KR102221880B1 - 수소첨가 석유 수지의 제조 방법 - Google Patents
수소첨가 석유 수지의 제조 방법 Download PDFInfo
- Publication number
- KR102221880B1 KR102221880B1 KR1020167016104A KR20167016104A KR102221880B1 KR 102221880 B1 KR102221880 B1 KR 102221880B1 KR 1020167016104 A KR1020167016104 A KR 1020167016104A KR 20167016104 A KR20167016104 A KR 20167016104A KR 102221880 B1 KR102221880 B1 KR 102221880B1
- Authority
- KR
- South Korea
- Prior art keywords
- petroleum resin
- hydrogenated petroleum
- reaction mixture
- less
- producing
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
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- 239000011347 resin Substances 0.000 title claims abstract description 73
- 229920005989 resin Polymers 0.000 title claims abstract description 73
- 239000003208 petroleum Substances 0.000 title claims abstract description 64
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 38
- 239000011541 reaction mixture Substances 0.000 claims abstract description 48
- 230000006837 decompression Effects 0.000 claims abstract description 42
- 238000000034 method Methods 0.000 claims abstract description 29
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 28
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims abstract description 26
- 238000010438 heat treatment Methods 0.000 claims abstract description 24
- -1 cyclopentadiene compound Chemical class 0.000 claims abstract description 18
- 238000012719 thermal polymerization Methods 0.000 claims abstract description 14
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 14
- 230000000379 polymerizing effect Effects 0.000 claims abstract description 3
- 239000002904 solvent Substances 0.000 claims description 20
- 229920001577 copolymer Polymers 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 238000006116 polymerization reaction Methods 0.000 description 26
- 239000010409 thin film Substances 0.000 description 14
- 241001417501 Lobotidae Species 0.000 description 11
- 230000008569 process Effects 0.000 description 11
- 239000004831 Hot glue Substances 0.000 description 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 6
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethylcyclohexane Chemical compound CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000000853 adhesive Substances 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000004807 desolvation Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- 230000006866 deterioration Effects 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- 238000005187 foaming Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- QEGNUYASOUJEHD-UHFFFAOYSA-N 1,1-dimethylcyclohexane Chemical compound CC1(C)CCCCC1 QEGNUYASOUJEHD-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 230000002542 deteriorative effect Effects 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- IQSUNBLELDRPEY-UHFFFAOYSA-N 1-ethylcyclopenta-1,3-diene Chemical compound CCC1=CC=CC1 IQSUNBLELDRPEY-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 229920005601 base polymer Polymers 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- NFWSQSCIDYBUOU-UHFFFAOYSA-N methylcyclopentadiene Chemical compound CC1=CC=CC1 NFWSQSCIDYBUOU-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000346 polystyrene-polyisoprene block-polystyrene Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 229920001935 styrene-ethylene-butadiene-styrene Polymers 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F6/00—Post-polymerisation treatments
- C08F6/06—Treatment of polymer solutions
- C08F6/10—Removal of volatile materials, e.g. solvents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F212/00—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
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F212/06—Hydrocarbons
- C08F212/08—Styrene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F232/00—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system
- C08F232/02—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having no condensed rings
- C08F232/06—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having no condensed rings having two or more carbon-to-carbon double bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F232/00—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system
- C08F232/08—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having condensed rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/04—Reduction, e.g. hydrogenation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2800/00—Copolymer characterised by the proportions of the comonomers expressed
- C08F2800/20—Copolymer characterised by the proportions of the comonomers expressed as weight or mass percentages
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JPJP-P-2013-267833 | 2013-12-25 | ||
| JP2013267833A JP6403951B2 (ja) | 2013-12-25 | 2013-12-25 | 水素添加石油樹脂の製造方法 |
