CN102010437A - Polyethylene glycol-modified glycosyl group-containing tetrasiloxane and synthesizing method thereof - Google Patents
Polyethylene glycol-modified glycosyl group-containing tetrasiloxane and synthesizing method thereof Download PDFInfo
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- CN102010437A CN102010437A CN201010534435.6A CN201010534435A CN102010437A CN 102010437 A CN102010437 A CN 102010437A CN 201010534435 A CN201010534435 A CN 201010534435A CN 102010437 A CN102010437 A CN 102010437A
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Abstract
The invention relates to polyethylene glycol-modified glycosyl group-containing tetrasiloxane, which has a structural general formula shown in the specifications, wherein n is equal to 1 to 15. The invention has the advantages that: the surface tension of water is obviously lowered; the aqueous solution of the polyethylene glycol-modified glycosyl group-containing tetrasiloxane has small contact angles on the surfaces of polytetrafluoroethylene and paraffin and high spreading performance; and the polyethylene glycol-modified glycosyl group-containing tetrasiloxane can be applied to the formula of a pesticide to serve as a high-efficiency wetting and spreading auxiliary agent.
Description
Technical field
The invention belongs to a kind of tensio-active agent and synthetic method, relate to a kind of poly ethyldiol modified the tetrasiloxane tensio-active agent and the synthetic method that contain glycosyl particularly.
Background technology
The existing method for preparing aminoethyl aminopropyl tetrasiloxane, as Kovyazin V.A. (Russian Journal of General Chemistry, 2003,73,1,383) reported a kind of method for preparing aminoethyl aminopropyl tetrasiloxane, carried out transesterification reaction by aminosilane and trimethyl silanol and obtain product.In this method synthetic ammonia ethyl aminopropyl tetrasilane process, the reaction raw materials trimethyl silanol is very unstable, makes reaction be difficult to control.Aminoethyl aminopropyl tetrasiloxane is water-soluble relatively poor in addition, can not use as tensio-active agent.
The present invention proposes the method for new synthetic ammonia ethyl aminopropyl tetrasiloxane, and and then by primary amine groups and sugared amidate action in the aminoethyl aminopropyl tetrasiloxane, secondary amine and low methoxypolyethylene glycol glycidyl ether alkylated reaction have synthesized the water-soluble good poly ethyldiol modified tetrasiloxane that contains glycosyl, by retrieval, this compounds and preparation method thereof does not appear in the newspapers.
Summary of the invention
At the deficiencies in the prior art, the purpose of this invention is to provide a kind of good water solubility, easy-operating poly ethyldiol modified tetrasiloxane that contains glycosyl and synthetic method of reaction in preparation process.
The general structure of the poly ethyldiol modified tetrasiloxane that contains glycosyl of the present invention is as follows:
Wherein, n=1～15, preferably 1～6.
The critical aggregate concentration of the poly ethyldiol modified tetrasiloxane aqueous solution that contains glycosyl is 3 * 10
-5～3 * 10
-4Mol/L, lowest surface tension is 20.0～22.0mN/m; The minimal contact angle of its aqueous solution on ptfe surface is 25～40 °, and the minimal contact angle on paraffin is 0～15 °.
Synthetic method of the present invention comprises the steps:
(1) aminoethyl aminopropyl tetrasiloxane is synthetic
With hexamethyldisiloxane, aminoethyl aminopropyl trimethoxysilane and catalyst mix, in temperature is 50～160 ℃, preferred 60～140 ℃ are reacted 1～6h down, make catalyst deactivation after reaction is finished, and underpressure distillation obtains colourless liquid aminoethyl aminopropyl tetrasiloxane;
Wherein the mol ratio of each material is: hexamethyldisiloxane: aminoethyl aminopropyl trimethoxysilane=1～15: 1, and preferred molar ratio is 2～10: 1; Catalyzer: hexamethyldisiloxane and aminopropyl trimethoxysilane mole sum=0.1～10: 100;
Described catalyzer is a basic catalyst, be selected from: alkali metal hydroxide such as sodium hydroxide, potassium hydroxide etc., quaternary phosphonium hydroxides such as silicon alkoxide such as sodium silanolate, silanol potassium such as Si butyl phosphonium hydroxides etc., quaternary ammonium hydroxide such as Tetramethylammonium hydroxide etc., silanol quaternary alkylphosphonium salt such as tetrabutyl silanol Phosphonium etc., silanol quaternary ammonium salt are tetrabutyl silanol ammoniums etc.
