CN104058976A - Preparation method of fluorine-containing cationic surfactant - Google Patents
Preparation method of fluorine-containing cationic surfactant Download PDFInfo
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- CN104058976A CN104058976A CN201410105456.4A CN201410105456A CN104058976A CN 104058976 A CN104058976 A CN 104058976A CN 201410105456 A CN201410105456 A CN 201410105456A CN 104058976 A CN104058976 A CN 104058976A
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- 229910052731 fluorine Inorganic materials 0.000 title claims abstract description 28
- 239000011737 fluorine Substances 0.000 title claims abstract description 28
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title claims abstract description 27
- 238000002360 preparation method Methods 0.000 title claims abstract description 18
- 239000003093 cationic surfactant Substances 0.000 title abstract 4
- 238000006243 chemical reaction Methods 0.000 claims abstract description 37
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000013638 trimer Substances 0.000 claims abstract description 13
- 239000003054 catalyst Substances 0.000 claims abstract description 12
- 150000001350 alkyl halides Chemical class 0.000 claims abstract description 10
- 239000000706 filtrate Substances 0.000 claims abstract description 9
- 239000002904 solvent Substances 0.000 claims abstract description 8
- 238000010534 nucleophilic substitution reaction Methods 0.000 claims abstract description 7
- 239000002994 raw material Substances 0.000 claims abstract description 6
- 239000012043 crude product Substances 0.000 claims abstract description 4
- 238000001914 filtration Methods 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims abstract description 4
- 239000003960 organic solvent Substances 0.000 claims abstract description 4
- 125000002091 cationic group Chemical group 0.000 claims description 25
- 239000013543 active substance Substances 0.000 claims description 24
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 15
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
- IPMWIVQWGGRTLD-UHFFFAOYSA-N n'-[2-(propylamino)ethyl]ethane-1,2-diamine Chemical class CCCNCCNCCN IPMWIVQWGGRTLD-UHFFFAOYSA-N 0.000 claims description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 claims description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- 230000006837 decompression Effects 0.000 claims description 8
- 238000004821 distillation Methods 0.000 claims description 8
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 8
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 claims description 6
- 230000035484 reaction time Effects 0.000 claims description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical group IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 5
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 5
- 235000015320 potassium carbonate Nutrition 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 4
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims description 4
- 150000003053 piperidines Chemical class 0.000 claims description 4
- 235000017550 sodium carbonate Nutrition 0.000 claims description 4
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 claims description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 2
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 abstract description 5
- 239000000654 additive Substances 0.000 abstract description 2
- 230000000996 additive effect Effects 0.000 abstract description 2
- 239000003995 emulsifying agent Substances 0.000 abstract description 2
- 238000001704 evaporation Methods 0.000 abstract description 2
- 230000008020 evaporation Effects 0.000 abstract description 2
- 239000008396 flotation agent Substances 0.000 abstract description 2
- 239000006260 foam Substances 0.000 abstract description 2
- 229910052751 metal Inorganic materials 0.000 abstract description 2
- 239000002184 metal Substances 0.000 abstract description 2
- OOFAEFCMEHZNGP-UHFFFAOYSA-N 1-n',1-n'-dimethylpropane-1,1-diamine Chemical compound CCC(N)N(C)C OOFAEFCMEHZNGP-UHFFFAOYSA-N 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 239000010779 crude oil Substances 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- 238000005580 one pot reaction Methods 0.000 abstract 1
- 239000012756 surface treatment agent Substances 0.000 abstract 1
- 238000003756 stirring Methods 0.000 description 16
- 239000000243 solution Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 6
- 238000000967 suction filtration Methods 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- 238000010792 warming Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N 1-nonene Chemical class CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 1
- -1 amine salt Chemical class 0.000 description 1
- 229960004050 aminobenzoic acid Drugs 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 150000002221 fluorine Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention provides a preparation method of a fluorine-containing cationic surfactant. The method includes following steps: employing hexafluoropropylene trimer and N,N-dimethylpropanediamine as raw materials; carrying out a nucleophilic substitution reaction with existence of an organic solvent and an alkali catalyst; adding haloalkane to carry out a quaternarization reaction; filtering a crude product; removing solvent out from a filtrate in a pressure-reducing distilling manner; and preparing the fluorine-containing cationic surfactant in a one-pot manner. The fluorine-containing cationic surfactant can be used as an emulsifier, a metal surface treatment agent, a leveling agent, an additive in a fire extinguishing agent, a foam flotation agent a crude oil evaporation-inhibiting agent or the like.
