CN113512197B - Preparation method of alkoxy-terminated polydimethylsiloxane - Google Patents
Preparation method of alkoxy-terminated polydimethylsiloxane Download PDFInfo
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- CN113512197B CN113512197B CN202110868098.2A CN202110868098A CN113512197B CN 113512197 B CN113512197 B CN 113512197B CN 202110868098 A CN202110868098 A CN 202110868098A CN 113512197 B CN113512197 B CN 113512197B
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- 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
- C08G77/04—Polysiloxanes
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- 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
- C08G77/04—Polysiloxanes
- C08G77/06—Preparatory processes
- C08G77/08—Preparatory processes characterised by the catalysts used
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- 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
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
- C08G77/18—Polysiloxanes containing silicon bound to oxygen-containing groups to alkoxy or aryloxy groups
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Abstract
The invention discloses a preparation method of alkoxy-terminated polydimethylsiloxane, which comprises the following steps: (1) heating DMC and hexamethyldisiloxane to 160-180 ℃, dripping phosphoric acid, stirring for 6-8 hours, and refluxing to remove water to obtain a silicophosphate terminator; (2) heating the linear body to 130-150 ℃, adding a potassium hydroxide aqueous solution, stirring for polycondensation reaction, monitoring the viscosity on line, adding the silicon phosphate terminating agent obtained in the step (1) before reaching the target viscosity, continuing to react for 5-50 minutes, vacuumizing, and distilling under reduced pressure to remove low-boiling-point substances to obtain the alpha, omega-dihydroxy polydimethylsiloxane with different viscosities. The alkoxy-terminated polydimethylsiloxane prepared by the preparation method of the alkoxy-terminated polydimethylsiloxane with the structure has high end-capping efficiency, convenient production process and better storage stability.
Description
Technical Field
The invention relates to the technical field of organosilicon polymerization, in particular to a preparation method of alkoxy-terminated polydimethylsiloxane.
Background
The traditional dealcoholized silicone rubber is generally prepared by taking 107 silicone rubber as a base rubber and matching with filler, a crosslinking agent, a catalyst, a coupling agent, a plasticizer and the like. Because organotin is used as a catalyst, a monoalkoxy polymer without crosslinking activity is easy to generate, and the problem of poor storage stability exists; if the titanate is used as the catalyst, the viscosity peak phenomenon can occur due to the pseudo-crosslinking state formed by the reaction of the titanate and the terminal hydroxyl of 107 silicon rubber, and the production efficiency is seriously influenced.
The alkoxy-terminated polydimethylsiloxane does not have a viscosity peak even when a titanate catalyst is used in the process of producing the alcohol-type adhesive, improves the production efficiency, improves the storage stability, and has transparent and non-turbid color after compounding and vulcanization.
Disclosure of Invention
The invention aims to provide a preparation method of alkoxy-terminated polydimethylsiloxane, and the prepared alkoxy-terminated polydimethylsiloxane has high end-capping efficiency, convenient production process and better storage stability.
In order to achieve the above object, the present invention provides a method for preparing alkoxy-terminated polydimethylsiloxane, comprising the steps of:
(1) heating DMC and hexamethyldisiloxane to 160-180 ℃, dripping phosphoric acid, stirring for 6-8 hours, and refluxing to remove water to obtain a silicophosphate terminator;
(2) heating the linear body to 130-150 ℃, adding a potassium hydroxide aqueous solution, stirring for polycondensation reaction, monitoring the viscosity on line, adding the silicon phosphate terminating agent obtained in the step (1) before reaching the target viscosity, continuing to react for 5-50 minutes, vacuumizing, and distilling under reduced pressure to remove low-boiling-point substances to obtain alpha, omega-dihydroxy polydimethylsiloxane with different viscosities;
(3) adding methyltrimethoxysilane, vinyl trimethoxysilane and a zinc acetylacetonate catalyst into a plastic barrel with a cover in a certain proportion, fully stirring and mixing for 30 minutes at normal temperature, sealing and standing for 24 hours, and taking out supernatant for later use;
(4) and (3) adding the prepared alpha and omega-dihydroxy polydimethylsiloxane, 100cs of dimethyl silicone oil, the end-capping agent prepared in the step (3) and the catalyst into a reaction kettle according to a certain proportion, and mixing for 60 minutes at normal temperature to obtain the alkoxy end-capped silicone oil.
