CN103467745B - The preparation method of terminal alkoxy polysiloxane - Google Patents

The preparation method of terminal alkoxy polysiloxane Download PDF

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CN103467745B
CN103467745B CN201310395394.0A CN201310395394A CN103467745B CN 103467745 B CN103467745 B CN 103467745B CN 201310395394 A CN201310395394 A CN 201310395394A CN 103467745 B CN103467745 B CN 103467745B
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silane
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polysiloxane
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terminal alkoxy
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CN103467745A (en
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杨鑫波
屈裴
熊婷
黄强
车国勇
李步春
王有治
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CHENGDU GUIBAO SCIENCE AND TECHNOLOGY INDUSTRIAL Co Ltd
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CHENGDU GUIBAO SCIENCE AND TECHNOLOGY INDUSTRIAL Co Ltd
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Abstract

The invention discloses a kind of preparation method of terminal alkoxy polysiloxane, comprise the following steps: step one: batching: component A: hydroxy-end capped polysiloxane; B component: organoalkoxysilane/or its partial hydrolystate with at least 3 alkoxyl groups; Component C: the organoalkoxysilane of ammonia alkyl; Step 2: component A, B, C are added in high speed dispersor, under rare gas element or vacuum, high-speed stirring; Step 3: material step 2 stirred is under rare gas element or vacuum, and temperature is 0 ~ 100 DEG C, places 0.5 ~ 24h, carries out terminal alkylations original position end capping, obtain terminal alkoxy polysiloxane.This preparation method adopts the organoalkoxysilane of ammonia alkyl as catalyzer, the polysiloxane that catalysis is hydroxy-end capped and organoalkoxysilane original position end-blocking, prepared terminal alkoxy polysiloxane viscosity B coefficent is little, and side reaction is few, and technique is simple, be easy to control, easy to operate, energy consumption is little.

Description

The preparation method of terminal alkoxy polysiloxane
Technical field
The invention belongs to polymeric material field, be specifically related to a kind of preparation method of terminal alkoxy polysiloxane.
Background technology
When terminal alkoxy polysiloxane meets moisture, alkoxyl group hydrolyzable, and then crosslinked polymer is solidified.Only discharging tasteless, neutral low molecule alcohols material in solidification process, to had no corrosive effect on metals such as copper, lead, zinc, is a kind of environmentally friendly macromolecular material.The dealcoholized type room temperature vulcanized silicone rubber product that based on it prepared by polymkeric substance, can can keep good physicals and electrical property in the environment of harshness, be widely used in the industries such as building, automobile, electric power, new forms of energy, electronic apparatus and fix as bonding, sealing, encapsulation, coating, components and parts.
The hydrolytic activity of neutral alcoxyl fundamental mode silane is very low, and has after hydroxy-terminated polysiloxane mix, very difficultly effectively forms terminal alkoxy polysiloxane.US3161614 discloses in anhydrous conditions, and hydroxy-terminated polysiloxane and chloride organoalkoxysilane react, and adds pyridine solvent as hydrogenchloride receptor, generates high boiling pyridine hydrochloride, with in reaching and the object of hydrogenchloride.Along with the development of closed-end technology, terminal alkoxy polysiloxane selects hydroxy-end capped polysiloxane and organoalkoxysilane original position end capping under certain catalysts conditions to obtain usually.Domestic and international patent and document mainly concentrate on the selection of catalyzer, and the mixture of US3542901 report organic amine compound, US3161614 carboxylic metallic salt and amine, EP070786 hydroxylamine derivative, US5352751 adopt alkali metal hydroxide, EP0564253 organolithium, CN1264404 Bronsted acid or the catalyzer such as Lewis acid, CN1283212 phosphate ester acid to there is lower catalysis alkoxyl group original position end capping.After end-blocking is ended, the acid that needs are corresponding or alkali make catalyst deactivation.In order to ensure the package stability of the finished product, the amount of deactivator must be accurately consistent with the amount of catalyzer, and during concrete end-blocking, often need use excessive deactivator.Because deactivator has higher equilibrium activity, so again must remove from product.Therefore, select a kind of suitable catalyzer, additionally do not add deactivator, just make terminal alkoxy polysiloxane have good storage stability, have very important significance.
