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Side chain type water-soluble polyquaternium and preparation method thereof

A technology of water-soluble poly and quaternary ammonium salts, applied in the fields of botanical equipment and methods, chemical instruments and methods, and preparation of organic compounds, can solve the problems of poor reaction selectivity and high cost, and achieve less waste and strong operability. , The preparation method is simple and controllable

Active Publication Date: 2019-01-25
DALIAN BIO CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the polyquaternium antibacterial material prepared by the above method has good antibacterial properties, the main raw materials used in the synthesis process all contain dihalides, which have disadvantages such as poor reaction selectivity and high cost, which limits its application to a certain extent.

Method used

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  • Side chain type water-soluble polyquaternium and preparation method thereof
  • Side chain type water-soluble polyquaternium and preparation method thereof
  • Side chain type water-soluble polyquaternium and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Embodiment 1: Preparation of 3-ethyl-oxetane-3-methoxyethyl didecyl tertiary amine

[0026] In a 500mL four-neck flask equipped with mechanical stirring, add 7.6g ethanolamine, 44.0g chlorodecane, 220mL tetrahydrofuran, 30.4g triethylamine, 0.2g potassium iodide, heat to 50-60°C for 8 hours, TLC detection shows After the reaction is completed, the temperature of the reaction solution is lowered to 25-30° C., and then 33.7 g of 3-p-toluenesulfonyloxymethyl-3-ethyl-oxetane and 12.6 g of triethylamine are added, and the reaction is kept for 24 hours. The reaction solution was added with water and stirred, then extracted with ethyl acetate, the combined ethyl acetate layers were washed and precipitated, the residue was recrystallized by adding 50% ethanol, and after drying, 39.5g of light yellow needle-shaped crystals were obtained, the yield was 72%, and the content was ≥98.0%. . 1 H NMR (CDCl 3 )δ:4.23~4.51(m,4H),3.82(s,2H),3.35(t,2H),2.63(t,4H),2.28(t,2H),1.64(m,2H),1....

Embodiment 2

[0027] Embodiment 2: Preparation of 3-ethyl-oxetane-3-methoxyethyl dihexadecyl tertiary amine

[0028] In a 500mL four-neck flask equipped with mechanical stirring, add 7.6g ethanolamine, 65.0g hexadecane chloride, 180mL N,N-dimethylformamide, 30.4g triethylamine, 0.3g potassium iodide, and heat to 50~ React at 60°C for 12 hours, TLC detection shows that the reaction is complete, lower the temperature of the reaction solution to 25-30°C, then add 33.7g 3-p-toluenesulfonyloxymethyl-3-ethyl-oxetane and 12.6g Triethylamine, heat preservation reaction for 24 hours, the reaction solution was added with water and stirred, then extracted with ethyl acetate, the combined ethyl acetate layers were washed and precipitated, the residue was recrystallized by adding 95% ethanol, and after drying, 47.5g light yellow powder was obtained. The rate is 63%, and the content is ≥98.0%. 1 H NMR (CDCl 3 )δ: 4.20~4.48(m,4H),3.79(s,2H),3.23(t,2H),2.45(t,4H),2.16(t,2H),1.52(m,2H),1.28~1.51 (m,56H),...

Embodiment 3

[0029] Embodiment 3: the preparation of compound (Ia)

[0030] In a 250mL four-necked bottle equipped with mechanical stirring and nitrogen protection device, add 0.70g of boron trifluoride ether, 0.16g of ethylene glycol and 25mL of anhydrous dichloromethane, cool down to 0-5°C, and keep dropping at this temperature Add 27.8 g of 3-ethyl-oxetane-3-methoxyethyldidecyl tertiary amine and 22.0 g of 3-ethyl-3-hydroxymethyl-oxetane to 100 mL of dichloromethane Solution, continue to stir at this temperature for 15 hours after the dropwise addition is completed, add 1g deionized water, 2g anhydrous sodium sulfate and 10g diatomaceous earth to the reaction solution, filter after stirring for half an hour, add dichloromethane to the filtrate Transfer 220mL of deionized water into a 500mL four-necked bottle equipped with a mechanical stirring and ventilating device, feed in methyl chloride gas under stirring, continue stirring for 1 hour after the ventilating is completed, then feed in...

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Abstract

The invention discloses side chain type water-soluble polyquaternium shown as a formula and a preparation method thereof. After ethanolamine and long-chain chloralkane are subjected to substitution reaction under an alkaline condition; a reaction solution is not treated and is subjected to the substitution reaction with 3-p-toluenesulfonyloxymethyl-3-ethyl-oxetane to generate a monomer containinga tertiary amine group; the monomer and a hydrophilic monomer are subjected to cationic ring-opening copolymerization under the action of an initiator and a co-initiator, and are treated through halomethane to obtain the side chain type water-soluble polyquaternium. The polyquaternium is novel in structure and low in toxicity and has good water solubility and a relatively strong bacterium-inhibition and antibacterial function; no bubbles are generated in a utilization process; the polyquaternium has a wide application prospect in the fields of industrial circulating water treatment, personal care products, papermaking, coating, metal processing, textiles and the like.

Description

technical field [0001] The invention relates to a side chain type water-soluble polyquaternary ammonium salt and a preparation method thereof, belonging to the field of fine chemicals. Background technique [0002] Industrial fungicides refer to preparations used to kill or inhibit the growth of microorganisms in the industrial field. Bactericides, bacteriostats, preservatives, antifungal agents, algicides, etc. used in industry are all called industrial fungicides. The fields mainly include industrial circulating water treatment, metal processing, pulp and paper, oil field, coatings, adhesives, personal care cleaning and polymer emulsion, etc. Industrial fungicides can generally be divided into two categories: oxidizing fungicides and non-oxidizing fungicides. Quaternary ammonium salt fungicides are a class of antibacterial surfactants and are one of the most widely used non-oxidizing fungicides. Currently widely used quaternary ammonium salt fungicides are organic small m...

Claims

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Application Information

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IPC IPC(8): C07C213/00C07C213/08C07C217/08C07D305/06A01N33/12A01P1/00A01P3/00C08G65/26
CPCA01N33/12C07C213/00C07C213/08C07C217/08C07D305/06C08G65/2618C08G2650/50
Inventor 赵建新杨兆辉宋宝华单忠峰杨红文赵林贾儒李龙杨平
Owner DALIAN BIO CHEM
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