The described method of catalyst deactivation that makes is: when catalyzer is alkali metal hydroxide, silicon alkoxide, adds sour catalyst neutralisation and make it inactivation; When catalyzer Wei quaternary phosphonium hydroxide, quaternary ammonium hydroxide, silanol quaternary alkylphosphonium salt, silanol quaternary ammonium salt, thermal degradation makes it inactivation.
(2) the poly ethyldiol modified tetrasiloxane that contains glycosyl is synthetic
Aminoethyl aminopropyl tetrasiloxane is mixed with glucono-lactone, lactobionic acid or lactobionic acid lactone, be dissolved in the low-carbon alcohol solvent, reflux temperature is reaction 3～10h down, obtain containing the tetrasiloxane of glycosyl, add the methoxypolyethylene glycol glycidyl ether again, reflux temperature is reaction 6～20h down, steams after reaction is finished to desolventize, and obtains the poly ethyldiol modified tetrasiloxane that contains glycosyl of light yellow liquid;
Wherein the mol ratio of each material is: aminoethyl aminopropyl tetrasiloxane: glucono-lactone, lactobionic acid or lactobionic acid lactone=1～2: 1, and preferred molar ratio is 1～1.5: 1; The tetrasiloxane that contains glycosyl: methoxypolyethylene glycol glycidyl ether=1～2: 1, preferred molar ratio is 1～1.5: 1; Solvent for use is a low-carbon alcohol, and preferred solvent is a dehydrated alcohol.
The poly ethyldiol modified tetrasiloxane that contains glycosyl of the present invention is a kind of tensio-active agent, can be used as the agricultural chemicals wetting aid and uses.
Compared with prior art, the present invention has the following advantages:
Synthetic method of the present invention has been avoided the uppity shortcoming of reaction that the raw material instability is caused in original technology, and catalyzer is cheap, and cost is low; (2) target compound of the present invention is a light yellow liquid, its structure warp
1The H nucleus magnetic resonance and
13The C nucleus magnetic resonance can obtain confirming, is a kind of novel organic silicon surfactant, and such target compound does not appear in the newspapers so far; (3) target compound surfactivity of the present invention is good, and the critical aggregate concentration of its aqueous solution is 3 * 10
-5～3 * 10
-4Mol/L, lowest surface tension is 20.0～22.0mN/m, less than like product; (4) target compound spreading property of the present invention is good, the minimal contact angle of its aqueous solution on ptfe surface is 25～40 °, minimal contact angle on paraffin is 0～15 °, can be used as the agricultural chemicals wetting aid to promote agricultural chemicals sprawling on plant leaf surface, improves drug effect.
Description of drawings
Fig. 1 is that the embodiment 2 poly ethyldiol modified tetrasiloxane structures that contain glycosyl are used
1The H nucleus magnetic resonance;
Fig. 2 is the poly ethyldiol modified tetrasiloxane structure product that contain glycosyl of embodiment 2
13The C nmr spectrum.
