CN113698844A - Epoxy-modified organosilicon compound, room-temperature moisture-curable composition, and preparation method and application thereof - Google Patents
Epoxy-modified organosilicon compound, room-temperature moisture-curable composition, and preparation method and application thereof Download PDFInfo
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- CN113698844A CN113698844A CN202111034643.4A CN202111034643A CN113698844A CN 113698844 A CN113698844 A CN 113698844A CN 202111034643 A CN202111034643 A CN 202111034643A CN 113698844 A CN113698844 A CN 113698844A
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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
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
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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
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions 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; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
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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
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions 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; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
- C09D183/06—Polysiloxanes containing silicon bound to oxygen-containing groups
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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
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2203/00—Applications
- C08L2203/20—Applications use in electrical or conductive gadgets
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2203/00—Applications
- C08L2203/20—Applications use in electrical or conductive gadgets
- C08L2203/202—Applications use in electrical or conductive gadgets use in electrical wires or wirecoating
Abstract
The invention discloses an epoxy modified organic silicon compound, a composition capable of being cured by moisture at room temperature, and a preparation method and application thereof. The epoxy modified organic silicon compound is prepared from epoxy resin, an epoxy resin curing agent and an alkoxy silane compound; epoxy resin reacts with an epoxy resin curing agent to generate an oligomer, the oligomer contains more hydroxyl, the oligomer reacts with alkoxy in alkoxy silane to obtain a product containing alkoxy silane active functional groups, the product has room temperature moisture curing performance similar to that of silicone sealant, can be stably placed for a long time under the condition of air isolation and cannot be cured, and after contacting with air, the product reacts with water in the air to slowly crosslink to form a cured product with certain strength. In order to accelerate the curing reaction, the epoxy modified organic silicon compound can be mixed with an organic tin catalyst or a titanate catalyst to prepare a single-component product which is cured quickly at room temperature, has high body strength and good adhesive force, and has low surface energy similar to organic silicon.
Description
Technical Field
The invention relates to an organic silicon compound, in particular to an epoxy modified organic silicon compound, a composition which contains the epoxy modified organic silicon compound and can be cured by moisture at room temperature, a preparation method and application thereof, belonging to the field of epoxy modified organic silicon compounds and application thereof.
Background
With the development of science and technology, electronic components such as PCB boards, sensitive circuits and the like become more and more delicate and have more and more rigorous requirements. The three-proofing (moisture-proof, mildew-proof and salt mist-proof) coating can provide long-term and reliable protection for components, and effectively improves the performance of products. In the three-proofing coating, silicone materials are used more and more widely due to their good overall properties compared to acrylic and epoxy materials, for example: the organosilicon material has excellent high and low temperature resistance and weather resistance, moderate hardness, low stress, excellent electrical property, good chemical resistance and good water resistance.
At present, the organic silicon coating materials on the market are various in forms, and can be divided into single-component products and double-component products according to the packaging mode. The two-component product, such as GT-912 organic silicon coating of Zhonghao Chenguang chemical research institute, has good comprehensive performance, but the two components are mixed according to a certain proportion when in use, so the construction is inconvenient. Single-component products, such as DC 1-2577 machine silicon conformal coating of Dow Corning in America, have good comprehensive performance and are widely applied, but the single-component products are pure organic silicon materials and are expensive; although the comprehensive performance of the phenyl silicone resin is good after curing, most of the phenyl silicone resin can be cured only by high temperature, and most of electronic components can not bear the high temperature required by curing, so that the phenyl silicone resin cannot be widely applied; although the organic silicon glass resin can realize single-component room temperature curing, the cured coating has low strength, large brittleness and poor adhesive force; the single-component room temperature vulcanized silicone rubber is rubbery after being cured, has low hardness and low strength, and thus cannot be basically applied.
Disclosure of Invention
One object of the present invention is to provide an epoxy-modified organosilicon compound.
It is another object of the present invention to provide a room temperature moisture curable composition.
It is another object of the present invention to provide a method for preparing the epoxy-modified organosilicon compounds and compositions.
The epoxy modified organosilicon compound and the composition are applied to the aspects of moisture resistance, dust prevention, water prevention, insulation and the like of electronic and electric appliances.
The above object of the present invention is achieved by the following technical solutions:
the invention provides an epoxy modified organic silicon compound which comprises the following components: epoxy resin, epoxy resin curing agent and alkoxy silane compound.
