Biquaternary ammonium salt-containing diamine or diol monomer, preparation method of monomer, water-based non-toxic antibacterial polyurethane emulsion prepared by monomer, and preparation method of emulsion

A technology of polyurethane emulsion and biquaternary ammonium salt, applied in the field of polyurethane emulsion, can solve the problems of weak cationic activity, limited application, cytotoxicity, etc., and achieve the effect of improving antibacterial effect.

Active Publication Date: 2013-12-04
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the weak cationic activity of the cationic water-based polyurethane tertiary amine group, the polyurethane emulsion has poor antibacterial properties, so the application in the field of antibacterial materials is greatly restricted, and the water-based polyurethane uses aromatic isocyanate, which has cell Toxicity, the application in food packaging, water treatment, medical and sanitation, biological materials and other fields will also be greatly restricted

Method used

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  • Biquaternary ammonium salt-containing diamine or diol monomer, preparation method of monomer, water-based non-toxic antibacterial polyurethane emulsion prepared by monomer, and preparation method of emulsion
  • Biquaternary ammonium salt-containing diamine or diol monomer, preparation method of monomer, water-based non-toxic antibacterial polyurethane emulsion prepared by monomer, and preparation method of emulsion
  • Biquaternary ammonium salt-containing diamine or diol monomer, preparation method of monomer, water-based non-toxic antibacterial polyurethane emulsion prepared by monomer, and preparation method of emulsion

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0090] After the amine group of DAPA is protected by conventional tert-butoxy group, it is dissolved in dichloromethane with NG1 at a molar ratio of 1.1:1.0, and then the temperature is lowered to 0°C or below, and 1.1 molar amount of DAPA is added. Double compound condensing agent, in which N, N'-dicyclohexylcarbodiimide: 1-hydroxybenzotriazole = 1.05: 1, react at room temperature for 24 hours, and obtain bis-quaternary ammonium salt diamine protected by tert-butoxy Add the bis-quaternary ammonium salt diamine protected by tert-butoxy to dissolve in methanol, then add ethyl acetate with saturated hydrogen chloride equal to the volume of methanol at room temperature, stir for 3 hours, and then use C18-RP reverse-phase silica gel column chromatography The double quaternary ammonium salt diamine monomer was purified by the method, and the eluent was water / methanol.

Embodiment 2

[0092] After the amine group of lysine is protected by conventional tert-butoxy group, it is dissolved in tetrahydrofuran with NG8 at a molar ratio of 1.05:1.0, and then the temperature is lowered to 0°C or below, and 1.05 times the molar amount of lysine is added Composite condensing agent, in which N, N'-dicyclohexylcarbodiimide: N-hydroxysuccinimide = 1.1: 1, react at room temperature for 36 hours to obtain bis-quaternary ammonium diamine protected by tert-butoxy; Butoxy-protected bis-quaternary ammonium diamine is dissolved in ethanol, then add ethyl acetate with saturated hydrogen chloride equal to the volume of ethanol at room temperature, stir for 3 hours, and purify by precipitation (methanol / petroleum ether) to obtain bis-quaternary ammonium salt diamine monomer. The proton nuclear magnetic resonance spectrum figure of this double quaternary ammonium salt diamine monomer is shown in figure 1 .

Embodiment 3

[0094] After the amine group of lysine is protected by conventional tert-butoxy group, it is dissolved in N,N dimethylformamide with NG12 at a molar ratio of 1.2:1.0, and then the temperature is lowered to 0°C or below, and lysine is added 1.2 times the molar weight of the compound condensing agent, where N, N'-dicyclohexylcarbodiimide:N-hydroxysuccinimide=1.3:1, reacted at room temperature for 36h, and obtained the biquaternary Ammonium salt diamine; add the bisquaternary ammonium salt diamine protected by tert-butoxy group into dichloromethane to dissolve, then add ethyl acetate with saturated hydrogen chloride equal to the volume of dichloromethane at room temperature, stir for 4 hours, and then use C18 -RP reverse-phase silica gel column chromatography to obtain bis-quaternary ammonium diamine monomer, and the eluent is water / methanol. The proton nuclear magnetic resonance spectrum figure of this double quaternary ammonium salt diamine monomer is shown in figure 2 .

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Abstract

The invention discloses a biquaternary ammonium salt-containing diamine or diol monomer with the following structural general formula, and also discloses a preparation method of the monomer, water-based non-toxic antibacterial polyurethane emulsion prepared by the monomer, and a preparation method of the emulsion. The biquaternary ammonium salt-containing diamine or diol monomer disclosed by the invention can easily serve as a chain extender with an antibacterial function to be introduced into polyurethane, so the antibacterial effect of the polyurethane is greatly improved; the biquaternary ammonium salt-containing diamine or diol monomer disclosed by the invention also can be introduced quantitatively as required so as to meet different antibacterial requirements; the water-based non-toxic antibacterial polyurethane emulsion disclosed by the invention has a unique multi-block structure and a suspended group with an excellent antibacterial effect, and can form a stable emulsion in water; the structure and the performance of the water-based non-toxic antibacterial polyurethane emulsion are easy to regulate and control; the water-based non-toxic antibacterial polyurethane emulsion has excellent biocompatibility, adhesion resistance, biomembrane formation resistance and antibacterial performance, and can be widely applied to antibacterial treatment in the fields of textile, plastic, food packaging, daily necessities, water treatment, medical treatment and public health and the like; and the preparation process of the water-based non-toxic antibacterial polyurethane emulsion is simple, mature in process, easy to control and convenient to industrialize.

Description

technical field [0001] The invention belongs to diamine or diol monomers containing diquaternary ammonium salts and polyurethane emulsions prepared from diamine or diol monomers containing diquaternary ammonium salts, including the technical field of preparation, in particular to a diquaternary ammonium salt-containing polyurethane emulsion Monomer of diamine or diol and preparation method thereof, water-based non-toxic antibacterial polyurethane emulsion prepared therefrom and preparation method thereof. Background technique [0002] As a new type of polymer material, polyurethane has been widely used in medical, health, food and other industrial fields due to its good biocompatibility and excellent physical and mechanical properties. Ordinary polyurethane body materials do not have antibacterial effect, but polyurethane molecules have strong designability and good tailorability, and can achieve multiple functions by introducing special functional groups, such as the introd...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C237/10C07C231/12C08G18/73C08G18/75C08G18/66C08G18/48C08G18/32C08G18/10
Inventor 谭鸿李洁华张怡傅强高云龙
Owner SICHUAN UNIV
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