CN104069772B - A kind of tetrasiloxane Gemini surface active agent of sugary amide group and method for making - Google Patents
A kind of tetrasiloxane Gemini surface active agent of sugary amide group and method for making Download PDFInfo
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- CN104069772B CN104069772B CN201410333957.8A CN201410333957A CN104069772B CN 104069772 B CN104069772 B CN 104069772B CN 201410333957 A CN201410333957 A CN 201410333957A CN 104069772 B CN104069772 B CN 104069772B
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- tetrasiloxane
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Abstract
The tetrasiloxane Gemini surface active agent of sugary amide group and a method for making, belong to organic compound synthesis technical field.This material forms the siliceous compound be obtained by reacting with oxygen, nitrogen or bond with carbon in the molecule.Its preparation method is obtained chloropropyl tetrasiloxane under an acidic catalyst effect by hexamethyldisiloxane and chloropropyl silane, obtained N-β-aminoalkyl-γ-aminopropyl tetrasiloxane is reacted by chloropropyl tetrasiloxane and alkyl diamine, react in low-carbon alcohol solvent with saccharic acid or saccharic acid lactone again, then diglycidylether is added, the tetrasiloxane Gemini surface active agent of obtained sugary amide group, it is not hydrolyzed in 6 months in water, is widely used in fields such as agricultural chemicals.
Description
Technical field
The present invention relates to silicoorganic compound preparation method field, especially relate to tetrasiloxane Gemini surface active agent of a kind of sugary amide group and preparation method thereof.
Background technology
Trisiloxane surfactant is except the character with conventional surfactants, also there is superiority more more than conventional surfactants, non-aqueous system can be applied to, there is lower surface tension, extremely low physiological-toxicity, especially there is good wetting and spreading etc.
Gemini surface active agent is by two traditional surfactant monomers by chemical bond, these two tensio-active agents are linked together at hydrophilic head base or near hydrophilic head base with spacer group, a kind of tensio-active agent formed, its distinguishing feature is that the corresponding surfactant monomer of ratio of the will low 1 ~ 2 order of magnitude.
Han Fu (Chinese patent 200410092453.8) reports a kind of method preparing glucosyacylamino modification trisiloxane surfactant, reacted by aminosilane and hexamethyldisiloxane and generate amino trisiloxanes, react with Gluconolactone again, generate glucosyacylamino trisiloxane surfactant.Chinese patent 200410092452.3 reports a kind of method preparing glucosyacylamino trisiloxanes Gemini surface active agent, is reacted by glucosyacylamino trisiloxanes and diglycidylether, generates glucosyacylamino trisiloxanes Gemini surface active agent.
In the trisiloxane surfactant of these sugary amide group, carbon chain linker group between trisiloxanes and glucose amide is very short, in the emulsion system of the Application Areass such as agricultural chemicals, need longer carbochain, increase its oil soluble, change the absorption property on oil/water interface.And this kind of trisiloxanes is easy to hydrolysis in aqueous, within general about one week, major part is hydrolyzed, even the trisiloxane surfactant of double type is also hydrolysis in about month, loses surfactivity, affects its use properties.
Summary of the invention
The hydrophobic grouping trisiloxanes of tensio-active agent is the object of the invention is to change into tetrasiloxane, and longer carbochain is introduced between siloxanes and sugared acid amides, and connect as double type tensio-active agent, provide that a kind of surface tension is low, biological degradability good, micelle-forming concentration is little, the preparation method of the oil soluble more by force and in aqueous not tetrasiloxane Gemini surface active agent of the sugary amide group of facile hydrolysis.
The molecular structural formula of the tetrasiloxane Gemini surface active agent of sugary amide group of the present invention is as follows:
Wherein, R
1for
-O(CH
2CH
2O)
n--O(CH
2)
sO-、
R
2for
R
3for
-(CH
2)
x-
R
4for
-H or
N is the integer of 1 ~ 6, and s is the integer of 3 ~ 8, and x is the integer of 3 ~ 6.
