CN117467455A - Carboxylic acid quaternary ammonium salt sodium sulfonate surfactant, and preparation method and application thereof - Google Patents
Carboxylic acid quaternary ammonium salt sodium sulfonate surfactant, and preparation method and application thereof Download PDFInfo
- Publication number
- CN117467455A CN117467455A CN202210853373.8A CN202210853373A CN117467455A CN 117467455 A CN117467455 A CN 117467455A CN 202210853373 A CN202210853373 A CN 202210853373A CN 117467455 A CN117467455 A CN 117467455A
- Authority
- CN
- China
- Prior art keywords
- quaternary ammonium
- sulfonate surfactant
- carboxylic acid
- ammonium salt
- sodium sulfonate
- 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.)
- Pending
Links
- 239000004094 surface-active agent Substances 0.000 title claims abstract description 76
- 239000011734 sodium Substances 0.000 title claims abstract description 71
- 229910052708 sodium Inorganic materials 0.000 title claims abstract description 61
- -1 Carboxylic acid quaternary ammonium salt Chemical class 0.000 title claims abstract description 54
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 title claims abstract description 45
- 238000002360 preparation method Methods 0.000 title abstract description 12
- 239000002904 solvent Substances 0.000 claims abstract description 18
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims abstract description 13
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 13
- 150000003141 primary amines Chemical class 0.000 claims abstract description 6
- 239000003995 emulsifying agent Substances 0.000 claims abstract description 4
- OSEJMOGPHHVJJG-UHFFFAOYSA-M sodium;2-chloroethanesulfonate;hydrate Chemical compound O.[Na+].[O-]S(=O)(=O)CCCl OSEJMOGPHHVJJG-UHFFFAOYSA-M 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 22
- 239000007806 chemical reaction intermediate Substances 0.000 claims description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- 238000003756 stirring Methods 0.000 claims description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 238000001953 recrystallisation Methods 0.000 claims description 6
- 238000000746 purification Methods 0.000 claims description 5
- 238000000926 separation method Methods 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 4
- 238000001704 evaporation Methods 0.000 claims description 3
- 150000003139 primary aliphatic amines Chemical class 0.000 claims description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- 238000005187 foaming Methods 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 239000003208 petroleum Substances 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 239000006260 foam Substances 0.000 abstract description 24
- 239000002994 raw material Substances 0.000 abstract description 6
- 239000003112 inhibitor Substances 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 59
- 238000010521 absorption reaction Methods 0.000 description 25
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 19
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 15
- 238000004458 analytical method Methods 0.000 description 8
- 230000005764 inhibitory process Effects 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- 239000000543 intermediate Substances 0.000 description 6
- 230000001804 emulsifying effect Effects 0.000 description 5
- 125000000542 sulfonic acid group Chemical group 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- 238000001819 mass spectrum Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000004140 cleaning Methods 0.000 description 3
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 150000003242 quaternary ammonium salts Chemical group 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 2
- 238000006277 sulfonation reaction Methods 0.000 description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- VEFLKXRACNJHOV-UHFFFAOYSA-N 1,3-dibromopropane Chemical compound BrCCCBr VEFLKXRACNJHOV-UHFFFAOYSA-N 0.000 description 1
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000002563 ionic surfactant Substances 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N monoethanolamine hydrochloride Natural products NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- LPUQAYUQRXPFSQ-DFWYDOINSA-M monosodium L-glutamate Chemical compound [Na+].[O-]C(=O)[C@@H](N)CCC(O)=O LPUQAYUQRXPFSQ-DFWYDOINSA-M 0.000 description 1
- 235000013923 monosodium glutamate Nutrition 0.000 description 1
- 239000004223 monosodium glutamate Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000004289 sodium hydrogen sulphite Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- AGGKEGLBGGJEBZ-UHFFFAOYSA-N tetramethylenedisulfotetramine Chemical compound C1N(S2(=O)=O)CN3S(=O)(=O)N1CN2C3 AGGKEGLBGGJEBZ-UHFFFAOYSA-N 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
- C09K23/28—Aminocarboxylic acids
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B08—CLEANING
- B08B—CLEANING IN GENERAL; PREVENTION OF FOULING IN GENERAL
- B08B3/00—Cleaning by methods involving the use or presence of liquid or steam
- B08B3/04—Cleaning involving contact with liquid
- B08B3/08—Cleaning involving contact with liquid the liquid having chemical or dissolving effect
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
- C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C309/13—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
- C07C309/14—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton containing amino groups bound to the carbon skeleton
-
- 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
- C09K23/18—Quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/62—Quaternary ammonium compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention belongs to the technical field of surfactants, and relates to a carboxylic acid quaternary ammonium salt sodium sulfonate surfactant, a preparation method and application thereof, wherein the molecular structural general formula of the carboxylic acid quaternary ammonium salt sodium sulfonate surfactant is as follows:the carboxylic acid quaternary ammonium salt sodium sulfonate surfactant is synthesized by the following raw materials in molar ratio: the molar ratio of the fatty primary amine to the alcohol solvent to the acrylic acid to the sodium 2-chloroethyl sulfonate monohydrate is 1: (10.6-19.6): (2.00-2.22): (1.00-1.11). The carboxylic acid quaternary ammonium salt sodium sulfonate surfactant can be used as a foam inhibitor, a low-foam surfactant or an emulsifier.
