CN110776641A - Preparation method of amino polyether modified polysiloxane - Google Patents
Preparation method of amino polyether modified polysiloxane Download PDFInfo
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- CN110776641A CN110776641A CN201911281321.2A CN201911281321A CN110776641A CN 110776641 A CN110776641 A CN 110776641A CN 201911281321 A CN201911281321 A CN 201911281321A CN 110776641 A CN110776641 A CN 110776641A
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
- C08G77/46—Block-or graft-polymers containing polysiloxane sequences containing polyether sequences
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Abstract
Adding hydrogen-containing silicone oil and a platinum catalyst into a container, stirring and mixing, heating in a water bath to 40-60 ℃, dropwise adding unsaturated ether into the container, continuously heating to 80-95 ℃, stirring and reacting for 5-7 hours under the conditions of nitrogen protection and reflux condensation, and removing unreacted substances through reduced pressure distillation after the reaction is finished to obtain epoxy polyether modified polysiloxane; and (3) stirring the epoxy polyether modified polysiloxane, heating to 55-70 ℃, dropwise adding diethylamine, reacting at a constant temperature for 3-5 hours, and removing unreacted substances by water pump reduced pressure distillation after the reaction is finished to obtain the amino polyether modified polysiloxane. The method can well control the reaction speed and improve the yield and the quality of the epoxy polyether modified polysiloxane.
Description
Technical Field
The invention relates to the technical field of textile softening agents, in particular to a preparation method of amino polyether modified polysiloxane.
Background
Amino modified polyether polysiloxane (amino modified polyether polysiloxane APEPS) is a hydrophilic organic silicon polymer, has nonionic hydrophilic groups, can be mixed and dissolved with water in any proportion without emulsification, has the functions of softness, antistatic property, wetting property and the like, and can be used for textile printing and dyeing, daily chemical industry and other aspects.
The existing amino polyether modified polysiloxane is generally prepared by an alkalization copolymerization method, the reaction process is not easy to control, and the modified amino polyether polysiloxane has the defects of uneven distribution of amino and polyether blocks in molecules, poor product quality and low yield.
Disclosure of Invention
In view of the above, there is a need to provide a method for preparing amino polyether modified polysiloxane, which can solve the problems of the prior art that the reaction process for preparing amino polyether modified polysiloxane is not easy to control and the yield is low.
A preparation method of amino polyether modified polysiloxane comprises the steps of,
preparing epoxy polyether modified polysiloxane: adding hydrogen-containing silicone oil with 0.18 mass percent of active hydrogen and a platinum catalyst into a container, stirring and mixing, heating in a water bath to 40-60 ℃, dropwise adding unsaturated ether into the container, continuously heating to 80-95 ℃, stirring and reacting for 5-7 hours under the conditions of nitrogen protection and reflux condensation, and removing unreacted substances through reduced pressure distillation after the reaction is finished to obtain epoxy polyether modified polysiloxane, wherein the unsaturated ether is a mixed solution of allyl alcohol polyoxyalkyl ether and allyl glycidyl ether, the molar ratio of the alcohol polyoxyalkyl ether to the allyl glycidyl ether in the unsaturated ether is 1: 6-1: 8, and the molar ratio of the hydrogen-containing silicone oil to the unsaturated ether is 1: 1.1-1: 1.3;
preparation of aminopolyether modified polysiloxane: and (2) stirring the epoxy polyether modified polysiloxane, heating to 55-70 ℃, dropwise adding diethylamine, reacting at a constant temperature for 3-5 hours, and removing unreacted substances by water pump reduced pressure distillation after the reaction is finished to obtain the amino polyether modified polysiloxane, wherein the molar ratio of the epoxy polyether modified polysiloxane to the diethylamine is 1: 1-1: 1.2.
Further, in the preparation method, in the step of preparing the epoxy polyether modified polysiloxane, the reaction temperature after the unsaturated ether is dripped into the container is 85 ℃, and the reaction time is 6 hours.
