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Phosphorus-containing polyurethane acrylate oligomer, and preparation method and application thereof

A technology of urethane acrylate and hydroxy acrylate, applied in the field of phosphorus-containing cyclic structure urethane acrylate oligomer and its synthesis, can solve the problems of short life, poor storage stability and the like

Active Publication Date: 2016-05-11
CHANGXING PHOTOELECTRIC MATERIAL +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Moreover, the existing LDI dry film photoresist itself has a high exposure speed, but its storage stability is poor and its life is short

Method used

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  • Phosphorus-containing polyurethane acrylate oligomer, and preparation method and application thereof
  • Phosphorus-containing polyurethane acrylate oligomer, and preparation method and application thereof
  • Phosphorus-containing polyurethane acrylate oligomer, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] (1) Synthesis of semi-adducts

[0052] Under the protection of nitrogen, 116.12 grams of hydroxyethyl acrylate and 1.0451 grams of dibutyltin dilaurate were added dropwise to 168.19 grams of hexamethylene diisocyanate. The reaction temperature was maintained at 40°C, and the concentration of -NCO in the system was monitored. -The NCO content is 50% of the initial content to obtain the semi-blocked semi-adduct A of diisocyanate;

[0053] (2) Synthesis of phosphate

[0054] Dissolve 268.35 grams of trimethylolpropane in toluene, add 153.33 grams of phosphorus oxychloride to the trimethylolpropane solution dropwise at 40°C, and react for 5 hours to obtain phosphate B;

[0055] (3) Synthesis of polyurethane acrylate oligomer

[0056] Under the protection of nitrogen, 312.18 grams of phosphoric acid ester B, 284.31 grams of semi-end-capped addition product A and 1.4216 grams of polymerization inhibitor p-hydroxyanisole were added to the reactor. The temperature was raised to 70°C and...

Embodiment 2

[0060] (1) Synthesis of semi-adducts

[0061] Under the protection of nitrogen, 116.12 grams of hydroxyethyl acrylate and 1.0451 grams of dibutyltin dilaurate were added dropwise to 168.19 grams of hexamethylene diisocyanate. The reaction temperature was maintained at 40°C, and the concentration of -NCO in the system was monitored until- The NCO content is 50% of the initial content to obtain the semi-blocked semi-adduct A of diisocyanate;

[0062] (2) Synthesis of phosphate

[0063] Dissolve 178.90 grams of trimethylolpropane in toluene, add 153.33 grams of phosphorus oxychloride to the trimethylolpropane solution dropwise at 40°C, and react for 5 hours to obtain phosphate B;

[0064] (3) Synthesis of polyurethane acrylate oligomer

[0065] Under the protection of nitrogen, 244 grams of phosphoric acid ester B, 284.31 grams of semi-end-capped addition product A and 1.4216 grams of polymerization inhibitor p-hydroxyanisole were added to the reactor. The temperature was raised to 70°C, ...

Embodiment 3

[0069] (1) Synthesis of semi-adducts

[0070] Under the protection of nitrogen, 130.14 grams of hydroxypropyl acrylate and 1.3100 grams of dibutyltin dilaurate were added dropwise to 168.20 grams of hexamethylene diisocyanate. The reaction temperature was maintained at 45°C and the -NCO concentration change in the system was monitored until -The NCO content is 50% of the initial content to obtain the semi-adduct A of diisocyanate;

[0071] (2) Synthesis of phosphate

[0072] Dissolve 268.35 grams of trimethylolpropane in toluene, add 229.995 grams of phosphorus oxychloride to the trimethylolpropane solution dropwise at 50°C, and react for 3.5 hours to obtain phosphoric acid ester B;

[0073] (3) Synthesis of polyurethane acrylate oligomer

[0074] Under the protection of nitrogen, 334.09 grams of phosphoric acid ester B, 298.34 grams of semi-end-capped addition product A and 1.4917 grams of polymerization inhibitor p-hydroxyanisole were added to the reactor, heated to 75°C, and added d...

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Abstract

The invention discloses a phosphorus-containing polyurethane acrylate oligomer, and a preparation method and an application thereof. The preparation method comprises the following steps: adding hydroxy acrylate and dibutyltin dilaurate to diisocyanate in a dropwise manner, controlling the reaction temperature, and monitoring the concentration change of -NCO in a system to obtain a semi-adduct of diisocyanate; dissolving polyol in toluene, adding an acylchloriration agent phosphorous oxychloride in a dropwise manner, and reacting to obtain cyclic phosphate B; and heating the cyclic phosphate B, the semi-adduct of diisocyanate and a polymerization inhibitor, adding a catalyst dissolved in acetone in a dropwise manner, and reacting to obtain phosphorus-containing annular structured polyurethane acrylate. The above product can be applied in photoimageable components. Introduction of an annular phosphate group in the design process of a molecular structure increases the adhesion of a dry film photoresistive resist on a metal substrate; and the method has the advantages of simple synthesis route, few side reactions, no pollution, and obtaining of the product with good performances without purification.

Description

Technical field [0001] The invention relates to a phosphorus-containing polyurethane acrylate oligomer, in particular to a phosphorus-containing cyclic structure polyurethane acrylate oligomer and a synthesis method thereof. Background technique [0002] Ultraviolet light (UV) curing technology is a new technology with high efficiency, energy saving and environmental protection. It refers to that the photoinitiator in the liquid UV material is excited to free radicals or cations under UV radiation, and the initiator material contains active groups (Unsaturated double bonds) chemical reactions (various types of polymerization and reactions), forming a solidified body structure. UV curing has its own unique characteristics and advantages, which are in full compliance with the "5E" principle: Energy (Energy Saving), Ecology (Environmental Protection), Economy (Economy), Efficiency (Efficient), Enabling (Multi-energy), with irreplaceable advantages. [0003] Among them, polyurethane a...

Claims

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Application Information

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IPC IPC(8): C07F9/6574G03F7/004G03F7/033
CPCC07F9/65742G03F7/004G03F7/033
Inventor 杨明雄林耿弘郑裕正李利涂伟萍卢明
Owner CHANGXING PHOTOELECTRIC MATERIAL
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