# US 2021/0080433 A1 · Qualitative and Quantitative Analysis Method for High Molecular Weight Additive by Using Size-Exclusion Chromatography-Pyrolysis-Gas Chromatography/Mass Spectrometry

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- Number: US 2021/0080433 A1
- Document ID: US20210080433A1
- Status: Published application
- Kind: A1
- Application number: 16/963,685
- Filed: 2019-10-10
- Published: 2021-03-18
- Earliest claimed: 2018-10-11
- Assignees: LG Chem, Ltd.
- Applicants: LG Chem, Ltd.
- Inventors: Seonyoung Jegal; Byoung Hyoun Kim; Dong Hyun Kim; Yura Lee; Hyun Sik You
- Web page: https://patentgrep.com/patent/US20210080433A1

## CPC

- G01N 30/12: by evaporation
- G01N 30/88: Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86
- G01N 30/7206: {interfaced to gas chromatograph (interfaces in general for introducing or extracting samples to be analysed with specially adapted mass spectrometer, see H01J49/04)}
- G01N 30/8631: {Peaks}
- G01N 2030/047: {external}
- G01N 2030/125: {pyrolising}
- G01N 2030/8405: {using pyrolysis}
- G01N 2030/885: {involving polymers}
- G01N: INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES (measuring or testing apparatus or processes other than immunoassay, involving enzymes or microorganisms C12M, C12Q)

## Abstract

A method for securing qualitative and quantitative information of a high molecular weight additive in a polymer resin sample is disclosed herein. In some embodiments, the method includes separating a fraction of a polymer resin sample using size exclusion chromatography (SEC), wherein the fraction corresponding to a high molecular weight additive, pyrolyzing the fraction in a pyrolysis-gas chromatography/mass spectrometer (Py-GC/MS) to obtain a mass spectrum of the pyrolyzed fraction; identifying a structure of the high molecular weight additive by comparing m/z values for fragment peaks in the mass spectrum to m/z values for fragment peaks in a mass spectrum of a standard, and determining the amount of the high molecular weight additive in the polymer resin sample, relative to the total weight of the polymer resin sample by comparing a sum of areas of the fragment peaks to a calibration line of the standard.

## Claims

### Claim 1

A method of analyzing a polymer resin sample, the polymer resins sample comprising a polymer resin and a high molecular weight additive containing a piperidine or a morpholine moiety, the method comprising:
separating a fraction of the polymer resin sample using size exclusion chromatography (SEC), wherein the fraction corresponding to the high molecular weight additive;
pyrolyzing the fraction in a pyrolysis-gas chromatography/mass spectrometer (Py-GC/MS) to obtain a mass spectrum of the pyrolyzed fraction;
identifying a structure of the high molecular weight additive by comparing m/z values for fragment peaks derived from the piperidine or the morpholine moiety in the mass spectrum to m/z values for fragment peaks derived from the piperidine or the mopholine moiety from a mass spectrum of a standard, the standard being a solution of the high molecular weight additive; and
determining the amount of the high molecular weight additive in the polymer resin sample, relative to the total weight of the polymer resin sample by comparing a sum of areas of the fragment peaks to a calibration line, where the calibration line represents a sum of areas of the fragment peaks in the standard as a function of concentration of the standard,
wherein the molecular weight of the high molecular weight additive is 1,000 to 4,000 g/mol.

### Claim 2

(canceled)

### Claim 3 (depends on 1)

The analysis method according to claim 1, wherein the high molecular weight additive is at least one hindered amine light stabilizer (HALS) selected from the group consisting of compounds of Formulas (I) to (III).

### Claim 4 (depends on 3)

The analysis method according to claim 3, wherein the hindered amine light stabilizer is the compound of Formula (I).

### Claim 5 (depends on 1)

The analysis method according to claim 1, wherein the high molecular weight additive is the compound of Formula (I), and
wherein the mass spectrum of the high molecular weight additive has the fragment peaks derived from the piperidine or the mopholine moiety at m/z values of 58, 98, 124 and 140.

### Claim 6 (depends on 1)

The analysis method according to claim 1, wherein the high molecular additive is present in an amount of 0.3 to 0.7% by weight based on the weight of the polymer resin sample.

### Claim 7 (depends on 1)

The analysis method according to claim 1, wherein the polymer resin is a water insoluble resin.

### Claim 8 (depends on 1)

The analysis method according to claim 1, wherein a mobile phase of the size exclusion chromatography (SEC) is a solvent selected from the group consisting of water, methanol, acetonitrile (AN) and tetrahydrofuran (THF).

### Claim 9 (depends on 1)

The analysis method according to claim 1, wherein in the size exclusion chromatography (SEC) the polymer resin sample is collected at 0.5 min to 1 min intervals in a range of 15 to 30 minutes after the start of the separation of the fraction.

### Claim 10 (depends on 1)

The analysis method according to claim 1, wherein the pyrolysis of the fraction is performed by raising the temperature from 100° C. to 800° C. at a rate of 50° C./sec to 80° C./sec.

### Claim 11 (depends on 10)

The analysis method according to claim 10, wherein the pyrolysis of the fraction is performed by raising the temperature from 100° C. to 600° C. at a rate of 60° C./sec and maintaining at 600° C. for 60 seconds.

### Claim 12 (depends on 1)

An analysis system for performing the method according to claim 1, comprising:
a size exclusion chromatography apparatus;
an automated sample collecting and injecting device;
a pyrolyzer; and
a gas chromatography and mass spectrometer.