CN105879773A - Organosilicone dimeric surfactant and synthetic method thereof - Google Patents
Organosilicone dimeric surfactant and synthetic method thereof Download PDFInfo
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- CN105879773A CN105879773A CN201610133278.5A CN201610133278A CN105879773A CN 105879773 A CN105879773 A CN 105879773A CN 201610133278 A CN201610133278 A CN 201610133278A CN 105879773 A CN105879773 A CN 105879773A
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- diglycidyl ether
- organic silicon
- aminoethylaminopropyl
- ion surfactant
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- 239000004094 surface-active agent Substances 0.000 title claims abstract description 58
- 238000010189 synthetic method Methods 0.000 title abstract description 7
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 54
- 239000010703 silicon Substances 0.000 claims abstract description 54
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 37
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims abstract description 32
- LRWZZZWJMFNZIK-UHFFFAOYSA-N 2-chloro-3-methyloxirane Chemical compound CC1OC1Cl LRWZZZWJMFNZIK-UHFFFAOYSA-N 0.000 claims abstract description 27
- 239000000463 material Substances 0.000 claims abstract description 25
- 238000006243 chemical reaction Methods 0.000 claims abstract description 22
- HSDVRWZKEDRBAG-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)hexoxymethyl]oxirane Chemical compound C1OC1COC(CCCCC)OCC1CO1 HSDVRWZKEDRBAG-UHFFFAOYSA-N 0.000 claims abstract description 18
- 150000001298 alcohols Chemical class 0.000 claims abstract description 18
- WGYKZJWCGVVSQN-UHFFFAOYSA-N mono-n-propyl amine Natural products CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims abstract description 16
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000002360 preparation method Methods 0.000 claims abstract description 16
- HBWKNXZESUPMFW-UHFFFAOYSA-N NCCNCCC[SiH2]O[SiH2]O[SiH2]O[SiH3] Chemical compound NCCNCCC[SiH2]O[SiH2]O[SiH2]O[SiH3] HBWKNXZESUPMFW-UHFFFAOYSA-N 0.000 claims abstract description 15
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 claims abstract description 12
- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 claims abstract description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 44
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 38
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 36
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 29
- 230000006837 decompression Effects 0.000 claims description 15
- 229960004756 ethanol Drugs 0.000 claims description 13
- -1 tetramethyl hydroxide Chemical compound 0.000 claims description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- 229960000935 dehydrated alcohol Drugs 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 229940073561 hexamethyldisiloxane Drugs 0.000 claims description 11
- 238000004821 distillation Methods 0.000 claims description 10
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 9
- RSNQKPMXXVDJFG-UHFFFAOYSA-N tetrasiloxane Chemical compound [SiH3]O[SiH2]O[SiH2]O[SiH3] RSNQKPMXXVDJFG-UHFFFAOYSA-N 0.000 claims description 9
- 238000010792 warming Methods 0.000 claims description 9
- UWFRVQVNYNPBEF-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-one Chemical group CCC(=O)C1=CC=C(C)C=C1C UWFRVQVNYNPBEF-UHFFFAOYSA-N 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 239000002808 molecular sieve Substances 0.000 claims description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 8
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 8
- 238000005406 washing Methods 0.000 claims description 8
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 7
- 238000002390 rotary evaporation Methods 0.000 claims description 7
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims description 7
- SEFYJVFBMNOLBK-UHFFFAOYSA-N 2-[2-[2-(oxiran-2-ylmethoxy)ethoxy]ethoxymethyl]oxirane Chemical compound C1OC1COCCOCCOCC1CO1 SEFYJVFBMNOLBK-UHFFFAOYSA-N 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 239000003921 oil Substances 0.000 claims description 5
- 208000035126 Facies Diseases 0.000 claims description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 4
- 238000013019 agitation Methods 0.000 claims description 4
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 4
- 239000007791 liquid phase Substances 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 230000007935 neutral effect Effects 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 239000012044 organic layer Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 3
- 235000019270 ammonium chloride Nutrition 0.000 claims description 3
- 239000006227 byproduct Substances 0.000 claims description 3
- 238000001704 evaporation Methods 0.000 claims description 3
