Polyesteramide Resins Research Articles

Synthesis and Characterization of Polyesteramide Resin from Acacia auriculiformis Seed Oil for Surface Coating Application

Synthesis and Characterization of Polyesteramide Resin from Acacia auriculiformis Seed Oil for Surface Coating Application

Leucaena leucocephala oil-based poly malate-amide nanocomposite coating material for anticorrosive applications

Abstract This article describes the synthesis of polyesteramide (PEA) resin from Leucaena leucocephala oil (LLO) obtained from seeds of L. leucocephala tree, locally grown in King Saud University Campus. LLO was transformed into amide diol by based catalyzed amidation reaction, followed by esterification reaction with malic acid (MA), that resulted in LLO-based PEA (LPEA). The synthesis was performed without using any solvent or catalyst. Fourier-transformation infrared spectroscopy and nuclear magnetic resonance confirmed the formation of LPEA by the introduction of amide and ester moieties. LPEA was further reinforced with nano graphene oxide (GO) and fabricated into nanocomposite corrosion protective coatings (LPEA/GO). LPEA/GO coatings obtained were tough, flexibility retentive and showed good corrosion resistance performance toward 3.5 w/w% NaCl medium. Thermogravimetric analysis confirmed good thermal stability of coatings with safe usage up to 200°C.

Polyesteramides Based on Linseed and Safflower Oils for Protective Coatings

Polyesteramide resins were obtained and evaluated as vehicles and the variations of film performance in relation to the amide linkage were studied. Treatment of either linseed or safflower oils with diethanolamine with catalytic amounts of alkali metal alkoxide under relatively mild conditions led to a substantially complete conversion to N,N-(hydroxyethyl) linseed amide (HELA) and N,N-(hydroxyethyl) safflower amide (HESA). Polymerization of the polyols with diadipyl aromatic amines (aniline, p-toluidine, p-aminophenol and p-aminobenzoic acid) was carried out to yield polyesteramide derivatives having interesting surface coating properties. Such a substitution was claimed to give much harder, tougher, more flexible films with excellent chemical resistance in comparison with alkyd resins of similar oil length. The study includes stoving films mechanical evaluation as gloss percent at 60ºC, adhesion, impact, pencil hardness and bending tests using mild steel plates. The films also possess excellent impact resistance, high scratch hardness values, excellent bending test and good adhesion.

Eco-friendly waterborne coating from bio-based polyester amide resin

The vegetable oil-based waterborne polyurethane coatings have gained significant interest due to low volatile organic compounds, and hence, this has been considered as a proper substitute to the commonly used solvent-borne coating systems. In the present work, we have developed the polyurethane coatings from diethanolamide of fatty acid and dicarboxylic acid (sebacic acid and succinic anhydride)-based poly(esteramide) resin as a diol along with 2,2′-dimethylol propionic acid and isophorone diisocyanate. The chemical structure of bio-based diol and PU coatings was elucidated by FTIR and 1H NMR spectroscopy. The polyurethane dispersions (PUDs) prepared were analysed by particle size analysis and stability. The mahua oil-based PUDs were coated on the metal panels and the cured material obtained was characterized by the physico-mechanical, chemical resistance and the thermal properties which were compared with the petroleum resource-based PUDs. The PUD coatings showed good physico-mechanical properties, chemical resistance and thermal stability. Hence, the dispersion prepared from bio-based diols may find application as eco-friendly coatings.

