CN104231274A - Surface activity organosilicon room-temperature ionic liquid and synthetic method thereof - Google Patents
Surface activity organosilicon room-temperature ionic liquid and synthetic method thereof Download PDFInfo
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- CN104231274A CN104231274A CN201410415121.2A CN201410415121A CN104231274A CN 104231274 A CN104231274 A CN 104231274A CN 201410415121 A CN201410415121 A CN 201410415121A CN 104231274 A CN104231274 A CN 104231274A
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Abstract
The invention discloses a surface activity organosilicon room-temperature ionic liquid having a molecular structural formula shown in the specification, wherein R=CPH2(P+1), P=1,2,3,4, m=0-20, and n=0,1. The surface activity organosilicon room-temperature ionic liquid has the advantages of high surface activity resistance, low melting point, high purity and simple synthesis processes and is free from contamination.
Description
Technical field
The present invention relates to a kind of surfactivity room temperature silicone ionic liquid and synthetic method.
Background technology
Surface-active ion liquid, owing to being integrated with the advantage of tensio-active agent and ionic liquid, has potential using value in the various fields such as enzyme catalysis, lubricant, heat-transfer medium and atmosphere storage.At present, surface-active ion liquid of less types, mainly based on the alkane imidazolyl of long-chain, pyridyl ionic liquid (J.Colloid Interface Sci., 2013,412,24-30).But the general surfactivity of this type of ionic liquid is poor and fusing point is higher.Obtain high surface and must ensure that alkane chain has certain length (12 ~ 18), and when alkane chain length is greater than 7, Van der Waals force between alkane chain makes the force of cohesion between molecule increase, and causes the fusing point of this type of ionic liquid sharply to raise, greatly limit its range of application.As Murray S.M. (Angew.Chem.Int.Ed., 2010,49,2755) reports [C
10minBF
4] fusing point be-4.2 DEG C, when long alkyl chains is increased to 16, [C
16minBF
4] fusing point be then increased to 49.6 DEG C.
In addition, the synthesis of current surface-active ion liquid adopts two-step approach mostly.As patent CN 1417407A discloses a kind of preparation method of the ionic liquid at room temperature containing unsaturated double-bond, first, synthesize the halogen containing N-alkyl glyoxaline cation by quaterisation; Then use desired anion (as acetate, nitrate radical, tetrafluoroborate) to displace halide-ions to synthesize object ion liquid then.This method complex operation, by product are many, separating-purifying is comparatively difficult, and intermediate in building-up process and product contain halogen, are easy to hydrolysis and then can cause environment and biological water pollution problem.
Summary of the invention
The object of the invention is to overcome the deficiencies in the prior art, a kind of high surface, low melting point be provided, purity is high and building-up process is simple, free of contamination surfactivity room temperature silicone ionic liquid and synthetic method.
The molecular structural formula of surfactivity room temperature silicone ionic liquid provided by the invention is as follows:
Wherein R=C
ph
2p+1, P=1,2,3,4, m=0-20, n=0,1
The synthetic method of surfactivity room temperature silicone ionic liquid provided by the invention comprises the following steps:
(1) cyclosiloxane, aminosilane and catalyzer are joined in hexamethyldisiloxane, pass into nitrogen, under violent stirring, at 103-300 DEG C, react 10-15 hour; Wherein, the mol ratio of cyclosiloxane, aminosilane and hexamethyldisiloxane is 2.3-3.3:1:6-10; The mole dosage of catalyzer is the 1.5-5% of cyclosiloxane, aminosilane and hexamethyldisiloxane mole sum; After reaction terminates, add sour catalyst neutralisation, underpressure distillation obtains amino silicones; The object passing into nitrogen is the moisture generation hydrolysis reaction in order to prevent in aminosilane and solvent, generates corresponding silanol condensation thing.
