IP Library Granted Patent US 11,827,753
Granted Patent B2
US 11,827,753 · App. 16/896,432 · Granted Nov 28, 2023

Highly pure halogenated rubbers

Inventors: Gilles Joseph Arsenault (Courtright, CA); David Thompson (London, CA); Clinton Lund (London, CA)
Assignee: ARLANXEO SINGAPORE PTE. LTD.
C08J3/07C08J3/21C08J3/24C08K5/098C08L23/283B29B9/06B29B9/065C08J2323/28
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 11,827,753
App. No.
16/896,432
Granted
Nov 28, 2023
Kind
B2
Abstract

The invention relates to a method to reduce or prevent agglomeration of particles of halogenated rubbers in aqueous media by LCST compounds as well as highly pure halogenated rubbers. The invention further relates to halogenated elastomer products comprising the same or derived therefrom.

Claims (30)

1. A slurry comprising:

a dispersion of particles of a halogenated elastomer in an aqueous medium; and

at least one lower critical solution temperature (LCST) compound having a cloud point of 0 to 100° C.;

wherein the LCST compound is present in an amount of 1 to 1,000 ppm measured with respect to an amount of the halogenated elastomer.

2. The slurry of claim 1 , wherein the slurry includes 1 to 2,000 ppm of antioxidant based on a total weight of the aqueous medium.

3. The slurry of claim 1 , wherein the halogenated elastomer comprise repeating units derived from at least one isoolefin and repeating units derived from at least one multiolefin.

4. The slurry of claim 3 , wherein the isoolefin includes an isoolefin having 4 to 16 carbon atoms, optionally wherein the isoolefin is isobutene.

5. The slurry of claim 4 , wherein the multiolefin includes isoprene, butadiene, 2-methylbutadiene, 2,4-dimethylbutadiene, piperyline, 3-methyl-1,3-pentadiene, 2,4-hexadiene, 2-neopentylbutadiene, 2-methyl-1,5-hexadiene, 2,5-dimethyl-2,4-hexadiene, 2-methyl-1,4-pentadiene, 4-butyl-1,3-pentadiene, 2,3-dimethyl-1,3-pentadiene, 2,3-dibutyl-1,3-pentadiene, 2-ethyl-1,3-pentadiene, 2-ethyl-1,3-butadiene, 2-methyl-1,6-heptadiene, cyclopentadiene, methylcyclopentadiene, cyclohexadiene or 1-vinyl-cyclohexadiene.

6. The slurry of claim 1 , wherein the halogenated elastomer comprises repeating units derived from isobutene and repeating units derived from isoprene.

7. The slurry of claim 1 , wherein the slurry comprises at least 20 of the particles per liter, wherein the particles have a particle size of 0.05 to 25 mm.

8. The slurry of claim 7 , wherein the slurry comprises at least 100 of the particles per liter, wherein the particles have a particle size of 0.3 to 10 mm.

9. The slurry of claim 8 , wherein the LOST compound has a cloud point of 15 to 80° C.

10. The slurry of claim 9 , wherein the slurry includes an organic diluent.

11. A mixture comprising:

a dispersion of particles of a halogenated elastomer in an aqueous medium;

at least one lower critical solution temperature (LOST) compound in the aqueous medium having a cloud point of 0 to 100° C.; and

an organic diluent;

wherein the mixture has a temperature of 50° C. to 100° C.

12. The mixture of claim 11 , wherein the halogenated elastomer comprises repeating units derived from isobutene and repeating units derived from isoprene.

13. The mixture of claim 12 , wherein the LCST compound is present in an amount of 1 to 5,000 ppm measured with respect to the amount of the halogenated elastomer.

14. The mixture of claim 11 , wherein the slurry includes 1 to 2,000 ppm of antioxidant based on a total weight of the aqueous medium.

