CN100489014C - Silicane terminated polysulfide rubber and its preparing method - Google Patents
Silicane terminated polysulfide rubber and its preparing method Download PDFInfo
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- CN100489014C CN100489014C CNB2006101239091A CN200610123909A CN100489014C CN 100489014 C CN100489014 C CN 100489014C CN B2006101239091 A CNB2006101239091 A CN B2006101239091A CN 200610123909 A CN200610123909 A CN 200610123909A CN 100489014 C CN100489014 C CN 100489014C
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- silicane
- polysulfide rubber
- terminated polysulfide
- thickol
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Abstract
This invention discloses the polysulphide rubber end-capped with silane and its preparation method. Its structural formula is: (I), R is the bivalent organic groups, including (II); R' is the hydrogen or the alkyl, R'' represents the molecular chain of the polysulfide rubber, X is the alkoxy that can be hydrolyzed, n is 1, 2 or 3; The preparation method is: the polysulphide rubber and the silicon with organic functional groups were mixed according to the mol ratio 1:1.5-2.5, and then reacted at 20-120 DEG C for 1-12h under the condition of the high pure inert gas. The polysulphide rubber end-capped with silane related in this invention was made up of lowpolymers or prepolymers which were nigger-brown or colorless, liquid state or semisolid, and their mean molecular weight is 1,200 ~ 12,000. The invention is characterized in that the technique of production is simple, the process is easy to control, the quality of the product is stable and the application is easy.
Description
Technical field
The present invention relates to thiorubber, be specifically related to a kind of silicane terminated polysulfide rubber that can be used as in fields such as seal gum, tackiness agent, coating and preparation method thereof.
Background technology
Thiorubber is successful at American Studies in nineteen twenty-seven, and its first trade names are Thiokol A.Through secular development, develop three major types type product in succession, comprise liquid polysulphide rubber, solid-state thiorubber and thiorubber emulsion, also develop simultaneously the thiorubber vulcanization system of five major types in succession, metal oxide-type, metal peroxides class, inorganic oxidizer class, organo-peroxide class, organic oxidizing agent class are arranged.
Thiorubber early is applied to the solid propellant bonding of rocket engine, is applied to the sealing of aircraft associated components subsequently, has obtained widespread use in automobile, freight container, building fields such as (as hollow glass production) again.Especially double glazing and freight container market have become the maximum user of thiorubber.Polysulfide sealant is mainly used in adhering and sealing, building joint, oil-bearing structure and the anticorrosion of steel structure sealing etc. of hollow glass production sealing and building industry member.China's polysulfide rubber sealant market year demand is about about 40,000 tons at present.
From the curing mechanism of the existing solidifying agent of thiorubber as can be seen, with the thiorubber is the seal gum that feedstock production forms, usually thiorubber host and attached dose of two components of solidifying agent are mixed by suitable proportion before use, this uses operation to make troubles to it temporarily.Some system curing speed is too slow, delays the time limit of constructing.And polysulfide rubber sealant is not good enough to the cementability of most of non-porous materials such as metal, glass, plastics.
Summary of the invention
The objective of the invention is to overcome the shortcoming of prior art, a kind of good characteristic that had both kept thickol polymer is provided, have easy to usely again, most of nonporosity material surfaces such as metal, glass, plastics are had the good directly silicane terminated polysulfide rubber of cohesive action.
Another object of the present invention is to the preparation method of the described silicane terminated polysulfide rubber of exercise question.
Purpose of the present invention is achieved through the following technical solutions.
A kind of silicane terminated polysulfide rubber, its structural formula is:
R′
(3-n)X
nSi-R-S～R＂～S-R-SiX
nR′
(3-n)
R is the organic group of divalence in the formula, as R=-CH
2-CH
2-CH
2-O-CH
2-CH (OH)-CH
2-
-CH
2-CH
2-CH
2-etc.; R ' is a hydrogen or alkyl, R, and " be to represent the thiorubber molecule segment, X is hydrolyzable alkoxyl group, and n is arbitrary integer of 1～3.
Described silicane terminated polysulfide rubber room temperature is met airborne moisture can hydrolysis form the silanol base, but dehydrated crosslinking, curing between the silanol base, the about 20min～24h of its surface drying time, about 2 hours～7 days of completely solidified time.
When described silicane terminated polysulfide rubber prepared, the molecular-weight average of used thiorubber was one or more the mixture in 1000～10000 the liquid or semi-solid thiorubber; Described silicane terminated polysulfide rubber molecular-weight average is that 1200～11000 liquid or semi-solid dark-brown is to colourless oligopolymer or prepolymer.
