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WO-2026096716-A1 - ORGANOMETALLIC COMPOUNDS FOR USE AS CHAIN TRANSFER AGENTS AND METHODS OF MAKING THE SAME

WO2026096716A1WO 2026096716 A1WO2026096716 A1WO 2026096716A1WO-2026096716-A1

Abstract

Embodiments are directed to an organometallic compound represented by the general formula, M[CH 2 CH(R 1 SiMe 2 X)(R 2 SiMe 2 X)] a , wherein M includes a zinc atom or an aluminum atom; R 1 and R 2 are independently a hydrocarbon chain comprising from 1 to 20 carbon atoms, X is a hydrogen atom or a vinyl group, and a is 2 or 3. Further embodiments are directed to methods for making the organometallic compound and methods for making polyolefin compounds utilizing the organometallic compound.

Inventors

  • SUN, LIXIN

Assignees

  • DOW GLOBAL TECHNOLOGIES LLC

Dates

Publication Date
20260507
Application Date
20251030
Priority Date
20241031

Claims (15)

  1. 1. An organometallic compound represented by the general formula, M[CH 2 CH(RiSiMe 2 X)(R 2 SiMe 2 X)] a , wherein: M comprises a zinc atom or an aluminum atom; Ri and R 2 are independently a hydrocarbon chain comprising from 1 to 20 carbon atoms; X is a hydrogen atom or a vinyl group; and a is 1, 2, or 3.
  2. 2 The organometallic compound of claim 1, wherein M is an aluminum atom and a is 3.
  3. 3 The organometallic compound of claim 1, wherein M is represented by the formula (NB)bM, wherein: NB is a norbornyl group derived from norbornene (NB), ethylidene norbornene (ENB), or dicyclopentadiene (DCPD); and b is 1 or 2.
  4. 4 The organometallic compound of claim 3, wherein M is represented by the general formula (NB)bAl and a + b is 3.
  5. 5 The organometallic compound of claim 3, wherein M is represented by the general formula (NB)bZn, where b is 1 and a is 1.
  6. 6 A method of making the organometallic compound of claim 1, the method comprising: combining a silane-containing compound and an aluminum- containing compound at a temperature from 100 °C to 150 °C for a duration from 1 hour to 5 hours to form a mono functional compound represented by the formula Al(RiSiMe 2 X)3; and contacting the monofunctional compound with the silane-containing compound, a catalyst, and an activator to form the organometallic compound.
  7. 7 The method of making the organometallic compound of claim 6, the method further comprising: 86262-WO-PCT/DOW 86262 WO 26 contacting a norbornene compound and dialkylzinc with a catalyst and an activator to form a dinorbonylzinc compound represented by the formula Zn(NB) 2 , where NB is a norbornyl group derived from norbornene (NB), ethylidene norbornene (ENB), or dicyclopentadiene (DCPD); and combining the mono functional compound and the dinorbonylzinc compound with the silane- containing compound, the catalyst, and the activator to form the organometallic compound.
  8. 8 A method for making a polyolefin compound, the method comprising: polymerizing olefins in the presence of the organometallic compound of any one of claims 1 to 5, a catalyst, and an activator to form the polyolefin compound, wherein: the polyolefin compound is represented by the formula, P 1 CH 2 CH(RiSiMe 2 X)(R 2 SiMe 2 X), and P 1 is a polyolefin.
  9. 9 The method of claim 8, wherein the polyolefin compound is represented by the formula A 1 P 1 CH 2 CH(RiSiMe 2 X)(R 2 SiMe 2 X), wherein: A 1 is selected from the group consisting of a vinyl group, a vinylidene group of the formula CH 2 =C(Y 1 )-, a vinylene group of the formula Y 1 CH=CH-, a mixture of a vinyl group and a vinylene group of the formula Y 1 CH=CH-, a mixture of a vinyl group and a vinylidene group of the formula CH 2 =C(Y 1 )-, a mixture of a vinylidene group of the formula CH 2 =C(Y 1 )- and a vinylene group of the formula Y 1 CH=CH-, and a mixture of a vinyl group, a vinylidene group of the formula CH 2 =C(Y 1 )-, and a vinylene group of the formula Y 1 CH=CH-; and Y 1 at each occurrence independently is a Ci to C30 hydrocarbyl group.
  10. 10 The method of any one of claims 6 to 9, wherein the catalyst is represented by the formula: wherein: X 1 is chosen from a halide, a N,N-dimethylamido, and a Ci-4 alkyl; and Ri - R? are independently a hydrogen, a halogen, a C1-20 alkyl, or a Ce- 2 o aryl. 86262-WO-PCT/DOW 86262 WO 27
  11. 11. The method of any one of claims 6 to 10, wherein the catalyst is represented by the formula:
  12. 12. The method of any one of claims 6 to 10, wherein the catalyst is represented by the formula: wherein: X 1 is chosen from a halide, a N,N-dimethylamido, and a Ci-4 alkyl; R f is a hydrogen, a halogen, a C1-20 alkyl, or a C6-20 aryl; f is 1 to 5; R c is a hydrogen, halogen, C1.20 alkyl, or C6-20 aryl; and c is 1 to 5.
  13. 13. The method of any one of claims 6 or 7, wherein the silane-containing compound comprises 7-octenyldimethylsilane, 5-hexenyldimethylsilane, allyldimethylsilane or combinations thereof.
  14. 14. The method of any one of claims 6 or 7, wherein the aluminum- containing compound is triisobutylaluminum.
  15. 15. The method of any one of claims 6 to 14, wherein the activator is represented by the formula [HNMe(Ci8H37)2][B(C6F5)4].

