2017

Open AccessArticle Characterization and Performance of Soy-Based Adhesives Cured with Epoxy Resin

by Nairong Chen, Peitao Zheng, Qinzhi Zeng, Qiaojia Lin and Jiuping Rao

Polymers 2017, 9(10), 514; doi:10.3390/polym9100514

Received: 27 August 2017 / Revised: 2 October 2017 / Accepted: 12 October 2017 / Published: 16 October 2017

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Abstract

Soy-based adhesives have attracted much attention recently because they are environmentally safe, low cost, and readily available. To improve the gluability and water resistance of soy-based adhesives, we prepared an enzyme-treated soy-based adhesive modified with an epoxy resin. We investigated the wet shear

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Soy-based adhesives have attracted much attention recently because they are environmentally safe, low cost, and readily available. To improve the gluability and water resistance of soy-based adhesives, we prepared an enzyme-treated soy-based adhesive modified with an epoxy resin. We investigated the wet shear strength of plywood bonded with the modified adhesive using the boiling-water test. Fourier transformed infrared spectroscopy (FTIR) and ¹H nuclear magnetic resonance analysis were used to characterize the reaction between epoxy groups and –NH₂ groups in the modified soy-based adhesives. FTIR analysis confirmed the cross-linking structure in the cured adhesives. Viscosity and the solid content of soy-based adhesives gradually increased with the increasing amount of epoxy resin, but had little effect on its operability. Wet shear strength of plywood samples increased as the amount of epoxy resin was increased, whereas the inverse trend was observed regarding the water absorption of cured adhesives. Compared to an unmodified adhesive, the addition of 30% of epoxy resin increased the wet shear strength of plywood samples by 58.3% (0.95 MPa), meeting the requirement of the Chinese National Standard for exterior plywood. Differential scanning calorimetry and thermogravimetric analysis showed the improved thermostability of the cured adhesives after curing at 160 °C. These results suggest that epoxy resin could effectively improve the performance of enzyme-treated soy-based adhesives, which might provide a new option for the preparation of soy-based adhesives with high gluability and water resistance. Full article

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Open AccessArticle Mechanism of Base-Catalyzed Resorcinol-Formaldehyde and Phenol-Resorcinol-Formaldehyde Condensation Reactions: A Theoretical Study

by Taohong Li, Ming Cao, Jiankun Liang, Xiaoguang Xie and Guanben Du

Polymers 2017, 9(9), 426; doi:10.3390/polym9090426

Received: 13 August 2017 / Revised: 1 September 2017 / Accepted: 5 September 2017 / Published: 7 September 2017

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Abstract

The base-catalyzed resorcinol-formaldehyde condensation reactions were theoretically investigated in this study by employing a quantum chemistry method. The condensation reaction includes two steps: (1) formation of the quinonemethide (QM) intermediate from hydroxymethylresorcinol; (2) Michael addition between the quinonemethide and resorcinol anion. The first

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The base-catalyzed resorcinol-formaldehyde condensation reactions were theoretically investigated in this study by employing a quantum chemistry method. The condensation reaction includes two steps: (1) formation of the quinonemethide (QM) intermediate from hydroxymethylresorcinol; (2) Michael addition between the quinonemethide and resorcinol anion. The first step is the rate-determining step. Two mechanisms, unimolecular elimination of the conjugate base (E1cb) and water-aided elimination (WAE), were identified for the formation of QM. The hydroxymethylresorcinol anion produces neutral QM while the dianion produces a quinonemethide anion (QMA). The calculated potential energy barriers suggested that the QMA formation is much more favorable. Although resorcinol-formaldehyde and phenol-formaldehyde condensations share a common mechanism, the former would be faster if the QMA participates in condensations. The potential energy barriers for formation of 2-QM, 4-QM, 6-QM, 2-QMA, and 4-QMA were calculated. The results show that the formations of 6-QM and 4-QMA have relatively lower energy barriers. This rationalized previous experimental observations that the 2,4-(2,6-) and 6,6′-(4,4′-) methylene linkages were dominant, whereas the 2,2′-linkage was almost absent. The resorcinol-phenol-formaldehyde co-condensations were also calculated. The cold-setting characteristic of phenol-resorcinol-formaldehyde co-condensed resin can be attributed to participation of resorcinol quinonemethides in condensations. Full article