Description
Technical Field
The invention relates to the technical field of surfactants, in particular to a carboxylic acid quaternary ammonium salt sodium sulfonate surfactant, and a preparation method and application thereof.
Background
The surfactant is known as industrial monosodium glutamate, and is a substance which has hydrophilic and lipophilic groups, can be directionally arranged on the surface of the solution, and can obviously reduce the surface tension of the solution. The surfactant is divided into an ionic surfactant, a nonionic surfactant and the like, and has great practical value. The low-foam surfactant is a surfactant product with low foam performance, which is embodied in industrial application, and can be used in the fields of industrial cleaning and the like.
In the prior art, a synthetic method (CN 109912506A) related to a symmetrical imidazoline Gemini surfactant is disclosed: fatty acid and diethylenetriamine are used as raw materials, dimethylbenzene is used as a solvent, zinc powder is used as a catalyst, the temperature is raised to 190-210 ℃ for reaction for 6-10h, and the intermediate is obtained by reduced pressure distillation at 130-150 ℃; dimethyl carbonate is added into the intermediate at 85 ℃ to react for 4-6 hours, the temperature is raised to 90 ℃, and 1, 3-dibromopropane is added to react for 6-8 hours. Another research discloses a sulfo-and phosphate-group-containing anionic surfactant and a synthetic method thereof (CN 109173920B): adding sodium bisulphite into a reactor, adding water, adding (E) -oct-4-ene-1, 8-diacid, introducing nitrogen, stirring and heating to 80-100 ℃ for reacting for 4-6 hours to obtain an intermediate A; adding an intermediate A, N-alkyl ethanolamine and a catalyst into a reactor, introducing nitrogen, stirring and heating to 100-140 ℃ for reacting for 3-5h to obtain a transparent solution intermediate B; adding the intermediate B and phosphoric acid into a reaction kettle, stirring and heating to 50-70 ℃ for reacting for 2-4h.
Up to now, sulfonate surfactants have not been widely used because of their relatively high synthetic cost. Meanwhile, the inventor also notices that the existing surfactant has the defects of foam inhibition performance, low foam performance and emulsifying performance, and the preparation technology process is complex.
Disclosure of Invention
Aiming at the defects of single variety, improved performance, complex preparation technology process and the like of the sulfonate surfactant in the existing production method, the invention aims at providing the carboxylic acid quaternary ammonium salt sodium sulfonate surfactant which has foam inhibition performance, low foam performance and the like.
The invention aims at providing a preparation method of a carboxylic acid quaternary ammonium salt sodium sulfonate surfactant, which is simple, easily available in raw material source and low in production cost.
The invention aims at providing an application of a carboxylic acid quaternary ammonium salt sodium sulfonate surfactant as a foam inhibitor, a low-foam surfactant or an emulsifier.
In order to achieve the above object, the present invention provides the following technical solutions:
in a first aspect of the present invention, there is provided a sodium carboxylate quaternary ammonium sulfonate surfactant having the general molecular structural formula (QH) of:
wherein n=12, 14, 16, 18;
C n H 2n+1 is a linear alkyl group;
specifically, the carboxylic acid quaternary ammonium salt sodium sulfonate surfactant is derived from the following structure:
formula QH-12:
formula QH-14:
formula QH-16:
formula QH-18:
research shows that if sodium sulfonate, carboxyl and quaternary ammonium salt groups are introduced into the molecular structure of the surfactant, the carboxylic acid quaternary ammonium salt sodium sulfonate surfactant with a novel structure is formed, and has good foam inhibition performance, surface activity, emulsifying performance and low foam performance.
In a second aspect of the present invention, there is provided a method for preparing the sodium carboxylate quaternary ammonium sulfonate surfactant of the first aspect, comprising the steps of:
s1: mixing fatty primary amine, an alcohol solvent and acrylic acid for reaction to obtain a reaction intermediate (ZT), wherein the structural general formula of the reaction intermediate (ZT) is as follows:
C n H2 n +]N(CH 2 CH 2 COOH) 2 ；
wherein n=12, 14, 16, 18;
C n H 2n+1 is a linear alkyl group;
s2: adding 2-chloroethyl sodium sulfonate monohydrate into a reaction intermediate ZT, and carrying out mixed reaction to obtain a carboxylic acid quaternary ammonium salt sodium sulfonate surfactant product QH; and evaporating the solvent from the product QH under normal pressure, and recrystallizing, separating and purifying by using an organic solvent to obtain the pure product QH (QH-12, QH-14, QH-16 or QH-18) of the sodium carboxylate quaternary ammonium sulfonate surfactant.
