6900-06-7Relevant articles and documents
Stumuli-responsive organogel based on poly(N-propargylamide)
Nomura, Ryoji,Yamada, Katsuhiro,Tabei, Junichi,Takakura, Yoshihito,Takigawa, Toshikazu,Masuda, Toshio
, p. 6939 - 6941 (2003)
The first example for a novel stimuli-responsive organogel that senses external stimuli and undergoes very quick volume change in isotropic organic solvents was demonstrated. It was evidenced that the volume change was driven by the conformational change of the framework between the helical and disordered structures. In addition, it was observed that the volume change occured more rapidly when the solvent was changed from CHCl3 to methanol and that this event could be monitored by the naked eye.
The first thiol-yne click chemistry approach for the preparation of liquid crystalline elastomers
Martella, Daniele,Parmeggiani, Camilla,Wiersma, Diederik Sybolt,Piol, Milagros,Oriol, Luis
, p. 9003 - 9010 (2015/09/01)
A thiol-yne click chemistry reaction is presented, for the first time, to prepare liquid crystalline elastomers. The synthetic strategy is based on two liquid crystalline monomers, one bearing an alkyne group and the second bearing two thiol groups, to cr
Development of a triazole-cure resin system for composites: Evaluation of alkyne curatives
Gorman, Irene E.,Willer, Rodney L.,Kemp, Lisa K.,Storey, Robson F.
experimental part, p. 2548 - 2558 (2012/08/13)
We are developing a resin system that cures via triazole ring formation (cycloaddition reaction of azides with terminal alkynes) instead of the traditional oxirane/amine reaction. The high exothermicity of the azido/alkyne reaction is expected to yield higher extents of reaction under ambient-cure conditions, making the resin system potentially suitable for out-of-autoclave curing processes. The difunctional azide-terminated resin, di(3-azido-2-hydroxypropyl) ether of bisphenol-A, was selected as the baseline diazide. A number of alkyne crosslinkers were synthesized and characterized, including propiolate esters of di- and trifunctional alcohols, propargyl esters of di- and trifunctional carboxylic acids, propargyl ethers of di- and trifunctional alcohols, and N,N,N′,N′-tetrapropargyl derivatives of primary diamines. Commercially available tripropargyl amine was also studied. Those systems employing a propiolate-based alkyne were found to be much more reactive toward the Huisgen 1,3-dipolar cycloaddition than the propargyl species. Curing energetics as a function of alkyne type, investigated through a dynamic differential scanning calorimetry approach, showed a distinct divide between the averaged activation energies of the propiolate and propargyl-type crosslinkers, 69.2-73.6 kJ/mol versus 82.3-86.4 kJ/mol, respectively. Cured network properties were readily manipulated through the incorporation of varying amounts of di- versus tri- and tetra-functional alkynes or through incorporation of soft alkylene and alkyleneoxy versus rigid aromatic polyalkynes. As expected, mechanical properties, e.g., the temperature of the tan δ peak in dynamic mechanical analysis, were found to increase with increasing crosslink density. These results have allowed us to select the most promising systems for scale-up and fabrication of samples of both pure resin and composites for traditional mechanical property testing, which will be reported in a subsequent paper.
