Method for determining impurities in polyalkylene ethers or polyalkylene amines and use thereof

Patent metadata

Field	Value
Publication number	US-12017154-B2
Application number	US-201916964389-A
Country	US
Kind code	B2
Filing date	Jan 25, 2019
Priority date	Jan 27, 2018
Publication date	Jun 25, 2024
Grant date	Jun 25, 2024

Abstract

Disclosed is a method for the determination of impurities in polyalkylene ethers and polyalkylene amines comprising the steps
i) introducing polyalkylene ethers or polyalkylene amines as an analyte into a chromatography column containing monolithic silica gel as a stationary phase, ii) eluting the analyte with a liquid elution agent having such a polarity that the analyte is in adsorptive equilibrium with the stationary phase during chromatography, iii) detecting the components of the analyte at the exit-side end of the chromatography column, receiving a chromatogram, which shows different components of the analyte and its qualitative amount depending on the elution time of the individual components, and iv) identifying bands in the chromatogram having a low height or area compared to the band with the largest height or area as an indication of the presence of impurities in the analyte.

The method allows in an easy manner to identify impurities in the sample. The method can be used for quality control but also for the preparative cleaning of the sample.

First claim

The invention claimed is:

1. A method for determining impurities in a polyalkylene ether or a polyalkylene amine consisting essentially of:
i) introducing an analyte comprising the polyalkylene ether or the polyalkylene amine into a chromatography column containing monolithic silica gel as a stationary phase, wherein the monolithic silica gel is a porous monolithic material comprising interconnected macropores and mesopores,
ii) eluting the analyte with a liquid elution agent having a polarity that the analyte is in adsorptive equilibrium with the stationary phase during chromatography,
iii) detecting individual components of the analyte at an exit-side end of the chromatography column containing monolithic silica gel, and receiving a chromatogram, the chromatogram showing individual components of the analyte depending on an elution time of the individual components, wherein the individual components are individual polyalkylene ethers or individual polyalkylene amines, and
iv) identifying and quantifying impurities in the chromatogram by band height or area comparison, wherein bands having a low height or area correspond to polyalkylene ether impurities or polyalkylene amine impurities in the analyte in comparison to a band with a largest height or area.

2. The method according to claim 1 , characterized in that the polyalkylene ether comprises a polyethylene glycol, or a polypropylene glycol, or a combination thereof.

3. The method according to claim 2 , wherein the polyethylene glycol or the polypropylene glycol include alkoxy end groups.

4. The method according to claim 1 , characterized in that the polyalkylene amine comprises an aliphatic polyoxazoline.

5. The method according to claim 1 , characterized in that the impurities in the polyalkylene ether are polyols whose mean molar mass is in a same range or below a mean molar mass of the polyalkylene ether to be analyzed, the impurities including alkylene diols and/or di- or trialkylene glycols.

6. The method according to claim 1 , characterized in that the impurities in the polyalkylene amine are polyamines whose mean molar mass is in a same range or below a mean molar mass of the polyalkylene amine to be analyzed, the impurities including alkylene diamines and/or di- or trialkyleneimine diamines.

7. The method according to claim 1 , wherein the monolithic silica gel is reversed phase, and an eluent contains water and an organic solvent in an amount that eluting of the analyte takes place as adsorption chromatography.

8. The method according to claim 7 , characterized in that the eluent contains water and acetonitrile.

9. The method according to claim 1 , characterized in that the method includes high-pressure liquid chromatography.

10. The method according to claim 1 , characterized in that a detection of the components of the analyte at the exit-side end of the chromatography column is carried out by light scattering detection (ELSD) or by UV/VIS spectroscopy.

11. The method according to claim 1 , characterized in that the height or area of the bands with a low height or area is less than 10% of the height or area of the band with the largest height or area.

12. The method according to claim 2 , wherein the polyethylene glycol or the polypropylene glycol include hydroxy end groups.

13. The method of claim 12 , wherein the hydroxy end groups are partially or completely etherified.

14. The method of claim 3 , wherein the polyethylene glycol or the polypropylene glycol include methoxy end groups.

15. The method of claim 4 , wherein the aliphatic polyoxazoline includes end groups selected from amino groups, hydroxy groups, alkyl groups, aryl groups, or a combination thereof.

16. The method of claim 15 , wherein the end groups include amino groups, and the amino groups are partially or completely alkylated.

17. The method of claim 1 , wherein an amount of the impurities of the polyalkylene ether or a the polyalkylene amine is not greater than 1%.

Assignees

• Friedrich Schiller Univ Jena Fsu
• Univ Jena Friedrich Schiller

Inventors

• Schubert Ulrich Sigmar
• Nischang Ivo
• Brunzel Michaela

Classifications

• B01J20/283

  based on silica · CPC title

• B01J20/291

  Gel sorbents · CPC title

• G01N2030/8872

  impurities · CPC title

• G01N2030/027

  Liquid chromatography · CPC title

• G01N30/8631

  Peaks · CPC title