CN111548501A - Preparation method of organic silicon surfactant containing amino acid - Google Patents
Preparation method of organic silicon surfactant containing amino acid Download PDFInfo
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Abstract
The invention relates to a preparation method of an organic silicon surfactant containing amino acid, which comprises the steps of reacting polyether modified amino silicone oil with acrylate or chloroacetate, and hydrolyzing under an alkaline condition to obtain the organic silicon surfactant containing amino acid. According to the invention, polyether modified amino silicone oil is adopted to react with acrylate or chloroacetate, and then alkaline hydrolysis is carried out to prepare the organic silicon surfactant containing amino acid, so that the reaction condition is simple, gel is not easy to generate in the reaction process, the product yield is high, the price is low, and the industrial production is facilitated; the surfactant prepared by the invention has the characteristics of organic silicon wetting spreadability, thermal stability, excellent biodegradability, greenness and safety.
Description
Technical Field
The invention belongs to the technical field of surfactants, and particularly relates to a preparation method of an organic silicon surfactant containing amino acid.
Background
The amino acid surfactant has the advantages of simple and easily obtained and reproducible preparation raw materials, relatively simple synthesis method, low toxicity, low irritation, easy biodegradation, good environmental compatibility and the like, and is widely researched and applied in the industries of food, biological pharmacy, daily chemicals, chemical industry and the like.
The organosilicon surfactant has the advantages of low surface tension, good wetting and spreading properties, strong thermal stability, large emulsifying effect, good compatibility, foaming, foam stabilizing and foam inhibiting effects, no toxicity and no side effect, and is widely used in the fields of textiles, cosmetics, plastics, coatings, agricultural chemicals, medicines, machining and the like.
The amino acid group is introduced into the organic silicon surfactant, so that the excellent biodegradability and green safety of amino acid can be maintained, and the characteristics of wetting spreadability and thermal stability of organic silicon can be maintained, so that the surfactant has higher use temperature and better permeability, and the application range of the surfactant is greatly improved.
At present, amino acid organic silicon surfactants are mainly prepared by reacting epoxy silicone oil with amino acid, patents CN107787343A and CN107636048A disclose that alpha, omega-glycidoxypropyl functionalized polysiloxane is reacted with amino in amino acid to prepare side chain amino acid modified organic silicon surfactants, DE10036532 discloses that polysiloxane with epoxy group is reacted with amino acid derivatives, the amino acid exists in a salt protection form or an ester form, and the conversion of the amino acid into a salt or an ester on an industrial scale requires additional reaction steps, so that the synthesis is inconvenient and expensive; EP2826806 discloses the production of amino acid modified siloxanes from quaternary amino acid salts. The formation of these amino acid salts requires two reaction steps: in a first step, the amino acid is converted into the potassium salt, and in a second step, the reaction with quaternary ammonium or phosphonium chloride gives the quaternary amino acid salt, the potassium chloride formed by the reaction being removed by precipitation by dispersion in a suitable medium. This process is therefore both inconvenient and expensive. EP2231753 uses the reaction of free amino acids with epoxy functional polysiloxanes in the presence of about 25-28% of an emulsifier. The reaction has certain requirements on the content and position of the epoxy silicone oil and certain requirements on reaction conditions, and the reaction process is easy to generate a gel phenomenon, so that the product yield is low, the price is high, and the industrial process is not facilitated.
The present invention has been made in view of the above circumstances.
Disclosure of Invention
In order to solve the problems in the prior art, the invention provides a preparation method of an organosilicon surfactant containing amino acid, and the preparation method is simple, high in yield, low in production cost, controllable in reaction conditions and difficult to generate gel in the reaction process.
In order to achieve the purpose, the invention adopts the following technical scheme:
polyether modified amino silicone oil reacts with acrylate or chloroacetate, and the mixture is hydrolyzed under alkaline condition to obtain the amino acid-containing organosilicon surfactant.
Further, the chemical equation occurring in preparing the amino acid-containing silicone surfactant is as follows:
or
Wherein R is CH3；R1Is H, CH3Or CH2＝CH；
R2Is CH2CH2CH2O(CH2CH2O) aR or
CH2CH2CH2O(CH2CH2O)b[(CH3)CHCH2]cR, a is an integer between 6 and 10, b is an integer between 6 and 10, and c is an integer between 2 and 6;
R3is CH2CH2COOR；R4Is H or CH2CH2COOR；R5Is CH2CH2COONa； R6Is H or CH2CH2COONa；R7Is CH2COOR；R8Is H or CH2COOR；R9Is CH2COONa；R10Is H or CH2COONa；
m is an integer between 10 and 200, n is an integer between 3 and 20, o is an integer between 2 and 8, and p is an integer between 1 and 3.
