Polybutadiene Modified by Addition of Thiols Containing Polar Groups

Marvel, C. S.; Clarke, Kevin; Inskip, H. K.; Taft, W. K.; Labbe, B. G.

doi:10.1021/ie50525a045

Cited by 13 publications

(3 citation statements)

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“…As reported in previous studies 16,17) , thiols with an ester group are more reactive in the free radical addition to double bonds than those with a free carboxylic group. The FD values substantially confirm this trend (Tab.…”

Section: Reaction Of Ema With Sbrsupporting

confidence: 68%

Functionalization of SBR copolymer by free radical addition of thiols

Romani

Passaglia

Aglietto³

et al. 1999

Macromol. Chem. Phys.

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SUMMARY: The reaction of the random styrene/butadiene copolymer (SBR) with two functional thiols (thioglycolic acid and its aliphatic ester) in the presence of free radical initiators is described. The reaction leads to addition of the thiol group to the vinyl double bonds of the 1,2-butadiene units of the copolymer with high selectivity. As a consequence the resulting macromolecules contain covalently bonded carboxylic or carboxylate groups. The influence of the reaction conditions on the relative probability of the addition reaction with respect to crosslinking, degradation and chain transfer reactions is discussed. The degree of functionalization (FD) can be modulated in the range from 1 to 10 mol-%.

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Section: Reaction Of Ema With Sbrsupporting

confidence: 68%

Functionalization of SBR copolymer by free radical addition of thiols

Romani

Passaglia

Aglietto³

et al. 1999

Macromol. Chem. Phys.

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“…Cunneen was looking for new cross-linking methodologies through the addition of dithiols or dithioacids (acting as inter-macromolecular bridges), or by using alkali bases on carboxy-functionalised NR (with thioglycolic acid, TGA). Marvel et al [11] and Serniuk et al, [12,13] in the same years, developed similar procedures in order to obtain oil-resistant rubbers; they used TGA, 2-mercaptoethanol and other polar thiols as functionalising agents for NR, PBs with different amounts of structural units, and SBR. The important role played by the radical initiator soon became evident, since the functionalisation degrees were much higher in presence of an initiator than when using bare UV light acting as a radical generator.…”

Section: Introductionmentioning

confidence: 99%

Thiol‐Ene Radical Addition of L‐Cysteine Derivatives to Low Molecular Weight Polybutadiene

Lotti

Coiai

Ciardelli

et al. 2009

Macro Chemistry & Physics

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The functionalisation of a low molecular weight, liquid 1,2‐polybutadiene (PBL) was performed by the addition of either N‐acetyl‐L‐cysteine or its methyl ester through the thiol‐ene radical reaction. The functionalisation runs were carried out in 1,4‐dioxane solution and in the presence of a free radical initiator (2,2′‐azobisisobutyrronitrile, AIBN). The initial feed ratio polymer/cysteine derivative/initiator was varied, in order to highlight the occurrence of side reactions and to understand their possible influence on the process. The 1H NMR determination of the functionalisation degree brought out high addition degrees of thiols, regardless of the initial thiol/double bonds ratio. This caused a drastic change in the macroscopic properties of the PBL with improved solubility in hydrophilic solvents (for instance in alkaline aqueous solutions) and impressive increase of the glass transition temperature. The propagation of chiral properties from the functionalising agents to the modified polymers was evaluated by polarimetry and circular dichroism in solution.magnified image

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“…Thiols containing polar groups were introduced to polybutadiene to improve the oil resistance with the minimum deleterious effect on low temperature properties (85). The products were similar to normal polybutadiene in low temperature properties but their improvement in oil resistance was less than would have been obtained with polar groups introduced by copolymerization as in nitrile rubbers.…”

Section: Other Synthetic Rubbersmentioning

confidence: 99%

Elastomers

Fisher¹

1954

Ind. Eng. Chem.

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Polybutadiene Modified by Addition of Thiols Containing Polar Groups

Cited by 13 publications

References 1 publication

Functionalization of SBR copolymer by free radical addition of thiols

Functionalization of SBR copolymer by free radical addition of thiols

Thiol‐Ene Radical Addition of L‐Cysteine Derivatives to Low Molecular Weight Polybutadiene

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