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Open AccessCommunication Synthesis of Humin-Phenol-Formaldehyde Adhesive

by Shimin Kang, Jinxia Fu, Gang Zhang, Wentao Zhang, Huibin Yin and Yongjun Xu

Polymers 2017, 9(8), 373; doi:10.3390/polym9080373

Received: 27 May 2017 / Revised: 11 August 2017 / Accepted: 14 August 2017 / Published: 18 August 2017

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Abstract

Humins are low-value-added byproducts from the biomass acid hydrolysis process. In the present work, humins were first employed as a phenol replacement for synthesis of modified phenol-formaldehyde adhesives through a two-step process. In this process, humins were first utilized to obtain alkaline soluble

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Humins are low-value-added byproducts from the biomass acid hydrolysis process. In the present work, humins were first employed as a phenol replacement for synthesis of modified phenol-formaldehyde adhesives through a two-step process. In this process, humins were first utilized to obtain alkaline soluble products, mainly consisting of phenolics, through a hydrothermal process. The obtained alkaline soluble products then reacted with phenol and formaldehyde to produce humin-phenol-formaldehyde adhesive (HPFA). The physicochemical properties of HPFA, including viscosity, bonding strength, pH, free formaldehyde level, free phenol level and solid content, met the requirements of the GB/T 14732-2006 Chinese National Standard. Full article

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Open AccessArticle Theoretical Study on Decomposition Mechanism of Insulating Epoxy Resin Cured by Anhydride

by Xiaoxing Zhang, Yunjian Wu, Xiaoyu Chen, Hao Wen and Song Xiao

Polymers 2017, 9(8), 341; doi:10.3390/polym9080341

Received: 11 July 2017 / Revised: 31 July 2017 / Accepted: 3 August 2017 / Published: 4 August 2017

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Abstract

High temperatures caused by partial discharge results in the decomposition of insulating epoxy resins in electrical equipment. In this paper, the ReaxFF force field is used to investigate the decomposition process of epoxy resins cured by anhydride and the formation mechanisms of small-molecule

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High temperatures caused by partial discharge results in the decomposition of insulating epoxy resins in electrical equipment. In this paper, the ReaxFF force field is used to investigate the decomposition process of epoxy resins cured by anhydride and the formation mechanisms of small-molecule gases. Results show that the initiation reaction is the cleavage of an ester bond linked with an epoxy resin. Produced by the decomposition of ester groups, CO₂ is the first and most abundant product. Meanwhile, CH₂O can be generated through three main ways, although the process still depends on the decomposition of epoxy functional groups. H₂O is produced by free radical collision and dehydration. The production of small-molecule gases has the following sequence: CO₂, CH₂O, CO, and H₂O. The produced gases have the following order according to amount: CO₂, CH₂O, H₂O, and CO. Full article

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Open AccessArticle Improve Performance of Soy Flour-Based Adhesive with a Lignin-Based Resin

by Xiaochun Zhang, Yuding Zhu, Youming Yu and Jiangang Song

Polymers 2017, 9(7), 261; doi:10.3390/polym9070261

Received: 10 May 2017 / Revised: 26 June 2017 / Accepted: 27 June 2017 / Published: 3 July 2017

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Abstract

A lignin-based resin (LB) was used to improve the performance of soy flour-based adhesives. Soy flour (SF), polyamidoamine-epichlorohydrin (PAE), and LB were used to develop a plywood adhesive. The solid content and viscosity of the adhesive, the functional groups, the thermo-stability, and the