Embodiment:
At first 1.62Kg hexamethyldisiloxane and 2.22Kg aminoethyl aminopropyl trimethoxysilane are mixed to join in the reactor, add 0.8g sodium hydroxide again and make catalyzer, 150 ℃ were reacted 6 hours, add the acetic acid catalyst neutralisation after reaction stops and making it inactivation, carry out underpressure distillation then, obtain aminoethyl aminopropyl tetrasiloxane.Aminoethyl aminopropyl tetrasiloxane that obtains and the glucono-lactone that waits mole number are dissolved in the dehydrated alcohol, are warming up to backflow, reacted 4 hours, adding waits the ethylene glycol monomethyl ether glycidyl ether of mole number again, continues reaction 6 hours, is cooled to room temperature, rotary evaporation is removed solvent, promptly obtains product.The product structure formula is as follows:
The lowest surface tension that records its aqueous solution with the K12 surface tension instrument is 20.2mN/m, and critical aggregate concentration is 3.0 * 10
-5Mol/L is 30 ° at the minimal contact angle of ptfe surface, and the minimal contact angle on paraffin is 0 °.
At first 16.2Kg hexamethyldisiloxane and 2.22Kg aminoethyl aminopropyl trimethoxysilane are mixed to join in the reactor, add 2.288Kg silanol potassium again and make catalyzer, 130 ℃ were reacted 5 hours, add the acetic acid catalyst neutralisation after reaction stops and making it inactivation, carry out underpressure distillation then, obtain aminoethyl aminopropyl tetrasiloxane.Aminoethyl aminopropyl tetrasiloxane that obtains and the glucono-lactone that waits mole number are dissolved in the dehydrated alcohol, be warming up to backflow, reacted 6 hours, adding waits the diethylene glycol dimethyl ether glycidyl ether of mole number again, continue reaction 10 hours, be cooled to room temperature, rotary evaporation is removed solvent, promptly obtains product.The product structure formula is as follows:
The lowest surface tension that records its aqueous solution with the K12 surface tension instrument is 20.6mN/m, and critical aggregate concentration is 6 * 10
-5Mol/L is 25 ° at the minimal contact angle of ptfe surface, and the minimal contact angle on paraffin is 0 °.
Embodiment 3
At first 12.96Kg hexamethyldisiloxane and 2.22Kg aminoethyl aminopropyl trimethoxysilane are mixed to join in the reactor, add 123.2g Si butyl phosphonium hydroxides again and make catalyzer, 90 ℃ were reacted 2 hours, reaction stops post-heating and is warming up to 110 ℃, make catalyst deactivation, carry out underpressure distillation then, obtain aminoethyl aminopropyl tetrasiloxane.Aminoethyl aminopropyl tetrasiloxane that obtains and the lactobionic acid that waits mole number are dissolved in the dehydrated alcohol, are warming up to backflow, reacted 8 hours, adding waits the triethylene glycol methyl ether glycidyl ether of mole number again, continues reaction 14 hours, is cooled to room temperature, rotary evaporation is removed solvent, promptly obtains product.The product structure formula is as follows:
The lowest surface tension that records its aqueous solution with the K12 surface tension instrument is 21mN/m, and critical aggregate concentration is 1 * 10
-4Mol/L is 35 ° at the minimal contact angle of ptfe surface, and the minimal contact angle on paraffin is 5 °.
Embodiment 4
At first 8.1Kg hexamethyldisiloxane and 2.22Kg aminoethyl aminopropyl trimethoxysilane are mixed to join in the reactor, add the 273g Tetramethylammonium hydroxide again and make catalyzer, 110 ℃ were reacted 2 hours, reaction stops post-heating and is warming up to 130 ℃, make catalyst deactivation, carry out underpressure distillation then, obtain aminoethyl aminopropyl tetrasiloxane.Aminoethyl aminopropyl tetrasiloxane that obtains and the glucono-lactone that waits mole number are dissolved in the dehydrated alcohol, be warming up to backflow, reacted 4 hours, adding waits the TEG methyl ether glycidyl ether of mole number again, continue reaction 12 hours, be cooled to room temperature, rotary evaporation is removed solvent, promptly obtains product.The product structure formula is as follows:
The lowest surface tension that records its aqueous solution with the K12 surface tension instrument is 20.8mN/m, and critical aggregate concentration is 9 * 10
-5Mol/L is 32 ° at the minimal contact angle of ptfe surface, and the minimal contact angle on paraffin is 12 °.
