# US 10,308,869 B2 · Liquid containing polymer marker, use of a polymer marker as authentication tool, and method and device for detecting a polymer marker dissolved in a liquid

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- Number: US 10,308,869 B2
- Document ID: US10308869B2
- Status: Granted
- Kind: B2
- Application number: 15/509,680
- Filed: 2015-09-25
- Published: 2018-06-21
- Granted: 2019-06-04
- Earliest claimed: 2014-09-30
- Assignees: Sicpa Holding SA
- Applicants: Sicpa Holding SA
- Inventors: Mia Milos-Schouwink; Agnieszka Kapalka; Jean-Luc Dorier; Lorenzo Sirigu; Lucia Giovanola; Paolo Schina; Silvia Baldi; Irma Disegna; Silvano Tori
- Web page: https://patentgrep.com/patent/US10308869B2

## CPC

- C09K 11/06: containing organic luminescent materials
- B01L 3/502715: {characterised by interfacing components, e.g. fluidic, electrical, optical or mechanical interfaces}
- B01L 3/502753: {characterised by bulk separation arrangements on lab-on-a-chip devices, e.g. for filtration or centrifugation}
- C10L 1/003: {Marking, e.g. coloration by addition of pigments}
- C10L 1/165: {from compounds containing aromatic monomers}
- G01N 1/4005: {by transferring a selected component through a membrane}
- G01N 1/4077: {by other techniques involving separation of suspended solids}
- G01N 21/643: {non-biological material}
- G01N 21/6489: {Photoluminescence of semiconductors}
- G01N 33/2882: {Markers}
- G01N 35/10: Devices for transferring samples {or any liquids} to, in, or from, the analysis apparatus, e.g. suction devices, injection devices {(G01N35/0099 takes precedence)}
- B01L 2200/0647: Handling flowable solids, e.g. microscopic beads, cells, particles
- B01L 2300/0681: Filter
- B01L 2300/1805: Conductive heating, heat from thermostatted solids is conducted to receptacles, e.g. heating plates, blocks
- B01L 2300/1894: Cooling means; Cryo cooling
- B01L 2400/06: Valves, specific forms thereof
- C09K 2211/1416: Condensed systems
- C09K 2211/1425: Non-condensed systems
- C10L 2230/16: Tracers which serve to track or identify the fuel component or fuel composition
- G01N 21/645: {Specially adapted constructive features of fluorimeters}
- G01N 2001/4016: {being a selective membrane, e.g. dialysis or osmosis}
- G01N 2001/4088: {filtration}
- G01N 2021/6439: {with indicators, stains, dyes, tags, labels, marks}
- G01N 2035/00207: {Handling bulk quantities of analyte}
- G01N 2035/00376: {Conductive heating, e.g. heated plates}
- G01N 2035/00445: {Other cooling arrangements}
- G01N 2035/00475: {Filters}
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- B01L: CHEMICAL OR PHYSICAL LABORATORY APPARATUS FOR GENERAL USE
- C10L: FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
- 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

The present invention relates to markers for liquids that can be used to authenticate the origin and genuineness of a liquid, preferably a bulk liquid such as fuel. For this purpose, the present invention teaches the use of a polymer capable of forming a semiconducting polymer particle (pdot) in the liquid in small amounts. The invention encompasses a liquid comprising a) a polymer that is capable of forming a semiconducting polymer particle (pdot), the concentration of the polymer being 10 ppm by weight or less, and b) an organic substance in an amount of 90% by weight or more. The invention furthermore envisages the use of such a polymer as an authenticating marker in a liquid, preferably a fuel, and a method for authenticating the genuineness and/or origin of a liquid comprising a polymer capable of forming a semiconducting polymer particle (pdot), comprising the steps i. concentrating, isolating and/or extracting the polymer capable of forming a semiconducting polymer particle (pdot); ii. aggregating the polymer or the polymer obtained in Step i. to form semiconducting polymer dots (pdots); iii. irradiating the formed pdots with electromagnetic radiation capable of exciting the pdots to emit electromagnetic radiation by fluorescence and/or phosphorescence, and iv. observing the electromagnetic radiation emitted in response to the exciting irradiation of step iii.

## Claims

### Claim 1

A method for authenticating the genuineness and/or origin of a liquid comprising a polymer capable of forming a semiconducting polymer particle (pdot), comprising the steps
i. concentrating, isolating and/or extracting a polymer capable of forming a semiconducting polymer particle (pdot);
ii. aggregating the polymer obtained in Step i. to form semiconducting polymer dots (pdots);
iii. irradiating the formed pdots with electromagnetic radiation capable of exciting the pdots to emit electromagnetic radiation by fluorescence and/or phosphorescence, and
iv. observing electromagnetic radiation emitted in response to the exciting irradiation of step iii, wherein if the observed electromagnetic radiation conforms to a parameter that is defined as indicative for the genuineness and/or origin of the liquid, a decision as to the authenticity and/or origin of the liquid is made.

### Claim 2 (depends on 1)

The method according to claim 1, wherein the liquid is a fuel and wherein the concentration of the polymer capable of forming a semiconductor particle is equal to or less than 10 ppm by weight.

### Claim 3 (depends on 1)

The method according to claim 1, wherein the method is implemented in a portable device.

### Claim 4 (depends on 1)

The method according to claim 1, wherein the aggregation of the polymer to form pdots is performed by re-precipitation using water and a water-miscible organic solvent; or by mini-emulsion using two or more non-miscible solvents and a surfactant.

### Claim 5 (depends on 1)

The method according to claim 1, which additionally comprises the following steps:
iii.a. irradiating the polymer capable of forming a semiconducting polymer particles, or a solution containing it, with electromagnetic radiation capable of exciting the polymers to emit electromagnetic radiation by fluorescence and/or phosphorescence, and
iv.a. observing the electromagnetic radiation emitted in response to the exciting irradiation of step iii.a.

### Claim 6 (depends on 5)

The method according to claim 5, which comprises further a step of comparing the electromagnetic radiation emitted by the polymer observed in step iv.a with the electromagnetic radiation emitted by the pdot observed in step iv.

### Claim 7 (depends on 5)

The method according to claim 5, wherein the polymer irradiated in step iii.a is present in a liquid to be evaluated for its genuineness and/or origin, is present in a water-soluble solvent other than the liquid to be evaluated for its genuineness and/or origin, or is present undissolved on a supporting surface.

### Claim 8 (depends on 1)

The method according to claim 1, wherein the polymer capable of forming a semiconducting polymer dot (pdot) contains a structural unit selected from structural units comprising a (9, 9, dioctyl-2,7-divinylenefluorenylene)-alt-co-(9,10-anthracene) moiety of formula (1) and structural units comprising a moiety of formula (102):