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US 5,962,703 AGranted
Functionalized bicyclic (meth)acrylate, a method of making a bicyclic (meth)acrylate, and its uses
AssigneeIvoclar AG
InventorsNorbert Moszner, Volker Rheinberger, Karin Vogel, Frank Zeuner
Life of this patent
Estimating the term…
Abstract
Functionalized bicyclic (meth)acrylates with norbornenyl or norbornadienyl groups are described, which may be cured with radicals at room temperature and are particularly suitable as an adhesion-promoting component of dental adhesives.
Claims5
A method of forming a dental material comprising:
- homopolymerizing or copolymerizing a bicyclic (meth)acrylate having formula I or formula II, a stereoisomeric compound, or a mixture thereof ##STR10## wherein A-B, T, U, V, W, X, Y, Z, R, R.sup.1, R.sup.2, R.sup.3, R.sup.4, n and m, independently of one another, having the following meanings:
- A-B=C--C or C.dbd.C;
- X=CH.sub.2, O, N--CO--OR, N--COR, N--CONR.sub.2 or N--SO.sub.2 R,
- where
- the individual groups R independently of one another are substituted or unsubstituted C.sub.1 - to C.sub.12 -alkyl or C.sub.6 - to C.sub.14 -aryl;
- Z=CH.sub.2 .dbd.CH--CO-- or CH.sub.2 .dbd.C(CH.sub.3)--CO--;
- V=C.sub.1 - to C.sub.6 -alkylenoxy, CH.sub.2 --S, CH.sub.2 --NH or COO--(C.sub.1 - to C.sub.6)-alkylenoxy;
- Y=H, C.sub.1 - to C.sub.12 -alkyl, C.sub.6 - to C.sub.14 -aryl, halogen, NO.sub.2, NR.sup.1.sub.2, OR.sup.1, CN, CO--R.sup.1, CO--NR.sup.1.sub.2, CO--OR.sup.1, SR.sup.1, SO.sub.2 R.sup.1 or SO.sub.3 R.sup.1,
- where
- the individual groups R.sup.1 independently of one another are H, substituted or unsubstituted C.sub.1 - to C.sub.12 -alkyl, C.sub.6 - to C.sub.14 -aryl or --(CH.sub.2 CH.sub.2 O).sub.n H with n=1 to 10;
- T=C.sub.1 - to C.sub.12 -alkyl, C.sub.6 - to C.sub.14 -aryl, halogen, NO.sub.2, NR.sup.2.sub.2, OR.sup.2, CN, CO--R.sup.2, CO--NR.sup.2.sub.2, CO--OR.sup.2, SR.sup.2, SO.sub.2 R.sup.2 or SO.sub.3 R.sup.2,
- where
- the individual groups R.sup.2 independently of one another are H, substituted or unsubstituted C.sub.1 - to C.sub.12 -alkyl, C.sub.6 - to C.sub.14 -aryl or --(CH.sub.2 CH.sub.2 O).sub.n H with n=1 to 10;
- or Y and T together=-CO--O--CO or --CO--NR.sup.3 --CO-,
- where
- R.sup.3 is H, substituted or unsubstituted C.sub.1 to C.sub.12 - alkyl, C.sub.6 - to C.sub.14 -aryl or --(CH.sub.2 CH.sub.2 O).sub.n H with n=1 to 10;
- U=C.sub.1 - to C.sub.12 -alkylenoxy, CO--NR.sup.4 --, CO--O or O,
- where
- R.sup.4 is H, substituted or unsubstituted C.sub.1 - to C.sub.12 -alkyl or C.sub.6 - to C.sub.14 -aryl;
- W=di- to tetra-substituted C.sub.1 - to C.sub.12 -alkylene, C.sub.6 - to C.sub.14 -arylene, C.sub.8 - to C.sub.16 -aralkylene or (--CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --).sub.n with n=1 to 10;
- and
- m 2 to 4, and
- to produce a dental material.
20 more elements
A dental material comprising a bicyclic (meth)acrylate having formula I or formula II, a stereoisomeric compound or homopolymers or copolymers or mixtures thereof:
- ##STR11## wherein A-B. T, U, V, W, X, Y, Z, R, R.sup.1, R.sup.2, R.sup.3, R.sup.4, n and m, independently of one another, having the following meanings:
- A-B=C--C or C.dbd.C;
- X=CH.sub.2, O, N--CO--OR, N--COR, N--CONR.sub.2 or N--SO.sub.2 R,
- where
- the individual groups R independently of one another are substituted or unsubstituted C.sub.1 - to C.sub.12 - alkyl or C.sub.6 - to C.sub.14 -aryl;
- Z=CH.sub.2 .dbd.CH--CO-- or CH.sub.2 .dbd.C(CH.sub.3)--CO--;
- V=C.sub.1 - to C.sub.6 -alkylenoxy, CH.sub.2 --S, CH.sub.2 --NH or COO--(C.sub.1 - to C.sub.6)-alkylenoxy
- Y=H, C.sub.1 - to C.sub.12 -alkyl, C.sub.6 - to C.sub.14 -aryl, halogen, NO.sub.2, NR.sup.1.sub.2, OR.sup.1, CN, CO--R.sup.1, CO--NR.sup.1.sub.2, CO--OR.sup.1, SR.sup.1, SO.sub.2 R.sup.1 or SO.sub.3 R.sup.2,
- where
- the individual groups R.sup.1 independently of one another are H, substituted or unsubstituted C.sub.1 - to C.sub.12 -alkyl- C.sub.6 - to C.sub.14 -aryl or --(CH.sub.2 CH.sub.2 O).sub.n H with n=1 to 10;
- T=C.sub.1 - to C.sub.2 -alkyl, C.sub.6 - to C.sub.14 -aryl, halogen, NO.sub.2, NR.sup.2.sub.2, OR.sup.2, CN, CO-R.sup.2, CO--NR.sup.2.sub.2, CO--OR.sup.2, SR.sup.2, SO.sub.2 R.sup.2 or SO.sub.3 R.sup.2,
- where
- the individual groups R.sup.2 independently of one another are H, substituted or unsubstituted C.sub.1 - to C.sub.12 -alkyl, C.sub.6 - to C.sub.14 -aryl or --(CH.sub.2 CH.sub.2 O).sub.n H with n=1 to 10:
- or Y and T together=--CO--O--CO or --CO--NR.sup.3 --CO--,
- where
- R.sup.3 is H, substituted or unsubstituted C.sub.1 - to C.sub.12 - alkyl, C.sub.6 - to C.sub.14 -aryl or --(CH.sub.2 CH.sub.2 O).sub.n H with n=1 to 10:
- U=C.sub.1 - to C.sub.12 -alkylenoxy, CO--NR.sup.4 --, CO--O or O,
- where
- R.sup.4 is H, substituted or unsubstituted C.sub.1 - to C.sub.12 -alkyl or C.sub.6 - to C.sub.14 -aryl;
- W=di- to tetra-substituted C.sub.1 - to C.sub.12 -alkylene, C.sub.6 - to C.sub.14 -arylene, C.sub.8 - to C.sub.16 -aralkylene or (--CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --).sub.n with n=1 to 10;
- and
- m=2to 4.
19 more elements
Dependencies are inferred from the claim text.