Melt/solution processable polyaniline with functionalized phosphate ester dopants and its thermoplastic blends

Abstract

Polyaniline (PANI) was doped with five novel dopants, 3-pentadecylphenylphosphoric acid (PDPPA), pentadecylphenyl(bis)phosphoric acid [PDP(bis)PA], monocardanylphosphoric acid (MCPA), dicardanylphosphoric acid (DCPA), and phosphorylated cashew nut shell liquid prepolymer (PCNSL) and the doping behavior was studied. All dopants were synthesized from inexpensive naturally existing monomers [obtained from cashew nut shell liquid (CNSL)] having a long hydrophobic hydrocarbon side chain in the meta position of the aromatic ring. These dopants can act as plasticizing cum protonating agents for PANI so that free-standing films of PANI could be prepared by both thermal processing and solution processing techniques. Protonation was performed either by mechanical mixing of emeraldine base and the dopant or by an in situ doping emulsion polymerization route using xylene or chloroform as the solvent. Further, conductive flexible blends of the protonated PANI with poly(vinyl chloride) (PVC) were also prepared and studied for their conductivity and related properties. The PANI-PDPPA complex obtained by the in situ doping emulsion polymerization route exhibited an exceptionally high degree of crystalline order and orientation. A maximum conductivity value of 1.8 S cm Ϫ1 was obtained for a PANI-PDPPA film hot-pressed at 120°C. On the other hand, dopants based on cardanol having an unsaturated side chain gave only lower values. This was understood to be due the capability of the saturated analog to contribute to the ordered arrangement of PANI, thus improving the crystallinity. The conductivity values further decreased when bulky/oligomeric dopants such as PCNSL were used. The thermoplastic blends with PVC exhibited an exceptionally low-level percolation threshold because of the plasticizing nature of the dopants. The doped polymers and blends were characterized by FTIR and UV-visible spectroscopic methods, four-probe conductivity measurements, XRD, SEM, TGA, and DSC.

Phosphorylation of bio-based compounds: the state of the art

“…The lubricity capacity of these compounds was evaluated through a High Frequency Another example of an original use of a CNSL phosphorylated derivative was reported by Paul and Pillai. 253 They prepared phosphoric acid additives for polyanilline (PANI) conducting polymers from different CNSL derivatives. These additives have a plasticization effect due to the pendant alkyl chain of CNSL derivatives and also a doping effect as the protons from phosphoric acid groups are labile and increase the conducting properties of the PANI polymers.…”

Synthesis of a kairomone and other chemicals from cardanol, a renewable resource

“…The overall synthesis of compound 5 from cardanol (2) is summarized in Scheme 1. The numbering assigned to cardanol (2) in Scheme 1, also applies to all target compounds, 5,6,7,8,9,10, and 13. E-Hexadec-2-ene (11) was not a target compound of this study but it was detected as a major product in the crude reaction mixture by GC-MS.…”

“…In addition, synthesis of novel cardanol based fulleropyrrolidines has also recently been reported [7]. Cardanol [8] or sulfonated cardanol [9][10][11] can be functionalized to form phenolic ethers, which are used as polymer additives [9][10][11] or in nanofibers [8]. Although cardanol has been exploited as a starting material, the application of homogeneous catalysis to its modification to more valuable compounds has rarely been described.…”

Challenges for Natural Monomers and Polymers: Novel Design Strategies and Engineering to Develop Advanced Polymers

“…3) for polyaniline [186][187][188][189][190][191]. These dopants are found to possess multiple functions of plasticization, emulsification, protonation and solubilization.…”