CN109721685A - A method of hydrogenated petroleum resin is prepared by raw material of dicyclopentadiene - Google Patents
A method of hydrogenated petroleum resin is prepared by raw material of dicyclopentadiene Download PDFInfo
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- CN109721685A CN109721685A CN201711025313.2A CN201711025313A CN109721685A CN 109721685 A CN109721685 A CN 109721685A CN 201711025313 A CN201711025313 A CN 201711025313A CN 109721685 A CN109721685 A CN 109721685A
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- petroleum resin
- raw material
- hydrogenated petroleum
- dicyclopentadiene
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- 239000011347 resin Substances 0.000 title claims abstract description 36
- 229920005989 resin Polymers 0.000 title claims abstract description 36
- 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 title claims abstract description 31
- 238000000034 method Methods 0.000 title claims abstract description 29
- 239000003208 petroleum Substances 0.000 title claims abstract description 26
- 239000002994 raw material Substances 0.000 title claims abstract description 22
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 17
- 239000003054 catalyst Substances 0.000 claims abstract description 16
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000005864 Sulphur Substances 0.000 claims abstract description 6
- 238000006477 desulfuration reaction Methods 0.000 claims abstract description 6
- 230000023556 desulfurization Effects 0.000 claims abstract description 6
- 239000012535 impurity Substances 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 238000006116 polymerization reaction Methods 0.000 claims description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- 239000000084 colloidal system Substances 0.000 claims description 11
- 239000000463 material Substances 0.000 claims description 10
- 239000003112 inhibitor Substances 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 6
- 229920000642 polymer Polymers 0.000 claims description 5
- 239000012530 fluid Substances 0.000 claims description 3
- 238000004064 recycling Methods 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 230000003068 static effect Effects 0.000 claims description 3
- -1 pentamethylene, hexamethylene Chemical group 0.000 claims description 2
- 239000011148 porous material Substances 0.000 claims description 2
- 229910052761 rare earth metal Inorganic materials 0.000 claims description 2
- 150000002910 rare earth metals Chemical class 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- HECLRDQVFMWTQS-UHFFFAOYSA-N Dicyclopentadiene Chemical compound C1C2C3CC=CC3C1C=C2 HECLRDQVFMWTQS-UHFFFAOYSA-N 0.000 claims 4
- 230000008901 benefit Effects 0.000 abstract description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 231100000614 poison Toxicity 0.000 description 4
- 230000007096 poisonous effect Effects 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229920002521 macromolecule Polymers 0.000 description 3
- 125000001741 organic sulfur group Chemical group 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- 235000005128 Sapium sebiferum Nutrition 0.000 description 2
- 244000057114 Sapium sebiferum Species 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 238000004220 aggregation Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 239000008601 oleoresin Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 239000004575 stone Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004831 Hot glue Substances 0.000 description 1
- 239000013032 Hydrocarbon resin Substances 0.000 description 1
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 238000004939 coking Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 229920006270 hydrocarbon resin Polymers 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- JRTYPQGPARWINR-UHFFFAOYSA-N palladium platinum Chemical group [Pd].[Pt] JRTYPQGPARWINR-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000002910 solid waste Substances 0.000 description 1
- WWNBZGLDODTKEM-UHFFFAOYSA-N sulfanylidenenickel Chemical class [Ni]=S WWNBZGLDODTKEM-UHFFFAOYSA-N 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Landscapes
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
The present invention discloses a kind of method for preparing hydrogenated petroleum resin as raw material using dicyclopentadiene, influence of the impurity such as gel and sulphur to hydrogenated petroleum resin is eliminated using desulfurization and hydrogenation technique, improve the service life of pretreatment catalyst and hydrogenation catalyst, reduce operating cost and equipment investment, obtain good hydrogenated petroleum resin, and it is able to maintain the stability of product quality, increase benefit.
Description
Technical field
The present invention relates to a kind of methods for preparing hydrogenated petroleum resin as raw material using dicyclopentadiene, in particular to using height
The control that Raney nickel removes macromolecule organic sulfur and polymerization process in DCPD resin solves the harmful poisonous substance of adding hydrogen into resin, system
The method of standby high-quality hydrogenated petroleum resin.
Background technique
Dicyclopentadiene (DCPD) hydrogenated resin is the high-end product of Petropols industry, cyclic structure is remained, with base
The active force of body polymer is greater than straight chain fatty hydrocarbon resin, and adhesive property is better than common C 5 hydrogenated resin, is particularly suitable for
Disposable hygienic material field: each hot melt adhesive such as food packaging articles, pressure sensitive adhesive tape, disposable paper diaper, sanltary towel.