Further, the polyether modified amino silicone oil is prepared by the following method:
(1) preparation of hydrogen-containing silicone oil: adding a methyl double-end socket, D4, hydrogen-containing D4 and a catalyst A into a reaction bottle, heating for reaction to obtain silicon oil, filtering acid resin out of the silicon oil, and distilling under reduced pressure to obtain hydrogen-containing silicon oil;
(2) preparing polyether modified amino silicone oil: adding the hydrogen-containing silicone oil into vinyl-terminated polyether and silicon methyl-terminated allylamine, then adding a catalyst B, heating to 120-130 ℃ for reaction, adding methanol after the reaction is carried out for 7-9h, and decompressing and distilling out low-boiling-point substances to obtain the polyether modified amino acid silicone oil.
Further, in the step (1), the molar ratio of the methyl double-end socket, the D4 and the hydrogen-containing D4 is 0.02-0.05:20-80: 2-10: 0.0000001-0.0000002.
Further, the temperature of the heating reaction in the step (1) is 80-120 ℃, and the reaction time is 6-10 h.
Further, the temperature of the temperature rise reaction in the step (1) is 100 ℃, and the reaction time is 8 hours.
Further, the catalyst A in the step (1) is a strong acid cation resin.
Further, the molar ratio of the mol of the hydrogen-containing silicone oil to the total mol of the vinyl-terminated polyether and the silicon methyl-terminated allylamine in the step (2) is 1: 1.0-1.2.
Further, the mol ratio of the vinyl-terminated polyether to the silicon methyl-terminated allylamine in the step (2) is 1: 1-100.
Further, the catalyst in the step (2) is Pt.
The chemical reaction equation in the synthesis of the polyether modified amino silicone oil is as follows:
compared with the prior art, the invention has the beneficial effects that:
according to the invention, polyether modified amino silicone oil is adopted to react with acrylate or chloroacetate, and then alkaline hydrolysis is carried out to prepare the organic silicon surfactant containing amino acid, so that the reaction condition is simple, gel is not easy to generate in the reaction process, the product yield is high, the price is low, the industrial production is facilitated, and the synthesis process is simple; the surfactant prepared by the invention has the characteristics of organic silicon wetting spreadability, thermal stability, excellent biodegradability, greenness and safety.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the technical solutions of the present invention will be described in detail below. It is to be understood that the described embodiments are merely exemplary of the invention, and not restrictive of the full scope of the invention. All other embodiments, which can be derived by a person skilled in the art from the examples given herein without any inventive step, are within the scope of the present invention.
Example 1
The polyether modified amino silicone oil of the embodiment is prepared by the following method:
(1) preparation of hydrogen-containing silicone oil: adding a methyl double-end socket, D4, hydrogen-containing D4 and catalyst A strong acid cation resin into a reaction bottle, wherein the molar ratio of the methyl double-end socket to the D4 to the hydrogen-containing D4 to the catalyst A is 0.02:80: 2: 0.0000002, heating for reaction at 80 ℃ for 10h to obtain silicone oil, filtering out acidic resin, and distilling under reduced pressure to obtain hydrogen-containing silicone oil;
(2) preparing polyether modified amino silicone oil: adding vinyl-terminated polyether and silicon methyl-terminated allylamine into the hydrogen-containing silicone oil, wherein the molecular weight of the vinyl-terminated polyether is 628, the EO chain segment is 12, the silicon methyl-terminated allylamine is N1-allyl-N1, N2, N2-tri (trimethylsilyl) ethane-1, 2-diamine, the molar ratio of the mole of the hydrogen-containing silicone oil to the total mole of the vinyl-terminated polyether and the silicon methyl-terminated allylamine is 1:1.0, the molar ratio of the vinyl-terminated polyether to the silicon methyl-terminated allylamine is 1:1, then adding a catalyst Pt, heating to 120 ℃ for reaction, adding methanol after the reaction is carried out for 9 hours, and decompressing and distilling out low-boiling-point substances to obtain the polyether modified amino acid silicone oil (compound A).