Preferably, the weight parts of the components are as follows: 80-120 parts of epoxy resin, 25-125 parts of epoxy resin curing agent and 100-200 parts of alkoxy silane compound;
more preferably, the weight parts of the components are as follows: 100 parts of epoxy resin, 25-100 parts of epoxy resin curing agent and 200 parts of alkoxy silane compound.
The epoxy resin includes but is not limited to any one of bisphenol A epoxy resin, bisphenol F epoxy resin or novolac epoxy resin or a mixture of more than one of the bisphenol A epoxy resin, the bisphenol F epoxy resin or the novolac epoxy resin according to any proportion.
The epoxy resin curing agent comprises but is not limited to any one or a mixture of more than one of polyether amine curing agent, fatty amine curing agent, anhydride curing agent or low molecular polyamide curing agent according to any proportion.
The alkoxy silane compound includes but is not limited to methyl trimethoxy silane, dimethyl dimethoxy silane, tetramethoxy silane, vinyl trimethoxy silane, phenyl trimethoxy silane and methacryloxy propyl trimethoxy silane, and the mixture of more than one of the methyl trimethoxy silane, the dimethyl dimethoxy silane, the tetramethoxy silane, the vinyl trimethoxy silane, the phenyl trimethoxy silane and the methacryloxy propyl trimethoxy silane is formed according to any proportion.
In another aspect of the present invention, there is provided a method for producing the epoxy-modified organosilicon compound, comprising: the components are uniformly mixed and react under the heating condition to obtain a uniform and transparent product with certain viscosity.
In order to achieve better preparation effect, the heating is preferably to 25-100 ℃, and more preferably to 80 ℃; the reaction time may be 4 to 48 hours, preferably 10 to 24 hours.
The epoxy resin and the epoxy resin curing agent react to generate oligomer, the generated oligomer contains more hydroxyl, then the hydroxyl reacts with alkoxy in the alkoxy silane to obtain the epoxy modified organic silicon compound which has alkoxy silane active functional groups and therefore has room temperature moisture curing performance similar to that of the silicone sealant.
In order to accelerate the curing reaction, the epoxy modified organic silicon compound can be mixed with an organic tin catalyst or a titanate catalyst to prepare a single-component product which can be cured quickly at room temperature.
Thus, the present invention further provides a room temperature moisture curable composition containing an epoxy-modified organosilicon compound, the composition comprising an epoxy-modified organosilicon compound, an organic solvent, and an organotin catalyst or titanate catalyst.
As a preferred embodiment of the present invention, the amounts of the components are preferably: 98 parts of organic solvent, 2 parts of epoxy modified organosilicon compound and 0.01 part of organic tin catalyst or titanate catalyst.
Wherein, the organic solvent can be any one or a mixture of more than one of toluene, xylene or ethyl acetate;
the organotin catalyst is preferably dibutyltin acetate.
The composition provided by the invention can be used in the field of electronic and electric appliances, and has the effects of moisture prevention, dust prevention, water prevention, insulation and the like. For example, the composition is sprayed or brushed on a bare wire, and after a solvent is volatilized, a certain protective layer can be formed within half an hour at room temperature, so that the bare wire has certain insulation, and the effects of protecting a circuit and enhancing the reliability of an electronic product are achieved.
Detailed Description
The invention will be further described with reference to specific embodiments, and the advantages and features of the invention will become apparent as the description proceeds. It is to be understood that the described embodiments are exemplary only and are not limiting upon the scope of the invention. It will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the invention, and that such changes and modifications may be within the scope of the invention.
EXAMPLE 1 preparation of epoxy-modified organosilicon Compound
According to the weight portion, 100 portions of bisphenol A epoxy resin, 25 portions of polyetheramine curing agent (D400) and 100 portions of methyltrimethoxysilane are uniformly mixed and reacted for 10 hours under the heating condition of 80 ℃, and then a light yellow, uniform and transparent product with certain viscosity is obtained.
The product prepared in this example can be stored in a sealed container at room temperature for a period of at least 6 months.
