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CN105833792B - fluorine-containing surfactant and preparation method thereof - Google Patents

fluorine-containing surfactant and preparation method thereof Download PDF

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CN105833792B
CN105833792B CN201511031679.1A CN201511031679A CN105833792B CN 105833792 B CN105833792 B CN 105833792B CN 201511031679 A CN201511031679 A CN 201511031679A CN 105833792 B CN105833792 B CN 105833792B
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fluorine
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CN105833792A (en
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史大阔
张永明
阎育才
王汉利
赵栋
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Shandong Dongyue Future Hydrogen Energy Materials Co Ltd
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    • 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
    • A—HUMAN NECESSITIES
    • A62—LIFE-SAVING; FIRE-FIGHTING
    • A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
    • A62D1/00—Fire-extinguishing compositions; Use of chemical substances in extinguishing fires
    • A62D1/0071—Foams
    • A62D1/0085—Foams containing perfluoroalkyl-terminated surfactant

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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)

Abstract

The present invention relates to a kind of fluorine-containing surfactants and preparation method thereof.A kind of fluorine-containing surfactant of the present invention, structural formula of compound are：(Ⅰ).Preparation process of the present invention is succinct, of low cost；Both sexes fluorocarbon surfactant has excellent emulsification, and the auxiliary agent as fluoro-containing macromolecule material polymerization uses, and can also be used in the finishing agent of paper, leather and fabric as emulsifier, while can be used with metal surface decontaminating cleaning agents.Different fluorine-containing surfactant stoste is configured easily with other surfaces context of vaccine administration in amphoteric surfactant simultaneously, applied to various aspects, is especially applied to the aqueous film-forming foam extinguishing agent of fire-fighting domain, main function is sprawled as foam stabilization, film forming.