Description
Technical field
The present invention relates to cats product field, be specifically related to a kind of preparation method of fluorine-containing cationic tensio-active agent.
Background technology
Fluorochemical surfactant has the characteristic of " three height ", " two hate ", has the outstanding features such as high surface, high thermal stability and high chemical stability, and along with the popularization of its application, demand domestic, world market increases day by day.Fluorochemical surfactant is divided into anion surfactant, cats product, amphoterics and the large class of nonionogenic tenside four.Fluorine-containing cationic tensio-active agent has good foaminess, be not subject to that pH value affects, the characteristic such as facile hydrolysis not, therefore becomes a main direction of studying.Fluorine-containing cationic tensio-active agent is mainly divided into amine salt type and the large class of quaternary two, and the widest with quaternary purposes.
Can be used for the synthetic fluorochemical surfactant with side chain taking oligomerization of hexafluoropropylene body as raw material.In patent CN101293860A, raw material is difficult to obtain to perfluorinated nonene oxygen base benzene sulfonyl chloride, and expensive.The productive rate of synthetic fluorine-containing cationic tensio-active agent is generally between 77.8-82.1%, and the activity of gained cationic surface agent is not high, and the surface tension under micelle-forming concentration is 21.7mN/m.In patent CN101293853A, desired raw material, to perfluorinated nonene aminobenzoic acid same price costliness, be difficult to obtain, and sulfur oxychloride toxicity is large, and environmental pollution is serious, and the complex process of this fluorine-containing cationic tensio-active agent is not easy to amplify and produces simultaneously.In patent CN101033205A, the surfactivity of the anionic fluorochemical surfactant of synthesized is poor, and under 0.1% concentration, surface tension is only 21mN/m.In patent JP2007060096, the surfactivity of the anionic fluorochemical surfactant of synthesized is higher, but the yield of product is lower, is only 65.2%.
Summary of the invention
The object of the invention is to overcome deficiency of the prior art, the preparation method that a kind of productive rate is high, be easy to the fluorine-containing cationic tensio-active agent that suitability for industrialized production, cheapness and surfactivity are high is provided.For achieving the above object, the present invention proposes " one kettle way " fluorine-containing cationic tensio-active agent processed.
Technical scheme of the present invention provides a kind of preparation method of fluorine-containing cationic tensio-active agent: with hexafluoropropylene trimer and N, N-dimethylated propyl diethylenetriamine is raw material, and under organic solvent and alkaline catalysts existence, 0-50oC carries out nucleophilic substitution reaction; After reaction finishes, add wherein haloalkane, 0-100oC carries out quaternary ammonium reaction, filtration of crude product, and filtrate decompression distillation removes desolventizing and obtains fluorine-containing cationic tensio-active agent.
Above-mentioned preparation method comprises following steps:
1) hexafluoropropylene trimer and alkaline catalysts are added in organic solvent and are stirred, after add N, N-dimethylated propyl diethylenetriamine, 0-50oC stirring reaction carries out nucleophilic substitution reaction for 0.5-10 hour;
2) in step 1) gained mixed solution, add haloalkane, quaternary ammonium reaction is carried out in 0-100oC reaction for 0.5-6 hour, filtration of crude product, and filtrate decompression distillation removes desolventizing and obtains fluorine-containing cationic tensio-active agent.
Some preferred embodiment in, above-mentioned steps 1) nucleophilic substitution reaction, temperature of reaction is 20-50oC, the reaction times is 4-8 hour; Step 2) described quaternary ammonium reaction temperature is 50-100oC, the reaction times is 2-4 hour.
In some embodiments, alkaline catalysts is selected from sodium carbonate, salt of wormwood, sodium bicarbonate, triethylamine, Trimethylamine 99, pyridine, piperidines or N-methyl piperidine.
In some embodiments, solvent is selected from ethyl acetate, acetone, tetrahydrofuran (THF), ether, methylene dichloride, DMF or pimelinketone.
In some embodiments, haloalkane is selected from methyl iodide, iodoethane, monobromethane, monobromethane or monochloroethane.
