IP Library Granted Patent US 11,359,039
Granted Patent B2
US 11,359,039 · App. 16/648,526 · Granted Jun 14, 2022

Polar comonomer enchainment in olefin polymerization reactions

Inventors: Tobin J. Marks (Evanston, IL); Jiazhen Chen (Evanston, IL); Tracy L. Lohr (Houston, TX)
Assignee: Northwestern University
C08F210/02C08F4/52C08F4/61927C08F2410/03
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 11,359,039
App. No.
16/648,526
Granted
Jun 14, 2022
Kind
B2
Abstract

A method for forming polar-functionalized polyolefins may comprise contacting an unsubstituted α-olefin monomer and an amino-olefin monomer of formula H 2 C═CH(CH 2 ) n (CHR) m NR′ 2 , wherein R is H or an unsubstituted linear or branched alkyl group having from 1 to 10 carbons, each R′ is an independently selected unsubstituted linear or branched alkyl group having from 1 to 10 carbons, m is an integer from 1 to 11, and n is an integer from 1 to 11, in the presence of a rare earth catalyst and a cocatalyst under conditions to induce a heteropolymerization reaction between the unsubstituted oc-olefin and amino-olefin monomers to provide a polar-functionalized poly olefin.

Claims (22)

1. A method for forming a polar-functionalized polyolefin, the method comprising contacting an unsubstituted α-olefin monomer and an amino-olefin monomer of formula H 2 C═CH(CH 2 ) 2 (CHR) m NR′ 2 , wherein R is H or an unsubstituted linear or branched alkyl group having from 1 to 10 carbons, each R′ is an independently selected unsubstituted linear or branched alkyl group having from 1 to 10 carbons, m is an integer from 0 to 11, and n is an integer from 1 to 11, in the presence of a rare earth catalyst and a cocatalyst under conditions to induce a heteropolymerization reaction between the unsubstituted α-olefin and amino-olefin monomers to provide a polar-functionalized polyolefin.

2. The method of claim 1 , wherein the amino-olefin monomer has formula H 2 C═CH(CH 2 ) n NR′ 2 , wherein each R′ is an independently selected unsubstituted linear or branched alkyl group having from 1 to 10 carbons and n is an integer from 1 to 11.

3. The method of claim 1 , wherein each R′ group of the amino-olefin monomer is the same.

4. The method of claim 2 , wherein the alkyl group of the amino-olefin monomer is a linear alkyl group.

5. The method of claim 1 , wherein the unsubstituted α-olefin monomer is of formula H 2 C═CHR, wherein R is selected from H and (CH 2 ) n CH 3 , wherein n is an integer between 0 and 10.

6. The method of claim 1 , wherein the unsubstituted α-olefin monomer is ethylene.

7. The method of claim 1 , wherein the rare earth catalyst is selected from a group consisting of a mononuclear organoscandium catalyst, a binuclear organoscandium catalyst, a mononuclear organoyttrium catalyst, a binuclear organoyttrium catalyst, a mononuclear organoytterbium catalyst, a binuclear organoytterbium catalyst a mononuclear organolutetium catalyst, a binuclear organolutetium catalyst, and combinations thereof.

8. The method of claim 7 , wherein the rare earth catalyst is of Formula 6 or Formula 7,

wherein M is selected from Sc, Y, Yb, and Lu and n is 0 or 2.

9. The method of claim 8 , wherein M is selected from Sc, Y, and Yb.

10. The method of claim 9 , wherein the rare earth catalyst is of Formula 6.

11. The method of claim 10 , wherein M is Sc.

12. The method of claim 1 , wherein the heteropolymerization reaction is carried out in the presence of an exogenous Lewis base.

13. The method of claim 12 , wherein the exogenous Lewis base is a tertiary amine.

14. A method for forming a polar-functionalized polyolefin, the method comprising contacting an olefin monomer of formula H 2 C═CHR, wherein R is selected from H and (CH 2 ) n CH 3 , wherein n is an integer between 0 and 10, and an amino-olefin monomer of formula H 2 C═CH(CH 2 ) n NR′ 2 , wherein each R′ is the same linear, unsubstituted alkyl group having from 1 to 10 carbons and n is an integer from 1 to 11, in the presence of a rare earth catalyst and a cocatalyst under conditions to induce a heteropolymerization reaction between the olefin and amino-olefin monomers to provide a polar-functionalized polyolefin, wherein the rare earth catalyst is of Formula 6 or Formula 7,

wherein M is selected from Sc, Y, Yb, and Lu and n is 0 or 2.

15. The method of claim 14 , wherein the olefin monomer is ethylene.

16. The method of claim 14 , wherein M is selected from Sc, Y, and Yb.

17. The method of claim 16 , wherein the rare earth catalyst is of Formula 6.

18. The method of claim 17 , wherein M is Sc.

19. The method of claim 14 , wherein the heteropolymerization reaction is carried out in the presence of an exogenous Lewis base.

20. The method of claim 19 , wherein the exogenous Lewis base is a tertiary amine.

Assignments (3)
CONFIRMATORY LICENSE Recorded Feb 6, 2025
From: NORTHWESTERN UNIVERSITY
To: NATIONAL SCIENCE FOUNDATION
Reel/Frame 070129/0383 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 19, 2020
From: MARKS, TOBIN J; CHEN, JIAZHEN; LOHR, TRACY L.
To: NORTHWESTERN UNIVERSITY
Reel/Frame 052699/0546 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 20, 2020
From: MARKS, TOBIN J; CHEN, JIAZHEN; LOHR, TRACY L.
To: NORTHWESTERN UNIVERSITY
Reel/Frame 052444/0252 →
Continuity (2)
Provisional Application 62568978 · Oct 6, 2017
Related Publication 20200223963A1 · Jul 16, 2020