The preparation method of silicane terminated polysulfide rubber: the preparation method of described silicane terminated polysulfide rubber, it is characterized in that thiorubber and the silane that the contains organic functional group mixed of 1:1.5～2.5 in molar ratio, under 20～120 ℃ of temperature, inert atmosphere conditions, react 1～12h, make silicane terminated polysulfide rubber.
The described silane that contains organic functional group is γ-glycidoxy propyl group alkoxyl silicone alkanes, its molecular formula as:
Perhaps be isocyanate group propyl group alkoxyl silicone alkanes, its molecular formula is as OCN-R-SiX
nR '
(3-n)R in described two molecular formula is the organic group of divalence, and R ' is a hydrogen or alkyl, and X is hydrolyzable alkoxyl group, and n is 1,2 or 3; It perhaps is the basic front three of chlorine third (first) (second) TMOS; It perhaps is chlorine third (first) ylmethyl diformazan (second) TMOS.
Described temperature of reaction is 20～120 ℃; Described reaction also adds the catalyzer that accounts for total reaction mixture weight 0.05～5%, and described catalyzer is trimethylamine or organic tin catalyzer.
The present invention be with the terminal sulfydryl of thiorubber molecular chain (SH) be converted into and contain an end capped thiorubber of hydrolyzable alkoxysilane group at least, promptly Silante terminated thiorubber, thereby changed the curing mechanism and the solidification process of thiorubber.Like this, not only change the bi-component package form before thiorubber is used, and changed the performance of thiorubber cured article, also further enlarged the Application Areas and the application level of thiorubber.
With respect to prior art, the present invention has following unusual effect:
1, the present invention with the terminal sulfydryl of thiorubber molecular chain (SH) be converted into and contain an end capped thiorubber of hydrolyzable alkoxysilane group at least, i.e. silicane terminated polysulfide rubber, thereby changed the curing mechanism and the solidification process of thiorubber.Thereby the present invention can change present bi-component polysulfide rubber seal glue into single component sulphur rubber seal gum, and is easy to use.
2, regulate with the curing speed of the seal gum of silicane terminated polysulfide rubber preparation easier than existing bi-component polysulfide rubber seal glue.
3, silicane terminated polysulfide rubber is because silane-modified, thermotolerance, hydrophobicity increase, particularly the cohesive action to most of nonporosity material surfaces such as metal, glass, plastics significantly improves, processing before need not these are bondd by sticking material, easy construction, range of application enlarges, and effect strengthens.
Embodiment
In order to understand the present invention better, the present invention is further illustrated below in conjunction with embodiment, but the scope of protection of present invention is not limited to the scope that embodiment represents.
Embodiment 1: the liquid polysulfide rubber 300.0g (0.1mol that will highly dewater, molecular weight 3000) γ-glycidyl ether oxygen propyl trimethoxy silicane with 47.2g (0.2mol) joins in the exsiccant reactor, and stir, add 0.35gDMP-30 again, continue to stir, system generation thermopositive reaction, temperature rises rapidly, and is not enough as temperature, is warming up to 80 ℃ of reaction 3h again, cool then, promptly obtain the end capped thickol polymer of Trimethoxy silane.Reactant and product and airborne moisture react in reaction process, during reinforced or discharging, and whole process all is in to be finished under the high pure nitrogen atmosphere protection.
The end capped thickol polymer of the Trimethoxy silane that obtains is the transparent flowable liquid of light brown, and adopting NDJ-1 type Rotary Viscosimeter to record its viscosity is 82000mPas; Place air surface drying time 4h.
Embodiment 2: the liquid polysulfide rubber 200.0g (0.1mol that will highly dewater, molecular weight 2000) γ-glycidyl ether oxygen propyl trimethoxy silicane with 59.0g (0.25mol) joins in the exsiccant reactor, and stir, add 1.5gDMP-30 again, continue to stir this system generation thermopositive reaction, temperature rises rapidly, the observing response temperature variation is at room temperature reacted 12h then, promptly obtains the end capped thickol polymer of Trimethoxy silane.Reactant and product and airborne moisture react in reaction process, during reinforced or discharging, and whole process all is in to be finished under the high pure nitrogen atmosphere protection.
The end capped thickol polymer of the Trimethoxy silane that obtains is the transparent flowable liquid of light brown, and adopting NDJ-1 type Rotary Viscosimeter to record its viscosity is 75000mPas; Place air surface drying time 2h.
