US 7,595,354 B2
Dental materials with unusual fluorine distribution
Norbert Moszner, Triesen (Liechtenstein); Urs Karl Fischer, Arbon (Switzerland); Volker M Rheinberger, Vaduz (Liechtenstein); Giancarlo Galli, Pescia (Italy); Marina Ragnoli, Collesalvetti (Italy); and Emo Chiellini, Pisa (Italy)
Assigned to Ivoclar Vivadent AG, Schaan (Liechtenstein)
Filed on Jan. 24, 2006, as Appl. No. 11/338,034.
Claims priority of application No. 05105472 (EP), filed on Jun. 21, 2005.
Prior Publication US 2006/0287458 A1, Dec. 21, 2006
Int. Cl. A61C 5/04 (2006.01); A61K 6/083 (2006.01); C08F 12/20 (2006.01); C08F 232/04 (2006.01)
U.S. Cl. 523—116  [523/118; 433/228.1; 526/242; 526/309] 19 Claims
 
1. A composition comprising
(A) at least one fluorinated vinylcyclopropane according to formula (I)

OG Complex Work Unit Drawing
wherein
R1 is H or —CO—O—(CH2CH2)p—R7,
R2 is H or forms together with R6 a —CH2—C(R9)(R10)—CH2— residue,
R3 is H,
R4 is H or forms together with R5 a —CH2—C(R9)(R10)—CH2— residue,
R5 is H, —CO—O—R8, —CO—O—(CH2CH2)p—R7 or forms together with R4 a —CH2—C(R9)(R10)—CH2— residue,
R6 is H, —CO—O—R8, —CO—O—(CH2CH2)p—R7 or forms together with R2 a —CH2—C(R9)(R10)—CH2— residue,
R7 is perfluorinated aliphatic or alicyclic C2-C20 group,
R8 is H, phenyl, benzyl, or a linear or branched aliphatic or alicyclic C1-C12 group,
R9 is a H, benzoyl, acetyl or a C1-C5-alkyl group,
R10 is H or a —CO—O—R8, and
p is 1, 2, 3, or 4,
provided that the compound of formula (I) comprises at least one —CO—O—(CH2CH2)p—R7 residue,
(B) at least one non-fluorinated vinylcyclopropane, and
(C) at least one bisphenol-A-ether di(meth)acrylate according to formula (II)

OG Complex Work Unit Drawing
wherein
R18 is H or CH3,
R19 is CH3 or CF3, and
y is a C2-C5-alkylen residue which is substituted by an OH group or is unsubstituted.