The preparation method of the tetrasiloxane Gemini surface active agent of sugary amide group of the present invention comprises the following steps:
1., by hexamethyldisiloxane, chloropropyl silane and an acidic catalyst, be 40 ~ 100 DEG C in temperature of reaction, preferably 50 ~ 80 DEG C when react; Wherein the mol ratio of hexamethyldisiloxane and chloropropyl silane is (1 ~ 20): 1, and preferably (2 ~ 10): 1, the mole dosage of an acidic catalyst is 0.3% ~ 25% of hexamethyldisiloxane and chloropropyl silane mole sum; After having reacted, make an acidic catalyst inactivation, elimination solid, underpressure distillation, obtain chloropropyl tetrasiloxane;
2. alkyl diamine and chloropropyl tetrasiloxane is 60 ~ 150 DEG C in temperature of reaction, preferably 80 ~ 120 DEG C when react; Wherein the mol ratio of alkyl diamine and chloropropyl tetrasiloxane is (1 ~ 20): 1, preferably (6 ~ 15): 1; After having reacted, mixture stratification, upper strata underpressure distillation, obtains N-β-aminoalkyl-γ-aminopropyl tetrasiloxane;
3.N-β-aminoalkyl-γ-aminopropyl tetrasiloxane and saccharic acid or saccharic acid lactone, make solvent in low-carbon alcohol, temperature of reaction is 60 ~ 150 DEG C, preferably 60 ~ 100 DEG C of reactions; Wherein the mol ratio of alkyl diamine and saccharic acid or saccharic acid lactone is 1 ~ 2: 1, preferably 1: 1; After having reacted, steaming desolventizes, and obtains the tetrasiloxane of sugary amide group;
4. the tetrasiloxane of sugary amide group and diglycidylether, make solvent in low-carbon alcohol, temperature of reaction is 60 ~ 150 DEG C, preferably 60 ~ 100 DEG C of reactions; Wherein the tetrasiloxane of sugary amide group and the mol ratio of diglycidylether are 2 ~ 3: 1, preferably 2: 1; After having reacted, steaming desolventizes, and obtains the tetrasiloxane Gemini surface active agent of sugary amide group.
Chloropropyl silane as above can comprise: r-chloropropyl trimethoxyl silane, chloropropyl triethoxysilane etc.
An acidic catalyst as above can comprise: the vitriol oil, acidic white earth etc.
Make an acidic catalyst inactivation be when an acidic catalyst is the vitriol oil as above, add alkali catalyst neutralisation, make it inactivation; When an acidic catalyst is acidic white earth, filter, make it removing.
Alkyl diamine as above can comprise: 1,3-propylene diamine, Putriscine, 1,5-pentamethylene diamine, 1,6-hexanediamine etc.
Saccharic acid as above or saccharic acid lactone can comprise: gluconic acid or Gluconolactone, lactobionic acid or lactobionolactone, mannonic acid or mannonic acid lactone etc.
Low-carbon alcohol as above can comprise: methyl alcohol, ethanol, n-propyl alcohol, Virahol etc.
Diglycidylether as above can comprise: Flexible Electrophilic hydrate is as ethylene glycol diglycidylether, diethylene glycol diglycidyl glyceryl ether, Triethylene Glycol Diglycidyl Ether, TEG diglycidylether, five Hexanediol diglycidyl ether, six ethylene glycol diglycidylethers etc., flexible hydrophobic compound is as propylene glycol diglycidylether, butanediol diglycidyl ether, neopentyl glycol diglycidyl glyceryl ether, hexanediol diglycidyl ether, heptanediol diglycidylether, ethohexadiol diglycidylether etc., rigidization compound is as resorcinol diglycidyl ether, xylyl alcohol diglycidylether etc.
The tetrasiloxane Gemini surface active agent of the sugary amide group prepared by the present invention, its advantage is combined the high biological degradability of the low surface tension of organic silicon surfactant, sugar surfactants and the high-level efficiency of Gemini surface active agent, and longer carbochain is introduced between tetrasiloxane and sugared acid amides, absorption property on oil/water interface is better, and its not facile hydrolysis in aqueous.Can be used as inert ingredient composition in formulation of pesticide.Its using method and other inert ingredient raw material similar.
Embodiment
Below in conjunction with embodiment, the present invention is made an explanation.