The reaction formula is:
in one or more embodiments, the molar ratio of primary aliphatic amine, alcohol solvent, acrylic acid, sodium 2-chloroethyl sulfonate monohydrate is 1: (10.6-19.6): (2.00-2.22): (1.00-1.11).
In one or more embodiments, in step S1, the primary fatty amine is dodecaprimary amine, tetradecprimary amine, hexadecprimary amine, octadecadprimary amine.
In one or more embodiments, in step S1, the alcohol solvent is any one or more of ethanol and isopropanol.
In one or more embodiments, in step S1, the reaction temperature is 60-80℃and the reaction time is 3-5 hours.
In one or more embodiments, in step S2, the organic solvent separated and purified by recrystallization is petroleum ether, methanol, ethyl acetate, or the like.
In one or more embodiments, in step S2, the reaction temperature is 60-80℃and the reaction time is 3-5 hours.
In a preferred embodiment, the preparation method of the carboxylic acid quaternary ammonium salt sodium sulfonate surfactant QH specifically comprises the following steps:
(1) Adding primary aliphatic amine into a reaction container, adding an alcohol solvent, heating and stirring at 60-80 ℃ to dissolve, adding acrylic acid in batches, and stirring at 60-80 ℃ to react for 3-5h after the addition is finished to obtain a reaction intermediate (ZT);
(2) Adding 2-chloroethyl sodium sulfonate monohydrate into a reaction intermediate ZT in batches, and stirring at 60-80 ℃ for reaction for 3-5 hours after the addition is finished to obtain a carboxylic acid quaternary ammonium salt sodium sulfonate surfactant product QH; the solvent is distilled off under normal pressure of the product QH, and then the product QH is recrystallized, separated and purified for 2 to 3 times by an organic solvent to obtain the pure product QH (QH-12, QH-14, QH-16 or QH-18) of the carboxylic acid quaternary ammonium salt sodium sulfonate type surfactant.
In the feeding, 3-5 batches of acrylic acid are added, and 3-5 batches of 2-chloroethyl sodium sulfonate monohydrate are added.
In a third aspect of the present invention, there is provided a sodium carboxylate quaternary ammonium sulfonate surfactant obtained by the above method.
In a fourth aspect of the present invention, there is provided the use of the above-described carboxylic acid quaternary ammonium salt sodium sulfonate surfactant as suds suppressors, low sudsing surfactants and emulsifiers. Such as industrial cleaning and metal workpiece cleaning.
The invention takes fatty primary amine as the main raw material of the carboxylic acid quaternary ammonium salt sodium sulfonate type surfactant, and in the synthesis of the carboxylic acid quaternary ammonium salt sodium sulfonate type surfactant, the sodium sulfonate group, the carboxyl group and the quaternary ammonium salt group are introduced into the molecular structure of the surfactant by sequentially adding acrylic acid and 2-chloroethyl sodium sulfonate monohydrate, so that the product has surface activity.
The specific embodiment of the invention has the following beneficial effects:
(i) According to the invention, the sodium sulfonate group, the carboxyl group and the quaternary ammonium salt group hydrophilic group are combined with lipophilic groups with different carbon chain lengths to form the novel-structure carboxylic acid quaternary ammonium salt sodium sulfonate surfactant, and the product has good surface activity.
(ii) The main raw material of the carboxylic acid quaternary ammonium salt sodium sulfonate surfactant is fatty primary amine, and has low cost and low production raw material cost.
(iii) The existing sulfonate surfactant is synthesized by sulfonation reaction mainly using chlorosulfonic acid, concentrated sulfuric acid, fuming sulfuric acid and sulfur trioxide as sulfonating reagents, and has the advantages of higher sulfonation reaction temperature, complex technical process, and high risk and corrosiveness. The synthesis method of the carboxylic acid quaternary ammonium salt sodium sulfonate surfactant is simple and is carried out at a lower temperature.
Drawings
FIG. 1 is an infrared spectrum of the product QH-12 of example 1.
FIG. 2 is a nuclear magnetic resonance spectrum of the product QH-12 of example 1.
FIG. 3 is a mass spectrum of the product QH-12 of example 1.
FIG. 4 is an infrared spectrum of the product QH-14 of example 2.
FIG. 5 is a nuclear magnetic resonance spectrum of the product QH-14 of example 2.
FIG. 6 is a mass spectrum of the product QH-14 of example 2.
FIG. 7 is an infrared spectrum of the product QH-16 of example 3.
FIG. 8 is a nuclear magnetic resonance spectrum of the product QH-16 of example 3.
FIG. 9 is a mass spectrum of the product QH-16 of example 3.
FIG. 10 is an infrared spectrum of the product QH-18 of example 4.
FIG. 11 is a nuclear magnetic resonance spectrum of the product QH-18 of example 4.
FIG. 12 is a mass spectrum of the product QH-18 of example 4.
FIG. 13 is a plot of the surface tension versus log concentration for product QH-12 of example 1.
