Skip to main content
SpringerLink
Log in

A novel polymethyl methacrylate (PMMA) with excellent optical and thermal properties-bearing hydroxyadamamtyl substituent

  • ORIGINAL PAPER
  • Published:
Polymer Bulletin Aims and scope Submit manuscript

Abstract

Polymethyl methacrylate (PMMA) is an important thermoplastic polymer and a versatile lithographic resist. However, the low heat resistance and low dry-etch resistance seriously restricts the application of PMMA in high-end devices and advanced nanolithography. Herein, methyl methacrylate (MMA) was copolymerized with two comonomers 1-adamantyl methacrylate (AdMA) and 1-acryloyloxy-3-hydroxyadamantane (HAdMA), and a series of copolymers P(AdMA-co-MMA) and P(HAdMA-co-MMA) with different contents of HAdMA were prepared. The UV–Vis, ellipsometer, DSC, TG, and TG–MS techniques were employed to investigate the effects of adamantyl and hydroxyadamantyl substituents on the optical and thermal properties of PMMA. The introduced hydroxyadamantyl not only significantly enhanced the refractive index, but also maintained the high transparency and low dispersion of PMMA. The glass transition temperature and thermal stability of PMMA were also greatly improved by the hydroxyadamantyl. The initial decomposition temperature of PMMA increased from 160 to about 260 ℃ after introducing 5% HAdMA. HAdMA was more effective than AdMA in improving the optical and thermal properties of PMMA. The novel P(HAdMA-co-MMA) copolymer has overcome the shortcomings of traditional PMMA and is anticipated to significantly broaden its range of applications.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10
Fig. 11

Similar content being viewed by others

References

  1. Ali U, Karim KJBA, Buang NA (2015) A review of the properties and applications of poly (methyl methacrylate) (PMMA). Polym Rev 55(4):678–705

    Article  CAS  Google Scholar 

  2. Khan A, Lee S, Jang T, Xiong Z, Zhang C, Tang J, Guo LJ, Li WD (2016) High-performance flexible transparent electrode with an embedded metal mesh fabricated by cost-effective solution process. Small 12(22):3021–3030

    Article  CAS  PubMed  Google Scholar 

  3. El-Gamal S, Ismail AM (2020) Electrical and optical properties of novel brilliant cresyl bluedye-doped poly (methyl methacrylate) as selectivecut-offlaser filters. Polym Int 69(12):1308–1318

    Article  CAS  Google Scholar 

  4. Shankar U, Gupta CR, Oberoi D, Singh BP, Kumar A, Bandyopadhyay A (2020) A facile way to synthesize an intrinsically ultraviolet-C resistant tough semiconducting polymeric glass for organic optoelectronic device application. Carbon 168:485–498

    Article  CAS  Google Scholar 

  5. Begum SA, Rane AV, Kanny K (2020) Applications of compatibilized polymer blends in automobile industry. Compat Polym Blends 20:563–593

    Article  Google Scholar 

  6. Tseng AA, Kuan C, Chen CD, Ma KJ (2003) Electron beam lithography in nanoscale fabrication: recent development. IEEE Trans Electron Packag Manuf 26(2):141–149

    Article  CAS  Google Scholar 

  7. Fredriksson H, Alaverdyan Y, Dmitriev A, Langhammer C, Sutherland DS, Zäch M, Kasemo B (2007) Hole-Mask colloidal lithography. Adv Mater 19(23):4297–4302

    Article  CAS  Google Scholar 

  8. Rahman F, Carbaugh DJ, Wright JT, Rajan P, Pandya SG, Kaya S (2020) A review of polymethyl methacrylate (PMMA) as a versatile lithographic resist – with emphasis on UV exposure. Microelectron Eng 224:111238

    Article  CAS  Google Scholar 

  9. Gangnaik AS, Georgiev YM, Holmes JD (2017) New Generation electron beam resists: a review. Chem Mater 29(5):1898–1917

    Article  CAS  Google Scholar 

  10. Gross S, Camozzo D, Di Noto V, Armelao L, Tondello E (2007) PMMA: a key macromolecular component for dielectric low-κ hybrid inorganic–organic polymer films. Eur Polym J 43(3):673–696

