IP Library Granted Patent US 11,208,408
Granted Patent B2
US 11,208,408 · App. 17/240,076 · Granted Dec 28, 2021

Method of controlling scale in aqueous systems

Inventor: Klin Aloysius Rodrigues (Signal Mountain, TN)
Assignee: Nouryon Chemicals International B.V.
C07D471/06C02F1/56C02F5/12C08F2/44C08K5/0041C09K11/06G01N21/643C02F2103/02C02F2209/003C02F2303/22C09K2211/1029
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Quick Facts
Patent No.
US 11,208,408
App. No.
17/240,076
Granted
Dec 28, 2021
Kind
B2
Abstract

A method of inhibiting scale in an industrial water system includes the steps of dosing the industrial water system with a water treatment polymer comprising at least 10 mol % of carboxylic acid monomer and a quaternized naphthalimide fluorescent monomer as disclosed herein, and then monitoring the fluorescence of the water system. The polymers are also useful for flocculation and coagulation in wastewater treatment.

Claims (55)

1. A quaternized fluorescent monomer comprising the structure:

wherein

R 4 is selected from H, hydroxy, alkoxy or C 1 -C 4 alk-O—(CHR 5 CH 2 O—)n;

R 5 is selected from H and C 1 -C 4 -alkyl;

n is 1-10; and

X − is an anionic counter ion;

and comprising less than 8 mol%, based on 100 mol% of total naphthalimide fluorescent monomer of the structure:

wherein R 4 is as defined above.

2. The quaternized fluorescent monomer of claim 1 , which comprises the structure:

wherein X − is an anionic counter ion;

and comprises less than 8 mol%, based on 100 mol% of total naphthalimide fluorescent monomer of the structure:

3. The quaternized fluorescent monomer of claim 2 , wherein X − is an anionic counterion selected from the group consisting of chloride, bromide, hydroxide, methosulphate, sulfate, sulfonate, carboxylate, phosphate, and phosphonate.

4. The quaternized fluorescent monomer of claim 1 , wherein X − is an anionic counterion selected from the group consisting of chloride, bromide, hydroxide, methosulphate, sulfate, sulfonate, carboxylate, phosphate, and phosphonate.

5. The quaternized fluorescent monomer of claim 1 , which comprises (a) N-(3-dimethylaminopropyl)-4-methoxy-1,8-naphthalimide, 2-hydroxy-3-(meth)allyloxypropyl quaternary salt comprising less than 5 mol% of (b) N-(3-dimethylaminopropyl)-4-methoxy-1,8-naphthalimide, based on 100 mol% of (a).

6. A polymer prepared by polymerizing the quaternized fluorescent monomer of claim 5 with other monomers.

7. The quaternized fluorescent monomer of claim 1 , which comprises (a) N-(3-dimethylaminopropyl)-4-methoxy-1,8-naphthalimide, 2-hydroxy-3-(meth)allyloxypropyl quaternary salt comprising less than 1.5 mol% of (b) N-(3-dimethylaminopropyl)-4-methoxy-1,8-naphthalimide, based on 100 mol% of (a).

8. A polymer prepared by polymerizing the quaternized fluorescent monomer of claim 7 with other monomers.

9. A polymer prepared by polymerizing the quaternized fluorescent monomer of claim 1 with other monomers.

10. The polymer according to claim 9 , wherein the other monomers are selected from the group consisting of cationic, anionic, and/or nonionic monomers.

11. The polymer according to claim 10 , wherein the quaternized fluorescent monomer is incorporated into the polymer to an extent equal to or greater than 90 mol%.

12. The polymer according to claim 10 , wherein the quaternized fluorescent monomer is incorporated into the polymer to an extent equal to or greater than 95 mol%.

13. A water treatment polymer formed from polymerizing a polymerization mixture comprising:

(i) at least one water-soluble carboxylic acid monomer, or salt or anhydride thereof, present in an amount of 10-99.999 mol% based on 100 mol% of the polymer;

(ii) the quaternized fluorescent monomer of claim 1 ; and

wherein the polymer chains of the water treatment polymer formed comprise 0.001 mol% to less than or equal to 10 mol% of the quaternized fluorescent monomer of claim 1 as unreacted monomer unincorporated into the polymer chains thereby indicating that said quaternized fluorescent monomer of claim 1 has been incorporated into said water treatment polymer to an extent equal to or greater than 90 mol%.

