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Journal of Polymer Research

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01-04-2024 | Original Paper

Preparation of oxidized polyethylene wax from polyethylene wax by SCCO₂-assisted foam method: structural characteristics, reaction mechanism and properties

Authors: Wen-Huan Qiao, Peng Gao, Shao-Kang Qian, Zhen-Yan Hu, Shuang Ji, Jun-Yang Yan, Gui-Ping Cao

Published in: Journal of Polymer Research | Issue 4/2024

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Abstract

Polyethylene wax (PEW) serves as a versatile material modifier, and the newly acquired polarity functions after functionalization are of great interest. Furthermore, exploring methods to enhance product purity further is necessary. The rate of reaction between oxygen and PEW depends on both the diffusion rate of oxygen in the polymer and the thermodynamic properties of the reaction. To address these challenges and investigate changes in reaction mechanisms and properties, we employed supercritical carbon dioxide foaming to facilitate PEW oxidation while utilizing DFT theory to calculate oxidation reaction pathways and thermodynamic properties. The acid value of foamed PEW at 16 MPa and 115 °C increased by a factor of 2.7 compared to non-foamed PEW after 6 h of oxidation, indicating that foaming acted as an aid during this process. The generation of −OH, C = O, −CHO, and −COOH during the oxidation process was mutually confirmed through comprehensive analysis including FTIR, NMR spectroscopy, as well as other characterizations and calculations. Oxidized PEW (OPE) exhibited a maximum reduction in water contact angle (WCA) by 49°, a maximum decrease in crystallinity by 26.32%, and an increase in water vapour permeability by 61.8%. As a compatibilizer at a dosage level of 2.5 wt%, OPE demonstrated optimal compatibility improvement. Overall, foaming techniques effectively assisted the oxidation process, offering new possibilities for optimizing the structure and properties of PEW with potential applications within materials science.

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Rapp G, Tireau J, Bussiere P-O, Chenal J-M, Rousset F, Chazeau L, Gardette J-L, Therias S (2019) Influence of the physical state of a polymer blend on thermal ageing. Polym Degrad Stab 163:161–173. https://doi.org/10.1016/j.polymdegradstab.2019.03.006CrossRef

Balzade Z, Sharif F, Reza S, Anbaran G (2022) Tailor-made functional polyolefins of complex architectures: Recent advances, applications, and prospects. Macromolecules 55:6938–6972. https://doi.org/10.1021/acs.macromol.2c00594CrossRef

Kim HK, Zhang G, Nam C, Chung TCM (2015) Characterization of polyethylene-graft-sulfonated polyarylsulfone proton exchange membranes for direct methanol fuel cell applications. Membranes 5:875–887. https://doi.org/10.3390/membranes5040875CrossRefPubMedPubMedCentral

Luo L, Liu P, Zhang K, Tang G, Hou H, Li B-G, Wang W-J (2020) Vinyl-functionalized polyolefins for fast photovoltaic cell encapsulation. ACS Appl Polym Mater 2:2571–2577. https://doi.org/10.1021/acsapm.0c00207CrossRef

Scholten PBV, Cartigny G, Grignard B, Debuigne A, Cramail H, Meier MAR, Detrembleur C (2021) Functional polyethylenes by organometallic-mediated radical polymerization of biobased carbonates. ACS Macro Lett 10:313–320. https://doi.org/10.1021/acsmacrolett.1c00037CrossRefPubMed

Wang W, Wang Y, Liu Z, Han Y, Wang C (2019) Study on application performance of oxidized polyethylene wax in powder coatings. Prog Org Coat 136:105294. https://doi.org/10.1016/j.porgcoat.2019.105294CrossRef

Wang Y-B, Nan C, Zhuo W, Zou C, Jiang H, Hao X-Q, Chen C, Song M-P (2023) Amine-imine nickel catalysts with pendant O-Donor groups for ethylene (Co)polymerization. Inorg Chem 62:5105–5113. https://doi.org/10.1021/acs.inorgchem.2c04240CrossRefPubMed

Chen Z, Leatherman MD, Daugulis O, Brookhart M (2017) Nickel-catalyzed copolymerization of ethylene and vinyltrialkoxysilanes: Catalytic production of cross-linkable polyethylene and elucidation of the chain-growth mechanism. J Am Chem Soc 139:16013–16022. https://doi.org/10.1021/jacs.7b10281CrossRefPubMed

Wang F, Chen C (2019) A continuing legend: the Brookhart-type α-diimine nickel and palladium catalysts. Polym Chem 10:2354–2369. https://doi.org/10.1039/C9PY00226JCrossRef

10.

