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Organic polymer and novel polymerizable compound

A technique for polymerizing compounds and polymer compositions, applied in the fields of organic chemistry, other chemical processes, chemical instruments and methods, etc., which can solve the problems of inefficiency, high cost, clumsy production methods, etc.

Inactive Publication Date: 2006-06-07
MITSUI CHEM INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, the production methods of these surface improvements are awkward and ineffective, resulting in high cost and in some instances safety problems

Method used

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  • Organic polymer and novel polymerizable compound
  • Organic polymer and novel polymerizable compound
  • Organic polymer and novel polymerizable compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0268] Synthesis of chloroethyloxazolidinone (referred to as "CEOZ") and N-methoxyethyl-N'-hydroxy-ethyl-ethyleneurea (abbreviated as "MHEU").

[0269] 97% sodium hydroxide (173.2 g, 4.20 mol), sodium bicarbonate (378.0 g, 4.50 mol) and water (1500 ml) were mixed to form a homogeneous solution.

[0270] Bis(2-chloroethyl)amine hydrochloride (750.0 g, 4.20 mol) was gradually added to the solution at an internal temperature of 30-50°C over 0.5 hours and aged at 40°C for 4 hours. Chloroform (0.5 L) was added to the reactant with stirring, and allowed to stand, and the lower organic layer was collected. The upper aqueous layer was extracted with 3 portions of 0.5 L of chloroform (total amount: 1.5 L) to collect organic components. These chloroform layers were combined, and the solvent was distilled off to obtain CEOZ (569.8 g, 3.55 mol, pure yield: 84.5%) with a purity of 93.2%.

[0271] The resulting CEOZ structure is characterized as follows:

[0272] 1 H-NMR → see figure 1...

Embodiment 2

[0280] Synthesis of N-methoxyethyl-N'-mercaptoethyl-ethyleneurea ("THEU" for short).

[0281] Phosphorus tribromide (58.0 g, 0.214 mol) was added dropwise to N-methoxyethyl-N'-hydroxyethyl-ethyleneurea (MHEU ) (110.0 g, 0.579 mol). Then it was aged at 50° C. for 2 hours. Chloroform (200 mL) was added to the reaction mixture, and water (50 mL) was added dropwise at an internal temperature of 60°C. The mixture was cooled to room temperature and the layers were separated. The resulting organic layer was concentrated under reduced pressure to obtain crude N-methoxyethyl-N'-bromoethyl-ethyleneurea (130.5 g, 0.520 mol, crude yield: 90%).

[0282] Add thiourea (69.6g, 0.914mol) and water (300mL) into crude N-methoxyethyl-N'-bromoethyl-ethyleneurea, then react at reflux (100-102°C) for 3 hours . Then the reactant was cooled to 40°C, 28% aqueous ammonia (148.0 g, 2.44 mol) was added dropwise at 40-46°C, and the resulting mixture was matured at 55°C for 3 hours.

[0283] After the...

Embodiment 3

[0288] Synthesis of N,N'-bis(hydroxyethyl)-ethyleneurea (abbreviated as "HEEU") and N,N'-bis(mercaptoethyl)-ethyleneurea (abbreviated as "DMEU").

[0289] CEOZ (568.0 g, 3.54 mol) with a purity of 93.2% was added dropwise to 2-aminoethanol (1180.0 g, 19.3 mol) at 105-110° C. over 1 hour. Then it was aged at 110° C. for 3 hours. It was then cooled and 97% aqueous sodium hydroxide (146.0 g, 3.54 mol) and water (220 ml) were added, followed by filtration. Anhydrous magnesium sulfate was added to the filtrate, and filtered again. The filtrate was passed through a silica gel column, and the silica gel column was rinsed with methanol. The silica gel column eluate and eluent (methanol solution) were combined, and the solvent, excess 2-aminoalcohol, etc. were distilled off under reduced pressure. The resulting concentrated residue was purified by silica gel column chromatography to obtain HEEU with a purity of 99% (469.4 g, 2.67 mol, pure yield: 75.4%).

[0290] The resulting stru...

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Abstract

An organic polymer having a water contact angle of 20° or less, preferably having a water contact angle of 7° or less has both high water wettability and high transparency. The organic polymer contains a partially polar structure with a dipole moment of 3 Debye or more, obtainable in particular from the polymerization of polymerizable compounds having an alkylene (thio)urea structure.

Description

technical field [0001] The present invention relates to organic polymers with high water wettability, molded or other molded products capable of providing organic polymers with high water wettability, antifouling materials, and antifogging materials composed of organic polymers, novel polymerizable compounds and compositions , moisture-proof materials, water-absorbent (liquid) materials and optical materials. All of these materials utilize organic polymers with high water wettability and molded or otherwise shaped products. technical background [0002] We know that a representative physical quantity expressing water wettability is the water contact angle. In general, substances with water contact angles lower than 90° are classified as hydrophilic materials, and substances with water contact angles greater than 90° are classified as hydrophobic materials. When the water wetting angle approaches 0° from 90°, the water wettability of the material is higher. [0003] High w...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D263/24C07D233/32C08F2/00C08F4/00C08F20/36C08G18/38C08G73/06C09K3/18G02B1/04
CPCC07D233/32C08F20/36C08G18/38C08G75/00
Inventor 冈﨑光树关亮一中塚史朗
Owner MITSUI CHEM INC
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