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Multifunctional double-curing linear polyurethane acrylate resin and preparation method thereof

A urethane acrylate, dual-curing linear technology, used in polyurea/polyurethane coatings, polyurea/polyurethane adhesives, adhesive types, etc. Incomplete curing and other problems, to achieve the effect of reducing volume shrinkage, increasing flexibility, and improving shrinkage

Inactive Publication Date: 2019-08-09
HUBEI SANJIANG AEROSPACE JIANGHE CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The invention provides a multi-functional dual-curing linear polyurethane acrylate resin and its preparation method. Its unique light-thermal dual-curing system can solve the problem of insufficient internal ultraviolet light irradiation of composite materials due to poor light transmittance, which causes surface curing rate and Problems of internal inconsistency, incomplete internal curing or uncured, at the same time, by adjusting the structure and ratio of isocyanate rigid segment and polybutadiene chain flexibility in urethane acrylate prepolymer, it can control the reaction rate and complement the volume change , comprehensive performance adjustment and other aspects have a good synergistic effect to meet the requirements of additive manufacturing for the viscosity and melting point of photosensitive resins, and greatly promote the popularization and application of polyurethane acrylate resin in composite material additive manufacturing

Method used

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  • Multifunctional double-curing linear polyurethane acrylate resin and preparation method thereof
  • Multifunctional double-curing linear polyurethane acrylate resin and preparation method thereof
  • Multifunctional double-curing linear polyurethane acrylate resin and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 2

[0044] Multi-functional dual-cure linear polyurethane acrylate resin and preparation method thereof:

[0045] The raw materials are:

[0046] Epoxidized hydroxyl-terminated polybutadiene 2000g, hydroxyl value 0.668mmol / g, epoxy value 2.5mmol / g, number average molecular weight 4200;

[0047] Toluene diisocyanate (TDI) 221.15g;

[0048] Hydroxypropyl methacrylate 101.06g;

[0049] p-methoxyphenol 20.41g;

[0050] Iron acetylacetonate 3.15g;

[0051] The specific preparation method is:

[0052] (1) Synthesis of intermediates: first add 20.41g p-methoxyphenol to 101.06g hydroxypropyl methacrylate and mix well; then add 3.15g iron acetylacetonate to 221.15g toluene diisocyanate (TDI) and mix well , and then drop isophorone diisocyanate into hydroxyacrylate at a rate of 3 drops / s, react at 50°C for 3h, and detect the NCO group content in the system by the di-n-butylamine method, when its mass percentage When the content is 50±1%, the intermediate is obtained;

[0053] (2) Pol...

Embodiment 3

[0056] Below in conjunction with embodiment, further illustrate the present invention.

[0057] Multi-functional dual-cure linear polyurethane acrylate resin and preparation method thereof:

[0058] The raw materials are:

[0059] Epoxidized hydroxyl-terminated polybutadiene 3600g, hydroxyl value 0.425mmol / g, epoxy value 1.5mmol / g, number average molecular weight 2500;

[0060] Hexamethylene diisocyanate (HDI) 360.45g;

[0061] Trimethylolpropane diacrylate (TMPDA) 188.06g;

[0062] 2,6-di-tert-butyl-4-methylphenol 26.12g;

[0063] Triphenyltin chloride 3.98g;

[0064] The specific preparation method is:

[0065] (1) Synthesis of intermediates: First, 26.12g of 2,6-di-tert-butyl-4-methylphenol was added to 188.06g of trimethylolpropane diacrylate and mixed evenly; then 3.98g of triphenyl chloride Tin was added to 360.45g of hexamethylene diisocyanate (HDI) and mixed evenly, then hexamethylene diisocyanate was added dropwise to the hydroxy acrylate at a rate of 5 drops / s,...

Embodiment 4

[0069] Below in conjunction with embodiment, further illustrate the present invention.

[0070] Multi-functional dual-cure linear polyurethane acrylate resin and preparation method thereof:

[0071] The raw materials are:

[0072] Epoxidized hydroxyl-terminated polybutadiene 100g, hydroxyl value 0.425mmol / g, epoxy value 3.5mmol / g, number average molecular weight 5000;

[0073] Dimer fatty acid diisocyanate (DDI) 10.24g;

[0074] 1,6-hexanediol diacrylate 8.06g;

[0075] Hydroquinone 0.145g;

[0076] Tris(ethoxyphenyl)bismuth 1.15g;

[0077] The specific preparation method is:

[0078] (1) Synthesis of intermediates: first add 0.145 g of hydroquinone to 8.06 g of 1,6-hexanediol diacrylate and mix evenly; then add 1.15 g of tris(ethoxyphenyl) bismuth to 10.24 g of diacrylate Mix well with polyfatty acid diisocyanate (DDI), then drop dimer fatty acid diisocyanate into 1,6-hexanediol diacrylate at a rate of 1 drop / s, and react at 50-60°C for 2-3 hours , detect the NCO group...

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Abstract

The invention discloses a multifunctional double-curing linear polyurethane acrylate resin and a preparation method thereof. The resin is prepared from the following raw materials by weight: 100 partsof epoxidized hydroxyl-terminated polybutadiene, 10-25 parts of diisocyanate, 5-12 parts of hydroxy acrylate and 0.1-2.0 parts of a polymerization inhibitor, and 0.1-2.0 parts of a catalyst. The preparation method includes: firstly synthesizing an intermediate: adding the polymerization inhibitor into metered hydroxy acrylate and mixing the substances evenly; then adding the catalyst into metereddiisocyanate and mixing the substances evenly, then adding diisocyanate dropwise into hydroxy acrylate, and carrying out reaction at 50-60DEG C for 2-3h; and finally, adding the intermediate dropwiseinto metered epoxidized hydroxyl-terminated polybutadiene, and carrying out reaction at 60-80DEG C for 2-6h, thus obtaining polyurethane acrylate. The resin provided by the invention can reduce the dosage of an acrylate type reactive diluent, can avoid incomplete internal curing, and meets the requirements of additive manufacturing for the viscosity, melting point and the like of photosensitive resin.

Description

technical field [0001] The invention relates to the field of photocurable oligomers, in particular to a multifunctional dual-cure linear polyurethane acrylate resin and a preparation method thereof. Background technique [0002] UV curing technology is widely used in coatings, inks, adhesives and other fields because of its fast curing rate, environmental friendliness, cost and energy savings. It is currently the most active and popular 3D printing technology. [0003] Polyurethane acrylate resin combines the excellent properties of polyurethane and acrylate, and has the high wear resistance, adhesion, flexibility, high peel strength and excellent low temperature resistance of polyurethane, as well as the excellent optical properties and weather resistance of polyacrylic acid. The main photosensitive material for stereolithography (SLA) additive manufacturing. Most photosensitive resin prepolymers are multifunctional macromolecular compounds containing groups such as C=C, C...

Claims

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Application Information

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IPC IPC(8): C08G18/69C08G18/67C09D175/14C09J175/14C09D11/101C09D11/102
CPCC08G18/67C08G18/69C09D11/101C09D11/102C09D175/14C09J175/14
Inventor 舒凯凯邓安华郑化田小东胡秋明谭赛杨理国刘敏臧雄王菲廖建萍
Owner HUBEI SANJIANG AEROSPACE JIANGHE CHEM TECH