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Fluorene multifunctional photoinitiator and preparation method and application thereof

A photoinitiator, multifunctional technology, applied in the field of photocuring, can solve the problem of low quantum absorption rate at long wavelengths, achieve high quantum absorption rate, improve initiation efficiency, and improve the effect of quantum absorption efficiency

Active Publication Date: 2019-01-04
CHANGZHOU TRONLY ADVANCED ELECTRONICS MATERIALS CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The main purpose of the present invention is to provide a kind of fluorene polyfunctional photoinitiator, its preparation method and its application, to solve the problem that existing photoinitiator exists to the quantum absorptivity of long wavelength is low

Method used

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  • Fluorene multifunctional photoinitiator and preparation method and application thereof
  • Fluorene multifunctional photoinitiator and preparation method and application thereof
  • Fluorene multifunctional photoinitiator and preparation method and application thereof

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preparation example Construction

[0044] Another aspect of the present application also provides a preparation method of the above-mentioned fluorene-based polyfunctional photoinitiator, the preparation method comprising: bromination reaction: reacting raw material a, bromination reagent and the first organic solvent with bromination reaction to obtain Intermediate product b, raw material a has the structure shown in formula (II),

[0045]

[0046] The intermediate product b has the structure of formula (Ⅲ),

[0047]

[0048] Substitution reaction: use the intermediate product b, a substitution reagent and a second organic solvent to undergo a substitution reaction to obtain a fluorene-based multifunctional photoinitiator.

[0049] According to the conventional understanding of those skilled in the art, the substituent group R in the structural formula shown in formula (II) and formula (III) 1 , R 2 , R 3 , R 4 And X has the same structure as the corresponding group in formula (I). The chemical reac...

preparation Embodiment 1

[0078] (1) Substitution reaction: Preparation of intermediate 1a.

[0079] Add 36.5g of raw material 1a, 18g of N-bromosuccinimide, and 100mL of propylene carbonate to a 500mL four-neck flask, stir at room temperature, follow the reaction of the liquid phase until the raw materials no longer change, and then slowly pour the materials into 1000g to Stirring while adding in deionized water, a large amount of solids precipitated, suction filtered, washed with water, and absolute ethanol to obtain 37.2g of intermediate 1a. The synthetic route is as follows:

[0080]

[0081] The structural characterization data of the intermediate product 1a are as follows: 1 H-NMR (CDCl 3 , 500MHz): 0.9146~1.0002(6H,t), 1.2878~1.3328(8H,m), 1.4844(6H,s), 1.8754~2.1045(5H,m), 7.5801~8.0837(6H,m).

[0082] MS(m / z):444(M+1) + .

[0083] (2) Substitution reaction: preparation of compound 1.

[0084]Add 22.2g of intermediate 1a, 50mL of methanol, and 14.0g of sodium methoxide into a 500mL fou...

preparation Embodiment 2

[0088] Step substitution reaction: Preparation of intermediate 2a.

[0089] Add 35.0g of raw material 2a, 18g of N-bromosuccinimide, and 100mL of propylene carbonate to a 500mL four-neck flask, stir at room temperature, follow the reaction of the liquid phase until the raw materials no longer change, and then slowly pour the materials into 1000g to In deionized water, stirring while adding, a large amount of solids precipitated out, suction filtered, washed with water, and absolute ethanol to obtain 36.8g of intermediate 2a. The synthetic route is as follows:

[0090]

[0091] The structural characterization data of the intermediate product 2a are as follows: 1 H-NMR (CDCl 3 , 500MHz): 1.3629 (6H, s), 1.6578 (6H, s), 2.3899-2.3835 (4H, t), 3.6703-3.6801 (4H, t), 7.5481-7.8997 (6H, m).

[0092] MS(m / z):429(M+1) + .

[0093] (2) Substitution reaction: preparation of compound 2.

[0094] Add 21.4g of intermediate 2a, 50mL of xylene, and 14.0g of sodium methoxide to a 500...

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Abstract

The invention provides a fluorene multifunctional photoinitiator and a preparation method and application thereof. The fluorene multifunctional photoinitiator has a structure represented by a formula(I), and X is -A-(X')n, wherein A is selected from a hetero atom, the hetero atom is selected from O, N or S, X' is selected from a C1-C20 linear or branched alkyl group, a C3-C8 cycloalkyl group anda C3-C8 cycloalkyl group-substituted C1-C10 alkyl group, or one or more carbon atoms in X are substituted by the hetero atom, and n is 1 or 2; R4 is a hydroxy group or an N-morpholinyl group. A heteroatom-containing substituent group is introduced to a side chain of a fluorene compound, red shifting of the absorption wavelength of the fluorene compound is facilitated, and thus the initiation efficiency of the compound can be improved. Furthermore, when one or more carbon atoms in the X' group are substituted by the hetero atom or other substituent groups contain the hetero atom, further improvement of the quantum absorption efficiency of the fluorene compound photoinitiator for long wavelength is facilitated.

Description

technical field [0001] The invention relates to the field of photocuring, in particular to a fluorene-based multifunctional photoinitiator, a preparation method and application thereof. Background technique [0002] Traditional small molecule photoinitiators have excellent photosensitivity and solubility, but there are problems such as easy migration of photolytic fragments and high volatility in practical applications. Attempts have been made to address these deficiencies by increasing the molecular weight of the compound, but an increase in molecular weight usually reduces the photoinitiation effect. [0003] Fluorene compounds have relatively large molecular weights, and their application in UV curing is well known in the art. Using it as a photoinitiator can overcome the problems faced by traditional small molecule photoinitiators. However, the problem faced by the fluorene compounds with large molecular weight is that the quantum absorptivity of the fluorene compound ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F2/48C07D295/108C07D295/112C07C319/14C07C221/00C07C225/22C07C45/64C07C49/84C09D4/02
CPCC07C45/63C07C45/64C07C49/84C07C221/00C07C225/22C07C319/14C07D295/108C07D295/112C08F2/48C09D4/00C09D7/00C09D11/101C07C323/22C07C49/83
Inventor 钱晓春胡春青于培培
Owner CHANGZHOU TRONLY ADVANCED ELECTRONICS MATERIALS CO LTD
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