Summary of the invention
The object of the invention is the preparation method that a kind of terminal alkoxy polysiloxane is provided for the deficiencies in the prior art, be characterized in the polysiloxane that the organoalkoxysilane catalysis of employing ammonia hydrocarbyl functional is hydroxy-end capped and organoalkoxysilane original position end-blocking.
In order to reach above-mentioned technique effect, the present invention takes following technical scheme:
A preparation method for terminal alkoxy polysiloxane, comprises the following steps:
Step one: batching: component A: hydroxy-end capped polysiloxane; B component: organoalkoxysilane/or its partial hydrolystate with at least 3 alkoxyl groups; Component C: the organoalkoxysilane with the ammonia alkyl of general formula [I],
general formula [I],
Wherein: R 1for having the alkyl of 1 ~ 8 carbon atom;
R 2for having the alkyl of 1 ~ 8 carbon atom;
R 3for hydrogen or alkyl or the-OR with 1 ~ 2 carbon atom 1or-OR 2group;
X is 0 or 1;
Step 2: component A, B, C are added in high speed dispersor, under rare gas element or vacuum (vacuum tightness is 0.08 ~ 0.099MPa), high-speed stirring;
Step 3: material step 2 stirred is under rare gas element or vacuum, and temperature is 0 ~ 100 DEG C, places 0.5 ~ 24h, carries out terminal alkylations original position end capping, obtain terminal alkoxy polysiloxane.
In above-mentioned preparation method, described component A preferably has the linear α of general formula [II], alpha, omega-dihydroxy polysiloxane:
HO-[R 2siO] n-H, general formula [II],
Wherein: R is the alkyl with 1 ~ 8 carbon atom; N has certain value, and it is 100 ~ 150000mPaS that this value corresponds to the hydroxy-end capped viscosity of polysiloxane when temperature 25 DEG C, and namely the viscosity of component A when temperature 25 DEG C is that 100 ~ 150000mPaS all can be used in the present invention.In the application of reality, in component A the value of n be all adopt first measure viscosity and R group after backstepping obtain the value of n.
In above-mentioned preparation method, described B component has the structural formula of general formula [III]:
R 4 msi (OR 5) 4-m, general formula [III],
Wherein: R 4for having alkyl or the aryl of 1 ~ 8 carbon atom; R 5for having the alkyl of 1 ~ 8 carbon atom; M is 0 or 1.
Be more specifically: described B component is at least one in methyltrimethoxy silane, Union carbide A-162, methyl tripropoxy silane, methyl three butoxy silane, tetramethoxy-silicane, tetraethoxysilane, tetrapropoxysilane, four butoxy silanes, ethyl trimethoxy silane, ethyl triethoxysilane, phenyltrimethoxysila,e, phenyl triethoxysilane, vinyltrimethoxy silane, vinyltriethoxysilane.
According to a preferred embodiment of the invention, described B component is at least one in tetramethoxy-silicane, tetraethoxysilane, methyltrimethoxy silane, Union carbide A-162, vinyltrimethoxy silane, vinyltriethoxysilane, phenyltrimethoxysila,e, phenyl triethoxysilane.
In above-mentioned preparation method, described component C has the structural formula of general formula [IV] or [V]:
general formula [IV];
general formula [V];
Wherein: R 1for having the alkyl of 1 ~ 8 carbon atom;
R 2for having the alkyl of 1 ~ 8 carbon atom;
R 3for alkyl or the-OR of hydrogen or 1 ~ 2 carbon atom 1or-OR 2group;
R 6for hydrogen or have the alkyl of 2 ~ 10 carbon atoms, aryl or aryl;
R 7for hydrogen or have the alkyl of 2 ~ 10 carbon atoms, aryl or aryl;
R 8for in the alkyl with 2 ~ 10 carbon atoms or the hydrocarbyl chain with 2 ~ 10 carbon atoms containing NH, O, H group;
X is 0 or 1.
