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Low polymerization volume shrinkage (meth)acrylate monomer without bisphenol A structure, preparation method and application thereof

A technology of volume shrinkage and acrylate, applied in dental preparations, dental prostheses, pharmaceutical formulations, etc., can solve problems such as low polymerization volume shrinkage, achieve high double bond conversion rate, small polymerization volume shrinkage, and mechanical properties Good results

Active Publication Date: 2016-10-05
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The purpose of the present invention is to provide a series of low-temperature and non-bisphenol-A structure-containing (meth)acrylate monomers that have large shrinkage in polymerization volume and potentially toxic bisphenol-A structure of existing dental restoration materials. Polymerized volume shrinkage (meth)acrylate macromonomer and its preparation method and application

Method used

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  • Low polymerization volume shrinkage (meth)acrylate monomer without bisphenol A structure, preparation method and application thereof
  • Low polymerization volume shrinkage (meth)acrylate monomer without bisphenol A structure, preparation method and application thereof
  • Low polymerization volume shrinkage (meth)acrylate monomer without bisphenol A structure, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Embodiment 1 ACD monomer

[0037] The preparation method of the present embodiment ACD monomer comprises the steps:

[0038] Step 1: Add 9.276g1,3-bis[2-(3,4-epoxycyclohex-1-yl)ethyl]tetramethyldisiloxane and 4.275g Methacrylic acid, add 100ml of dichloromethane, 0.050g N,N-dimethylbenzylamine, 0.06g hydroquinone, reflux and stir at 90°C for 24 hours, cool to room temperature, and then carry out acid solution on the reaction product Washing lye washing purification treatment.

[0039] The product was characterized by infrared and NMR:

[0040] 1 H-NMR (400MHz, CCl 3 D): δ6.14(s, 2H), δ5.60(s, 2H), δ3.95-3.15(m, 4H), δ2.01(s, 6H), δ1.90-1.45(m, 14H) ), δ1.45-1.20 (m, 8H), 0.50 (t, 12H).

[0041] FT-IR: ν(cm -1 ) 3648-3134, 2920, 2854, 1720, 1637, 1253, 1173, 795, 650.

Embodiment 2

[0042] Example 2 Polymerization volume shrinkage of dental resin containing ACD monomer

[0043] In this example, the ACD monomer was mixed with the diluent TEGDMA commonly used in dental restoration materials, and the resin system Bis-GMA / TEGDMA commonly used in dental restoration materials was used as a control group to study the polymerization volume shrinkage of the prepared resin after curing.

[0044] The resin formula and the results of polymerization volume shrinkage are shown in Table 1 to Table 2.

[0045] Table 1 Resin composition containing ACD monomer

[0046]

[0047] Table 2 Polymerization volume shrinkage of resin system containing ACD monomer and reference resin system

[0048]

[0049] It can be seen that, compared with Bis-GMA, the resin system with ACD monomer content of 51.2% has the lowest polymerization shrinkage.

[0050] The polymerization shrinkage is mainly caused by the change of the distance between molecules before and after the polymeriza...

Embodiment 3

[0051] Embodiment 3 Contains the mechanical properties of ACD monomer dental resin

[0052] In this example, on the basis of Example 3, the cured mechanical properties of the resin system prepared in Example 3 were studied.

[0053] The mechanical performance test results are shown in Table 3.

[0054] Table 3 Mechanical properties of the resin system containing ACD monomer and the reference resin system

[0055]

[0056] It can be seen that, compared with Bis-GMA, the mechanical properties of the resin system containing ACD monomer have decreased, but it still meets the application standards of dental restoration resins.

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Abstract

The invention discloses a (meth)acrylic acid ester monomer without bisphenol A structure and low polymerization volume shrinkage, its preparation method and application. The (meth)acrylate macromonomer without bisphenol A structure prepared by the invention can be used as an organic monomer component of dental restorative materials. The macromonomer has the characteristics of large molecular weight, large molecular volume, and no bisphenol A structure. Therefore, the macromonomer has a small polymerization volume shrinkage during polymerization, and can reduce the presence of dental materials with a bisphenol A structure on the human body. potential hazards.

Description

technical field [0001] The invention relates to a series of monomers that can be used as photoinitiated polymerization systems, in particular to a series of (meth)acrylic ester monomers without bisphenol A structure and low polymerization volume shrinkage, as well as its preparation method and application. Background technique [0002] At the end of the 19th century, American dentist Miller first proposed the bacterial mechanism of dental caries in his book Microorganisms in the Human Mouth, that is, bacteria ferment sugar to produce acid, which leads to demineralization of tooth enamel and caries. After dental caries occurs, the tooth itself cannot repair itself, and the diseased part can only be removed through dental surgery, and then filled with certain restoration materials. Due to the wide application range, convenient use, low price, and large modification space of composite resin-based restoration materials; at the same time, because composite resin can be directly b...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F7/08A61K6/083
Inventor 何经纬梁晓旭刘芳
Owner SOUTH CHINA UNIV OF TECH
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