(2) amino silicones and short chain organic acid, under low boiling point solvent effect, reacts 6-10 hour at 15-80 DEG C; Wherein the mol ratio of amino silicones and short chain organic acid is 1:1.05-3; After reaction terminates, rotary evaporation is except desolventizing, and vacuum-drying 3-5 hour, obtains surfactivity room temperature silicone ionic liquid;
In step described above (1), the mol ratio of cyclosiloxane, aminosilane and hexamethyldisiloxane is preferably 2.3-3:1:6-8; The mole dosage of catalyzer is preferably the 2-3% of cyclosiloxane, aminosilane and hexamethyldisiloxane mole sum.In step (2), the mol ratio of amino silicones and short chain organic acid is preferably 1:1.05-2.1.
Catalyzer in step described above (1) comprises: alkaline carbonate, as sodium carbonate, salt of wormwood etc.; Thanomin, as monoethanolamine, diethanolamine, trolamine etc.; Alkoxy compound, as sodium methylate, sodium ethylate, sodium isopropylate etc.
Cyclosiloxane in step described above (1) comprises: hexamethyl cyclotrisiloxane, octamethylcyclotetrasiloxane or decamethylcyclopentaandoxane.
Aminosilane in step described above (1) comprises: γ-aminopropyltrimethoxysilane, γ-aminopropyl triethoxysilane, N-β (aminoethyl)-γ-aminopropyltrimethoxysilane or N-β (aminoethyl)-γ-aminopropyl triethoxysilane etc.The employing of these aminosilanes is conducive to synthesizing the high polysiloxane of the amino with high surfaces activity.
In step described above (1), acid is HCl, HNO
3or H
2sO
4.
In step described above (1), temperature of reaction is preferably 103-230 DEG C; In step (2), temperature of reaction is preferably 35-60 DEG C.
Short chain organic carboxyl acid in step described above (2) is acetic acid, propionic acid, butanic acid or positive valeric acid.Low boiling point solvent is methylene dichloride, ether, acetone, ethyl acetate etc.
The amino silicones with alkalescence is reacted by acid-base neutralisation with acid organic carboxyl acid by the present invention, prepares and has surface-active room temperature silicone ionic liquid.This ionic liquid has the feature of ionic silicone surfactant, has higher surface tension in aqueous, significantly can reduce the surface tension of water to 19-21mN/m, and critical aggregation concentration is in aqueous 3.1-19.6 mmol/L; It can form the vesicular aggregates body with strong Assembling Behavior in aqueous, and this aggregate can be used as the template of nano materials, also can be used as the carrier of transmission medicine.
The method of synthetic surface active organosilicon ionic liquid at room temperature of the present invention, its advantage is: 1) that intermolecular cohesion is low and have the amino silicones of strong-hydrophobicity and organic carboxyl acid and carry out reaction and carry out synthesizing organo-silicon ionic liquid at room temperature, the surfactivity of product is higher, fusing point is lower, and range of application is wider.2) carry out synthetic surface active chamber temperature ionic liquid by acid-base neutralisation single stage method, reaction process is simple to operate, by product is few, product is easily purified, atom utilization is high, cost is low, be conducive to large-scale industrial production.3) whole reaction process is not containing halogen, and Environmental compatibility is good.
Accompanying drawing explanation
Fig. 1 is the product aminopropylpolysiloxane ammonium acetate of the embodiment of the present invention 1
1hNMR schemes.
Fig. 2 is that the surface tension of the product aminopropylpolysiloxane ammonium acetate of the embodiment of the present invention 1 is with concentration curve.
Embodiment
Embodiment 1
By the γ-aminopropyltrimethoxysilane of the hexamethyl cyclotrisiloxane of 51.17g (0.23mol), 17.93g (0.1mol), and the sodium carbonate of 1.27g (0.012mol) puts into the four-hole boiling flask of the hexamethyldisiloxane that 81.20g (0.5mol) is housed, at N
2protection under mixture is heated to 103 DEG C, stirring reaction, after 10 hours, adds hydrochloric acid catalyst neutralisation.Resistates obtains product aminopropylpolysiloxane by underpressure distillation, records primary amine value by potentiometric titration.Add the acetic acid of 1.05 times moles according to the mole number of primary amine value, make solvent with methylene dichloride, react 10 hours at 15 DEG C.Rotary evaporation is except desolventizing, and vacuum-drying 3 hours, obtains product aminopropylpolysiloxane ammonium acetate.Recording its lowest surface tension in aqueous by PROCESSOR TENSIOMETER K-12 surface tension instrument is 21.0mN/m, and critical aggregation concentration is 19.6mmol/L.
