CN102584646A - N-(3-perfluor hexyl sulfamide) propyl-N, N, N-trimethyl ammonium iodide as well as preparation and application thereof - Google Patents

N-(3-perfluor hexyl sulfamide) propyl-N, N, N-trimethyl ammonium iodide as well as preparation and application thereof Download PDF

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CN102584646A
CN102584646A CN2011104515427A CN201110451542A CN102584646A CN 102584646 A CN102584646 A CN 102584646A CN 2011104515427 A CN2011104515427 A CN 2011104515427A CN 201110451542 A CN201110451542 A CN 201110451542A CN 102584646 A CN102584646 A CN 102584646A
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perfluoro hexyl
ammonium iodide
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史鸿鑫
邱小丽
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Zhejiang University of Technology ZJUT
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Abstract

The invention discloses N-(3-perfluor hexyl sulfamide) propyl-N, N, N-trimethyl ammonium iodide as well as preparation and an application of the N-(3-perfluor hexyl sulfamide) propyl-N, N, N-trimethyl ammonium iodide. The structure of the N-(3-perfluor hexyl sulfamide) propyl-N, N, N-trimethyl ammonium iodide is shown as the formula (I), and the N-(3-perfluor hexyl sulfamide) propyl-N, N, N-trimethyl ammonium iodide can be prepared through a simple method. The surface activity of the prepared N-(3-perfluor hexyl sulfamide) propyl-N, N, N-trimethyl ammonium iodide is high, and the N-(3-perfluor hexyl sulfamide) propyl-N, N, N-trimethyl ammonium iodide can be used as surfactants and has wide application prospects.

Description

N-(3-perfluoro hexyl sulfoamido) propyl group-N, N, N-trimethylammonium ammonium iodide and preparation thereof and application
(1) technical field
The present invention relates to the perfluoro hexyl quaternary surfactant.
(2) background technology
Fluorine surfactant is compared with conventional surfactants, and outstanding performance is " three height, two are hated ".Be high surface, high heat-resistant stability and unreactiveness, not only hydrophobic but also hate oil [New Chemical Materials, 2004,32 (8): 46], the high surface of fluorine surfactant is because its intermolecular Van der Waals force is little, has caused the intensive surface adsorption.The fluorine surfactant not only avidity to water is little, and is also not high to the avidity of hydrocarbon polymer, therefore formed the characteristic of hydrophobic and oil repellent.In addition, because of C-F bond energy (4.9 * 10 5Jmol -1) greater than the bond energy (4.2 * 10 of c h bond 5Jmol -1), the C-F key is than c h bond easy fracture not.Fluorine atom because of fluorine atom volume ratio Wasserstoffatoms is big, makes the C-C key be protected because of the shielding effect of fluorine atom after replacing Wasserstoffatoms, and more stable.This has determined the high heat-resistant stability and the unreactiveness of fluorine surfactant.
PFO sulfonyl compound (PFOS), it has potential disadvantageous effect [Analytical Chemistry, 2002,74:584-590] to human health and environment, and [chemical progress, 2006,18 (6): 808-813.] just progressively are eliminated.The substitute of PFOS is all set about seeking by various countries; Minnesota Mining and Manufacturing Company's research and development replace PFOS with perfluoro butyl sulfonic acid (PFBS) and have obtained phasic results [3M Technical Data Bullet in Environmental; Health; Safety, and Regulatory (EHSR) Profile of Perfluorobutane Sulfonate (PFBS), 2007].It is the surfactant [Acta PhySico-Chimica Sinica, 2009,25 (12): 2409-2412] of raw material that people such as Yang Baiqin also develop with PFBS.Perfluoro hexyl sulfonyl compound (PFHS) has identical reactive group with PFOS, PFBS; And different pharmacokinetic data (short half-life) and lower toxicity [Chinese chemical information weekly, 2009, (15)] are arranged than PFOS; Can be used as its substitute; And should have than PFBS and better refuse oily effect [weaving is learned, 1984,5 (1): 59-61].
N, N, N-trimethylammonium-N-(N '-perfluorinated octyl sulfuryl amine base) propyl group ammonium iodide is the fluorochemical surfactant of excellent performance, can be used for " light-water " fire foam, but receives the restriction of PFOS and disabled.With containing C 3And C 4The synthetic quaternary ammonium salt of perfluorochemical because the full-fluorine group carbochain is too short, its surfactivity is not high, and is not good at the spreading property on oils surface, can't substitute C 8PFOS class " light-water " fire foam.With perfluoro hexyl sulfonic acid fluoride (C 6F 13SO 2F) be raw material, replace disabled full-fluorine octyl sulfuryl fluoride, the preparation quaternary ammonium salt also is not in the news.
(3) summary of the invention
One of the object of the invention provides a kind of perfluoro hexyl quaternary ammonium salt N-(3-perfluoro hexyl sulfoamido) propyl group-N with high surface, N, N-trimethylammonium ammonium iodide.
Two of the object of the invention provides a kind of simple perfluor quaternary ammonium salt N-(3-perfluoro hexyl sulfoamido) propyl group-N, N, the preparation method of N-trimethylammonium ammonium iodide.
For realizing the foregoing invention purpose, the technical scheme that the present invention adopts is:
N-of the present invention (3-perfluoro hexyl sulfoamido) propyl group-N, N, N-trimethylammonium ammonium iodide, structure is suc as formula shown in (I):
Figure BDA0000126581390000021
The invention provides the described N-of a kind of preparation (3-perfluoro hexyl sulfoamido) propyl group-N, N, the method for N-trimethylammonium ammonium iodide, said method comprises the steps:
(1) with the N shown in perfluoro hexyl sulfonic acid fluoride shown in the formula (II) and the formula (III); N-dimethyl--1, the 3-tn is a raw material, in the presence of acid binding agent; In aprotic organic solvent; Carry out sulfonamide reaction in-10～150 ℃, reaction finishes after neutralization obtains the N shown in the formula (IV), N-dimethyl--N '-perfluoro hexyl alkylsulfonyl tn;
(2) N; N-dimethyl--N '-perfluoro hexyl alkylsulfonyl tn again with the methyl iodide shown in the formula V in aprotic organic solvent; Carry out quaterisation 1～24h in-10～100 ℃; Reaction solution obtains the N-shown in the formula (I) (3-perfluoro hexyl sulfoamido) propyl group-N, N, N-trimethylammonium ammonium iodide through separation and purification;
Figure BDA0000126581390000031
In the step of the present invention (1), raw material perfluoro hexyl sulfonic acid fluoride and N, N-dimethyl--1, the 3-tn can use the commercial goods.Described perfluoro hexyl sulfonic acid fluoride and N, N-dimethyl--1, the ratio of the amount of substance of 3-tn is 1: 0.5～5, and proportioning is 1: 1.6～2.5 preferably, and best proportioning is 1: 1.6.
The described acid binding agent of step of the present invention (1) is organic bases or mineral alkali; Like n n dimetylaniline, diethylamine, Trimethylamine 99, triethylamine, N-methyl piperidine, N, N-xylidene(s), pyridine, piperidines, yellow soda ash, sodium hydroxide, sodium hydrogencarbonate, salt of wormwood, Pottasium Hydroxide, saleratus or its any several kinds mixture; Preferred acid binding agent is triethylamine, piperidines or sodium hydrogencarbonate; More preferably acid binding agent is a triethylamine.Among the present invention, the ratio of the amount of substance of said perfluoro hexyl sulfonic acid fluoride and acid binding agent is 1: 0.1～5, and the ratio of the preferable perfluoro hexyl sulfonic acid fluoride and the amount of substance of acid binding agent is 1: 1～5; The ratio of the best perfluoro hexyl sulfonic acid fluoride and the amount of substance of acid binding agent is 1: 1～2.
It is one of following that the described aprotic organic solvent of step of the present invention (1) can be selected from: toluene, benzene, acetonitrile, N; Dinethylformamide, N; N-N,N-DIMETHYLACETAMIDE, DMSO 99.8MIN., acetone, tetramethylene sulfone, 1,2-ethylene dichloride, chloroform, ETHYLE ACETATE, trichloroethane, methylene dichloride, chlorobenzene, dichlorobenzene, oil of mirbane, ether, isopropyl ether, THF or furans etc.; Preferred aprotic organic solvent is ETHYLE ACETATE, N, dinethylformamide or acetonitrile; Preferred aprotic organic solvent is an ETHYLE ACETATE.The volumetric usage of aprotic organic solvent is counted 0.5～10ml/g with the quality of perfluoro hexyl sulfonic acid fluoride described in the step of the present invention (1), is preferably 0.5～5ml/g.
Described perfluoro hexyl sulfonic acid fluoride of step of the present invention (1) and N, N-dimethyl--1, the temperature of reaction of the sulfonamide reaction of 3-tn is-10～150 ℃, the reaction times is 0.5～20h; Preferred temperature of reaction is-5～15 ℃, and the preferred reaction times is 4～15h; Optimal reaction temperature is 0～10 ℃, and optimum reacting time is 8～10h.
Step of the present invention (1) is after reacting completely, and reaction solution needs can obtain midbody N through conventional separation method then, N-dimethyl--N '-perfluoro hexyl alkylsulfonyl tn through neutralizing treatment.
In the step of the present invention (2), described N, the ratio of the amount of substance of N-dimethyl--N '-perfluoro hexyl alkylsulfonyl tn and methyl iodide is 1: 1～5, and proportioning is 1: 1.6～2.5 preferably, and best proportioning is 1: 1.7.
It is one of following that the described aprotic organic solvent of step of the present invention (2) can be selected from: toluene, benzene, acetonitrile, N; Dinethylformamide, N; N-N,N-DIMETHYLACETAMIDE, DMSO 99.8MIN., acetone, tetramethylene sulfone, 1,2-ethylene dichloride, chloroform, ETHYLE ACETATE, trichloroethane, methylene dichloride, chlorobenzene, dichlorobenzene, oil of mirbane, ether, isopropyl ether, THF or furans etc.; Preferred aprotic organic solvent is tetracol phenixin or N, dinethylformamide; Preferred aprotic organic solvent is a tetracol phenixin.The volumetric usage of aprotic organic solvent described in the step of the present invention (2) is with N, and the quality of N-dimethyl--N '-perfluoro hexyl alkylsulfonyl tn is counted 0.5～5ml/g, is preferably 1～4ml/g.
The described N of step of the present invention (2), the temperature of reaction of the quaterisation of N-dimethyl--N '-perfluoro hexyl alkylsulfonyl tn and methyl iodide is 0～100 ℃, the reaction times is 0.5～10h; Preferred temperature of reaction is 25～100 ℃, and the preferred reaction times is 4～10h; More preferably temperature of reaction is 40～80 ℃, and more preferably the reaction times is 4～8h; Optimal reaction temperature is 40～60 ℃, and optimum reacting time is 4～5h.
Step of the present invention (2) is after reaction finishes; Adopt the ordinary method separation and purification can obtain title product, for example can adopt following method to carry out separation and purification: the gained reaction solution joins and separates out solid, decompress filter in the sherwood oil; Filter cake is used the industrial spirit recrystallization; Obtain title product N-(3-perfluoro hexyl sulfoamido) propyl group-N, N, N-trimethylammonium ammonium iodide.
The N-that the present invention makes (3-perfluoro hexyl sulfoamido) propyl group-N; N; N-trimethylammonium ammonium iodide surfactivity is high; Useful as surfactants is widely used in fire-fighting medium, emulsifying agent, coating brightening agent, oilfield foaming agent, fabric and comprises the water and oil repellent agent of leather and paper, the fields such as water and oil repellent agent of crust.
Beneficial effect of the present invention is mainly reflected in: the propyl group-N perfluoro hexyl quaternary ammonium salt perfluoro hexyl sulfoamido that a kind of brand new is provided); N, N-trimethylammonium ammonium iodide, this compound surfactivity is high; Perfluorinated octyl sulfuryl amine base than similar structures) propyl group-N; N, N-trimethylammonium ammonium iodide foaming properties have and significantly improve, and have a extensive future; Compound method of the present invention is simple.
(4) embodiment
Below in conjunction with specific embodiment the present invention is described further, but protection scope of the present invention is not limited in this.
The perfluoro hexyl sulfonic acid fluoride that the embodiment of the invention is used inspires confidence in Economic development ltd available from the Wuhan moral, N, and N-dimethyl--1, the 3-tn is available from Quzhou Xi Er chemical industry ltd.
Embodiment 1
Be equipped with in the four-hole boiling flask of whisking appliance, TM, tap funnel and reflux condensing tube at 250mL, add 50mL (0.5mol) ETHYLE ACETATE, 5.06g (0.05mol) H 2NC 3H 6N (CH 3) 2, 10.1g (0.1mol) triethylamine stirs, and is cooled to 0 ℃, drips 40.2g (0.10mol) C gradually 6F 13SO 2F controls about 30min and dropwises, and continues stirring reaction 4h.Neutralize about pH=7.5, decompress filter, vacuum-drying obtains white powder N, N-dimethyl--N '-perfluoro hexyl alkylsulfonyl tn, fusing point is 130 ℃, yield 80.4%.
FT-IR(cm -1)：3529、3035、2956、2873、1643、1365、1292、1247、1196、1142、1092、984、879。
1H-NMR?δ(CDCl 3，ppm)：3.32(m，2H)，2.76(t，2H)，2.52(s，6H)，，1.81(m，2H)。
MS (ESPI) spectrum: m/z=485.1.
Embodiment 2
React according to embodiment 1, still, solvent 50mL ETHYLE ACETATE changes 150mL N, dinethylformamide, H into 2NC 3H 6N (CH 3) 2Consumption change 51.0g (0.5mol) into, the 10.1g triethylamine changes 42.5g piperidines (0.46mol) into, temperature of reaction changes 150 ℃ into, the reaction times changes 20h into.N, N-dimethyl--N '-perfluoro hexyl alkylsulfonyl tn yield 88.2%.
Embodiment 3
React according to embodiment 1, still, solvent 50mL ETHYLE ACETATE changes 75mL N, dinethylformamide, H into 2NC 3H 6N (CH 3) 2Consumption change 25.5g (0.25mol) into, the 10.1g triethylamine changes 42.0g sodium hydrogencarbonate (0.5mol) into, temperature of reaction changes 50 ℃ into, the reaction times changes 15h into.N, N-dimethyl--N '-perfluoro hexyl alkylsulfonyl tn yield 82.0%.
Embodiment 4
React according to embodiment 1, still, solvent 50mL ETHYLE ACETATE changes 26mL acetonitrile, H into 2NC 3H 6N (CH 3) 2Consumption change 16.3g (0.16mol) into, the 10.1g triethylamine changes 20.2g triethylamine (0.2mol) into, temperature of reaction changes 10 ℃ into, the reaction times changes 10h into.N, N-dimethyl--N '-perfluoro hexyl alkylsulfonyl tn yield 90.2%.
Embodiment 5
Be equipped with in the four-hole boiling flask of whisking appliance, TM, tap funnel and reflux condensing tube at 250mL, add 24mL (2.5mol) tetracol phenixin, 24.2g (0.05mol) N, N-dimethyl--N '-perfluoro hexyl alkylsulfonyl tn, 7.1g (0.05mol) methyl iodide.0 ℃ of about 0.5h of following stirring reaction, the reactant that obtains joins in the 30mL sherwood oil and separates out solid, decompress filter; Filter cake is used the industrial spirit recrystallization, obtains N-(3-perfluoro hexyl sulfoamido) propyl group-N, N; N-trimethylammonium ammonium iodide white powder, 170 ℃ of fusing points, yield 71.6%.
FT-IR(cm -1)：3466、3021、2869、1363、1241、1208、1149、1082、958、892。
1H-NMR?δ(CDCl 3，ppm)：3.43(m，2H)，3.30(m，2H)，3.16(s，9H)，，2.07(m，2H)。
MS (ESPI) spectrum: m/z=499.1.
Embodiment 6
React according to embodiment 5, but the 24mL tetracol phenixin changes 77mL N into, dinethylformamide, the consumption of methyl iodide change 35.5g (0.25mol) into, and temperature of reaction changes 100 ℃ into, and the reaction times changes 10h into.N-(3-perfluoro hexyl sulfoamido) propyl group-N, N, N-trimethylammonium ammonium iodide yield 90.2%.
Embodiment 7
React according to embodiment 5, but the 24mL tetracol phenixin changes 39mL N into, dinethylformamide, the consumption of methyl iodide change 17.75g (0.125mol) into, and temperature of reaction changes 80 ℃ into, and the reaction times changes 8h into.N-(3-perfluoro hexyl sulfoamido) propyl group-N, N, N-trimethylammonium ammonium iodide yield 95.8%.
Embodiment 8
React according to embodiment 5, but the tetracol phenixin consumption changes 48mL into, the consumption of methyl iodide changes 12.04g (0.085mol) into, and temperature of reaction changes 50 ℃ into, and the reaction times changes 5h into.N-(3-perfluoro hexyl sulfoamido) propyl group-N, N, N-trimethylammonium ammonium iodide yield 97.5%.
Embodiment 9: the pasta spreading property
According to embodiment 5 synthetic N-(the 3-perfluoro hexyl sulfoamido) propyl group-N that obtain, N, N-trimethylammonium ammonium iodide is mixed with the 3.5mmol/L aqueous solution.At diameter 9cm, hold the 25mL hexanaphthene in the petridish of height 1.4cm, with the 10mL syringe fluorine surfactant aqueous solution is added drop-wise to oil surface, observe and sprawl situation, should make sight line equal during observation with pasta.N-(3-perfluoro hexyl sulfoamido) propyl group-N, N, the water-soluble fluid power of N-trimethylammonium ammonium iodide are at the hexanaphthene surface spreading, and the maximum maintenance dose on the hexanaphthene surface is 0.16mL.
Embodiment 10: foaming properties
According to embodiment 5 synthetic N-(the 3-perfluoro hexyl sulfoamido) propyl group-N that obtain, N, N-trimethylammonium ammonium iodide is mixed with the 3.5mmol/L aqueous solution, gets 13mL and adds in the 100mL tool plug graduated cylinder.After the fierce vibration, foam height 80mL, half foam life period are 18h.
Experimental procedure is the same, and difference is to adopt N-(3-perfluorinated octyl sulfuryl amine base) propyl group-N, N; N-trimethylammonium ammonium iodide replacement N-(3-perfluoro hexyl sulfoamido) propyl group-N, N, N-trimethylammonium ammonium iodide; The foam height of corresponding gained is 55mL, and half foam life period is 3h.
Therefore, N-of the present invention (3-perfluoro hexyl sulfoamido) propyl group-N, N, the foaming properties of N-trimethylammonium ammonium iodide be than N-(3-perfluorinated octyl sulfuryl amine base) propyl group-N, and N, N-trimethylammonium ammonium iodide have and significantly improve.

Claims (10)

  1. (1.N-3-perfluoro hexyl sulfoamido) propyl group-N, N, N-trimethylammonium ammonium iodide, structure is suc as formula shown in (I):
  2. 2. one kind prepares N-as claimed in claim 1 (3-perfluoro hexyl sulfoamido) propyl group-N, N, and the method for N-trimethylammonium ammonium iodide, said method comprises the steps:
    (1) with the N shown in perfluoro hexyl sulfonic acid fluoride shown in the formula (II) and the formula (III); N-dimethyl--1, the 3-tn is a raw material, in the presence of acid binding agent; In aprotic organic solvent; Carry out sulfonamide reaction in-10～150 ℃, reaction finishes after neutralization obtains the N shown in the formula (IV), N-dimethyl--N '-perfluoro hexyl alkylsulfonyl tn;
    (2) N; N-dimethyl--N '-perfluoro hexyl alkylsulfonyl tn again with the methyl iodide shown in the formula V in aprotic organic solvent; Carry out quaterisation 1～24h in-10～100 ℃; Reaction solution obtains the N-shown in the formula (I) (3-perfluoro hexyl sulfoamido) propyl group-N, N, N-trimethylammonium ammonium iodide through separation and purification;
  3. 3. preparation N-as claimed in claim 2 (3-perfluoro hexyl sulfoamido) propyl group-N; N; The method of N-trimethylammonium ammonium iodide; It is characterized in that: described acid binding agent is selected from following a kind of or any several kinds combination: n n dimetylaniline, diethylamine, Trimethylamine 99, triethylamine, N-methyl piperidine, N, N-xylidene(s), pyridine, piperidines, yellow soda ash, sodium hydroxide, sodium hydrogencarbonate, salt of wormwood, Pottasium Hydroxide, saleratus.
  4. 4. preparation N-as claimed in claim 2 (3-perfluoro hexyl sulfoamido) propyl group-N; N; The method of N-trimethylammonium ammonium iodide; It is characterized in that: step (1) and the described aprotic organic solvent of step (2) independently are selected from one of following separately: toluene, benzene, acetonitrile, N; Dinethylformamide, DMAC N,N, DMSO 99.8MIN., acetone, tetramethylene sulfone, 1,2-ethylene dichloride, chloroform, ETHYLE ACETATE, trichloroethane, methylene dichloride, chlorobenzene, dichlorobenzene, oil of mirbane, ether, isopropyl ether, THF, furans.
  5. 5. like the described preparation of one of claim 2～4 N-(3-perfluoro hexyl sulfoamido) propyl group-N; N, the method for N-trimethylammonium ammonium iodide is characterized in that: in the described step (1); Perfluoro hexyl sulfonic acid fluoride and N; N-dimethyl--1, the ratio of the amount of substance of 3-tn, acid binding agent is 1: 0.5～5: 0.1～5, the volumetric usage of said aprotic organic solvent is counted 0.5～10ml/g with the quality of perfluoro hexyl sulfonic acid fluoride; In the said step (2); N; N-dimethyl--N '-perfluoro hexyl alkylsulfonyl tn is 1: 1～5 with the ratio of the amount of substance of methyl iodide, and the volumetric usage of said aprotic organic solvent is with N, and the quality of N-dimethyl--N '-perfluoro hexyl alkylsulfonyl tn is counted 0.5～5ml/g.
  6. 6. preparation N-as claimed in claim 5 (3-perfluoro hexyl sulfoamido) propyl group-N; N, the method for N-trimethylammonium ammonium iodide is characterized in that: in the described step (1); Perfluoro hexyl sulfonic acid fluoride and N; N-dimethyl--1, the ratio of the amount of substance of 3-tn, acid binding agent is 1: 1.6～2.5: 1～5, the volumetric usage of said aprotic organic solvent is counted 0.5～5ml/g with the quality of perfluoro hexyl sulfonic acid fluoride; In the said step (2); N; N-dimethyl--N '-perfluoro hexyl alkylsulfonyl tn is 1: 1.6～2.5 with the ratio of the amount of substance of methyl iodide, and the volumetric usage of said aprotic organic solvent is with N, and the quality of N-dimethyl--N '-perfluoro hexyl alkylsulfonyl tn is counted 1～4ml/g.
  7. 7. preparation N-as claimed in claim 6 (3-perfluoro hexyl sulfoamido) propyl group-N, N, the method for N-trimethylammonium ammonium iodide; It is characterized in that: in the described step (1); Perfluoro hexyl sulfonic acid fluoride and N, N-dimethyl--1, the ratio of the amount of substance of 3-tn, acid binding agent is 1: 1.6: 1～2; In the said step (2), N, N-dimethyl--N '-perfluoro hexyl alkylsulfonyl tn is 1: 1.7 with the ratio of the amount of substance of methyl iodide.
  8. 8. like the described preparation of one of claim 2～4 N-(3-perfluoro hexyl sulfoamido) propyl group-N, N, the method for N-trimethylammonium ammonium iodide is characterized in that: the temperature of reaction of the described sulfonamide reaction of step (1) is-5～15 ℃, and the reaction times is 4～15h; The temperature of reaction of the described quaterisation of step (2) is 25～100 ℃, and the reaction times is 4～10h.
  9. 9. preparation N-as claimed in claim 7 (3-perfluoro hexyl sulfoamido) propyl group-N, N, the method for N-trimethylammonium ammonium iodide is characterized in that: the temperature of reaction of the described sulfonamide reaction of step (1) is 0～10 ℃, and the reaction times is 8～10h; The temperature of reaction of the described quaterisation of step (2) is 40～80 ℃, and the reaction times is 4～8h.
  10. 10. N-as claimed in claim 1 (3-perfluoro hexyl sulfoamido) propyl group-N, N, N-trimethylammonium ammonium iodide is as The Usage of Surfactant.
CN2011104515427A 2011-12-29 2011-12-29 N-(3-perfluor hexyl sulfamide) propyl-N, N, N-trimethyl ammonium iodide as well as preparation and application thereof Pending CN102584646A (en)

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CN102974265A (en) * 2012-12-04 2013-03-20 浙江工业大学 Preparation method and application of fluorooxa-containing sulfate type anionic surfactant
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
CN105727825A (en) * 2016-03-08 2016-07-06 肖进新 Compounding of carbon-4 fluoride surfactant and application of compound system preparation method of carbon-4 fluoride surfactant to aqueous film forming foam extinguishing agent

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彭历 等: "全氟己基磺酰类化合物的合成及表面性能", 《消防科学与技术》 *

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102924345A (en) * 2012-10-11 2013-02-13 浙江工业大学 Preparation method and application of branched fluorine-containing cationic surfactant
CN102974265A (en) * 2012-12-04 2013-03-20 浙江工业大学 Preparation method and application of fluorooxa-containing sulfate type anionic surfactant
CN102974265B (en) * 2012-12-04 2014-11-12 浙江工业大学 Preparation method and application of fluorooxa-containing sulfate type anionic surfactant
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
CN105017097B (en) * 2015-07-07 2017-03-29 武汉市化学工业研究所有限责任公司 Surfactant N carboxyethyls, the preparation method of 3 dimethylamino-propyl perfluoro hexyl sulfonamide of N
CN105727825A (en) * 2016-03-08 2016-07-06 肖进新 Compounding of carbon-4 fluoride surfactant and application of compound system preparation method of carbon-4 fluoride surfactant to aqueous film forming foam extinguishing agent
CN105727825B (en) * 2016-03-08 2018-08-07 肖进新 4 fluorinated surfactant of carbon compounding and its application in aqueous film-forming foam extinguishing agent

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Application publication date: 20120718