CN109593510A - Alkoxy end-capped organosilicon polymer, preparation method and single-component de-alcoholized organosilicon sealant - Google Patents
Alkoxy end-capped organosilicon polymer, preparation method and single-component de-alcoholized organosilicon sealant Download PDFInfo
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- CN109593510A CN109593510A CN201811541524.6A CN201811541524A CN109593510A CN 109593510 A CN109593510 A CN 109593510A CN 201811541524 A CN201811541524 A CN 201811541524A CN 109593510 A CN109593510 A CN 109593510A
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
- C09J183/04—Polysiloxanes
- C09J183/06—Polysiloxanes containing silicon bound to oxygen-containing 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
- C08G77/38—Polysiloxanes modified by chemical after-treatment
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/04—Non-macromolecular additives inorganic
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
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- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
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- Polymers & Plastics (AREA)
- Sealing Material Composition (AREA)
Abstract
The present invention provides a kind of alkoxy end-capped organosilicon polymers, and the polydiorganosiloxanewith for containing vinyl by both ends and the alkoxy silane containing hydrogen-based are reacted under the action of platinum catalyst and obtained.Present invention also provides a kind of preparation methods of alkoxy end-capped organosilicon polymer.Present invention also provides a kind of single-component de-alcoholized organosilicon sealants, including base rubber, crosslinking agent, catalyst and filler, wherein base rubber is organosilicon polymer alkoxy end-capped described in above scheme.Base rubber of the alkoxy end-capped organosilicon polymer provided by the present application as dealcoholized type organosilicon sealant, can make dealcoholized type organosilicon sealant stability preferable, have extraordinary storage period.
Description
Technical field
The present invention relates to sealant technical fields, more particularly to a kind of alkoxy end-capped organosilicon polymer, its preparation
Method and single-component de-alcoholized organosilicon sealant.
Background technique
For traditional single-component de-alcoholized organosilicon sealant mainly with α, alpha, omega-dihydroxy polydimethyl siloxane is base rubber,
With methyltrimethoxysilane, vinyltrimethoxysilane, tetraethoxysilane etc. for crosslinking agent, butyl titanate etc. is to urge
Agent, white carbon black, calcium carbonate etc. are made of filler.Single-component de-alcoholized organosilicon sealant is methanol due to the small molecule of removing
Or ethyl alcohol, corrosion-free to substrate, harm to the human body is also smaller, therefore application is more and more extensive.But with α, the poly- diformazan of alpha, omega-dihydroxy
Radical siloxane be base rubber single-component de-alcoholized organosilicon sealant in process of production, hydroxyl can be acted on titanate catalyst
Viscosity peak is generated, viscosity will rise rapidly in a short time, although the later period can be gradually reduced recovery normally, will lead to life
Produce be difficult to control, viscosity increase after stirring when also result in colloid temperature rise, it is serious will lead to sizing material crosslinking scrap.
Replace hydroxy-end capped dimethyl silicone polymer can be effective using alkoxy end-capped dimethyl silicone polymer
Avoid the generation on viscosity peak.The Chinese patent of Publication No. CN106674524A uses hydroxy-end capped polysiloxanes and has
The silsesquioxane and end capping reaction catalyst of at least three alkoxy react under certain condition obtains alkoxy end-capped poly- two
Methylsiloxane.US3175993 is by hydrogeneous organopolysiloxane and the alkoxy silane containing vinyl in platinum catalyst condition
Under obtained a kind of alkoxy end-capped organopolysiloxane.The Chinese patent of Publication No. CN104479132A passes through dihydroxy
Dimethyl silicone polymer is reacted with dimethyldichlorosilane, and obtained product adds alkoxy silane reaction again, has obtained alcoxyl
The polymer of base sealing end.Therefore it provides a kind of using alkoxy end-capped polydiorganosiloxanewith as the base of organic sealant
Glue is of great significance.
Summary of the invention
Present invention solves the technical problem that be to provide a kind of alkoxy end-capped organosilicon polymer, it is provided by the present application
Base rubber of the organosilicon polymer as dealcoholized type sealant can make sealant have extraordinary storage period, and storage period is up to 2
Year.
