Method for producing modified polymer and hydrogenated product thereof
A method for producing a modified polymer or a hydrogenated product thereof, includes polymerizing a monomer in a polymerization solvent which includes a hydrocarbon-based solvent, using a polymerization initiator to obtain a reaction solution. A functional group is introduced into the modified polymer or the hydrogenated product thereof, using a compound having the functional group protected with a silyl group. The reaction solution is separated into a solvent fraction including the hydrocarbon-based solvent, and a solid fraction including the modified polymer or the hydrogenated product thereof. The solvent fraction separated from the reaction solution is distilled to obtain a low-boiling fraction including the hydrocarbon-based solvent and a silanol compound. At least part of the silanol compound is removed from the low-boiling fraction by liquid-liquid extraction. At least part of a raffinate of the low-boiling fraction is recycled as a polymerization solvent.
1. A method for producing a modified polymer or a hydrogenated product thereof, the method comprising:
polymerizing a monomer comprising at least one of a conjugated diene or an aromatic vinyl compound in a polymerization solvent which includes a hydrocarbon-based solvent, using a polymerization initiator which includes an active organometal to obtain a reaction solution in which the modified polymer or the hydrogenated product thereof is dissolved in the polymerization solvent;
introducing a functional group into at least one of a main chain or a side chain of the modified polymer or the hydrogenated product thereof, using a compound having the functional group protected with a silyl group as a polymerization initiator, as a functional group-introducing monomer, or as a polymerization terminator;
separating the reaction solution into a solvent fraction including the hydrocarbon-based solvent, and a solid fraction including the modified polymer or the hydrogenated product thereof;
distilling the solvent fraction separated from the reaction solution to obtain a low-boiling fraction including the hydrocarbon-based solvent and a silanol compound, a content of the silanol compound in the low-boiling fraction being in a range from 200 ppm to 10% by mass;
removing at least part of the silanol compound from the low-boiling fraction by liquid-liquid extraction using the low-boiling fraction and an extraction solvent; and
recycling at least part of a raffinate of the low-boiling fraction from which the at least part of the silanol compound has been removed by the liquid-liquid extraction, as a polymerization solvent.
2. The method according to claim 1 , wherein the silanol compound is at least one of trimethylsilanol, ethyldimethylsilanol, diethylmethylsilanol, dimethylpropylsilanol, dimethylisopropylsilanol, ethylmethylpropylsilanol, ethylmethylisopropylsilanol, triethylsilanol, n-butyldimethylsilanol, sec-buthyldimethylsilanol, or tert-butyldimethylsilanol.
3. The method according to claim 1 , wherein the extraction solvent used for the liquid-liquid extraction is water.
4. The method according to claim 1 , wherein a content of the low-boiling fraction in the solvent fraction is in a range from 0.1% to 20% by mass before distilling the solvent fraction.
5. The method according to claim 1 , wherein a weight ratio (Me/Mb) of the extraction solvent (Me) to the low-boiling fraction (Mb) is in a range from 0.5 to 10 when removing the at least part of the silanol compound from the low-boiling fraction.
6. The method according to claim 1 , wherein a content of the silanol compound in the at least part of the raffinate that is recycled as the polymerization solvent is 200 ppm or less by mass.
7. The method according to claim 1 ,
wherein a randomizer is used for polymerizing the monomer, and at least part of the randomizer is included in the low-boiling fraction, and
wherein the method further comprises:
separating the randomizer from the low-boiling fraction after distilling the solvent fraction and before removing the silanol compound, or after removing the silanol compound.
8. The method according to claim 2 , wherein the extraction solvent used for the liquid-liquid extraction is water.
9. The method according to claim 2 , wherein a content of the low-boiling fraction in the solvent fraction is in a range from 0.1% to 20% by mass before distilling the solvent fraction.
10. The method according to claim 2 , wherein a weight ratio (Me/Mb) of the extraction solvent (Me) to the low-boiling fraction (Mb) is in a range from 0.5 to 10 when removing the at least part of the silanol compound from the low-boiling fraction.
11. The method according to claim 2 , wherein a content of the silanol compound in the at least part of the raffinate that is recycled as the polymerization solvent is 200 ppm or less by mass.
12. The method according to claim 2 ,
wherein a randomizer is used for polymerizing the monomer, and at least part of the randomizer is included in the low-boiling fraction, and
wherein the method further comprises:
separating the randomizer from the low-boiling fraction after distilling the solvent fraction and before removing the silanol compound, or after removing the silanol compound.
13. The method according to claim 8 , wherein a content of the low-boiling fraction in the solvent fraction is in a range from 0.1% to 20% by mass before distilling the solvent fraction.
14. The method according to claim 8 , wherein a weight ratio (Me/Mb) of the extraction solvent (Me) to the low-boiling fraction (Mb) is in a range from 0.5 to 10 when removing the at least part of the silanol compound from the low-boiling fraction.
15. The method according to claim 8 , wherein a content of the silanol compound in the at least part of the raffinate that is recycled as the polymerization solvent is 200 ppm or less by mass.
16. The method according to claim 8 ,
wherein a randomizer is used for polymerizing the monomer, and at least part of the randomizer is included in the low-boiling fraction, and
wherein the method further comprises:
separating the randomizer from the low-boiling fraction after distilling the solvent fraction and before removing the silanol compound, or after removing the silanol compound.
17. The method according to claim 13 , wherein a weight ratio (Me/Mb) of the extraction solvent (Me) to the low-boiling fraction (Mb) is in a range from 0.5 to 10 when removing the at least part of the silanol compound from the low-boiling fraction.
18. The method according to claim 17 , wherein a content of the silanol compound in the at least part of the raffinate that is recycled as the polymerization solvent is 200 ppm or less by mass.
19. The method according to claim 17 ,
wherein a randomizer is used for polymerizing the monomer, and at least part of the randomizer is included in the low-boiling fraction, and
wherein the method further comprises:
separating the randomizer from the low-boiling fraction after distilling the solvent fraction and before removing the silanol compound, or after removing the silanol compound.