CN111040175A - Polyether modified siloxane and synthesis method thereof - Google Patents
Polyether modified siloxane and synthesis method thereof Download PDFInfo
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- CN111040175A CN111040175A CN201911365539.6A CN201911365539A CN111040175A CN 111040175 A CN111040175 A CN 111040175A CN 201911365539 A CN201911365539 A CN 201911365539A CN 111040175 A CN111040175 A CN 111040175A
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- 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
The invention relates to the technical field of synthesis of polyether modified siloxane, and particularly relates to polyether modified siloxane and a synthesis method thereof. The synthesis method of the polyether modified siloxane comprises the steps of mixing hydrogen-containing polysiloxane, polyether containing allyl, amine auxiliary agent, protective agent and catalyst and reacting after removing gas increasing by-product formation to form the polyether modified siloxane. The synthesis method not only reduces the dosage of the catalyst, but also ensures the normal operation of the silicon-hydrogen reaction, inhibits the side reaction, ensures that the polyether has low isomerization degree, and obviously reduces the content of aldehyde ketone in the product.
Description
Technical Field
The invention relates to the technical field of synthesis of polyether modified siloxane, and particularly relates to polyether modified siloxane and a synthesis method thereof.
Background
The current commercial process for the production of polyether modified silicones is hydrosilylation, which is described many times in the literature, for example US7157541 and US 4855379. The catalyst commonly used in hydrosilylation is a platinum compound, and chloroplatinic acid is most widely used in the existing mature industrial production.
The above-described hydrosilylation reaction process has side reactions. The method mainly comprises two aspects: firstly, hydroxyl (OH) in the polyether and a silicon hydride (≡ SiH) functional group in the silicon-containing polysiloxane are subjected to dehydrogenation coupling to form an SiOC functional group, and the SiOC functional group is easy to hydrolyze; the other is that the olefinic bond in the allyl polyether has rearrangement reaction and then cleavage reaction during hydrosilylation, and propionaldehyde and acetone with odor are formed. And the aldehyde ketone produced can further react with hydroxyl in the polyether to form acetal; the acetal formed can be further reacted with SiOC. These side reactions can lead to product instability, structural cross-linking, and high viscosity.
In the prior art, although there are improvements to the above-mentioned method, for example, amine-based promoters are used, and the reactivity of the platinum catalyst is significantly reduced when amine-based promoters are used. In the platinum catalyst system used in the prior art, allyl is easy to isomerize, so that the allyl is more stable by reducing the use amount of the platinum catalyst. However, generally, hydrosilylation cannot be performed normally by reducing the amount of platinum catalyst used. In addition, the side reactions still occur in the prior art, so that the aldehyde ketone content in the product is still high, and the performance of the product is influenced.
In view of this, the invention is particularly proposed.
Disclosure of Invention
The invention aims to provide polyether modified siloxane and a synthesis method thereof. The method provided by the invention can ensure normal operation of hydrosilylation while reducing the dosage of the catalyst, inhibit side reactions and obviously reduce the content of aldehyde ketone in the product.
The invention is realized by the following steps:
in a first aspect, embodiments provide a method for synthesizing polyether modified siloxane, including mixing and reacting hydrogen-containing polysiloxane, allyl-containing polyether, amine assistant, protective agent and catalyst to form the polyether modified siloxane after removing gas increasing byproduct formation.
In an alternative embodiment, the step of removing the gas that increases the formation of byproducts comprises: mixing the hydrogen-containing polysiloxane, the allyl-containing polyether, the amine auxiliary agent and the protective agent, stirring and vacuumizing to form a vacuum condition, and then introducing inert gas to make the gas atmosphere of the reaction become inert gas atmosphere;
preferably, the step of reacting comprises: after forming an inert gas atmosphere, heating the mixed solution of the hydrogen-containing polysiloxane, the allyl-containing polyether, the amine auxiliary agent and the protective agent to a reaction temperature, and then adding a catalyst to carry out a reaction;
preferably, the pressure after vacuum pumping is-1.00 to-0.098 MPa;
preferably, the reaction temperature is less than or equal to 100 ℃, and preferably 80-90 ℃;
preferably, the reaction time is 1 to 2 hours.