EXAMPLE 2 preparation of epoxy-modified organosilicon Compound
According to parts by weight, 100 parts of bisphenol A epoxy resin, 20 parts of polyetheramine curing agent (D400), 25 parts of polyetheramine curing agent (D2000), 80 parts of methyltrimethoxysilane and 20 parts of dimethyldimethoxysilane are uniformly mixed and react for 10 hours under the heating condition of 80 ℃ to obtain a light yellow, uniform and transparent product with certain viscosity.
The product prepared in this example can be stored in a sealed container at room temperature for a period of at least 6 months.
EXAMPLE 3 preparation of epoxy-modified organosilicon Compound
According to the weight portion, 100 portions of bisphenol A epoxy resin, 125 portions of polyether amine curing agent (D2000) and 125 portions of vinyl trimethoxy silane are evenly mixed and reacted for 20 hours under the heating condition of 80 ℃, and then a light yellow, uniform and transparent product with certain viscosity is obtained.
The product prepared in this example can be stored in a sealed container at room temperature for a period of at least 6 months.
EXAMPLE 4 preparation of epoxy-modified organosilicon Compound
According to the weight portion, 100 portions of bisphenol F epoxy resin, 40 portions of methyl hexahydrophthalic anhydride, 5 portions of DMP-30 and 200 portions of methacryloxypropyl trimethoxy silane are evenly mixed and react for 10 hours under the heating condition of 100 ℃ to obtain a light yellow, uniform and transparent product with certain viscosity.
The product prepared in this example can be stored in a sealed container at room temperature for a period of at least 6 months.
EXAMPLE 5 preparation of epoxy-modified organosilicon Compound
According to the weight portion, 100 portions of bisphenol F epoxy resin, 25 portions of low molecular polyamide curing agent, 3 portions of DMP-30, 80 portions of dimethyl dimethoxy silane and 120 portions of tetramethoxy silane are evenly mixed and react for 24 hours at 25 ℃ to obtain a yellow, uniform and transparent product with certain viscosity.
The product prepared in this example can be stored in a sealed container at room temperature for a period of at least 6 months.
EXAMPLE 6 preparation of epoxy-modified organosilicon Compound
According to the weight portion, 100 portions of bisphenol F epoxy resin, 100 portions of aliphatic amine curing agent and 100 portions of methyltrimethoxysilane are evenly mixed and react for 24 hours at 25 ℃ to obtain a yellow, uniform and transparent product with certain viscosity.
The product prepared in this example can be stored in a sealed container at room temperature for a period of at least 6 months.
EXAMPLE 7 preparation of epoxy-modified organosilicon Compound
According to the weight portion, 100 portions of bisphenol F epoxy resin, 100 portions of aliphatic amine curing agent and 150 portions of phenyl trimethoxy silane are evenly mixed and react for 24 hours at 80 ℃ to obtain a yellow, uniform and transparent product with certain viscosity.
The product prepared in this example can be stored in a sealed container at room temperature for a period of at least 6 months.
Experimental example 1 Performance test and application experiment of epoxy-modified organosilicon Compound
98 parts by weight of xylene, 2 parts by weight of the product of example 1 and 0.01 part by weight of dibutyltin acetate are prepared into a 2% solution, the solution is sprayed on the surface of an aluminum plate, the surface is dried after 20 minutes under the condition of 25 ℃ and 70% RH, a paint film with the thickness of about 50um is formed after the solution is continuously cured for 24 hours at room temperature, the adhesion is tested according to the national standard GB/T9286-1998, the surface resistance is tested according to the IPC-TM-6502.6.3.4A standard, the breakdown strength is tested according to the national standard GB1981.2-2003, and a cold and hot impact test is carried out according to the IPC-TM-6502.6.7.1A standard, and the performance test results are shown in Table 1.
98 parts by weight of xylene, 2 parts by weight of the product of example 2 and 0.01 part by weight of dibutyltin acetate are prepared into a 2% solution, the solution is sprayed on the surface of an aluminum plate, the surface is dried after 25 minutes under the condition of 25 ℃ and 70% RH, a paint film with the thickness of about 50um is formed after the solution is continuously cured for 24 hours at room temperature, the adhesion is tested according to the national standard GB/T9286-1998, the surface resistance is tested according to the IPC-TM-6502.6.3.4A standard, the breakdown strength is tested according to the national standard GB1981.2-2003, and a cold and hot impact test is carried out according to the IPC-TM-6502.6.7.1A standard, and the performance test results are shown in Table 1.