FIG. 14 is a plot of the surface tension versus concentration log for product QH-14 of example 2.
FIG. 15 is a plot of the surface tension versus concentration log for product QH-16 of example 3.
FIG. 16 is a plot of the surface tension versus concentration log for product QH-18 of example 4.
Detailed Description
The following detailed description is given by way of illustration, and in order to make the technical solution of the present invention more clearly understood by those skilled in the art, the technical solution of the present invention will be described in detail with reference to specific examples and experimental examples.
Example 1
(1) Preparation of sodium carboxylate Quaternary ammonium sulfonate surfactant (product QH-12):
1) 185.35g of dodecyl amine, 800g of isopropyl alcohol and stirring at 75 ℃ are added into a reaction vessel to be dissolved, 154.9g of acrylic acid is added in 5 batches, and stirring is carried out at 75 ℃ for 4 hours to obtain a reaction intermediate ZT-12.
2) 197.8g of 2-chloroethyl sodium sulfonate monohydrate is added into a reaction intermediate ZT-12 in 5 batches, and after the addition is finished, the mixture is stirred and reacted for 4 hours at 75 ℃ to obtain a carboxylic acid quaternary ammonium salt sodium sulfonate surfactant product QH-12; the solvent of the product QH-12 is distilled off under normal pressure, and then ethyl acetate is used for recrystallization, separation and purification for 2 times, thus obtaining the pure product QH-12 of the carboxylic acid quaternary ammonium salt sodium sulfonate surfactant.
Pure QH-12 was subjected to infrared analysis (fig. 1): 3610cm -1 (peak 1) is an O-H stretching vibration absorption peak, 2923cm -1 (peak 2) asymmetric stretching vibration absorption peak of methylene, 2854cm -1 (peak 3) symmetrical stretching vibration peak of methylene, 1732cm -1 (peak 4) C=O stretching vibration absorption peak in carboxyl group, 1398cm -1 (peak 5) symmetrical flexural vibration of methylene group, 1203cm -1 (peak 6) C-N stretching vibrationAbsorption peak, 1056cm -1 (peak 7) is an asymmetric stretching vibration absorption peak of sulfonic acid group S=O, 721cm -1 (peak 8) is a vibration in the methylene basal plane of 599cm -1 (peak 9) is the telescopic vibration absorption peak of S-O.
Pure QH-12 was subjected to nuclear magnetic analysis (FIG. 2): 1 H NMR(400MHz,CD 3 OD),δ:0.8820-0.9163(3H,t,J＝6.86Hz,-CH 3 ),1.2954(18H,s,CH 3 (CH 2 ) 9 CH 2 CH 2 N-),1.7458-1.7829(2H,t,J＝7.42Hz,CH 3 (CH 2 ) 9 CH 2 CH 2 N-),2.6323-2.6645(4H,t,J＝6.44Hz,2×-NCH 2 CH 2 COOH),3.1837-3.2244(6H,t,J＝8.14Hz,-NCH 2 CH 2 SO 3 Na andCH 3 (CH 2 ) 10 CH 2 N-),3.8046-3.8454(4H,t,J＝8.16Hz,2×-CH 2 CH 2 COOH)ppm.
mass spectrometry analysis was performed on pure QH-12 (fig. 3): HRMS (ESI) (negative) M/z: [ M-Na ] + ] - Calcd for C 20 H 39 O 7 NSCl,472.2136；Found 472.2721.
The reaction formula is:
example 2
(1) Preparation of sodium carboxylate Quaternary ammonium sulfonate surfactant (product QH-14):
1) 213.4g of tetramine, 800g of isopropanol and 75 ℃ are added into a reaction vessel, heated, stirred and dissolved, 154.9g of acrylic acid is added in 5 batches, stirred and reacted for 4 hours at 75 ℃ to obtain a reaction intermediate ZT-14.
2) 197.8g of 2-chloroethyl sodium sulfonate monohydrate is added into a reaction intermediate ZT-14 in 5 batches, and after the addition is finished, the mixture is stirred and reacted for 4 hours at 75 ℃ to obtain a carboxylic acid quaternary ammonium salt sodium sulfonate surfactant product QH-14; the solvent of the product QH-14 is distilled off under normal pressure, and then ethyl acetate is used for recrystallization, separation and purification for 2 times, thus obtaining the pure product QH-14 of the carboxylic acid quaternary ammonium salt sodium sulfonate surfactant.
Pure QH-14 was subjected to infrared analysis (fig. 4): 3610cm -1 (peak 1) is an O-H stretching vibration absorption peak, 2923cm -1 (peak 2) asymmetric stretching vibration absorption peak of methylene, 2854cm -1 (peak 3) symmetrical stretching vibration peak of methylene, 1730cm -1 (peak 4) C=O stretching vibration absorption peak in carboxyl, 1467cm -1 (peak 5) asymmetric flexural vibration of methylene group, 1396cm -1 (peak 6) symmetrical flexural vibration of methylene group, 1203cm -1 (peak 7) C-N telescopic vibration absorption peak, 1056cm -1 (peak 8) is an asymmetric stretching vibration absorption peak of sulfonic acid group S=O, 721cm -1 (peak 9) is a methylene basal plane internal rocking vibration 594cm -1 (peak 10) is the telescopic vibration absorption peak of S-O.