Preferably, in the step (1), the mass ratio of DMC, hexamethyldisiloxane to phosphoric acid is (60-80): (5-15): (10-20).
Preferably, in the step (1), the stirring speed is 200-.
Preferably, in the step (2), the mass concentration of the potassium hydroxide aqueous solution is 10%, and the mass ratio of the linear body, the potassium hydroxide aqueous solution and the silicon phosphate terminator is 40000:1 (1.5-2.0).
Preferably, in the step (2), the target viscosity is 1000-50000 mPas.
Preferably, in the step (3), the mass ratio of the methyltrimethoxysilane to the vinyltrimethoxysilane to the zinc acetylacetonate is (1.0-3.0) to (0.5-1.5) to (0.015-0.030).
Preferably, in the step (3), the stirring speed during the stirring reaction is 400-800 r/min.
Preferably, in the step (3), the stirring and mixing time is 0.5 to 1.0 hour, and the sealing and standing time is more than 24 hours before use.
Preferably, in the step (4), the mass ratio of the alpha, omega-dihydroxy polydimethylsiloxane, the dimethyl silicone oil and the end-capping reagent prepared in the step (3) is (80-90): (5-15): (1.5-3.0).
Preferably, in the step (4), the stirring reaction is performed at room temperature for 60-80 minutes, and the stirring speed during the stirring reaction is 600-900 r/min.
The invention has the beneficial effects that:
according to the invention, methyltrimethoxysilane and vinyl trimethoxysilane are used as end sealing agents, zinc acetylacetonate is used as a catalyst, a linear body is used as a base material to prepare alpha and omega-dihydroxy polydimethylsiloxane, then the polydimethylsiloxane is modified and terminated by using a functional material to prepare alkoxy-terminated polydimethylsiloxane, and the alkoxy-terminated polydimethylsiloxane with different viscosities can be prepared according to the alpha and omega-dihydroxy polydimethylsiloxane with different viscosities, so that the preparation method has the advantages of high end-capping efficiency, convenience in production process and better storage stability.
The alkoxy polydimethylsiloxane prepared by using the zinc acetylacetonate as the catalyst has very high end-capping rate, very small addition amount and simple processing technology, omits the process steps of heating reaction and catalyst removal, and has very high stability through an aging test, and the storage period can reach 12 months.
The technical solution of the present invention is further described in detail by the accompanying drawings and embodiments.
Detailed Description
The present invention will be further described with reference to examples in which various chemicals and reagents are commercially available unless otherwise specified.
Example 1
Alkoxy-terminated polydimethylsiloxane was prepared as follows:
(1) and (2) mixing DMC and hexamethyldisiloxane, heating to 170 ℃, dropwise adding phosphoric acid, stirring at the speed of 300r/min for 7 hours, and refluxing to remove water to obtain the silicophosphate terminator, wherein the mass ratio of DMC, hexamethyldisiloxane to phosphoric acid is 70:10: 15.
(2) Heating the linear body to 150 ℃, adding a potassium hydroxide aqueous solution with the mass concentration of 10%, stirring for polycondensation reaction, monitoring the viscosity on line, adding the silicon phosphate terminating agent obtained in the step (1) before the target viscosity is 1000mPa & s, continuing to react for 50 minutes, vacuumizing, decompressing and distilling to remove low-boiling-point substances to obtain the hydroxyl silicone oil, wherein the mass ratio of the linear body to the potassium hydroxide aqueous solution to the silicon phosphate terminating agent is 40000:1: 1.5.
(3) Adding methyltrimethoxysilane, vinyl trimethoxysilane and a zinc acetylacetonate catalyst into a plastic barrel with a cover in a certain proportion, fully stirring and mixing for 30 minutes at normal temperature, sealing and standing for 24 hours, and taking out supernatant for later use, wherein the mass ratio of the methyltrimethoxysilane to the vinyl trimethoxysilane to the zinc acetylacetonate is 2.0:1.2: 0.32.
