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Dual luminous water-based polyurethane paint based on chromophores in hydroxyl-terminated polylactic acid and preparation method thereof

A water-based polyurethane and hydroxypolylactic acid technology, applied in the preparation of luminescent materials, luminescent coatings, organic compounds, etc., can solve the problems of small molecule migration, poor luminescence stability and durability, and increased cost, and reduce the use and distribution of organic solvents. Wide and adjustable effect with long-lasting luminous performance

Inactive Publication Date: 2017-03-15
UNIV OF SCI & TECH OF CHINA
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  • Summary
  • Abstract
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  • Claims
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Problems solved by technology

Chinese patent 201310509518.3 discloses a fluorescent paint prepared by compounding fluorescent powder with epoxy resin, deionized water and other additives. However, since the fluorescent powder used has certain radiation on the body, it cannot be exposed to more; Moreover, this fluorescent powder is an inorganic substance, and the luminous paint obtained by blending with an organic polymer resin has compatibility and storage stability problems. cause safety hazard
[0003] Chinese patent 201510712140.6 discloses a preparation method of luminous water-based polyurethane coatings. The hydroxyl-terminated compound containing fluorescent groups is used as a chain extender to react with isocyanate, and is embedded in the structural unit of water-based polyurethane in the form of chemical bonds, which solves the problem of blending and compounding. Poor compatibility between fluorescent agent and water-based polyurethane, easy migration and precipitation during use
However, the small molecules with chromophores introduced by the above method for preparing luminescent coatings have relatively large side groups such as benzene rings and condensed rings. As a chain extender, there is a problem of ester solubility in the polyurethane chain, and organic solvents need to be added to complete the polymerization. This brings inconvenience to large-scale industrial production, and the introduction of a large number of organic solvents will also increase the cost

Method used

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  • Dual luminous water-based polyurethane paint based on chromophores in hydroxyl-terminated polylactic acid and preparation method thereof
  • Dual luminous water-based polyurethane paint based on chromophores in hydroxyl-terminated polylactic acid and preparation method thereof
  • Dual luminous water-based polyurethane paint based on chromophores in hydroxyl-terminated polylactic acid and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] 1. Add 4g of 4-fluorobenzophenone, 10.5g of 2-methylaminoethanol and 4.14g of potassium carbonate into a 250mL three-necked flask, stir with a magnetic stirrer and heat up to 130°C, react for 12 hours, and cool down to end the reaction . Add 100 mL of deionized water into the flask, stir at room temperature for 1 hour, a solid precipitates, and filter under reduced pressure to obtain a light yellow solid. The product was dried in a vacuum oven to obtain 3.22 g of a pale yellow product (4-((2-hydroxyethyl)(methyl)amino)phenyl)benzophenone (NBP), with a yield of 0.63. The product is soluble in dichloromethane, ethyl acetate and other solvents.

[0040] 2. In N 2 Under protection, add 0.3g initiator (4-((2-hydroxyethyl)(methyl)amino)phenyl)benzophenone (NBP), 29.7g D successively to the reaction flask with magnetic stirring bar, L-lactide, 0.6g n-hexane solution of stannous octoate. The reaction vial was sealed and immersed in an oil bath at 130°C for reaction. When t...

Embodiment 2

[0048] 1. Add 5.4g of 4,4-dichlorobenzophenone, 11.25g of 2-methylaminoethanol and 4.44g of potassium carbonate into a 250mL three-neck flask, stir with a magnetic stirrer, heat up to 130°C, and react for 12 hours , cooling down to end the reaction. After cooling down to room temperature, 120 mL of deionized water was added and stirred at room temperature for 1 hour. After an oily precipitate appeared, the water layer was separated from the oily precipitate to obtain a brownish-yellow oil. Use ethyl acetate:petroleum ether at a volume ratio of 2:1 as the eluent, separate and purify with a chromatographic column (200-300 mesh silica gel) to obtain a light yellow solution; use vacuum distillation to remove the solvent to obtain a yellow powder Finally, it was dried in a vacuum oven to obtain 3.40 g of yellow product (4-chlorophenyl) (4-((2-hydroxyethyl)(methyl)amino)benzophenone (NBP-Cl ), the productive rate is 0.55. This product is soluble in solvents such as dichloromethane,...