Embodiment 5
At first 24.3Kg hexamethyldisiloxane and 2.22Kg aminoethyl aminopropyl trimethoxysilane are mixed to join in the reactor, add 260.8g tetramethyl-silanol Phosphonium again and make catalyzer, 70 ℃ were reacted 4 hours, reaction stops post-heating and is warming up to 110 ℃, make catalyst deactivation, carry out underpressure distillation then, obtain aminoethyl aminopropyl tetrasiloxane.Aminoethyl aminopropyl tetrasiloxane that obtains and the lactobionic acid lactone that waits mole number are dissolved in the dehydrated alcohol, be warming up to backflow, reacted 10 hours, adding waits the five ethylene glycol methyl ether glycidyl ether of mole number again, continue reaction 18 hours, be cooled to room temperature, rotary evaporation is removed solvent, promptly obtains product.The product structure formula is as follows:
The lowest surface tension that records its aqueous solution with the K12 surface tension instrument is lower than 22mN/m, and critical aggregate concentration is 3 * 10
-4Mol/L is 40 ° at the minimal contact angle of ptfe surface, and the minimal contact angle on paraffin is 15 °.
Embodiment 6
At first 16.2Kg hexamethyldisiloxane and 2.22Kg aminoethyl aminopropyl trimethoxysilane are mixed to join in the reactor, add 4.679Kg tetramethylsilane hydramine again and make catalyzer, 60 ℃ were reacted 5 hours, reaction stops post-heating and is warming up to 130 ℃, make catalyst deactivation, carry out underpressure distillation then, obtain aminoethyl aminopropyl tetrasiloxane.Aminoethyl aminopropyl tetrasiloxane that obtains and the glucono-lactone that waits mole number are dissolved in the dehydrated alcohol, be warming up to backflow, reacted 6 hours, adding waits six ethylene glycol monomethyl ether glycidyl ethers of mole number again, continue reaction 16 hours, be cooled to room temperature, rotary evaporation is removed solvent, promptly obtains product.The product structure formula is as follows:
The lowest surface tension that records its aqueous solution with the K12 surface tension instrument is about 21.5mN/m, and critical aggregate concentration is 2 * 10
-4Mol/L is 37 ° at the minimal contact angle of ptfe surface, and the minimal contact angle on paraffin is 10 °.
Claims (14)
1. poly ethyldiol modified tetrasiloxane that contains glycosyl is characterized in that general structure is as follows:
Wherein, n=1～15.
2. a kind of poly ethyldiol modified tetrasiloxane that contains glycosyl as claimed in claim 1 is characterized in that described n=1～6.
3. a kind of poly ethyldiol modified tetrasiloxane that contains glycosyl as claimed in claim 1 or 2 is characterized in that the critical aggregate concentration of the poly ethyldiol modified tetrasiloxane aqueous solution that contains glycosyl is 3 * 10
-5～3 * 10
-4Mol/L, lowest surface tension is 20.0～22.0mN/m; The minimal contact angle of its aqueous solution on ptfe surface is 25～40 °, and the minimal contact angle on paraffin is 0～15 °.
