CN107597019A - A kind of amino-acid modified organic silicon surfactant of Bola types and preparation method thereof - Google Patents
A kind of amino-acid modified organic silicon surfactant of Bola types and preparation method thereof Download PDFInfo
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Abstract
A kind of amino-acid modified organic silicon surfactant of Bola types and preparation method thereof, belongs to technical field of chemistry and chemical engineering.Step：With cyclosiloxane, 1,3 pairs of (3 aminopropyl) 1,1,3,3 tetramethyl disiloxanes are raw material, using catalyst reaction, after reaction terminates, make catalyst inactivation, then are evaporated under reduced pressure and remove unreacted raw material, obtain double amino-terminated polysiloxanes；It is that raw material reacts in the presence of low-carbon alcoholic solvent by obtained double amino-terminated polysiloxanes and methyl acrylate, after the completion of reaction, low-carbon alcoholic solvent is evaporated off, obtains double aminopropanoate type polysiloxanes；Double aminopropanoate type polysiloxanes will be obtained to react in the presence of low-carbon alcoholic solvent with sodium hydroxide solution, after the completion of reaction, low-carbon alcoholic solvent is evaporated off, obtains finished product.Extend use range；Without tired, preparation cost is cheap for preparation process letter.
Description
Technical field
The invention belongs to technical field of chemistry and chemical engineering, and in particular to a kind of surfactant, more particularly to a kind of Bola types
Amino-acid modified organic silicon surfactant, and further relate to its preparation method.
Background technology
Bola type surfactants are to be formed by two hydrophilic polar groups by one or more hydrophobic chain links
Compound, compared with traditional surfactant, Bola type surfactants have high-temperature stability, and chemical stability is good, more
High dissolubility, abundant phase behavior (aggregation that variform is formed in aqueous phase) etc..
Synthesis hydrophilic base disclosed in the A of Chinese patent publication No. CN 102240521 (a kind of Bola types surfactant) is
Quaternary Bola type surfactants；What Xu Xiaomin (printing and dyeing assistant, 2013,30,5) was introduced is that synthesis hydrophilic base is carboxylic acid type
Surfactant；The hydrophobic group of these Bola type surfactants is mainly alkane chain.Bola type organic silicon surfactants are
One kind of Bola type surfactants, because it had both had the performance of Bola type surfactants, again there is organosilyl surface to live
The performance of property agent, thus there is potential application in some special dimensions.Chinese patent notification number CN104645877B synthesis is a kind of
Bola type organic silicon modified by polyether surfactants.The hydrophilic group of the Bola type organic silicon surfactants of foregoing synthesis is poly-
Ether.
Because amino acid surfactant has, properties of product are gentle, toxicity is relatively low, nonirritant, biological degradability and ring
The strong points such as border compatibility, thus had a wide range of applications in industries such as food, medicine and cosmetics.Research and development at present
It is N- alkyl amino acids surfactant and N- acyl amino acid surfactants to compare more amino acid surfactants, but
The hydrophobic grouping of above-mentioned amino acid surfactant is alkane chain.
Therefore, in view of the problems such as amino-acid modified organic silicon surfactant of existing preparation Bola types is of less types, exploitation
The amino-acid modified organic silicon surfactant of novel B ola types simultaneously studies its preparation method and has positive effect, will be described below
Technical scheme be caused under this background.
The content of the invention
Top priority of the present invention is that providing one kind contributes to abundant Bola types kinds of surfactants and structure novelty
The amino-acid modified organic silicon surfactant of Bola types.
Another task of the present invention is to provide a kind of preparation of the amino-acid modified organic silicon surfactant of Bola types
Method, this method technical process is brief, and preparation cost is cheap and is satisfied industrial amplification production requirement and can ensure system
The standby amino-acid modified organic silicon surfactant of Bola types possesses excellent surface-active and can be gathered into aqueous poly-
Collective and be satisfied medicine, the application requirement of biotechnology field.
To embody the top priority for completing the present invention, concrete technical scheme provided by the invention is：A kind of Bola types amino
Sour modified silicone surfactants, its general structure are as follows：
In formula：M is 1-200 integer.
In one particular embodiment of the present invention, the amino-acid modified organic silicon surfactant of Bola types is water-soluble
The lowest surface tension of liquid is 24 to 43mN/m and critical micelle concentration is 50 to 380mg/L in aqueous.
