CN111234773B - Silicone sealant with high environmental adaptability - Google Patents
Silicone sealant with high environmental adaptability Download PDFInfo
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- CN111234773B CN111234773B CN202010160338.9A CN202010160338A CN111234773B CN 111234773 B CN111234773 B CN 111234773B CN 202010160338 A CN202010160338 A CN 202010160338A CN 111234773 B CN111234773 B CN 111234773B
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
- C09J183/04—Polysiloxanes
- C09J183/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/22—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
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
- C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
- C08G77/388—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing nitrogen
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K2201/00—Specific properties of additives
- C08K2201/014—Additives containing two or more different additives of the same subgroup in C08K
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- Chemical Kinetics & Catalysis (AREA)
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Abstract
The invention relates to a silicone sealant with high environmental adaptability, which comprises the following components in parts by mass: the silicone sealant prepared by the invention has high environmental adaptability, can be completely cured within hours or even tens of minutes under a heating condition, has no special requirements on curing environments (elements such as nitrogen, phosphorus, sulfur, tin and the like), and can realize surface drying while the interior of the body is subjected to thermosetting in a thermosetting process. Meanwhile, by adopting the coupling agent structure recommended by the invention, the product hardly contains volatile micromolecular substances after being cured, so that the reliability and the environmental protection of the product are greatly improved.
Description
Technical Field
The invention relates to a silicone sealant with high environmental adaptability, belonging to the field of organic silicon materials.
Technical Field
The organosilicon material has been widely used in various industries because of its excellent heat resistance, cold resistance, dielectric properties, ozone resistance, and weathering resistance, and can be used for a long time at-60 ℃ (or lower) to +250 ℃ (or higher). There are two main types of curing of conventional silicone sealants: condensation type and addition type.
Condensation type silicone sealants, i.e., moisture-cured silicone sealants, are exposed to air and first absorb moisture from the air to effect surface cross-linking curing, which can be several minutes or hours, but also often takes several days to achieve deep cure because of the need to absorb moisture. The advantage is that it is suitable for use in unheated environments, but the disadvantage is that it requires long deep cure times.
The addition type silicone sealant can meet the scene needing short-time rapid curing, and can be completely cured within several hours at the temperature of 100 ℃ and 150 ℃. However, the curing characteristic is harsh on the environment, and elements such as nitrogen, phosphorus, sulfur, tin and the like and compounds thereof cannot be contained in the curing environment, so that the catalyst is poisoned to influence the curing of the glue.
The invention aims to provide a silicone sealant which can be completely cured within several hours or even tens of minutes and has no special requirements on curing environments (nitrogen, phosphorus, sulfur, tin and other elements). The silicone sealant adopts the mutual matching of acrylic acid modified organic silicon main body resin and acrylic acid modified organic silicon cross-linking agent, and realizes free radical polymerization under the catalysis of peroxide, thereby achieving the effect of curing, cross-linking and sealing. Meanwhile, the surface curing is inhibited due to the fact that free radical polymerization is easy to encounter the action of surface oxygen inhibition, and an oxygen absorbent is provided for matching, so that the surface can be dried while the interior of the body is thermally cured in the thermal curing process of the prepared silicone sealant.
Disclosure of Invention
A silicone sealant with high environmental adaptability comprises the following components in parts by mass:
| acrylic acid modified organic silicon main body resin | 100 portions of |
| Multifunctional acrylic acid modified organosilicon crosslinking agent | 2 to 10 portions of |
| Monofunctional acrylic diluents | 5 to 30 parts of |
| Coupling agent | 2 to 8 portions of |
| Peroxides and their use in the preparation of pharmaceutical preparations | 1 to 7 parts of |
| Oxygen absorbent | 2 to 7 portions of |
The acrylic modified organic silicon main body resin is characterized in that the acrylic modified organic silicon main body resin is prepared by referring to the method disclosed in patent CN109777121A, but one of the raw materials is replaced by Hexamethylene Diisocyanate (HDI):
(1) hexamethylene Diisocyanate (HDI), pentaerythritol triacrylate and dibutyltin dilaurate as catalysts in a molar ratio of 1: (2-3): (0.001-0.05) to obtain a substance (I) with three-functionality acrylate structures at two ends, wherein the reaction equation is as follows:
(2) and (2) adding a substance with three-functionality acrylate structures at two ends, hydrogen-terminated silicone oil and an isopropanol solution catalyst of chloroplatinic acid in a molar ratio of (2-4): 1: (0.001-0.05) carrying out hydrosilylation reaction to obtain the linear acrylic acid modified organic silicon main body resin.
