CN111454662B - Room-temperature-curable organic silicon resin conformal coating and preparation method thereof - Google Patents
Room-temperature-curable organic silicon resin conformal coating and preparation method thereof Download PDFInfo
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- 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
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Abstract
The invention discloses a room temperature curable organic silicon resin conformal coating and a preparation method thereof, wherein the room temperature curable organic silicon resin conformal coating is mainly prepared from the following raw materials: hydroxymethyl organic silicon resin, alkoxy-terminated phenyl silicone oil, a cross-linking agent and a catalyst. According to the invention, the organic silicon resin is modified to obtain the organic silicon resin conformal coating with the introduced difunctional chain links, the toughness of the silicon resin is increased, and the organic silicon resin conformal coating contains a tin catalyst, so that the organic silicon resin conformal coating is cured at room temperature.
Description
Technical Field
The invention belongs to the field of organic silicon resin materials, and particularly relates to an organic silicon resin conformal coating capable of being cured at room temperature and a preparation method thereof.
Background
The organic silicon material is polysiloxane which is formed by taking a unique structure of silicon-oxygen bond (-Si-O-Si-) as a framework, has the performances of inorganic and organic materials, has the basic properties of good weather resistance, high and low temperature resistance and the like, and has the excellent characteristics of electrical insulation, oxidation resistance stability, hydrophobicity, corrosion resistance, no toxicity, no odor, physiological inertia and the like. The material is not only used in special industries such as aerospace, military and the like, but also widely applied in various industries such as organic synthesis, building materials, illumination, daily chemicals, household appliances, textile finishing, automobiles, mechanical manufacturing, papermaking, medical engineering and the like, and is an indispensable novel chemical material in modern industry.
In recent years, organic silicon materials have been developed as the main type of electronic device conformal materials due to their good high and low temperature resistance and good electrical insulation properties.
At present, the common organosilicon dressing material is usually a silicon rubber product, and is cured by contacting with moisture in air when in use, but the dressing coating is not flame-retardant, and has lower hardness and strength after curing, so the application is limited to a certain extent. The strength and hardness of the cured organic silicon resin coating are good, but the coating is often required to be cured at high temperature without modification, the toughness of the cured coating is poor, and the coating is easy to crack under high-temperature and low-temperature impact, so that the application requirement cannot be met.
At present, the idea of copolymerizing a linear polymer to a phenyl silicone resin in the prior art is utilized to increase the flexibility of the silicone resin, so that the silicone resin is modified. For example, chinese patent publication No. CN102304323A discloses a room temperature curable phenyl silicone conformal coating, which mainly comprises a block copolymer of phenyl silicone and linear polysiloxane or a block copolymer of methylphenyl silicone and linear polysiloxane, alkoxysilane, an organic titanium compound, an auxiliary agent, a solvent, and the like, and has high transparency and toughness after curing; chinese patent with publication number CN101591504A discloses a single-component organosilicon flame-retardant conformal coating, which is prepared from a block polymer of phenyl silicone resin and linear polysiloxane, a cross-linking agent, a flame retardant and a solvent, and has different hardness, elasticity and thermoplasticity; the Chinese invention patent with the publication number of CN110317343A discloses a single-component room-temperature curing organic silicon resin containing MQ structural units and a preparation method thereof, wherein the organic silicon resin is obtained by adding alkyl alkoxy silane to carry out end capping in the presence of a catalyst after condensation reaction of hydrogen-containing MQ silicon resin and phenyl hydroxyl silicone oil or phenyl hydroxyl silicone resin.
From the three patents of the invention, the technical route adopted when the organic silicon resin is modified in the prior art is as follows: the idea of copolymerizing the linear polymer to the phenyl silicone resin is utilized to increase the toughness of the silicone resin. However, this technical route has the following drawbacks: due to the existence of benzene ring in phenyl silicone resin, steric hindrance of phenyl silicone resin is increased, so that the phenyl silicone resin has harsh reaction conditions during polymerization of linear polymer, for example, in CN102304323A, nitrogen (inert gas) is required for reaction conditions, reaction time is long (reaction time is long), toluene is added (solvent is additionally required), and solvent is distilled out under reduced pressure (process step is long); CN110317343A added Pt catalyst and dibutyltin dilaurate (two catalysts), added toluene (solvent is needed), and vacuum depreciated (long process step). In addition, the phenyl silicone resin has larger steric hindrance, which easily causes the uneven structure of the product and affects the performance of the product.
Therefore, the development of a silicone coating material which is convenient to use and high in cost performance has become necessary.