Description

fluorine-containing surfactant and preparation method thereof
Technical Field
The invention relates to a fluorine-containing surfactant and a preparation method thereof.
Technical Field
The surfactant has various types and classification forms, is widely applied nowadays, and is most widely used, wherein the most used surfactant is a hydrocarbon surfactant, and a hydrophobic group is a hydrocarbon alkyl group. When the hydrogen atoms at the hydrophobic end of the hydrocarbon surfactant are completely or partially substituted by fluorine atoms, the hydrocarbon surfactant is formed. The conversion of hydrocarbon surfactants to fluorocarbon surfactants results in qualitative improvements in surface properties. The fluorocarbon surfactant belongs to a special surfactant, plays a special important role in daily chemical industry, and is the highest surface activity so far. It has the characteristics of three high and two hydrophobic (high surface activity, high thermal stability, high chemical stability and hydrophobic and oleophobic properties). The application field of the fluorocarbon surfactant is very wide, and the fluorocarbon surfactant is widely applied to the fields of chemistry, petroleum, electronics, textile, papermaking, printing ink, fire fighting and the like.
The fluorocarbon surfactant has a main structure of a fluorocarbon chain form, and the widely applied perfluoro straight-chain alkanes such as PFOA and PFOS at present are applied to a plurality of fields, but the fluorocarbon surfactant and the PFOA are found to have very high biological accumulation capacity after long-term use and are extremely difficult to degrade in the environment. For the continuing environmental hazard of perfluorinated surfactants of the C8 class (PFOA/PFOS), the Stockholm convention has classified them as Persistent Organic Pollutants (POPs). The main challenge currently faced is to find a suitable alternative that retains its superior surface activity and spreading properties while reducing environmental pollution through natural degradation. The invention adopts fluoroether structure to replace perfluorocarbon chain structure, and makes series research to obtain expected effect.
Disclosure of Invention
The invention aims to provide a fluorine-containing surfactant and a preparation method thereof, wherein the surfactant adopts a perfluoropolyether chain to replace the traditional perfluoroalkyl chain, is easy to degrade and is environment-friendly; the fluorocarbon surfactant is applied to complex formulation, is widely applied to the industries of fire fighting, oil extraction and the like, and is particularly used as an aqueous film-forming foam extinguishing agent. The product of the invention has simple preparation process, low cost and good industrial application prospect.
The invention relates to a fluorine-containing surfactant, the structural formula of the compound is as follows:
wherein
X is H or a halogen element;
m is an integer of 1 to 5; n is an integer of 1 to 10;
R1is hydrogen, methyl or alkyl of 2 to 6 carbon atoms;
R2and R3Are each an alkyl group of 1 to 6 carbon atoms;
a is O-, (CH)2)pCOO‐Or (CH)2)pSO3 ‐(ii) a Wherein p is an integer from 1 to 10.
m is 2 and n is 2-4.
R1 is hydrogen or methyl.
The compound has a surface tension of not more than 16mN/m in an aqueous solution having a concentration of 0.1%.
The preparation method of the fluorine-containing surfactant comprises the following steps:
dissolving primary amine in a dichloromethane or tetrahydrofuran solvent, adding alkali, dropwise adding solutions III, IV or V at the temperature of 30-60 ℃, and reacting the obtained sulfonamide product with a quaternizing agent to obtain a final fluorocarbon surfactant;
the chemical equation is as follows:
wherein,
the preparation steps of III are as follows: dropwise adding the raw material II into a solvent which is added with carbonate in advance for reaction within 1-5 hours, adding an acid solution, refluxing at 130-180 ℃, carrying out reduced pressure distillation to obtain a mixed solution of a main product III and water, separating to remove a water layer, drying, and filtering to obtain a pure product of the product III for later use;
the preparation steps of IV are as follows: dissolving a raw material III in a halothane solvent, introducing fluorine gas at the temperature of-40 ℃, decompressing and rectifying until the reaction is finished to obtain a product IV for later use, or taking II as a raw material, introducing the fluorine gas to react to obtain reaction liquid, decompressing and rectifying to obtain a product IV for later use;
the preparation steps of V are as follows: placing the raw material III and chlorine gas in a high-pressure reaction kettle for reaction, controlling the temperature at 70-120 ℃, controlling the reaction time at 6-12 hours, and rectifying after the reaction is finished to obtain a product V for later use;
the chemical equation is as follows:
in the step (1), the raw material II is dripped into a solvent in which carbonate is added in advance to react, the reaction temperature is controlled between 20 ℃ and 80 ℃, and the reaction time is controlled between 4 hours and 10 hours.
The carbonate comprises one or more of sodium carbonate, potassium carbonate, lithium carbonate, cesium carbonate, magnesium carbonate, sodium bicarbonate or potassium bicarbonate.
The solvent comprises one or more of ethylene glycol dimethyl ether, ethylene glycol diethyl ether, diethylene glycol dimethyl ether or tetraethylene glycol dimethyl ether.
The quaternizing agent is hydrogen peroxide or chloroalkyl carboxylate or chloroalkyl sulfonate.
The fluorine-containing surfactant is applied to the fields of fire fighting, oil fields, chemical industry, spinning or papermaking.
The preparation steps of the fluorine-containing surfactant are as follows:
dissolving alkyl-substituted primary amine in a dichloromethane or tetrahydrofuran solvent, adding an organic base or an inorganic base, dropwise adding a solution III, IV or V at the temperature of 30-60 ℃, controlling the reaction time to be 5-20 hours, and reacting the obtained sulfonamide product with hydrogen peroxide, chloroalkyl carboxylate, chloroalkyl sulfonate or sultone respectively to obtain the final amphoteric fluorocarbon surfactant.
