CN111253908A - Preparation method of dealcoholized sealant - Google Patents
Preparation method of dealcoholized sealant Download PDFInfo
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- CN111253908A CN111253908A CN202010112957.0A CN202010112957A CN111253908A CN 111253908 A CN111253908 A CN 111253908A CN 202010112957 A CN202010112957 A CN 202010112957A CN 111253908 A CN111253908 A CN 111253908A
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- sealant
- dealcoholized
- reacting
- preparation
- coupling agent
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- 239000000565 sealant Substances 0.000 title claims abstract description 51
- 238000002360 preparation method Methods 0.000 title claims abstract description 24
- UMXXGDJOCQSQBV-UHFFFAOYSA-N n-ethyl-n-(triethoxysilylmethyl)ethanamine Chemical compound CCO[Si](OCC)(OCC)CN(CC)CC UMXXGDJOCQSQBV-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000006087 Silane Coupling Agent Substances 0.000 claims abstract description 13
- 239000000463 material Substances 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims description 12
- IXQMGECVDWVOFK-UHFFFAOYSA-N dichloromethyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C(Cl)Cl IXQMGECVDWVOFK-UHFFFAOYSA-N 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 229920001296 polysiloxane Polymers 0.000 claims description 7
- 239000004205 dimethyl polysiloxane Substances 0.000 claims description 4
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims description 4
- -1 polydimethylsiloxane Polymers 0.000 claims description 4
- SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical compound C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 claims description 2
- KOVKEDGZABFDPF-UHFFFAOYSA-N n-(triethoxysilylmethyl)aniline Chemical compound CCO[Si](OCC)(OCC)CNC1=CC=CC=C1 KOVKEDGZABFDPF-UHFFFAOYSA-N 0.000 claims 1
- VNBLTKHUCJLFSB-UHFFFAOYSA-N n-(trimethoxysilylmethyl)aniline Chemical compound CO[Si](OC)(OC)CNC1=CC=CC=C1 VNBLTKHUCJLFSB-UHFFFAOYSA-N 0.000 claims 1
- 239000003292 glue Substances 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 6
- 230000000694 effects Effects 0.000 description 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- KRJRKEPWQOASJN-UHFFFAOYSA-N aniline;trimethoxy(methyl)silane Chemical compound NC1=CC=CC=C1.CO[Si](C)(OC)OC KRJRKEPWQOASJN-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BTXFTCVNWMNXKH-UHFFFAOYSA-N NC1=CC=CC=C1.CCO[Si](C)(OCC)OCC Chemical compound NC1=CC=CC=C1.CCO[Si](C)(OCC)OCC BTXFTCVNWMNXKH-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- 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
- C09J183/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
-
- 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
- C08G77/06—Preparatory processes
-
- 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
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/24—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen halogen-containing groups
-
- 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
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Sealing Material Composition (AREA)
Abstract
The invention particularly relates to a preparation method of dealcoholized sealant, which comprises the following steps of (1) uniformly mixing diethylaminomethyl triethoxysilane and α silane coupling agent, reacting to obtain a pretreatment product, and (2) mixing the pretreatment product and a base material, vacuumizing and reacting to obtain the dealcoholized sealant.
Description
Technical Field
The invention particularly relates to a preparation method of dealcoholized sealant.
Background
The types of the common organosilicon sealant mainly comprise dealkalized type, dealcoholized type and dealkylated oxime type, wherein the dealcoholized sealant is neutral and has the advantages of cleanness, no toxicity, no corrosiveness, lower cost price, good bonding performance to materials such as glass, metal and the like.
However, most dealcoholization type organosilicon single-component sealants in the market at present adopt hydroxyl-terminated organosilicon, such as glue 107 (α, omega-dihydroxy polydimethylsiloxane) as a raw material, and the organosilicon sealant prepared by taking the hydroxyl-terminated organosilicon as the raw material has high activity, can generate viscosity peak in the process of producing the dealcoholization type organosilicon sealant, influences the yield and the performance of products, brings troubles to production and even has the risk of product curing in a reaction kettle.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to provide a preparation method of a dealcoholized sealant. By the preparation method, the viscosity peak is eliminated in the preparation process of the dealcoholized sealant, and the quality and the production efficiency of the product are effectively improved.
The invention adopts the following technical scheme.
The preparation method of the dealcoholized sealant comprises the following steps:
(1) uniformly mixing diethylaminomethyl triethoxysilane and α silane coupling agent, and reacting to obtain a pretreated product;
(2) and mixing the pretreated product and the base material, vacuumizing and reacting to obtain the dealcoholized sealant.