Embodiment 3: the liquid polysulfide rubber 200.0g (0.2mol that will highly dewater, molecular weight is 1000) join in the exsiccant reactor with γ-glycidyl ether oxygen propyl trimethoxy silicane of 59.0g (0.30mol), and stir, add 0.3gDMP-30 again, continue to stir this system generation thermopositive reaction, temperature rises rapidly, not enough as temperature, be warming up to 80 ℃ of reaction 3h again, promptly obtain the end capped thickol polymer of Trimethoxy silane.Reactant and product and airborne moisture react in reaction process, during reinforced or discharging, and whole process all is in to be finished under the high pure nitrogen atmosphere protection.
The end capped thickol polymer of the Trimethoxy silane that obtains is the transparent flowable liquid of light brown, and adopting NDJ-1 type Rotary Viscosimeter to record its viscosity is 68000mPas; Place air surface drying time 5h.
Embodiment 4: the liquid polysulfide rubber 750.0g (0.1mol that will highly dewater, molecular weight is 7500) join in the exsiccant reactor with γ-glycidyl ether oxygen propyl trimethoxy silicane of 70.8g (0.25mol), and stir, add 1.5gDMP-30 again, continue to stir this system generation thermopositive reaction, temperature rises rapidly, the observing response temperature variation, temperature control to 40 ℃ reaction 6h promptly obtains the end capped thickol polymer of Trimethoxy silane then.Reactant and product and airborne moisture react in reaction process, during reinforced or discharging, and whole process all is in to be finished under the high pure nitrogen atmosphere protection.
The end capped thickol polymer of the Trimethoxy silane that obtains is the transparent flowable liquid of light brown, and adopting NDJ-1 type Rotary Viscosimeter to record its viscosity is 98000mPas; Place air surface drying time 4h.
Embodiment 5: the liquid polysulfide rubber 750.0g (0.1mol that will highly dewater, molecular weight is 7500) join in the exsiccant reactor with γ-glycidyl ether oxygen propyl methyl dimethoxysilane of 55.0g (0.25mol), and stir, add 0.85gDMP-30 again, continue to stir this system generation thermopositive reaction, temperature rises rapidly, the observing response temperature variation, temperature control to 40 ℃ reaction 10h promptly obtains the end capped thickol polymer of methyl dimethoxysilane then.Reactant and product and airborne moisture react in reaction process, during reinforced or discharging, and whole process all is in to be finished under the high pure nitrogen atmosphere protection.
The end capped thickol polymer of the methyl dimethoxysilane that obtains is the transparent flowable liquid of light brown, and adopting NDJ-1 type Rotary Viscosimeter to record its viscosity is 89000mPas; Place air surface drying time 12h.
Embodiment 6: the liquid polysulfide rubber 750.0g (0.1mol that will highly dewater; molecular weight is 7500) under the high pure nitrogen atmosphere protection, join in the exsiccant reactor with γ-glycidyl ether oxygen propyl three ethoxy silane of 69.5g (0.25mol); and stir; add 0.84gDMP-30 again; continue to stir; this system generation thermopositive reaction; temperature rises rapidly; the observing response temperature variation; temperature control to 60 ℃ reaction 6h promptly obtains holding the end capped thickol polymer of triethoxyl silane then.Reactant and product and airborne moisture react in reaction process, during reinforced or discharging, and whole process all is in to be finished under the high pure nitrogen atmosphere protection.
Obtaining holding the end capped thickol polymer of triethoxyl silane is the transparent flowable liquid of light brown, and adopting NDJ-1 type Rotary Viscosimeter to record its viscosity is 83000mPas; Place air surface drying time 16h.
Embodiment 7: the liquid polysulfide rubber 200.0g (0.2mol that will highly dewater; molecular weight 1000) the isocyanate group propyl group trimethoxy silane with 102.5g (0.5mol) joins in the exsiccant reactor under the high pure nitrogen atmosphere protection; and stir; add the 0.9g dibutyl tin laurate again; continue to stir, this system generation thermopositive reaction, temperature rises rapidly; slowly be warming up to 120 ℃ of reaction 1h then, promptly obtain the end capped thiorubber of Trimethoxy silane.Reactant and product and airborne moisture react in reaction process, during reinforced or discharging, and whole process all is in to be finished under the high pure nitrogen atmosphere protection.
Obtaining holding the end capped thickol polymer of Trimethoxy silane is the transparent flowable liquid of light brown, and adopting NDJ-1 type Rotary Viscosimeter to record its viscosity is 62000mPas; Place air surface drying time 20min.