To embody another task for completing the present invention, technical scheme provided by the invention is：A kind of Bola types amino acid changes
The preparation method of property organic silicon surfactant, comprises the following steps：
(1) preparation of double amino-terminated polysiloxanes
With cyclosiloxane, double (the 3- aminopropyls) -1 of 1,3-, 1,3,3- tetramethyl disiloxane is raw material, utilizes catalyst
Reaction, and controlling reaction temperature and control reaction time, after reaction terminates, make catalyst inactivation, then be evaporated under reduced pressure removal not
The raw material of reaction, obtain double amino-terminated polysiloxanes；
(2) preparation of double aminopropanoate type polysiloxanes
The double amino-terminated polysiloxanes and methyl acrylate obtained using step (1) are raw material in the presence of low-carbon alcoholic solvent
Reaction, and the reaction temperature in the presence of low alcoholic solvent and reaction time are controlled, after the completion of reaction, low-carbon alcoholic solvent is evaporated off, obtains
To double aminopropanoate type polysiloxanes；
(3) preparation of the amino-acid modified organic silicon surfactant of Bola types
Step (2) is obtained into double aminopropanoate type polysiloxanes and sodium hydroxide solution in the presence of low-carbon alcoholic solvent
Reaction, and the reaction temperature in the presence of low alcoholic solvent and reaction time are controlled, after the completion of reaction, low-carbon alcoholic solvent is evaporated off, obtains
To the amino-acid modified organic silicon surfactant of Bola types.
In another specific embodiment of the present invention, double (the 3- aminopropans of cyclosiloxane and 1,3- described in step (1)
Base) mol ratio of -1,1,3,3- tetramethyl disiloxanes and catalyst three is 1-20:1:0.01-0.1；Described control
Reaction temperature be by reaction temperature control be 20-120 DEG C, it is described control the reaction time be by the reaction time control be 1-50h.
In another specific embodiment of the present invention, described cyclosiloxane is hexamethyl cyclotrisiloxane, eight alkyl
Cyclotetrasiloxane, decamethylcyclopentaandoxane or the siloxanes of ten diformazan basic ring six.
In another specific embodiment of the present invention, described catalyst is alkali metal hydroxide, silicon alkoxide, season
Ammonium alkali, quaternary phosphonium hydroxides, silanol quaternary ammonium salt or silanol quaternary alkylphosphonium salt；Wherein, it is described to refer to catalyst inactivation：When catalyst is alkali gold
When belonging to any one in hydroxide and silicon alkoxide, add acid and catalyst is neutralized and makes catalyst inactivation, and work as catalyst
For any one in quaternary ammonium base, quaternary phosphonium hydroxides, silanol quaternary ammonium salt and silanol quaternary alkylphosphonium salt when, carry out heat resolve and lose catalyst
It is living.
In the also specific embodiment of the present invention, described alkali metal hydroxide is sodium hydroxide or hydrogen-oxygen
Change potassium；Described silicon alkoxide is sodium silanolate or silanol potassium；Described quaternary ammonium base is TMAH；The quaternary phosphonium hydroxides are
Si butyl phosphonium hydroxides；Described silanol quaternary ammonium salt is tetramethyl silanol ammonium；Described silanol quaternary alkylphosphonium salt is tetrabutyl silanol Phosphonium.
The present invention's and then in a specific embodiment, double amino-terminated polysiloxanes described in step (2) and
The mol ratio of both methyl acrylates is 1:2；Reaction temperature and reaction time in the presence of described control low-carbon alcoholic solvent are
It is the reflux temperature of solvent by reaction temperature control, will controls in the reaction time as 1-20h；The low-carbon alcoholic solvent is methanol, second
Alcohol, propyl alcohol or isopropanol.
The present invention again more and a specific embodiment in, double aminopropanoate types described in step (3) gather
The mol ratio of both siloxanes and sodium hydroxide solution is 1:2；The quality % specific concentrations of the sodium hydroxide solution be 20% to
50%；The described reaction temperature controlled in the presence of low-carbon alcoholic solvent and reaction time are returning for solvent by reaction temperature control
Temperature is flowed, will be controlled in the reaction time as 2-20h；The low-carbon alcoholic solvent is methanol, ethanol, propyl alcohol or isopropanol.
