SynopsisA novel oligomeric compound has been synthesized by reacting 1,3 bis-(3-aminophenoxy)benzene (APB) with p-benzoquinone. A dark reddish brown product has been characterized using W, IR, and N M R spectra, and elmental analysis. It, too, adheres to metals, as does another polyetheramine-p-benzoquinone polymer synthesized in Part I [ B o g . Org. Coating, 15, 63 (1987)], and becomes nonwettable after heat curing. However, its moisture adsorption is only 0.1% by weight, as against 3% for the latter product. This makes it a likely candidate for insulating electronic components from moisture.+For Part I, see Ref. 4.
SYNOPSISSeveral diamine-p -benzoquinone polymer/oligomers were synthesized to find those that exhibited superior properties, in addition to being able to displace water from wet, rusty steel surfaces. Unfortunately, many of these were found to be insoluble in most commonly used solvents and a few to be insoluble in all 34 solvents used in polymer solubility studies. The reason for this low solubility is believed to be the extremely regular structure of the polymers.
Proteins are the most underrated and under-used polymers: their impressive properties include infusibility, great mechanical strength and inherent adhesive capability due to a highly flexible backbone and many functional side chains. The notion of moisture sensitivity of proteins is not universally true. Barnacle cement (which can adhere to Teflon) and mussel and clam byssus, all of which are 99% protein, set in the presence of water and resist enzymatic as well as chemical degradation at ambient temperature. This observation suggests that proteins that are capable of tight three-dimensional cross-linking can overcome sensitivity to moisture and enzymatic attack. It should then be possible to achieve similar resistance by appropriate chemical manipulation of proteins, leading to cross-linking. We have achieved such a result with an ordinary protein, commercially available gelatin, which was chemically modified and then epoxidized. When cured such a material binds to metals and plastics. Any protein that has modifiable amino acids can be used for this purpose.
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