Disclosure of Invention
In order to solve the problems, the invention provides a room temperature curable silicone resin conformal coating and a preparation method thereof.
In order to achieve the purpose, the invention adopts the following technical scheme:
a room temperature curable silicone resin conformal coating is prepared from the following raw materials: hydroxymethyl organic silicon resin liquid, alkoxy end-capping phenyl silicone oil, end-capping agent and catalyst,
wherein the structural formula of the hydroxymethyl organosilicon resin in the hydroxymethyl organosilicon resin liquid is as follows:
the structural formula of the alkoxy-terminated phenyl silicone oil is as follows:
the structural formula of the obtained room-temperature-curable organic silicon resin conformal coating is as follows:
further, the catalyst is dibutyltin dilaurate.
Further, the cross-linking agent is monomethyltrimethoxysilane.
A preparation method of a room temperature curable silicone resin conformal coating comprises the following steps:
s1, preparing hydroxymethyl organic silicon resin liquid: putting a reaction monomer and a solvent into a reaction kettle, dropwise adding a mixture of concentrated HCl and distilled water at room temperature, heating to 60 ℃ after dropwise adding, performing reflux reaction for 5 hours, heating to 70-80 ℃, evaporating methanol and water generated by the reaction, then heating to 110 ℃, performing reflux reaction for 8 hours, cooling to 60 ℃, adding hexamethyldisilazane, heating to 110 ℃, concentrating to a resin solution with a solid content of 60%, and cooling for later use, wherein the reaction monomer is one or more of methyltrimethoxysilane, ethyl orthosilicate and dimethyldimethoxysilane;
s2, preparing alkoxy-terminated phenyl silicone oil: uniformly mixing octamethylcyclotetrasiloxane, octaphenylcyclotetrasiloxane, end-capping reagent and alkali glue, then reacting for 5h at 150 ℃, heating to 180 ℃, reacting for 30min, and then performing vacuum reduction for 8 hours at the temperature to obtain alkoxy end-capped phenyl silicone oil;
s3, preparing the room temperature curable silicone resin conformal coating: adding the hydroxymethyl organic silicon resin liquid, alkoxy end-capped phenyl silicone oil and a catalyst into a reaction kettle, performing reflux reaction for half an hour, cooling, filtering, adding a cross-linking agent, and uniformly stirring to obtain a product.
Further, in S1, the solvent is one or both of toluene and xylene.
Further, in S1, the obtained hydroxymethyl silicone resin liquid has a solid content of 60%.
Further, in S1, raw materials for preparing the hydroxymethyl organosilicon resin liquid: the mass ratio of the reaction monomer to the solvent to the concentrated HCl is 40-60:60-40:0.5-1.5, and the amount of the distilled water is 5-10 times of that of the concentrated HCl.
Further, in S2, the end-capping agent is 1, 3-dimethoxy-1, 1,3, 3-tetramethyldisiloxane.
Further, in S2, the weight ratio of octamethylcyclotetrasiloxane, octaphenylcyclotetrasiloxane, alkali gum and 1, 3-dimethoxy-1, 1,3, 3-tetramethyldisiloxane is 70-80:20-32:0.5-2: 1-5.
Furthermore, in S3, the weight ratio of the hydroxymethyl organosilicon resin liquid to the alkoxy-terminated phenyl silicone oil to the dibutyltin dilaurate is 70-90:10-30:0.05-0.1, and the crosslinking agent accounts for 3-8% of the content of the hydroxymethyl organosilicon resin liquid.
Compared with the prior art, the invention has the beneficial effects that:
(1) the raw materials selected for the organic silicon resin conformal coating capable of being cured at room temperature mainly comprise hydroxymethyl organic silicon resin and alkoxy end-capped phenyl silicone oil, the hydroxymethyl organic silicon resin has no benzene ring and small steric hindrance and is copolymerized with the alkoxy end-capped phenyl silicone oil to form a block structure, the alkoxy end-capped phenyl silicone oil contains benzene rings but is a linear polymer, so the steric hindrance of the alkoxy end-capped phenyl silicone oil is also small, the two substances are used as the raw materials, the steric hindrance of a reactant is reduced, and the reaction is easier, and the preparation method can be seen from the above invention, in the whole preparation process, only a solvent toluene or xylene is used when the hydroxymethyl organic silicon resin liquid is prepared, no additional solvent is added in the subsequent preparation process, and in the step of directly preparing a product, the reactant is added into a reaction kettle in a pot, the reaction temperature is reflux reaction, no inert gas is used for protection, and the product can be directly obtained without vacuum distillation of the solvent because no additional solvent is added, so that the preparation process is simple.