Because the amino-acid modified organic silicon surfactant of Bola types provided by the invention is as belonging to a kind of new organic
Silicon surface active agent, thus the species of abundant organic silicon surfactant is able to, extend use range；Due to preparation process
Letter prepares that cost is cheap without tired, thus can meet industrial amplification production requirement and can make the Bola type ammonia of acquisition
Base acid modified silicone surfactants possess excellent surface-active and can be gathered into aggregation in aqueous, so as to answer
For in medicine, biotechnology field.
Embodiment
Such scheme is described further below in conjunction with specific embodiment.It should be understood that these embodiments are to be used to illustrate
The present invention and be not limited to limit the scope of the present invention, all equivalent transformations done according to spirit of the invention or modification, all should
It is included within the scope of the present invention.The implementation condition used in embodiment can do further tune according to actual conditions
Whole, unreceipted implementation condition is usually the condition in normal experiment.
The amino-acid modified organic silicon surfactant of Bola types of structures shown below formula is prepared respectively by four implementations
Example is illustrated.
Wherein m is 1-200 integer.
Embodiment 1
The preparation of double amino-terminated polysiloxanes
Addition hexamethyl cyclotrisiloxane 55.6Kg (250mol) in a kettle, 1,3- double (3- aminopropyls) -1,1,
3,3- tetramethyl disiloxane 12.4Kg (50mol), TMAH 0.45Kg (5mol), dissolve by heating, temperature control
At 20 DEG C, after reacting 50h, 140 DEG C are warming up to, makes catalyst inactivation, rectification under vacuum removes excess raw material and obtains double aminopropyl envelopes
Hold polysiloxanes 67.9Kg (50mol).
The preparation of bis-amino acid methyl esters type polysiloxanes
Above-mentioned double amino-terminated polysiloxanes 67.9Kg (50mol), methyl acrylate 8.6Kg are added in a kettle
(100mol), using ethanol as solvent, 1h is reacted at a reflux temperature, steams etoh solvent, obtain bis-amino acid methyl esters type and gather
Siloxanes 76.5Kg (50mol)
The preparation of the amino-acid modified organic silicon surfactant of Bola types
Above-mentioned bis-amino acid methyl esters type polysiloxanes 76.5Kg (50mol) is added in a kettle and 20% sodium hydroxide is molten
Liquid 20Kg (100mol), using methanol as solvent, reacts 20h at a reflux temperature, steams methanol, Bola is obtained after vacuum drying
The amino-acid modified organic silicon surfactant 77.3Kg (50mol) of type, the minimum table for its aqueous solution surveyed with K12 surface tension instruments
Face tension force is 37mN/m, critical micelle concentration 275mg/L.
Embodiment 2
The preparation of double amino-terminated polysiloxanes
Addition octamethylcy-clotetrasiloxane 222.5Kg (750mol) in a kettle, 1,3- double (3- aminopropyls) -1,1,
3,3- tetramethyl disiloxane 12.4Kg (50mol), tetramethyl silanol ammonium 0.18Kg (0.5mol), dissolve by heating, temperature control
At 60 DEG C, after reacting 25h, 140 DEG C are warming up to, makes catalyst inactivation, rectification under vacuum removes excess raw material and obtains double aminopropyl envelopes
Hold polysiloxanes 234.4Kg (50mol).
The preparation of bis-amino acid methyl esters type polysiloxanes
Above-mentioned double amino-terminated polysiloxanes 234.4Kg (50mol), methyl acrylate 8.6Kg are added in a kettle
(100mol), using methanol as solvent, 20h is reacted at a reflux temperature, steams solvent methanol, obtain bis-amino acid methyl esters type and gather
Siloxanes 243Kg (50mol)
The preparation of the amino-acid modified organic silicon surfactant of Bola types
Above-mentioned bis-amino acid methyl esters type polysiloxanes 243Kg (50mol) is added in a kettle and 50% sodium hydroxide is molten
Liquid 8Kg (100mol), using ethanol as solvent, reacts 2h at a reflux temperature, steams ethanol, Bola types are obtained after vacuum drying
Amino-acid modified organic silicon surfactant 243.8Kg (50mol), the minimum table for its aqueous solution surveyed with K12 surface tension instruments
Face tension force is 28mN/m, critical micelle concentration 134mg/L.