Be more specifically: described component C is γ-aminopropyltrimethoxysilane, γ-aminopropyl triethoxysilane, N-β-(aminoethyl)-γ-aminopropyltrimethoxysilane, N-β-(aminoethyl)-γ-aminopropyl triethoxysilane, N-β-(aminoethyl)-γ-aminopropyltriethoxy dimethoxysilane, N-β-(aminoethyl)-γ-aminopropyltriethoxy diethoxy silane, N-cyclohexyl-γ-aminopropyltrimethoxysilane, N-cyclohexyl-γ-aminopropyl triethoxysilane, diethylin oxypropyl trimethyl silane, diethylin propyl-triethoxysilicane, aniline propyl trimethoxy silicane, imidazolylpropyl Trimethoxy silane, imidazolylpropyl triethoxyl silane, piperidinylpropyl Trimethoxy silane, piperidinylpropyl triethoxyl silane, piperazinopropyl Trimethoxy silane, piperazinopropyl triethoxyl silane, morpholinyl propyl Trimethoxy silane, morpholinyl propyl triethoxyl silane, pyrrolidinylpropyl Trimethoxy silane, at least one in pyrrolidinylpropyl triethoxyl silane.
As the preferred embodiments of the present invention, preferably: described component C is at least one in γ-aminopropyltrimethoxysilane, γ-aminopropyl triethoxysilane, N-β-(aminoethyl)-γ-aminopropyltrimethoxysilane, N-β-(aminoethyl)-γ-aminopropyltriethoxy dimethoxysilane, N-cyclohexyl-γ-aminopropyltrimethoxysilane, imidazolylpropyl triethoxyl silane, piperidinylpropyl triethoxyl silane, piperazinopropyl triethoxyl silane, morpholinyl propyl Trimethoxy silane, pyrrolidinylpropyl triethoxyl silane.
In above-mentioned preparation method, the mass ratio of described component A, B component, component C is 100:(0.5 ~ 10): (0.01 ~ 10).
As the preferred embodiments of the present invention, preferably: the mass ratio of described component A, B component, component C is 100:(1 ~ 8): (0.1 ~ 6).
In above-mentioned preparation method, the rotating speed stirred in step 2 is 200 ~ 3000r/min, and churning time is 1 ~ 30min.
As the preferred embodiments of the present invention, preferably: in step 3, temperature is 20 ~ 60 DEG C, storage period is 1 ~ 12h.
The present invention compared with prior art, has following beneficial effect:
(1) this preparation method adopts the organoalkoxysilane of ammonia alkyl as catalyzer, the polysiloxane that catalysis is hydroxy-end capped and organoalkoxysilane original position end-blocking, without the need to being removed by catalyzer after having reacted, reduces the operation steps of preparation method.
(2) the terminal alkoxy polysiloxane viscosity B coefficent prepared by the method is little, and side reaction is few, and technique is simple, be easy to control, easy to operate, energy consumption is little, can be widely used in that single-component de-alcoholized room temperature vulcanized organosilicon sealing material is full-automatic to be produced greatly.
(3) after this preparation method only needs each component fully to mix, at 0 ~ 100 DEG C, can react obtained terminal alkoxy polysiloxane, reaction conditions is easy to control, and operation steps is simple.
Accompanying drawing explanation
The hydroxy-end capped polysiloxane that Fig. 1 adopts for embodiment 1 1h NMR schemes.
Fig. 2 is the terminal alkoxy polysiloxane that obtains of embodiment 1 1h NMR schemes.
Embodiment
Below in conjunction with embodiments of the invention, the invention will be further elaborated.
The performance test of terminal alkoxy polysiloxane prepared by embodiments of the invention:
1) organopolysiloxane viscosity is tested by GB/T10247-2008;
2) by quick tiron chemical process, inspection end-blocking effect;
3) by JY/T007-1996 superconducting pulse Fourier transform nuclear magnetic resonance spectral method general rule, polysiloxane end-functionalization situation is characterized.
Embodiment 1:
In high speed dispersor, add the α of 100 mass parts viscosity (25 DEG C) 650mPas being cooled to room temperature through 100 DEG C of decompression dehydration 3h, alpha, omega-dihydroxy polydimethyl siloxane, its proton nmr spectra ( 1h NMR) see accompanying drawing 1.Add 4 mass parts methyltrimethoxy silanes, 2 mass parts vinyltrimethoxy silanes, after mixing, institute's viscosimetric is 473mPas; Add 1 mass parts γ-aminopropyltrimethoxysilane, 2 mass parts N-β-(aminoethyl)-γ-aminopropyltrimethoxysilane, under protection of inert gas, with 2000r/min high-speed stirring 2min.2h is placed in lower 50 DEG C of protection of inert gas, by quick tiron chemical process inspection end-blocking situation, without viscosity peak phenomenon.The viscosity of gained terminal alkoxy polysiloxane is 478mPas, its 1hNMR is shown in accompanying drawing 2.Continue placement under protection of inert gas 30 days, institute's viscosimetric is 482mPas. 1h NMR analyzes, α, and alpha, omega-dihydroxy polydimethyl siloxane, after end alkoxy group, disappears at the silicone hydroxyl peak at δ=1.9ppm place, occurs alcoxyl base peak at δ=3.6ppm place.