- 230000008020 evaporation Effects 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 claims 1
- 239000004593 Epoxy Substances 0.000 claims 1
- ODJZWVFLHZHURI-UHFFFAOYSA-M [Br-].C(CCC)[P+](CCCC)(CCCC)CCCC.[NH4+].[Br-] Chemical compound [Br-].C(CCC)[P+](CCCC)(CCCC)CCCC.[NH4+].[Br-] ODJZWVFLHZHURI-UHFFFAOYSA-M 0.000 claims 1
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- SXGBREZGMJVYRL-UHFFFAOYSA-N butan-1-amine;hydrobromide Chemical compound [Br-].CCCC[NH3+] SXGBREZGMJVYRL-UHFFFAOYSA-N 0.000 claims 1
- VIRPUNZTLGQDDV-UHFFFAOYSA-N chloro propanoate Chemical compound CCC(=O)OCl VIRPUNZTLGQDDV-UHFFFAOYSA-N 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 abstract description 5
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 5
- HSRJKNPTNIJEKV-UHFFFAOYSA-N Guaifenesin Chemical compound COC1=CC=CC=C1OCC(O)CO HSRJKNPTNIJEKV-UHFFFAOYSA-N 0.000 abstract description 3
- 239000012467 final product Substances 0.000 abstract 1
- 238000012360 testing method Methods 0.000 description 18
- 230000002776 aggregation Effects 0.000 description 5
- 238000004220 aggregation Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910002808 Si–O–Si Inorganic materials 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 125000005647 linker group Chemical group 0.000 description 3
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- UMILHIMHKXVDGH-UHFFFAOYSA-N Triethylene glycol diglycidyl ether Chemical compound C1OC1COCCOCCOCCOCC1CO1 UMILHIMHKXVDGH-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- CHFHBMNTTXFQSM-UHFFFAOYSA-N azane;n-ethyl-3-trimethoxysilylpropan-1-amine Chemical compound N.CCNCCC[Si](OC)(OC)OC CHFHBMNTTXFQSM-UHFFFAOYSA-N 0.000 description 2
- 229960005237 etoglucid Drugs 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- 238000012795 verification Methods 0.000 description 2
- LYCAIKOWRPUZTN-NMQOAUCRSA-N 1,2-dideuteriooxyethane Chemical compound [2H]OCCO[2H] LYCAIKOWRPUZTN-NMQOAUCRSA-N 0.000 description 1
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- QUGFDTDMXRLLBM-UHFFFAOYSA-N 3-[2-aminoethyl(silyloxysilyloxysilyloxy)silyl]propan-1-amine Chemical class NCC[SiH](O[SiH2]O[SiH2]O[SiH3])CCCN QUGFDTDMXRLLBM-UHFFFAOYSA-N 0.000 description 1
- HRYADZDELYSHIZ-UHFFFAOYSA-N 3-silyloxysilyloxysilyloxysilylpropan-1-amine Chemical compound NCCC[SiH2]O[SiH2]O[SiH2]O[SiH3] HRYADZDELYSHIZ-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 229910008045 Si-Si Inorganic materials 0.000 description 1
- 229910006411 Si—Si Inorganic materials 0.000 description 1
- BQODPTQLXVVEJG-UHFFFAOYSA-N [O].C=C Chemical group [O].C=C BQODPTQLXVVEJG-UHFFFAOYSA-N 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 229910021419 crystalline silicon Inorganic materials 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000001165 hydrophobic group Chemical group 0.000 description 1
- 238000006459 hydrosilylation reaction Methods 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000003754 machining Methods 0.000 description 1
- SWGZAKPJNWCPRY-UHFFFAOYSA-N methyl-bis(trimethylsilyloxy)silicon Chemical compound C[Si](C)(C)O[Si](C)O[Si](C)(C)C SWGZAKPJNWCPRY-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 230000035935 pregnancy Effects 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- UHUUYVZLXJHWDV-UHFFFAOYSA-N trimethyl(methylsilyloxy)silane Chemical compound C[SiH2]O[Si](C)(C)C UHUUYVZLXJHWDV-UHFFFAOYSA-N 0.000 description 1
- ZQTYRTSKQFQYPQ-UHFFFAOYSA-N trisiloxane Chemical compound [SiH3]O[SiH2]O[SiH3] ZQTYRTSKQFQYPQ-UHFFFAOYSA-N 0.000 description 1
- 238000009941 weaving Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
Abstract
A kind of organic silicon double-ion surfactant and its synthetic method, it is related to organic silicon double-ion surfactant and its synthetic method. It is trisiloxanes Gemini surface active agent to be solved the problem of oil-soluble is poor, facile hydrolysis. The structural formula of the organic silicon double-ion surfactant is as follows:
Wherein n=1,2 or 3. Preparation method are as follows: aminoethylaminopropyl tetrasiloxane is prepared with hexamethyldisiloxane, aminoethyl amino propyl trimethoxy silane reaction, then reacts to obtain four silicon methoxycarbonyl propyl amine of 2- benzyl alkene ethyl -3- with benzaldehyde; Again with epoxychloropropane and α, alpha, omega-dihydroxy alcohols material prepares Hexanediol diglycidyl ether; Four silicon methoxycarbonyl propyl amine of 2- benzyl alkene ethyl -3- is reacted with corresponding glycerin ether to obtain the final product. Interfacial tension of the surfactant in water phase is 22.9~23.5mN/m, and CAC value is 8.56 × 10-5~3.28 × 10-4, is not hydrolyzed in 6 months. It can be used for each field of industrial or agricultural.
