CN105368063A - Stably stored single-component dealcoholized room temperature vulcanized silicone rubber - Google Patents
Stably stored single-component dealcoholized room temperature vulcanized silicone rubber Download PDFInfo
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- CN105368063A CN105368063A CN201510867263.7A CN201510867263A CN105368063A CN 105368063 A CN105368063 A CN 105368063A CN 201510867263 A CN201510867263 A CN 201510867263A CN 105368063 A CN105368063 A CN 105368063A
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Abstract
The invention provides stably stored single-component dealcoholized room temperature vulcanized silicone rubber. The rubber comprises alkoxyalkyl-terminated polysiloxane, a plasticizer, gas phase fumed silica, a hydroxyl scavenger, a crosslinking agent, a silane coupling agent and a catalyst. By using a silicon-containing heterocyclic compound as the hydroxyl scavenger to scavenge hydroxyl and free alcohol in the dealcoholized room temperature vulcanized silicone rubber, the storage period of the single-component dealcoholized silicone rubber can be remarkably improved, and the silicon nitrogen heterocyclic compound is good in compatibility with an alcohol type silicone sealant, so that no other side effects are available and meanwhile, the adhesion of the base material can be effectively improved.
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 scavenging agent, belong to organosilicon new material technology field.
Background technology
Discharge alcohol in single-component dealcoholization-type room temperature vulcanized silicone rubber sulfidation, compared to depickling type and ketoxime removing type, there is environmental protection, free from corrosion advantage.Electronic apparatus and building trade can be widely used in, the trend that the sizing agent alcohol type seal gum as a kind of environmental protection will be future market application.But its ubiquity problem namely, its curability declines gradually along with the prolongation of period of storage not even sulfuration, major cause be free alcohol in dealcoholysis alcohol type room temperature vulcanized silicone rubber under the existence of organo-metallic catalyst with polysiloxane generation equilibration reaction, form (the CH without crosslinked function
3o) (CH
3)
2siO
1/2end group.
For the modal method storage period of improving dealcoholized type room temperature vulcanized silicone rubber adds hydroxyl scavenging agent exactly, remove the hydroxyl in dealcoholized type room temperature vulcanized silicone rubber and free alcohol.Wherein modal is add hexamethyldisilazane class as hydroxyl scavenging agent, but in the process of preparation, hexamethyldisilazane can act on and discharge ammonia, causes corrosion to materials such as copper, affects the production curing performance of dealcoholized type room temperature vulcanized silicone rubber simultaneously.
Patent US4489191 is added in dealcoholized type room temperature vulcanized silicone rubber using triethoxy hydrogen silane as hydroxyl scavenging agent, due to can hydrogen be discharged in preparation process, therefore also need to add ethylenic unsaturation hydro carbons as hydrogen scavenging agent, and unsaturated olefin add the xanthochromia easily causing dealcoholized type room temperature vulcanized rubber.
Summary of the invention
In view of this, the technical problem to be solved in the present invention novel dealcoholized type room temperature vulcanized silicone rubber that is to provide a kind of storage time long and a kind of hydroxyl scavenging agent.The single-component dealcoholization-type room temperature vulcanized silicone rubber that the invention provides shelf-stable comprises following component:
Wherein said hydroxyl scavenging agent is silicon heterocyclic compound.
Described silicon heterocyclic compound is preferably silicon nitrogen heterocyclic.
Described silicon heterocyclic compound is preferably nitrogen heterocyclic penta silane, and structural formula is as follows:
Wherein R is C1 ~ C10 alkyl, is preferably methyl or ethyl.
The polysiloxane of described alkoxyalkyl end-blocking is preferably terminal methyl group dimethoxy polydimethylsiloxane, and its structural formula is:
Wherein n is the integer of 100 ~ 1500, and when 25 DEG C, viscosity is 0.8 ~ 150Pas.
Described softening agent is inert polysiloxane, and be preferably the polydimethylsiloxane of methyl blocking, when 25 DEG C, kinematic viscosity is 0.1 ~ 20Pas.
Described gas-phase silica comprise in hydrophilic gas-phase silica, hydrophobic type gas-phase silica any one, its specific surface area is 100 ~ 300m
2/ g.