(4) Adding the prepared alpha, omega-dihydroxy polydimethylsiloxane, 100cs of dimethyl silicone oil and the end-capping agent and catalyst prepared in the step (3) into a reaction kettle according to a certain proportion, and mixing for 60 minutes at normal temperature to obtain alkoxy end-capped silicone oil, wherein the mass ratio of the alpha, omega-dihydroxy polydimethylsiloxane to the dimethyl silicone oil to the end-capping agent prepared in the step (3) is 95:5.0: 2.5. The stirring reaction process comprises: stirring and reacting for 60-80 minutes at normal temperature, wherein the stirring speed during the stirring and reacting is 600-900 r/min.
Example 2
Alkoxy-terminated polydimethylsiloxane was prepared as follows:
(1) and (2) mixing DMC and hexamethyldisiloxane, heating to 170 ℃, dropwise adding phosphoric acid, stirring at the speed of 300r/min for 7 hours, and refluxing to remove water to obtain the silicophosphate terminator, wherein the mass ratio of DMC, hexamethyldisiloxane to phosphoric acid is 70:10: 15.
(2) Heating the linear body to 150 ℃, adding a potassium hydroxide aqueous solution with the mass concentration of 10%, stirring for polycondensation reaction, monitoring the viscosity on line, adding the silicon phosphate terminating agent obtained in the step (1) before the viscosity reaches the target viscosity of 20000mPa & s, continuing to react for 50 minutes, vacuumizing, decompressing and distilling to remove low-boiling-point substances to obtain the hydroxyl silicone oil, wherein the mass ratio of the linear body to the potassium hydroxide aqueous solution to the silicon phosphate terminating agent is 40000:1: 1.5.
(3) Adding methyltrimethoxysilane, vinyl trimethoxysilane and a zinc acetylacetonate catalyst into a plastic barrel with a cover in a certain proportion, fully stirring and mixing for 30 minutes at normal temperature, sealing and standing for 24 hours, and taking out supernatant for later use, wherein the mass ratio of the methyltrimethoxysilane to the vinyl trimethoxysilane to the zinc acetylacetonate is 2.0:1.2: 0.32.
(4) Adding the prepared alpha, omega-dihydroxy polydimethylsiloxane, 100cs of dimethyl silicone oil, the prepared end-capping reagent prepared in the step (3) and a catalyst into a reaction kettle according to a certain proportion, and mixing for 60 minutes at normal temperature to obtain alkoxy end-capped silicone oil, wherein the mass ratio of the alpha, omega-dihydroxy polydimethylsiloxane, the dimethyl silicone oil to the end-capping reagent prepared in the step (3) is 80:20: 2.5. The stirring reaction process comprises: stirring and reacting for 60-80 minutes at normal temperature, wherein the stirring speed during the stirring and reacting is 600-900 r/min.
Example 3
Alkoxy-terminated polydimethylsiloxanes were prepared according to the following procedure:
(1) and (2) mixing DMC and hexamethyldisiloxane, heating to 170 ℃, dropwise adding phosphoric acid, stirring at the speed of 300r/min for 7 hours, and refluxing to remove water to obtain the silicophosphate terminator, wherein the mass ratio of DMC, hexamethyldisiloxane to phosphoric acid is 70:10: 15.
(2) Heating the linear body to 150 ℃, adding a potassium hydroxide aqueous solution with the mass concentration of 10%, stirring for polycondensation reaction, monitoring the viscosity on line, adding the silicon phosphate terminating agent obtained in the step (1) before the viscosity reaches the target viscosity of 20000mPa & s, continuing to react for 50 minutes, vacuumizing, distilling under reduced pressure to remove low-boiling-point substances to obtain the hydroxyl silicone oil, wherein the mass ratio of the linear body to the potassium hydroxide aqueous solution to the silicon phosphate terminating agent is 40000:1: 1.5.
(3) Adding methyltrimethoxysilane, vinyl trimethoxysilane and a zinc acetylacetonate catalyst into a plastic barrel with a cover in a certain proportion, fully stirring and mixing for 30 minutes at normal temperature, sealing and standing for 24 hours, and taking out supernatant for later use, wherein the mass ratio of the methyltrimethoxysilane to the vinyl trimethoxysilane to the zinc acetylacetonate is 2.0:1.2: 0.32.