Description
Technical field
The present invention relates to organic silicon double-ion surfactant and synthetic method thereof.
Background technology
Organic silicon double-ion surfactant is as a kind of novel surfactant that organosilicon new material grows up, and extensively
General being applied to each field of industrial or agricultural, such surfactant has hydrophobic group (Si-O-Si, Si-C-Si or Si-Si) than passing
The carbochain hydrophobicity of system is higher, has the capillary ability of excellent reduction, is widely used in weaving, cosmetics, moulds
The industries such as material, coating, agricultural chemicals, medicine, automobile and machining.Existing synthesizing organo-silicon Gemini surface active
The method of agent is more, and such as 2015, yellow good celestial being waited in (" preparation of nonionic trisiloxanes Gemini surface active agent and property
Can ", printing and dyeing assistant, 2015,32 (10), 21-25.) disclose a kind of nonionic trisiloxanes Gemini surface active agent (NTSGS)
And base preparation method, the method is that 1,1,1,3,5,5,5-heptamethyltrisiloxane (MDHM) and pi-allyl gather under platinum catalysis
Oxygen ethylene polyethenoxy ether (F6) prepares hydroxyl terminated polyether modification trisiloxanes (HPEMTS) through hydrosilylation,
Carry out esterification synthesis with maleic anhydride (MA) again, obtain nonionic trisiloxanes Gemini surface active agent.This three silicon
The carbon chain linker group of the Gemini surface active agent of oxygen alkane is the shortest, and oil-soluble is poor, and this kind of trisiloxanes is the most very
Easily hydrolysis, the major part hydrolysis of general two weeks, even the trisiloxane surfactant of double type is also left at one month
Right hydrolysis, affects its serviceability.
Summary of the invention
The oil-soluble that the present invention is to solve existing trisiloxanes Gemini surface active agent is poor, the technical problem of facile hydrolysis, and
A kind of organic silicon double-ion surfactant and synthetic method thereof are provided.
The structural formula of the organic silicon double-ion surfactant of the present invention is as follows:
Wherein n=1,2 or 3.
The preparation method of above-mentioned organic silicon double-ion surfactant is as follows:
One, it is 1:(10～20 by the mol ratio of aminoethylaminopropyl trimethoxy silane Yu hexamethyl disiloxane), by ammonia
Ethylaminopropyl trimethoxy silane adds in reactor with hexamethyl disiloxane, then adds tetramethyl hydrogen-oxygen in reactor
Change ammonium is as catalyst, and the addition of catalyst is the 0.1～0.5% of the amount of the material of aminoethylaminopropyl trimethoxy silane,
Being passed through nitrogen protection, oil bath heats to 80～90 DEG C, back flow reaction 4～5h, reclaims unreacted hexamethyl two silicon
Oxygen alkane, distillation of then reducing pressure, obtain aminoethylaminopropyl tetrasiloxane；
Two, weigh the aminoethylaminopropyl tetrasiloxane that step one obtains to react with benzaldehyde, wherein aminoethylaminopropyl four silicon
Oxygen alkane and benzaldehyde mol ratio 1:(1～1.3), first aminoethylaminopropyl tetrasiloxane is added in reactor, add dry
Dry molecular sieve and dehydrated alcohol, stirring is warming up to 40～70 DEG C, starts to drip the ethanol solution of benzaldehyde, drip complete
After be continuously heating to backflow, back flow reaction 40～60 minutes, stopped reaction, filter out molecular sieve, and use dehydrated alcohol
Rinse, merge organic facies anhydrous sodium sulfate and be dried, ethanol evaporation is removed, obtains intermediate 2-benzyl alkene ethyl-3-
Four silicon methoxycarbonyl propyl amine；
Three, by epoxychloropropane and α, ω dihydroxy alcohols substance reaction, prepare Hexanediol diglycidyl ether；Wherein contain
Having α, ω dihydroxy alcohols material is ethylene glycol, diethylene glycol or 2,2'-ethylenedioxybis(ethanol).；
Wherein prepare specifically comprising the following steps that of Hexanediol diglycidyl ether to weigh into epoxychloropropane, sodium hydroxide, four fourths