14. The polymer of claim 13 , wherein said quaternized fluorescent monomer is incorporated into the polymer to the extent of at least 95 mol%.

15. The polymer of claim 13 , wherein the polymerization mixture comprises (a) N-(3-dimethylaminopropyl)-4-methoxy-1,8-naphthalimide, 2-hydroxy-3-(meth)allyloxypropyl quaternary salt comprising less than 5 mol% of (b) N-(3-dimethylaminopropyl)-4-methoxy-1,8-naphthalimide, based on 100 mol% of (a).

16. The polymer of claim 15 , wherein (a) is incorporated into the polymer to the extent of at least 95 mol%.

17. The polymer of claim 13 , wherein the polymerization mixture comprises (a) N-(3-dimethylaminopropyl)-4-methoxy-1,8-naphthalimide, 2-hydroxy-3-(meth)allyloxypropyl quaternary salt comprising less than 1.5 mol% of (b) N-(3-dimethylaminopropyl)-4-methoxy-1,8-naphthalimide, based on 100 mol% of (a).

18. The polymer of claim 17 , wherein (a) is incorporated into the polymer to the extent of at least 98 mol%.

19. A process of preparing a water treatment polymer, the process comprising the following steps:

(a) polymerizing a polymerization mixture comprising:

(i) at least one water-soluble carboxylic acid monomer, or salt or anhydride thereof, present in an amount of 10-99.999 mol% based on 100 mol% of the polymer;

(ii) the quaternized fluorescent monomer of claim 1 ; and

(b) wherein the polymer chains of the water treatment polymer formed comprise 0.001 mol% to less than or equal to 10 mol% of the quaternized fluorescent monomer of claim 1 as unreacted monomer unincorporated into the polymer chains thereby indicating that said quaternized fluorescent monomer of claim 1 has been incorporated into said water treatment polymer to an extent equal to or greater than 90 mol%.

20. A method of controlling scale in a water system, the method comprising the steps of:

(a) dosing the water system with a water treatment polymer according to claim 13 ; and

(b) monitoring the fluorescent signal emitted from said water system.

21. A method for coagulation or flocculation in a water treatment system, the method comprising the steps of:

(a) dosing the water treatment system with the water treatment polymer according to claim 13 ; and

(b) monitoring the fluorescent signal emitted from the water treatment system.

22. A method for determining whether a given location has been cleaned comprising the steps of:

(a) applying the water treatment polymer according to claim 13 to the location;

(b) cleaning the location at least once; and

(c) measuring fluorescence at the location after said cleaning, which, presence, if detected, indicates that additional cleaning is needed.

23. A method of controlling scale in a water system, the method comprising the steps of:

(a) dosing the water system with a water treatment polymer according to claim 9 ; and

(b) monitoring the fluorescent signal emitted from said water system.

24. A method for coagulation or flocculation in a water treatment system, the method comprising the steps of:

(a) dosing the water treatment system with the water treatment polymer according to claim 9 ; and

(b) monitoring the fluorescent signal emitted from the water treatment system.

25. A method for determining whether a given location has been cleaned comprising the steps of:

(a) applying the water treatment polymer according to claim 9 to the location;

(b) cleaning the location at least once; and

(c) measuring fluorescence at the location after said cleaning, which, presence, if detected, indicates that additional cleaning is needed.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 26, 2021
From: RODRIGUES, KLIN ALOYSIUS
To: NOURYON CHEMICALS INTERNATIONAL B.V.
Reel/Frame 056039/0603 →
Priority Claims (1)
EP 19194577 · Aug 30, 2019 · regional
Continuity (3)
Continuation In Part 17258896
Provisional Application 62853624 · May 28, 2019
Related Publication 20210253461A1 · Aug 19, 2021