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A lignin-based resin (LB) was used to improve the performance of soy flour-based adhesives. Soy flour (SF), polyamidoamine-epichlorohydrin (PAE), and LB were used to develop a plywood adhesive. The solid content and viscosity of the adhesive, the functional groups, the thermo-stability, and the crystallinity of the cured adhesives were characterized, and the performance of the resultant adhesive was evaluated by fabricating three-ply plywood. Results showed that the LB and PAE mixture used to modify the SF adhesive improved both dry and wet bond strength by 66.3% and 184.2%, respectively. Therefore, the PAE improved the wet bond strength, and the LB improved the dry bond strength. The improvement was attributed to: (1) the reaction of LB/PAE with the functions of the soy protein to form a cross-linking network; (2) a polycondensation reaction between the LB molecules improved the crosslinking density of the adhesive to form an interpenetration structure with cross-linked proteins; and (3) the easy penetration of the LB into the wood surface that enhanced interlocking between the wood and adhesive. Furthermore, the denser structure created by the LB and the PAE mixture improved thermal stability and decreased the crystallinity of the cured adhesive. The use of the LB and the PAE mixture increased the solid content by 35.5%, while still making its viscosity acceptable for industrial applications. Full article

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Open AccessArticle Controlled Light Cross-Linking Technique to Prepare Healable Materials

by Soliman Abdalla, Fahad Al-Marzouki, Abdullah Obaid and Fatma Bahabri

Polymers 2017, 9(6), 241; doi:10.3390/polym9060241

Received: 25 April 2017 / Revised: 19 June 2017 / Accepted: 19 June 2017 / Published: 21 June 2017

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Abstract

Detection of defects, damages and cracks in structural polymers is very difficult, and even if they are detected, they will be very hard to be repaired. This is because different kinds of stress can reduce the mechanical efficiency of structural and functional thermosetting

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Detection of defects, damages and cracks in structural polymers is very difficult, and even if they are detected, they will be very hard to be repaired. This is because different kinds of stress can reduce the mechanical efficiency of structural and functional thermosetting composite materials and they can damage the polymer matrix, thus reducing the purposed properties. General healing processes use thermal energy “alone” to heal these materials, thus impairing the intended properties of the materials. Therefore, we present a thermal healing ability that can be switched-on and/or -off at desire using illumination by photon energy (visible and ultra violet). By this technique, one can control local heal while keeping the efficiency of the material nearly unchanged. Furan-based cross-linker chemically reacts (forward- and reverse-reaction) with short-chains of maleimide-substituted poly(lauryl methacrylate) to form robust chemical bonds. This permits us to perform local control over thermally induced de- and/or re-cross-linking techniques. One can extend and apply this technique to cover micro-devices, coating-techniques, fine lithography, micro- and nano-fabrication processes, etc. Therefore, the present work developed a suitable technology with structural polymeric material, which has the ability to self-heal cracks (and damages) and recover structural function. Full article

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Open AccessArticle The Preparation and Characterization of Pyrolysis Bio-Oil-Resorcinol-Aldehyde Resin Cold-Set Adhesives for Wood Construction

by Xueyong Ren, Hongzhen Cai, Hongshuang Du and Jianmin Chang

Polymers 2017, 9(6), 232; doi:10.3390/polym9060232

Received: 28 April 2017 / Revised: 14 June 2017 / Accepted: 15 June 2017 / Published: 18 June 2017

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Abstract

Resorcinol-formaldehyde (RF) resin is a kind of excellent exterior-grade wood structural adhesive, which can be conveniently cold-set for various applications. In order to decrease the production cost, pyrolysis bio-oil from renewable bioresources was used to replace resorcinol to synthesize the bio-oil-resorcinol-aldehyde (BRF) resin.