Description

86262-WO-PCT/DOW 86262 WO 1 ORGANOMETALLIC COMPOUNDS FOR USE AS CHAIN TRANSFER AGENTS AND METHODS OF MAKING THE SAME CROSS REFERENCE TO RELATED APPLICATION [0001] This application claims priority to U.S. Provisional Application Serial No. 63/714,243 filed October 31, 2024, the entire disclosure of which is hereby incorporated by reference. TECHNICAL FIELD [0002] Embodiments described herein generally relate to organometallic compounds and, more specifically, to organometallic compounds for use as chain transfer agents, methods of making the same, and methods of making polyolefin compounds that utilize the same. BACKGROUND [0003] In recent years, advances in polymer design have been seen with the use of compositions capable of chain transfer. For example, chain transfer agents (CTA) may cause termination of polymer chain growth and amounts to a transfer of a growing polymer from a catalyst to the CTA. CTAs may enable the production of novel olefin block copolymers (OBCs) through transfer of growing polymer chains back and forth between catalyst(s) and CTA. Compositions capable of chain transfer may be simple metal alkyls, such as diethylzinc and triethylaluminum. CTAs are important in the production of polyolefins, as CTAs enable the synthesis of polyolefins having desirable functional groups and/or architectures. [0004] Accordingly, there is a need for improved organometallic compounds that may be used as CTAs to enable production of such polyolefins, as well as methods of making such organometallic compounds. SUMMARY [0005] The embodiments of the present disclosure meet this need by utilizing a bifunctional organometallic compound. This results in a CTA that provides for the production polyolefins having relatively complex architectures as compared to polyolefins produces using monofunctional CTAs. As described herein, according to one or more embodiments, the organometallic compound may be bifunctional. 86262-WO-PCT/DOW 86262 WO 2 [0006] In one embodiment, an organometallic compound is represented by the general formula M[CH2CH(RiSiMe2X)(R2SiMe2X)]a, wherein: M comprises a zinc atom or an aluminum atom; Ri and R2 are independently a hydrocarbon chain comprising from 1 to 20 carbon atoms; X is a hydrogen atom or a vinyl group; and a is 2 or 3. [0007] Additional features and advantages of the embodiments will be set forth in the detailed description and, in part, will be readily apparent to persons of ordinary skill in the art from that description, which includes the accompanying drawing and claims, or recognized by practicing the described embodiments. [0008] It is to be understood that both the preceding general description and the following detailed description describe various embodiments and are intended to provide an overview or framework for understanding the nature and character of the claimed subject matter. [0009] The drawings are included to provide a further understanding of the embodiments and, together with the detailed description, serve to explain the principles and operations of the claimed subject matter. However, the embodiments depicted in the drawings are illustrative and exemplary in nature, and not intended to limit the claimed subject matter. BRIEF DESCRIPTION OF THE DRAWINGS [0010] The following detailed description may be better understood when read in conjunction with the following drawing, in which: [0011] FIG. 1A depicts a nuclear magnetic resonance (NMR) spectrum of Example 1, according to one or more embodiments of the present disclosure; [0012] FIG. IB depicts a NMR spectrum of Example 1, according to one or more embodiments of the present disclosure; [0013] FIG. 2 depicts a gas chromatography-mass spectrometry (GC-MS) spectrum of Example 1, according to one or more embodiments of the present disclosure; [0014] FIG. 3 depicts a NMR spectrum of Example 2, according to one or more embodiments of the present disclosure; and 86262-WO-PCT/DOW 86262 WO 3 [0015] FIG. 4. depicts a GC-MS spectrum of Example 2, according to one or more embodiments of the present disclosure. [0016] Reference will now be made in greater detail to various embodiments, some of which are illustrated in the accompanying drawing. DETAILED DESCRIPTION [0017] Specific embodiments of the present application will now be described. The disclosure may be embodied in different forms and should not be construed as limited to the embodiments set forth in this disclosure. Rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the scope of the subject matter to those skilled in the art. [0018] DEFINITIONS [0019] Unless stated to the contrary, implicit from the context, or customary in the art, all test methods are current as of the filing date of this disclosure. [0020] It is noted that the various details described in this disclosure should not be taken to imply that these details relate to elements that are essential components of the various embodiment