Embodiment 1
Hexamethyldisiloxane 1.62kg is added, r-chloropropyl trimethoxyl silane 1.99kg, vitriol oil 0.006kg in reactor 1, react 4 hours at temperature 40 DEG C, hydro-oxidation sodium makes catalyst deactivation, solids removed by filtration, and underpressure distillation obtains chloropropyl tetrasiloxane.In reactor 2, add chloropropyl tetrasiloxane 3.73kg, 1,3-propylene diamine 0.74kg, is heated to 60 DEG C, reacts 4 hours, mixture stratification, upper strata underpressure distillation, obtains N-β-aminopropyl-γ-aminopropyl tetrasiloxane.In reactor 3, add N-β-aminopropyl-γ-aminopropyl tetrasiloxane 4.10kg, Gluconolactone 1.78kg, with methanol as solvent, be heated to 60 DEG C, react 8 hours.Add ethylene glycol diglycidylether 0.87kg again, continue reaction 12 hours.Steaming desolventizes methyl alcohol, obtains the tetrasiloxane Gemini surface active agent of sugary amide group.Record it not to be hydrolyzed in 6 months in water.
Embodiment 2
In reactor 1, add hexamethyldisiloxane 8.12kg, r-chloropropyl trimethoxyl silane 1.99kg, acidic white earth 0.10kg, react 4 hours under temperature 50 C, Filtration of catalyst, underpressure distillation obtains chloropropyl tetrasiloxane.In reactor 2, add chloropropyl tetrasiloxane 3.73kg, Putriscine 2.64kg, be heated to 80 DEG C, react 3 hours, mixture stratification, upper strata underpressure distillation, obtain N-β-ammonia butyl-γ-aminopropyl tetrasiloxane.In reactor 3, add N-β-ammonia butyl-γ-aminopropyl tetrasiloxane 4.24kg, gluconic acid 1.96kg, with ethanol as solvent, be heated to 70 DEG C, react 8 hours.Add propylene glycol diglycidylether 0.94kg again, continue reaction 12 hours.Steaming desolventizes ethanol, obtains the tetrasiloxane Gemini surface active agent of sugary amide group.Record it not to be hydrolyzed in 6 months in water.
Embodiment 3
Hexamethyldisiloxane 16.24kg is added, r-chloropropyl trimethoxyl silane 1.99kg, vitriol oil 0.54kg in reactor 1, react 4 hours under temperature 60 C, hydro-oxidation sodium makes catalyst deactivation, solids removed by filtration, and underpressure distillation obtains chloropropyl tetrasiloxane.In reactor 2, add chloropropyl tetrasiloxane 3.73kg, 1,5-pentamethylene diamine 6.12kg, is heated to 90 DEG C, reacts 2 hours, mixture stratification, upper strata underpressure distillation, obtains N-β-ammonia amyl group-γ-aminopropyl tetrasiloxane.In reactor 3, add N-β-ammonia amyl group-γ-aminopropyl tetrasiloxane 4.38kg, mannonic acid lactone 1.78kg, with methanol as solvent, be heated to 80 DEG C, react 10 hours.Add butanediol diglycidyl ether 1.01kg again, continue reaction 12 hours.Steaming desolventizes methyl alcohol, obtains the tetrasiloxane Gemini surface active agent of sugary amide group.Record it not to be hydrolyzed in 6 months in water.
Embodiment 4
In reactor 1, add hexamethyldisiloxane 32.48kg, r-chloropropyl trimethoxyl silane 1.99kg, acidic white earth 5.59kg, react 4 hours under temperature 70 C, Filtration of catalyst, underpressure distillation obtains chloropropyl tetrasiloxane.In reactor 2, add chloropropyl tetrasiloxane 3.73kg, 1,6-hexanediamine 11.6kg, is heated to 100 DEG C, reacts 1 hour, mixture stratification, upper strata underpressure distillation, obtains N-β-ammonia hexyl-γ-aminopropyl tetrasiloxane.In reactor 3, add N-β-ammonia hexyl-γ-aminopropyl tetrasiloxane 4.52kg, mannonic acid 1.96kg, with ethanol as solvent, be heated to 90 DEG C, react 10 hours.Add neopentyl glycol diglycidyl glyceryl ether 1.08kg again, continue reaction 12 hours.Steaming desolventizes ethanol, obtains the tetrasiloxane Gemini surface active agent of sugary amide group.Record it not to be hydrolyzed in 6 months in water.