Preferably, the mass ratio of the diethylaminomethyl triethoxysilane to the α silane coupling agent is 1-5: 1-5.
Preferably, the α silane coupling agent has the chemical formula Xa-CH3-aSi(OR)3Wherein a is more than or equal to 1 and less than or equal to 3, and X is NH2-、Cl-、HS-、CH2＝C(CH3) COO-and CH2OCHCH2O-、C6H5NH-and NH2(CH2)6One or more of NH-; r is CH3-and C2H5-one or both of.
Preferably, the α silane coupling agent is one or more of dichloromethyl triethoxysilane, aniline methyl trimethoxysilane, aniline methyl triethoxysilane and hexamethylene diamine methyl triethoxysilane.
Further preferably, the α silane coupling agent is dichloromethyltriethoxysilane.
In the invention, the diethylaminomethyl triethoxysilane is positioned on the α carbon, and the electronic effect of a functional group is more easily transferred to a silicon atom, so that an alkoxy group RO-directly connected with the silicon atom becomes active and is easy to generate chemical reaction, and therefore, the silicon rubber can play the role of a coupling agent and a similar catalyst at room temperature, when the diethylaminomethyl triethoxysilane contacts with hydroxyl on the surface of a base material, the chemical reaction can be generated, so that the viscosity of a system is rapidly increased, namely, a viscosity peak is generated, wherein the viscosity peak refers to the viscosity peak in the first few minutes of the reaction, in order to avoid the phenomenon, the diethylaminomethyl triethoxysilane and the α silane coupling agent are pretreated, α silane coupling agent can consume a part of active amino groups, and the reaction of the diethylaminomethyl triethoxysilane and the base material is reduced, so that the viscosity peak is reduced or eliminated.
Preferably, the mass ratio of the pretreatment product to the base stock is 1: (5-10).
Preferably, the binder is a hydroxyl terminated silicone.
Further preferably, the hydroxyl-terminated silicone is α, omega-dihydroxy polydimethylsiloxane.
In the present invention, the base material may be selected from hydroxyl terminated silicones or base materials prepared from hydroxyl terminated silicones, such as a 107 gum prepared from α, omega-dihydroxy polydimethylsiloxane, having a viscosity of 1000cps (25 ℃, 50% RH).
Other binders prepared from hydroxyl terminated silicones can also be selected by those skilled in the art.
Preferably, step (1) is carried out at 10-100 ℃ for 0.5-24 hours.
Preferably, the step (2) is carried out for 1 to 2 hours under the vacuum degree of-0.08 to 0. lMPa.
The dealcoholized sealant prepared by the method.
The invention has the beneficial effects that:
(1) the invention reduces the activity of the diethylamino methyl triethoxysilane by reacting the diethylamino methyl triethoxysilane with the α silane coupling agent for pretreatment, thereby achieving the effects of shielding part of active groups and reducing viscosity peak;
(2) the dealcoholized sealant does not generate a viscosity peak or only generates a slight viscosity peak in the preparation process of the dealcoholized sealant, can effectively improve the quality and the production efficiency of products, has simple and convenient preparation method process and high efficiency, and has a prospect in the preparation and the production of the sealant.
Detailed Description
The present invention will be described in detail below with reference to specific embodiments.
Example 1
The preparation method of the dealcoholized sealant comprises the following steps:
(1) uniformly mixing 10g of diethylaminomethyl triethoxysilane and 10g of dichloromethyl triethoxysilane, and reacting at 25 ℃ for 50 minutes to obtain a pretreated product;
(2) and (3) mixing 20g of the pretreatment product with 100g of 107 glue with the viscosity of 1000cps (25 ℃, 50% RH), vacuumizing to the vacuum degree of 0.lMPa, and reacting for 1 hour to obtain the dealcoholized sealant.
Example 2
The preparation method of the dealcoholized sealant comprises the following steps:
(1) uniformly mixing 10g of diethylaminomethyl triethoxysilane and 5g of dichloromethyl triethoxy silicon, and reacting at 25 ℃ for 50 minutes to obtain a pretreatment product;
(2) mixing 15g of the pretreatment product with 100g of 107 glue with the viscosity of 1000cps (25 ℃, 50% RH), vacuumizing to the vacuum degree of 0.lMPa, and reacting for 2 hours to obtain the dealcoholized sealant.