It is in chain and cyclic structure since Petropols molecular weight is bigger, polymer molecule is stretched in catalyst surface,
High spatial petroleum steric hindrance is formd, unsaturated bond hydrogenation reaction activation energy is high, so that reaction condition is become harsh, hydrogenation reaction needs
It is carried out under the conditions of high temperature, high pressure and high activated catalyst.Many companies use noble metal during adding hydrogen into resin both at home and abroad
Loaded catalyst, active component are mainly selected from Pd, Rh, Ru, Re, Pt, and wherein supported palladium system and palladium-platinum group catalyst are outstanding
Feature is that start-up temperature is low plus hydrogen degrading activity is low, adds hydrogen yield high.Its weakness outstanding is, easy poisoning sensitive to impurity
Inactivation, therefore the influence for eliminating harmful poisonous substance is that can hydrogenation of petroleum resin industrialized key.
The poisonous substance of hydrogenation of petroleum resin is generally gel, sulphur and some heavy metals, and the prior art is such as thus
US4384080A, US728569, CN105175633A, CN104877077A, CN102746458A, CN201110060730.7 and
CN105175633A etc. is mostly using hydrodesulfurization, absorption desulfurization (activated clay, zinc oxide, iron oxide or alkali-earth metal modified
Resin the influence of poisonous substance is eliminated by adsorbing) or Combined stone oleoresin hydrotreating method.
The prior art has certain effect, but in the stability of practical operation, production cost and product (with for adding hydrogen
Resin raw material fluctuation) etc. exist it is obvious insufficient, it is ineffective to gum-treated such as hydrodesulfurization higher cost；Absorption
Method loss of material is larger, solid waste is difficult to handle, and group technology process is complicated, at high cost etc..In addition resin in hydrogenation reaction by
It is higher in temperature, gel can be generated because oligomeric, coking material is covered on catalyst surface and is deposited in duct, reduces catalyst
Activity.
It can be seen that solving the problems, such as objectionable impurities without simple effective method in the prior art.Inventor is through studying
It was found that DCPD adding hydrogen into resin technique is selected the lower high-nickel catalyst of price, is faced in hydrogen atmosphere under the conditions of relatively mild
It can achieve the purpose that remove macromolecule organic sulfur, Simultaneous hydrogenation process selection has the dilute of extremely strong peace and quiet dispersibility to colloid
Great soil group matter polymerization inhibitor can effectively prevent the generation and aggregation of colloid, realize the long-term operation of hydrogenation catalyst.
Summary of the invention
For overcome the deficiencies in the prior art, the purpose of the present invention is to provide one kind prepares hydrogenation stone with dicyclopentadiene
The method of oleoresin, its technical problems to be solved are miscellaneous using effective sulfur method and hydrogenation technique elimination gel and sulphur etc.
The influence of matter improves the service life of pretreatment catalyst and hydrogenation catalyst, reduces operating cost and equipment investment, obtains excellent
The hydrogenated petroleum resin of matter, and it is able to maintain the stability of product quality, increase benefit.It is concrete scheme of the invention below.
A method of hydrogenated petroleum resin is prepared with dicyclopentadiene, is mainly comprised the steps that
1) after DCPD raw material is mixed with organic solvent continually by with static mixing original part tubular reactor in into
The mass ratio of row heat polymerization, generation Petropols, DCPD and solvent is 1: (1~5), reaction temperature are 230~270 DEG C,
Reaction pressure is 1.0~3.0MPa, and the residence time is 180~360min；
2) fixed bed for passing through filling high-nickel catalyst by the DCPD polymer fluid that step 1) obtains, in the atmosphere for facing hydrogen
Except the objectionable impurities such as sulphur in raw material, operating pressure is 0.1~1.0MPa, and desulfurization temperature is 60~100 DEG C, and air speed is 1~8h-1；
3) colloid polymerization inhibitor is added by the processed Petropols of step 2), is the reaction of Pd fixed bed hydrogenation by catalyst
The hydrogenated petroleum resin of high-quality is obtained, colloid polymerization inhibitor dosage is 0.05~0.2wt% of Petropols, Petropols and hydrogen
Molar ratio be 1: (2~5), air speed 0.3-2.0h-1, reaction pressure be 8.0~15.0MPa, reaction temperature be 170~250
℃。
4) material obtained by step 3) tower reactor after rectifying column rectifying recycling design obtains the non-hydrogenated petroleum tree of high-quality
Rouge, tower top obtain solvent, and operating pressure is 0.01~0.08MPa, and tower top temperature is 40~90 DEG C, and bottom temperature is 140~200
DEG C, reflux ratio is 1~10.
Above-mentioned steps 1) organic solvent is any one of pentamethylene, hexamethylene, benzene,toluene,xylene.
Above-mentioned steps 1) mass ratio of the DCPD raw material and solvent is preferably 1: (1~2).
