Synthesis, Photopolymerization, and Adhesive Properties of New Bisphosphonic Acid Monomers for Dental Application

被引:38
作者
Catel, Yohann [1 ]
Degrange, Michel [2 ]
Le Pluart, Loic [1 ]
Madec, Pierre-Jean [1 ]
Pham, Thi-Nhan [1 ]
Chen, Fei [3 ]
Cook, Wayne D. [3 ]
机构
[1] Univ Caen Basse Normandie, CNRS, ENSICAEN, Lab Chim Mol & Thioorgan, F-14050 Caen, France
[2] Univ Paris 05, Unite Rech Biomat & Interfaces, Fac Chirurg Dentaire, F-92120 Montrouge, France
[3] Monash Univ, Dept Mat Engn, Clayton, Vic 3800, Australia
关键词
acrylamide; adhesives; bisphosphonic acid; dental polymers; photopolymerization; synthesis; HYDROLYTIC STABILITY; DEGRADATION; POLYMERIZATION; CONVERSION; KINETICS; BREAST;
D O I
10.1002/pola.23575
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
Four new monomers, 3-(N-methylacrylamido)propylidenebisphosphonic acid, 3-(N-propyl-acrylamido)propylidenebisphosphonic acid, 3-(N-hexylacrylamido)propylidenebisphosphonic acid, and 3-(N-octylacrylamido)propylidenebisphosphonic acid, have been synthesized in good yields and fully characterized by H-1, C-13, P-31 NMR, and HRMS. The copolymerization of these monomers with N,N'-diethyl-1,3-bis(acrylamido)propane (DEBAAP) has been investigated with differential scanning calorimetry. These mixtures show a higher reactivity than DEBAAP. New self-etch dental primers, based on these acrylamide monomers, have been formulated. Dentin shear bond strength measurements have shown that primers based on these bisphosphonic acids assure a strong bond between the tooth substance and a dental composite. (C) 2009 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 47: 5258-5271, 2009
引用
收藏
页码:5258 / 5271
页数:14
相关论文
共 32 条
[1]   Reductive amination of aldehydes and ketones with sodium triacetoxyborohydride. Studies on direct and indirect reductive amination procedures [J].
AbdelMagid, AF ;
Carson, KG ;
Harris, BD ;
Maryanoff, CA ;
Shah, RD .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (11) :3849-3862
[2]   Arylphosphonic acid-functionalized polyelectrolytes as fuel cell membrane material [J].
Bock, Thorsten ;
Moehwald, Helmut ;
Mulhaupt, Rolf .
MACROMOLECULAR CHEMISTRY AND PHYSICS, 2007, 208 (13) :1324-1340
[3]  
Boissier S, 2000, CANCER RES, V60, P2949
[4]   Dental adhesion review: Aging and stability of the bonded interface [J].
Breschi, Loyenzo ;
Mazzoni, Annalisa ;
Ruggeri, Alessandra ;
Cadenaro, Milena ;
Di Lenarda, Robeyto ;
Dorigo, Elettya De Stefano .
DENTAL MATERIALS, 2008, 24 (01) :90-101
[5]   Degree of conversion and permeability of dental adhesives [J].
Cadenaro, M ;
Antoniolli, F ;
Sauro, S ;
Tay, FR ;
Di Lenarda, R ;
Prati, C ;
Biasotto, M ;
Contardo, L ;
Breschi, L .
EUROPEAN JOURNAL OF ORAL SCIENCES, 2005, 113 (06) :525-530
[6]   Synthesis, Photopolymerization and Adhesive Properties of New Hydrolytically Stable Phosphonic Acids for Dental Applications [J].
Catel, Yohann ;
Degrange, Michel ;
Le Pluart, Loic ;
Madec, Pierre-Jean ;
Pham, Thi-Nhan ;
Picton, Luc .
JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2008, 46 (21) :7074-7090
[7]   Synthesis of novel phosphonated tritpodal ligands for actinides chelation therapy [J].
Chaleix, Vincent ;
Lecouvey, Marc .
TETRAHEDRON LETTERS, 2007, 48 (04) :703-706
[8]   KINETICS AND PROPERTIES OF A PHOTOPOLYMERIZED DIMETHACRYLATE OLIGOMER [J].
COOK, WD .
JOURNAL OF APPLIED POLYMER SCIENCE, 1991, 42 (08) :2209-2222
[9]   THERMAL ASPECTS OF THE KINETICS OF DIMETHACRYLATE PHOTOPOLYMERIZATION [J].
COOK, WD .
POLYMER, 1992, 33 (10) :2152-2161
[10]   A critical review of the durability of adhesion to tooth tissue: Methods and results [J].
De Munck, J ;
Van Landuyt, K ;
Peumans, M ;
Poitevin, A ;
Lambrechts, P ;
Braem, M ;
Van Meerbeek, B .
JOURNAL OF DENTAL RESEARCH, 2005, 84 (02) :118-132