CN111100241A - Hydrogenated petroleum resin prepared by taking dicyclopentadiene as raw material and preparation method thereof - Google Patents
Hydrogenated petroleum resin prepared by taking dicyclopentadiene as raw material and preparation method thereof Download PDFInfo
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- CN111100241A CN111100241A CN201811246968.7A CN201811246968A CN111100241A CN 111100241 A CN111100241 A CN 111100241A CN 201811246968 A CN201811246968 A CN 201811246968A CN 111100241 A CN111100241 A CN 111100241A
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- 229920005989 resin Polymers 0.000 title claims abstract description 64
- 239000011347 resin Substances 0.000 title claims abstract description 64
- 239000003208 petroleum Substances 0.000 title claims abstract description 61
- 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 41
- 239000002994 raw material Substances 0.000 title claims abstract description 24
- 238000002360 preparation method Methods 0.000 title abstract description 7
- 238000006243 chemical reaction Methods 0.000 claims abstract description 54
- 238000000034 method Methods 0.000 claims abstract description 37
- 238000012719 thermal polymerization Methods 0.000 claims abstract description 24
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 22
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 18
- 239000003054 catalyst Substances 0.000 claims abstract description 17
- 239000000463 material Substances 0.000 claims abstract description 17
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 10
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical group [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 9
- 238000004321 preservation Methods 0.000 claims description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 5
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 4
- 239000008096 xylene Substances 0.000 claims description 4
- 239000011148 porous material Substances 0.000 claims description 3
- 230000003068 static effect Effects 0.000 claims description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- 230000009471 action Effects 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 230000008569 process Effects 0.000 abstract description 16
- 239000012535 impurity Substances 0.000 abstract description 6
- 238000009826 distribution Methods 0.000 abstract description 4
- 239000007788 liquid Substances 0.000 abstract description 4
- 231100000572 poisoning Toxicity 0.000 abstract description 2
- 230000000607 poisoning effect Effects 0.000 abstract description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 10
- 230000000694 effects Effects 0.000 description 4
- 230000008901 benefit Effects 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 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
- 239000000571 coke Substances 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000002952 polymeric resin Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000002390 adhesive tape Substances 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 239000002910 solid waste Substances 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
- C08F240/00—Copolymers of hydrocarbons and mineral oils, e.g. petroleum resins
-
- 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
- C08F2/00—Processes of polymerisation
-
- 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
Abstract
The invention discloses a hydrogenated petroleum resin prepared by taking dicyclopentadiene as a raw material and a preparation method thereof. According to the invention, through stability control of the dicyclopentadiene thermal polymerization process and a multi-stage continuous polymerization process, the temperature, material concentration and material concentration uniformity in the thermal polymerization reaction are controlled, on one hand, the content of gel and other impurities in the obtained petroleum resin polymerization liquid meets the hydrogenation reaction requirement, the prepared petroleum resin can be directly used for the hydrogenation reaction, and the subsequent process flow does not need to treat the materials so as to prevent the poisoning problem of the hydrogenation catalyst in the hydrogenation stage of the petroleum resin caused by the impurities. On the other hand, the uniformity of the concentration of the reaction materials and the uniform temperature distribution at the same cross section inside the reaction materials are ensured, so that the dicyclopentadiene completely participates in the thermal polymerization reaction, and the reaction yield is improved.
Description
Technical Field
The invention relates to a hydrogenated petroleum resin prepared by taking dicyclopentadiene as a raw material and a preparation method thereof, in particular to a method for preparing the hydrogenated petroleum resin by controlling the stability of the thermal polymerization process of the dicyclopentadiene and a multi-stage continuous polymerization process.
Background
With the further advancement of the environmental protection concept and the upgrading and upgrading of terminal products, the national industrial structure is adjusted, and the industries of coating and adhesive are transformed and upgraded, so that the market demand on high-quality petroleum resin, namely hydrogenated petroleum resin, is increased, and more high-quality petroleum resin is imperatively produced. At present, high-quality petroleum resin in international market has chroma less than 2# and softening point over 100 deg.c, and is prepared with hydrogenated petroleum resin technology. The dicyclopentadiene (DCPD) hydrogenated petroleum resin is high-quality petroleum resin obtained by polymerizing, hydrogenating and post-treating DCPD, has the advantages of light color, no peculiar smell, strong stability and the like, and is widely applied to the aspects of outdoor sealants, disposable sanitary products, medical adhesive tapes, polyolefin modifiers and the like.