Embodiment 2
By the γ-aminopropyltrimethoxysilane of the hexamethyl cyclotrisiloxane of 73.41g (0.33mol), 17.93g (0.1mol), and the sodium carbonate of 3.29g (0.031mol) puts into the four-hole boiling flask of the hexamethyldisiloxane that 129.92g (0.8mol) is housed, at N
2protection under mixture is heated to 103 DEG C, stirring reaction, after 15 hours, adds hydrochloric acid catalyst neutralisation.Resistates obtains product aminopropylpolysiloxane by underpressure distillation, records primary amine value by potentiometric titration.Add the propionic acid of 1.05 times moles according to the mole number of primary amine value, make solvent with methylene dichloride, react 8 hours at 40 DEG C.Rotary evaporation is except desolventizing, and vacuum-drying 4 hours, obtains product aminopropylpolysiloxane propionic acid ammonium.Recording its lowest surface tension in aqueous by PROCESSOR TENSIOMETER K-12 surface tension instrument is 20.6mN/m, and critical aggregation concentration is 15.2mmol/L.
Embodiment 3
By N-β (the aminoethyl)-γ-aminopropyltrimethoxysilane of the hexamethyl cyclotrisiloxane of 66.74g (0.30mol), 22.24g (0.10mol), and the four-hole boiling flask of the hexamethyldisiloxane that 81.20g (0.5mol) is housed put into by the trolamine of 4.03g (0.027mol), at N
2protection under mixture is heated to 200 DEG C, stirring reaction, after 12 hours, adds HNO
3catalyst neutralisation.Resistates obtains product aminoethylaminopropyl polysiloxane by underpressure distillation, records primary amine value by potentiometric titration.Add the acetic acid of 2.10 times moles according to the mole number of primary amine value, make solvent with ether, react 10 hours at 35 DEG C.Rotary evaporation is except desolventizing, and vacuum-drying 3 hours, obtains product aminoethylaminopropyl polysiloxane ammonium acetate.Recording its lowest surface tension in aqueous by PROCESSOR TENSIOMETER K-12 surface tension instrument is 20.4mN/m, and critical aggregation concentration is 13.6mmol/L.
Embodiment 4
By the γ-aminopropyl triethoxysilane of the octamethylcyclotetrasiloxane of 74.16g (0.25mol), 22.13g (0.1mol), and the salt of wormwood of 1.09g (0.011mol) puts into the four-hole boiling flask of the hexamethyldisiloxane that 81.20g (0.5mol) is housed, at N
2protection under mixture is heated to 230 DEG C, stirring reaction, after 10 hours, adds HNO
3catalyst neutralisation.Resistates obtains product aminopropylpolysiloxane by underpressure distillation, records primary amine value by potentiometric titration.Add the acetic acid of 1.5 times moles according to the mole number of primary amine value, make solvent with methylene dichloride, react 7 hours at 40 DEG C.Rotary evaporation is except desolventizing, and vacuum-drying 3 hours, obtains product aminopropylpolysiloxane ammonium acetate.Recording its lowest surface tension in aqueous by PROCESSOR TENSIOMETER K-12 surface tension instrument is 21.0mN/m, and critical aggregation concentration is 9.6mmol/L.
