Polyether compound and gas separation membrane

[0166]Example

[0167]Hereinafter, the present invention will be specifically described in Examples and Comparative Examples. Hereinafter, as long as there is no specification, "part" is the weight reference. In addition, the test, the evaluation is as follows.

[0168][Number average molecular weight (MN) and molecular weight distribution (Mw / Mn)]

[0169]The measurement was carried out by a polystyrene conversion by a gel permeation chromatography (GPC) of tetrahydrofuran as a solvent. In addition, using HLC-8320 (TOSOH Co., Ltd.) as the measurement instrument, the column is used in series with two TSKGEL SUPER MULTIPORE HZ-H (TOSOH), the detector uses the difference in lightgicking Ri-8320 and UV visible test count (UV- The wavelength is set to 254 nm) (TOSOH system).

[0170][NMR) Determination]

[0171]First, 30 mg of the polyether compound as a sample was added to 1.0 ml of deuterated dimethyl sulfoxide, and oscillated for 1 hour, thereby uniformly dissolving. Then, the obtained solution was measured by NMR, obtained1H-NMR spectrum, refers to the structure of the polyether compound according to the general method. The NMR device uses JEOL JNM-EX400WB spectrometers (399.78 MHz for 1H, 100.53 MHz for 13C), or Bruker Avance III 500MHz spectrometer (500.13 MHz for 1 h, 125.77 MHz for 13C).

[0172]Manufacturing Example A

[0173](Activity anionic polymerization of epideol)

[0174]2.84 g of tetra-n-butlammonium and 50 ml of toluene were added to 0 ° C in a glass reactor which was replaced with argon. Next, a solution of 1.256 g of triethyl aluminum (1.1 equivalent to the azide nitrid n-butlammonium) was added to reflect it for 15 minutes to obtain a catalyst composition. 15.0 g of epichlorohydrin was added to the obtained catalyst composition, and the polymerization was carried out at 0 ° C. After the polymerization reaction, the viscosity of the solution was slowly increased. After 12 hours, a small amount of water was injected in the polymerization reaction liquid, and the reaction was terminated. The resulting polymerized reaction liquid was washed with an aqueous hydrochloric acid aqueous hydrochloride, thereby performing a slag removal treatment of catalyst residue, and washed with ion-exchanged water, dried at 50 ° C for 12 hours. The yield of colorless and transparent oil-like substances thus obtained is 14.9 g. Further, the obtained substance was 1580 by using a number average molecular weight (Mn) of GPC measured by the difference, which was 1.21, and the molecular weight distribution (MW / Mn) was 1.21. The resulting material was not detected by the UV visible detection of the GPC. The oil-like substance, which can be considered above, is a laminated nitrogen group in the polymerization, and a oligomer (an average 17) (hereinafter referred to as polyethelcohol A) having a hydroxyl group having a hydroxyl group (hereinafter referred to as polyethel alcohol A) at the end of the polymerization. .

[0175]Manufacturing Example B

[0176](Based on clicking chemistry to polysperliofliter glycol A)

[0177]1.5 g of the polytegliol A and 10 ml of dimethylformamide were added to a glass reactor exchanged with argon, maintained at room temperature. Next, 0.287 g of bromide (I), 0.347 g of pentamethylethyltride and 0.053 g of 1,7-octadikarne were added in the above solution, and at room temperature for 48 hours. The polymeric reaction solution obtained by toluene is extracted, and the organic phase is cleaned with an ion exchange, thereby performing a slag-residue treatment of catalyst residue, dried at 50 ° C for 12 hours. The yield of colorless and transparent oil-like substances thus obtained is 1.4 g. Further, the obtained substance was 1.26 by using a number average molecular weight (Mn) of GPC measured by the difference of the difference. The obtained substance was also detected by the ultraviolet visible detection of GPC, indicating the formation of 1,2,3-triazole ring. In addition, through1H-NMR confirmed that the triazole ring has been introduced.

[0178]The above-mentioned oily substances are the azide groups of the end of the polytegliol A and 1,7-octane-coupled, and the polymerization of the polyethylene chloride A occurs, and the two ends have a hydroxyl. Polyethethool B (according to GPC is an average 30).