4. as the synthetic method of each described a kind of poly ethyldiol modified tetrasiloxane that contains glycosyl of claim 1-3, it is characterized in that comprising the steps:
(1) aminoethyl aminopropyl tetrasiloxane is synthetic
With hexamethyldisiloxane, aminoethyl aminopropyl trimethoxysilane and catalyst mix, be 50～160 ℃ in temperature, following reaction 1～6h makes catalyst deactivation after reaction is finished, and underpressure distillation obtains colourless liquid aminoethyl aminopropyl tetrasiloxane;
Wherein the mol ratio of each material is: hexamethyldisiloxane: aminoethyl aminopropyl trimethoxysilane=1～15: 1, and catalyzer: hexamethyldisiloxane and aminopropyl trimethoxysilane mole sum=0.1～10: 100;
(2) the poly ethyldiol modified tetrasiloxane that contains glycosyl is synthetic
Aminoethyl aminopropyl tetrasiloxane is mixed with glucono-lactone, lactobionic acid or lactobionic acid lactone, be dissolved in the low-carbon alcohol solvent, reflux temperature is reaction 3～10h down, obtain containing the tetrasiloxane of glycosyl, add the methoxypolyethylene glycol glycidyl ether again, reflux temperature is reaction 6～20h down, steams after reaction is finished to desolventize, and obtains the poly ethyldiol modified tetrasiloxane that contains glycosyl of light yellow liquid;
Wherein the mol ratio of each material is: aminoethyl aminopropyl tetrasiloxane: glucono-lactone, lactobionic acid or lactobionic acid lactone=1～2: 1, contain the tetrasiloxane of glycosyl: methoxypolyethylene glycol glycidyl ether=1～2: 1.
5. the synthetic method of a kind of poly ethyldiol modified tetrasiloxane that contains glycosyl as claimed in claim 4 is characterized in that described step (1) temperature of reaction is 60～140 ℃.
6. the synthetic method of a kind of poly ethyldiol modified tetrasiloxane that contains glycosyl as claimed in claim 4 is characterized in that hexamethyldisiloxane in the described step (1): aminoethyl aminopropyl trimethoxysilane=2～10: 1.
7. the synthetic method of a kind of poly ethyldiol modified tetrasiloxane that contains glycosyl as claimed in claim 4 is characterized in that the described catalyzer of step (1) is a basic catalyst.
8. the synthetic method of a kind of poly ethyldiol modified tetrasiloxane that contains glycosyl as claimed in claim 7, it is characterized in that described basic catalyst be alkali metal hydroxide, silicon alkoxide, quaternary phosphonium hydroxide,, quaternary ammonium hydroxide, silanol quaternary alkylphosphonium salt or silanol quaternary ammonium salt.
9. the synthetic method of a kind of poly ethyldiol modified tetrasiloxane that contains glycosyl as claimed in claim 8, it is characterized in that described alkali metal hydroxide is sodium hydroxide or potassium hydroxide, silicon alkoxide is that sodium silanolate or silanol potassium quaternary phosphonium hydroxide are Si butyl phosphonium hydroxides, quaternary ammonium hydroxide is a Tetramethylammonium hydroxide, the silanol quaternary alkylphosphonium salt is a tetrabutyl silanol Phosphonium, and the silanol quaternary ammonium salt is a tetrabutyl silanol ammonium.
10. the synthetic method of a kind of poly ethyldiol modified tetrasiloxane that contains glycosyl as claimed in claim 4, it is characterized in that the described method of catalyst deactivation that makes of step (1) is: when catalyzer is alkali metal hydroxide or silicon alkoxide, adds sour catalyst neutralisation and make it inactivation; When catalyzer Wei quaternary phosphonium hydroxide, quaternary ammonium hydroxide, silanol quaternary alkylphosphonium salt or silanol quaternary ammonium salt, thermal degradation makes it inactivation.
11. the synthetic method of a kind of poly ethyldiol modified tetrasiloxane that contains glycosyl as claimed in claim 4, it is characterized in that aminoethyl aminopropyl tetrasiloxane in the step (2): the mol ratio of glucono-lactone, lactobionic acid or lactobionic acid lactone is 1～1.5: 1.
12. the synthetic method of a kind of poly ethyldiol modified tetrasiloxane that contains glycosyl as claimed in claim 4 is characterized in that containing in the step (2) tetrasiloxane of glycosyl: the methoxypolyethylene glycol glycidyl ether be 1～1.5: 1.
