IP Library Granted Patent US 11,840,624
Granted Patent B2
US 11,840,624 · App. 17/111,682 · Granted Dec 12, 2023

Methods for forming stereospecific, polar functionalized polypropylene

Inventors: Tobin J. Marks (Evanston, IL); Minglu Huang (Evanston, IL); Yanshan Gao (Evanston, IL)
Assignee: Northwestern Unversity
C08L23/36C08F4/52C08F4/76
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Quick Facts
Patent No.
US 11,840,624
App. No.
17/111,682
Granted
Dec 12, 2023
Kind
B2
Abstract

Methods for forming polar-functionalized isotactic and syndiotactic polypropylenes are provided, including amino-functionalized polypropylene. In embodiments, such a method comprises contacting a propylene monomer and a polar monomer comprising an amine group in the presence of an organozirconium catalyst and in the absence of a masking reagent, under conditions to induce a polymerization reaction between the propylene and polar monomers, thereby forming polar-functionalized polypropylene.

Claims (21)

1. A method for forming polar-functionalized polypropylene, the method comprising contacting a propylene monomer and a polar monomer comprising an amine group in the presence of an organozirconium catalyst and in the absence of AlBu i 3 and/or in the absence of methylaluminoxane, under conditions to induce a polymerization reaction between the propylene and polar monomers, thereby forming polar-functionalized polypropylene.

2. The method of claim 1 , wherein the amine group has formula NR 2 , wherein each R is an independently selected unsubstituted linear alkyl group or an unsubstituted branched alkyl group.

3. The method of claim 2 , wherein each R is an independently selected unsubstituted linear alkyl group.

4. The method of claim 3 , wherein the amine group has formula N(CH 2 CH 2 CH 3 ) 2 .

5. The method of claim 1 , wherein the amine group is covalently bound via a linear alkyl group having no more than 7 carbon atoms.

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

7. The method of claim 6 , wherein each R is an independently selected unsubstituted linear alkyl group.

8. The method of claim 7 , wherein the polar monomer has formula H 2 C═CH(CH 2 ) n N(CH 2 CH 2 CH 3 ) 2 .

9. The method of claim 8 , wherein n is from 1 to 7.

10. The method of claim 1 , wherein the organozirconium catalyst is SBIZrMe 2 or FluZrMe 2 .

11. The method of claim 10 , wherein the polar monomer has formula H 2 C═CH(CH 2 ) n N(CH 2 CH 2 CH 3 ) 2 .

12. The method of claim 11 , wherein n is from 1 to 7.

13. The method of claim 7 , wherein the polar-functionalized polypropylene exhibits a pentad isotacticity mmmm of at least 75% or a pentad syndiotacticity rrrr of at least 70%.

14. A method for forming polar-functionalized polypropylene, the method comprising contacting a propylene monomer and a polar monomer comprising an amine group in the presence of an organozirconium catalyst, under conditions to induce a polymerization reaction between the propylene and polar monomers, thereby forming polar-functionalized polypropylene, wherein the polar-functionalized polypropylene is syndiotactic.

15. The method of claim 14 , wherein the polar-functionalized polypropylene exhibits a pentad syndiotacticity rrrr of at least 70%.

16. The method of claim 15 , wherein the organozirconium catalyst is FluZrMe 2 and the polar monomer has formula H 2 C═CH(CH 2 ) n NR 2 , wherein each R is an independently selected unsubstituted linear alkyl group and n is an integer from 1 to 11.

17. The method of claim 16 , wherein the polar monomer has formula H 2 C═CH(CH 2 ) n N(CH 2 CH 2 CH 3 ) 2 and n is from 1 to 7.

18. The method of claim 1 , wherein the contacting step is further conducted in the absence of any masking reagent capable of binding to the amine group of the polar monomer.

19. The method of claim 14 , wherein the contacting step is conducted in the absence of AlBu i 3 and in the absence of methylaluminoxane.

20. The method of claim 19 , wherein the contacting step is further conducted in the absence of any masking reagent capable of binding to the amine group of the polar monomer.

21. The method of claim 1 , wherein the organozirconium catalyst is SBIZrMe 2 and the polar monomer has formula H 2 C═CH(CH 2 ) 6 N(CH 2 CH 2 CH 3 ) 2 .

Assignments (2)
CONFIRMATORY LICENSE Recorded Jan 30, 2025
From: NORTHWESTERN UNIVERSITY
To: NATIONAL SCIENCE FOUNDATION
Reel/Frame 070058/0455 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 10, 2021
From: MARKS, TOBIN J.; HUANG, MINGLU; GAO, YANSHAN
To: NORTHWESTERN UNIVERSITY
Reel/Frame 057143/0988 →
Continuity (2)
Provisional Application 62943384 · Dec 4, 2019
Related Publication 20210171753A1 · Jun 10, 2021