The polymerization of DCPD generally does not use catalysts, the cross-linking reaction is easy to occur during heating, the production process of the DCPD petroleum resin at present is an intermittent or semi-continuous process, the production equipment is a kettle type reactor, a loop (multi-kettle series) reactor and a tower type reactor, and the existing mode is adopted, because the temperature and the concentration of reactants cannot be effectively controlled, not only is oligomer gel inevitably generated in a polymerization solution, but also the branching of the polymer resin is serious, and the hydrogenation difficulty of the subsequent resin is further improved. In addition, DCPD can not completely react, and they are easy to polymerize and coke during hydrogenation reaction, and the coke is covered on the catalyst surface and deposited in the catalyst pore channels, which results in the reduction of catalyst activity and poor catalytic performance. These incompletely reacted feeds therefore also need to be treated before hydrogenation. In the prior art, for example, US4384080A, US728569, CN105175633A, CN104877077A, CN102746458A, CN201110060730.7 and the like mostly adopt a combined petroleum resin hydrotreating method, including two-stage processes of adsorption and hydrogenation, although the combined petroleum resin hydrotreating method has certain effects, the combined petroleum resin hydrotreating method has obvious defects in the aspects of actual operation, production cost, product stability and the like, and has poor gel removal effect; on the other hand, the adsorption method has the disadvantages of large material loss, difficult treatment of solid wastes, complex combined process flow, high cost and the like. The high-softening-point and insoluble polymer generated by DCPD polymerization also becomes dark quickly, so the research focus of DCPD polymerization is mainly the stability control and post-treatment process (removing gel and oligomer) of the thermal polymerization process.
In order to reduce gel generation and prevent implosion, in the prior art, for example, CN102086252A uses a polymerization kettle as a reactor, and adopts a polymerization liquid external circulation mode, but the method has high energy consumption, large polymerization temperature change, and certain influence on product quality. Therefore, the prior art has no simple and effective method for solving the problem of impurities such as gel, and the polymerized petroleum resin can be further used for hydrogenation reaction only by carrying out complicated pretreatment.
Disclosure of Invention
In order to overcome the defects in the prior art, the invention aims to provide hydrogenated petroleum resin prepared by using DCPD as a raw material and a preparation method thereof, which improve the yield of products and ensure that no gel and other impurities exist in petroleum resin polymerization liquid through the stability control of a thermal polymerization process and a multi-stage continuous polymerization process, and the prepared petroleum resin can be directly used for hydrogenation reaction, so that high-quality hydrogenated petroleum resin can be obtained while the service life of a catalyst is prolonged, the energy consumption and the equipment investment are reduced, the stability of the product quality can be maintained, and the benefit is increased.
The following is a specific embodiment of the present invention.
A method for preparing hydrogenated petroleum resin by taking DCPD as raw material mainly comprises the following steps:
1) DCPD polymerization: after mixing materials consisting of DCPD raw materials and organic solvents, continuously carrying out preheating reaction and thermal polymerization reaction by two sections of tubular reactors with static mixing elements; then carrying out heat preservation reaction on the materials in a kettle type reactor, and filtering to obtain a petroleum resin solution; wherein: in the tubular reactor, a tube pass medium is a material, a shell pass medium is heat conduction oil, the mass ratio of a DCPD raw material to a solvent is 1: 1-5, the preheating reaction temperature is 170-220 ℃, the preheating reaction pressure is 1.0-3.0 MPa, the preheating reaction residence time is 30-60 min, the thermal polymerization reaction temperature is 220-260 ℃, the thermal polymerization reaction pressure is 1.0-3.0 MPa, the thermal polymerization reaction residence time is 60-120 min, the heat preservation reaction temperature is 240-260 ℃, the heat preservation reaction pressure is 1.0-3.0 MPa, and the heat preservation reaction residence time is 120-240 min;
2) hydrogenation of petroleum resin solution: carrying out hydrogenation reaction on the petroleum resin solution obtained in the step 1) under the action of a catalyst, and recovering a solvent from the obtained material to obtain hydrogenated petroleum resin; wherein: the molar ratio of the petroleum resin to the hydrogen is 1: 2-5, the dosage of the catalyst is 0.5-3.0 wt% of the petroleum resin, the reaction time is 120-300 min, the reaction pressure is 4.0-10.0 MPa, and the reaction temperature is 170-250 ℃.