Further, in the preparation method, diethylamine is added dropwise in the preparation step of the amino polyether modified polysiloxane, and then the reaction temperature is kept at 60 ℃ and the reaction time is 4 hours.
Further, the preparation method is characterized in that the molar ratio of the hydrogen-containing silicone oil to the unsaturated ether is 1: 1.2.
Further, according to the preparation method, isopropanol is added before the step of continuously heating to 80-95 ℃ in the preparation process of the epoxy polyether modified polysiloxane, and the mass of the isopropanol accounts for 4.2-5% of the total mass of the hydrogen-containing silicone oil and the unsaturated ether.
Further, in the preparation method, the addition amount of the platinum catalyst is 5-20 ppm of the total mass of the hydrogen-containing silicone oil and the unsaturated ether.
Further, in the above preparation method, the platinum catalyst is a chloroplatinic acid solution.
According to the invention, hydrogen-containing silicone oil, allyl alcohol polyoxyalkyl ether and allyl glycidyl ether are adopted to react under the action of a platinum catalyst to generate intermediate epoxy polyether modified polysiloxane, and the epoxy polyether modified polysiloxane and diethylamine are subjected to ring-opening amination reaction to generate epoxy polyether modified polysiloxane. The method can well control the reaction speed and improve the yield and the quality of the epoxy polyether modified polysiloxane.
Drawings
FIG. 1 shows an infrared spectrum of an aminopolyether-modified polysiloxane obtained in example 1 of the present invention.
Detailed Description
These and other aspects of embodiments of the invention will be apparent from and elucidated with reference to the following description. In the description and drawings, particular embodiments of the invention have been disclosed in detail as being indicative of some of the ways in which the principles of the embodiments of the invention may be practiced, but it is understood that the scope of the embodiments of the invention is not limited correspondingly. On the contrary, the embodiments of the invention include all changes, modifications and equivalents coming within the spirit and terms of the claims appended hereto.
The preparation method of the aminopolyether modified polysiloxane in the embodiment of the invention can be divided into two steps, wherein the first step is to prepare the epoxy polyether modified polysiloxane, and the second step is to prepare the aminopolyether modified polysiloxane based on the epoxy polyether modified polysiloxane.
In the step of preparing the epoxy polyether modified polysiloxane, the raw materials adopted are hydrogen-containing silicone oil and unsaturated ether with the active hydrogen mass fraction of 0.18%. Wherein, the chemical formula of the hydrogen-containing silicone oil is as follows:
m and n are integers of 1-50.
The unsaturated ether is allyl alcohol polyoxyalkyl ether and allyl glycidyl etherAnd (3) mixing the oil ethers according to a molar ratio of 1: 6-1: 6.5 to control the grafting ratio of the allyl glycidyl ether to the allyl alcohol polyoxyalkyl ether in the reaction process. In this reaction, the alcohol polyoxyalkyl ether has the chemical formula CH
2＝CHCH
2O(C
2H
4O)
a(CH
3H
6)
bR, a is an integer of 2-200, b is an integer of 0-100, R is H or alkyl;
the allyl glycidyl ether has the formula:
in the raw materials for preparing the epoxy polyether modified polysiloxane, the molar ratio of the hydrogen-containing silicone oil to the unsaturated ether is 1: 1.1-1: 1.3, namely the dosage of the unsaturated ether is slightly excessive compared with the hydrogen-containing silicone oil, so that the hydrogen-containing silicone oil can be fully reacted, and the grafting ratio of allyl glycidyl ether and allyl alcohol polyoxyalkyl ether is improved.
Adding hydrogen-containing silicone oil with 0.18% of active hydrogen by mass and a platinum catalyst into a container, stirring and mixing, heating in a water bath to 40-60 ℃ for preheating, then dropwise adding unsaturated ether into the container, continuously heating to 80-95 ℃, stirring and reacting for 5-7 hours under the conditions of nitrogen protection and reflux condensation, and removing unreacted substances through reduced pressure distillation after the reaction is finished to obtain the epoxy polyether modified polysiloxane. The platinum catalyst adopts chloroplatinic acid solution in the reaction process. The addition amount of the platinum catalyst is 5-20 ppm of the total mass of the hydrogen-containing silicone oil and the unsaturated ether.