Embodiment 5
Hexamethyldisiloxane 1.62kg is added, chloropropyl triethoxysilane 2.41kg, vitriol oil 0.20kg in reactor 1, react 3 hours at temperature 80 DEG C, hydro-oxidation sodium makes catalyst deactivation, solids removed by filtration, and underpressure distillation obtains chloropropyl tetrasiloxane.In reactor 2, add chloropropyl tetrasiloxane 3.73kg, 1,3-propylene diamine 8.88kg, is heated to 110 DEG C, reacts 4 hours, mixture stratification, upper strata underpressure distillation, obtains N-β-aminopropyl-γ-aminopropyl tetrasiloxane.In reactor 3, add N-β-aminopropyl-γ-aminopropyl tetrasiloxane 4.10kg, lactobionolactone 3.40kg, with methanol as solvent, be heated to 100 DEG C, react 8 hours.Add diethylene glycol diglycidyl glyceryl ether 1.09kg again, continue reaction 12 hours.Steaming desolventizes methyl alcohol, obtains the tetrasiloxane Gemini surface active agent of sugary amide group.Record it not to be hydrolyzed in 6 months in water.
Embodiment 6
In reactor 1, add hexamethyldisiloxane 8.12kg, chloropropyl triethoxysilane 2.41kg, acidic white earth 3.19kg, react 3 hours at temperature 80 DEG C, Filtration of catalyst, underpressure distillation obtains chloropropyl tetrasiloxane.In reactor 2, add chloropropyl tetrasiloxane 3.73kg, Putriscine 13.2kg, be heated to 120 DEG C, react 3 hours, mixture stratification, upper strata underpressure distillation, obtain N-β-ammonia butyl-γ-aminopropyl tetrasiloxane.In reactor 3, add N-β-ammonia butyl-γ-aminopropyl tetrasiloxane 4.24kg, lactobionic acid 3.58kg, with ethanol as solvent, be heated to 120 DEG C, react 8 hours.Add Triethylene Glycol Diglycidyl Ether 1.31kg again, continue reaction 12 hours.Steaming desolventizes ethanol, obtains the tetrasiloxane Gemini surface active agent of sugary amide group.Record it not to be hydrolyzed in 6 months in water.
Embodiment 7
Hexamethyldisiloxane 16.24kg is added, chloropropyl triethoxysilane 2.41kg, vitriol oil 2.70kg in reactor 1, react 3 hours at temperature 90 DEG C, hydro-oxidation sodium makes catalyst deactivation, solids removed by filtration, and underpressure distillation obtains chloropropyl tetrasiloxane.In reactor 2, add chloropropyl tetrasiloxane 3.73kg, 1,5-pentamethylene diamine 18.36kg, is heated to 130 DEG C, reacts 2 hours, mixture stratification, upper strata underpressure distillation, obtains N-β-ammonia amyl group-γ-aminopropyl tetrasiloxane.In reactor 3, add N-β-ammonia amyl group-γ-aminopropyl tetrasiloxane 4.38kg, lactobionolactone 3.40kg, with methanol as solvent, be heated to 140 DEG C, react 9 hours.Add resorcinol diglycidyl ether 1.12kg again, continue reaction 12 hours.Steaming desolventizes methyl alcohol, obtains the tetrasiloxane Gemini surface active agent of sugary amide group.Record it not to be hydrolyzed in 6 months in water.
Embodiment 8
In reactor 1, add hexamethyldisiloxane 32.48kg, chloropropyl triethoxysilane 2.41kg, acidic white earth 27.93kg, react 2 hours at temperature 100 DEG C, Filtration of catalyst, underpressure distillation obtains chloropropyl tetrasiloxane.In reactor 2, add chloropropyl tetrasiloxane 3.73kg, 1,6-hexanediamine 23.2kg, is heated to 150 DEG C, reacts 1 hour, mixture stratification, upper strata underpressure distillation, obtains N-β-ammonia hexyl-γ-aminopropyl tetrasiloxane.In reactor 3, add N-β-ammonia hexyl-γ-aminopropyl tetrasiloxane 4.52kg, lactobionic acid 3.58kg, with ethanol as solvent, be heated to 150 DEG C, react 9 hours.Add xylyl alcohol diglycidylether 1.26kg again, continue reaction 12 hours.Steaming desolventizes ethanol, obtains the tetrasiloxane Gemini surface active agent of sugary amide group.Record it not to be hydrolyzed in 6 months in water.
