Polymerizable compositions with acylgermanium compounds

• US 7,605,190 B2
• Filed: 09/26/2007
• Issued: 10/20/2009
• Est. Priority Date: 09/27/2006
• Status: Active Grant

• Current Assignee: Ivoclar Vivadent AG
• Original Assignee: Ivoclar Vivadent AG
• Inventors: Moszner, Norbert, Fischer, Urs Karl, Liska, Robert, Gruber, Heinrich, Salz, Ulrich, Ganster, Beate
• Primary Examiner(s): McClendon; Sanza L
• Application Number:
  US11/902,865
• Publication Number:
  US 20080277814A1
• Time in Patent Office: 755 Days
• Field of Search: 522/33, 522/66, 522/168, 522/170, 522/113, 522/120, 522/121, 522/122, 522/134, 522/143, 522/144, 522/178, 522/182, 556/87, 523/105, 523/109, 523/111, 523/113, 523/114, 523/115, 523/116, 523/117, 523/118, 523/120
• US Class Current: 522/66
• CPC Class Codes: A61K 6/887 Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: C08F 2/50 with sensitising agents
• CPC Class Codes: C08F 4/72 selected from metals not provided for in group C08F4/44 C08F4/54 - C08F4/70 take precedence
• CPC Class Codes: C08L 33/00 Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
• CPC Class Codes: Y10S 522/908 Dental utility

Abstract

Composition with at least one polymerizable binder and at least one polymerization initiator, which contains at least one acylgermanium compound according to general Formula (I),

in which R⁰ is a substituted or unsubstituted C_1-18-alkyl radical or an acyl group; R¹ and R² are H, an acyl group or have one of the meanings given for R³; R³ is a branched or linear C_1-18-alkyl radical which can be unsubstituted or substituted one or more times by —O—, —NH—, —NR—, —S— or interrupted by other groups, trimethylsilyl, hal-(CH₃)₂Si—[OSi(CH₃)₂]_r⁻, (CH₃)₃Si—[OSi(CH₃)₂]_r—, —COOH, —COO—R¹⁰, —CO—NR¹¹R¹², —CO-vinyl, —CO-phenyl, phenyl-C_1-4-alkyl, phenyl, naphthyl or biphenyl, C_5-12 cycloalkyl, a 5 or 6-membered O, S or N-containing heterocyclic ring, halogen, OH, an aromatic C_6-30 radical which can be substituted or unsubstituted and/or interrupted by O, S or —NR—, or a branched, cyclic or linear C_1-20 alkyl, -alkenyl, -alkoxy or -alkenoxy radical; m is 1, 2 or 3; n is 0 or 1 and p is 0 or 1; wherein in each case two of the radicals R⁰, R¹, R² or R³ can be connected to each other accompanied by the formulation of a 5 to 8 member ring; and the use of acylegermanium compounds of Formula (I), for example, as initiator for radical polymerization.

Claims

1. A composition with at least one polymerizable binder and at least one polymerization initiator, the composition comprising at least one acylgermanium compound according to Formula (I),

2. The composition according to claim 1, wherein

R⁰ is C_1-18 alkyl, C_2-18 alkenyl, wherein these radicals can be unsubstituted or substituted one or more times by halogen, —

OR¹⁰, —

OCO—

R¹⁰, —

OCO-hal, —

COO—

R¹⁰, —

CH═

CH—

CO—

OR¹⁰, —

N(R¹¹)—

CO—

R¹⁰, —

N(R¹¹)—

CO-hal, —

C(C_1-4-alkyl)=C(C_1-4-alkyl)-CO—

OR¹⁰, —

CO—

NR¹¹R¹²—

CH═

CH-phenyl, —

C(C_1-4-alkyl)=C(C_1-4-alkyl)phenyl, C_3-12 cycloalkyl, C_2-18 alkenyl, phenyl-C_1-4-alkyl, phenyl, naphthyl, antryl, biphenyl, a 5 or 6-membered O, S or N-containing heterocyclic ring, wherein all named ring systems can be unsubstituted or substituted by 1 to 5 halogen atoms, C_1-8 alkyl, C_1-8 alkoxy and/or C_1-8 alkylthio radicals, or

5. The composition according to claim 1, wherein the polymerizable groups are selected from vinyl, styryl, (meth)acrylate, (meth)acrylamide or N-alkylacrylamide.

6. The composition according to claim 1, wherein the radicals R², R³, R⁶, R⁷ and R⁸ are substituted with 1 to 3 polymerizable groups.

7. The composition according to claim 1, comprising 0.001 to 5 weight % of the acylgermane of Formula (I).

8. The composition according to claim 1, wherein the polymerizable binder comprises at least one radically polymerizable monomer and/or prepolymer.

9. The composition according to claim 8, wherein the binder comprises a mono- or multifunctional (meth)acrylate, or a mixture thereof.

10. The composition according to claim 8, comprising at least one radically ring-opening polymerizable monomer.

11. The composition according to claim 1, wherein the binder comprises a mixture of mono- and/or multifunctional mercapto compounds and di- and/or multifunctional unsaturated monomers.

12. The composition according to claim 1, comprising at least one further initiator for radical polymerization.

13. The composition according to claim 1, comprising at least one further initiator for cationic polymerization.

14. The composition according to claim 1, further comprising a filler.

15. The composition according to claim 1, further comprising at least one additive which is selected from stabilizers, UV absorbers, slip additives, wetting agents, dispersants, adhesion promoters, matting and brightening agents, leveling agents and film-forming auxiliaries, antiskinning agents, light-protection agents, corrosion-protection agents, flame retardants, antioxidants, optical brighteners, flow improvers, thickeners and anti-foaming agents.

16. The composition of claim 1, comprising:

0.001 to 5 weight % acylgermanium compound according to Formula (I),

5 to 99.9 weight % polymerizable binder, and

0 to 90 weight % filler.

17. The composition according to claim 16, comprising 0 to 50 weight % of a further additive.

18. A combination for the preparation of dental moldings, the combination comprising:

the composition according to claim 1; and

an LED light source.

19. The combination according to claim 18, wherein the LED light source has a wavelength in the range from 400 to 550 nm and the acylgermanium compound has an activation wavelength in the range from 400 to 550 nm.

20. A method for the preparation of a molding, comprising:

molding the composition according to claim 1 into a body with the desired shape; and

at least partially curing the body.

21. The method according to claim 20, comprising shaping the body so as to form one or more of:

a dental crown, bridge, inlay or artificial tooth.

3. A composition with at least one polymerizable binder and at least one polymerization initiator, the composition comprising at least one acylgermanium compound according to Formula (II),

4. A composition with at least one polymerizable binder and at least one polymerization initiator, the composition comprising at least an acylgermanium compound according to Formula (III):