Spirodiol dienoic acid ester and preparation method thereof

A technology of spirodiol dienoate and spirodiol, which is applied in the field of diol ester compounds and their preparation, and in the field of spirodiol ester compounds and their preparation, can solve the problem of low product purity and yield, Problems such as secondary pollution and difficult recovery of solvents

Pending Publication Date: 2020-07-07
SHANGHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the performance of the existing macromolecular crosslinking agents, especially the crosslinking agents polymerized by high-strength vinyl monomers, is not ideal, and the purity and yield of the prepared products are not high, and the solvent used in the preparation process is not easy to recycle. will cause secondary pollution

Method used

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  • Spirodiol dienoic acid ester and preparation method thereof
  • Spirodiol dienoic acid ester and preparation method thereof
  • Spirodiol dienoic acid ester and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] In the present embodiment, a kind of preparation method of spirodiol dienoate comprises the steps:

[0036] a. Pour a certain amount of reactant A spirodiol (SPG) into a 250ml three-necked flask, then add 20mL of mixed solvent, the volume ratio of toluene and tetrahydrofuran in the mixed solvent is 9:1, connect the three-necked flask to the condenser device, heat the three-necked flask to 65-75°C and stir for a certain period of time. After the spirodiol is completely dissolved and the solution becomes clear and transparent, add a small amount of anhydrous copper sulfate and p-hydroxyanisole, and then add the reactant methacrylic acid , finally add catalyst p-toluenesulfonic acid, make spirodiol and enoic acid as reactants, mix with mixed solvent to form reactant system; wherein the quality of anhydrous copper sulfate, p-hydroxyanisole and p-toluenesulfonic acid is 0.0083g respectively , 0.009g and 0.059g, the moles of spirodiol and methacrylic acid are respectively 0.0...

Embodiment 2

[0044] This embodiment is basically the same as Embodiment 1, especially in that:

[0045] In the present embodiment, a kind of preparation method of spirodiol dienoate comprises the steps:

[0046] a. Pour a certain amount of reactant A spiroglycol (SPG) into a 250ml three-necked flask, then add 20mL of mixed solvent, the volume ratio of toluene and tetrahydrofuran in the mixed solvent is 3:1, connect the three-necked flask to the condenser device, heat the three-necked flask to 65-75°C and stir for a certain period of time. After the spirodiol is completely dissolved and the solution becomes clear and transparent, add a small amount of anhydrous copper sulfate and p-hydroxyanisole, and then add the reactant methacrylic acid , finally add catalyst p-toluenesulfonic acid, make spirodiol and enoic acid as reactants, mix with mixed solvent to form reactant system; wherein the quality of anhydrous copper sulfate, p-hydroxyanisole and p-toluenesulfonic acid is 0.0085g respectively...

Embodiment 3

[0052] This embodiment is basically the same as the previous embodiment, and the special features are:

[0053] In the present embodiment, a kind of preparation method of spirodiol dienoate comprises the steps:

[0054] a. Pour a certain amount of reactant A spiroglycol (SPG) into a 250ml three-necked flask, then add 20mL of mixed solvent, the volume ratio of toluene and tetrahydrofuran in the mixed solvent is 3:1, connect the three-necked flask to the condenser device, heat the three-necked flask to 65-75°C and stir for a certain period of time. After the spirodiol is completely dissolved and the solution becomes clear and transparent, add p-hydroxyanisole as a polymerization inhibitor, then add the reactant methacrylic acid, and finally add Catalyst p-toluenesulfonic acid, make spirodiol and alkenoic acid as reactant, mix with mixed solvent to form reactant system; Wherein the quality of p-hydroxyanisole and p-toluenesulfonic acid are respectively 0.059g and 0.0176g, spirodi...

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Abstract

The invention discloses spirodiol dienoic acid ester and a preparation method thereof. A spirodiol dienoic acid ester substance is prepared in a mixed solvent system, reactants adopt spirodiol and olefine acid monomers and includes but is not limited to acrylic acid and methacrylic acid, and the spirodiol dienoic acid ester is characterized in that the structure has a carboxyl group and a double bond. The esterification reaction between the two reactants is carried out in a mixed solvent, two hydroxyl groups at two ends of the reactant spirodiol respectively react with carboxyl groups on the reactant olefine acid to form ester bonds, and the obtained product is the spirodiol diolefine acid ester. The spirodiol is dihydric alcohol with an alicyclic structure; the resin prepared by the spirodiol is superior to fatty diol in the aspects of heat resistance, solvent resistance and the like, and has the advantage that aromatic diol is difficult to reach in the aspect of yellowing resistance,and the macromolecule obtained by reaction has carbon-carbon double bonds at two ends, can be used as a cross-linking agent in polymerization reaction, has a spiro ring in the molecule, and can alsoprovide excellent mechanical properties.

Description

technical field [0001] The invention relates to a diol ester compound and a preparation method thereof, in particular to a spirodiol ester compound and a preparation method thereof, which are applied in the technical field of macromolecular crosslinking agents. Background technique [0002] The full name of spirodiol is β,β,β',β'-tetramethyl-2,5,8,10-tetraoxaspiro[5,5]undecane-3,9-diethanol, which is a A diol with a special structure, because of the aliphatic spiro ring structure in its molecule, it is superior to aliphatic diols in heat resistance and solvent resistance, and has the unmatched advantages of aromatic diols in yellowing resistance , so in polyester, polyurethane and other resin systems and many other polymer synthesis, the overall performance of the material can be improved by partially replacing other diols. [0003] Cross-linking agent is an additive that can transform linear or slightly branched macromolecules into a three-dimensional network structure, th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/10C08F22/20
CPCC07D493/10
Inventor 刘引烽晏伟刘元驰吴昊李志强丁超郜辉宇
Owner SHANGHAI UNIV
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