IP Library Granted Patent US 11,879,031
Granted Patent B2
US 11,879,031 · App. 17/076,955 · Granted Jan 23, 2024

Low critical solution temperature purification of oxazoline polymer solutions

Inventor: Daniel F. Varnell (Wilmington, DE)
Assignee: Solenis Technologies, L.P.
C08F6/12B01D17/042C08F6/28C08F20/56B01D2257/80
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Quick Facts
Patent No.
US 11,879,031
App. No.
17/076,955
Granted
Jan 23, 2024
Kind
B2
Abstract

Provided are methods for the purification of polymer solutions. In particular, the method enables the separation of impurities from an oxazoline polymer solution by raising the temperature of the polymer solution above its lower critical solution temperature (LCST), wherein a water rich phase and a polymer rich phase separation occurs. The phases are then separated with the polymer rich phase containing a lower amount of impurities than before separation.

Claims (30)

1. A method for the purification of a polymer solution comprising the steps of:

a) providing a polymer solution comprising water and an oxazoline polymer having a weight average molecular weight greater than about 5000 g/mol, and one or more impurities,

b) raising the temperature of the polymer solution from a first temperature to a second temperature that is above a lower critical solution temperature (LCST), wherein the polymer solution separates into a predominantly water phase and a polymer-rich phase;

c) separating the water phase from the polymer phase;

d) cooling the polymer phase to a third temperature such that a purified soluble polymer solution forms and has an amount of the one or more impurities that is less than an amount of the one or more impurities present in the polymer solution; and

e) optionally repeating steps b), c) and d).

2. The method according to claim 1 , wherein the polymer solution comprises poly-2-ethyl oxazoline.

3. The method according to claim 1 , wherein the impurities can be residual monomers and oligomers, initiators, production aids, and non-polymeric materials.

4. The method of claim 3 , wherein the level of oligomers in the final polymer layer on a basis of the weight of the polymer has been reduced by greater than 50 wt %.

5. The method of claim 4 , wherein the level of oligomers in the final polymer layer on a basis of the weight of the polymer has been reduced by greater than 65 wt %.

6. The method of claim 5 , wherein the level of oligomers in the final polymer layer on a basis of the weight of the polymer has been reduced by greater than 75 wt %.

7. The method according to claim 1 , wherein the second temperature of step b) is from about 65° C. to about 85° C.

8. The method according to claim 1 , wherein step d) comprises cooling the polymer phase via the addition of water.

9. The method according to claim 1 , the viscosity of the polymer phase is between 10 and 2000 cps.

10. The method of claim 1 , wherein the weight average molecular weight of the polymer is greater than about 50,000 g/mol and optionally greater than about 200,000 g/mol.

11. The method of claim 1 , further comprising the step of drying the polymer phase subsequent to step d).

12. The method of claim 1 , wherein the polymer solution is provided as a continuous feed.

13. The method of claim 1 , wherein the polymer solution further comprises a water soluble aluminum salt.

14. The method of claim 1 , wherein the total amount of impurities in the final polymer layer on a basis of the weight of the polymer is reduced by greater than 50%.

15. The method of claim 14 , wherein the total amount of impurities in the final polymer layer on a basis of the weight of the polymer is reduced by greater than 65 wt %.

16. The method of claim 15 , wherein the total amount of impurities in the final polymer layer on a basis of the weight of the polymer is reduced by greater than 75 wt %.

17. A method for the purification of poly-2-ethyl oxazoline (PEOx) comprising the steps of:

a) providing an aqueous solution containing one or more impurities and PEOx;

b) raising the temperature of the aqueous solution from a first temperature to a second temperature that is a lower critical solution temperature, wherein the aqueous solution separates into a water phase and a polymer rich phase;

c) separating the polymer rich phase from the water phase; wherein the polymer rich phase is more dense and contains a predominance of the PEOx polymer and the water phase contains a portion of the one or more impurities;

d) cooling the polymer phase to a third temperature allowing the polymer phase to return to an aqueous solution; and

e) optionally repeating steps b), c) and d).

