CN106928058A - 烷基酚聚氧乙烯醚酯化物的甲醛缩聚体及其制备方法 - Google Patents
烷基酚聚氧乙烯醚酯化物的甲醛缩聚体及其制备方法 Download PDFInfo
- Publication number
- CN106928058A CN106928058A CN201710186438.7A CN201710186438A CN106928058A CN 106928058 A CN106928058 A CN 106928058A CN 201710186438 A CN201710186438 A CN 201710186438A CN 106928058 A CN106928058 A CN 106928058A
- Authority
- CN
- China
- Prior art keywords
- alkylphenol
- formaldehyde
- catalyst
- polycondensate
- action
- 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.)
- Granted
Links
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 title claims abstract description 208
- 229920000642 polymer Polymers 0.000 title claims abstract description 46
- 238000009833 condensation Methods 0.000 title claims abstract description 31
- 230000005494 condensation Effects 0.000 title claims abstract description 31
- 238000002360 preparation method Methods 0.000 title claims abstract description 22
- 241001272567 Hominoidea Species 0.000 title abstract 3
- 150000007942 carboxylates Chemical class 0.000 title abstract 3
- 238000006243 chemical reaction Methods 0.000 claims abstract description 35
- 239000002002 slurry Substances 0.000 claims abstract description 35
- 150000008065 acid anhydrides Chemical class 0.000 claims abstract description 19
- 239000002245 particle Substances 0.000 claims abstract description 14
- 238000006068 polycondensation reaction Methods 0.000 claims abstract description 14
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 11
- 238000005886 esterification reaction Methods 0.000 claims abstract description 9
- 239000000126 substance Substances 0.000 claims abstract description 9
- -1 alkyl phenol Chemical compound 0.000 claims abstract description 5
- 239000011949 solid catalyst Substances 0.000 claims abstract description 5
- 230000032050 esterification Effects 0.000 claims abstract 2
- 239000003054 catalyst Substances 0.000 claims description 37
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 claims description 22
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 21
- GFAJOMHUNNCCJQ-UHFFFAOYSA-N 1,3-dioxetane Chemical compound C1OCO1 GFAJOMHUNNCCJQ-UHFFFAOYSA-N 0.000 claims description 20
- 125000002947 alkylene group Chemical group 0.000 claims description 19
- 229920001289 polyvinyl ether Polymers 0.000 claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- 239000003377 acid catalyst Substances 0.000 claims description 15
- 239000013638 trimer Substances 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- 238000010438 heat treatment Methods 0.000 claims description 12
- 229940051841 polyoxyethylene ether Drugs 0.000 claims description 11
- 229920000056 polyoxyethylene ether Polymers 0.000 claims description 11
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 238000010992 reflux Methods 0.000 claims description 7
- 238000007142 ring opening reaction Methods 0.000 claims description 7
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 6
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 6
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 229920002866 paraformaldehyde Polymers 0.000 claims description 6
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 3
- ZEYLTQYYYOQOJR-UHFFFAOYSA-N [Mo+2]=O.[O-2].[Zr+4].[O-2].[O-2] Chemical compound [Mo+2]=O.[O-2].[Zr+4].[O-2].[O-2] ZEYLTQYYYOQOJR-UHFFFAOYSA-N 0.000 claims description 3
- XKNZTYYAKKNCDJ-UHFFFAOYSA-N [O-2].[Zr+4].[W+2]=O.[O-2].[O-2] Chemical compound [O-2].[Zr+4].[W+2]=O.[O-2].[O-2] XKNZTYYAKKNCDJ-UHFFFAOYSA-N 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 3
- 150000002989 phenols Chemical class 0.000 claims description 3
- 229940014800 succinic anhydride Drugs 0.000 claims description 3
- 238000012644 addition polymerization Methods 0.000 claims description 2
- 239000008098 formaldehyde solution Substances 0.000 claims description 2
- 238000004062 sedimentation Methods 0.000 abstract description 22
- 230000000694 effects Effects 0.000 abstract description 13
- 239000002994 raw material Substances 0.000 abstract description 5
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 238000007560 sedimentation technique Methods 0.000 abstract 1
- 239000003921 oil Substances 0.000 description 33
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 14
- IGFHQQFPSIBGKE-UHFFFAOYSA-N 4-nonylphenol Chemical compound CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 12
- 238000004523 catalytic cracking Methods 0.000 description 12
- 239000000047 product Substances 0.000 description 10