The preparation method of the organosilicon surfactant containing amino acid in the embodiment is as follows:
100g (ammonia value, 0.39mmol/g) of polyether modified amino silicone oil (compound A) and 100mL of isopropanol were added to a 250mL reaction flask, 1.8g (20.5mmol) of methyl acrylate was added dropwise to the reaction vessel over 1 hour, and the reaction temperature was kept at about 25 ℃ because the reaction was exothermic. After 5h of reaction, removing excessive raw materials and solvent by rotary evaporation, drying in vacuum to obtain light yellow viscous liquid, then adding 100mL of isopropanol and 2.43g (19.4mmol) of 32% sodium hydroxide solution, heating and refluxing for 5h, filtering to obtain a liquid product, removing the solvent by rotary evaporation, and drying in vacuum to obtain 96.8g of the amino acid-containing organosilicon surfactant (compound 1a) with the yield of 95.0%, wherein the reaction equation is as follows:
example 2
The polyether-modified amino silicone oil of this example was prepared in the same manner as in example 1.
The preparation method of the organosilicon surfactant containing amino acid in the embodiment is as follows:
100g (ammonia value, 0.39mmol/g) of polyether modified amino silicone oil (compound A) and 100mL of isopropanol were added to a 250mL reaction flask, 3.6g (41.0mmol) of methyl acrylate was added dropwise to the reaction vessel over 2 hours, and the reaction temperature was kept at about 25 ℃ because the reaction was exothermic. After 10h of reaction, removing excessive raw materials and solvent by rotary evaporation, drying in vacuum to obtain yellow viscous liquid, then adding 100mL of isopropanol and 4.86g (38.9mmol) of 32% sodium hydroxide solution, heating and refluxing for 5h, filtering to obtain liquid product, removing solvent by rotary evaporation, and drying in vacuum to obtain 95.9g of the amino acid-containing organosilicon surfactant (compound 1 b' and compound 1b) with the yield of 92.4%, wherein the reaction equation is as follows:
example 3
The polyether modified amino silicone oil of the embodiment is prepared by the following method:
(1) preparation of hydrogen-containing silicone oil: adding a methyl double-end socket, D4, hydrogen-containing D4 and catalyst A strong acid cation resin into a reaction bottle, wherein the molar ratio of the methyl double-end socket to the D4 to the hydrogen-containing D4 to the catalyst A is 0.035:40: 6: 0.00000015, heating for reaction at 100 ℃ for 8h to obtain silicone oil, filtering out acidic resin, and distilling under reduced pressure to obtain hydrogen-containing silicone oil;
(2) preparing polyether modified amino silicone oil: adding vinyl-terminated polyether and silicon methyl-terminated allylamine into the hydrogen-containing silicone oil, wherein the molecular weight of the vinyl-terminated polyether is 628, the EO chain segment is 12, the silicon methyl-terminated allylamine is N1-allyl-N1, N2, N2-tri (trimethylsilyl) ethane-1, 2-diamine, the molar ratio of the mole of the hydrogen-containing silicone oil to the total mole of the vinyl-terminated polyether and the silicon methyl-terminated allylamine is 1:1.1, the molar ratio of the vinyl-terminated polyether to the silicon methyl-terminated allylamine is 1:50, then adding a catalyst Pt, heating to 125 ℃ for reaction, adding methanol after the reaction is carried out for 8 hours, and decompressing and distilling out low-boiling-point substances to obtain the polyether modified amino acid silicone oil (compound A).
The preparation method of the organosilicon surfactant containing amino acid in the embodiment is as follows:
100g (ammonia value, 0.39mmol/g) of polyether modified amino silicone oil (compound A) and 100mL of isopropanol were added to a 250mL reaction flask, 5.4g (61.4mmol) of methyl acrylate was added dropwise to the reaction vessel over 3 hours, and the reaction temperature was kept at about 25 ℃ because the reaction was exothermic. After 20h of reaction, removing excessive raw materials and solvent by rotary evaporation, drying in vacuum to obtain yellow viscous liquid, then adding 100mL of isopropanol and 7.29g (58.5mmol) of 32% sodium hydroxide solution, heating and refluxing for 5h, filtering to obtain a liquid product, removing the solvent by rotary evaporation, and drying in vacuum to obtain 96.6g of the amino acid-containing organosilicon surfactant (compound 1c) with a yield of 91.5%, wherein the reaction equation is as follows:
example 4
The polyether-modified amino silicone oil of this example was prepared in the same manner as in example 3.