In an alternative embodiment, the step of passing the inert gas comprises: introducing the inert gas from the bottom of the mixed solution of the hydrogen-containing polysiloxane, the allyl-containing polyether, the amine assistant and the protective agent, so that the pressure is recovered to be normal, and the gas atmosphere of the reaction is the inert gas atmosphere;
preferably, before heating the mixed solution, the operation of vacuumizing and then introducing the inert gas is repeated at least once.
In an alternative embodiment, the inert gas is any one of nitrogen, argon and helium, preferably nitrogen.
In alternative embodiments, the protective agent is an alcohol;
preferably, the alcohol is at least one of monohydric alcohol and dihydric alcohol;
preferably, the monohydric alcohol comprises at least one of ethanol and isopropanol;
preferably, the glycol comprises at least one of diethylene glycol and dipropylene glycol;
preferably, the amount of the protecting agent is not more than 5% of the total amount of the hydrogenpolysiloxane and the allyl group-containing polyether.
In an alternative embodiment, the catalyst is a platinum-containing catalyst, preferably chloroplatinic acid;
preferably, the amount of the catalyst is less than or equal to 5ppm and the amount of the catalyst is more than or equal to 3 ppm.
In an alternative embodiment, the amine adjuvant comprises a hydroxyl-substituted amine adjuvant and/or an alkyl-substituted amine adjuvant;
preferably, the alkyl-substituted amine adjuvant comprises N-diethylisobutanolamine;
preferably, the hydroxy-substituted amine adjuvant comprises at least one of N, N-dibutylethanolamine and triisopropanolamine;
preferably, the amine auxiliary agent is used in an amount of 500-2000 ppm.
In an alternative embodiment, the content of ring bodies in the hydrogenpolysiloxane is less than or equal to 0.3%; preferably less than or equal to 0.1%;
the average molecular weight of the allyl-containing polyether is 1500-2500.
In a second aspect, embodiments provide a polyether modified siloxane prepared by the method of synthesizing a polyether modified siloxane according to any one of the preceding embodiments,
preferably, the polyether modified siloxane has an aldehyde ketone content of 0.001% (wt%);
preferably, the transparency of the polyether modified siloxane is more than or equal to 90 percent;
preferably, the color of the polyether modified siloxane is less than or equal to 15.
The invention has the following beneficial effects: the synthesis method provided by the invention not only reduces the dosage of the catalyst, but also ensures the normal operation of the silicon-hydrogen reaction, inhibits side reaction, ensures that the polyether has low isomerization degree, obviously reduces the content of aldehyde ketone in the product, has low odor and chroma of the prepared product, has good appearance and stable storage property, and simultaneously has simple process and less pollution.
Detailed Description
In order to make the objects, technical solutions and advantages of the embodiments of the present invention clearer, the technical solutions in the embodiments of the present invention will be clearly and completely described below. The examples, in which specific conditions are not specified, were conducted under conventional conditions or conditions recommended by the manufacturer. The reagents or instruments used are not indicated by the manufacturer, and are all conventional products available commercially.
The features and properties of the present invention are described in further detail below with reference to examples.
The embodiment of the invention provides a synthesis method of polyether modified siloxane, which comprises the following steps: comprises mixing hydrogen-containing polysiloxane, polyether containing allyl, amine auxiliary agent, protective agent and catalyst, and reacting to obtain the polyether modified siloxane. After gas generated by increasing byproducts is removed and under the action of a protective agent, the dosage of the catalyst can be reduced, the progress of the hydrosilylation reaction is promoted, the side reaction can be inhibited, and the content of aldehyde ketone in the product is obviously reduced.