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Resorcinol-formaldehyde (RF) resin is a kind of excellent exterior-grade wood structural adhesive, which can be conveniently cold-set for various applications. In order to decrease the production cost, pyrolysis bio-oil from renewable bioresources was used to replace resorcinol to synthesize the bio-oil-resorcinol-aldehyde (BRF) resin. The effect of replacing resorcinol with bio-oil on the properties, bonding performance, and characterization of resorcinol-aldehyde resin was comparatively investigated. A higher solid content and viscosity, albeit a lower shear strength, was found when the replacement ratio of bio-oil increased. The bonding performance of BRF with 10 and 20 wt % bio-oil was close to that of the pure RF resin. However, the trends of being less cross-linked, more easily decomposed, but more porous were found when the substitution ratio of bio-oil was higher than 20 wt %. Interestingly, it was found that the wood failure values of the BRF resins with bio-oil of no more than 20 wt % were slightly higher than that of the pure RF resin. On the whole, BRF resins with 20 wt % bio-oil is recommended as a wood structural adhesive, comprehensively considering the bio-oil substitution ratio and resin properties. The results obtained here showed that pyrolysis bio-oil is a promising green raw material for the production of RF resin with lower cost. Full article

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Open AccessArticle Analysis of the Cross-Linking Reaction of Lignin with Triethyl Phosphate by MALDI-TOF and ¹³C NMR

by María Cecilia Basso, Antonio Pizzi, Luc Delmotte and Soliman Abdalla

Polymers 2017, 9(6), 206; doi:10.3390/polym9060206

Received: 4 April 2017 / Revised: 31 May 2017 / Accepted: 2 June 2017 / Published: 4 June 2017

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Abstract

The reaction of condensation and cross-linking of desulfurized kraft lignin with triethyl phosphate (TEP) was explored. Catechol, a simple model of the aromatic ring of lignin, and glycerol, a model compound of the aliphatic hydroyl groups of the side chain of lignin, were

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The reaction of condensation and cross-linking of desulfurized kraft lignin with triethyl phosphate (TEP) was explored. Catechol, a simple model of the aromatic ring of lignin, and glycerol, a model compound of the aliphatic hydroyl groups of the side chain of lignin, were employed under similar reaction conditions. Solid state cross-polarisation/magic-angle spinning (CP-MAS) ¹³C NMR and matrix assisted laser desorption ionization time-of-flight (MALDI-TOF) spectroscopy studies showed that polycondensation occurs on phenolic hydroxyl groups of lignin, as well as on aliphatic hydroxyls groups of its side chain. The reactions appear to be favoured by higher temperatures and in the presence of ammonia. Preliminary adhesion tests on wood shown good hydrophobicity properties of the surface treated with lignin-TEP-based resin. Initial application tests carried out at high temperature demonstrated as good performance as metallic coating. Full article

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Open AccessArticle New Mechanism Proposed for the Base-Catalyzed Urea–Formaldehyde Condensation Reactions: A Theoretical Study

by Taohong Li, Ming Cao, Jiankun Liang, Xiaoguang Xie and Guanben Du

Polymers 2017, 9(6), 203; doi:10.3390/polym9060203

Received: 12 May 2017 / Revised: 27 May 2017 / Accepted: 27 May 2017 / Published: 2 June 2017

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Abstract

Base-catalyzed urea–formaldehyde condensation reactions were investigated by using a quantum chemistry method. It was found that monomethylolurea or N,N’-dimethylolurea can produce the methyleneurea intermediate (–HN–CO–N=CH₂) with the catalysis of base. The E1cb (unimolecular elimination of conjugate base) mechanism

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Base-catalyzed urea–formaldehyde condensation reactions were investigated by using a quantum chemistry method. It was found that monomethylolurea or N,N’-dimethylolurea can produce the methyleneurea intermediate (–HN–CO–N=CH₂) with the catalysis of base. The E1cb (unimolecular elimination of conjugate base) mechanism was identified for the formation of such an intermediate. The potential energy barrier was theoretically predicted to be 59.6 kJ/mol for the E1cb step, which is about half of that of previously proposed S_N2 (bimolecular nucleophilic substitution) mechanism. In the subsequentcondensation reactions, Michael addition reactions that lead to different condensed structures can occur between the methyleneurea intermediate and the anions produced from methylolureas under alkaline conditions. Based on the theoretical calculations on the kinetics and thermodynamics of the selected reactions, the competitive formations of methylene linkages, ether linkages and uron were discussed in combination with our previous experimental observations. Full article