Example 8: the liquid polysulfide rubber 750.0g (0.2mol that will highly dewater; molecular weight 7500) the isocyanate group propyl group trimethoxy silane with 75.6g (0.4mol) joins in the exsiccant reactor under the high pure nitrogen atmosphere protection; and stir; add the 2.4g dibutyl tin laurate again; continue to stir, this system generation thermopositive reaction, temperature rises rapidly; slowly be warming up to 40 ℃ of reaction 10h then, promptly obtain the end capped thiorubber of Trimethoxy silane.Reactant and product and airborne moisture react in reaction process, during reinforced or discharging, and whole process all is in to be finished under the high-purity argon gas atmosphere protection.The end capped thickol polymer of the Trimethoxy silane that obtains is the transparent flowable liquid of light brown, and adopting NDJ-1 type Rotary Viscosimeter to record its viscosity is 95000mPas; Place air surface drying time 3h.
Embodiment 9: the liquid polysulfide rubber 300.0g (0.1mol that will highly dewater, molecular weight 3000) r-chloropropyl trimethoxyl silane with 38.9g (0.2mol) joins in the exsiccant reactor, and stir, add the 15.8g pyridine again as catalysis, continue to stir, system generation thermopositive reaction, temperature rises rapidly, not enough as temperature, be warming up to 60 ℃ of reaction 5h again, cool then, filter, remove solid matter, obtain the end capped thickol polymer of flowable Trimethoxy silane of light brown.Reactant and product and airborne moisture react in reaction process, during reinforced or discharging, and whole process all is in to be finished under the high pure nitrogen atmosphere protection.
The end capped thickol polymer of the Trimethoxy silane that obtains is the transparent flowable liquid of light brown, and adopting NDJ-1 type Rotary Viscosimeter to record its viscosity is 75000mPas; Place air surface drying time 4h.
Embodiment 10: the liquid polysulfide rubber 400.0g (0.1mol that will highly dewater, molecular weight 4000) chloropropylmethyldimethoxysilane with 35.7g (0.2mol) joins in the exsiccant reactor, and stir, add the 15.8g pyridine again, continue to stir, system generation thermopositive reaction, temperature rises rapidly, not enough as temperature, be warming up to 80 ℃ of reaction 3h again, cool then, filter, remove solid matter, obtain the end capped thickol polymer of flowable methyl dimethoxysilane of light brown.Reactant and product and airborne moisture react in reaction process, during reinforced or discharging, and whole process all is in to be finished under the high-purity carbon dioxide atmosphere protection.
The end capped thickol polymer of the methyl dimethoxysilane that obtains is the transparent flowable liquid of light brown, and adopting NDJ-1 type Rotary Viscosimeter to record its viscosity is 85000mPas; Place air surface drying time 5h.
By thiorubber is carried out the silanization modification, obtain to contain at least a hydrolyzable alkoxysilane-terminated thiorubber, in a single day its end siloxanes meets airborne moisture, then can hydrolysis generate the silanol base, dewater again between the silanol base and form Si-O-Si key, finally form the solid-state reticulated structure of rubber-like of a complexity, reach the effect of expection.This Silante terminated thiorubber can be widely used as seal gum, binding agent and coating etc., compares with traditional thiorubber, has characteristics such as easy to use, that adhesive power is high, the curing speed regulation range is big, wide adaptability, thermotolerance and hydrophobicity are good.
Claims (9)
1, a kind of silicane terminated polysulfide rubber is characterized in that its structural formula is:
R′
(3-n)X
nSi-R-S～R＂～S-R-SiX
nR′
(3-n)
R is the organic group of divalence in the formula, R=-CH
2-CH
2-CH
2-O-CH
2-CH (OH)-CH
2-, R ' is a hydrogen or alkyl, R, and " be to represent the thiorubber molecule segment, X is hydrolyzable alkoxyl group, and n is 1,2 or 3.
2, silicane terminated polysulfide rubber according to claim 1, it is characterized in that described silicane terminated polysulfide rubber room temperature is met airborne moisture can hydrolysis form silanol base, dehydrated crosslinking, curing between the silanol base, surface drying time is 20min～24h, 2 hours～7 days completely solidified time.
3, silicane terminated polysulfide rubber according to claim 1 is characterized in that, described silicane terminated polysulfide rubber is that molecular-weight average is one or more the mixture in 1000～10000 the liquid or semi-solid thiorubber.