Specifically, hydrogen-containing polysiloxane, polyether containing allyl, amine assistant and protective agent are added into a reactor, the reactor is stirred and vacuumized to form a vacuum condition, the final pressure is-1.00 to-0.098 MPa (gauge pressure), and then inert gas is introduced from the bottom of the mixed liquid of the hydrogen-containing polysiloxane, the polyether containing allyl, the amine assistant and the protective agent, so that the pressure is recovered to be normal, and the atmosphere of the reaction is changed into inert gas atmosphere. The inert gas is introduced from the bottom of the mixed solution, so that air, oxygen and the like which are mixed in the mixed solution can be replaced by the inert gas, and all gases which influence the formation of the polyether modified siloxane or increase the formation of byproducts in the reactor are completely removed, so that the side reaction is further inhibited, and the formation of the byproducts is reduced. And the pressure recovery to normal means that the pressure is recovered to normal pressure or slight positive pressure.
Further, the inert gas is any one of nitrogen, argon and helium, and preferably nitrogen. The nitrogen can better promote the forward reaction and reduce the side reaction.
Preferably, the evacuation is repeated and then the operation of introducing the inert gas is repeated at least once. Namely, after the operation, the vacuum pumping is carried out again, so that the gas in the reactor is exhausted, then the inert gas is introduced, and the inert gas is filled in the reactor, so that the gas which is formed by increasing the byproducts in the reactor can be exhausted more thoroughly, and the amount of the byproducts in the production is further reduced. Finally, after the inert gas was introduced, the pressure was changed to normal pressure.
Then, heating the mixed solution to the reaction temperature which is less than or equal to 100 ℃, preferably 80-90 ℃, then adding a catalyst, and keeping the reaction temperature for reaction for 1-2 hours.
By adopting the operation, the normal operation of the hydrosilylation reaction can be further ensured, the content of aldehyde ketone in the product is reduced, the chroma of the product is reduced, and the quality of the product is improved.
Further, the protective agent is an alcohol substance; specifically, the alcohol substance is at least one of monohydric alcohol and dihydric alcohol; for example, the monohydric alcohol includes at least one of ethanol and isopropanol, and the dihydric alcohol includes at least one of diethylene glycol and dipropylene glycol. Further, the amount of the protecting agent is not more than 5% of the total amount of the hydrogenpolysiloxane and the allyl group-containing polyether. The protective agent adopts the materials and the dosage, so that the dosage of the catalyst can be reduced, the smooth reaction is ensured, the side reaction is reduced, and the generation of byproducts is inhibited.
Further, the catalyst is a platinum-containing catalyst, preferably chloroplatinic acid; preferably, the amount of the catalyst is less than or equal to 5ppm and the amount of the catalyst is more than or equal to 3 ppm. By adopting the method, the using amount of the catalyst is reduced, but the reaction can still be smoothly carried out, the side reaction is also inhibited, and the content of the by-product is reduced. Meanwhile, the inventor finds that when the catalyst is excessive, the side reaction is increased, the content of aldehyde ketone in the product is increased, and if the catalyst is too little, the reaction cannot be normally carried out.
Further, the amine auxiliary agent comprises a hydroxyl-substituted amine auxiliary agent and/or an alkyl-substituted amine auxiliary agent; preferably, the alkyl-substituted amine adjuvant comprises N-diethylisobutanolamine, and preferably, the hydroxyl-substituted amine adjuvant comprises at least one of N, N-dibutylethanolamine and triisopropanolamine; preferably, the amine auxiliary is used in an amount of 500-2000 ppm.
Furthermore, the content of the ring bodies in the hydrogenpolysiloxane is less than or equal to 0.3 percent; preferably less than or equal to 0.1%; the hydrogenpolysiloxane has less ring body content and can meet the increasingly severe environmental requirements.
The average molecular weight of the allyl-containing polyether is 1500-2500.
Further, the embodiment of the invention also provides polyether modified siloxane, which is prepared by the synthesis method of the polyether modified siloxane, wherein the aldehyde ketone content of the polyether modified siloxane is less than or equal to 0.001% (wt%), the transparency is greater than or equal to 90%, and the chroma is less than or equal to 15.
