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Fluorescent dye monomer, fluorescent copolymer emulsion and preparation method thereof

A technology of fluorescent dyes and polyurethane emulsions, applied in the field of fluorescent dye monomers, can solve problems such as affecting the mechanical properties of waterborne polyurethanes

Inactive Publication Date: 2019-01-29
JIANGSU LIWENJIA CHEM +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, connecting the fluorescent chromophore to the main chain of waterborne polyurethane in a block manner will affect the mechanical properties of the original waterborne polyurethane

Method used

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  • Fluorescent dye monomer, fluorescent copolymer emulsion and preparation method thereof
  • Fluorescent dye monomer, fluorescent copolymer emulsion and preparation method thereof

Examples

Experimental program
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preparation example Construction

[0015] The fluorescent dye monomer is prepared by reacting a naphthalene anhydride compound and a hydroxyl functional agent to obtain a dihydroxy-containing intermediate product, and then the intermediate product is subjected to a substitution reaction with a nucleophilic agent. Specifically, the preparation method of the fluorescent dye monomer comprises the following steps:

[0016] S11, dissolving the naphthalene anhydride compound and the hydroxyl functional reagent in the first solvent, and reacting at the first reaction temperature for the first reaction time to obtain an intermediate product;

[0017] S12, dissolving the intermediate product and the nucleophile in a second solvent, and reacting at a second reaction temperature for a second reaction time to prepare a fluorescent dye monomer.

[0018] In step S11, the naphthalene anhydride compound is halogenated naphthalene anhydride and its derivatives, such as: 4-chloro-1,8-naphthalene anhydride, 4-bromo-1,8-naphthalen...

Embodiment 1

[0053] Embodiment 1—copolymerization fluorescent polyurethane emulsion

[0054] (1) Synthesis of fluorescent dye monomer (A): 4.16 grams of 4-bromo-1,8-naphthalene anhydride, 4.10 grams of 2-amino-1,3-propanediol and 100 milliliters of ethanol are added in a single-necked flask, stirred and heated to React at 80°C for 4 hours. The ethanol was distilled off under reduced pressure, and then 300 ml of water was added, followed by standing, filtering, washing the filter cake with water three times and vacuum drying to obtain the intermediate product I.

[0055] Add 3.5 grams of intermediate product I, 1.62 grams of sodium methoxide and 80 milliliters of methanol into a one-necked flask, stir and raise the temperature to 75° C. for 5 hours. Methanol was distilled off under reduced pressure, and then 200 ml of water was added, followed by standing, filtering, washing the filter cake with water three times and vacuum drying to obtain the fluorescent dye monomer (A).

[0056] (2) Pr...

Embodiment 2

[0058] Embodiment 2—copolymerization fluorescent polyurethane emulsion

[0059] (1) Synthesis of fluorescent dye monomer (A): same as in Example 1.

[0060] (2) Preparation of copolymerized fluorescent polyurethane emulsion: Add 10 grams of isophorone diisocyanate, 12.5 grams of N210 and 2 drops of stannous octoate into a three-necked flask, stir and react at 80°C for 1.5 hours; then add 1.34 grams of dihydroxy Methylbutyric acid, 1.2 g of neopentyl glycol and 0.23 g of fluorescent dye monomer (A) were reacted at 80°C for 4 hours; after cooling down to 30°C, 5 ml of acetone was added to stir to reduce viscosity, and then 1 g of triethylamine was added to neutralize After 30 minutes, 75 milliliters of water was added, stirred for 40 minutes, and acetone was evaporated under reduced pressure to obtain a copolymerized fluorescent polyurethane emulsion.

[0061] The properties of the obtained fluorescent emulsion are shown in Table 1, and the color fastness to light of the corres...

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Abstract

The invention relates to a fluorochrome monomer, copolymeric fluorescent polyurethane emulsion and copolymeric fluorescent polyurethane-acrylic ester copolymer emulsion as well as preparation methods thereof. The dihydroxy-containing fluorochrome monomer is firstly synthesized, the dihydroxy-containing fluorochrome monomer is used as a chain extender and applied to a chain extension reaction of an aqueous polyurethane prepolymer, and after phase inversion, the copolymeric fluorescent polyurethane emulsion is prepared. In addition, the copolymeric fluorescent polyurethane emulsion and an alkene monomer are used for preparing the copolymeric fluorescent polyurethane-acrylic ester copolymer emulsion by emulsion grafting and copolymerization. A fluorescent chromophore group in the polymer emulsion is used as a side group and is bonded to a molecular chain; the polymer emulsion can be used as aqueous film forming resin, and widely applied to the fields of aqueous fluorescent paint, aqueous fluorescent ink, traffic sign, false proof mark, special clothes, leather, etc.

Description

technical field [0001] The invention relates to a fluorescent dye monomer, a copolymerized fluorescent polyurethane emulsion, a copolymerized fluorescent polyurethane-acrylate copolymer emulsion and a preparation method thereof. Background technique [0002] At present, fluorescent polymer emulsions are obtained by blending fluorescent compounds with traditional polymer emulsions. Due to their advantages of energy saving, environmental protection, non-combustibility, and low cost, they have been used as film-forming resins in coatings, adhesives, printing and dyeing, and fabric finishing agents. field is applied. However, due to the poor compatibility between fluorescent compounds and polymer emulsions, the migration and aggregation of fluorescent compounds often occur during the use of the product, resulting in defects such as uneven color, poor color fastness to light, and reduced mechanical properties of the final product. Thereby limiting the wide application of this ty...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D221/14C09B57/08C09B69/10C09K11/06C08F283/00C08G18/12C08G18/30
Inventor 金青君李勃天王吉帅阚成友李翔刘勇
Owner JIANGSU LIWENJIA CHEM
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