Non-isocyanate-based polyurethane monomer, thermosetting non-isocyanate-based shape memory polyurethane and preparation and recycling methods of non-isocyanate-based polyurethane monomer and thermosetting non-isocyanate-based shape memory polyurethane

A non-isocyanate and polyurethane monomer technology, applied in the direction of organic chemistry, can solve the problems of no recycling performance and poor mechanical properties, and achieve good shape recovery rate, improved mechanical strength, and good shape memory performance.

Pending Publication Date: 2022-07-22
LANZHOU INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the mechanical properties of non-isocyanate polyurethanes currently synthesized are poor, which limits the application of non-isocyanate polyurethanes; moreover, the synthesized non-isocyanate polyurethanes are thermosetting polyurethanes cross-linked by covalent bonds, while thermosetting polymers cross-linked by covalent bonds are currently are generally not recyclable

Method used

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  • Non-isocyanate-based polyurethane monomer, thermosetting non-isocyanate-based shape memory polyurethane and preparation and recycling methods of non-isocyanate-based polyurethane monomer and thermosetting non-isocyanate-based shape memory polyurethane
  • Non-isocyanate-based polyurethane monomer, thermosetting non-isocyanate-based shape memory polyurethane and preparation and recycling methods of non-isocyanate-based polyurethane monomer and thermosetting non-isocyanate-based shape memory polyurethane
  • Non-isocyanate-based polyurethane monomer, thermosetting non-isocyanate-based shape memory polyurethane and preparation and recycling methods of non-isocyanate-based polyurethane monomer and thermosetting non-isocyanate-based shape memory polyurethane

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preparation example Construction

[0033] The present invention provides the preparation method of the non-isocyanate-based polyurethane monomer described in the above technical solution, comprising the following steps:

[0034] The non-isocyanate-based polyurethane monomer is obtained by mixing the cyclic carbonate with double bond, thiol and photoinitiator under ultraviolet light irradiation to carry out a click reaction.

[0035] In the present invention, the cyclic carbonate with double bond is ethylene ethylene carbonate (4-Vinyl-1,3-dioxolan-2-one) or has the structure shown in formula IV, in formula IV, R 3 is -H or -CH 3 :

[0036]

[0037] The present invention has no special requirements on the source of the cyclic carbonate with double bonds, and can be prepared by using commercially available products well-known to those skilled in the art or by using a preparation method well-known to those skilled in the art; in the present invention , when the cyclic carbonate with double bond has the struct...

Embodiment 1

[0056] A kind of non-isocyanate group polyurethane monomer, preparation method is as follows:

[0057] Mix 2.7g of ethylene ethylene carbonate, 2.9g of pentaerythritol tetra-3-mercaptopropionate and 60mg of photoinitiator (2,2-dimethoxy-2-phenylacetophenone) and mix well. The liquid is placed under an ultraviolet lamp (the wavelength of ultraviolet light is 365nm, and the irradiation intensity is 30mw / cm -2 ) reaction 10min, obtain the monomer with four five-membered cyclic carbonates, i.e. non-isocyanate based polyurethane monomer, the reaction formula is as follows:

[0058]

[0059] A thermosetting non-isocyanate-based shape memory polyurethane, the preparation method is as follows:

[0060] Add 15 mL of DMF solvent to the above-mentioned non-isocyanate-based polyurethane monomer (with four five-membered cyclic carbonates) and mechanically stir until uniformly mixed to obtain a non-isocyanate-based polyurethane monomer solution; 2.043 g of isophorone di The amine was a...

Embodiment 2

[0063] A kind of non-isocyanate group polyurethane monomer, preparation method is as follows:

[0064] 2.8 g of hydroxymethyldioxolane, 1.9 g of dimethacrylic anhydride and 47 mg of toluenesulfonic acid were mixed in N 2 The cyclic carbonate with double bonds was synthesized by reacting at 135 °C for 6 h; the obtained cyclic carbonate with double bonds, 2.1 g of 3,6-dioxa-1,8-octanedithiol and 60 mg of The photoinitiator (2,2-dimethoxy-2-phenylacetophenone) is mixed evenly, and the mixed liquid is placed under an ultraviolet lamp (the wavelength of ultraviolet light is 365nm, and the irradiation intensity is 30mw / cm -2 ) reaction 5min, synthesizing the monomer with bicyclic carbonate, i.e. non-isocyanate based polyurethane monomer, the reaction formula is as follows:

[0065]

[0066] A thermosetting non-isocyanate-based shape memory polyurethane, the preparation method is as follows:

[0067] Add 15 mL of DMF solvent to the above-mentioned non-isocyanate-based polyuretha...

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Abstract

The invention provides a non-isocyanate-based polyurethane monomer and thermosetting non-isocyanate-based shape memory polyurethane as well as preparation and recycling methods thereof, and relates to the technical field of polyurethane synthesis. The non-isocyanate group polyurethane monomer provided by the invention has a structure as shown in a formula I to a formula III. The non-isocyanate-based polyurethane monomer provided by the invention has a plurality of five-membered cyclic carbonates, and polyurethane generated after a cross-linking reaction with polybasic primary amine has a shape memory effect and is programmable in shape; the polyurethane has excellent mechanical properties, and is high-strength non-isocyanate-based polyurethane; recycling can be achieved through simple hot pressing, and therefore durability and environment friendliness are achieved. According to the preparation method of the non-isocyanate polyurethane monomer, cyclic carbonate with double bonds and mercaptan are subjected to a click reaction to prepare the polyurethane monomer with multiple five-membered cyclic carbonate, the reaction is rapid and efficient, and the reaction time does not exceed 10 min.

Description

technical field [0001] The invention relates to the technical field of polyurethane synthesis, in particular to a non-isocyanate-based polyurethane monomer and a thermosetting non-isocyanate-based shape memory polyurethane and a preparation and recycling method thereof. Background technique [0002] Shape memory polymer material refers to a smart material with a specific initial shape that can restore its initial shape after being deformed under certain conditions and stimulated by external conditions such as heat, light, electricity, and magnetism. Shape memory polyurethane material is an important class of materials. Traditional shape memory polyurethane materials are usually polymerized from polyols and isocyanates, in which isocyanates are usually synthesized by phosgene method. Phosgene is very toxic, causing serious environmental pollution, and isocyanates themselves are also highly toxic. Therefore, exploring non-isocyanate polyurethanes synthesis is becoming more an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D317/36C08G71/04C08J11/04C08L75/04
CPCC07D317/36C08G71/04C08J11/04C08G2280/00C08J2375/04
Inventor 陈守兵张梓明张耀明王廷梅王齐华陶立明
Owner LANZHOU INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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