# US 2020/0399404 A1 · Petroleum resin, hydrogenated petroleum resin, and production method for hydrogenated petroleum resin > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2020/0399404 A1 - Document ID: US20200399404A1 - Status: Published application - Kind: A1 - Application number: 16/978,532 - Filed: 2019-03-08 - Published: 2020-12-24 - Earliest claimed: 2018-03-08 - Assignees: Idemitsu Kosan Co., Ltd. - Applicants: Idemitsu Kosan Co.,Ltd. - Inventors: Kiyohiko YOKOTA; Kenji KOBAYASHI; Masakatsu KUROKI - Web page: https://patentgrep.com/patent/US20200399404A1 ## CPC - C08F 8/04: Reduction, e.g. hydrogenation - C08F 6/005: {from solid polymers} - C08F 212/08: Styrene - C08F 232/08: having condensed rings (coumarone-indene polymers C08F244/00) - C09J 11/08: Macromolecular additives - C09J 125/08: Copolymers of styrene (C09J129/08, C09J135/06, C09J155/02 take precedence) - C09J 145/00: Adhesives based on homopolymers or copolymers of compounds having no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic or in a heterocyclic system; Adhesives based on derivatives of such polymers (based on polymers of cyclic esters of polyfunctional acids C09J131/00; based on polymers of cyclic anhydrides or imides C09J135/00) - C09J 2301/304: the adhesive being heat-activatable, i.e. not tacky at temperatures inferior to 30°C - C09J 2301/414: presence of a copolymer - C09J 2423/00: Presence of polyolefin - C09J 2425/00: Presence of styrenic polymer - C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS - C09J: ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES (preparation of glue or gelatine C09H) ## Abstract The present invention relates to a petroleum resin having the content of a volatile organic compound component of less than 100 wt ppm; and a hydrogenated petroleum resin having the content of a volatile organic compound component of less than 100 wt ppm. ## Claims ### Claim at position 1 1: A petroleum resin having the content of a volatile organic compound component of less than 100 wt ppm. ### Claim at position 2 (depends on 1) 2: The petroleum resin according to claim 1, wherein the petroleum resin comprises a copolymer of a cyclopentadiene-based compound and a vinyl aromatic compound. ### Claim at position 3 (depends on 2) 3: The petroleum resin according to claim 2, wherein the copolymer is one resulting from thermal polymerization of the cyclopentadiene-based compound and the vinyl aromatic compound. ### Claim at position 4 4: A hydrogenated petroleum resin having the content of a volatile organic compound component of less than 100 wt ppm. ### Claim at position 5 (depends on 4) 5: The hydrogenated petroleum resin according to claim 4, wherein the content of the volatile organic compound component is less than 10 wt ppm. ### Claim at position 6 (depends on 4) 6: The hydrogenated petroleum resin according to claim 4, wherein the hydrogenated petroleum resin is produced by hydrogenating a petroleum resin having a content of a volatile organic compound component of less than 100 wt ppm. ### Claim at position 7 (depends on 6) 7: The hydrogenated petroleum resin according to claim 6, wherein the petroleum resin is one resulting from thermal polymerization of at least one selected from the group consisting of cyclopentadiene and dicyclopentadiene, and styrene. ### Claim at position 8 (depends on 1) 8: A hot melt adhesive composition comprising at least one selected from the group consisting of the petroleum resin according to claim 1 and a hydrogenated petroleum resin produced from hydrogenating the petroleum resin. ### Claim at position 9 (depends on 8) 9: The hot melt adhesive composition according to claim 8, further comprising a thermoplastic compound. ### Claim at position 10 (depends on 9) 10: The hot melt adhesive composition according to claim 9, wherein the thermoplastic compound is at least one selected from the group consisting of a styrene polymer, an ethylene-vinyl acetate copolymer (EVA), a styrene-butadiene-styrene block copolymer (SBS), a styrene-isoprene-styrene block copolymer (SIS), a natural rubber, an amorphous poly-α-olefin (APAO), a styrene-ethylene-butylene-styrene rubber (SEBS), and a styrene-ethylene-propylene-styrene rubber (SEPS). ### Claim at position 11 11: A method for producing a hydrogenated petroleum resin comprising a copolymerization reaction step of subjecting a cyclopentadiene-based compound and a vinyl aromatic compound to a copolymerization reaction in the presence of a polymerization solvent; a step of performing a removal treatment of a volatile component which is contained in a copolymerization reaction product liquid obtained in the copolymerization reaction step, to obtain a petroleum resin; a hydrogenation reaction step of subjecting the petroleum resin to a hydrogenation reaction in the presence of a hydrogenation solvent; a step of performing a removal treatment of an unreacted component and a volatile component which are contained in a hydrogenation reaction product liquid obtained in the hydrogenation reaction step, to obtain a hydrogenated petroleum resin concentrate; and a removal step of a volatile organic compound component by removing a volatile organic compound component from the hydrogenated petroleum resin concentrate, to obtain a hydrogenated petroleum resin containing 6 to 10% by mass of a hydrogenated low-molecular weight material, wherein the removal step of a volatile organic compound component is constituted of a first step of supplying the hydrogenated petroleum resin into a thin film distillation apparatus, to control the content of the volatile organic compound component to less than 2,000 wt ppm; and a second step of supplying the hydrogenated petroleum resin having passed the first step into a nitrogen-stripping apparatus or a steam distillation apparatus, to control the content of the volatile organic compound component to less than 100 wt ppm. ### Claim at position 12 (depends on 11) 12: The method for producing a hydrogenated petroleum resin according to claim 11, wherein the content of the hydrogenated low-molecular weight material which is contained in the hydrogenated petroleum resin in the hydrogenated petroleum resin concentrate is 7 to 13% by mass in 100% by mass of the hydrogenated petroleum resin containing the hydrogenated low molecular material. ### Claim at position 13 (depends on 11) 13: The method for producing a hydrogenated petroleum resin according to claim 11, wherein in the thin film distillation apparatus, a treatment temperature is 100 to 300° C., a treatment pressure is 0.1 to 15 kPa, and a treatment time is 5 to 180 minutes. ### Claim at position 14 (depends on 11) 14: The method for producing a hydrogenated petroleum resin according to claim 11, wherein in the nitrogen-stripping apparatus or the steam distillation apparatus, a treatment temperature is 150 to 300° C., a treatment pressure is 0.5 to 150 kPa, a nitrogen or steam flow rate is 100 to 1,000,000 mL/min relative to 100% by mass of the hydrogenated petroleum resin, and a treatment time is 10 to 180 minutes. ### Claim at position 15 (depends on 11) 15: The method for producing a hydrogenated petroleum resin according to claim 11, wherein a molecular weight of the hydrogenated low-molecular weight material which is contained in the hydrogenated petroleum resin is 200 to 350. ### Claim at position 16 (depends on 11) 16: The method for producing a hydrogenated petroleum resin according to claim 11, wherein the nitrogen-stripping apparatus is a rotary evaporator or a flash drum, and the steam distillation apparatus is a flash drum or a stripping tower.