Synthesis of polyurethane dispersion from polyesteramide polyol

Purpose The study aims to synthesise polyurethane dispersion from polyesteramide polyol. The polyesteramide polyol is a novel polyol for the synthesis of polyurethane dispersion. Design/methodology/approach Polyesteramide polyol has been synthesised from phthalic anhydride and fatty amide of mustard oil. Aminolysis of mustard oil had been carried out with diethanolamine. The novel polyurethane dispersion had been synthesised using a polyesteramide polyol as a precursor. Isophorone diisocyanate was used as an isocyanate component and polyurethane dispersion (PUDs) had been synthesised by an anionic method where DMPA was introduced to introduce –COOH groups as via grafting to the resin backbone. Triethylamine was used for neutralisation and, hence, for further dispersion in water. Hydroxyl ethyl methacrylate was used for the synthesis to introduce unsaturation in the backbone of PUDs. The coating was made by an UV curing process. The coating was characterised for mechanical properties, chemical properties, thermal properties as well as stain resistance. Findings The polyurethane dispersion formed through it has ester and amide linkage present in it. The acetone process is used for its synthesis. The nuclear magnetic resonance spectroscopy confirms the successful formation of polyesteramide polyol and PUDs. Even though long aliphatic chains present in polyol which may impart hydrophobicity the synthesis PUDs well dispersed in water. It is observed as the coating made from it have hardness and scratch resistance properties. The coating also exhibits good stain resistance properties. Practical implications The method is an easy one to synthesise polyurethane dispersion from polyesteramide polyol, which is based on ester and amide linkage. Originality/value To the best of the authors’ knowledge, this is the first report on synthesised polyurethane dispersion from polyesteramide polyol. The polyesteramide resin already proves its excellence and upcoming technology in the coating industry. Here, they are incorporated into the synthesis of polyurethane dispersion.

Synthesis of tetra(2,2-hydroxyethylene) terephthalamide from PET waste and its application in synthesis of polyesteramide coating

PurposeThe purpose of this paper is to discuss the synthesis of polyesteramide resin from the monomer obtained from poly (ethylene terephthalate) (PET) waste and study of the structure – property relation for the same in polyesteramide coating. The purpose is also not only to just target the polymeric waste but also to study the effect of the structure of monomer obtained from such waste in final coating.Design/methodology/approachPET waste was depolymerised using diethanolamine to tetra(2,2-hydroxyethylene) terephthalamide (THETA). Four functional hydroxyl terminated monomers were generated having amide linkage as a structural part. THETA was used for the synthesis of polyesteramide resin along with fatty amide of oil, and concentration of the THETA was varied. The synthesised polyesteramide resin was cured with MF resin and tested for physico-chemical, thermal and anticorrosive properties.FindingsPET was successfully depolymerised to monomeric level using diethanolamine as a reactive agent. It is observed that as the concentration of THETA increases, the hardness of the coating increases, as aromatic concentration increases in the coating. The amide linkage helps to improve adhesion as well as hydrophobicity because an aliphatic long chain of fatty amide and aromatic linkage of THETA helps in improving anticorrosive properties of the coating.Practical implicationsThis method is the useful key to solve the polymeric waste problem. PET can be easily depolymerised using diethanolamine and polyesteramide resin synthesised from it. Hence, waste material can be converted into the coating by reacting it with renewable resources.Originality/valueTo the best of the authors’ knowledge, this is the first study which uses THETA as a monomer for the synthesis of polyesteramide resin and study of its various concentrations on coating properties. The coating is obtained from waste material; hence, polymeric waste issue is also solved, and dependency on the petroleum resources to obtain raw materials for coating is also depleted partially. The study also helps to understand the effect of the structure of monomers on the properties of the coating.

Preparation and characterization of polyester amide resin derived from Nigerian soya bean oil and its performance evaluation as binder for surface coatings

Polymeric systems based on polyesteramides (PEA) are high performance materials, which combine the useful properties of polyester and polyamide resins. In this work, a new modified polyesteramide resin was prepared and evaluated as binder for surface coating.The resin was synthesised by the reaction of N,N-bis-(2-hydroxyethyl) soya bean oil fatty acid amide (HESFAA) as a source of the polyol and as preservative against microbiological attack, with phthalic anhydride as the ingredient source of the polybasic acid. The measured acid value of the resin was found to be 7 mg KOH/g, which indicates the complete formation of the resin. The structure of the resin was confirmed by FT-IR spectral studies. The results show that the modification enhances both phyisco-mechanical and chemical properties of the PEA. From the analyses carried out, the synthesized resin could be suitable as binder for different types of paint. Keywords: Binder, Phthalic anhydride, Polyester amide, Soya bean oil fatty acid

Anticorrosive coating of polyesteramide resin by functionalized ZnO- Al 2 O 3 -Fly ash composite and functionalized multiwalled carbon nanotubes