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Open AccessArticle Investigation on the Influence of Chain Extenders on the Performance of One-Component Moisture-Curable Polyurethane Adhesives

by Chen Tan, Teija Tirri and Carl-Eric Wilen

Polymers 2017, 9(5), 184; doi:10.3390/polym9050184

Received: 2 April 2017 / Revised: 15 May 2017 / Accepted: 16 May 2017 / Published: 21 May 2017

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Abstract

In this work, a number of chain extended moisture-curable urethane prepolymers were synthesized in order to develop isocyanate terminated urethane prepolymer formulations that would simultaneously display both high adhesive strength and low viscosity. Proton nuclear magnetic resonance spectroscopy (¹H-NMR), size exclusion

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In this work, a number of chain extended moisture-curable urethane prepolymers were synthesized in order to develop isocyanate terminated urethane prepolymer formulations that would simultaneously display both high adhesive strength and low viscosity. Proton nuclear magnetic resonance spectroscopy (¹H-NMR), size exclusion chromatography (SEC), differential scanning calorimetry (DSC), and Brookfield viscometry were utilized for characterizing the prepared urethane prepolymers. In addition, the adhesion strength of the cured prepolymers was determined by tensile shear strength test according to the DIN EN (Deutsches Institut für Normung, the German Institute for Standardization) 1465 standard. Especially, the role of different types of linear (butanediol, pentanediol) and branched chain extenders (dipropyleneglycol (di-PPG), tripropyleneglycol (tri-PPG) and the influence of their dosage on the degree of microphase separation between hard segments (HS) and soft segments (SS) in urethane prepolymers were studied. Furthermore, the benefits of utilizing either a one-step versus a two-step polymerization process were investigated. The results revealed that the extent of phase separation of different urethane prepolymers was dependent on the extent of hydrogen bonding interactions which was extensively studied by attenuated total reflectance infrared spectroscopy (ATR-FTIR). The incorporation of branched chain extenders (di-PPG and tri-PPG) did not result in notable phase separation between hard segments and soft segments, while linear chain extenders (pentanediol and butanediol) readily promoted phase separation. The degree of phase separation was particularly pronounced for butanediol, and when the linear chain extender ratio was higher than or equal to 0.74. Compared with a two-stage process, one-stage process produced more randomly distributed polymer chains with highly dispersed hard segments. Thus, urethane prepolymers exhibiting strong adhesive strength with simultaneously low viscosity were successfully developed by systematic adjustment of structural parameters. Full article

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Open AccessArticle Soy-Based Adhesive Cross-Linked by Phenol-Formaldehyde-Glutaraldehyde

by Zhigang Wu, Xuedong Xi, Hong Lei and Guanben Du

Polymers 2017, 9(5), 169; doi:10.3390/polym9050169

Received: 10 March 2017 / Revised: 2 May 2017 / Accepted: 5 May 2017 / Published: 8 May 2017

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Abstract

To prepare a low-formaldehyde soy-based adhesive with good water resistance, phenol-formaldehyde modified with glutaraldehyde (PFG) with lower free phenol and free formaldehyde contents was used to cross-link the soy-based adhesive. The results showed that the mechanical properties and water resistance of plywood prepared

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To prepare a low-formaldehyde soy-based adhesive with good water resistance, phenol-formaldehyde modified with glutaraldehyde (PFG) with lower free phenol and free formaldehyde contents was used to cross-link the soy-based adhesive. The results showed that the mechanical properties and water resistance of plywood prepared with soy-based adhesive with PFG was better than that of plywood with the same amount of phenol-formaldehyde (PF). The reaction between phenol and glutaraldehyde was proved by ¹³C-NMR. Under the optimized preparation conditions for plywood, that is to say, press temperature 160 °C, press time 4 min and resin loading 320 g·m⁻², type I plywood could be prepared with 9% PFG as a cross-linker of soy-based adhesive. The Differential Scanning Calorimetry (DSC) result confirmed the cross-linking reaction between soy-based adhesive and PFG or PF. The activation energy of soy-based adhesive with cross-linker PFG was higher than that with PF resin. Full article

