Light-induced yellowing of selectively 13C-enriched dehydrogenation polymers (DHPs). Part 2. NMR assignments and photoyellowing of aromatic ring 1-, 3-, 4-, and 5-13C DHPs

Nordic Pulp and Paper Research Journal

Volumn 19, Issue 1, 2004, Pages 44-52

  Parkås, Jim ^a   Paulsson, Magnus ^a,d   Terashima, Noritsugu ^a,e   Westermark, Ulla ^b   Ralph, Sally ^c,f  

^a CHALMERS UNIVERSITY OF TECHNOLOGY   (Sweden)

^b LULEÅ UNIVERSITY OF TECHNOLOGY   (Sweden)

^c US Forest Products Laboratory   (United States)

^d Stora Corporate Research AB   (Sweden)

^e Stora Enso Research ^*  (Japan)

^f FOREST PRODUCTS LABORATORY   (United States)

Author keywords

13C enrichment; Chromophores; Dehydrogenation polymer; DHP; NMR; Photoyellowing; Signal assignments

Indexed keywords

DEHYDROGENATION; IRRADIATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOTOCHEMICAL REACTIONS; THERMOMECHANICAL PULP;

13C-ENRICHMENTS; PHOTOYELLOWING; SIGNAL ASSIGNMENTS;

POLYMERS;

CHEMICALS; DEHYDROGENATION; END GROUPS; NUCLEAR MAGNETIC RESONANCE; POLYMERS; RADIATION EFFECTS; STRUCTURES; YELLOWING;

EID: 1942443161     PISSN: 02832631     EISSN: None     Source Type: Journal    
DOI: 10.3183/npprj-2004-19-01-p044-052     Document Type: Article

References (47)