Embodiment 3
The preparation of double amino-terminated polysiloxanes
Addition decamethylcyclopentaandoxane 370.8Kg (1000mol) in a kettle, 1,3- double (3- aminopropyls) -1,
1,3,3- tetramethyl disiloxane 12.4Kg (50mol), sodium hydroxide 0.1Kg (2.5mol), are dissolved by heating, and temperature control exists
120 DEG C, after reacting 1h, acid adding neutralizes, and makes catalyst inactivation, and rectification under vacuum removes excess raw material and obtains the poly- silicon of double aminopropyls end-blockings
Oxygen alkane 382.4Kg (50mol).
The preparation of bis-amino acid methyl esters type polysiloxanes
Above-mentioned double amino-terminated polysiloxanes 382.4Kg (50mol), methyl acrylate 8.6Kg are added in a kettle
(100mol), using propyl alcohol as solvent, 10h is reacted at a reflux temperature, steam solvent propyl alcohol, obtain bis-amino acid methyl esters type and gather
Siloxanes 391.0 (50mol)
The preparation of the amino-acid modified organic silicon surfactant of Bola types
Above-mentioned bis-amino acid methyl esters type polysiloxanes 391.0Kg (50mol) and 30% sodium hydroxide are added in a kettle
Solution 13.3Kg (100mol), using isopropanol as solvent, reacts 5h at a reflux temperature, isopropanol is steamed, after vacuum drying
The amino-acid modified organic silicon surfactant 391.8Kg (50mol) of Bola types is obtained, its surveyed with K12 surface tension instruments is water-soluble
The lowest surface tension of liquid is 24mN/m, critical micelle concentration 50mg/L.
Embodiment 4
The preparation of double amino-terminated polysiloxanes
Add ten diformazan basic ring six siloxanes 22.2Kg (50mol) in a kettle, 1,3- double (3- aminopropyls) -1,1,
3,3- tetramethyl disiloxane 12.4Kg (50mol), Si butyl phosphonium hydroxides 0.27Kg (1.0mol), dissolve by heating, temperature control
System after reacting 15h, is warming up to 140 DEG C at 100 DEG C, makes catalyst inactivation, and rectification under vacuum removes excess raw material and obtains double aminopropyls
Terminated polysiloxane 34.6Kg (50mol).
The preparation of bis-amino acid methyl esters type polysiloxanes
Above-mentioned double amino-terminated polysiloxanes 34.6Kg (50mol), methyl acrylate 8.6Kg are added in a kettle
(100mol), using isopropanol as solvent, 5h is reacted at a reflux temperature, steam solvent isopropanol, obtain bis-amino acid methyl esters
Type polysiloxanes 43.2Kg (50mol).
The preparation of the amino-acid modified organic silicon surfactant of Bola types
Above-mentioned bis-amino acid methyl esters type polysiloxanes 43.2Kg (50mol) is added in a kettle and 40% sodium hydroxide is molten
Liquid 10.0Kg (100mol), using propyl alcohol as solvent, reacts 10h at a reflux temperature, steams propyl alcohol, is obtained after vacuum drying
The amino-acid modified organic silicon surfactant 391.8Kg (50mol) of Bola types, its aqueous solution surveyed with K12 surface tension instruments
Lowest surface tension is 43mN/m, critical micelle concentration 380mg/L.
Claims (9)
1. a kind of amino-acid modified organic silicon surfactant of Bola types, it is characterised in that its general structure is as follows：
In formula：M is 1-200 integer.
2. a kind of amino-acid modified organic silicon surfactant of Bola types according to claim 1, it is characterised in that described
The lowest surface tension of the aqueous solution of the amino-acid modified organic silicon surfactant of Bola types is 24 to 43mN/m and water-soluble
Critical micelle concentration is 50 to 380mg/L in liquid.