Abstract In accordance to synthesis of sustainable coating, the carboxyl terminated Polyesteramide resin is synthesized from fatty amide of palm oil. To improve the performance of the coating the ZnO-Al 2 O 3 -fly ash composite and functional Multiwall Carbon nanotubes (MWCNTs) were added to the system. The ZnO-Al 2 O 3 -fly ash composite was treated with amine-silane to develop the amino functionality on the periphery. The MWCNT’s were treated to develop the carboxyl functionality. The presence of functionality on the ZnO-Al 2 O 3 -fly ash composite and MWCNT enable the chemical bonding of same to the coating matrix, improving the performance of the coating. ZnO-Al 2 O 3 - fly ash composites were characterised by FTIR, SEM analysis and XRD to confirm the modification. Also singular and synergistic effect chemically bonded nanocomposite to the coating system was studied by varying the composite ratio as 5% (w/w) & 10% (w/w), MWCNTs ratio individually 0.25% (w/w) & 0.5% (w/w) and in combination of both. The anticorrosive properties were improved, impedance value increases from 100 M (ohms) to 10 G (ohms) in EIS measurement. As well as hardness of the coating increases from H to 4H, scratch resistance increases from 2 kg to 3.1 kg.

Synthesis and Characterisation of New Modified Anti-microbial Polyesteramide Resins by Partial Replacement with the Ingredient Source of The Polybasic Acid Based on Tetrabromophthalic Anhydride for Organic Surface Coatings

Synthesis and Characterisation of New Modified Anti-microbial Polyesteramide Resins by Partial Replacement with the Ingredient Source of The Polybasic Acid Based on Tetrabromophthalic Anhydride for Organic Surface Coatings

Development of Castor Oil Based Poly(urethane‐esteramide)/TiO2 Nanocomposites as Anticorrosive and Antimicrobial Coatings

Castor oil based polyesteramide (CPEA) resin has been successfully synthesized by the condensation polymerization of N‐N‐bis (2‐hydroxyethyl) castor oil fatty amide (HECA) with terephthalic acid and further modified with different percentages of 7, 9, 11, and 13 wt.% of toluene‐2,4‐diisocyanate (TDI) to obtain poly(urethane‐esteramide) (UCPEA), via addition polymerization. TiO2 (0.1, 0.2, 0.3, 0.4, and 0.5 wt%) nanoparticles were dispersed in UCPEA resin. The structural elucidation of HECA, CPEA, and UCPEA has been carried out using FT‐IR, 1H‐NMR, and 13C‐NMR spectroscopic techniques while physicochemical and physicomechanical properties were investigated by standard methods. Thermal stability and molecular weight of UCPEA have been assessed by thermogravimetric analysis (TGA) and gel permeation chromatography (GPC), respectively. Furthermore, the corrosion behavior of UCPEA coatings on mild steel has been investigated by potentiodynamic polarization measurements in different corrosive environments (3.5 wt% HCl, 5 wt% NaCl, 3.5 wt% NaOH, and tap water) at room temperature and surface analysis by scanning electron microscope (SEM) and energy dispersive X‐ray (EDX). The antibacterial activities of the UCPEA were tested against bacteria and fungi by agar disc diffusion method. The results of this study have revealed that UCPEA nanocomposite coatings exhibit good physicomechanical, anticorrosion and antimicrobial properties, which can be safely used up to 200°C.

Polyesteramide resin from PET waste and fatty amide

Purpose – The purpose of this paper is synthesis of polyesteramide resin from jatropha oil and monomer from recycling of poly(ethylene terephthalate) (PET) to get the excellent benefit of individual structure. Along with the synthesis of polyesteramide resin, this research work will also help in recycling of PET waste and help for the conversion of monomer obtained from recycling of PET to value-added application. Design/methodology/approach – Polyesteramide resin was synthesized by conventional method, i.e. by converting jatropha oil to corresponding fatty amide, i.e. hydroxyl ethyl jatropha oil fatty acid amide (HEJA), and treating it with dicarboxylic acid, i.e. sebacic acid but bis(2-hydroxyethyl) terepthalamide (BHETA) is added, i.e. monomer of PET, and then resin synthesis is carried out. Synthesized resin is cured with isocyanate and used for coating application. Coating is characterized for physical, mechanical, thermal and anticorrosive properties. Findings – Coating shows excellent balance of flexibility and hardness due to structural difference in BHETA and HEJA. Aromatic structure of BHETA was helpful for increasing hardness and for retardation of degradation, and at the same time, aliphatic structure of HEJA was helpful for increasing flexibility of the coating. Amide linkage present in both help for better adhesion of coating to metal surface, which also helps to improve the mechanical properties and anticorrosive properties. Practical implications – This method is the practical solution for synthesis of polyesteramide resin and then coating from PET waste and jatropha oil. Hence the method developed is simple and it helps for recycling of PET waste and conversion of recycled product to value-added material. Originality/value – To the best of the authors’ knowledge, this is the first study which use jatropha oil (fatty amide of jatropha oil) and PET waste (monomer of PET waste) simultaneously for the synthesis of polyesteramide resin and then coating.