Described linking agent is one or more in methyltrimethoxy silane, Union carbide A-162, vinyltrimethoxy silane, vinyltriethoxysilane, phenyltrimethoxysila,e, phenyl triethoxysilane.
Described catalyzer be dibutyl tin dilaurate, dibutyl tin acetate, dioctyl tin cinnamic acid tin, two (dodecyl sulphur) dibutyl tin, stannous octoate, two fourth methyl ethyl diketone tin, dibutyl methyl aceto acetate 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, under acid catalyst effect, carries out intramolecular cyclization reaction, the reaction times is 5-20h, be preferably 8-10h, fractionate out by-product alcohol in reaction process, stopped reaction when not regeneration alcohol, and distillation obtains target product simultaneously; Described silane compound is shown below:
Wherein n=2 ~ 4, n is integer, and n is preferably 3; R is C1 ~ C10 alkyl, is preferably methyl or ethyl.
Described acid is the one in trifluoromethanesulfonic acid, fluosulfonic acid, Phenylsulfonic acid, methylsulfonic acid, is preferably trifluoromethanesulfonic acid.
Wherein the mol ratio of acid catalyst and silane compound is 1: 100 ~ 10000, is preferably 1: 200 ~ 2000.
Compared to prior art, the invention provides single-component dealcoholization-type rubber composition and have the following advantages:
1) the present invention to adopt containing silicon heterocyclic compound as hydroxyl scavenging agent, significantly can improve single-component dealcoholization-type silicon rubber storage period;
2) the siliceous nitrogen heterocyclic adopted and alcohol type silicone sealant Miscibility good, even effectively substrate bonding can be improved without other negative impacts, under reason is hydroxyl scavenging agent room temperature, it just can react with free alcohol in system, generate aminosilane reaction equation to be shown below, and aminosilane a kind of tackifier that dealcoholized type room temperature vulcanized silicone rubber is conventional just.
Accompanying drawing explanation
Fig. 1 is nitrogen heterocyclic penta silane prepared by embodiment 1.
Embodiment
Below by embodiment, concrete description is done to this aspect; what be necessary to herein means out is that following examples are only used to further illustrate the present invention; can not be interpreted as limiting the scope of the invention, the person skilled in the art in this field can make nonessential improvement and adjustment according to the present invention.
Embodiment 1
Get 200g aminopropyl trimethoxysilane in flask, start stirring and be warming up to and occur reflux state, be added dropwise to 0.2g trifluoromethanesulfonic acid, start clock reaction 8h, use condenser to collect by-product carbinol simultaneously.React complete, distill under vacuum tightness 0.6KPa, according to nuclear-magnetism
1hNMR analyzes, and obtains object product 178g, yield 89% at 100-105 DEG C of cut.Target product structural formula is as follows:
1HNMR(CDCl
3)：0.62(t，2H)，1.24(m，H)，1.60(m，2H)，2.7(t，2H)，3.56(s，6H)。
Embodiment 2
Get 200g aminopropyl triethoxysilane in flask, start stirring and be warming up to and occur reflux state, be added dropwise to 0.2g trifluoromethanesulfonic acid, start clock reaction 12h, fractionate out coproduct ethanol simultaneously.React complete, distill under vacuum tightness 0.6KPa, according to nuclear-magnetism
1hNMR analyzes, and obtains object product 170g, yield 85% at 105-115 DEG C of cut.Target product structural formula is as follows:
1HNMR(CDCl
3)：0.62(t，2H)，1.2(m，H)，1.68(m，2H)，2.7(t，2H)，3.75(m，10H)。
Embodiment 3
Get 200g aminopropyl tripropoxy silane in flask, start stirring and be warming up to and occur reflux state, be added dropwise to 0.2g Phenylsulfonic acid, start clock reaction 15h, use condenser to collect by product propyl alcohol simultaneously.React complete, distill under vacuum tightness 0.6KPa, according to nuclear-magnetism
1hNMR analyzes, and obtains object product 164g, yield 82% at 109-120 DEG C of cut.Target product structural formula is as follows:
1HNMR(CDCl
3)：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 polydimethylsiloxanes; Add the polydimethylsiloxane 20 parts of 0.3Pas methyl blocking, the hydrophobic gas-phase silica 10 parts of specific surface area 150 stirs 30min under vacuum tightness > 0.09Mpa condition; Then the material of methyltrimethoxy silane 5 parts, aminopropyl triethoxysilane 1 part, 1 part of embodiment 1 synthesis is added, 0.2 part, dibutyl ethyl-diacetyl-acetate tin, 30min clock is stirred under vacuum tightness > 0.09Mpa condition, make the transparent alcohol type silicone sealant compositions of single-component to load in sealed rubber pipe, product performance test result refers to table 1