Embodiment 2:
In high speed dispersor, add the α of 600 mass parts viscosity (25 DEG C) 17700mPas being cooled to room temperature through 100 DEG C of decompression dehydration 3h, the α of alpha, omega-dihydroxy polydimethyl siloxane and 60 mass parts viscosity (25 DEG C) 150000mPas, alpha, omega-dihydroxy polydimethyl siloxane, 24 mass parts tetraethoxysilanes, 6 mass parts phenyltrimethoxysila,e are added after dispersed, after mixing, institute's viscosimetric is 18600mPas; Add 4 mass parts N-β-(aminoethyl)-γ-aminopropyltriethoxy dimethoxysilane, 5 mass parts imidazolylpropyl triethoxyl silanes, under keeping vacuum tightness 0.08 ~ 0.099MPa condition, with 1500r/min high-speed stirring 5min.Keep vacuum tightness 0.08 ~ 0.099MPa, at 30 DEG C, place 4h, by quick tiron chemical process inspection end-blocking situation, without viscosity peak phenomenon.The viscosity of gained terminal alkoxy polysiloxane is 19400mPas.Continue placement under protection of inert gas 30 days, institute's viscosimetric is 19700mPas.Warp 1h NMR analyzes, not containing silicone hydroxyl.
Embodiment 3:
In high speed dispersor, add the α of 1000 mass parts viscosity (25 DEG C) 49500mPas, alpha, omega-dihydroxy polydimethyl siloxane, 10 mass parts vinyltrimethoxy silanes, 30 mass parts Union carbide A-162s, after mixing, institute's viscosimetric is 42800mPas; Add 1 mass parts N-cyclohexyl-γ-aminopropyltrimethoxysilane, 2 mass parts piperidinylpropyl triethoxyl silanes, 2 mass parts piperazinopropyl triethoxyl silanes, under protection of inert gas, with 800r/min high-speed stirring 15min.Under protection of inert gas, place 6h in 25 DEG C, by quick tiron chemical process inspection end-blocking situation, without viscosity peak phenomenon.The viscosity of gained terminal alkoxy polysiloxane is 47700mPas.Continue placement under protection of inert gas 30 days, institute's viscosimetric is 47900mPas.Warp 1h NMR analyzes, not containing silicone hydroxyl.
Embodiment 4:
In high speed dispersor, add the α of 3000 mass parts viscosity (25 DEG C) 78900mPas, the α of alpha, omega-dihydroxy polydimethyl siloxane and 30 mass parts viscosity (25 DEG C) 100mPas, alpha, omega-dihydroxy polydimethyl siloxane, 45 mass parts vinyltriethoxysilanes, 30 mass parts phenyl triethoxysilanes, 15 mass parts tetraethoxysilanes are added after dispersed, after mixing, institute's viscosimetric is 71200mPas; Add 5 mass parts morpholinyl propyl Trimethoxy silanes, 4 mass parts pyrrolidinylpropyl triethoxyl silanes, under protection of inert gas, with 400r/min high-speed stirring 25min.Under protection of inert gas, place 8h in 40 DEG C, by quick tiron chemical process inspection end-blocking situation, without viscosity peak phenomenon.The viscosity of gained terminal alkoxy polysiloxane is 76500mPas.Continue placement under protection of inert gas 30 days, institute's viscosimetric is 77100mPas.Warp 1h NMR analyzes, not containing silicone hydroxyl.
Comparative example 1:
Do not add γ-aminopropyltrimethoxysilane, N-β-(aminoethyl)-γ-aminopropyltrimethoxysilane, repeat embodiment 1.Place 30 days under protection of inert gas, add quick tiron, occur obvious viscosity peak phenomenon immediately.
