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Polymerizable lignin-based macromolecular photoinitiator, preparation method and applications thereof

A photoinitiator, lignin-based technology, applied in the field of photocuring, can solve the problems of complex synthesis, few functional groups, high risk or high cost, and achieve improved comprehensive performance, improved macroscopic performance, and high photoinitiated activity. Effect

Active Publication Date: 2020-03-03
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this method is applicable to fewer types of photoinitiators and the polymerizable photoinitiators obtained through the chemical modification of small molecule photoinitiators have fewer functional groups on their molecular skeletons and less photoinitiating activity. In addition, the synthesis process of this type of initiator often has defects such as relatively complicated synthesis, high risk or cost, and poor storage stability, making it difficult to promote in practical applications

Method used

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  • Polymerizable lignin-based macromolecular photoinitiator, preparation method and applications thereof
  • Polymerizable lignin-based macromolecular photoinitiator, preparation method and applications thereof
  • Polymerizable lignin-based macromolecular photoinitiator, preparation method and applications thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0064] This embodiment provides an ester-soluble polymerizable lignin-based macromolecular photoinitiator L-AC-2959, which is prepared according to the following steps:

[0065] 1) Dissolve 20 g of alkaline lignin in 1 mol / L aqueous sodium hydroxide solution to make the lignin content 25% (w / w), and then add 21.3 mL of triethylamine to the above solution. The above solution was placed in an ice-water mixed bath and the temperature was controlled at 0-5°C. Under vigorous stirring, a mixed solution of 9.05 g of acryloyl chloride and dichloromethane (18 mL) was slowly added dropwise. After the dropwise addition was completed, the reaction was continued at this temperature for a period of time. The pH of the obtained reaction solution was adjusted to 7 with hydrochloric acid, and a large amount of brown-black solids were precipitated. The precipitates were obtained by filtration and dried to obtain a crude product (L-AC).

[0066]

[0067] Wherein, n1 and n4 are natural number...

Embodiment 2

[0074] Similar to step 3) of Example 1, add 8.0 g of the product obtained in step 2) of Example 1 and 5.0 g of the product obtained in step 1) of Example 1 and 300 mL of dimethyl sulfoxide solvent in a 500 mL there-necked flask, and then in the above-mentioned Add 0.1 mol / L sodium hydroxide dropwise to the solution to adjust the pH between 8 and 9, heat to 80°C and react under this condition for 4 hours. After the reaction, cool down naturally, adjust the pH of the reaction solution to 7 with hydrochloric acid, then wash the reaction solution with a small amount of water, filter, retain the brown aqueous solution, and then use a dialysis membrane with a molecular weight cut-off of 5kDa for 7 days to remove residual small molecules. Photoinitiators, solvents, salts formed, and other impurities. The resulting brown aqueous solution in the dialysis membrane was poured into a large watch glass and dried under vacuum at 30°C for 7 days to obtain the pure final product L-AC-2959.

...

Embodiment 3

[0077] This example provides an ester-soluble polymerizable lignin-based macromolecular photoinitiator L-11ene-2959, which is prepared according to the following steps:

[0078] 1) Dissolve 20 g of alkaline lignin in 1 mol / L aqueous sodium hydroxide solution to make the lignin content 25% (w / w), and then add 21.3 mL of triethylamine to the above solution. The above solution was placed in an ice-water mixed bath and the temperature was controlled at 0-5°C. Under vigorous stirring, a mixed solution of 20.2 g of undecylenoyl chloride and dichloromethane (40 mL) was slowly added dropwise. After the dropwise addition was completed, the reaction was continued at this temperature for a period of time. The pH of the obtained reaction solution was adjusted to 7 with hydrochloric acid, and then unreacted unreacted acid chloride and the by-product undecylenic acid were extracted with a large amount of petroleum ether, and finally the crude product (L-11ene) was obtained by filtration and...

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Abstract

The invention discloses a polymerizable lignin-based macromolecular photoinitiator, a preparation method and applications thereof, wherein the structure formula of the polymerizable lignin-based macromolecular photoinitiator is represented by the following formula I, wherein the group defined in the specification is a terminal-hydroxyl-free molecular skeleton of lignin, M1 is a terminal-hydroxyl-free and halogen-atom-free molecular skeleton after epoxy haloalkane is subjected to an epoxy ring-opening reaction, M2 is an acyl-chloride-free and double-bond-free molecular skeleton of a solubilizing compound, M3 is a hydroxyl-free molecular skeleton of a cracking type photoinitiator, n1 and n3 are natural numbers of greater than or equal to 1, n2 is an integer of greater than or equal to 0, andthe sum of n1, n2 and n3 is the number of the terminal hydroxyl groups of lignin. The invention also discloses a preparation method and applications of the photoinitiator. The photoinitiator disclosed by the invention has characteristics of good ester solubility, good polymerizability, high photo-initiation activity, good thermal stability, good storage performance, low viscosity, low mobility, low toxicity and no volatilization.

Description

technical field [0001] The invention relates to the field of light curing technology. More specifically, it relates to a polymerizable lignin-based macromolecular photoinitiator and its preparation method and application. Background technique [0002] Photocuring technology is a high-efficiency, energy-saving, environmentally friendly, high-quality material surface treatment technology, known as a new technology for the green industry in the 21st century. At present, it has been widely used in printing, packaging, advertising, building materials and other industries. Its products mainly include UV inks, UV adhesives, photosensitive printing plates, photoresists, light rapid prototyping materials, etc. In recent years, with the expansion of demand for high-end user-customized products, especially the huge application prospects in life sciences, 3D printing based on optical technology has been recognized by people for its high printing accuracy, fast printing speed, and high...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08H7/00C08F2/48C08F289/00C08F222/20C08F220/32B33Y70/00C09D175/14C09D7/65
CPCB33Y70/00C08F2/48C08F289/00C08H6/00C09D175/14C09D7/65C08F220/32C08L97/005
Inventor 赵榆霞刘源黄星张雪琴张云龙张玉玺施盟泉
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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