CN105368063B - It is a kind of to store stable single-component dealcoholization-type room temperature vulcanized silicone rubber - Google Patents
It is a kind of to store stable single-component dealcoholization-type room temperature vulcanized silicone rubber Download PDFInfo
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Abstract
The present invention provides a kind of novel single-component dealcoholization-type room temperature vulcanized silicone rubber, the silicon rubber includes the polysiloxanes of alkoxyalkyl sealing end, plasticizer, gas-phase silica, hydroxyl scavenger, crosslinking agent, silane coupling agent, catalyst, the present invention is used containing silicon heterocyclic compound as hydroxyl scavenger, to remove the hydroxyl and free alcohol in dealcoholized type room temperature vulcanized silicone rubber, single-component dealcoholization-type silicon rubber storage period can be significantly improved, and silicon nitrogen heterocyclic and alcohol type silicone sealant Miscibility are good, no other negative effects can effectively improve substrate bonding simultaneously.
Description
Technical field
The present invention relates to the preparation method of a kind of novel single-component dealcoholization-type room temperature vulcanized silicone rubber and hydroxyl scavenger,
Belong to organosilicon new material technology field.
Background technique
Alcohol is released in single-component dealcoholization-type room temperature vulcanized silicone rubber sulfidation, compared to depickling type and ketoxime removing type,
Have the advantages that environmentally friendly, free from corrosion.It can be widely applied to electronic apparatus and building trade, as a kind of environmentally protective adhesive
Alcohol type sealant by be future market application trend.But its generally existing problem that is, its curability with storage
The extension of time and be gradually reduced or even do not vulcanize, main cause is that the free alcohol in dealcoholysis alcohol type room temperature vulcanized silicone rubber is having
Equilibration reaction occurs with polysiloxanes in the presence of organic metal catalyst, forms (the CH without crosslinking function3O)(CH3)2SiO1/2
End group.
It is exactly to add hydroxyl scavenger to improve the storage period most common method of dealcoholized type room temperature vulcanized silicone rubber, comes clear
Except the hydroxyl and free alcohol in dealcoholized type room temperature vulcanized silicone rubber.One of the most common is addition hexamethyldisilazane class conduct
Hydroxyl scavenger, but during preparation, hexamethyldisilazane can act on and release ammonia, cause corruption to materials such as copper
Erosion, while influencing the production curing performance of dealcoholized type room temperature vulcanized silicone rubber.
Patent US4489191 is added to dealcoholized type room temperature vulcanized silicone rubber using triethoxy hydrogen silane as hydroxyl scavenger
In, since hydrogen can be released during the preparation process, also need to be added ethylenic unsaturation hydro carbons as hydrogen scavenger, and insatiable hunger
The xanthochromia of dealcoholized type room temperature vulcanized rubber is be easy to cause with the addition of alkene.
Summary of the invention
In view of this, the technical problem to be solved in the present invention is that providing a kind of novel dealcoholized type room temperature that storage time is long
Sulphurated siliastic and a kind of hydroxyl scavenger.The present invention, which provides, stores stable single-component dealcoholization-type room temperature vulcanized silicone rubber packet
Include following components:
Wherein the hydroxyl scavenger is silicon heterocyclic compound.
The silicon heterocyclic compound is preferably silicon nitrogen heterocyclic.
The silicon heterocyclic compound is preferably penta silane of azacyclo-, and structural formula is as follows:
Wherein R is C1~C10 alkyl, preferably methyl or ethyl.
The polysiloxanes of the alkoxyalkyl sealing end is preferably terminal methyl group dimethoxy dimethyl silicone polymer,
Structural formula are as follows:
The wherein integer that n is 100~1500, viscosity is 0.8~150Pas at 25 DEG C.
The plasticizer is inert polysiloxane, the preferably dimethyl silicone polymer of methyl blocking, and 25 DEG C of whens move
Viscosity is 0.1~20Pas.
The gas-phase silica includes hydrophilic gas-phase silica, any one in hydrophobic type gas-phase silica,
Specific surface area is 100~300m2/g。
The crosslinking agent is methyltrimethoxysilane, methyltriethoxysilane, vinyltrimethoxysilane, second
One or more of alkenyl triethoxysilane, phenyltrimethoxysila,e, phenyl triethoxysilane.
The catalyst is dibutyl tin dilaurate, dibutyl tin acetate, dioctyl tin cinnamic acid tin, two (ten
Dialkyl group sulphur) dibutyl tin, stannous octoate, two fourth acetylacetone,2,4-pentanedione tin, dibutyl ethyl acetoacetate tin one or more.