Pure QH-14 was subjected to nuclear magnetic analysis (FIG. 5): 1 H NMR(400MHz,CD 3 OD),δ:0.8816-0.9159(3H,t,J＝6.86Hz,-CH 3 ),1.2896(22H,s,CH 3 (CH 2 ) 11 CH 2 CH 2 N-),1.7455-1.7821(2H,t,J＝7.32Hz,CH 3 (CH 2 ) 11 CH 2 CH 2 N-),2.6302-2.6624(4H,t,J＝6.44Hz,2×-NCH 2 CH 2 COOH),3.1834-3.2241(6H,t,J＝8.14Hz,-NCH 2 CH 2 SO 3 Na and CH 3 (CH 2 ) 12 CH 2 N-)3.8041-3.8449(4H,t,J＝8.16Hz,2×-NCH 2 CH 2 COOH)ppm.
mass spectrometry analysis was performed on pure QH-14 (fig. 6): HRMS (ESI) (negative) M/z: [ M-H ] + ] - Calcd for C 22 H 42 O 7 NSClNa,522.2268；Found 522.3053.[M-Na + ] - Calcd for C 22 H 43 O 7 NSCl,500.2449；Found 500.3057.[M-Na + -Cl - -H + ] - Calcd for C 22 H 42 O 7 NS,464.2682；Found 464.3166.
The reaction formula is:
example 3
(1) Preparation of sodium carboxylate Quaternary ammonium sulfonate surfactant (product QH-16):
1) 241.46g of hexadecylamine, 800g of isopropanol and 75 ℃ are added into a reaction vessel, heated, stirred and dissolved, 154.9g of acrylic acid is added in 5 batches, and stirred and reacted for 4 hours at 75 ℃ to obtain a reaction intermediate ZT-16.
2) 197.8g of 2-chloroethyl sodium sulfonate monohydrate is added into a reaction intermediate ZT-16 in 5 batches, and after the addition is finished, the mixture is stirred and reacted for 4 hours at 75 ℃ to obtain a carboxylic acid quaternary ammonium salt sodium sulfonate surfactant product QH-16; the solvent of the product QH-16 is distilled off under normal pressure, and then ethyl acetate is used for recrystallization, separation and purification for 2 times, thus obtaining the pure product QH-16 of the carboxylic acid quaternary ammonium salt sodium sulfonate surfactant.
Pure QH-16 was subjected to infrared analysis (fig. 7): 3612cm -1 (peak 1) is an O-H stretching vibration absorption peak, 2922cm -1 (peak 2) asymmetric stretching vibration absorption peak of methylene, 2852cm -1 (peak 3) symmetrical stretching vibration peak of methylene, 1732cm -1 (peak 4) C=O stretching vibration absorption peak in carboxyl, 1467cm -1 (peak 5) asymmetric flexural vibration of methylene group, 1398cm -1 (peak 6) symmetrical flexural vibration of methylene, 1205cm -1 (peak 7) C-N telescopic vibration absorption peak, 1056cm -1 (peak 8) is an asymmetric stretching vibration absorption peak of sulfonic acid group S=O, 721cm -1 (peak 9) is a vibration of 599cm in the methylene basal plane -1 (peak 10) is the telescopic vibration absorption peak of S-O.
Pure QH-16 was subjected to nuclear magnetic analysis (FIG. 8): 1 H NMR(400MHz,CD 3 OD),δ:0.8830-0.9171(3H,t,J＝6.82Hz,-CH 3 ),1.2885(26H,s,CH 3 (CH 2 ) 13 CH 2 CH 2 N-),1.7467-1.7828(2H,t,J＝7.22Hz,CH 3 (CH 2 ) 13 CH 2 CH 2 N-),2.6372-2.6693(4H,t,J＝6.42Hz,2×-NCH 2 CH 2 COOH),3.1839-3.2247(6H,t,J＝8.16Hz,-NCH 2 CH 2 SO 3 Na and CH 3 (CH 2 ) 14 CH 2 N-),3.8047-3.8455(4H,t,J＝8.16Hz,2×-NCH 2 CH 2 COOH)ppm.
pure QH-16 was mass analyzed (fig. 9): HRMS (ESI) (negative) M/z: [ M-H ] + ] - Calcd for C 24 H 46 O 7 NSClNa,550.2581；Found 550.3295.[M-Na + ] - Calcd for C 24 H 47 O 7 NSCl,528.2762；Found 528.3354.[M-Na + -Cl - -H + ] - Calcd for C 24 H 46 O 7 NS,492.2995；Found 492.3395.
