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Phthalonitrile and amino acid cyclic peptide copolymer resin and preparation method thereof

A technology of cyclic peptide copolymer resin and phthalonitrile, which is applied in the field of bio-based thermosetting resin, can solve the problems of volatilization of small molecule curing agent, easy phase separation, low high temperature resistance, etc., so as to improve curing efficiency and cost. Low cost, high crosslink density effect

Active Publication Date: 2022-03-29
SICHUAN UNIV
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

However, due to the inertness of the cyano group, intrinsic phthalonitrile takes a long time to form a polymer even under high temperature, which brings disadvantages such as high energy consumption and long time consumption to the actual production process.
In order to solve this problem, the researchers proposed a technical measure of adding curing components. Although adding a curing agent can improve the curing speed of phthalonitrile resin to a certain extent, it also reduces the curing conditions (arylamine, phenolic hydroxyl, organic resin, etc.) Lewis acids and bases such as acids, ammonium salts, and metal salts can be used as curing agents to promote the rapid curing of phthalonitrile resins), but small molecule curing agents will inevitably volatilize during the curing process, resulting in a large number of bubbles in the material and It is easy to produce phase separation, thereby reducing the crosslinking density and low temperature resistance

Method used

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  • Phthalonitrile and amino acid cyclic peptide copolymer resin and preparation method thereof
  • Phthalonitrile and amino acid cyclic peptide copolymer resin and preparation method thereof
  • Phthalonitrile and amino acid cyclic peptide copolymer resin and preparation method thereof

Examples

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preparation example Construction

[0050]For the preparation method of phthalonitrile monomer with structural formula I-1, see Keller TM, Dominguez DD. High temperature resorcinol-based phthalonitrile polymer [J]. Polymer, 2005, 46(13): 4614-4618.

[0051] For the preparation method of phthalonitrile monomers with structural formulas I-2~I-4, see Liao S, Wu H, He X, etal. Promoting effect of methylne / methylene moiety of bisphenol E / F onphthalonitrile resin curing: Expanding the Structural design route of phthalonitrile resin [J]. Polymer, 2020, 210: 123001.

[0052] For the preparation method of phthalonitrile monomer with structural formula I-5, see Peng W, Yao F, Hu J, et al. Renewable protein-based monomer for thermosets: a case study on phthalonitrile resin [J]. Green Chemistry, 2018, 20(22):5158-5168.

[0053] The preparation method of the phthalonitrile monomer whose structural formula is I-6 refers to Keller T M. Synthesis and polymerization of multiple aromatic ether phthalonitriles [J]. Chemistry of m...

Embodiment 1

[0058] In this example, a copolymer resin of phthalonitrile and amino acid cyclic peptide was prepared by using resorcinol-type bis-phthalonitrile monomer and tyrosine cyclic dipeptide as raw materials, and resorcinol-type bis-phthalonitrile The chemical structural formula of forminonitrile monomer and tyrosine cyclic dipeptide is as follows:

[0059] Resorcinol type bisphthalonitrile monomer:

[0060] Tyrosine cyclic dipeptide:

[0061] Phthalonitrile and amino acid cyclic peptide copolymerization resin in the present embodiment are obtained through the following steps:

[0062] The two raw materials, resorcinol-type diphthalonitrile monomer and tyrosine cyclic dipeptide, were added to a single-necked flask with a magnetic stirrer in a ratio of 3:7, and added 5 times The solvent N,N-dimethylformamide of the total mass of the two raw materials. After the dissolution was complete, the solution was stirred at room temperature for 12 hours, then the solution was removed by...

Embodiment 2

[0072] In this example, bisphenol A type diphthalonitrile monomer and alanine cyclopeptide are used as raw materials to prepare phthalonitrile and amino acid cyclopeptide copolymer resin, bisphenol A type bisphthalonitrile monomer Body, alanine cyclic peptide chemical structure formula is as follows:

[0073] Bisphenol A type bisphthalonitrile monomer:

[0074] Alanine cyclic peptide:

[0075] Phthalonitrile and amino acid cyclic peptide copolymerization resin in the present embodiment are obtained through the following steps:

[0076] Add the two raw materials bisphenol A-type diphthalonitrile monomer and alanine cyclopeptide into a single-necked flask with a magnetic stirrer at a ratio of 1:4, and add 5 times the amount of the two The solvent tetrahydrofuran of the total mass of raw materials. After the dissolution was complete, the solution was stirred at room temperature for 12 hours, then the solution was removed by rotary evaporation at 60°C, and the residue was p...

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Abstract

The invention discloses a phthalonitrile-amino acid cyclic peptide copolymer resin and a preparation method thereof. The phthalonitrile-amino acid cyclic peptide copolymer resin is blended with phthalonitrile monomers and amino acid cyclic peptides as raw materials It is formed by post-curing, and the ratio of the amount of the phthalonitrile monomer to the amino acid cyclic peptide is 1: (1-9). The preparation method of the copolymer resin is to measure and weigh the phthalonitrile monomer and the amino acid cyclic peptide according to the ratio of their substances, dissolve them in a solvent and mix them uniformly, then dry and remove the solvent to obtain a blend, and then The blend is cured at less than the decomposition temperature of the blend. The copolymerization resin of phthalonitrile and amino acid cyclic peptide provided by the invention is a high-performance bio-based thermosetting resin with high crosslink density and excellent high temperature resistance, thermal stability, thermo-oxygen stability and chemical corrosion resistance.

Description

technical field [0001] The invention belongs to the field of bio-based thermosetting resins, and relates to a copolymer resin of phthalonitrile and amino acid cyclic peptide and a preparation method thereof. Background technique [0002] Thermosetting resins are mainly formed from reactive low-molecular prepolymers or polymers with reactive groups through cross-linking and curing reactions of reactive groups, and form bulk polymers during processing and molding. Thermosetting resin has high modulus, high strength, high heat resistance and chemical resistance due to its highly cross-linked structure after curing, so it is widely used in coatings, adhesives, composite materials and electronic components and other fields . [0003] However, traditional thermosetting resins are mostly based on petroleum-based resources, and the extensive use of petroleum-based resources has caused environmental problems such as resource shortage and excessive carbon dioxide emissions. In order...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G73/06
CPCC08G73/0672C08G73/0633
Inventor 杨刚曾科何弦吴浩陈梦豪胡江淮
Owner SICHUAN UNIV
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