CN1644584A - Production of tri(4-isocyanate benzyl) thiophosphate - Google Patents
Production of tri(4-isocyanate benzyl) thiophosphate Download PDFInfo
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- CN1644584A CN1644584A CN 200410067672 CN200410067672A CN1644584A CN 1644584 A CN1644584 A CN 1644584A CN 200410067672 CN200410067672 CN 200410067672 CN 200410067672 A CN200410067672 A CN 200410067672A CN 1644584 A CN1644584 A CN 1644584A
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- inert
- thiophosphate
- trichloromethyl
- carbonate
- inert organic
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 18
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 title claims description 6
- 239000012948 isocyanate Substances 0.000 title claims description 4
- 238000000034 method Methods 0.000 claims abstract description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 13
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 11
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 claims description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 9
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 claims description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 5
- 229940117955 isoamyl acetate Drugs 0.000 claims description 5
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 4
- PPXUHEORWJQRHJ-UHFFFAOYSA-N ethyl isovalerate Chemical compound CCOC(=O)CC(C)C PPXUHEORWJQRHJ-UHFFFAOYSA-N 0.000 claims description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 claims description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 229940072049 amyl acetate Drugs 0.000 claims description 2
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 claims description 2
- 229940043232 butyl acetate Drugs 0.000 claims description 2
- 238000000354 decomposition reaction Methods 0.000 claims description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- 229940093499 ethyl acetate Drugs 0.000 claims description 2
- 150000008282 halocarbons Chemical class 0.000 claims description 2
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 claims description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims description 2
- 239000003208 petroleum Substances 0.000 claims description 2
- 229940090181 propyl acetate Drugs 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 238000003912 environmental pollution Methods 0.000 abstract description 3
- KGLSETWPYVUTQX-UHFFFAOYSA-N tris(4-isocyanatophenoxy)-sulfanylidene-$l^{5}-phosphane Chemical compound C1=CC(N=C=O)=CC=C1OP(=S)(OC=1C=CC(=CC=1)N=C=O)OC1=CC=C(N=C=O)C=C1 KGLSETWPYVUTQX-UHFFFAOYSA-N 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- WDQNIWFZKXZFAY-UHFFFAOYSA-M fentin acetate Chemical compound CC([O-])=O.C1=CC=CC=C1[Sn+](C=1C=CC=CC=1)C1=CC=CC=C1 WDQNIWFZKXZFAY-UHFFFAOYSA-M 0.000 description 9
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 6
- 239000000853 adhesive Substances 0.000 description 6
- 230000001070 adhesive effect Effects 0.000 description 6
- 239000007787 solid Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229920001228 polyisocyanate Polymers 0.000 description 4
- 239000005056 polyisocyanate Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 210000003298 dental enamel Anatomy 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 238000002834 transmittance Methods 0.000 description 2
- MBUAAMOJATXYKR-UHFFFAOYSA-N 4-bis(4-aminophenoxy)phosphinothioyloxyaniline Chemical compound C1=CC(N)=CC=C1OP(=S)(OC=1C=CC(N)=CC=1)OC1=CC=C(N)C=C1 MBUAAMOJATXYKR-UHFFFAOYSA-N 0.000 description 1
- SNLFYGIUTYKKOE-UHFFFAOYSA-N 4-n,4-n-bis(4-aminophenyl)benzene-1,4-diamine Chemical compound C1=CC(N)=CC=C1N(C=1C=CC(N)=CC=1)C1=CC=C(N)C=C1 SNLFYGIUTYKKOE-UHFFFAOYSA-N 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000001354 calcium citrate Substances 0.000 description 1
- MVPPADPHJFYWMZ-IDEBNGHGSA-N chlorobenzene Chemical group Cl[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 MVPPADPHJFYWMZ-IDEBNGHGSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
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Abstract
Production of trithiophosphate (4-isocyanic ester group phenyl ) achieves simple and safety process, high production efficiency and no environmental pollution.