    Article  CAS  Google Scholar 

  11. Sun H, Chan CW, Wang Y, Yao X, Mu X, Lu X, Zhou J, Cai Z, Ren K (2019) Reliable and reusable whole polypropylene plastic microfluidic devices for a rapid, low-cost antimicrobial susceptibility test. Lab Chip 19(17):2915–2924

    Article  CAS  PubMed  Google Scholar 

  12. Dore C, Osmond J, Mihi A (2018) A water-processable cellulose-based resist for advanced nanofabrication. Nanoscale 10(37):17884–17892

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  13. Carbaugh DJ, Pandya SG, Wright JT, Kaya S, Rahman F (2017) Enhancing the dry-etch resistance of polymethyl methacrylate patterned with electron beam lithography. J Vac Sci Technol B Nanotechnol Microelectron 35(4):041602

    Article  Google Scholar 

  14. Lewis SM, Hunt MS, DeRose GA, Alty HR, Li J, Wertheim A, De Rose L, Timco GA, Scherer A, Yeates SG, Winpenny REP (2019) Plasma-Etched pattern transfer of sub-10 nm structures using a metal-organic resist and helium ion beam lithography. Nano Lett 19(9):6043–6048

    Article  CAS  PubMed  Google Scholar 

  15. Kerber GL, Kleinsasser AW, Bumble B (2009) Fabrication of submicrometer high current density Nb/Al-ALNx/Nb junctions. IEEE Trans Appl Supercond 19(3):159–166

    Article  CAS  Google Scholar 

  16. Stoneham AM, Matthews JR, Ford IJ (2004) Innovative materials for fusion power plant structures: separating functions. J Phys: Condens Matter 16(27):2597-S2621

    Google Scholar 

  17. Wang F, Diesendruck CE (2018) Polyphthalaldehyde: synthesis, derivatives, and applications. Macromol Rapid Commun 39(2):1700519

    Article  Google Scholar 

  18. Turchanin A, Gölzhäuser A (2012) Carbon nanomembranes from self-assembled monolayers: functional surfaces without bulk. Prog Surf Sci 87(5–8):108–162

    Article  CAS  Google Scholar 

  19. Demir MM, Koynov K, Akbey Ü, Bubeck C, Park I, Lieberwirth I, Wegner G (2007) Optical properties of composites of PMMA and surface-modified zincite nanoparticles. Macromolecules 40(4):1089–1100

    Article  CAS  Google Scholar 

  20. Rezaei F, Abbasi-Firouzjah M, Shokri B (2014) Investigation of antibacterial and wettability behaviours of plasma-modified PMMA films for application in ophthalmology. J Phys D Appl Phys 47(8):085401

    Article  CAS  Google Scholar 

  21. Tsai C-W, Wang J-C, Li F-N, Chang Y-C, Wu K-H (2016) Synthesis of adamantane-containing methacrylate polymers: characterization of thermal, mechanical, dielectric and optical properties. Mater Express 6(3):220–228

    Article  CAS  Google Scholar 

  22. Tang L, Zhang J, Tang Y, Kong J, Liu T, Gu J (2021) Polymer matrix wave-transparent composites: a review. J Mater Sci Technol 75:225–251

    Article  CAS  Google Scholar 

  23. Wu Z, He J, Yang H, Yang S (2022) Progress in aromatic polyimide films for electronic applications. Polymers 14(6):1269

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  24. Cho MJ, Choi DH, Sullivan PA, Akelaitis AJP, Dalton LR (2008) Recent progress in second-order nonlinear optical polymers and dendrimers. Prog Polym Sci 33(11):1013–1058

    Article  CAS  Google Scholar 

  25. Tsai C-W, Wu K-H, Wang J-C, Shih C-C (2017) Synthesis, characterization, and properties of petroleum-based methacrylate polymers derived from tricyclodecane for microelectronics and optoelectronics applications. J Ind Eng Chem 53:143–154

