Fluorescent Polyurethane Emulsion Based on Diketopyrrolopyrrole Derivatives

Abstract

The invention relates to a fluorescent polyurethane emulsion, in particular to a fluorescent polyurethane emulsion based on a diketopyrrolopyrrole derivative. The fluorescent polyurethane emulsion has higher fluorescence intensity and higher molecular weight, and further, the fluorescence effect after film forming is better. The fluorescent polyurethane emulsion is more expected to be applied to the fields of anti-counterfeit marking, medical treatment, fluorescent paint and the like.

Description

technical field

[0001] The invention relates to a fluorescent polyurethane emulsion, in particular to a fluorescent polyurethane emulsion based on diketopyrrolopyrrole derivatives. Background technique

[0002] Fluorescent polymer material is a functional polymer material that emits fluorescence under ultraviolet light. In recent years, good progress has been made in the research and application of fluorescent sensors, drug carriers, fluorescent imaging, and fluorescent probes. Since the traditional water-based fluorescent polyurethane system is generally formed by blending fluorescent pigments and polyurethane emulsion, the stability of the system itself, the solvent elution resistance and the color fastness to light of the product are poor.

[0003] Due to the poor compatibility between ordinary fluorescent pigment / dye molecules and polyurethane macromolecules, the method based on physical coating cannot completely prevent the migration and diffusion of fluorescent dye mol...

Examples

Embodiment 1

[0038]

[0039] (1) Under the protection of dry nitrogen, place 0.0001mol of the compound shown in formula Ia and 15mol of dehydrated diphenylmethane diisocyanate (MDI) in a reactor with a temperature control device and a stirring device, stir and heat up to 60°C-80°C, keep in this state for 6 hours, cool, and dry to constant weight to obtain mixture a;

[0040] (2) Add 2 mol of polypropylene glycol (Mw=500 to 3,000), 1 mol of 2,2-dimethylol propionic acid (DMPA), 1.5 mol of 1,4-butanediol and 0.001 mol of 0.2% dibutyltin dilaurate (Catalyst) added to the reaction with the above mixture a, stirred at 20°C to 30°C for 2 hours to 7 hours, then added 5mol triethanolamine to the reactor and stirred at 60°C to 70°C for at least 30 minutes, then added Stir and emulsify with water to obtain the target substance (abbreviated as "DPP-1WPU(A)"), whose fluorescence spectrum is shown in figure 1 ..

Embodiment 2

[0042]

[0043] (1) Under the protection of dry nitrogen, 0.001mol of the compound shown in formula Ib and 0.8mol of toluene-2,4-diisocyanate (TDI) after dehydration are placed in a reactor with a temperature control device and a stirring device, Stir and heat up to 60°C to 80°C, keep in this state for 6 hours, cool, and dry to constant weight to obtain mixture b;

[0044] (2) 0.1mol polypropylene glycol (Mw=500~3,000), 0.01mol DMPA, 1mol pentylene glycol and 0.076mol of 0.2% dibutyltin dilaurate (catalyst) are added to the reaction with the above mixture b, 20 Stir at ℃~30℃ for 2 hours~7 hours, then add 5mol triethylamine to the reactor and stir at 60℃~70℃ for at least 30 minutes, then add water to stir and emulsify to obtain the target product (abbreviated as "DPP- 2WPU"), its fluorescence spectrum is shown in figure 1 ..

