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Adhesive monomer and method for improving adhesion strength between dental zirconia and resin

A kind of cohesive, monomeric technology, applied in the direction of dentistry, dental preparations, dental prosthesis, etc., can solve the problem of high price of functional monomers, and achieve the effect of improving bonding strength and good biocompatibility

Inactive Publication Date: 2014-02-26
NANJING UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] But at present, due to patent restrictions, the above functional monomers are expensive, so it is necessary to develop new adhesive functional monomers

Method used

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  • Adhesive monomer and method for improving adhesion strength between dental zirconia and resin
  • Adhesive monomer and method for improving adhesion strength between dental zirconia and resin
  • Adhesive monomer and method for improving adhesion strength between dental zirconia and resin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] The synthetic steps of adhesive monomer H are as follows:

[0053]

[0054] Step (a):

[0055] A chloroform solution containing 6.91 g (0.04 mol) of m-chloroperoxybenzoic acid was added to a chloroform solution containing 6.14 g (0.05 mol) of 1,5-cyclooctadiene A, and stirred at room temperature for 18 hours. After the reaction, wash with aqueous sodium bisulfite, then with aqueous sodium bicarbonate, and finally with distilled water until neutral. The solvent was removed from the organic layer to obtain an oily liquid, and the oily liquid product B was obtained by column chromatography.

[0056] Step (b):

[0057] Dissolve 5g (0.04mol) of product B in a mixture of 100mL 1,4-dioxane and 75mL of water, add 11.4g (0.05mol) of periodic acid, and stir at room temperature for two hours. After the reaction was finished, it was washed with water, and then extracted with dichloromethane, and the solvent was removed from the organic layer to obtain an oily product C.

[0...

Embodiment 2

[0069] The synthesis steps of adhesive monomer H1 are as follows:

[0070]

[0071] Step (a) to step (e): Same as Example 1.

[0072] Step (f):

[0073] The product F (2.0g, 0.007mol) and S 8 O (7.6 g, 0.028 mol) dissolved in 10 mL of CS 2 In the dark, stir and reflux for two hours. After the reaction, the solvent was removed by rotary evaporation, and the yellow oily product G1 was obtained by separation by column chromatography.

[0074] Step (g):

[0075] Dissolve the product G1 (0.005mol) in 10 mL of ether, add LiAlH to the ether mixture in batches under ice-cooling 4 (0.020mol), stirred for two hours, and then sequentially added ammonium chloride aqueous solution, ether extraction. The organic phase was evaporated to remove the solvent, and the yellow oily product H1 was obtained by separation by column chromatography.

Embodiment 3

[0077] The synthetic steps of binding monomer H2 are as follows:

[0078]

[0079] Step (a) to step (e): Same as Example 1.

[0080] Step (f):

[0081] Under the protection of nitrogen, add activated zinc powder (0.52g, 0.008mol), product F (2.0g, 0.007mol) and 20mL of anhydrous ether to the three-necked flask with reflux stirring successively, and then add dropwise to the reaction system 10mL dissolved in Cl 3 CCOCl (1.5g, 0.008mol) and POCl 3 (1.22g, 0.008mol) in anhydrous ether solution, refluxed and stirred for two hours, and filtered to remove the solid to obtain the ether solution of product G2.

[0082] Step (g):

[0083] Synthesis of H2: Add NaHCO to the ether solution of product G2 3 aqueous solution, stirred, and extracted with ether. The organic phase was evaporated to remove the solvent, and the yellow oily product H2 was obtained by separation by column chromatography.

[0084] Taking the adhesive monomer H as an example, the structure and performance ar...

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Abstract

The invention discloses an adhesive monomer and a method for improving adhesion strength between dental zirconia and resin. The adhesive monomer is prepared from 1, 5-cyclooctadiene by performing epoxidation, ring-opening reaction, redox, exterification and the like, the main chain of the adhesive monomer is a n-octane carbon chain with one end of acrylic ester and the other end of phosphate ester, the forth position and the fifth position on the carbon chain are respectively connected with a R group which represents hydroxyl, sulfydryl or carboxyl, and the adhesive monomer has the structural formula shown in the description. The adhesive monomer helps to improve the adhesion strength between dental zirconia ceramic and resin, has the same improving effect with common 10-MDP-containing zirconia primer coating products in current market, has relatively good biological compatibility, is qualified in cytotoxicity tests, and has important application value during tooth repairing processing.

Description

[0001] technical field [0002] The invention relates to the field of organic synthesis and the bonding performance field of high-strength non-silicate ceramics, in particular to a bonding monomer and a method for improving the bonding strength of dental zirconia ceramics and resin. Background technique [0003] Zirconia has the reputation of "ceramic steel", which stands out among many dental all-ceramic materials and greatly broadens the indications of all-ceramic restorations. Like other types of all-ceramic materials, the bonding strength of composite resin alone is not enough, so it must be used in combination with adhesives. Resin cement is the preferred cement for zirconia all-ceramic restorations. Compared with other types of all-ceramic materials, although zirconia ceramics have unique advantages in mechanical properties, due to its high chemical inertness, measures such as HF acid etching and silanization used in other types of all-ceramic materials have great impa...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/09A61K6/083
Inventor 鲁艺谢海峰周鑫陈志浩章非敏孙为银
Owner NANJING UNIV
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