Chemical polymerization of pyrrole in the presence of ketone–formaldehyde resins

Kızılcan, Nilgün; Ustamehmetoğlu, Belkıs

doi:10.1002/app.21437

Cited by 28 publications

(18 citation statements)

References 15 publications

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“…Chain extended resin had different solubilities, melting points and self-extinguishing property. The chemical and electro-induced oxidation of ketonic resin in the presence of ceric ammonium nitrate have been reported (Ustamehmetoglu et al, 2001(Ustamehmetoglu et al, , 2004Kızılcan and Ustamehmetoglu, 2005;Kızılcan et al, 2011).…”

Section: Introductionmentioning

confidence: 98%

Chain extended vinyl aniline modified cyclohexanone formaldehyde resin

Kızılcan

Ateş²

2013

Pigment &Amp; Resin Technology

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Purpose -The purpose of this paper was as follows. The in situ chemical oxidation (ICO) of vinyl aniline modified cyclohexanone formaldehyde resin (CFVAnR) in the presence of potassium persulphate salt (K 2 S 2 O 8 ) was accomplished in dimethyl sulphoxide (DMSO) solutions at 358C and 708C. The chemical composition and structure of the oxidized CFVAnR were characterised by nuclear magnetic resonance ( 1 H-NMR) spectroscopy, Fourier transform infrared (FT-IR) spectroscopy, DSC, TGA and SEM. Design/methodology/approach -The reactive vinyl and amine groups of the cyclohexanone formaldehyde resin were reacted in the presence of potassium persulphate. CFVAn resin was dissolved in DMSO inside a round bottom flask immersed in a water bath thermostated at reaction temperature of 358C and 708C, respectively. Solution of K 2 S 2 O 8 was prepared in DMSO and this was added into the resin solution.Findings -It was shown that the vinyl groups in the resin were reacted easily with persulphate salt to obtain chain extended CFVAnR (CECFVAnR). The oxidised 4-vinyl aniline modified cyclohexanone-formaldehyde resin has solublity in organic solvents.Research limitations/implications -The reaction mixture must be stirred continuously. Temperature should be controlled to prevent the thermal polymerisation of vinyl group and higher branching of amino groups. The persulphate ion (S 2 O 22 8 ) has a standard oxidation potential, but when activated by heat (40-608C). Furthermore, sulphate radical can react with water or hydroxide to produce hydroxyl radical (ZOH). When persulphate is used for in situ chemical oxidation (ISCO) application at relatively low temperatures (e.g. , 208C), the oxidation reactions are usually less aggressive due to a slow generation rate of SO 2 4 . Practical implications -This study provides technical information for the synthesis of chain extended resins. The modified resins contain vinyl groups. The chemical radical system has been used to polymerise these vinyl groups and resins with much higher molecular weight might be produced. The resins may also promote the adhesive strength of a coating and corrosion inhibition to metal surfaces of a coating. Social implications -This resin will be used for the preparation of AB-and ABA-type block copolymers. These block copolymers may exhibit different properties due to incorporation of ketonic resins into the block copolymer structure. Originality/value -Chain extended CFVAnR (CECFVAnR) was synthesised by one step reduction-oxidation reaction, at 358C (CECFVAnR1) and 708C (CECFVAnR2) in the presence of potassium persulphate salt. These soluble resins may overcome difficulties in the applications of polymers and open new application areas. Therefore, the chain extended vinyl aniline modified resin may find a number of new application areas as well as existing UV curable resin and polymer applications.

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Section: Introductionmentioning

confidence: 98%

Chain extended vinyl aniline modified cyclohexanone formaldehyde resin

Kızılcan

Ateş²

2013

Pigment &Amp; Resin Technology

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“…Ketonic resins are used as a resin in the ink and paint sector in an intensive adhesion. Many successful products that use ketonic resins in this direction are commercially and domestically available (15)(16). However, their use in polyurethane adhesives has not been the subject to date due to the fact that ketonic resins are more difficult to access than polyols and the costs associated therewith are high.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Reactive Polyurethane Adhesives and Studying the Effect of Ketonic Resins

