Isosorbide derivative and nest and fissure sealing agent based on isosorbide structure

A pit and fissure sealing and isosorbide technology, which is applied in the field of medical oral biomaterials, can solve the problems of high price, staying, and increasing the cost of patient treatment.

Active Publication Date: 2022-04-29
SHANGHAI NINTH PEOPLES HOSPITAL SHANGHAI JIAO TONG UNIV SCHOOL OF MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, a large amount of diluent (ISDB: TEGDMA = 29.5: 69.5 (wt%)) is added to the material during the preparation process, which is very unfavorable for reducing the polymerization shrinkage of the material (Dent. Mater. 2020, 36, 157); in addition, different Structured isosorbide molecule-based matrix monomers or diluents have been developed and studied, such as isosorbide-glycidyl dimethacrylate (Eur.Polym.J.2017,92,338), dimethacrylate-3, 3-isosorbide dipropyl ester (Eur.Polym.J.2019,112,629), isosorbide-biscarbamate-methacrylate (J.Appl.Polym.Sci.2017, DOI:10.1002 / APP.44591), isosorbide-dimethacrylate (J.Mech.Behav.Biomed.Mater.2019, 100, 103371), etc., but they are still in the theoretical research stage, and there is no bio-based, low Related work reports on polymerized shrinkage pit and fissure sealant molding products
[0006] In addition, currently clinically used pit and fissure sealants mainly come from 3M Company of the United States, Shokaze Co., Ltd. of Japan, and SDI Company of Australia, etc. These imported materials are expensive, which increases the treatment cost of patients

Method used

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  • Isosorbide derivative and nest and fissure sealing agent based on isosorbide structure
  • Isosorbide derivative and nest and fissure sealing agent based on isosorbide structure
  • Isosorbide derivative and nest and fissure sealing agent based on isosorbide structure

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Example 1: Preparation of isosorbide-based matrix isosorbide-bis{succinic acid mono[2-[(2-methyl-acryloyl)oxy]ethyl]ester} ester (HEMA-ISO-HEMA)

[0048]

[0049] Add 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC.HCl, 23.61g, 0.123mol) to the 1000mL three-necked flask with a stirring bar, dichloromethane (DCM, 500mL), triethylamine (Et 3 N, 24.92g, 0.246mol) and triethylaminosuccinic acid mono[2-[(2-methyl-acryloyl)oxy]ethyl] ester 2 (23.63g, 0.102mol), after stirring for 30min, add isosorbide 1 (5 g, 0.034 mol) and 4-dimethylaminopyridine (DMAP, 0.84 g, 0.0068 mol).

[0050] A reflux condenser was connected to the reaction bottle, and the temperature was raised to about 45°C for reflux reaction for 24 hours. Stop the reaction, wash the reaction solution with water and saturated sodium bicarbonate solution, separate the organic phase, and dry it with anhydrous sodium sulfate until the liquid becomes clear. After suction filtration, the filtrate wa...

Embodiment 2

[0053] Example 2: Preparation of isosorbide-based diluent isosorbide-bismethacrylate (IBM)

[0054]

[0055] Isosorbide (5.01g, 0.034mol), Et 3 N (14.56g, 0.144mol) and DMAP (0.42g, 3.4mmol) were added to a 250mL three-necked bottle with a pre-magnetic sub, and 30mL anhydrous CH 2 Cl 2 Stir to dissolve. The reaction flask was placed in an ice-water bath at 0°C, and methacryloyl chloride (11.92 g, 0.114 mol) was slowly added dropwise. After the dropwise addition, the reaction temperature naturally returned to room temperature, and the reaction was carried out overnight.

[0056] Add water to quench the reaction, separate the organic phase, CH 2 Cl 2 Extract the aqueous phase once. Combine the organic phases with anhydrous Na 2 SO 4 After drying, it was spin-dried, and after silica gel column chromatography (eluent: n-hexane / dichloromethane / methanol (v / v / v=100 / 300 / 5)), 5.14g of transparent colorless liquid product IBM was obtained, yield 53.55 %. Product of IBM 1 H...

Embodiment 3

[0059] Example 3: Silanization modification of dental glass powder

[0060] Prepare 50mL of 60% ethanol-water solution, adjust the pH to 3-4 with acetic acid, add 1g of γ-MPS and stir evenly, then add 10g of glass powder, stir at room temperature for 1h, and heat at 70°C for 1h. The solvent was evaporated under reduced pressure at 65-70°C, and the remaining powder mixture was reacted and dried at 120°C. The dried powder was washed with ethanol, centrifuged, and the lower precipitate was vacuum-dried at 40°C. The infrared spectrum of the dental glass powder modified by the silane coupling agent is as follows: Figure 5 shown.

[0061] FT-IR:ν(cm -1 ):2962(=C-H),1726(C=O).

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Abstract

The invention provides an isosorbide derivative and a pit and fissure sealing agent based on an isosorbide structure, and the pit and fissure sealing agent based on the isosorbide structure comprises an isosorbide-based matrix and an isosorbide-based diluent, the isosorbide-based matrix is at least one of isosorbide-bis {succinic acid mono [2-[(2-methyl-acryloyl) oxygen] ethyl] ester} ester or isosorbide-bis [succinic acid mono (2-acryloyl oxygen ethyl ester)] ester; the isosorbide-based diluent is at least one of isosorbide-dimethacrylate and isosorbide-diallyl carbonate, and the isosorbide-based diluent is at least one of isosorbide-dimethacrylate and isosorbide-diallyl carbonate. According to the pit and fissure sealing agent, the low-viscosity large-molecular-weight monomer is selected as the matrix, the adding proportion of the low-molecular-weight diluent is greatly reduced, and therefore the pit and fissure sealing agent has lower double bond density and is beneficial to reducing polymerization shrinkage in material curing and the micro-leakage degree after curing.

Description

technical field [0001] The application belongs to the technical field of medical oral biomaterials, and in particular relates to an isosorbide derivative and a pit and fissure sealant based on the isosorbide structure. Background technique [0002] Pit and fissure sealants, as one of the important ways to prevent pit and fissure caries of deciduous molars, have been clinically used for decades. 3M ESPE Clinpro, which is widely used clinically TM Sealant is a resin-type socket based on bisphenol-A diglycidyl methacrylate (Bis-GMA) as the matrix and triethylene glycol dimethacrylate (Triethylene Glycol Dimethacrylate, TEGDMA) as the diluent Fissure sealant, with good fluidity and rapid photocrosslinking effect, can reach small fissures and gaps, and form a barrier between pits and fissures and the oral environment after curing by light to achieve sealing effect. [0003] However, while exerting a high-efficiency sealing effect, 3M ESPE Clinpro TM Sealant also has the defe...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/04C08F222/20C08F220/34A61K6/20A61K6/62A61K6/69A61K6/71A61K6/74A61K6/75A61K6/76
CPCC07D493/04C08F222/102A61K6/20A61K6/62A61K6/76A61K6/71A61K6/74A61K6/75A61K6/69C08F220/34
Inventor 孙皎崔怡楠杨甦刘昕隋佰延
Owner SHANGHAI NINTH PEOPLES HOSPITAL SHANGHAI JIAO TONG UNIV SCHOOL OF MEDICINE
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