The present invention additionally provides a kind of preparation method of silicon heterocyclic compound simultaneously, comprising:
Silane compound is heated to reflux state, carries out intramolecular cyclization reaction under acid catalyst effect, when reaction
Between be 5-20h, preferably 8-10h, fractionate out by-product alcohol simultaneously in reaction process, stop reaction when not regenerating alcohol, and
Distillation obtains target product；The silane compound is shown below:
Wherein n=2~4, n are integer, and n is preferably 3；R is C1~C10 alkyl, preferably methyl or ethyl.
The acid is one of trifluoromethanesulfonic acid, fluosulfonic acid, benzene sulfonic acid, methanesulfonic acid, preferably trifluoromethanesulfonic acid.
Wherein the molar ratio of acid catalyst and silane compound is 1: 100~10000, preferably 1: 200~2000.
Compared with the prior art, the present invention provides single-component dealcoholization-type silicone rubber compound and has the advantage that
1) present invention, as hydroxyl scavenger, can significantly improve single-component dealcoholization-type silicon rubber using containing silicon heterocyclic compound
Storage period；
2) siliceous nitrogen heterocyclic used by and alcohol type silicone sealant Miscibility are good, no other negative effects
Even substrate bonding can be effectively improved, reason be hydroxyl scavenger at room temperature it can react with free alcohol in system, give birth to
It is shown below at amino silane reaction equation, and amino silane is exactly a kind of dealcoholized type room temperature vulcanized silicone rubber commonly increasing
Stick.
Detailed description of the invention
Fig. 1 is penta silane of azacyclo- prepared by embodiment 1.
Specific embodiment
Specific description is done to present aspect below by embodiment, it is necessary to which indicated herein is that following embodiment is served only for
Invention is further explained, should not be understood as limiting the scope of the invention, the person skilled in the art in the field
Nonessential modifications and adaptations can be made according to the present invention.
Embodiment 1
It takes 200g aminopropyl trimethoxysilane into flask, starts to stir to be warming up to reflux state occur, be added dropwise to
0.2g trifluoromethanesulfonic acid starts clock reaction 8h, while collecting by-product carbinol using condenser.End of reaction, in vacuum degree
It is distilled under 0.6KPa, according to nuclear-magnetism1HNMR analysis, obtains purpose product 178g, yield 89% in 100-105 DEG C of fraction.
Target product structural formula is as follows:
1HNMR(CDCl3): 0.62 (t, 2H), 1.24 (m, H), 1.60 (m, 2H), 2.7 (t, 2H), 3.56 (s, 6H).
Embodiment 2
It takes 200g aminopropyl triethoxysilane into flask, starts to stir to be warming up to reflux state occur, be added dropwise to
0.2g trifluoromethanesulfonic acid starts clock reaction 12h, while fractionating out coproduct ethanol.End of reaction, at vacuum degree 0.6KPa
It is distilled, according to nuclear-magnetism1HNMR analysis, obtains purpose product 170g, yield 85% in 105-115 DEG C of fraction.Target product
Structural formula is as follows:
1HNMR(CDCl3): 0.62 (t, 2H), 1.2 (m, H), 1.68 (m, 2H), 2.7 (t, 2H), 3.75 (m, 10H).
Embodiment 3
It takes 200g aminopropyl tripropoxy silane into flask, starts to stir to be warming up to reflux state occur, be added dropwise to
0.2g benzene sulfonic acid starts clock reaction 15h, while collecting by-product propyl alcohol using condenser.End of reaction, in vacuum degree
It is distilled under 0.6KPa, according to nuclear-magnetism1HNMR analysis, obtains purpose product 164g, yield 82% in 109-120 DEG C of fraction.
Target product structural formula is as follows:
1HNMR(CDCl3): 0.63 (t, 2H), 1.2 (m, H), 1.70 (m, 2H), 2.7 (t, 2H), 4.32 (m, 14H).