In view of this, containing vinyl by both ends this application provides a kind of alkoxy end-capped organosilicon polymer
Polydiorganosiloxanewith and alkoxy silane containing hydrogen-based react under the action of platinum catalyst to be obtained.
Preferably, the organic group in the polydiorganosiloxanewith of vinyl is contained in methyl and phenyl in the both ends
One or two；The both ends contain the polydiorganosiloxanewith of vinyl viscosity be 10mPas~
200000mPas, contents of ethylene are 0.01wt%~5wt%.
Preferably, the alkoxy silane containing hydrogen-based is selected from trimethoxy hydrogen silane, triethoxy hydrogen silane, methyl
In dimethoxy hydrogen silane, methyl diethoxy hydrogen silane, dimethyl methyl oxygroup hydrogen silane and dimethylethyloxy hydrogen silane
It is one or more.
Preferably, the platinum catalyst is selected from the platinum catalyst and divinyl of the alcoholic solution of chloroplatinic acid, tetrahydrofuran coordination
One of platinum catalyst of base tetramethyl siloxanes coordination is a variety of.
Preferably, the additional amount of the platinum catalyst is the polydiorganosiloxanewith and the alkoxy silane total amount
0.5ppm~10ppm.
Preferably, the molal quantity of the vinyl in the polydiorganosiloxanewith and the hydrogen-based in the alkoxy silane
Ratio is 1:(1~1.5).
Present invention also provides a kind of preparation methods of alkoxy end-capped organosilicon polymer, comprising:
The polydiorganosiloxanewith of vinyl and alkoxy silane containing hydrogen-based are contained into platinum catalyst in both ends
Effect is lower to carry out addition reaction, obtains alkoxy end-capped organosilicon polymer.
Preferably, the addition reaction carries out under nitrogen protection, and the temperature of the addition reaction is 40~100 DEG C.
Present invention also provides a kind of single-component de-alcoholized organosilicon sealant, including base rubber, crosslinking agent, catalyst and fill out
Material, which is characterized in that the base rubber is described in organosilicon polymer or above scheme alkoxy end-capped described in above scheme
Preparation method prepared by alkoxy end-capped organosilicon polymer.
This application provides a kind of alkoxy end-capped organosilicon polymer, contain the poly- two organic of vinyl by both ends
Radical siloxane and alkoxy silane containing hydrogen-based react under the action of platinum catalyst to be obtained.Alkoxy envelope provided by the present application
The organosilicon polymer at end by both ends contain the polydiorganosiloxanewith of vinyl and alkoxy silane containing hydrogen-based into
Row addition reaction has obtained a kind of alkoxy end-capped organosilicon polymer, the dealcoholized type which is formulated
Sealant has extraordinary storage period, and storage period was up to 2 years, and the simple process, and no coupling product generates, the alkoxy of synthesis
For the organosilicon polymer of sealing end without post-processing, product is also more stable.
Specific embodiment
For a further understanding of the present invention, the preferred embodiment of the invention is described below with reference to embodiment, still
It should be appreciated that these descriptions are only further explanation the features and advantages of the present invention, rather than to the claims in the present invention
Limitation.
In view of dealcoholized type organosilicon sealant with α, alpha, omega-dihydroxy polydimethyl siloxane is asking for base rubber complex process
Topic, this application provides a kind of alkoxy end-capped organosilicon polymers and preparation method thereof, which, which is used as, has
The base rubber of machine silicone sealant, stability is good, so that organosilicon sealant has extraordinary storage period.Specifically, the present invention is real
It applies example and discloses a kind of alkoxy end-capped organosilicon polymer, the polydiorganosiloxanewith for containing vinyl by both ends and contain
There is the alkoxy silane of hydrogen-based to react under the action of platinum catalyst to obtain.
The structural formula of alkoxy end-capped organosilicon polymer provided by the present application is more specifically:
Wherein, R1For methoxy or ethoxy, y 1,2 or 3, x 0,1 or 2, and x+y=3；
R2Selected from one or both of methyl and phenyl；
N is the integer more than or equal to 1.
