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Fluorene-based polyfunctional photoinitiator, preparation method and application thereof

A photoinitiator and multi-functionality technology, which is applied in the field of photocuring, can solve the problems of low quantum absorption rate of long wavelengths, achieve high quantum absorption rate, improve initiation efficiency, and improve quantum absorption efficiency.

Active Publication Date: 2020-05-19
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-based polyfunctional photoinitiator, preparation method and application thereof
  • Fluorene-based polyfunctional photoinitiator, preparation method and application thereof
  • Fluorene-based polyfunctional photoinitiator, preparation method and application thereof

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preparation example Construction

[0044] Another aspect of the present application also provides a method for preparing the above-mentioned fluorene-based multifunctional photoinitiator. The preparation method includes: bromination reaction: bromination reaction of raw material a, bromination reagent and first organic solvent to obtain The intermediate product b and the raw material a have the structure shown in formula (II),

[0045]

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

[0047]

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

[0049] According to the conventional understanding of those skilled in the art, the substituent 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 reaction process of the above...

specific Embodiment approach

[0075] The present invention will be further described in detail below in conjunction with specific embodiments, but it should not be understood as a limitation to the protection scope of the present invention.

[0076] 1. Preparation of photoinitiator.

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-necked flask, stir at room temperature, and follow the liquid phase until the raw materials no longer change, then slowly pour the materials into 1000g. In ionized water, stirring while adding, a large amount of solids precipitate out, filtered with suction, washed with water, and absolute ethanol to obtain 37.2 g of intermediate 1a. The synthetic route is as follows:

[0080]

[0081] The structural characterization data of the intermediate product 1a is 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 to a 500mL four-necked f...

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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, its preparation method and its application. Background technique [0002] Traditional small molecule photoinitiators have excellent photosensitivity and solubility, but in practical applications there are problems such as easy migration of photolysis fragments and high volatility. People try to solve these shortcomings by increasing the molecular weight of the compound, but the increase in molecular weight usually reduces the photoinitiation effect. [0003] Fluorene compounds have a relatively large molecular weight, 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 fluorene compounds with large molecular weight is that the fluorene compound initiator has a low quantum absorption rate for long w...

Claims

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Application Information

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Patent Type & Authority Patents(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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