Skip to main content
SpringerLink
Log in

Enhanced degradation of cellulose acetate film containing diphenyliodonium salt–benzophenone

  • Published:
Cellulose Aims and scope Submit manuscript

Abstract

Cellulose acetate (degree of substitution 2.45) films containing diphenyliodonium salt and benzophenone were prepared and their degradative behavior was examined under simulated solar exposure. Acetic acid generation from the films under irradiation was greater in the co-presence of diphenyliodonium salt and benzophenone than in the sole presence of diphenyliodonium salt. Photosensitization and free-radical oxidization, which are followed by Brønsted acid generation, were postulated as the mechanism for the observed increase of deacetylation. The patterns of decreased molecular weight were different between the films with the diphenyliodonium salt and those with benzophenone; while the films with the diphenyliodonium salt kept a relatively constant molecular-weight distribution, the polydispersity increased in the films with benzophenone during the degradation. Since the synthesized characteristics of those two different patterns of change in molecular-weight distribution were observed in the co-presence of the diphenyliodonium salt and benzophenone, each additive appeared to act independently to lead to main-chain cleavage of cellulose acetate. Therefore, decrease in the molecular weight of cellulose acetate by diphenyliodonium salt did not seem to be enhanced in the co-presence with benzophenone.

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
Scheme 1
Scheme 2
Scheme 3
Scheme 4

Similar content being viewed by others

Abbreviations

BP:

Benzophenone

CA:

Cellulose acetate

DPI:

Diphenyliodonium trifluoromethanesulfonate

M n :

Number-average molecular weight

M w :

Weight-average molecular weight

SEC:

Size exclusion chromatography

References

  • Buchanan CM, Gardner RM, Komarek RJ (1993) Aerobic biodegradation of cellulose acetate. J Appl Polym Sci 47:1709–1719

    Article  CAS  Google Scholar 

  • Dektar JL, Hacker NP (1990) Photochemistry of diaryliodonium salts. J Org Chem 55:639–647

    Article  CAS  Google Scholar 

  • Dektar JL, Hacker NP (1991) Comparison of the photochemistry of diarylchloronium, diarylbromonium, and diaryliodonium salts. J Org Chem 56:1838–1844

    Article  CAS  Google Scholar 

  • Fouassier J-P, Ruhlmann D, Takimoto Y, Harada M, Kawabata M (1993) New three-component initiation systems in UV curing: a time-resolved laser-spectroscopy investigation. J Polym Sci Part A: Polym Chem 31:2245–2248

    Article  CAS  Google Scholar 

  • Gu J-D, Eberiel DT, McCarthy SP, Gross RA (1993a) Cellulose acetate biodegradability upon exposure to simulated aerobic compostiong and anaerobic bioreactor environments. J Environ Polym Degrad 1:143–153

    Article  CAS  Google Scholar 

  • Gu J-D, Eberiel DT, McCarthy SP, Gross RA (1993b) Degradation and mineralization of cellulose acetate in simulated thermophilic compost environments. J Environ Polym Degrad 1:281–291

    Article  CAS  Google Scholar 

  • Hiller LA Jr (1953) The reaction of cellulose acetate with acetic acid and water. J Polym Sci 10:385–423

    Article  CAS  Google Scholar 

  • Hosono K, Kanazawa A, Mori H, Endo T (2006) Degradative behaviour of cellulose acetate film in the presence of photoacid generator. J Adhes Soc Jpn 42:350–355

    CAS  Google Scholar 

  • Kaczmarek H, Kaminska A, Swiatek M, Sanyal S (2000) Photoinitiated degradation of polystyrene in the presence of low-molecular organic compounds. Eur Polym J 36:1167–1173

    Article  CAS  Google Scholar 

  • Komarek RJ, Gardner RM, Buchanan CM, Gedon S (1993) Biodegradation of radiolabeled cellulose acetate and cellulose propionate. J Appl Polym Sci 50:1739–1746

    Article  CAS  Google Scholar 

  • Lin CS, Liu WL, Chiu YS, Ho S-Y (1992) Benzophenone-sensitized photodegradation of polystyrene films under atmospheric conditions. Polym Degrad Stab 38:125–130