3. a kind of preparation method of the amino-acid modified organic silicon surfactant of Bola types as claimed in claim 1, its feature
It is to comprise the following steps：
(1) preparation of double amino-terminated polysiloxanes
With cyclosiloxane, double (the 3- aminopropyls) -1 of 1,3-, 1,3,3- tetramethyl disiloxane is raw material, anti-using catalyst
Should, and controlling reaction temperature and control the reaction time, reaction terminate after, make catalyst inactivation, then be evaporated under reduced pressure remove it is not anti-
The raw material answered, obtain double amino-terminated polysiloxanes；
(2) preparation of double aminopropanoate type polysiloxanes
Using the double amino-terminated polysiloxanes and methyl acrylate that step (1) obtains as raw material in the presence of low-carbon alcoholic solvent it is anti-
Should, and the reaction temperature in the presence of low alcoholic solvent and reaction time are controlled, after the completion of reaction, low-carbon alcoholic solvent is evaporated off, obtains
Double aminopropanoate type polysiloxanes；
(3) preparation of the amino-acid modified organic silicon surfactant of Bola types
By step (2) obtain double aminopropanoate type polysiloxanes and sodium hydroxide solution in the presence of low-carbon alcoholic solvent it is anti-
Should, and the reaction temperature in the presence of low alcoholic solvent and reaction time are controlled, after the completion of reaction, low-carbon alcoholic solvent is evaporated off, obtains
The amino-acid modified organic silicon surfactant of Bola types.
4. a kind of preparation method of amino-acid modified organic silicon surfactant of Bola types according to claim 3, it is special
Sign be cyclosiloxane described in step (1) (3- aminopropyls) -1,1,3,3- tetramethyl disiloxanes double with 1,3- and
The mol ratio of catalyst three is 1-20:1:0.01-0.1；Described controlling reaction temperature be by reaction temperature control be 20-
120 DEG C, it is described control the reaction time be by the reaction time control be 1-50h.
5. a kind of preparation method of amino-acid modified organic silicon surfactant of Bola types according to claim 3 or 4, its
Be characterised by described cyclosiloxane be hexamethyl cyclotrisiloxane, eight alkyl cyclotetrasiloxanes, decamethylcyclopentaandoxane or
The siloxanes of ten diformazan basic ring six.
6. a kind of preparation method of amino-acid modified organic silicon surfactant of Bola types according to claim 3 or 4, its
It is characterised by that described catalyst is alkali metal hydroxide, silicon alkoxide, quaternary ammonium base, quaternary phosphonium hydroxides, silanol quaternary ammonium salt or silanol season
Phosphonium salt；Wherein, it is described to refer to catalyst inactivation：When catalyst is any one in alkali metal hydroxide and silicon alkoxide
When, add acid and catalyst is neutralized and makes catalyst inactivation, and when catalyst is quaternary ammonium base, quaternary phosphonium hydroxides, silanol quaternary ammonium salt and silicon
During any one in Chun quaternary alkylphosphonium salts, carry out heat resolve and make catalyst inactivation.
7. a kind of preparation method of amino-acid modified organic silicon surfactant of Bola types according to claim 6, it is special
Sign is that described alkali metal hydroxide is sodium hydroxide or potassium hydroxide；Described silicon alkoxide is sodium silanolate or silanol potassium；
Described quaternary ammonium base is TMAH；The quaternary phosphonium hydroxides are Si butyl phosphonium hydroxides；Described silanol quaternary ammonium salt is
Tetramethyl silanol ammonium；Described silanol quaternary alkylphosphonium salt is tetrabutyl silanol Phosphonium.
8. a kind of preparation method of amino-acid modified organic silicon surfactant of Bola types according to claim 3, it is special
Sign is that the mol ratio of both double amino-terminated polysiloxanes and methyl acrylate described in step (2) is 1:2；Described control
Reaction temperature and reaction time in the presence of low-carbon alcoholic solvent processed are by the reflux temperature that reaction temperature control is solvent, will be reacted
Time control is 1-20h；The low-carbon alcoholic solvent is methanol, ethanol, propyl alcohol or isopropanol.
9. a kind of preparation method of amino-acid modified organic silicon surfactant of Bola types according to claim 3, it is special
Sign is that the mol ratio of both double aminopropanoate type polysiloxanes and sodium hydroxide solution described in step (3) is 1:2；
The quality % specific concentrations of the sodium hydroxide solution are 20% to 50%；Reaction temperature in the presence of described control low-carbon alcoholic solvent
Degree and reaction time are by the reflux temperature that reaction temperature control is solvent, will be controlled in the reaction time as 2-20h；The low-carbon alcohols
Solvent is methanol, ethanol, propyl alcohol or isopropanol.
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| CN111992134A (en) * | 2020-09-22 | 2020-11-27 | 陕西科技大学 | Polycarboxyl amphoteric Bola type surfactant and preparation method thereof |
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| CN115087430A (en) * | 2019-12-20 | 2022-09-20 | 艾德凡斯化学公司 | Surfactant for health care products |
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