The reaction temperature is controlled to be 80-95 ℃, so that the activity of the platinum catalyst in the reaction is highest, the allyl glycidyl ether cannot generate a self-polymerization phenomenon, and the yield of the epoxy polyether modified polysiloxane is improved.
The specific reaction formula is as follows:
furthermore, in the preparation process of the epoxy polyether modified polysiloxane, a proper amount of isopropanol is added before the step of continuously heating to 80-95 ℃ to serve as a stabilizer, and the mass of the isopropanol accounts for 4.2-4.8% of the total mass of the hydrogen-containing silicone oil and the unsaturated ether.
The amino polyether modified polysiloxane is prepared by reacting the prepared epoxy polyether modified polysiloxane with diethylamine. The reaction steps are as follows:
and (3) placing the prepared epoxy polyether modified polysiloxane into a container, stirring and heating to 55-70 ℃, dropwise adding diethylamine, reacting at constant temperature for 3-5 hours, and removing unreacted substances by water pump reduced pressure distillation after the reaction is finished to obtain the amino polyether modified polysiloxane. In the reaction, the reaction temperature is controlled to be 55-70 ℃, if the temperature is too high, the diethylamine is decomposed, the reaction temperature is too low, the reaction rate is reduced, and the reaction time is prolonged. And the content of the diethylamine is equal to or slightly higher than that of the epoxy polyether modified polysiloxane so as to ensure that the reaction is sufficient, for example, the molar ratio of the diethylamine to the epoxy polyether modified polysiloxane is 1: 1-1: 1.2.
The reaction formula of the amino polyether modified polysiloxane is as follows:
Example 1
100 g of hydrogen-containing silicone oil with the active hydrogen of which the mass fraction is 0.18 percent is added into a dry four-neck flask provided with a reflux condenser tube, a stirrer, a dropping funnel and a thermometer, then 10 ml of isopropanol is added to serve as a stabilizer and six drops of a catalyst chloroplatinic acid solution, the temperature is raised in a stirring water bath, and the air in the flask is driven away by introducing nitrogen. When the temperature is raised to 50 ℃, a mixed solution of 36 g of allyl alcohol polyoxyalkyl ether and 21 g of allyl glycidyl ether is dripped into the flask through the dropping funnel, and the temperature is kept constant for six hours after the temperature is raised to 85 ℃ in a water bath. After the reaction was completed, unreacted materials were distilled off under reduced pressure to obtain 154.33 g of a pale yellow transparent liquid epoxy polyether-modified polysiloxane in a yield of 98.3%.
154.33 g of epoxy polyether modified polysiloxane is stirred and heated to 60 ℃, 10 g of diethylamine is dripped into a flask by a dropping funnel to react for four hours at constant temperature, after the reaction is finished, a water pump is used for carrying out reduced pressure distillation to remove unreacted substances, 158.90 g of light yellow transparent liquid amino polyether modified polysiloxane is obtained, and the yield reaches 96.7%.
