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Dental compositions comprising addition-fragmentation agents

A technology of composition and fracture agent, which is applied in the direction of dentistry, dental prosthesis, dental preparations, etc., and can solve problems such as interface damage

Active Publication Date: 2014-04-16
3M INNOVATIVE PROPERTIES CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Such forces can lead to failure of the interface between the tooth and the polymeric material, resulting in physical gaps and subsequent microleakage in the tooth cavity

Method used

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  • Dental compositions comprising addition-fragmentation agents
  • Dental compositions comprising addition-fragmentation agents
  • Dental compositions comprising addition-fragmentation agents

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0365] Preparation of Example 1-AFM-glutarate

[0366]

[0367] In an approximately 25 mL amber bottle equipped with a magnetic stir bar, charge AFM-1 (5.00 g, 10.95 mmol) and glutaric anhydride (2.50 g, 21.91 mmol). The vial was covered with a piece of aluminum foil with three small holes to vent the reaction to air. The reaction was heated to 100°C with stirring. After 25.25 hours, the reaction was cooled to room temperature and sampled. according to 1 HNMR analysis showed a small amount of glutaric acid remaining. The reaction was heated back to 100°C with stirring. After an additional 24 hours, the reaction was cooled to room temperature. 1 H NMR analysis confirmed the AFM-glutarate structure as a mixture of isomers. AFM-glutarate (7.39 g, 10.8 mmol, 99%) was obtained as a very viscous, very pale yellow oil.

example 2

[0368]Preparation of Example 2-AFM-phosphate

[0369]

[0370] In a glass jar equipped with a magnetic stir bar, phosphorus pentoxide (2.06 g, 0.00725 mol) was suspended in dichloromethane. AFM-1 (6.6 g, 0.0144 mol) was added and the mixture was stirred at room temperature for 4 hours. Water (0.25 g, 0.014 mol) was then added and the mixture became clear leaving a small amount of undissolved residue separating at the bottom of the jar. Stirring was continued for 3 hours, and the mixture was then left undisturbed at room temperature overnight. The clear portion of the top mixture was decanted into a round bottom flask, then the solvent was removed in a rotary evaporator to afford a clear pale yellow viscous liquid. The yield of the reaction was 85%. The structure of the product was confirmed by 1H and 31P NMR.

example 3

[0371] Preparation of Example 3-AFM-succinate

[0372]

[0373] A 50 mL round bottom flask equipped with a magnetic stir bar and dry air blanket was charged with AFM-1 (5.95 g, 0.013 mol), succinic anhydride (2.55 g, o.255 mol) DMAP (80 mg) BHT (8 mg). The flask was heated in an oil bath at 95-100° C. for 5 hours with continuous stirring. The heat was turned off and the product was collected in essentially 100% yield as a clear pale yellow liquid. The structure of AFM-succinate was confirmed by 1H and 13C NMR.

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Abstract

A curable dental composition comprising an addition-fragmentation agent and a curable dental resin is disclosed.

Description

[0001] Cross References to Related Applications [0002] This application claims the benefit of US Provisional Patent Application 61 / 526,437, filed August 23, 2011, the disclosure of which is incorporated herein by reference in its entirety. Background technique [0003] Curable polymeric materials are used in a variety of dental applications including restoratives, cements, adhesives, and the like. Often, such materials shrink when cured. This is especially problematic when the material is in a confined environment, such as in dental fillings or restoratives. Dimensional changes upon contraction while in a constrained environment can create strains within the material that are typically translated into stresses on the surrounding environment (eg teeth). Such forces can lead to failure of the interface between the tooth and the polymeric material, resulting in physical gaps and subsequent microleakage in the tooth cavity. Alternatively, such forces may cause fractures with...

Claims

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Application Information

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IPC IPC(8): A61K6/00A61K6/083
CPCA61K6/0023A61K6/083A61K6/0835A61K6/30A61K6/889A61K6/887C08L33/10A61C19/003C08L33/08
Inventor G·D·乔利A·S·阿比尔雅曼B·D·克雷格A·法尔萨菲J·D·奥克斯曼L·R·克雷普斯基W·H·莫泽S·尤特
Owner 3M INNOVATIVE PROPERTIES CO
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