Fatty acids based transparent polyurethane films and coatings

• Synthesis of polyesteramide from palmitic acid and dimer fatty acid. • Biobased transparent PU films and coatings. • Eco-friendly PU coatings. • Dimer fatty acid as a substitute to conventional dicarboxylic acids or anhydrides. Renewable resources used in the preparation of polymers are falling in the class of biomaterials which are rich in hydrocarbons and most of the times obtained from parts of profusely available agriculture feedstock. Use of non-edible vegetable oils and their fatty acids are currently the raw materials focused in synthesizing polymeric materials as renewable sources due to increasing economic and environmental concerns of petroleums. The current oil based polymers are prepared by consuming petroleum based anhydrides and dicarboxylic acids. With this investigation, we tried to substitute almost all components of petroleum feed stock by renewable sources in preparation of polyol. Initially palmitic acid was used as a renewable source to prepare palmitamide by amidation reaction. Further amide was converted into the polyesteramide resin (PEPAD) by reacting it with another renewable resource, i.e. dimer fatty acid which is the dimerized product of unsaturated fatty acids of vegetable oils. Structure of the prepared resin was confirmed by spectroscopic techniques and resin was also characterized by end group analysis like hydroxyl and acid values. The molecular weight of PEPAD was ranged between 2590 and 2760 g mol −1 . Palmitic acid based polyesteramide was used to prepare polyurethanes by varying amount of diisocyanate. The transparent polyurethane films and coatings were obtained and examined for water absorption, contact angle, hardness, coating properties, solvent, acid and alkali resistances. The thermal properties of the polyurethane films were estimated by TGA and discussed. It was found that change in NCO content affected on transparency as well flexibility of the prepared films. It also noticed that thermal stability was shifted toward higher range by increasing mole (NCO/OH) ratios due to formation of urea linkages.

NEW ANTIMICROBIAL COATING COMPOSITIONS BASED ON 3,6-DICHLORO BEZO[B]THIOPHENE-2-CARBONYL GLUTAMIC ACID. (DCBTGA) . MODIFIED POLYESTERAMIDE RESINS AS BINDER FOR INDUSTRIAL APPLICATIONS

Thiophene and their derivatives products are some of the oldest and best known class of nitrogen and sulphur containing compounds. In recent years there has been considerable interest in the thiophene -based family of materials due to the wide range of antimicrobial activity properties when incorporated into polymers and their composites. In this research new modified polyesteramide resin compositions which are prepared by partial replacement of phthalic anhydride (PA) with 3,6-dichloro bezo[b]- thiophene-2carbonyl glutamic acid (DCBTGA), as a new source of the dibasic acid and as preservative against microbiological attack with N, N- bis - (2-hydroxyethyl) linseed oil fatty acid amide (HELA) as source of polyol. These new source of dicarboxylic acid materials and new modified polyesteramide resin are confirmed by IR and NMR spectral analysis. The coating performance of the resins is evaluated using international standard test methods (ASTM) and involved the measurement of phyisco- mechanical properties such as viscosity, drying time, specular gloss, pencil hardness, adhesion, flexibility and The results show that the modification enhances both phyisco- mechanical and chemical properties The new antimicrobial polyesteramide resins is characterized using standard (Kathon LX biocide) in different excess – OH formulations to reach the best formula against bacteria and fungi. The studies showed promising results as biocide coatings.