Base ammonium bromide and containing α, ω dihydroxy alcohols material, wherein the mass ratio of epoxychloropropane and sodium hydroxide be 1:(1～
1.1), the amount of the material of tetrabutyl ammonium bromide is the 0.5～1.5% of epoxychloropropane, containing α, ω dihydroxy alcohols material
It is 1:(2～4 with the mol ratio of epoxychloropropane), first epoxychloropropane, sodium hydroxide and tetrabutyl ammonium bromide are added
In reactor, then being placed on by reactor in the frozen water of 0 DEG C, dropping is containing α, ω dihydroxy alcohols thing under agitation
Matter, after dropping, is warming up to 40～45 DEG C, reacts 1～4 hour, then filters, by liquid phase saturated ammonium chloride
Solution washing is to neutral, after layering, organic layer liquid is dried with anhydrous magnesium sulfate, then normal pressure steams dichloromethane and mistake
Measure epoxychloropropane, then decompression is distilled off unreacted α, ω dihydroxy alcohols material and by-product, distillation of then reducing pressure
Obtain Hexanediol diglycidyl ether；Wherein decompression distill out the condition of Ethylene glycol diglycidyl ether be temperature be 125 DEG C,
Vacuum is 3～5mmHg；Decompression distill out the condition of diethylene glycol diglycidyl ether be temperature be 162 DEG C, vacuum
It is 3～5mmHg；Decompression distill out the condition of triethylene glycol diglycidylether be temperature be 204 DEG C, vacuum is 3
mmHg；
Four, it is 1:(2～3 by the mol ratio of Hexanediol diglycidyl ether Yu 2-benzyl alkene ethyl-3-four silicon methoxycarbonyl propyl amine),
By Hexanediol diglycidyl ether and 2-benzyl alkene ethyl-3-four silicon methoxycarbonyl propyl amine solvent in dehydrated alcohol, heating 50～
80 DEG C, reacting 10～24 hours, be then cooled to room temperature, rotary evaporation removes ethanol, by remaining mixture normal hexane
After washing, then rotary evaporation removes normal hexane, obtains the organic silicon double-ion surfactant containing phenyl imido tetrasiloxane.
The organic silicon double-ion surfactant of the present invention is with linker for diglycidyl ether and 2-benzyl alkene ethyl-3-four silicon first
Oxygen propyl group amine reacts open loop after the dimerization tetrasiloxane surfactant obtained, linker glycerin ether molecular chain length length and reaction
Obtaining hydroxy functional group makes surfactant hydrophilic increase, simultaneously the tetrasiloxane side chain of this surfactant and phenyl ring
Functional group constitutes lipophilic group, adds oil-soluble, improves surfactant absorption property on oil/water interface,
Being measured tension force by surface tension instrument, this surfactant interfacial tension in aqueous phase is 22.9～23.5mN/m, and this is permissible
Ensure that they are strongly adsorbed in air liquid interface.The critical aggregation concentration CAC value of this surfactant is the least simultaneously, for
8.56×10-5～3.28 × 10-4, show that this kind of Gemini surface active agent is easily assembled, be 10 in concentration-5Time assemble,
This super ability of aggregation is the distinguishing feature of dimeric surfactant.
The organic silicon double-ion surfactant good stability of the present invention, does not hydrolyzes in 6 months in water, can be as insecticides adjuvant
Composition is in pesticide.Synthetic method of the present invention is simple, and reaction condition is gentle, and easy and simple to handle easily controllable, post processing is simple
Being not required to, through repeatedly washing extraction, be distilled by decompression and i.e. can get corresponding product, product is easily isolated.
Accompanying drawing explanation
Fig. 1 is the infrared spectrogram of the organic silicon double-ion surfactant that test 1 obtains；
Fig. 2 is the surface tension the obtained logarithm with concentration of the organic silicon double-ion surfactant that test 1,2 and 3 obtains
Graph of relation.
Detailed description of the invention
Detailed description of the invention one: the structural formula of the organic silicon double-ion surfactant of present embodiment is as follows:
Wherein n=1,2 or 3.