The reaction formula is:
example 4
(1) Preparation of sodium carboxylate Quaternary ammonium sulfonate surfactant (product QH-18):
1) 269.51g of octadecylamine, 800g of isopropyl alcohol and heating, stirring and dissolving at 75 ℃, adding 154.9g of acrylic acid in 5 batches, stirring and reacting for 4 hours at 75 ℃ to obtain a reaction intermediate ZT-18.
2) 197.8g of 2-chloroethyl sodium sulfonate monohydrate is added into a reaction intermediate ZT-18 in 5 batches, and after the addition is finished, the mixture is stirred and reacted for 4 hours at 75 ℃ to obtain a carboxylic acid quaternary ammonium salt sodium sulfonate surfactant product QH-18; the solvent of the product QH-18 is distilled off under normal pressure, and then methanol is used for recrystallization, separation and purification for 3 times, thus obtaining the pure product QH-18 of the sodium carboxylate quaternary ammonium sulfonate surfactant.
Pure QH-18 was subjected to infrared analysis (fig. 10): 3462cm -1 (peak 1) is a stretching vibration peak of O-H, 2918cm -1 (peak 2) asymmetric stretching vibration absorption peak of methylene, 2850cm -1 (peak 3) symmetrical stretching vibration peak of methylene, 1716cm -1 (peak 4) isC=o stretching vibration absorption peak 1560cm -1 (peak 5) asymmetric stretching vibration absorption peak of C-O, 1471cm -1 (peak 6) asymmetric flexural vibration of methylene group, 1396cm -1 (peak 7) symmetrical flexural vibration of methylene, 1205cm -1 (peak 8) C-N telescopic vibration absorption peak, 1172cm -1 (peak 9) symmetrical telescopic vibration absorption peak of sulfonic acid group S=O, 1062cm -1 (peak 10) is an asymmetric stretching vibration absorption peak of sulfonic acid group S=O, 721cm -1 (peak 11) is a methylene basal plane internal rocking vibration 594cm -1 (peak 12) is a telescopic vibration absorption peak of S-O, 516cm -1 (peak 13) is the flexural vibration absorption peak of O-H.
Pure QH-18 was subjected to nuclear magnetic analysis (FIG. 11): 1 H NMR(400MHz,CD 3 OD),δ:0.8835-0.9178(3H,t,J＝6.86Hz,-CH 3 ),1.2884(30H,s,CH 3 (CH 2 ) 15 CH 2 CH 2 N-),1.7499-1.7852(2H,t,J＝7.06Hz,CH 3 (CH 2 ) 15 CH 2 CH 2 N-),2.6520-2.6841(4H,t,J＝6.42Hz,2×-NCH 2 CH 2 COOH),3.1810-3.2218(6H,t,J＝8.16Hz,-NCH 2 CH 2 SO 3 Na and CH 3 (CH 2 ) 16 CH 2 N-),3.8030-3.8438(4H,t,J＝8.16Hz,2×-NCH 2 CH 2 COOH)ppm.
pure QH-18 was mass analyzed (fig. 12): HRMS (ESI) (Negative) M/z: [ M-Na ] + ] - Calcd for C 26 H 51 O 7 NSCl,556.3075；Found556.3919.
The reaction formula is:
experimental example 1
Foam inhibition performance tests were carried out on pure products QH (QH-12, QH-14, QH-16 or QH-18) of sodium carboxylate quaternary ammonium sulfonate surfactants synthesized in examples 1 to 4: 10 mL of 0.5% (mass fraction) aqueous solution of sodium dodecyl benzene sulfonate (LBS) and a certain mass of sample were taken at room temperature, poured into a 100mL stoppered cylinder, stoppered and vigorously shaken up and down for 20 times, and the volume (mL) of foam produced was recorded. The foam inhibition value (E) can be used for measuring the foam inhibition capacity of the sample.
E＝(V 0 -V 1 )/V 0
Wherein V is 0 Foam volume (mL) at blank test is shown; v (V) 1 Foam volume (mL) at the time of sample addition is shown.
The foam inhibition properties of the pure products QH (QH-12, QH-14, QH-16 or QH-18) and OP-10 (commercial products) of the sodium carboxylate quaternary ammonium sulfonate surfactants were compared and are shown in Table 1. It can be seen that the carboxylic acid quaternary ammonium salt sodium sulfonate surfactant QH (QH-12, QH-14, QH-16 or QH-18) prepared in examples 1-4 has a certain foam inhibition capability.
Table 1 bubble inhibiting properties of the samples
Experimental example 2
Emulsifying capacity: at room temperature, 20mL of a sample aqueous solution of pure product QH (QH-12, QH-14, QH-16 or QH-18) of the carboxylic acid quaternary ammonium salt sodium sulfonate surfactant prepared in examples 1 to 4 (mass fraction) or an aqueous solution of OP-10 (commercial product) and 20mL of liquid paraffin were taken, poured into a 100mL cylinder with a stopper, the stopper was plugged, vigorously shaken 5 times, allowed to stand for 1min, repeated 5 times, and the time for separating 10 mL of water was measured.
