CN108586749A - A kind of additional organosilicon resin and preparation method thereof - Google Patents
A kind of additional organosilicon resin and preparation method thereof Download PDFInfo
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- CN108586749A CN108586749A CN201810493359.5A CN201810493359A CN108586749A CN 108586749 A CN108586749 A CN 108586749A CN 201810493359 A CN201810493359 A CN 201810493359A CN 108586749 A CN108586749 A CN 108586749A
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- preparation
- additional organosilicon
- organosilicon resin
- clotetrasiloxane
- octamethylcy
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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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Abstract
The present invention provides a kind of additional organosilicon resins of offer and preparation method thereof, including：A) aminomethyl phenyl dimethoxysilane, t etram-ethyltetravinylcyclotetrasiloxane, octamethylcy-clotetrasiloxane and catalyst are mixed, obtain mixed solution；B the mixed solution) is heated to 130~155 DEG C, 0.5~5h is kept the temperature, obtains additional organosilicon resin.Aminomethyl phenyl dimethoxysilane can enhance the mechanical property of silicones.T etram-ethyltetravinylcyclotetrasiloxane imparts the stronger respond of silicone molecules chain, improves the adhesiveness of resin.Octamethylcy-clotetrasiloxane effectively adjusts the compliance of silicone molecules chain, avoids the influence of rigid radical and more crosslinking points to processing performance.These types of specified raw material is used cooperatively, synergistic effect, and obtaining preferably comprehensive mechanical property for additional organosilicon resin, there is facilitation, the additional organosilicon resin finally prepared to have preferably mechanical property.
Description
Technical field
The present invention relates to organic chemical synthesis technical field more particularly to a kind of additional organosilicon resin and its preparation sides
Method.
Background technology
Additional organosilicon resin has good heat-resisting, weather-proof, radiation resistance, can be used for bonding plastics, metal, rubber
Glue etc..From the forties in last century industrial products come out since, additional organosilicon resin electric and electronic, chemical instruments, automobile,
The fields such as machinery are widely applied.
Traditional add-on type silicone material mostly uses the polydimethylsiloxane of ethenyl blocking as base rubber, methyl hydrogen
Polysiloxanes is made under the action of catalyst as crosslinking agent.But the mechanical property of add-on type silicone material obtained compared with
Difference is easy to happen rupture, cannot be satisfied the requirement in the high performances areas application such as aerospace.
Invention content
In view of this, the technical problem to be solved in the present invention is to provide a kind of additional organosilicon resin and its preparation side
The comprehensive mechanical property of method, additional organosilicon resin made from preparation method using the present invention is more excellent.
The present invention provides a kind of preparation methods of additional organosilicon resin, include the following steps：
A) by aminomethyl phenyl dimethoxysilane, t etram-ethyltetravinylcyclotetrasiloxane, octamethylcy-clotetrasiloxane and
Catalyst mixes, and obtains mixed solution；
B the mixed solution) is heated to 130~155 DEG C, 0.5~5h is kept the temperature, obtains additional organosilicon resin.
Preferably, step A) in, the mixing is specially：
Aminomethyl phenyl dimethoxysilane, t etram-ethyltetravinylcyclotetrasiloxane and octamethylcy-clotetrasiloxane are stirred
After mixing 5~30min, catalyst is added.
Preferably, the rotating speed being stirred is 20~300r/min.
Preferably, the aminomethyl phenyl dimethoxysilane, t etram-ethyltetravinylcyclotetrasiloxane, four silicon of prestox ring
The ratio of the amount of the substance of oxygen alkane and catalyst is 0.01~50：0.1~1.2：40~95：0.05~3.
Preferably, the catalyst is selected from dibutyl tin laurate, sodium hydrate solid, potassium hydroxide solid, tetramethyl
One kind in base ammonium hydroxide and tetrabutylammonium hydroxide.
Preferably, step B) in, the rate of the heating is 1~10 DEG C/min.
Preferably, step B) in, after keeping the temperature 0.5~5h, further include：By the solution decompression distillation after 0.5~5h of heat preservation, drop
It is mild to filter.
Preferably, the pressure of the vacuum distillation is 5~20kPa.
Preferably, the mode of the cooling is natural cooling, water condensation or cooling liquid condensing.
The present invention also provides a kind of additional organosilicon resins prepared by preparation method described above.