Example 1
The embodiment of the invention provides a synthesis method of polyether modified siloxane, which comprises the following steps:
s1, synthesizing to obtain hydrogenous polysiloxane;
to a 250ml three-necked flask equipped with a mechanical stirrer were added 11.5g of high hydrogen silicone oil (hydrogen content 1.5%), 135.3g of octamethylcyclotetrasiloxane, 3.2g of hexamethyldisiloxane and 6.0g of solid acid, and the temperature was raised to 60 ℃ and maintained for 4 hours. And (3) filtering the material after the reaction through an inorganic membrane, and removing low-boiling-point components from the filtrate by using a distiller to obtain a target product.
S2, synthesizing polyether modified siloxane;
to a 250ml round bottom flask equipped with a mechanical stirrer and a dry nitrogen line were added 80.0g of acetyl terminated allyl polyether 1(Mn 4000, EO (ethylene oxide) mass fraction 40%, PO (propylene oxide) mass fraction 60%), 33.0g of acetyl terminated allyl polyether 2(Mn 600, EO (ethylene oxide) mass fraction 90%, PO (propylene oxide) mass fraction 10%), 37.0g of hydrogenpolysiloxane (MD 80D' 8M) and 500ppm of N, N-dimethylethanolamine and 1.5g of isopropanol (protective agent). Stirring and vacuumizing, introducing nitrogen when the vacuum reaches-0.1 MPa to ensure that the reaction gas atmosphere is inert gas atmosphere and the pressure is normal, and carrying out the steps for three times. Heating the reaction system to 85 ℃, adding 5ppm chloroplatinic acid, keeping the temperature for 1h, stirring for half an hour, and reacting to obtain 150g polyether modified siloxane copolymer.
In this example, the average molecular weight of the allyl group-containing polyether was (80.0+33.0)/[ (80.0/4000) + (33.0/600) ] -1507.
Examples 2 to 4
The operation, conditions and raw material selection of the synthesis of polyether modified siloxane provided in examples 2-4 are the same as those of the examples, except that the amount of the materials is different, as shown in table 1.
TABLE 1 amounts of materials
| Amine auxiliary | Amount of protectant | Catalyst and process for preparing same | N2Replacement of | |
| ppm | ％ | ppm | Number of times | |
| Example 2 | 1000* | 1 | 5 | 4 |
| Example 3 | 500 | 3 | 5 | 2 |
| Example 4 | 500 | 1 | 4 | 3 |
The amine assistant is triisopropanolamine
Comparative examples 1 to 4
The operation, conditions and raw material selection of the synthesis of the polyether modified siloxane provided in comparative examples 1 to 4 are the same as those of the examples, except that the amount of the materials used is different, as shown in table 2.
TABLE 2 amounts of materials
Experimental example 1
The polyether modified siloxane synthesized in the examples 1-4 and the comparative examples 1-4 is subjected to performance detection, and the detection method comprises the following steps:
transparent time: adding catalyst to start timing, and stopping timing after the system is transparent.
Transparency: according to the method of 4.2 in GB/T1721-2008 "determination of appearance and transparency of varnish, clear oil and diluent".
Chroma: the general method is measured according to the chromaticity of the chemical reagent GBT 605-.
Aldehyde ketone content: the detection is carried out by a nuclear magnetic hydrogen spectrum quantitative internal standard method, and the detection result is shown in table 3.
TABLE 3 test results
According toAs shown in Table 3, it is understood that in example 1 and comparative example 3, the amount of the catalyst is reduced to effectively reduce the content of the aldehyde ketone. As can be seen from example 1 and comparative example 1, only the amount of catalyst used was reduced, and N was not performed2The reaction did not proceed normally by displacement. As can be seen from example 3 and comparative example 2, the addition of a certain amount of the protective agent can effectively reduce the aldehyde ketone content of the product.
In summary, the embodiment of the invention adopts the protective agent, controls the reaction atmosphere to be the vacuum condition and the inert gas atmosphere, and reduces the dosage of the catalyst, so that the side reaction of the product can be reduced, the content of the aldehyde ketone in the product can be reduced, and the quality of the product can be ensured.