Zhong L, Zheng H, Du C, Du W, Liao G, Cheung CS, Gao H (2020) Thermally robust α-diimine nickel and palladium catalysts with constrained space for ethylene (co)polymerizations. J Catal 384:208–217. https://doi.org/10.1016/j.jcat.2020.02.022CrossRef

11.

Franssen NMG, Reek JNH, de Bruin B (2013) Synthesis of functional ‘polyolefins’: state of the art and remaining challenges. Chem Soc Rev 42:5809–5832. https://doi.org/10.1039/C3CS60032GCrossRefPubMed

12.

Yuan C, Zhou Y, Zhu Y, Hu S, Liang J, Luo Z, Gao B, Zeng T, Zhang Y, Li J, Huang S, Han Z, Yang X, Yang Y, Meng P, Hu J, He J, Yuan H, Li Q (2022) Improved high-temperature electrical properties of polymeric material by grafting modification. ACS Sustain Chem Eng 10:8685–8693. https://doi.org/10.1021/acssuschemeng.1c08417CrossRef

13.

Zhang Y, Li X, Zhu W, Liu P, Ren J, Chen S, Hu Y, Zhou G (2022) A multi-functional chromone-modified polyethylene obtained by metal-free C-H activation. Polym Chem 13:1437–1445. https://doi.org/10.1039/D1PY01604KCrossRef

14.

Gong Y, Wang S-H, Zhang Z-Y, Yang X-L, Yang Z-G, Yang H-G (2021) Degradation of sunlight exposure on the high-density polyethylene (HDPE) pipes for transportation of natural gases. Polym Degrad Stab 194:109752. https://doi.org/10.1016/j.polymdegradstab.2021.109752CrossRef

15.

Liu J, Qin S, Wang G, Zhang H, Zhou H, Gao Y (2021) Batch foaming of ultra-high molecular weight polyethylene with supercritical carbon dioxide: Influence of temperature and pressure. Polym Test 93:106974. https://doi.org/10.1016/j.polymertesting.2020.106974CrossRef

16.

Chen L, Malollari KG, Uliana A, Sanchez D, Messersmith PB, Hartwig JF (2021) Selective, catalytic oxidations of C-H bonds in polyethylenes produce functional materials with enhanced adhesion. Chem 7:137–145. https://doi.org/10.1016/j.chempr.2020.11.020CrossRef

17.

Ahn Y, Colin X, Roma G (2021) Atomic scale mechanisms controlling the oxidation of polyethylene: a first principles study. Polymers 13:2143–2160. https://doi.org/10.3390/polym13132143CrossRefPubMedPubMedCentral

18.

Chen L, Malollari KG, Uliana A, Hartwig JF (2021) Ruthenium-catalyzed, chemoselective and regioselective oxidation of polyisobutene. J Am Chem Soc 143:4531–4535. https://doi.org/10.1021/jacs.1c00125CrossRefPubMed

19.

Jiang X-L, Liu T, Xu Z-M, Zhao L, Hu G-H, Yuan W-K (2009) Effects of crystal structure on the foaming of isotactic polypropylene using supercritical carbon dioxide as a foaming agent. J Supercrit Fluids 48:167–175. https://doi.org/10.1016/j.supflu.2008.10.006CrossRef

20.

Sun H, Pei X, Ruan H, Song F, Wang T, Wang Q, Wang C (2023) “Partition method”-inspired fabrication of hierarchically porous polyetherimide via supercritical CO₂ foaming: achieving efficient adsorption of carbon dioxide. Ind Eng Chem Res 62:3844–3852. https://doi.org/10.1021/acs.iecr.2c03803CrossRef

21.

Gong C, Zheng H, Huang P, Xu L, Su Y, Zheng W, Zhao Y (2023) Supercritical CO₂ foaming of lightweight polyolefin elastomer/trans-polyoctylene rubber composite foams with extra-soft and anti-shrinkage performance. Ind Eng Chem Res 62:6214–6223. https://doi.org/10.1021/acs.iecr.3c00025CrossRef

22.

Mees MA, McAllister TD, Curia S, Howdle SM, Hoogenboom R (2023) Modification of linear polyethylenimine with supercritical CO₂: From fluorescent materials to covalent cross-links. Macromolecules 56:2841–2851. https://doi.org/10.1021/acs.macromol.2c02443CrossRef

23.