Embodiment 5
100 parts of 20Pas terminal methyl group dimethoxy polydimethylsiloxanes; Add the polydimethylsiloxane 20 parts of 0.3Pas methyl blocking, the hydrophobic gas-phase silica 10 parts of specific surface area 150 stirs 30min under vacuum tightness > 0.09Mpa condition; Then the material of methyltrimethoxy silane 5 parts, aminopropyl triethoxysilane 1 part, 1 part of 2-in-1 one-tenth of embodiment is added, 0.2 part, dibutyl ethyl-diacetyl-acetate tin, 30min clock is stirred under vacuum tightness > 0.09Mpa condition, make the transparent alcohol type silicone sealant compositions of single-component to load in sealed rubber pipe, product performance test result refers to table 1
Embodiment 6
100 parts of 20Pas terminal methyl group dimethoxy polydimethylsiloxanes; Add the polydimethylsiloxane 20 parts of 0.3Pas methyl blocking, the hydrophobic gas-phase silica 10 parts of specific surface area 150 stirs 30min under vacuum tightness > 0.09Mpa condition; Then the material of methyltrimethoxy silane 5 parts, aminopropyl triethoxysilane 1 part, 1 part of embodiment 3 synthesis is added, 0.2 part, dibutyl ethyl-diacetyl-acetate tin, 30min clock is stirred under vacuum tightness > 0.09Mpa condition, make the transparent alcohol type silicone sealant compositions of single-component to load in sealed rubber pipe, product performance test result refers to table 1
Comparative example 1
100 parts of 20pas terminal methyl group dimethoxy polydimethylsiloxanes; Add the polydimethylsiloxane 20 parts of 0.3Pas methyl blocking, the hydrophobic gas-phase silica 10 parts of specific surface area 150 stirs 30min under vacuum tightness > 0.09Mpa condition; Then methyltrimethoxy silane 5 parts, aminopropyl triethoxysilane 1 part, 1 part of hexamethyldisilazane is added, 0.2 part, dibutyl ethyl-diacetyl-acetate tin stirs 30min clock under vacuum tightness > 0.09Mpa condition, make the transparent alcohol type silicone sealant compositions of single-component to load in sealed rubber pipe, product performance test result refers to table 1
Comparative example 2
100 parts of 20pas terminal methyl group dimethoxy polydimethylsiloxanes; Add the polydimethylsiloxane 20 parts of 0.3Pas methyl blocking, the hydrophobic gas-phase silica 10 parts of specific surface area 150 stirs 30min under vacuum tightness > 0.09Mpa condition; Then methyltrimethoxy silane 5 parts, aminopropyl triethoxysilane 1 part, 1 part of triethoxy hydrogen silicon is added, 0.2 part, dibutyl ethyl-diacetyl-acetate tin, 30min clock is stirred under vacuum tightness > 0.09Mpa condition, make the transparent alcohol type silicone sealant compositions of single-component to load in sealed rubber pipe, product performance test result refers to table 1
Comparative example 3
100 parts of 20pas terminal methyl group dimethoxy polydimethylsiloxanes; Add the polydimethylsiloxane 20 parts of 0.3Pas methyl blocking, the hydrophobic gas-phase silica 10 parts of specific surface area 150 stirs 30min under vacuum tightness > 0.09Mpa condition; Then methyltrimethoxy silane 5 parts, aminopropyl triethoxysilane 1 part, 1 part of isocyanate group propyl trimethoxy silicane is added, 0.2 part, dibutyl ethyl-diacetyl-acetate tin, 30min is stirred under vacuum tightness > 0.09Mpa condition, make the transparent alcohol type silicone sealant compositions of single-component to load in sealed rubber pipe, product performance test result refers to table 1
Testing method:
The single-component transparent dealcoholysis alcohol type room temperature vulcanized silicone rubber obtained is carried out performance test by the present invention, and detailed process is as follows:
1) employing standard No. is the surface drying time of national standard to the transparent dealcoholized type room temperature vulcanized silicone rubber of the single-component obtained, the test of aluminum oxide base material I-shaped sheet cementability of GB/T13477-2002;
2) be that the hardness of national standard to the transparent dealcoholized type room temperature vulcanized silicone rubber of the single-component obtained of GB/T531.1-2008 is tested according to standard No.;
3) transparent for the single-component of preparation dealcoholized type room temperature vulcanized silicone rubber is carried out in sebific duct respectively 50 DEG C of surroundings, 70 DEG C one week, room temperature condition stores and detects single-component dealcoholization-type room temperature vulcanized silicone rubber situation storage period under three kinds of conditions in 1 year.
