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Polymerizable polyurethane associative thickener with side group at tail end as well as preparation method and application of polymerizable polyurethane associative thickener

An associative thickener and polymeric technology, applied in the industrial field, can solve the problems of easy migration, penetration, coating performance damage, shortening coating life, etc., and achieve good thickening effect and good thickening performance , viscosity and relaxation time increase

Active Publication Date: 2020-11-17
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] Polyurethane associative thickeners rely on purely physical association networks to achieve thickening, which can better meet the storage, transportation, or use of general water-based paints, adhesives, emulsions and other systems, but the product After use, it is unstable in the cured paint film, and it is prone to migration and penetration. Especially when the water-based coating is washed or soaked in rainwater, this kind of hydrophilic additive is easier to dissolve and migrate because it has not been chemically cross-linked. The performance of the layer will cause damage, thereby shortening the life of the coating, etc.

Method used

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  • Polymerizable polyurethane associative thickener with side group at tail end as well as preparation method and application of polymerizable polyurethane associative thickener
  • Polymerizable polyurethane associative thickener with side group at tail end as well as preparation method and application of polymerizable polyurethane associative thickener
  • Polymerizable polyurethane associative thickener with side group at tail end as well as preparation method and application of polymerizable polyurethane associative thickener

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] (1) Preparation of stearic acid (n=18) modified glycidyl methacrylate end-capping agent:

[0050] Under the protection of nitrogen, add 20g (70.28mmol) stearic acid, 10.03g (70.51mmol) glycidyl methacrylate, 30mg triethylamine, 50mg methyl hydroquinone in the three-necked flask of 150ml, be warming up to 110 ℃, React for 5 hours (the acid value of the monitoring system is lower than 0.1mgKOH / g). After the reaction is completed, the crude product is purified several times in petroleum ether to obtain a pure hydroxyl-bearing end-capping agent.

[0051] (2) Synthesis of polymerizable polyurethane associative thickener with methacrylate side groups at the end: 46.88g PEG (20000, m=454) was put into a 500ml three-necked flask, and 300ml of toluene was added to heat up to 110 After 4 hours of azeotropic distillation (azeotropic point 97°C), cool down to 50°C, add 2.60g (11.72mmol) of IPDI and 98.96mg of catalyst dibutyltin dilaurate, raise the temperature to 90°C and continu...

Embodiment 2

[0069] (1) Preparation of hexadecanoic acid (n=16) modified glycidyl methacrylate end-capping agent:

[0070] Under nitrogen protection, in the there-necked flask of 150ml, add 25g (97.50mmol) hexadecanoic acid, 13.93g (98mmol) glycidyl methacrylate, 38.93mg benzyl trimethyl ammonium chloride, 69.65mg BHT, Raise the temperature to 110 degrees and react for 2 hours (the acid value of the monitoring system is lower than 0.1mgKOH / g). After the reaction is completed, filter and recrystallize the crude product several times with petroleum ether to obtain a pure end-capping agent.

[0071] (2) Synthesis of polymerizable polyurethane associative thickener with methacrylate side groups at the end: 56.57g PEG (6000, m=136) was put into a 500ml three-necked flask, and 300ml of toluene was added to heat up to 120 After 3 hours of azeotropic distillation (azeotropic point 97°C), cool down to 50°C, add 2.11g (12.57mmol) of HDI and 117.36mg of catalyst stannous octoate, raise the temperatu...

Embodiment 3

[0082] (1) Preparation of myristyl acid (n=14) modified glycidyl methacrylate end-capping agent:

[0083] Under nitrogen protection, add 23g (100.71mmol) tetradecyl acid, 14.36g (101mmol) glycidyl methacrylate, 37.36mg hexadecyltrimethylammonium bromide, 71.80mg to the three-necked flask of 150ml For p-hydroxyanisole, the temperature was raised to 110 degrees to react for 3.5 hours (the acid value of the monitoring system was lower than 0.1mgKOH / g). After the reaction was completed, it was filtered, and the crude product was recrystallized several times with petroleum ether to finally obtain a relatively pure end-capping agent.

[0084] (2) Synthesis of polymerizable polyurethane associative thickener with methacrylate side groups at the end: put 90.13g PEG (10000, m=227) into a 500ml three-necked flask, add 300ml toluene and heat up to 125 After 2.5 hours of azeotropic distillation (azeotropic point 97°C), cool down to 50°C, add 3.38g (13.52mmol) MDI and 93.51mg catalyst bis...

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Abstract

The invention discloses a polymerizable polyurethane associative thickener with a side group at the tail end as well as a preparation method and application of the polymerizable polyurethane associative thickener. The preparation method comprises the following steps: under the protection of nitrogen, mixing long-chain alkyl acid and glycidyl acrylate, adding a first catalyst and a polymerization inhibitor, heating to 80-130 DEG C, and reacting for 2-12 hours; recrystallizing the crude product to prepare a long-carbon-chain polymerizable end-capping reagent with a side group; then preparing a polyurethane prepolymer; adding a long-carbon-chain polymerizable end-capping reagent and a polymerization inhibitor of side groups, heating the mixture to 80-120 DEG C, reacting for 10-24 hours, purifying the obtained polymer, and drying the polymer. In the invention, the polymerizable polyurethane associative thickener with the side group at the tail end can be used as a rheology modifier in UV water-based emulsion, paint, ink and adhesive. The polymerizable polyurethane associative thickener with the side group at the tail end has double functions of thickening and polymerization reaction.

Description

technical field [0001] The invention relates to an associative polyurethane thickener, in particular to a polyurethane associative thickener with photoinitiated free radical polymerization activity, in particular to a terminal with a vinyl side group and a long-chain alkyl group, A polyurethane associative thickener that can undergo free radical polymerization under ultraviolet light; this polymerizable polyurethane thickener not only has the thickening effect of general polyurethane thickeners, but also has the characteristics of photoinitiated polymerization; it is especially suitable for UV In the industrial fields of emulsions, coatings, adhesives, inks, etc., the behavior of pre-tackification and post-crosslinking curing can be realized. Background technique [0002] Thickener, as a common rheology modifier, is widely used in industrial fields. Adding a small amount of thickener to industrial products such as water-based paints, emulsions, inks, and adhesives can signi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G18/66C08G18/48C08G18/10C08G18/30C08J3/03C09D7/43C09J11/08C09D11/00C08F2/48
CPCC08F2/48C08G18/10C08G18/4825C08J3/03C09D11/00C09J11/08C09D7/43C08G18/2805
Inventor 任碧野关涛
Owner SOUTH CHINA UNIV OF TECH