Xiang Y, Li X-h, Yeh J-t (2022) Multistage drawing scCO₂-assisted ultrahigh molecular weight polyethylene/activated nanocarbon fibers and their performance. J Polym Res 29:78. https://doi.org/10.1007/s10965-022-02918-6CrossRef

24.

Gao P, Qiao W-H, Hu Z-Y, Yang B-C, Cao C-Y, Fu Y, Xia Y, Wang C-X, Cao G-P, Lv H (2023) Hydrolysis of polyethylene terephthalate by ZSM-5 combined with supercritical carbon dioxide under neutral environment. Polym Degrad Stab. https://doi.org/10.1016/j.polymdegradstab.2023.110590CrossRef

25.

Li Z, Liu L, Wang Z, Gao P, Li GK (2023) Synthesis and application of mesoporous materials: Process status, technical problems, and development prospects: a mini-review. Energy Fuels 37:3413–3427. https://doi.org/10.1021/acs.energyfuels.2c03882CrossRef

26.

Xu J-K, Zhang L, Li D-L, Bao J-B, Wang Z-B (2020) Foaming of poly(3-hydroxybutyrate-co-3-hydroxyvalerate) with supercritical carbon dioxide: foaming performance and crystallization behavior. ACS Omega 5:9839–9845. https://doi.org/10.1021/acsomega.9b04501CrossRefPubMedPubMedCentral

27.

Nofar M, Ameli A, Park CB (2015) Development of polylactide bead foams with double crystal melting peaks. Polymer 69:83–94. https://doi.org/10.1016/j.polymer.2015.05.048CrossRef

28.

Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Petersson GA, Nakatsuji H (2016) Gaussian 16, Revision C.01; Gaussian, Inc. Wallingford, CT

29.

Zhao Y, Truhlar DG (2008) The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06 functionals and 12 other functionals. Theoret Chem Acc 119:525–525. https://doi.org/10.1007/s00214-007-0401-8CrossRef

30.

Hariharan PC, Pople JA (1974) Accuracy of AH_n equilibrium geometries by single determinant molecular orbital theory. Mol Phys. 27:209–214. https://doi.org/10.1080/00268977400100171CrossRef

31.

Petersson GA, Bennett A, Tensfeldt TG, Al-Laham MA, Shirley WA, Mantzaris J (1988) ChemInform abstract: a complete basis set model chemistry. Part 1. The total energies of closed-shell atoms and hydrides of the first-row elements. ChemInform. https://doi.org/10.1002/chin.198845003CrossRef

32.

Grimme S, Antony J, Ehrlich S, Krieg H (2010) A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu. J Chem Phys 132:154104. https://doi.org/10.1063/1.3382344CrossRefPubMed

33.

Grimme S, Ehrlich S, Goerigk L (2011) Effect of the damping function in dispersion corrected density functional theory. J Comput Chem 32:1456–1465. https://doi.org/10.1002/jcc.21759CrossRefPubMed

34.

Fukui K (1981) The path of chemical reactions - the IRC approach. Acc Chem Res 14:363–368. https://doi.org/10.1021/ar00072a001CrossRef

35.

Gonzalez C, Schlegel HB (1990) Reaction path following in mass-weighted internal coordinates. J Phys Chem 94:5523–5527. https://doi.org/10.1021/j100377a021CrossRef

36.

Dennington R, Keith TA, Millam JM (2016) Gauss View, Version 6; Semichem Inc. Shawnee Mission, KS

37.

Rastogi A, Terry AE, Mathot VBF, Rastogi S (2005) A study of thermodynamically favorable crystals in branched polymers: a disentangled and crystallizable interphase. Macromolecules 38:4744–4754. https://doi.org/10.1021/ma048023bCrossRef

38.

Ahn Y, Roma G, Colin X (2022) Elucidating the role of alkoxy radicals in polyethylene radio-oxidation kinetics. Macromolecules 55:8676–8684. https://doi.org/10.1021/acs.macromol.2c01135CrossRef

39.

Wu Z, Kong L, Hu H, Tian S, Xiong Y (2015) Adsorption performance of hollow spherical sludge carbon prepared from sewage sludge and polystyrene foam wastes. ACS Sustain Chem Eng 3:552–558. https://doi.org/10.1021/sc500840bCrossRef

40.

Kořená L, Slovák V, Zelenková G, Zelenka T (2023) The effect of porosity and particle size on the kinetics of porous carbon xerogels surface oxidation. Carbon 206:303–313. https://doi.org/10.1016/j.carbon.2023.02.057CrossRef

41.

