8 Oleochemistry Products
251
iodine consumed by 100 grams of substance) represents a key feature for the effective
plasticizing behaviour in PVC or other plastics.
On the other hand, palm oil is not advisable as plasticizers feedstock, as it has a
very low double bonds content, while linseed oil, characterized by the highest I.N.,
is largely used for this scope.
ESBO, with its very low I.N. (<1 gI 2 /100 g, i.e. 0.04 mol double bonds in each
molecule), has been claimed as a primary plasticizer in PVC.
Beyond its plasticizer function, ESBO has revealed to be a thermal stabilizer for
PVC: this dual function in PVC resin was the key to success for its wide application.
PVC is sensitive to thermal degradation during processing at high temperatures.
Therefore, thermal ageing, to eliminate HCl by radical free reaction, is required.
ESBO has the ability to substitute labile chlorines [105], by the reaction between the
epoxide ring and hydrogen chloride generated by PVC degradation. This reaction
provides to make more stable PVC towards further dehydrochlorination, preserving
its colour and properties.
Plasticizers are also prepared by ring-opening reaction of epoxidized vegetable
oils leading to acetylated vegetable oils. Satisfactory plasticizing properties are
described for these compounds.
Many companies manufactured and sold epoxy-based plasticizers in order to
compete with petro-based ones: the main are Varteco, Nexdeum, Vanderputte
Oleochemicals.
With commercial name Vikoflex
® , PVC and PLA plasticizers are sold by Arkema,
based on ESBO and epoxidized esters [60]. Novance developed Radia
® plasticizers based on soybean and rapeseed oils [191]. Kalfex
® , Nexo
® , Resiflex
® and
Lankroflex
® are famous examples of epoxy plasticizers, which lead the market in
Southern America [27].
8.5.7 Other Epoxidized Oil
Epoxidized palm oil (EPO) was used as plasticizers in toughening and aiding the
melt-processing of poly (lactic acid) (PLA) [212]. At various loadings, they were melt
compounded with PLA and hot pressed into 3-mm sheets for impact strength testing.
From the torque and stock temperature curves obtained during compounding, both
plasticizers rapidly reduced the torque and stock temperature. While EPO readily
supports the processing and toughens PLA, higher content of ESO is needed to
perform correspondingly. These improvements suggest the potential of using EPO
and ESO as plasticizer substitutes which shall contribute to the PLA processing
industry [209].
An oligomer of a diepoxy (diglycidyl ether of bisphenol-A, DGEBA) and an
aromatic diamine (MCDEA) have been used as reactive plasticizers for polycarbonate
(PC). A small amount of PC chain scission occurred during this blending process,
probably due to the transesterification of the PC carbonate group by the hydroxyl
group of the DGEBA oligomer. The addition of DGEBA to PC was found to greatly
251
iodine consumed by 100 grams of substance) represents a key feature for the effective
plasticizing behaviour in PVC or other plastics.
On the other hand, palm oil is not advisable as plasticizers feedstock, as it has a
very low double bonds content, while linseed oil, characterized by the highest I.N.,
is largely used for this scope.
ESBO, with its very low I.N. (<1 gI 2 /100 g, i.e. 0.04 mol double bonds in each
molecule), has been claimed as a primary plasticizer in PVC.
Beyond its plasticizer function, ESBO has revealed to be a thermal stabilizer for
PVC: this dual function in PVC resin was the key to success for its wide application.
PVC is sensitive to thermal degradation during processing at high temperatures.
Therefore, thermal ageing, to eliminate HCl by radical free reaction, is required.
ESBO has the ability to substitute labile chlorines [105], by the reaction between the
epoxide ring and hydrogen chloride generated by PVC degradation. This reaction
provides to make more stable PVC towards further dehydrochlorination, preserving
its colour and properties.
Plasticizers are also prepared by ring-opening reaction of epoxidized vegetable
oils leading to acetylated vegetable oils. Satisfactory plasticizing properties are
described for these compounds.
Many companies manufactured and sold epoxy-based plasticizers in order to
compete with petro-based ones: the main are Varteco, Nexdeum, Vanderputte
Oleochemicals.
With commercial name Vikoflex
® , PVC and PLA plasticizers are sold by Arkema,
based on ESBO and epoxidized esters [60]. Novance developed Radia
® plasticizers based on soybean and rapeseed oils [191]. Kalfex
® , Nexo
® , Resiflex
® and
Lankroflex
® are famous examples of epoxy plasticizers, which lead the market in
Southern America [27].
8.5.7 Other Epoxidized Oil
Epoxidized palm oil (EPO) was used as plasticizers in toughening and aiding the
melt-processing of poly (lactic acid) (PLA) [212]. At various loadings, they were melt
compounded with PLA and hot pressed into 3-mm sheets for impact strength testing.
From the torque and stock temperature curves obtained during compounding, both
plasticizers rapidly reduced the torque and stock temperature. While EPO readily
supports the processing and toughens PLA, higher content of ESO is needed to
perform correspondingly. These improvements suggest the potential of using EPO
and ESO as plasticizer substitutes which shall contribute to the PLA processing
industry [209].
An oligomer of a diepoxy (diglycidyl ether of bisphenol-A, DGEBA) and an
aromatic diamine (MCDEA) have been used as reactive plasticizers for polycarbonate
(PC). A small amount of PC chain scission occurred during this blending process,
probably due to the transesterification of the PC carbonate group by the hydroxyl
group of the DGEBA oligomer. The addition of DGEBA to PC was found to greatly