Restor Dent Endod.  2012 May;37(2):96-102.

Effect of CQ-amine ratio on the degree of conversion in resin monomers with binary and ternary photoinitiation systems

• Moon HJ
• Shin DH

Abstract

OBJECTIVES
This study evaluated the effect of camphorquinone (CQ)-amine ratio on the C=C double bond conversion of resins with binary and ternary photoinitiation systems.
MATERIALS AND METHODS
Two monomer mixtures (37.5 Bis-GMA/37.5 Bis-EMA/25 TEGDMA) with binary systems (CQ/DMAEMA in weight ratio, group A [0.5/1.0] and B [1.0/0.5]) and four mixtures with ternary system (CQ/OPPI/DMAEMA, group C [0.1/1.0/0.1], D [0.1/1.0/0.2], E [0.2/1.0/0.1] and F [0.2/1.0/0.2]) were tested: 1 : 2 or 2 : 1 CQ-amine ratio in binary system, while 1 : 1 ratio was added in ternary system. The monomer mixture was cured for 5, 20, 40, and 300 sec with a Demetron 400 curing unit (Demetron). After each exposure time, degree of conversion (DC) was estimated using Fourier transform infrared (FTIR) spectrophotometer (Nicolet 520, Nicolet Instrument Corp.). The results were analyzed by ANOVA followed by Scheffe test, with p = 0.05 as the level of significance.
RESULTS
DC (%) was expressed in the order of curing time (5, 20, 40, and 300 sec). Group A (14.63 +/- 10.42, 25.23 +/- 6.32, 51.62 +/- 2.69, 68.52 +/- 2.77); Group B (4.04 +/- 6.23, 16.56 +/- 3.38, 37.95 +/- 2.79, 64.48 +/- 1.21); Group C (16.87 +/- 5.72, 55.47 +/- 2.75, 60.83 +/- 2.07, 68.32 +/- 3.31); Group D (23.77 +/- 1.64, 61.05 +/- 1.82, 65.13 +/- 2.09, 71.87 +/- 1.17); Group E (28.66 +/- 2.92, 56.68 +/- 1.33, 60.66 +/- 1.17, 68.78 +/- 1.30); Group F (39.74 +/- 6.31, 61.07 +/- 2.58, 64.22 +/- 2.29, 69.94 +/- 2.15).
CONCLUSION
All the monomers with ternary photoinitiation system showed higher DC than the ones with binary system, until 40 sec. Concerning about the effect of CQ-amine ratio on the DC, group A converted into polymer more than group B in binary system. However, there was no significant difference among groups with ternary system, except group C when cured for 5 sec only.

Keyword

CQ-amine ratio; Degree of conversion; Monomer; Photoinitiation system

MeSH Terms

Camphor
Fourier Analysis
Polymers
Camphor
Polymers

Reference

1. Ferracane JL, Greener EH. The effect of resin formulation on the degree of conversion and mechanical properties of dental restorative resins. J Biomed Mater Res. 1986. 20:121–131.

2. Wataha JC, Hanks CT, Strawn SE, Fat JC. Cytotoxicity of components of resins and other dental restorative materials. J Oral Rehabil. 1994. 21:453–462.

3. Imazato S, Tarumi H, Kobayashi K, Hiraguri H, Oda K, Tsuchitani Y. Relationship between the degree of conversion and internal discoloration of light-activated composite. Dent Mater J. 1995. 14:23–30.

4. Liu VA, Bhatia SN. Three-dimensional photopatterning of hydrogels containing living cells. Biomed Microdev. 2002. 4:257–266.

5. Fisher JP, Dean D, Mikos AG. Photocrosslinking characteristics and mechanical properties of diethyl fumarate/poly (propylene fumarate) biomaterials. Biomaterials. 2002. 23:4333–4343.

6. Dart EC, Nemcek J. Photopolymerisable composition. Great Britain Patent Specification. 1408265. 1971. Japanese Patent No. Toku-Kou-Sho 54-10986 (1979).

7. Tsai L, Charney E. The triplet states of alpha-dicarbonyls. Camphorquinone. J Phys Chem. 1969. 73:2462–2463.

8. Stansbury JW. Curing dental resins and composites by photopolymerization. J Esthet Dent. 2000. 12:300–308.

9. Jakubiak J, Allonas X, Fouassier JP, Sionkowska A, Andrzejewska E, Linden LA, Rabek JF. Camphorquinone-amines photoinitating systems for the initiation of free radical polymerization. Polymer. 2003. 44:5219–5226.

10. Davidenko N, Garcia O, Sastre R. Photopolymerization kinetics of dimethacrylate-based light-cured dental resins. J Appl Polym Sci. 2005. 97:1016–1023.

11. Yoshida K, Greener EH. Effects of two amine reducing agents on the degree of conversion and physical properties of an unfilled light-cured resin. Dent Mater. 1993. 9:246–251.

12. Schneider LF, Cavalcante LM, Consani S, Ferracane JL. Effect of co-initiator ratio on the polymer properties of experimental resin composites formulated with camphorquinone and phenyl-propanedione. Dent Mater. 2009. 25:369–375.

