High-molecular-weight compound and method for producing same, composition and method for producing same, resin composition, additive for lubricating oil, and lubricating oil

Patent metadata

Field	Value
Publication number	US-12297301-B2
Application number	US-202117460140-A
Country	US
Kind code	B2
Filing date	Aug 27, 2021
Priority date	Mar 29, 2019
Publication date	May 13, 2025
Grant date	May 13, 2025

Abstract

A high-molecular-weight compound having a plurality of polymer chains linked through a divalent or higher-valent linking group, in which the divalent or higher-valent linking group has a thiol group and at least one of a thioether structure and a thiourethane structure, and a ratio of an absolute weight-average molecular weight to a relative weight-average molecular weight (absolute Mw/relative Mw) of the high-molecular-weight compound is 1.25 or more; and a method for producing the same are provided.

First claim

What is claimed is:

1. A high-molecular-weight compound comprising a plurality of polymer chains linked through a divalent or higher-valent linking group and having a moiety derived from a polyfunctional thiol compound (A) and a moiety derived from a compound (B) having a reactive group that reacts with a thiol group,
wherein the divalent or higher-valent linking group has a thiol group and at least one of a thioether structure and a thiourethane structure,
a ratio of an absolute weight-average molecular weight to a relative weight-average molecular weight (absolute Mw/relative Mw) of the high-molecular-weight compound is 1.25 or more, and
a relative Mw of the high-molecular-weight compound is 15,000 or more and 350,000 or less,
the high-molecular-weight compound satisfies Formulae (11) and (12),
r ×( f A −1)×( f B −1)<1.2  (11)

r =( f B ×y )/( f A ×x )  (12)

wherein, in Formula (11), f A is an average number of thiol groups per molecule of the polyfunctional thiol compound (A), f B is an average number of reactive groups per molecule of the compound (B), f A is 2.0 or more and f B is 1.2 or more, provided that a case where only the compound (A) having two thiol groups and only the compound (B) having two reactive groups are used is excluded, and r is a value calculated by Formula (12) when a molar ratio of the moiety derived from the polyfunctional thiol compound (A) to the moiety derived from the compound (B) is defined as x:y.

2. The high-molecular-weight compound according to claim 1 , wherein the divalent or higher-valent linking group includes at least one of structures represented by Formulae (1) and (2),

wherein, in Formula (1), R 1 and R 2 are each independently a hydrogen atom, a monovalent hydrocarbon group, a hydroxyl group, or a monovalent electron-withdrawing group, and R 3 is an oxygen atom, a divalent hydrocarbon group, or a divalent electron-withdrawing group, in Formula (2), X is an oxygen atom or a sulfur atom, and in Formulae (1) and (2), -* is a bond.

3. The high-molecular-weight compound according to claim 1 , wherein the divalent or higher-valent linking group has 1 to 300 thiol groups per molecule of the high-molecular-weight compound.

4. The high-molecular-weight compound according to claim 1 , wherein the absolute Mw/relative Mw is 3.00 or less.

5. A method for producing the high-molecular-weight compound of claim 1 , comprising:
a step of reacting the polyfunctional thiol compound (A) with the compound (B) having a reactive group that reacts with a thiol group to obtain a chain transfer agent (F) having a thiol group; and
a step of polymerizing vinyl-based compounds in the presence of the chain transfer agent (F) having a thiol group and a radical polymerization initiator to obtain a high-molecular-weight compound,
wherein the method comprises a step of reacting the polyfunctional thiol compound (A) and the compound (B) having a reactive group that reacts with a thiol group under conditions satisfying Formulae (13) and (14),
r ′×( f A −1)×( f B −1)<1.2  (13)

r ′=( f B ×y ′)/( f A ×x ′)  (14)

wherein, in Formula (13), f A is an average number of thiol groups per molecule of the polyfunctional thiol compound (A), f B is an average number of reactive groups per molecule of the compound (B), f A is 2.0 or more and f B is 1.2 or more, provided that a case where only the compound (A) having two thiol groups and only the compound (B) having two reactive groups are used is excluded, and r′ is a value calculated by Formula (14) when a molar ratio of the polyfunctional thiol compound (A) to the compound (B) is x′:y′.