Example 3
The preparation method of the dealcoholized sealant comprises the following steps:
(1) uniformly mixing 10g of diethylaminomethyl triethoxysilane and 5g of dichloromethyl triethoxy silicon, and reacting at 80 ℃ for 50 minutes to obtain a pretreatment product;
(2) mixing 15g of the pretreatment product with 100g of 107 glue with the viscosity of 1000cps (25 ℃, 50% RH), vacuumizing to the vacuum degree of 0.lMPa, and reacting for 1 hour to obtain the dealcoholized sealant.
Example 4
The preparation method of the dealcoholized sealant comprises the following steps:
(1) uniformly mixing 10g of diethylaminomethyl triethoxysilane and 10g of dichloromethyl triethoxysilane, and reacting at 80 ℃ for 2 hours to obtain a pretreated product;
(2) and (3) mixing 20g of the pretreatment product with 100g of 107 glue with the viscosity of 1000cps (25 ℃, 50% RH), vacuumizing to the vacuum degree of 0.lMPa, and reacting for 1 hour to obtain the dealcoholized sealant.
Example 5
The preparation method of the dealcoholized sealant comprises the following steps:
(1) 2g of diethylaminomethyl triethoxysilane and 10g of aniline methyl trimethoxysilane are mixed uniformly and reacted for 0.5 hour at 100 ℃ to obtain a pretreated product;
(2) mixing 10g of the pretreatment product with 100g of 107 glue with the viscosity of 1000cps (25 ℃, 50% RH), vacuumizing to the vacuum degree of-0.08 MPa, and reacting for 2 hours to obtain the dealcoholized sealant.
Example 6
The preparation method of the dealcoholized sealant comprises the following steps:
(1) uniformly mixing 10g of diethylamino methyl triethoxysilane and 2g of hexamethylene diamine methyl triethoxysilane, and reacting at 10 ℃ for 24 hours to obtain a pretreated product;
(2) mixing 10g of the pretreatment product with 100g of 107 glue with the viscosity of 1000cps (25 ℃, 50% RH), vacuumizing to the vacuum degree of-0.08 MPa, and reacting for 2 hours to obtain the dealcoholized sealant.
Comparative example 1
The preparation method of the dealcoholized sealant comprises the following steps:
10g of diethylaminomethyltriethoxysilane, 5g of dichloromethyltriethoxysilane and 100g of 107 glue with the viscosity of 1000cps (25 ℃, 50 percent RH) are uniformly mixed, and the mixture is vacuumized at 25 ℃ until the vacuum degree is 0.lMPa and reacted for 1 hour to obtain the dealcoholized sealant.
Comparative example 2
The preparation method of the dealcoholized sealant comprises the following steps:
(1) uniformly mixing 10g of diethylaminomethyl triethoxysilane and 5g of dichloromethyl triethoxy silicon, and reacting at 5 ℃ for 50 minutes to obtain a pretreatment product;
(2) and (3) uniformly mixing 15g of the pretreatment product and 100g of 107 glue with the viscosity of 1000cps (25 ℃, 50% RH), vacuumizing to 0.lMPa, and reacting for 1 hour to obtain the dealcoholized sealant.
Comparative example 3
The preparation method of the dealcoholized sealant comprises the following steps:
(1) uniformly mixing 10g of diethylaminomethyl triethoxysilane and 5g of dichloromethyl triethoxy silicon, and reacting at 80 ℃ for 10 minutes to obtain a pretreatment product;
(2) mixing 15g of the pretreatment product with 100g of 107 glue with the viscosity of 1000cps (25 ℃, 50% RH), vacuumizing to the vacuum degree of 0.lMPa, and reacting for 1 hour to obtain the dealcoholized sealant.
Comparative example 4
The preparation method of the dealcoholized sealant comprises the following steps:
10g of diethylaminomethyl triethoxysilane and 100g of 107 glue with the viscosity of 1000cps (25 ℃, 50% RH) are mixed, and the mixture is vacuumized until the vacuum degree is 0.lMPa, and the mixture reacts for 1 hour to obtain the dealcoholized sealant.
Viscosity detection
According to the national standard GB/T2794-2013, the viscosity of the dealcoholized sealants of examples 1-4 and comparative examples 1-4 in the preparation process is monitored under the standard conditions, and the obtained results are shown in Table 1.
TABLE 1
As can be seen from Table 1, the dealcoholized sealants of examples 1 to 6 had smooth reaction processes and no viscosity peaks, while the dealcoholized sealants of comparative examples 1 to 4 had severe viscosity peaks during the preparation process, and the glue was gelled, and the product was cured in the reaction kettle.