98 parts by weight of toluene, 2 parts by weight of the product of example 3 and 0.01 part by weight of dibutyltin acetate are prepared into a 2% solution, the solution is sprayed on the surface of an aluminum plate, the surface is dried after 42 minutes under the condition of 25 ℃ and 70% RH, a paint film with the thickness of about 50um is formed after the curing at room temperature for 24 hours, the adhesion is tested according to the national standard GB/T9286-1998, the surface resistance is tested according to the IPC-TM-6502.6.3.4A standard, the breakdown strength is tested according to the national standard GB1981.2-2003, and the cold and hot impact test is carried out according to the IPC-TM-6502.6.7.1A standard, and the performance test results are shown in Table 1.
98 parts by weight of toluene, 2 parts by weight of the product of example 4 and 0.01 part by weight of dibutyltin acetate are prepared into a 2% solution, the solution is sprayed on the surface of an aluminum plate, the surface drying can be carried out in 29 minutes under the condition of 25 ℃ and 70% RH, a paint film with the thickness of about 50um is formed after the curing at room temperature for 24 hours, the adhesion is tested according to the national standard GB/T9286-1998, the surface resistance is tested according to the IPC-TM-6502.6.3.4A standard, the breakdown strength is tested according to the national standard GB1981.2-2003, and the cold and hot impact test is carried out according to the IPC-TM-6502.6.7.1A standard, and the performance test results are shown in Table 1.
78 parts by weight of toluene, 20 parts by weight of ethyl acetate, 2 parts by weight of the product of example 5 and 0.01 part by weight of dibutyltin acetate are prepared into a 2% solution, the solution is sprayed on the surface of an aluminum plate, the surface of the aluminum plate can be dried after 18 minutes under the conditions of 25 ℃ and 70% RH, a paint film with the thickness of about 50um is formed after the aluminum plate is continuously cured for 24 hours at room temperature, the adhesion is tested according to the national standard GB/T9286-1998, the surface resistance is tested according to the IPC-TM-6502.6.3.4A standard, the breakdown strength is tested according to the national standard GB1981.2-2003, and the cold and hot impact test is carried out according to the IPC-TM-6502.6.7.1A standard, and the performance test results are shown in Table 1.
78 parts by weight of toluene, 20 parts by weight of ethyl acetate, 2 parts by weight of the product of example 6 and 0.01 part by weight of dibutyltin acetate are prepared into a 2% solution, the solution is sprayed on the surface of an aluminum plate, the surface of the aluminum plate can be dried after 20 minutes under the conditions of 25 ℃ and 70% RH, a paint film with the thickness of about 50um is formed after the aluminum plate is continuously cured for 24 hours at room temperature, the adhesion is tested according to the national standard GB/T9286-1998, the surface resistance is tested according to the IPC-TM-6502.6.3.4A standard, the breakdown strength is tested according to the national standard GB1981.2-2003, and the cold and hot impact test is carried out according to the IPC-TM-6502.6.7.1A standard, and the performance test results are shown in Table 1.
98 parts by weight of toluene, 2 parts by weight of the product of example 7 and 0.01 part by weight of dibutyltin acetate are prepared into a 2% solution, the solution is sprayed on the surface of an aluminum plate, the surface is dried after 35 minutes under the condition of 25 ℃ and 70% RH, a paint film with the thickness of about 50um is formed after the curing at room temperature for 24 hours, the adhesion is tested according to the national standard GB/T9286-1998, the surface resistance is tested according to the IPC-TM-6502.6.3.4A standard, the breakdown strength is tested according to the national standard GB1981.2-2003, and the cold and hot impact test is carried out according to the IPC-TM-6502.6.7.1A standard, and the performance test results are shown in Table 1.
Table 1 results of testing various properties of the products prepared in examples 1 to 7
| Example 1 | Example 2 | Example 3 | Example 4 | Example 5 | Example 6 | Example 7 | |
| Product storage time | >6 months old | >6 months old | >6 months old | >6 months old | >6 months old | >6 months old | >6 months old |
| Time to surface dry | 20 minutes | 25 minutes | 42 minutes | 29 minutes | 18 minutes | 20 minutes | 35 minutes |
| Adhesion force | By passing | By passing | By passing | By passing | By passing | By passing | By passing |
| Surface resistance | 2.5×1016′Ω | 2.5×1016′Ω | 2.5×1016′Ω | 2.6×1016′Ω | 2.3×1016′Ω | 2.5×1016′Ω | 2.5×1016′Ω |
| Breakdown strength | 2.8kV/mm | 2.8kV/mm | 2.8kV/mm | 3.0kV/mm | 2.8kV/mm | 2.8kV/mm | 2.8kV/mm |
| Cold and hot shock | OK | OK | OK | OK | OK | OK | OK |
Claims (10)
1. An epoxy-modified organosilicon compound, characterized by comprising the following components: epoxy resin, epoxy resin curing agent and alkoxy silane compound.