4, silicane terminated polysulfide rubber according to claim 1 is characterized in that, described silicane terminated polysulfide rubber molecular-weight average is that 1200～11000 liquid or semi-solid dark-brown is to colourless oligopolymer or prepolymer.
5, silicane terminated polysulfide rubber according to claim 1, it is characterized in that described silicane terminated polysulfide rubber is the end capped thickol polymer of Trimethoxy silane, the end capped thickol polymer of triethoxyl silane, the end capped thickol polymer of methyl dimethoxysilane, the end capped thickol polymer of methyldiethoxysilane, the end capped thickol polymer of methoxyl group dimethylsilane or the end capped thickol polymer of oxyethyl group dimethylsilane.
6, the preparation method of the described silicane terminated polysulfide rubber of claim 1, it is characterized in that thiorubber and the silane that the contains organic functional group mixed of 1:1.5～2.5 in molar ratio, under 20～120 ℃ of temperature, inert atmosphere conditions, react 1～12h, make silicane terminated polysulfide rubber.
7, according to the preparation method of the described silicane terminated polysulfide rubber of claim 6, the described silane that contains organic functional group is γ-glycidyl ether oxygen propyl alkoxyl silicone alkanes, and its molecular formula is
Perhaps be isocyanate group propyl group alkoxyl silicone alkanes, its molecular formula is as OCN-R-SiX
nR '
(3-n)R in described two molecular formula is the organic group of divalence, and R ' is a hydrogen or alkyl, and X is hydrolyzable alkoxyl group, and n is 1,2 or 3.
8, according to the preparation method of the described middle silicane terminated polysulfide rubber of claim 6, it is characterized in that described reaction also adds the catalyzer that accounts for total reaction mixture weight 0.05～5%, described catalyzer is trimethylamine or organic tin catalyzer.
9, according to the preparation method of the described middle silicane terminated polysulfide rubber of claim 6, it is characterized in that described inert atmosphere is high pure nitrogen atmosphere, high-purity argon gas atmosphere or high-purity carbon dioxide atmosphere.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2006101239091A CN100489014C (en) | 2006-11-30 | 2006-11-30 | Silicane terminated polysulfide rubber and its preparing method |
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|---|---|---|---|
| CNB2006101239091A CN100489014C (en) | 2006-11-30 | 2006-11-30 | Silicane terminated polysulfide rubber and its preparing method |
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|---|---|
| CN1978489A CN1978489A (en) | 2007-06-13 |
| CN100489014C true CN100489014C (en) | 2009-05-20 |
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Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102277125B (en) * | 2011-08-31 | 2013-09-18 | 辽宁双强塑胶科技开发有限公司 | Flame-retardant polysulfide sealant and preparation method thereof |
| CN103059800B (en) * | 2012-12-26 | 2014-11-12 | 华南理工大学 | Silane-terminiated polysulfide rubber sealant and preparation method thereof |
| CN114621442A (en) * | 2022-05-05 | 2022-06-14 | 郑州恩德富新材料科技有限公司 | Novel silane-terminated polysulfide rubber and synthesis method thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1112980A (en) * | 1994-02-01 | 1995-12-06 | 明治制果株式会社 | Dye adhesion preventing agent and method for treating previously dyed fibers or textile goods using the agent |
| US20050272852A1 (en) * | 2004-06-02 | 2005-12-08 | Sandstrom Paul H | Natural rubber-rich composition and tire with tread thereof |
-
2006
- 2006-11-30 CN CNB2006101239091A patent/CN100489014C/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1112980A (en) * | 1994-02-01 | 1995-12-06 | 明治制果株式会社 | Dye adhesion preventing agent and method for treating previously dyed fibers or textile goods using the agent |
| US20050272852A1 (en) * | 2004-06-02 | 2005-12-08 | Sandstrom Paul H | Natural rubber-rich composition and tire with tread thereof |
Non-Patent Citations (2)
| Title |
|---|
| 有机硅改性密封剂研究进展. 马仁杰，王自新，魏克超，王玲.化学推进剂与高分子材料，第3卷第1期. 2005 |
| 有机硅改性密封剂研究进展. 马仁杰，王自新，魏克超，王玲.化学推进剂与高分子材料，第3卷第1期. 2005 * |
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Assignee: Guangzhou Xinzhan Silicone Co., Ltd. Assignor: South China University of Technology Contract record no.: 2010440001532 Denomination of invention: Silicane terminated polysulfide rubber, and its preparing method Granted publication date: 20090520 License type: Exclusive License Open date: 20070613 Record date: 20101221 |
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