(2) The invention modifies the organic silicon resin to obtain the organic silicon resin conformal coating with the structure shown in the following formula, as can be seen from the structural formula shown in the following formula, difunctional chain links are introduced, so that the toughness of the silicon resin is increased, compared with the prior art that linear polymers are used for copolymerizing the silicon resin, alkoxy end-capped phenyl silicone oil is used for copolymerizing hydroxymethyl organic silicon resin, because the positions of phenyl groups are different, the reaction is easier to carry out from the preparation process on one hand, and because the positions of the phenyl groups are different, the spatial structure distribution of the product is more uniform on the other hand, so that the flexibility of the product is further improved,
(3) according to the room temperature curable silicone resin conformal coating, no flame retardant is added, and the silicone resin is modified by introducing alkoxy end-capped phenyl silicone oil, so that a certain amount of phenyl groups are introduced on linear chain links, and the flame retardance of the product is improved.
Drawings
FIG. 1 is an infrared spectrum of a hydroxymethyl silicone resin;
FIG. 2 is an infrared spectrum of alkoxy-terminated phenyl silicone oil;
FIG. 3 is an infrared spectrum of the product of the present invention.
Detailed Description
The present invention will be further described with reference to the following examples, which are intended to illustrate only some, but not all, of the embodiments of the present invention. All other embodiments that can be obtained by a person skilled in the art based on the embodiments of the present invention without any creative effort belong to the protection scope of the present invention.
Example 1
Preparing hydroxymethyl organic silicon resin: putting a mixture of 80g of ethyl orthosilicate, 20g of methyltrimethoxysilane and 140g of toluene into a reaction kettle, dropwise adding a mixture of 2g of concentrated HCl and 20g of distilled water at room temperature, heating to 60 ℃ for reflux reaction for 5 hours after dropwise adding is finished, heating to 70-80 ℃ to evaporate methanol and water generated by the reaction, then heating to 110 ℃ for reflux reaction for 8 hours, cooling to 60 ℃, adding 3g of hexamethyldisilazane to neutralize HCl, heating to 110 ℃ again, concentrating to a resin liquid with the solid content of 50%, and cooling for later use;
preparation of alkoxy-terminated phenyl silicone oil: uniformly mixing 100g of octamethylcyclotetrasiloxane, 40g of octaphenylcyclotetrasiloxane, 2g of 1, 3-dimethoxy-1, 1,3, 3-tetramethyldisiloxane and 2g of alkali glue, then reacting at 150 ℃ for 5 hours, heating to 180 ℃ for 30min, and then carrying out vacuum reduction at the temperature for 8 hours to obtain phenyl silicone oil with the phenyl content of 22% and the viscosity of 1.5 ten thousand;
preparing a block silicone resin conformal coating: adding 80g of hydroxymethyl organic silicon resin liquid into a reaction kettle, adding 10g of alkoxy-terminated phenyl silicone oil into the reaction kettle, adding 0.05g of dibutyltin dilaurate into the reaction kettle, carrying out reflux reaction for half an hour, cooling, filtering, adding 4g of monomethyltrimethoxysilane, and uniformly stirring to obtain a colorless and transparent liquid product.
The obtained hydroxymethylThe silicone-based resin, alkoxy-terminated phenyl silicone oil and the product were subjected to infrared analysis, respectively, as shown in FIGS. 1 to 3. As can be seen from FIG. 1, the height is 1257 cm-1，842 cm-1，756cm-1All show obvious absorption peaks, which indicates that the product contains Me3SiO group, wherein Me is methyl at 1078 cm-1The double peak is the characteristic absorption peak of Si-O-Si and is in 3444 cm-1The absorption peak at (A) is a hydroxyl group peak. As can be seen from FIG. 2, 2964cm-1The absorption peak is the C-H stretching vibration peak of the benzene ring; 1431 cm-1Has a sharp absorption peak of Si-C6H5Stretching vibration peak of middle benzene ring; at 1772-1955 cm-1The characteristic absorption peak of phenyl is at 4 continuous small attraction peaks; 1000-1150 cm-1The broad peak is the Si-O-Si stretching vibration absorption peak and is the characteristic absorption peak of the silicone resin. The C-O bond of the methoxy group has an absorption peak at 1200-1000 but is located at 1000-1150 cm-1The broad peak of Si-O-Si in (B) covers, although it is not clearly seen, the broad peak in FIG. 2 is also found to be significantly broader than the Si-O-Si peak in FIG. 1 and is located at 1257 cm-1，842 cm-1，760cm-1The methyl peaks are all in, which shows that the methoxy phenyl silicone oil is synthesized. As can be seen from FIG. 3, 2964cm-1The absorption peak is the C-H stretching vibration peak of the benzene ring; 1431 cm-1Has a sharp absorption peak of Si-C6H5Stretching vibration peak of middle benzene ring; at 1772-1955 cm-1The characteristic absorption peak of phenyl is at 4 continuous small attraction peaks; 1000-1150 cm-1The broad peak is the Si-O-Si stretching vibration absorption peak and is the characteristic absorption peak of the silicone resin. And 3444 cm-1The peak at hydroxyl group disappeared, indicating that the hydroxyl group reaction was complete.