18. The method of claim 17 , wherein the impurities can be residual monomers and oligomers, initiators, production aids, and non-polymeric materials.

19. The method of claim 18 , wherein the impurity is residual oligomers.

20. The method of claim 17 , wherein the impurities of the polymer rich phase is reduced by up to 50% of the initial aqueous solution.

Assignments (11)
SECURITY INTEREST Recorded Nov 14, 2025
From: CHEM-AQUA, INC.; DIVERSEY, INC.; DIVERSEY TASKI, INC.; INNOVATIVE WATER CARE, LLC; NCH CORPORATION; NCH LIFE SCIENCES LLC; SOLENIS TECHNOLOGIES, L.P.
To: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS NOTES COLLATERAL AGENT
Reel/Frame 073570/0838 →
RELEASE OF SECURITY INTEREST Recorded Nov 14, 2025
From: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS NOTES COLLATERAL AGENT
To: BIRKO CORPORATION; DIVERSEY, INC.; DIVERSEY TASKI, INC.; INNOVATIVE WATER CARE, LLC; SOLENIS TECHNOLOGIES, L.P.
Reel/Frame 073564/0864 →
SECURITY AGREEMENT (NOTES) Recorded Oct 10, 2025
From: DIVERSEY, INC.; DIVERSEY TASKI, INC.; INNOVATIVE WATER CARE, LLC; SOLENIS TECHNOLOGIES, L.P.
To: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS NOTES COLLATERAL AGENT
Reel/Frame 073061/0885 →
RELEASE OF 2023 NOTES PATENT SECURITY INTERESTS Recorded Oct 10, 2025
From: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A.
To: BIRKO CORPORATION; DIVERSEY, INC.; DIVERSEY TASKI, INC.; INNOVATIVE WATER CARE, LLC; SOLENIS TECHNOLOGIES, L.P.
Reel/Frame 073074/0198 →
SECURITY AGREEMENT (2024 NOTES) Recorded Jun 24, 2024
From: BIRKO CORPORATION; DIVERSEY, INC.; DIVERSEY TASKI, INC.; INNOVATIVE WATER CARE, LLC; SOLENIS TECHNOLOGIES, L.P.
To: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS NOTES COLLATERAL AGENT
Reel/Frame 067824/0278 →
2023 NOTES PATENT SECURITY AGREEMENT Recorded Jul 7, 2023
From: BIRKO CORPORATION; SOLENIS TECHNOLOGIES, L.P.; INNOVATIVE WATER CARE, LLC; DIVERSEY, INC.; DIVERSEY TASKI, INC.; INNOVATIVE WATER CARE GLOBAL CORPORATION
To: BANK OF NEW YORK MELLON TRUST COMPANY, N.A.
Reel/Frame 064225/0170 →
SECURITY AGREEMENT (NOTES) Recorded Sep 14, 2022
From: SOLENIS TECHNOLOGIES, L.P.; INNOVATIVE WATER CARE, LLC
To: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A. AS COLLATERAL AGENT
Reel/Frame 061432/0821 →
NOTES SECURITY AGREEMENT Recorded Nov 10, 2021
From: INNOVATIVE WATER CARE, LLC; SOLENIS TECHNOLOGIES, L.P.
To: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A.
Reel/Frame 058103/0066 →
TERM LOAN PATENT SECURITY AGREEMENT Recorded Nov 10, 2021
From: INNOVATIVE WATER CARE, LLC; SOLENIS TECHNOLOGIES, L.P.
To: GOLDMAN SACHS BANK USA
Reel/Frame 058102/0407 →
ABL PATENT SECURITY AGREEMENT Recorded Nov 10, 2021
From: INNOVATIVE WATER CARE, LLC; SOLENIS TECHNOLOGIES, L.P.
To: BANK OF AMERICA, N.A.
Reel/Frame 058102/0122 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 22, 2020
From: VARNELL, DANIEL F.
To: SOLENIS TECHNOLOGIES, L.P.
Reel/Frame 054135/0125 →
Continuity (1)
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