The present invention provides a kind of preparation methods of additional organosilicon resin, include the following steps：
A) by aminomethyl phenyl dimethoxysilane, t etram-ethyltetravinylcyclotetrasiloxane, octamethylcy-clotetrasiloxane and
Catalyst mixes, and obtains mixed solution；
B the mixed solution) is heated to 130~155 DEG C, 0.5~5h is kept the temperature, obtains additional organosilicon resin.
Wherein, the addition of aminomethyl phenyl dimethoxysilane can enhance the mechanical properties such as stretching, the tearing of silicones.
T etram-ethyltetravinylcyclotetrasiloxane imparts the stronger respond of silicone molecules chain, improves the adhesiveness of resin.
Octamethylcy-clotetrasiloxane can effectively be adjusted the compliance of silicone molecules chain, avoid rigid radical and more
Influence of the crosslinking points to processing performance.These types of specified raw material is used cooperatively, synergistic effect, for additional organosilicon resin
Obtaining preferably comprehensive mechanical property has facilitation.The additional organosilicon resin finally prepared has preferably mechanical property
Can, it can be applied to the high performances areas such as aerospace.
The experimental results showed that it is half that additional organosilicon resin provided by the invention, which has excellent mechanical property, appearance,
Transparent flowability liquid, the shore hardness after solidification are 30~60HA, and fracture strength is 2.4~7.0MPa, elongation at break
It is 200~380%, tearing strength is 8~16kN/m.
Specific implementation mode
Below in conjunction with the embodiment of the present invention, technical scheme of the present invention is clearly and completely described, it is clear that institute
The embodiment of description is only a part of the embodiment of the present invention, instead of all the embodiments.Based on the embodiments of the present invention,
Every other embodiment obtained by those of ordinary skill in the art without making creative efforts, belongs to this hair
The range of bright protection.
The present invention provides a kind of preparation methods of additional organosilicon resin, include the following steps：
A) by aminomethyl phenyl dimethoxysilane, t etram-ethyltetravinylcyclotetrasiloxane, octamethylcy-clotetrasiloxane and
Catalyst mixes, and obtains mixed solution；
B the mixed solution) is heated to 130~155 DEG C, 0.5~5h is kept the temperature, obtains additional organosilicon resin.
The present invention is first by the organosilan containing phenyl, t etram-ethyltetravinylcyclotetrasiloxane, four silica of prestox ring
Alkane and catalyst mixing, obtain mixed solution.Preferably, specially：By the organosilan containing phenyl, tetramethyl tetravinyl
After cyclotetrasiloxane and octamethylcy-clotetrasiloxane mixing, catalyst is added.
The temperature of the mixing is preferably 10~30 DEG C.In certain embodiments of the present invention, the temperature of the mixing is
Room temperature.The time of the mixing is preferably 5~30min.In certain embodiments of the present invention, the time of the mixing is
15min or 20min.The mixing is preferably stirred.The rotating speed being stirred is preferably 20~300r/min.At this
In some embodiments of invention, the rotating speed being stirred is 60r/min, 80r/min or 90r/min.The present invention is to described
Mixed equipment has no special limitation, is preferably mixed in a kettle.
Phenyl can be introduced into additional organosilicon strand by the addition of the aminomethyl phenyl dimethoxysilane,
Enhance the mechanical properties such as stretching, the tearing of silicones.Double bond in t etram-ethyltetravinylcyclotetrasiloxane imparts organosilicon
The stronger respond of strand, improves the adhesiveness of resin.The methyl of small steric hindrance can be to having in octamethylcy-clotetrasiloxane
The compliance of machine silicon strand is effectively adjusted, and the shadow of rigid radical and more crosslinking points to processing performance is avoided
It rings.These types of specified raw material is used cooperatively, synergistic effect, and preferably comprehensive mechanical property is obtained for additional organosilicon resin
There can be facilitation.The additional organosilicon resin finally prepared has preferably mechanical property, can be applied to aerospace
Contour performances areas.
The catalyst is selected from dibutyl tin laurate, sodium hydrate solid, potassium hydroxide solid, tetramethyl hydroxide
One kind in ammonium and tetrabutylammonium hydroxide.
In the present invention, the aminomethyl phenyl dimethoxysilane, t etram-ethyltetravinylcyclotetrasiloxane, prestox ring
The ratio of the amount of the substance of tetrasiloxane and catalyst is preferably 0.01~50：0.1~1.2：40~95：0.05~3.In the present invention
Some embodiments in, the aminomethyl phenyl dimethoxysilane, t etram-ethyltetravinylcyclotetrasiloxane, four silicon of prestox ring
The ratio of the amount of the substance of oxygen alkane and catalyst is 5：0.1：70：1、2：0.2：50：0.5 or 50：1.2：50：3.