The reaction temperature in the step (1) is 30-80 ℃.
In the step (2), the reaction temperature is 80-120 ℃, and the reaction time is 3-6 hours.
In the step (2), the catalyst of the isopropanol solution of chloroplatinic acid is the isopropanol solution of chloroplatinic acid, and the concentration range of the chloroplatinic acid is 0.03 mol/L-0.07 mol/L.
In the step (2), the molecular weight of the hydrogen-terminated silicone oil is 2000-8000;
the multifunctional acrylic acid modified organosilicon crosslinking agent is selected from one or two of the following self-made structure (II) and structure (III). The structure is as follows:
the multifunctional acrylic acid modified organic silicon cross-linking agent has the beneficial effects that: the molecule introduces an organic silicon structure, the compatibility of the cross-linking agent and the main resin is enhanced, and products with transparency requirements can be prepared. And the introduction of the organic silicon structure can improve the heat resistance of the cross-linking agent, so that the temperature resistance of the final product is improved. Meanwhile, after modification by introducing silicone, we found that the skin irritation feeling was much reduced.
The monofunctional acrylic diluent can be one or a mixture of more of beta-hydroxyethyl methacrylate, hydroxypropyl methacrylate, butyl acrylate, octyl methacrylate and lauryl methacrylate;
the preparation process of the coupling agent is as follows: toluene is used as a solvent (the mass ratio of the toluene to a solute is 1:1), and a hydrosilylation reaction is carried out on vinyl trimethoxy silane, allyl methacrylate, allyl glycidyl ether, 1, 3, 5, 7-tetramethylcyclotetrasiloxane and a chloroplatinic acid/isopropanol solution catalyst according to a molar ratio of 1:1:2:1 (0.001-0.05), wherein the reaction temperature is 80-120 ℃, and the reaction time is 3-6 hours. After the reaction is finished, removing the solvent through reduced pressure distillation to obtain the coupling agent with the following structure:
the coupling agent adopting the structure has the beneficial effects that: firstly, molecules contain an organic silicon structure and have good compatibility with a main body structure; secondly, the molecules contain acrylate and epoxy groups, and can participate in the cross-linking structure of the main body, and after the product is cured, free small molecules basically do not exist, so that the influence on the use environment is less; thirdly, the structure contains alkoxy and epoxy, and can meet the requirements of interface bonding in different environments.
The peroxide is one or more of benzoyl peroxide, benzoyl peroxide tert-butyl ester, methyl ethyl ketone peroxide, dicumyl peroxide, tert-butyl perbenzoate, Trigonox B, Trigonox 21S, Trigonox 42S, Trigonox F and Trigonox D;
the oxygen absorbent is one or more of 2- (2- (2-methoxyethoxy) ethoxy) acetic acid, triethanolamine, triethylamine, dimethylaniline, N-isoamyl dimethylaminobenzoate and Michler's ketone; on the basis of the invention, according to the performance requirements, a proper amount of plasticizer and filler, including functional filler fluorescent agent, antioxidant and the like, can be added.
The preparation process of the silicone sealant with high environmental adaptability comprises the following steps: uniformly mixing a multifunctional acrylic acid modified organic silicon cross-linking agent, a monofunctional acrylic acid diluent, a coupling agent, peroxide and an oxygen absorbent, adding an acrylic acid modified organic silicon main body resin into the mixture, uniformly mixing the mixture again, filling the mixture, and placing the mixture in a freezing environment for low-temperature storage.
