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Tri-functionality quaternary ammonium salt epoxy (methyl) acrylate monomer, and preparation method thereof

A trifunctional, acrylate technology, applied in the preparation of aminohydroxy compounds, chemical instruments and methods, preparation of organic compounds, etc. Good effect, increased potential for the treatment of caries, good plasticity effect

Inactive Publication Date: 2015-10-07
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] However, the molecular structure of MDPB and DMAE-CB only contains a methacrylate structure, and the crosslinking rate is limited when polymerized with the resin matrix monomer. Excessively high content of MDPB and DMAE-CB in the material will cause the performance of the material to be affected. impact, uncrosslinked antimicrobial monomers may also bleed out of resin-based materials, which is not conducive to oral health, and these two monomers are difficult to coexist with hydrophobic bismethacrylate monomers commonly used in dental restoration materials such as TEGDMA. mixing and other issues

Method used

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  • Tri-functionality quaternary ammonium salt epoxy (methyl) acrylate monomer, and preparation method thereof
  • Tri-functionality quaternary ammonium salt epoxy (methyl) acrylate monomer, and preparation method thereof
  • Tri-functionality quaternary ammonium salt epoxy (methyl) acrylate monomer, and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Step 1: Preparation of N,N,N,N,N-pentamethyldiethylenetriamine epoxy quaternary ammonium salt

[0028] Add 0.3mol epichlorohydrin and 1,4-dioxane to a two-necked flask equipped with a magneton for dilution, and add 0.1mol N,N,N,N,N-pentamethyl dropwise while stirring in an ice-water bath A mixture of diethylenetriamine and 1,4-dioxane. Finish dripping within 1h. Continue to react for 5h after dropping. Immediately after the reaction was completed, it was suction filtered, washed with a solvent, and vacuum-dried to obtain white crystals of epoxy quaternary ammonium salt.

[0029] Step 2: Trifunctional quaternary ammonium salt epoxy (meth)acrylate monomer

[0030] Add 0.1mol epoxy quaternary ammonium salt, cyclohexane and 2wt% hydroquinone into a three-necked flask equipped with magnetons. The temperature was raised to 80° C., and 0.3 mol of methacrylic acid was continuously added dropwise through a constant pressure dropping funnel under stirring. After the dropwise...

Embodiment 2

[0032] Step 1: Preparation of N,N,N,N,N-pentaethyldiethylenetriamine epoxy quaternary ammonium salt

[0033] Add 0.6mol epichlorohydrin and anhydrous ether to a two-necked flask equipped with magnets for dilution, and add 0.1mol N,N,N,N,N-pentaethyldiethylene dropwise while stirring in an ice-water bath A mixture of triamine and anhydrous ether. Finished dripping within 1.5h. Continue to react for 4h after dropping. Immediately after the reaction was completed, it was suction filtered, washed with a solvent, and vacuum-dried to obtain white crystals of epoxy quaternary ammonium salt.

[0034] Step 2: Preparation of trifunctional quaternary ammonium salt epoxy (meth)acrylate monomer

[0035] Add 0.1mol of epoxy quaternary ammonium salt, toluene and 2wt% p-hydroxyanisole in a three-necked flask equipped with a magneton. The temperature was raised to 85° C., and 0.3 mol of methacrylic acid was continuously added dropwise through a constant pressure dropping funnel under stirr...

Embodiment 3

[0037] Step 1: Preparation of N,N,N,N,N-pentapropyldiethylenetriamine epoxy quaternary ammonium salt

[0038] Add 0.6mol epichlorohydrin and tetrahydrofuran to a two-necked flask equipped with magnets for dilution, and add 0.1mol N,N,N,N,N-pentapropyldiethylenetriamine dropwise while stirring in an ice-water bath and tetrahydrofuran mixture. Finish dripping within 2h. Continue to react for 3h after dropping. Immediately after the reaction was completed, it was suction filtered, washed with a solvent, and vacuum-dried to obtain white crystals of epoxy quaternary ammonium salt.

[0039] Step 2: Preparation of trifunctional quaternary ammonium salt epoxy (meth)acrylate monomer

[0040]Add 0.1mol of epoxy quaternary ammonium salt, cyclohexanone and 2wt% methyl hydroquinone into a three-necked flask equipped with magnetons. The temperature was raised to 90° C., and 0.3 mol of methacrylic acid was continuously added dropwise through a constant pressure dropping funnel under stir...

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Abstract

The invention relates to a monomer can be applied to a light initiated polymerization system, and more specifically relates to a tri-functionality quaternary ammonium salt epoxy (methyl) acrylate monomer, and a preparation method thereof. The structure of the tri-functionality quaternary ammonium salt epoxy (methyl) acrylate monomer is represented by a formula in the invention, wherein R1-R7 are used for representing alkyl, cycloalkyl, vinyl, or benzyl, and R8 is used for representing methyl or hydrogen. The prepared novel epoxy (methyl) acrylate monomer is a light-cured resin monomer, can be prepared into a mixed slurry with appropriate viscosity; and the mixed slurry can be applied to defect repairing of teeth after solidification under specific light irradiation. The preparation method is simple; the color of an obtained tooth material is beautiful, strength is high, bonding retention effect is excellent, plasticity is excellent, and grinding and polishing can be carried out after solidification. According to the preparation method, antibacterial groups are introduced into the tri-functionality quaternary ammonium salt epoxy (methyl) acrylate monomer, so that potential curing effect on carious tooth is increased.

Description

technical field [0001] The invention relates to a monomer that can be used as a photoinitiated polymerization system, in particular to a class of trifunctional quaternary ammonium salt epoxy (meth)acrylate monomer and a preparation method thereof. Background technique [0002] Photocurable composite resin was introduced into the dental field in the 1960s. It is mainly composed of resin matrix, inorganic filler and photoinitiation system, and the preparation process is simple. The material has the advantages of beautiful color, high strength, good bonding and retention effect, good plasticity, and can be polished and polished after curing; by preparing a mixed slurry with an appropriate viscosity and curing it after specific light irradiation, it can be used Restoration of tooth defects. Therefore, it has received extensive attention in the field of dental restoration. In recent years, people have conducted in-depth research on improving the wear resistance and polymerizati...

Claims

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Application Information

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IPC IPC(8): C07C213/00C07C219/08A61K6/083A61K31/785A61P1/02
Inventor 王克敏张楠陈佳杰殷杰伟任子叶
Owner CHANGZHOU UNIV
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