Capped dual-headed organoaluminum compositions

Patent metadata

Field	Value
Publication number	US-11613600-B2
Application number	US-201816959008-A
Country	US
Kind code	B2
Filing date	Dec 27, 2018
Priority date	Dec 29, 2017
Publication date	Mar 28, 2023
Grant date	Mar 28, 2023

Abstract

The present disclosure relates to a capped dual-headed organoaluminum composition having the formula (I) and processes to prepare the same. In at least one aspect, the capped dual-headed organoaluminum compositions can be used in olefin polymerization.

First claim

What is claimed is:

1. A composition of formula (I):

wherein:
n is a number from 1 to 100;
Y is a linking group composed of a linear, branched, or cyclic C 4 to C 100 hydrocarbylene group that optionally includes at least one heteroatom and that is aliphatic or aromatic, wherein Y comprises two points of attachment to Al atoms and at least one of the two points of attachment is —CH 2 —;
each R group is independently a substituted or unsubstituted aryl group or a substituted or unsubstituted cyclic alkyl group containing, optionally, at least one heteroatom; and
two R groups attached to the same Al can be optionally covalently linked together.

2. The composition of claim 1 , wherein each R group is independently selected from the group consisting of the following structures CG1 to CG4:

wherein:
each R 1 is independently hydrogen or a C 1 to C 20 alkyl group;
each X 2 , X 3 , X 4 , and X 5 is independently hydrogen, a substituted or unsubstituted C 1 to C 20 alkyl, alkylene or alkylidene group, or a substituted or unsubstituted C 6 to C 20 aryl group;
each X 2 , X 3 , X 4 , and X 5 optionally includes at least one heteroatom; and
in each of structures CG1 to CG3, two of the groups selected from X 2 , X 3 , X 4 , and X 5 may optionally join to form cyclic structures.

3. The composition of claim 1 , wherein each R group is independently selected from the group consisting of the following structures CG5 to CG13:

wherein each R 1 is independently hydrogen or a C 1 to C 20 alkyl group.

4. The composition of claim 1 , wherein each R group is CG5 or CG12.

5. The composition of claim 1 , wherein Y has the formula (II):
—CH 2 CH 2 (CHR 2 ) m CH 2 CH 2 —  (II),

wherein:
R 2 is hydrogen or a C 1 to C 20 alkyl or aryl group; and
m is a number from 0 to 20.

6. The composition of claim 1 , wherein Y has the formula (III):
—CH 2 CH 2 —Z—CH 2 CH 2 —  (III),

wherein:
Z is a C 4 to C 100 hydrocarbylene group comprising at least one aliphatic or aromatic ring and, optionally, includes at least one heteroatom.

7. The composition of claim 1 , wherein Y is a derivative of a linking agent selected from the group consisting of 1,9-decadiene, 1,4-pentadiene, divinylbenzene, divinyldiphenylsilane, divinyldimethylsilane, 1,4-bis(dimethyl(vinyl)silyl)benzene, 1,5-bis(dimethyl(vinyl)silyl)pentane, and 1,3-divinylcyclopentane.

8. The composition of claim 1 , wherein n is a number from 1 to 10.

9. The composition of claim 8 , wherein n is a number from 1 to 3.

10. A process for preparing a composition, the process comprising:
(a) combining an aluminum compound, a linking agent, a capping agent, and an optional solvent at a temperature of from 50° C. to 200° C. for a time from 30 minutes to 200 hours, and
(b) obtaining the composition, wherein:
the aluminum compound has the formula Al(J) 3 , wherein each J group is independently hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl or heteroaryl group, wherein at least one J group is a hydrogen or an acyclic alkyl group and, optionally, two J groups can be covalently linked together;
the linking agent is a C 4 to C 100 hydrocarbon comprising either at least two vinyl groups or a vinyl group and a cyclic olefin group and, optionally, includes at least one heteroatom; and
the capping agent is a substituted or unsubstituted cyclic olefin.

11. The process of claim 10 , wherein the capping agent is selected from the group consisting of the following structures CA1 to CA4:

wherein:
each X 2 , X 3 , X 4 , and X 5 is independently hydrogen, a substituted or unsubstituted C 1 to C 20 alkyl, alkylene or alkylidene group, or a substituted or unsubstituted C 6 to C 20 aryl group;
each X 2 , X 3 , X 4 , and X 5 optionally includes at least one heteroatom; and
in each of structure CA1 to CA3, two of the groups selected from X 2 , X 3 , X 4 , and X 5 may optionally join to form cyclic structures.

12. The process of claim 11 , wherein the capping agent is selected from the group consisting of the following structures CG5 to CG10:

13. The process of claim 12 , wherein the capping agent is CG5 or CG9.

14. The process of claim 10 , wherein the aluminum compound is triisobutylaluminum or diisobutylaluminum hydride.

15. The process of claim 10 , wherein the linking agent is selected from the group consisting of 1,9-decadiene, 1,4-pentadiene, divinylbenzene, divinyldiphenylsilane, divinyldimethylsilane, 1,4-bis(dimethyl(vinyl)silyl)benzene, 1,5-bis(dimethyl(vinyl)silyl)pentane, and 1,3-divinylcyclopentane.

16. A composition comprising the reaction product of: an aluminum compound, a linking agent, a capping agent, and an optional solvent, wherein:
the aluminum compound has the formula Al(J) 3 , wherein each J group is independently hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl or heteroaryl group, wherein at least one J group is a hydrogen or an acyclic alkyl group, and optionally, two J groups can be covalently linked together;
the linking agent is a C 4 to C 100 hydrocarbon comprising either at least two vinyl groups or a vinyl group and a cyclic olefin group and, optionally, includes at least one heteroatom; and
the capping agent is a substituted or unsubstituted cyclic olefin.

17. A polymerization process for preparing a polymer composition, the process comprising: (a) contacting at least one olefin monomer with a catalyst composition, wherein the catalyst composition comprises the reaction product of at least one catalyst precursor, at least one co-catalyst, and the composition of claim 1 , and (b) obtaining the polymer composition.

18. A polymer composition prepared by the process of claim 17 , wherein the polymer composition comprises two aluminum termini.

19. A process for preparing a polymer or a polymer mixture by converting polymer-Al bonds of the polymer composition of claim 18 using either a chemical reagent or high temperature.

Assignees

• Dow Global Technologies Llc

Inventors

• Sun Lixin
• Szuromi Endre
• Klosin Jerzy
• Carnahan Edmund M
• Patton Jasson T
• Liao Longyan

Classifications

• C08F4/65908

  in combination with an ionising compound other than alumoxane, e.g. (C6F5)4B-X+ · CPC title

• B01J21/02

  Boron or aluminium; Oxides or hydroxides thereof · CPC title

• C08F2438/00

  Living radical polymerisation · CPC title

• C07F7/00

  Compounds containing elements of Groups 4 or 14 of the Periodic Table · CPC title

• C07F5/062 Primary

  Al linked exclusively to C · CPC title