Claims (11)
1. a preparation method for the tetrasiloxane Gemini surface active agent of sugary amide group, is characterized in that comprising the steps:
(1) by hexamethyldisiloxane, chloropropyl silane and an acidic catalyst, react when temperature of reaction is 40 ~ 100 DEG C; Wherein the mol ratio of hexamethyldisiloxane and chloropropyl silane is (1 ~ 20): 1, and the mole dosage of an acidic catalyst is 0.3% ~ 25% of hexamethyldisiloxane and chloropropyl silane mole sum; After having reacted, make an acidic catalyst inactivation, elimination solid, underpressure distillation, obtain chloropropyl tetrasiloxane;
(2) alkyl diamine and chloropropyl tetrasiloxane, react when temperature of reaction is 60 ~ 150 DEG C; Wherein the mol ratio of alkyl diamine and chloropropyl tetrasiloxane is (1 ~ 20): 1; After having reacted, mixture stratification, upper strata underpressure distillation, obtains N-β-aminoalkyl-γ-aminopropyl tetrasiloxane;
(3) N-β-aminoalkyl-γ-aminopropyl tetrasiloxane and saccharic acid or saccharic acid lactone, make solvent with low-carbon alcohol, react when temperature of reaction is 60 ~ 150 DEG C; Wherein the mol ratio of alkyl diamine and saccharic acid or saccharic acid lactone is 1 ~ 2: 1; After having reacted, steaming desolventizes, and obtains the tetrasiloxane of sugary amide group;
(4) tetrasiloxane of sugary amide group and diglycidylether, make solvent with low-carbon alcohol, temperature of reaction is 60 ~ 150 DEG C of reactions; Wherein the tetrasiloxane of sugary amide group and the mol ratio of diglycidylether are 2 ~ 3: 1; After having reacted, steaming desolventizes, and obtains the tetrasiloxane Gemini surface active agent of sugary amide group;
The molecular structural formula of the tetrasiloxane Gemini surface active agent of described sugary amide group is as follows:
Wherein, R
1for
R
2for
R
3for
-(CH
2)
x-
R
4for
-H or
N is the integer of 1 ~ 6, and s is the integer of 3 ~ 8, and x is the integer of 3 ~ 6.
2. the preparation method of the tetrasiloxane Gemini surface active agent of a kind of sugary amide group as claimed in claim 1, is characterized in that described chloropropyl silane is r-chloropropyl trimethoxyl silane, chloropropyl triethoxysilane.
3. the preparation method of the tetrasiloxane Gemini surface active agent of a kind of sugary amide group as claimed in claim 1, is characterized in that described an acidic catalyst is the vitriol oil, acidic white earth.
4. the preparation method of the tetrasiloxane Gemini surface active agent of a kind of sugary amide group as claimed in claim 1, is characterized in that the described an acidic catalyst inactivation that makes is when an acidic catalyst is the vitriol oil, adds alkali catalyst neutralisation, make it inactivation; When an acidic catalyst is acidic white earth, filter, make it removing.
5. the preparation method of the tetrasiloxane Gemini surface active agent of a kind of sugary amide group as claimed in claim 1, is characterized in that described alkyl diamine is 1,3-propylene diamine, Putriscine, 1,5-pentamethylene diamine, 1,6-hexanediamine.
6. the preparation method of the tetrasiloxane Gemini surface active agent of a kind of sugary amide group as claimed in claim 1, is characterized in that described saccharic acid or saccharic acid lactone are gluconic acid or Gluconolactone, lactobionic acid or lactobionolactone, mannonic acid or mannonic acid lactone.
7. the preparation method of the tetrasiloxane Gemini surface active agent of a kind of sugary amide group as claimed in claim 1, is characterized in that described low-carbon alcohol is methyl alcohol, ethanol, n-propyl alcohol, Virahol.