Embodiment 3

[0057] 1. Add 6.0g of 1-(4-chlorophenyl)-3-phenylpropane-1,3-dione, 14.47g of 2-methylaminoethanol and 6.2g of potassium carbonate into a 250mL three-necked flask and stir with a magnetic force Stir in a container, and heat up to 130° C., react for 12 hours, and cool down to complete the reaction. Add 150 mL of deionized water into the flask, stir at room temperature for 1 hour, and a solid precipitates, which is filtered under reduced pressure to obtain a light yellow solid. The product was placed in a vacuum oven and dried to obtain 4.13g of light yellow product 1-(4-((2-hydroxyethyl)(methyl)amino)phenyl)-3-phenylpropane-1,3-dione ( HMP), the yield was 0.60. The product is soluble in dichloromethane, ethyl acetate and other solvents.

[0058] 2. In N 2Under protection, add 0.9g initiator 1-(4-((2-hydroxyethyl)(methyl)amino)phenyl)-3-phenylpropane-1,3 - Diketone, 17.1g D, L-lactide, 0.36g n-hexane solution of stannous octoate, seal the reaction bottle and immerse it in an...

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Abstract

The invention discloses a preparation method of a dual luminous water-based polyurethane paint based on chromophores in hydroxyl-terminated polylactic acid. The preparation method is characterized by comprising the following steps: initiating D,L-lactide to perform ring-opening polymerization by means of synthesized small molecule alcohol having fluorescence / phosphorescence dual emitting chromophores, thereby preparing hydroxyl-terminated polylactic acid having a fluorescence / room temperature phosphorescence dual emitting function; then reacting with large molecule dibasic alcohol, diisocyanate, small molecule dibasic alcohol and hydrophilic chain extender to prepare a dual luminous water-based polyurethane prepolymer emulsion; and finally, adding defoaming agent, leveling agent, thickener and deionized water, and compounding to prepare the water-based polyurethane paint having a dual luminescence function. According to the method disclosed by the invention, the prepared water-based polyurethane paint having a dual luminescence function can emit bright blue-green fluorescence and green phosphorescence under the condition of ultraviolet irradiation; the chromophore content can be regulated and controlled in a wide range; and a formed paint film has the advantages of high pencil hardness, strong adhesion, favorable shock resistance and water resistance, low chromophore migration possibility and lasting luminescence.

Description

technical field [0001] The invention belongs to the technical field of functional water-based polyurethane materials, and in particular relates to a double-luminescent water-based polyurethane paint based on chromophores in hydroxyl polylactic acid and a preparation method thereof. Background technique [0002] Luminous paints are widely used in daily life, such as for fire safety, traffic instructions, advertising signs, luminous fabrics, etc. The traditional method is to blend small molecule luminescent materials with resins, solvents and various additives to make luminescent paints. Chinese patent 201310509518.3 discloses a fluorescent paint prepared by compounding fluorescent powder with epoxy resin, deionized water and other additives. However, since the fluorescent powder used has certain radiation on the body, it cannot be exposed to more; Moreover, this fluorescent powder is an inorganic substance, and the luminous paint obtained by blending with an organic polymer ...

Claims

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Application Information

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IPC IPC(8): C09D175/06C09D5/22C08G18/42C08G63/08C08G63/85C07C221/00C07C225/22C09K11/06
CPCC09D175/06C07C221/00C08G18/428C08G63/08C08G63/823C09D5/22C09K11/06C09K2211/1007
Inventor 张兴元黄晓雯戎佳萌孙伟王涛
Owner UNIV OF SCI & TECH OF CHINA
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