Patent EP-2489344-A1 (EP)
Inventor: SALZ ULRICH DR
IPC: A61K6/896
Filed: 2011-02-15
Abstract: Dental restorative material comprises: (a) at least one antimicrobially active polymer (I) or a filler i.e. surface-modified with (I); (b) at least one radically polymerizable monomer; and (c) at least one initiator for the radical polymerization. Dental restorative material comprises: (a) at least one antimicrobially active polymer of formula ([AG] m-R1-Z-SP-Y1-R2-[WG] p) (I) or a filler i.e. surface-modified with (I); (b) at least one radically polymerizable monomer; and (c) at least one initiator for the radical polymerization. R1, R2 : 6-14C aromatic radical (optionally substituted), absent, and/or linear or branched 1-20C alkylene radical which can be interrupted one or more times by O, S, NH, N +>R3 2, SiR3 2, OSiR3 2, CONH, CONR3, COO and/or OCONH; R3 : phenyl (optionally substituted), linear or branched 1-20C alkyl radical, or benzyl radical; AG : an anchor group comprising -P((OR11a)(OR11b))=O, -O-P((=O)(OR11b))-OR11a, or -O-P((OR11a)(OR11b))=O; either R11a, R11b : H, alkyl, aryl or -Si(alkyl) 3, where alkyl is preferably methyl, ethyl, n-propyl or i-propyl; or R11a : H; or R11b : alkyl, -C((OH)(=O)), trimellitic acid group of formula (a1), 5,6-dicarboxy-1,3-dioxo-isoindolin-2-yl, -C(=O)-O-C(=O)-, trimellitic acid anhydride group of formula (b1), 1,3,5,7-tetraoxofuro[3,4-f]isoindol-6-yl, 2,5-dioxotetrahydrofuran-3-yl, -S(=O) 2-OH, or -S(=O) 2-OR12; R12 : -Si(alkyl) 3, alkyl (preferably methyl, ethyl, n-propyl or i-propyl), -N=C=O, -O-C(=O)-H, -NH-C(=O)-OH, -O-C(=O)-CH 2-C(=O)-CH 3, -C(=O)-CH 2-C(=O)-O-CH 3, -C(=O)-H, or -HC(OR13a)-OR13b; either R13, R13a, R13b : alkyl (preferably methyl, ethyl, n-propyl or i-propyl); or R13aR13b : 4-7 (preferably 5) membered ring system, where one of the oxygen atoms can be replaced by N or -C(=NH)-O-R14; R14 : alkyl (preferably methyl, ethyl, n-propyl, i-propyl, n-butyl or t-butyl), (2,5-dioxooxazolidin-3-yl)oxycarbonyl, (2,4-dioxo-5-sulfo-oxazolidin-3-yl)oxycarbonyl, 2,5-dioxopyrrolidin-1-yl, or -N=C=N-R15; R15 : optionally substituted alkyl or cycloalkyl group, preferably 3-dimethylaminopropyl, i-propyl or cyclohexyl, -Si(H) 2-R16, or -Si(R16) 2-H; R16 : alkoxy (preferably methoxy, ethoxy or propoxy), aryloxy (both preferred), Cl, alkyl, aryl, or -Si((R17a)(R17c))-R17b; R17a : alkoxy (preferably methoxy, ethoxy, or propoxy), aryloxy, Cl or OH; R17b, R17c : alkoxy (preferably methoxy, ethoxy, or propoxy), aryloxy, Cl, OH, alkyl, aryl, -S-H, or -S-S-R18; R18 : alkyl, aryl, arylalkyl, -P((OR19a)(OR19b))=S, -O-P((=S)(OR19b))-R19a or -O-P((OR19a)(OR19b))=S, preferably methyl, ethyl, n-propyl, i-propyl, n-butyl, t-butyl, phenyl, biphenyl or alkylphenyl; either R19a, R19b : H, alkyl (preferably methyl, ethyl, n-propyl or i-propyl), aryl or -Si(alkyl) 3; or R19a : H; or R19b : alkyl, or -C(=O)-S-R20; R20 : optionally substituted alkyl (preferably -CH 2-CH 2-NH 2or -CH 2-CH(NH 2)-COOH), -NH-C(=S)-CH 3, triazine thione group of formula (c1), triazine dithione group of formula (d1), or thiouracil group of formula (e1); R21 : H or alkyl (preferably methyl, ethyl, n-propyl or i-propyl); SP : a polymeric spacer, preferably polyethylene glycol, polypropylene glycol, polyglycerol, polyalkyloxazoline, polyethyleneimine, polyacrylic acid, polymethacrylic acid, polyvinyl alcohol, polyvinyl acetate, poly-(2-hydroxyethyl) acrylate, poly-(2-hydroxyethyl)methacrylate, hydrophilic polypeptide, polyoxazoline, polyalkylene, polyester, polyamide, polyurea, polyurethane, polycyanoacrylate, polyacrylate, polyacrylic ester, polymethacrylate, or polymethacrylic ester, groups, polymethacrylic ester groups, N-alkylated polyethyleneimine groups, N-alkylated polyethyleneimine, N-alkylated vinylpyridine, polysaccharide, polyaminosaccharide, or their copolymers; WG : an antimicrobially active group; Y1, Z : absent, O, S, NH, N +>R3 2, ester, amide or urethane group; m : 1-4; and p : 1-3. [Image].