Synthesis of macromolecular antioxidants by reaction of aromatic amines with epoxidized polyisoprene, 3. Reaction of 4‐anilinoaniline with epoxidized 1,4‐polyisoprene

Abstract

4-Anilinoaniline (6) reacts with epoxidized 1 ,rl-polyisoprene in toluene under phenol catalysis. Secondary cyclization reactions are detected at longer reaction times ( z 18 h). However, the kinetic results, obtained at the beginning of the reaction and for limited phenol concentrations, agree with a mechanism involving a trimolecular transition state and a concerted transfer. a) Parts I and 2: ~f .~,~) . b, Present address:

Preparation and characterization of biopolymers comprising chitosan-grafted-ENR via acid-induced reaction of ENR50 with chitosan

“…This is the likely reason why there is very limited number of reports in the literature on homogenous (liquid-liquid phase) or semi-heterogeneous (liquid-solid phase) reaction condition involving chitosan and ENR. Furthermore, ENR is known to undergo ring-opening and double bond cleavage reactions [20][21][22][23][24][25]. To date, there is no report on the stability of the microstructure of ENR in conditions with different concentrations of acid.…”

Chemical modification of polydienes in latex medium: Study of epoxidation and ring opening of oxiranes

“…The reactivity of nucleophilic reagents toward epoxidized 1,4‐polyisoprene latexes was studied. The objective was to determine whether the nucleophilic reagents that were shown to be able to add onto the epoxidized units of epoxidized rubbers in solution5–10 could also react with the same polymers in latex conditions. The study was achieved with ENR latexes, but also with ELIR latexes coming from LIR‐700 latex, a synthetic rubber latex prepared by emulsification of a synthesized 1,4‐polyisoprene.…”

“…This modification is important due to the great reactivity of oxirane rings toward nucleophilic reagents. For example, reactions with amine,5 carboxylic acid,6, 7 alcohol,8, 9 and phosphoric acid derivatives,10, 11 have been studied on epoxidized polyisoprene in solution.…”

Base‐Induced Sequential Cyclization–Rearrangement of Enantioenriched 3‐Aminoalkanoates to Five‐ and Seven‐Membered Lactams

“…Cleavage of oxirane rings of epoxidized natural rubber with various nucleophiles has attracted some interest in recent decades owing to the potential applications of the modified rubbers. So far, drug release polymers,1 vulcanized rubbers,2 antioxidant polymers,3 photocrosslinkable elastomers4 and flame resistant rubbers5, 6 have been prepared by chemical modification of epoxidized polyisoprenes.…”

“…Ring opening of epoxidized units under neutral and mild conditions generally requires the use of a catalyst. Thus, addition of acids and amines to oxirane rings of epoxidized polyisoprenes is conveniently catalyzed by onium salts,1, 7 Brönsted acids and phenolic acids 3, 8–10. However, no catalyst is used in the case of phosphate acid derivatives which provide acidic protons by self‐dissociation equilibrium 6…”