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Frontiers of Environmental Science & Engineering

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Front. Environ. Sci. Eng.    2024, Vol. 18 Issue (10) : 128    https://doi.org/10.1007/s11783-024-1888-0
Thermal degradation and hydrolysis depolymerization of printing ink components for plastic packaging in recycling processes: a review
Jinyang Guo(), Cong Luo, Zhi Kai Chong, Ayah Alassali, Kerstin Kuchta()
Circular Resource Engineering and Management (CREM), Hamburg University of Technology (TUHH), 21079 Hamburg, Germany
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Abstract

● Identifies and elucidates the concurrent thermal degradation and hydrolysis of common binders in flexible plastic packaging during mechanical recycling.

● Reveals that thermal degradation for a variety of binder resins begins between 200–300 °C, with hydrolysis potentially intensified by humidity from cleaning processes.

● Demonstrates how the compatibility between binder resins and polyolefin affects the quality of recycled plastics, emphasizing this issue regarding immiscibility.

● Underscores the influence of binder resins and their degradation products on the efficacy of advanced recycling methods like selective dissolution-precipitation and pyrolysis.

This review covers the decomposition mechanisms of various printing ink binder resins, with a particular focus on their behavior under extrusion conditions in the mechanical recycling process of polyolefin (PO) based plastic packaging. Thermal degradation and hydrolysis of the nitrocellulose (NC) ─ the most used binder for flexographic surface printing on single-layer flexible plastic packaging, occur concurrently during the mechanical recycling process under 160–210 °C. For other printing ink binders, polyurethane (PU) noticeable degradation takes place between 200 and 300 °C, mostly above 250 °C. However, with the involvement of humidity, degradation by hydrolysis can start from 150 °C. A similar effect is also discovered with the cellulose acetate (CA) derivatives, which are thermally stable until 300 °C and can be hydrolyzed at 100 °C. The thermal stability of polyvinyl butyral (PVB) is not influenced by humidity, with thermal stability ranging from 170 to 260 °C, depending on different types. Ultraviolet (UV)-cured acrylics are thermally stable until 400 °C. The hydrolysis degradation can take place at room temperature. Moreover, this review covers the thermal stability of different colorants used for printing ink application and elaborates on several thermal-stable alternatives of some common colors. This study further reviews how the binder resin affects the quality of recyclates, revealing it to be not only induced by the degradation of the binder resin but also by the immiscibility between the plastic and binder resin. In advanced recycling processes, mainly selective dissolution-precipitation and pyrolysis, the presence of binder resin and its degradation products could still affect the quality of the product. This review accentuates the imperative need for in-depth research to unravel the impact of printing ink constituents on the quality of recycled products.
Keywords Plastic recycling      Flexible packaging      Polymer degradation      Green chemistry     
Corresponding Author(s): Jinyang Guo,Kerstin Kuchta   
Issue Date: 06 August 2024
 Cite this article:   
Jinyang Guo,Cong Luo,Zhi Kai Chong, et al. Thermal degradation and hydrolysis depolymerization of printing ink components for plastic packaging in recycling processes: a review[J]. Front. Environ. Sci. Eng., 2024, 18(10): 128.
 URL:  
https://academic.hep.com.cn/fese/EN/10.1007/s11783-024-1888-0
https://academic.hep.com.cn/fese/EN/Y2024/V18/I10/128
Binder resin Application Source
Nitrocellulose (NC) Printing ink for flexible plastic packaging Guo et al. (2023b); Ügdüler et al. (2023); Kaedin-Koppers (2023)
Polyurethane (PU) Printing ink for flexible plastic packaging (currently mainly for multilayer plastic packaging) Akindoyo et al. (2016); Kaedin-Koppers (2023); Szabo (2002)
Polyvinyl butyral (PVB) Printing ink for flexible plastic packaging (flexographic and gravure printing) Rathschlag (2021); Hancock (1993)
Polyamide (PA) Mainly used as a co-binder or OPV Hinden and Whyzmuzis (1973); Szabo (2002); Ramadan et al. (2019)
Cellulose acetate (CA) and derivatives Mainly used as overprint varnish Yu and Gray (1998); Flick (1999); Yu and Gray (1998); Meng et al. (2017); Robert (2015)
Polymethyl methacrylate (PMMA) Mainly used for screen printing for textile Kuo et al. (2022)
