Bi-functionality-degree acrylic ester cross-linking agent and application thereof to 3D printing

An acrylate and acrylate technology, applied in the field of light-curing 3D printing rapid prototyping to prepare polymer materials, can solve problems such as immaturity

Active Publication Date: 2016-02-03
殷若瑜
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In fact, due to the above characteristics, the current application of 3D printing technology mainly focuses on the production of toys and models, and it is far from mature to use as structural products.

Method used

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  • Bi-functionality-degree acrylic ester cross-linking agent and application thereof to 3D printing
  • Bi-functionality-degree acrylic ester cross-linking agent and application thereof to 3D printing
  • Bi-functionality-degree acrylic ester cross-linking agent and application thereof to 3D printing

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1 2

[0042] The synthesis of embodiment 1 difunctionality methacrylate crosslinking agent

[0043] 1) Preparation of dihydroxy Diels-Alder adducts:

[0044] Under nitrogen protection, 12.7g (0.1mol) N-methylolmaleimide (CAS: 5063-96-7), 19.6g furfuryl alcohol (0.2mol) (CAS: 98-00-0), 200ml of ethyl acetate was added into a 500ml three-neck flask, and under magnetic stirring, the reaction was carried out at reflux temperature (about 77° C.) and protected from light for 24 hours. After the reaction, cool, filter with suction, collect the filter cake, wash with cold ethyl acetate three times, collect the filter cake, and vacuum-dry at 30°C to constant weight to obtain the target product as a white solid powder with a yield of 83%. The structure of the product was confirmed by spectral characterization, and its NMR spectrum is shown in the attached figure 1 .

[0045] 2) Preparation of difunctional methacrylate crosslinking agent

[0046] Under nitrogen protection, 22.5g (0.1mol) o...

Embodiment 2 2

[0047] Synthesis of embodiment 2 difunctionality acrylate crosslinking agent

[0048] 1) Preparation of dihydroxy Diels-Alder adducts:

[0049] Under nitrogen protection, 14.1g (0.1mol) N-hydroxyethylmaleimide (CAS: 1585-90-6), 24.5g furfuryl alcohol (0.4mol) (CAS: 98-00-0), 250ml of ethyl acetate was added into a 500ml three-necked flask, and reacted at 60°C in the dark for 48 hours under magnetic stirring. After the reaction, cool, filter with suction, collect the filter cake, wash with cold ethyl acetate three times, collect the filter cake, and vacuum-dry at 30°C to constant weight to obtain the target product as a white solid powder with a yield of 81%. The structure of the product was confirmed by 1H NMR spectrum, and its 1H NMR spectrum was omitted.

[0050] 2) Preparation of difunctional acrylate crosslinking agent

[0051] Under the protection of nitrogen, successively add 23.9g (0.1mol) of the dihydroxy Diels-Alder adduct obtained in the above step (1), 15.8g (0.2...

Embodiment 3 2

[0052] Synthesis of embodiment 3 difunctionality acrylate crosslinking agent

[0053] 1) Preparation of dihydroxy Diels-Alder adducts:

[0054] Under nitrogen protection, 12.7g (0.1mol) N-methylolmaleimide (CAS: 5063-96-7), 9.8g furfuryl alcohol (0.1mol) (CAS: 98-00-0), 300ml of ethyl acetate was added into a 500ml three-neck flask, and under magnetic stirring, the reaction was carried out at reflux temperature (about 77° C.) and protected from light for 48 hours. After the reaction, cool, filter with suction, collect the filter cake, wash with cold ethyl acetate three times, collect the filter cake, and vacuum-dry at 30°C to constant weight to obtain the target product as a white solid powder with a yield of 83%. Spectral characterization confirmed the structure of the product, and its NMR spectrum was omitted.

[0055] 2) Preparation of difunctional acrylate crosslinking agent

[0056] Under nitrogen protection, 22.5g (0.1mol) of the dihydroxy Diels-Alder adduct obtained ...

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Abstract

The invention relates to the field of high molecular materials for photocuring 3D printing fast forming equipment and aims to provide a bi-functionality-degree acrylic ester cross-linking agent and application thereof to 3D printing. According to the preparation steps, under protection of nitrogen, furfuryl alcohol, N-hydroxyalkyl maleimide and solvent react, and suction filtration, washing and vacuum drying are carried out on the reaction product to obtain a dihydroxy-terminated Diels-Alder addition product; the addition product is dissolved into the solvent, a pyridine catalyst and acid anhydride are added, the mixture reacts, methyl alcohol is added, the mixture continues to react, methylene chloride is used for dissolving the product, and organic phases are collected to obtain a final product. The initial raw materials are wide in source, the preparation process and purification are simple, and the cross-linking agent is suitable for industrial production process; the product has universality, and the prepared vinyl polymer has excellent mechanical performance and solvent resistant performance of a thermosetting material at normal temperature, and has a recovery processing characteristic of thermoplastic at high temperature; use performance of the product is met, and the application is important breakthrough of the 3D printing material equipment technology.

Description

technical field [0001] The invention relates to the field of photocuring 3D printing rapid prototyping to prepare polymer materials, in particular to a difunctional acrylate crosslinking agent, its preparation method and 3D printing to prepare reversible crosslinked polymer materials. Background technique [0002] Generally, according to different physical and chemical properties, plastics can be divided into two types: thermosetting and thermoplastic. Among them, thermosetting plastics such as epoxy resin, etc., undergo chemical reactions during processing and molding to form a three-dimensional network structure, which endows the material with many advantages, such as shape, dimensional stability, excellent physical and mechanical properties, excellent solvent resistance and aging resistance, etc. . On the other hand, because of its insoluble and infusible three-dimensional network structure, the product cannot be recycled and remolded after use. Therefore, the tradition...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F222/22C08F220/44C08F212/08C08F220/14C08F226/10C08F220/28C08F2/48C07D491/08
Inventor 闵玉勤张兴宏杜滨阳洪佳丽王浩仁黄伟
Owner 殷若瑜
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