화학공학소재연구정보센터
홈 로그인 로그아웃 연락처 사이트맵
Polymer(Korea), Vol.30, No.6, 538-544, November, 2006
Export Citation
비스페놀 A를 함유하지 않은 치과용 신규 프리폴리머의 합성 및 유기 매트릭스의 제조
Synthesis of Novel Prepolymers Containing No Bisphenol A and Preparation of Organic Matrices for Dental Applications
손준식, 이기백, 박귀덕, 김재진, 안광덕, 김중현1, 한동근†
  • 한국과학기술연구원 생체재료연구센터
  • 1연세대학교 화학공학과
Jun Sik Son, Ki Baek Lee, Kwideok Park, Jae-Jin Kim, Kwang-Duk Ahn, Jung Hyun Kim1, and Dong Keun Han†
  • Biomaterials Research Center, Korea Institute of Science and Technology, P.O. Box 131, Cheongryang, Seoul 130-650, Korea
  • 1Department of Chemical Engineering, Yonsei University, 134 Shinchon-dong, Seodaemun-gu, Seoul 120-749, Korea
E-mail:
초록
치과용 재료로 사용되고 있는 환경호르몬으로 추정되는 비스페놀 A를 함유한 2,2-bis[4-(2'-hydroxy- 3'-methacryloyloxypropoxy)phenyl]propane(Bis-GMA)을 대체할 수 있는 화학적 구조가 Bis-GMA와 유사한 2종류의 신규 2관능성 methacrylated prepolymer인 170-2MA와 631-2MA를 합성하였다. 이렇게 합성된 prepolymer를 희석제와 다른 단량체를 혼합하여 새로운 치과용 유기 매트릭스를 제조하였으며, 신규 prepolymer의 수율과 점도 및 화학적 구조와 유기 매트릭스의 물리적 및 기계적 물성을 평가하였다. 비스페놀 A를 함유하지 않은 2종류의 에폭시 화합물과 methacrylic acid의 개환반응에 의해서 각각 methacrylation하여 합성된 prepolymer는 90% 이상의 높은 반응 수율을 보였으며 control인 Bis-GMA에 비해서 상대적으로 낮은 점도를 보였다. 또한 합성된 methacrylated prepolymer는 Bis-GMA와 유사한 화학적 구조임을 1H-NMR과 FTIR 분석결과로부터 확인하였다. 2종류의 합성 prepolymer를 이용하여 제조한 유기 매트릭스의 경화시간, 중합 수축률, 광전환율, 중합깊이 및 압축강도는 control인 Bis-GMA를 함유한 것에 비해서 비슷하거나 약간 더 우수한 특성을 나타내었다. 따라서 본 연구에서 합성한 비스페놀 A를 함유하지 않은 170-2MA와 631-2MA prepolymer는 현재 사용중인 Bis-GMA를 대체할 수 있는 새로운 치과용 고분자재료로 충분히 적용이 가능할 것으로 사료된다.
Two kinds of novel bifunctional methacrylated prepolymers (170-2MA and 631-2MA) which have similar structure with 2,2-bis[4-(2'-hydroxy-3'-methacryloyloxypropoxy)phenyl]propane (Bis-GMA) was synthesized for dental applications as an alternative to Bis-GMA containing bisphenol A that is doubtful as an endocrine disrupter. The organic matrices were prepared by mixing a diluent and/or a monomer with the synthesized methacrylated prepolymers. The yield, viscosity, and chemical structures of the prepolymers and the physical and mechanical properties of the organic matrices were evaluated. The yields of the prepolymers synthesized through a ring-opening reaction of epoxy compound and methacrylic acid were above 90% and the viscosities of the prepolymers were much lower than that of the Bis-GMA control. From the results of 1H-NMR and FTIR analyses, the chemical structures of the prepolymers were similar to that of Bis-GMA. In addition, the curing time, polymerization shrinkage, photoconversion, polymerization depth, and compressive strength of the organic matrices formulated with 170-2MA and 631-2MA prepolymers exhibited comparable to or better than those of the existing Bis-GMA-based one. These results suggest that the novel methacrylated prepolymers which have no endocrine disrupter can be an alternative to Bis-GMA and be applicable to dental polymer materials.
Keywords:dental materials;endocrine disrupter;Bis-GMA;bisphenol A;methacrylated prepolymer
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