Example 2
Preparing hydroxymethyl organic silicon resin: putting 70g of ethyl orthosilicate, 10g of dimethyl dimethoxysilane and 120g of xylene mixture into a reaction kettle, dropwise adding 1g of concentrated HCl +8g of distilled water mixture at room temperature, heating to 60 ℃ for reflux reaction for 5 hours after dropwise adding, heating to 70-80 ℃ to evaporate methanol and water generated by the reaction, then heating to 110 ℃ for reflux reaction for 8 hours, cooling to 60 ℃, adding 3g of hexamethyldisilazane to neutralize HCl, heating to 110 ℃ again, concentrating to a resin liquid with a solid content of 50%, and cooling for later use;
preparation of alkoxy-terminated phenyl silicone oil: uniformly mixing 140g of octamethylcyclotetrasiloxane, 40g of octaphenylcyclotetrasiloxane, 6g of 1, 3-dimethoxy-1, 1,3, 3-tetramethyldisiloxane and 1.5g of alkali glue, then reacting at 150 ℃ for 5 hours, heating to 180 ℃ for reaction for 30min, and then carrying out vacuum reduction for 8 hours at the temperature to obtain phenyl silicone oil with the phenyl content of 16% and the viscosity of 1 ten thousand;
preparing a block silicone resin conformal coating: 70g of hydroxymethyl organic silicon resin liquid is added into a reaction kettle, 15g of alkoxy end-capped phenyl silicone oil is added into the reaction kettle, 0.08g of dibutyltin dilaurate is added for reflux reaction for half an hour, the temperature is reduced, the filtration is carried out, 2.1g of monomethyltrimethoxysilane is added, the mixture is stirred evenly and packaged to obtain the product.
Example 3
Preparing hydroxymethyl organic silicon resin: putting a mixture of 100g of tetraethoxysilane and 150g of toluene into a reaction kettle, dropwise adding a mixture of 3g of concentrated HCl and 15g of distilled water at room temperature, heating to 60 ℃ for reflux reaction for 5 hours after dropwise adding is finished, heating to 70-80 ℃ to evaporate methanol and water generated by the reaction, then heating to 110 ℃ for reflux reaction for 8 hours, cooling to 60 ℃, adding 3g of hexamethyldisilazane for neutralizing HCl, heating to 110 ℃ again, concentrating to a resin liquid with 50% of solid content, and cooling for later use;
preparation of alkoxy-terminated phenyl silicone oil: uniformly mixing 140g of octamethylcyclotetrasiloxane, 80g of octaphenylcyclotetrasiloxane, 2g of 1, 3-dimethoxy-1, 1,3, 3-tetramethyldisiloxane and 4g of alkali glue, then reacting at 150 ℃ for 5 hours, heating to 180 ℃ for 30min, and then carrying out vacuum reduction at the temperature for 8 hours to obtain alkoxy-terminated phenyl silicone oil; obtaining phenyl silicone oil with the phenyl content of 28 percent and the viscosity of 1.2 ten thousand; preparing a block silicone resin conformal coating: adding 90g of hydroxymethyl organic silicon resin liquid into a reaction kettle, adding 30g of alkoxy end-capped phenyl silicone oil into the reaction kettle, adding 0.1g of dibutyltin dilaurate into the reaction kettle, carrying out reflux reaction for half an hour, cooling, filtering, adding 7.2g of monomethyltrimethoxysilane, stirring uniformly, and packaging to obtain the product.
The coating materials obtained in examples 1 to 3 were tested for their properties, and the test methods and test results are shown in Table 1. As can be seen from the detection results in Table 1, the product is transparent liquid in appearance, and the surface drying time of the product is 5 min; on the premise of not adding any flame retardant, the flame retardant grade of the flame retardant can reach 94V 1; the product of the invention has excellent flexibility.
