CN106084182A - 一种储存稳定的缩二脲多异氰酸酯的制备方法 - Google Patents
一种储存稳定的缩二脲多异氰酸酯的制备方法 Download PDFInfo
- Publication number
- CN106084182A CN106084182A CN201610430486.1A CN201610430486A CN106084182A CN 106084182 A CN106084182 A CN 106084182A CN 201610430486 A CN201610430486 A CN 201610430486A CN 106084182 A CN106084182 A CN 106084182A
- Authority
- CN
- China
- Prior art keywords
- biuret
- polyisocyanates
- reaction
- diisocyanate
- metal complex
- 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
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 title claims abstract description 100
- 239000005056 polyisocyanate Substances 0.000 title claims abstract description 64
- 229920001228 polyisocyanate Polymers 0.000 title claims abstract description 64
- 238000002360 preparation method Methods 0.000 title claims abstract description 24
- 238000006243 chemical reaction Methods 0.000 claims abstract description 43
- 238000000034 method Methods 0.000 claims abstract description 18
- -1 N heterocyclic carbene metal complex Chemical class 0.000 claims abstract description 14
- 238000003860 storage Methods 0.000 claims abstract description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000000178 monomer Substances 0.000 claims description 33
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 31
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 30
- 125000005442 diisocyanate group Chemical group 0.000 claims description 17
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 239000007787 solid Substances 0.000 claims description 10
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 9
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- KYIMHWNKQXQBDG-UHFFFAOYSA-N N=C=O.N=C=O.CCCCCC Chemical compound N=C=O.N=C=O.CCCCCC KYIMHWNKQXQBDG-UHFFFAOYSA-N 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
- 229910052741 iridium Inorganic materials 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 229910052707 ruthenium Inorganic materials 0.000 claims description 2
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims 1
- 239000004643 cyanate ester Substances 0.000 claims 1
- 239000000047 product Substances 0.000 description 46
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
- 239000012295 chemical reaction liquid Substances 0.000 description 24
- 239000003795 chemical substances by application Substances 0.000 description 18
- 239000010409 thin film Substances 0.000 description 17
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 238000000926 separation method Methods 0.000 description 12
- SNAMIIGIIUQQSP-UHFFFAOYSA-N bis(6-methylheptyl) hydrogen phosphate Chemical compound CC(C)CCCCCOP(O)(=O)OCCCCCC(C)C SNAMIIGIIUQQSP-UHFFFAOYSA-N 0.000 description 11
- 238000007664 blowing Methods 0.000 description 11
- 230000035484 reaction time Effects 0.000 description 11
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 10
- 238000005204 segregation Methods 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 9
- 239000012528 membrane Substances 0.000 description 9
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 8
- 230000008020 evaporation Effects 0.000 description 8
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 8
- 239000012948 isocyanate Substances 0.000 description 7
- 150000002513 isocyanates Chemical class 0.000 description 7
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 0 CC*(C1*(C2*(C)(C)C=C*2C)(N)N=C)C=C*1I Chemical compound CC*(C1*(C2*(C)(C)C=C*2C)(N)N=C)C=C*1I 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 229920002396 Polyurea Polymers 0.000 description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 150000003509 tertiary alcohols Chemical class 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- ADLVDYMTBOSDFE-UHFFFAOYSA-N 5-chloro-6-nitroisoindole-1,3-dione Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC2=C1C(=O)NC2=O ADLVDYMTBOSDFE-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000007848 Bronsted acid Substances 0.000 description 1
- XZDKNHHUPYCECT-UHFFFAOYSA-N CC[N]1(C2)C=C[N]2(C)C1[Ar](C)(C(N(C)C=C1)[N]1(CC)I)Cl Chemical compound CC[N]1(C2)C=C[N]2(C)C1[Ar](C)(C(N(C)C=C1)[N]1(CC)I)Cl XZDKNHHUPYCECT-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
- 241001597008 Nomeidae Species 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 238000005304 joining Methods 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000010200 validation analysis Methods 0.000 description 1
- 239000006200 vaporizer Substances 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/7806—Nitrogen containing -N-C=0 groups
- C08G18/7818—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups
- C08G18/7831—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups containing biuret groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