Embodiment 4
100 parts of 20Pas terminal methyl group dimethoxy dimethyl silicone polymers；It is added poly- the two of 0.3Pas methyl blocking
20 parts of methylsiloxane, 10 parts of hydrophobic gas-phase silica of specific surface area 150 stirred under the conditions of vacuum degree > 0.09Mpa
30min；Then the substance of 5 parts of methyltrimethoxysilane, the synthesis of 1 part, 1 part embodiment 1 of aminopropyl triethoxysilane is added,
0.2 part of dibutyl ethyl diacetoacetate tin stirs 30min clock under the conditions of vacuum degree > 0.09Mpa, it is transparent that one-component is made
Alcohol type silicone sealant compositions are fitted into sealed rubber pipe, and see Table 1 for details for properties of product test result
Embodiment 5
100 parts of 20Pas terminal methyl group dimethoxy dimethyl silicone polymers；It is added poly- the two of 0.3Pas methyl blocking
20 parts of methylsiloxane, 10 parts of hydrophobic gas-phase silica of specific surface area 150 stirred under the conditions of vacuum degree > 0.09Mpa
30min；Then the substance of 5 parts of methyltrimethoxysilane, the synthesis of 1 part, 1 part embodiment 2 of aminopropyl triethoxysilane is added,
0.2 part of dibutyl ethyl diacetoacetate tin stirs 30min clock under the conditions of vacuum degree > 0.09Mpa, it is transparent that one-component is made
Alcohol type silicone sealant compositions are fitted into sealed rubber pipe, and see Table 1 for details for properties of product test result
Embodiment 6
100 parts of 20Pas terminal methyl group dimethoxy dimethyl silicone polymers；It is added poly- the two of 0.3Pas methyl blocking
20 parts of methylsiloxane, 10 parts of hydrophobic gas-phase silica of specific surface area 150 stirred under the conditions of vacuum degree > 0.09Mpa
30min；Then the substance of 5 parts of methyltrimethoxysilane, the synthesis of 1 part, 1 part embodiment 3 of aminopropyl triethoxysilane is added,
0.2 part of dibutyl ethyl diacetoacetate tin stirs 30min clock under the conditions of vacuum degree > 0.09Mpa, it is transparent that one-component is made
Alcohol type silicone sealant compositions are fitted into sealed rubber pipe, and see Table 1 for details for properties of product test result
Comparative example 1
100 parts of 20pas terminal methyl group dimethoxy dimethyl silicone polymers；The poly- diformazan of 0.3Pas methyl blocking is added
20 parts of radical siloxane, 10 parts of hydrophobic gas-phase silica of specific surface area 150 stir 30min under the conditions of vacuum degree > 0.09Mpa；
Then 1 part, 1 part 5 parts of methyltrimethoxysilane, aminopropyl triethoxysilane hexamethyldisilazane, dibutyl two is added
0.2 part of ethyl acetoacetate tin is stirred 30min clock under the conditions of vacuum degree > 0.09Mpa, and it is organic that the transparent alcohol type of one-component is made
Silicone sealant composition is fitted into sealed rubber pipe, and see Table 1 for details for properties of product test result
Comparative example 2
100 parts of 20pas terminal methyl group dimethoxy dimethyl silicone polymers；The poly- diformazan of 0.3Pas methyl blocking is added
20 parts of radical siloxane, 10 parts of hydrophobic gas-phase silica of specific surface area 150 stir 30min under the conditions of vacuum degree > 0.09Mpa；
Then 1 part, 1 part 5 parts of methyltrimethoxysilane, aminopropyl triethoxysilane triethoxy hydrogen silicon, dibutyl diethyl is added
0.2 part of ethyl acetoacetic acid ethyl ester tin stirs 30min clock under the conditions of vacuum degree > 0.09Mpa, the transparent alcohol type organosilicon of one-component is made
Sealant composition is fitted into sealed rubber pipe, and see Table 1 for details for properties of product test result
Comparative example 3
100 parts of 20pas terminal methyl group dimethoxy dimethyl silicone polymers；The poly- diformazan of 0.3Pas methyl blocking is added
20 parts of radical siloxane, 10 parts of hydrophobic gas-phase silica of specific surface area 150 stir 30min under the conditions of vacuum degree > 0.09Mpa；
Then 1 part, 1 part 5 parts of methyltrimethoxysilane, aminopropyl triethoxysilane isocyanate group propyl trimethoxy silicon is added
Alkane, 0.2 part of dibutyl ethyl diacetoacetate tin stir 30min under the conditions of vacuum degree > 0.09Mpa, it is saturating that one-component are made
Bright alcohol type silicone sealant compositions are fitted into sealed rubber pipe, and see Table 1 for details for properties of product test result
Test method:
The transparent dealcoholysis alcohol type room temperature vulcanized silicone rubber of obtained one-component is tested for the property by the present invention, and detailed process is such as
Under:
1) using standard No. is the national standard of GB/T 13477-2002 to the transparent dealcoholized type room temperature sulphur of obtained one-component
The surface drying time of SiClx rubber, the test of aluminum oxide base material I-shaped piece cementability；
2) according to the national standard that standard No. is GB/T531.1-2008 to the transparent dealcoholized type room temperature sulphur of obtained one-component
The hardness of SiClx rubber is tested；
3) the transparent dealcoholized type room temperature vulcanized silicone rubber of the one-component of preparation is carried out respectively in sebific duct 50 DEG C of surroundings, 70
DEG C one week, room temperature condition stores 1 year and detects single-component dealcoholization-type room temperature vulcanized silicone rubber storage period situation under the conditions of three kinds.
