IP Library Granted Patent US 12,122,797
Granted Patent B2
US 12,122,797 · App. 17/612,469 · Granted Oct 22, 2024

Organosilane, ionic organosilane, membrane composition, and membrane

Inventors: Claire Hartmann-Thompson (Lake Elmo, MN); Marina M. Kaplun (Woodbury, MN)
Assignee: 3M Innovative Properties Company
C07F7/081C08F212/08C08K5/5406
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 12,122,797
App. No.
17/612,469
Granted
Oct 22, 2024
Kind
B2
Abstract

A dihaloorganosilane is represented by the formula (I): Each X independently represents Cl, Br, or I. Each Ar 1 independently represents a phenylene group optionally substituted by 1 to 4 alkyl groups selected from methyl or ethyl. Each R 1 independently represents an alkylene group having from 2 to 18 carbon atoms. Each R 2 independently represents methyl or ethyl. Each R 3 independently represents an alkylene group having from 1 to 18 carbon atoms. Each R 4 independently represents an alkylene group having from 2 to 18 carbon atoms, and n is an integer in a range of 0 to 5, inclusive. Ionic organosilanes preparable from the dihaloorganosilanes are represented by the formula (II): Membrane compositions and membranes containing the ionic organosilanes are also disclosed.

Claims (54)

1. A dihaloorganosilane represented by the formula:

wherein:

each X independently represents Cl, Br, or I;

each Ar 1 independently represents a phenylene group optionally substituted by 1 to 4 alkyl groups selected from methyl or ethyl;

each R 1 independently represents an alkylene group having from 2 to 18 carbon atoms;

each R 2 independently represents methyl or ethyl;

each R 3 independently represents an alkylene group having from 1 to 18 carbon atoms;

each R 4 independently represents an alkylene group having from 2 to 18 carbon atoms; and

n is an integer in a range of 0 to 5, inclusive.

2. The dihaloorganosilane of claim 1 , wherein each R 1 independently represents an alkylene group having 2 or 3 carbon atoms.

3. The dihaloorganosilane of claim 1 , wherein each R 3 independently represents an alkylene group having from 2 to 4 carbon atoms.

4. The dihaloorganosilane of claim 1 , wherein each R 4 independently represents an alkylene group having from 6 to 10 carbon atoms.

5. The dihaloorganosilane of claim 1 , wherein n=0.

6. The dihaloorganosilane of claim 1 , wherein n=1.

7. An ionic organosilane represented by the formula:

wherein:

each X independently represents Cl, Br, or I;

each Ar 1 independently represents a phenylene group optionally substituted by 1 to 4 alkyl groups selected from methyl or ethyl;

each R 1 independently represents an alkylene group having from 2 to 18 carbon atoms;

each R 2 independently represents methyl or ethyl;

each R 3 independently represents an alkylene group having from 1 to 18 carbon atoms;

each R 4 independently represents an alkylene group having from 2 to 18 carbon atoms;

each R 5 independently represents H or methyl;

each R 6 independently represents alkyl having from 1 to 4 carbon atoms, or allyl; and

n is an integer in a range of 0 to 5, inclusive.

8. The ionic organosilane of claim 7 , wherein each R 1 independently represents an alkylene group having 2 or 3 carbon atoms.

9. The ionic organosilane of claim 7 , wherein each R 3 independently represents an alkylene group having from 2 to 4 carbon atoms.

10. The ionic organosilane of claim 7 , wherein each R 4 independently represents an alkylene group having from 6 to 10 carbon atoms.

11. The ionic organosilane of claim 7 , wherein n=0.

12. The ionic organosilane of claim 7 , wherein n=1.

13. A membrane composition comprising components:

(a) a copolymer comprising the divalent monomer units:

wherein:

R 5 represents H or methyl;

R 6 represents alkyl having from 1 to 4 carbon atoms, or allyl; and

X represents Cl, Br, or I, and

wherein monomer unit (i) and monomer unit (ii) are present in a respective mole ratio of 1.5:1 to 3:1; and

(b) an ionic organosilane compound represented by the formula:

wherein:

each Ar 1 independently represents a phenylene group optionally substituted by 1 to 4 alkyl groups selected from methyl or ethyl;

each R 1 independently represents an alkylene group having from 2 to 18 carbon atoms;

each R 2 independently represents methyl or ethyl;

each R 3 independently represents an alkylene group having from 1 to 18 carbon atoms;

each R 4 independently represents an alkylene group having from 2 to 18 carbon atoms; and

n is an integer in a range of 0 to 5, inclusive; and

wherein component (a) and component (b) are present in a respective weight ratio in a range of 99.5:0.5 to 98:2.

14. The membrane composition of claim 13 , wherein each R 1 independently represents an alkylene group having 2 or 3 carbon atoms.

15. The membrane composition of claim 13 , wherein each R 3 independently represents an alkylene group having from 2 to 4 carbon atoms.

16. The membrane composition of claim 13 , wherein each R 4 independently represents an alkylene group having from 6 to 10 carbon atoms.

17. The membrane composition of claim 13 , wherein n=0.

18. The membrane composition of claim 13 , wherein n=1.

19. The membrane composition of claim 13 , wherein R 6 represents alkyl having from 1 to 4 carbon atoms.

20. The membrane composition of claim 13 , wherein R 6 represents allyl.

21. A membrane comprising the membrane composition of claim 13 .

Assignments (2)
CONFIRMATORY LICENSE Recorded Jul 17, 2024
From: 3M COMPANY
To: US DEPARTMENT OF ENERGY
Reel/Frame 068410/0695 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 18, 2021
From: HARTMANN-THOMPSON, CLAIRE; KAPLUN, MARINA M.
To: 3M INNOVATIVE PROPERTIES COMPANY
Reel/Frame 058189/0114 →
Continuity (2)
Provisional Application 62862327 · Jun 17, 2019
Related Publication 20220251120A1 · Aug 11, 2022