(4) Adding the prepared alpha, omega-dihydroxy polydimethylsiloxane, 100cs of dimethyl silicone oil and the end-capping agent and catalyst prepared in the step (3) into a reaction kettle according to a certain proportion, and mixing for 60 minutes at normal temperature to obtain alkoxy end-capped silicone oil, wherein the mass ratio of the alpha, omega-dihydroxy polydimethylsiloxane to the dimethyl silicone oil to the end-capping agent prepared in the step (3) is 87:10: 3.0. The stirring reaction process comprises: stirring and reacting for 60-80 minutes at normal temperature, wherein the stirring speed during the stirring and reacting is 600-900 r/min.
Example 4
Alkoxy-terminated polydimethylsiloxanes were prepared according to the following procedure:
(1) and (2) mixing DMC and hexamethyldisiloxane, heating to 170 ℃, dropwise adding phosphoric acid, stirring at the speed of 300r/min for 7 hours, and refluxing to remove water to obtain the silicophosphate terminator, wherein the mass ratio of DMC, hexamethyldisiloxane to phosphoric acid is 70:10: 15.
(2) Heating the linear body to 150 ℃, adding a potassium hydroxide aqueous solution with the mass concentration of 10%, stirring for polycondensation reaction, monitoring the viscosity on line, adding the silicon phosphate terminating agent obtained in the step (1) before the viscosity reaches 50000mPa & s, continuing to react for 40 minutes, vacuumizing, decompressing and distilling to remove low-boiling-point substances to obtain the hydroxyl silicone oil, wherein the mass ratio of the linear body to the potassium hydroxide aqueous solution to the silicon phosphate terminating agent is 40000:1: 1.5.
(3) Adding methyltrimethoxysilane, vinyl trimethoxysilane and a zinc acetylacetonate catalyst into a plastic barrel with a cover in a certain proportion, fully stirring and mixing for 30 minutes at normal temperature, sealing and standing for 24 hours, and taking out supernatant for later use, wherein the mass ratio of the methyltrimethoxysilane to the vinyl trimethoxysilane to the zinc acetylacetonate is 2.0:1.2: 0.32.
(4) Adding the prepared alpha, omega-dihydroxy polydimethylsiloxane, 100cs of dimethyl silicone oil and the end-capping agent and catalyst prepared in the step (3) into a reaction kettle according to a certain proportion, and mixing for 60 minutes at normal temperature to obtain alkoxy end-capped silicone oil, wherein the mass ratio of the alpha, omega-dihydroxy polydimethylsiloxane to the dimethyl silicone oil to the end-capping agent prepared in the step (3) is 84:14: 2.0. The stirring reaction process comprises: stirring and reacting for 60-80 minutes at normal temperature, wherein the stirring speed during the stirring and reacting is 600-900 r/min.
Comparative examples 1 to 4
(1) In four examples, alpha, omega-dihydroxypolydimethylsiloxanes of different viscosities were prepared.
(2) In the four examples, the mass ratio of the alpha, omega-dihydroxy polydimethylsiloxane, the simethicone and the end-capping reagent prepared in step (3) is different, and alkoxy end-capped polydimethylsiloxanes with different viscosities are prepared.
(3) The storage stability of alkoxypolydimethylsiloxanes of different viscosities is utilized.
Performance test
The viscosity, capping rate and storage stability of the products obtained in examples 1 to 4 were measured, respectively.
The viscosity is tested by a rotary viscometer according to GB/T10427-2008.
The end capping rate test method comprises the following steps: a certain amount of alkoxy-terminated polydimethylsiloxane is weighed, 0.5% of butyl titanate is added, and after full stirring, the existence of gel is observed.