The poly- two organic groups silicon of vinyl is contained at above-mentioned alkoxy end-capped organosilicon polymer in order to obtain, the both ends
Organic group in oxygen alkane is selected from one or both of methyl and phenyl；Contain the poly- two organic groups silicon oxygen of vinyl in the both ends
The viscosity of alkane is 10mPas~200000mPas, and contents of ethylene is 0.01wt%~5wt%.In a particular embodiment,
The polydiorganosiloxanewith that vinyl is contained at the both ends is vinyl-terminated silicone fluid.
The alkoxy silane containing hydrogen-based is selected from trimethoxy hydrogen silane, triethoxy hydrogen silane, methyl dimethoxy oxygen
One of base hydrogen silane, methyl diethoxy hydrogen silane, dimethyl methyl oxygroup hydrogen silane and dimethylethyloxy hydrogen silane or
A variety of, structural formula is respectively as follows:
In a particular embodiment, the alkoxy silane containing hydrogen-based is selected from trimethoxy hydrogen silane, methyl dimethoxy oxygen
One of base hydrogen silane, methyl diethoxy hydrogen silane and dimethylethyloxy hydrogen silane.The polydiorganosiloxanewith
In vinyl and the alkoxy silane in hydrogen-based molar ratio be 1:(1~1.5)；In a particular embodiment, described poly-
The molar ratio of the hydrogen-based in vinyl and the alkoxy silane in diorganosiloxane is 1:(1.1~1.3).The platinum
Catalyst is selected from the platinum of the alcoholic solution of chloroplatinic acid, the platinum catalyst of tetrahydrofuran coordination and the coordination of divinyl tetramethyl siloxanes
One of catalyst is a variety of.In this application, the additional amount of the platinum catalyst be the polydiorganosiloxanewith and
0.5ppm~10ppm of the alkoxy silane total amount；In a particular embodiment, the additional amount of the platinum catalyst is total amount
2ppm~8ppm.
Meanwhile present invention also provides the preparation methods of alkoxy end-capped organosilicon polymer, comprising:
The polydiorganosiloxanewith of vinyl and alkoxy silane containing hydrogen-based are contained into platinum catalyst in both ends
Effect is lower to carry out addition reaction, obtains alkoxy end-capped organosilicon polymer.
In the above preparation method, raw material has been carried out detailed description, herein without repeating.
In preparation method, the polydiorganosiloxanewith and the alkoxy silane are sent out under the action of platinum catalyst
Addition reaction is given birth to, the reaction carries out under nitrogen protection, and the temperature of the reaction is 40~100 DEG C.
Present invention also provides a kind of single-component dealcoholization-type organic silicon sealant, including base rubber, crosslinking agent, catalyst and fill out
Material, the base rubber is preparation method institute described in organosilicon polymer or above scheme alkoxy end-capped described in above scheme
The alkoxy end-capped organosilicon polymer of preparation.
In above-mentioned single-component dealcoholization-type organic silicon sealant, the crosslinking agent, catalyst and filler are this field skill
Additive known to art personnel, to this application without particularly limiting.
The present invention by both ends contain vinyl polydiorganosiloxanewith and hydrogeneous alkoxy silane carry out addition it is anti-
It answers, has obtained a kind of alkoxy end-capped organosilicon polymer, the dealcoholized type sealant as made of the polymer formulation has non-
Often good storage period, storage period can achieve 2 years, and the dealcoholized type made using hydroxy-end capped dimethyl silicone polymer as base rubber is close
Sealing storage period is no more than 1 year.The simple process simultaneously, no coupling product generate, the alkoxy end-capped polymerizable organosilicon of synthesis
For object without post-processing, product is also more stable.
It is poly- to alkoxy end-capped organosilicon provided by the invention below with reference to embodiment for a further understanding of the present invention
It closes object to be described in detail, protection scope of the present invention is not limited by the following examples.
Embodiment 1
By the front three of vinyl-terminated silicone fluid (contents of ethylene 1%) and 5.42 mass parts of the 100mPas of 100 mass parts
Oxygroup hydrogen silane (molar ratio of hydrogen and vinyl is 1.2) is added in reaction kettle, is added 5ppm platinum catalyst, is protected in nitrogen
It is warming up to 80 DEG C of reaction 10h under shield, obtains alkoxy end-capped organosilicon polymer, the viscosity of the product is 140mPas.
