Acrylic acid or methylpropenoic acid rosin derivative ester synthesis method

A technology of methacrylic acid rosin and rosin derivatives, which is applied in the field of synthesis of rosin derivatives to achieve the effect of maintaining stability, not easy to add reaction, and high activity

Inactive Publication Date: 2009-07-29
INST OF CHEM IND OF FOREST PROD CHINESE ACAD OF FORESTRY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For the esterification of rosin or rosin derivatives containing hydroxyl functional groups with methacrylic acid or acrylate, due to the polymerization reaction of methacrylic acid or acrylic acid at high temperature, the conventional high-temperature synthesis method is not suitable

Method used

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  • Acrylic acid or methylpropenoic acid rosin derivative ester synthesis method
  • Acrylic acid or methylpropenoic acid rosin derivative ester synthesis method
  • Acrylic acid or methylpropenoic acid rosin derivative ester synthesis method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] The synthesis of acrylic acid or rosin derivative ester of methacrylic acid comprises the following steps,

[0051] One of the rosin derivatives containing hydroxyl functional groups, the hydroxyl value is 80-150mgKOH / g, the acid-binding agent and the polymerization inhibitor are dissolved in an aprotic solvent, and the aprotic solvent used is benzene, dichloromethane, One of toluene and tetrahydrofuran, and the water content of the solvent is less than 0.02%, add methacryloyl chloride or acryloyl chloride, heat to make the reaction temperature 0-85°C, for example, the temperature can be selected as: 5°C, 10°C, 15°C ℃, 20℃, 25℃, 30℃, 35℃, 40℃, 45℃, 50℃, 52℃, 55℃, 60℃, 65℃, 70℃, 75℃, 80℃, react for 0.5-10 hours, The time can be selected as: 0.5 hours, 1 hour, 1.5 hours, 2 hours, 2.5 hours, 3 hours, 3.5 hours, 4 hours, 4.5 hours, 4.8 hours, so that the hydroxyl groups in the rosin derivatives are esterified, which can be based on infrared spectroscopy In the process, the...

Embodiment 2

[0054] Synthesis of Hydrogenated Rosin Acrylate:

[0055] Hydrogenated abietyl alcohol (purchased from Eastman Chemical Ltd): Its main components are dehydroabietyl alcohol, dihydroabietyl alcohol and tetrahydroabietyl alcohol, and some unreacted esters.

[0056]

[0057] Dehydroabietyl Alcohol Dihydroabietyl Alcohol Tetrahydroabietyl Alcohol

[0058] The synthetic method of hydrogenated rosin acrylate:

[0059] Dissolve 10g of hydrogenated abietyl alcohol (hydroxyl value, 158mgKOH / g), 3.12g (0.03mol) of acid-binding agent triethylamine and 0.0027g of polymerization inhibitor p-hydroxyanisole in 20g of aprotic solvent tetrahydrofuran, and add acryloyl chloride 2.79g (0.03mol), the reaction is carried out in a four-necked flask equipped with a stirrer, a reflux tube, and a thermometer, heated so that the reaction temperature is at 40°C, and the stirring speed is 150rpm, reacted for 5 hours, filtered out the precipitate, and the resulting filtrate was passed through The sol...

Embodiment 3

[0066] Synthesis of Hydrogenated Rosin Methacrylate

[0067] The synthesis of hydrogenated rosin methacrylate comprises the following steps:

[0068] Hydrogenated abietyl alcohol 10g (hydroxyl value, 158mgKOH / g), acid-binding agent 4-N, N-dimethylaminopyridine 3.67g (0.03mol) and polymerization inhibitor hydroquinone 0.0027g were dissolved in 20g aprotic Add 3.14g (0.03mol) of methacrylic acid chloride to the solvent dichloromethane, heat to make the reaction temperature at 40°C, react for 5 hours, filter off the precipitate, and remove the solvent from the obtained filtrate by vacuum extraction to obtain methacrylic acid hydrogenated rosin Esters (hydroxyl value, 18 mgKOH / g).

[0069]

[0070] Dehydroabietyl Methacrylate Dihydroabietyl Methacrylate Tetrahydroabietyl Methacrylate

[0071] Infrared, gas and mass analysis of products such as Figure 8-12 .

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Abstract

The invention discloses a method for synthesizing acrylic acid or methacrylic acid vinsol ester, comprising the following steps: one of vinsols containing hydroxide radical functional groups, acid-binding agent and addition type polymerization inhibitor are dissolved in non-proton transfer solvent, methacrylic chloride or acryloyl chloride is added into the mixed solution, the reaction temperature is 0-85 DEG C, and the reaction time is 0.5-10h; then, the precipitate is filtered, and vacuum extraction is carried out on the obtained filter liquor to remove solvent, so that acrylic acid or methacrylic acid vinsol ester can be obtained; the mass of the non-proton transfer solvent is 100-500% of that of the vinsol; the molal weight of the methacrylic chloride or the acryloyl chloride is 100-500% of that of hydroxide radical of the vinsol containing hydroxide radical functional groups; the dosage of the acid-binding agent is 100-500% of the molal weight of the hydroxide radical of the vinsol containing hydroxide radical functional groups. The synthesized acrylic acid or methacrylic acid vinsol ester can be used for having free radical polymerization reaction, can be applied to the fields such as paint, adhesive, printing ink, paper making, etc. The method has high technical efficiency and good stability of the product.

Description

technical field [0001] The invention relates to the synthesis of a class of rosin derivatives capable of radical polymerization, and mainly relates to a synthesis method of a class of acrylic acid or methacrylic acid rosin derivative esters. Background technique [0002] Rosin is an important renewable resource with a wide range of uses. It involves many sectors of the national economy, such as papermaking, soap, ink, paint, synthetic rubber, adhesives, electronics, food, medicine, machinery, pesticides, spices, etc. Rosin is a mixture of various resin acids and fatty acids. Resin acid is the main component of rosin, and it is also a general term for a class of compounds. It is basically a tricyclic phenanthrene skeleton of a monobasic acid containing two double bonds in structure, and it can basically be used in C 20 h 30 o 2 Indicates that its structure has the following types: [0003] [0004] Abietic acid L-pimaric acid Palusic acid [0005] [0006] Isolev...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09F1/04
Inventor 储富祥王基夫林明涛王春鹏金立维陈日清刘美虹
Owner INST OF CHEM IND OF FOREST PROD CHINESE ACAD OF FORESTRY
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