In some embodiments, hexafluoropropylene trimer, N, the mol ratio of N-dimethylated propyl diethylenetriamine, alkaline catalysts, haloalkane is 1:1-3:1-2:1-4.
Other preferred embodiment in, hexafluoropropylene trimer, N, the mol ratio of N-dimethylated propyl diethylenetriamine, alkaline catalysts, haloalkane is 1:1.2-1.5:1.2-1.5:1.5-2.5.
The present invention also provides the prepared fluorine-containing cationic tensio-active agent according to above-mentioned preparation method.
Fluorine-containing cationic tensio-active agent prepared by the preparation method of fluorine-containing cationic tensio-active agent of the present invention, can be applied in emulsifying agent, metal conditioner, flow agent, fire-fighting medium additive, foam flotation agents or oil evaporation inhibitor.
The term "or" that the present invention uses represents alternatives, if suitable, they can be combined, and that is to say, term "or" comprises each listed independent alternatives and their combination.For example, " alkaline catalysts is selected from sodium carbonate, salt of wormwood, sodium bicarbonate, triethylamine, Trimethylamine 99, pyridine, piperidines or N-methyl piperidine " represents that alkaline catalysts can be the one among sodium carbonate, salt of wormwood, sodium bicarbonate, triethylamine, Trimethylamine 99, pyridine, piperidines, N-methyl piperidine, can be also its more than one combination.
Unless clearly state in contrast, otherwise all scopes that the present invention quotes comprised end value.For example, " 0-100oC carries out quaternary ammonium reaction " represents that the scope of the temperature T of quaternary ammonium reaction is 0oC≤T≤100oC.
Preparation method of the present invention adopts " one kettle way ", and method is simple, and reaction yield is high, makes fluorine-containing cationic tensio-active agent surfactivity high.
Embodiment
The following stated be the preferred embodiment of the present invention, what the present invention protected is not limited to following preferred implementation.It should be pointed out that on the basis of conceiving in these innovation and creation for a person skilled in the art, some distortion and the improvement made, all belong to protection scope of the present invention.
Embodiment 1
In the there-necked flask of 100mL, add sodium carbonate 5.3g, acetonitrile 30mL and hexafluoropropylene trimer 22.5g, after stirring, add N, N-dimethylated propyl diethylenetriamine 5.1g, stirring reaction 8 hours under 20oC; Then in above-mentioned reaction solution, add monobromethane 5.5g, be warming up to 100oC stirring reaction 4 hours.By reaction solution suction filtration, filtrate decompression distillation is removed solvent and is obtained fluorine-containing cationic tensio-active agent, yield 96.2%.
It is 0.1% the aqueous solution that products obtained therefrom is configured to massfraction, and surface tension is 18.8mN/m when 25oC after testing.
Embodiment 2
In the there-necked flask of 100mL, add sodium carbonate 8.0g, acetone 30mL and hexafluoropropylene trimer 22.5g, after stirring, add N, N-dimethylated propyl diethylenetriamine 10.2g, stirring reaction 5 hours under 10oC; Then in above-mentioned reaction solution, add methyl iodide 8.5g, be warming up to 50oC stirring reaction 2 hours.By reaction solution suction filtration, filtrate decompression distillation is removed solvent and is obtained fluorine-containing cationic tensio-active agent, yield 95.5%.
It is 0.1% the aqueous solution that products obtained therefrom is configured to massfraction, and surface tension is 18.9mN/m when 25oC after testing.
Embodiment 3
In the there-necked flask of 100mL, add triethylamine 7.6g, ethyl acetate 30mL and hexafluoropropylene trimer 22.5g, after stirring, add N, N-dimethylated propyl diethylenetriamine 15.3g, stirring reaction 5 hours under 40oC; Then in above-mentioned reaction solution, add monobromethane 9.0g, be cooled to 30oC stirring reaction 1 hour.By reaction solution suction filtration, filtrate decompression distillation is removed solvent and is obtained fluorine-containing cationic tensio-active agent, yield 97.3%.
It is 0.1% the aqueous solution that products obtained therefrom is configured to massfraction, and surface tension is 18.8mN/m when 25oC after testing.