The invention has the beneficial effects that: the silicone sealant product has high environmental adaptability, can be completely cured within several hours or even dozens of minutes under the heating condition, and has no special requirements on the curing environment (elements such as nitrogen, phosphorus, sulfur, tin and the like). Meanwhile, by adopting the coupling agent structure recommended by the invention, the product hardly contains volatile micromolecular substances after being cured, so that the reliability and the environmental protection of the product are greatly improved. The surface curing is inhibited due to the fact that free radical polymerization is easy to encounter the action of surface oxygen inhibition, and an oxygen absorbent is provided for compounding, so that the surface can be dried while the interior of a body is thermally cured in the thermal curing process of the prepared silicone sealant.
DETAILED DESCRIPTION OF EMBODIMENT (S) OF INVENTION
The invention is described below by way of examples, which are intended to illustrate the invention and are not intended to limit its application.
Example 1 preparation of acrylic modified Silicone base resin one
Mixing hexamethylene diisocyanate, pentaerythritol triacrylate and dibutyltin dilaurate according to a molar ratio of 1:2: 0.01, and reacting for 2h at 60 ℃ to prepare a substance (I) with two ends having a multifunctional acrylate structure; adding a substance (I) with two ends having a multifunctional acrylate structure, hydrogen-terminated silicone oil with molecular weight of 2000 and isopropanol solution catalyst of chloroplatinic acid (calculated by platinum atoms) according to a molar ratio of 2.5: 1: 0.01 reacts for 4 hours at the temperature of 90 ℃ to prepare the acrylic modified organic silicon main body resin I.
Example 2 preparation of acrylic modified Silicone host resin two
Mixing hexamethylene diisocyanate, pentaerythritol triacrylate and dibutyltin dilaurate according to a molar ratio of 1:2: 0.02 mixing, reacting for 2h at 50 ℃ to prepare a substance (I) with two ends having a multifunctional acrylate structure; adding a substance (I) with two ends having a multifunctional acrylate structure, terminal hydrogen silicone oil with molecular weight of 8000, and an isopropanol solution catalyst of chloroplatinic acid (calculated by platinum atoms) according to a molar ratio of 2:1: 0.03 reacting for 4h at 80 ℃ to obtain the second acrylic modified organic silicon main body resin.
Example 3 preparation of multifunctional acrylic-modified Silicone crosslinker Structure (II)
Mixing hexamethylene diisocyanate, pentaerythritol triacrylate and dibutyltin dilaurate according to a molar ratio of 1:2: 0.01, and reacting for 2h at 60 ℃ to obtain a substance (I) with two ends having a multifunctional acrylate structure. After cooling to room temperature, adding a substance (I) with two ends having a multifunctional acrylate structure, a hydrogen-containing double-end socket and a chloroplatinic acid isopropanol solution catalyst (calculated by platinum atoms) according to a molar ratio of 2.5: 1: 0.02 reacting for 6h at 80 ℃ to obtain the multifunctional acrylic acid modified organosilicon crosslinking agent structure (II).
Example 4 preparation of multifunctional acrylic-modified Silicone crosslinker Structure (III)
Adding allyl methacrylate and toluene in a mass ratio of 1:1 into a reaction kettle, adding an isopropanol solution catalyst (calculated by platinum atoms) of chloroplatinic acid (the molar ratio of the catalyst to the allyl methacrylate is 100:0.5), heating to 50 ℃, stirring for reaction for 10 minutes, then dropwise adding a toluene solution of 1, 3, 5, 7-tetramethylcyclotetrasiloxane (the mass fraction of the 1, 3, 5, 7-tetramethylcyclotetrasiloxane is 50%, and the molar ratio of the 1, 3, 5, 7-tetramethylcyclotetrasiloxane to the allyl methacrylate is 1:6), heating to 80 ℃, and reacting for 5 hours. And after the reaction is finished, carrying out reduced pressure distillation to remove the toluene solvent and unreacted micromolecules, thus obtaining the multifunctional acrylic acid modified organosilicon crosslinking agent structure (III).