Wherein the preparation steps of III are as follows: dropwise adding the raw material II into a solvent which is added with carbonate in advance within 1-5 hours, controlling the reaction temperature to be 20-80 ℃, controlling the reaction time to be 4-10 hours, adding an acid aqueous solution, controlling the molar ratio of acid to the raw material II to be 1-5, refluxing for 1-5 hours at 130-180 ℃, then carrying out reduced pressure distillation to obtain a mixed solution of a product III and water, separating to remove a water layer, drying, and carrying out reduced pressure rectification on the filtered solution to obtain a pure product of the product III;
the preparation steps of IV are as follows: dissolving a raw material III in a halothane solvent, introducing fluorine gas at the temperature of-40 ℃, decompressing and rectifying until the reaction is finished to obtain a product IV for later use, or taking II as a raw material, introducing the fluorine gas at the temperature of 20-100 ℃ for reaction to obtain a reaction liquid, decompressing and rectifying to obtain the product IV for later use;
the preparation steps of V are as follows: and (3) placing the raw material III and chlorine gas into a high-pressure reaction kettle under the pressure of 0.5-5 MPa for reaction, controlling the temperature at 70-120 ℃ and the reaction time at 6-12 hours, and rectifying after the reaction is finished to obtain a product V.
Compared with the prior art, the invention has the following beneficial effects:
the preparation process is simple and low in cost; the amphoteric fluorocarbon surfactant has excellent emulsifying effect, can be used as an auxiliary agent for polymerization of fluorine-containing high polymer materials, can also be used as an emulsifier in finishing agents of paper, leather and fabrics, and can be used with a metal surface decontamination cleaning agent. Meanwhile, the amphoteric surfactant is easy to be compatible with other surfactants, different fluorine-containing surfactant stock solutions are prepared, and the amphoteric surfactant is applied to various aspects, particularly applied to an aqueous film-forming foam extinguishing agent in the field of fire fighting and mainly used for stabilizing foam and spreading a formed film.
Drawings
FIG. 1 shows Ia of example 11H NMR spectrum
Detailed Description
The present invention is further illustrated by the following examples, but the embodiments of the present invention are not limited thereto, and those skilled in the art can make some insubstantial modifications and adjustments according to the disclosure of the present invention, and still fall within the scope of the present invention.
Example 1
(1) Adding 120g of anhydrous sodium carbonate into a 3L three-necked bottle, then adding 1000mL of tetraethylene glycol dimethyl ether, slowly dropwise adding 680g of raw material IIa, controlling the dropwise adding time to be 2 hours, controlling the temperature to be below 50 ℃, continuing to react for 3 hours after the dropwise adding is finished, then adding 150g of 85% phosphoric acid and 150g of deionized water, heating to 150 ℃, carrying out reflux reaction for 2 hours, then distilling out a mixture of the product IIIa and water by reduced pressure distillation, separating and drying, and carrying out reduced pressure rectification again to obtain the product IIIa580g with the yield of 92%.
(2) Dissolving 101g of N, N-dimethyl propane diamine in 500mL of dichloromethane in a 2L three-necked bottle, adding 110g of triethylamine, dropwise adding a dichloromethane (400mL) solution of a raw material IIIa (580g) in ice bath, dropwise adding within 1 hour, removing the ice bath, heating to room temperature, continuing to react for 3 hours, evaporating dichloromethane after the reaction is finished, adding 1L of ethyl acetate, washing with deionized water (300mL multiplied by 3), washing, drying an organic layer with anhydrous sodium sulfate, filtering, evaporating the solution to dryness to obtain 566g of a VIa crude product, wherein the yield is 86%.
(3) And putting 566g of the obtained intermediate VIa and 108g of sodium chloroacetate in a 3L three-necked bottle, adding 1000mL of ethanol, then adding 1mL of triethylamine and 2mL of water, carrying out reflux reaction for 24 hours, filtering insoluble substances after the reaction is finished, and evaporating the filtrate under reduced pressure to dryness to obtain 606g of the product Ia with the yield of 98%.
Ib in FIG. 11H NMR spectrum.
The chemical equation is as follows:
example 2
This example is the same as example 1, except that:
the step (3) is as follows: and (3) putting 100g of the obtained intermediate VIa and 20g of hydrogen peroxide (30%) in a 1L three-necked bottle, performing reflux reaction, adding hydrogen peroxide with the same equivalent weight every 8 hours, after the reaction is finished for 24 hours, adding 0.04g of manganese dioxide, continuing the reaction for 3 hours, testing whether hydrogen peroxide residue exists by using a starch potassium iodide test paper, filtering, and evaporating the filtrate under reduced pressure to dryness to obtain 94g of a product Ib with the yield of 92%.
The chemical equation is as follows:
example 3
This example is the same as example 1, except that:
the step (1) is as follows: adding 120g of anhydrous sodium carbonate into a 3L three-necked bottle, then adding 1000mL of tetraethylene glycol dimethyl ether, slowly adding 680g of a raw material II dropwise, controlling the dropwise adding time to be 2 hours, controlling the temperature to be below 40 ℃, continuing to react for 3 hours after the dropwise adding is finished, then adding 350g of 65% sulfuric acid, heating to 150 ℃, carrying out reflux reaction for 2 hours, then distilling out a mixture of a product IIIa and water through reduced pressure distillation, separating and drying, and carrying out reduced pressure rectification again to obtain 501g of a product, wherein the yield is 79%.
The chemical equation is as follows:
example 4
This example is the same as example 1, except that:
the step (1) is as follows: adding 120g of anhydrous sodium carbonate into a 3L three-necked bottle, then adding 1000mL of tetraethylene glycol dimethyl ether, slowly adding 680g of a raw material II dropwise, controlling the dropwise adding time to be 2 hours, controlling the temperature to be below 40 ℃, continuing to react for 3 hours after the dropwise adding is finished, then adding 270g of concentrated hydrochloric acid, stirring and reacting for 1 hour at room temperature, then heating to 150 ℃, performing reflux reaction for 5 hours, then evaporating a mixture of a product IIIa and water through reduced pressure distillation, washing the mixture to be neutral through multiple times of water washing, drying and rectifying the mixture under reduced pressure again to obtain 565g of the product, wherein the yield is 89%.