Table 1
It is saturating to can be seen that the one-component being prepared using different hydroxyl scavengers according to the performance data that upper table is tested
Bright alcohol type silicone seal initial performance, including surface drying time, hardness are almost the same.But pass through 50 DEG C, 70 DEG C of accelerated ageing realities
Test and room temperature natural aging result can be seen that using this patent preparation hydroxyl scavenger glue example 4-6 performance it is basic
It is unchanged, and using the comparison example of other hydroxyl scavengers such as silazane with longer storage duration, surface drying time significantly prolongs
Long, hardness is substantially reduced or even can not solidify.Thus illustrate, hydroxyl scavenger provided by the invention is to raising single-component dealcoholization-type
The storage stability significant effect of room temperature vulcanized silicone rubber.
Claims (11)
1. a kind of single-component dealcoholization-type room temperature vulcanized silicone rubber, which is characterized in that including following components:
100 mass parts of polysiloxanes of alkoxyalkyl sealing end
Plasticizer 0-100 mass parts
Gas-phase silica 5-40 mass parts
Hydroxyl scavenger 0.5-5 mass parts
Crosslinking agent 0-8 mass parts
Silane coupling agent 0.5-5 mass parts
Catalyst 0.1-3 mass parts；
The hydroxyl scavenger is silicon heterocyclic compound.
2. single-component dealcoholization-type room temperature vulcanized silicone rubber as described in claim 1, which is characterized in that the silicon heterocyclic compound
Object is silicon nitrogen heterocyclic.
3. single-component dealcoholization-type room temperature vulcanized silicone rubber as claimed in claim 2, which is characterized in that the silicon heterocyclic compound
Object is penta silane of azacyclo-, and structural formula is as follows:
Wherein R is C1-C10 alkyl.
4. single-component dealcoholization-type room temperature vulcanized silicone rubber as claimed in claim 3, which is characterized in that the R be methyl or
Ethyl.
5. single-component dealcoholization-type room temperature vulcanized silicone rubber as described in claim 1, which is characterized in that the alkoxyalkyl sealing end
Polysiloxanes be preferably terminal methyl group dimethoxy dimethyl silicone polymer, structural formula are as follows:
The wherein integer that n is 100 ~ 1500, viscosity is 0.8-150 Pa s at 25 DEG C.
6. single-component dealcoholization-type room temperature vulcanized silicone rubber as described in claim 1, which is characterized in that the plasticizer is lazy
Property polysiloxanes.
7. single-component dealcoholization-type room temperature vulcanized silicone rubber as described in claim 1, which is characterized in that the crosslinking agent is first
Base trimethoxy silane, methyltriethoxysilane, vinyltrimethoxysilane, vinyltriethoxysilane, phenyl three
One or more of methoxy silane, phenyl triethoxysilane.
8. single-component dealcoholization-type room temperature vulcanized silicone rubber as described in claim 1, which is characterized in that the catalyst is two
Butyl tin dilaurate tin, dibutyl tin acetate, dioctyl tin cinnamic acid tin, two (dodecyl sulphur) dibutyl tins, octanoic acid are sub-
Tin, two fourth acetylacetone,2,4-pentanedione tin, dibutyl ethyl acetoacetate tin are one or more kinds of.
9. single-component dealcoholization-type room temperature vulcanized silicone rubber as claimed in claim 3, which is characterized in that the silicon heterocyclic compound
Object the preparation method is as follows:
Silane compound is heated to reflux state, carries out intramolecular cyclization reaction under acid catalyst effect, the reaction time is
5-20h fractionates out by-product alcohol simultaneously in reaction process, stops reaction when not regenerating alcohol, and distill and obtain target product；
The silane compound is shown below:
, wherein n=3.
10. single-component dealcoholization-type room temperature vulcanized silicone rubber as claimed in claim 9, which is characterized in that the acid is trifluoro
One of methanesulfonic acid, fluosulfonic acid, benzene sulfonic acid, methanesulfonic acid.
11. single-component dealcoholization-type room temperature vulcanized silicone rubber as claimed in claim 9, which is characterized in that the acid catalyst
Molar ratio with silane compound is 1:100-10000.
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| JP2024055241A (en) * | 2022-10-07 | 2024-04-18 | 信越化学工業株式会社 | Room temperature curable organopolysiloxane composition |
| CN116254001B (en) * | 2022-12-27 | 2024-06-07 | 湖北环宇化工有限公司 | Dealcoholized RTV-1 silicone rubber with good storage stability and preparation method thereof |
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Effective date of registration: 20191216 Address after: 311600, No. 8 Fenghe Road, Xiaya Town, Jiande City, Hangzhou City, Zhejiang Province Patentee after: Zhejiang Lide Silicone Material Co., Ltd. Address before: Jiande City, Zhejiang province 311600 Riverside Road No. 1 Xin'an building Patentee before: Xin'an Chemical Industry Group Co., Ltd., Zhejiang |