Synthesis and performance of phenolic polybutadiene‐bound stabilizers

Abstract

An antioxidant derivative, 6-sulfanylhexyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propanoate, was synthesized and examined. With a radical initiator, the addition of this compound to pending vinyls of OH-telechelic, low molecular weight liquid polybutadiene (LBH) was performed to various degrees of conversion to form polymeric antioxidants (PAOs) in which the phenolic moiety was separated from the main chain by a spacer [OCH 2 CH 2 OSO (CH 2 ) 6 OOOCOO]. Pure, unstabilized LBH was mixed in several ratios with PAOs, Irganox 1520, and Irganox 1076, and the oxidation stabilities of these mixtures, determined by thermogravimetric analysis and differential scanning calorimetry, were compared. Probably because of their good compatibility with LBH, PAOs exhibited equal or better effectiveness than commercial antioxidants of the Irganox type.

Extraction resistance and mechanism of a macromolecular hindered phenol antioxidant in natural rubber

“…[6][7][8][9][10] The polymer include natural rubber, [11][12][13] polyolefin, [14][15][16] polybutadiene, [17][18][19] and others. 10,20,21 Podesva et al 22,23 synthesized a polymerbound antioxidant by free-radical addition reaction between a sterically hindered phenolic antioxidant with a sulfanyl group and OH-telechelic polybutadiene. The results showed that the antioxidant had better antioxidative performance and long-term persistence than the commercial antioxidant Irganox 1076.…”

Synthesis and characterization of polyhydroxylated polybutadiene binding 2,2′‐thiobis(4‐methyl‐6‐tert‐butylphenol) with isophorone diisocyanate

“…Due to low thermal stability, poor migration resistance and poor extraction resistance, the physical loss of low molecular weight antioxidant was large during polymer processing and long‐term service, which severely restricted its applications. In order to overcome the problem, macromolecular antioxidant had attracted much attention in recent years . For example, Kim synthesized several kinds of polymeric antioxidants by copolymerization or homopolymerization of functional monomers containing hindered phenol.…”

“…In order to overcome the problem, macromolecular antioxidant had attracted much attention in recent years. [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15] For example, synthesized several kinds of polymeric antioxidants by copolymerization or homopolymerization of functional monomers containing hindered phenol. El-Wakil et al [9][10][11][12] studied the grafting of o-aminophenol, 1,2-phenylenediamine,1,5-diaminonaphthalene, and N-(4-aminodiphenyl methane) acrylamide onto natural rubber.…”

“…El-Wakil et al [9][10][11][12] studied the grafting of o-aminophenol, 1,2-phenylenediamine,1,5-diaminonaphthalene, and N-(4-aminodiphenyl methane) acrylamide onto natural rubber. Podesva 13,14 synthesized a polymer-bound antioxidant by free radical addition reaction between a hindered phenolic antioxidant with a sulfanyl group and hydroxylterminated polybutadiene. The thermal stability and extraction resistance of the obtained macromolecular antioxidants were improved obviously.…”

Synthesis and Thermo-Oxidative Aging Resistance of Hydroxyl Terminated Polybutadiene Bound 2,2-Thiobis(4-methyl-6-tert-butylphenol)

“…Pode s sva and coworkers investigated the attachment of phenolic antioxidant with a sulfanyl group to the pendent vinyls of hydroxyl terminated polybutadiene (HTPB) by free radical addition, and the results showed that antioxidant effect of the prepared antioxidant was superior to low molecular weight antioxidant due to persist in polymer matrix [27,28] . Thus, 2,2-Thiobis (4-methyl-6-tert-butylphenol) (TPH) is an important antioxidant of sterically hindered phenol.…”