IP Library Granted Patent US 9,862,811
Granted Patent B2
US 9,862,811 · App. 14/804,660 · Granted Jan 9, 2018

Methods for synthesizing stabilized polymers of chlorotrifluoroethylene and products manufactured using such polymers

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Quick Facts
Patent No.
US 9,862,811
App. No.
14/804,660
Granted
Jan 9, 2018
Kind
B2
Abstract

Methods for synthesizing stabilized polymers of chlorotrifluoroethylene and products manufactured using such polymers are disclosed herein. In one exemplary embodiment, a method for synthesizing chlorotrifluoroethylene (CTFE)-based polymers includes reacting, in the presence of an initiator and in a reaction medium at a pH of about 1.5 to about 2.5, one or more monomers comprising CTFE and after an amount of polymerization reaction time has passed, adding a neutralizing agent to the reaction medium to increase the pH of the reaction medium to within a range of about 1.8 to about 6.0.

Claims (29)

1. A method for synthesizing chlorotrifluoroethylene (CTFE)-based polymers comprising:

reacting, in the presence of an initiator and in a reaction medium at a pH of about 1.5 to about 2.5, one or more monomers comprising CTFE; and

after an amount of polymerization reaction time has passed, adding a neutralizing agent to the reaction medium to increase the pH of the reaction medium to within a range of about 1.8 to about 6.0.

2. The method of claim 1 , wherein adding the neutralizing agent comprises adding an aqueous base or a buffer solution.

3. The method of claim 2 , wherein adding the neutralizing agent comprises adding the neutralizing agent after an amount of polymerization reaction time of about 1 hour to about 24 hours has passed.

4. The method of claim 3 , wherein adding the neutralizing agent comprises adding the neutralizing agent after an amount of polymerization reaction time of about 1 hour to about 12 hours has passed.

5. The method of claim 3 , wherein adding the neutralizing agent comprises adding a buffer solution having a pH of about 3.0 to about 7.0 after the amount of polymerization reaction time has passed.

6. The method of claim 5 , wherein adding the buffer solution comprises adding an aqueous solution that is selected from the group consisting of: acetate, citrate, phosphate, and lactate solutions, and mixtures thereof, after the amount of polymerization reaction time has passed.

7. The method of claim 6 , wherein adding the buffer solution comprises adding an aqueous solution that is selected from the group consisting of: ammonium lactate, sodium lactate, and potassium lactate solutions, and mixtures thereof, after the amount of polymerization reaction time has passed.

8. The method of claim 7 , wherein adding the buffer solution comprises adding an aqueous ammonium lactate solution after the amount of polymerization reaction time has passed.

9. The method of claim 8 , wherein adding the buffer solution comprising adding an aqueous ammonium lactate solution wherein a concentration of the ammonium lactate in the solution is from about 5 to about 75 weight-% based on total solution weight.

10. The method of claim 9 , wherein adding the buffer solution comprising adding an aqueous ammonium lactate solution wherein a concentration of the ammonium lactate in the solution is from about 40 to about 65 weight-% based on total solution weight.

11. The method of claim 9 , wherein adding the ammonium lactate solution comprises adding about 1.0 to about 5.0 mole-% of ammonium lactate based on the one or more monomers.

12. The method of claim 11 , wherein adding the ammonium lactate solution comprises adding about 1.0 to about 2.0 mole-% of ammonium lactate based on the one or more monomers.

13. The method of claim 3 , wherein adding the neutralizing agent comprises adding an aqueous base solution comprising sodium hydroxide or potassium hydroxide after the amount of polymerization reaction time has passed.

14. The method of claim 1 , wherein reacting one or more monomers comprising CTFE comprises reacting one or more monomers comprising CTFE and one or more monomers selected from the group consisting of: vinylidene fluoride, 1,2-difluoroethylene, vinylidene chloride, 1,1-dichlorodifluoroethylene, 1,2-dichlorodifluoroethylene, 1-chloro-1-fluoroethylene, tetrafluoroethylene, trifluoroethylene, vinyl fluoride, hexafluoropropylene, hexafluoroisobutylene, perfluorobutylethylene, pentafluoropropene, 3,3,3-trifluoro-1-propene, 2,3,3,3-tetrafluoropropene, 1,3,3,3-tetrafluoropropene, fluorinated vinyl ethers, fluorinated allyl ethers, fluorinated dioxoles, olefins, and functionalized olefins, and combinations thereof.

15. The method of claim 1 , wherein adding the neutralizing agent comprises adding the neutralizing agent at a reaction pressure of about 50 psi g to about 150 psi g .

16. The method of claim 1 , further comprising performing a heat-up/cool-down procedure after adding the neutralizing agent.

17. The method of claim 1 , further comprising filtering and drying a CTFE-based polymer product after adding the neutralizing agent.

18. The method of claim 17 , further comprising thermally processing the CTFE-based polymer product after filtering and drying the CTFE-based polymer product.

19. A method for synthesizing chlorotrifluoroethylene (CTFE)-based polymers comprising:

reacting, in the presence of an initiator and in a reaction medium at a pH of about 1.5 to about 2.5, one or more monomers comprising CTFE;

after a polymerization reaction time of about 1 hour to about 24 hours has passed, adding a neutralizing agent comprising a buffer solution comprising an aqueous ammonium lactate solution to the reaction medium to increase the pH of the reaction medium to within a range of about 1.8 to about 6.0, wherein the aqueous ammonium lactate solution comprises ammonium lactate in an amount from about 5 to about 75 weight-% based on total weight of the solution, and wherein adding the ammonium lactate solution comprises adding about 1.0 to about 5.0 mole-% of ammonium lactate based on the one or more monomers; and

filtering and drying a CTFE-based polymer product after adding the neutralizing agent.

20. A method for manufacturing a chlorotrifluoroethylene (CTFE)-based polymer product comprising:

reacting, in the presence of an initiator and in a reaction medium at a pH of about 1.5 to about 2.5, one or more monomers comprising CTFE;

after a polymerization reaction time of about 1 hour to about 12 hours has passed, adding a neutralizing agent comprising a buffer solution comprising an aqueous ammonium lactate solution to the reaction medium to increase the pH of the reaction medium to within a range of about 1.8 to about 5.0, wherein the aqueous ammonium lactate solution comprises ammonium lactate in an amount from about 40 to about 65 weight-% based on total weight of the solution, and wherein adding the ammonium lactate solution comprises adding about 1.0 to about 2.0 mole-% of ammonium lactate based on the one or more monomers;

filtering and drying a CTFE-based polymer product after adding the neutralizing agent; and

thermally processing the CTFE-based polymer product after filtering and drying the CTFE-based polymer product at a temperature of about 275° C. to about 325° C.

Assignments (2)
SECURITY INTEREST Recorded Jan 12, 2026
From: SOLSTICE ADVANCED MATERIALS US, INC.
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 074569/0260 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 21, 2015
From: THENAPPAN, ALAGAPPAN; RAINAL, ERIC
To: HONEYWELL INTERNATIONAL INC.
Reel/Frame 036143/0091 →