IP Library Granted Patent US 11,352,453
Granted Patent B2
US 11,352,453 · App. 16/762,595 · Granted Jun 7, 2022

Catalyst for olefin polymerization and production method for polar group-containing olefin-based polymers

Inventors: Kyoko Nozaki (Tokyo, JP); Shingo Ito (Tokyo, JP); Junichi Kuroda (Oita, JP); Yoshikuni Okumura (Oita, JP); Shinya Hayashi (Oita, JP); Yumiko Minami (Tokyo, JP); Minoru Kobayashi (Yokkaichi, JP); Yuichiro Yasukawa (Kawasaki, JP)
Assignees: THE UNIVERSITY OF TOKYO; SHOWA DENKO K.K.; JAPAN POLYETHYLENE CORPORATION
C08F16/38C07F15/006C08F4/80C08F4/7031C08F218/02
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Quick Facts
Patent No.
US 11,352,453
App. No.
16/762,595
Granted
Jun 7, 2022
Kind
B2
Abstract

A catalyst for olefin polymerization that contains a metal complex represented by general formula (C1) and a method for producing polyethylene, a copolymer of ethylene and an olefin having a polar group represented by general formula (1), or a copolymer of ethylene, an olefin having a polar group represented by general formula (1) and another monomer, using the aforementioned metal complex as a polymerization catalyst, wherein the symbols in formula (C1) and formula (1) are as defined in the specification.

Claims (17)

1. A catalyst for olefin polymerization containing a metal complex represented by the following general formula (C1):

wherein, M represents Pd, X represents a phosphorous atom (P) or arsenic atom (As), Y represents a divalent group selected from a substituted or unsubstituted methylene group (—CH 2 —), substituted or unsubstituted imino group (—NH—), oxy group (—O—) or substituted or unsubstituted silylene group (—SiH 2 —), R 5 represents a substituent selected from the group consisting of a hydrogen atom, halogen atom, hydrocarbon group having 1 to 30 carbon atoms, hydrocarbon group having 1 to 30 carbon atoms substituted with a halogen atom, hydrocarbon group having 2 to 30 carbon atoms substituted with an alkoxy group having 1 to 10 carbon atoms, hydrocarbon group having 7 to 30 carbon atoms substituted with an aryloxy group having 6 to 20 carbon atoms, hydrocarbon group having 3 to 30 carbon atoms substituted with an amido group having 2 to 10 carbon atoms, alkoxy group having 1 to 30 carbon atoms, aryloxy group having 6 to 30 carbon atoms, and acyloxy group having 2 to 10 carbon atoms, R 6 and R 7 respectively and independently represent an alkoxy group, aryloxy group, silyl group, amino group or hydrocarbon group having 1 to 120 carbon atoms optionally substituted with one or more substituents selected from a halogen atom, alkoxy group or aryloxy group, at least one of R 6 and R 7 represents a tertiary alkyl group represented by general formula (2):

wherein, R 8 , R 9 and R 10 respectively and independently represent a hydrocarbon group having 1 to 30 carbon atoms, R 8 , R 9 and R 10 may respectively bond to form a ring structure, and in the formula, bonds between the carbon atom and X in general formula (C1) are also indicated, R 6 and R 7 may respectively bond to form a ring structure, L represents an electron donating ligand, and q represents ½, 1 or 2.

2. The catalyst for olefin polymerization according to claim 1 , wherein R 6 and R 7 respectively and independently represent a tertiary alkyl group represented by general formula (2).

3. The catalyst for olefin polymerization according to claim 1 , wherein the tertiary alkyl group represented by general formula (2) is a t-butyl group, 1-adamantyl group, 2-methyl-2-butyl group, 2-methyl-2-pentyl group, 2-benzyl-2-propyl group, 2,5-dimethyl-2-hexyl group, 3-methyl-3-pentyl group or 2,3,3-trimethyl-2-butyl group.

4. The catalyst for olefin polymerization according to claim 1 , wherein Y in general formula (C1) represents a methylene group.

5. The catalyst for olefin polymerization according to claim 1 , wherein R 5 in general formula (C1) represents a methyl group, benzyl group, methoxy group, 2-acetoamidophenyl group or acetyloxy group.

6. A production method comprising conducting polymerization in the presence of a metal complex represented by general formula (C1) as a polymerization catalyst:

wherein, the symbols in the formula having the same meanings as the description of claim 1 , for producing polyethylene, a copolymer of ethylene and an olefin having a polar group represented by general formula (1):

wherein, R 1 represents a substituent selected from the group consisting of a hydroxy group, alkoxy group having 1 to 10 carbon atoms, aryloxy group having 6 to 20 carbon atoms, acyl group having 2 to 10 carbon atoms, ester group having 2 to 10 carbon atoms, oxycarbonyl group: R—O—(C═O)—, where R represents an organic group, acyloxy group having 2 to 10 carbon atoms, amino group, substituted amino group having 1 to 12 carbon atoms, substituted amido group having 2 to 12 carbon atoms, substituted pyridyl group having 5 to 10 carbon atoms, substituted pyrrolidyl group having 4 to 10 carbon atoms, substituted piperidyl group having 5 to 10 carbon atoms, substituted hydrofuryl group having 4 to 10 carbon atoms, substituted imidazolyl group having 4 to 10 carbon atoms, mercapto group, alkylthio group having 1 to 10 carbon atoms, arylthio group having 6 to 10 carbon atoms, epoxy group and a halogen atom, and n represents 0 or an arbitrary integer selected from 1 to 6, or a copolymer of ethylene, an olefin having a polar group represented by the aforementioned formula (1) and another monomer.

7. The production method according to claim 6 , wherein n in general formula (1) represents 0.

8. The production method according to claim 6 , wherein n in general formula (1) represents 1.

9. The production method according to claim 6 , wherein R 6 and R 7 respectively and independently represent a tertiary alkyl group represented by general formula (2).

10. The production method according to claim 6 , wherein the tertiary alkyl group represented by general formula (2) is a t-butyl group, 1-adamantyl group, 2-methyl-2-butyl group, 2-methyl-2-pentyl group, 2-benzyl-2-propyl group, 2,5-dimethyl-2-hexyl group, 3-methyl-3-pentyl group or 2,3,3-trimethyl-2-butyl group.

11. The production method according to claim 6 , wherein Y in general formula (C1) represents a methylene group.

12. The production method according to claim 6 , wherein a polymerization temperature is 100-180° C.

13. The production method according to claim 6 , wherein R 5 in general formula (C1) represents a methyl group, benzyl group, methoxy group, 2-acetoamidophenyl group or acetyloxy group.

Assignments (3)
CHANGE OF ADDRESS Recorded Feb 14, 2024
From: RESONAC CORPORATION
To: RESONAC CORPORATION
Reel/Frame 066599/0037 →
CHANGE OF NAME Recorded Jun 23, 2023
From: SHOWA DENKO K.K.
To: RESONAC CORPORATION
Reel/Frame 064082/0513 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 8, 2020
From: NOZAKI, KYOKO; ITO, SHINGO; KURODA, JUNICHI; OKUMURA, YOSHIKUNI; HAYASHI, SHINYA; MINAMI, YUMIKO; KOBAYASHI, MINORU; YASUKAWA, YUICHIRO
To: THE UNIVERSITY OF TOKYO; SHOWA DENKO K. K.; JAPAN POLYETHYLENE CORPORATION
Reel/Frame 052611/0014 →