摘要(英) |
This study presents a novel low-migration photocurable ink material suitable for printing on food and pharmaceutical packaging. In recent years, with the rise of food safety awareness, the ink industry has been actively seeking ink materials with low migration characteristics to avoid chemical materials affecting food safety. Commonly used commercial photoinitiators, such as benzophenone (BP), isopropylthioxanthone (ITX), both have odors and can easily migrate from printed products, thereby affecting human health. To overcome the hazards affacted by these photoinitiators, this study proposes a method that copolymerizes photoinitiating units with epoxidized soybean oil (ESBO) and introduces acrylic units to form a network of polymer during the photopolymerization reaction (Norrish reaction), achieving low migration effects rates.
The developed products, ESBOa-BP and ESBOa-TX, which introduce photoinitiators and acrylic units into ESBO, achieve migration rates of 0.7% and 0.2%, respectively, when used as photoinitiators in acrylic resin polymerization. Whereas benzophenone as a photoinitiator itself has the migration rate as high as 87%, and ITX has displayed 62.9% of migration rate which is a drastic difference compared to our proposed results. Additionally, by binding photoinitiating units with monomer and copolymerizing with other functionalized units, further reduction in the migration of photoinitiating units was achieved. The migration rates for pGLa-BP and pGLa-TX reached 1.5% and 2.6%, respectively.
Given that the aforementioned photoinitiating units undergo photopolymerization (Norrish reaction) for photocuring, requiring the addition of amine synergists for effective curing, the industry seeks to simplify this process. By binding the amine synergist to the epoxy soybean oil containing photoinitiating and acrylic units, a low-migration, self-curing photoinitiator can be achieved. ESBOa-BPN, which combines low migration and self-curing characteristics, has a migration rate of 1.0%. Similarly, binding the amine synergist with monomer also achieves this effect, exemplified by pGLa-BPN, which has a migration rate of 1.0%. Moreover, using ITX as the photoinitiator unit in pGLa-TXN, the migration rate reaches 0.3%.
The modified photoinitiating units proposed in this paper can solve the current migration rate issues in the photocuring industry. By also binding the amine synergist to the backbone, further improvement of the initiator is possible, presenting a promising outlook for industrial applications. |
參考文獻 |
1. X. Ren; W. Liu; Q. Yao; S. Wang; W. Liu; H. Gu; D. Wang; J. Fan; X. Peng, Dyes Pigm., 2022, 200, 110133.
2. H. Bahria; Y. Erbil, Dyes Pigm., 2016, 134, 442–447.
3. C. Wang; K. Yan; X. Luo; S. Jin; L. Wang; J. Luo; J. Zheng, Color. Technol., 2021, 137, 348–360.
4. https://www.businessresearchinsights.com/market-reports/thick-layer-photoresists-market-105988
5. https://www.maximizemarketresearch.com/market-report/global-photoinitiators-market/72157/
6. M. A. Lago; A. Rodriguez; R. Sendon; J. Bustos; M.T. Nieto; P. Paseiro, Food Additives& Contaminants Part A, 2015, 32, 779-798.
7. H.F. Gruber, Progress in Polymer Science, 1992, 17, 953-1044.
8. B. G. W. Norrish; C. H. Bamford, Nature, 1936, 138, 1016.
9. A. Allushi; C. Kutahya; C. Aydogan; J. Kreutzer; G. Yilmaz; Y. Yagci, Polym. Chem., 2017, 8, 1972.
10. M. K. Trivedi; A. Branton; D. Trivedi; G. Nayak; G. Saikia; S. Jana, Science Journal of Analytical Chemistry, 2015, 3, 109-114.
11. N. Khemiri; S. Messaoudi; M. Abderrabba; G. Spighi; M. AndréGaveau; M. Briant; B. Soep; J. M. Mestdagh; M. Hochlaf; L. Poisson, The Journal of Physical Chemistry. A, 2015, 119, 5901-6154.