Description
Technical Field
The invention belongs to a method for producing tris (4-isocyanatophenyl) thiophosphate, and particularly relates to a method for industrially producing tris (4-isocyanatophenyl) thiophosphate by reacting triaminotriphenyl thiophosphate with bis (trichloromethyl) carbonate.
Background
Polyisocyanate adhesives are widely used because they have high adhesive strength and are particularly suitable for adhesion of metals to rubbers, fibers, and the like. Such as Desmodur RF and Desmodur RFE adhesives from Bayer, Germany, Hartdur E333 and Hartdur F256 from Chongzhou Chongshu chemical company, Hartdur F215. Tris (4-Isocyanatophenyl) Thiophosphate (Tris- (4-Isocyanatophenyl) -Thiophosphate, TPTI for short) is the main component of this polyisocyanate adhesive, and is described in patents GB930918, GB1094321, US 5576558.
Currently, the industrial production of TPTI has been by phosgene process, which requires the use of excess highly toxic phosgene, which has significant disadvantages:
(1) phosgene has great danger in the processes of preparation, storage and use, and generally does not allow storage and transportation, so the phosgene must be used while being prepared; as an organic highly toxic article (public safety industry Standard GA58-1993, number: A2155) of the people's republic of China, its production and use are under strict restrictions.
(2) The phosgenation reaction has high temperature, high pressure, long technological process, complicated technology, strict requirement on equipment and management, and easy environmental pollution and safety accident.
Disclosure of Invention
The invention aims to solve the problems of complex process, harsh reaction conditions, serious pollution and the like in the prior art, and provides a production method of tris (4-isocyanatophenyl) thiophosphate (TPTI) which has simple and safe process, mild reaction conditions, high yield and no environmental pollution.
The TPTI is prepared through one-step reaction of triaminotriphenyl thiophosphate (Tris- (4-Aminophenyl) -thiophosphate, hereinafter abbreviated as TPTA) and bis (trichloromethyl) carbonate (bis (trichloromethyl) carbonate, hereinafter abbreviated as BTC) in inert organic solvent.
The synthesis reaction equation of the TPTI is as follows:
the production process comprises the following steps:
(1) preparing an inert organic solution of TPTA, wherein the concentration is 1-50% (mass percentage concentration), and the more appropriate concentration is 5-20%;
(2) preparing an inert organic solution of BTC, wherein the concentration is 1-50% (mass percentage concentration), and the more proper concentration is 5-30%;
(3) putting the BTC inert organic solution into a reaction kettle at normal temperature, introducing nitrogen for protection, and slowly putting the TPTA inert organic solution under cooling; stirring and reacting for 2-3 hours after the feeding is finished until the reaction is finished;
(4) and after the reaction is finished, removing the solvent to obtain the solid product TPTI.
In the above production method, the ratio of the amounts of TPTA and BTC is 0.1-1: 1, preferably 0.2-0.8: 1.
In the above production method, the inert organic solution should be a substance that does not cause decomposition of BTC, and includes inert hydrocarbons, inert halogenated hydrocarbons, inert esters, inert ethers, and the like, such as: petroleum ether, cyclohexane, n-hexane, xylene, toluene, dichloromethane, 1, 2-dichloroethane, carbon tetrachloride, chlorobenzene, o-dichlorobenzene, ethyl acetate, propyl acetate, amyl acetate, isoamyl acetate, butyl acetate, ethyl isovalerate, tetrahydrofuran, cyclohexanone or a mixture thereof.
In the above production method, a suitable catalyst may be added simultaneously with TPTA to promote the rapid progress of the reaction. The catalyst is mainly organic alkali catalyst, such as diethylamine, trimethylamine, triethylamine, N-dimethylaniline, pyridine, dimethylformamide and the like. The addition amount of the catalyst is 0-5% of the mass of the TPTA.
