IP Library Granted Patent US 9,758,611
Granted Patent B2
US 9,758,611 · App. 15/101,383 · Granted Sep 12, 2017

Process for recovering brominated styrene-butadiene copolymer from an organic solvent

Inventors: Daniel A. Beaudoin (Midland, MI); John W. Hull, Jr. (Midland, MI); Michal E. Porter (Midland, MI); William G. Stobby (Ann Arbor, MI); Gerald F. Billovitz (Midland, MI); Timothy J. Young (Bay City, MI)
Assignee: Dow Global Technologies LLC
C08F236/16C08C2/06C08J9/0061C08L9/06C08J2201/03C08J2325/04C08J2409/06
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Quick Facts
Patent No.
US 9,758,611
App. No.
15/101,383
Granted
Sep 12, 2017
Kind
B2
Abstract

Brominated styrene-butadiene copolymers are recovered from solution in an organic solvent. The copolymer solution is mixed with a liquid non-solvent in the presence of a suspension stabilizer to form a dispersion. The dispersion is heated to vaporize the organic solvent. This process produces precipitated copolymer particles having useful particle sizes, which can be easily used in downstream applications.

Claims (23)

1. A process for recovering a brominated styrene-butadiene polymer from an organic solvent comprising

(1) forming a mixture of A) a solution of the brominated styrene-butadiene polymer dissolved in the organic solvent and B) a liquid non-solvent, in the presence of C) at least one organic suspension stabilizer, wherein:

a) the brominated styrene-butadiene copolymer is soluble to the extent of no greater than 5 parts by weight per 100 parts by weight of the liquid non-solvent at the temperature at which step (3) is performed,

b) solvent and liquid non-solvent are soluble in each other to the extent of no more than about 5 parts by weight of one per 100 parts by weight of the other at the temperature at which step (3) is performed,

c) the liquid non-solvent has a boiling temperature at atmospheric pressure at least 10° C. greater than the lower of i) the boiling temperature of the organic solvent and ii), if the liquid non-solvent forms an azeotrope with the organic solvent which azeotrope has a lower boiling temperature than the organic solvent by itself, the boiling temperature of the azeotrope,

d) the volume ratio of A) to B) in the mixture formed in step (1) is no greater than 1:1, and

e) at the time step (1) is performed, the temperature of each of A) and B) is at least 10° C. below the lower of i) the boiling temperature of the organic solvent at atmospheric pressure and ii), if the organic solvent forms an azeotrope with the liquid non-solvent which azeotrope has a lower boiling temperature than the organic solvent by itself, the boiling temperature of such azeotrope;

(2) agitating the mixture of A), B) and C) to form droplets of A) dispersed in B);

(3) heating the dispersion formed in step (2) to a temperature below the boiling temperature of the liquid non-solvent but sufficient to vaporize the organic solvent by itself or as an azeotrope with the liquid non-solvent, such that the organic solvent vaporizes and is removed from the dispersion and the brominated styrene-butadiene copolymer precipitates to form particles, and

(4) removing the precipitated particles of brominated styrene-butadiene copolymer from the liquid non-solvent.

2. The process of claim 1 , wherein the liquid non-solvent does not form an azeotrope with the organic solvent, and the liquid non-solvent has a boiling temperature at least 15° C. higher than the boiling temperature of the organic solvent.

3. The process of claim 2 wherein the organic solvent has a boiling temperature of 35 to 80° C.

4. The process of claim 2 wherein the organic solvent includes one or more of carbon tetrachloride, chloroform, dichloromethane, 1,2-dichloroethane, hexane, cyclohexane, cyclooctane, isooctane, isohexane, and benzene.

5. The process of claim 1 wherein the organic solvent forms an azeotrope with the liquid non-solvent, which azeotrope has a boiling temperature lower than that of the organic solvent by itself, and the boiling temperature of the liquid non-solvent is at least 15° C. higher than the boiling temperature of the azeotrope.

6. The process of claim 5 wherein the organic solvent is toluene or a chlorinated benzene.

7. The process of claim 1 wherein the liquid non-solvent is water.

8. The process of claim 1 wherein the suspension stabilizer includes at least one anionic, cationic, or nonionic surfactant.

9. The process of claim 8 wherein the surfactant includes at least one fatty acid sulfate salt, fatty acid sulfonate salt, poly(oxyethylene) alkyl ether sulfate, poly(oxyethylene) alkyl sulfonate, alkali metal salt of a fatty acid, or ammonium salt of a fatty acid.

10. The process of claim 1 wherein the suspension stabilizer includes at least one water-soluble organic polymer.

11. The process of claim 10 , wherein the water-soluble organic polymer is methyl cellulose, hydroxypropylmethyl cellulose, poly(vinyl pyrrolidone), poly(vinyl alcohol), poly(ethylene glycol), poly(ethylene oxide) or a mixture of any two or more thereof.

12. The process of claim 1 , wherein the volume ratio of A) to B) in step 1) is no greater than 0.25:1.

13. The process of claim 1 , wherein at least a portion of the particles formed when the brominated styrene-butadiene copolymer precipitates in the liquid non-solvent to form agglomerates having longest dimensions from 500 μm to 15 mm.

14. The process of claim 13 , further comprising crushing or grinding the agglomerates to form a powder having a volume average particle size of 20 to 500 μm.

Assignments (5)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 10, 2024
From: DOW GLOBAL TECHNOLOGIES LLC
To: THE DOW CHEMICAL COMPANY
Reel/Frame 069923/0030 →
CHANGE OF LEGAL ENTITY Recorded Sep 10, 2024
From: DDP SPECIALTY ELECTRONIC MATERIALS US, INC
To: DDP SPECIALTY ELECTRONIC MATERIALS US, LLC
Reel/Frame 068907/0881 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 10, 2024
From: THE DOW CHEMICAL COMPANY
To: DDP SPECIALTY ELECTRONIC MATERIALS US, INC
Reel/Frame 068922/0001 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 9, 2017
From: BEAUDOIN, DANIEL A.; HULL, JOHN W., JR.; PORTER, MICHAL E.; STOBBY, WILLIAM G.; BILLOVITZ, GERALD F.; YOUNG, TIMOTHY J.
To: DOW GLOBAL TECHNOLOGIES LLC
Reel/Frame 043249/0389 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 2, 2016
From: BEAUDOIN, DANIEL A.; HULL, JOHN W., J; PORTER, MICHAL E.; STOBBY, WILLIAM G.; BILLOVITZ, GERALD F.; YOUNG, TIMOTHY J.
To: DOW GLOBAL TECHNOLOGIES LLC
Reel/Frame 038791/0548 →
Continuity (2)
Provisional Application 61921499 · Dec 29, 2013
Related Publication 20160304649A1 · Oct 20, 2016