The experimental data are shown in table 2. As can be seen, the sodium carboxylate quaternary ammonium sulfonate surfactant QH (QH-12, QH-14, QH-16 or QH-18) synthesized in examples 1-4 has a good emulsifying capacity.
Table 2 emulsifying capacity of samples
| Product(s) | Time to split(s) |
| Product QH-12 | 251 |
| Product QH-14 | 196 |
| Product QH-16 | 180 |
| Product QH-18 | 153 |
| OP-10 | 684 |
Experimental example 3
Foamability and foam stability: 80mL of an aqueous solution of the product QH (QH-12, QH-14, QH-16 or QH-18) was prepared at room temperature at a molar concentration of 0.001 mol/L. 20mL of the removed solution was placed in a 100mL stoppered cylinder and incubated in a constant temperature water bath at 25℃for 10 minutes. Shaking vigorously for 20 times, standing in a water bath, and recording the initial volume value (H 0 ) Volume number of foam after 5 minutes (H 5 ) The time (t 1/2 Defined as half-life).
The experimental data are shown in table 3. Compared with sodium dodecyl benzene sulfonate, the product QH (QH-12, QH-14, QH-16 or QH-18) has lower foamability and better foam stability. The carboxylic acid quaternary ammonium salt sodium sulfonate surfactant QH (QH-12, QH-14, QH-16 or QH-18) is illustrated as a low foaming surfactant.
Table 3 foamability and foam stability of samples
Experimental example 4
Surface tension test: measuring surface tension by platinum hanging ring method to obtain surface tension (gamma) -log curve (see fig. 13-16), and further obtaining Critical Micelle Concentration (CMC), and surface tension (gamma) under CMC CMC )、C 20 、pC 20 CMC/C 20 (see Table 4). As can be seen, the surface properties of the product QH (QH-12, QH-14, QH-16 or QH-18) are better.
TABLE 4 surface Performance parameters
| Product(s) | CMC(mol·L -1 ) | γ CMC (mN·m -1 ) | C 20 (mol·L -1 ) | pC 20 | CMC/C 20 |
| Product QH-12 | 3.73×10 -4 | 34.1 | 4.69×10 -5 | 4.33 | 7.95 |
| Product QH-14 | 1.73×10 -4 | 28.0 | 2.34×10 -5 | 4.63 | 7.39 |
| Product QH-16 | 2.56×10 -4 | 33.4 | 6.29×10 -5 | 4.20 | 4.07 |
| Product QH-18 | 1.99×10 -4 | 34.6 | 2.19×10 -5 | 4.11 | 9.09 |
The foregoing description is only of the preferred embodiments of the invention and is not intended to limit the invention. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (10)
1. The carboxylic acid quaternary ammonium salt sodium sulfonate surfactant is characterized in that the molecular structural general formula QH is:
wherein n=12, 14, 16, 18;
C n H 2n+1 is a straight chain alkyl group.
2. The method for preparing the carboxylic acid quaternary ammonium salt sodium sulfonate surfactant according to claim 1, which is characterized by comprising the following steps:
s1: mixing fatty primary amine, an alcohol solvent and acrylic acid for reaction to obtain a reaction intermediate ZT, wherein the structural general formula of the reaction intermediate ZT is as follows:
C n H 2n+1 N(CH 2 CH 2 COOH) 2 ；
wherein n=12, 14, 16, 18;
C n H 2n+1 is a linear alkyl group;
s2: adding 2-chloroethyl sodium sulfonate monohydrate into the reaction intermediate ZT, and carrying out mixed reaction to obtain a carboxylic acid quaternary ammonium salt sodium sulfonate surfactant product QH; and (3) evaporating the solvent from the product QH under normal pressure, and recrystallizing, separating and purifying by using an organic solvent to obtain the pure product QH of the carboxylic acid quaternary ammonium salt sodium sulfonate surfactant.
3. The method for preparing the carboxylic acid quaternary ammonium salt sodium sulfonate surfactant according to claim 2, wherein the molar ratio of the fatty primary amine to the alcohol solvent to the acrylic acid to the sodium 2-chloroethyl sulfonate monohydrate is 1:10.6 to 19.6:2.00 to 2.22:1.00 to 1.11.
4. The method for preparing a sodium carboxylate quaternary ammonium sulfonate surfactant according to claim 2, wherein in the step S1, the primary fatty amine is dodecaprimary amine, tetradecyl primary amine, hexadecyl primary amine or octadecyl primary amine.
5. The method for preparing a sodium sulfonate surfactant of a quaternary ammonium carboxylate salt as claimed in claim 2, wherein in the step S1, the alcohol solvent is one or more of ethanol and isopropanol.
6. The method for preparing a sodium carboxylate quaternary ammonium sulfonate surfactant according to claim 2, wherein in the step S1, the reaction temperature is 60-80 ℃ and the reaction time is 3-5h.
7. The method for preparing a sodium carboxylate quaternary ammonium sulfonate surfactant according to claim 2, wherein in the step S2, the organic solvent for recrystallization, separation and purification is petroleum ether, methanol or ethyl acetate.
