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A kind of unsaturated polyester prepolymer containing ketone group and its preparation method and application

A prepolymer and unsaturated technology, which is applied in the field of organic compound preparation, can solve the problem of difficult separation of protective reagents and achieve good application prospects, mild synthesis conditions, and wide selection of raw materials.

Active Publication Date: 2019-03-22
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The technical problem to be solved in the present invention is: in order to solve the problem that the protection reagent is not easy to separate after deprotection in the amino protection process, the present invention provides a ketone-containing unsaturated polyester prepolymer

Method used

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  • A kind of unsaturated polyester prepolymer containing ketone group and its preparation method and application
  • A kind of unsaturated polyester prepolymer containing ketone group and its preparation method and application
  • A kind of unsaturated polyester prepolymer containing ketone group and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] (1) Synthetic diacetoacetate, as shown in the following formula:

[0033]

[0034]Add butanediol (9.0g, 0.1mol), ethyl acetoacetate (65g, 0.5mol), p-toluenesulfonic acid (0.28 g) and 100 mL of benzene. Azeotrope at a temperature of 90°C for 2 hours to remove water, then distill off the solvent, remove the ethanol generated by the reaction at high temperature, and raise the temperature to 130°C for 6 hours under normal pressure. After the reaction, 200 mL of ethyl acetate was added, washed 3 times with 5% aqueous sodium bicarbonate solution, 100 mL each time, and then washed 3 times with deionized water, and dried overnight by adding anhydrous magnesium sulfate to the organic phase. After anhydrous magnesium sulfate was filtered off, the solvent was distilled off under reduced pressure, and an oil pump was distilled under reduced pressure to obtain 23 g of colorless oily diacetoacetate with a yield of 65%. attached figure 1 Butanediol diacetoacetate 1 (bisacetoace...

Embodiment 2

[0039] (1) Synthetic diacetoacetate, as shown in the following formula:

[0040]

[0041] The number-average relative molecular mass of polyethylene glycol PEG400 is 400, and the average value of x is about 9.

[0042] In a 250mL flask equipped with a stirring rotor, an oil-water separator, a spherical condenser, and a drier, add PEG400 (10g, 0.025mol), ethyl acetoacetate (16g, 0.125mol), 732 type strongly acidic cation exchange resin (3.4 g) and 100 mL of benzene. Azeotrope at a temperature of 90°C for 2 hours to remove water, then distill off the solvent, remove the ethanol generated by the reaction at high temperature, and raise the temperature to 130°C for 6 hours under normal pressure. After the reaction, filter, and wash the ion exchange resin with a small amount of ethyl acetate, and incorporate into the filtrate. The filtrate was distilled under reduced pressure to remove the solvent and excess ethyl acetoacetate to obtain 14.8 g of colorless or light yellow oily ...

Embodiment 3

[0047] (1) Synthetic diacetoacetate, as shown in the following formula:

[0048]

[0049] The number-average relative molecular mass of polyethylene glycol PEG400 is 400, and the average value of x is about 9.

[0050] In a 250mL flask equipped with a stirring rotor, an oil-water separator, a spherical condenser, and a drier, add PEG400 (10g, 0.025mol), ethyl acetoacetate (16g, 0.125mol), 732 type strongly acidic cation exchange resin (3.4 g) and 100 mL of benzene. Azeotrope at a temperature of 90°C for 2 hours to remove water, then distill off the solvent, remove the ethanol generated by the reaction at high temperature, and raise the temperature to 130°C for 6 hours under normal pressure. After the reaction, filter, and wash the ion exchange resin with a small amount of ethyl acetate, and incorporate into the filtrate. The filtrate was distilled under reduced pressure to remove the solvent and excess ethyl acetoacetate to obtain 14.6 g of colorless or light yellow oily ...

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Abstract

The invention relates to the field of organic compound preparation, in particular to an unsaturated polyester prepolymer containing a ketone group, and a preparation method and use of the unsaturated polyester prepolymer. The preparation method comprises the steps of enabling dihydric alcohol and ethyl acetoacetate to be subjected to a transesterification reaction, so as to obtain diacetyl acetate; enabling the diacetyl acetate and binary aromatic aldehyde, which are taken as monomers, to be subjected to a Knoevengel reaction under the catalysis of secondary amine / acetic acid, so as to obtain the unsaturated polyester prepolymer containing the ketone group. The prepolymer is subjected to a curing reaction, so as to obtain thermosetting unsaturated polyester resin containing the ketone group. When the thermosetting unsaturated polyester resin is used as an amino protection reagent, resin can be directly filtered out from a reaction solution after deprotection, so that the aftertreatment process is simple and convenient. The unsaturated polyester prepolymer containing the ketone group has the advantages of wide raw material selection range, low price, simple synthesis route and mild synthesis conditions, thus having good application prospect.

Description

technical field [0001] The invention relates to the field of preparation of organic compounds, in particular to a ketone group-containing unsaturated polyester prepolymer and its preparation method and application. Background technique [0002] Unsaturated polyester in the general sense refers to an oligomer formed by polycondensation of unsaturated dibasic acid or anhydride and diol, saturated dibasic acid or anhydride and diol, which can be further copolymerized with vinyl monomers. together to form a thermosetting resin. A typical example is maleic anhydride, phthalic anhydride and 1,2-propanediol as the main raw materials to synthesize unsaturated polyester, with styrene as the crosslinking monomer. In addition, epoxy resin end groups can be converted into methacrylate groups to obtain vinyl ester resins, which can also be regarded as a special unsaturated polyester resin. Such resins are currently widely used in the preparation of resin-based composites, but rarely us...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G16/02C07C67/343C07C69/738
CPCC07C67/343C07C69/738C08G16/0225
Inventor 孔立智
Owner CHANGZHOU UNIV
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