Embodiment 2
By the three of the vinyl-terminated silicone fluid (contents of ethylene 0.4%) of the 500mPas of 100 mass parts and 2.01 mass parts
Methoxyl group hydrogen silane (molar ratio of hydrogen and vinyl is 1.1) is added in reaction kettle, 2ppm platinum catalyst is added, in nitrogen
It is warming up to 80 DEG C of reactions under protection for 24 hours, obtains alkoxy end-capped organosilicon polymer, which is 730mPas.
Embodiment 3
By the first of vinyl-terminated silicone fluid (contents of ethylene 0.3%) and 1.4 mass parts of the 1000mPas of 100 mass parts
Base dimethoxy hydrogen silane (molar ratio of hydrogen and vinyl is 1.2) is added in reaction kettle, adds 5ppm platinum catalyst,
It is warming up to 60 DEG C of reaction 12h under nitrogen protection, obtains alkoxy end-capped organosilicon polymer, which is
1320mPa·s。
Embodiment 4
By the vinyl-terminated silicone fluid (contents of ethylene 0.19%, phenyl content 10%) of the 10000mPas of 100 mass parts
It is added in reaction kettle with the methyl diethoxy hydrogen silane (molar ratio of hydrogen and vinyl is 1.3) of 1.21 mass parts, then plus
Enter 8ppm platinum catalyst, is warming up to 100 DEG C of reaction 8h under nitrogen protection, obtains alkoxy end-capped organosilicon polymer, it should
Product viscosity is 14960mPas.
Embodiment 5
By the vinyl-terminated silicone fluid (contents of ethylene 0.054%) of the 100000mPas of 100 mass parts and 0.27 mass
The trimethoxy hydrogen silane (molar ratio of hydrogen and vinyl is 1.2) of part is added in reaction kettle, adds 5ppm platinum catalyst,
It is warming up to 80 DEG C of reaction 12h under nitrogen protection, obtains alkoxy end-capped organosilicon polymer, which is
138710mPa·s。
Embodiment 6
By the vinyl-terminated silicone fluid (contents of ethylene 0.04%) of the 165000mPas of 100 mass parts and 0.24 mass parts
Dimethylethyloxy hydrogen silane (molar ratio of hydrogen and vinyl be 1.5) be added in reaction kettle, add 5ppm platinum catalysis
Agent is warming up to 70 DEG C of reaction 16h under nitrogen protection, obtains alkoxy end-capped organosilicon polymer, which is
194240mPa·s。
Embodiment 7
The alkoxy end-capped organosilicon polymer that 100 parts of embodiments 3 are synthesized is added 15 as sealing end base rubber wherein
Part white carbon black, 4 parts of methyltrimethoxysilane, 0.8 part of γ-glycidyl ether oxygen propyl trimethoxy silicane, butyl titanate
It 1.5 parts, is filled in plastic tube after mixing under vacuum conditions, the aging in 70 DEG C of baking ovens after sealing.
Comparative example 1
By the α of 1500mPas, 100 parts of alpha, omega-dihydroxy polydimethyl siloxane, 15 parts of white carbon blacks, methyl trimethoxy is added
4 parts of oxysilane, 0.8 part of γ-glycidyl ether oxygen propyl trimethoxy silicane, 1.5 parts of butyl titanate, under vacuum conditions
It is filled in plastic tube after mixing, the aging in 70 DEG C of baking ovens after sealing.
The ageing properties tables of data of 1 embodiment 7 of table and the sealant of comparative example preparation
| Group | Embodiment 7 | Comparative example 1 |
| Before aging (surface drying time, min) | 8 | 6 |
| 70 DEG C × 7 days (surface drying time, min) | 9 | 8 |
| 70 DEG C × 14 days (surface drying time, min) | 8 | 30 |
| 70 DEG C × 21 days (surface drying time, min) | 10 | Do not solidify |
| 70 DEG C × 28 days (surface drying time, min) | 9 | Do not solidify |
From table 1 it follows that the single-component de-alcoholized organosilicon obtained using alkoxy end-capped polymer as base rubber is close
Sealing aging 28 days at 70 DEG C, without significant change, and with α, alpha, omega-dihydroxy polydimethyl siloxane obtains surface drying time for base rubber
To single-component de-alcoholized organosilicon sealant very big decaying just has occurred in surface drying time after aging 14 days at 70 DEG C.
