P-nitrocinnamic acid modified rapid-reactivity associated thickener as well as preparation method and application thereof

A technology of p-nitrocinnamic acid and associative thickener, which is applied in the field of UV fast-responsive associative thickener and its preparation, can solve the problems of inconspicuous lifting, insufficient distance and photoreactivity, and achieve application Wide range, improved thickening efficiency, and reduced dosage

Active Publication Date: 2022-07-15
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although these associative polymers have their own hydrophobic structure and can increase the viscosity under ultraviolet radiation, due to the problems of the distance between the coumarin and azophenyl groups in the aqueous solution and the insufficient photoreactivity, resulting in short radiation The improvement over time is not obvious

Method used

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  • P-nitrocinnamic acid modified rapid-reactivity associated thickener as well as preparation method and application thereof
  • P-nitrocinnamic acid modified rapid-reactivity associated thickener as well as preparation method and application thereof
  • P-nitrocinnamic acid modified rapid-reactivity associated thickener as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] A preparation method of a fast-reactive associative thickener modified with p-nitrocinnamic acid, comprising the following steps:

[0044] (1) 0.50g (3.40mmol) of p-nitrocinnamic acid, 1.35g (5.10mmol) of 12-bromo-1-dodecanol, 0.82g (7.65mmol) of anhydrous sodium carbonate were dissolved in 10ml of 2- Butanone was added to a 50ml high vacuum thick-walled reaction flask. After blowing out the air in the bottle with nitrogen, the reaction was performed by heating to 85° C. in an oil bath under a nitrogen atmosphere for 15 hours. The reaction end point was confirmed by thin layer chromatography (TLC), the solvent in the reaction flask was removed under reduced pressure, extracted with dichloromethane and saturated brine, and concentrated. The concentrated liquid was dried to obtain a white paste-like solid, which was n-dodecanol p-nitrocinnamic acid, and the yield was 91%.

[0045] The obtained n-dodecanol p-nitrocinnamate is dissolved in CDCl 3 The 1H NMR spectrum data...

Embodiment 2

[0067] A preparation method of a fast-reactive associative thickener modified with p-nitrocinnamic acid, comprising the following steps:

[0068] (1) 0.50g (3.40mmol) of p-nitrocinnamic acid, 0.93g (5.10mmol) of 6-bromo-1-hexanol, 1.06g (7.65mmol) of anhydrous potassium carbonate were dissolved in 10ml of acetone solvent , added to a 50ml high-vacuum thick-walled reaction flask. After blowing out the air in the bottle with nitrogen, the reaction was performed by heating to 80° C. in an oil bath under a nitrogen atmosphere for 17 hours. The reaction end point was determined by thin layer chromatography, the solvent in the reaction flask was removed under reduced pressure, extracted with dichloromethane and saturated brine, and concentrated. The concentrated liquid was dried to obtain a white paste-like solid, which was n-hexanol p-nitrocinnamic acid, and the yield was 93%.

[0069] (2) 7.36g (2.51mmol) of n-hexanol p-nitrocinnamate, 0.36g (3.70mmol) of 4-pentynoic acid, 0.062...

Embodiment 3

[0085] A preparation method of a fast-reactive associative thickener modified with p-nitrocinnamic acid, comprising the following steps:

[0086](1) 0.78g (4.00mmol) of p-nitrocinnamic acid, 1.60g (6.00mmol) of 12-bromo-1-dodecanol, 1.31g (8.5mmol) of anhydrous potassium carbonate were dissolved in 15ml of N, N-dimethylformamide solvent was added to a 50ml high vacuum thick-walled reaction flask. Under an argon atmosphere, the oil bath was heated to 75 °C for 18 h. The reaction end point was determined by thin layer chromatography, the solvent in the reaction flask was removed under reduced pressure, extracted with dichloromethane and saturated brine, and concentrated. The concentrated liquid was dried to obtain a white paste-like solid, which was n-dodecanol p-nitrocinnamic acid, and the yield was 93%.

[0087] (2) 0.90g (2.38mmol) of n-dodecanol p-nitrocinnamic acid, 0.37g (3.80) of 4-pentynoic acid, 0.065g (0.54mmol) of DMAP and 15ml of anhydrous tetrahydrofuran were adde...

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Abstract

The invention discloses a p-nitrocinnamic acid modified rapid reactive associative thickener as well as a preparation method and application thereof. The preparation method comprises the following steps: starting from p-nitrocinnamic acid, sequentially carrying out nucleophilic substitution reaction on p-nitrocinnamic acid and halogenated fatty alcohol to prepare a p-nitrocinnamic acid substituted fatty alcohol end-capping reagent intermediate, and then carrying out esterification reaction on the p-nitrocinnamic acid substituted fatty alcohol end-capping reagent intermediate and 4-pentynoic acid to prepare a p-nitrocinnamic acid end-capping reagent containing terminal alkynyl; hydroxyl-terminated polyethylene glycol is used as an initial polymer, and an azido-terminated precursor polymer is synthesized through a two-step reaction. A click chemical synthesis strategy is used, and p-nitro cinnamic acid groups are efficiently modified to two ends of a hydrophilic polyethylene glycol main chain to obtain the p-nitro modified reactive associative polymer. An aqueous solution (with the concentration of 3 wt%) of the compound is subjected to a photodimerization reaction under the irradiation of 365nm ultraviolet light, and under a 25.8 mw/cm < 2 > light source, the viscosity of the solution is increased by 614 times after the solution is irradiated for 75s compared with that before the solution is irradiated.

Description

technical field [0001] The invention relates to an associative thickener with UV photo-promoting reactivity, in particular to a UV fast-reactive associative thickener modified with p-nitrocinnamic acid and a preparation method thereof; the thickener It is a kind of solution that can rapidly increase the viscosity of solution under ultraviolet radiation; it is especially suitable for the industrial fields of water-based UV formulations such as emulsions, coatings, adhesives, inks, etc. to control the rheological properties of the system; it belongs to the field of water-based thickeners. Background technique [0002] Associative thickeners are commonly used in industry as rheological additives, and are used in food and beverage, cosmetics, inks, coatings, leather and other fields. The control of rheological properties in these products affects the final properties and applications of the products, and the market for rheological additives has shown an increasing trend in recen...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G65/338C08G65/333C08G65/325C08G65/334C09D11/00C09D7/43C09J11/08C08J3/03C08L101/00C08L71/02
CPCC08G65/338C08G65/33389C08G65/325C08G65/3346C09D11/00C09D7/43C09J11/08C08J3/03C08J2300/00C08J2471/02
Inventor 任碧野王玲
Owner SOUTH CHINA UNIV OF TECH
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