Embodiment 5
By N-β (the aminoethyl)-γ-aminopropyl triethoxysilane of the octamethylcyclotetrasiloxane of 74.16g (0.25mol), 26.44g (0.1mol), and the diethanolamine of 3.57g (0.034mol) puts into the four-hole boiling flask of the hexamethyldisiloxane that 81.20g (0.5mol) is housed, at N
2protection under mixture is heated to 230 DEG C, stirring reaction, after 13 hours, adds the hydrochloric acid catalyst neutralisation of 10wt%.Resistates obtains product aminoethylaminopropyl polysiloxane by underpressure distillation, records primary amine value by potentiometric titration.Add the butanic acid of 3 times moles according to the mole number of primary amine value, with acetone as solvent, react 5 hours at 60 DEG C.Rotary evaporation is except desolventizing, and vacuum-drying 5 hours, obtains product aminoethylaminopropyl polysiloxane butyric acid ammonium.Recording its lowest surface tension in aqueous by PROCESSOR TENSIOMETER K-12 surface tension instrument is 19.8mN/m, and critical aggregation concentration is 6.3mmol/L.
Embodiment 6
By the γ-aminopropyl triethoxysilane of the decamethylcyclopentaandoxane of 92.69g (0.25mol), 22.13g (0.1mol), and the sodium ethylate of 3.95g (0.058mol) puts into the four-hole boiling flask of the hexamethyldisiloxane that 129.92g (0.8mol) is housed, at N
2protection under mixture is heated to 300 DEG C, stirring reaction, after 15 hours, adds H
2sO
4catalyst neutralisation.Resistates obtains product aminopropylpolysiloxane by underpressure distillation, records primary amine value by potentiometric titration.Add the positive valeric acid of 1.05 times moles according to the mole number of primary amine value, make solvent by ethyl acetate, react 4 hours at 80 DEG C.Rotary evaporation is except desolventizing, and vacuum-drying 5 hours, obtains product aminopropylpolysiloxane ammonium valerianate.Recording its lowest surface tension in aqueous by PROCESSOR TENSIOMETERK-12 surface tension instrument is 19.1mN/m, and critical aggregation concentration is 4.8mmol/L.
Embodiment 7
By N-β (the aminoethyl)-γ-aminopropyl triethoxysilane of the decamethylcyclopentaandoxane of 122.35g (0.33mol), 26.44g (0.1mol), and the sodium carbonate of 7.63g (0.072mol) puts into the four-hole boiling flask of the hexamethyldisiloxane that 162.4g (1.0mol) is housed, at N
2protection under mixture is heated to 300 DEG C, stirring reaction, after 15 hours, adds H
2sO
4catalyst neutralisation.Resistates obtains product aminoethylaminopropyl polysiloxane by underpressure distillation, records primary amine value by potentiometric titration.Add the propionic acid of 2.10 times moles according to the mole number of primary amine value, make solvent by ethyl acetate, react 10 hours at 80 DEG C.Rotary evaporation is except desolventizing, and vacuum-drying 5 hours, obtains product aminoethylaminopropyl polysiloxane propionic acid ammonium.Recording its lowest surface tension in aqueous by PROCESSOR TENSIOMETER K-12 surface tension instrument is 19.3mN/m, and critical aggregation concentration is 3.1mmol/L.
Claims (14)
1. a surfactivity room temperature silicone ionic liquid, is characterized in that the molecular structural formula of surfactivity room temperature silicone ionic liquid is as follows:
Wherein R=C
ph
2p+1, P=1,2,3,4, m=0-20, n=0,1.
2. the synthetic method of a kind of surfactivity room temperature silicone ionic liquid as claimed in claim 1, is characterized in that comprising the following steps:
(1) cyclosiloxane, aminosilane and catalyzer are joined in hexamethyldisiloxane, pass into nitrogen, under violent stirring, at 103-300 DEG C, react 10-15 hour; Wherein, the mol ratio of cyclosiloxane, aminosilane and hexamethyldisiloxane is 2.3-3.3:1:6-10; The mole dosage of catalyzer is the 1.5-5% of cyclosiloxane, aminosilane and hexamethyldisiloxane mole sum; After reaction terminates, add sour catalyst neutralisation, underpressure distillation obtains amino silicones; The object passing into nitrogen is the moisture generation hydrolysis reaction in order to prevent in aminosilane and solvent, generates corresponding silanol condensation thing.