Gardette M, Perthue A, Gardette J-L, Janecska T, Földes E, Pukánszky B, Therias S (2013) Photo- and thermal-oxidation of polyethylene: Comparison of mechanisms and influence of unsaturation content. Polym Degrad Stab 98:2383–2390. https://doi.org/10.1016/j.polymdegradstab.2013.07.017CrossRef

42.

Furtak-Wrona K, Cornaton M, Durand D, Dauvois V, Roujou JL, Esnouf S, Ferry M (2019) Temperature and LET effects on radiation-induced modifications in non-perfect polyethylenes. Polym Degrad Stab 162:66–75. https://doi.org/10.1016/j.polymdegradstab.2019.02.002CrossRef

43.

Van Deynse A, Cools P, Leys C, Morent R, De Geyter N (2015) Surface modification of polyethylene in an argon atmospheric pressure plasma jet. Surf Coat Technol 276:384–390. https://doi.org/10.1016/j.surfcoat.2015.06.041CrossRef

44.

Peyroux J, Dubois M, Tomasella E, Batisse N, Kharitonov AP, Flahaut D, Romana L, Thomas P (2016) Surface modification of low-density polyethylene packaging film via direct fluorination. Surf Coat Technol 292:144–154. https://doi.org/10.1016/j.surfcoat.2016.03.021CrossRef

45.

Yang Q, Yu C (2023) multiscale interfacial interactions in graphene-asphalt nanocomposites: Implications for asphalt pavement material applications. ACS Appl Nano Mater 6:13048–13062. https://doi.org/10.1021/acsanm.3c01784CrossRef

46.

Braun B, Dorgan JR, Dec SF (2006) Infrared spectroscopic determination of lactide concentration in polylactide: an improved methodology. Macromolecules 39:9302–9310. https://doi.org/10.1021/ma061922aCrossRef

47.

Sivagurunathan P, Hajasharif P (2016) FTIR study of hydrogen bonding between substituted benzyl alcohols and acrylic esters. Arab J Chem 9:S1410–S1415. https://doi.org/10.1016/j.arabjc.2012.03.007CrossRef

48.

Chołuj M, Luis JM, Bartkowiak W, Zaleśny R (2022) Infrared spectra of hydrogen-bonded molecular complexes under spatial confinement. Front Chem. https://doi.org/10.3389/fchem.2021.801426CrossRefPubMedPubMedCentral

49.

Han P, Yan R, Wei Y, Li L, Luo J, Pan Y, Wang B, Lin J, Wan S, Xiong H, Wang Y, Wang S (2023) mechanistic insights into radical-induced selective oxidation of methane over nonmetallic boron nitride catalysts. J Am Chem Soc 145:10564–10575. https://doi.org/10.1021/jacs.2c13648CrossRefPubMed

50.

Yang K, Li J, Zhao Z, Liu Z (2023) Observation of induction period and oxygenated intermediates in methane oxidation over Pt catalyst. iScience 26:107061. https://doi.org/10.1016/j.isci.2023.107061CrossRefPubMedPubMedCentral

51.

Shi JX, Ciccia NR, Pal S, Kim DD, Brunn JN, Lizandara-Pueyo C, Ernst M, Haydl AM, Messersmith PB, Helms BA, Hartwig JF (2023) Chemical modification of oxidized polyethylene enables access to functional polyethylenes with greater reuse. J Am Chem Soc 145:21527–21537. https://doi.org/10.1021/jacs.3c07186CrossRefPubMed

52.

Sun Z, Zheng S, Wang J, Ge MF, Wang D (2001) first experimental observation on different ionic states of the tert-butoxy [(CH₃)₃CO·] radical. Chem Eur J 7:2995–2999. https://doi.org/10.1002/1521-3765(20010716)7:14%3c2995::AID-CHEM2995%3e3.0.CO;2-DCrossRefPubMed

53.

Nozawa-Kumada K, Ojima T, Inagi M, Shigeno M, Kondo Y (2020) Di-tert-butyl peroxide (DTBP)-mediated oxysilylation of unsaturated carboxylic acids for the synthesis of silyl lactones. Org Lett 22:9591–9596. https://doi.org/10.1021/acs.orglett.0c03640CrossRefPubMed

54.

Bracco P, Costa L, Luda MP, Billingham N (2018) A review of experimental studies of the role of free-radicals in polyethylene oxidation. Polym Degrad Stab 155:67–83. https://doi.org/10.1016/j.polymdegradstab.2018.07.011CrossRef

55.