Above-mentioned steps 1) reaction temperature is preferably 240~260 DEG C, and reaction pressure is preferably 1.5~2.0MPa, is stopped
Time is preferably 240~300min.
Above-mentioned steps 2) the high-nickel catalyst content is preferably 40~80wt%, and average pore size is preferably 2.0~20.0
Nanometer.
Above-mentioned steps 2) operating pressure is preferably 0.3~0.5MPa, and desulfurization temperature is preferably 80~90 DEG C, and air speed is most
It is well 2~4h-1.
Above-mentioned steps 3) the colloid polymerization inhibitor is preferably YS-NX7000A (main component is Nano Rare-earth Materials), dosage
Preferably 0.1~0.15wt% of Petropols.
Above-mentioned steps 3) molar ratio of the Petropols and hydrogen is preferably 1: (3~4), air speed are preferably 0.5-1.0h-
1, reaction pressure is preferably 9.0~11.0MPa, and reaction temperature is preferably 200~220 DEG C.
Above-mentioned steps 1) and the step 3) organic solvent be preferably one of toluene and dimethylbenzene.
Above-mentioned steps 4) in, operating pressure is preferably 0.2~0.6MPa, and tower top temperature is preferably 50~60 DEG C, tower reactor temperature
Preferably 150~180 DEG C of degree, reflux ratio is preferably 2~5.
In the present invention, inventor has found that selecting in the lower high-nickel catalyst removing DCPD resin of price
Macromolecule organic sulfur (content 8-20PPM), key be Nickel Content In Catalyst height, Sulfur tolerance is good, in facing hydrogen atmosphere lead to
Chemical action is crossed, more nickel sulfides can be formed at a lower temperature, greatly improve pretreatment potentiality and service life, hence it is evident that
Reduce operating cost.Simultaneous hydrogenation process selection has the terres rares matter polymerization inhibitor of extremely strong peace and quiet dispersibility to colloid, can be with
The generation and aggregation for effectively preventing colloid, realize the long-term operation of hydrogenation catalyst.
Below by specific embodiment, the invention will be further described, and resin yield involved in each embodiment calculates
Formula is as follows:
Specific embodiment
[Examples 1 to 10]
The dicyclopentadiene that Examples 1 to 10 uses isolated thick dicyclopentadiene in light dydrocarbon separator produces
Product.Its component is shown in Table 1.
Table 1.
| Component | Content (wt.%) |
| CPD | 0.3 |
| DCPD | 84.0 |
| NB | 9.5 |
| Carbon six | 1.2 |
| It is other | 5.0 |
Thick dicyclopentadiene carries out handling synthesizing hydrogenated Petropols according to following procedure:
1) after DCPD raw material is mixed with organic solvent continually by with static mixing original part tubular reactor in into
Row heat polymerization generates Petropols；
2) fixed bed for passing through filling high-nickel catalyst by the DCPD polymer fluid that step 1) obtains, in the atmosphere for facing hydrogen
Except the objectionable impurities such as sulphur in raw material；
3) colloid polymerization inhibitor is added by the processed Petropols of step 2), is the reaction of Pd fixed bed hydrogenation by catalyst
Obtain the hydrogenated petroleum resin of high-quality；
4) material obtained by step 3) tower reactor after rectifying column rectifying recycling design obtains the non-hydrogenated petroleum tree of high-quality
Rouge, tower top obtain solvent.
Each process process condition is shown in Table 2, table 3 and table 4, is formed using gas chromatographic analysis material, the result is shown in tables
5.Table 2.
Table 3.
Table 4.
Table 5.
Claims (10)
1. a kind of method for preparing hydrogenated petroleum resin as raw material using dicyclopentadiene, it is characterised in that the following steps are included:
1) it is hot continually by being carried out in the tubular reactor with static mixing original part after DCPD raw material is mixed with organic solvent
The mass ratio of polymerization reaction, generation Petropols, DCPD and solvent is 1: (1~5), reaction temperature are 230~270 DEG C, reaction
Pressure is 1.0~3.0MPa, and the residence time is 180~360min；
2) the DCPD polymer fluid obtained by step 1) is removed former by the fixed bed of filling high-nickel catalyst in the atmosphere for facing hydrogen
The objectionable impurities such as sulphur in material, operating pressure are 0.1~1.0MPa, and desulfurization temperature is 60~100 DEG C, and air speed is 1~8h-1；
3) colloid polymerization inhibitor is added by the processed Petropols of step 2), is that Pd fixed bed hydrogenation reacts to obtain by catalyst
The hydrogenated petroleum resin of high-quality, colloid polymerization inhibitor dosage are 0.05~0.2wt% of Petropols, and Petropols and hydrogen rub
You are than being 1: (2~5), air speed 0.3-2.0h-1, reaction pressure are 8.0~15.0MPa, and reaction temperature is 170~250 DEG C；
4) material obtained by step 3) tower reactor after rectifying column rectifying recycling design obtains the hydrogenated petroleum resin of high-quality, tower
Top obtains solvent, and operating pressure is 0.01~0.08MPa, and tower top temperature is 40~90 DEG C, and bottom temperature is 140~200 DEG C, returns
Stream is than being 1~10.