The stability test method comprises the following steps: the viscosity change of each product was measured before and after 7 days of oven aging at 70 degrees, and the test results are shown in table 1:
table 1 viscosity test structure
As can be seen from Table 1, the low viscosity alkoxy-terminated polydimethylsiloxanes prepared in examples 1-4 of the present invention have good viscosity change, good end-capping rate, and good stability. From the end capping rate test, all products have no gel, which indicates that the end capping efficiency of the catalyst is extremely high, and hydroxyl groups in the products are basically eliminated. From the change of viscosity after the end capping of the product, the viscosity does not rise, which shows that the catalyst has moderate activity and does not have viscosity peak. According to the aging test of 70 ℃ for 7 days, the viscosity of the product is not changed greatly, the viscosity change rate is about 6%, which shows that the product has good stability after end sealing, and the stability of glue making in the later period is greatly improved.
Finally, it should be noted that: the above embodiments are only intended to illustrate the technical solution of the present invention and not to limit the same, and although the present invention is described in detail with reference to the preferred embodiments, those of ordinary skill in the art should understand that: modifications and equivalents may be made to the disclosed embodiments without departing from the spirit and scope of the present invention.
Claims (8)
1. A preparation method of alkoxy-terminated polydimethylsiloxane is characterized by comprising the following steps:
(1) heating DMC and hexamethyldisiloxane to 160-180 ℃, dripping phosphoric acid, stirring for 6-8 hours, and refluxing to remove water to obtain a silicophosphate terminator;
(2) heating the linear body to 130-150 ℃, adding a potassium hydroxide aqueous solution, stirring for polycondensation reaction, monitoring the viscosity on line, adding the silicon phosphate terminating agent obtained in the step (1) before reaching the target viscosity, continuing to react for 5-50 minutes, vacuumizing, and distilling under reduced pressure to remove low-boiling-point substances to obtain alpha, omega-dihydroxy polydimethylsiloxane with different viscosities; the target viscosity is 20000-50000 mPas;
(3) adding methyltrimethoxysilane, vinyl trimethoxysilane and a zinc acetylacetonate catalyst into a plastic barrel with a cover in a certain proportion, fully stirring and mixing for 30 minutes at normal temperature, sealing and standing for 24 hours, and taking out supernatant for later use; the mass ratio of the methyltrimethoxysilane to the vinyl trimethoxy silane to the zinc acetylacetonate is (1.0-3.0) to (0.5-1.5) to (0.015-0.030);
(4) and (3) adding the prepared alpha and omega-dihydroxy polydimethylsiloxane, 100cs of dimethyl silicone oil, the end-capping agent prepared in the step (3) and the catalyst into a reaction kettle according to a certain proportion, and mixing for 60 minutes at normal temperature to obtain the alkoxy end-capped silicone oil.
2. The method according to claim 1, wherein the alkoxy-terminated polydimethylsiloxane further comprises: in the step (1), the mass ratio of DMC, hexamethyldisiloxane to phosphoric acid is (60-80): 5-15): 10-20.
3. The method according to claim 1, wherein the alkoxy-terminated polydimethylsiloxane further comprises: in the step (1), the stirring speed is 200-400 r/min.
4. The method according to claim 1, wherein the alkoxy-terminated polydimethylsiloxane further comprises: in the step (2), the mass concentration of the potassium hydroxide aqueous solution is 10%, and the mass ratio of the linear body, the potassium hydroxide aqueous solution and the silicon phosphate terminator is 40000:1 (1.5-2.0).
5. The method according to claim 1, wherein the alkoxy-terminated polydimethylsiloxane further comprises: in the step (3), the stirring speed during the stirring reaction is 400-800 r/min.
6. The method according to claim 1, wherein the alkoxy-terminated polydimethylsiloxane further comprises: in the step (3), the stirring and mixing time is 0.5-1.0 hour, and the sealing and standing time is more than 24 hours for use.
7. The method according to claim 1, wherein the alkoxy-terminated polydimethylsiloxane further comprises: in the step (4), the mass ratio of the alpha, omega-dihydroxy polydimethylsiloxane, the dimethyl silicone oil and the end-capping agent prepared in the step (3) is (80-90): (5-15): 1.5-3.0).
8. The method according to claim 1, wherein the alkoxy-terminated polydimethylsiloxane further comprises: in the step (4), the stirring reaction process is that the stirring reaction is carried out at normal temperature for 60-80 minutes, and the stirring speed during the stirring reaction is 600-900 r/min.
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