2. The epoxy-modified organosilicon compound according to claim 1, wherein the weight parts of the components are: 80-120 parts of epoxy resin, 25-125 parts of epoxy resin curing agent and 100-200 parts of alkoxy silane compound.
3. The epoxy-modified organosilicon compound according to claim 2, wherein the weight parts of the components are: 100 parts of epoxy resin, 25-100 parts of epoxy resin curing agent and 200 parts of alkoxy silane compound.
4. The epoxy-modified organosilicon compound of any of claims 1 to 3, wherein the epoxy resin includes, but is not limited to, any one or more of bisphenol A epoxy resin, bisphenol F epoxy resin, or novolac epoxy resin in any proportion;
the epoxy resin curing agent comprises but is not limited to any one or a mixture of more than one of polyether amine curing agent, fatty amine curing agent, anhydride curing agent or low molecular polyamide curing agent according to any proportion;
the alkoxy silane compound includes but is not limited to methyl trimethoxy silane, dimethyl dimethoxy silane, tetramethoxy silane, vinyl trimethoxy silane, phenyl trimethoxy silane and methacryloxy propyl trimethoxy silane, and the mixture of more than one of the methyl trimethoxy silane, the dimethyl dimethoxy silane, the tetramethoxy silane, the vinyl trimethoxy silane, the phenyl trimethoxy silane and the methacryloxy propyl trimethoxy silane is formed according to any proportion.
5. A process for producing the epoxy-modified organosilicon compound according to any of claims 1 to 3, comprising: mixing the above components, and reacting under heating.
6. A method according to claim 5, wherein the heating is to 25-100 ℃, preferably to 80 ℃; the reaction time is 4 to 48 hours, preferably 10 to 24 hours.
7. A room temperature moisture curable composition comprising the epoxy-modified organosilicon compound of claim 1, an organic solvent, and an organotin catalyst or titanate catalyst;
preferably, the amounts of the components are as follows: 2 parts of the epoxy-modified organosilicon compound according to claim 1, 98 parts of an organic solvent, and 0.01 part of an organotin catalyst or a titanate catalyst.
8. The composition of claim 7, wherein the organic solvent is any one or a mixture of more than one of toluene, xylene or ethyl acetate;
the organic tin catalyst is dibutyl tin acetate.
9. Use of the epoxy-modified organosilicon compound of any of claims 1 to 3 for moisture-, dust-, water-or insulation of products; preferably, the product is an electronic appliance product.
10. Use of a composition according to claim 7 or 8 for moisture-, dust-, water-or insulation of a product; preferably, the product is an electronic appliance product.
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| CN111592824A (en) * | 2020-05-25 | 2020-08-28 | 上海牛元工贸有限公司 | Moisture-curing liquid composition for reinforcing and waterproofing joint mixture and preparation method and application thereof |
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2021
- 2021-09-03 CN CN202111034643.4A patent/CN113698844B/en active Active
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| JPH10298405A (en) * | 1997-04-25 | 1998-11-10 | Yuka Shell Epoxy Kk | Epoxy resin composition and cured product composite |
| CN1468271A (en) * | 2000-12-18 | 2004-01-14 | 小西株式会社 | One-pack moisture-curing epoxy resin composition |
| CN1468270A (en) * | 2000-12-18 | 2004-01-14 | С����������ʽ���� | One-pack moisture-curable epoxy resin composition |
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| CN111592824A (en) * | 2020-05-25 | 2020-08-28 | 上海牛元工贸有限公司 | Moisture-curing liquid composition for reinforcing and waterproofing joint mixture and preparation method and application thereof |
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| 韩航等: "湿气固化硅烷封端树脂密封胶的国内研究进展及其阻燃功能化", 《化工新型材料》 * |
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