Polybutylene terephthalate modified with dimer acid methyl ester derived from fatty acid methyl esters and its use as a hot‐melt adhesive

Kim, A Ryeon; Park, Min Su; Lee, Sang-Jun; Ra, Mirae; Shin, Jihoon; Kim, Young‐Wun

doi:10.1002/app.48474

Cited by 10 publications

(7 citation statements)

References 42 publications

(59 reference statements)

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“…The synthesis and properties of TPCs comprising hard (i.e., semicrystalline) alkyl terephthalate units and soft blocks based on DFA derivatives (e.g., acids or diols) have been explored in the literature. − Nevertheless, these materials have been generated exclusively from virgin monomer feeds (i.e., dimethyl terephthalate, ethylene glycol, DFA). The most relevant reports to date are a patent , and a recent publication that disclose the multistep preparation of polyol oligomers from rPET and DFAs intended as precursors to polyurethanes.…”

Section: Introductionmentioning

confidence: 99%

Bio-Based Upcycling of Poly(ethylene terephthalate) Waste for the Preparation of High-Performance Thermoplastic Copolyesters

2022

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Thermoplastic copolyesters occupy an important segment in the materials market, finding use in a wide range of engineering plastic applications. This fact owes itself to the versatility underlying the synthetic preparation. However, the industry relies nearly exclusively on virgin feedstocks that are derived from fossil-based resources. With a keen interest in improving the deleterious environmental impact of this material class, we combine postconsumer recycled PET (rPET) with a bioderived dimer fatty acid (DFA) building block for the synthesis of segmented thermoplastic copolyesters (TPCs) via solvent-free melt polycondensation. The influence of (i) catalyst type, (ii) hard block (i.e., PET) precursor, and (iii) soft block (i.e., DFA) content on the microstructure and mechanical properties of TPCs was assessed. Samples that exhibit equivalent mechanical strength and segment distribution are accessible using either pristine bis-hydroxy ethylene terephthalate (BHET) or rPET as starting materials. Screening of reaction conditions and composition space within this context was performed with small-scale (2 g) reactions. Further optimization of reaction conditions in terms of catalyst concentration and ethylene glycol deconstruction agent content allowed for the upscaled synthesis (100 g) of engineering-grade TPCs in a custom-built reactor. We believe that our results contribute to a new paradigm in the efforts for more responsible manufacturing practices for TPCs and provide an additional outlet for the efficient handling of end-of-life, recyclable plastics.

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Section: Introductionmentioning

confidence: 99%

Bio-Based Upcycling of Poly(ethylene terephthalate) Waste for the Preparation of High-Performance Thermoplastic Copolyesters

2022

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“…All these materials are produced from petroleum-based compounds. To reduce dependence on petroleum resources, among them, polyols are the most likely to be replaced by biomass polyols derived from plants such as castor oil [ 4 , 5 ] and dimer acid-based derivatives [ 6 ]. Moreover, CO 2 -based polyols are another available resource [ 7 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Properties of Moisture-Cured Reactive Polyurethane Containing Castor Oil and Oxime Compounds

Wu¹

2020

Polymers

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Reactive polyurethane hot-melt resin (moisture-cured reactive polyurethane, PUR) could successfully be prepared from poly(tetramethylene ether) glycol (PTMG), castor oil and dimethylglyoxime (DMG) by one or two-stage synthesis. Fourier-transform infrared spectroscopy (FTIR) analysis showed that the synthesis resins belonged to NCO-capped castor oil-based polyurethane. The thermal behaviors of the cured PUR were analyzed by differential scanning calorimeter (DSC) and dynamic mechanical analyzer (DMA) instruments. The results showed that the cured resin provided remeltable properties under the dosages of 3 wt% DMG. Furthermore, the phenomenon could be proved by FTIR analysis according to the characteristic absorption peak of NCO groups after the cured resin was heated. Comparing different syntheses, the resin prepared by one-stage synthesis showed random distribution of DMG with PUR structure and that prepared by two-stage synthesis had distribution of DMG with branching structure in the prepolymer. The former obtained lower remeltable temperatures from 90 to 130 °C than the latter temperatures, which had temperatures above 125 °C. The tensile test showed that all of the PUR films exhibited typical tough behavior. Thus, the cured resin with DMG dosages of 3 wt% provided remeltable and mechanical properties at the same time. Overall, the crosslinking density and numbers of dynamic bonds should be kept in balance for preparation of remeltable PUR.

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“…The carbonyl peaks of the ester bands of the DMT unit shifted from 1718 cm À1 . [79][80][81][82] The heat flow traces of the copolymers in the temperature range of -50 to 250 C are shown in Figure 3. The melting point (T m ) is set as the top of the endothermic peak in the reheating traces.…”

Section: Copolymer Characterizationmentioning

confidence: 99%

Sustainable castor oil-based semi-aromatic copolyesters with high strength and low hydrolysis

Wang

Mao

Chen

et al. 2023

Textile Research Journal

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Hot-melt adhesives are solid adhesives that are converted to a melting state for application to substrates and on cooling efficiently sets up the bond. Due to low or no volatile organic compound emissions, hot-melt adhesives are extensively used in various applications. Poly(trimethylene terephthalate- co-adipate) copolymers containing dimethyl terephthalate, adipic acid, and 1,3-propanediol along with varying amounts of castor oil were synthesized by one-step melt polymerization as hot-melt adhesives. The structure, composition, and thermal properties of these samples were analyzed, and all samples showed excellent thermal stability with Td-5% values above 300°C. Differential scanning calorimetry measurements showed tunable melting temperatures of the copolymers in the range of 80–180°C, which increased with the content of dimethyl terephthalate and decreased with increasing amounts of castor oil. The incorporation of castor oil as soft segments enhanced the flexibility of the molecular chain, indicating an increment in the elongation rate while decreasing the stress at the break and glass transition temperatures. Rheological examinations showed significant increments in the viscosity at lower angular frequencies with the introduction of castor oil; this was attributed to the entanglement caused by the multifunctional groups of castor oil with dangling chains in the segments. As the angular frequency increased, the viscosities of the samples decreased almost linearly, revealing good applicability in the melting process of the copolymers, which presented controllable melting viscosities under different process conditions. The T-peel test was used to investigate the adhesion properties of the copolymers, and the copolymer with 50/50 molar ratio of dimethyl terephthalate/adipic acid with 3 mol% castor oil PT(T50A50)-C3 exhibited excellent binding capacity between the copolymer and poly(ethylene terephthalate) fabric with a peel strength of 2624.5 N m−1. Moreover, PT(T50A50)-C3 shows low moisture absorption, good hydrolysis resistance, and relatively low hardness, which indicates its high potential for application in hot-melt adhesives on polyester fabrics with high strength, good tactile quality, and long service life.

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Polybutylene terephthalate modified with dimer acid methyl ester derived from fatty acid methyl esters and its use as a hot‐melt adhesive

Cited by 10 publications

References 42 publications

Bio-Based Upcycling of Poly(ethylene terephthalate) Waste for the Preparation of High-Performance Thermoplastic Copolyesters

Bio-Based Upcycling of Poly(ethylene terephthalate) Waste for the Preparation of High-Performance Thermoplastic Copolyesters

Synthesis and Properties of Moisture-Cured Reactive Polyurethane Containing Castor Oil and Oxime Compounds

Sustainable castor oil-based semi-aromatic copolyesters with high strength and low hydrolysis

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