The infrared test result by liquid film method is shown in FIG. 1, wherein the peak value is 1108.39cm
-1is-Si-O-Si-functional group absorption peak, 805.06cm
-1is-Si-CH 3-absorption peak; 1260.84cm
-1Is the-C-O-contraction vibration peak; 3484.45cm
-1-NH-contraction vibration peak; 1373.65cm-1 is the-NH-bending vibration peak. As can be seen from FIG. 1, this reaction produced an aminopolyether-modified polysiloxane
Example 2
100 g of hydrogen-containing silicone oil with the active hydrogen of which the mass fraction is 0.18 percent is added into a dry four-neck flask provided with a reflux condenser tube, a stirrer, a dropping funnel and a thermometer, 10 drops of 10 ml of isopropanol serving as a stabilizer and a catalyst chloroplatinic acid solution are added, the temperature is raised in a stirring water bath, and the air in the flask is driven away by introducing nitrogen. When the temperature is raised to 40 ℃, a mixed solution of 36 g of allyl alcohol polyoxyalkyl ether and 25 g of allyl glycidyl ether is dripped into the flask through the dropping funnel, and the temperature is kept constant for 5 hours after the temperature is raised to 85 ℃ in a water bath. After the reaction, unreacted materials were distilled off under reduced pressure to obtain 152.95 g of a pale yellow transparent liquid epoxy polyether-modified polysiloxane with a yield of 95%.
152.95 g of epoxy polyether modified polysiloxane is stirred and heated to 55 ℃, 13 g of diethylamine is dripped into a flask by a dropping funnel to react for four hours at constant temperature, after the reaction is finished, a water pump is used for carrying out reduced pressure distillation to remove unreacted substances, 152.67 g of light yellow transparent liquid amino polyether modified polysiloxane is obtained, and the yield is 92%.
Example 3
100 g of hydrogen-containing silicone oil with the active hydrogen of which the mass fraction is 0.18 percent is added into a dry four-neck flask provided with a reflux condenser tube, a stirrer, a dropping funnel and a thermometer, 9 ml of isopropanol is added to be used as a stabilizer and 8 drops of a catalyst chloroplatinic acid solution, the temperature is raised in a stirring water bath, and the air in the flask is driven away by introducing nitrogen. When the temperature was raised to 60 ℃, a mixture of 36 g of allyl alcohol polyoxyalkyl ether and 27.4 g of allyl glycidyl ether was dropped into the flask from the dropping funnel, and the temperature was maintained for 7 hours after the temperature was raised to 95 ℃ in a water bath. After the reaction was completed, unreacted materials were distilled off under reduced pressure to obtain 150.33 g of a pale yellow transparent liquid epoxy polyether-modified polysiloxane in a yield of 93%.
150.33 g of epoxy polyether modified polysiloxane is stirred and heated to 60 ℃, 12 g of diethylamine is dripped into a flask by a dropping funnel, the reaction is carried out for 5 hours at constant temperature, after the reaction is finished, unreacted materials are removed by water pump reduced pressure distillation, 146.09 g of light yellow transparent liquid amino polyether modified polysiloxane is obtained, and the yield is 90%.
In the three embodiments, the modified amino polyether polysiloxane generated by the reaction has transparent appearance and good quality, and the yield can reach over 90 percent. And amination reaction can be carried out at normal temperature, the whole reaction process is easy to control, the yield is high, and impurities are few.
In the description herein, references to the description of the term "one embodiment," "some embodiments," "an example," "a specific example," or "some examples," etc., mean that a particular feature, structure, material, or characteristic described in connection with the embodiment or example is included in at least one embodiment or example of the invention. In this specification, the schematic representations of the terms used above do not necessarily refer to the same embodiment or example. Furthermore, the particular features, structures, materials, or characteristics described may be combined in any suitable manner in any one or more embodiments or examples.
The above-mentioned embodiments only express several embodiments of the present invention, and the description thereof is more specific and detailed, but not construed as limiting the scope of the present invention. It should be noted that, for a person skilled in the art, several variations and modifications can be made without departing from the inventive concept, which falls within the scope of the present invention. Therefore, the protection scope of the present patent shall be subject to the appended claims.