The organic solvent in the step 1) is selected from any one of cyclopentane, cyclohexane, benzene, toluene and xylene; more preferably, the organic solvent is toluene or xylene;
the mass ratio of the DCPD raw material to the solvent in the step 1) is preferably 1: 1-2;
the preheating reaction temperature in the step 1) is preferably 190-200 ℃, the preheating reaction pressure is preferably 1.5-2.0 MPa, and the preheating reaction residence time is preferably 40-50 min;
the thermal polymerization temperature in the step 1) is preferably 240-250 ℃, the thermal polymerization pressure is preferably 1.5-2.0 MPa, and the thermal polymerization residence time is preferably 80-100 min;
the heat preservation reaction temperature in the step 1) is preferably 240-260 ℃, the heat preservation reaction pressure is preferably 1.5-2.0 MPa, and the heat preservation reaction residence time is preferably 160-200 min;
the catalyst in the step 2) is preferably a skeletal nickel catalyst; more preferably, in the skeletal nickel catalyst, the content of nickel is preferably 40-80 wt%, and the average pore diameter is preferably 2.0-20.0 nm;
the dosage of the catalyst in the step 2) is preferably 1.0-2.0 wt% of the petroleum resin, the reaction time is preferably 180-240 min, the reaction pressure is preferably 6.0-8.0 MPa, the reaction temperature is preferably 200-220 ℃, and the molar ratio of the petroleum resin to the hydrogen is preferably 1: 3-4;
the invention also provides a hydrogenated petroleum resin obtained by the preparation method.
In the process of preparing hydrogenated petroleum resin by taking DCPD as a raw material, gel generated in the first-step polymerization is a main factor influencing the performance of a hydrogenation catalyst in the thermal polymerization reaction, the existing equipment and process are adopted for carrying out the thermal polymerization reaction, and because the temperature and the concentration of reactants cannot be effectively controlled, a raw material molecular chain excessively expands in a very short time to generate a gel effect, so that not only is low polymer gel inevitably generated in petroleum resin polymerization liquid, but also the branched chain of the polymer resin is serious, and the hydrogenation difficulty of the subsequent petroleum resin is further improved. The inventor researches and discovers that the thermal polymerization reaction of DCPD is firstly initiated by depolymerization of DCPD to Cyclopentadiene (CPD) at a certain temperature, and then the reaction is strongly exothermic due to the higher concentration of CPD in the initial stage. If the amount of the CPD generated by depolymerization is controlled in the first step, a tubular reactor is adopted in the second step, and heat conduction oil is selected as a shell pass medium to carry out heat exchange and temperature control; meanwhile, a high-efficiency static mixing element is installed on the tube side with the medium as the material, so that the uniformity of the concentration of the reaction material and the uniform temperature distribution at the same internal section are ensured. The problem of gel can be effectively solved through the control of the thermal polymerization process, materials do not need to be treated in the subsequent process so as to prevent the poisoning problem of the hydrogenation catalyst in the hydrogenation stage of the petroleum resin caused by impurities, and the DCPD is enabled to be completely involved in the reaction, so that the reaction yield is improved.
The method for preparing hydrogenated petroleum resin by using DCPD as raw material has the advantages that the stability of the thermal polymerization process is controlled by changing the traditional petroleum resin polymerization process, and the multi-stage continuous polymerization process is adopted, so that on one hand, the obtained petroleum resin solves the problem of gel impurities, can be directly used for hydrogenation reaction without complex pretreatment, and improves the efficiency, stability and service life of the catalyst used in the hydrogenation reaction; on the other hand, because the DCPD raw materials are all involved in the reaction, the petroleum resin yield of the thermal polymerization reaction is also obviously improved.
Drawings
FIG. 1 is a process flow diagram of the present invention.
Detailed Description
The invention is further illustrated by the following figures and detailed description of the embodiments, wherein the resin yield calculation formula is as follows:
it should be noted that the following examples are merely illustrative of embodiments of the present invention and are not intended to limit the scope of the present invention.
Example [ 1 to 10 ]
The technological process of the embodiments 1 to 10 is shown in figure 1, the raw material W1 is a DCPD-rich material, the main composition of which is shown in table 1, and the product W2 is hydrogenated petroleum resin prepared by the preparation method provided by the invention. In the examples, the process conditions of the pre-reactor, the thermal polymerization reactor, the holding reactor and the hydrogenation reactor are shown in tables 2, 3, 4 and 5, respectively, wherein the hydrogenation reaction uses a skeletal nickel catalyst. After the reaction was completed, the petroleum resin samples were weighed and analyzed for various indices (softening point, molecular weight distribution, bromine number, etc.), and the results are shown in Table 6. Determining resin product molecular weight distribution index (M) by gel chromatographyw/Mn) The softening point was analyzed by the ring and sphere method GB/2294, and the bromine number was analyzed by the iodometry method (SWB 2301-62).
Table 1.
| Components | Content (wt.%) |
| CPD | 0.3 |
| DCPD | 84.0 |
| NB | 9.5 |
| Others | 6.2 |
Table 2.
