액정성 에폭시 아크릴레이트 합성 및 특성

김영철; 노종범; 이범재; Young Chul Kim; Jong Beom Roh; Bum Jae Lee

Journal of the Korean Industrial and Engineering Chemistry, Vol.13, No.6, 538-543, October, 2002

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액정성 에폭시 아크릴레이트 합성 및 특성

Synthesis and Characterization of Liquid Crystalline Epoxy Acrylate

김영철 ^†, 노종범, 이범재 ¹

한국화학연구원 신뢰성평가센터, 대전 305-600
¹충남대학교 공과대학 공업화학과, 대전 305-764

Young Chul Kim^†, Jong Beom Roh, and Bum Jae Lee¹

Reliability Assessment Center, Korea Research Institute of Chemical Technology, Daejeon 305-600, Korea
¹Department of Chemical Engineering, Chungnam National University, Daejeon 305-764, Korea

E-mail:

초록

4.4'-Dihydroxy-α-methylstilbene을 주쇄로 하여 액정성을 나타내는 열경화형 에폭시 올리고머의 양말단에 아크릴기를 도입하여 광경화형 에폭시 아크릴레이트 올리고머를 제조하고 액정거동과 광경화 반응성을 검토하였다. 4,4'-Dihydroxy methylstilbene과 epichlorohydrin을 반응시켜 4,4'-dihydroxy methylstilbene diglycidyl ether를 제조한 후, 톨루엔을 반응희석제로 사용하여 상이동촉매 하에서 acrylic acid와 12 h 반응시켜 4,4'-dihydroxy methylstilbene glycerolate diacrylate를 제조하였다. 제조된 에폭시 아크릴레이트 올리고머는 상온에서 49 ℃ 영역까지 smectic 액정상을 나타내었다. 제조된 에폭시 아크릴레이트 올리고머에 반응희석제를 사용하여 광경화 반응을 하였을 경우 소량의 광개시제에서도 높은 전환율의 광경화 반응이 이루어졌다.

Liquid crystalline(LC) epoxy acrylate containing the mesongenic core of α-methylstilbene was synthesized. The epoxy oligomers were synthesized with 4.4'-dihydroxy-α-methylstilbene and epichlorohydrin. The epoxy acrylate oligomer was synthesized from epoxy oligomer and acrylic acid in the presence of a reaction medium and a phase transfer catalyst for 12 h. The synthesized epoxy acrylate oligomer showed smectic LC phase from room temperature to near 50 ℃ compared with the nematic epoxy oligomer. UV-photo curing of synthesized epoxy acrylate with a reactive diluent photo-initiator was performed. The synthesized epoxy acrylate showed high photo-reactivity.

Keywords:acrylate;UV cure;smectic;stilbene;liquid crystalline

[References]

Schultz JW, Chartoff RP, Polymer, 39(2), 319 (1998)
Lin QH, Yee AF, Sue HJ, Earls JD, Hefner RE, J. Polym. Sci. B: Polym. Phys., 35(14), 2363 (1997)
Ochi M, Takashima H, Polymer, 42(6), 2379 (2001)
Ribera D, Mantecon A, Serra A, Macromol. Chem. Phys., 202, 1658 (2001)
Carfagna C, Amendola E, Giamberini M, Filiprov AG, Bauer RS, Liq. Cryst., 13, 571 (1993)
Amendola E, Carfagna C, Giamberini M, Pisaniello G, Macromol. Chem. Phys., 196, 1577 (1995)
Mormann W, Zimmermann J, Irle C, Polym. Prepr., 34, 704 (1993)
Carfagna C, Amendola E, Giamberini M, Macromol. Chem. Phys., 195, 279 (1994)
Carfagna C, Amendola E, giamberini M, Compos. Struct., 27, 37 (1994)
Broer DJ, Finkelmann H, Kondo K, Makromol. Chem., 189, 185 (1988)
Ullett JS, Chartoff RP, Schultz JW, Bhatt JC, Dotrong M, Pogue RT, Solid Freeform Fabrication Proceedings, Septemper, 471 (1996)
Korner H, Shiota A, Bunning TJ, Ober CK, Science, 272(5259), 252 (1996)
Zaheer SH, Rao NS, Kacker IK, J. Chem. Soc., 3360 (1954)
Carfagna C, Amendola E, Giamberini M, Hakemi H, Pane S, Polym. Int., 44, 465 (1997)
Liu W, Carfagna C, Macromol. Rapid Commun., 22, 1058 (2001)
Percec V, Mol. Cryst. Liq. Cryst., 205, 47 (1991)
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Pielichowski J, Czub P, Angew. Makromol. Chem., 251, 1 (1997)
Oldring PKT, Chemical & Technology of UV&EB formulation for Coatings, Inks & Paints, Chemical & Technology of UV&EB Formulation for Coatings, Inks & Paints, II, 30 (1991)
Gardner H, Johns J, U.S. Patent, 4,414,367 (1983)

[Referenced By]

[Related Articles]

[1] Schultz JW, Chartoff RP, Polymer, 39(2), 319 (1998)

[2] Lin QH, Yee AF, Sue HJ, Earls JD, Hefner RE, J. Polym. Sci. B: Polym. Phys., 35(14), 2363 (1997)

[3] Ochi M, Takashima H, Polymer, 42(6), 2379 (2001)

[4] Ribera D, Mantecon A, Serra A, Macromol. Chem. Phys., 202, 1658 (2001)

[5] Carfagna C, Amendola E, Giamberini M, Filiprov AG, Bauer RS, Liq. Cryst., 13, 571 (1993)

[6] Amendola E, Carfagna C, Giamberini M, Pisaniello G, Macromol. Chem. Phys., 196, 1577 (1995)

[7] Mormann W, Zimmermann J, Irle C, Polym. Prepr., 34, 704 (1993)

[8] Carfagna C, Amendola E, Giamberini M, Macromol. Chem. Phys., 195, 279 (1994)

[9] Carfagna C, Amendola E, giamberini M, Compos. Struct., 27, 37 (1994)

[10] Broer DJ, Finkelmann H, Kondo K, Makromol. Chem., 189, 185 (1988)

[11] Ullett JS, Chartoff RP, Schultz JW, Bhatt JC, Dotrong M, Pogue RT, Solid Freeform Fabrication Proceedings, Septemper, 471 (1996)

[12] Korner H, Shiota A, Bunning TJ, Ober CK, Science, 272(5259), 252 (1996)

[13] Zaheer SH, Rao NS, Kacker IK, J. Chem. Soc., 3360 (1954)

[14] Carfagna C, Amendola E, Giamberini M, Hakemi H, Pane S, Polym. Int., 44, 465 (1997)

[15] Liu W, Carfagna C, Macromol. Rapid Commun., 22, 1058 (2001)

[16] Percec V, Mol. Cryst. Liq. Cryst., 205, 47 (1991)

[17] Robert E, David A, U.S. Patent, 5,723,693 (1998)

[18] Pielichowski J, Czub P, Angew. Makromol. Chem., 251, 1 (1997)

[19] Oldring PKT, Chemical & Technology of UV&EB formulation for Coatings, Inks & Paints, Chemical & Technology of UV&EB Formulation for Coatings, Inks & Paints, II, 30 (1991)

[20] Gardner H, Johns J, U.S. Patent, 4,414,367 (1983)