8. the preparation method of the tetrasiloxane Gemini surface active agent of a kind of sugary amide group as claimed in claim 1, is characterized in that described diglycidylether is Flexible Electrophilic hydrate, flexible hydrophobic compound or rigidization compound.
9. the preparation method of the tetrasiloxane Gemini surface active agent of a kind of sugary amide group as claimed in claim 8, is characterized in that described Flexible Electrophilic hydrate is ethylene glycol diglycidylether, diethylene glycol diglycidyl glyceryl ether, Triethylene Glycol Diglycidyl Ether, TEG diglycidylether, five Hexanediol diglycidyl ether or six ethylene glycol diglycidylethers.
10. the preparation method of the tetrasiloxane Gemini surface active agent of a kind of sugary amide group as claimed in claim 8, is characterized in that described flexible hydrophobic compound is propylene glycol diglycidylether, butanediol diglycidyl ether, neopentyl glycol diglycidyl glyceryl ether, hexanediol diglycidyl ether, heptanediol diglycidylether or ethohexadiol diglycidylether.
The preparation method of the tetrasiloxane Gemini surface active agent of 11. a kind of sugary amide group as claimed in claim 8, is characterized in that described rigidization compound is resorcinol diglycidyl ether or xylyl alcohol diglycidylether.
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| CN105273198A (en) * | 2015-07-07 | 2016-01-27 | 常熟理工学院 | Preparation method of Gemini type glycosyl modified polysiloxane |
| CN105013392A (en) * | 2015-07-09 | 2015-11-04 | 广州大学 | Easily biodegraded organosilicon surfactant and preparation method thereof |
| CN106311075B (en) * | 2016-08-15 | 2018-10-19 | 常熟理工学院 | A kind of cyclosiloxane surfactant and preparation method thereof |
| CN107266487B (en) * | 2017-06-20 | 2019-03-22 | 汕头大学 | A kind of quaternary tetrasiloxane Gemini surface active agent and its preparation |
| CN110361941B (en) * | 2019-07-05 | 2023-02-03 | 上海新阳半导体材料股份有限公司 | Positive photoresist stripping liquid, preparation method and application thereof |
| CN110412838B (en) * | 2019-07-05 | 2023-02-21 | 上海新阳半导体材料股份有限公司 | High-selectivity stripping liquid, preparation method and application thereof |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1660883A (en) * | 2004-12-28 | 2005-08-31 | 中国日用化学工业研究院 | Polyglycol modified trisilicate containing glucose amide group and preparation method |
| CN102492146A (en) * | 2011-12-07 | 2012-06-13 | 北京工商大学 | Method for preparing polysiloxane containing alkyl and glucosamide |
| 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 |
| CN103752211A (en) * | 2014-02-14 | 2014-04-30 | 北京工商大学 | Trisiloxane quaternary ammonium salt containing glucosamine groups and preparation method |
-
2014
- 2014-07-15 CN CN201410333957.8A patent/CN104069772B/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1660883A (en) * | 2004-12-28 | 2005-08-31 | 中国日用化学工业研究院 | Polyglycol modified trisilicate containing glucose amide group and preparation method |
| CN102492146A (en) * | 2011-12-07 | 2012-06-13 | 北京工商大学 | Method for preparing polysiloxane containing alkyl and glucosamide |
| 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 |
| CN103752211A (en) * | 2014-02-14 | 2014-04-30 | 北京工商大学 | Trisiloxane quaternary ammonium salt containing glucosamine groups and preparation method |
Non-Patent Citations (2)
| Title |
|---|
| Adsorption and Aggregation Behavior of Tetrasiloxane-Tailed Surfactants Containing Oligo(ethylene oxide) Methyl Ether and a Sugar Moiety;Guoyong Wang等;《Journal of Physical Chemistry B》;20110317;第115卷(第14期);3811-3818 * |
| Adsorption and Aggregation Behaviors of Tetrasiloxane-Tailed Gemini Surfactants with (EO)m Spacers;Wang Guoyong等;《JOURNAL OF PHYSICAL CHEMISTRY BJOURNAL OF PHYSICAL CHEMISTRY B》;20130225;第117卷(第11期);第3155页合成路线1 * |
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Granted publication date: 20151209 Termination date: 20160715 |