After obtaining mixed solution, the mixed solution is heated to 130~155 DEG C, 0.5~5h is kept the temperature, obtains add-on type
Organic siliconresin.
In the present invention, the temperature of the heating is 130~155 DEG C.In certain embodiments of the present invention, the heating
Temperature be 145 DEG C or 150 DEG C.The present invention has no the rate of the heating special limitation, preferably 1~10 DEG C/min.
In certain embodiments of the present invention, the rate of the heating is 5 DEG C/min or 10 DEG C/min.The time of the heat preservation is 0.5
~5h.In certain embodiments of the present invention, the time of the heat preservation is 4h or 3h.The process of the heat preservation is also the mistake of reaction
Journey.The present invention has no the equipment of the reaction special limitation, is preferably reacted in a kettle.
After 0.5~5h of the heat preservation, preferably further include：By solution decompression distillation, cooling and the pumping after 0.5~5h of heat preservation
Filter.
The pressure of the vacuum distillation is preferably 5~20kPa.In certain embodiments of the present invention, the vacuum distillation
Pressure be 5kPa or 10kPa.The time of the vacuum distillation is preferably 0.5~3h.In certain embodiments of the present invention, institute
The time for stating vacuum distillation is 1h or 1.5h.
Temperature after the cooling is preferably room temperature.The mode of the cooling is preferably natural cooling, water condensation or cooling
Liquid condensing.
Preferably further include that toluene is added to be dissolved before the suction filtration.It is special that the present invention has no the dosage of the toluene
Limitation, the product after the cooling can be completely dissolved.
The effect of the suction filtration is to remove large granular impurity.The suction filtration is preferably filtered with sand core funnel.By filtering
Obtained filtrate is additional organosilicon resin.
The present invention has no special limitation to the source of above-mentioned used material component, can be general commercially available.
The present invention also provides a kind of additional organosilicon resins prepared by preparation method described above.
The additional organosilicon resin has structure shown in formula (I)：
Wherein, 50≤x≤600,2≤x≤40,200≤x≤1300.
It is translucent flowability liquid that additional organosilicon resin provided by the invention, which has excellent mechanical property, appearance,
Body, the shore hardness after solidification are 30~60HA, and fracture strength is 2.4~7.0MPa, and elongation at break is 200~380%, is torn
Resistance to spalling is 8~16kN/m.
The present invention provides a kind of preparation methods of additional organosilicon resin, include the following steps：
A) by aminomethyl phenyl dimethoxysilane, t etram-ethyltetravinylcyclotetrasiloxane, octamethylcy-clotetrasiloxane and
Catalyst mixes, and obtains mixed solution；
B the mixed solution) is heated to 130~155 DEG C, 0.5~5h is kept the temperature, obtains additional organosilicon resin.
Wherein, the addition of aminomethyl phenyl dimethoxysilane can enhance the mechanical properties such as stretching, the tearing of silicones.
T etram-ethyltetravinylcyclotetrasiloxane imparts the stronger respond of silicone molecules chain, improves the adhesiveness of resin.
Octamethylcy-clotetrasiloxane can effectively be adjusted the compliance of silicone molecules chain, avoid rigid radical and more
Influence of the crosslinking points to processing performance.These types of specified raw material is used cooperatively, synergistic effect, for additional organosilicon resin
Obtaining preferably comprehensive mechanical property has facilitation.The additional organosilicon resin finally prepared has preferably mechanical property
Can, it can be applied to the high performances areas such as aerospace.
The experimental results showed that it is half that additional organosilicon resin provided by the invention, which has excellent mechanical property, appearance,
Transparent flowability liquid, the shore hardness after solidification are 30~60HA, and fracture strength is 2.4~7.0MPa, elongation at break
It is 200~380%, tearing strength is 8~16kN/m.
In order to further illustrate the present invention, with reference to embodiments to a kind of additional organosilicon resin provided by the invention
And preparation method thereof be described in detail, but limiting the scope of the present invention cannot be understood as.
