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Water-soluble polyester monomer as well as preparation method and application thereof

A water-soluble polyester and monomer technology, applied in the field of water-soluble polyester, can solve the problems of WPET environmental protection and non-toxic and side effects reduction, poor water resistance of coating film, storage stability, poor water solubility, etc., and achieve good adaptability , Improve water resistance, simple preparation process

Active Publication Date: 2022-05-24
SHENYANG POLYTECHNIC UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The former requires amine neutralization during the preparation process, which reduces the environmental protection and non-toxic side effects of WPET
At the same time, this type of polyester has problems such as storage stability and poor water solubility.
The latter introduces hydrophilic sulfonic acid groups into the polyester molecular chain, and the prepared WPET can be quickly dissolved in water without vigorous stirring and adding other additives, which is more environmentally friendly than the former. Water solubility and storage stability, so the development prospect of sulfonate type WPET is broad, but its polyester molecular chain contains more hydrophilic groups, and the water resistance of the coating film is poor

Method used

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  • Water-soluble polyester monomer as well as preparation method and application thereof
  • Water-soluble polyester monomer as well as preparation method and application thereof
  • Water-soluble polyester monomer as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Epoxycyclohexane, oxalic acid and ethylene glycol titanium are mixed in the refining kettle in a molar ratio of 1:0.2:0.01 and stirred, N 2 Protected, reacted at 30 °C for 2 h, washed, concentrated and purified the epoxycyclohexane functional monomer (B1), the conversion rate was 99.4%, and the NMR H spectrum was as follows figure 1 shown. 1 H NMR (500 MHz, Chloroform ) δ 4.24 (s, 13H), 3.65 (s, 16H), 3.51–3.35 (m, 2H), 3.51–3.06 (m, 49H), 1.94 (d, J = 5.0 Hz, 34H), 1.80 (s, 12H), 1.75 (s, 14H), 1.68 (s, 22H), 1.61 (d, J = 10.0 Hz, 31H), 1.31 (s, 8H), 1.30 – 1.16 (m, 131H), 1.10 (s, 11H).

[0031] The structural formula of epoxy cyclohexane functional monomer (B1) is:

[0032] .

Embodiment 2

[0034] Epoxycyclohexane, malonic acid and ethylene glycol antimony were mixed in the refining kettle in a molar ratio of 1:0.5:0.1 and stirred, N 2 Protected, reacted at 50 °C for 4 h, washed, concentrated and purified epoxycyclohexane functional monomer (B2), the conversion rate was 99.6%, and the NMR H spectrum was as follows figure 2 shown. 1 H NMR (500 MHz, Chloroform ) δ 4.42 (s, 7H), 4.36 (s, 6H), 3.44 (s, 13H), 3.35 (d, J = 6.7 Hz, 9H), 2.72 (s, 5H), 2.29 (s, 7H), 1.94 (s, 9H), 1.81 (s, 6H), 1.76 (d, J = 5.0 Hz, 13H), 1.68 (s, 5H), 1.62 (d, J = 10.0 Hz, 12H), 1.36 (s, 8H), 1.32 (s, 4H), 1.25 (d, J = 15.0 Hz, 17H), 1.22 – 1.15 (m, 27H), 1.10 (s, 8H).

[0035] The structural formula of epoxy cyclohexane functional monomer (B2) is:

[0036] .

Embodiment 3

[0038] Epoxycyclohexane, succinic acid and imidazole column aromatic hydrocarbon ionic liquid were mixed in the refining kettle in a molar ratio of 1:0.3:0.08 and stirred, N 2 Protected, reacted at 40 °C for 3 h, washed, concentrated and purified the epoxycyclohexane functional monomer (B3), the conversion rate was 99.3%, and the NMR H spectrum was as follows image 3 shown. 1 H NMR (500 MHz, Chloroform ) δ 4.32 (s, 10H), 3.53 (s, 10H), 3.41 (s, 12H), 3.36 (s, 5H), 2.96 (s, 13H), 2.70 (d, J = 6.3 Hz, 22H), 2.27 (s, 10H), 1.94 (s, 14H), 1.81 (s, 9H), 1.76 (d, J = 5.0 Hz, 20H), 1.68 (s, 8H), 1.62 (d, J = 10.0 Hz, 18H), 1.41 (s, 10H), 1.32 (s, 6H), 1.25(d, J = 15.0 Hz, 25H), 1.22 – 1.15 (m, 41H), 1.10 (s, 7H).

[0039] The structural formula of epoxy cyclohexane functional monomer (B3) is:

[0040] .

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PUM

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Abstract

The invention relates to a water-soluble polyester monomer and a preparation method and application thereof, a basic unit of the polyester monomer is obtained by reaction of a modified monomer and cyclohexene oxide, and the method comprises the following steps: reacting cyclohexene oxide and the modified monomer according to a certain weight ratio under the catalytic action of imidazole column aromatic hydrocarbon ionic liquid to obtain the water-soluble polyester monomer. And preparing the water-soluble polyester monomer capable of improving the film coating performance of the water-soluble polyester. The imidazole column aromatic hydrocarbon ionic liquid is used as a catalyst, so that the preparation conditions of the water-soluble polyester monomer are effectively reduced, and the water-soluble polyester monomer can be obtained under relatively mild conditions. Meanwhile, the cyclohexene oxide functional monomer obtained by the reaction can efficiently improve the film coating performance of the water-soluble polyester.

Description

technical field [0001] The invention relates to the technical field of water-soluble polyester, in particular to a water-soluble polyester monomer and a preparation method and application thereof. Background technique [0002] Polyester is a polymer formed by polycondensation of polyacid and polyol. It has good gloss, stability, flexibility, weather resistance, solvent resistance and substrate adhesion. It is widely used in coatings, adhesives, Ink and chemical fiber and other fields. However, polyesters widely used in various fields in the market are usually oil-soluble and contain a large amount of volatile organic solvents (VOCs), which pollute the environment and endanger human health. Low-toxicity, non-polluting water-soluble polyester (WPET) is becoming more and more popular. [0003] The water-based polyester is usually the introduction of a hydrophilic group into the polyester. According to the type of the introduced hydrophilic group, it is divided into two catego...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/38C07C69/36C07C69/40C07C69/44C07C67/26C08G63/688
CPCC07C69/38C07C69/36C07C69/40C07C69/44C08G63/6886C07C2601/14Y02P20/54
Inventor 王海玥李继新邓倩郭立颖宋晓慧孙屹亭马子斐
Owner SHENYANG POLYTECHNIC UNIV
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