TABLE 1 tests of the properties of the coating materials obtained in examples 1 to 3
Claims (9)
1. The room temperature curable silicone resin conformal coating is characterized by being mainly prepared from the following raw materials: hydroxymethyl organic silicon resin, alkoxy end-capped phenyl silicone oil, a cross-linking agent and a catalyst,
wherein the structural formula of the hydroxymethyl organic silicon resin is as follows:
the structural formula of the alkoxy-terminated phenyl silicone oil is as follows:
the structural formula of the room temperature curable organic silicon resin conformal coating is as follows:
2. the room temperature curable silicone resin conformal coating of claim 1, wherein the catalyst is dibutyltin dilaurate and the cross-linking agent is monomethyltrimethoxysilane.
3. A preparation method of a room temperature curable silicone resin conformal coating is characterized by comprising the following steps:
s1, preparing hydroxymethyl organic silicon resin liquid: putting a reaction monomer and a solvent into a reaction kettle, dropwise adding a mixture of concentrated HCl and distilled water at room temperature, heating to 60 ℃ after dropwise adding, performing reflux reaction for 5 hours, heating to 70-80 ℃, evaporating methanol and water generated by the reaction, then heating to 110 ℃, performing reflux reaction for 8 hours, cooling to 60 ℃, adding hexamethyldisilazane, heating to 110 ℃, concentrating to a resin solution with a solid content of 60%, and cooling for later use, wherein the reaction monomer is one or more of methyltrimethoxysilane, ethyl orthosilicate and dimethyldimethoxysilane;
s2, preparing alkoxy-terminated phenyl silicone oil: uniformly mixing octamethylcyclotetrasiloxane, octaphenylcyclotetrasiloxane, end-capping reagent and alkali glue, then reacting for 5h at 150 ℃, heating to 180 ℃, reacting for 30min, and then performing vacuum reduction for 8 hours at the temperature to obtain alkoxy end-capped phenyl silicone oil;
s3, preparing the room temperature curable silicone resin conformal coating: adding the hydroxymethyl organic silicon resin liquid, alkoxy end-capped phenyl silicone oil and a catalyst into a reaction kettle, performing reflux reaction for half an hour, cooling, filtering, adding a cross-linking agent, and uniformly stirring to obtain a product.
4. The method for preparing room temperature curable silicone resin conformal coating material according to claim 3, wherein in S1, the solvent is one or both of toluene and xylene.
5. The method for preparing room temperature curable silicone resin conformal coating material according to claim 3, wherein in S1, the obtained hydroxymethyl silicone resin liquid has a solid content of 60%.
6. The method for preparing room temperature curable silicone resin conformal coating according to claim 3, wherein in S1, raw materials for preparing hydroxymethyl silicone resin liquid: the mass ratio of the reaction monomer to the solvent to the concentrated HCl is 40-60:60-40:0.5-1.5, and the amount of the distilled water is 5-10 times of that of the concentrated HCl.
7. The method of claim 3, wherein the end-capping agent is 1, 3-dimethoxy-1, 1,3, 3-tetramethyldisiloxane as the end-capping agent in S2.
8. The method for preparing room temperature curable silicone resin conformal coating material according to claim 7, wherein in S2, the weight ratio of octamethylcyclotetrasiloxane, octaphenylcyclotetrasiloxane, alkali gum and 1, 3-dimethoxy-1, 1,3, 3-tetramethyldisiloxane is 70-80:20-32:0.5-2: 1-5.
9. The method for preparing the room temperature curable silicone resin conformal coating material according to claim 3, wherein in S3, the weight ratio of the hydroxymethyl silicone resin liquid to the alkoxy-terminated phenyl silicone oil to the dibutyltin dilaurate is 70-90:10-30:0.05-0.1, and the crosslinking agent accounts for 3-8% of the content of the hydroxymethyl silicone resin liquid.
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| CN109232894B (en) * | 2018-09-21 | 2021-04-06 | 广州天宸高新材料有限公司 | Methoxy-terminated methylphenyl polysiloxane resin, organic silicon coating adhesive, preparation method and application |
| CN110317343B (en) * | 2019-07-04 | 2021-10-22 | 中蓝晨光化工有限公司 | Single-component room-temperature curing organic silicon resin containing MQ structural unit and preparation method thereof |
| CN111440531A (en) * | 2020-05-14 | 2020-07-24 | 成都拓利科技股份有限公司 | Solvent-free moisture-curing type organic silicon coating and preparation method thereof |
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