Embodiment 1
Weigh 0.5mol aminomethyl phenyls dimethoxysilane, 0.01mol t etram-ethyltetravinylcyclotetrasiloxanes and 7mol
Octamethylcy-clotetrasiloxane is added in reaction kettle, at room temperature, 15min is mixed with the speed of 60r/min.It is added the two of 0.1mol
Dibutyl tin laurate, and system is warming up to 145 DEG C with the rate of 5 DEG C/min, keep the temperature 4h.By the solution after heat preservation in 5kPa
Lower vacuum distillation 1h.Then, cooled to room temperature is added toluene, is filtered with sand core funnel after dissolving, and gained filtrate is to add
It is molded organic siliconresin.
According to GB/T 531.1-2008《Vulcanized rubber or thermoplastic elastomer penetration hardness test method part 1：Shore
Hardometer method (Shao Er hardness)》Standard measures the shore hardness of the additional organosilicon resin after solidification, the results showed that, this reality
The shore hardness for applying the additional organosilicon resin after example solidification is 44HA；According to GB/T 528-2009《Vulcanized rubber or thermoplastic
The measurement of property rubber tensile ess-strain performance》Standard measures the fracture strength of the additional organosilicon resin after solidification and breaks
Split elongation, the results showed that, the fracture strength of the additional organosilicon resin after the present embodiment solidification is 4.5MPa, extension at break
Rate is 350%；According to GB/T 529-2008《Vulcanized rubber or thermoplastic elastomer tearing strength measurement (trousers shape, square and
Crescent sample)》Standard measures the tearing strength of the additional organosilicon resin after solidification, the results showed that, the present embodiment solidification
The tearing strength of additional organosilicon resin afterwards is 12kN/m.
Embodiment 2
Weigh 0.2mol aminomethyl phenyls dimethoxysilane, 0.02mol t etram-ethyltetravinylcyclotetrasiloxanes and 5mol
Octamethylcy-clotetrasiloxane is added in reaction kettle, at room temperature, 20min is mixed with the speed of 80r/min.It is added 0.05mol's
Dibutyl tin laurate, and system is warming up to 150 DEG C with the rate of 10 DEG C/min, keep the temperature 3h.Solution after heat preservation is existed
It is evaporated under reduced pressure 1.5h under 10kPa.Then, cooled to room temperature is added toluene, is filtered with sand core funnel after dissolving, gained filter
Liquid is additional organosilicon resin.
According to GB/T 531.1-2008《Vulcanized rubber or thermoplastic elastomer penetration hardness test method part 1：Shore
Hardometer method (Shao Er hardness)》Standard measures the shore hardness of the additional organosilicon resin after solidification, the results showed that, this reality
The shore hardness for applying the additional organosilicon resin after example solidification is 52HA；According to GB/T 528-2009《Vulcanized rubber or thermoplastic
The measurement of property rubber tensile ess-strain performance》Standard measures the fracture strength of the additional organosilicon resin after solidification and breaks
Split elongation, the results showed that, the fracture strength of the additional organosilicon resin after the present embodiment solidification is 5.3MPa, extension at break
Rate is 280%；According to GB/T 529-2008《Vulcanized rubber or thermoplastic elastomer tearing strength measurement (trousers shape, square and
Crescent sample)》Standard measures the tearing strength of the additional organosilicon resin after solidification, the results showed that, the present embodiment solidification
The tearing strength of additional organosilicon resin afterwards is 13kN/m.
Embodiment 3
Weigh 5mol aminomethyl phenyls dimethoxysilane, 0.12mol t etram-ethyltetravinylcyclotetrasiloxanes and 5mol eight
Methyl cyclotetrasiloxane is added in reaction kettle, at room temperature, 20min is mixed with the speed of 90r/min.The February of 0.3mol is added
Dilaurylate, and system is warming up to 150 DEG C with the rate of 10 DEG C/min, keep the temperature 3h.By the solution after heat preservation in 10kPa
Lower vacuum distillation 1.5h.Then, cooled to room temperature is added toluene, is filtered with sand core funnel after dissolving, gained filtrate is
Additional organosilicon resin.
According to GB/T 531.1-2008《Vulcanized rubber or thermoplastic elastomer penetration hardness test method part 1：Shore
Hardometer method (Shao Er hardness)》Standard measures the shore hardness of the additional organosilicon resin after solidification, the results showed that, this reality
The shore hardness for applying the additional organosilicon resin after example solidification is 60HA；According to GB/T 528-2009《Vulcanized rubber or thermoplastic
The measurement of property rubber tensile ess-strain performance》Standard measures the fracture strength of the additional organosilicon resin after solidification and breaks
Split elongation, the results showed that, the fracture strength of the additional organosilicon resin after the present embodiment solidification is 7.0MPa, extension at break
Rate is 380%；According to GB/T 529-2008《Vulcanized rubber or thermoplastic elastomer tearing strength measurement (trousers shape, square and
Crescent sample)》Standard measures the tearing strength of the additional organosilicon resin after solidification, the results showed that, the present embodiment solidification
The tearing strength of additional organosilicon resin afterwards is 16kN/m.