    Article  CAS  Google Scholar 

  • Malm CJ, Tanghe LJ, Laird BC (1950) Primary hydroxyl groups in hydrolyzed cellulose acetate. J Am Chem Soc 72:2674–2678

    Article  CAS  Google Scholar 

  • Manivannan G, Fouassier JP (1991) Primary processes in the photosensitized polymerization of cationic monomers. J Polym Sci Part A Polym Chem 29:1113–1124

    Article  CAS  Google Scholar 

  • Merlin A, Fouassier J-P (1980) Photochemical investigations into cellulosic materials. I. Free radical generation in cellulose by photosensitized excitation. Angew Makromol Chem 86:109–121

    Article  CAS  Google Scholar 

  • Merlin A, Fouassier J-P (1982) Photochemical investigations into cellulosic materials. IV. Photosensitized free radical generation in cellulose acetate and oligosaccharide compounds. Angew Makromol Chem 108:185–195

    Article  CAS  Google Scholar 

  • Millan MD, Locklin J, Fulghum T, Baba A, Advincula RC (2005) Polymer thin film photodegradation and photochemical crosslinking: FT-IR imaging, evanescent waveguide spectroscopy, and QCM investigations. Polymer 46:5556–5568

    Article  CAS  Google Scholar 

  • Pappas SP, Pappas BC, Gatechair LR, Jilek JH, Wolfram S (1984a) Photoinitiation of cationic polymerization. IV. Direct and sensitized photolysis of aryl iodonium and sulfonium salts. Polym Photochem 5:1–22

    Article  CAS  Google Scholar 

  • Pappas SP, Gatechair LR, Jilek JH (1984b) Photoinitiation of cationic polymerization III. Photosensitization of diphenyliodonium and triphenylsulfonium salts. J Polym Sci Polym Chem Ed 22:77–84

    Article  CAS  Google Scholar 

  • Puls J, Altaner C, Saake B (2004) Degradation and modification of cellulose acetates by biological systems. Macromol Symp 208:239–253

    Article  CAS  Google Scholar 

  • Sakai K, Moriyoshi K (1997) Biodegradation of synthetic polymer. Biodegradation of cellulose acetate. Kagaku to Kogyo (Tokyo, Jpn) 71:490–496

    CAS  Google Scholar 

  • Taylor LJ, Tobias JW (1977) Accelerated photo-oxidation of polyethylene. I. Screening of degradation-sensitizing additives. J Appl Polym Sci 21:1273–1281

    Article  CAS  Google Scholar 

  • Torikai A, Takeuchi T, Fueki K (1983) Photodegradation of polystyrene and polystyrene containing benzophenone. Polym Photochem 3:307–320

    Article  CAS  Google Scholar 

  • Yagci Y, Reetz I (1998) Externally stimulated initiator systems for cationic polymerization. Prog Polym Sci 23:1485–1538

    Article  CAS  Google Scholar 

  • Yamashita Y, Endo T (2004a) Deterioration behavior of cellulose acetate films in acidic or basic aqueous solutions. J Appl Polym Sci 91:3354–3361

    Article  CAS  Google Scholar 

  • Yamashita Y, Endo T (2004b) Effect of hydrophilic polymers on degradation behavior of cellulose acetate by phosphoric acid. J Adhes Soc Jpn 40:368–379

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Faculty of Engineering, Yamagata University, 4-3-16 Jonan, Yonezawa, Yamagata, 992-8510, Japan

    Kiyoshi Hosono, Akihiko Kanazawa, Hideharu Mori & Takeshi Endo

  2. Research and Development Planning Division, Japan Tobacco Inc., 2-2-1 Toranomon, Minato-ku, Tokyo, 105-8422, Japan

    Kiyoshi Hosono

  3. Molecular Engineering Institute, Kinki University, 11-6 Kayanomori, Iizuka, Fukuoka, 820-8555, Japan

    Takeshi Endo

Authors
  1. Kiyoshi Hosono
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Akihiko Kanazawa
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Hideharu Mori
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Takeshi Endo
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Kiyoshi Hosono.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Hosono, K., Kanazawa, A., Mori, H. et al. Enhanced degradation of cellulose acetate film containing diphenyliodonium salt–benzophenone. Cellulose 14, 529–537 (2007). https://doi.org/10.1007/s10570-007-9127-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10570-007-9127-y

Keywords

Search

Navigation