Method for producing hydrogenated polymer by using plurality of solvents

Patent metadata

Field	Value
Publication number	US-2025257156-A1
Application number	US-202318855070-A
Country	US
Kind code	A1
Filing date	Apr 10, 2023
Priority date	Apr 11, 2022
Publication date	Aug 14, 2025
Grant date	—

Abstract

Provided is a hydrogenation method using a solvent that satisfactorily dissolves a polymer before and after hydrogenation. A method for producing a hydrogenated polymer by hydrogenating the aromatic ring of an aromatic vinyl compound-based polymer includes performing a hydrogenation reaction using the aromatic vinyl compound-based polymer, a solvent, and a hydrogenation catalyst, wherein the solvent is a mixed solvent containing at least one first solvent and at least one second solvent, and the Hansen solubility parameter (HSP) value of the mixed solvent 1) falls within a Hansen sphere on a three-dimensional space consisting of δd, δp, and δh axes of the aromatic vinyl compound-based polymer before hydrogenation, and 2) falls within a Hansen sphere on a three-dimensional space consisting of δd, δp, and δh axes of the aromatic vinyl compound-based polymer after hydrogenation.

First claim

1 . A method for producing a hydrogenated polymer by hydrogenating an aromatic ring of an aromatic vinyl compound-based polymer, the method comprising performing hydrogenation reaction using the aromatic vinyl compound-based polymer, a solvent, and a hydrogenation catalyst,
wherein the solvent is a solvent mixture containing at least one type of first solvent and at least one type of second solvent, and wherein Hansen solubility parameter (HSP) value of the solvent mixture: 1. falls within a Hansen sphere in a three-dimensional space consisting of δd, δp, and δh axes of the aromatic vinyl compound-based polymer before the hydrogenation; and 2. falls within a Hansen sphere in a three-dimensional space consisting of δd, δp, and δh axes of the aromatic vinyl compound-based polymer after the hydrogenation.

2 . A method for producing a hydrogenated polymer by hydrogenating an aromatic ring of an aromatic vinyl compound-based polymer, the method comprising performing hydrogenation reaction using the aromatic vinyl compound-based polymer, a solvent, and a hydrogenation catalyst,
wherein the solvent is a solvent mixture containing at least one type of first solvent and at least one type of second solvent, wherein Hansen solubility parameters (HSP) of the at least one type of first solvent are each as follows: δd: 10-20; δp: 1-15; and δh: 1-25, wherein HSP of the at least one type of second solvent are each as follows: δd: 10-20; δp: 0 to less than 1; and δh: 0-2, wherein the weight ratio of the at least one type of first solvent to the at least one type of second solvent (first: second ratio) is 1:9-9:1, and wherein the first solvent is a solvent selected from the group consisting of an ester solvent, an aromatic solvent, a monocyclic monoterpene, and a dioxane.

3 . The method according to claim 1 , wherein a weight ratio of the at least one type of first solvent to the at least one type of second solvent (first: second ratio) is 1:9-9:1.

4 . The method according to claim 1 , further comprising obtaining a Hansen sphere of the aromatic vinyl compound-based polymer before the hydrogenation and a Hansen sphere of the aromatic vinyl compound-based polymer after the hydrogenation.

5 . The method according to claim 1 , wherein HSP of the solvent mixture are each as follows:
δd: 15.6-16.7; δp: 0.3-4.7; and δh: 0.5-5.8.

6 . The method according to claim 1 , wherein the at least one type of first solvent comprises one or more selected from the group consisting of methyl acetate, ethyl acetate, butyl acetate, methyl isobutyrate, methyl propionate, and propylene glycol monomethyl ether acetate.

7 . The method according to claim 1 , wherein the at least one type of second solvent comprises one or more selected from the group consisting of a saturated hydrocarbon solvent and a hydrogenated product of monocyclic monoterpene.

8 . The method according to claim 1 , wherein the at least one type of second solvent comprises one or more selected from the group consisting of cyclohexane, a C7-C15 monoalkylcyclohexane, a C8-C15 dialkylcyclohexane, a C9-C15 trialkylcyclohexane, a C10-C15 tetraalkylcyclohexane, cyclooctane, a C9-C15 monoalkylcyclooctane, a C10-C15 dialkylcyclooctane, a C11-C15 trialkylcyclooctane, a C12-C15 tetraalkylcyclooctane, n-octane, and n-decane.

9 . The method according to claim 1 , wherein the at least one type of second solvent comprises a C9 alkylcyclohexane and/or a C10 alkylcyclohexane.

10 . The method according to claim 1 , wherein the first solvent has a boiling point of 50° C. or higher and an ignition point of 400° C. or higher.

11 . The method according to claim 1 , wherein the second solvent has a boiling point of 80° C. or higher and an ignition point of 230° C. or higher.

12 . The method according to claim 1 , wherein the aromatic vinyl compound-based polymer comprises one or more selected from the group consisting of a copolymer of styrene and butadiene, a copolymer of styrene and isoprene, a copolymer of styrene and methyl methacrylate, a copolymer of styrene and maleic anhydride, a copolymer of styrene and vinyl acetate, and polystyrene.

13 . The method according to claim 1 , comprising forming a polymeric resin by devolatilization extrusion after the hydrogenation reaction.

14 . The method according to claim 1 ,
further comprising a concentration step between the hydrogenation reaction and the devolatilization extrusion.

15 . The method according to claim 1 , wherein the hydrogenation catalyst is a solid catalyst loaded with one or more selected from the group consisting of palladium, platinum, ruthenium, rhodium, and nickel.

16 . The method according to claim 2 , wherein HSP of the solvent mixture are each as follows:
δd: 15.6-16.7; δp: 0.3-4.7; and δh: 0.5-5.8.

17 . The method according to claim 2 , wherein the at least one type of first solvent comprises one or more selected from the group consisting of methyl acetate, ethyl acetate, butyl acetate, methyl isobutyrate, methyl propionate, and propylene glycol monomethyl ether acetate.

18 . The method according to claim 2 , wherein the at least one type of second solvent comprises one or more selected from the group consisting of a saturated hydrocarbon solvent and a hydrogenated product of monocyclic monoterpene.

19 . The method according to claim 2 , wherein the at least one type of second solvent comprises one or more selected from the group consisting of cyclohexane, a C7-C15 monoalkylcyclohexane, a C8-C15 dialkylcyclohexane, a C9-C15 trialkylcyclohexane, a C10-C15 tetraalkylcyclohexane, cyclooctane, a C9-C15 monoalkylcyclooctane, a C10-C15 dialkylcyclooctane, a C11-C15 trialkylcyclooctane, a C12-C15 tetraalkylcyclooctane, n-octane, and n-decane.

20 . The method according to claim 2 , wherein the at least one type of second solvent comprises a C9 alkylcyclohexane and/or a C10 alkylcyclohexane.

Assignees

• Mitsubishi Gas Chemical Co

Inventors

• Sato Hideyuki
• ARAI Hirokatsu
• Nakamura Yusuke
• MATSUSHITA Miru
• Kato Noriyuki

Classifications

• C08F2810/00

  Chemical modification of a polymer · CPC title

• C08F297/04

  polymerising vinyl aromatic monomers and conjugated dienes · CPC title

• C08C19/02

  Hydrogenation · CPC title

• C08F220/14

  Methyl esters {, e.g. methyl (meth)acrylate} · CPC title

• C08F222/06

  Maleic anhydride · CPC title