13. the synthetic method of a kind of poly ethyldiol modified tetrasiloxane that contains glycosyl as claimed in claim 4 is characterized in that solvent for use is a low-carbon alcohol in the step (2).
14. the synthetic method of a kind of poly ethyldiol modified tetrasiloxane that contains glycosyl as claimed in claim 13 is characterized in that described low-carbon alcohol is a dehydrated alcohol.
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102382211A (en) * | 2011-08-30 | 2012-03-21 | 中科院广州化学有限公司 | Polymerizable nonionic silicone surfactant, its preparation method and its application |
| CN102614807A (en) * | 2012-03-07 | 2012-08-01 | 中国日用化学工业研究院 | Tetrasiloxane contained dimeric glycosyl surfactant and synthesis method |
| CN102614808A (en) * | 2012-03-08 | 2012-08-01 | 齐齐哈尔大学 | Organic silicon double-ion surfactant and preparation method thereof |
| CN104072562A (en) * | 2014-07-15 | 2014-10-01 | 北京工商大学 | Ethyoxyl modified saccharine acylamino contained tetra-siloxane and preparation method |
| CN104072563A (en) * | 2014-07-15 | 2014-10-01 | 北京工商大学 | Tetrasiloxane containing sugar acylamino and preparation method |
| CN104084084A (en) * | 2014-07-15 | 2014-10-08 | 北京工商大学 | Surfactant containing alkyl glucosamide and preparation method of surfactant |
| CN104084085A (en) * | 2014-07-15 | 2014-10-08 | 北京工商大学 | Ethyoxyl modified alkyl glucosamide surfactant and preparation method thereof |
| CN104610338B (en) * | 2015-01-13 | 2017-07-14 | 常熟理工学院 | Glycosyl amide is modified tetrasiloxane and preparation method thereof |
| CN107698615A (en) * | 2017-09-13 | 2018-02-16 | 常熟理工学院 | A kind of amino-acid modified tetrasiloxane surfactant and preparation method thereof |
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| CN102382211A (en) * | 2011-08-30 | 2012-03-21 | 中科院广州化学有限公司 | Polymerizable nonionic silicone surfactant, its preparation method and its application |
| CN102382211B (en) * | 2011-08-30 | 2013-01-02 | 中科院广州化学有限公司 | Polymerizable nonionic silicone surfactant, preparation method and application thereof |
| CN102614807A (en) * | 2012-03-07 | 2012-08-01 | 中国日用化学工业研究院 | Tetrasiloxane contained dimeric glycosyl surfactant and synthesis method |
| CN102614808A (en) * | 2012-03-08 | 2012-08-01 | 齐齐哈尔大学 | Organic silicon double-ion surfactant and preparation method thereof |
| CN102614808B (en) * | 2012-03-08 | 2013-11-20 | 齐齐哈尔大学 | Organic silicon double-ion surfactant and preparation method thereof |
| CN104072562A (en) * | 2014-07-15 | 2014-10-01 | 北京工商大学 | Ethyoxyl modified saccharine acylamino contained tetra-siloxane and preparation method |
| CN104072563A (en) * | 2014-07-15 | 2014-10-01 | 北京工商大学 | Tetrasiloxane containing sugar acylamino and preparation method |
| CN104084084A (en) * | 2014-07-15 | 2014-10-08 | 北京工商大学 | Surfactant containing alkyl glucosamide and preparation method of surfactant |
| CN104084085A (en) * | 2014-07-15 | 2014-10-08 | 北京工商大学 | Ethyoxyl modified alkyl glucosamide surfactant and preparation method thereof |
| CN104610338B (en) * | 2015-01-13 | 2017-07-14 | 常熟理工学院 | Glycosyl amide is modified tetrasiloxane and preparation method thereof |
| CN107698615A (en) * | 2017-09-13 | 2018-02-16 | 常熟理工学院 | A kind of amino-acid modified tetrasiloxane surfactant and preparation method thereof |
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Application publication date: 20110413 |