Köken

Aydın

2020

Journal of the Turkish Chemical Society Section A: Chemistry

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In this study, the effects of cyclohexanone formaldehyde ketonic resin (CFR) with different montmorillonite (MM) content (from 0,5 to 3 wt%) on the viscosity, initial adhesion strength, and temperature resistance of polyurethane one-component adhesives were investigated. In situ MM modified cyclohexanone formaldehyde resin (MM-CFR) was used as polyol into formulation with a specified weight ratio (rate of 10% by weight of polyether polyol). One-shot technique was used for synthesis. CFR with varying montmorillonite (MM) content were incorporated blank polyurethane was synthesized using polyether polyol and polymeric 4,4'-methylene diphenyl diisocyanate (p-MDI). In experimental studies, the ratio of the isocyanate groups (NCO) to the hydroxyl group (OH) was 4.84. Reaction completion was followed by FTIR spectroscopy. Chloroparaffin was used as a plasticizer to adjust the viscosity and to reduce the fragile structure of the product. The NCO % values of the synthesized adhesive PU were measured by titration. When TGA data were examined, it was found that the heat resistance of the product increased with the addition of CFR and MM-CFR. As a result, it has been determined that the adhesion properties and thermal resistance were improved with the use of ketonic resins in one component reactive adhesives.

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“…PNVCz, Cz-modified methyl ethyl ketone formaldehyde resin (MEKFR) and PNVCz-MEKFR copolymer were obtained on pyrite surface and then their photoactivity and inhibition on the corrosion and photo corrosion of pyrite were investigated (Ustamehmeto glu et al, 2013). The conductivity, solubility and thermal behaviour of the copolymers of polypyrrole and ketonic resin were investigated (Kızılcan and Ustamehmeto glu, 2005).…”

Section: Introductionmentioning

confidence: 99%

Electrochemical synthesis and characterization of copolymers of N-vinyl carbazole and methyl ethyl ketone formaldehyde resin

Ustamehmetoğlu

Köken

Kızılcan

et al. 2020

PRT

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Purpose The purpose of this paper is to produce non-conductive copolymers of N-vinyl carbazole (NVCz) and methyl ethyl ketone formaldehyde resin (MEKFR) by the electroinduced Ce (IV) polymerization method and the electrochemical oxidization of the formed copolymer to produce their conductive green form. The non-conductive and conductive copolymers were characterized by using Fourier transform infrared, solid-state conductivity and spectroelectrochemical, chronoamperometric, cyclovoltammetric and electrochemical impedance spectroscopic measurements. Design/methodology/approach The chronoamperometric electropolymerization of white, insulator form of the copolymer of NVCz and MEKFR (copolymer 1) on to Pt electrode was carried out and the green coloured film of the MEKFR-ox-NVCz copolymer (copolymer 11) was produced in the doped and conductive form. All reactions were performed in dichloromethane containing 0.1 M BU4NClO4. Copolymer 11 films obtained on the surface of the working electrode were removed and washed in acetonitrile and dried at room temperature before characterization. The results were compared with the copolymer obtained by electrochemical oxidation of MEKF-R and NVCz (copolymer 2). Findings The insulating copolymer of NVCz and MEKFR (copolymer 1) was produced by the electroinduced Ce (IV) polymerization method and converted into the conductive form electrochemically on the surface of the Pt electrode (copolymer 11). The polymers were characterized by electrochemical, spectrophotometric and conductivity measurements. The ionization potentials, optical band gap, peak potentials Ep, doping degree and specific capacitance of the copolymer 11 were obtained. The conductivity of the copolymer 11 is lower than the PNVCz and higher than the copolymer obtained by electrochemical oxidation of MEKF-R and NVCz (copolymer 2). The copolymer 11 has a lower onset potential than PNVCz and the copolymer 1 and slightly higher band gap than PNVCz. The capacitive behaviours of the copolymer 11 were very close to PNVCz. Research limitations/implications This study focuses on obtaining a green and conductive form of the copolymer of NVCz and MEKFR with the electrochemical method by using a white and insulator form of the same copolymer. Practical implications This work provides technical information for the synthesis of conducting copolymer of NVCz and MEKFR. Social implications These copolymers may be in the field of PNVCz applications such as photoconductivity and corrosion inhibition. Originality/value Electroinduced Ce (IV) MEKFR redox system was applied for the polymerization of NVCz monomer to produce the copolymer 1. The conductive copolymer 11 was synthesized through electrochemical oxidative coupling of the carbazole groups of the copolymer 1.

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Chemical polymerization of pyrrole in the presence of ketone–formaldehyde resins

Cited by 28 publications

References 15 publications

Chain extended vinyl aniline modified cyclohexanone formaldehyde resin

Chain extended vinyl aniline modified cyclohexanone formaldehyde resin

Synthesis of Reactive Polyurethane Adhesives and Studying the Effect of Ketonic Resins

Electrochemical synthesis and characterization of copolymers of N-vinyl carbazole and methyl ethyl ketone formaldehyde resin

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