Table 3.
| Temperature of thermal polymerization/. degree.C | Thermal polymerizationstress/Mpa | Residence time/min for thermal polymerization | |
| Example 1 | 220 | 1.0 | 120 |
| Example 2 | 250 | 1.6 | 90 |
| Example 3 | 230 | 1.5 | 100 |
| Example 4 | 245 | 1.6 | 95 |
| Example 5 | 246 | 1.8 | 80 |
| Example 6 | 244 | 1.7 | 88 |
| Example 7 | 242 | 1.6 | 92 |
| Example 8 | 248 | 1.9 | 85 |
| Example 9 | 240 | 2.0 | 98 |
| Example 10 | 260 | 3.0 | 60 |
Table 4.
| The reaction temperature/DEG C is kept constant | Reaction pressure/Mpa of thermal insulation | Residence time/min of heat preservation reaction | |
| Example 1 | 240 | 1.0 | 240 |
| Example 2 | 251 | 1.6 | 190 |
| Example 3 | 253 | 1.5 | 200 |
| Example 4 | 251 | 1.6 | 180 |
| Example 5 | 255 | 1.8 | 160 |
| Example 6 | 250 | 1.7 | 170 |
| Example 7 | 252 | 1.6 | 175 |
| Example 8 | 254 | 1.9 | 165 |
| Example 9 | 245 | 2.0 | 185 |
| Example 10 | 260 | 3.0 | 120 |
TABLE 5
Table 6.
Claims (11)
1. A method for preparing hydrogenated petroleum resin by taking dicyclopentadiene as a raw material is characterized by comprising the following steps:
1) polymerization of dicyclopentadiene: mixing a material consisting of a dicyclopentadiene raw material and an organic solvent, and then continuously carrying out a preheating reaction and a thermal polymerization reaction through two sections of tubular reactors with static mixing elements; then carrying out heat preservation reaction on the materials in a kettle type reactor, and filtering to obtain a petroleum resin solution; wherein the mass ratio of the dicyclopentadiene to the solvent is 1: 1-5, the preheating reaction temperature is 170-;
2) hydrogenation of petroleum resin solution: carrying out hydrogenation reaction on the petroleum resin solution obtained in the step 1) under the action of a catalyst, and recovering a solvent from the obtained material to obtain hydrogenated petroleum resin; wherein the molar ratio of the petroleum resin to the hydrogen is 1: 2-5, the dosage of the catalyst is 0.5-3.0 wt% of the petroleum resin, the reaction time is 120-300 min, the reaction pressure is 4.0-10.0 MPa, and the reaction temperature is 170-250 ℃.
2. The method for preparing hydrogenated petroleum resin using dicyclopentadiene as a raw material as set forth in claim 1, wherein in step 1), the organic solvent is any one of cyclopentane, cyclohexane, benzene, toluene and xylene.
3. The method for preparing a hydrogenated petroleum resin using dicyclopentadiene as a raw material according to claim 1 or claim 2, wherein in step 1), the organic solvent is toluene or xylene.
4. The method for preparing the hydrogenated petroleum resin by using the dicyclopentadiene as the raw material according to claim 1, wherein the mass ratio of the dicyclopentadiene raw material to the solvent in the step 1) is 1: 1-2.
5. The method as claimed in claim 1, wherein the preheating reaction temperature is 190-.
6. The method for preparing hydrogenated petroleum resin using dicyclopentadiene as a raw material according to claim 1, wherein in step 1), the thermal polymerization temperature is 240 to 250 ℃, the reaction pressure is 1.5 to 2.0MPa, and the residence time is 80 to 100 min.
7. The method for preparing hydrogenated petroleum resin by using dicyclopentadiene as a raw material according to claim 1, wherein in the step 1), the reaction temperature is 240 to 260 ℃, the reaction pressure is 1.5 to 2.0MPa, and the reaction residence time is 160 to 200 min.
8. The method for preparing hydrogenated petroleum resin using dicyclopentadiene as a raw material according to claim 1, wherein in step 2), the catalyst is a skeletal nickel catalyst.
9. The method of claim 8, wherein the nickel content of the skeletal nickel catalyst is 40-80 wt%, and the average pore diameter is 2.0-20.0 nm.
10. The method for preparing the hydrogenated petroleum resin by using the dicyclopentadiene as the raw material according to claim 1, wherein in the step 2), the amount of the catalyst is 1.0-2.0 wt% of the petroleum resin, the reaction time is 180-240 min, the reaction pressure is 6.0-8.0 MPa, the reaction temperature is 200-220 ℃, and the molar ratio of the petroleum resin to the hydrogen is 1: 3-4.
11. A hydrogenated petroleum resin obtained by the production method according to any one of claims 1 to 10.
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| KR20170038404A (en) * | 2015-09-30 | 2017-04-07 | 코오롱인더스트리 주식회사 | Petroleum Resin and Process of Preparing for the Same |
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| CN108003291A (en) * | 2016-10-28 | 2018-05-08 | 中国石油化工股份有限公司 | A kind of method that hydrogenated petroleum resin is prepared using dicyclopentadiene as raw material |
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2018
- 2018-10-25 CN CN201811246968.7A patent/CN111100241A/en active Pending
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