Embodiment 3

[0046]

[0047] (1) Under the protection of dry nitrogen, place 0.01 mol of the compound shown in formula Ic and 3.8 mol of MDI after dehydration in a reactor with a temperature control device and a stirring device, stir and heat up to 60°C to 80°C, Keep in this state for 6 hours, cool and dry to constant weight to obtain mixture c;

[0048] (2) 18mol polyethylene glycol (Mw=500~3,000), 1.8mol DMPA, 35mol glycerol and 2.023mol of 0.2% dibutyltin dilaurate (catalyst) are added to the reaction of the above mixture c, Stir at 20°C to 30°C for 2 hours to 7 hours, then add 6mol triethylamine to the reactor and stir at 60°C to 70°C for at least 30 minutes, then add water to stir and emulsify to obtain the target product (abbreviated as "DPP -3WPU").

technical field

[0001] The invention relates to a fluorescent polyurethane emulsion, in particular to a fluorescent polyurethane emulsion based on diketopyrrolopyrrole derivatives. Background technique

[0002] Fluorescent polymer material is a functional polymer material that emits fluorescence under ultraviolet light. In recent years, good progress has been made in the research and application of fluorescent sensors, drug carriers, fluorescent imaging, and fluorescent probes. Since the traditional water-based fluorescent polyurethane system is generally formed by blending fluorescent pigments and polyurethane emulsion, the stability of the system itself, the solvent elution resistance and the color fastness to light of the product are poor.

[0003] Due to the poor compatibility between ordinary fluorescent pigment / dye molecules and polyurethane macromolecules, the method based on physical coating cannot completely prevent the migration and diffusion of fluorescent dye mol...

Examples

Embodiment 1

[0038]

[0039] (1) Under the protection of dry nitrogen, place 0.0001mol of the compound shown in formula Ia and 15mol of dehydrated diphenylmethane diisocyanate (MDI) in a reactor with a temperature control device and a stirring device, stir and heat up to 60°C-80°C, keep in this state for 6 hours, cool, and dry to constant weight to obtain mixture a;

[0040] (2) Add 2 mol of polypropylene glycol (Mw=500 to 3,000), 1 mol of 2,2-dimethylol propionic acid (DMPA), 1.5 mol of 1,4-butanediol and 0.001 mol of 0.2% dibutyltin dilaurate (Catalyst) added to the reaction with the above mixture a, stirred at 20°C to 30°C for 2 hours to 7 hours, then added 5mol triethanolamine to the reactor and stirred at 60°C to 70°C for at least 30 minutes, then added Stir and emulsify with water to obtain the target substance (abbreviated as "DPP-1WPU(A)"), whose fluorescence spectrum is shown in figure 1 ..

Embodiment 2

[0042]

[0043] (1) Under the protection of dry nitrogen, 0.001mol of the compound shown in formula Ib and 0.8mol of toluene-2,4-diisocyanate (TDI) after dehydration are placed in a reactor with a temperature control device and a stirring device, Stir and heat up to 60°C to 80°C, keep in this state for 6 hours, cool, and dry to constant weight to obtain mixture b;

[0044] (2) 0.1mol polypropylene glycol (Mw=500~3,000), 0.01mol DMPA, 1mol pentylene glycol and 0.076mol of 0.2% dibutyltin dilaurate (catalyst) are added to the reaction with the above mixture b, 20 Stir at ℃~30℃ for 2 hours~7 hours, then add 5mol triethylamine to the reactor and stir at 60℃~70℃ for at least 30 minutes, then add water to stir and emulsify to obtain the target product (abbreviated as "DPP- 2WPU"), its fluorescence spectrum is shown in figure 1 ..

Embodiment 3

[0046]

[0047] (1) Under the protection of dry nitrogen, place 0.01 mol of the compound shown in formula Ic and 3.8 mol of MDI after dehydration in a reactor with a temperature control device and a stirring device, stir and heat up to 60°C to 80°C, Keep in this state for 6 hours, cool and dry to constant weight to obtain mixture c;

[0048] (2) 18mol polyethylene glycol (Mw=500~3,000), 1.8mol DMPA, 35mol glycerol and 2.023mol of 0.2% dibutyltin dilaurate (catalyst) are added to the reaction of the above mixture c, Stir at 20°C to 30°C for 2 hours to 7 hours, then add 6mol triethylamine to the reactor and stir at 60°C to 70°C for at least 30 minutes, then add water to stir and emulsify to obtain the target product (abbreviated as "DPP -3WPU").

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