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Open AccessArticle Preparation, Characterization and Mechanical Properties of Bio-Based Polyurethane Adhesives from Isocyanate-Functionalized Cellulose Acetate and Castor Oil for Bonding Wood

by Adrián Tenorio-Alfonso, María Carmen Sánchez and José M. Franco

Polymers 2017, 9(4), 132; doi:10.3390/polym9040132

Received: 6 March 2017 / Revised: 29 March 2017 / Accepted: 3 April 2017 / Published: 5 April 2017

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Abstract

Nowadays, different types of natural carbohydrates such as sugars, starch, cellulose and their derivatives are widely used as renewable raw materials. Vegetable oils are also considered as promising raw materials to be used in the synthesis of high quality products in different applications,

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Nowadays, different types of natural carbohydrates such as sugars, starch, cellulose and their derivatives are widely used as renewable raw materials. Vegetable oils are also considered as promising raw materials to be used in the synthesis of high quality products in different applications, including in the adhesive field. According to this, several bio-based formulations with adhesion properties were synthesized first by inducing the functionalization of cellulose acetate with 1,6-hexamethylene diisocyanate and then mixing the resulting biopolymer with a variable amount of castor oil, from 20% to 70% (wt). These bio-based adhesives were mechanically characterized by means of small-amplitude oscillatory torsion measurements, at different temperatures, and standardized tests to evaluate tension loading (ASTM-D906) and peel strength (ASTM-D903). In addition, thermal properties and stability of the synthesized bio-polyurethane formulations were also analyzed through differential scanning calorimetry and thermal gravimetric analysis. As a result, the performance of these bio-polyurethane products as wood adhesives were compared and analyzed. Bio-polyurethane formulations exhibited a simple thermo-rheological behavior below a critical temperature of around 80–100 °C depending on the castor oil/cellulose acetate weight ratio. Formulation with medium castor oil/biopolymer weight ratio (50:50 % wt) showed the most suitable mechanical properties and adhesion performance for bonding wood. Full article

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Open AccessArticle The Influence of pH on the Melamine-Dimethylurea-Formaldehyde Co-Condensations: A Quantitative ¹³C-NMR Study

by Ming Cao, Taohong Li, Jiankun Liang and Guanben Du

Polymers 2017, 9(3), 109; doi:10.3390/polym9030109

Received: 22 February 2017 / Revised: 13 March 2017 / Accepted: 15 March 2017 / Published: 17 March 2017

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Abstract

1,3-dimethylurea (DMU) was used to mimic urea and to model melamine-urea-formaldehyde (MUF) co-condensation reactions. The products of 1,3-dimethylurea-formaldehyde (DMUF), melamine-formaldehyde (MF), and melamine-1,3-dimethylurea-formaldehyde (MDMUF) reactions under alkaline and weak acidic conditions were compared by performing quantitative carbon-13 nuclear magnetic resonance (¹³C-NMR)

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1,3-dimethylurea (DMU) was used to mimic urea and to model melamine-urea-formaldehyde (MUF) co-condensation reactions. The products of 1,3-dimethylurea-formaldehyde (DMUF), melamine-formaldehyde (MF), and melamine-1,3-dimethylurea-formaldehyde (MDMUF) reactions under alkaline and weak acidic conditions were compared by performing quantitative carbon-13 nuclear magnetic resonance (¹³C-NMR) analysis. The effect of pH on the co-condensation reactions was clarified. With the presence of the methyl groups in DMU, the appearance or absence of the featured signal at 54–55 ppm can be used to identify the co-condensed methylene linkage –N(–CH₃) –CH₂–NH–. Under alkaline condition, MDMUF reactions produced primarily MF polymers and the featured signal at 54–55 ppm was absent. Even though the co-condensations concurrently occurred, undistinguishable and very minor condensed structures with ether linkage were formed. Differently, under weak acidic condition, the relative content of co-condensed methylene carbons accounts for over 40%, indicating the MDMUF co-condensation reactions were much more competitive than the self-condensations. The formation of reactive carbocation intermediate was proposed to rationalize the results. Full article

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