to the iron surface and expect that the bond strength would depend on the nature of the amine–quinone functional group and the number of groups adsorbing to the iron surface.…”

Section: Discussionmentioning

confidence: 90%

“…Our experience with amine–quinone polyurethanes was that the thermal decomposition temperature was less than 300 °C 7, 9. The diol monomer, 2,5‐ bis( N ‐2‐hydroxyethyl‐ N ‐methylamino)‐1,4‐benzoquinone decomposed when heated to its melting point of 167 °C 14. This led to a concern that the 2,5‐diamino‐1,4‐benzoquinone group might be thermally unstable, although this was not the case.…”

Section: Discussionmentioning

confidence: 99%

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Amine–quinone polyimides

Han

Nikles

2001

J. Polym. Sci. A Polym. Chem.

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Two dianiline monomers were prepared by the reaction of either 4,4Јmethylenedianiline or 4,4Ј-oxydianiline with 1,4-benzoquinone. These monomers were used to synthesize a series of amine-quinone polyimides by condensation with either 3,3Ј,4,4Ј-benzophenonetetracarboxylic dianhydride or 4,4Ј-(hexafluoroisopropylidene) diphthalic anhydride to make the corresponding polyamic acid. The polyamic acids were converted to the polyimides by thermal imidization at 290°C. The amine-quinone polyimides gave freestanding films with tensile strengths in the range of 90 to 150 MPa and Young's moduli of 0.9 to 1.5 GPa. The thermal decomposition temperature under nitrogen was 440 to 480°C and the glass-transition temperature was in the range of 280 to 310°C. The amine-quinone polyimides had the excellent thermal and mechanical properties that one expects for polyimides.

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Section: Introductionmentioning

confidence: 61%

Section: Discussionmentioning

confidence: 90%

Section: Discussionmentioning

confidence: 99%

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Amine–quinone polyimides

Han

Nikles

2001

J. Polym. Sci. A Polym. Chem.

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“…4 They also promoted the adhesion of epoxy to steel. 5 Curiosity led us to explore the possibility of replacing the amine group with a thioether group. We have developed the synthesis of a sulfur-quinone diol monomer and die preparation of polyurethanes containing this sulfurquinone monomer.…”

Section: A Sulfur-quinone Diol Monomer 25-bis-(2-hydroxyethylthio)-mentioning

confidence: 99%

Sulfur-Quinone Polyurethanes and the Protection of Iron against Corrosion

Helm

Nikles

et al. 2003

ACS Symposium Series

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A sulfur-quinone diol monomer, 2,5-bis-(2-hydroxyethylthio)-1,4-benzoquinone (SQM-2), was prepared by the reaction of 2-mercaptoethanol with 1,4-benzoquinone.SQM-2 and polycaprolactone diol (M n = 1250) were condensed with toluene diisocyanate to give a sulfur-quinone polyurethanes, SQPU-1, containing 7 mole percent SQM-2. SQPU-1 was coated onto an iron square and exposed to either 0.1 M sodium chloride electrolyte or substitute ocean water. Electrochemical impedance spectroscopy monitored any degradation of the coatings and showed that the sulfur-quinone polyurethane protected the iron against corrosion. Reflectance absorption infrared spectroscopy showed that the chemisorbed sulfur-quinone functional group lies parallel to the iron surface.For more than a decade polymers containing the 2,5-diamino-1,4-benzoquinone functional group have been of interest, since Erhan's observation that this class polymers have a strong affinity for the surface of iron. 1 They found that the amine-quinone polymers could displace moisture from the surface of iron, making it hydrophobic. If the amine-quinone polymers would prevent moisture from adsorbing onto the iron surface, then they would inhibit corrosion. Indeed, they reported salt-spray testing data showing that aminequinone polymers prevent corrosion. 2 We have synthesized amine-quinone polyurethanes by condensing the amine-quinone monomer, 2,5-bis(N-2-hydroxyethyl-N-methylamino)-1,4-benzoquinone, and an oligomeric diol monomer (e.g., polycaprolactone diol, 168

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Laccase-induced derivatization of unprotected amino acid L-tryptophan by coupling with p-hydroquinone 2,5-dihydroxy-N-(2-hydroxyethyl)-benzamide

et al. 2006

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We have studied the enzymatic derivatization of amino acids by use of the polyphenol oxidase laccase. Derivatization of L-tryptophan was achieved by enzymatic crosslinking with the laccase substrate 2,5-dihydroxy-N-(2-hydroxyethyl)-benzamide. The main product (yield up to 70%) was identified as the quinoid compound 2-[2-(2-hydroxy-ethylcarbamoyl)-3,6-dioxo-cyclohexa-1,4-dienylamino]-3-(1H-indol-3-yl)- propionic acid and demonstrates that laccase-catalyzed C-N-coupling occurred on the amino group of the aliphatic side chain. These enzyme based reactions provide a simple and fast method for the derivatization of unprotected amino acids.

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Quinone-amine polyurethanes: novel corrosion-inhibiting coupling agents for bonding epoxy to steel

Cited by 6 publications

References 27 publications

Amine–quinone polyimides

Amine–quinone polyimides

Sulfur-Quinone Polyurethanes and the Protection of Iron against Corrosion

Laccase-induced derivatization of unprotected amino acid L-tryptophan by coupling with p-hydroquinone 2,5-dihydroxy-N-(2-hydroxyethyl)-benzamide

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