Change of terminal type of alkylphenol formaldehyde resole by thermal treatment

Sung-Seen Choi; Ok-Bae Kim

Journal of Industrial and Engineering Chemistry, Vol.30, 120-126, October, 2015

DOI10.1016/j.jiec.2015.05.012 Export Citation

Change of terminal type of alkylphenol formaldehyde resole by thermal treatment

Sung-Seen Choi^†, and Ok-Bae Kim

Department of Chemistry, Sejong University, 209 Neungdong-ro, Gwangjin-gu, Seoul 143-747, Republic of Korea

E-mail:

Resole was thermally treated and was analyzed using atmospheric pressure chemical ionization-mass spectrometry (APCI.MS) to investigate the microstructural changes by heating. After thermal treatment, relative abundances of resoles having methylol (A) and hydrogen (H) terminals decreased whereas those of resoles having o-methylene quinone (Q) and aldehyde (K) terminals increased. Some resole species having AA- and HH-terminals were absolutely disappeared. Disappearance of H-terminal is due to reaction with A-terminal. Decrement or disappearance of A-terminal can be explained by conversion to Q- or K-terminal. Increase and new formation of K-terminal can be explained by conversion of Aterminal and dissociation of E-linkage.

Keywords:Resole;Microstructural analysis;Thermal treatment;Terminal change;APCI-MS

[References]

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Choi SS, Jang JH, Polymer, 39(23), 5861 (1998)
Choi SS, Bull. Korean Chem. Soc., 20, 203 (1999)
Choi SS, Polym. Adv. Technol., 12, 567 (2001)
Choi SS, Polym. Adv. Technol., 13, 94 (2002)
Cho G, Choi SS, Kim IS, Korea Polym. J., 5(3), 133 (1997)
Duin M, Souphanthong A, Rubber Chem. Technol., 68, 717 (1995)
Choi SS, Cho G, J. Appl. Polym. Sci., 68(11), 1811 (1998)
Choi SS, Korea Polym. J., 7(1), 30 (1999)
Choi SS, Ha SH, Woo CS, Elastomer, 40, 284 (2005)
Hopmans EC, Schouten S, Pancost RD, van der Meer MTJ, Damste JSS, Rapid Commun. Mass Spectrom., 14, 585 (2000)
Singh G, Gutierrez A, Xu K, Blair IA, Anal. Chem., 72, 3007 (2000)
Rauha JP, Vuorela H, Kostiainen RJ, Mass Spectrom., 36, 1269 (2001)
Byrdwell WC, Lipids, 36, 327 (2001)
Holcapek M, Jandera P, Zderadicka P, Hruba L, J. Chromatogr. A, 1010, 195 (2003)
Block C, Polym. Degrad. Stabil., 91, 3163 (2006)
Schouten S, Huguet C, Hopmans EC, Kienhuis MVM, Damste JSS, Anal. Chem., 79, 2940 (2007)
Choi SS, Song MJ, Rapid Commun. Mass Spectrom., 22, 2580 (2008)
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Choi SS, Kim JC, Rapid Commun. Mass Spectrom., 23, 3969 (2009)
Choi SS, Kim JC, Carbohydr. Res., 345, 408 (2010)
Choi SS, Kim YK, Kim OB, An SC, Shin MW, Maeng SJ, Choi GS, Bull. Korean Chem. Soc., 31, 2383 (2010)
Choi SS, Kim YK, Kim OB, An SG, Shin MW, Maeng SJ, Choi GS, Bull. Korean Chem. Soc., 32, 1055 (2011)
Choi SS, Jang JH, Polym. Test, 30, 673 (2011)
van Breemen RB, Dong L, Pajkovic ND, Int. J. Mass Spectrom., 312, 163 (2012)
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[1] Magnus FL, Hamed GR, Rubber Chem. Technol., 64, 65 (1991)

[2] Dargaville TR, Guerzoni FN, Looney MG, Shipp DA, Solomon DH, Zhang XQ, J. Polym. Sci. A: Polym. Chem., 35(8), 1399 (1997)

[3] Choi SS, J. Polym. Sci. A: Polym. Chem., 36(9), 1355 (1998)

[4] Choi SS, Jang JH, Polymer, 39(23), 5861 (1998)

[5] Choi SS, Bull. Korean Chem. Soc., 20, 203 (1999)

[6] Choi SS, Polym. Adv. Technol., 12, 567 (2001)

[7] Choi SS, Polym. Adv. Technol., 13, 94 (2002)

[8] Cho G, Choi SS, Kim IS, Korea Polym. J., 5(3), 133 (1997)

[9] Duin M, Souphanthong A, Rubber Chem. Technol., 68, 717 (1995)

[10] Choi SS, Cho G, J. Appl. Polym. Sci., 68(11), 1811 (1998)

[11] Choi SS, Korea Polym. J., 7(1), 30 (1999)

[12] Choi SS, Ha SH, Woo CS, Elastomer, 40, 284 (2005)

[13] Hopmans EC, Schouten S, Pancost RD, van der Meer MTJ, Damste JSS, Rapid Commun. Mass Spectrom., 14, 585 (2000)

[14] Singh G, Gutierrez A, Xu K, Blair IA, Anal. Chem., 72, 3007 (2000)

[15] Rauha JP, Vuorela H, Kostiainen RJ, Mass Spectrom., 36, 1269 (2001)

[16] Byrdwell WC, Lipids, 36, 327 (2001)

[17] Holcapek M, Jandera P, Zderadicka P, Hruba L, J. Chromatogr. A, 1010, 195 (2003)

[18] Block C, Polym. Degrad. Stabil., 91, 3163 (2006)

[19] Schouten S, Huguet C, Hopmans EC, Kienhuis MVM, Damste JSS, Anal. Chem., 79, 2940 (2007)

[20] Choi SS, Song MJ, Rapid Commun. Mass Spectrom., 22, 2580 (2008)

[21] Choi SS, Song MJ, Bull. Korean Chem. Soc., 29, 1847 (2008)

[22] Choi SS, Kim JC, Rapid Commun. Mass Spectrom., 23, 3969 (2009)

[23] Choi SS, Kim JC, Carbohydr. Res., 345, 408 (2010)

[24] Choi SS, Kim YK, Kim OB, An SC, Shin MW, Maeng SJ, Choi GS, Bull. Korean Chem. Soc., 31, 2383 (2010)

[25] Choi SS, Kim YK, Kim OB, An SG, Shin MW, Maeng SJ, Choi GS, Bull. Korean Chem. Soc., 32, 1055 (2011)

[26] Choi SS, Jang JH, Polym. Test, 30, 673 (2011)

[27] van Breemen RB, Dong L, Pajkovic ND, Int. J. Mass Spectrom., 312, 163 (2012)

[28] Choi SS, Kim OB, Kim Y, Polym. Test, 32, 366 (2013)

[29] Jung CW, Garrou PE, Organometallics, 1, 658 (1982)

[30] Davis JL, Barteau MA, Surf. Sci., 235, 235 (1990)

[31] Magram SJ, Taylor HA, J. Chem. Phys., 9, 755 (1941)

[32] Nimlos MR, Qian X, Johnson DK, Himmel ME, Prepr. Pap. Am. Chem. Soc., Div. Fuel Chem., 49, 866 (2004)