The preparation method of the organosilicon surfactant containing amino acid in the embodiment is as follows:
100g (ammonia value, 0.39mmol/g) of polyether modified amino silicone oil (compound A) and 100mL of isopropanol are added into a 250mL reaction bottle, 2.57g (20.5mmol) of 32% sodium hydroxide solution and 2.23g (20.5mmol) are simultaneously added into the reaction vessel dropwise within 1h, and the pH value of the system is kept at about 10. After 4 hours of reaction, removing excessive raw materials and solvent by rotary evaporation, drying in vacuum to obtain light yellow viscous liquid, then adding 100mL of isopropanol and 2.43g (19.4mmol) of 32% sodium hydroxide solution, heating and refluxing for 5 hours, filtering to obtain a liquid product, removing the solvent by rotary evaporation, and drying in vacuum to obtain 97.9g of the amino acid-containing organosilicon surfactant (compound 2a) with the yield of 96.4%, wherein the reaction equation is as follows:
example 5
The polyether modified amino silicone oil of the embodiment is prepared by the following method:
(1) preparation of hydrogen-containing silicone oil: adding a methyl double-end socket, D4, hydrogen-containing D4 and catalyst A strong acid cation resin into a reaction bottle, wherein the molar ratio of the methyl double-end socket to the D4 to the hydrogen-containing D4 to the catalyst A is 0.05:20: 10: 0.0000001, heating for reaction at 120 ℃ for 6 hours to obtain silicone oil, filtering out acid resin, and distilling under reduced pressure to obtain hydrogen-containing silicone oil;
(2) preparing polyether modified amino silicone oil: adding vinyl-terminated polyether and silicon methyl-terminated allylamine into the hydrogen-containing silicone oil, wherein the molecular weight of the vinyl-terminated polyether is 628, the EO chain segment is 12, the silicon methyl-terminated allylamine is N1-allyl-N1, N2, N2-tri (trimethylsilyl) ethane-1, 2-diamine, the molar ratio of the mole of the hydrogen-containing silicone oil to the total mole of the vinyl-terminated polyether and the silicon methyl-terminated allylamine is 1:1.2, the molar ratio of the vinyl-terminated polyether to the silicon methyl-terminated allylamine is 1:100, then adding a catalyst Pt, heating to 80 ℃ for reaction, adding methanol after the reaction is carried out for 7 hours, and decompressing and distilling out low-boiling-point substances to obtain the polyether modified amino acid silicone oil (compound A).
The preparation method of the organosilicon surfactant containing amino acid in the embodiment is as follows:
100g (ammonia value, 0.39mmol/g) of polyether modified amino silicone oil (compound A) and 100mL of isopropanol are added into a 250mL reaction bottle, 5.14g (41.0mmol) and 4.46g (41.0mmol) of 32% sodium hydroxide solution are simultaneously added into the reaction vessel dropwise within 1h, and the pH value of the system is kept at about 10. After 10h of reaction, the excess starting material and solvent were removed by rotary evaporation, vacuum dried to give a yellow viscous liquid, then 100mL of isopropanol and 4.87g (39.0mmol) of 32% sodium hydroxide solution were added, heated under reflux for 5h, filtered to give a liquid product, and then the solvent was removed by rotary evaporation, vacuum dried to give 95.7g of the amino acid-containing organosilicon surfactant (compound 2 b' and compound 2b) in 92.8% yield, according to the following equation:
example 6
The polyether modified amino silicone oil of this example was prepared in the same manner as in example 5.
The preparation method of the organosilicon surfactant containing amino acid in the embodiment is as follows:
100g (ammonia value, 0.39mmol/g) of polyether modified amino silicone oil (compound A) and 100mL of isopropanol are added into a 250mL reaction bottle, 7.7g (61.4mmol) and 6.68g (61.4mmol) of 32% sodium hydroxide solution are simultaneously added into the reaction vessel dropwise within 1h, and the pH value of the system is kept at about 10. After 20h of reaction, removing excessive raw materials and solvent by rotary evaporation, drying in vacuum to obtain yellow viscous liquid, then adding 100mL of isopropanol and 7.29g (58.5mmol) of 32% sodium hydroxide solution, heating and refluxing for 5h, filtering to obtain liquid product, removing solvent by rotary evaporation, and drying in vacuum to obtain 95.5g of the amino acid-containing organosilicon surfactant (compound 2c) with a yield of 91.2%, wherein the reaction equation is as follows:
example 7
The preparation method of the polyether modified amino silicone oil in the embodiment is the same as that in the embodiment 1, and the experimental parameters are properly adjusted to obtain the polyether modified amino silicone oil, wherein p in the molecular formula of the polyether modified amino silicone oil is 2 or 3, and the corresponding amino acid silicone surfactant is prepared by adopting the preparation method of any one of the amino acid silicone surfactants in the embodiments 1 to 6.