The chemical equation is as follows:
example 5
(1) Putting 210g of raw materials IIIa and 500mL of perfluoro-n-hexane into a 1L high-pressure reaction kettle, replacing with nitrogen for 3 times, reducing the temperature to 0 ℃, and then slowly introducing 5% of F in batches2/N2Stopping introducing gas when the pressure of the reaction kettle is increased to 1.5MPa every time, carrying out reaction at intervals of 30 minutes every batch, stopping introducing the fluorine gas after the total pressure of the fluorine gas is reduced to reaction equivalent, continuing the reaction for 1 hour, and carrying out reduced pressure rectification on the reaction liquid to obtain 190g of the product IVa with the yield of 87%.
(2) Dissolving 33g of N, N-dimethyl propane diamine in 200mL of dichloromethane in a 2L three-necked bottle, adding 36g of triethylamine, dropwise adding a dichloromethane (200mL) solution of a raw material IVa (190g) in an ice bath, dropwise adding within 1 hour, removing the ice bath, heating to room temperature, continuing to react for 3 hours, evaporating the dichloromethane after the reaction is finished, adding 1L of ethyl acetate, washing with deionized water (300mL multiplied by 3), washing, drying with anhydrous sodium sulfate of an organic layer, filtering, and evaporating the solution to obtain 185g of a crude product of VIb, wherein the yield is 86%.
(3) Putting 180g of the intermediate VIa and 34g of sodium chloroacetate obtained in the step of putting the intermediate VIa and the sodium chloroacetate into a 1L three-necked bottle, adding 300mL of ethanol, then adding 1mL of triethylamine and 2mL of water, carrying out reflux reaction for 24 hours, filtering insoluble substances after the reaction is finished, and evaporating the filtrate under reduced pressure to obtain the product Ic193g with the yield of 98%.
Wherein IIIa in step (1) is obtained by the method of example 1.
The chemical equation is as follows:
example 6
This example is the same as example 5, except that:
the step (3) is as follows: putting 102g of the obtained intermediate VIb and 20g of hydrogen peroxide (30%) into a 1L three-necked bottle, performing reflux reaction, adding hydrogen peroxide with the same equivalent weight every 8 hours, after the reaction is finished for 24 hours, adding 0.04g of manganese dioxide, continuing the reaction for 3 hours, testing whether hydrogen peroxide residue exists by using a starch potassium iodide test paper, filtering, and evaporating the filtrate under reduced pressure to dryness to obtain 88g of a product Id with the yield of 86%.
The chemical equation is as follows:
example 7
This example is the same as example 5, except that:
the step (1) is as follows: placing 33g of raw material IIa and 300mL of perfluoro-n-hexane in a 1L high-pressure reaction kettle, replacing with nitrogen for 3 times, reducing the temperature to 0 ℃, then slowly introducing fluorine gas, stopping introducing the gas when the pressure of the reaction kettle is increased to 1.5MPa, reacting at 0 ℃ for 5 hours, heating to 50 ℃, continuing to react for 5 hours, emptying the internal pressure of the reaction kettle after the reaction is finished, and carrying out reduced pressure rectification on the reaction liquid to obtain a product IVa25g with the yield of 76%.
The chemical equation is as follows:
example 8
(1) Putting 210g of raw material IIIa into a 1L high-pressure reaction kettle, replacing with nitrogen for 3 times, slowly introducing dry chlorine, closing a chlorine feeding hole after the internal pressure of the reaction kettle reaches 8.5MPa, raising the temperature to 70 ℃, reacting for 6 hours, and then carrying out reduced pressure rectification on reaction liquid to obtain 145g of product Va with the yield of 65%.
(2) In a 2L three-necked bottle, 24g of N, N-dimethyl propane diamine is dissolved in 100mL of dichloromethane, 24g of triethylamine is added, a raw material Va (140g) dichloromethane (100mL) solution is dropwise added under ice bath, the dropwise addition is completed within 1 hour, the ice bath is removed, the temperature is raised to room temperature, the reaction is continued for 3 hours, after the reaction is completed, the dichloromethane is evaporated to dryness, 1L of ethyl acetate is added, then deionized water is added for washing (300mL multiplied by 3), and washing is carried out, an organic layer is dried by anhydrous sodium sulfate, filtering is carried out, the solution is evaporated to dryness to obtain 140g of a crude product of VIc, and.
(3) And (3) putting 135g of the obtained intermediate VIc and 26g of sodium chloroacetate in a 1L three-necked bottle into a reaction bottle, adding 400mL of ethanol, then adding 1.5mL of triethylamine and 2mL of water, carrying out reflux reaction for 24 hours, filtering insoluble substances after the reaction is finished, and evaporating the filtrate under reduced pressure to dryness to obtain 105g of the product Ie with the yield of 97%.
Wherein IIIa in step (1) is obtained by the method of example 1.
The chemical equation is as follows:
example 9
This example is the same as example 8, except that:
the step (3) is as follows: and (3) putting 100g of the obtained intermediate VIc and 20g of hydrogen peroxide (30%) into a 1L three-necked bottle, performing reflux reaction, adding hydrogen peroxide with the same equivalent weight every 8 hours, after the reaction is finished for 24 hours, adding 0.04g of manganese dioxide, continuing the reaction for 3 hours, testing whether hydrogen peroxide residue exists by using a starch potassium iodide test paper, filtering, and evaporating filtrate under reduced pressure to dryness to obtain 98g of a product If, wherein the yield is 96%.
The reaction equation is as follows:
example 10
And (3) putting 100g of the obtained intermediate VIa and 25g of chloromethyl sodium sulfonate into a 1L three-necked bottle, adding 300mL of ethanol, then adding 1mL of triethylamine and 2mL of water, carrying out reflux reaction for 24 hours, filtering insoluble substances after the reaction is finished, and evaporating the filtrate under reduced pressure to dryness to obtain 115g of the product Ig, wherein the yield is 95%.
VIa in example 10 was prepared according to the method of VIa of example 1.
The chemical equation is as follows:

Claims (10)

1. A fluorosurfactant having the formula:
（Ⅰ）
wherein
X is H or a halogen element;
m is an integer of 1 to 5; n is an integer of 1 to 10;
R1is hydrogen, methyl or alkyl of 2 to 6 carbon atoms;
R2and R3Are each an alkyl group of 1 to 6 carbon atoms;
a is O-or (CH)2)pSO3 -(ii) a Wherein p is an integer from 1 to 10.
2. The fluorosurfactant of claim 1 wherein m is 2 and n is 2-4.
3. The fluorosurfactant of claim 1 wherein-R is characterized by1Is hydrogen or methyl.
4. The fluorosurfactant of claim 1 wherein the compound has a surface tension of no greater than 16mN/m in a 0.1% aqueous solution.
5. A method of preparing the fluorosurfactant of claim 1 comprising the steps of:
dissolving primary amine in a dichloromethane or tetrahydrofuran solvent, adding alkali, dropwise adding solutions III, IV or V at the temperature of 30-60 ℃, and reacting the obtained sulfonamide product with a quaternizing agent to obtain a final fluorocarbon surfactant;
；
wherein,
the preparation steps of III are as follows: dropwise adding the raw material II into a solvent which is added with carbonate in advance for reaction within 1-5 hours, adding an acid solution, refluxing at 130-180 ℃, carrying out reduced pressure distillation to obtain a mixed solution of a main product III and water, separating to remove a water layer, drying, and filtering to obtain a pure product of the product III for later use;
the preparation steps of IV are as follows: dissolving a raw material III in a halothane solvent, introducing fluorine gas at the temperature of-40 ℃, decompressing and rectifying until the reaction is finished to obtain a product IV for later use, or introducing the fluorine gas to react by taking II as a raw material to obtain a reaction liquid, decompressing and rectifying to obtain the product IV for later use;
the preparation steps of V are as follows: placing the raw material III and chlorine gas in a high-pressure reaction kettle for reaction, controlling the temperature at 70-120 ℃, controlling the reaction time at 6-12 hours, and rectifying after the reaction is finished to obtain a product V for later use;
。
6. the method for preparing a fluorine-containing surfactant according to claim 5, wherein in the step (1), the raw material II is added dropwise into the solvent into which the carbonate is previously added to react, the reaction temperature is controlled to be 20-80 ℃, and the reaction time is controlled to be 4-10 hours.
7. The method of claim 5, wherein the carbonate salt comprises one or more of sodium carbonate, potassium carbonate, lithium carbonate, cesium carbonate, magnesium carbonate, sodium bicarbonate, or potassium bicarbonate.
8. The method according to claim 5, wherein the solvent comprises one or more of ethylene glycol dimethyl ether, ethylene glycol diethyl ether, diethylene glycol dimethyl ether, and tetraethylene glycol dimethyl ether.
9. The method for preparing a fluorine-containing surfactant according to claim 5, wherein the quaternizing agent is hydrogen peroxide or chloroalkyl carboxylate or chloroalkyl sulfonate.
10. Use of the fluorosurfactant of claim 1 in the fields of fire fighting, oil field, chemical, textile or paper making.
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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999041292A1 (en) * 1998-02-13 1999-08-19 E.I. Du Pont De Nemours And Company Fluorinated ionomers and their uses
CN102389745A (en) * 2011-08-15 2012-03-28 华中师范大学 Preparation method of fluorine-containing double-type cationic surfactant and use thereof
CN102500087A (en) * 2011-10-24 2012-06-20 徐衡 Method for preparing perfluorohexane surfactant serving as main agent of aqueous film-forming extinguishing agent directly
CN102633688A (en) * 2012-04-13 2012-08-15 华东理工大学 Perfluorovinyl ether sulfonate as well as preparation method and application thereof
CN105017097A (en) * 2015-07-07 2015-11-04 武汉市化学工业研究所有限责任公司 Preparation method for surfactant N-carboxyethyl, N-3-dimethylaminopropyl-perfluoro hexyl sulfonamide