Iring M, Tüdős F, Fodor Z, Kelen T (1980) The thermo-oxidative degradation of polyolefines—Part 10. Correlation between the formation of carboxyl groups and scission in the oxidation of polyethylene in the melt phase. Polym Degrad Stab 2:143–153. https://doi.org/10.1016/0141-3910(80)90036-1CrossRef

56.

Price GJ, Keen F, Clifton AA (1996) Sonochemically-assisted modification of polyethylene surfaces. Macromolecules 29:5664–5670. https://doi.org/10.1021/ma951812wCrossRef

57.

Jiang X, Yu H, Frayne R, Unal O, Strother CM (2002) Surface functionalization of polyethylene for magnetic resonance signal-enhancing coating materials. Chem Mater 14:1914–1920. https://doi.org/10.1021/cm010261nCrossRef

58.

Suresh B, Maruthamuthu S, Khare A, Palanisamy N, Muralidharan VS, Ragunathan R, Kannan M, Pandiyaraj KN (2011) Influence of thermal oxidation on surface and thermo-mechanical properties of polyethylene. J Polym Res 18:2175–2184. https://doi.org/10.1007/s10965-011-9628-0CrossRef

59.

Liu M, Zhao M, Yang S, Zhang Y, Zhou Y, Zhang J (2023) Facile casting preparation of hydrophilic coordinated PVA–Zn ion coatings with strong adhesion and high water tolerance. Prog Org Coat 182:107601. https://doi.org/10.1016/j.porgcoat.2023.107601CrossRef

60.

Wunderlich B, Czornyj G (1977) A study of equilibrium melting of polyethylene. Macromolecules 10:906–913. https://doi.org/10.1021/ma60059a006CrossRef

61.

Sharma V, Paulbudhe U, Bachhar N, Chikkali SH, Kumaraswamy G (2023) Polyethylene-grafted sheet-like silsesquioxane nanocomposites with unprecedented adhesion to polar substrates. ACS Appl Polym Mater. https://doi.org/10.1021/acsapm.3c00649CrossRefPubMed

62.

Jeong C, Starr FW, Beers KL, Douglas JF (2023) Influence of functionalization on the crystallinity and basic thermodynamic properties of polyethylene. Macromolecules 56:3873–3883. https://doi.org/10.1021/acs.macromol.2c02569CrossRef

63.

Li S, Ju W, Sun W-h, Su Y, Müller AJ, Wang D (2022) Fractionated crystallization behavior of low-molecular-weight polyethylene grafted onto SiO₂ nanoparticles. ACS Applied Polymer Materials 4:7841–7851. https://doi.org/10.1021/acsapm.2c01394CrossRef

64.

Ge Q, Gang C, Yuan W, Yangyang Q, Chunfa L (2023) Preparation and performance of high-barrier transparent paper-based materials via multi-coating technology. Acta Mater Compos Sin 40:1484–1493. https://doi.org/10.13801/j.cnki.fhclxb.20220414.002CrossRef

65.

Röhrl M, Ködel JF, Timmins RL, Callsen C, Aksit M, Fink MF, Seibt S, Weidinger A, Battagliarin G, Ruckdäschel H, Schobert R, Breu J, Biersack B (2023) New functional polymer materials via click chemistry-based modification of cellulose acetate. ACS Omega 8:9889–9895. https://doi.org/10.1021/acsomega.2c06811CrossRefPubMedPubMedCentral

66.

Yu W, Gao X, Liu H, Wang X, Zhang X (2021) Preparation of polyethylene terephthalate/polyketone/graphene oxide composite fibers: Implications for high-performance polymer composites modified with carbon nanomaterials. ACS Appl Nano Mater 4:9768–9778. https://doi.org/10.1021/acsanm.1c02187CrossRef

Title: Preparation of oxidized polyethylene wax from polyethylene wax by SCCO2-assisted foam method: structural characteristics, reaction mechanism and properties
Authors: Wen-Huan Qiao
Peng Gao
Shao-Kang Qian
Zhen-Yan Hu
Shuang Ji
Jun-Yang Yan
Gui-Ping Cao
Publication date: 01-04-2024
Publisher: Springer Netherlands
Published in: Journal of Polymer Research / Issue 4/2024
Print ISSN: 1022-9760
Electronic ISSN: 1572-8935
DOI: https://doi.org/10.1007/s10965-024-03959-9

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