Test example 1
The prepared amino acid-containing silicone surfactants were subjected to the following performance tests, respectively, and the results are shown in table 1.
TABLE 1
| Compound (I) | Wettability | Spreadability | Biodegradability | Thermal stability |
| Compound 1a | 2 | 2 | 1 | 1 |
| Compound 1b | 2 | 2 | 2 | 2 |
| Compound 1c | 1 | 1 | 2 | 2 |
| Compound 2a | 2 | 2 | 2 | 1 |
| Compound 2b | 2 | 2 | 2 | 1 |
| Compound 2c | 1 | 1 | 2 | 1 |
Note: the numbers 1-5 in the table identify the order of the highest and lowest performance, with 1 being the best, 5 being the worst, and the higher the number the worse the performance.
The inventors also performed the above experiments on other compounds, and the results were substantially consistent and, due to the limited space, are not listed.
The above description is only for the specific embodiments of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art can easily conceive of the changes or substitutions within the technical scope of the present invention, and all the changes or substitutions should be covered within the scope of the present invention. Therefore, the protection scope of the present invention shall be subject to the protection scope of the appended claims.
Claims (10)
1. The preparation method of the organic silicon surfactant containing the amino acid is characterized in that polyether modified amino silicone oil reacts with acrylate or chloroacetate, and the mixture is hydrolyzed under the alkaline condition to obtain the organic silicon surfactant containing the amino acid.
2. The method of preparing an amino acid-containing silicone surfactant according to claim 1, wherein the chemical equation occurring in preparing the amino acid-containing silicone surfactant is as follows:
wherein R is CH3；R1Is H, CH3Or CH2＝CH；
R2Is CH2CH2CH2O(CH2CH2O) aR or
CH2CH2CH2O(CH2CH2O)b[(CH3)CHCH2]cR, a is an integer between 6 and 10, b is an integer between 6 and 10, and c is an integer between 2 and 6;
R3is CH2CH2COOR；R4Is H or CH2CH2COOR；R5Is CH2CH2COONa；R6Is H or CH2CH2COONa；R7Is CH2COOR；R8Is H or CH2COOR；R9Is CH2COONa；R10Is H or CH2COONa；
m is an integer between 10 and 200, n is an integer between 3 and 20, o is an integer between 2 and 8, and p is an integer between 1 and 3.
3. The method for preparing an amino acid-containing silicone surfactant according to claim 1 or 2, wherein the polyether-modified amino silicone oil is prepared by the following method:
(1) preparation of hydrogen-containing silicone oil: adding a methyl double-end socket, D4, hydrogen-containing D4 and a catalyst A into a reaction bottle, heating for reaction to obtain silicon oil, filtering acid resin out of the silicon oil, and distilling under reduced pressure to obtain hydrogen-containing silicon oil;
(2) preparing polyether modified amino silicone oil: adding the hydrogen-containing silicone oil into vinyl-terminated polyether and silicon methyl-terminated allylamine, then adding a catalyst B, heating to 120-130 ℃ for reaction, adding methanol after the reaction is carried out for 7-9h, and decompressing and distilling out low-boiling-point substances to obtain the polyether modified amino acid silicone oil.
4. The method for preparing organosilicon surfactant containing amino acid according to claim 3, wherein the molar ratio of methyl double head, D4, hydrogen-containing D4 and catalyst A in step (1) is 0.02-0.05:20-80: 2-10: 0.0000001-0.0000002.
5. The process for preparing the organosilicon surfactant containing amino acids according to claim 3, wherein the temperature of the temperature-raising reaction in step (1) is 80-120 ℃ and the reaction time is 6-10 hours.
6. The process for producing an amino acid-containing silicone surfactant according to claim 5, wherein the temperature of the temperature-raising reaction in step (1) is 100 ℃ and the reaction time is 8 hours.
7. The process for producing an amino acid-containing silicone surfactant according to claim 3, wherein the catalyst A in the step (1) is a strongly acidic cationic resin.
8. The process for producing an amino acid-containing silicone surfactant according to claim 3, wherein the molar ratio of the moles of hydrogen-containing silicone oil to the total moles of vinyl-terminated polyether and silylterminated allylamine in step (2) is 1:1.0 to 1.2.
9. The process for preparing an amino acid-containing silicone surfactant according to claim 8, wherein the molar ratio of the vinyl-terminated polyether to the silylmethyl-terminated allylamine in step (2) is 1:1 to 100.
10. The process for producing an amino acid-containing silicone surfactant according to claim 3, wherein the catalyst in step (2) is Pt.
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