Compared with the existing phosgenation production technology, the production method of the invention has the following advantages:
(1) the production method adopts 'green chemical' BTC which is a stable and nontoxic solid crystal at normal temperature, is convenient to store and transport, is safe to use, has no pollution, is nontoxic and is environment-friendly.
(2) When BTC raw material is used for production, the feeding and metering are accurate, the reverse dropwise addition reaction and theequivalent reaction which cannot be realized by gas phosgene can be realized, the reaction time is short, the reaction condition is mild, and the yield is high.
(3) The method has the advantages of simple production process, use of conventional equipment, omission of phosgene generation equipment and storage and transportation equipment, simple and safe operation, low operation cost and suitability for industrial production.
The TPTI produced by the invention can be prepared into the polyisocyanate adhesive by adding solvents such as ethyl acetate, acetone, methyl ethyl ketone or dichloromethane and the like.
The drawings of the invention are illustrated as follows:
the instrument name: nexus 870 Fourier transform Infrared Spectroscopy (Nexus 870 FT-IR), Nicolet instruments USA. KBr pellets, sample size about 0.7 mg.
FIG. 1 is an infrared spectrum of a TPTI sample which is produced by Bayer, Germany and which has been subjected to a refining treatment; the abscissa of the graph is the wave number σ (cm)-1) And the ordinate is the transmittance T.
FIG. 2 is an infrared spectrum of a TPTI product obtained by the method of the present invention, in which the abscissa is the wave number σ (cm)-1) And the ordinate is the transmittance T.
Specific examples of the present invention are as follows, but the present invention is not limited to only the following examples.
Example 1:
200kg of 1, 2-dichloroethane and 25kg of TPTA are put into a 500L enamel reaction kettle and heated to be dissolved for later use.
200kg of 1, 2-dichloroethane and 50kg of BTC were put into a 1000L enamel reactor, stirred and dissolved, 9kg of a 1, 2-dichloroethane solution of triethylamine (containing 0.8kg of triethylamine) was added thereto, and nitrogen gas was introduced thereinto. Then, a solution of TPTA in 1, 2-dichloroethane was slowly added from the 500L reactor, and the reaction was refluxed for 2 hours at an elevated temperature. Introducing nitrogen to evaporate the 1, 2-dichloroethane to obtain 29.1kg of light yellow solid, wherein the melting point is 82.5-84.5 ℃, and the content of the 1, 2-dichloroethane is 3%. After refinement, 27.6kg of white solid was obtained with a yield of 92.0%. The melting point is 83.5-86.0 ℃, and the isocyanate content is 27.0%. The solid can be directly added with proper solvent to prepare the polyisocyanate adhesive with corresponding concentration.
In the examples, the mass ratio of TPTI to BTC was 0.38: 1.
Example 2:
in a 1000L reactor, 200kg of isoamyl acetate and 60kg of BTC were charged and dissolved by stirring. 10kg of an isoamyl acetate solution of triethylamine (containing 0.9kg of triethylamine) was added thereto, and nitrogen gas was introduced thereinto. 235kg of isoamyl acetate solution of TAPA prepared as in example 1 was then added slowly. The subsequent operation was the same as in example 1. The yield thereof was found to be 96.4%.
In the examples, the mass ratio of TPTI to BTC was 0.32: 1.
Example 3:
the procedure is as in example 1, except that the inert organic solvent is chlorobenzene. The yield thereof was found to be 98.0%.
Example 4:
200kg of 1, 2-dichloroethane and 75kg of BTC were put into a 1000L enamel reactor, and dissolved by introducing nitrogen gasand stirring. Then, a solution of TPTA in 1, 2-dichloroethane was slowly added from the 500L reactor (same as in example 1), and the reaction was refluxed at an increased temperature for 2 hours. Nitrogen is introduced to evaporate the 1, 2-dichloroethane, and 27.9kg of white solid is obtained after the product is refined, and the yield is 93.0 percent.
In the examples, the ratio of the amounts of TPTI to BTC was 0.25: 1.