The above description of the embodiment is only used to help understand the method for the present invention and its core ideas.It should be pointed out that pair
For those skilled in the art, without departing from the principle of the present invention, the present invention can also be carried out
Some improvements and modifications, these improvements and modifications also fall within the scope of protection of the claims of the present invention.
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 readily 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 scope of cause.
Claims (9)
1. a kind of alkoxy end-capped organosilicon polymer, the polydiorganosiloxanewith for containing vinyl by both ends and contain hydrogen
The alkoxy silane of base reacts under the action of platinum catalyst to be obtained.
2. organosilicon polymer according to claim 1, which is characterized in that it is poly- two organic to contain vinyl in the both ends
Organic group in radical siloxane is selected from one or both of methyl and phenyl；Contain poly- two organic group of vinyl in the both ends
The viscosity of siloxanes is 10mPas~200000mPas, and contents of ethylene is 0.01wt%~5wt%.
3. organosilicon polymer according to claim 1, which is characterized in that the alkoxy silane containing hydrogen-based is selected from
Trimethoxy hydrogen silane, triethoxy hydrogen silane, methyl dimethoxy oxygroup hydrogen silane, methyl diethoxy hydrogen silane, dimethyl methyl
One of oxygroup hydrogen silane and dimethylethyloxy hydrogen silane are a variety of.
4. organosilicon polymer according to claim 1, which is characterized in that the alcohol that the platinum catalyst is selected from chloroplatinic acid is molten
One of platinum catalyst of liquid, the platinum catalyst of tetrahydrofuran coordination and the coordination of divinyl tetramethyl siloxanes is a variety of.
5. organosilicon polymer according to claim 1 or 4, which is characterized in that the additional amount of the platinum catalyst is institute
State 0.5ppm~10ppm of polydiorganosiloxanewith and the alkoxy silane total amount.
6. organosilicon polymer according to claim 1, which is characterized in that the ethylene in the polydiorganosiloxanewith
The molal quantity ratio of hydrogen-based in base and the alkoxy silane is 1:(1~1.5).
7. a kind of preparation method of alkoxy end-capped organosilicon polymer, comprising:
The polydiorganosiloxanewith of vinyl and alkoxy silane containing hydrogen-based are contained into the effect of platinum catalyst in both ends
Lower carry out addition reaction, obtains alkoxy end-capped organosilicon polymer.
8. preparation method according to claim 7, which is characterized in that the addition reaction carries out under nitrogen protection, institute
The temperature for stating addition reaction is 40~100 DEG C.
9. a kind of single-component de-alcoholized organosilicon sealant, including base rubber, crosslinking agent, catalyst and filler, which is characterized in that institute
Stating base rubber is any one of the described in any item alkoxy end-capped organosilicon polymers of claim 1~6 or claim 7~8
Alkoxy end-capped organosilicon polymer prepared by the preparation method.
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| CN110878142A (en) * | 2019-11-29 | 2020-03-13 | 湖北新蓝天新材料股份有限公司 | Synthesis method of alkoxy-terminated polysiloxane and alkoxy-terminated polysiloxane |
| CN112143451A (en) * | 2020-10-13 | 2020-12-29 | 广州市高士实业有限公司 | Single-component dealcoholized room temperature vulcanized silicone sealant and preparation method thereof |
| CN112898948A (en) * | 2021-01-20 | 2021-06-04 | 广州机械科学研究院有限公司 | Single-component transparent organosilicon sealant and preparation method and application thereof |
| CN114106335A (en) * | 2021-12-20 | 2022-03-01 | 杭州之江有机硅化工有限公司 | Alkoxy-terminated polysiloxane polymer and preparation method thereof |
| CN115260985A (en) * | 2022-08-26 | 2022-11-01 | 韦尔通(厦门)科技股份有限公司 | Two-component low-viscosity high-heat-conductivity pouring sealant and preparation method and application thereof |
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| CN115991875A (en) * | 2023-02-15 | 2023-04-21 | 杭州之江有机硅化工有限公司 | Titanate catalyst for dealcoholized room temperature vulcanized silicone rubber and preparation method thereof |
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