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999041292A1 (en) * 1998-02-13 1999-08-19 E.I. Du Pont De Nemours And Company Fluorinated ionomers and their uses
CN102389745A (en) * 2011-08-15 2012-03-28 华中师范大学 Preparation method of fluorine-containing double-type cationic surfactant and use thereof
CN102500087A (en) * 2011-10-24 2012-06-20 徐衡 Method for preparing perfluorohexane surfactant serving as main agent of aqueous film-forming extinguishing agent directly
CN102633688A (en) * 2012-04-13 2012-08-15 华东理工大学 Perfluorovinyl ether sulfonate as well as preparation method and application thereof
CN105017097A (en) * 2015-07-07 2015-11-04 武汉市化学工业研究所有限责任公司 Preparation method for surfactant N-carboxyethyl, N-3-dimethylaminopropyl-perfluoro hexyl sulfonamide

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Address before: 256401 Tangshan, Shandong, Huantai Town, Zibo

Applicant before: Shandong Dongyue Shenzhou New Material Co., Ltd.

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Address after: 256401 Dongyue fluorosilicone Material Industrial Park, Tangshan Town, Huantai, Zibo, Shandong

Patentee after: Shandong Dongyue future hydrogen energy materials Co., Ltd

Address before: 256401 Dongyue fluorosilicone Material Industrial Park, Tangshan Town, Huantai, Zibo, Shandong

Patentee before: Shandong Dongyue future hydrogen energy materials Co.,Ltd.