2. a kind of method for preparing hydrogenated petroleum resin as raw material using dicyclopentadiene, feature exist according to claim 1
In the step 1) organic solvent be any one of pentamethylene, hexamethylene, benzene,toluene,xylene.
3. a kind of method for preparing hydrogenated petroleum resin as raw material using dicyclopentadiene, feature exist according to claim 1
In the mass ratio of step 1) the DCPD raw material and solvent be 1: (1~2).
4. a kind of method for preparing hydrogenated petroleum resin as raw material using dicyclopentadiene, feature exist according to claim 1
It is 240~260 DEG C in the step 1) reaction temperature, reaction pressure is 1.5~2.0MPa, and the residence time is 240~300min.
5. a kind of method for preparing hydrogenated petroleum resin as raw material using dicyclopentadiene, feature exist according to claim 1
It is 40~80wt% in step 2) the high-nickel catalyst content, average pore size is 2.0~20.0 nanometers.
6. a kind of method for preparing hydrogenated petroleum resin as raw material using dicyclopentadiene, feature exist according to claim 1
It is 0.3~0.5MPa in step 2) operating pressure, desulfurization temperature is 80~90 DEG C, and air speed is 2~4h-1。
7. a kind of method for preparing hydrogenated petroleum resin as raw material using dicyclopentadiene, feature exist according to claim 1
It is YS-NX7000A (main component is Nano Rare-earth Materials) in step 3) the colloid polymerization inhibitor, dosage is Petropols
0.1~0.15wt%.
8. a kind of method for preparing hydrogenated petroleum resin as raw material using dicyclopentadiene, feature exist according to claim 1
In the molar ratio of step 3) Petropols and hydrogen be 1: (3~4), air speed 0.5-1.0h-1, reaction pressure be 9.0~
11.0MPa, reaction temperature are 200~220 DEG C.
9. a kind of method for preparing hydrogenated petroleum resin as raw material using dicyclopentadiene, feature exist according to claim 1
The organic solvent described in step 1 and step 3 is preferably one of toluene and dimethylbenzene.
10. a kind of method for preparing hydrogenated petroleum resin as raw material using dicyclopentadiene, feature exist according to claim 1
It is preferably 0.2~0.6MPa in the step 4) operating pressure, tower top temperature is preferably 50~60 DEG C, and bottom temperature is preferably
150~180 DEG C, reflux ratio is preferably 2~5.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201711025313.2A CN109721685A (en) | 2017-10-27 | 2017-10-27 | A method of hydrogenated petroleum resin is prepared by raw material of dicyclopentadiene |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201711025313.2A CN109721685A (en) | 2017-10-27 | 2017-10-27 | A method of hydrogenated petroleum resin is prepared by raw material of dicyclopentadiene |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102516461A (en) * | 2011-10-25 | 2012-06-27 | 中国海洋石油总公司 | Preparation method of light-color hydrogenated dicyclopentadiene petroleum resin with high softening point |
| CN105585666A (en) * | 2014-10-22 | 2016-05-18 | 中国石油化工股份有限公司 | A preparing method of dicyclopentadiene hydrogenated petroleum resin |
| CN106008819A (en) * | 2016-07-07 | 2016-10-12 | 朗盈科技（北京）有限公司 | Production device and method of low-chroma C9 hydrogenated petroleum resin |
| KR20170038404A (en) * | 2015-09-30 | 2017-04-07 | 코오롱인더스트리 주식회사 | Petroleum Resin and Process of Preparing for the Same |
-
2017
- 2017-10-27 CN CN201711025313.2A patent/CN109721685A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102516461A (en) * | 2011-10-25 | 2012-06-27 | 中国海洋石油总公司 | Preparation method of light-color hydrogenated dicyclopentadiene petroleum resin with high softening point |
| CN105585666A (en) * | 2014-10-22 | 2016-05-18 | 中国石油化工股份有限公司 | A preparing method of dicyclopentadiene hydrogenated petroleum resin |
| KR20170038404A (en) * | 2015-09-30 | 2017-04-07 | 코오롱인더스트리 주식회사 | Petroleum Resin and Process of Preparing for the Same |
| CN106008819A (en) * | 2016-07-07 | 2016-10-12 | 朗盈科技（北京）有限公司 | Production device and method of low-chroma C9 hydrogenated petroleum resin |
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Application publication date: 20190507 |