Example 5:
the procedure is as in example 3, except that 1.0kg of dimethylformamide is used as catalyst. The yield thereof was found to be 89.1%.
Claims (6)
1. The invention belongs to a method for producing tri (4-isocyanate phenyl) thiophosphate. The production process comprises the following steps: tri-amino triphenyl thiophosphate reacts with bis (trichloromethyl) carbonate in an inert organic solvent to synthesize the tri (4-isocyanate phenyl) thiophosphate in one step.
2. The method of claim 1, wherein the concentration of the inert organic solution of triaminotriphenylphosphorothioate is 1-50% (mass percentage concentration), preferably 5-20%.
3. The method according to claim 1, wherein the concentration of the prepared di (trichloromethyl) carbonate inert organic solution is 1-50% (mass percentage concentration), preferably 5-30%.
4. The process of claim 1, wherein the mass ratio of triaminotriphenylphosphorothioate to bis (trichloromethyl) carbonate is 0.1-1: 1, preferably 0.2-0.8: 1.
5. The method of claim 1, wherein the inert organic solution is a substance that does not initiate the decomposition of the bis (trichloromethyl) carbonate, and the inert organic solution comprises inert hydrocarbons, inert halogenated hydrocarbons, inert esters, inert ethers, and the like, such as: petroleum ether, cyclohexane, n-hexane, xylene, toluene, dichloromethane, 1, 2-dichloroethane, carbon tetrachloride, chlorobenzene, o-dichlorobenzene, ethyl acetate, propyl acetate, amyl acetate, isoamyl acetate, butyl acetate, ethyl isovalerate, tetrahydrofuran, cyclohexanone or a mixture thereof.
6. A process as claimed in claim 1, wherein a suitable catalyst is added simultaneously with the triaminotriphenylphosphorothionate to promote rapid reaction. The catalyst is mainly organic alkali catalyst, such as diethylamine, trimethylamine, triethylamine, N-dimethylaniline, pyridine, dimethylformamide and the like. The addition amount of the catalyst is 0-5% of the mass of the triaminotriphenyl thiophosphate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200410067672 CN1644584B (en) | 2004-11-01 | 2004-11-01 | Production of tri(4-isocyanate benzyl) thiophosphate |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200410067672 CN1644584B (en) | 2004-11-01 | 2004-11-01 | Production of tri(4-isocyanate benzyl) thiophosphate |
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| Publication Number | Publication Date |
|---|---|
| CN1644584A true CN1644584A (en) | 2005-07-27 |
| CN1644584B CN1644584B (en) | 2010-05-26 |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114106047A (en) * | 2021-11-24 | 2022-03-01 | 中节能万润股份有限公司 | Novel phosphine-containing isocyanate electrolyte additive and application thereof |
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2004
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114106047A (en) * | 2021-11-24 | 2022-03-01 | 中节能万润股份有限公司 | Novel phosphine-containing isocyanate electrolyte additive and application thereof |
| CN114106047B (en) * | 2021-11-24 | 2024-01-26 | 中节能万润股份有限公司 | Phosphine-containing isocyanate electrolyte additive and application thereof |
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| Publication number | Publication date |
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| CN1644584B (en) | 2010-05-26 |
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Effective date of registration: 20160726 Address after: 262737 Weifang Binhai Economic Development Zone, the Yellow River, West Street, No. 06933, No. Patentee after: Shandong Chongshun Chemical Co., Ltd. Address before: 314423 Spring Road, Haining Agricultural Comprehensive Development Zone, Jiaxing, Zhejiang Patentee before: Haining Chongshun Chemical Co., Ltd. |
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Address after: 262737 Weifang Binhai Economic Development Zone, the Yellow River, West Street, No. 06933, No. Patentee after: Shandong Chong Shunxin Mstar Technology Ltd Address before: 262737 Weifang Binhai Economic Development Zone, the Yellow River, West Street, No. 06933, No. Patentee before: Shandong Chongshun Chemical Co., Ltd. |
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