Claims (7)
1. A preparation method of amino polyether modified polysiloxane is characterized by comprising the following steps,
preparing epoxy polyether modified polysiloxane: adding hydrogen-containing silicone oil with 0.18 mass percent of active hydrogen and a platinum catalyst into a container, stirring and mixing, heating in a water bath to 40-60 ℃, dropwise adding unsaturated ether into the container, continuously heating to 80-95 ℃, stirring and reacting for 5-7 hours under the conditions of nitrogen protection and reflux condensation, and removing unreacted substances through reduced pressure distillation after the reaction is finished to obtain epoxy polyether modified polysiloxane, wherein the unsaturated ether is a mixed solution of allyl alcohol polyoxyalkyl ether and allyl glycidyl ether, the molar ratio of the alcohol polyoxyalkyl ether to the allyl glycidyl ether in the unsaturated ether is 1: 6-1: 8, and the molar ratio of the hydrogen-containing silicone oil to the unsaturated ether is 1: 1.1-1: 1.3;
preparation of aminopolyether modified polysiloxane: and (2) stirring the epoxy polyether modified polysiloxane, heating to 55-70 ℃, dropwise adding diethylamine, reacting at a constant temperature for 3-5 hours, and removing unreacted substances by water pump reduced pressure distillation after the reaction is finished to obtain the amino polyether modified polysiloxane, wherein the molar ratio of the epoxy polyether modified polysiloxane to the diethylamine is 1: 1-1: 1.2.
2. The method of producing an aminopolyether-modified polysiloxane according to claim 1, wherein in the step of producing the epoxy polyether-modified polysiloxane, the reaction temperature after dropping an unsaturated ether into a vessel is 85 ℃ and the reaction time is 6 hours.
3. The method for producing an aminopolyether-modified polysiloxane according to claim 1, wherein in the step of producing the aminopolyether-modified polysiloxane, diethylamine is added dropwise and then the reaction temperature is 60 ℃ and the reaction time is 4 hours.
4. The method for producing the aminopolyether-modified polysiloxane of claim 1, wherein the molar ratio of the hydrogen-containing silicone oil to the unsaturated ether is 1: 1.2.
5. The method for preparing amino polyether modified polysiloxane according to claim 1, wherein isopropanol is further added before the step of continuously raising the temperature to 80-95 ℃ in the preparation process of the epoxy polyether modified polysiloxane, and the mass of the isopropanol accounts for 4.2-5% of the total mass of the hydrogen-containing silicone oil and the unsaturated ether.
6. The method for preparing the aminopolyether modified polysiloxane of claim 1, wherein the addition amount of the platinum catalyst is 5-20 ppm of the total mass of the hydrogen-containing silicone oil and the unsaturated ether.
7. The method for producing the aminopolyether-modified polysiloxane of claim 1, wherein the platinum catalyst is a chloroplatinic acid solution.
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Cited By (4)
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| CN112142977A (en) * | 2020-09-15 | 2020-12-29 | 江西省科学院能源研究所 | Synthesis method of amino/stearamido modified polysiloxane |
| CN113004793A (en) * | 2021-03-25 | 2021-06-22 | 江西蓝星星火有机硅有限公司 | Heat-conducting phase-change material and application thereof |
| CN116159010A (en) * | 2023-03-20 | 2023-05-26 | 广州市柏凡生物科技有限公司 | Amino acid moisturizing and oil-controlling facial cleanser and preparation method thereof |
| CN116769133A (en) * | 2023-06-02 | 2023-09-19 | 东莞方德泡绵制品厂有限公司 | Production process of new energy automobile interior damping material |
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| CN112142977A (en) * | 2020-09-15 | 2020-12-29 | 江西省科学院能源研究所 | Synthesis method of amino/stearamido modified polysiloxane |
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| CN116159010B (en) * | 2023-03-20 | 2024-01-26 | 广州市柏凡生物科技有限公司 | Amino acid moisturizing and oil-controlling facial cleanser and preparation method thereof |
| CN116769133A (en) * | 2023-06-02 | 2023-09-19 | 东莞方德泡绵制品厂有限公司 | Production process of new energy automobile interior damping material |
| CN116769133B (en) * | 2023-06-02 | 2023-12-15 | 东莞方德泡绵制品厂有限公司 | Production process of new energy automobile interior damping material |
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