EXAMPLE 5 preparation of Silicone sealants
4g of the acrylic acid modified organosilicon crosslinking agent structure (II) prepared in example 3, 20g of beta-hydroxyethyl methacrylate, 10g of butyl acrylate, 3g of the coupling agent, 5g of benzoyl peroxide and 5g of 2- (2- (2-methoxyethoxy) ethoxy) acetic acid are mixed and stirred uniformly, 100g of the acrylic acid modified organosilicon main body resin I is added, and after mixing uniformly again, filling is carried out, and the mixture is placed in a freezing environment for low-temperature storage.
EXAMPLE 6 preparation of Silicone sealants
10g of the acrylic acid modified organosilicon crosslinking agent structure (III) prepared in example 4, 6g of hydroxypropyl methacrylate, 4g of octyl methacrylate, 5g of coupling agent, 7g of Trigonox 21S and 7g of triethylamine are mixed and stirred uniformly, then 100g of acrylic acid modified organosilicon main body resin II is added, and after mixing uniformly again, filling is carried out, and the mixture is placed in a freezing environment for low-temperature storage.
EXAMPLE 7 preparation of Silicone sealants
2g of the acrylic modified silicone crosslinker structure (II) prepared in example 3, 1g of the acrylic modified silicone crosslinker structure (III) prepared in example 4, 5g of lauryl methacrylate, 8g of a coupling agent, 1g of Trigonox 42S, 2g of Trigonox F and 5g of N, N-dimethylaminobenzoate are mixed and stirred uniformly, then 100g of the acrylic modified silicone host resin II is added, mixed uniformly again, filled and placed in a freezing environment for low-temperature storage.
Comparative example 1 preparation of Silicone sealant
10g of the acrylic modified silicone cross-linking agent structure (III) prepared in example 4, 6g of hydroxypropyl methacrylate, 4g of octyl methacrylate, 5g of coupling agent, 1g of benzoyl peroxide and 6g of Trigonox 21S were mixed and stirred uniformly, then 100g of the acrylic modified silicone main body resin II was added, mixed uniformly again, filled, and placed in a freezing environment for low-temperature storage.
Comparative example 2 preparation of Silicone sealant
Mixing and stirring 10g of pentaerythritol triacrylate, 6g of hydroxypropyl methacrylate, 4g of octyl methacrylate, 5g of a coupling agent, 7g of Trigonox 21S and 7g of triethylamine uniformly, adding 100g of acrylic acid modified organic silicon main body resin II, mixing uniformly again, filling, and placing in a freezing environment for low-temperature storage.
Comparative example 3 preparation of Silicone sealant
4g of the acrylic acid modified organosilicon crosslinking agent structure (II) prepared in example 3, 20g of beta-hydroxyethyl methacrylate, 10g of butyl acrylate, 3g of the coupling agent, 5g of benzoyl peroxide and 5g of 2- (2- (2-methoxyethoxy) ethoxy) acetic acid were mixed and stirred uniformly, then 100g of the acrylic acid modified organosilicon main body resin I and 1g of sublimed sulfur were added, and after mixing uniformly again, filling was carried out, and the mixture was placed in a freezing environment for low-temperature storage.
Test method
Preparing the prepared silicone sealant into a sample sheet with the thickness of 2mm, placing the sample sheet into an oven for curing, taking out the sample sheet after curing at 150 ℃/30min, observing the curing condition of the sealant, and the surface drying condition (the surface drying is verified by finger touch), wherein the verification result is as follows:
from the comparison of the above results, it can be seen that:
the comparison of the examples with comparative example 1 shows that the addition of an oxygen getter helps to overcome the barrier effect of surface oxygen inhibition encountered during curing of silicone sealants.
The comparison between the examples and the comparative example 2 shows that the self-made acrylic modified organosilicon crosslinking agent of the invention has better compatibility with the main resin, and can promote the compatibility of the diluent with the main resin.
The comparison result between the example and the comparative example 3 shows that the introduction of sublimed sulfur in the formula does not affect the curing of the silicone sealant of the invention, and the introduction of amine oxygen absorbent in the invention does not affect the curing of the product, thus showing that the product of the invention has high adaptability to the environment.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the scope of the present invention, which is intended to cover all modifications, equivalents, improvements, etc. within the spirit and scope of the present invention.
