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Preparation method of fluorescent waterborne polyurethane emulsion based on chromophore in diisocyanate

A technology of diisocyanate and water-based polyurethane, applied in luminescent materials, chemical instruments and methods, organic chemistry, etc., can solve the problems of color variety, fluorescent function, vividness, migration resistance and weather resistance, and insufficient content of fluorescent conjugated groups control, complex reaction and other issues, to achieve the effect of good fluorescence intensity persistence, not easy to migrate, and uniform distribution

Active Publication Date: 2013-06-26
UNIV OF SCI & TECH OF CHINA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the limitation of the solubility of small molecule fluorescent pigments or dyes in water, the compatibility of fluorescent pigments or dye particles with water-based polyurethane, the migration of fluorescent pigments or dye particles during the use of materials, etc., the obtained products have fluorescent functions. Current water-based polyurethane materials are deficient in color variety, fluorescent function, vividness, migration resistance and weather resistance, and some small molecule fluorescent pigments or heavy metals in dyes will also bring certain environmental problems
[0004] Chinese patent 200910308614.5 discloses a water-soluble fluorescent conjugated polymer and its synthesis method, which is mainly carried out by introducing a hydrophobic conjugated main chain and a hydrophilic ionic functional group side chain. During the synthesis process, acetone, A variety of organic solvents such as ether, DMF, and methanol, the reaction is more complicated and takes a long time, and the content of fluorescent conjugated groups in the polymer is uncontrollable
Therefore, this synthetic method is basically not suitable for the synthesis and preparation of fluorescent waterborne polyurethane.

Method used

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  • Preparation method of fluorescent waterborne polyurethane emulsion based on chromophore in diisocyanate
  • Preparation method of fluorescent waterborne polyurethane emulsion based on chromophore in diisocyanate
  • Preparation method of fluorescent waterborne polyurethane emulsion based on chromophore in diisocyanate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Add 10.00 grams of HDI and 9.88 grams of FL into a three-necked flask, add 60 milliliters of N,N-dimethylformamide as a solvent, and then add 0.01 grams of DBTDL as a catalyst, react at 60°C for 5 hours under mechanical stirring, and cool to 30 The solvent was distilled off under reduced pressure at ℃, and then the product was washed with acetone for 3 times, and the washed product was placed in a vacuum oven and dried to constant weight to obtain fluorescent diisocyanate FLDI.

[0048] 36.00 g of PTMG (M n =2000) into a 500ml three-necked flask, dehydrated at 115°C for 1 hour and then cooled to 50°C. Take 7.95 grams of fluorescent diisocyanate FLDI and 15.60 grams of IPDI into a three-necked flask, stir and react at 85°C for 3 hours, then add 3.70 grams of hydrophilic chain extender DMPA, 2.80 grams of BDO, 0.02 grams of DBTDL and 45.00 grams of methyl ethyl ketone. Stir and react at 75°C for 3 hours, then cool down to 30°C, transfer the reaction product to a high-spe...

Embodiment 2

[0053] Add 6.00 g of p-phenylene diisocyanate and 20 ml of N,N-dimethylformamide into a three-necked flask, raise the temperature to 30°C, add ST6.60 g and 30 ml of N,N-dimethylformamide dropwise under mechanical stirring The solution is controlled to be added dropwise in half an hour. After keeping the reaction at 30°C for 2 hours, the solvent was distilled off under reduced pressure, and the product was washed once with dichloromethane. The washed product was placed in a vacuum drying oven and dried to constant weight to obtain fluorescent diisocyanate STDI.

[0054] Add 10.00 g of HDI trimer and 20 ml of N,N-dimethylformamide into a three-necked flask, raise the temperature to 30°C, add 2.84 g of AN and 6 ml of N,N-dimethylformamide dropwise under mechanical stirring Solution, control the dropwise addition in half an hour. After keeping the reaction at 30°C for 2 hours, the solvent was distilled off under reduced pressure, and the product was washed once with dichlorometha...

Embodiment 3

[0058] Add 25.00 grams of HDI trimer and 30 milliliters of N,N-dimethylformamide into a 250-mL three-necked flask, raise the temperature to 30 ° C, protect with nitrogen, and add 4.50 grams of Azure A1 and 30 milliliters of N , The solution of N-dimethylformamide was added dropwise in half an hour. After keeping the reaction at 30°C for 2 hours, the solvent was distilled off under reduced pressure, and the product was washed once with acetone. The washed product was placed in a vacuum drying oven and dried to constant weight to obtain fluorescent diisocyanate AADI.

[0059] 60.00 grams of PPG (M n =1000) into a 500mL three-necked flask, dehydrated at 120°C for 1 hour and then cooled to 50°C. Take 18.00 grams of fluorescent diisocyanate AADI, 35.00 grams of TDI, and 0.03 grams of DBTDL into a three-necked flask, stir and react at 80°C for 3 hours, then add 7.20 grams of hydrophilic chain extender DMPA, 8.60 grams of DEG and 90.00 grams of acetone , constant temperature was st...

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Abstract

The invention discloses a preparation method of a fluorescent waterborne polyurethane emulsion based on chromophore in diisocyanate. The preparation method is characterized by comprising the following steps of: enabling monoamine or monohydric alcohol containing fluorescent chromophore to be reacted with isocyanate, or enabling diamine or dihydric alcohol containing the fluorescent chromophore to be reacted with diisocyanate with a symmetric structure to synthesize diisocyanate containing the fluorescent chromophore, and then combining the diisocyanate containing the fluorescent chromophore with common diisocyanate to partially or completely substitute for the common diisocyanate to prepare the fluorescent waterborne polyurethane. According to the preparation method disclosed by the invention, the hard segment content and type of the prepared fluorescent waterborne polyurethane and the content (2-40wt%) of the fluorescent chromophore are controllable by adjusting the types and proportions of the diisocyanate and a chain extender, and the prepared fluorescent waterborne polyurethane has the advantages that the fluorescent chromophore is uniformly distributed and difficult to migrate, the fluorescent intensity is good in durability, and improvement in terms of optical, thermal and certain functional characteristics can be achieved while the fluorescent property is achieved.

Description

technical field [0001] The invention belongs to the technical field of water-based polyurethane materials, and in particular relates to the synthesis of diisocyanates with fluorescent chromophores and the preparation method of fluorescent water-based polyurethane emulsions formed by using the diisocyanates to partially or completely replace common diisocyanates. Background technique [0002] Since water-based polyurethane uses water as the dispersion medium, it has outstanding environmental protection advantages and excellent comprehensive performance. In recent years, it has gradually replaced solvent-based polyurethane. Giving fluorescent function to water-based polyurethane can greatly increase its application in water-based paints, water-based dyes, water-based inks, textiles, environmental testing, medical research and other fields. [0003] The existing general methods for synthesizing water-soluble fluorescent polymers include reacting the reactive functional groups o...

Claims

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Application Information

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IPC IPC(8): C08G18/78C08G18/66C09K11/06C07D493/10C07D279/18
Inventor 张兴元李军配周静李发萍
Owner UNIV OF SCI & TECH OF CHINA
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