1. -1 Raman/IR band to p-quinones and its implications to the mechanism of color reversion in mechanical pulps, J. Wood Chem. Technol. 18(4), 381.
2. Alves, V.L., Drumond, M.G., Stefani, G.M., Chen, C.-L. and Piló-Veloso, D. (2000): Synthesis of new trimeric lignin model compounds containing 5-5′ and β-0-4′ substructures, and their characterization by 1D and 2D NMR techniques, J. Braz. Chem. Soc. 11(5), 467.
3. Argyropoulos, D.S., Heitner, C. and Schmidt, J.A. (1995): Observation of quinonoid groups during the light-induced yellowing of softwood mechanical pulp, Res. Chem. Intermed. 9(3-5), 263.
4. 1H NMR spectroscopy, Pap. Puu 62(11), 669.
5. Capretti, G., Castellan, A., Choudhury, H., Davidson, R.S., Noutary, C., Origgi, S. and Trichet, V. (1994): Application of fluorescence spectroscopy to a study of lignin chemistry, Proc. 3rd European Workshop on Lignocellulosics and Pulp, Stockholm, Sweden, August 28-31, 159.
6. Davidson, R.S. (1996): The photodegradation of some naturally occuring polymers, J. Photochem. Photobiol. B 33(1), 3.
7. Deyama, T., Ikawa, T., Kitagawa, S. and Nishibe, S. (1987a): The constituents of Eucommia ulmoides Oliv. V. Isolation of dihydroxydehydrodiconiferyl alcohol isomers and phenolic compounds, Chem. Pherm. Bull. 35(5), 1785.
8. Deyama, T., Ikawa, T., Kitagawa, S. and Nishibe, S. (1987b): The constituents of Eucommia ulmoides Oliv. VI. Isolation of a new sesquilignan and neolignan glycosides, Chem. Pherm. Bull. 35(5), 1803.
9. Drumond, M., Aoyama, M., Chen, C.-L. and Robert, D. (1989): Substituent effects on the C-13 chemical shifts of aromatic carbons in biphenyl type lignin model compounds, J. Wood Chem. Technol. 9(4), 421.
10. 13C NMR substituent chemical shift additivity rule, Holzforschung 46(2), 127.
11. Forsskåhl, I., Tylli, H., Olkkonen, C. and Janson, J. (1991): Photochemistry of quinones and hydroquinones on solid matrices, Proc. 6th Int. Symp. Wood Pulp. Chem., Melbourne, Australia, April 29-May 3, Vol. 2, 325.
12. Forsskåhl, I. (2000): In: "Forest Products Chemistry", Brightness reversion. Edited P. Stenius. Fapet Oy, Helsinki, Finland, pp. 279-332.
13. Gellerstedt, G. and Pettersson, E.-L. (1977): Light-induced oxidation of lignin. Part 2. The oxidative degradation of aromatic rings, Svensk Papperstidn. 80(1), 15.
14. Gratzl, J.S. (1985): Lichtinduzierte Vergilbung von Zellstoffen - Ursachen und Verhütung, Papier, 39(10A), V14.
15. Heitner, C. (1993): In: "Photochemistry of Lignocellulosic Materials", Light-induced yellowing of wood-containing papers. Edited C. Heitner and J.C. Scaiano. ACS Symposium Series 531, Washington, DC, USA, pp. 2-26.
16. Heitner, C. and Min, T. (1987): The effect of sulphite treatment on the brightness and bleachability of chemithermomechanical pulp, Cellul. Chem. Technol. 21 (3), 289.
17. Hemmingson, J.A. and Morgan, K.R. (1990): A CP/MAS carbon-13 NMR study of photodegraded newsprint, Holzforschung 44(2), 127.
18. Hirashima, H and Sumimoto, M. (1994): A basic chromophore and leucochromophore in mechanical pulps: possible repetition of photochemical reduction-oxidation-reduction, Tappi J. 77(1), 146.
19. Karhunen, P., Rummakko, P., Sipilä, J. and Brunow, G. (1995): Dibenzodioxocins; A novel type of linkage in softwood lignin, Tetrahedron Lett. 36(1), 169.
20. Landucci, L.L. and Ralph, S.A. (1997): Assessment of lignin model quality in lignin chemical shift assignments - Substituent and solvent effects, J. Wood Chem. Technol. 17(4), 361.
21. Lanzalunga, O. and Bletti, M. (2000): Photo- and radiation chemical induced degradation of lignin model compounds, J. Photochem. Photobiol. B 56(2-3), 85.
22. Leary, G.J. (1968a): The yellowing of wood by light: Part II, Tappi 51 (6), 257.
23. Leary, G.J. (1968b): Photochemical production of quinoid structures in wood, Nature 217(5129), 672.
24. Leary, G.J. (1994): Recent progress in understanding and inhibiting the light-induced yellowing, J. Pulp Paper Sci. 20(8), J154.
25. Lebo, S.E., Lonsky, W.F.W., McDonough,T.J., Medvecz, P.J. and Dimmel, D.R. (1990): The occurrence and formation of ortto-quinonoid lignin structures in white spruce refiner mechanical pulp, J. Pulp Paper Sci. 16(5), J139.
26. Lin, S.Y. and Kringstad, K. (1971): Some reactions in the photoinduced discoloration of lignin, Norsk Skogsind. 25(9), 252.
27. 13C NMR spectroscopic studies of phenylcoumaran and 1,2-diarylpropane type lignin model compounds, Holzforschung 46(1), 39.
28. Nimz, H.H. and Lüdemann, H.-D. (1976): Kohlenstoff-13-NMR-Spektren von Ligninen, 6. Lignin- und DHP-Acetate, Holzforschung 30(2), 33.
29. Nishibe, S., Tsukamoto, H. and Hisada, S. (1984): Effects of O-methylation and O-glucosylation on carbon-13 nuclear magnetic resonance chemical shifts of matairesinol, (+)-pinoresinol and (+)-epipinoresinol, Chem. Pharm. Bull. 32(11), 4653.
30. Okusa, K., Miyakoshi, T. and Chen, C.-L. (1996): Comparative studies on dehydrogenative polymerization of coniferyl alcohol by laccases and peroxidases, Holzforschung 50(1), 15.
31. 13C-NMR spectral studies of isolated lignins, J. Wood Chem. Technol. 14(4), 483.
32. Pan, X. and Ragauskas, A.J. (1997): Photoyellowing of mechanical pulps: Mechanism and prevention, Proc. 9th Int. Symp. Wood Pulp. Chem., Montréal, Canada, June 9-12, 97-1.
33. 13C), Nord. Pulp Paper Res. J.19(1), 29.
34. Paulsson, M. and Ragauskas, A.J. (1998): Chemical modification of lignin-rich paper. Part 8. Effect of light source on the accelerated light-induced yellowing of untreated and acetylated high-yield pulps, Nord. Pulp Pap. Res. J. 13(2), 132.
35. Ragauskas, A.J. (1993): In: "Photochemistry of Lignocellulosic Materials", Photoreactivity of ligninlike quinoid structures. Edited C. Heitner and J.C. Scaiano. ACS Symposium Series 531, Washington, DC, USA, pp. 77-85.
36. Ralph, S.A, Ralph, J., Landucci, W.L., and Landucci, L.L. (1998): NMR Database of Lignin and Cell Wall Model Compounds. Available over Internet at http://www.dfrc.ars.usda.gov/software.html.
37. Schmidt, J.A. and Heitner, C. (1995): Light-induced yellowing of mechanical and ultra-high yield pulps. Part 3. Comparison of softwood TMP, softwood CTMP and aspen CTMP, J. Wood Chem.Technol. 15(2), 223.
38. Sjöholm, R., Holmbom, B. and Åkerback, N. (1992): Studies of the photodegradation of spruce lignin by NMR spectroscopy, J. Wood Chem. Technol. 12(1), 35.
39. 13C NMR, Holzforschung 49(6), 521.
40. Terashima, N., Ralph, S.A. and Landucci, L.L. (1996a): New facile synthesis of monolignol glucosides; p-glucocoumaryl alcohol, coniferin and syringin, Holzforschung 50(2), 151.
41. Terashima, N., Atalla, R.H., Ralph, S.A., Landucci, L.L., Lapierre, C. and Monties, B. (1996b): New preparations of lignin polymer models under conditions that approximate cell wall lignification. II. Structural characterization of the models by thioacidolysis, Holzforschung 50(1), 9.
42. 13C-enrichment of position 1 and 3 of guaiacyl nucleus. Annual Meeting of Japan Wood Research Society, Gifu, Japan, April 2.
43. 13C-enriched at position 4 or 5 of the guaiacyl ring, Holzforschung 57(5), 485.
44. Zhang, L. and Gellerstedt, G. (1994a): Reactive structures in wood and high-yield pulps. IV, Daylight-induced oxidation of stilbene structures in the solid state, Acta Chem. Scand. 48(6), 490.
45. Zhang, L. and Gellerstedt, G. (1994b): Quinoid lignin chromophores and their contribution to photoyellowing, Proc. 3rd European Workshop on Lignocellulosics and Pulp, Stockholm, Sweden, August 28-31, 293.
46. Zhang, L. and Gellerstedt, G. (1998): Quinone chromophores and their contribution to photoyellowing in lignin, Proc. 5th European Workshop on Lignocellulosics and Pulp, Aveiro, Portugal, August 30-September 2, 285.
47. Zhu, J.H., Olmstead, J.A. and Gray, D.G. (1995): Fluorescent detection of o-quinones formed in lignin-containing pulps during irradiation, J. Wood Chem. Technol. 15(1), 43.