Detailed description of the invention two: the preparation method of the organic silicon double-ion surfactant described in detailed description of the invention one is as follows:
One, it is 1:(10～20 by the mol ratio of aminoethylaminopropyl trimethoxy silane Yu hexamethyl disiloxane), by ammonia
Ethylaminopropyl trimethoxy silane adds in reactor with hexamethyl disiloxane, then adds tetramethyl hydrogen-oxygen in reactor
Change ammonium as catalyst, the addition of catalyst be the amount of the material of aminoethylaminopropyl trimethoxy silane 0.1～
0.5%, it is passed through nitrogen protection, oil bath heats to 80～90 DEG C, and back flow reaction 4～5h reclaims unreacted pregnancy
Base disiloxane, distillation of then reducing pressure, obtain aminoethylaminopropyl tetrasiloxane；
Two, weigh the aminoethylaminopropyl tetrasiloxane that step one obtains to react with benzaldehyde, wherein aminoethylaminopropyl four silicon
Oxygen alkane and benzaldehyde mol ratio 1:(1～1.3), first aminoethylaminopropyl tetrasiloxane is added in reactor, add dry
Dry molecular sieve and dehydrated alcohol, stirring is warming up to 40～70 DEG C, starts to drip the ethanol solution of benzaldehyde, drip complete
After be continuously heating to backflow, back flow reaction 40～60 minutes, stopped reaction, filter out molecular sieve, and use dehydrated alcohol
Rinse, merge organic facies anhydrous sodium sulfate and be dried, ethanol evaporation is removed, obtains intermediate 2-benzyl alkene ethyl-3-
Four silicon methoxycarbonyl propyl amine；
Three, by epoxychloropropane and α, ω dihydroxy alcohols substance reaction, prepare Hexanediol diglycidyl ether；Wherein contain
Having α, ω dihydroxy alcohols material is ethylene glycol, diethylene glycol or 2,2'-ethylenedioxybis(ethanol).；
Four, it is 1:(2～3 by the mol ratio of Hexanediol diglycidyl ether Yu 2-benzyl alkene ethyl-3-four silicon methoxycarbonyl propyl amine),
By Hexanediol diglycidyl ether and 2-benzyl alkene ethyl-3-four silicon methoxycarbonyl propyl amine solvent in dehydrated alcohol, heating 50～
80 DEG C, reacting 10～24 hours, be then cooled to room temperature, rotary evaporation removes ethanol, by remaining mixture normal hexane
After washing, then rotary evaporation removes normal hexane, obtains the organic silicon double-ion surfactant containing phenyl imido tetrasiloxane.
Detailed description of the invention three: present embodiment, unlike detailed description of the invention two, prepares glycol two contracting in step 3
Specifically comprising the following steps that of water glycerin ether weighs into epoxychloropropane, sodium hydroxide, tetrabutyl ammonium bromide and contains α, ω bis-
Hydroxy alcohols material, wherein epoxychloropropane is 1:(1～1.1 with the mass ratio of sodium hydroxide), tetrabutyl ammonium bromide
The amount of material is the 0.5～1.5% of epoxychloropropane, containing the mol ratio of α, ω dihydroxy alcohols material Yu epoxychloropropane
For 1:(2～4), first epoxychloropropane, sodium hydroxide and tetrabutyl ammonium bromide are joined in reactor, then will reaction
Device is placed in the frozen water of 0 DEG C, and dropping is containing α, ω dihydroxy alcohols material under agitation, after dropping, heats up
To 40～45 DEG C, react 1～4 hour, then filter, by liquid phase with saturated aqueous ammonium chloride washing to neutral, point
After Ceng by organic layer liquid with anhydrous magnesium sulfate after drying, then normal pressure steams dichloromethane and excess epoxy chloropropane, then reduces pressure
Unreacted α, ω dihydroxy alcohols material and by-product are distilled off, and then decompression distillation obtains Hexanediol diglycidyl ether；
Wherein Hexanediol diglycidyl ether is Ethylene glycol diglycidyl ether, diethylene glycol diglycidyl ether or 2,2'-ethylenedioxybis(ethanol). 2-glycidyl
Ether；Wherein decompression distill out the condition of Ethylene glycol diglycidyl ether be temperature be 125 DEG C, vacuum is 3～5mmHg；
Decompression distill out the condition of diethylene glycol diglycidyl ether be temperature be 162 DEG C, vacuum is 3～5mmHg；Decompression is steamed
Distillate the condition of triethylene glycol diglycidylether be temperature be 204 DEG C, vacuum is 3mmHg；Other be embodied as
Mode two is identical.
Detailed description of the invention four: aminoethyl ammonia third in present embodiment step one unlike detailed description of the invention two or three
Base trimethoxy silane is 1:(12～15 with the mol ratio of hexamethyl disiloxane).Other with detailed description of the invention two or
Three is identical.
Detailed description of the invention five: aminoethyl in present embodiment step 2 unlike one of detailed description of the invention two to four
Aminopropyl tetrasiloxane and benzaldehyde mol ratio 1:1.1.Other is identical with one of detailed description of the invention two to four.
Detailed description of the invention six: glycol two in present embodiment step 4 unlike one of detailed description of the invention two to five
Glycidyl ether is 1:2.5 with the mol ratio of 2-benzyl alkene ethyl-3-four silicon methoxycarbonyl propyl amine.Other is with detailed description of the invention two
Identical to one of five.