The foregoing description of the disclosed embodiments enables those skilled in the art to implement or use the present invention.
Various modifications to these embodiments will be apparent to those skilled in the art, as defined herein
General Principle can be realized in other embodiments without departing from the spirit or scope of the present invention.Therefore, of the invention
It is not intended to be limited to the embodiments shown herein, and is to fit to and the principles and novel features disclosed herein phase one
The widest range caused.
Claims (10)
1. a kind of preparation method of additional organosilicon resin, includes the following steps：
A) by aminomethyl phenyl dimethoxysilane, t etram-ethyltetravinylcyclotetrasiloxane, octamethylcy-clotetrasiloxane and catalysis
Agent mixes, and obtains mixed solution；
B the mixed solution) is heated to 130~155 DEG C, 0.5~5h is kept the temperature, obtains additional organosilicon resin.
2. preparation method according to claim 1, which is characterized in that step A) in, the mixing is specially：
Aminomethyl phenyl dimethoxysilane, t etram-ethyltetravinylcyclotetrasiloxane and octamethylcy-clotetrasiloxane are stirred
After 5~30min, catalyst is added.
3. preparation method according to claim 2, which is characterized in that the rotating speed being stirred is 20~300r/
min。
4. preparation method according to claim 1, which is characterized in that the aminomethyl phenyl dimethoxysilane, tetramethyl
The ratio of the amount of the substance of tetravinyl cyclotetrasiloxane, octamethylcy-clotetrasiloxane and catalyst is 0.01~50：0.1~1.2：
40~95：0.05~3.
5. preparation method according to claim 1, which is characterized in that the catalyst be selected from dibutyl tin laurate,
One kind in sodium hydrate solid, potassium hydroxide solid, tetramethylammonium hydroxide and tetrabutylammonium hydroxide.
6. preparation method according to claim 1, which is characterized in that step B) in, the rate of the heating is 1~10
℃/min。
7. preparation method according to claim 1, which is characterized in that step B) in, after keeping the temperature 0.5~5h, further include：It will
It keeps the temperature the solution decompression distillation after 0.5~5h, cooling and filters.
8. preparation method according to claim 7, which is characterized in that the pressure of the vacuum distillation is 5~20kPa.
9. preparation method according to claim 7, which is characterized in that the mode of the cooling is natural cooling, water condensation
Or cooling liquid condensing.
10. additional organosilicon resin prepared by claim 1~9 any one preparation method.
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| CN201810493359.5A CN108586749A (en) | 2018-05-22 | 2018-05-22 | A kind of additional organosilicon resin and preparation method thereof |
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ID=63632292
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111363516A (en) * | 2020-03-26 | 2020-07-03 | 烟台德邦科技有限公司 | Ultraviolet-curing organic silicon coating adhesive and preparation method thereof |
| CN114958201A (en) * | 2022-06-28 | 2022-08-30 | 苏州皇冠涂料科技发展有限公司 | High-thermal-hardness and super-wear-resistant organic silicon non-stick baking paint and preparation method thereof |
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| CN102432883A (en) * | 2011-09-09 | 2012-05-02 | 汕头市骏码凯撒有限公司 | Preparation method of phenyl vinyl silicone oil |
| CN105622944A (en) * | 2016-03-30 | 2016-06-01 | 科凯精细化工（上海）有限公司 | Quaternized organic silicone oil and preparation method thereof |
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| CN102432883A (en) * | 2011-09-09 | 2012-05-02 | 汕头市骏码凯撒有限公司 | Preparation method of phenyl vinyl silicone oil |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111363516A (en) * | 2020-03-26 | 2020-07-03 | 烟台德邦科技有限公司 | Ultraviolet-curing organic silicon coating adhesive and preparation method thereof |
| CN114958201A (en) * | 2022-06-28 | 2022-08-30 | 苏州皇冠涂料科技发展有限公司 | High-thermal-hardness and super-wear-resistant organic silicon non-stick baking paint and preparation method thereof |
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Application publication date: 20180928 |