    Article  CAS  Google Scholar 

  26. Wu K-H, Tsai C-W, Huang W-C, Hung W-C (2021) Structural design and characterization of tricycloalkyl-containing methacrylate with methyl methacrylate copolymers. Mater Sci Eng, B 267:115088

    Article  CAS  Google Scholar 

  27. Wu W, Ouyang Q, He L, Huang Q (2022) Optical and thermal properties of polymethyl methacrylate (PMMA) bearing phenyl and adamantyl substituents. Colloids Surf A 653:130018

    Article  CAS  Google Scholar 

  28. Rakhshani MR, Mansouri-Birjandi MA (2017) High sensitivity plasmonic refractive index sensing and its application for human blood group identification. Sens Actuators B Chem 249:168–176

    Article  CAS  Google Scholar 

  29. Liu J-G, Ueda M (2009) High refractive index polymers: fundamental research and practical applications. J Mater Chem 19(47):8907–8919

    Article  CAS  Google Scholar 

  30. Lü C, Yang B (2009) High refractive index organic–inorganic nanocomposites: design, synthesis and application. J Mater Chem 19(19):2884–2901

    Article  Google Scholar 

  31. Higashihara T, Ueda M (2015) Recent progress in high refractive index polymers. Macromolecules 48(7):1915–1929

    Article  CAS  Google Scholar 

  32. Eppig T, Rawer A, Hoffmann P, Langenbucher A, Schroder S (2020) On the chromatic dispersion of hydrophobic and hydrophilic intraocular lenses. Optom Vis Sci 97(4):305–313

    Article  PubMed  Google Scholar 

  33. Arabeche K, Delbreilh L, Adhikari R, Michler GH, Hiltner A, Baer E, Saiter J-M (2012) Study of the cooperativity at the glass transition temperature in PC/PMMA multilayered films: influence of thickness reduction from macro- to nanoscale. Polymer 53(6):1355–1361

    Article  CAS  Google Scholar 

Download references

Acknowledgment

This work was supported by the Ningbo “3315 Plan” Innovation Team Project (2018A-03-A) and Top Talent Project.

Funding

Ningbo “3315 Plan”, Innovation Team Project, 2018A-03-A, Top Talent Project.

Author information

Authors and Affiliations

  1. Engineering Laboratory of Advanced Energy Materials, Ningbo Institute of Materials Technology and Engineering, Chinese Academy of Sciences, Ningbo, 315201, People’s Republic of China

    Weilong Wu, Shihao Feng, Qin Ouyang, Zengzhuan Yang, Liu He & Qing Huang

  2. College of Chemical Engineering, Zhejiang University of Technology, Hangzhou, 310000, Zhejiang, People’s Republic of China

    Weilong Wu

  3. School of Physics, Henan Normal University, Xinxiang, 453007, People’s Republic of China

    Shihao Feng

  4. Yongjiang Lab Y LAB, Ningbo, 315202, Zhejiang, People’s Republic of China

    Weilong Wu

Authors
  1. Weilong Wu
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Shihao Feng
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Qin Ouyang
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Zengzhuan Yang
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Liu He
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Qing Huang
    View author publications

    You can also search for this author in PubMed Google Scholar

Contributions

Weilong Wu is mainly responsible for formal analysis, investigation, data collation, writing—manuscript preparation, and visualization. Shihao Feng is mainly responsible for validation and visualization. Qin Ouyang is mainly responsible for conceptualization, writing—review and editing, supervision, and visualization. Zengzhuan Yang is mainly responsible for validation. Liu He is mainly responsible for resources and supervision. Qing Huang is mainly responsible for supervision and project administration.

Corresponding author

Correspondence to Qin Ouyang.

Ethics declarations

Conflict of interest

There are no conflicts to declare.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Wu, W., Feng, S., Ouyang, Q. et al. A novel polymethyl methacrylate (PMMA) with excellent optical and thermal properties-bearing hydroxyadamamtyl substituent. Polym. Bull. (2024). https://doi.org/10.1007/s00289-024-05286-x

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s00289-024-05286-x

Keywords

Search

Navigation