- C07C273/1872—Preparation of compounds comprising a -N-C(O)-N-C(O)-N- moiety
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyurethanes Or Polyureas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
产品编号 | 固含量/% | 起始单体含量/wt% | 25℃储存240天单体含量/wt% |
实施例1 | 75 | 0.08 | 0.14 |
实施例2 | 75 | 0.08 | 0.13 |
实施例3 | 75 | 0.10 | 0.17 |
实施例4 | 75 | 0.09 | 0.14 |
实施例5 | 75 | 0.10 | 0.16 |
实施例6 | 75 | 0.12 | 0.17 |
实施例7 | 75 | 0.13 | 0.18 |
对比例1 | 75 | 0.14 | 0.45 |
对比例2 | 75 | 0.15 | 0.42 |
对比例3 | 75 | 0.15 | 0.42 |
对比例4 | 75 | 0.14 | 0.41 |
Claims (9)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201610430486.1A CN106084182B (zh) | 2016-06-17 | 2016-06-17 | 一种储存稳定的缩二脲多异氰酸酯的制备方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201610430486.1A CN106084182B (zh) | 2016-06-17 | 2016-06-17 | 一种储存稳定的缩二脲多异氰酸酯的制备方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN106084182A true CN106084182A (zh) | 2016-11-09 |
CN106084182B CN106084182B (zh) | 2018-10-19 |
Family
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Family Applications (1)
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CN201610430486.1A Active CN106084182B (zh) | 2016-06-17 | 2016-06-17 | 一种储存稳定的缩二脲多异氰酸酯的制备方法 |
Country Status (1)
Country | Link |
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CN (1) | CN106084182B (zh) |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1460685A (en) * | 1974-08-01 | 1977-01-06 | Bayer Ag | Biuret polyisocyanate mixture stabilised against monomer reversion |
CN1128256A (zh) * | 1994-12-09 | 1996-08-07 | Basf公司 | 含缩二脲的聚异氰酸酯的制备方法 |
CN103724234A (zh) * | 2014-01-03 | 2014-04-16 | 万华化学集团股份有限公司 | 一种制备含有缩二脲的聚异氰酸酯的方法 |
KR101493269B1 (ko) * | 2014-09-17 | 2015-02-16 | 애경화학 주식회사 | 저장성이 향상된 뷰렛 그룹 함유 알리파틱 폴리이소시아네이트의 제조방법 |
-
2016
- 2016-06-17 CN CN201610430486.1A patent/CN106084182B/zh active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1460685A (en) * | 1974-08-01 | 1977-01-06 | Bayer Ag | Biuret polyisocyanate mixture stabilised against monomer reversion |
CN1128256A (zh) * | 1994-12-09 | 1996-08-07 | Basf公司 | 含缩二脲的聚异氰酸酯的制备方法 |
CN103724234A (zh) * | 2014-01-03 | 2014-04-16 | 万华化学集团股份有限公司 | 一种制备含有缩二脲的聚异氰酸酯的方法 |
KR101493269B1 (ko) * | 2014-09-17 | 2015-02-16 | 애경화학 주식회사 | 저장성이 향상된 뷰렛 그룹 함유 알리파틱 폴리이소시아네이트의 제조방법 |
Non-Patent Citations (7)
Title |
---|
BOHM V.P.W.等: "Nickel-catalyzed cross-coupling of aryl chlorides with aryl Grignard reagents", 《ANGEWANDTE CHEMIE-INTERNATIONAL EDITION》 * |
DS MCGUINNESS等: "Synthesis and Reaction Chemistry of Mixed Ligand Methylpalladium—Carbene Complexes", 《CHEMINFORM》 * |
LIU Q.X.等: "Synthesis, crystal structure and photophysical properties of N-heterocyclic carbene Pd(II), Pt(II) complexes and iodine adduct", 《POLYHEDRON》 * |
MAGILL A.M.等: "Palladium(II) complexes containing mono-, bi- and tridentate carbene ligands. Synthesis, characterisation and application as catalysts in C-C coupling reactions", 《JOURNAL OF ORGANOMETALLIC CHEMISTRY》 * |
杨亮茹 等: "螯合型氮杂环卡宾金属化合物的研究进展", 《有机化学》 * |
柳清湘 等: "N-杂环卡宾及其金属络合物的性质和合成方法", 《化学研究与应用》 * |
祝钧 等: "β-内酰胺卡宾在有机合成中的应用", 《化学试剂》 * |
Also Published As
Publication number | Publication date |
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CN106084182B (zh) | 2018-10-19 |
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TA01 | Transfer of patent application right |
Effective date of registration: 20161116 Address after: 264002 Yantai economic and Technological Development Zone, Shandong, Tian Shan Road, No. 17 Applicant after: Wanhua Chemical Group Co.,Ltd. Address before: 264002 Yantai economic and Technological Development Zone, Shandong, Tian Shan Road, No. 17 Applicant before: Wanhua Chemical Group Co.,Ltd. Applicant before: Wanhua chemical (Ningbo) Co.,Ltd. |
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Application publication date: 20161109 Assignee: Wanhua chemical (Ningbo) Co.,Ltd. Assignor: Wanhua Chemical Group Co.,Ltd. Contract record no.: 2017990000326 Denomination of invention: Preparation method of biuret polyisocyanate with storage stability License type: Common License Record date: 20170818 |
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Denomination of invention: A preparation method of storage stable biuret polyisocyanate Effective date of registration: 20211123 Granted publication date: 20181019 Pledgee: Bank of China Limited by Share Ltd. Yantai branch Pledgor: Wanhua Chemical Group Co.,Ltd. Registration number: Y2021980013026 |
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Date of cancellation: 20220622 Granted publication date: 20181019 Pledgee: Bank of China Limited by Share Ltd. Yantai branch Pledgor: Wanhua Chemical Group Co.,Ltd. Registration number: Y2021980013026 |