Preparation and evaluation of a new anti-corrosive coating based on asphalt cement blended with polyesteramide resin for steel protection

Asphalt cement is a material commonly used in coating applications due to its good adhesion properties and relatively low cost. Unfortunately it has the drawback of being slow to dry. Long polyesteramide resin (PEA) is predominantly used for air-dry and force-dry industrial coatings onto metal surfaces, yet is considered to be a relatively weak material. This paper focuses on the potential synergy of mixing asphalt cement, of penetration grade 60/70, with polyesteramide resin to produce industrial coatings for steel applications, with the aim of overcoming the slow drying time of the asphalt cement and the relative weakness of PEA resin. To achieve this aim, PEA resin was mixed with asphalt cement in a range of concentrations from 3 to 12% (w/w). The prepared coating blends were characterised physically using scanning electron microscopy (SEM), while the performance of the coatings were evaluated for mechanical properties and corrosion resistance in selective chemical reagents, following complete immersion for the duration of 84 days. The results obtained concluded that generally, a blend of asphalt cement and polyesteramide resin produces an effective material for industrial coating applications. Also, 9% and 12% PEA resin content produced high-quality anti-corrosive material as compared to virgin asphalt cement. The degree of modification depends upon the properties of the asphalt and the content level of the polyesteramide.

Anticandidal activity of cobalt containing sunflower oil‐based polymer

Bioactive metal cobalt containing sunflower oil‐based polyesteramide resin was developed by condensation polymerization reaction among oil‐derived sunflower fatty amide diol, adipic acid, and cobalt chloride. Microwave‐assisted synthesis was used throughout the reaction as it enhances reaction rate, gives higher yield, and greater purity of the products. Spectroscopic techniques, such as Fourier transform infrared spectroscopy and proton‐nuclear magnetic resonance, have been used to establish the structure of the polymers. Presence of cobalt in polymer has been confirmed through atomic absorption spectroscopy. Standard laboratory methods such as acid value, hydroxyl value, saponification value, iodine value, specific gravity, and viscosity were used to study the physicochemical characteristics of the polymers. Thermal behavior of the polymer was analyzed using thermogravimetry/differential thermal analysis. The synthesized polymers were evaluated for their biological activity. This study indicates that the synthesized polymer has significant antifungal activity against Candida, including azole‐resistant strains, advocating further investigation for clinical applications in the treatment of fungal infections. POLYM. ENG. SCI., 53:2650–2658, 2013. © 2013 Society of Plastics Engineers

Synthesis and characterisation of new modified anti‐corrosive polyesteramide resins by partial replacement of the ingredient source of the polybasic acid for organic surface coatings

PurposePolymeric systems based on polyesteramides (PEA) are high performance materials, which combine the useful properties of polyester and polyamide resins, and find many applications, most importantly as protective surface coatings. The purpose of this paper is to characterise and evaluate new modified anti‐corrosive PEA resins for use in protective coating formulations.Design/methodology/approachIn the study report here, new modified PEA compositions were prepared and evaluated as vehicles for surface coating. The PEA resins were obtained by means of a condensation polymerisation reaction between phthalic anhydride (PA) and N,N‐bis‐(2‐hydroxyethyl) linseed oil fatty acid amide (HELA) as the ingredient source of the polyol used. The phthalic anhydride was partially replaced with N‐phthaloylglutamic acid NPGA as the ingredient source of the dibasic acid. The structure of the resin was confirmed by FT‐IR spectral studies. Coatings of 50±5 μm thickness were applied to the surface of glass panels and mild steel strips by means of a brush. The coating performance of the resins was evaluated using international standard test methods and involved the measurement of phyisco‐mechanical properties and chemical resistance.FindingsThe tests carried out revealed that the modified PEA based on N‐phthaloylglutamic acid (NPGA) enhanced both phyisco‐mechanical and chemical properties. Also, the resins were incorporated within primer formulations and evaluated as anti‐corrosive single coatings. The results illustrate that the introduction of N‐phthaloylglutamic acid, within the resin structure, improved the film performance and enhances the corrosion resistance performance of PEA resins.Practical implicationsThe modified PEA compounds can be used as binder in paint formulations to improve chemical, physical and corrosion resistance properties.Originality/valueModified PEA resins are cheaper and can be used to replace other more expensive binders. These modified PEA resins can compensate successfully for the presence of many the anticorrosive paint formulations and thus lower the costs. The main advantage of these binders is that they combine the properties of both polyester and polyamide resins based on nitrogenous compound, are of lower cost, and they also overcome the disadvantages of both its counterparts. Also, they can be applied in other industrial applications.