The above description is only a preferred embodiment of the present invention and is not intended to limit the present invention, and various modifications and changes may be made by those skilled in the art. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (10)
1. The synthesis method of the polyether modified siloxane is characterized by comprising the step of carrying out reaction by utilizing hydrogen-containing polysiloxane, polyether containing allyl, amine auxiliary agent, protective agent and catalyst after removing gas formed by increasing byproducts to form the polyether modified siloxane.
2. The method of claim 1, wherein the step of removing gases that increase byproduct formation comprises: mixing the hydrogen-containing polysiloxane, the allyl-containing polyether, the amine auxiliary agent and the protective agent, stirring and vacuumizing to form a vacuum condition, and then introducing inert gas to make the gas atmosphere of the reaction become inert gas atmosphere;
preferably, the step of reacting comprises: after forming an inert gas atmosphere, heating the mixed solution of the hydrogen-containing polysiloxane, the allyl-containing polyether, the amine auxiliary agent and the protective agent to a reaction temperature, and then adding a catalyst to carry out a reaction;
preferably, the pressure after vacuum pumping is-1.00 to-0.098 MPa;
preferably, the reaction temperature is less than or equal to 100 ℃, and preferably 80-90 ℃;
preferably, the reaction time is 1 to 2 hours.
3. The method for synthesizing polyether modified siloxane according to claim 2, wherein the step of introducing the inert gas comprises: introducing the inert gas from the bottom of the mixed solution to recover the pressure, wherein the gas atmosphere of the reaction is the inert gas atmosphere;
preferably, before heating the mixed solution, the operation of vacuumizing and then introducing the inert gas is repeated at least once.
4. The method for synthesizing polyether modified siloxane according to claim 3, wherein the inert gas is any one of nitrogen, argon and helium, preferably nitrogen.
5. The method for synthesizing polyether modified siloxane according to any one of claims 1-4, wherein the protective agent is alcohol;
preferably, the alcohol is at least one of monohydric alcohol and dihydric alcohol;
preferably, the monohydric alcohol comprises at least one of ethanol and isopropanol;
preferably, the glycol comprises at least one of diethylene glycol and dipropylene glycol;
preferably, the amount of the protective agent is not more than 5% of the total amount of the hydrogenpolysiloxane and the allyl group-containing polyether;
preferably, the amount of the catalyst is less than or equal to 5ppm and the amount of the catalyst is more than or equal to 3 ppm.
6. The method for synthesizing polyether modified siloxane according to any one of claims 1-4, wherein the catalyst is platinum-containing catalyst, preferably chloroplatinic acid.
7. The method for synthesizing polyether modified siloxane according to any one of claims 1 to 4, wherein the amine assistant comprises a hydroxyl-substituted amine assistant and/or an alkyl-substituted amine assistant;
preferably, the alkyl-substituted amine adjuvant comprises N-diethylisobutanolamine;
preferably, the hydroxy-substituted amine adjuvant comprises at least one of N, N-dibutylethanolamine and triisopropanolamine;
preferably, the amine auxiliary agent is used in an amount of 500-2000 ppm.
8. The method for synthesizing polyether modified siloxane according to any one of claims 1-4, wherein the content of cyclic bodies in the hydrogenpolysiloxane is less than or equal to 0.3%; preferably 0.1% or less.
9. The method for synthesizing polyether modified siloxane according to any one of claims 1 to 4, wherein the average molecular weight of the allyl-containing polyether is 1500-2500.
10. Polyether modified siloxane, characterized in that it is prepared by the method for synthesizing polyether modified siloxane according to any one of claims 1 to 9;
preferably, the aldehyde ketone content of the polyether modified siloxane is less than or equal to 0.001 percent;
preferably, the transparency of the polyether modified siloxane is more than or equal to 90 percent;
preferably, the color of the polyether modified siloxane is less than or equal to 15.
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Cited By (1)
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| CN111875802A (en) * | 2020-06-19 | 2020-11-03 | 上海抚佳精细化工有限公司 | Application of amine stabilizer in preparation of hydrophilic silicone oil with stable viscosity and preparation method of hydrophilic silicone oil |
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