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Tert-butyloxycarboryl protected acid-sensitive epoxy monomer as well as synthesis method and application thereof

A technology of tert-butoxycarbonyl and epoxy monomers, which is applied in the field of acid-sensitive epoxy monomers protected by tert-butoxycarbonyl and their synthesis, can solve the problems of lack of functionality, lack of reactive functional groups and the like, Achieve versatility, high added value, and low resolution

Pending Publication Date: 2022-07-26
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, common epoxy monomers lack reactive functional groups, which makes epoxy-based polymers only used as general-purpose materials without functionality, and compared with traditional polyolefin materials, epoxy-based Polymers do not have advantages in cost and mechanical properties

Method used

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  • Tert-butyloxycarboryl protected acid-sensitive epoxy monomer as well as synthesis method and application thereof
  • Tert-butyloxycarboryl protected acid-sensitive epoxy monomer as well as synthesis method and application thereof
  • Tert-butyloxycarboryl protected acid-sensitive epoxy monomer as well as synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0076] The structure and synthesis route of epoxy monomer A are as follows:

[0077]

[0078] Under nitrogen atmosphere, 68.25 g (1 molar equivalent) of tert-butoxyformyl chloride was added dropwise to 49 g of 1-hydroxy-3-cyclohexene, and 43.5 g (1.1 molar equivalent) of pyridine was added dropwise. After 1 h of reaction at room temperature, 200 ml of dichloromethane and 200 ml of deionized water were added to the reaction solution, the product was extracted into the dichloromethane phase, and the organic phase was washed three times with deionized water, anhydrous Na 2 SO 4 After drying, dichloromethane was removed by rotary evaporation, and then distilled under reduced pressure to obtain raw material a.

[0079] Dissolve raw material a in 1 L of dichloromethane, add 110 g (purity of 85 wt%, 1.2 molar equivalent) m-chloroperoxybenzoic acid (m-CPBA), react at room temperature for 12 h, add saturated NaSO 3 Solution until starch potassium iodide test paper does not turn blue...

Embodiment 2

[0081] The structure and synthesis route of epoxy monomer B are as follows:

[0082]

[0083] At 0°C, 48.5 g of 3-aminocyclohexene was added to a mixed solution of 500 ml of dioxane and 300 ml (2M aqueous solution, 1.2 molar equivalent) sodium hydroxide solution, and 130 ml ( 1.1 molar equivalents) di-tert-butyl dicarbonate. After the reaction was stirred at room temperature for 5 h, 300 ml of deionized water was added, and the pH value was adjusted to 3 with 1.5 N hydrochloric acid. The reaction solution was extracted with ethyl acetate (3×200ml), washed with saturated NaCl solution 3 times, and anhydrous Na 2 SO 4 After drying, ethyl acetate was removed by rotary evaporation and then distilled under reduced pressure to obtain raw material b.

[0084] Dissolve raw material b in 1 L of dichloromethane, add 97.5 g (purity of 85 wt%, 1.2 molar equivalent) m-chloroperoxybenzoic acid (m-CPBA), and react at room temperature for 12 h, then add saturated NaSO 3 Solution until ...

Embodiment 3

[0086] The structure and synthesis route of epoxy monomer C are as follows:

[0087]

[0088] The epoxy monomer C can be obtained by the same synthesis method as in Example 1, except that the 1-hydroxy-3-cyclohexene in the carbonation reaction is changed to 4-vinylphenol. by as image 3 As can be seen from the shown proton nuclear magnetic resonance spectrum, epoxy monomer C was obtained.

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Abstract

The invention discloses a t-butyloxycarboryl protected acid-sensitive epoxy monomer, the chemical formula of which is shown as one of formulas (1) to (3), and R3 is one of formulas A to D. The invention also discloses a synthesis method of the t-butyloxycarboryl protected acid-sensitive epoxy monomer, and application of the t-butyloxycarboryl protected acid-sensitive epoxy monomer in preparation of t-butyloxycarboryl protected acid-sensitive polymer. The acid-sensitive epoxy monomer with the tert-butyloxycarboryl protection, provided by the invention, can respond to a pH value, especially an acidic environment, so that an obtained polymer material has stimuli responsiveness. Therefore, the tert-butyloxycarboryl protected acid-sensitive polymer can be used in the field of chemical amplification of photoresists, so that the acid-sensitive polymer is endowed with more functionality and higher additional value.

Description

technical field [0001] The invention relates to the field of organic compounds, in particular to a tert-butoxycarbonyl-protected acid-sensitive epoxy monomer and a synthesis method and application thereof. Background technique [0002] Epoxy compounds are a class of highly reactive polymerizable monomers, which can be homopolymerized under the catalysis of metal or metal-free catalysts to obtain polyethers, and can also be copolymerized with small molecules such as carbon monoxide and carbon dioxide to obtain more rigid polyesters and polymers. Carbonates (J. Am. Chem. Soc. 2020, 142, 12245; Angew. Chem. Int. Ed. 2020, 59, 2; Macromolecules 2021, 54, 9427; CN201710046977.0; CN200610154860.6). Epoxy-based polymers are a typical class of degradable polymers because the main chain has chemical bonds and groups that are easy to break. However, common epoxy monomers lack reactive functional groups, which makes epoxy-based polymers can only be used as general-purpose materials wi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D303/16C07D303/48C07D301/14C08G63/00C08G64/34C08G65/22G03F7/004
CPCC07D303/48C07D303/16C07D301/14C08G64/34C08G65/22C08G63/00G03F7/004
Inventor 伍广朋陆新宇张瑞生
Owner ZHEJIANG UNIV
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