화학공학소재연구정보센터
Polymer(Korea), Vol.28, No.6, 531-537, November, 2004
하프-에스터 아크릴레이트를 이용한 광경화형 에폭시 변성 아크릴레이트의 합성과 물성
Synthesis and Properties of Photocurable Epoxy Modified Acrylates Using Half-Ester Acrylates
E-mail:
초록
다양한 하프-에스터 아크릴레이트를 합성하기 위하여 다양한 산 무수물에 2-하이드록시에틸 아크릴레이트 (2-hydroxyethyl acrylate)를 반응시켰다. 합성된 하프-에스터 아크릴레이트에 지방족 에폭시 화합물인 네오펜틸글리콜 디글리시딜에테르 (neopentylglycol diglycidylether)를 반응시켜 광경화형 에폭시 변성 아크릴레이트를 제조하였다. 점도는 헥사하이드로프탈산 무수물 (hexahydrophthalic anhydride)을 사용하여 반응시킨 네오펜틸글리콜 디글리시딜에테르-헥사하이드로프탈산 무수물 (NP-HA)이 가장 높았다. 또한 헥사하이드로프탈산 무수물을 사용한 네오펜틸글리콜 디글리시딜에테르-헥사하이드로프탈산 무수물의 광경화물은 비교적 다른 산 무수물을 사용하여 제조한 에폭시 변성 아크릴레이트의 광경화물보다 경도, 인장 강도가 우수하였으며, 5% 무게 감소 온도도 높은 것으로 보아 열적으로 안정하다는 것을 알 수 있었다. 황변 지수값은 숙신산 무수물 (succinic anhydride)을 사용하여 반응시킨 네오펜틸글리콜 디글리시딜에테르-숙신산 무수물 (NP-SA)이 가장 낮았다.
Various half-ester acrylates were prepared from anhydrides and 2-hydroxyethyl acrylate. Photocurable epoxy modified acrylates were prepared from synthesized half-ester acrylate and neopentylglycol diglycidylether. Physical properties such as hardness, yellowing, tensile strength and elongation were tested and compared as the structure of oligomer in cured-film differs. It was found that viscosity of neopentylglycol diglycidylether-hexahydrophthalic anhydride (NP-HA) was highest. Hardness and tensile strength of photocrosslinked neopentylglycol diglycidylether-hexahydrophthalic anhydride were better than those of other photocrosslinked epoxy acrylates. And 5% weight loss temperature of photocrosslinked neopentylglycol diglycidylether-hexahydrophthalic anhydride was higher than those of other photocrosslinked epoxy acrylates. Value of yellow index of photocrosslinked neopentylglycol diglycidyl ether-succinic anhydride (NP-SA) was lower than the other products.
  1. Braithwaite M, Davidson S, Holman R, Lowe C, Oldring PKT, Salim MS, Wall C, "Chemistry & Technology of UV & EB Formulation for Coatings, Inks & Paints", P.K.T. Oldring, Editor, SITA Technology, London (1991)
  2. Pappas SP, "Radiation Curing", Plenum, New York (1992)
  3. Pappas SP, "UV Curing: Science and Technology", Technology Marketing Corporation, Connecticut (1983)
  4. Jung JC, Polym.(Korea), 10(6), 570 (1986)
  5. Hoyle CE, Kinstle JF, "Radiation Curing of Polymeric Materials", American Chemical Society, Washigton DC (1990)
  6. Orcel G, Vanpoulle S, Barraud JY, Boniort JY, Overton B, Wire, 46, 206 (1996)
  7. Rodas AH, Bretas RES, Reggianni A, J. Mater. Sci., 21, 3025 (1986) 
  8. Lin SB, Tsay SY, Spechhard TA, Hwang KKS, Jezerc JJ, Cooper SL, Chem. Eng. Commun., 30, 251 (1984)
  9. Speckhard TA, Hwang KKS, Lin SB, Tsay SY, Koshiba M, Ding YS, Cooper SL, J. Appl. Polym. Sci., 30, 647 (1985) 
  10. Ali MA, Khan MA, Ali KM, J. Appl. Polym. Sci., 60(6), 879 (1996) 
  11. Yoo JW, Kim DS, Polym.(Korea), 23(3), 376 (1999)
  12. Kim HD, Lee DJ, Choi JH, Park CC, Polym.(Korea), 18(1), 38 (1994)
  13. Lee KH, Kim BK, Korea Polym. J., 4(1), 1 (1996)
  14. Kim HD, Kang SG, Ha CS, J. Appl. Polym. Sci., 46, 1339 (1992) 
  15. Otsubo Y, Amari T, Watanabe K, J. Appl. Polym. Sci., 29, 4071 (1984) 
  16. Matynia T, Kutyla R, Bukat K, Pienkowska B, J. Appl. Polym. Sci., 55(11), 1583 (1995) 
  17. Bajpai M, Shukla V, Kumar A, Progress in Organic Coatings, 44, 271 (2002) 
  18. Maruno T, Ishibashi S, Nakamura K, J. Polym. Sci. A: Polym. Chem., 32(16), 3211 (1994) 
  19. Shi WF, Ranby B, J. Appl. Polym. Sci., 51(6), 1129 (1994) 
  20. Williams TR, J. Appl. Polym. Sci., 31, 1293 (1986) 
  21. Bongiovanni R, Malucelli G, Sangermano M, Priola A, Prog. Org. Coat., 36, 70 (1999) 
  22. Kim JK, Kim DK, Hwang JY, J. Korean Ind. Eng. Chem., 14, 6 (2003)
  23. Lim JK, Kim DK, Kim WG, J. Korean Ind. Eng. Chem., 15(2), 225 (2004)
  24. Kim YC, Roh JB, Lee BJ, J. Korean Ind. Eng. Chem., 13(6), 538 (2002)
  25. Hong JW, Park MY, Kim HK, Kim Y, Choi HK, J. Korean Ind. Eng. Chem., 11(6), 693 (2000)
  26. Hong JW, Lee HW, J. Korean Ind. Eng. Chem., 5(5), 857 (1994)
  27. Kim DK, Lim JK, Kim WG, J. Korean Ind. Eng. Chem., 15, 749 (2004)