PREPARATION AND EVALUATION OF NEW ANTI-CORROSIVE COATING BASED ON ASPHALT CEMENT (60/70) BLENDED WITH POLYESTERAMIDE RESIN FOR STEEL PROTECTION

The blending of a resin with asphalt cement is a simple method for improving the properties of anti-corrosive paints for the protection of steel. This paper outlines the potential of using asphalt cement blended with polyesteramide resin, for use in paints. Asphalt cement is the most extensively used economic coating material, whereas long polyesteramide resins are predominantly used for air, and force-dry, industrial coatings on metal surfaces. The aim of the research was to blend the two materials together with the objective of reinforcing the positive properties of the resin and attempting to compensate for the resins areas of weakness. The formation of modified functional asphalt cement was based on the fine dispersion of a polyesteramide resin within the asphalt cement, for which the chemical composition of the cement is of key importance. The degree of modification depends on the properties, content and nature of the polyesteramide. The coating blend was characterised using scanning electron microscopy (SEM) and the performance of the coating blend panel was evaluated for mechanical properties and corrosion resistance. The results obtained confirmed that blends of asphalt cement and polyesteramide resin were effective binder materials for industrial coating applications.

Albizia Benth Oil Maleinised Polyesteramides: Synthesis, Structure, and Characteristics

Albizia benth oil (ABO) has been employed in the preparation of polyesteramide resin via the condensation of hydroxyethylamide derivatives of ABO fatty acids and phthalic anhydride. The maleinised Albizia benth oil polyesteramide was prepared, using maleinised hydroxyethylamide derivatives of ABO obtained by appending maleate half esters onto the hydroxyethylamide derivative of ABO and phthalic anhydride. Structural elucidation and characterisation of the products carried out revealed that maleic anhydride can successfully be used to modify polyesteramides, to improve its properties such as drying, flexibility, scratch hardness, impact resistance, chemical resistance, and lower curing temperature.

Synthesis and characterization of poly(styrene‐co‐maleic anhydride) modified pyridine polyesteramide coating from sustainable resource

PurposeThe purpose of this paper is to develop pyridine polyesteramide coatings from Linseed (Linum ussitatissimum) seeds oil for the utilisation of a sustainable resource as coating material, as well as to improve the coating properties.Design/methodology/approachLinseed oil was first converted into N,N bis 2‐hydroxyethyl linseed oil fatty amide (HELA). The resin was synthesized by the reaction of linseed oil fatty amide diol with 2,3‐pyridine di carboxylic acid to develop pyridine polyesteramide (Py‐PEA) and further treated with poly(styrene‐co‐maleic anhydride)(SMA) in different phr (part per hundred part of resin). The structural elucidation of Py‐PEA was carried out by FT‐IR, 1H‐NMR and 13C‐NMR spectral techniques. The thermal stability and curing behaviour of the resin were determined by differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA), respectively. The physico‐mechanical and anticorrosive properties were investigated by standard laboratory methods.FindingsThe authors developed a good anticorrosive coating material from sustainable resource. The physico‐mechanical and anticorrosive performance evaluation exhibited satisfactory results. The approach facilitated curing to occur at ambient temperature and the thermal studies revealed that Py‐PEA‐SMA‐45 might be safely used up to 140°C.Practical implicationsPoly(styrene‐co‐maleic anhydride) modified pyridine polyesteramide coatings showed the highest scratch hardness 3.0 kg, flexibility (1/8 inch canonical mandrel bend test) and gloss at 45° is 62‐64. Among all, Py‐PEA‐SMA 45 showed the best physico‐mechanical and chemical resistance performance. Thus, the resin may be used as an effective coating material.Originality/valueThe paper shows that the synthesis of polyesteramide resin from vegetable oil provides a new way to utilize a renewable resource based raw material.

A Polyesteramide Resin from Jatropha curcas Seed Oil for Anticorrosive Coating

A Polyesteramide Resin from Jatropha curcas Seed Oil for Anticorrosive Coating