Comparative example 2:
Add 2.5 mass parts dibutylamine and replace N-cyclohexyl-γ-aminopropyltrimethoxysilane, piperidinylpropyl triethoxyl silane, piperazinopropyl triethoxyl silane, repeat embodiment 3, by quick tiron chemical process inspection end-blocking situation, without viscosity peak phenomenon.The viscosity of gained terminal alkoxy polysiloxane is 49500mPas.Continue placement under protection of inert gas 30 days, institute's viscosimetric is 57900mPas, and viscosity B coefficent is more than 10%.
Although with reference to explanatory embodiment of the present invention, invention has been described here, above-described embodiment is only the present invention's preferably embodiment, embodiments of the present invention are not restricted to the described embodiments, should be appreciated that, those skilled in the art can design a lot of other amendment and embodiment, these amendments and embodiment will drop within spirit disclosed in the present application and spirit.

Claims (6)

1. a preparation method for terminal alkoxy polysiloxane, is characterized in that comprising the following steps:
Step one: batching: component A: hydroxy-end capped polysiloxane, B component: organoalkoxysilane/or its partial hydrolystate with at least 3 alkoxyl groups, component C: γ-aminopropyltrimethoxysilane, N-β-(aminoethyl)-γ-aminopropyltrimethoxysilane, N-β-(aminoethyl)-γ-aminopropyl triethoxysilane, N-β-(aminoethyl)-γ-aminopropyltriethoxy dimethoxysilane, N-β-(aminoethyl)-γ-aminopropyltriethoxy diethoxy silane, N-cyclohexyl-γ-aminopropyltrimethoxysilane, N-cyclohexyl-γ-aminopropyl triethoxysilane, diethylin oxypropyl trimethyl silane, diethylin propyl-triethoxysilicane, aniline propyl trimethoxy silicane, imidazolylpropyl Trimethoxy silane, imidazolylpropyl triethoxyl silane, piperidinylpropyl Trimethoxy silane, piperidinylpropyl triethoxyl silane, piperazinopropyl Trimethoxy silane, piperazinopropyl triethoxyl silane, morpholinyl propyl Trimethoxy silane, morpholinyl propyl triethoxyl silane, pyrrolidinylpropyl Trimethoxy silane, at least one in pyrrolidinylpropyl triethoxyl silane,
Step 2: component A, B, C are added in high speed dispersor, under rare gas element or vacuum, high-speed stirring;
Step 3: material step 2 stirred is under rare gas element or vacuum, and temperature is 0 ~ 100 DEG C, places 0.5 ~ 24h, carries out terminal alkylations original position end capping, obtain terminal alkoxy polysiloxane.
2. the preparation method of terminal alkoxy polysiloxane according to claim 1, is characterized in that described component A is for having the linear α of general formula [II], alpha, omega-dihydroxy polysiloxane:
HO-[R 2siO] n-H, general formula [II],
Wherein: R is the alkyl with 1 ~ 8 carbon atom; N has certain value, and it is 100 ~ 150000mPaS that this value corresponds to the hydroxy-end capped viscosity of polysiloxane when temperature 25 DEG C.
3. the preparation method of terminal alkoxy polysiloxane according to claim 1, is characterized in that described B component has the structural formula of general formula [III]:
R 4 msi (OR 5) 4-m, general formula [III],
Wherein: R 4for having alkyl or the aryl of 1 ~ 8 carbon atom; R 5for having the alkyl of 1 ~ 8 carbon atom; M is 0 or 1.
4. the preparation method of terminal alkoxy polysiloxane according to claim 3, is characterized in that described B component is at least one in methyltrimethoxy silane, Union carbide A-162, methyl tripropoxy silane, methyl three butoxy silane, tetramethoxy-silicane, tetraethoxysilane, tetrapropoxysilane, four butoxy silanes, ethyl trimethoxy silane, ethyl triethoxysilane, phenyltrimethoxysila,e, phenyl triethoxysilane, vinyltrimethoxy silane, vinyltriethoxysilane.
5. the preparation method of terminal alkoxy polysiloxane according to claim 1, is characterized in that the mass ratio of described component A, B component, component C is 100:(0.5 ~ 10): (0.01 ~ 10).
6. the preparation method of terminal alkoxy polysiloxane according to claim 1, it is characterized in that the rotating speed stirred in step 2 is 200 ~ 3000r/min, churning time is 1 ~ 30min.
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