Production method for hydrogenated petroleum resin

Patent metadata

Field	Value
Publication number	US-11220563-B2
Application number	US-201816493920-A
Country	US
Kind code	B2
Filing date	Mar 8, 2018
Priority date	Mar 16, 2017
Publication date	Jan 11, 2022
Grant date	Jan 11, 2022

Abstract

To provide a novel production method for a hydrogenated petroleum resin that does not cause filter clogging and is also capable of suppressing a significant decrease in catalytic activity in hydrogenation in a production method for a dicyclopentadiene/vinyl aromatic compound-based hydrogenated resin to be used as a tackifier. A production method for a dicyclopentadiene/vinyl aromatic compound-based hydrogenated petroleum resin, in which a reaction product obtained by reacting a dicyclopentadiene with a vinyl aromatic compound is subjected to thermal polymerization, thereby obtaining a thermal polymerization reaction product, followed by hydrogenation thereof, characterized in that as the thermal polymerization reaction product, an oligomer-removed thermal polymerization reaction product obtained by removing a dicyclopentadiene oligomer from the thermal polymerization reaction product is used as a hydrogenation raw material.

First claim

The invention claimed is:

1. A method of producing a dicyclopentadiene/vinyl aromatic compound-based hydrogenated petroleum resin, the method comprising:
subjecting a reaction product obtained by reacting a dicyclopentadiene with a vinyl aromatic compound to thermal polymerization, to obtain a thermal polymerization reaction product; and then
hydrogenating the thermal polymerization reaction product,
wherein, as the thermal polymerization reaction product, an oligomer-removed thermal polymerization reaction product is obtained by removing a dicyclopentadiene oligomer from the thermal polymerization reaction product and used as a hydrogenation raw material, and
wherein the hydrogenation raw material is obtained by removing the dicyclopentadiene oligomer by contacting the dicyclopentadiene oligomer in the thermal polymerization reaction product with an adsorbent.

2. The method of claim 1 , wherein the hydrogenation raw material is obtained by
cooling the thermal polymerization reaction product to 10 to 40° C., to obtain a deposited material, and
removing the dicyclopentadiene oligomer by performing solid-liquid separation of the deposited material.

3. The method of claim 1 , wherein the adsorbent is at least one type selected from the group consisting of an activated clay, a silica gel, a silica-alumina, an activated alumina, an activated carbon, a zeolite, and a diatomaceous earth.

4. The method of claim 1 , wherein the hydrogenation raw material has a turbidity at 25° C. of 12 NTU or less.

5. The method of claim 1 , wherein the hydrogenating uses a palladium-supported catalyst.

6. The method of claim 1 , wherein the vinyl aromatic compound is a compound represented by formula (1):

wherein R 1 is a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or an aralkyl group, and
the reaction product is a material comprising a phenylnorbornene derivative represented by formula (2):

wherein R 1 is a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or an aralkyl group.

7. The method of claim 1 , wherein the adsorbent comprises activated clay, a silica gel, a silica-alumina, an activated alumina, an activated carbon, a zeolite, a diatomaceous earth, or a mixture of two or more of any of these.

8. A method of producing a dicyclopentadiene/vinyl aromatic compound-based hydrogenated petroleum resin, the method comprising:
subjecting a reaction product obtained by reacting a dicyclopentadiene with a vinyl aromatic compound to thermal polymerization, to obtain a thermal polymerization reaction product; and then
hydrogenating the thermal polymerization reaction product,
wherein, as the thermal polymerization reaction product, an oligomer-removed thermal polymerization reaction product is obtained by removing a dicyclopentadiene oligomer from the thermal polymerization reaction product and used as a hydrogenation raw material, and
wherein the vinyl aromatic compound is of formula (1):

wherein R 1 is a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or an aralkyl group, and
wherein the reaction product comprises a phenylnorbornene of formula (2):

wherein R 1 is a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or an aralkyl group.

9. The method of claim 8 , wherein the hydrogenation raw material is obtained by
cooling the thermal polymerization reaction product to a temperature in a range of from 10 to 40° C., to obtain a deposited material, and
removing the dicyclopentadiene oligomer by performing solid-liquid separation of the deposited material.

10. The method of claim 8 , wherein the adsorbent is at least one type selected from the group consisting of an activated clay, a silica gel, a silica-alumina, an activated alumina, an activated carbon, a zeolite, and a diatomaceous earth.

11. The method of claim 8 , wherein the adsorbent comprises activated clay, a silica gel, a silica-alumina, an activated alumina, an activated carbon, a zeolite, a diatomaceous earth, or a mixture of two or more of any of these.

12. The method of claim 8 , wherein, in the phenylnorbornene of formula (2), R 1 is a hydrogen atom.

13. The method of claim 8 , wherein, in the phenylnorbornene of formula (2), R 1 is an alkyl group.

14. The method of claim 8 , wherein, in the phenylnorbornene of formula (2), R 1 is a cycloalkyl group.

15. The method of claim 8 , wherein, in the phenylnorbornene of formula (2), R 1 is a cycloalkyl group.

16. The method of claim 8 , wherein, in the phenylnorbornene of formula (2), R 1 is an aryl group.

17. The method of claim 8 , wherein, in the phenylnorbornene of formula (2), R 1 is an aralkyl group.

18. The method of claim 8 , wherein the hydrogenation raw material has a turbidity at 25° C. of 12 NTU or less.

19. The method of claim 8 , wherein the hydrogenating uses a palladium-supported catalyst.

20. The method of claim 8 , wherein the adsorbent comprises an activated alumina.

Assignees

• Maruzen Petrochem Co Ltd

Inventors

• Matsushita Keisuke
• IIZIMA Yoshikazu
• Hayashi Tomoki

Classifications

• C08F8/04 Primary

  Reduction, e.g. hydrogenation · CPC title

• C08F32/08 Primary

  having two condensed rings (coumarone-indene polymers C08F244/00) · CPC title

• C08F12/00

  Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring · CPC title

• C08F232/08

  having condensed rings (coumarone-indene polymers C08F244/00) · CPC title

• C08F212/08

  Styrene · CPC title