13. Musanje L, Ferracane JL, Sakaguchi RL. Determination of the optimal photoinitiator concentration in dental composites based on essential material properties. Dent Mater. 2009. 25:994–1000.

14. Moszner N, Fischer UK, Ganster B, Liska R, Rheinberger V. Benzoyl germanium derivatives as novel visible light photoinitiators for dental materials. Dent Mater. 2008. 24:901–907.

15. Rueggeberg FA, Ergle JW, Lockwood PE. Effect of photoinitiator level on properties of a light-cured and post-cure heated model resin system. Dent Mater. 1997. 13:360–364.

16. Park YJ, Chae KH, Rawls HR. Development of a new photoinitiation system for dental light-cure composite resins. Dent Mater. 1999. 15:120–127.

17. Fujisawa S, Kadoma Y, Masuhara E. Effects of photoinitiators for the visible-light resin system on hemolysis of dog erythrocytes and lipid peroxidation of their components. J Dent Res. 1986. 65:1186–1190.

18. Sun GJ, Chae KH. Properties of 2,3-butanedione and 1-phenyl-1,2-propanedione as new photosensitizers for visible light cured dental resin composites. Polymer. 2000. 41:6205–6212.

19. Jakubiak J, Wrzyszczyński A, Lindén LÅ, Rabek JF. The role of amines in the camphorquinone photoinitiated polymerization of multifunctional monomer. J Macromol Sci A. 2007. 44:239–242.

20. Davidenko N, Garcia O, Sastre R. Photopolymerization kinetics of dimethacrylate-based light-cured dental resins. J Appl Polym Sci. 2005. 97:1016–1023.

21. Jakubiak J, Sionkowska A, Lindén LÅ, Rabek JF. Isothermal photo differential scanning calorimetry: cross-linking polymerization of multifunctional monomers in presence of visible light photoinitiators. J Therm Anal Calor. 2001. 65:435–443.

22. Bowen RL, Argentar H. Tertiary aromatic amine accelerators with molecular weights above 400. J Dent Res. 1972. 51:473–482.

23. Ogunyinka A, Palin WM, Shortall AC, Marquis PM. Photoinitiation chemistry affects light transmission and degree of conversion of curing experimental dental resin composites. Dent Mater. 2007. 23:807–813.

24. Cohen SG, Chao HM. Photoreduction of aromatic ketones by amine. Studies of quantum yields and mechanism. J Am Chem Soc. 1968. 90:165–173.

25. Antonucci JM, Venz S. Tertiary amine salts and complexes as chemical and photochemical accelerators. J Dent Res. 1987. 66:128. Abstract #170.

26. Tanoue N, Matsumura H, Atsuta M. The influence of ultraviolet radiation intensity on curing depth of photoactivated composite veneering materials. J Oral Rehab. 1998. 25:770–775.

27. Allen NS. Photoinitiators for UV and visible curing of coatings: mechanism and properties. J Photochem Photobiol A Chem. 1996. 100:101–107.

28. Shin DH, Rawls HR. Degree of conversion and color stability of the light curing resin with new photoinitiator systems. Dent Mater. 2009. 25:1030–1038.

29. He JH, Mendoza VS. Synthesis and study of a novel hybrid UV photoinitiator: p-benzoyldiphenyliodonium hexafluorophosphate (PhCOPhl + PhPF). J Polym Sci A: Polym Chem. 1996. 34:2809–2816.

30. Kim CG, Moon HJ, Shin DH. Optimal combination of 3-component photoinitiation system to increase the degree of conversion of resin monomers. J Korean Acad Conserv Dent. 2011. 36:313–323.

31. Vallo CI. Flexural strength distribution of a PMMA-based bone cement. J Biomed Mater Res. 2002. 63:226–236.

32. Park J, Ye Q, Topp EM, Misra A, Kieweg SL, Spencer P. Effect of photoinitiator system and water content on dynamic mechanical properties of a light-cured bisGMA/HEMA dental resin. J Biomed Mater Res A. 2010. 93:1245–1251.

33. Brandt WC, Schneider LF, Frollini E, Correr-Sobrinho L, Sinhoreti MA. Effect of different photo-initiators and light curing units on degree of conversion of composites. Braz Oral Res. 2010. 24:263–270.

34. Cook WD. Photopolymerization kinetics of dimethacrylates using the camphorquinone/amine initiator system. Polymer. 1992. 33:600–609.

35. Guo X, Wang Y, Spencer P, Ye Q, Yao X. Effects of water content and initiator composition on photopolymerization of a model BisGMA/HEMA resin. Dent Mater. 2008. 24:824–831.

36. Padon KS, Scranton AB. A mechanistic investigation of a three-component radical photoinitiator system comprising methylene blue, n-methyldiethanolamine, and diphenyliodonium chloride. J Polym Sci A Polym Chem. 2000. 38:2057–2066.

37. Moin Jan C, Nomura Y, Urabe H, Okazaki M, Shintani H. The relationship between leachability of polymerization initiator and degree of conversion of visible light-cured resin. J Biomed Mater Res. 2001. 58:42–46.