(2) amino silicones and short chain organic acid, under low boiling point solvent effect, reacts 6-10 hour at 15-80 DEG C; Wherein the mol ratio of amino silicones and short chain organic acid is 1:1.05-3; After reaction terminates, rotary evaporation is except desolventizing, and vacuum-drying 3-5 hour, obtains surfactivity room temperature silicone ionic liquid.
3. the synthetic method of a kind of surfactivity room temperature silicone ionic liquid as claimed in claim 1, is characterized in that the mol ratio of cyclosiloxane, aminosilane and hexamethyldisiloxane in described step (1) is 2.3-3:1:6-8.
4. the synthetic method of a kind of surfactivity room temperature silicone ionic liquid as claimed in claim 1, is characterized in that the mole dosage of catalyzer in described step (1) is the 2-3% of cyclosiloxane, aminosilane and hexamethyldisiloxane mole sum.
5. the synthetic method of a kind of surfactivity room temperature silicone ionic liquid as claimed in claim 1, is characterized in that in described step (1), temperature of reaction is 103-230 DEG C.
6. the synthetic method of a kind of surfactivity room temperature silicone ionic liquid as claimed in claim 1, is characterized in that the catalyzer in described step (1) comprises alkaline carbonate, thanomin or alkoxy compound.
7. the synthetic method of a kind of surfactivity room temperature silicone ionic liquid as claimed in claim 6, is characterized in that described alkaline carbonate is sodium carbonate or salt of wormwood; Thanomin is monoethanolamine, diethanolamine or trolamine; Alkoxy compound is in order to sodium methylate, sodium ethylate or sodium isopropylate.
8. the synthetic method of a kind of surfactivity room temperature silicone ionic liquid as claimed in claim 1, is characterized in that the cyclosiloxane in described step (1) comprises hexamethyl cyclotrisiloxane, octamethylcyclotetrasiloxane or decamethylcyclopentaandoxane.
9. the synthetic method of a kind of surfactivity room temperature silicone ionic liquid as claimed in claim 1, is characterized in that the aminosilane in described step (1) comprises γ-aminopropyltrimethoxysilane, γ-aminopropyl triethoxysilane, N-β (aminoethyl)-γ-aminopropyltrimethoxysilane or N-β (aminoethyl)-γ-aminopropyl triethoxysilane.
10. the synthetic method of a kind of surfactivity room temperature silicone ionic liquid as claimed in claim 1, is characterized in that in described step (1), acid is HCl, HNO
3or H
2sO
4.
The synthetic method of 11. a kind of surfactivity room temperature silicone ionic liquids as claimed in claim 1, is characterized in that the short chain organic carboxyl acid in described step (2) is acetic acid, propionic acid, butanic acid or positive valeric acid.
The synthetic method of 12. a kind of surfactivity room temperature silicone ionic liquids as claimed in claim 1, the low boiling point solvent stated described in it is characterized in that in step (2) is methylene dichloride, ether, acetone or ethyl acetate.
The synthetic method of 13. a kind of surfactivity room temperature silicone ionic liquids as claimed in claim 1, is characterized in that in described step (2), temperature of reaction is 35-60 DEG C.
The synthetic method of 14. a kind of surfactivity room temperature silicone ionic liquids as claimed in claim 1, is characterized in that the mol ratio of amino silicones and short chain organic acid in described step (2) is 1:1.05-2.1.
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| CN105461930A (en) * | 2015-12-15 | 2016-04-06 | 上海华谊精细化工有限公司 | Anti-pollution coating composition and preparation thereof and application to low surface energy antifouling paint |
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| WO2022083851A1 (en) * | 2020-10-20 | 2022-04-28 | Wacker Chemie Ag | Process for synthesizing alkoxy group-containing aminosiloxanes |
| CN114316293A (en) * | 2021-10-09 | 2022-04-12 | 中国科学院过程工程研究所 | Method for improving surface hydrophobicity of biomass by using siloxane ionic liquid |
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