Table 1
Performance data according to upper table test can be found out, the single-component transparent alcohol type silicone seal initial performance using different hydroxyl scavenging agents to prepare, comprises surface drying time, hardness is basically identical.But can be found out by 50 DEG C, 70 DEG C accelerated aging tests and room temperature weather aging result, the performance of the hydroxyl scavenging agent glue example 4-6 adopting this patent to prepare is substantially unchanged, and adopting the comparison example of other hydroxyl scavenging agents such as silazane along with longer storage duration, surface drying time significant prolongation, hardness obviously reduce even cannot solidify.Illustrate thus, hydroxyl scavenging agent provided by the invention is to the package stability Be very effective improving single-component dealcoholization-type room temperature vulcanized silicone rubber.
Claims (10)
1. a novel single-component dealcoholization-type room temperature vulcanized silicone rubber, is characterized in that, comprises following component:
Described hydroxyl scavenging agent is silicon heterocyclic compound.
2. novel single-component dealcoholization-type room temperature vulcanized silicone rubber as claimed in claim 1, it is characterized in that, described silicon heterocyclic compound is preferably silicon nitrogen heterocyclic.
3. novel single-component dealcoholization-type room temperature vulcanized silicone rubber as claimed in claim 2, is characterized in that, described silicon heterocyclic compound is preferably nitrogen heterocyclic penta silane, and structural formula is as follows:
Wherein R is C1 ~ C10 alkyl, is preferably methyl or ethyl.
4. novel single-component dealcoholization-type room temperature vulcanized silicone rubber as claimed in claim 1, is characterized in that, the polysiloxane of described alkoxyalkyl end-blocking is preferably terminal methyl group dimethoxy polydimethylsiloxane, and its structural formula is:
Wherein n is the integer of 100 ~ 1500, and when 25 DEG C, viscosity is 0.8 ~ 150Pas.
5. novel single-component dealcoholization-type room temperature vulcanized silicone rubber as claimed in claim 1, is characterized in that, described softening agent is inert polysiloxane.
6. novel single-component dealcoholization-type room temperature vulcanized silicone rubber as claimed in claim 1, it is characterized in that, described linking agent is one or more in methyltrimethoxy silane, Union carbide A-162, vinyltrimethoxy silane, vinyltriethoxysilane, phenyltrimethoxysila,e, phenyl triethoxysilane.
7. novel single-component dealcoholization-type room temperature vulcanized silicone rubber as claimed in claim 1, it is characterized in that, described catalyzer be dibutyl tin dilaurate, dibutyl tin acetate, dioctyl tin cinnamic acid tin, two (dodecyl sulphur) dibutyl tin, stannous octoate, two fourth methyl ethyl diketone tin, dibutyl methyl aceto acetate tin one or more.
8. the preparation method of the silicon heterocyclic compound as described in right 1, comprising:
Silane compound is heated to reflux state, under acid catalyst effect, carries out intramolecular cyclization reaction, the reaction times is 5-20h, fractionates out by-product alcohol in reaction process simultaneously, stopped reaction when not regeneration alcohol, and distillation obtains target product; Described silane compound is shown below:
Wherein n=2 ~ 4, n is integer, and n is preferably 3.