Embodiment 4
In the there-necked flask of 100mL, add pyridine 8.7g, tetrahydrofuran (THF) 30mL and hexafluoropropylene trimer 22.5g, after stirring, add N, N-dimethylated propyl diethylenetriamine 6.3g, stirring reaction 4 hours under 0oC; Then in above-mentioned reaction solution, add methyl iodide 14.2g, be warming up to 60oC stirring reaction 6 hours.By reaction solution suction filtration, filtrate decompression distillation is removed solvent and is obtained fluorine-containing cationic tensio-active agent, yield 95.8%.
It is 0.1% the aqueous solution that products obtained therefrom is configured to massfraction, and surface tension is 18.8mN/m when 25oC after testing.
Embodiment 5
In the there-necked flask of 100mL, add salt of wormwood 15.3g, ether 30mL and hexafluoropropylene trimer 22.5g, after stirring, add N, N-dimethylated propyl diethylenetriamine 7.8g, stirring reaction 0.5 hour under 50oC; Then in above-mentioned reaction solution, add methyl iodide 21.3g, be warming up to 60oC stirring reaction 0.5 hour.By reaction solution suction filtration, filtrate decompression distillation is removed solvent and is obtained fluorine-containing cationic tensio-active agent, yield 96.7%.
It is 0.1% the aqueous solution that products obtained therefrom is configured to massfraction, and surface tension is 19.0mN/m when 25oC after testing.
From embodiment of the present invention 1-5, technical scheme operational path of the present invention is simple, reaction conditions gentleness, and yield is up to 95-97%; The surfactivity of the fluorine-containing cationic tensio-active agent of synthesized is high simultaneously, and when 25oC, massfraction is that the surface tension of 0.1% aqueous solution is 18.8-19.0mN/m.
Claims (9)
1. a preparation method for fluorine-containing cationic tensio-active agent, is characterized in that: with hexafluoropropylene trimer and N, N-dimethylated propyl diethylenetriamine is raw material, and under organic solvent and alkaline catalysts existence, 0-50oC carries out nucleophilic substitution reaction; After reaction finishes, add wherein haloalkane, 0-100oC carries out quaternary ammonium reaction, filtration of crude product, and filtrate decompression distillation removes desolventizing and obtains fluorine-containing cationic tensio-active agent.
2. preparation method according to claim 1, is characterized in that the nucleophilic substitution reaction time is 0.5-10 hour; Carrying out the quaternary ammonium reaction time is 0.5-6 hour.
3. preparation method according to claim 1, is characterized in that, described alkaline catalysts is selected from sodium carbonate, salt of wormwood, sodium bicarbonate, triethylamine, Trimethylamine 99, pyridine, piperidines or N-methyl piperidine or its combination.
4. preparation method according to claim 1, is characterized in that, described solvent is selected from ethyl acetate, acetone, tetrahydrofuran (THF), ether, methylene dichloride, DMF or pimelinketone or its combination.
5. preparation method according to claim 1, is characterized in that, described haloalkane is selected from methyl iodide, iodoethane, monobromethane, monobromethane or monochloroethane.
6. preparation method according to claim 1, is characterized in that, the temperature of reaction of described nucleophilic substitution reaction is 20-50oC, and the reaction times is 4-8 hour; The temperature of reaction of quaternary ammonium reaction is 50-100oC, and the reaction times is 2-4 hour.
7. preparation method according to claim 1 and 2, is characterized in that, described hexafluoropropylene trimer, N, and the mol ratio of N-dimethylated propyl diethylenetriamine, alkaline catalysts, haloalkane is 1:1-3:1-2:1-4.
8. preparation method according to claim 8, is characterized in that, described hexafluoropropylene trimer, N, and the mol ratio of N-dimethylated propyl diethylenetriamine, alkaline catalysts, haloalkane is 1:1.2-1.5:1.2-1.5:1.5-2.5.
9. the fluorine-containing cationic tensio-active agent of preparing according to the method described in arbitrary of claim 1-8.
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| CN110818650A (en) * | 2018-08-09 | 2020-02-21 | 乳源东阳光氟有限公司 | Perfluoropolyether biquaternary ammonium salt and preparation method and application thereof |
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|---|---|---|---|---|
| CN110818650A (en) * | 2018-08-09 | 2020-02-21 | 乳源东阳光氟有限公司 | Perfluoropolyether biquaternary ammonium salt and preparation method and application thereof |
| CN110818650B (en) * | 2018-08-09 | 2022-09-27 | 乳源东阳光氟有限公司 | Perfluoropolyether biquaternary ammonium salt and preparation method and application thereof |
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