Dental composition based on silicone crosslinkable by cation process
AssigneeRhodia Chimie
InventorJean-Marc Frances
Life of this patent
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Abstract
The invention concerns dental compositions. Said composition comprises (1) a silicone crosslinkable and/or polymerizable by cation process; (2) an efficient amount of at least an initiator such as onium borate; (3) at least a photosensitizer ; and (4) a dental filler present in the composition in a proportion of at least 10 wt. % relative to the composition total weight. Said dental compositions are useful for making dental prostheses or for dental restoration.
Claims6
A process for the preparation of a dental prosthesis or dental restoration, comprising the step of shaping and curing a low shrinking polymerizable or crosslinkable dental composition comprising a mixture of:
- (1) at least one crosslinkable and/or polymerizable silicone oligomer or polymer which is liquid at room temperature or which is heat-meltable at a temperature of less than 100° C., and which comprises:
- at least one unit of formula (FS):
- wherein:
- a=0.1 or 2,
- R0, identical or different, represents an alkyl, cycloalkyl, aryl, vinyl, hydrogeno or alkoxy radical,
- Z, identical or different, is an organic substituent comprising at least one reactive epoxy, or alkenyl ether or oxetane or dioxolane or carbonate functional group,
- and at least two silicon atoms,
- (2) at least one aromatic hydrocarbon photosensitizer, having a residual light absorption of between 200 and 500 nm, and selected from the group consisting of the following formulae (VIII), (X). (XII) and (XXII):
- thioxanthones of formula (VIII):
- wherein:
- m=0 to 8,
- R17, identical or different substituent(s) on the aromatic nucleus (nuclei), represent a linear C1-C12 alkyl radical, a branched C1-C12 alkyl radical, a C6-C12 cycloalkyl radical, a radical Ar1, a halogen atom, an —OH, —CN, —NO2, —COOR6, —CHO, Ophenyl, —CF3, —SR6, —Sphenyl, —SO2phenyl, Oalkenyl, or —SiR63 group;
- xanthones of formula (X):
- wherein p=0 to 8
- anthracene of formula (XII):
- wherein=0 to 10, and
- biscoumarins of formula (XXII):
- wherein:
- R18, identical or different, has the same meaning as R17 above or represents a group:
- —NR62, wherein R6 represents a linear C1-C12 alkyl radical,
- (3) at least one dental filler present in a proportion of at least 10% by weight relative to the total weight of the composition, and
- (4) an effective quantity of at least one borate-type photoinitiator, whose borate residue is:
- 1′:
- [B(C6F5)4]−
- 2′:
- [(C6F5)2BF2]−
- 3′:
- [B(C6H4CF3)4]−
- 4′:
- [B(C6F4OCF3)4]−
- 5′:
- [B(C6H3(CF3)2)4]−
- 6′:
- [B(C6H3F2)4]−
- 7′:
- [C6F5BF3]−
- wherein the cationic entity of the borate is:
- [(Φ)2I]+
- [C8H17—O-Φ-I-Φ]+
- [(Φ-CH3)2I]+
- [C12H25-Φ-I-Φ]+
- [(C8H17—O-Φ)2I]+
- [(C8H17—O-Φ-I-Φ)]+
- [(Φ)3S]+
- [(Φ)2-S-Φ-O—C8H17]+[(CH3-Φ-I-Φ-CH(CH3)2]+
- [(Φ-S-Φ-S-(Φ)2]+
- [(C12H25- Φ)2I]+
- [(CH3-Φ-I-Φ-OC2H5]+;
- and
- wherein the composition has a volumetric polymerization and/or crosslinking shrinkage of less than 1.5% v/v.
A process for the preparation of a dental prosthesis or dental restoration, comprising the step of shaping and curing a low shrinking polymerizable or crosslinkable dental composition comprising a mixture of:
- (1) at least one crosslinkable and/or polymerizable silicone oligomer or polymer which is liquid at room temperature or which is heat-meltable at a temperature of less than 100° C., and which comprises:
- at least one unit of formula (FS):
- wherein:
- a=0,1 or 2,
- R0, identical or different, represents an alkyl, cycloalkyl, aryl, vinyl, hydrogeno or alkoxy radical,
- Z, identical or different, is an organic substituent comprising at least one reactive epoxy, or alkenyl ether or oxetane or dioxolane or carbonate functional group,
- and at least two silicon atoms,
- (2) at least one aromatic hydrocarbon photosensitizer, and
- (4) an effective quantity of at least one borate-type photoinitiator, whose borate residue is:
- 1′:
- [B(C6F5)4]−
- 2′:
- [(C6F5)2BF2]−
- 3′:
- [B(C6H4CF3)4]−
- 4′:
- [B(C6F4OCF3)4]−
- 5′:
- [B(C6H3(CF3)2)4]−
- 6′:
- [B(C6H3F2)4]−
- 7′:
- [C6F5BF3]−
- wherein the cationic entity of the borate is:
- [(Φ)2I]+
- [C8H17—O-Φ-I-Φ]+
- [(Φ-CH3)2I]+
- [C12H25-Φ-I-Φ]+
- [(C8H17—O-Φ)2I]+
- [(C8H17—O-Φ-I-Φ)]+
- [(Φ)3S]+
- [(Φ)2-S-Φ-O—C8H17]+[(CH3-Φ-I-Φ-CH(CH3)2]+
- [Φ-S-Φ-S-(Φ)2]+
- [(C12H25-Φ)2I]+
- [(CH3-Φ-I-Φ-OC2H5]+
- wherein the composition has a volumetric polymerization and/or crosslinking shrinkage of less than 1.5% v/v. and wherein the photosensitizer is 3,3′-carbonylbis(7-diethylaminocoumarin) or 3,3′-carbonylbis(7-methoxycoumarin).
Dependencies are inferred from the claim text.