9. preparation method as claimed in claim 8, it is characterized in that, described acid is the one in trifluoromethanesulfonic acid, fluosulfonic acid, Phenylsulfonic acid, methylsulfonic acid.
10. preparation method as claimed in claim 8, it is characterized in that, described acid catalyst and the mol ratio of silane compound are 1: 100 ~ 10000, are preferably 1: 200 ~ 2000.
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| CN106047273A (en) * | 2016-05-15 | 2016-10-26 | 浙江新安化工集团股份有限公司 | Novel stabilizing agent and application thereof in dealcoholized RTV-1 silicone rubber composition |
| CN106190012A (en) * | 2016-08-08 | 2016-12-07 | 广州机械科学研究院有限公司 | A kind of transparent high intensity Self-leveling piptonychia alcohol type single-component organic silicon glue and preparation method thereof |
| CN109280533A (en) * | 2018-08-09 | 2019-01-29 | 广州市高士实业有限公司 | Single-component dealcoholization-type transparent silicone sealant and its preparation method and application |
| CN109762511A (en) * | 2018-12-25 | 2019-05-17 | 广州市高士实业有限公司 | A kind of single-component dealcoholization-type room temperature sealing silicone sulfide glue and preparation method thereof |
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| CN111378402A (en) * | 2020-04-10 | 2020-07-07 | 山东宝龙达实业集团有限公司 | Preparation method and application of hydroxyl scavenging agent |
| CN111592651A (en) * | 2019-12-31 | 2020-08-28 | 杭州师范大学 | Low-hydroxyl hydrogen-containing vinyl phenyl organic silicon resin and preparation method thereof |
| CN114174454A (en) * | 2019-07-17 | 2022-03-11 | 信越化学工业株式会社 | Ultraviolet-curable organopolysiloxane composition |
| WO2024040689A1 (en) * | 2022-08-25 | 2024-02-29 | 江西天永诚高分子材料有限公司 | Dealcoholization-type room temperature vulcanized silicone rubber and preparation method therefor |
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| CN109762511A (en) * | 2018-12-25 | 2019-05-17 | 广州市高士实业有限公司 | A kind of single-component dealcoholization-type room temperature sealing silicone sulfide glue and preparation method thereof |
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| CN110003842A (en) * | 2019-01-24 | 2019-07-12 | 烟台德邦科技有限公司 | A kind of single-component dealcoholization-type room-temperature vulcanized organic polyorganosiloxane composition |
| CN110003842B (en) * | 2019-01-24 | 2021-05-04 | 烟台德邦科技股份有限公司 | Single-component dealcoholized room temperature vulcanized organopolysiloxane composition |
| CN114174454A (en) * | 2019-07-17 | 2022-03-11 | 信越化学工业株式会社 | Ultraviolet-curable organopolysiloxane composition |
| CN110734738A (en) * | 2019-10-10 | 2020-01-31 | 烟台德邦科技有限公司 | organosilicon three-proofing adhesive and preparation process thereof |
| CN111592651A (en) * | 2019-12-31 | 2020-08-28 | 杭州师范大学 | Low-hydroxyl hydrogen-containing vinyl phenyl organic silicon resin and preparation method thereof |
| CN111592651B (en) * | 2019-12-31 | 2022-02-01 | 杭州师范大学 | Low-hydroxyl hydrogen-containing vinyl phenyl organic silicon resin and preparation method thereof |
| CN111378402A (en) * | 2020-04-10 | 2020-07-07 | 山东宝龙达实业集团有限公司 | Preparation method and application of hydroxyl scavenging agent |
| CN111378402B (en) * | 2020-04-10 | 2021-01-12 | 山东宝龙达实业集团有限公司 | Preparation method and application of hydroxyl scavenging agent |
| WO2024040689A1 (en) * | 2022-08-25 | 2024-02-29 | 江西天永诚高分子材料有限公司 | Dealcoholization-type room temperature vulcanized silicone rubber and preparation method therefor |
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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 |