Detailed description of the invention seven: glycol two in present embodiment step 4 unlike one of detailed description of the invention two to six
Glycidyl ether is 1:2.5 with the mol ratio of 2-benzyl alkene ethyl-3-four silicon methoxycarbonyl propyl amine.Other is with detailed description of the invention two
Identical to one of six.
By following verification experimental verification beneficial effects of the present invention:
Test 1: the preparation method of the organic silicon double-ion surfactant of this test is as follows:
One, it is 1:18 by the mol ratio of aminoethylaminopropyl trimethoxy silane Yu hexamethyl disiloxane, by aminoethyl ammonia
Propyl trimethoxy silicane adds in 150mL there-necked flask with hexamethyl disiloxane, then adds tetramethyl in there-necked flask
Base ammonium hydroxide is as catalyst, and the addition of Tetramethylammonium hydroxide is the material of aminoethylaminopropyl trimethoxy silane
The 0.1% of amount, is passed through nitrogen protection, and oil bath heats to 90 DEG C, and back flow reaction 4 hours reclaims unreacted six
Tetramethyldisiloxane, then 150 DEG C/6mmHg of decompression distillation, obtains aminoethylaminopropyl tetrasiloxane；This aminoethyl
Aminopropyl tetrasiloxane is weak yellow liquid；The reaction of this step can be expressed from the next:
Wherein Me represents methyl.
Two, aminoethylaminopropyl tetrasiloxane and benzaldehyde that step one obtains, wherein aminoethylaminopropyl tetrasiloxane are weighed
With benzaldehyde mol ratio 1:1.05, first 15.3 grams of aminoethylaminopropyl tetrasiloxanes are added in 150mL there-necked flask,
Adding 5 grams of dry molecular sieves and 70mL dehydrated alcohol, stirring is warming up to 40 DEG C, starts to drip the ethanol of benzaldehyde
Solution (wherein benzaldehyde is 1:5 with the volume ratio of ethanol), drips and complete follow-up continuing is warming up to 90 DEG C, back flow reaction
40 minutes, stopped reaction, filter out molecular sieve, and use 30mL dehydrated alcohol to rinse 3 times, merge organic facies nothing
Aqueous sodium persulfate is dried, and is removed by ethanol distillation, obtains intermediate 2-benzyl alkene ethyl-3-four silicon methoxycarbonyl propyl amine；This step
Rapid reaction can be expressed from the next:
Three, weigh into epoxychloropropane, sodium hydroxide, tetrabutyl ammonium bromide and ethylene glycol, wherein epoxychloropropane with
The mass ratio of granular sodium hydroxide is 1:1.1, and the amount of the material of tetrabutyl ammonium bromide is the 1.5% of epoxychloropropane, second
Glycol is 1:2.5 with the mol ratio of epoxychloropropane, first epoxychloropropane, sodium hydroxide and tetrabutyl ammonium bromide is joined
In 200mL there-necked flask, then reactor is placed in the frozen water of 0 DEG C, drips ethylene glycol under agitation, drip
Bi Hou, is warming up to 45 DEG C, reacts 1 hour, then filters, by liquid phase with saturated aqueous ammonium chloride washing to neutral,
After layering organic layer liquid is dried with anhydrous magnesium sulfate, then normal pressure steams dichloromethane and excess epoxy chloropropane, then
Temperature is 125 DEG C, vacuum is decompression distillation under conditions of 3～5mmHg, obtains Ethylene glycol diglycidyl ether.Should
Step can be expressed from the next:
Four, it is 2.5:1 by the mol ratio of Ethylene glycol diglycidyl ether Yu 2-benzyl alkene ethyl-3-four silicon methoxycarbonyl propyl amine, will
Ethylene glycol diglycidyl ether and 2-benzyl alkene ethyl-3-four silicon methoxycarbonyl propyl amine solvent, in 50mL dehydrated alcohol, heat
80 DEG C of backflows are also reacted 10 hours, are then cooled to room temperature, and rotary evaporation removes ethanol, by remaining mixture normal hexane
After washing, continue rotation and boil off except normal hexane, obtain the organic silicon double-ion surfactant containing phenyl imido tetrasiloxane.This table
Face activating agent is weak yellow liquid.The reaction of this step can be expressed from the next:
The infrared spectrogram (FT-IR) of the organic silicon double-ion surfactant containing phenyl imido tetrasiloxane of this test preparation
As it is shown in figure 1, it will be seen from figure 1 that 3300cm-1(m, ν=O-H) it is hydroxyl stretching vibration peak, 3079cm-1(s, ν=C-H)
The hydrocarbon stretching vibration of phenyl ring；2936cm-1And 2855cm-1(m, ν-CH3, ν-CH2) the hydrocarbon flexible of methyl and methylene shake
Dynamic, 1634cm-1(s, ν=C=N) it is C=N stretching vibration peak, 1609～1469cm-1(s, νC=C) phenyl ring skeletal vibration, 1437
cm-1～1398cm-1(m, δ sCH3, δ sCH2) methyl and the bending vibration of methylene；1369cm-1(s, ν=C-N) it is C-N