8. The method for preparing a sodium carboxylate quaternary ammonium sulfonate surfactant according to claim 2, wherein in the step S2, the reaction temperature is 60-80 ℃ and the reaction time is 3-5h.
9. The method for preparing the carboxylic acid quaternary ammonium salt sodium sulfonate surfactant according to claim 2, which is characterized by comprising the following steps:
(1) Adding primary aliphatic amine into a reaction container, adding an alcohol solvent, heating and stirring at 60-80 ℃ to dissolve, adding acrylic acid in batches, and stirring at 60-80 ℃ to react for 3-5h after the addition is finished to obtain a reaction intermediate ZT;
(2) Adding 2-chloroethyl sodium sulfonate monohydrate into the reaction intermediate ZT in batches, and stirring at 60-80 ℃ for reaction for 3-5 hours after the addition is finished to obtain a carboxylic acid quaternary ammonium salt sodium sulfonate surfactant product QH; and (3) evaporating the solvent from the product QH under normal pressure, and then recrystallizing, separating and purifying the product QH for 2 to 3 times by using an organic solvent to obtain the pure product QH of the carboxylic acid quaternary ammonium salt sodium sulfonate surfactant.
10. Use of a sodium carboxylate quaternary ammonium sulfonate surfactant according to claim 1 as a suds suppressor, a low foaming surfactant or an emulsifier.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210853373.8A CN117467455A (en) | 2022-07-20 | 2022-07-20 | Carboxylic acid quaternary ammonium salt sodium sulfonate surfactant, and preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210853373.8A CN117467455A (en) | 2022-07-20 | 2022-07-20 | Carboxylic acid quaternary ammonium salt sodium sulfonate surfactant, and preparation method and application thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN117467455A true CN117467455A (en) | 2024-01-30 |
Family
ID=89624291
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202210853373.8A Pending CN117467455A (en) | 2022-07-20 | 2022-07-20 | Carboxylic acid quaternary ammonium salt sodium sulfonate surfactant, and preparation method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN117467455A (en) |
-
2022
- 2022-07-20 CN CN202210853373.8A patent/CN117467455A/en active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN113083152B (en) | Carboxylic acid sulfonic acid type surfactant, and preparation method and application thereof | |
| CN115058254B (en) | Carboxylate sulfonate surfactant and preparation method and application thereof | |
| CN115584268A (en) | Disulfonic acid betaine viscoelastic surfactant, preparation method and application | |
| US3376333A (en) | Sulfuric acid esters of linear secondary alcohol ethoxylates and salts thereof and method of producing same | |
| AU642949B2 (en) | Process for the preparation of beta-substituted sulphonic acids and/or sulphonates | |
| CN117467455A (en) | Carboxylic acid quaternary ammonium salt sodium sulfonate surfactant, and preparation method and application thereof | |
| US2508652A (en) | Di-nu-substituted piperazine derivatives and method of preparing same | |
| CN114957052B (en) | Polyamide sulfonic acid type surfactant, and preparation method and application thereof | |
| CN115872908B (en) | Sodium amide carboxylate sulfonate surfactant, and preparation method and application thereof | |
| US2541260A (en) | Di-n-alkoxy substituted piperazine derivatives and method of preparing same | |
| CN113105373A (en) | Tertiary amine sulfonic acid surfactant, and preparation method and application thereof | |
| CN115141127A (en) | Sodium tertiary amine carboxylate sulfonate surfactant, and preparation method and application thereof | |
| CN116082202B (en) | Primary amide sulfonic acid type surfactant, and preparation method and application thereof | |
| CN115232035B (en) | Di-tertiary amine bisamide sulfonic acid type surfactant and preparation method and application thereof | |
| CN115716789B (en) | Primary amide sodium carboxylate tertiary amine surfactant, and preparation method and application thereof | |
| CN117402627A (en) | Tertiary amine amidosulfonic acid type surfactant, preparation method and application thereof | |
| CN113750906B (en) | Amphoteric surfactant and preparation method and application thereof | |
| CN115894309A (en) | Tertiary amine quaternary ammonium salt sulfonic acid surfactant, and preparation method and application thereof | |
| CN113694823B (en) | Secondary amide sulfonic acid surfactant, and preparation method and application thereof | |
| CN116903510A (en) | Tri-head-based surfactant and preparation method and application thereof | |
| US3657347A (en) | Production of long chain amines by reacting monoethanolamine monoisopropanolamine and/or ethylenediamine with long chain straight chain secondary chlorides | |
| CN115746876A (en) | Low-foam surfactant and preparation method and application thereof | |
| CN115925587A (en) | Tertiary amine dianion surfactant and preparation method and application thereof | |
| CN115368915A (en) | Quaternary ammonium carboxylate sodium sulfonate surfactant, and preparation method and application thereof | |
| CN116813520A (en) | Amphoteric heterocyclic surfactant, and preparation method and application thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |