CN102585208A - P-perfluorous nonene oxygen group benzene sulfonic acid polyethylene glycol ester and preparation method as well as application thereof - Google Patents
P-perfluorous nonene oxygen group benzene sulfonic acid polyethylene glycol ester and preparation method as well as application thereof Download PDFInfo
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- CN102585208A CN102585208A CN2011104550670A CN201110455067A CN102585208A CN 102585208 A CN102585208 A CN 102585208A CN 2011104550670 A CN2011104550670 A CN 2011104550670A CN 201110455067 A CN201110455067 A CN 201110455067A CN 102585208 A CN102585208 A CN 102585208A
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Abstract
The invention discloses a p-perfluorous nonene oxygen group benzene sulfonic acid polyethylene glycol ester and a preparation method as well as application thereof. The structure of the p-perfluorous nonene oxygen group benzene sulfonic acid polyethylene glycol ester is shown in a formula (I) or formula (II), or the p-perfluorous nonene oxygen group benzene sulfonic acid polyethylene glycol ester is a mixture of compounds shown in the formula (I) and the formula (II). The p-perfluorous nonene oxygen group benzene sulfonic acid polyethylene glycol ester provided by the invention has high surface activity, can be used as a surface active agent and has wide application.
Description
(1) technical field
The present invention relates to a kind of p-perfluorinated nonene oxygen base Phenylsulfonic acid macrogol ester.
(2) background technology
Fluorine surfactant is compared with conventional surfactants, and outstanding performance is " three height, two are hated ", i.e. 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.
Fluorine carbon hydrophobic group tensio-active agent is the highest a kind of of surfactivity in the tensio-active agent so far, and its mass percent is that the surface tension of 0.01% left and right sides aqueous solution can be reduced to 15～20mN/m [Hangzhou chemical industry, 2010,40 (1): 10-14].The unionization in the aqueous solution of non-ion fluorin carbon surface active agent, by some amount contain that oxygen-ether linkage and/or hydroxyl constitute, the polar group chain length has directly influenced the surfactivity behavior of fluorocarbon surfactant.Polyoxyethylene glycol (PEG-n) is the linear ether of a kind of polyvalent alcohol of straight chain, can be used as the polar group of nonionogenic tenside.Jin Xin etc. have synthesized polyoxyethylene glycol glucoside fatty ester nonionogenic tenside, the about 35mN/m of its aqueous solution surface tension [Dalian University of Technology's journal, 2003,43 (1): 37-41].The report of relevant polyoxyethylene glycol sulphonate type fluorocarbon surfactant is few, and Ceng Yuhua has synthesized the perfluoro alkyl sulfonic acid macrogol ester with perfluoroalkyl SULPHURYL CHLORIDE and polyoxyethylene glycol, but because sulfonate group is prone to alkaline hydrolysis, R
FCarbochain oversize, surfactivity is not high, aqueous solution surface-tension energy reach 31mN/m [fluorocarbon surfactant [M]. Beijing: Chemical Industry Press, 2001:93].With p-perfluorinated nonene oxygen base benzene sulfonyl chloride (PFNPSC) and polyoxyethylene glycol (PEG-n) is raw material, and synthetic p-perfluorinated nonene oxygen base Phenylsulfonic acid macrogol ester (PFNPS-PEG-n) tensio-active agent does not also appear in the newspapers.
(3) summary of the invention
One of the object of the invention provides a kind of p-perfluorinated nonene oxygen base Phenylsulfonic acid macrogol ester with high surface.
Two of the object of the invention provides a kind of preparation method of simple p-perfluorinated nonene oxygen base Phenylsulfonic acid macrogol ester.
For realizing the foregoing invention purpose, the technical scheme that the present invention adopts is:
P-perfluorinated nonene oxygen base Phenylsulfonic acid macrogol ester of the present invention, its structure is suc as formula perhaps it is the mixture of compound shown in formula (I) and the formula (II) shown in (I) or the formula (II):
Wherein the span of the MV of n is 2～45, and the span of the MV of preferred n is 4～27, and more preferably the span of the MV of n is 10～22.
The invention provides a kind of method for preparing described p-perfluorinated nonene oxygen base Phenylsulfonic acid macrogol ester; Said method comprises: the polyoxyethylene glycol with shown in perfluorinated nonene oxygen base benzene sulfonyl chloride shown in the formula (II) and the formula (III) is a raw material; In the presence of acid binding agent, in aprotic organic solvent, carry out esterification in-10～150 ℃; Remove solvent under reaction 0.5～24h afterreaction liquid reduced pressure, obtain p-perfluorinated nonene oxygen base Phenylsulfonic acid macrogol ester;
Raw material perfluorinated nonene oxygen base benzene sulfonyl chloride and polyoxyethylene glycol that the present invention uses are the commercial goods.The raw material polyoxyethylene glycol is a mixture, representes with polyoxyethylene glycol-k, and k is the molecular-weight average of polyoxyethylene glycol, is meant that like polyoxyethylene glycol-600 molecular-weight average is 600 polyoxyethylene glycol.When calculating the mole number of polyoxyethylene glycol-k, adopt the molecular weight of molecular-weight average as this polyoxyethylene glycol.Among the present invention, the molecular-weight average of polyoxyethylene glycol is 100-2000 (MV that is n is 2～45), and preferred molecular-weight average is 200-1200 (MV that is n is 4～27), and more preferably molecular-weight average is 10～22 (MV that is n is 400～1000).2 primary hydroxyls of polyoxyethylene glycol all are active reactive groups; When p-perfluorinated nonene oxygen base benzene sulfonyl chloride and polyoxyethylene glycol reaction; 2 hydroxyls of polyoxyethylene glycol can with the effect of p-perfluorinated nonene oxygen base benzene sulfonyl chloride, what obtain is the mixture of p-perfluorinated nonene oxygen base Phenylsulfonic acid polyoxyethylene glycol monoesters and dibasic acid esters.When the mol ratio of p-perfluorinated nonene oxygen base benzene sulfonyl chloride and polyoxyethylene glycol hour, as less than 1, be main with p-perfluorinated nonene oxygen base Phenylsulfonic acid polyoxyethylene glycol monoesters in the mixture.When the mol ratio of p-perfluorinated nonene oxygen base benzene sulfonyl chloride and polyoxyethylene glycol is big, as greater than 2, be main with p-perfluorinated nonene oxygen base Phenylsulfonic acid polyoxyethylene glycol dibasic acid esters in the mixture.Polyoxyethylene glycol of the present invention is 1: 1～5 with the ratio of the amount of substance of p-perfluorinated nonene oxygen base benzene sulfonyl chloride, and proportioning is 1: 1.1～3 preferably, and best proportioning is 1: 1.1～2.
Acid binding agent of the present invention 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 be mixture arbitrarily, and preferred acid binding agent is triethylamine, piperidines or sodium hydrogencarbonate.Among the present invention; The ratio of the amount of substance of p-perfluorinated nonene oxygen base benzene sulfonyl chloride and acid binding agent is 1: 1～5; The ratio of the preferable p-perfluorinated nonene oxygen base benzene sulfonyl chloride and the amount of substance of acid binding agent is 1: 1～3, and the ratio of the best p-perfluorinated nonene oxygen base benzene sulfonyl chloride and the amount of substance of acid binding agent is 1: 1～2.
Aprotic organic solvent of the present invention is selected from following a kind of or any several kinds combination: 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.Among the present invention, the volumetric usage of said aprotic organic solvent is counted 1～10ml/g with the quality of p-perfluorinated nonene oxygen base benzene sulfonyl chloride, is preferably 1～5ml/g.
The reaction of p-perfluorinated nonene oxygen base benzene sulfonyl chloride of the present invention and polyoxyethylene glycol, preferred temperature of reaction is 10～150 ℃, the preferred reaction times is 1～24h; Preferred temperature of reaction is 15～85 ℃, and the preferred reaction times is 4～15h; Optimal reaction temperature is 25～40 ℃, and optimum reacting time is 8～10h.
P-perfluorinated nonene oxygen base Phenylsulfonic acid macrogol ester surfactivity of the present invention is high; Useful as surfactants is widely used in emulsifying agent, whipping 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: a kind of perfluorinated nonene base nonionogenic tenside p-perfluorinated nonene oxygen base Phenylsulfonic acid macrogol ester of brand new is provided, and this compound surfactivity is high, has broad application prospects; Compound method of the present invention is simple.
(4) description of drawings
Fig. 1 is four kinds of p-perfluorinated nonene oxygen base Phenylsulfonic acid macrogol esters (PFNPS-PEG-k) aqueous solution lather volume and the concentration curve that the embodiment of the invention makes.
Fig. 2 is four kinds of p-perfluorinated nonene oxygen base Phenylsulfonic acid macrogol esters (PFNPS-PEG-k) aqueous solution half foam life period and the concentration curve that the embodiment of the invention makes.
(5) 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 perfluorinated nonene oxygen base benzene sulfonyl chloride that the embodiment of the invention is used is available from Lianyun Harbour Thailand tall and erect novel material ltd, and polyoxyethylene glycol is available from Gao Nan chemical plant, PVG.
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; 30g (0.05mol) polyoxyethylene glycol-600,5.06g (0.05mol) triethylamine stirs; Be cooled to 10 ℃, slowly drip the 50mL CCl of 31.1g (0.05mol) p-perfluorinated nonene oxygen base benzene sulfonyl chloride
4Solution is controlled about 30min and is dropwised, and continues stirring reaction 24h down at 10 ℃.Underpressure distillation removes solvent, obtains yellow thickness lotion (mixture of monoesters and dibasic acid esters).20 ℃ of surface tension that record 0.5g/L product water solution are 22.6mN/m.
Product structure characterizes:
FT-IR(KBr，cm-1)：3424、2873、1663、1488、1282、1180、1092、971、838、737。
19F?NMR?δ(CDCl
3)：-169.8、-167.7、-72.8、-71.5、-56.3。
React according to embodiment 1; But solvent 50mL ETHYLE ACETATE changes 150mL N, dinethylformamide into; The consumption of p-perfluorinated nonene oxygen base benzene sulfonyl chloride changes 155.67g (0.25mol) into; 5.06g triethylamine changes 42.5g piperidines (0.50mol) into, temperature of reaction changes 150 ℃ into, and the reaction times changes 1h into.
Obtain yellow thickness lotion (mixture of monoesters and dibasic acid esters), 20 ℃ of surface tension that record 0.5g/L product water solution are 20.6mN/m.
Embodiment 3
React according to embodiment 1; But solvent 50mL ETHYLE ACETATE changes 75mL N, dinethylformamide into; The consumption of p-perfluorinated nonene oxygen base benzene sulfonyl chloride changes 34.2g (0.055mol) into; 5.06g triethylamine changes 13.9g sodium hydrogencarbonate (0.165mol) into, temperature of reaction changes 50 ℃ into, and the reaction times changes 7h into.
Obtain yellow thickness lotion (mixture of monoesters and dibasic acid esters), 20 ℃ of surface tension that record 0.5g/L product water solution are 21.5mN/m.
React according to embodiment 1, still, solvent 50mL ETHYLE ACETATE changes the 26mL acetonitrile into; The consumption of p-perfluorinated nonene oxygen base benzene sulfonyl chloride changes 62.2g (0.10mol) into; 5.06g triethylamine changes 20.2g triethylamine (0.20mol) into, temperature of reaction changes 30 ℃ into, and the reaction times changes 9h into.
Obtain yellow thickness lotion (mixture of monoesters and dibasic acid esters), 20 ℃ of surface tension that record 0.5g/L product water solution are 20.1mN/m.
Embodiment 5
React according to embodiment 1; But 30g polyoxyethylene glycol-600 changes 10g polyoxyethylene glycol-200 (0.05mol) into, and 50mL (0.5mol) ETHYLE ACETATE changes the 26mL acetonitrile into; The consumption of p-perfluorinated nonene oxygen base benzene sulfonyl chloride changes 34.2g (0.055mol) into; 5.06g triethylamine changes 11.1g triethylamine (0.10mol) into, temperature of reaction changes 30 ℃ into, and the reaction times changes 9h into.
Obtain yellow thickness lotion (mixture of monoesters and dibasic acid esters), 20 ℃ of surface tension that record 0.5g/L product water solution are 26.0mN/m.
React according to embodiment 5, still, 10g polyoxyethylene glycol-200 changes 20g polyoxyethylene glycol-400 (0.05mol) into, obtains yellow thickness lotion (mixture of monoesters and dibasic acid esters), and 20 ℃ of surface tension that record 0.5g/L product water solution are 21.6mN/m.
Embodiment 7
React according to embodiment 5, still, 10g polyoxyethylene glycol-200 changes 40g polyoxyethylene glycol-800 (0.05mol) into, obtains yellow thickness lotion (mixture of monoesters and dibasic acid esters), and 20 ℃ of surface tension that record 0.5g/L product water solution are 23.4mN/m.
React according to embodiment 5, still, 10g polyoxyethylene glycol-200 changes 50g polyoxyethylene glycol-1000 (0.05mol) into, obtains yellow thickness lotion (mixture of monoesters and dibasic acid esters), and 20 ℃ of surface tension that record 0.5g/L product water solution are 24.1mN/m.
Embodiment 9
React according to embodiment 5, still, 10g polyoxyethylene glycol-200 changes 100g polyoxyethylene glycol-2000 (0.05mol) into, obtains yellow thickness lotion (mixture of monoesters and dibasic acid esters), and 20 ℃ of surface tension that record 0.5g/L product water solution are 28.9mN/m.
Respectively with the product of embodiment 6, embodiment 4, embodiment 7 and embodiment 8; Preparation 20mL p-perfluorinated nonene oxygen base Phenylsulfonic acid macrogol ester (PFNPS-PEG-k) aqueous solution adopts the foaming properties of 4 kinds of PFNPS-PEG-k of succusion test at 25 ℃ of following different concns.Vibration 3min, the failure of oscillations, the record lather volume is M, liquid volume is N, the time T when the record liquid level reaches (20+N)/2 volume
1/2Be the lather collapse transformation period.The concentration of p-perfluorinated nonene oxygen base Phenylsulfonic acid polyoxyethylene glycol aqueous solution of ester and the relation of lather volume are as shown in Figure 1.The concentration of p-perfluorinated nonene oxygen base Phenylsulfonic acid polyoxyethylene glycol aqueous solution of ester and the relation of lather volume are as shown in Figure 2.
Embodiment 11
The product (PFNPS-PEG-k) of getting embodiment 6, embodiment 4, embodiment 7 and embodiment 8 respectively is mixed with the 1g/L aqueous solution; Get these aqueous solution of 40mL respectively in 100mL tool plug graduated cylinder, add 40mL benzene, fiercely vibrate 5 times; Leave standstill 1min; Repeat aforesaid operations 5 times, the back timing is left standstill in the 5th vibration, and the time T of 10mL water told in record
10mL(min).The T of 4 kinds of products
10mL(min) being respectively PFNPS-PEG-200 is 9.30min, and PFNPS-PEG-400 is 10.99min, and PFNPS-PEG-600 is 11.36min, and PFNPS-PEG-1000 is 15.56min.
Claims (10)
1.p-perfluorinated nonene oxygen base Phenylsulfonic acid macrogol ester, its structure is suc as formula perhaps it is the mixture of compound shown in formula (I) and the formula (II) shown in (I) or the formula (II):
Wherein the span of the MV of n is 2～45.
2. p-perfluorinated nonene oxygen base Phenylsulfonic acid macrogol ester as claimed in claim 1, it is characterized in that: the span of the MV of n is 4～27.
3. method for preparing p-perfluorinated nonene oxygen base Phenylsulfonic acid macrogol ester as claimed in claim 1; Comprise: the polyoxyethylene glycol with shown in perfluorinated nonene oxygen base benzene sulfonyl chloride shown in the formula (II) and the formula (III) is a raw material; In the presence of acid binding agent, in aprotic organic solvent, carry out esterification in-10～150 ℃; Remove solvent under reaction 0.5～24h afterreaction liquid reduced pressure, obtain p-perfluorinated nonene oxygen base Phenylsulfonic acid macrogol ester;
In the formula (III), the definition cotype (I) of n or formula (II).
4. the method for preparing p-perfluorinated nonene oxygen base Phenylsulfonic acid macrogol ester as claimed in claim 3; It is characterized in that: described aprotic organic solvent is selected from following a kind of or any several kinds combination: 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, furans.
5. the method for preparing p-perfluorinated nonene oxygen base Phenylsulfonic acid macrogol ester as claimed in claim 3; 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.
6. like the described method for preparing p-perfluorinated nonene oxygen base Phenylsulfonic acid macrogol ester of one of claim 3～5; It is characterized in that: the ratio of the amount of substance of described polyoxyethylene glycol and p-perfluorinated nonene oxygen base benzene sulfonyl chloride is 1: 1.1～3; The ratio of the amount of substance of p-perfluorinated nonene oxygen base benzene sulfonyl chloride and acid binding agent is 1: 1～3, and the volumetric usage of said aprotic organic solvent is counted 1～5ml/g with the quality of p-perfluorinated nonene oxygen base benzene sulfonyl chloride.
7. the method for preparing p-perfluorinated nonene oxygen base Phenylsulfonic acid macrogol ester as claimed in claim 6; It is characterized in that: the ratio of the amount of substance of described polyoxyethylene glycol and p-perfluorinated nonene oxygen base benzene sulfonyl chloride is 1: 1.1～2, and the ratio of the amount of substance of p-perfluorinated nonene oxygen base benzene sulfonyl chloride and acid binding agent is 1: 1～2.
8. like the described method for preparing p-perfluorinated nonene oxygen base Phenylsulfonic acid macrogol ester of one of claim 3～5, it is characterized in that: temperature of reaction is 15～85 ℃, and the reaction times is 4～15h.
9. the method for preparing p-perfluorinated nonene oxygen base Phenylsulfonic acid macrogol ester as claimed in claim 7, it is characterized in that: temperature of reaction is 25～40 ℃, the reaction times is 8～10h.
10. p-perfluorinated nonene oxygen base Phenylsulfonic acid macrogol ester as claimed in claim 1 is as The Usage of Surfactant.
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| CN103611472A (en) * | 2013-12-11 | 2014-03-05 | 浙江工业大学 | Preparation method and application of fluorine-containing surfactant |
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