Stretching vibration peak, 1248cm-1(s, δ s=Si-Me3)Si-Me3In-CH3Antisymmetric stretching vibration absworption peak, 1087cm-1
(s, ν=Si-O-Si) it is the stretching vibration absworption peak of Si-O-Si key, 845cm-1～729cm-1(s, δ s=Si-Me3) it is Si-Me3
Characteristic absorption peak.The structural formula of the organic silicon double-ion surfactant demonstrating this test preparation is:
Test 2: in this test step 3 unlike test 1, ethylene glycol is replaced by diethylene glycol, obtains containing phenyl imido four
The organic silicon double-ion surfactant of siloxanes.Other are identical with test 1, obtain the organosilicon containing phenyl imido tetrasiloxane
Gemini surface active agent represents with GS-4.Its molecular structural formula is as follows:
Test 3: in this test step 3 unlike test 1, ethylene glycol is replaced by 2,2'-ethylenedioxybis(ethanol)., obtains containing phenyl imido four
The organic silicon double-ion surfactant of siloxanes.Other are identical with test 1, obtain the organosilicon containing phenyl imido tetrasiloxane
Gemini surface active agent represents with GS-6.Based structures formula is as follows:
The relation curve of the surface tension of the organic silicon double-ion surfactant that test 1,2 and 3 obtains and the logarithm of concentration is such as
Shown in Fig. 2, wherein lowest surface tension γcacBeing determined by the level value of concentration curve, critical aggregation concentration CAC is by surface
Tensions versus concentration curve break determines.The organosilicone gemini surface activity of test 1,2 and 3 preparation obtained by Fig. 2
Surface tension and the critical aggregation concentration CAC value of agent are listed in the following table.
The surface tension of table 1 organic silicon double-ion surfactant and critical aggregation concentration CAC value
| Gemini surface active agent | GS-2 | GS-4 | GS-6 |
| CAC mol/L | 8.56×10-5 | 2.83×10-4 | 3.28×10-4 |
| γcac mN/m | 22.9 | 23.2 | 23.5 |
The organic silicon double-ion surfactant of test 1,2 and 3 preparation is investigated over time by mensuration surface tension
Water-disintegrable, test shows the water-disintegrable the not strongest of these three surfactant, does not hydrolyzes in water in 6 months.
Claims (7)
1. an organic silicon double-ion surfactant, it is characterised in that the structural formula of this surfactant is as follows:
Wherein n=1,2 or 3.
2. the method for the preparation a kind of organic silicon double-ion surfactant described in claim 1, it is characterised in that the method by with
Lower step is carried out:
One, it is 1:(10～20 by the mol ratio of aminoethylaminopropyl trimethoxy silane Yu hexamethyl disiloxane), by ammonia second
Base aminopropyl trimethoxysilane adds in reactor with hexamethyl disiloxane, then adds tetramethyl hydroxide in reactor
Ammonium is as catalyst, and the addition of catalyst is the 0.1～0.5% of the amount of the material of aminoethylaminopropyl trimethoxy silane, logical
Entering nitrogen protection, oil bath heats to 80～90 DEG C, and back flow reaction 4～5h reclaims unreacted hexamethyl disiloxane,
Then reduce pressure distillation, obtain aminoethylaminopropyl tetrasiloxane；
Two, weigh the aminoethylaminopropyl tetrasiloxane that step one obtains to react with benzaldehyde, wherein aminoethylaminopropyl four silicon
Oxygen alkane and benzaldehyde mol ratio 1:(1～1.3), first aminoethylaminopropyl tetrasiloxane is added in reactor, add dry
Molecular sieve and dehydrated alcohol, stirring be warming up to 40～70 DEG C, start to drip the ethanol solution of benzaldehyde, drip complete follow-up
Continuous being warming up to is refluxed, back flow reaction 40～60 minutes, and stopped reaction filters out molecular sieve, and uses dehydrated alcohol to rinse,
Merge organic facies anhydrous sodium sulfate to be dried, ethanol evaporation is removed, obtains intermediate 2-benzyl alkene ethyl-3-four silicon methoxy
Propyl group amine；
Three, by epoxychloropropane and α, ω dihydroxy alcohols substance reaction, prepare Hexanediol diglycidyl ether；Wherein contain
α, ω dihydroxy alcohols material is ethylene glycol, diethylene glycol or 2,2'-ethylenedioxybis(ethanol).；
Four, it is 1:(2～3 by the mol ratio of Hexanediol diglycidyl ether Yu 2-benzyl alkene ethyl-3-four silicon methoxycarbonyl propyl amine), will
Hexanediol diglycidyl ether and 2-benzyl alkene ethyl-3-four silicon methoxycarbonyl propyl amine solvent, in dehydrated alcohol, heat 50～80 DEG C,
Reacting 10～24 hours, be then cooled to room temperature, rotary evaporation removes ethanol, after remaining mixture is washed with normal hexane,
Rotary evaporation removes normal hexane again, obtains the organic silicon double-ion surfactant containing phenyl imido tetrasiloxane.