- 150000001875 compounds Chemical group 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- QMRFMPKHFZDFGG-UHFFFAOYSA-N 2,6-bis(hydroxymethyl)-4-nonylphenol Chemical compound CCCCCCCCCC1=CC(CO)=C(O)C(CO)=C1 QMRFMPKHFZDFGG-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 239000012752 auxiliary agent Substances 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 238000004321 preservation Methods 0.000 description 2
- 239000011973 solid acid Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 239000011345 viscous material Substances 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000012496 blank sample Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 230000001502 supplementing effect Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
- C07C37/20—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms using aldehydes or ketones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/02—Preparation of ethers from oxiranes
- C07C41/03—Preparation of ethers from oxiranes by reaction of oxirane rings with hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G29/00—Refining of hydrocarbon oils, in the absence of hydrogen, with other chemicals
- C10G29/20—Organic compounds not containing metal atoms
- C10G29/22—Organic compounds not containing metal atoms containing oxygen as the only hetero atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Abstract
Description
Claims (10)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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CN201710186438.7A CN106928058B (zh) | 2017-03-24 | 2017-03-24 | 烷基酚聚氧乙烯醚酯化物的甲醛缩聚体及其制备方法 |
Applications Claiming Priority (1)
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CN201710186438.7A CN106928058B (zh) | 2017-03-24 | 2017-03-24 | 烷基酚聚氧乙烯醚酯化物的甲醛缩聚体及其制备方法 |
Publications (2)
Publication Number | Publication Date |
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CN106928058A true CN106928058A (zh) | 2017-07-07 |
CN106928058B CN106928058B (zh) | 2020-08-04 |
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CN201710186438.7A Active CN106928058B (zh) | 2017-03-24 | 2017-03-24 | 烷基酚聚氧乙烯醚酯化物的甲醛缩聚体及其制备方法 |
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107794077A (zh) * | 2017-11-16 | 2018-03-13 | 上海鑫灵精细化工有限公司 | 一种油浆沉降剂及其制备方法 |
CN113046115A (zh) * | 2021-03-02 | 2021-06-29 | 金浦新材料股份有限公司 | 催化裂化油浆沉降剂及其应用 |
CN113501953A (zh) * | 2021-07-23 | 2021-10-15 | 中山市钧纬新材料科技有限公司 | 一种梳状烷基酚聚氧乙烯醚阴离子型水性分散剂及其制备方法 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3919429A (en) * | 1972-01-18 | 1975-11-11 | Hoechst Ag | Dispersing and wetting agents for use in organic biocides |
US4416754A (en) * | 1981-08-24 | 1983-11-22 | Exxon Research And Engineering Co. | Compositions and process for dedusting solids-containing hydrocarbon oils |
-
2017
- 2017-03-24 CN CN201710186438.7A patent/CN106928058B/zh active Active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3919429A (en) * | 1972-01-18 | 1975-11-11 | Hoechst Ag | Dispersing and wetting agents for use in organic biocides |
US4416754A (en) * | 1981-08-24 | 1983-11-22 | Exxon Research And Engineering Co. | Compositions and process for dedusting solids-containing hydrocarbon oils |
Non-Patent Citations (3)
Title |
---|
杨芳 等: "壬基酚聚氧乙烯醚二聚和三聚表面活性剂的合成及表面性质", 《高等学校化学学报》 * |
谢剑妹: "新型表面活性剂的合成及其乳化性能的研究", 《中国优秀硕士学位论文全文数据库 工程科技Ⅰ辑》 * |
黄文轩: "第18讲:表面活性剂的特性及应用:乳化剂和破乳化剂", 《石油商技》 * |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107794077A (zh) * | 2017-11-16 | 2018-03-13 | 上海鑫灵精细化工有限公司 | 一种油浆沉降剂及其制备方法 |
CN113046115A (zh) * | 2021-03-02 | 2021-06-29 | 金浦新材料股份有限公司 | 催化裂化油浆沉降剂及其应用 |
CN113046115B (zh) * | 2021-03-02 | 2022-05-27 | 金浦新材料股份有限公司 | 催化裂化油浆沉降剂及其应用 |
CN113501953A (zh) * | 2021-07-23 | 2021-10-15 | 中山市钧纬新材料科技有限公司 | 一种梳状烷基酚聚氧乙烯醚阴离子型水性分散剂及其制备方法 |
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Application publication date: 20170707 Assignee: WEIHAI XIANGYU TECHNOLOGY CO.,LTD. Assignor: WEIHAI XIANGZE NEW MATERIAL TECHNOLOGY CO.,LTD. Contract record no.: X2022980014709 Denomination of invention: Formaldehyde polycondensate of alkylphenol polyoxyethylene ether ester and preparation method thereof Granted publication date: 20200804 License type: Exclusive License Record date: 20220909 |
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Effective date of registration: 20231108 Address after: No. 1 Hangzhou Road, Economic Development Zone, Wendeng District, Weihai City, Shandong Province, 264400 Patentee after: WEIHAI XIANGYU TECHNOLOGY CO.,LTD. Address before: Room 212 and 213, Building B, 205 Zhuhai Road, Wendeng Economic Development Zone, Weihai City, Shandong Province, 264400 Patentee before: WEIHAI XIANGZE NEW MATERIAL TECHNOLOGY CO.,LTD. |