Claims (4)
1. The silicone sealant with high environmental adaptability is characterized by comprising the following components in parts by mass: 100 parts of acrylic acid modified organic silicon main body resin, 2-10 parts of multifunctional acrylic acid modified organic silicon cross-linking agent, 5-30 parts of monofunctional acrylic acid diluent, 2-8 parts of coupling agent, 1-7 parts of peroxide and 2-7 parts of oxygen absorbent;
the multifunctional acrylic acid modified organosilicon crosslinking agent is one of a structure (II) or a structure (III), and the structural formula is as follows:
the oxygen absorbent is one or more of 2- (2- (2-methoxyethoxy) ethoxy) acetic acid, triethanolamine, triethylamine, dimethylaniline, N-isoamyl dimethylaminobenzoate and Michler's ketone.
2. The silicone sealant according to claim 1, wherein the method for synthesizing the acrylic modified silicone host resin comprises: hexamethylene diisocyanate, pentaerythritol triacrylate and dibutyltin dilaurate as catalysts in a molar ratio of 1: (2-3): (0.001-0.05) reacting at 30-80 ℃ to obtain a substance with three-functionality acrylate structures at two ends, and reacting the substance with three-functionality acrylate structures at two ends, hydrogen-terminated silicone oil and an isopropanol solution catalyst of chloroplatinic acid in a molar ratio of (2-4): 1: (0.001-0.05) carrying out hydrosilylation reaction at the temperature of 80-120 ℃ for 3-6 hours to obtain linear acrylic acid modified organic silicon main body resin; the concentration range of the isopropanol solution of the chloroplatinic acid is 0.03-0.07 mol/L, and the molecular weight of the hydrogen-terminated silicone oil is 2000-8000.
3. The silicone sealant according to claim 1, wherein the monofunctional acrylic diluent is one or a mixture of beta-hydroxyethyl methacrylate, hydroxypropyl methacrylate, butyl acrylate, octyl methacrylate, lauryl methacrylate; the peroxide is one or more of benzoyl peroxide, benzoyl peroxide tert-butyl ester, methyl ethyl ketone peroxide, dicumyl peroxide, tert-butyl perbenzoate, Trigonox B, Trigonox 21S, Trigonox 42S, Trigonox F and Trigonox D.
4. The silicone sealant according to claim 1, wherein the coupling agent is prepared by the following process: carrying out hydrosilylation reaction on toluene serving as a solvent and an isopropanol solution catalyst of 1:1 solute mass ratio of vinyl trimethoxy silane, allyl methacrylate, allyl glycidyl ether, 1, 3, 5, 7-tetramethylcyclotetrasiloxane and chloroplatinic acid according to a molar ratio of 1:1:2:1 (0.001-0.05), wherein the reaction temperature is 80-120 ℃, and the reaction time is 3-6 hours; the molecular formula of the coupling agent is as follows:
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013080741A1 (en) * | 2011-11-30 | 2013-06-06 | セントラル硝子株式会社 | Photopolymerizable composition and pattern forming method using same |
| CN104204950A (en) * | 2012-06-15 | 2014-12-10 | 第一毛织株式会社 | Photocurable composition, barrier layer including same, and encapsulated device including same |
| CN109777121A (en) * | 2018-12-18 | 2019-05-21 | 中科院广州化学有限公司南雄材料生产基地 | A kind of preparation method of ultraviolet curing organic silicon wear resistant resin |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013080741A1 (en) * | 2011-11-30 | 2013-06-06 | セントラル硝子株式会社 | Photopolymerizable composition and pattern forming method using same |
| CN104204950A (en) * | 2012-06-15 | 2014-12-10 | 第一毛织株式会社 | Photocurable composition, barrier layer including same, and encapsulated device including same |
| CN109777121A (en) * | 2018-12-18 | 2019-05-21 | 中科院广州化学有限公司南雄材料生产基地 | A kind of preparation method of ultraviolet curing organic silicon wear resistant resin |
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