The preparation method of a kind of organic silicon double-ion surfactant the most according to claim 2, it is characterised in that step
Prepare specifically comprising the following steps that of Hexanediol diglycidyl ether in three to weigh into epoxychloropropane, sodium hydroxide, tetrabutyl phosphonium bromide
Ammonium and containing α, ω dihydroxy alcohols material, wherein epoxychloropropane is 1:(1～1.1 with the mass ratio of sodium hydroxide), four
The amount of the material of butylammonium bromide is the 0.5～1.5% of epoxychloropropane, containing α, ω dihydroxy alcohols material and epoxy chloropropionate
The mol ratio of alkane is 1:(2～4), first epoxychloropropane, sodium hydroxide and tetrabutyl ammonium bromide are joined in reactor,
Being placed on by reactor in the frozen water of 0 DEG C, dropping is containing α, ω dihydroxy alcohols material under agitation again, after dropping,
It is warming up to 40～45 DEG C, reacts 1～4 hour, then filter, by liquid phase with saturated aqueous ammonium chloride washing to neutral,
After layering by organic layer liquid with anhydrous magnesium sulfate after drying, then normal pressure steams dichloromethane and excess epoxy chloropropane, then subtracts
Pressure is distilled off unreacted α, ω dihydroxy alcohols material and by-product, and then decompression distillation obtains Hexanediol diglycidyl ether；
Wherein Hexanediol diglycidyl ether is Ethylene glycol diglycidyl ether, diethylene glycol diglycidyl ether or 2,2'-ethylenedioxybis(ethanol). 2-glycidyl
Ether.
4. according to the preparation method of a kind of organic silicon double-ion surfactant described in Claims 2 or 3, it is characterised in that
Decompression distill out the condition of Ethylene glycol diglycidyl ether be temperature be 125 DEG C, vacuum is 3～5mmHg；Decompression distillation
Go out the condition of diethylene glycol diglycidyl ether be temperature be 162 DEG C, vacuum is 3～5mmHg；Decompression distills out 2,2'-ethylenedioxybis(ethanol).
The condition of diglycidyl ether be temperature be 204 DEG C, vacuum is 3mmHg.
5. according to the preparation method of a kind of organic silicon double-ion surfactant described in Claims 2 or 3, it is characterised in that
In step one, aminoethylaminopropyl trimethoxy silane is 1:(12～15 with the mol ratio of hexamethyl disiloxane).
6. according to the preparation method of a kind of organic silicon double-ion surfactant described in Claims 2 or 3, it is characterised in that
Aminoethylaminopropyl tetrasiloxane and benzaldehyde mol ratio 1:1.1 in step 2.
7. according to the preparation method of a kind of organic silicon double-ion surfactant described in Claims 2 or 3, it is characterised in that
In step 4, Hexanediol diglycidyl ether is 1:2.5 with the mol ratio of 2-benzyl alkene ethyl-3-four silicon methoxycarbonyl propyl amine.
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| CN113845893A (en) * | 2021-10-22 | 2021-12-28 | 中国石油化工股份有限公司 | Salt-resistant low-tension foaming agent composition and preparation method and application thereof |
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| CA2129806A1 (en) * | 1993-09-06 | 1995-03-07 | Klaus-Dieter Klein | Silanes with hydrophilic groups, their synthesis and use as surfactants in aqueous media |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107266487A (en) * | 2017-06-20 | 2017-10-20 | 汕头大学 | A kind of quaternary tetrasiloxane Gemini surface active agent and its preparation |
| CN107266487B (en) * | 2017-06-20 | 2019-03-22 | 汕头大学 | A kind of quaternary tetrasiloxane Gemini surface active agent and its preparation |
| CN113845893A (en) * | 2021-10-22 | 2021-12-28 | 中国石油化工股份有限公司 | Salt-resistant low-tension foaming agent composition and preparation method and application thereof |
| CN113845893B (en) * | 2021-10-22 | 2023-03-14 | 中国石油化工股份有限公司 | Salt-resistant low-tension foaming agent composition and preparation method and application thereof |
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