12. Kanerva L.; Elsner P.; Wahlberg J.E.; Maibach H.I., Handbook of occupational dermatology, 2012.
13. Carroll G.T.; Turro N.J.; Koberstein J.T., J Colloid Interface Sci, 2010, 351, 556-560.
14. Zucchi S.; Bluthgen N.; Ieronimo A.; Fent K., Toxicol Appl Pharmacol, 2011, 250, 137-146.
15. A. Anadón; D. Bell; M. L. Binderup; W. Bursch; L. Castle; R. Crebelli; K. H. Engel; R. Franz; N. Gontard; T. Haertlé; T. Husøy; K. D. Jany; C. Leclercq; J. C. Lhuguenot; W. Mennes; M. R. Milana; K. Pfaff; K. Svensson; F. Toldrá; R. Waring; D. Wölfle, The EFSA Journal, 2009, 1104, 1-30.
16. N. F. Nikitas; P. L. Gkizis; C. G. Kokotos, Org. Biomol. Chem., 2021, 19, 5237.
17. R. M. Montoya; R. L. Vargas; O. A. Aguilar, Annals of Global Health, 2018, 84, 225-238.
18. M. Pagac; J. Hajnys; Q.-P. Ma; L. Jancar; J. Jansa; P. Stefek; J. Mesicek, Polymers, 2021, 13, 598.
19. T. Gencoglu; B. Graff; F. Morlet-Savary; J. Lalev´ee; D. Avci, ChemistrySelect, 2021, 6, 5743–5751.
20. A. Mau; T.H. Le; C. Dietlin; T.-T. Bui; B. Graff; F. Dumur; F. Goubard; J. Lalevee, Polym. Chem., 2020, 11, 7221–7234.
21. G. Foli; M. Degli Esposti; D. Morselli; P. Fabbri Macromol, Rapid Commun., 2020, 41, 1900660.
22. Y. Nakagawa; K. Tayama, Arch Toxicol, 2002, 76, 727-731.
23. S. Liu; H. Chen; Y. Zhang; K. Sun; Y. Xu; F. Morlet-Savary; B. Graff; G. Noirbent; C. Pigot; D. Brunel; M. Nechab; D. Gigmes; P. Xiao; F. Dumur; J. Lalevee, Polymers, 2020, 12, 1394.
24. J. Yang; W. Liao; Y. Xiong; Q. Wu; X. Wang; Z. Li; H. Tang, Dyes Pigm., 2018, 148, 16-24.
25. M. Degirmenci; I. Cianga; G. Hizal; Y. Yagci, Polymer Preprints, 2002, 43, 22-23.
26. G. Temel; N. Arsi; Y. Yagci, polymer Bulletin, 2006, 57, 51-56.
27. J. Wei; H. Wang; X. Jiamg; J. Yin, Macromolecules, 2007, 40, 2344-2351.
28. D. K. Baltaa; Ö. Karahanb; D. Avci; N. Arsua, Progress in Organic Coatings, 2014, 78, 200-207.
29. W. Li; J. Nie; Y. Y. Zhao; X. Q. Zhu, Journal of Photochemistry & Photobiology, A: Chemistry, 2024, 455, 115785.
30. L. Guadagno; L. Vertuccio; C. Naddeo; E. Calabrese; G. Barra; M. Raimondo; A. Sorrentino; W. H. Binder; P. Michael; S. Rana, Polymers, 2019, 11, 903.
31. Y. Xia; R. C. Larock, Green Chem, 2010, 12, 1893.
32. S. Z. Erhan; B. K. Sharma; Z. Liu; A. Adhvaryu, J Agric Food Chem, 2008, 56, 8919.
33. B. K. Sharma; Z. Liu; A. Adhvaryu; S. Z. Erhan, J Agric Food Chem, 2008, 56, 3049.
34. A. Luo; X. Jiang; J. Yin, Polymer, 2012, 53, 2183-2189.
35. J. Yang; X. X. Yin; J. Nie, 2019, CN 110294737 A.
36. M. Aydin; N. Arsu; Y. Y. Macromol, Rapid Commun. 2003, 24, 718–723. |