15. The mixture of claim 12 , wherein the LCST compound has a cloud point of 15 to 80° C.

16. The mixture of claim 15 , wherein the organic diluent includes one or more hydrocarbons selected from the group consisting of propane, isobutane, pentane, methycyclopentane, isohexane, 2-methylpentane, 3-methylpentane, 2-methylbutane, 2,2-dimethylbutane, 2,3-dimethylbutane, 2-methylhexane, 3-methylhexane, 3-ethylpentane, 2,2-dimethylpentane, 2,3-dimethylpentane, 2,4-dimethylpentane, 3,3-dimethyl pentane, 2-methylheptane, 3-ethylhexane, 2,5-dimethylhexane, 2,2,4,-trimethylpentane, octane, heptane, butane, ethane, methane, nonane, decane, dodecane, undecane, hexane, methyl cyclohexane, cyclopropane, cyclobutane, cyclopentane, methylcyclopentane, 1,1-dimethylcyclopentane, cis-1,2-dimethylcyclopentane, trans-1,2-dimethylcyclopentane, trans-1,3-dimethyl-cyclopentane, ethylcyclopentane, cyclohexane, and methylcyclohexane.

17. The mixture of claim 16 , wherein the organic diluent includes the hydrocarbon and a hydrochlorocarbon.

18. The mixture of claim 17 , wherein the hydrochlorocarbon includes dichloromethane.

19. A slurry comprising:

a dispersion of particles of a halogenated elastomer in an aqueous medium; and

at least one lower critical solution temperature (LOST) compound having a cloud point of 0 to 100° C.;

wherein the at least on LOST compound is selected from the group consisting of: poly(N-isopropylacrylamide), poly(N-isopropylacrylamide-co-N,N-dimethylacrylamide, poly(N-isopropylacrylamide)-alt-2-hydroxyethylmethacrylate, poly(N-vinylcaprolactam), poly(N,N-diethylacrylamide), poly[2-(dimethylamino)ethyl methacrylate], poly(2-oxazoline) glyhalogenated elastomer, poly(3-ethyl-N-vinyl-2-pyrrolidone), hydroxylbutyl chitosan, polyoxyethylene sorbitan monostearate, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monooleate, methyl cellulose having a viscosity of 25 to 4000 cp (measured at 2 wt. % in water at 20° C.), hydroxypropyl cellulose, hydroxyethyl methylcellulose, hydroxypropyl methylcellulose, poly(ethylene glycol) methacrylate having 2 to 6 ethylene glycol units, polyethyleneglycol-co-polypropylene glycol, polyethyleneglycol-co-polypropylene glycol, ethoxylated iso-013H27-alcohols, polyethylene glycol having 4 to 50 ethyleneglycol units, polypropylene glycol having 4 to 30 propyleneglycol units, polyethylene glycol monomethyl ether having 4 to 50 ethyleneglycol units, polyethylene glycol dimethyl ether having 4 to 50 ethyleneglycol units, polyethylene glycol monoethyl ether having 4 to 50 ethyleneglycol units, polyethylene glycol diethyl ether having 4 to 50 ethyleneglycol units, polypropylene glycol monomethyl ether having 4 to 50 propyleneglycol units, polypropylene glycol dimethyl ether having 4 to 50 propyleneglycol units, polypropylene glycol monoethyl ether having 4 to 50 propyleneglycol units, and polypropylene glycol diethyl ether having 4 to 50 propyleneglycol units.

20. The slurry of claim 19 , wherein the LCST compound comprises a cellulose-containing compound selected from the methyl cellulose, the hydroxypropyl cellulose, the hydroxyethyl methylcellulose and the hydroxypropyl methylcellulose; wherein the cellulose-containing compound has a degree of substitution of 1.2 to 2.5.

Assignments (3)
CHANGE OF NAME Recorded Oct 5, 2020
From: LANXESS BUTYL PTE. LTD.
To: ARLANXEO SINGAPORE PTE. LTD.
Reel/Frame 053979/0047 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 1, 2020
From: LANXESS INC.
To: LANXESS BUTYL PTE. LTD.
Reel/Frame 053944/0060 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 29, 2020
From: THOMPSON, DAVID B.; ARSENAULT, GILLES; LUND, CLINTON
To: LANXESS INC.
Reel/Frame 053921/0249 →
Priority Claims (5)
EP 13199466 · Dec 23, 2013 · regional
EP 14160794 · Mar 19, 2014 · regional
EP 14160795 · Mar 19, 2014 · regional
EP 14175053 · Jun 30, 2014 · regional
EP 14175964 · Jul 7, 2014 · regional
Continuity (2)
Continuation 15107511
Related Publication 20200299465A1 · Sep 24, 2020