| PCT/JP2014/080585 WO2015098370A1 (ja) | 2013-12-25 | 2014-11-19 | 水素添加石油樹脂の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20160102995A KR20160102995A (ko) | 2016-08-31 |
| KR102221880B1 true KR102221880B1 (ko) | 2021-03-03 |
Family
ID=53478244
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020167016104A Active KR102221880B1 (ko) | 2013-12-25 | 2014-11-19 | 수소첨가 석유 수지의 제조 방법 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US9644043B2 (enExample) |
| JP (1) | JP6403951B2 (enExample) |
| KR (1) | KR102221880B1 (enExample) |
| CN (1) | CN105849136B (enExample) |
| MY (1) | MY174155A (enExample) |
| SA (1) | SA516371384B1 (enExample) |
| SG (1) | SG11201604930WA (enExample) |
| TW (1) | TWI636067B (enExample) |
| WO (1) | WO2015098370A1 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106008819B (zh) * | 2016-07-07 | 2018-02-06 | 朗盈科技(北京)有限公司 | 一种低色度碳九加氢石油树脂的生产装置及生产方法 |
| EP3763755B1 (en) * | 2018-03-08 | 2025-05-07 | Idemitsu Kosan Co.,Ltd. | Petroleum resin, hydrogenated petroleum resin, and production method for hydrogenated petroleum resin |
| KR20200138207A (ko) | 2018-03-28 | 2020-12-09 | 마루젠 세끼유가가꾸 가부시키가이샤 | 수소 첨가 석유 수지의 탈취 방법 및 수소 첨가 석유 수지의 제조 방법 |
| WO2019189295A1 (ja) * | 2018-03-28 | 2019-10-03 | 丸善石油化学株式会社 | 水素添加石油樹脂の製造方法 |
| US11753566B2 (en) | 2019-01-31 | 2023-09-12 | Synthomer Adhesive Technologies Llc | Low volatile tackifier compositions |
| CN112827201B (zh) * | 2019-11-29 | 2024-09-10 | 天津天大天海化工新技术有限公司 | 一种乙烯副产c9原料处理系统和处理方法 |
| KR20220093123A (ko) * | 2019-12-13 | 2022-07-05 | 마루젠 세끼유가가꾸 가부시키가이샤 | 다이사이클로펜타다이엔과 바이닐 방향족 화합물의 공중합 수지의 제조 방법 |
| EP4130055A4 (en) | 2020-03-31 | 2024-04-24 | Eneos Corporation | METHOD FOR PRODUCING PETROLEUM RESIN FOR HOT MELT ADHESIVE, AND METHOD FOR PRODUCING HYDROGENATED PETROLEUM RESIN |
| KR20230008036A (ko) * | 2020-04-14 | 2023-01-13 | 이데미쓰 고산 가부시키가이샤 | 수소화 석유 수지 펠릿 및 수소화 석유 수지 펠릿의 제조 방법 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001316455A (ja) | 2000-04-28 | 2001-11-13 | Nippon Zeon Co Ltd | 脂環構造含有重合体の製造方法および成形体 |
| JP2011074373A (ja) | 2009-09-04 | 2011-04-14 | Idemitsu Kosan Co Ltd | 重合溶液の揮発成分除去装置、その方法、および、重合装置 |
| JP2012251051A (ja) | 2011-06-01 | 2012-12-20 | Idemitsu Kosan Co Ltd | 水添石油樹脂ペレットの製造方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5398383A (en) * | 1977-02-08 | 1978-08-28 | Nippon Zeon Co Ltd | Continuous production of cyclopentadiene resin and oil |
| JPH0251502A (ja) * | 1988-08-15 | 1990-02-21 | Idemitsu Petrochem Co Ltd | 石油樹脂の製造方法 |
| DE69820894T2 (de) * | 1997-10-23 | 2004-12-30 | Zeon Corp. | Thermoplastisches Ringöffnungspolymer auf der Basis von Dicyclopentadien, hydrierte Derivate davon und Verfahren zur Herstellung von beiden |
| AU2001236000A1 (en) * | 2000-03-01 | 2001-09-12 | Bayer A.G. | Process for producing hydrogenated unsaturated ring-containing hydrocarbon polymer |
| EP1574526A4 (en) | 2002-12-20 | 2007-06-06 | Idemitsu Kosan Co | METHOD FOR THE PRODUCTION OF HYDROGENATED PETROLEUM RESIN |
| JP5105326B2 (ja) * | 2007-04-19 | 2012-12-26 | 昭和電工株式会社 | 水素化方法及び石油化学プロセス |
| JP5845001B2 (ja) * | 2011-06-01 | 2016-01-20 | 出光興産株式会社 | 水添石油樹脂の製造方法、および、水添石油樹脂ペレットの製造プラント |
-
2013
- 2013-12-25 JP JP2013267833A patent/JP6403951B2/ja active Active
-
2014
- 2014-11-19 CN CN201480070881.2A patent/CN105849136B/zh active Active
- 2014-11-19 SG SG11201604930WA patent/SG11201604930WA/en unknown
- 2014-11-19 KR KR1020167016104A patent/KR102221880B1/ko active Active
- 2014-11-19 MY MYPI2016702324A patent/MY174155A/en unknown
- 2014-11-19 US US15/107,738 patent/US9644043B2/en not_active Expired - Fee Related
- 2014-11-19 WO PCT/JP2014/080585 patent/WO2015098370A1/ja not_active Ceased
- 2014-12-04 TW TW103142177A patent/TWI636067B/zh active
-
2016
- 2016-06-22 SA SA516371384A patent/SA516371384B1/ar unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001316455A (ja) | 2000-04-28 | 2001-11-13 | Nippon Zeon Co Ltd | 脂環構造含有重合体の製造方法および成形体 |
| JP2011074373A (ja) | 2009-09-04 | 2011-04-14 | Idemitsu Kosan Co Ltd | 重合溶液の揮発成分除去装置、その方法、および、重合装置 |
| JP2012251051A (ja) | 2011-06-01 | 2012-12-20 | Idemitsu Kosan Co Ltd | 水添石油樹脂ペレットの製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| US20160319047A1 (en) | 2016-11-03 |
| TWI636067B (zh) | 2018-09-21 |
| SA516371384B1 (ar) | 2018-06-04 |
| CN105849136A (zh) | 2016-08-10 |
| SG11201604930WA (en) | 2016-08-30 |
| US9644043B2 (en) | 2017-05-09 |
| MY174155A (en) | 2020-03-11 |
| JP2015124246A (ja) | 2015-07-06 |
| WO2015098370A1 (ja) | 2015-07-02 |
| TW201529608A (zh) | 2015-08-01 |
| CN105849136B (zh) | 2019-06-14 |
| KR20160102995A (ko) | 2016-08-31 |
| JP6403951B2 (ja) | 2018-10-10 |
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Patent event date: 20160616 Patent event code: PA01051R01D Comment text: International Patent Application |
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Patent event code: PA02012R01D Patent event date: 20190827 Comment text: Request for Examination of Application |
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