6. The method for producing a high-molecular-weight compound according to claim 5 , wherein the reactive group that reacts with a thiol group is one or more selected from the group consisting of an acrylate group, a glycidyl group, and an isocyanate group.

7. The high-molecular-weight compound according to claim 1 , wherein the composition satisfies f A +f B >4.0.

8. The high-molecular-weight compound according to claim 1 , wherein the reactive group that reacts with a thiol group is one or more selected from the group consisting of an acrylate group, a glycidyl group, and an isocyanate group.

9. The high-molecular-weight compound according to claim 1 , wherein the composition is a chain transfer agent in a radical polymerization reaction system.

10. The method for producing the high-molecular-weight compound according to claim 5 , wherein the composition satisfies f A +f B >4.0.

11. The method for producing the high-molecular-weight compound according to claim 5 , wherein the polyfunctional thiol compound (A) is reacted with the compound (B) having a reactive group that reacts with a thiol group in the presence of a catalyst (C).

12. The method for producing the high-molecular-weight compound according to claim 5 ,
wherein the amount of solvent at a starting time of the reaction between the polyfunctional thiol compound (A) and the compound (B) having a reactive group that reacts with a thiol group is 50% by mass or less of a total mass of the polyfunctional thiol compound (A) and the compound (B) having a reactive group that reacts with a thiol group, and
an external temperature during the reaction between the polyfunctional thiol compound (A) and the compound (B) having a reactive group that reacts with a thiol group is 10° C. to 50° C.

13. A resin composition comprising:
the high-molecular-weight compound according to claim 1 ; and
a thermoplastic resin.

14. The resin composition according to claim 13 , wherein a mass ratio of the high-molecular-weight compound or the composition to the thermoplastic resin ((high-molecular-weight compound or composition)/thermoplastic resin) is 0.1/99.9 to 95/5.

15. An additive for a lubricating oil, wherein the additive for a lubricating oil comprises a high-molecular-weight compound,
the high-molecular-weight compound comprising:
a plurality of polymer chains linked through a divalent or higher-valent linking group and having a moiety derived from a polyfunctional thiol compound (A) and a moiety derived from a compound (B) having a reactive group that reacts with a thiol group,
wherein the divalent or higher-valent linking group has a thiol group and at least one of a thioether structure and a thiourethane structure,
a ratio of an absolute weight-average molecular weight to a relative weight-average molecular weight (absolute Mw/relative Mw) of the high-molecular-weight compound is 1.25 or more, and
a relative Mw of the high-molecular-weight compound is 15,000 or more and 45,000 or less,
the high-molecular-weight compound satisfies Formulae (11) and (12),
r ×( f A −1)×( f B −1)<1.2  (11)

r =( f B ×y )/( f A ×x )  (12)

wherein, in Formula (11), f A is an average number of thiol groups per molecule of the polyfunctional thiol compound (A), f B is an average number of reactive groups per molecule of the compound (B), f A is 2.0 or more and f B is 1.2 or more, provided that a case where only the compound (A) having two thiol groups and only the compound (B) having two reactive groups are used is excluded, and r is a value calculated by Formula (12) when a molar ratio of the moiety derived from the polyfunctional thiol compound (A) to the moiety derived from the compound (B) is defined as x:y.

16. A lubricating oil comprising the additive for a lubricating oil,
wherein the lubricating oil comprises a high-molecul

Assignees

• Mitsubishi Chem Corp

Inventors

• Chatani Shunsuke
• Miyahara Yuki
• Niino Hiroshi
• IKAWA Masashi
• Okada Haruki
• Fujie Fumiko

Classifications

• C10N2030/68

  Shear stability · CPC title

• C10M151/04 Primary

  Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds · CPC title

• C10N2030/02

  Pour-point; Viscosity index · CPC title

• C10M2221/02

  Macromolecular compounds obtained by reactions of monomers involving only carbon-to-carbon unsaturated bonds · CPC title

• C10M2203/003

  used as base material · CPC title