Claims (10)
1. The preparation method of the dealcoholized sealant is characterized by comprising the following steps:
(1) uniformly mixing diethylaminomethyl triethoxysilane and α silane coupling agent, and reacting to obtain a pretreated product;
(2) and mixing the pretreated product and the base material, vacuumizing and reacting to obtain the dealcoholized sealant.
2. The method of dealcoholizing the sealant according to claim 1, wherein the mass ratio of the diethylaminomethyltriethoxysilane to the α silane coupling agent is 1-5: 1-5.
3. The method of claim 1 or 2 wherein said α silane coupling agent has the formula Xa-CH3-aSi(OR)3Wherein a is more than or equal to 1 and less than or equal to 3, and X is NH2-、Cl-、HS-、CH2＝C(CH3) COO-and CH2OCHCH2O-、C6H5NH-and NH2(CH2)6One or more of NH-; r is CH3-and C2H5-one or both of.
4. The method of dealcoholizing a sealant according to claim 3 wherein the α silane coupling agent is one or more of dichloromethyltriethoxysilane, anilinomethyltrimethoxysilane, anilinomethyltriethoxysilane, and hexamethylenediaminomethyltriethoxysilane.
5. The method of dealcoholizing a sealant according to claim 1, wherein the mass ratio of the pretreatment product to the base is 1: (5-10).
6. The method of a dealcoholization type sealant according to claim 1 or 5, wherein the base is a hydroxyl terminated silicone.
7. The method of a dealcoholization type sealant according to claim 6, wherein the hydroxyl terminated silicone is α, omega-dihydroxy polydimethylsiloxane.
8. The method of dealcoholizing the sealant according to claim 1, wherein the step (1) is carried out at 10 to 100 ℃ for 0.5 to 24 hours.
9. The method for preparing the dealcoholization type sealant according to claim 1, wherein the step (2) is carried out under a vacuum degree of-0.08 to 0.lMPa for 1 to 2 hours.
10. A dealcoholized sealant prepared according to the method of any one of claims 1 to 9.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010112957.0A CN111253908B (en) | 2020-02-24 | 2020-02-24 | Preparation method of dealcoholized sealant |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010112957.0A CN111253908B (en) | 2020-02-24 | 2020-02-24 | Preparation method of dealcoholized sealant |
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| CN111253908A true CN111253908A (en) | 2020-06-09 |
| CN111253908B CN111253908B (en) | 2021-11-30 |
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1629209A (en) * | 2003-12-17 | 2005-06-22 | 北京三辰化工有限公司 | Method for preparing electronic-grade single-component dealcoholizing-type room temperature cured silicon rubber by non-high-temperature vacuum dewatering method |
| CN1749301A (en) * | 2004-09-14 | 2006-03-22 | 刘兴宏 | High adhesive strength silicone rubber crosslinking curing agent |
| CN1749300A (en) * | 2004-09-14 | 2006-03-22 | 刘兴宏 | Colorless transparent silicone rubber crosslinking curing agent |
| CN101200594A (en) * | 2006-12-15 | 2008-06-18 | 比亚迪股份有限公司 | Monocomponent dealcoholized cold curing silicon rubber |
| CN107739590A (en) * | 2017-10-30 | 2018-02-27 | 董林妤 | A kind of rapid curing solar energy silica gel and preparation method thereof |
-
2020
- 2020-02-24 CN CN202010112957.0A patent/CN111253908B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1629209A (en) * | 2003-12-17 | 2005-06-22 | 北京三辰化工有限公司 | Method for preparing electronic-grade single-component dealcoholizing-type room temperature cured silicon rubber by non-high-temperature vacuum dewatering method |
| CN1749301A (en) * | 2004-09-14 | 2006-03-22 | 刘兴宏 | High adhesive strength silicone rubber crosslinking curing agent |
| CN1749300A (en) * | 2004-09-14 | 2006-03-22 | 刘兴宏 | Colorless transparent silicone rubber crosslinking curing agent |
| CN101200594A (en) * | 2006-12-15 | 2008-06-18 | 比亚迪股份有限公司 | Monocomponent dealcoholized cold curing silicon rubber |
| CN107739590A (en) * | 2017-10-30 | 2018-02-27 | 董林妤 | A kind of rapid curing solar energy silica gel and preparation method thereof |
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Denomination of invention: Preparation method of alcohol free sealant Granted publication date: 20211130 Pledgee: Jiangmen Rural Commercial Bank Co.,Ltd. Offshore Branch Pledgor: Guangdong Shengtang New Materials Technology Co.,Ltd. Registration number: Y2024980039480 |