폴리에스터계 분체도료용 경화제 N1,N1,N4,N4-Tetrakis(hydroxethyl) cyclohexane-trans-1,4-dicarboxamide의 제조 및 특성

정홍련; 허준; 이완진; 김형진; 임형수; Hong-Ryun Jung; Joon Heo; Wan-Jin Lee; Hyung Jin Kim; Hyung Soo Lim

Journal of the Korean Industrial and Engineering Chemistry, Vol.20, No.2, 195-200, April, 2009

Preparation and Properties of N1,N1,N4,N4-Tetrakis(hydroxyethyl)cyclohexanetrans-1,4-dicarboxamide as a Crosslinker of Polyester Powder Coatings

정홍련, 허준, 이완진 , 김형진 ^†, 임형수¹

전남대학교 응용화학공학부 기능성나노신화학소재사업단
¹리트머스화학(주)

Hong-Ryun Jung, Joon Heo, Wan-Jin Lee , Hyung Jin Kim^†, and Hyung Soo Lim¹

Center for Functional Nano Fine Chemicals, School of Applied Chemical Engineering, Chonnam National University, Gwangju 500-757, Korea
¹Litmus Chemicals Co. Ltd., Muan-gun, Jeonnam 534-902, Korea

E-mail:

초록

폴리에스터계 분체도료용 경화제로 사용하기 위하여 상업용 β-hydroxyalkylamide (β-HAA)의 주사슬에 cyclohexane 고리가 도입된 N1,N1,N4,N4-tetrakis(hydroxyethyl)cyclohexane-1,4-dicarboxamide (Cy-β-HAA)를 dimethyl trans-1,4-cyclohexanedicarboxylate과 diethanolamine로부터 높은 수율로 합성하고 NMR, MS 및 FT-IR 스펙트럼으로 구조를 확인하였다. 합성된 Cy-β-HAA는 기존의 β-HAA에 비하여 열적 안정성이 우수할 뿐만 아니라, 폴리에스터 분체 도료의 경화제로 사용했을 시 β-HAA를 사용한 것에 비해 더 매끄러운 도막이 형성되었으며 도막 표면에 핀홀(pinhole)의 생성이 감소되었다.

To develop a crosslinker for the polyester powder coatings, N1,N1,N4,N4-tetrakis(hydroxyethyl)cyclohexane-1,4-dicarboxamide (Cy-β-HAA), incorporated with a cyclohexane ring within the main chain of commercial β-hydroxyalkylamide (β-HAA), was prepared from the amidation of dimethyl trans-1,4-cyclohexanedicarboxylate and diethanolamine in the presence of NaOCH3. The structure of Cy-β-HAA was confirmed by its NMR, FT-IR and ESI-MS spectra. Cy-β-HAA was thermally more stable than β-HAA. When Cy-β-HAA was used as a crosslinker for the polyester powder coatings, it provided the smooth coating surface and reduced the formation of pinholes in the coating surface with comparison with β-HAA.

Keywords:β-hydroxyalkylamide;β-HAA;N1.N1.N4.N4-tetrakis(hydroxyethyl)cyclohexane-1.4-dicarboxamide;powder coatings;crosslinker

[References]

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Mafi R, Mirabedini SM, Attar MM, Moradian S, Prog. Org. Coat., 54, 164 (2005)
Belder EG, Rutten HJJ, Perera DY, Prog. Org. Coat., 42, 142 (2001)
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Lee SH, Park TW, Lee JO, Polymer (Korea), 23, 293 (1999)
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Parra DF, Mercuri LP, Matos JR, Brito HF, Romano RR, Thermochim. Acta, 386(2), 143 (2002)
Okadaa K, Yamaguchi K, Takeda H, Prog. Org. Coat., 34, 169 (1997)
van der Linde R, Belder EG, Perera DY, Prog. Org. Coat., 40, 215 (2000)
Vechot L, Bombard I, Laurent P, Lieto J, Int. J. Therm. Sci., 45, 86 (2006)
Misev TA, van der Linde R, Prog. Org. Coat., 34, 160 (1998)
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Bodanszky M, Peptide Chemistry: A Practical Textbook, Springer, New York (1988)
Hudson D, J. Org. Chem., 53, 617 (1988)
Madbouly SA, Eldin AFS, Mansour AA, Eur. Polym. J., 43, 2462 (2007)

[Related Articles]

[1] Howell DM, Powder Coatings: The Technology, Formulation and Application of Powder Coatings, ed Sanders JD, 1, John Wiley and Sons, London, UK (2000)

[2] Mafi R, Mirabedini SM, Attar MM, Moradian S, Prog. Org. Coat., 54, 164 (2005)

[3] Belder EG, Rutten HJJ, Perera DY, Prog. Org. Coat., 42, 142 (2001)

[4] Utech B, A Guide to High-performance Powder Coating, Society of Manufacturing Engineers, Michigan (2002)

[5] Lee SH, Park TW, Lee JO, Polymer (Korea), 23, 293 (1999)

[6] Dearth RS, Roseler RR, Nodelman NH, Schmitt PD, U.S. Patent 5,202,406 (1993)

[7] Mafi R, Mirabedini SM, Naderi R, Attar MM, Corros. Sci., 50, 3280 (2008)

[8] Parra DF, Mercuri LP, Matos JR, Brito HF, Romano RR, Thermochim. Acta, 386(2), 143 (2002)

[9] Okadaa K, Yamaguchi K, Takeda H, Prog. Org. Coat., 34, 169 (1997)

[10] van der Linde R, Belder EG, Perera DY, Prog. Org. Coat., 40, 215 (2000)

[11] Vechot L, Bombard I, Laurent P, Lieto J, Int. J. Therm. Sci., 45, 86 (2006)

[12] Misev TA, van der Linde R, Prog. Org. Coat., 34, 160 (1998)

[13] Roman F, Montserrat S, Prog. Org, Coat., 56, 311 (2006)

[14] Schlaefer FW, European Patent, 473,380, A1 (1991)

[15] Noordover BAJ, van Staalduinen VG, Duchateau R, Koning CE, van Benthem RATM, Mak M, Heise A, Frissen AE, van Haveren J, Biomacromolecules, 7, 3406 (2007)

[16] Palanisamy A, Rao BS, Prog. Org. Coat., 56, 297 (2006)

[17] Cho YH, J. Korean Ind. Eng. Chem., 4(1), 1 (1993)

[18] Wang FJ, Martinuzzi R, Zhu J, Powder Technol., 150(1), 20 (2005)

[19] Bodanszky M, Peptide Chemistry: A Practical Textbook, Springer, New York (1988)

[20] Hudson D, J. Org. Chem., 53, 617 (1988)

[21] Madbouly SA, Eldin AFS, Mansour AA, Eur. Polym. J., 43, 2462 (2007)