Unlock instant, AI-driven research and patent intelligence for your innovation.

Synthetic method of oral adhesive methacryloyl decyl dihydrogen phosphate

A technology of methacryloyl decyl dihydrogen phosphate and methacryloyl decyl dihydrogen phosphate, which is applied in the field of synthesis using trimethyl phosphite as a phosphorylation reagent, can solve the problem of unseen yield Reporting and other issues to achieve the effect of avoiding complicated operations, mild conditions, and environmental friendliness

Inactive Publication Date: 2016-05-04
CHANGCHUN UNIV OF TECH
View PDF3 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In 2008, Liu Lian et al. [2] The synthesis method of methacryloyl decyl dihydrogen phosphate was studied in detail, and the results were published in the journal "Biomedical Engineering": using α-methacrylic acid, 1,10-decanediol as raw materials, p-toluene Sulfonic acid is used as a catalyst, and the precursor 10-hydroxydecyl methacrylate is synthesized; phosphorus oxychloride is used as a phosphorylation reagent, and cyclohexane and tetrahydrofuran are used as solvents to phosphorylate 10-hydroxydecyl methacrylate, but each step Yields are not reported

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Synthetic method of oral adhesive methacryloyl decyl dihydrogen phosphate
  • Synthetic method of oral adhesive methacryloyl decyl dihydrogen phosphate
  • Synthetic method of oral adhesive methacryloyl decyl dihydrogen phosphate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] (1) Preparation of intermediate 10-hydroxydecyl methacrylate: In a single-necked flask, add raw materials methacrylic acid and 1,10-decanediol, the molar ratio of the two is 1.0:1.1; catalyst p-toluenesulfonic acid Accounting for 1.4% of the total mass of raw materials, the polymerization inhibitor hydroquinone accounts for 0.9% of the total mass of raw materials, the reaction temperature is 80 ° C, and the reaction time is 6 hours. Solvent-free direct vacuum distillation is carried out through a vacuum distillation device. , by methacrylic acid with CH 2 Cl 2 The molar ratio is 1:50 by adding CH 2 Cl 2 Dilute the resulting product, and then use a mass concentration of 5% NaHCO 3 Wash with aqueous solution until neutral, then wash with distilled water 3 times, anhydrous MgSO 4 Drying and purification through a silica gel column yielded 10-hydroxydecyl methacrylate with a yield of 51.3%;

[0023] (2) Preparation of methacryloyl decyl dimethoxy phosphate: by 10-hydro...

Embodiment 2

[0027] (1) Preparation of the intermediate 10-hydroxydecyl methacrylate: the catalyst p-toluenesulfonic acid accounts for 2.1% of the total mass of raw materials, the polymerization inhibitor hydroquinone accounts for 0.9% of the total mass of raw materials, and the reaction temperature is 80 ° C. All the other are with embodiment 1, yield 54.1%;

[0028] (2) Preparation of methacryloyl decyl dimethoxy phosphate: same as Example 1;

[0029] (3) Preparation of methacryloyl decyl dihydrogen phosphate: at room temperature, according to the molar ratio of methacryloyl decyl dimethoxy phosphate to trimethylbromosilane (TMSBr) is 1:3.0, the Trimethylbromosilane (TMSBr) was added dropwise into the three-necked flask at a rate of 0.1mL / min, and the molar ratio of methacryloyldecyldimethoxyphosphate to allyltrimethylbromosilane was 1:1, then add allyl trimethylbromosilane dropwise into the three-necked flask at a rate of 0.1mL / min, after the dropwise addition, react at room temperatur...

Embodiment 3

[0031] (1) Preparation of intermediate 10-hydroxydecyl methacrylate: catalyst p-toluenesulfonic acid, polymerization inhibitor hydroquinone; catalyst p-toluenesulfonic acid accounts for 5.0% of the total mass of raw materials, polymerization inhibitor hydroquinone Account for 0.9% of the raw material gross mass, all the other are with embodiment 1, yield 59.3%;

[0032] (2) Preparation of methacryloyl decyl dimethoxy phosphate: same as Example 1;

[0033] (3) Preparation of methacryloyl decyl dihydrogen phosphate: according to the molar ratio of methacryloyl decyl dimethoxy phosphate to trimethylbromosilane (TMSBr) is 1:3.3, trimethyl Bromosilane (TMSBr) was added dropwise into a three-necked flask, and the molar ratio of methacryloyldecyldimethoxyphosphate to allyltrimethylbromosilane was 1:1.5, and then allyltrimethyl Bromosilane was added dropwise into the three-necked flask, and after the dropwise addition was completed, the reaction was carried out at room temperature fo...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention provides a synthetic method of 10-methacryloyloxydecyl dihydrogen phosphate. The method comprises the steps of preparing an intermediate 10-hydroxyldecanoyl methacrylate, preparing 10-methacryloyloxydecyl dimethoxy phosphate, and preparing the above target product. In the monoester synthesis process, a solvent-free reduced pressure distillation technology is adopted for the first time, so the environmental pollution problem caused by the use of an organic solvent is avoided, the cost is reduced, and unreacted raw materials can be recycled; in the phosphorylation process, trimethyl phosphite is adopted as an acylation reagent for the first time, and the reaction is carried out at room temperature under mild conditions, so the energy consumption is reduced, the environmental pollution problem caused by phosphorous oxychloride and other acylating agents is avoided, and the unreacted raw material 10-hydroxyldecanoyl methacrylate can be recycled; and a freeze-drying technology adopted in hydrolysis post-treatment avoids complicated operation of column chromatography and the mass use of an organic solvent, realizes low cost, environmental protection, mild reaction conditions, high product yield reaching 87.0% and high product purity, and is suitable for industrial production.

Description

technical field [0001] The invention relates to a synthesis method of oral adhesive methacryloyl decyl dihydrogen phosphate (MDP), especially a synthesis method using trimethyl phosphite as a phosphorylation reagent. Background technique [0002] Methacryloyl decyl dihydrogen phosphate (10-methacryloyloxydecyldihydrogenphosphate, MDP) is currently widely used in self-etching oral adhesive adhesive monomer, has good adhesion to metal, can be combined with nickel, chromium , cobalt and other metal oxide layers to produce chemical bonds, the phosphate monoester group in the molecule can form a stable complex with calcium ions in teeth, and can also form hydrogen bonds with collagen, that is, with enamel, dentin, each All kinds of dental alloys and dental ceramics have good bonding properties. [0003] Most of the research on methacryloyl decyl dihydrogen phosphate and its homologues at home and abroad focuses on its adhesive properties, such as in China, Liu Xiaoqing, Chen Zhi...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/09
Inventor 石富强和翠红吴广峰张龙
Owner CHANGCHUN UNIV OF TECH