Polyvinyl acetate (PVA) Mainly used for ink jet printing (i.e., paper) Zhang et al. (2015); Lamminmäki et al. (2011)
Polyacrylic resin Mainly used label, including in-mold labeling (IML) of rigid packaging material Duan et al. (2017); Robert (2015)
Tab.1  Common binder resins for printing inks according to Guo et al. (2023b) and Ügdüler et al. (2023)
Fig.1  Chemical structures of common printing ink binders (a) nitrocellulose, (b) polyurethane (aliphatic), (c) polyvinyl butyral, (d) cellulose acetate propionate, (e) polyamide, (f) upper: acrylate monomer, lower: acrylate polymer after UV curing (crosslinking).
Fig.2  Depolymerization reactions of polycondensate polymer.
Fig.3  Thermal decomposition and hydrolysis reactions of nitrocellulose, summarized based on Katoh et al. (2010); Rychlý et al. (2012); Wei et al. (2019).
Proportion Degradation product Source
Major (> 10%) NO2, NO, CO, CO2, H2O, char Klein et al. (1950); MWolfrom et al. (1955); Gelernter et al. (1956); Eyer et al. (2007); Rychlý et al. (2012)
Minor (5%–10%) HCOOH, HCHO, (HCO)2 Gelernter et al. (1956); Wolfrom and Arsenault (1960)
Trace (less than 10%) HCN, N2, N2O, CH3CHO, (H2C)2CO, CH3=CHCHO, CH4, H2C=CH2, CH2OH, CH2CH2OH, HCONH2 Klein et al. (1950); Wolfrom et al. (1955); Wolfrom and Arsenault (1960); Meyer et al. (2007)
Tab.2  Degradation products of NC, based on Dauerman and Tajima (1968); Wei et al. (2019)
Functional groups Dissociation temperature (°C)
Allophanate 80–120
Biuret 100–125
Urethane 160–200
Urea 140–250
Tab.3  Functional groups in polyurethane that possibly degrade under extrusion temperature (Oenema et al., 2022)
Fig.4  Hydrolysis mechanism of PU, summarized based on Mondal and Martin (2012); Datta and Włoch (2017).
Functional group Wavelength (cm−1) Degradation temperature (°C)
C–H (benzene ring) 918 280–300
C–N 1220 175
N–H 1531 175
C=C (benzene ring) 1604.4 280–300
C=O 1620 175
C=O 1665 35°C hydrolysis
C=O 1739 175
C=O 1800 175
Isocyanate (–N=C=O) 2274 200 in air, 250 in N2
Isocyanate (–N=C=O) 2276 RT-200
Isocyanate (–N=C=O) 2280 320–350
CO2 2340 200 in air, 250 in N2
Methylene (polyether polyol) 2873 340–360
Methylene (polyether polyol) 2929 340–360
Methyl (polyether polyol) 2979.5 340–360
N–H 3310 175
N–H 3326 100–200
N–H 3389 280–300
Polyol 3600 200 in air, 250 in N2
Tab.4  Degradation temperature of different functional groups in PU and their accordingly wavelength under FTIR, Summarized by Mondal and Martin (2012); Jiao et al. (2013); Sui et al. (2014); He et al. (2016)
Fig.5  Thermal stability of different pigments (name demonstrated following the Color Index naming method) applied in printing ink for plastics (P-Pigment, R-Red, Y-Yellow, B-Blue, V-Violet, G-Green, O-Orange, Bk-Black, numbers are the color index (C.I.) numbers), adapted from Guo et al. (2023a).
Binder resin Degradation behavior Impact on recyclate quality
NC Complete degradation unknown
PU Partially degradation when humidity involved Decrease in tensile strength
PVB No degradation Slightly decrease the melting temperature and increase the degree of crystallinityDecrease the notch impact strength
UV-acrylics Partially degradation when humidity involved Generating more carboxyl groups facilitates the degradation of PO, with an unknown quality impact
CA derivatives Partially degradation when humidity involved Decreasing the melt temperature and degree of crystallinityIncreasing in tensile strength and decreasing in elastic modulus
PA Partially degradation when humidity involved Slightly increase in MFISlightly decreasing in the degree of crystallinity
Tab.5  Degradation behaviors in extrusion process and potential impact on recyclate quality of common binder resins for plastic printing ink
Binder resin Degradation products Reaction condition Source
PU Gas including H2, NH3, H2O, CO, and CO2, nitrogen-containing hydrocarbons (i.e., nitrile), high molecular compounds including polyaromatics, polyesters, polyethers, etc. Various, above 250 °C Oenema et al. (2022)
PVB Acetic acid, butanoic acid, furan,butanal, butenal, butanol 360–450 °C Liau et al. (1996)
PA Caprolactam, hydrocarbons, and N-Containing hydrocarbons, 400–600 °C, 1–1.15 bar with Zeolite catalyst Bockhorn et al. (2001); Zakharyan and Maksimov (2022)
Acrylics Different tertiary ether, ketone, alcohols, and acrylate monomers 400 °C Matsubara et al. (2002); Belbakra et al. (2021)
Cellulose acetate derivatives CO, CO2, methyl acetate, butyric acid, methyl butyrate, ketene, acetaldehyde, CAB oligomer 400–600 °C Gongwer et al. (1997)
Tab.6  Possible reaction conditions and products of binder resins except nitrocellulose (NC) in pyrolysis process
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